CN114014764A - 含有三亚苯基团的有机化合物、电致发光器件和显示装置 - Google Patents
含有三亚苯基团的有机化合物、电致发光器件和显示装置 Download PDFInfo
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- CN114014764A CN114014764A CN202111355621.8A CN202111355621A CN114014764A CN 114014764 A CN114014764 A CN 114014764A CN 202111355621 A CN202111355621 A CN 202111355621A CN 114014764 A CN114014764 A CN 114014764A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 36
- 125000005580 triphenylene group Chemical group 0.000 title claims description 7
- 230000005525 hole transport Effects 0.000 claims abstract description 21
- 230000000903 blocking effect Effects 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 22
- -1 benzofluorenyl Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 20
- 230000015572 biosynthetic process Effects 0.000 description 68
- 238000003786 synthesis reaction Methods 0.000 description 68
- 239000010410 layer Substances 0.000 description 43
- 238000001514 detection method Methods 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
- 229940125904 compound 1 Drugs 0.000 description 16
- 238000001819 mass spectrum Methods 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000005266 diarylamine group Chemical group 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 4
- 229940126639 Compound 33 Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 4
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 4
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229940126086 compound 21 Drugs 0.000 description 4
- 229940127271 compound 49 Drugs 0.000 description 4
- 229940126179 compound 72 Drugs 0.000 description 4
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 3
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- KVPWXMUWMNYFON-UHFFFAOYSA-N (7-naphthalen-2-yltriphenylen-2-yl)boronic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=C2C=3C=CC(=CC=3C3=CC=CC=C3C2=C1)B(O)O KVPWXMUWMNYFON-UHFFFAOYSA-N 0.000 description 1
- MSBNELVKHUKSPY-UHFFFAOYSA-N 1,2-dibromo-4,5-diphenylbenzene Chemical group C=1C=CC=CC=1C=1C=C(Br)C(Br)=CC=1C1=CC=CC=C1 MSBNELVKHUKSPY-UHFFFAOYSA-N 0.000 description 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PLAKKSAFIZVHJP-UHFFFAOYSA-N 2-bromo-1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C(Br)=C1 PLAKKSAFIZVHJP-UHFFFAOYSA-N 0.000 description 1
