CN113620817B - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
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- CN113620817B CN113620817B CN202010390245.5A CN202010390245A CN113620817B CN 113620817 B CN113620817 B CN 113620817B CN 202010390245 A CN202010390245 A CN 202010390245A CN 113620817 B CN113620817 B CN 113620817B
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- 239000000463 material Substances 0.000 claims abstract description 56
- 230000000903 blocking effect Effects 0.000 claims abstract description 31
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 239000010410 layer Substances 0.000 claims description 105
- -1 cyano, carbonyl Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 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 abstract description 7
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- 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 12
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- 239000000243 solution Substances 0.000 description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
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- VECLPBKDHAALGQ-UHFFFAOYSA-N 3-bromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 VECLPBKDHAALGQ-UHFFFAOYSA-N 0.000 description 5
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- ALEDFYPQEIOLQU-UHFFFAOYSA-N 1-bromo-4-(2-phenylphenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 ALEDFYPQEIOLQU-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
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- 239000000543 intermediate Substances 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
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- 230000015556 catabolic process Effects 0.000 description 2
- 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 2
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- 238000006731 degradation reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- 241000720974 Protium Species 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
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- 230000003321 amplification Effects 0.000 description 1
- 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 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 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
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 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 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C07C2601/14—The ring being saturated
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- 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
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Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I, in the structure of the compound, a parent triarylamine group can effectively regulate and control the three-dimensional structure of molecules, the stacking density of the molecules is improved, and simultaneously, a substituent Ar is introduced into the 1-position of a naphthalene ring, so that the ortho-position steric hindrance can be regulated, the torsion degree of the molecules can be effectively regulated and controlled, and the crystallinity of the molecules is reduced. The introduction of the terphenyl substituent group in a specific connection mode can effectively improve the refractive index of the material, and when the compound disclosed by the invention is used in an organic electroluminescent device, particularly used as an electron blocking layer material, the current efficiency of the device can be effectively improved to achieve the best effect.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, organic Light Emitting Diodes (OLEDs) have been developed rapidly, and have been in the spotlight in the field of information display, which is mainly benefited by that OLED devices can use three primary colors of high saturation red, green and blue to prepare a full-color display device, and the color gorgeous, light, thin and soft performance can be achieved without an additional backlight source. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like.
The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
Various organic materials have been developed, and various peculiar device structures are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property, and sensitizes the luminophor in an energy transfer mode, so that higher luminous efficiency can be realized.
As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc.
Therefore, there is a need in the art to develop an organic electroluminescent material capable of improving the luminous efficiency of the device, reducing the driving voltage, and prolonging the service life.
Disclosure of Invention
The invention aims to provide a compound, which is applied to an organic electroluminescent device and can effectively reduce the driving voltage and improve the luminous efficiency of the device.
To achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound which has a structure shown in a formula I;
in the formula I, ar is selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; ar is preferably one of a substituted or unsubstituted C6-C20 aryl group and a substituted or unsubstituted C3-C20 heteroaryl group;
In the formula I, X is selected from O, S, C (any one of CH 3)2; preferably, X is O or C (any one of CH 3)2;
In formula I, R 1 represents a single substituent to the maximum permissible substituent, and each is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and when R 1 is plural, adjacent R 1 may be fused;
when the above groups are present, the substituent groups are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic or fused ring aryl, C3-C30 monocyclic or fused ring heteroaryl.
Further, the compound of the present invention has a structure represented by the following formula II or formula III:
In the formulas II and III, ar and R 1 are defined as in the formula I.
Further preferably, in the above formulas i, ii and iii, the Ar is selected from any one of the following substituted or unsubstituted groups:
still more preferably, the Ar is selected from any one of the following substituted or unsubstituted groups:
Wherein the wavy line Represents the site of attachment,
When the above groups are present, the substituent groups are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic or fused ring aryl, C3-C30 monocyclic or fused ring heteroaryl.
