JP2003313547A - Organic electroluminescent device material and organic electroluminescent device using the same - Google Patents
Organic electroluminescent device material and organic electroluminescent device using the sameInfo
- Publication number
- JP2003313547A JP2003313547A JP2002116935A JP2002116935A JP2003313547A JP 2003313547 A JP2003313547 A JP 2003313547A JP 2002116935 A JP2002116935 A JP 2002116935A JP 2002116935 A JP2002116935 A JP 2002116935A JP 2003313547 A JP2003313547 A JP 2003313547A
- Authority
- JP
- Japan
- Prior art keywords
- organic
- integer
- electroluminescence device
- compound
- organic electroluminescence
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 239000010409 thin film Substances 0.000 claims abstract description 20
- 238000005401 electroluminescence Methods 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 8
- -1 perfluorophenylene group Chemical group 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000002484 inorganic compounds Chemical class 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000010408 film Substances 0.000 description 29
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 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 18
- 239000013078 crystal Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
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- 229910052786 argon Inorganic materials 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
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- BEKHDAJTCOSDPJ-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-phenylbenzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=CC=CC=C1 BEKHDAJTCOSDPJ-UHFFFAOYSA-N 0.000 description 7
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
- 230000032258 transport Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 4
- 239000000843 powder Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 2
- OPYHNLNYCRZOGY-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-iodobenzene Chemical compound FC1=C(F)C(F)=C(I)C(F)=C1F OPYHNLNYCRZOGY-UHFFFAOYSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
- QFTZULJNRAHOIY-UHFFFAOYSA-N 1,4-dibromo-2,3,5,6-tetrafluorobenzene Chemical compound FC1=C(F)C(Br)=C(F)C(F)=C1Br QFTZULJNRAHOIY-UHFFFAOYSA-N 0.000 description 2
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 2
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical class C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910017109 AlON Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 229910004205 SiNX Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
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- 238000010791 quenching Methods 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
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- PQYIVUDIIIJJDM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-thiadiazole Chemical compound C1=CC=C2C(C3=NN=C(S3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 PQYIVUDIIIJJDM-UHFFFAOYSA-N 0.000 description 1
- KXJIIWGGVZEGBD-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylphenyl)aniline Chemical compound CC1=CC=CC=C1N(C=1C(=CC=CC=1)C)C1=CC=CC=C1C KXJIIWGGVZEGBD-UHFFFAOYSA-N 0.000 description 1
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- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- MWKLOMOIKCPLOY-UHFFFAOYSA-N 3,5-dinaphthalen-1-yl-1h-1,2,4-triazole Chemical compound C1=CC=C2C(C3=NN=C(N3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MWKLOMOIKCPLOY-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HLLICFJUWSZHRJ-UHFFFAOYSA-N tioxidazole Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)SC2=C1 HLLICFJUWSZHRJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-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
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】
【課題】 色純度が高く、青色系に発光する有機エレク
トロルミネッセンス素子を提供可能な有機ＥＬ素子用材
料及びそれを用いた有機ＥＬ素子を提供する。
【解決手段】 フッ素置換フェニル基又はフェニレン基
が窒素に結合した特定構造を有する化合物からなる有機
ＥＬ素子用材料、及び、陰極と陽極間に一層又は複数層
からなる有機薄膜層が挟持されている有機ＥＬ素子にお
いて、該有機薄膜層の少なくとも１層が、前記有機ＥＬ
素子用材料を含有する有機ＥＬ素子である。(57) [Problem] To provide an organic EL element material capable of providing an organic electroluminescence element having high color purity and emitting blue light, and an organic EL element using the same. SOLUTION: An organic EL element material composed of a compound having a specific structure in which a fluorine-substituted phenyl group or a phenylene group is bonded to nitrogen, and an organic thin film layer composed of one or more layers is sandwiched between a cathode and an anode. In the organic EL device, at least one of the organic thin film layers is the organic EL device.
An organic EL device containing a device material.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、有機エレクトロル
ミネッセンス素子用材料及びそれを用いた有機エレクト
ロルミネッセンス素子（有機ＥＬ素子）に関し、特に、
色純度が高く、青色系に発光する有機ＥＬ素子に関する
ものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a material for an organic electroluminescence device and an organic electroluminescence device (organic EL device) using the material, and more particularly,
The present invention relates to an organic EL device having high color purity and emitting blue light.
【０００２】[0002]
【従来の技術】有機物質を使用した有機ＥＬ素子は、固
体発光型の安価な大面積フルカラー表示素子としての用
途が有望視され、多くの開発が行われている。一般に、
有機ＥＬ素子は、発光層及び該層を挟んだ一対の対向電
極から構成されている。有機ＥＬ素子の発光は、両電極
間に電界が印加されると、陰極側から電子が注入され、
陽極側から正孔が注入され、電子が発光層において正孔
と再結合し、励起状態を生成し、励起状態が基底状態に
戻る際にエネルギーを光として放出する現象である。発
光材料としてはトリス（８−キノリノラート）アルミニ
ウム錯体等のキレート錯体、クマリン誘導体、テトラフ
ェニルブタジエン誘導体、ビススチリルアリーレン誘導
体、オキサジアゾール誘導体等の発光材料が知られてお
り、それらからは青色から赤色までの可視領域の発光が
得られることが報告されており、カラー表示素子の実現
が期待されている（例えば、特開平８−２３９６５５号
公報、特開平７−１３８５６１号公報、特開平３−２０
０２８９号公報等）。2. Description of the Related Art An organic EL element using an organic substance is expected to be used as a solid-state light emitting inexpensive large area full color display element, and many developments have been made. In general,
The organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. In the light emission of the organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode side,
This is a phenomenon in which holes are injected from the anode side, electrons are recombined with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state. Known light emitting materials include chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, and oxadiazole derivatives, and from them, blue to red. It has been reported that light emission in the visible region up to is obtained, and realization of a color display element is expected (for example, JP-A-8-239655, JP-A-7-138561 and JP-A-3-20).
No. 0289, etc.).
【０００３】最近では、有機ＥＬ素子ディスプレイの実
用化が開始されているものの、フルカラー表示素子は開
発途中である。特に、色純度及び発光効率が高く、青色
系に発光する有機ＥＬ素子が求められている。これらを
解決しようとするものとして、例えば、特開平８−１２
６００号公報には、青色発光材料としてフェニルアント
ラセン誘導体を用いた素子開示されている。フェニルア
ントラセン誘導体は、青色発光材料として用いられ、通
常、トリス（８−キノリノラート）アルミニウム（Ａｌ
ｑ）錯体層との前記青色材料層の積層体として用いられ
るが、発光効率、寿命、青色純度が実用に用いられるレ
ベルとしては不十分であった。特開２００１−２８８４
６２号公報には、アミン系芳香族化合物を発光層に用い
た青色発光素子が開示されているが、発光効率が２〜４
ｃｄ／Ａと不十分であった。特開２００１−１６０４８
９号公報には、アザフルオランテン化合物を発光層に添
加した素子が開示されているが、黄色から緑色の発光と
なり、十分に色純度の高い青色を発光するに至っていな
い。Recently, the organic EL element display has been put into practical use, but a full-color display element is under development. In particular, there is a demand for an organic EL element that has high color purity and luminous efficiency and emits blue light. As an attempt to solve these problems, for example, Japanese Patent Laid-Open No. 8-12
Japanese Patent Publication No. 600 discloses an element using a phenylanthracene derivative as a blue light emitting material. Phenylanthracene derivatives are used as blue light emitting materials, and are usually tris (8-quinolinolato) aluminum (Al
q) It is used as a laminate of the blue material layer with the complex layer, but the luminous efficiency, the life, and the blue purity were not sufficient as the levels for practical use. JP 2001-2884A
Japanese Patent Laid-Open No. 62-62 discloses a blue light emitting device using an amine-based aromatic compound in a light emitting layer, but has a luminous efficiency of 2 to 4
cd / A was insufficient. JP 2001-16048 A
Japanese Patent Publication No. 9 discloses an element in which an azafluoranthene compound is added to a light emitting layer, but it emits light from yellow to green and does not yet emit blue light having sufficiently high color purity.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、前記の課題
を解決するためになされたもので、色純度が高く、青色
系に発光する有機ＥＬ素子用材料及びそれを利用した有
機ＥＬ素子を提供することである。DISCLOSURE OF THE INVENTION The present invention has been made to solve the above problems, and provides an organic EL device material having high color purity and emitting blue light and an organic EL device using the same. Is to provide.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、前記課題
を解決するために鋭意検討した結果、フッ素置換フェニ
ル基又はフェニレン基が窒素に結合した特定構造を有す
る化合物をホスト材料として用いることにより、青色純
度が高い有機ＥＬ素子が得られることを見出し本発明を
解決するに至った。Means for Solving the Problems As a result of intensive studies for solving the above problems, the inventors have used a compound having a specific structure in which a fluorine-substituted phenyl group or a phenylene group is bonded to nitrogen as a host material. As a result, they have found that an organic EL device with high blue purity can be obtained, and have solved the present invention.
【０００６】すなわち、本発明は、下記一般式（１）で
表される化合物からなる有機ＥＬ素子用材料を提供する
ものである。That is, the present invention provides a material for an organic EL device comprising a compound represented by the following general formula (1).
【化５】
〔（１）式中、ｎは１〜３の整数、ｍは０〜２の整数で
ある。Ａｒ1 、Ａｒ2 及びＡｒ3 は、それぞれ独立に、[Chemical 5] [In the formula (1), n is an integer of 1 to 3 and m is an integer of 0 to 2. Ar 1 , Ar 2 and Ar 3 are each independently
【化６】
（ｐは０〜３の整数、ａは０〜５の整数、ｂは０〜４の
整数）で表され、互いに同一でも異なっていてもよい。
Ａｒ4 及びＡｒ5 は、それぞれ独立に、[Chemical 6] (P is an integer of 0 to 3, a is an integer of 0 to 5 and b is an integer of 0 to 4), and may be the same or different.
Ar 4 and Ar 5 are each independently
【化７】
（ｑは０〜３の整数、ｃ及びｄは、それぞれ０〜４の整
数）で表され、互いに同一でも異なっていてもよい。Ａ
ｒ6 及びＡｒ7 は、それぞれ独立に、[Chemical 7] (Q is an integer of 0 to 3 and c and d are each an integer of 0 to 4) and may be the same or different. A
r 6 and Ar 7 are each independently
【化８】
（ｒは０〜３の整数、ｅは０〜５の整数、ｆは０〜４の
整数）で表され、互いに同一でも異なっていてもよい。
ただし、（１）式中のフェニル基又はフェニレン基のう
ち、少なくとも一つはパーフルオロフェニル基又はパー
フルオロフェニレン基である。また、式中のフェニル基
又はフェニレン基は、フッ素以外の置換基で置換されて
いてもよい。また、隣接する基であるＡｒ1 とＡｒ6 、
Ａｒ4 とＡｒ7 、Ａｒ4 とＡｒ6 、Ａｒ5 とＡｒ7 、Ａ
ｒ3 とＡｒ5 、Ａｒ2 とＡｒ3 は、それぞれ単結合又は
アルキレン基で互いに結合していてもよい。〕[Chemical 8] (R is an integer of 0 to 3, e is an integer of 0 to 5 and f is an integer of 0 to 4) and may be the same or different.
