TWI611003B - 用於電子裝置之化合物類 - Google Patents
用於電子裝置之化合物類 Download PDFInfo
- Publication number
- TWI611003B TWI611003B TW102131558A TW102131558A TWI611003B TW I611003 B TWI611003 B TW I611003B TW 102131558 A TW102131558 A TW 102131558A TW 102131558 A TW102131558 A TW 102131558A TW I611003 B TWI611003 B TW I611003B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- groups
- aromatic
- substituted
- atoms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 112
- 125000003118 aryl group Chemical group 0.000 claims description 106
- -1 spiroindolyl Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000412 dendrimer Substances 0.000 claims description 16
- 229920000736 dendritic polymer Polymers 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
- 239000010410 layer Substances 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 41
- 239000007787 solid Substances 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- 239000012153 distilled water Substances 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000002019 doping agent Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000005266 diarylamine group Chemical group 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 150000004032 porphyrins Chemical class 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- IULUNTXBHHKFFR-UHFFFAOYSA-N 4-methyl-n,n-diphenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 IULUNTXBHHKFFR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- OMMRSCXBBGEIGA-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-4-methylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 OMMRSCXBBGEIGA-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 2
- DDJNQLVBMMNGAU-UHFFFAOYSA-N 2-(1-phenylnaphthalen-2-yl)propan-2-ol Chemical compound CC(C)(O)C1=CC=C2C=CC=CC2=C1C1=CC=CC=C1 DDJNQLVBMMNGAU-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- MHIITNFQDPFSES-UHFFFAOYSA-N 25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4,6,8(27),9,11,13,15,17,19,21,23-tridecaene Chemical compound N1C(C=C2C3=CC=CC=C3C(C=C3NC(=C4)C=C3)=N2)=CC=C1C=C1C=CC4=N1 MHIITNFQDPFSES-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(CC)(*C(C)(*)N*)C(C(CC*)=C(C)C(C)*(C)[C@](C)(*)CC)=C(C)C Chemical compound CCC(CC)(*C(C)(*)N*)C(C(CC*)=C(C)C(C)*(C)[C@](C)(*)CC)=C(C)C 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QVBBVTKKBJWGAU-UHFFFAOYSA-N NN.C1=CC=C2C=CC=3C=CC=C4C5=C(C1=C2C43)C=CC=C5 Chemical compound NN.C1=CC=C2C=CC=3C=CC=C4C5=C(C1=C2C43)C=CC=C5 QVBBVTKKBJWGAU-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001398 aluminium Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- BFDOJPZIKWNDLI-UHFFFAOYSA-N diphenyl-(1-phenylnaphthalen-2-yl)methanol Chemical compound C=1C=CC=CC=1C(C=1C(=C2C=CC=CC2=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFDOJPZIKWNDLI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- DOZCTPAUYJQGBD-UHFFFAOYSA-N indeno[1,2-b]indole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4N=C3C2=C1 DOZCTPAUYJQGBD-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- DAUCSGSCDZOKLE-UHFFFAOYSA-N methyl 1-bromonaphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(Br)C(C(=O)OC)=CC=C21 DAUCSGSCDZOKLE-UHFFFAOYSA-N 0.000 description 2
- FISOOVFVWPYVDL-UHFFFAOYSA-N methyl 1-phenylnaphthalene-2-carboxylate Chemical compound COC(=O)C1=CC=C2C=CC=CC2=C1C1=CC=CC=C1 FISOOVFVWPYVDL-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 1
- WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- AGSGBXQHMGBCBO-UHFFFAOYSA-N 1H-diazasilole Chemical compound N1C=C[SiH]=N1 AGSGBXQHMGBCBO-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- LPHIYKWSEYTCLW-UHFFFAOYSA-N 1h-azaborole Chemical class N1B=CC=C1 LPHIYKWSEYTCLW-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical class C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- OKXVARYIKDXAEO-UHFFFAOYSA-N 2,3,3-trimethylbutan-2-ol Chemical compound CC(C)(C)C(C)(C)O OKXVARYIKDXAEO-UHFFFAOYSA-N 0.000 description 1
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- KJCRNHQXMXUTEB-UHFFFAOYSA-N 69637-93-0 Chemical compound C1=CC=C2N=C(N=C3NC=4C(=CC=CC=4)NC3=N3)C3=NC2=C1 KJCRNHQXMXUTEB-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- CRCGRIHEUHJGDC-UHFFFAOYSA-N C=C.CC1=CC=CC=C1C Chemical group C=C.CC1=CC=CC=C1C CRCGRIHEUHJGDC-UHFFFAOYSA-N 0.000 description 1
- UOKKCSDFCKMVSM-UHFFFAOYSA-N CCCCCCCCSS(C(C(CC)CCCC)SCCCCCC)(SCCCCCCC)(SC1CCCCCCC1)(SC2CCCCCC2)SC3CCCCC3 Chemical compound CCCCCCCCSS(C(C(CC)CCCC)SCCCCCC)(SCCCCCCC)(SC1CCCCCCC1)(SC2CCCCCC2)SC3CCCCC3 UOKKCSDFCKMVSM-UHFFFAOYSA-N 0.000 description 1
- LNSXRXFBSDRILE-UHFFFAOYSA-N Cucurbitacin Natural products CC(=O)OC(C)(C)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C)(C)C(O)C(O)CC4(C)C3(C)C(=O)CC12C LNSXRXFBSDRILE-UHFFFAOYSA-N 0.000 description 1
- CVKKIVYBGGDJCR-SXDZHWHFSA-N Cucurbitacin B Natural products CC(=O)OC(C)(C)C=CC(=O)[C@@](C)(O)[C@@H]1[C@@H](O)C[C@]2(C)C3=CC[C@@H]4C(C)(C)C(=O)[C@H](O)C[C@@]4(C)[C@@H]3CC(=O)[C@@]12C CVKKIVYBGGDJCR-SXDZHWHFSA-N 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HIAXGCOZOIPYFT-UHFFFAOYSA-N [Ru].N1C=CC2=CC=CC=C12 Chemical group [Ru].N1C=CC2=CC=CC=C12 HIAXGCOZOIPYFT-UHFFFAOYSA-N 0.000 description 1
