CN113557229A - 新型化合物及包含其的有机发光器件 - Google Patents
新型化合物及包含其的有机发光器件 Download PDFInfo
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- CN113557229A CN113557229A CN202080018306.3A CN202080018306A CN113557229A CN 113557229 A CN113557229 A CN 113557229A CN 202080018306 A CN202080018306 A CN 202080018306A CN 113557229 A CN113557229 A CN 113557229A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 239000000126 substance Substances 0.000 claims abstract description 70
- 239000010410 layer Substances 0.000 claims description 148
- -1 naphthylphenyl Chemical group 0.000 claims description 63
- 239000012044 organic layer Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 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 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- MXVLMYZRJAHEIS-UHFFFAOYSA-N 1-(2-phenylphenyl)naphthalene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 MXVLMYZRJAHEIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000005580 triphenylene group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 37
- 239000007924 injection Substances 0.000 abstract description 37
- 230000005525 hole transport Effects 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 18
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000004519 manufacturing process Methods 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 230000032258 transport Effects 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 11
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- SNODDSKGKSSVGF-UHFFFAOYSA-N BrC1=CC=CC=C1N1C2=CC=CC=C2C2=C1C=CC(=C2)C1=CC=CC=C1 Chemical compound BrC1=CC=CC=C1N1C2=CC=CC=C2C2=C1C=CC(=C2)C1=CC=CC=C1 SNODDSKGKSSVGF-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- TXNNQTOWOCDWAM-UHFFFAOYSA-N C=1(C=CC=CC=1)C1=CC=C2C3=C(C=CC=C3)N(C2=C1)C1=C(C=CC=C1)Br Chemical compound C=1(C=CC=CC=1)C1=CC=C2C3=C(C=CC=C3)N(C2=C1)C1=C(C=CC=C1)Br TXNNQTOWOCDWAM-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- 239000003599 detergent Substances 0.000 description 2
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- 238000001704 evaporation Methods 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 238000012423 maintenance Methods 0.000 description 2
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- 150000004706 metal oxides Chemical class 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