However, at least one of the phenyl groups or phenylene groups in the formula (1) is a perfluorophenyl group or a perfluorophenylene group. Further, the phenyl group or phenylene group in the formula may be substituted with a substituent other than fluorine. In addition, adjacent groups Ar 1 and Ar 6 ,
Ar 4 and Ar 7 , Ar 4 and Ar 6 , Ar 5 and Ar 7 , A
r 3 and Ar 5 , and Ar 2 and Ar 3 may be bonded to each other by a single bond or an alkylene group. ]
【０００７】また、本発明は、陰極と陽極間に一層又は
複数層からなる有機薄膜層が挟持されている有機ＥＬ素
子において、該有機薄膜層の少なくとも１層が、前記有
機ＥＬ素子用材料を含有する有機ＥＬ素子を提供するも
のである。Further, in the present invention, in an organic EL element in which an organic thin film layer composed of one layer or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers is made of the material for the organic EL element. An organic EL device containing the same is provided.
【０００８】[0008]
【発明の実施の形態】本発明の有機ＥＬ素子用材料は、
下記一般式（１）で表される化合物からなる。BEST MODE FOR CARRYING OUT THE INVENTION The material for an organic EL device of the present invention is
It comprises a compound represented by the following general formula (1).
【化９】
（１）式中、ｎは１〜３の整数、ｍは０〜２の整数であ
る。[Chemical 9] In the formula (1), n is an integer of 1 to 3 and m is an integer of 0 to 2.
【０００９】Ａｒ1 、Ａｒ2 及びＡｒ3 は、それぞれ独
立に、Ar 1 , Ar 2 and Ar 3 are each independently
【化１０】
（ｐは０〜３の整数、好ましくは１〜２の整数、ａは０
〜５の整数、好ましくは３〜５の整数、ｂは０〜４の整
数、好ましくは３〜４の整数）で表され、互いに同一で
も異なっていてもよい。Ａｒ4 及びＡｒ5 は、それぞれ
独立に、[Chemical 10] (P is an integer of 0 to 3, preferably 1 to 2 and a is 0.
Is an integer of -5, preferably an integer of 3-5, and b is an integer of 0-4, preferably an integer of 3-4) and may be the same or different. Ar 4 and Ar 5 are each independently
【化１１】
（ｑは０〜３の整数、好ましくは１〜２の整数、ｃ及び
ｄは、それぞれ０〜４の整数、好ましくは３〜４の整
数）で表され、互いに同一でも異なっていてもよい。Ａ
ｒ6 及びＡｒ7 は、それぞれ独立に、[Chemical 11] (Q is an integer of 0 to 3, preferably 1 to 2 and c and d are each an integer of 0 to 4, preferably 3 to 4) and may be the same or different. A
r 6 and Ar 7 are each independently
【化１２】
（ｒは０〜３の整数、、好ましくは１〜２の整数、ｅは
０〜５の整数、好ましくは３〜５の整数、ｆは０〜４の
整数、好ましくは３〜４の整数）で表され、互いに同一
でも異なっていてもよい。ただし、（１）式中のフェニ
ル基又はフェニレン基のうち、少なくとも一つはパーフ
ルオロフェニル基又はパーフルオロフェニレン基であ
る。また、式中のフェニル基又はフェニレン基は、フッ
素以外の置換基で置換されていてもよい。さらに、隣接
する基であるＡｒ1 とＡｒ6 、Ａｒ4 とＡｒ7 、Ａｒ4
とＡｒ6、Ａｒ5 とＡｒ7 、Ａｒ3 とＡｒ5 、Ａｒ2 と
Ａｒ3 は、それぞれ単結合又はアルキレン基（例えば、
メチレン基、エチレン基、プロピレン基等）で互いに結
合していてもよい。[Chemical 12] (R is an integer of 0-3, preferably an integer of 1-2, e is an integer of 0-5, preferably an integer of 3-5, f is an integer of 0-4, preferably an integer of 3-4) And may be the same or different from each other. However, at least one of the phenyl groups or phenylene groups in the formula (1) is a perfluorophenyl group or a perfluorophenylene group. Further, the phenyl group or phenylene group in the formula may be substituted with a substituent other than fluorine. Furthermore, adjacent groups Ar 1 and Ar 6 , Ar 4 and Ar 7 , Ar 4
And Ar 6 , Ar 5 and Ar 7 , Ar 3 and Ar 5 , Ar 2 and Ar 3 are each a single bond or an alkylene group (for example,
Methylene group, ethylene group, propylene group, etc.).
【００１０】上記一般式（１）におけるフッ素以外の置
換基としては、塩素、臭素のハロゲン原子、カルバゾー
ル基、ヒドロキシル基、置換もしくは無置換のアミノ
基、ニトロ基、シアノ基、シリル基、トリフルオロメチ
ル基、カルボニル基、カルボキシル基、置換もしくは無
置換のアルキル基、置換もしくは無置換のアルケニル
基、置換もしくは無置換のアリールアルキル基、置換も
しくは無置換の芳香族基、置換もしくは無置換のヘテロ
芳香族複素環基、置換もしくは無置換のアラルキル基、
置換もしくは無置換のアリールオキシ基、置換もしくは
無置換のアルキルオキシ基等が挙げられる。これらのう
ち、メチル基、パーフルオロフェニレン基、フェニル
基、ナフチル基、ピリジル基、ピラジル基、ピリミジル
基、アダマンチル基、インドリジル基、アザインドリジ
ル基、シアノ基、カルバゾイル基、インドリル基が好ま
しい。Substituents other than fluorine in the above general formula (1) include chlorine, bromine halogen atoms, carbazole groups, hydroxyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, silyl groups and trifluoro groups. Methyl group, carbonyl group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted arylalkyl group, substituted or unsubstituted aromatic group, substituted or unsubstituted heteroaromatic Group heterocyclic groups, substituted or unsubstituted aralkyl groups,
Examples thereof include a substituted or unsubstituted aryloxy group and a substituted or unsubstituted alkyloxy group. Of these, a methyl group, a perfluorophenylene group, a phenyl group, a naphthyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, an adamantyl group, an indolizyl group, an azaindolidyl group, a cyano group, a carbazoyl group, and an indolyl group are preferable.
【００１１】本発明の一般式（１）で表される化合物の
具体例を以下に示すが、これら例示化合物に限定される
ものではない。Specific examples of the compound represented by the general formula (1) of the present invention are shown below, but the compounds are not limited to these exemplified compounds.
【化１３】 [Chemical 13]
【００１２】[0012]
【化１４】 [Chemical 14]
【００１３】本発明の一般式（１）の化合物は、１重項
のエネルギーギャップが２．８〜３．８ｅＶであり、
２．９〜３．６ｅＶであると好ましい。本発明の有機Ｅ
Ｌ素子は、陰極と陽極間に一層又は複数層からなる有機
薄膜層が挟持されている有機ＥＬ素子において、該有機
薄膜層の少なくとも１層が、前記一般式（１）の化合物
からなる有機ＥＬ素子用材料を含有する。また、有機Ｅ
Ｌ素子の発光層に、前記一般式（１）の化合物からなる
有機ＥＬ素子用材料を含有すると好ましい。本発明の有
機ＥＬ素子は、青色系発光し、その純度が（０．１２，
０．１０）〜（０．１７，０．２０）と高いものであ
る。これは、本発明の一般式（１）の化合物からなる有
機ＥＬ素子用材料が、広いエネルギーギャップを有して
いるからである。本発明の有機ＥＬ素子用材料は、有機
ＥＬ素子のホスト材料であると好ましい。このホスト材
料とは、正孔と電子の注入が可能であって、正孔と電子
が輸送され、再結合して蛍光を発する機能を有するもの
である。The compound of the general formula (1) of the present invention has a singlet energy gap of 2.8 to 3.8 eV,
It is preferably 2.9 to 3.6 eV. Organic E of the present invention
The L element is an organic EL element in which an organic thin film layer composed of one layer or a plurality of layers is sandwiched between a cathode and an anode, and at least one layer of the organic thin film layer is an organic EL element comprising the compound of the general formula (1). Contains element materials. In addition, organic E
It is preferable that the light emitting layer of the L element contains an organic EL element material comprising the compound of the general formula (1). The organic EL device of the present invention emits blue light and has a purity of (0.12,
It is as high as 0.10) to (0.17, 0.20). This is because the material for organic EL devices comprising the compound of the general formula (1) of the present invention has a wide energy gap. The material for an organic EL device of the present invention is preferably a host material for an organic EL device. This host material is capable of injecting holes and electrons, and has a function of transporting holes and electrons and recombining to emit fluorescence.
【００１４】また、本発明の一般式（１）の化合物は、
１重項のエネルギーギャップが２．８〜３．８ｅＶと高
く、３重項のエネルギーギャップも高いと考えられ、燐
光素子用の有機ホスト材料としても有用である。ここ
で、燐光素子とは、３重項準位のエネルギー状態から基
底１重項準位の状態への遷移に基づく発光の強度が他の
物質に比べて高い物質、例えば、周期律表７〜１１族か
ら選ばれる少なくとも１つの金属を含む有機金属錯体な
どの燐光物質を含む、いわゆる燐光を利用した有機電界
発光素子のことである。有機ＥＬ素子の発光層におい
て、生成される分子励起子には、１重項励起子と三重項
励起子とが混合していて、１重項励起子及び３重項励起
子は、一般的には１：３の割合で、３重項励起子の方が
多く生成されていると言われている。また、通常の蛍光
を使った有機ＥＬ素子では、発光に寄与する励起子は１
重項励起子であって、３重項励起子は非発光性である。
このため、３重項励起子は最終的には熱として消費され
てしまい、生成率の低い１重項励起子から発光が生じて
いる。したがって、有機ＥＬ素子においては、正孔と電
子との再結合によって発生するエネルギーのうち、３重
項励起子の方へ移動したエネルギーは大きい損失となっ
ている。The compound of the general formula (1) of the present invention is
It is considered that the singlet energy gap is as high as 2.8 to 3.8 eV and the triplet energy gap is also high, and it is also useful as an organic host material for a phosphorescent device. Here, the phosphorescent device is a substance having a higher emission intensity based on the transition from the triplet level energy state to the ground singlet level state than other substances, for example, Periodic Table 7 to An organic electroluminescence device utilizing so-called phosphorescence, which contains a phosphorescent substance such as an organometallic complex containing at least one metal selected from Group 11. In the light emitting layer of the organic EL device, singlet excitons and triplet excitons are mixed in the generated molecular excitons, and the singlet excitons and the triplet excitons are generally It is said that the triplet excitons are generated more in the ratio of 1: 3. Further, in an organic EL element using ordinary fluorescence, the number of excitons contributing to light emission is 1
Triplet excitons, which are triplet excitons, are non-emissive.