- BQVLBVDKRFQMCK-UHFFFAOYSA-N [S].C(#CC)SC(C#CSC#CCC)CC Chemical compound [S].C(#CC)SC(C#CSC#CCC)CC BQVLBVDKRFQMCK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000001904 cucurbitacins Chemical class 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000007858 diazaphosphole derivatives Chemical class 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- PIGAXYFCLPQWOD-UHFFFAOYSA-N dihydrocucurbitacin I Natural products CC12C(=O)CC3(C)C(C(C)(O)C(=O)CCC(C)(O)C)C(O)CC3(C)C1CC=C1C2C=C(O)C(=O)C1(C)C PIGAXYFCLPQWOD-UHFFFAOYSA-N 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- NWPWGNPPZVZAKO-UHFFFAOYSA-N fluoren-1-one Chemical compound C1=CC=C2C3=CC=CC(=O)C3=CC2=C1 NWPWGNPPZVZAKO-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920006150 hyperbranched polyester Polymers 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- XYUVUTPIRQLXDM-UHFFFAOYSA-N indeno[1,2-b]fluoren-11-amine Chemical compound C1=CC=CC2=C3C=C4C(C(=C3C=C12)N)=C1C=CC=CC1=C4 XYUVUTPIRQLXDM-UHFFFAOYSA-N 0.000 description 1
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical class C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- ZXUVIGYTEAQUBH-UHFFFAOYSA-N phosphoric acid;potassium;hydrate Chemical compound O.[K].OP(O)(O)=O ZXUVIGYTEAQUBH-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
- C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3488—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/404—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing boron or phosphorus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thin Film Transistor (AREA)
- Indole Compounds (AREA)
Abstract
本發明關於適合用於電子裝置之化合物類,較佳是用於有機電激發光裝置者。
Description
本發明關於一種化合物、該化合物在電子裝置中之用途、及包含該化合物之電子裝置。
在目前重要的是,發展可用以在一或多項相關之點(諸如功率效率、使用期限或所發射之光的色彩座標)上獲得電子裝置之改良性質的化合物。
依照本發明,電子裝置一詞通常用來表示包含有機材料之電子裝置。特別地,這些是用來表示有機積體電路(OICs)、有機場效應電晶體(OFETs)、有機薄膜電晶體(OTFTs)、有機發光電晶體(OLETs)、有機太陽能電池(OSCs)、有機光學偵測器、有機感光器、有機場淬熄裝置(OFQDs)、有機發光電化學電池(OLECs)、有機雷射二極體(O-雷射)及有機電激發光裝置(OLEDs)。
特別重要的是要提供化合物以供用於最後提及之已知為OLEDs之電子裝置中。OLEDs之一般構造及功能原則
對精於此技藝之人士是已知的且特別是在US 4539507、US 5151629、EP 0676461及WO 1998/27136中描述。
關於OLEDs之效能數據,尤其是鑒於廣泛的商業用途,例如在顯示器中或作為光源上,仍需要另外的改良。就此而論,特別重要的是該OLEDs之使用期限、效率及操作電壓以及所達成之色彩值。特別地,在發藍光之OLEDs的情況中,關於該裝置之使用期限有改良的潛力。
就此而論,最重要的是在該OLED中作為摻雜劑或作為發射用化合物之化合物的選擇。
由該先前技藝已知多種用於此目的之化合物,尤其是含一或多個縮合芳香基之芳香基胺。
在此可藉由例舉在WO 2008/006449及WO 2010/012328中所揭示之化合物而提及,其是基於茚並茀主幹,其中該等苯基之一係經延伸以形成較大之芳香基,例如形成萘基或芘基。該等化合物另外含有胺基,其代表隨意經取代之二苯基胺基。
雖然在上述申請案中所揭示之化合物是有價值之功能化合物,彼等還不能理想地適合作為在OLEDs中之深藍光發射劑。特別地,不斷增加的需求意味對於核心裝置的參數(諸如功率效率及使用期限)的改良有持續的需要。
以下定義之新穎化合物達成此技術目的。
其中:Ar1在每一情況下,相同地或不同地,係選自具有5至30個芳香族環原子之芳香族或雜芳香族環系統,其可經一或多個基團R1取代;
Ar2在每一情況下,相同地或不同地,是具有10至30個芳香族環原子之芳香基或雜芳香基,其可經一或多個基團R1取代;Ara在每一情況下,相同地或不同地,是具有5至30個芳香族環原子之芳香基或雜芳香基,其可經一或多個基團R1取代;R1在每一情況下,相同地或不同地是H、D、F、Cl、Br、I、C(=O)R2、CN、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、具有1至20個C原子之直鏈烷基、烷氧基或硫烷基或具有3至20個C原子之分枝或環狀烷基、烷氧基或硫烷基或具有2至20個C原子之烯基或炔基(其中上述基團可分別經一或多個基團R2取代且其中上述基團之一或多個CH2基團可經-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SO或SO2代替且其中上述基團之一或多個H原子可經D、F、Cl、Br、I、CN或NO2代替)、或在每一情況下可經一或多個基團R2取代之具有5至30個芳香族環原子之芳香族或雜芳香族環系統或可經一或多個基團R2取代之具有5至30個芳香族環原子之芳香基氧基或雜芳香基氧基,其中二或多個基團R1可彼此連
接且可形成一環;R2在每一情況下,相同地或不同地是H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、具有1至20個C原子之直鏈烷基、烷氧基或硫烷基或具有3至20個C原子之分枝或環狀烷基、烷氧基或硫烷基或具有2至20個C原子之烯基或炔基(其中上述基團可分別經一或多個基團R3取代且其中在上述基團中之一或多個CH2基團可經-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2代替且其中上述基團之一或多個H原子可經D、F、Cl、Br、I、CN或NO2代替)、或在每一情況下可經一或多個基團R3取代之具有5至30個芳香族環原子之芳香族或雜芳香族環系統或可經一或多個基團R3取代之具有5至30個芳香族環原子之芳香基氧基或雜芳香基氧基,其中二或多個基團R2可彼此連接且可形成一環;R3在每一情況下,相同地或不同地是H、D、F或具有1至20個C原子之脂肪族、芳香族或雜芳香族有機基團,此外,其中一或多個H原子可經D或F代替;二或多個取代基R3在
此可彼此連接且形成一環;X在每一情況下,相同地或不同地是BR1、C(R1)2、C(R1)2-C(R1)2、Si(R1)2、Si(R1)2-Si(R1)2、C=O、C=NR1、C=C(R1)2、C(=O)N(R1)、O、S、S=O、SO2、NR1、PR1或P(=O)R1;a等於0或1;b等於0、1或2;m、n、o、p、q及r在每一情況中,相同地或不同地是0或1;其中在彼等為0之情況下,基團R1鍵結在對應基團X所鍵結之相關位置上;其中m和n之合等於1或2,且o和p之合等於1或2,且q和r之合等於1或2。
該化合物高度適合用於OLEDs中。尤其,彼適合用以作為發射深藍光之發射劑化合物。尤其,在用於OLEDs時,彼導致該裝置之使用期限及/或功率效率之改良。
以下給予供本申請案之目的所適用之用語的一般定義。
在本發明之觀念中,芳香基含有6至60個芳香族環原子;在本發明之觀念中,雜芳香基含有5至60個芳香族環原子,而其至少一者是雜原子。該雜原子較佳選自N、O及S。這表示基本的定義。若在本發明之描述中指出其他較佳者,例如關於芳香族環原子之數目或所存在之雜原子,則這些是適用的。
芳香基或雜芳香基在此被用來表示簡單之芳香族環(亦即苯)或簡單之雜芳香族環(例如吡啶、嘧啶或噻吩)或縮合的(環狀)芳香族或雜芳香族多環(例如萘、菲、醌或咔唑)。在本發明之觀念中,縮合的(環狀)芳香族或雜芳香族多環係由二或更多簡單的芳香族或雜芳香族環互相縮合所構成者。
在每一情況中可經上述基團取代且可經由任何所要之位置連接該芳香族或雜芳香族環系統的芳香基或雜芳香基尤其被用來表示由以下衍生之基團:苯、萘、蒽、菲、芘、二氫芘、苯并[a]菲、苝、1,2-苯并苊、苯并蒽、苯并菲、稠四苯、稠五苯、苯并芘、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻、啡、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡并咪唑、喹啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、異唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、苯并嗒、嘧啶、苯并嘧啶、喹啉、吡、啡、啶、吖咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌
呤、喋啶、吲及苯并噻二唑。
依照本發明定義之芳香基氧基用來表示經由氧原子鍵結之如以上定義的芳香基。類似的定義適用於雜芳香基氧基。
在本發明觀念中,芳香族環系統含有6至60個C原子於該環系統中。在本發明觀念中,雜芳香族環系統含有5至60個芳香族環原子,其至少一者是雜原子。該雜原子係較佳選自N、O及/或S。在本發明觀念中,芳香族或雜芳香族環系統意圖用來表示一種系統,其無需僅含有芳香基或雜芳香基,反而在此之外,其中多個芳香基或雜芳香基可藉由非芳香族單元(較佳地,少於10%之該等原子並非H),諸如sp3-混成之C、Si、N或O原子、sp2-混成之C或N原子、或sp-混成之C原子連接。因此,例如,諸如9,9'-螺雙茀、9,9'-二芳香基茀、三芳香基胺、二芳香基醚、二苯乙烯等系統也意圖被採用以作為本發明觀念中之芳香族環系統,如同其中之二或多個芳香基係例如藉由線性或環狀烷基、烯基或炔基或藉由矽烷基連接的系統。另外,其中之二或多個芳香基或雜芳香基經由單鍵彼此連接之系統也被採用以作為本發明觀念中之芳香族或雜芳香族環系統,例如諸如聯苯、聯三苯或二苯基三等系統。
在每一情況中也可經如上定義之基團所取代且可經由任何想要之位置連接該芳香族或雜芳香族基團之具有5-60個芳香族環原子之芳香族或雜芳香族環系統特別是用來表示衍生自以下之基團:苯、萘、蒽、苯並蒽、菲、苯並
菲、芘、苯并[a]菲、苝、1,2-苯并苊、稠四苯、稠五苯、苯並芘、聯苯、伸聯苯、聯三苯、伸聯三苯、聯四苯、茀、螺聯茀、二氫菲、二氫芘、四氫芘、順式-或反式-茚并茀、參茚并苯、異參茚并苯、螺參茚并苯、螺異參茚并苯、呋喃、苯并呋喃、異苯并呋喃、二苯並呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、異喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻、啡、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡并咪唑、喹啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、異唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、苯并嗒、嘧啶、苯并嘧啶、喹啉、1,5-二吖蒽、2,7-二吖芘、2,3-二吖芘、1,6-二吖芘、1,8-二吖芘、4,5-二吖芘、4,5,9,10-四吖芘、吡、啡、啡、啡噻、茀賓(fluorubin)、啶、吖咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、喋啶、吲及苯并噻二唑,或這些基團之組合物。
為供本發明之目的,具有1至40個C原子之直鏈烷基或具有3至40個C原子之分枝或環狀烷基或具有2至