Still further preferred, R 1 above is selected from hydrogen, deuterium, or the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole group, perylene group, fluoranthenyl, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrenyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, trimeric indenyl group, heterotrimeric indenyl group, spirotrimeric indenyl group, spiroheterotrimeric indenyl group, furyl group, benzofuryl group, spiro isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthizolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridazolyl, anthracenozolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrene, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazolyl, 1,2,3, 4-tetrazolyl, 1, 3-tetrazolyl, 1,3, 4-tetrazolyl, 1, 3-thiazinyl, a combination thereof, or a combination thereof.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are not repeated as shown above.
In the present invention, the monocyclic aryl group means that one or at least two phenyl groups are contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are connected through a single bond, such as phenyl, biphenyl, terphenyl and the like; condensed ring aryl means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other, but the common ring edges are condensed with each other, such as naphthyl, anthracenyl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are connected by a single bond, such as pyridine, furan, thiophene, etc.; fused ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl rings, such as, illustratively, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the present invention, the expression of chemical elements includes the concept of isotopes having the same chemical properties, for example, hydrogen (H) includes 1 H (protium or H), 2 H (deuterium or D), and the like; carbon (C) includes 12C、13 C and the like.
In the present invention, the C1-C20 chain alkyl group is preferably a C1-C10 chain alkyl group, more preferably a C1-C6 chain alkyl group, and examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, n-pentyl, n-heptyl, n-nonyl, n-decyl and the like.
In the present invention, the C3-C20 cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
In the present invention, the substituted or unsubstituted C6-C30 aryl group or C6-C30 condensed ring aryl group, preferably C6-C30 aryl group, more preferably C6-C20 aryl group, preferably the aryl group is a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl.
In the present invention, the substituted or unsubstituted C3-C30 heteroaryl or C3-C30 fused ring heteroaryl, preferably C3-C30 heteroaryl, further preferably C4-C20 heteroaryl, preferably the heteroaryl is furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
Further, the compounds of the general formula of the present invention may preferably be represented by the following specific structural compounds represented by C1-C126, which are representative only:
it is a further object of the present invention to provide the use of a compound according to one of the objects, said compound being useful in an organic electronic device.
Preferably, the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper, preferably an organic electroluminescent device.
Preferably, the compounds are used as electron blocking layer materials in the organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one compound according to one of the objects.
Preferably, the organic layer comprises an electron blocking layer containing at least one compound of one of the purposes.
Specifically, another technical scheme of the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of luminous functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the electron blocking layer contains at least one compound.
More specifically, the organic electroluminescent device will be described in detail.
The OLED device includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), and aromatic amine derivatives as shown below in HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-51 may also be used to dope one or more of HI-1 through HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-24 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The light-emitting layer host material is selected from, but not limited to, one or more of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of YPD-1 through YPD-11 listed below.
In one aspect of the invention, the light-emitting layer employs a technique of thermally activating delayed fluorescence emission. The host material of the light-emitting layer is selected from, but not limited to, one or more of the above-mentioned PH-1 to PH-85.
The organic electroluminescent device of the present invention includes an electron transport region between a light emitting layer and a cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed by applying the compound of the present invention to a multi-layer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-65 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-65 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-65 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following:
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca、Mg。
In the invention, the locus marks in the formula I are shown as the following formula:
The specific reasons for the excellent properties of the compounds of the present invention are not clear, and it is presumed that the following reasons are possible:
In the compound mother nucleus structure, the substituent Ar is introduced into the 1-position of the naphthalene ring, so that the ortho-position steric hindrance can be regulated, the torsion degree of the molecule can be effectively regulated and controlled to reduce the crystallinity of the molecule, the 2-position is substituted with the aromatic amine group, and the introduction of the trisubstituted structure on the aromatic amine group can effectively regulate and control the three-dimensional structure of the molecule, so that the stacking density of the molecule is improved. Meanwhile, a terphenyl substituent group is introduced in a specific connection mode and is matched with a dibenzoheterocycle group for use, so that the molecular structure of the compound is ensured to extend in a rod shape, and the refractive index of the material can be effectively improved. When the compound is applied to an organic electroluminescent device, particularly used as an electron blocking layer, the light extraction efficiency of the organic electroluminescent device can be improved, so that the current efficiency of the device is improved to achieve the best effect.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The synthetic route of the compound shown in the general formula I is as follows:
Wherein X, R 1, ar have the same definition as the symbols in formula I; pd 2(dba)3 represents tris (dibenzyl acetone) dipalladium (0), IPr.HCl represents 1, bis (2, diisopropylphenyl) chloride, naOBu-t represents sodium tert-butoxide, and (t-Bu) 3 P represents tri-tert-butylphosphine.