- RDBHQZLQCUALTF-UHFFFAOYSA-N 4-(4-anilinophenyl)aniline Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1 RDBHQZLQCUALTF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- C07C211/54—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 two or three six-membered aromatic rings
-
- 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
- C07C211/44—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 only one six-membered aromatic ring
- C07C211/52—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 only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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Abstract
本发明提供一种含有三亚苯基团的有机化合物、电致发光器件和显示装置,本发明的有机化合物可以用做OLED发光器件的电子阻挡层材料和空穴传输材料,使得器件具有较低的驱动电压和较高的电流效率。
Description
技术领域
本发明属于电致发光领域,特别涉及一种有机化合物、有机电致发光器件和显示装置,尤其涉及一种含有三亚苯基团的有机化合物、电致发光器件和显示装置。
背景技术
当前,有机电致发光(OLED)显示技术已经在智能手机,平板电脑等领域获得应用,进一步还将向电视等大尺寸应用领域扩展。在近30年的发展过程中,人们研制出了各种性能优良的OLED材料,并通过对器件结构的不同设计,和对器件寿命、效率等性能的优化,加快了OLED的商业化进程,使得OLED在显示和照明领域得到了广泛应用。
空穴层、发光层以及其他有机功能层材料的选择也对器件的电流效率、驱动电压以及寿命产生较大的影响,目前仍在探索具有更高性能的功能层材料。
因此,为了满足人们对于OLED器件的更高要求,本领域亟待开发更多种类、更高性能的OLED材料。
发明内容
针对现有技术的不足,本发明的目的在于提供一种有机化合物、有机电致发光器件和显示装置,特别是提供一种含有三亚苯基团的有机化合物、电致发光器件和显示装置。本发明的有机化合物可以用做OLED发光器件的电子阻挡层材料和空穴传输层材料。
为达此目的,本发明采用以下技术方案:
一方面,本发明提供一种有机化合物,所述有机化合物具有式I所示结构:
R1、R2、R3和R4独立地选自H、F、CN、D(氘)、取代或未取代的C1~C6的烷基、取代或未取代的C1~C6的烷氧基、取代或未取代的C6~C40芳基;
所述取代或未取代的基团中含有取代基时,所述取代基选自F、CN、D(氘)、C1~C6的烷基、C1~C6的烷氧基、C6~C40芳基。
优选地,所述C6~C40的芳基选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、芴基、苯并芴基、二苯并芴基、萘并芴基、芘基、苝基、螺芴基、三亚苯基、荧蒽基、氢化苯并蒽基、茚并芴基、苯并茚并芴基、二苯并茚并芴基、萘并芴基、苯并萘并芴基中的一个或者二个以上基团的组合。
优选地,所述C5~C40的杂芳基选自二苯并呋喃基、二苯并噻吩基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯并二苯并呋喃基、二苯并二苯并噻吩基、萘并二苯并呋喃基、萘并二苯并噻吩基、苯并萘并二苯并呋喃基或苯并萘并二苯并噻吩基。
优选地,Ar1和Ar2相同。
优选地,Ar1和Ar2不相同。
优选地,Ar1和Ar2独立地选自 其中R每次出现时为氢、C1-C5(例如C1、C2、C3、C4或C5)烷基或C6-C12(例如C6、C7、C8、C9、C10、C11或C12)芳基,X为O或S,波浪线代表基团的连接位点。
优选地,Ar1和Ar2其中至少一个选自取代或未取代的C5~C40的杂芳基。
进一步优选地,Ar1和Ar2其中至少一个选自三亚苯基或者荧蒽基。
优选地,所述有机化合物具有式I-1所示结构:
其中R11,R12独立地选自H、取代或未取代C6~C20的芳基,所述取代或未取代的基团中含有取代基时,所述取代基选自F、CN、D(氘)、C1~C6的烷基、C1~C6的烷氧基、C6~C40芳基。
进一步优选地,所述有机化合物具有式I-2所示的结构:
其中R11、R12、R13和R14独立地选自H、取代或未取代C6~C20的芳基,所述取代或未取代的基团中含有取代基时,所述取代基选自F、CN、D(氘)、C1~C6的烷基、C1~C6的烷氧基、C6~C40芳基。
在本发明中,基团的限定中限定了碳原子数的范围,其碳原子数为所限定范围内的任一整数,例如C6-C40芳基,代表芳基的碳原子数可以是6-40所包含的范围内的任意整数,例如6、8、10、15、20、30、35、38或40等,其他基团的碳原子数限定范围依次类推具有相同的含义。