40個C原子之烯基或炔基(其中在這些之外,個別之H原子或CH2基團可經上述之在該等基團定義下的基團所取代)較佳被採用以表示以下基團:甲基、乙基、正-丙基、異-丙基、正-丁基、異-丁基、第二-丁基、第三-丁基、2-甲基丁基、正-戊基、第二-戊基、環戊基、新戊基、正-己基、環己基、新己基、正-庚基、環庚基、正-辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1至40個C原子之烷氧基或硫烷基較佳被採用以表示甲氧基、三氟甲氧基、乙氧基、正-丙氧基、異-丙氧基、正-丁氧基、異-丁氧基、第二-丁氧基、第三-丁氧基、正-戊氧基、第二-戊氧基、2-甲基丁氧基、正-己氧基、環己氧基、正-庚氧基、環庚氧基、正-辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正-丙硫基、異-丙硫基、正-丁硫基、異-丁硫基、第二-丁硫基、第三-丁硫基、正-戊硫基、第二-戊硫基、正-己硫基、環己硫基、正-庚硫基、環庚硫基、正-辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫
基、庚炔硫基或辛炔硫基。
Ar1在每一情況下,相同地或不同地,係較佳地選自具有5至24個芳香族環原子之芳香族或雜芳香族環系統,其可經一或多個基團R1取代。Ar1特佳地是具有6至18個芳香族環原子之芳香族或雜芳香族環系統,其可經一或多個基團R1取代。
Ar1另外較佳地是具有6至16個芳香族環原子之芳香基或雜芳香基,其可經一或多個基團R1取代。
Ar1在每一情況下,相同地或不同地,係極特佳地選自苯基、萘基、蒽基、菲基、芘基、三苯基烯基、苯并[a]菲基、聯苯基、聯三苯基、茀基、螺聯茀基、咔唑基、二
苯并呋喃、二苯并苯硫基或西拉茀基(silafluorenyl)、彼分別可經一或多個基團R1所取代。
Ar1在每一情況中,另外較佳地係在式中相同地被選擇。
Ar2在每一情況下,相同地或不同地,較佳地選自具有10至22個芳香族環原子之芳香基,其可經一或多個基團R1取代,特佳地選自具有10至18個芳香族環原子之芳香基,其可經一或多個基團R1取代。
其中對該式之基團的鍵結位置可以是在任何想要之位置上且其中該基團可經一或多個基團R1取代。該橋X與Ar2及苯基較佳形成五或六員環,特佳是五員環。
Ar2另外較佳地在每一情況中係相同地被選擇。
對於式(III)之化合物,基團Ar2較佳經一或多個選自具有5至30個芳香族環原子之芳香族或雜芳香族環系統(其可經一或多個基團R2取代)之基團R1取代。在式(III)左邊之基團Ar2特佳經一或多個選自具有5至30個芳香族環原子之芳香族或雜芳香族環系統(其可經一或多個基團R2取代)之基團R1取代。該基團Ar2之取代基R1,尤其是在式(III)左邊之基團Ar2的取代基R1特佳是具有6至16個芳香族環原子之芳香基或雜芳香基,其可經一或多個基團R2取代。
該基團Ara較佳地在每一情況中,相同地或不同地,係芳香基或雜芳香基,其具有5至18個芳香族環原子,特佳地5至14個芳香族環原子,極特加地5至10個芳香族環原子,其中Ara可經一或多個基團R1取代。
Ara另外較佳示芳香基,其具有6至18個芳香族環原子,特佳地6至14個芳香族環原子,極特佳地6至10個芳香族環原子,其中Ara可經一或多個基團R1取代。
Ara另外較佳地在每一情況中係相同地被選擇。
基團X在每一情況下,相同地或不同地,較佳是C(R1)2、C(R1)2-C(R1)2、Si(R1)2、Si(R1)2-Si(R1)2、O、S、NR1或PR1。X在每一情況下,相同地或不同地,特佳是
C(R1)2或Si(R1)2,極特佳是C(R1)2。
R1在每一情況下,相同地或不同地是H、D、F、CN、Si(R2)3、N(R2)2、具有1至20個C原子之直鏈烷基或烷氧基或具有3至20個C原子之分枝或環狀烷基或烷氧基(其中上述基團可分別經一或多個基團R2取代且其中在上述基團中之一或多個CH2基團可經-C≡C-、-R2C=CR2-、Si(R2)2、C=O、C=NR2、-NR2-、-O-、-S-、-C(=O)O-或-C(=O)NR2-代替)、或在每一情況下可經一或多個基團R2取代之具有5至20個芳香族環原子之芳香族或雜芳香族環系統,其中二或多個基團R1可彼此連接且可形成一環。
R1在每一情況中,相同地或不同地,特佳地選自H、D、F、CN、Si(R2)3、具有1至8個C原子之直鏈烷基或具有3至8個C原子之分枝或環狀烷基(其中該烷基可分別經一或多個基團R2取代且其中在該烷基中之一或多個CH2基團可經-C≡C-、-R2C=CR2-、Si(R2)2、C=O或-O-代替)、或在每一情況下可經一或多個基團R2取代之具有6至16個芳香族環原子之芳香基或雜芳香基。
與基團X(尤其是表示C(R1)2之基團X)鍵結的R1在每一情況中,相同地或不同地,較佳選自可經一或多個基團R2取代之具有1至10個C原子的烷基及可經一或多個基團R2取代之具有6至12個芳香族環原子的芳香族或雜芳香族環系統。與該同一基團X鍵結之二基團R1尤其是在表示C(R1)2之基團X的情況中可彼此形成一環。
R2在每一情況中,相同地或不同地,較佳是H、D、F、CN、Si(R3)3、N(R3)2、具有1至20個C原子之直鏈烷基或烷氧基或具有3至20個C碳原子之分枝或環狀烷基或烷氧基(其中上述基團可分別經一或多個基團R3取代且其中在上述基團中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-代替)、或在每一情況下可經一或多個基團R3取代之具有5至20個芳香族環原子之芳香族或雜芳香族環系統,其中二或多個基團R2可彼此連接且可形成一環。
R2在每一情況中,相同地或不同地,特佳選自H、D、F、CN、具有1至8個C原子之直鏈烷基或具有3至8個C碳原子之分枝或環狀烷基(其中該烷基可分別經一或多個基團R2取代且其中在該烷基中之一或多個CH2基團可經-C≡C-、-R3C=CR3-、Si(R3)2、C=O或-O-代替)、或在每一情況下可經一或多個基團R3取代之具有6至16個芳香族環原子之芳香基或雜芳香基。
a另外較佳等於1。
b另外較佳等於2。
m和n之合另外較佳等於1。
o和p之合另外較佳等於1。
q和r之合另外較佳等於1。
m及p另外較佳等於1且n及o另外較佳等於0。
n及o另外較佳等於1且m及p另外較佳等於0。
其中所出現之符號及指數係如同以上所定義的。以上對該等符號及指數所指明之較佳具體例係較佳適用的。
在以上各式中,m及p較佳等於1且n及o較佳等於0。二擇一地,在以上各式中,n及o較佳等於1且m及p較佳等於0。
其中所出現之符號及指數係如同以上所定義的且其中Ara可鍵結在芳香基端基之任何想要的閒置位置上且其中該芳香基端基可在每一其他閒置位置上經基團R1取代。
以上對該等符號及指數所指明之較佳具體例,尤其是對於Ara者,係較佳適用的。
在以上各式中,m及p較佳等於1且n及o較佳等於0。二擇一地,在以上各式中,n及o較佳等於1且m及p較佳等於0。
其中所出現之符號及指數係如同以上所定義的。以上對於符號及指數所指明之較佳具體例係較佳地適用。
在所繪製之式(III-1)至(III-4)之中,特佳的是式(III-1)。
對上述之各式而言,m及p較佳等於1且n及o較佳等於0。二擇一地,對上述之各式而言,n及o較佳等於1且m及p較佳等於0。對上述之各式而言,q還較佳等於0且r還較佳等於1。二擇一地,對上述之各式而言,q等於1且r較佳等於0。
對上述之各式而言,所繪製之基團R1之至少一者(較佳是在該氮原子左邊之單元上的基團R1之至少一者)還較佳地選自可經一或多個基團R2取代之具有5至30個芳香族環原子之芳香族或雜芳香族環系統,特佳地選自可經一或多個基團R2取代之具有6至16個芳香族環
原子之芳香基或雜芳香基。
依本發明之化合物的實例顯示於下表中。
依照本發明之化合物可藉由精於此技藝之人士所普遍已知的有機製備化學方法所合成。較佳被利用之反應的實例是鹵化及過渡金屬催化之偶合反應,較佳是鈴木偶合及巴哈法氏偶合。
製備該等化合物之說明性的一般合成途徑顯示於下。
依照流程1之方法開始於三芳香基胺基化合物,其在
該三個芳香基之二者上含有反應基團。帶有用於形成橋X的先質的雙芳香基化合物可經由過渡金屬催化之反應(例如鈴木反應),偶合於這些位置中。在隨後之環化反應中,該橋X被導入。可以進行另外之官能化反應,以獲得依照本發明之最終化合物。
依照流程2之方法開始於橋接的三芳香基化合物,較佳是茚并茀化合物。此在第一步驟中例如藉由溴化以被官能化。基團Ar隨後藉由過渡金屬催化之偶合反應(例如藉由鈴木偶合)被導入。在另外之在該母構造之相對邊上選擇性官能化之後,可經由另外之偶合反應(例如巴哈法氏偶合),導入二芳香基胺基。可以進行另外之官能化反應以獲得依照本發明之最終化合物。
在依照流程3之方法中,首先製備該茚并茀衍生物,然後官能化,且隨後在二段巴哈法氏偶合中反應,其中分別使用不同之胺衍生物。以此方式,可以獲得在該中心氮原子上含有三個不同基團之化合物,尤其是式(III)之化合物。
本發明因此另外關於一種製備式(I)、(II)或(III)之化合物的方法,其特徵在於利用一或多種有機金屬偶合方法。
較佳是選自巴哈法氏偶合及鈴木偶合之偶合方法。
依照上述本發明之化合物,尤其是經反應性離去基團(諸如溴、碘、氯、硼酸或硼酸酯)所取代之化合物可被用來作為用於製造對應之寡聚物、樹枝狀聚合物或聚合物之單體。適合之反應性離去基團是例如溴、碘、氯、硼酸、硼酸酯類、胺類、具有末端C-C雙鍵或C-C三鍵之烯基或炔基、氧環乙烷、氧環丁烷、進行環加成(例如1,3-二極性環加成)之基團(例如二烯類或疊氮化物)、羧酸衍生物、醇類及矽烷類。
本發明因此另外關於含有式(I)、(II)或(III)之一或多種化合物之寡聚物、聚合物或樹枝狀聚合物,其中與該聚合物、寡聚物或樹枝狀聚合物之鍵結可定位在經R1或R2取代之式(I)、(II)或(III)中的任何所要位置上。依照式(I)、(II)或(III)之化合物的鏈接,該化合物是該寡聚物或聚合物之側鏈的構成分子或該主鏈之構成分子。在本發明觀念中,寡聚物是要用來表示一種由至少三個單體單元所構成之化合物。在本發明觀念中,聚合物是要用來表示一種由至少十個單體單元所構成之化合物。依照本發明之聚合物、寡聚物或樹枝狀聚合物可是共軛的、部份共軛的或非共軛的。依照本發明之寡聚物或聚合物可以是線性的、分枝的或樹枝狀的。在以線性方式鏈接之結構中,式(I)、(II)或(III)之單元可彼此直接鏈接或彼等可經由二價基團,例如經由經取代或未經取代之伸烷基,經由雜原子或經由二價芳香族或雜芳香族基團彼此鏈接。在分枝及樹枝狀構造中,例如,式
(I)、(II)或(III)之三或多個單元可經由三價或多價基團,例如經由三價或多價芳香族或雜芳香族基團鏈接,以形成分枝或樹枝狀寡聚物或聚合物。
如上述較佳地,式(I)、(II)或(III)之化合物適用於在寡聚物、樹枝狀聚合物及聚合物中之式(I)、(II)或(III)的重覆單元。
為要製備該寡聚物或聚合物,依照本發明之單體被均聚合或與另外之單體共聚合。適合且較佳之共單體係選自茀類(例如依照EP 842208或WO 2000/22026)、螺聯茀類(例如依照EP 707020、EP 894107或WO 2006/061181)、對-伸苯基類(例如依照WO 1992/18552)、咔唑類(例如依照WO 2004/070772或WO 2004/113468)、噻吩類(例如依照EP 1028136)、二氫菲類(例如依照WO 2005/014689或WO 2007/006383)、順式-及反式-茚並茀類(例如依照WO 2004/041901或WO 2004/113412)、酮類(例如依照WO 2005/040302)、菲類(例如依照WO 2005/104264或WO 2007/017066)或多種這些單元。該聚合物、寡聚物及樹枝狀聚合物也經常含有另外之單元,例如發射(螢光或磷光)單元,例如乙烯基三芳香基胺類(例如依照WO 2007/068325)或磷光金屬錯合物(例如依照WO 2006/003000)及/或電荷輸送單元,尤其是那些以三芳香基胺類為底質者。
依照本發明之聚合物、寡聚物及樹枝狀聚合物具有有利的性質,尤其是長的使用期限、高的效率及良好的色彩
座標。
依照本發明之聚合物及寡聚物通常是藉由一或多種形式之單體之聚合而製備,該等單體之至少一種單體成為該聚合物中之式(I)、(II)或(III)的重複單元。合適的聚合反應對精於此技藝之人士是已知的且在文獻中描述。特別適合且較佳之獲得C-C或C-N鏈接的聚合反應是以下者:(A)鈴木聚合;(B)山本聚合;(C)史帝勒(STILLE)聚合;及(D)哈特維格-巴哈法氏(HARTWIG-BUCHWALD)聚合
可藉由這些方法所實施該聚合的方式及稍後該聚合物可由反應介質分離出且純化之方式對精於此技藝之人士是已知的且被詳細描述於文獻中,例如於WO 2003/048225、WO 2004/037887及WO 2004/037887中。
本發明因此也關於一種製備依本發明之聚合物、寡聚物及樹枝狀聚合物的方法,其特徵在於彼等係藉由鈴木聚合、山本聚合、史帝勒聚合或哈特維格-巴哈法氏聚合製備。依本發明之樹枝狀聚合物可藉由精於此技藝之人士已知的方法或類似方法製備。適合的方法描述於文獻,諸如於Frechet, Jean M. J.; Hawker, Craig J., "Hyperbranched Polyphenylene and hyperbranched polyesters: new soluble, three-dimensional, reactive polymers", Reactive & Functional Polymers(1995), 26(1-3), 127-36; Janssen, H.