Therefore, the triplet excitons are eventually consumed as heat, and the singlet excitons having a low production rate emit light. Therefore, in the organic EL element, of the energy generated by the recombination of holes and electrons, the energy transferred to the triplet excitons causes a large loss.
【００１５】このため、本発明の化合物を燐光素子に利
用することにより、３重項励起子のエネルギーを発光に
使用できるので、蛍光を使った素子の３倍の発光効率の
得られると考えられる。また、本発明の化合物は、燐光
素子の発光層に用いると、該層に含まれる７〜１１族か
ら選ばれる金属を含有する燐光性有機金属錯体の励起３
重項準位より高いエネルギー状態の励起３重項準位を有
し、さらに安定な薄膜形状を与え、高いガラス転移温度
（Ｔｇ：８０〜１６０℃）を有し、正孔及び／又は電子
を効率よく輸送することができ、電気化学的かつ化学的
に安定であり、トラップとなったり発光を消光したりす
る不純物が製造時や使用時に発生しにくいと考えられ
る。Therefore, when the compound of the present invention is used in a phosphorescent device, the energy of triplet excitons can be used for light emission, so that it is considered that the emission efficiency three times that of a device using fluorescence can be obtained. . When the compound of the present invention is used in a light emitting layer of a phosphorescent device, it excites a phosphorescent organometallic complex containing a metal selected from Groups 7 to 11 contained in the layer.
It has an excited triplet level in an energy state higher than the singlet level, gives a more stable thin film shape, has a high glass transition temperature (Tg: 80 to 160 ° C.), and has holes and / or electrons. It is considered that it can be efficiently transported, is electrochemically and chemically stable, and that impurities that become traps or quench light emission are unlikely to be generated during production or use.
【００１６】本発明の有機ＥＬ素子は、前記したように
陽極と陰極間に一層もしくは多層の有機薄膜層を形成し
た素子である。一層型の場合、陽極と陰極との間に発光
層を設けている。発光層は、発光材料を含有し、それに
加えて陽極から注入した正孔、もしくは陰極から注入し
た電子を発光材料まで輸送させるために、正孔注入材料
もしくは電子注入材料を含有してもよい。また、発光材
料は、極めて高い蛍光量子効率、高い正孔輸送能力及び
電子輸送能力を併せ持ち、均一な薄膜を形成することが
好ましい。多層型の有機ＥＬ素子としては、（陽極／正
孔注入層／発光層／陰極）、（陽極／発光層／電子注入
層／陰極）、（陽極／正孔注入層／発光層／電子注入層
／陰極）等の多層構成で積層したものがある。The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between the anode and the cathode as described above. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material for transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. Further, it is preferable that the light emitting material has extremely high fluorescence quantum efficiency, high hole transporting ability and electron transporting ability, and forms a uniform thin film. The multilayer organic EL device includes (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / light emitting layer / electron injection layer). / Cathode) and the like.
【００１７】発光層には、必要に応じて、本発明の一般
式（１）の化合物に加えてさらなる公知のホスト材料、
発光材料、ドーピング材料、正孔注入材料や電子注入材
料を使用し、組み合わせて使用することもできる。有機
ＥＬ素子は、多層構造にすることにより、クエンチング
による輝度や寿命の低下を防ぐことができ、他のドーピ
ング材料により、発光輝度や発光効率を向上させたり、
燐光発光に寄与する他のドーピング材料と組み合わせて
用いることにより、従来の発光輝度や発光効率を向上さ
せることができる。また、本発明の有機ＥＬ素子におけ
る正孔注入層、発光層、電子注入層は、それぞれ二層以
上の層構成により形成されてもよい。その際、正孔注入
層の場合、電極から正孔を注入する層を正孔注入層、正
孔注入層から正孔を受け取り発光層まで正孔を輸送する
層を正孔輸送層と呼ぶ。同様に、電子注入層の場合、電
極から電子を注入する層を電子注入層、電子注入層から
電子を受け取り発光層まで電子を輸送する層を電子輸送
層と呼ぶ。これらの各層は、材料のエネルギー準位、耐
熱性、有機薄膜層もしくは金属電極との密着性等の各要
因により選択されて使用される。本発明の有機ＥＬ素子
は、電子輸送層や正孔輸送層が、一般式（１）の化合物
からなる有機ＥＬ素子用材料を含有してもよい。In the light emitting layer, if necessary, in addition to the compound of the general formula (1) of the present invention, a further known host material,
A light emitting material, a doping material, a hole injecting material and an electron injecting material can be used and can be used in combination. When the organic EL element has a multi-layer structure, it is possible to prevent a decrease in brightness and life due to quenching, and it is possible to improve emission brightness and emission efficiency by using another doping material.
By using it in combination with another doping material that contributes to phosphorescence, conventional emission brightness and emission efficiency can be improved. Further, the hole injection layer, the light emitting layer, and the electron injection layer in the organic EL device of the present invention may each be formed by a layer structure of two or more layers. In that case, in the case of a hole injection layer, a layer that injects holes from the electrode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer is called a hole transport layer. Similarly, in the case of the electron injection layer, the layer that injects electrons from the electrode is called an electron injection layer, and the layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on various factors such as the energy level of the material, heat resistance, and adhesion to the organic thin film layer or the metal electrode. In the organic EL device of the present invention, the electron transport layer and the hole transport layer may contain a material for an organic EL device, which is composed of the compound of the general formula (1).
【００１８】本発明の一般式（１）の化合物と共に有機
薄膜層に使用できる発光材料又はホスト材料としては、
アントラセン、ナフタレン、フェナントレン、ピレン、
テトラセン、コロネン、クリセン、フルオレセイン、ペ
リレン、フタロペリレン、ナフタロペリレン、ペリノ
ン、フタロペリノン、ナフタロペリノン、ジフェニルブ
タジエン、テトラフェニルブタジエン、クマリン、オキ
サジアゾール、アルダジン、ビスベンゾキサゾリン、ビ
ススチリル、ピラジン、シクロペンタジエン、キノリン
金属錯体、アミノキノリン金属錯体、ベンゾキノリン金
属錯体、イミン、ジフェニルエチレン、ビニルアントラ
セン、ジアミノアントラセン、ジアミノカルバゾール、
ピラン、チオピラン、ポリメチン、メロシアニン、イミ
ダゾールキレート化オキシノイド化合物、キナクリド
ン、ルブレン、スチルベン系誘導体及び蛍光色素等が挙
げられるが、これらに限定されるものではない。As the light emitting material or host material which can be used in the organic thin film layer together with the compound of the general formula (1) of the present invention,
Anthracene, naphthalene, phenanthrene, pyrene,
Tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex , Aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminoanthracene, diaminocarbazole,
Examples thereof include, but are not limited to, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compound, quinacridone, rubrene, stilbene derivative and fluorescent dye.
【００１９】正孔注入材料としては、正孔を輸送する能
力を持ち、陽極からの正孔注入効果、発光層又は発光材
料に対して優れた正孔注入効果を有し、発光層で生成し
た励起子の電子注入層又は電子注入材料への移動を防止
し、かつ薄膜形成能力の優れた化合物が好ましい。具体
的には、フタロシアニン誘導体、ナフタロシアニン誘導
体、ポルフィリン誘導体、オキサゾール、オキサジアゾ
ール、トリアゾール、イミダゾール、イミダゾロン、イ
ミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒ
ドロイミダゾール、オキサゾール、オキサジアゾール、
ヒドラゾン、アシルヒドラゾン、ポリアリールアルカ
ン、スチルベン、ブタジエン、ベンジジン型トリフェニ
ルアミン、スチリルアミン型トリフェニルアミン、ジア
ミン型トリフェニルアミン等と、それらの誘導体、及び
ポリビニルカルバゾール、ポリシラン、導電性高分子等
の高分子材料が挙げられるが、これらに限定されるもの
ではない。The hole-injecting material has a capability of transporting holes, has a hole-injecting effect from the anode, and an excellent hole-injecting effect to the light-emitting layer or the light-emitting material, and is produced in the light-emitting layer. A compound that prevents excitons from moving to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole,
Hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and their derivatives, and polyvinylcarbazole, polysilane, conductive polymers, etc. Examples thereof include polymeric materials, but the present invention is not limited thereto.
【００２０】これらの正孔注入材料の中で、さらに効果
的な正孔注入材料は、芳香族三級アミン誘導体又はフタ
ロシアニン誘導体である。芳香族三級アミン誘導体の具
体例としては、トリフェニルアミン、トリトリルアミ
ン、トリルジフェニルアミン、Ｎ，Ｎ’−ジフェニル−
Ｎ，Ｎ’−（３−メチルフェニル）−１，１’−ビフェ
ニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−（４
−メチルフェニル）−１，１’−フェニル−４，４’−
ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−（４−メチルフェニ
ル）−１，１’−ビフェニル−４，４’−ジアミン、
Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジナフチル−１，
１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−
（メチルフェニル）−Ｎ，Ｎ’−（４−ｎ−ブチルフェ
ニル）−フェナントレン−９，１０−ジアミン、Ｎ，Ｎ
−ビス（４−ジ−４−トリルアミノフェニル）−４−フ
ェニル−シクロヘキサン等、又はこれらの芳香族三級ア
ミン骨格を有したオリゴマーもしくはポリマーである
が、これらに限定されるものではない。フタロシアニン
（Ｐｃ）誘導体の具体例は、Ｈ2 Ｐｃ、ＣｕＰｃ、Ｃｏ
Ｐｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、Ｍｎ
Ｐｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、Ｃ
ｌＳｎＰｃ、Ｃｌ2 ＳｉＰｃ、（ＨＯ）ＡｌＰｃ、（Ｈ
Ｏ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰｃ、Ｇ
ａＰｃ−Ｏ−ＧａＰｃ等のフタロシアニン誘導体及びナ
フタロシアニン誘導体であるが、これらに限定されるも
のではない。Among these hole injecting materials, more effective hole injecting materials are aromatic tertiary amine derivatives or phthalocyanine derivatives. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tritolylamine, tolyldiphenylamine, N, N′-diphenyl-
N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N, N', N '-(4
-Methylphenyl) -1,1'-phenyl-4,4'-
Diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-biphenyl-4,4'-diamine,
N, N'-diphenyl-N, N'-dinaphthyl-1,
1'-biphenyl-4,4'-diamine, N, N'-
(Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N
-Bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane and the like, or oligomers or polymers having these aromatic tertiary amine skeletons, but not limited thereto. Specific examples of the phthalocyanine (Pc) derivative include H 2 Pc, CuPc and Co.