优选地,所述有机化合物为如下化合物中的任意一种:
在本发明中,所述有机化合物的的合成路径如下:
当R1和R4相同,R2和R3相同时,可以采用以下合成路线:
另一方面,本发明提供一种电子阻挡层,所述电子阻挡层包括如上所述的有机化合物。
另一方面,本发明提供了一种空穴传输层,所述空穴传输层包括如上所述的有机化合物。
另一方面,本发明提供了一种有机电致发光器件,所述有机电致发光器件中包括如上所述的有机化合物。
优选地,所述有机电致发光器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,以及所述有机薄膜层包括如上所述的有机化合物。
优选地,所述有机薄膜层包括电子阻挡层,所述电子阻挡层包括如上所述的有机化合物。
优选地,所述有机电致发光器件包括空穴传输层。
优选地,所述空穴传输层包括如上所述的有机化合物。
另一方面,本发明提供一种显示装置,所述显示装置包括如上所述的有机电致发光器件。
相对于现有技术,本发明具有以下有益效果:
本发明的有机化合物可以用作OLED器件的电子阻挡层,和空穴传输层,用于改善材料性能,利用本申请化合物用作OLED器件的电子阻挡层所制备的有机电致发光器件具有较长的寿命,利用本申请化合物用作OLED器件的空穴传输层所制备的有机电致发光器件具有较高的效率。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
合成实施例1化合物1的合成
(1)中间体M-1-1的合成:
250毫升三口瓶,氮气保护,加入50毫升甲苯,30毫升乙醇,15毫升水,再加入2.36克(0.01mol)邻二溴苯,2.72克(0.01mol)三亚苯-2-硼酸,2.12克(0.02mol)碳酸钠,0.115克(0.0001mol)四三苯基膦钯,缓慢升温至60℃反应4小时,再升温至回流反应4小时,降温,加水分液,有机层水洗后,硫酸镁干燥,过滤除去硫酸镁后,减压除去溶剂,得到的固体柱层析分离,石油醚洗脱,得到M-1-1所示中间体2.7克。
对M-1-1所示中间体进行了质谱检测,m/z最大的两个峰为:382、384,确定产品分子式为C24H15Br。
(2)化合物1的合成:
500毫升三口瓶,氮气保护,加入200毫升干燥的甲苯,3.83克(0.01mol)M-1-1所示化合物,3.21克(0.01mol)二联苯胺,0.0575克(0.0001mol)Pd(dba)2(双二亚苄基丙酮钯),0.4克(0.0002mol)含有10%三叔丁基膦的甲苯溶液,1.44克(0.015mol)叔丁醇钠,加热至回流反应6小时,降温,加水分液,有机层水洗至中性,硫酸镁干燥,过滤除去硫酸镁后,浓缩至干,硅胶柱层析分离,石油醚:乙酸乙酯=10:0.5(体积比)洗脱,得到化合物1为5.1克。
对化合物1进行了质谱检测,确定分子m/z为:623。
对化合物1进行了核磁检测,数据解析如下:1H-NMR(瑞士Bruker公司,AvanceⅡ400MHz核磁共振波谱仪,CDCl3),δ9.58(m,1H),δ9.10(d,1H),δ8.68(d,1H),δ8.40(m,1H),δ8.31(m,1H),δ8.11(m,1H),δ7.78~7.60(m,8H),δ7.59~7.34(m,18H),δ7.15(m,1H)。
合成实施例2化合物5的合成
(1)中间体M-5-1的合成:
合成方法参照实施例1中,中间体M-1-1的合成,只是将其中的三亚苯-2-硼酸换成7-(2-萘基)-三亚苯-2-硼酸,得到M-5-1所示中间体。
对M-5-1所示中间体进行了质谱检测,m/z最大的两个峰为:508、510,确定产品分子式为C34H21Br。
(2)化合物5的合成:
合成方法参照实施例1中化合物1的合成,只是将其中的中间体M-1-1换成中间体M-5-1,将其中的二联苯胺换成N-苯基联苯胺,得到化合物5。
对化合物5进行了质谱检测,确定分子m/z为:673。
合成实施例3化合物21的合成
(1)中间体M-21-1的合成:
250毫升三口瓶,氮气保护,加入80毫升干燥的甲苯,2.54克(0.015mol)联苯胺,3.89克(0.01mol)2-溴-6,6,12,12-四甲基-6,12-二氢吲哚并[1,2-b]芴,0.0575克(0.0001mol)Pd(dba)2(双二亚苄基丙酮钯),0.4克(0.0002mol)含有10%三叔丁基膦的甲苯溶液,1.44克(0.015mol)叔丁醇钠,加热至回流反应8小时,降温,加水分液,有机层用2%的盐酸洗涤2次,水洗至中性,硫酸镁干燥,过滤除去硫酸镁后,浓缩至干,甲醇和甲苯混合溶剂重结晶,得到式M-21-1所示中间体3.1克。
对式M-21-1所示中间体进行了质谱检测,确定分子m/z为:477。
(2)化合物21的合成:
合成方法参照实施例1中化合物1的合成,只是将其中的二联苯胺换成M-21-1所示中间体,得到化合物21。
对化合物21进行了质谱检测,确定分子m/z为:779。
合成实施例4化合物33的合成
(1)中间体M-33-1的合成:
参照中间体M-21-1的合成,只是选用相应的溴代物和胺,得到中间体M-33-1。
对式M-33-1所示中间体进行了质谱检测,确定分子m/z为:369。
(2)化合物33的合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物33。