M.: Meijer, E. W., "The synthesis and characterization of dendritic molecules", Materials Science and Technology (1999), 20(Synthesis of Polymers), 403-458; Tomalia, Donald A., "Dendrimer molecules", Scientific American (1995), 272(5), 62-6; WO 2002/067343 A1及WO 2005/026144 A1中。
為處理該液相所得之依本發明的化合物,例如藉由旋轉塗覆或藉由印刷方法,依照本發明之化合物的調合物是需要的。這些調合物可以是例如溶液、分散液或乳濁液。較佳可以使用用於本目的之二或多種溶劑之混合物。適合且較佳之溶劑是例如甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、1,3,5-三甲苯、1,2,3,4-四氫萘、藜蘆素、THF、甲基-THF、THP、氯苯、二、苯氧基甲苯(尤其是3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲基乙酯、二氫茚、苯甲酸甲酯、NMP、對-異丙基甲苯、苯基乙基醚、1,4-二異丙基苯、二苯甲基醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、
1,1-雙(3,4-二甲基苯基)乙烷或這些溶劑之混合物。
本發明因此另外關於一種調合物,尤其是溶液、分散液或乳濁液,其包含至少一種式(I)、(II)或(III)之化合物或含有至少一種式(I)、(II)或(III)之單元的至少一種聚合物、寡聚物或樹枝狀聚合物、及至少一種溶劑,較佳是有機溶劑。可製備此型溶液之方式對精於此技藝之人士是已知的且經描述於例如WO 2002/072714、WO 2003/019694及其中所引證之文獻中。
依照本發明之式(I)、(II)或(III)的化合物適用於電子裝置,尤其是有機電激發光裝置(OLEDs)中。依照該取代,該等化合物用在不同功能及層中。
本發明因此另外關於該式(I)、(II)或(III)之化合物在電子裝置中之用途及關於包含該式(I)、(II)或(III)之一或多種化合物的電子裝置本身。該電子裝置在此較佳選自有機積體電路(OICs)、有機場效應電晶體(OFETs)、有機薄膜電晶體(OTFTs)、有機發光電晶體(OLETs)、有機太陽能電池(OSCs)、有機光學偵測器、有機感光器、有機場淬熄裝置(OFQDs)、有機發光電化學電池(OLECs)、有機雷射二極體(O-雷射)及特佳是有機電激發光裝置(OLEDs)。
特佳是包含陽極、陰極及至少一發光層之有機電激發光裝置,其特徵在於至少一有機層包含該式(I)、(II)或(III)之至少一種化合物。
除了該陰極、陽極及發光層之外,該有機電激發光裝
置也可包含另外之層。這些在每一情況中是選自例如一或多個電洞注射層、電洞輸送層、電洞阻擋層、電子輸送層、電子注射層、電子阻擋層、激子阻擋層、中間層、電荷產生層(IDMC 2003,Taiwan;Session 21 OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having Charge Generation Layer)及/或有機或無機p/n接面。然而,應指出:每一這些層不需一定要存在且各層之選擇總是依照所用之化合物而定,尤其是依照該電激發光裝置是螢光或磷光而定。
該有機電激發光裝置之各層的順序較佳是如下:陽極-電洞注射層-電洞輸送層-發光層-電子輸送層-電子注射層-陰極。在此應再次指出:並非全部之該等層必須存在,及/或在這些之外,可以存在另外的層。
依照本發明之有機電激發光裝置包含多個發光層。在此情況中,這些發光層特佳在380奈米至750奈米之間共具有多個發射極大值,而使整體為白光發射,亦即在該發光層中使用多種發射化合物,其能發螢光或磷光且其發射藍或黃或橘或紅光。特佳是三層系統,亦即具有三個發光層之系統,其中這些層之至少一者較佳包含該式(I)、(II)或(III)之至少一種化合物且其中此三層顯現出藍、綠及橘或紅光發射(基本結構參見例如WO 2005/011013)。依照本發明之化合物可二擇一地及/或另外地也存在於電洞輸送層或其他層中。應注意:對於白光
產生而言,在廣波長範圍內發射之個別使用的發射劑化合物也可以是合適的,用以代替多種發射顏色之發射劑化合物。
該式(I)、(II)或(III)之化合物較佳用在發光層中。特別地,該式(I)、(II)或(III)之化合物適合用來作為發光材料(摻雜劑)。
依照本發明之化合物特別適合用來作為藍光發射之發射劑化合物。有關之電子裝置可包含單一發光層(其包含依照本發明之化合物)或彼可包含二或多個發光層。在此,另外之發光層可包含依照本發明之一或多種化合物或二擇一地包含其他化合物。
若依照本發明之化合物被用來作為發光層中之發光材料,則彼較佳與一或多種主材料混合使用。在包含主材料及摻雜劑之系統中的主材料用來表示在該系統中較高比例存在之成份。在包含一主材料及多種摻雜劑之系統的情況中,該主材料用來表示在該混合物中佔最高比例之成份。
在該發光層之混合物中,依照本發明之化合物的比例是在0.1至50.0體積%之間,較佳在0.5至20.0體積%之間,特佳在1.0至10.0體積%之間。對應地,該主材料的比例是50.0至99.9體積%之間,較佳在80.0至99.5體積%之間,特佳在90.0至99.0體積%之間。
與依照本發明之材料混合使用之較佳的主材料(基質材料)係選自以下類別:聚寡亞芳基類(例如依照EP 676461之2,2',7,7'-四苯基螺聯茀或二萘蒽),特別是含
縮合芳香基團之寡聚亞芳基類、寡聚亞芳基亞乙烯類(例如依照EP 676461之DPVBi或螺-DPVBi),多極(polypodal)金屬錯合物(例如依照WO 2004/081017),導電洞化合物(例如依照WO 2004/058911),導電子化合物,特別是酮類、氧化膦類、亞碸類等(例如依照WO 2005/084081及WO 2005/084082)、構型異構物類(例如依照WO 2006/048268)、硼酸衍生物(例如依照WO 2006/117052)或苯并蒽類(例如依照WO 2008/145239)。特佳之基質材料係選自以下類別:寡聚亞芳基類(其包含萘、蒽、苯并蒽及/或芘或這些化合物之構型異構物)、寡聚亞芳基亞乙烯類、酮類、氧化膦類及亞碸類。極特佳之基質化合物係選自以下類別:寡聚亞芳基類,其包含蒽、苯并蒽、苯并菲及/或芘或這些化合物之構型異構物。在本發明觀念中,寡聚亞芳基類意圖用來表示至少有三個芳香基或亞芳香基互相鍵結之化合物。
依照該取代形式,依照本發明之化合物也可用在其他層中,例如作為在電洞注射或電洞輸送層中之電洞輸送材料或作為在發光層中之主材料,較佳作為用於磷光發射劑之主材料。
通常,在依照本發明之有機電激發光裝置中作為對應之官能材料的較佳材料類別在以下指明。
適合之磷光摻雜劑特別是在適合激發時發光(較佳在可見光區)的化合物,且在此之外還含有至少一種原子,
其原子數大於20,較佳大於38且小於84,特佳大於56且小於80。所用之螢光摻雜劑較佳是含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪的化合物,特別是含銥、鉑或銅之化合物。
為本發明之目的,所有的銥、鉑或銅之發光錯合物被視為磷光化合物。
上述之磷光摻雜劑的實例揭示於申請案WO 2000/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 2005/033244、WO 2005/019373及US 2005/0258742中。
通常,如依照關於磷光OLEDs之先前技藝所用的及如精於有機電激發光裝置領域之技藝之人士所已知的所有磷光錯合物是適合用於依照本發明之裝置中。精於該技藝之人士也將能在沒有發明步驟之情況下將另外之磷光錯合物與依照本發明之化合物結合用於OLEDs中。
在依照本發明之化合物以外,較佳之螢光摻雜劑係選自該芳香基胺類。在本發明觀念中,芳香基胺或芳香族胺係用來表示含有三個直接鍵結於該氮原子之經取代或未經取代之芳香族或雜芳香族環系統的化合物。這些芳香族或雜芳香族環系統之至少一者較佳是縮合的環系統,特佳是具有至少14個芳香族環原子者。其較佳實例是芳香族蒽胺類、芳香族蒽二胺類、芳香族芘胺類、芳香族芘二胺類、芳香族苯并[a]菲胺類或芳香族苯并[a]菲二胺類。芳香族蒽胺用來表示一種化合物,其中一個二芳香基胺基直
接鍵結於蒽基,較佳於9-位置上。芳香族蒽二胺用來表示一種化合物,其中二個二芳香基胺基直接鍵結於蒽基,較佳於9,10-位置上。芳香族芘胺類、芳香族芘二胺類、芳香族苯并[a]菲胺類或芳香族苯并[a]菲二胺類定義與以上類同,其中該二芳香基胺基較佳鍵結於該芘之1-位置或1,6-位置上。
與螢光摻雜劑一同使用之較佳的基質材料在以上指明。
用於磷光摻雜劑之較佳基質材料是芳香族胺類(尤其是三芳香基胺類,例如依照US 2005/0069729者)、咔唑衍生物(例如CBP,N,N-雙咔唑基聯苯)或依照WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851之化合物、橋接咔唑衍生物(例如依照WO 2011/088877及WO 2011/128017者)、茚并咔唑衍生物(例如依照WO 2010/136109及WO 2011/000455者)、吖咔唑衍生物(例如依照EP 1617710、EP 1617711、EP 1731584、JP 2005/347160者)、吲哚并咔唑衍生物(例如依照WO 2007/063754或WO 2008/056746者)、酮類(例如依照WO 2004/093207或WO 2010/006680)、氧化膦類、亞碸類及碸類(例如依照WO 2005/003253者)、寡聚之亞苯基類、雙極性基質材料(例如依照WO 2007/137725者)、矽烷類(例如依照WO 2005/111172者)、吖硼勒類(azaboroles)或硼酸酯類(例如依照WO 2006/117052者)、三嗪衍生物
(例如依照WO 2010/015306、WO 2007/063754或WO 2008/056746者)、鋅錯合物(例如依照EP 652273或WO 2009/062578者)、鋁錯合物(例如BAlq)、二氮雜矽勒(diazasilole)及四氮雜矽勒(tetraazasilole)衍生物(例如依照WO 2010/054729者)、二吖磷勒(diazaphosphole)衍生物(例如依照WO 2010/054730者)及鋁錯合物(例如BAlq)。
在依照本發明之化合物以外,如在依照本發明之有機電激發光裝置之電洞注射或電洞輸送層或電子阻擋層或在電子輸送層中可見的,適合的電荷輸送材料是例如在Y.Shirota等人.,Chem.Rev.2007,107(4),953-1010中所揭示之化合物或如依照先前技藝之在這些層中所利用的其他材料。
在依照本發明之電激發光裝置中之電洞輸送、電洞注射或電子阻擋層中可用的較佳電洞輸送材料的實例是茚并茀胺類及衍生物(例如依照WO 06/122630或WO 06/100896者)、在EP 1661888中所揭示之胺衍生物、六吖三亞苯基衍生物(例如依照WO 01/049806者)、含縮合芳族環的胺衍生物(例如依照US 5,061,569者)、在WO 95/09147中所揭示之胺衍生物、單苯并茚并茀胺類(例如依照WO 08/006449者)或二苯并茚并茀胺類(例如依照WO 07/140847者)。另外合適之電洞輸送及電洞注射材料是以上所描繪之化合物的衍生物,如在JP 2001/226331、EP 676461、EP 650955、WO 01/049806、
US 4780536、WO 98/30071、EP 891121、EP 1661888、JP 2006/253445、EP 650955、WO 06/073054及US 5061569中揭示者。
該有機電激發光裝置之陰極較佳包含具有低的功函數之金屬、包含多種金屬諸如鹼土金屬、鹼金屬、主族金屬或鑭系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)之金屬合金或多層結構體。包含鹼金屬或鹼土金屬及銀之合金,例如包含鎂及銀之合金也是適合的。在多層結構體的情況中,在該等金屬之外,具有相對高的功函數之另外的金屬,諸如Ag或Al也可被使用,在此情況中,通常使用金屬混合物,諸如Ca/Ag、Mg/Ag或Ba/Ag。也較佳在金屬陰極與該有機半導體之間導入具有高介電常數之材料的薄中間層。適合此目的者是例如鹼金屬氟化物或鹼土金屬氟化物,但也可以是對應之氧化物或碳酸鹽類(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。另外,喹啉酸鋰(LiQ)可供此目的之用。此層之層厚度較佳在0.5至5奈米之間。
陽極較佳包含具有高功函數之材料。該陽極相對於真空較佳具有大於4.5eV之功函數。適合於此目的者一方面是具有高還原氧化電勢之金屬諸如Ag、Pt或Au。另一方面,金屬/金屬氧化物電極(例如Al/Ni/NiOx、Al/PtOx)也可以是較佳的。對於某些應用而言,該等電極之至少一者必須是透明的或部份透明的,以促進該有機材料(有機太陽能電池)之照射或光之耦合輸出