Pc, NiPc, ZnPc, PdPc, FePc, Mn
Pc, ClAlPc, ClGaPc, ClInPc, C
lSnPc, Cl 2 SiPc, (HO) AlPc, (H
O) GaPc, VOPc, TiOPc, MoOPc, G
It is a phthalocyanine derivative such as aPc-O-GaPc and a naphthalocyanine derivative, but is not limited thereto.
【００２１】電子注入材料としては、電子を輸送する能
力を持ち、陰極からの電子注入効果、発光層又は発光材
料に対して優れた電子注入効果を有し、発光層で生成し
た励起子の正孔注入層への移動を防止し、かつ薄膜形成
能力の優れた化合物が好ましい。具体的には、フルオレ
ノン、アントラキノジメタン、ジフェノキノン、チオピ
ランジオキシド、オキサゾール、オキサジアゾール、ト
リアゾール、イミダゾール、ペリレンテトラカルボン
酸、キノキサリン、フレオレニリデンメタン、アントラ
キノジメタン、アントロン等とそれらの誘導体が挙げら
れるが、これらに限定されるものではない。The electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode and an excellent electron injecting effect to the light emitting layer or the light emitting material, and the excitons generated in the light emitting layer are positively charged. A compound that prevents migration to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, quinoxaline, fluorenylidene methane, anthraquinodimethane, anthrone and the like. However, the present invention is not limited to these.
【００２２】これらの電子注入材料の中で、さらに効果
的な電子注入材料は、金属錯体化合物又は含窒素五員環
誘導体である。金属錯体化合物の具体例は、８−ヒドロ
キシキノリナートリチウム、ビス（８−ヒドロキシキノ
リナート）亜鉛、ビス（８−ヒドロキシキノリナート）
銅、ビス（８−ヒドロキシキノリナート）マンガン、ト
リス（８−ヒドロキシキノリナート）アルミニウム、ト
リス（２−メチル−８−ヒドロキシキノリナート）アル
ミニウム、トリス（８−ヒドロキシキノリナート）ガリ
ウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナー
ト）ベリリウム、ビス（１０−ヒドロキシベンゾ［ｈ］
キノリナート）亜鉛、ビス（２−メチル−８−キノリナ
ート）クロロガリウム、ビス（２−メチル−８−キノリ
ナート）（ｏ−クレゾラート）ガリウム、ビス（２−メ
チル−８−キノリナート）（１−ナフトラート）アルミ
ニウム、ビス（２−メチル−８−キノリナート）（２−
ナフトラート）ガリウム等が挙げられるが、これらに限
定されるものではない。Among these electron injecting materials, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specific examples of the metal complex compound include lithium 8-hydroxyquinolinate, bis (8-hydroxyquinolinate) zinc, and bis (8-hydroxyquinolinate).
Copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis (10-hydroxybenzo [h] quinolinate) beryllium, bis (10-hydroxybenzo [h]
Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinate) (2-
Examples thereof include, but are not limited to, naphtholate) gallium and the like.
【００２３】また、含窒素五員誘導体は、オキサゾー
ル、チアゾール、オキサジアゾール、チアジアゾールも
しくはトリアゾール誘導体が好ましい。具体的には、
２，５−ビス（１−フェニル）−１，３，４−オキサゾ
ール、ジメチルＰＯＰＯＰ、２，５−ビス（１−フェニ
ル）−１，３，４−チアゾール、２，５−ビス（１−フ
ェニル）−１，３，４−オキサジアゾール、２−（４’
−ｔｅｒｔ−ブチルフェニル）−５−( ４”−ビフェニ
ル) １，３，４−オキサジアゾール、２，５−ビス（１
−ナフチル）−１，３，４−オキサジアゾール、１，４
−ビス［２−( ５−フェニルオキサジアゾリル) ］ベン
ゼン、１，４−ビス［２−( ５−フェニルオキサジアゾ
リル) −４−ｔｅｒｔ−ブチルベンゼン］、２−（４’
−ｔｅｒｔ−ブチルフェニル）−５−( ４”−ビフェニ
ル) −１，３，４−チアジアゾール、２，５−ビス（１
−ナフチル）−１，３，４−チアジアゾール、１，４−
ビス［２−( ５−フェニルチアジアゾリル) ］ベンゼ
ン、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(
４”−ビフェニル) −１，３，４−トリアゾール、２，
５−ビス（１−ナフチル）−１，３，４−トリアゾー
ル、１，４−ビス［２−( ５−フェニルトリアゾリル)
］ベンゼン等が挙げられるが、これらに限定されるも
のではない。The nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative. In particular,
2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) ) -1,3,4-Oxadiazole, 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-oxadiazole, 1,4
-Bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-thiadiazole, 1,4-
Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (
4 "-biphenyl) -1,3,4-triazole, 2,
5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)
Examples thereof include, but are not limited to, benzene and the like.
【００２４】また、正孔注入材料に電子受容物質を、電
子注入材料に電子供与性物質を添加することにより電荷
注入性を向上させることもできる。本発明の有機ＥＬ素
子の陽極に使用される導電性材料としては、４ｅＶより
大きな仕事関数を持つものが適しており、炭素、アルミ
ニウム、バナジウム、鉄、コバルト、ニッケル、タング
ステン、銀、金、白金、パラジウム等及びそれらの合
金、ＩＴＯ基板、ＮＥＳＡ基板に使用される酸化スズ、
酸化インジウム等の酸化金属、さらにはポリチオフェン
やポリピロール等の有機導電性樹脂が用いられる。陰極
に使用される導電性物質としては、４ｅＶより小さな仕
事関数を持つものが適しており、マグネシウム、カルシ
ウム、錫、鉛、チタニウム、イットリウム、リチウム、
ルテニウム、マンガン、アルミニウム等及びそれらの合
金が用いられるが、これらに限定されるものではない。
合金としては、マグネシウム／銀、マグネシウム／イン
ジウム、リチウム／アルミニウム等が代表例として挙げ
られるが、これらに限定されるものではない。合金の比
率は、蒸着源の温度、雰囲気、真空度等により制御さ
れ、適切な比率に選択される。陽極及び陰極は、必要が
あれば二層以上の層構成により形成されていてもよい。The charge injecting property can be improved by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material. As the conductive material used for the anode of the organic EL device of the present invention, those having a work function larger than 4 eV are suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum. , Palladium and alloys thereof, tin oxide used for ITO substrates, NESA substrates,
A metal oxide such as indium oxide, or an organic conductive resin such as polythiophene or polypyrrole is used. As the conductive material used for the cathode, one having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium,
Ruthenium, manganese, aluminum, etc., and alloys thereof are used, but not limited to these.
Typical examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, etc., but are not limited to these. The alloy ratio is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected as an appropriate ratio. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.
【００２５】本発明の有機ＥＬ素子は、少なくとも一方
の電極と前記有機薄膜層との間に無機化合物層を有して
いてもよい。無機化合物層に使用される好ましい無機化
合物としては、アルカリ金属酸化物、アルカリ土類酸化
物、希土類酸化物、アルカリ金属ハロゲン化物、アルカ
リ土類ハロゲン化物、希土類ハロゲン化物、ＳｉＯX、
ＡｌＯX 、ＳｉＮX 、ＳｉＯＮ、ＡｌＯＮ、ＧｅＯX 、
ＬｉＯX 、ＬｉＯＮ、ＴｉＯX 、ＴｉＯＮ、ＴａＯX 、
ＴａＯＮ、ＴａＮX 、Ｃなど各種酸化物、窒化物、酸化
窒化物である。特に陽極に接する層の成分としては、Ｓ
ｉＯX 、ＡｌＯ X 、ＳｉＮX 、ＳｉＯＮ、ＡｌＯＮ、Ｇ
ｅＯX 、Ｃが安定な注入界面層を形成して好ましい。ま
た、特に陰極に接する層の成分としては、ＬｉＦ、Ｍｇ
Ｆ2 、ＣａＦ2 、ＭｇＦ2 、ＮａＦが好ましい。At least one of the organic EL devices of the present invention is
Having an inorganic compound layer between the electrode and the organic thin film layer
You may stay. Preferred mineralization used for inorganic compound layers
Compounds include alkali metal oxides and alkaline earth oxides
Compounds, rare earth oxides, alkali metal halides, alkali
Re-earth halide, rare earth halide, SiOX,
AlOX, SiNX, SiON, AlON, GeOX,
LiOX, LiON, TiOX, TiON, TaOX,
TaON, TaNX, C, various oxides, nitrides, oxidation
It is a nitride. In particular, the component of the layer in contact with the anode is S
iOX, AlO X, SiNX, SiON, AlON, G
eOX, C form a stable injection interface layer, which is preferable. Well
In particular, as the component of the layer in contact with the cathode, LiF, Mg
F2, CaF2, MgF2, NaF are preferred.
【００２６】本発明の有機ＥＬ素子は、効率良く発光さ
せるために、少なくとも一方の面は素子の発光波長領域
において充分透明にすることが望ましい。また、基板も
透明であることが望ましい。透明電極は、上記の導電性
材料を使用して、蒸着やスパッタリング等の方法で所定
の透光性が確保するように設定する。発光面の電極は、
光透過率を１０％以上にすることが望ましい。基板は、
機械的、熱的強度を有し、透明性を有するものであれば
限定されるものではないが、ガラス基板及び透明性樹脂
フィルムが挙げられる。透明性樹脂フィルムとしては、
ポリエチレン、エチレン−酢酸ビニル共重合体、エチレ
ン−ビニルアルコール共重合体、ポリプロピレン、ポリ
スチレン、ポリメチルメタアクリレート、ポリ塩化ビニ
ル、ポリビニルアルコール、ポリビニルブチラール、ナ
イロン、ポリエーテルエーテルケトン、ポリサルホン、
ポリエーテルサルフォン、テトラフルオロエチレン−パ
ーフルオロアルキルビニルエーテル共重合体、ポリビニ
ルフルオライド、テトラフルオロエチレン−エチレン共
重合体、テトラフルオロエチレン−ヘキサフルオロプロ
ピレン共重合体、ポリクロロトリフルオロエチレン、ポ
リビニリデンフルオライド、ポリエステル、ポリカーボ
ネート、ポリウレタン、ポリイミド、ポリエーテルイミ
ド、ポリイミド、ポリプロピレン等が挙げられる。In order to make the organic EL device of the present invention emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the emission wavelength region of the device. It is also desirable that the substrate is transparent. The transparent electrode is made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrodes on the light emitting surface are
It is desirable that the light transmittance is 10% or more. The board is
Although it is not limited as long as it has mechanical and thermal strength and transparency, examples thereof include a glass substrate and a transparent resin film. As a transparent resin film,
Polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethylmethacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone, polysulfone,
Polyether sulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidenefluor Ride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene and the like can be mentioned.