More specifically, the present invention provides, as an example, a specific synthesis method of representative compounds, such as solvents and reagents used in the following synthesis examples, e.g., 3-bromo-9, 9-dimethylfluorene, 1, bis (2, diisopropylphenyl) chloride imipillar, tris (dibenzyl acetone) dipalladium (0), toluene, methanol, ethanol, tri-t-butylphosphine, sodium t-butoxide, etc., all of which can be purchased or customized from domestic chemical product markets, e.g., from national pharmaceutical groups reagent company, sigma-Aldrich company, beloward reagent company, and intermediates M1 to M7 are customized by reagent companies. In addition, the person skilled in the art can synthesize the compounds by known methods.
Synthesis example 1: synthesis of Compound C1
15G of P1, 17.17g of 4-bromoterphenyl, 0.51g of tris (dibenzylideneacetone) dipalladium, 0.46g IPr.HCl,600mL g of toluene and 16.40g of sodium tert-butoxide are added into a 1L single-port bottle, the vacuum is pumped, nitrogen is exchanged for 3 times, and the reaction temperature is raised to 90 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluting agent, adding methanol, stirring for 1 hr, vacuum filtering to obtain crude product, decocting with methanol/ethyl acetate for 2 hr, and filtering to obtain white powder M1.
Into a 1L single-necked flask, 10g of M1, 7.14g of 3-bromo-9, 9-dimethylfluorene, 0.92g of tris (dibenzylideneacetone) dipalladium, 1mL of tri-tert-butylphosphine, 600mL of toluene and 5.79g of sodium tert-butoxide were added, the mixture was evacuated and nitrogen was replaced for 3 times, and the reaction was warmed to 110℃for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane=10:1, yielding white powder C1.
M/Z theory: 689.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 690.3.
Synthesis example 2: synthesis of Compound C3
15G of P1, 21.41g of 4-bromotetrabiphenyl, 0.51g of tris (dibenzylideneacetone) dipalladium, 0.46g IPr.HCl,600mL g of toluene and 16.40g of sodium tert-butoxide are added into a 1L single-port bottle, the vacuum is pumped, nitrogen is exchanged for 3 times, and the reaction temperature is raised to 90 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluting agent, adding methanol, stirring for 1 hr, vacuum filtering to obtain crude product, decocting with methanol/ethyl acetate for 2 hr, and filtering to obtain white powder M2.
13G of M2, 8.02g of 3-bromo-9, 9-dimethylfluorene, 1.04g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 6.55g of sodium tert-butoxide are added into a 1L single-necked flask, the mixture is vacuumized and replaced with nitrogen for 3 times, and the temperature of the mixture is raised to 110 ℃ for reaction for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give a white powder C3.
M/Z theory: 765.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 766.3.
Synthesis example 3: synthesis of Compound C19
In a 1L single-necked flask, 15g of M1, 9.76g of 2-bromo-dibenzofuran, 1.38g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 8.68g of sodium tert-butoxide were added, the reaction was warmed to 110℃and reacted for 6 hours by changing the nitrogen gas under vacuum for 3 times. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give a white powder C19.
M/Z theory: 663.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 664.3.
Synthesis example 4: synthesis of Compound C55
In a 1L single-necked flask, 15g of P2, 15.48g of 4-boric acid-dibenzothiophene, 1.57g of tetraphenylphosphine palladium, 18.73g of potassium carbonate, 400mL of toluene and 200mL of water were added, the mixture was evacuated and replaced with nitrogen 3 times, and the reaction was warmed to reflux for 5 hours. After the reaction, the reaction was stopped. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding n-hexane, stirring for 1h, suction filtering to obtain a crude product, and recrystallizing with toluene/ethanol to obtain an intermediate M3.