(OLEDs、O-雷射)。在此,較佳之陽極材料是導電混合金屬氧化物。特佳是氧化銦錫(ITO)或氧化銦鋅(IZO)。另外較佳是導電之摻雜有機材料,尤其是導電之摻雜聚合物。
該裝置合適地按照應用被構成,提供接點且最後被密封,因為依照本發明之裝置的使用期限在水及/或空氣之存在下被縮短。
在一較佳具體例中,依照本發明之有機電激發光裝置特徵在於利用昇華方法塗覆一或多層,其中該等材料係藉由在真空昇華單元中,在低於10-5毫巴(較佳低於10-6毫巴)之起初壓力下,氣相沉積以施加。然而,在此該起初壓力也可能甚至更低,例如低於10-7毫巴。
同樣地,較佳是有機電激發光裝置,其特徵在於利用OVPD(有機氣相沉積)程序或藉助於載劑氣體昇華以塗覆一或多層,其中該等材料係在10-5毫巴至1巴間之壓力下被施加。此方法之特殊情況是該OVJP(有機蒸氣噴射印刷)方法,其中該材料經由噴嘴直接施加且因此被結構化(例如M.S.Arnold等人.,Appl.Phys.Lett. 2008,92,053301)。
另外較佳是有機電激發光裝置,其特徵在於例如藉由以下方式由溶液製造一或多層:旋轉塗覆,或利用任何所要之印刷方法,例如屏蔽印刷、快乾印刷、噴嘴印刷或平版印刷,但特佳利用LITI(光感應熱成像之熱傳印刷)或噴墨印刷。該式(I)、(II)或(III)之可溶化合物對
此目的而言是需要的。經由該等化合物之合適的取代,可以達成高的溶解度。
為供製造依照本發明之有機電激發光裝置,另外較佳由溶液施加一或多層且藉由昇華方法施加一或多層。
依照本發明,包含依照本發明之一或多種化合物的電子裝置可在顯示器中被利用,在照明應用中作為光源且在醫療及/或美容應用(例如光療)中作為光源。
以下可行實例用來圖解且說明本發明。
4-溴甲苯及二苯基胺是市售的。2-氯-5-萘-1-基對苯二甲酸二乙酯之合成係描述於WO 2010/012328 A1中。
7,7,13,13-四甲基-N-(7,7,13,13-四甲基-7,13-二氫苯并[g]茚并[1,2-b]茀-11-基)-N-(對-甲苯基)-7,13-二氫苯并[g]茚并[1,2-b]茀-11-胺(I)之合成
在本文所描述之合成以外,在文獻中所描述之另外的合成對精於此技藝之人士是可用的。二苯基胺(88.34克,520毫莫耳)及4-溴甲苯(82.0克,470毫莫耳)溶在900毫升甲苯中。然後將三-鄰-甲苯基膦(1.46克,4.7毫莫耳)、乙酸鈀(II)(0.53克,2.4毫莫耳)及第三丁氧基鈉(69.1克,700毫莫耳)添加於該反應溶液,而後該反應溶液在迴流下加熱3天。該混合物在室溫下用甲苯及蒸餾水加大體積、該有機相被分離出,且該水相利用甲苯萃取多次。該有機相使用MgSO4乾燥,通過AlOx過濾且蒸發。使用庚烷使殘留物沉澱且由異丙醇中結晶出,獲得無色固體狀之(4-甲基苯基)二苯基胺(85.7克,70%理論)。
雙-(4-溴苯基)-對-甲苯基胺(Ib)
(4-甲基苯基)二苯基胺(85.2克,330毫莫耳)溶在1升DCM中且冷卻至0℃。N-溴丁烯二醯亞胺(117克,660毫莫耳)在攪拌下,以使該反應溫度不超過5℃之速率,分小份地添加。該反應混合物在冰浴中加溫至室溫過夜。然後添加500毫升之10%的Na2SO3溶液,且分離各相。水相以DCM萃取多次。該有機相以蒸餾水清洗,乾燥且除去溶劑。所得之固體由1-丁醇再結經多次,獲得129克之無色固體(94%理論)。
4-甲基-N,N-雙(4-(4,4,5,5-四甲基-1,3,2-二氧雜硼雜五員環(dioxaborolan)-2-基)-苯基苯胺(Ic)
雙-(4-溴苯基)-對-甲苯基胺(128克,310毫莫耳)及雙甲基第三丁基甲醇化二硼烷(195克,770毫莫耳)溶於1.5升THF中。然後將乙酸鉀(241克,2460毫莫耳)及1,1'-雙(二苯基膦基)二茂鐵鈀(II)二氯化物*DCM(7.52克,9.2毫莫耳)添加至該反應溶液,該反應溶液而後在迴流下加熱6天。在冷卻至室溫後,該批份用DCM及蒸餾水加大體積,且該水相以DCM萃取多次。經結合的有機相以蒸餾水清洗且在使用MgSO4乾燥之後,通過AlOx過濾。該溶劑在大氣壓下移除。所得固體以庚烷及乙腈清洗,獲得110克淺灰色粉末(70%理論)。
4',4'"-(對-甲苯基氮雜二基(tolylazandiyl)雙(4-(萘-1-基)-[1,1'-聯苯]-2,5-二羧酸)四乙酯(Id)
4-甲基-N,N-雙(4-(4,4,5,5-四甲基-1,3,2-二氧雜硼雜五員環-2-基)苯基苯胺(110克,215毫莫耳)及2-氯-5-萘-1-基對苯二甲酸二乙酯(189克,495毫莫耳)溶在1.2升甲苯中,且添加四(三苯基膦)鈀(4.97克,4.3毫莫耳)及2-二環己基膦基-2',6'-二甲氧基聯苯(3.53克,8.6毫莫耳)。隨後,將氫氧化四乙基銨(20%於H2O中)(450毫升,645毫莫耳)添加於該反應溶液中。該批份在迴流下加熱7小時,冷卻至室溫且以蒸餾水加大體
積。在相分離後,該水相以甲苯萃取多次。經結合之有機相以蒸餾水清洗,利用MgSO4乾燥且經AlOx過濾。使該有機相蒸發以獲得深橘色之黏稠油且藉由層析法(矽膠,庚烷/THF 85:15)純化以獲得147克(72%理論)之鮮黃色固體狀的4',4'"-(對-甲苯基氮雜二基(tolylazandiyl)雙(4-(萘-1-基)-[1,1'-聯苯]-2,5-二羧酸)四乙酯。
2-[4'-{[2',5'-雙-(1-羥基-1-甲基乙基)-4'-萘-1-基聯苯-4-基]-對-甲苯胺基}-5-(1-羥基-1-甲基乙基)-4-萘-1-基聯苯-2-基]丙-2-醇(Ie)
4',4'"-(對-甲苯基氮雜二基(tolylazandiyl)雙(4-(萘-1-基)-[1,1'-聯苯]-2,5-二羧酸)四乙酯(147克,154毫莫耳)溶在750毫升之THF中,且在0℃下添加氯化甲基鎂(20%之於THF中的溶液)(617毫升,1700毫莫耳)。使該反應溶液在冰浴中加溫至室溫過夜。該批份使用飽和NH4Cl溶液小心地水解且使用4%氫氯酸中和。該混合物以蒸餾水加大體積且徹底地以甲苯萃取。經結合之有機相以蒸餾水清洗多次且以NaHCO3清洗一次且利用MgSO4乾燥。在真空移除該溶劑之後,獲得淺米色固體。此固體以庚烷/異丙醇混合物清洗,獲得136克(98%理論)之無色固體狀的2-[4'-{[2',5'-雙-(1-羥基-1-甲基乙基)-4'-萘-1-基聯苯-4-基]-對-甲苯胺基}-5-(1-羥基-1-甲
基乙基)-4-萘-1-基聯苯-2-基]丙-2-醇。
7,7,13,13-四甲基-N-(7,7,13,13-四甲基-7,13-二氫苯并[g]茚并[1,2-b]茀-11-基)-N-(對-甲苯基)-7,13-二氫苯并[g]茚并[1,2-b]茀-11-胺(I)(合成實例1)
2-[4'-{[2',5'-雙-(1-羥基-1-甲基乙基)-4'-萘-1-基聯苯-4-基]-對-甲苯胺基}-5-(1-羥基-1-甲基乙基)-4-萘-1-基聯苯-2-基]丙-2-醇(135克,151毫莫耳)溶在1.3升之DCM中,且在-20℃下添加甲烷磺酸(69毫升,1060毫莫耳)及多磷酸(156克,1350毫莫耳)。使該反應溶液加溫至室溫過夜。所沉澱之黃色固體被濾出且藉由索司勒(Soxhlett)萃取法及隨後之昇華來純化,獲得47.4克之黃色固體(38%理論)。
7,7,13,13-四甲基-5-苯基-7,13-二氫苯并[g]茚并[1,2-b]茀(IIa)
12.8克(103毫莫耳)之苯硼酸、37.7克(86毫莫耳)之5-溴-7,7,13,13-四甲基-7,13-二氫苯并[g]茚并[1,2-b]茀及29.7克(215毫莫耳)之K2CO3懸浮於500毫升之甲苯/水(1:1)中。將0.99克(0.86毫莫耳)之四(三苯基膦)鈀添加至該懸浮液中,且該反應混合物在迴流下加熱16小時。冷卻後,該反應混合物以乙酸乙酯稀釋,該有機相被分離出,以100毫升之水清洗3次且隨後蒸發至乾。在與甲苯一同通過矽膠過濾以該粗製之產物後,殘留之殘餘物由庚烷/甲苯再結晶。產率是29.2克(78%理論)。
11-溴-7,7,13,13-四甲基-5-苯基-7,13-二氫苯并[g]茚并[1,2-b]茀(IIb)
29.2克(67毫莫耳)之7,7,13,13-四甲基-5-苯基-7,13-二氫苯并[g]茚并[1,2-b]茀(IIa)溶在500毫升之CHCl3中,且在-10℃下緩慢添加溶於500毫升之CHCl3中之10.8克(67毫莫耳)之溴。當反應完成時,添加水,且有機相被分離出、乾燥且蒸發。粗製之產物隨後藉由與熱庚烷/甲苯(5:1)一同攪拌多次而清洗。產率:30.5克(89%)之白色固體狀之產物。
9.74克之二-對-甲苯基安(49.4毫莫耳)、11-溴-7,7,13,13-四甲基-5-苯基-7,13-二氫苯并[g]茚并[1,2-b]茀(IIb)(41.1毫莫耳)溶於500毫升之甲苯中。該溶液經脫氣且以氬氣飽和。然後添加2.5毫升(2.5毫莫耳)之1M的三-第三丁基膦溶液及0.355克(1.23毫莫耳)之乙酸鈀(II)。隨後添加11.9克之第三丁氧化鈉(124毫莫耳)。該混合物在保護性氣體環境下加熱沸騰12小時。隨後將水添加至該混合物,該有機相以水清洗3次,利用Na2SO4乾燥且在旋轉蒸發器中蒸發。在該粗製產物與甲苯通過矽膠而過濾後,殘留之殘餘物由庚烷/甲苯再
結晶且最後在高真空下昇華。純度是99.9%。產率是15.2克(58%理論)。
1-(9,9-二甲基-9H-茀-2-基)-2-萘酸乙酯(i-a)
1-溴萘-2-羧酸甲酯(150克,563毫莫耳)、9,9-二甲基-9H-茀-2-基硼酸酯(148.9克,619毫莫耳)及磷酸鉀單水合物(286克,1.182莫耳)溶於1.2升之甲苯及1升水的混合物中,且添加乙酸鈀(1.28克,5.6毫莫耳)及三-鄰-甲苯基膦(3.5克,11.3毫莫耳)。該批份在迴流下加熱過夜,冷卻至室溫且以蒸餾水加大體積。在相分離後,該水相以甲苯萃取多次。經結合之有機相以蒸餾水清洗,利用硫酸鎂乾燥且通過氧化鋁過濾。該有機相蒸發成橘色油,獲得213克之產物(99%理論)。
1-(7-溴-9,9-二甲基-9H-茀-2-基)-2-萘酸乙酯(i-b)
(i-a)(122克,295毫莫耳)溶在1升之氯仿中且冷卻至0℃。在0.5升之氯仿中所成的二溴溶液(14.4毫
升,280毫莫耳)在攪拌下以使該反應溫度不致超過5℃之速率下逐滴添加。該反應混合物在冰浴中被加溫至室溫過夜。添加500毫升之10%的硫代硫酸鈉溶液,且分離各相。在相分離後,水相以氯仿萃取多次。經結合之有機相以蒸餾水清洗,利用硫酸鎂乾燥且通過氧化鋁過濾。該有機相被蒸發成無色油,獲得128克之產物(95%理論)。
2-(1-(7-溴-9,9-二甲基-9H-茀-2-基)萘-2-基)丙-2-醇(i-c)
(i-b)(80克,175毫莫耳)及氯化鈰(III)(48克,247毫莫耳)溶在800毫升之THF中,且在0℃下添加氯化甲基鎂(於THF中所成之3M溶液)(146毫升,437毫莫耳)。使該反應溶液在冰浴中加溫至室溫過夜。該批份使用飽和NH4Cl溶液小心地水解且使用4%之氫氯酸中和。該混合物以蒸餾水加大體積且以甲苯徹底地萃取。經結合之有機相以蒸餾水清洗多次且以碳酸氫鈉溶液清洗一次且利用硫酸鎂乾燥。在真空中移除溶劑後,獲得淡米色固體。此由庚烷/甲苯混合物中再結晶,獲得69克(86%理論)之無色固體。
11-溴-7,7,13,13-四甲基-7,13-二氫苯并[g]茚并[1,2-b]茀(i)
(i-c)(61克,133毫莫耳)溶於300毫升之DCM中,且在0℃下添加甲烷磺酸(60毫升,933毫莫耳)及
多磷酸(91克,933毫莫耳)。使該反應溶液加溫至室溫過夜。該混合物以乙醇加大體積且被蒸發。該殘留物溶在甲苯中,以NaOH溶液及蒸餾水清洗且利用硫酸鎂乾燥。在真空中移除溶劑後,該固體由乙醇中再結晶,獲得55克黃色固體(93%理論)。
1-苯基萘-2-羧酸甲酯(ii-a)
1-溴萘-2-羧酸甲酯(70.0克,264毫莫耳)、苯基硼酸(38.6克,317毫莫耳)及磷酸鉀單水合物(182克,792毫莫耳)溶於0.2升之甲苯、0.2升之二烷及0.2升之水的混合物中,且乙酸鈀(1.18克,5.3毫莫耳)及三-鄰-甲苯基膦(3.2克,10.6毫莫耳)。該批份在迴流下加熱過夜,冷卻至室溫且以蒸餾水加大體積。在相分離後,該水相以甲苯萃取多次。經結合之有機相以蒸餾水清洗,利用硫酸鎂乾燥且通過氧化鋁過濾。該有機相蒸發成橘色油,獲得69克之產物(99%理論)。
2-(1-苯基萘-2-基)丙-2-醇(ii-b)
(ii-a)(69克,264毫莫耳)及氯化鈰(III)(71克,291毫莫耳)溶在500毫升之THF中,且在0℃下添加氯化甲基鎂(於THF中所成之3M溶液)(308毫升,925毫莫耳)。使該反應溶液在冰浴中加溫至室溫過夜。該批份使用飽和NH4Cl溶液小心地水解且使用4%之氫氯酸中和。該混合物以蒸餾水加大體積且以甲苯徹底地萃取。經結合之有機相以蒸餾水清洗多次且以碳酸氫鈉溶液清洗一次且利用硫酸鎂乾燥。在真空中移除溶劑後,獲得
淡米色固體。此由庚烷/甲苯混合物中再結晶,獲得52克(75%理論)之無色固體。
7,7-二甲基-7H-苯并[c]茀(ii-1)
(ii-b)(52克,198毫莫耳)溶於500毫升之DCM中,且在0℃下添加甲烷磺酸(64毫升,991毫莫耳)及多磷酸(77克,793毫莫耳)。使該反應溶液加溫至室溫過夜。該混合物以乙醇加大體積且被蒸發。該殘留物溶在甲苯中,以NaOH溶液及蒸餾水清洗且利用硫酸鎂乾燥。在真空中移除溶劑後,該固體由乙醇中再結晶,獲得44克黃色固體(91%理論)。