【００２７】本発明の有機ＥＬ素子は、温度、湿度、雰
囲気等に対する安定性の向上のために、素子の表面に保
護層を設けたり、シリコンオイル、樹脂等により素子全
体を保護することも可能である。本発明の有機ＥＬ素子
の各層の形成は、真空蒸着、スパッタリング、プラズ
マ、イオンプレーティング等の乾式成膜法やスピンコー
ティング、ディッピング、フローコーティング等の湿式
成膜法のいずれの方法を適用することができる。各層の
膜厚は特に限定されるものではないが、適切な膜厚に設
定する必要がある。膜厚が厚すぎると、一定の光出力を
得るために大きな印加電圧が必要になり発光効率が悪く
なる。膜厚が薄すぎるとピンホール等が発生して、電界
を印加しても充分な発光輝度が得られない。通常の膜厚
は５ｎｍ〜１０μｍの範囲が適しているが、１０ｎｍ〜
０．２μｍの範囲がさらに好ましい。In the organic EL device of the present invention, a protective layer may be provided on the surface of the device or the entire device may be protected by silicone oil, resin or the like in order to improve stability against temperature, humidity, atmosphere and the like. Is. For formation of each layer of the organic EL device of the present invention, any one of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating and wet film forming methods such as spin coating, dipping and flow coating can be applied. You can Although the film thickness of each layer is not particularly limited, it is necessary to set an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, and the light emission efficiency deteriorates. If the film thickness is too thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. The normal film thickness is preferably in the range of 5 nm to 10 μm, but 10 nm to
The range of 0.2 μm is more preferable.
【００２８】湿式成膜法の場合、各層を形成する材料
を、エタノール、クロロホルム、テトラヒドロフラン、
ジオキサン等の適切な溶媒に溶解又は分散させて薄膜を
形成するが、その溶媒はいずれであってもよい。また、
いずれの層においても、成膜性向上、膜のピンホール防
止等のため適切な樹脂や添加剤を使用してもよい。使用
の可能な樹脂としては、ポリスチレン、ポリカーボネー
ト、ポリアリレート、ポリエステル、ポリアミド、ポリ
ウレタン、ポリスルフォン、ポリメチルメタクリレー
ト、ポリメチルアクリレート、セルロース等の絶縁性樹
脂及びそれらの共重合体、ポリ−Ｎ−ビニルカルバゾー
ル、ポリシラン等の光導電性樹脂、ポリチオフェン、ポ
リピロール等の導電性樹脂が挙げられる。また、添加剤
としては、酸化防止剤、紫外線吸収剤、可塑剤等が挙げ
られる。以上のように、有機ＥＬ素子の有機薄膜層に本
発明の一般式（１）の化合物を用いることにより、色純
度が高く、青色系に発光する有機ＥＬ素子を得ることが
でき、この有機ＥＬ素子は、例えば電子写真感光体、壁
掛けテレビ用フラットパネルディスプレイ等の平面発光
体、複写機、プリンター、液晶ディスプレイのバックラ
イト又は計器類等の光源、表示板、標識灯、アクセサリ
ー等に好適に用いられる。In the case of the wet film forming method, the material forming each layer is ethanol, chloroform, tetrahydrofuran,
The thin film is formed by dissolving or dispersing in a suitable solvent such as dioxane, and any solvent may be used. Also,
Appropriate resins and additives may be used in any of the layers in order to improve film-forming properties and prevent pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Further, examples of the additive include an antioxidant, an ultraviolet absorber, a plasticizer and the like. As described above, by using the compound of the general formula (1) of the present invention for the organic thin film layer of the organic EL element, an organic EL element having high color purity and emitting blue light can be obtained. The element is preferably used for, for example, an electrophotographic photoconductor, a flat light emitter such as a flat panel display for a wall-mounted TV, a copying machine, a printer, a light source of a backlight of a liquid crystal display or instruments, a display plate, a marker lamp, an accessory, and the like. To be
【００２９】[0029]
【実施例】次に、実施例を用いて本発明をさらに詳しく
説明するが、本発明はこれらの実施例に限定されるもの
ではない。
合成例１（化合物（Ａ２）の合成）
化合物（Ａ２）の合成経路を以下に示す。EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Synthesis Example 1 (Synthesis of Compound (A2)) A synthetic route of the compound (A2) is shown below.
【化１５】
※式中、ベンゼン環内にＦが記載されているものは、フ
ッ素以外の基に結合した結合手以外の全ての水素がフッ
素で置換されていることを示す。[Chemical 15] * In the formula, the case where F is described in the benzene ring indicates that all hydrogens other than the bond bonded to the group other than fluorine are replaced with fluorine.
【００３０】（１）Ｎ，Ｎ’−ペンタフルオロフェニル
−１，４−フェニレンジアミンの合成
アルゴン気流下、冷却管付き１Ｌ三口フラスコ中に、
１，４−フェニレンジアミン１０．８ｇ（０．１ｍｏ
ｌ）、ブロモペンタフルオロベンゼン４９．３ｇ（０．
２ｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラ
ジウム１．４ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチル
ホスフィン０．６ｇ（３ｍｏｌ％）、ｔ−ブトキシナト
リウム１９．２ｇ（０．２ｍｏｌ）、乾燥トルエン５０
０ｍＬを加えた後、１００℃にて一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄し、目的とするＮ，Ｎ’−ペンタフルオロフ
ェニル−１，４−フェニレンジアミン１７．６ｇ（収率
４０％）を得た。
（２）化合物（Ａ２）の合成
アルゴン気流下、冷却管付き２００ｍＬ三口フラスコ中
に、Ｎ，Ｎ’−ペンタフルオロフェニル−１，４−フェ
ニレンジアミン４．４ｇ（１０ｍｍｏｌ）、４−ブロモ
ノナフルオロビフェニル８．７ｇ（２２ｍｍｏｌ）、ト
リス（ジベンジリデンアセトン）ジパラジウム０．１４
ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチルホスフィン
０．０６ｇ（３ｍｏｌ％）、ｔ−ブトキシナトリウム
２．１ｇ（２２ｍｍｏｌ）、乾燥トルエン１００ｍＬを
加えた後、１００℃にて一晩加熱攪拌した。反応終了
後、析出した結晶を濾取し、メタノール１００ｍＬにて
洗浄し、白色粉末８．５ｇ（収率８０％）を得た。この
ものは、ＮＭＲ、ＩＲ及びＦＤ−ＭＳ（フィールドディ
フュージョンマススペクトル）の測定により、化合物
（Ａ２）と同定した。また、ＦＤ−ＭＳの測定結果を以
下に示す。
FD-MS, calcd forＣ42Ｈ4 Ｆ28Ｎ2 = 1068, found, m/z
=1068
さらに、得られた化合物をトルエンに溶解し、１０-5ｍ
ｏｌ／リットルの溶液とし、分光光度計（日立社製Ｕ３
４１０）にて吸収スペクトルを計測し、吸収端の波長よ
り換算しエネルギーギャップの値を求め、表１に示し
た。(1) Synthesis of N, N'-pentafluorophenyl-1,4-phenylenediamine In a 1 L three-necked flask equipped with a cooling tube under a stream of argon,
1,4-Phenylenediamine 10.8g (0.1mo
l), 49.3 g of bromopentafluorobenzene (0.
2 mol), tris (dibenzylideneacetone) dipalladium 1.4 g (1.5 mol%), tri-t-butylphosphine 0.6 g (3 mol%), t-butoxy sodium 19.2 g (0.2 mol), dry toluene. Fifty
After adding 0 mL, the mixture was heated with stirring at 100 ° C. overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L to obtain 17.6 g (yield 40%) of the target N, N'-pentafluorophenyl-1,4-phenylenediamine. (2) Synthesis of Compound (A2) 4.4 g (10 mmol) of N, N′-pentafluorophenyl-1,4-phenylenediamine and 4-bromononafluorobiphenyl were placed in a 200 mL three-necked flask equipped with a cooling tube under an argon stream. 8.7 g (22 mmol), tris (dibenzylideneacetone) dipalladium 0.14
g (1.5 mol%), tri-t-butylphosphine 0.06 g (3 mol%), sodium t-butoxy 2.1 g (22 mmol), and dry toluene 100 mL were added, and then the mixture was heated with stirring at 100 ° C. overnight. . After completion of the reaction, the precipitated crystals were collected by filtration and washed with 100 mL of methanol to obtain 8.5 g of white powder (yield 80%). This was identified as the compound (A2) by the measurement of NMR, IR and FD-MS (field diffusion mass spectrum). The measurement results of FD-MS are shown below. FD-MS, calcd for C 42 H 4 F 28 N 2 = 1068, found, m / z
= 1068 Further, the obtained compound was dissolved in toluene to obtain 10 -5 m
ol / liter solution and spectrophotometer (U3 manufactured by Hitachi Ltd.
The absorption spectrum was measured at 410), converted from the wavelength at the absorption edge, and the value of the energy gap was determined.
【００３１】合成例２（化合物（Ａ７）の合成） 化合物（Ａ７）の合成経路を以下に示す。Synthesis Example 2 (Synthesis of Compound (A7)) The synthetic route of the compound (A7) is shown below.