In a 1L single-necked flask, 18g of M3, 17.17g of 4-bromoterphenyl, 0.51g of tris (dibenzylideneacetone) dipalladium, 0.46g IPr.HCl,600mL g of toluene and 16.40g of sodium tert-butoxide were added, the reaction was warmed to 90℃and then reacted for 6 hours by changing the nitrogen gas to 3 times under vacuum. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent with toluene eluent, adding methanol, stirring for 1 hr, vacuum filtering to obtain crude product, washing with methanol/ethyl acetate for 2 hr, and filtering to obtain pale yellow powder M4.
Into a 1L single-port bottle, 12g of M4, 7.67g of 3-bromo-9, 9-dimethylfluorene, 0.99g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 6.25g of sodium tert-butoxide are added, the vacuum is pumped, nitrogen is exchanged for 3 times, and the reaction temperature is raised to 110 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give a pale yellow powder C55.
M/Z theory: 745.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 746.3.
Synthesis example 5: synthesis of Compound C59
In a 1L single-port flask, 12g of M4, 5.34g of 2-bromo-dibenzofuran, 0.99g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 6.25g of sodium tert-butoxide were added, the mixture was evacuated and replaced with nitrogen 3 times, and the reaction was warmed to 110℃for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give pale yellow powder C59.
M/Z theory: 719.2; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 720.2.
Synthesis example 6: synthesis of Compound C81
In a 1L single-necked flask, 15g of P2, 14.39g of 3-boric acid-dibenzofuran, 1.57g of tetraphenylphosphine palladium, 18.73g of potassium carbonate, 400mL of toluene and 200mL of water were added, the mixture was evacuated and replaced with nitrogen 3 times, and the reaction was warmed to reflux for 5 hours. After the reaction, the reaction was stopped. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding n-hexane, stirring for 1h, filtering to obtain a crude product, and recrystallizing with toluene/ethanol to obtain an intermediate M5.
15G of M5, 14.95g of 4-bromoterphenyl, 0.44g of tris (dibenzylideneacetone) dipalladium, 0.41g IPr.HCl,600mL g of toluene, 13.85g of sodium tert-butoxide, and 3 times of vacuum nitrogen exchange are added into a 1L single-port bottle, and the reaction is heated to 90 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent with toluene eluent, adding methanol, stirring for 1 hr, vacuum filtering to obtain crude product, washing with methanol/ethyl acetate for 2 hr, and filtering to obtain pale yellow powder M6.
Into a 1L single-port bottle, 12g of M6, 7.90g of 2-bromo-9, 9-dimethylfluorene, 1.02g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 6.44g of sodium tert-butoxide are added, the mixture is vacuumized and replaced with nitrogen for 3 times, and the temperature is raised to 110 ℃ for reaction for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give pale yellow powder C81.
M/Z theory: 729.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 730.3.
Synthesis example 7: synthesis of Compound C110
15G of P2, 13.44g of 4-diphenyl borate, 1.57g of tetraphenylphosphine palladium, 18.73g of potassium carbonate, 400mL of toluene and 200mL of water are added into a 1L single-necked flask, the mixture is vacuumized and replaced with nitrogen for 3 times, and the reaction temperature is raised to reflux reaction for 5 hours. After the reaction, the reaction was stopped. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding n-hexane, stirring for 1h, filtering to obtain a crude product, and recrystallizing with toluene/ethanol to obtain an intermediate M7.
13G of M7, 13.57g of 4-bromoterphenyl, 0.40g of tris (dibenzylideneacetone) dipalladium, 0.37g IPr.HCl,600mL g of toluene and 12.69g of sodium tert-butoxide are added into a 1L single-port bottle, the vacuum is pumped, nitrogen is exchanged for 3 times, and the reaction temperature is raised to 90 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluting agent, adding methanol, stirring for 1 hr, vacuum filtering to obtain crude product, decocting with methanol/ethyl acetate for 2 hr, and filtering to obtain white powder M8.