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- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 1
- VTNULXUEOJMRKZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2H-tetrazol-5-ylmethyl)benzamide Chemical compound N=1NN=NC=1CNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O VTNULXUEOJMRKZ-UHFFFAOYSA-N 0.000 description 1
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 1
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- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WGFFJKJOCAOKHU-UHFFFAOYSA-N BrC1=CC=CC=C1N1C2=CC=C(C=C2C2=C1C=CC=C2)C1=CC=C2C(=C1)C=CC=C2 Chemical compound BrC1=CC=CC=C1N1C2=CC=C(C=C2C2=C1C=CC=C2)C1=CC=C2C(=C1)C=CC=C2 WGFFJKJOCAOKHU-UHFFFAOYSA-N 0.000 description 1
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- ASHLSBBYHHZBEU-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C3C4=CC=CC=C4N(C3=CC=C2)C5=CC=CC=C5Br Chemical compound C1=CC=C(C=C1)C2=C3C4=CC=CC=C4N(C3=CC=C2)C5=CC=CC=C5Br ASHLSBBYHHZBEU-UHFFFAOYSA-N 0.000 description 1
- OLJIYDNXBMZFDK-UHFFFAOYSA-N C1=CC=C2C(=C1)C=CC=C2C3=CC4=C(C=C3)N(C5=CC=CC=C54)C6=CC=CC=C6Br Chemical compound C1=CC=C2C(=C1)C=CC=C2C3=CC4=C(C=C3)N(C5=CC=CC=C54)C6=CC=CC=C6Br OLJIYDNXBMZFDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
本发明提供由化学式1表示的化合物及包含其的有机发光器件。由上述化学式1表示的化合物可以用作空穴注入、空穴传输、电子抑制、发光、电子传输或电子注入的材料。
Description
技术领域
与相关申请的相互引用
本申请主张基于2019年9月3日的韩国专利申请第10-2019-0109118号的优先权,包含该韩国专利申请的文献中公开的全部内容作为本说明书的一部分。
本发明涉及新型化合物及包含其的有机发光器件。
背景技术
通常情况下,有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件具有宽视角、优异的对比度、快速响应时间,亮度、驱动电压和响应速度特性优异,因此正在进行大量的研究。
有机发光器件通常具有包括阳极和阴极以及位于上述阳极与阴极之间的有机物层的结构。为了提高有机发光器件的效率和稳定性,上述有机物层大多情况下由分别利用不同的物质构成的多层结构形成,例如,可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言,如果在两电极之间施加电压,则空穴从阳极注入有机物层,电子从阴极注入有机物层,当所注入的空穴和电子相遇时会形成激子(exciton),该激子重新跃迁至基态时就会发出光。
对用于如上所述的有机发光器件的有机物,持续要求开发新的材料。
现有技术文献
专利文献
(专利文献1)韩国专利公开号第10-2000-0051826号
发明内容
技术课题
本发明涉及新型有机发光材料及包含其的有机发光器件。
课题的解决方法
本发明提供由下述化学式1表示的化合物:
[化学式1]
在上述化学式1中,
Ar1和Ar2各自独立地为取代或未取代的C6-60芳基:或者取代或未取代的包含选自N、O和S中的任一个或更多个的C2-60杂芳基,
R1至R4各自独立地为氢、氘、取代或未取代的C1-60烷基、或者取代或未取代的C6-60芳基,但R1至R4中的至少一个为取代或未取代的C6-60芳基。
另外,本发明提供一种有机发光器件,其中,包括:第一电极;与上述第一电极对置而具备的第二电极;以及具备在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。
发明效果
由上述化学式1表示的化合物可以用作有机发光器件的有机物层的材料,在有机发光器件中可以实现效率的提高、较低的驱动电压和/或寿命特性的提高。特别是,由上述化学式1表示的化合物可以用作空穴注入、空穴传输、电子抑制、发光、电子传输或电子注入的材料。
附图说明