【化１６】 [Chemical 16]
【００３２】（１）４’−ブロモ−２，３，４，５，６
−ペンタフルオロビフェニルの合成
アルゴン気流下、冷却管付き５００ｍＬ三口フラスコ中
に、ヨードペンタフルオロベンゼン３２．３ｇ（０．１
１ｍｏｌ）、４−ブロモフェニルボロン酸２０．８ｇ
（０．１ｍｍｏｌ）、テトラキス（トリフェニルホスフ
ィン）パラジウム１．６ｇ（１．５ｍｏｌ％）、炭酸ナ
トリウム０．１５ｇ（０．３ｍｏｌ）、トルエン２００
ｍＬ、水１５０ｍＬを加えた後、一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄した。この粗結晶は、酢酸エチルにて再結晶
により精製し、目的とする４’−ブロモ−２，３，４，
５，６−ペンタフルオロビフェニル２７．５ｇ（収率８
５％）を得た。
（２）化合物（Ａ７）の合成
アルゴン気流下、冷却管付き５００ｍＬ三口フラスコ中
に、４，４’−ジアミノオクタフルオロビフェニル３．
２ｇ（１０ｍｍｏｌ）、４’−ブロモ−２，３，４，
５，６−ペンタフルオロビフェニル１６．１ｇ（５０ｍ
ｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラジ
ウム０．１４ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチル
ホスフィン０．０６ｇ（３ｍｏｌ％）、ｔ−ブトキシナ
トリウム４．８ｇ（５０ｍｍｏｌ）、乾燥トルエン３０
０ｍＬを加えた後、１００℃にて一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄し、黄色粉末９．０ｇ（収率７０％）を得
た。このものは、ＮＭＲ、ＩＲ及びＦＤ−ＭＳの測定に
より、化合物（Ａ７）と同定した。また、ＦＤ−ＭＳの
測定結果を以下に示す。
FD-MS, calcd forＣ60Ｈ16Ｆ28Ｎ2 = 1296, found, m/z
=1296
さらに、得られた化合物について合成例１と同様にして
エネルギーギャップの値を求め、表１に示した。(1) 4'-bromo-2,3,4,5,6
-Synthesis of pentafluorobiphenyl In a 500 mL three-necked flask equipped with a cooling tube under an argon stream, 32.3 g of iodopentafluorobenzene (0.1
1 mol), 4-bromophenylboronic acid 20.8 g
(0.1 mmol), tetrakis (triphenylphosphine) palladium 1.6 g (1.5 mol%), sodium carbonate 0.15 g (0.3 mol), toluene 200
After adding mL and water (150 mL), the mixture was heated with stirring overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L. The crude crystals were purified by recrystallization from ethyl acetate to obtain the desired 4'-bromo-2,3,4,4.
27.5 g of 5,6-pentafluorobiphenyl (yield 8
5%) was obtained. (2) Synthesis of compound (A7) 4,4′-diaminooctafluorobiphenyl was added to a 500 mL three-necked flask equipped with a cooling tube under an argon stream.
2 g (10 mmol), 4'-bromo-2,3,4
5,6-Pentafluorobiphenyl 16.1 g (50 m
mol), tris (dibenzylideneacetone) dipalladium 0.14 g (1.5 mol%), tri-t-butylphosphine 0.06 g (3 mol%), sodium t-butoxide 4.8 g (50 mmol), dry toluene 30.
After adding 0 mL, the mixture was heated with stirring at 100 ° C. overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L to obtain 9.0 g of a yellow powder (yield 70%). This compound was identified as a compound (A7) by measurement of NMR, IR and FD-MS. The measurement results of FD-MS are shown below. FD-MS, calcd for C 60 H 16 F 28 N 2 = 1296, found, m / z
Further, the energy gap value of the obtained compound was determined in the same manner as in Synthesis Example 1 and shown in Table 1.
【００３３】合成例３（化合物（Ｂ３）の合成） 化合物（Ｂ３）の合成経路を以下に示す。Synthesis Example 3 (Synthesis of Compound (B3)) The synthetic route of the compound (B3) is shown below.
【化１７】 [Chemical 17]
【００３４】（１）４’−ブロモ−２，３，４，５，６
−ペンタフルオロビフェニルの合成
アルゴン気流下、冷却管付き５００ｍＬ三口フラスコ中
に、ヨードペンタフルオロベンゼン３２．３ｇ（０．１
１ｍｏｌ）、４−ブロモフェニルボロン酸２０．８ｇ
（０．１ｍｍｏｌ）、テトラキス（トリフェニルホスフ
ィン）パラジウム１．６ｇ（１．５ｍｏｌ％）、炭酸ナ
トリウム０．１５ｇ（０．３ｍｏｌ）、トルエン２００
ｍＬ、水１５０ｍＬを加えた後、一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄した。この粗結晶は、酢酸エチルにて再結晶
により精製し、目的とする４’−ブロモ−２，３，４，
５，６−ペンタフルオロビフェニル２７．５ｇ（収率８
５％）を得た。
（２）ジ（２’，３’，４’，５’，６’−ペンタフル
オロビフェニル）アミンの合成
アルゴン気流下、冷却管付き１Ｌ三口フラスコ中に、ベ
ンジルアミン４．３ｇ（０．０４ｍｏｌ）、４’−ブロ
モ−２，３，４，５，６−ペンタフルオロビフェニル２
５．８ｇ（０．０８ｍｏｌ）、トリス（ジベンジリデン
アセトン）ジパラジウム０．６ｇ（１．５ｍｏｌ％）、
トリ−ｔ−ブチルホスフィン０．２ｇ（３ｍｏｌ％）、
ｔ−ブトキシナトリウム９．６ｇ（０．１ｍｏｌ）、乾
燥トルエン３００ｍＬを加えた後、１００℃にて一晩加
熱攪拌した。反応終了後、析出した結晶を濾取し、メタ
ノール１００ｍＬにて洗浄し、粗結晶を得た。３００ｍ
Ｌ一口フラスコに、上記粗結晶、Ｐｄ−Ｃ（１０％）
１．６ｇ、クロロホルム１００ｍＬ、エタノール２０ｍ
Ｌを加えた。次に、水素ガス２Ｌが充填された風船（名
称：ガス袋）を装着した３方コックをフラスコに取り付
け，真空ポンプを用いてフラスコ系内を水素ガスで１０
回置換した。減った水素ガスを新たに充填し，水素ガス
の容積を再び２Ｌにした後，室温で一晩、激しく溶液を
攪拌した。反応終了後、ジクロロメタン５０ｍＬを加
え、触媒をろ別した。ろ液を留去し，得られた残さにト
ルエン１５０ｍＬを加え，乾燥管を装着して８５℃まで
昇温し溶解させた後，一晩放置して室温まで徐冷するこ
とにより再結晶化させた。析出した結晶を濾別し，５０
℃で真空乾燥することにより、目的とするジ（２’，
３’，４’，５’，６’−ペンタフルオロビフェニル）
アミン１８ｇ（収率９０％）を得た。(1) 4'-bromo-2,3,4,5,6
-Synthesis of pentafluorobiphenyl In a 500 mL three-necked flask equipped with a cooling tube under an argon stream, 32.3 g of iodopentafluorobenzene (0.1
1 mol), 4-bromophenylboronic acid 20.8 g
(0.1 mmol), tetrakis (triphenylphosphine) palladium 1.6 g (1.5 mol%), sodium carbonate 0.15 g (0.3 mol), toluene 200
After adding mL and water (150 mL), the mixture was heated with stirring overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L. The crude crystals were purified by recrystallization from ethyl acetate to obtain the desired 4'-bromo-2,3,4,4.
27.5 g of 5,6-pentafluorobiphenyl (yield 8
5%) was obtained. (2) Synthesis of di (2 ′, 3 ′, 4 ′, 5 ′, 6′-pentafluorobiphenyl) amine In a 1 L three-necked flask equipped with a cooling tube under an argon stream, 4.3 g (0.04 mol) of benzylamine was used. 4'-bromo-2,3,4,5,6-pentafluorobiphenyl 2
5.8 g (0.08 mol), tris (dibenzylideneacetone) dipalladium 0.6 g (1.5 mol%),
0.2 g (3 mol%) tri-t-butylphosphine,
After adding 9.6 g (0.1 mol) of sodium t-butoxy and 300 mL of dry toluene, the mixture was heated with stirring at 100 ° C. overnight. After completion of the reaction, the precipitated crystals were collected by filtration and washed with 100 mL of methanol to obtain crude crystals. 300m
In a L one-necked flask, the above crude crystals, Pd-C (10%)
1.6 g, chloroform 100 mL, ethanol 20 m
L was added. Next, a 3-way cock equipped with a balloon (name: gas bag) filled with 2 L of hydrogen gas was attached to the flask, and the inside of the flask system was filled with hydrogen gas using a vacuum pump.
Replaced twice. The reduced hydrogen gas was newly charged and the volume of the hydrogen gas was changed to 2 L again, and then the solution was vigorously stirred overnight at room temperature. After the reaction was completed, 50 mL of dichloromethane was added and the catalyst was filtered off. The filtrate was distilled off, 150 mL of toluene was added to the obtained residue, a drying tube was attached, the temperature was raised to 85 ° C. to dissolve, and the mixture was left overnight and gradually cooled to room temperature for recrystallization. It was The precipitated crystals are filtered off,
The desired di (2 ',
3 ', 4', 5 ', 6'-pentafluorobiphenyl)
18 g (yield 90%) of amine was obtained.
【００３５】（３）ジ（２’，３’，４’，５’，６’
−ペンタフルオロビフェニル）−４−ブロモテトラフル
オロフェニルアミンの合成
アルゴン気流下、冷却管付き１Ｌ三口フラスコ中に、
１，４−ジブロモテトラフルオロベンゼン９．２ｇ
（０．０３ｍｏｌ）、ジ（２’，３’，４’，５’，
６’−ペンタフルオロビフェニル）アミン１５．０ｇ
（０．０３ｍｏｌ）、トリス（ジベンジリデンアセト
ン）ジパラジウム０．４２ｇ（１．５ｍｏｌ％）、トリ
−ｔ−ブチルホスフィン０．１８ｇ（３ｍｏｌ％）、ｔ
−ブトキシナトリウム２．９ｇ（０．０３ｍｍｏｌ）、
乾燥トルエン３００ｍＬを加えた後、１００℃にて一晩
加熱攪拌した。反応終了後、析出した結晶を濾取し、メ
タノール１００ｍＬ、塩化メチレン１００ｍＬにて洗浄
し、目的とするジ（２’，３’，４’，５’，６’−ペ
ンタフルオロビフェニル）−４−ブロモテトラフルオロ
フェニルアミン７．６ｇ（収率３５％）を得た。
（４）化合物（Ｂ３）の合成
アルゴン気流下、冷却管付き２００ｍＬ三口フラスコ中
に、ジ（２’，３’，４’，５’，６’−ペンタフルオ
ロビフェニル）−４−ブロモテトラフルオロフェニルア
ミン７．３ｇ（１０ｍｍｏｌ）、アニリン０．４ｇ（４
ｍｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラ
ジウム０．０６ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチ
ルホスフィン０．０２ｇ（３ｍｏｌ％）、ｔ−ブトキシ
ナトリウム１．０ｇ（１０ｍｍｏｌ）、乾燥トルエン５
０ｍＬを加えた後、１００℃にて一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄し、黄色粉末２．８ｇ（収率５０％）を得
た。このものは、ＮＭＲ、ＩＲ及びＦＤ−ＭＳの測定に
より、化合物（Ｂ３）と同定した。また、ＦＤ−ＭＳの
測定結果を以下に示す。
FD-MS, calcd forＣ66Ｈ21Ｆ28Ｎ3 = 1387, found, m/z
=1387
さらに、得られた化合物について合成例１と同様にして
エネルギーギャップの値を求め、表１に示した。(3) Di (2 ', 3', 4 ', 5', 6 '
Synthesis of -pentafluorobiphenyl) -4-bromotetrafluorophenylamine In a 1 L three-necked flask equipped with a cooling tube under an argon stream,
9.2 g of 1,4-dibromotetrafluorobenzene
(0.03 mol), di (2 ', 3', 4 ', 5',
6'-pentafluorobiphenyl) amine 15.0 g
(0.03 mol), tris (dibenzylideneacetone) dipalladium 0.42 g (1.5 mol%), tri-t-butylphosphine 0.18 g (3 mol%), t
-2.9 g (0.03 mmol) of butoxy sodium,
After adding 300 mL of dry toluene, the mixture was heated with stirring at 100 ° C. overnight. After the reaction was completed, the precipitated crystals were collected by filtration, washed with 100 mL of methanol and 100 mL of methylene chloride, and the target di (2 ′, 3 ′, 4 ′, 5 ′, 6′-pentafluorobiphenyl) -4- 7.6 g (yield 35%) of bromotetrafluorophenylamine was obtained. (4) Synthesis of compound (B3) Di (2 ', 3', 4 ', 5', 6'-pentafluorobiphenyl) -4-bromotetrafluorophenyl in a 200 mL three-necked flask equipped with a cooling tube under an argon stream. Amine 7.3 g (10 mmol), aniline 0.4 g (4
mmol), tris (dibenzylideneacetone) dipalladium 0.06 g (1.5 mol%), tri-t-butylphosphine 0.02 g (3 mol%), sodium t-butoxy 1.0 g (10 mmol), dry toluene 5
After adding 0 mL, the mixture was heated with stirring at 100 ° C. overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L to obtain 2.8 g of yellow powder (yield 50%). This was identified as the compound (B3) by measurement of NMR, IR and FD-MS. The measurement results of FD-MS are shown below. FD-MS, calcd for C 66 H 21 F 28 N 3 = 1387, found, m / z
Further, the energy gap value of the obtained compound was determined in the same manner as in Synthesis Example 1 and shown in Table 1.