二苯基(1-苯基萘-2-基)甲醇(ii-c)
(ii-a)(35克,133毫莫耳)及氯化鈰(III)(36克,146毫莫耳)溶在250毫升之THF中,且在0℃下添加氯化苯基鎂(於THF中所成之3M溶液)(150毫升,450毫莫耳)。使該反應溶液在冰浴中加溫至室溫過夜。該批份使用飽和NH4Cl溶液小心地水解且使用4%之氫氯
酸中和。該混合物以蒸餾水加大體積且以甲苯徹底地萃取。經結合之有機相以蒸餾水清洗多次且以碳酸氫鈉溶液清洗一次且利用硫酸鎂乾燥。在真空中移除溶劑後,獲得淡米色固體。此由庚烷/甲苯中再結晶,獲得41克(80%理論)之無色固體。
與(ii-1)類似地合成建構嵌段(ii-2),產率為88%。
依照以下之文獻程序:Organic Letters, 2009, Vol. 11, No. 20, 4588-4591合成7H-苯并[c]茀。
7H-苯并[c]茀(38克,176毫莫耳)、1,5-二溴戊烷(40.5克,176毫莫耳)及溴化四丁基銨(32.3克,100毫莫耳)溶於0.5升甲苯中。添加0.5升之3M NaOH溶液,且該反應混合物在迴流下煮沸過夜。該反應混合物冷卻至室溫,分離各相,該水相以甲苯萃取3次。該有機相以蒸餾水清洗,乾燥且清除溶劑。所得之固體由甲苯/庚
烷再結晶,獲得31克之無色固體(62%理論)。
5-溴-7,7-二甲基-7H-苯并[c]茀(iii-a)
(ii-1)(38.2克,156毫莫耳)溶在0.3升之氯仿中且冷卻至0℃。在0.2升之氯仿中所成的二溴溶液(117克,660毫莫耳)在攪拌下以使該反應溫度不致超過5℃之速率下逐滴添加。該反應混合物在冰浴中被加溫至室溫過夜。添加200毫升之10%的硫代硫酸鈉溶液,且分離各相。水相以DCM萃取多次。有機相以蒸餾水清洗,乾燥且清除溶劑。所得之固體由甲苯/庚烷再結晶,獲得50克之無色固體(99%理論)。
7,7-二甲基-5-苯基-7H-苯并[c]茀(iii-b)
(iii-a)(28.5克,88毫莫耳)、苯基硼酸(13.2克,106毫莫耳)及碳酸鉀(30.5克,220毫莫耳)溶於150毫升之甲苯及150毫升之水的混合物中,且添加四(三苯基膦)鈀(1.02克,0.9毫莫耳)。該批份在迴流下加熱過夜,冷卻至室溫且以蒸餾水加大體積。在相分離後,該水相以甲苯萃取多次。經結合之有機相以蒸餾水清
洗,利用硫酸鎂乾燥且通過AlOx及矽膠過濾。該有機相蒸發,且所得之固體以乙醇清洗,獲得25.9克之產物(92%理論)。
9-溴-7,7-二甲基-5-苯基-7H-苯并[c]茀(iii)
(iii-b)(25.8克,81毫莫耳)溶於0.15升之氯仿中且冷卻至0℃。在0.1升之氯仿中所成的二溴溶液(13.6克,85毫莫耳)在攪拌下以使該反應溫度不致超過5℃之速率下逐滴添加。該反應混合物在冰浴中被加溫至室溫過夜。添加100毫升之10%的硫代硫酸鈉溶液,且分離各相。水相以DCM萃取多次。有機相以蒸餾水清洗,乾燥且清除溶劑。所得之固體由甲苯/庚烷再結晶,獲得22克之無色固體(62%理論)。
N-苯基-7,7,13,13-四甲基-7,13-二氫苯并[g]茚并[1,2-b]茀-11-胺(iv)
i(37克,84.2毫莫耳)及苯胺(8.6克,92.6毫莫耳)溶於500毫升甲苯中。該溶液經脫氣且以氬氣飽和。然後添加4.1克(5.1毫莫耳)之Pd(dppf)Cl2。隨後添加24.3克之第三丁氧化鈉(253毫莫耳)。該反應混合物在保護性氣體環境中沸騰加熱12小時。隨後將水添加至該混合物,該有機相以水清洗3次,利用Na2SO4乾燥且在旋轉蒸發器中蒸發。在粗製產物與甲苯通過矽膠以過濾後,殘留之殘餘物由庚烷/甲苯再結晶。產率是31克(77%理論)。
7,7,13,13-四甲基-N-(7,7-二甲基-5-苯基-7H-苯并[c]茀-9-基)-N-苯基-7,13-二氫苯并[g]茚并[1,2-b]茀-11-胺(III)(合成實例37)
iv(20克,44.3毫莫耳)及iii(18.6克,46.5毫莫耳)溶於500毫升之甲苯中。該溶液經脫氣且以氬氣飽
和。然後添加2.5毫升(2.5毫莫耳)之1M的三-第三丁基膦溶液及0.355克(1.23毫莫耳)之乙酸鈀(II)。隨後添加11.9克之第三丁氧化鈉(124毫莫耳)。該反應混合物在保護性氣體環境下加熱沸騰12小時。隨後將水添加至該混合物,該有機相以水清洗3次,利用Na2SO4乾燥且在旋轉蒸發器中蒸發。在該粗製產物與甲苯通過矽膠而過濾後,殘留之殘餘物由庚烷/甲苯再結晶且最後在高真空下昇華。純度是99.9%。產率是21克(62%理論)。
依照本發明之OLEDs及依照先前技藝之OLEDs係藉由依照WO 04/058911之一般方法製造,該方法適用於在本文中所述之狀況(層厚度變化、材料)。
在以下實例中呈現多種OLEDs之數據(參見表1至3)。所用之基材是以結構化之ITO(氧化銦錫)塗覆之厚度50奈米的玻璃片。該OLEDs原則上具有以下層結構:基材/緩衝層(20奈米)/電洞注射層(HIL,5奈米)/電洞輸送層(HTL,30奈米)/發光層(EML,20奈米)/電子輸送層(ETL,30奈米)/電子注射層(LiQ,1奈米)且最後是陰極。該陰極係藉由厚度100奈米之鋁層所形成。厚度20奈米之Clevios P VP A1 4083(可由Heraeus Clevios GmbH,Leverkusen購得)層係藉由旋轉塗覆施加以作為緩衝層。所有其餘的材料係在真空室中藉由熱蒸氣沉積施加。該OLEDs之EML及ETL的結構係顯示於表1中。所用之材料係顯示於表3中。
該發光層(EML)總是由至少一種基質材料(主材料
=H)及發射用摻雜劑(摻雜劑=D)構成,該摻雜劑以某一體積比例藉由共蒸發與該基質材料摻混。諸如H1:D1(95%:5%)之表示方式在此意為材料H1在該層中之含量為95%之體積比例且D1在該層中之含量為5%之體積比例。同樣地,該電子輸送層也可由二種材料之混合物構成。
該OLEDs特徵在於標準方法。為供此目的,該電激發光之光譜被記錄,電流效率(測量單位是cd/A)及外部量子效率(EQE,測量單位是%)作為發光密度之函數係由電流/電壓/發光密度特徵線(IUL特徵線)假設朗伯發射特徵所計算的,且最終決定該組件之有效期。該電激發光之光譜在1000cd/m2之發光密度被記錄,且該CIE 1931 x及y色座標係由此計算。表示方式EQE @ 1000cd/m2指明在1000cd/m2之操作發光密度下之外部量子效率。使用期限LT50@ 60mA/cm2是在60mA/cm2之電流密度下該起初亮度(cd/m2)已降至一半時所經過之時間。對多種OLEDs所得之數據摘述於表2中。
依照本發明之化合物特別適合作為藍螢光摻雜劑。所用之比較用摻雜劑是由先前技藝(WO 2006/108497及WO 2008/006449)已知摻雜劑V-D1及V-D2。摻雜劑D3、D4、D5、D6及D7被測量以作為依照本發明之實例。
該結果顯示具有長的使用期限(LT50)的有效的OLEDs(外部量子效率)可利用依照本發明之具有深藍發射的化合物來獲得。
藉由比較,由先前技藝已知的摻雜劑V-D1及V-D2在效率及使用期限顯現出明顯差的值。
Claims (16)
- 一種式(I)、(II)或(III)之化合物,
- 如申請專利範圍第1項之化合物,其中Ar1在每一情況下,相同地或不同地,係選自苯基、萘基、蒽基、菲基、芘基、三苯基烯基、苯并[a]菲基、聯苯基、聯三苯基、茀基、螺聯茀基、咔唑基、二苯并呋喃基、二苯并噻吩基或西拉茀基(silafluorenyl)、彼等分別可經一或多個基團R1所取代。
- 如申請專利範圍第1至2項中任一項之化合物,其中Ara是具有6至18個芳香族環原子之芳香基,其可經一或多個基團R1取代。
- 如申請專利範圍第1至2項中任一項之化合物,其中在式(III)中,Ar2係經一或多個基團R1取代,該基團R1係選自具有5至30個芳香族環原子之芳香族或雜芳香族環系統,彼可經一或多個基團R2取代。
- 如申請專利範圍第1至2項中任一項之化合物,其中該X在每一情況下相同地或不同地是C(R1)2或Si(R1)2。
- 如申請專利範圍第1至2項中任一項之化合物,其 中R1在每一情況下,相同地或不同地,係選自H、D、F、CN、Si(R2)3、具有1至8個C原子之直鏈烷基或具有3至8個C原子之分枝或環狀烷基(其中該烷基可分別經一或多個基團R2取代且其中該烷基之一或多個CH2基團可經-C≡C-、-R2C=CR2-、Si(R2)2、C=O或-O-代替)、或具有6至16個芳香族環原子之芳香基或雜芳香基(其在每一情況下可經一或多個基團R2取代)。
- 如申請專利範圍第1至2項中任一項之化合物,其中a等於1。
- 如申請專利範圍第1至2項中任一項之化合物,其中b等於2。
- 如申請專利範圍第1至2項中任一項之化合物,其中m和n之合等於1。
- 如申請專利範圍第1至2項中任一項之化合物,其中o和p之合等於1。
- 如申請專利範圍第1至2項中任一項之化合物,其中q和r之合等於1。
- 一種寡聚物、聚合物或樹枝狀聚合物,其含有一或多種如申請專利範圍第1至11項中任一項之化合物,其中與該聚合物、寡聚物或樹枝狀聚合物之鍵結可定位在可經R1或R2取代之式(I)、(II)或(III)的任何所欲之位置。
- 一種調合物,其包含至少一種如申請專利範圍第1至11項中任一項的化合物或至少一種如申請專利範圍第 12項之聚合物、寡聚物或樹枝狀聚合物及至少一種溶劑。
- 一種電子裝置,其係選自有機積體電路(O-ICs)、有機場效應電晶體(O-FETs)、有機薄膜電晶體(O-TFTs)、有機發光電晶體(O-LETs)、有機太陽能電池(O-SCs)、有機光學偵測器、有機感光器、有機場淬熄裝置(O-FQDs)、發光電化學電池(LECs)、有機雷射二極體(O-雷射)及有機電激發光裝置(OLEDs),其特徵在於包含至少一種如申請專利範圍第1至11項中任一項的化合物或至少一種如申請專利範圍第12項之聚合物、寡聚物或樹枝狀聚合物。
- 如申請專利範圍第14項之電子裝置,其係選自有機電激發光裝置,其中利用如申請專利範圍第1至11項中任一項之化合物或如申請專利範圍第12項之聚合物、寡聚物或樹枝狀聚合物作為在發光層中之發光材料。
- 一種用於製備如申請專利範圍第1至11項中任一項之化合物的方法,其特徵在於利用一或多種有機金屬偶合方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12006239 | 2012-09-04 | ||
??12006239.3 | 2012-09-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201432021A TW201432021A (zh) | 2014-08-16 |
TWI611003B true TWI611003B (zh) | 2018-01-11 |
Family
ID=47002481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW102131558A TWI611003B (zh) | 2012-09-04 | 2013-09-02 | 用於電子裝置之化合物類 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10439145B2 (zh) |
EP (1) | EP2892876B1 (zh) |
JP (1) | JP6284940B2 (zh) |
KR (1) | KR102143742B1 (zh) |
CN (1) | CN104684886B (zh) |
TW (1) | TWI611003B (zh) |
WO (1) | WO2014037077A1 (zh) |
Families Citing this family (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102232993B1 (ko) * | 2012-11-02 | 2021-03-29 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 |
US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
US9748494B2 (en) | 2013-07-01 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic apparatus |
CN105993083B (zh) | 2013-12-20 | 2018-07-03 | Udc 爱尔兰有限责任公司 | 具有极短衰变时间的高效oled装置 |
KR102273046B1 (ko) * | 2014-07-04 | 2021-07-06 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
EP3188271B1 (en) * | 2014-08-26 | 2022-05-04 | Idemitsu Kosan Co., Ltd | Organic electroluminescent element and electronic device |
WO2016056640A1 (ja) * | 2014-10-09 | 2016-04-14 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