图1图示了由基板1、阳极2、电子抑制层3、发光层4和阴极5构成的有机发光器件的例子。
图2图示了由基板1、阳极2、空穴注入层6、空穴传输层7、电子抑制层3、发光层4、空穴阻挡层8、电子传输层9、电子注入层10和阴极4构成的有机发光器件的例子。
具体实施方式
下面,为了帮助理解本发明而更详细地进行说明。
本发明提供由上述化学式1表示的化合物。
在本说明书中,“取代或未取代的”这一用语是指被选自氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;烷氧基;芳氧基;烷基硫基(alkyl thioxy);芳基硫基( aryl thioxy);烷基磺酰基(alkyl sulfoxy);芳基磺酰基(aryl sulfoxy);甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;或者包含N、O和S原子中的1个以上的杂芳基中的1个以上的取代基取代或未取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。例如,“2个以上的取代基连接而成的取代基”可以为联苯基。即,联苯基可以为芳基,也可以被解释为2个苯基连接而成的取代基。
在本说明书中,羰基的碳原子数没有特别限定,但优选碳原子数为1至40。具体而言,可以为如下结构的化合物,但并不限定于此。
在本说明书中,酯基中,酯基的氧可以被碳原子数1至25的直链、支链或环状的烷基、或者碳原子数6至25的芳基取代。具体而言,可以为下述结构式的化合物,但并不限定于此。
在本说明书中,酰亚胺基的碳原子数没有特别限定,但优选碳原子数为1至25。具体而言,可以为如下结构的化合物,但并不限定于此。
在本说明书中,甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但并不限定于此。
在本说明书中,硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但并不限定于此。
在本说明书中,作为卤素基团的例子,有氟、氯、溴或碘。
在本说明书中,上述烷基可以为直链或支链,碳原子数没有特别限定,但优选为1至40。根据一实施方式,上述烷基的碳原子数为1至20。根据另一实施方式,上述烷基的碳原子数为1至10。根据另一实施方式,上述烷基的碳原子数为1至6。作为烷基的具体例,有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但并不限定于此。
在本说明书中,上述烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至40。根据一实施方式,上述烯基的碳原子数为2至20。根据另一实施方式,上述烯基的碳原子数为2至10。根据另一实施方式,上述烯基的碳原子数为2至6。作为具体例,有乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等,但并不限定于此。
在本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基,根据一实施方式,上述环烷基的碳原子数为3至30。根据另一实施方式,上述环烷基的碳原子数为3至20。根据另一实施方式,上述环烷基的碳原子数为3至6。具体而言,有环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但并不限定于此。
在本说明书中,芳基没有特别限定,但优选为碳原子数6至60的芳基,可以为单环芳基或多环芳基。根据一实施方式,上述芳基的碳原子数为6至30。根据一实施方式,上述芳基的碳原子数为6至20。关于上述芳基,作为单环芳基,可以为苯基、联苯基、三联苯基等,但并不限定于此。作为上述多环芳基,可以为萘基、蒽基、菲基、芘基、苝基、基、芴基等,但并不限定于此。
在本说明书中,杂芳基是包含O、N、Si和S中的1个以上作为杂原子的杂芳基,碳原子数没有特别限定,但优选碳原子数为2至60。根据一实施方式,上述杂芳基的碳原子数为6至30。根据一实施方式,上述杂芳基的碳原子数为6至20。作为杂芳基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基(phenanthroline)、异唑基、噻二唑基、吩噻嗪基和二苯并呋喃基等,但不仅限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基、芳基胺基中的芳基与上述芳基的例示相同。在本说明书中,芳烷基、烷基芳基、烷基胺基中的烷基与上述烷基的例示相同。在本说明书中,杂芳基胺中的杂芳基可以适用上述的关于杂芳基的说明。在本说明书中,芳烯基中的烯基与上述烯基的例示相同。在本说明书中,亚芳基为2价基团,除此以外,可以适用上述的关于芳基的说明。在本说明书中,亚杂芳基为2价基团,除此以外,可以适用上述关于杂芳基的说明。在本说明书中,烃环不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述的关于芳基或环烷基的说明。在本说明书中,杂芳基不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述的关于杂芳基的说明。
优选地,上述化学式1可以由下述化学式1-1至化学式1-4中的任一个表示:
[化学式1-1]
[化学式1-2]
[化学式1-3]
[化学式1-4]