Into a 1L single-port bottle, 12g of M8, 8.79g of 3-bromo-9, 9-dimethylfluorene, 1.05g of tris (dibenzylideneacetone) dipalladium, 2mL of tri-tert-butylphosphine, 600mL of toluene and 6.61g of sodium tert-butoxide are added, the vacuum is pumped, nitrogen is exchanged for 3 times, and the reaction temperature is raised to 110 ℃ for 6 hours. After the reaction, the reaction was stopped. Cooling to room temperature, subjecting the reaction solution to 100-200 mesh silica gel column chromatography, removing solvent by toluene eluent, adding methanol, stirring for 1 hr, and suction filtering to obtain crude product. Separating and purifying by column chromatography, wherein petroleum ether is used as the leaching agent: dichloromethane (10:1) to give white powder C110.
M/Z theory: 715.3; ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) M/Z actual measurement values: 716.3.
Device example 1
The embodiment 1 provides a method for preparing an organic electroluminescent device, which specifically comprises the following steps:
After sonicating the glass plate coated with the ITO transparent conductive layer (as anode) in a commercial cleaner, rinsing in deionized water, and washing in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X 10 -5 Pa, and vacuum evaporating HT-4:HI-3 (97/3,w/w) mixture on the anode layer film as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
Vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 60nm;
And vacuum evaporating the compound C1 on the hole transport layer to obtain an electron blocking layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 60nm.
Vacuum evaporating a luminescent layer of the device on the electron blocking layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-59 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye RPD-8 is set to be 3% of the main material, and the total evaporation film thickness is 40nm;
vacuum evaporating electron transport layer materials ET-61 and ET-57 of the device on the luminescent layer, wherein the mass ratio of the electron transport layer materials to the ET-57 is 1:1, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 25nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
Device examples 2-7 differ from device example 1 only in the replacement of the inventive compound C1 used in the electron blocking layer with other inventive compounds, see in particular table 1.
The organic electroluminescent devices provided in comparative examples 1 to 6 were fabricated by the same procedure as in example 1, except that the material compound C1 of the present invention used in the electron blocking layer was replaced with the compounds R1 to R6 of the prior art, respectively, and the structural formulae of the specific compounds were as follows:
Performance test:
(1) The driving voltage and current efficiency and the lifetime of the organic electroluminescent devices manufactured in examples and comparative examples were measured using a digital source meter (Keithley 2400) and a luminance meter (ST-86 LA luminance meter, university of beijing photoelectric instrumentation factory) at the same luminance. Specifically, the voltage was increased at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reached 5000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency;
(2) The lifetime test of LT97 is as follows: the time in hours for the luminance of the organic electroluminescent device to drop to 97% was measured using a luminance meter at 5000cd/m 2 luminance with a constant current.
The results of the performance test are shown in Table 1.
Table 1:
As can be seen from the data in table 1, when the compound of the present invention is used as an electron blocking layer material of an organic electroluminescent device under the condition that the material schemes and the preparation processes of other functional layers in the structure of the organic electroluminescent device are completely the same, when the device brightness reaches 5000cd/m 2, the driving voltage is as low as below 4.3V, the current efficiency is as high as above 19cd/a, and LT97 reaches above 18h, which are all superior to those of the comparative example device using the compound of the present invention as an electron blocking layer material, and therefore, the device using the compound of the present invention has significant performance advantages in terms of both reducing the driving voltage and improving the current efficiency.
The compound R1 adopted in the comparative example 1 is different from the compound of the invention in that the spirofluorene group has increased molecular rigidity and higher sublimation temperature of the material compared with the compound of the invention, and is not suitable for practical application; at the same time, as the molecular volume is increased, the rod-shaped orientation degree of the material is reduced, the refractive index of the material is reduced, and the transmission capability is reduced; in particular, the refractive index is lower than the heteroatom-containing compounds of the present invention. When the compound R1 is used as an electron blocking layer material of an organic electroluminescent device, the driving voltage of the device is 4.94V, and the current efficiency is 18.47cd/A. This is attributable to the weaker hole transport property of the compound R1 itself, and the drive voltage increases; and the refractive index is low, thereby causing a decrease in light extraction efficiency.