CN105753629B (zh) * | 2015-01-07 | 2018-11-16 | 机光科技股份有限公司 | 化合物和使用其的有机电致发光装置 |
US9812649B2 (en) * | 2015-02-17 | 2017-11-07 | Luminescence Technology Corp. | Indenotriphenylene-based amine derivative for organic electroluminescent device |
KR20240058993A (ko) | 2015-06-03 | 2024-05-07 | 유디씨 아일랜드 리미티드 | 매우 짧은 붕괴 시간을 갖는 고효율 oled 소자 |
US9537103B1 (en) * | 2015-08-14 | 2017-01-03 | Luminescence Technology Corporation | Material for organic electroluminescence device and organic electroluminescence device using the same |
CN107849444A (zh) | 2015-08-28 | 2018-03-27 | 默克专利有限公司 | 用于电子器件的化合物 |
CN105198875B (zh) * | 2015-08-31 | 2017-07-04 | 吉林奥来德光电材料股份有限公司 | 一种新的芳香族胺类化合物及其制备与应用 |
KR102487494B1 (ko) * | 2015-10-20 | 2023-01-12 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102611417B1 (ko) * | 2016-01-25 | 2023-12-07 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
EP3411455B1 (de) | 2016-02-05 | 2020-10-21 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
EP3481796B1 (en) | 2016-07-08 | 2021-02-17 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
CN109890787A (zh) | 2016-11-02 | 2019-06-14 | 默克专利有限公司 | 用于电子器件的材料 |
WO2018087020A1 (en) | 2016-11-08 | 2018-05-17 | Merck Patent Gmbh | Compounds for electronic devices |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
KR102528638B1 (ko) | 2016-11-25 | 2023-05-03 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자 (oled) 를 위한 물질로서의 비스벤조푸란-융합된 인데노[1,2-b]플루오렌 유도체 및 관련된 화합물 |
WO2018095888A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
CN108129431B (zh) * | 2016-12-01 | 2023-04-07 | 北京鼎材科技有限公司 | 一种芴并萘并呋喃衍生物及其应用 |
US11261291B2 (en) | 2016-12-22 | 2022-03-01 | Merck Patent Gmbh | Materials for electronic devices |
WO2018134392A1 (en) | 2017-01-23 | 2018-07-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018141706A1 (de) | 2017-02-02 | 2018-08-09 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018158232A1 (en) | 2017-03-01 | 2018-09-07 | Merck Patent Gmbh | Organic electroluminescent device |
WO2018157981A1 (de) | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
KR102585423B1 (ko) | 2017-04-25 | 2023-10-05 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
KR102174388B1 (ko) * | 2017-05-12 | 2020-11-04 | 주식회사 엘지화학 | 고리 화합물 및 이를 포함하는 유기 발광 소자 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
CN110770363A (zh) | 2017-06-26 | 2020-02-07 | 默克专利有限公司 | 均质混合物 |
US20200136045A1 (en) | 2017-06-28 | 2020-04-30 | Merck Patent Gmbh | Materials for electronic devices |
CN109206376A (zh) * | 2017-06-30 | 2019-01-15 | 固安鼎材科技有限公司 | 稠杂环取代的苯并茚并芴衍生物及其应用 |
US20200212301A1 (en) | 2017-07-28 | 2020-07-02 | Merck Patent Gmbh | Spirobifluorene derivatives for use in electronic devices |
CN107501101A (zh) * | 2017-08-30 | 2017-12-22 | 华南理工大学 | 一种含萘并茚芴单元的有机发光小分子材料及其制备方法与应用 |
KR102746068B1 (ko) * | 2017-09-08 | 2024-12-24 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
KR102735842B1 (ko) * | 2017-09-08 | 2024-11-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
CN108675975A (zh) | 2017-10-17 | 2018-10-19 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
CN107879968B (zh) * | 2017-11-14 | 2021-03-16 | 华南协同创新研究院 | 一类含极性取代基团萘并茚咔唑单元的发光材料及其制备与应用 |
KR20200090817A (ko) | 2017-11-23 | 2020-07-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
TWI820057B (zh) | 2017-11-24 | 2023-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI838352B (zh) | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
WO2019115577A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Substituted aromatic amines for use in organic electroluminescent devices |
US20210036245A1 (en) | 2017-12-20 | 2021-02-04 | Merck Patent Gmbh | Heteroaromatic compounds |
TW201938761A (zh) | 2018-03-06 | 2019-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI802656B (zh) | 2018-03-06 | 2023-05-21 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
US20210020843A1 (en) | 2018-03-16 | 2021-01-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TWI823993B (zh) | 2018-08-28 | 2023-12-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP3844243B1 (en) | 2018-08-28 | 2022-06-22 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TWI837167B (zh) | 2018-08-28 | 2024-04-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP3850055A1 (en) | 2018-09-12 | 2021-07-21 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TW202030192A (zh) | 2018-10-31 | 2020-08-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
WO2020208051A1 (en) | 2019-04-11 | 2020-10-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20200133138A (ko) * | 2019-05-17 | 2020-11-26 | 삼성디스플레이 주식회사 | 아릴아민 화합물 및 이를 포함한 유기 발광 소자 |
CN110563763A (zh) * | 2019-09-29 | 2019-12-13 | 上海天马有机发光显示技术有限公司 | 一种化合物及其应用 |
CN114641482A (zh) | 2019-11-04 | 2022-06-17 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
TW202200529A (zh) | 2020-03-13 | 2022-01-01 | 德商麥克專利有限公司 | 有機電致發光裝置 |
KR20220157456A (ko) | 2020-03-23 | 2022-11-29 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
TW202216952A (zh) | 2020-07-22 | 2022-05-01 | 德商麥克專利有限公司 | 用於有機電發光裝置之材料 |
CN115885599A (zh) | 2020-07-22 | 2023-03-31 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI727889B (zh) * | 2020-09-16 | 2021-05-11 | 晶宜科技股份有限公司 | 有機電激發光裝置及其材料 |
TW202237797A (zh) | 2020-11-30 | 2022-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
KR20230165916A (ko) | 2021-04-09 | 2023-12-05 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
TW202309243A (zh) | 2021-04-09 | 2023-03-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TW202309242A (zh) | 2021-04-09 | 2023-03-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP4079742A1 (de) | 2021-04-14 | 2022-10-26 | Merck Patent GmbH | Metallkomplexe |
CN117355364A (zh) | 2021-05-21 | 2024-01-05 | 默克专利有限公司 | 用于连续纯化至少一种功能材料的方法和用于连续纯化至少一种功能材料的装置 |