在上述化学式1-1至化学式1-4中,
对于Ar1、Ar2和R1至R4的说明与化学式1中的定义相同。
优选地,Ar1和Ar2可以各自独立地为取代或未取代的C6-30芳基;或者取代或未取代的包含选自N、O和S中的任一个或更多个的C2-30杂芳基,
更优选地,Ar1和Ar2可以各自独立地为苯基、联苯基、三联苯基、被5个氘取代的联苯基、萘基、萘基苯基、二甲基芴基、二苯基芴基、三亚苯基、菲基苯基、萘基联苯基、苯基二甲基芴基、二苯并呋喃基或二苯并噻吩基,
最优选地,Ar1和Ar2可以各自独立地为选自下述基团中的任一个:
优选地,R1至R4各自独立地为氢、取代或未取代的C1-10烷基、或者取代或未取代的C6-20芳基,但R1至R4中的至少一个可以为取代或未取代的C6-20芳基,
更优选地,R1至R4各自独立地为氢、苯基、联苯基、萘基、菲基、或者被1个叔丁基取代的苯基,R1至R4中的至少一个可以为苯基、联苯基、萘基、菲基、或者被1个叔丁基取代的苯基,
最优选地,R1至R4可以各自独立地为氢、或者选自下述基团中的任一个,R1至R4中的至少一个可以为选自下述基团中的一个:
优选地,R1至R4中的一个为苯基、联苯基、萘基、菲基、或者被1个叔丁基取代的苯基,其余可以为氢,
更优选地,R1至R4中的一个为选自下述基团中的任一个,其余可以为氢:
由上述化学式1表示的化合物的代表性的例子如下所示:
作为一个例子,由上述化学式1表示的化合物可以通过如下述反应式1所示的制造方法进行制造,除此以外的其余化合物也可以通过类似的方法进行制造。
[反应式1]
在上述反应式1中,Ar1、Ar2和R1至R4与上述化学式1中的定义相同,X为卤素,优选地,X为氯或溴。
上述反应式1为铃木偶联反应,优选在钯催化剂和碱的存在下进行,用于铃木偶联反应的反应基团可以根据该领域中已知的那样进行变更。上述制造方法可以在后述的制造例中更具体化。
另外,本发明提供包含由上述化学式1表示的化合物的有机发光器件。作为一个例子,本发明提供一种有机发光器件,其中,包括:第一电极;与上述第一电极对置而具备的第二电极;以及具备在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。
本发明的有机发光器件的有机物层可以由单层结构形成,还可以由层叠有2层以上的有机物层的多层结构形成。例如,本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、电子抑制层、发光层、空穴阻挡层、电子传输层、电子注入层等作为有机物层的结构。但是,有机发光器件的结构并不限定于此,可以包括更少数量的有机物层。
另外,上述有机物层可以包括电子抑制层和发光层,上述电子抑制层或发光层可以包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括空穴传输层、空穴注入层、同时进行空穴传输和空穴注入的层、以及电子抑制层,上述空穴传输层、空穴注入层、同时进行空穴传输和空穴注入的层、或电子抑制层可以包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括空穴传输层、空穴注入层、电子抑制层、发光层、空穴阻挡层、电子传输层和电子注入层,上述空穴传输层、空穴注入层、电子抑制层、发光层、空穴阻挡层、电子传输层、或电子注入层可以包含由上述化学式1表示的化合物。
另外,根据本发明的有机发光器件可以是在基板上依次层叠有阳极、1层以上的有机物层和阴极的结构(正常型(normal type))的有机发光器件。此外,根据本发明的有机发光器件可以是在基板上依次层叠有阴极、1层以上的有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。例如,根据本发明的一实施例的有机发光器件的结构例示于图1和图2。
图1图示了由基板1、阳极2、电子抑制层3、发光层4和阴极5构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述电子抑制层或发光层中。
图2图示了由基板1、阳极2、空穴注入层6、空穴传输层7、电子抑制层3、发光层4、空穴阻挡层8、电子传输层9、电子注入层10和阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述空穴注入层、空穴传输层、电子抑制层或发光层中。
根据本发明的有机发光器件除了上述有机物层中的1层以上包含由上述化学式1表示的化合物以外,可以利用该技术领域中已知的材料和方法进行制造。此外,在上述有机发光器件包括复数个有机物层的情况下,上述有机物层可以由相同的物质或不同的物质形成。
例如,根据本发明的有机发光器件可以通过在基板上依次层叠第一电极、有机物层和第二电极而制造。这时,可以如下制造:利用溅射法(sputtering)或电子束蒸发法(e-beam evaporation)之类的PVD(physical Vapor Deposition:物理气相沉积)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机物层,之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。
另外,由上述化学式1表示的化合物在制造有机发光器件时不仅可以利用真空蒸镀法,还可以利用溶液涂布法来形成有机物层。在这里,所谓溶液涂布法是指旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但不仅限于此。