The compound R2 adopted in the comparative example 2 is different from the compound of the invention in that the terphenyl substituent is connected in a meta-position mode, the rod-shaped orientation of molecules is destroyed, and the refractive index of the material is not higher than that of the compound of the invention; meanwhile, the meta-position connection mode also reduces the carrier transmission performance; when the compound is used as an electron blocking layer material of an organic electroluminescent device, the driving voltage of the device is 5.12V, the current efficiency is 16.12cd/A, and the voltage and current efficiency are poor, which can be attributed to lower refractive index and lower transmission performance caused by the molecular configuration of the compound R2, so that the photoelectric performance is reduced.
The compounds R3 and R4 used in comparative example 3 and comparative example 4 are different from the compounds of the present invention in that phenanthrene groups are introduced into the structures of the compounds R3 and R4, the triplet energy level of the material is low, and annihilation of the excited state energy is easily caused. When the compounds R3 and R4 are used as electron blocking layer materials of the organic electroluminescent device, the current efficiency of the device is lower than that of the device prepared by adopting the compound, because the electron blocking layer is adjacent to the light emitting layer and needs to have the function of blocking excitons, and the compounds R3 and R4 have lower triplet energy levels, after electrons and holes form excitons in the light emitting layer, the excitons are transferred to the electron blocking layer so as to cause annihilation of energy, and the efficiency of the device is reduced.
Compared with the compound disclosed by the invention, the compound R5 adopted in the comparative example 5 is different in that the structure of the compound R5 adopts the biphenyl, so that the molecular orientation is weakened, and the refractive index of the material is reduced; compound R5 has a refractive index of 1.76, tested at 628nm, which is significantly lower than 1.82 of compound C1 of the invention. When the compound R5 is used as an electron blocking layer material of an organic electroluminescent device, the current efficiency of the device is lower than that of a device manufactured using the compound of the present invention, which is due to the decrease in refractive index, resulting in the decrease in light extraction efficiency.
Compared with the compound disclosed by the invention, the compound R6 adopted in the comparative example 6 is different in that naphthalene is adopted in the structure of the compound R6, the hole transmission performance of the material is obviously reduced compared with that of the compound disclosed by the invention, and meanwhile, the substitution in the ortho position can effectively regulate the torsion degree of molecules so as to reduce the crystallinity of the molecules. When the compound R6 is used as an electron blocking layer material of an organic electroluminescent device, the voltage of the device is higher, and the current efficiency of the device is lower than that of a device prepared by using the compound of the present invention, which is caused by the degradation of the transmission property, thereby resulting in the degradation of the device.
The experimental data show that the novel organic material provided by the invention is used as an electron blocking material of an organic electroluminescent device, is obviously improved compared with the prior art, is an organic luminescent functional material with good performance, and has a wide application prospect.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (9)
1. A compound of the general formula having the structure shown in formula I;
In the formula I, ar is selected from any one of the following substituted or unsubstituted groups:
Wherein the wavy line Represents a ligation site;
In formula I, X is selected from O, S, C (any one of CH 3)2;
In the formula I, R 1 represents a single substituent to the maximum permissible substituent, and each is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and when R 1 is a plurality, adjacent R 1 can be connected in a condensed manner;
when the above groups are present, the substituent groups are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic or fused ring aryl, C3-C30 monocyclic or fused ring heteroaryl.
2. The compound of claim 1, wherein X is selected from O or C (CH 3)2.
3. The compound of claim 1 having any one of the structures of formulas ii and iii below:
In the formulas II and III, ar and R 1 are defined as in the formula I.
4. A compound according to any one of claims 1 to 3, wherein Ar is selected from any one of the following substituted or unsubstituted groups:
Wherein the wavy line Represents the site of attachment,
When the above groups are present, the substituent groups are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic or fused ring aryl, C3-C30 monocyclic or fused ring heteroaryl.
5. The compound of claim 1, having the structure shown below:
6. use of a compound according to any one of claims 1-5 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper.
7. Use of a compound according to claim 6 as an electron blocking layer material in an organic electroluminescent device.
8. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 8, wherein the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the electron blocking layer contains the compound according to any one of claims 1 to 5.
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