对化合物33进行了质谱检测,确定分子m/z为:671。
合成实施例5化合物37的合成
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物37。
对化合物37进行了质谱检测,确定分子m/z为:771。
合成实施例6化合物45的合成
(1)中间体M-45-1的合成:
参照中间体M-1-1的合成,只是用3-溴-4-碘甲苯代替邻二溴苯,反应条件为60℃反应8小时,得到中间体M-45-1。
对式M-45-1所示中间体进行了质谱检测,m/z最大的两个峰为:396、398,确定产品分子式为:C25H17Br。
(2)化合物45的合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物45。
对化合物45进行了质谱检测,确定分子m/z为:637。
合成实施例7化合物49的合成
(1)中间体M-49-1的合成:
参照中间体M-1-1的合成,只是用4,5-二苯基-1,2-二溴苯代替邻二溴苯,得到中间体M-49-1。
对式M-49-1所示中间体进行了质谱检测,m/z最大的两个峰为:534、536,确定产品分子式为:C36H23Br。
(2)化合物49的合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物49。
对化合物49进行了质谱检测,确定分子m/z为:775。
合成实施例8化合物56的合成
(1)中间体M-56-1的合成:
参照中间体M-45-1的合成,只是选用相应的溴代物(碘代物),得到中间体M-56-1。
对式M-56-1所示中间体进行了质谱检测,m/z最大的两个峰为:442、440,确定产品分子式为:C27H21BrO。
(2)化合物56的合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物56。对化合物56进行了质谱检测,确定分子m/z为:681。
合成实施例9化合物66的合成
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物66。对化合物66进行了质谱检测,确定分子m/z为:763。
合成实施例10化合物72的合成
(1)中间体M-72-1的合成:
参照中间体M-21-1的合成,只是选用相应的溴代物和胺,得到中间体M-72-1。
对式M-72-1所示中间体进行了质谱检测,确定分子m/z为:487。
(2)化合物72合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物72。
对化合物72进行了质谱检测,确定分子m/z为:789。
合成实施例11化合物76的合成
(1)中间体M-76-1的合成:
参照中间体M-21-1的合成,只是选用相应的溴代物和胺,得到中间体M-76-1。
对式M-76-1所示中间体进行了质谱检测,确定分子m/z为:501。
(2)化合物76合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物76。
对化合物76进行了质谱检测,确定分子m/z为:803。
合成实施例12化合物91的合成
(1)中间体M-91-1的合成:
参照中间体M-21-1的合成,只是选用相应的溴代物和胺,得到中间体M-91-1。
对式M-91-1所示中间体进行了质谱检测,确定分子m/z为:577。
(2)化合物91合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物91。
对化合物91进行了质谱检测,确定分子m/z为:879。
合成实施例13化合物106的合成
(1)中间体M-106-1的合成:
参照中间体M-21-1的合成,只是选用相应的溴代物和胺,得到中间体M-106-1。
对式M-106-1所示中间体进行了质谱检测,确定分子m/z为:425。
(2)化合物106合成:
参照化合物1的合成,只是选用相应的溴代物和二芳胺,得到化合物106。
对化合物106进行了质谱检测,确定分子m/z为:727。
本发明中的其它化合物,可以参照以上方法,结合本领域公知常识合成,不再一一列出。
器件实施例中所用的材料:
器件实施例1
实施例选用本申请的化合物作为有机电致发光器件中的空穴传输材料,比较实施例选用HT-1~HT-4作为有机电致发光器件中的空穴传输材料。
有机电致发光器件结构为:ITO/HIL02(80nm)/空穴传输材料(35nm)/EM1(30nm)/TPBI(30nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下:
将涂布了ITO透明导电层(作为阳极)的玻璃基板在清洗剂中进行超声处理,然后在去离子水中冲洗,再在丙酮与乙醇混合溶剂中超声除油,再在洁净环境下烘烤至完全除水,用紫外光和臭氧清洗,并用低能阳离子束轰击表面,以改善表面的性质,提高与空穴注入层的结合能力;
将上述玻璃基板置于真空腔内,抽真空至1×10-5~9×10-4Pa,在阳极上真空蒸镀HIL02作为空穴注入层,蒸镀速率0.01nm/s,蒸镀膜厚为80nm;
在空穴注入层上分别真空蒸镀本申请化合物或对比材料作为空穴传输层,蒸镀速率为0.01nm/s,蒸镀膜厚为35nm;
在空穴传输层之上真空蒸镀EM1作为器件的有机发光层,蒸镀速率为0.01nm/s,蒸镀总膜厚为30nm;