【００３６】合成例４（化合物（Ｂ８）の合成） 化合物（Ｂ８）の合成経路を以下に示す。Synthesis Example 4 (Synthesis of Compound (B8)) The synthetic route of the compound (B8) is shown below.
【化１８】 [Chemical 18]
【００３７】（１）ジペンタフルオロフェニルアミンの
合成
アルゴン気流下、冷却管付き１００Ｌ三口フラスコ中
に、ペンタフルオロアニリン１８．３ｇ（０．１ｍｏ
ｌ）、ブロモペンタフルオロベンゼン６．２ｇ（０．０
５ｍｏｌ）、トリス（ジベンジリデンアセトン）ジパラ
ジウム０．７ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチル
ホスフィン０．３ｇ（３ｍｏｌ％）、ｔ−ブトキシナト
リウム５．８ｇ（０．０６ｍｏｌ）、乾燥トルエン２０
０ｍＬを加えた後、１００℃にて一晩加熱攪拌した。反
応終了後、析出した結晶を濾取し、メタノール１００ｍ
Ｌにて洗浄し、目的とするジペンタフルオロフェニルア
ミン１０．３ｇ（収率９０％）を得た。
（２）ジペンタフルオロフェニル−４−ブロモテトラフ
ルオロフェニルアミンの合成
アルゴン気流下、冷却管付き５００ｍＬ三口フラスコ中
に、１，４−ジブロモテトラフルオロベンゼン９．２ｇ
（０．０３ｍｏｌ）、ジペンタフルオロフェニルアミン
６．８ｇ（０．０３ｍｏｌ）、トリス（ジベンジリデン
アセトン）ジパラジウム０．４２ｇ（１．５ｍｏｌ
％）、トリ−ｔ−ブチルホスフィン０．１８ｇ（３ｍｏ
ｌ％）、ｔ−ブトキシナトリウム２．９ｇ（０．０３ｍ
ｍｏｌ）、乾燥トルエン２００ｍＬを加えた後、１００
℃にて一晩加熱攪拌した。反応終了後、析出した結晶を
濾取し、メタノール１００ｍＬ、塩化メチレン１００ｍ
Ｌにて洗浄し、目的とするジペンタフルオロフェニル−
４−ブロモテトラフルオロフェニルアミン７．８ｇ（収
率４５％）を得た。
（３）化合物（Ｂ８）の合成
アルゴン気流下、冷却管付き２００ｍＬ三口フラスコ中
に、ジペンタフルオロフェニル−４−ブロモテトラフル
オロフェニルアミン５．８ｇ（１０ｍｍｏｌ）、ジペン
タフルオロフェニルアミン０．７ｇ（４ｍｍｏｌ）、ト
リス（ジベンジリデンアセトン）ジパラジウム０．０６
ｇ（１．５ｍｏｌ％）、トリ−ｔ−ブチルホスフィン
０．０２ｇ（３ｍｏｌ％）、ｔ−ブトキシナトリウム
１．０ｇ（１０ｍｍｏｌ）、乾燥トルエン５０ｍＬを加
えた後、１００℃にて一晩加熱攪拌した。反応終了後、
析出した結晶を濾取し、メタノール１００ｍＬにて洗浄
し、黄色粉末２．８ｇ（収率６０％）を得た。このもの
は、ＮＭＲ、ＩＲ及びＦＤ−ＭＳの測定により、化合物
（Ｂ８）と同定した。また、ＦＤ−ＭＳの測定結果を以
下に示す。
FD-MS, calcd forＣ42Ｆ33Ｎ3 = 1173, found, m/z=117
3
さらに、得られた化合物について合成例１と同様にして
エネルギーギャップの値を求め、表１に示した。(1) Synthesis of dipentafluorophenylamine 18.3 g (0.1 mo) of pentafluoroaniline was placed in a 100 L three-necked flask equipped with a cooling tube under an argon stream.
l), 6.2 g of bromopentafluorobenzene (0.0
5 mol), tris (dibenzylideneacetone) dipalladium 0.7 g (1.5 mol%), tri-t-butylphosphine 0.3 g (3 mol%), sodium t-butoxy 5.8 g (0.06 mol), dry toluene 20
After adding 0 mL, the mixture was heated with stirring at 100 ° C. overnight. After completion of the reaction, the precipitated crystals are collected by filtration and methanol 100m
It was washed with L to obtain 10.3 g (yield 90%) of the target dipentafluorophenylamine. (2) Synthesis of dipentafluorophenyl-4-bromotetrafluorophenylamine 9.2 g of 1,4-dibromotetrafluorobenzene in a 500 mL three-necked flask equipped with a cooling tube under a stream of argon.
(0.03 mol), dipentafluorophenylamine 6.8 g (0.03 mol), tris (dibenzylideneacetone) dipalladium 0.42 g (1.5 mol)
%), 0.18 g of tri-t-butylphosphine (3 mo
1%), sodium tert-butoxide (2.9 g, 0.03 m)
mol), and after adding 200 mL of dry toluene, 100
The mixture was heated with stirring at 0 ° C overnight. After completion of the reaction, the precipitated crystals were collected by filtration, methanol 100 mL, methylene chloride 100 m
After washing with L, the target dipentafluorophenyl-
7.8 g (yield 45%) of 4-bromotetrafluorophenylamine was obtained. (3) Synthesis of compound (B8) In a 200 mL three-necked flask equipped with a cooling tube under an argon stream, 5.8 g (10 mmol) of dipentafluorophenyl-4-bromotetrafluorophenylamine and 0.7 g of dipentafluorophenylamine ( 4 mmol), tris (dibenzylideneacetone) dipalladium 0.06
After adding g (1.5 mol%), tri-t-butylphosphine 0.02 g (3 mol%), sodium t-butoxide 1.0 g (10 mmol) and dry toluene 50 mL, the mixture was heated and stirred at 100 ° C. overnight. . After the reaction,
The precipitated crystals were collected by filtration and washed with 100 mL of methanol to obtain 2.8 g (yield 60%) of yellow powder. This compound was identified as a compound (B8) by measurement of NMR, IR and FD-MS. The measurement results of FD-MS are shown below. FD-MS, calcd for C 42 F 33 N 3 = 1173, found, m / z = 117
3 Further, the energy gap value of the obtained compound was determined in the same manner as in Synthesis Example 1 and shown in Table 1.
【００３８】[0038]
【表１】 [Table 1]
【００３９】実施例１
２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極付
きガラス基板（ジオマティック社製）をイソプロピルア
ルコール中で超音波洗浄を５分間行なった後、ＵＶオゾ
ン洗浄を３０分間行なった。洗浄後の透明電極ライン付
きガラス基板を真空蒸着装置の基板ホルダーに装着し、
まず透明電極ラインが形成されている側の面上に前記透
明電極を覆うようにして膜厚６０ｎｍのＮ，Ｎ’−ビス
（Ｎ，Ｎ’−ジフェニル−４−アミノフェニル）−Ｎ，
Ｎ−ジフェニル−４，４’−ジアミノ−１，１’−ビフ
ェニル膜（ＴＰＤ２３２膜）を成膜した。このＴＰＤ２
３２膜は、正孔注入層として機能する。次に、このＴＰ
Ｄ２３２膜上に膜厚２０ｎｍの４，４’−ビス［Ｎ−
（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル膜
（ＮＰＤ膜）を成膜した。このＮＰＤ膜は正孔輸送層と
して機能する。さらに、このＮＰＤ膜上に膜厚４０ｎｍ
の上記化合物（Ａ２）を蒸着し成膜した。この時、同時
に下記化合物（Ｄ１）を、（Ａ２）：（Ｄ１）の重量比
４０：３で蒸着した。なお、化合物（Ｄ１）は、青色を
発光させるため、１重項のエネルギーが２．７９ｅＶと
低い発光性分子である。化合物（Ａ２）と（Ｄ１）との
混合膜は、発光層として機能する。この膜上に膜厚２０
ｎｍで下記Ｂａｌｑ（Ｍｅはメチル基）を成膜した。Ｂ
ａｌｑ膜は、電子注入層として機能する。この後、還元
性ドーパントであるＬｉ（Ｌｉ源：サエスゲッター社
製）とＡｌｑを二元蒸着させ、第２の電子注入層（陰
極）としてＡｌｑ：Ｌｉ膜（膜厚１０ｎｍ）を形成し
た。このＡｌｑ：Ｌｉ膜上に金属Ａｌを蒸着させ金属陰
極を形成し有機ＥＬ素子を製造した。この素子は、直流
電圧５．２Ｖで発光輝度１５５ｃｄ／ｍ2 、発光効率
５．８ｃｄ／Ａの高効率な青色発光が得られた。また、
色度座標は（０．１５，０．１７）であり、色純度が高
かった。Example 1 A glass substrate (manufactured by Geomatic) with an ITO transparent electrode having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. . Mount the glass substrate with the transparent electrode line after cleaning on the substrate holder of the vacuum evaporation system,
First, N, N′-bis (N, N′-diphenyl-4-aminophenyl) -N, having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
An N-diphenyl-4,4′-diamino-1,1′-biphenyl film (TPD232 film) was formed. This TPD2
The 32nd film functions as a hole injection layer. Next, this TP
On the D232 film, 4,4'-bis [N-
A (1-naphthyl) -N-phenylamino] biphenyl film (NPD film) was formed. This NPD film functions as a hole transport layer. Furthermore, a film thickness of 40 nm is formed on this NPD film.