WO2023036976A1 (en) | 2021-09-13 | 2023-03-16 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052314A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052272A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP4410074A1 (de) | 2021-09-28 | 2024-08-07 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
EP4437814A1 (de) | 2021-11-25 | 2024-10-02 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
CN118354991A (zh) | 2021-12-21 | 2024-07-16 | 默克专利有限公司 | 用于制备氘化的有机化合物的方法 |
WO2023152346A1 (de) | 2022-02-14 | 2023-08-17 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023208899A1 (en) | 2022-04-28 | 2023-11-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20250011205A (ko) | 2022-05-18 | 2025-01-21 | 메르크 파텐트 게엠베하 | 중수소화 유기 화합물의 제조를 위한 방법 |
CN119452060A (zh) | 2022-07-11 | 2025-02-14 | 默克专利有限公司 | 用于电子器件的材料 |
WO2024033282A1 (en) | 2022-08-09 | 2024-02-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW202438505A (zh) | 2022-12-19 | 2024-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置之材料 |
WO2024132993A1 (de) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024133048A1 (en) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Method for preparing deuterated aromatic compounds |
WO2024170605A1 (en) | 2023-02-17 | 2024-08-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2024218109A1 (de) | 2023-04-20 | 2024-10-24 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024225370A1 (ja) * | 2023-04-27 | 2024-10-31 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子、及び電子機器 |
WO2024240725A1 (de) | 2023-05-25 | 2024-11-28 | Merck Patent Gmbh | Tris[1,2,4]triazolo[1,5-a:1',5'-c:1'',5''-e][1,3,5]triazin-derivate zur verwendung in organischen elektrolumineszenzvorrichtungen |
WO2025012253A1 (en) | 2023-07-12 | 2025-01-16 | Merck Patent Gmbh | Materials for electronic devices |
WO2025021855A1 (de) | 2023-07-27 | 2025-01-30 | Merck Patent Gmbh | Materialien für organische lichtemittierende vorrichtungen und organische sensoren |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200640837A (en) * | 2005-03-18 | 2006-12-01 | Idemitsu Kosan Co | Aromatic amine derivative and organic electroluminescence device utilizing the same |
TW200808683A (en) * | 2006-07-11 | 2008-02-16 | Merck Patent Gmbh | Novel materials for organic electroluminescent devices |
TW200815313A (en) * | 2006-06-02 | 2008-04-01 | Merck Patent Gmbh | Novel materials for organic electroluminescent devices |
TW200951101A (en) * | 2008-05-19 | 2009-12-16 | Merck Patent Gmbh | Compounds for electronic devices |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006108497A1 (de) * | 2005-04-14 | 2006-10-19 | Merck Patent Gmbh | Verbindungen für organische elektronische vorrichtungen |
DE102006015183A1 (de) * | 2006-04-01 | 2007-10-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101003851B1 (ko) * | 2008-06-18 | 2010-12-23 | (주)씨에스엘쏠라 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
DE102008033943A1 (de) * | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008054141A1 (de) * | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005290A1 (de) * | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102009005288A1 (de) * | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8980442B2 (en) * | 2009-03-19 | 2015-03-17 | Mitsui Chemicals, Inc. | Aromatic amine derivative and organic electroluminescent element using same |
KR101324782B1 (ko) | 2010-01-14 | 2013-10-31 | (주)씨에스엘쏠라 | 유기 광소자 및 이를 위한 유기 광합물 |
KR20110121147A (ko) | 2010-04-30 | 2011-11-07 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
-
2013
- 2013-08-06 CN CN201380045932.1A patent/CN104684886B/zh active Active
- 2013-08-06 EP EP13748265.9A patent/EP2892876B1/de active Active
- 2013-08-06 WO PCT/EP2013/002343 patent/WO2014037077A1/de active Application Filing
- 2013-08-06 US US14/425,373 patent/US10439145B2/en active Active
- 2013-08-06 JP JP2015530308A patent/JP6284940B2/ja active Active
- 2013-08-06 KR KR1020157008598A patent/KR102143742B1/ko active IP Right Grant
- 2013-09-02 TW TW102131558A patent/TWI611003B/zh active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200640837A (en) * | 2005-03-18 | 2006-12-01 | Idemitsu Kosan Co | Aromatic amine derivative and organic electroluminescence device utilizing the same |
TW200815313A (en) * | 2006-06-02 | 2008-04-01 | Merck Patent Gmbh | Novel materials for organic electroluminescent devices |
TW200808683A (en) * | 2006-07-11 | 2008-02-16 | Merck Patent Gmbh | Novel materials for organic electroluminescent devices |
TW200951101A (en) * | 2008-05-19 | 2009-12-16 | Merck Patent Gmbh | Compounds for electronic devices |
Also Published As
Publication number | Publication date |
---|---|
WO2014037077A1 (de) | 2014-03-13 |
KR102143742B1 (ko) | 2020-08-12 |
EP2892876B1 (de) | 2018-11-07 |
JP2015534543A (ja) | 2015-12-03 |
JP6284940B2 (ja) | 2018-02-28 |
CN104684886A (zh) | 2015-06-03 |
US10439145B2 (en) | 2019-10-08 |
TW201432021A (zh) | 2014-08-16 |
US20150255720A1 (en) | 2015-09-10 |
EP2892876A1 (de) | 2015-07-15 |
KR20150048883A (ko) | 2015-05-07 |
CN104684886B (zh) | 2017-07-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI611003B (zh) | 用於電子裝置之化合物類 | |
TWI762451B (zh) | 用於電子裝置之化合物 | |
TWI639590B (zh) | 電子裝置用材料 | |
TWI664171B (zh) | 用於電子裝置之材料 | |
TWI721001B (zh) | 用於有機電致發光裝置之材料 | |
CN105980518B (zh) | 化合物和有机电子器件 | |
CN104781247B (zh) | 用于电子器件的材料 | |
CN104884572B (zh) | 用于电子器件的材料 | |
TWI677486B (zh) | 化合物與有機電子裝置 | |
CN105814170B (zh) | 电子器件的材料 | |
TWI646171B (zh) | 化合物與有機電子裝置 | |
CN104837808B (zh) | 用于电子器件的材料 | |
CN111051294B (zh) | 用于电子器件的材料 | |
CN107949561A (zh) | 用于有机电致发光器件的吩噁嗪衍生物 | |
TW201722890A (zh) | 用於電子裝置之材料 | |
CN118126004A (zh) | 用于电子器件的基于螺二芴衍生物的材料 | |
TWI705062B (zh) | 電子裝置用的材料 |