在有机发光层之上真空蒸镀TPBI作为有机电致发光器件的电子传输层;其蒸镀速率为0.01nm/s,蒸镀总膜厚为30nm;
在电子传输层上真空蒸镀0.5nm的LiF、150nm的Al作为电子注入层和阴极。
其他实施例和对比例与实施例1不同之处仅在于使用的空穴传输材料如表1所示。
对于如上器件实施例和对比例得到的器件进行了亮度、驱动电压、电流效率的性能表征,使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析系统测试。
有机电致发光器件性能结果见表1。
表1
由表1中的数据可知,使用本申请化合作为空穴传输材料的有机电致发光器件,降低驱动电压,使其低至4.92V以下,电流效率在1.08cd/A以上,尤其化合物66~106对应的器件,驱动电压大幅度降低的同时,效率有较大提升,使得驱动电压低至4.11V以下,同时电流效率高达1.42cd/A以上。
器件实施例14
实施例选用本申请的化合物作为有机电致发光器件中的电子阻挡层材料,比较实施例选用HT-1~HT-2作为有机电致发光器件中的电子阻挡层材料。
有机电致发光器件结构为:ITO/HIL02(80nm)/NPB(35nm)/电子阻挡层(15nm)//EM1(30nm)/TPBI(30nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下:
将涂布了ITO透明导电层(作为阳极)的玻璃基板在清洗剂中进行超声处理,然后在去离子水中冲洗,再在丙酮与乙醇混合溶剂中超声除油,再在洁净环境下烘烤至完全除水,用紫外光和臭氧清洗,并用低能阳离子束轰击表面,以改善表面的性质,提高与空穴注入层的结合能力;
将上述玻璃基板置于真空腔内,抽真空至1×10-5~9×10-4Pa,在阳极上真空蒸镀HIL02作为空穴注入层,蒸镀速率0.01nm/s,蒸镀膜厚为80nm;
在空穴注入层上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.01nm/s,蒸镀膜厚为35nm;
在空穴传输层之上分别真空蒸镀本发明化合物和对比化合物作为器件的电子阻挡层,蒸镀速率为0.01nm/s,蒸镀总膜厚为15nm;
在电子阻挡层之上真空蒸镀EM1作为器件的有机发光层,蒸镀速率为0.01nm/s,蒸镀总膜厚为30nm;
在有机发光层之上真空蒸镀TPBI作为有机电致发光器件的电子传输层;其蒸镀速率为0.01nm/s,蒸镀总膜厚为30nm;
在电子传输层上真空蒸镀0.5nm的LiF、150nm的Al作为电子注入层和阴极。
实施例15-18和对比例3-4与实施例14相比区别仅在于使用的电子阻挡材料如表2所示。
对于如上器件实施例和对比例得到的器件进行了亮度、驱动电压、电流效率和LT95的性能表征,使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析系统测试。LT95是指保持初始亮度1000cd/m2时的电流密度不变,器件亮度降为初始亮度95%时所需要的时间(小时),测试结果如表2所示。
表2
由表2中的数据可知,使用本申请化合作为电子阻挡材料的有机电致发光器件,降低驱动电压,使其低至5.02V以下,电流效率在1.09cd/A以上,寿命达到44h以上。
申请人声明,本发明通过上述实施例来说明本发明的有机化合物、有机电致发光器件和显示装置,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
2.根据权利要求1所述的有机化合物,其特征在于,所述C6~C40的芳基选自苯基、联苯基、三联苯基、萘基、蒽基、菲基、芴基、苯并芴基、二苯并芴基、萘并芴基、芘基、苝基、螺芴基、三亚苯基、荧蒽基、氢化苯并蒽基、茚并芴基、苯并茚并芴基、二苯并茚并芴基、萘并芴基、苯并萘并芴基中的一个或者二个以上基团的组合;
优选地,所述C5~C40的杂芳基选自二苯并呋喃基、二苯并噻吩基、苯并二苯并呋喃基、苯并二苯并噻吩基、二苯并二苯并呋喃基、二苯并二苯并噻吩基、萘并二苯并呋喃基、萘并二苯并噻吩基、苯并萘并二苯并呋喃基或苯并萘并二苯并噻吩基。
4.根据权利要求1-3中任一项所述的有机化合物,其特征在于,Ar1和Ar2其中至少一个选自取代或未取代的C5~C40的杂芳基;
进一步优选地,Ar1和Ar2其中至少一个选自三亚苯基或者荧蒽基。
7.一种电子阻挡层,其特征在于,所述电子阻挡层包括如权利要求1-6中任一项所述的有机化合物。
8.一种有机空穴传输层,其特征在于,所述空穴传输层包括如权利要求1-6中任一项所述的有机化合物。
9.一种有机电致发光器件,其特征在于,所述有机电致发光器件中包括如权利要求1-6中任一项所述的有机化合物;
优选地,所述有机电致发光器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,以及所述有机薄膜层包括如权利要求1-6中任一项所述的有机化合物;
优选地,所述有机薄膜层包括电子阻挡层,所述电子阻挡层包括如权利要求1-6中任一项所述的有机化合物;
优选地,所述有机电致发光器件包括空穴传输层;
优选地,所述空穴传输层包括如权利要求1-6中任一项所述的有机化合物。
10.一种显示装置,其特征在于,所述显示装置包括如权利要求9所述的有机电致发光器件。
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