The above compound (A2) was deposited to form a film. At this time, the following compound (D1) was simultaneously deposited at a weight ratio of (A2) :( D1) of 40: 3. Since the compound (D1) emits blue light, it has a low singlet energy of 2.79 eV and is a light-emitting molecule. The mixed film of the compounds (A2) and (D1) functions as a light emitting layer. A film thickness of 20 on this film
The following Balq (Me is a methyl group) was deposited at nm. B
The alq film functions as an electron injection layer. After that, Li (Li source: manufactured by SAES Getter Co., Ltd.) which is a reducing dopant and Alq were binary-deposited to form an Alq: Li film (film thickness 10 nm) as a second electron injection layer (cathode). Metal Al was vapor-deposited on this Alq: Li film to form a metal cathode, and an organic EL device was manufactured. With this device, highly efficient blue light emission with a light emission luminance of 155 cd / m 2 and a light emission efficiency of 5.8 cd / A was obtained at a DC voltage of 5.2 V. Also,
The chromaticity coordinate was (0.15, 0.17), and the color purity was high.
【００４０】[0040]
【化１９】 [Chemical 19]
【００４１】実施例２〜４
実施例１において、化合物（Ａ２）の代わりに、表２に
記載の化合物を用いた以外は同様にして有機ＥＬ素子を
作製し、同様に直流電圧、発光輝度、発光効率、発光
色、色純度を測定し表２に示した。Examples 2 to 4 Organic EL devices were produced in the same manner as in Example 1 except that the compounds shown in Table 2 were used instead of the compound (A2), and the direct current voltage, the emission luminance, and Luminous efficiency, luminescent color and color purity were measured and are shown in Table 2.
【００４２】比較例１
実施例１において、化合物（Ａ２）の代わりに、従来公
知の化合物である下記化合物ＢＣｚを用いた以外は同様
にして有機ＥＬ素子を作製し、同様に直流電圧、発光輝
度、発光効率、発光色、色純度を測定し表２に示した。Comparative Example 1 An organic EL device was prepared in the same manner as in Example 1 except that the following compound BCz, which was a conventionally known compound, was used in place of the compound (A2). The emission efficiency, emission color, and color purity were measured and are shown in Table 2.
【化２０】 [Chemical 20]
【００４３】比較例２
実施例１において、化合物（Ａ２）の代わりに、特開２
００１−２８８４６２号公報に記載の下記化合物（Ｃ
２）を用いた以外は同様にして有機ＥＬ素子を作製し、
同様に直流電圧、発光輝度、発光効率、発光色、色純度
を測定し表２に示した。Comparative Example 2 Instead of the compound (A2) in Example 1, JP-A 2
The following compounds described in JP-A-001-288462 (C
An organic EL device was prepared in the same manner except that 2) was used.
Similarly, the DC voltage, the emission luminance, the emission efficiency, the emission color, and the color purity were measured and shown in Table 2.
【化２１】 [Chemical 21]
【００４４】[0044]
【表２】 [Table 2]
【００４５】表２に示したように、比較例の従来公知の
化合物ＢＣｚ及び（Ｃ２）に対して、本発明の化合物を
用いた有機ＥＬ素子は、低電圧駆動であり、かつ高効率
の青色発光が得られる。また、本発明の化合物は、エネ
ルギーギャップが広いので、エネルギーギャップの広い
発光性分子を発光層に混合し発光させることができる。As shown in Table 2, in contrast to the conventionally known compounds BCz and (C2) of the comparative example, the organic EL device using the compound of the present invention was driven at a low voltage and had a high efficiency blue color. Luminescence is obtained. Further, since the compound of the present invention has a wide energy gap, it is possible to mix luminescent molecules having a wide energy gap into the luminescent layer to emit light.
【００４６】[0046]
【発明の効果】以上詳細に説明したように、本発明の一
般式（１）で表される化合物からなる有機エレクトロル
ミネッセンス素子用材料を利用すると、発光効率及び色
純度が高く、青色系に発光する有機エレクトロルミネッ
センス素子が得られる。このため、本発明の有機エレク
トロルミネッセンス素子は、各種電子機器の光源等とし
て極めて有用である。As described in detail above, when the material for an organic electroluminescence device comprising the compound represented by the general formula (1) of the present invention is used, the luminous efficiency and color purity are high, and blue light is emitted. Thus, an organic electroluminescence device that can be obtained is obtained. Therefore, the organic electroluminescent element of the present invention is extremely useful as a light source for various electronic devices.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｈ０５Ｂ 33/22 Ｈ０５Ｂ 33/22 Ａ Ｃ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 7 Identification code FI theme code (reference) H05B 33/22 H05B 33/22 AC
Claims (8)
なる有機エレクトロルミネッセンス素子用材料。 【化１】 〔（１）式中、ｎは１〜３の整数、ｍは０〜２の整数で
ある。Ａｒ1 、Ａｒ2 及びＡｒ3 は、それぞれ独立に、 【化２】 （ｐは０〜３の整数、ａは０〜５の整数、ｂは０〜４の
整数）で表され、互いに同一でも異なっていてもよい。
Ａｒ4 及びＡｒ5 は、それぞれ独立に、 【化３】 （ｑは０〜３の整数、ｃ及びｄは、それぞれ０〜４の整
数）で表され、互いに同一でも異なっていてもよい。Ａ
ｒ6 及びＡｒ7 は、それぞれ独立に、 【化４】 （ｒは０〜３の整数、ｅは０〜５の整数、ｆは０〜４の
整数）で表され、互いに同一でも異なっていてもよい。
ただし、（１）式中のフェニル基又はフェニレン基のう
ち、少なくとも一つはパーフルオロフェニル基又はパー
フルオロフェニレン基である。また、式中のフェニル基
又はフェニレン基は、フッ素以外の置換基で置換されて
いてもよい。また、隣接する基であるＡｒ1 とＡｒ6 、
Ａｒ4 とＡｒ7 、Ａｒ4 とＡｒ6 、Ａｒ5 とＡｒ7 、Ａ
ｒ3 とＡｒ5 、Ａｒ2 とＡｒ3 は、それぞれ単結合又は
アルキレン基で互いに結合していてもよい。〕1. A material for an organic electroluminescence device comprising a compound represented by the following general formula (1). [Chemical 1] [In the formula (1), n is an integer of 1 to 3 and m is an integer of 0 to 2. Ar 1 , Ar 2 and Ar 3 are each independently (P is an integer of 0 to 3, a is an integer of 0 to 5 and b is an integer of 0 to 4), and may be the same or different.
Ar 4 and Ar 5 are each independently (Q is an integer of 0 to 3 and c and d are each an integer of 0 to 4) and may be the same or different. A
r 6 and Ar 7 are each independently (R is an integer of 0 to 3, e is an integer of 0 to 5 and f is an integer of 0 to 4) and may be the same or different.
However, at least one of the phenyl groups or phenylene groups in the formula (1) is a perfluorophenyl group or a perfluorophenylene group. Further, the phenyl group or phenylene group in the formula may be substituted with a substituent other than fluorine. In addition, adjacent groups Ar 1 and Ar 6 ,
Ar 4 and Ar 7 , Ar 4 and Ar 6 , Ar 5 and Ar 7 , A
r 3 and Ar 5 , and Ar 2 and Ar 3 may be bonded to each other by a single bond or an alkylene group. ]
ネルギーギャップが２．８〜３．８ｅＶである請求項１
に記載の有機エレクトロルミネッセンス素子用材料。2. The singlet energy gap of the compound of the general formula (1) is 2.8 to 3.8 eV.
The material for an organic electroluminescent device according to item 1.
有機薄膜層が挟持されている有機エレクトロルミネッセ
ンス素子において、該有機薄膜層の少なくとも１層が、
請求項１に記載の有機エレクトロルミネッセンス素子用
材料を含有する有機エレクトロルミネッセンス素子。3. In an organic electroluminescence device in which an organic thin film layer consisting of one or a plurality of layers is sandwiched between a cathode and an anode, at least one of the organic thin film layers comprises
An organic electroluminescence device containing the material for organic electroluminescence device according to claim 1.
有機薄膜層が挟持されている有機エレクトロルミネッセ
ンス素子において、発光層が、請求項１に記載の有機エ
レクトロルミネッセンス素子用材料を含有する有機エレ
クトロルミネッセンス素子。4. In an organic electroluminescence device having an organic thin film layer consisting of one layer or a plurality of layers sandwiched between a cathode and an anode, the light emitting layer contains an organic electroluminescence device material according to claim 1. Electroluminescent device.
用材料の１重項のエネルギーギャップが２．８〜３．８
ｅＶである請求項４に記載の有機エレクトロルミネッセ
ンス素子。5. The singlet energy gap of the material for an organic electroluminescence device is 2.8 to 3.8.
The organic electroluminescent element according to claim 4, which is eV.
用材料が、有機ホスト材料である請求項３又は４に記載
の有機エレクトロルミネッセンス素子。6. The organic electroluminescence device according to claim 3, wherein the material for the organic electroluminescence device is an organic host material.
との間に無機化合物層を有する請求項３〜６のいずれか
に記載の有機エレクトロルミネッセンス素子。7. The organic electroluminescence device according to claim 3, further comprising an inorganic compound layer between at least one electrode and the organic thin film layer.
に記載の有機エレクトロルミネッセンス素子。8. The organic electroluminescence device according to claim 3, which emits blue light.
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| JP2002116935A JP2003313547A (en) | 2002-04-19 | 2002-04-19 | Organic electroluminescent device material and organic electroluminescent device using the same |
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|---|---|---|---|
| JP2002116935A JP2003313547A (en) | 2002-04-19 | 2002-04-19 | Organic electroluminescent device material and organic electroluminescent device using the same |
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| JP2003313547A true JP2003313547A (en) | 2003-11-06 |
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| Country | Link |
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| JP (1) | JP2003313547A (en) |
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