除了这些方法以外,也可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件(WO 2003/012890)。但是,制造方法并不限定于此。
作为一个例子,上述第一电极为阳极,上述第二电极为阴极,或者上述第一电极为阴极,上述第二电极为阳极。
作为上述阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为上述阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:Al或SnO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等,但不仅限于此。
作为上述阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为上述阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金;LiF/Al或LiO2/Al等多层结构物质等,但不仅限于此。
上述空穴注入层是注入来自电极的空穴的层,作为空穴注入物质,优选为如下化合物:具有传输空穴的能力,具有注入来自阳极的空穴的效果,具有对于发光层或发光材料的优异的空穴注入效果,防止发光层中生成的激子向电子注入层或电子注入材料迁移,而且薄膜形成能力优异的化合物。优选空穴注入物质的HOMO(最高占有分子轨道,highestoccupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体例,有金属卟啉(porphyrin)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚噻吩系导电性高分子等,但不仅限于此。
上述空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层,空穴传输物质是能够接收来自阳极或空穴注入层的空穴并将其转移至发光层的物质,对空穴的迁移率大的物质是合适的。作为具体例,可以使用芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等,但不仅限于此。
上述电子抑制层是为了防止从阴极注入的电子不在发光层中再结合而转移至空穴传输层,从而置于空穴传输层与发光层之间的层,也称为电子阻挡层。电子抑制层优选与电子传输层相比亲电子能力较小的物质。优选地,可以包含由上述化学式1表示的化合物作为电子抑制层的物质。
上述发光物质是能够从空穴传输层和电子传输层分别接收空穴和电子并使它们结合而发出可见光区域的光的物质,优选对于荧光或磷光的量子效率高的物质。作为具体例,有8-羟基喹啉铝配合物(Alq3);咔唑系化合物;二聚苯乙烯基(dimerized styryl)化合物;BAlq;10-羟基苯并喹啉-金属化合物;苯并唑、苯并噻唑及苯并咪唑系化合物;聚(对亚苯基亚乙烯基)(PPV)系高分子;螺环(spiro)化合物;聚芴;红荧烯等,但不仅限于此。
上述发光层可以包含主体材料和掺杂剂材料。主体材料有芳香族稠环衍生物或含杂环化合物等。具体而言,作为芳香族稠环衍生物,有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,作为含杂环化合物,有咔唑衍生物、二苯并呋喃衍生物、梯型呋喃化合物嘧啶衍生物等,但并不限定于此。
作为掺杂剂材料,有芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体而言,芳香族胺衍生物是具有取代或未取代的芳基氨基的芳香族稠环衍生物,有具有芳基氨基的芘、蒽、二茚并芘等,苯乙烯基胺化合物是在取代或未取代的芳基胺上取代有至少1个芳基乙烯基的化合物,被选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的1个或2个以上的取代基取代或未取代。具体而言,有苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等,但并不限定于此。此外,作为金属配合物,有铱配合物、铂配合物等,但并不限定于此。
上述空穴阻挡层是为了防止从阳极注入的空穴不在发光层中再结合而转移至电子传输层,从而置于电子传输层与发光层之间的层,也称为空穴抑制层。空穴阻挡层优选电离能大的物质。
上述电子传输层是从电子注入层接收电子并将电子传输至发光层的层,电子传输物质是能够从阴极良好地接收电子并将其转移至发光层的物质,对于电子的迁移率大的物质是合适的。作为具体例,有8-羟基喹啉的Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄酮-金属配合物等,但不仅限于此。电子传输层可以如现有技术中所使用的那样与任意期望的阴极物质一同使用。特别是,合适的阴极物质例子是具有低功函数,且伴有铝层或银层的通常的物质。具体为铯、钡、钙、镱和钐,在各情况下均伴有铝层或银层。
上述电子注入层是注入来自电极的电子的层,优选为如下化合物:具有传输电子的能力,具有注入来自阴极的电子的效果,具有对于发光层或发光材料的优异的电子注入效果,防止发光层中生成的激子向空穴注入层迁移,而且薄膜形成能力优异的化合物。具体而言,有芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、以及含氮五元环衍生物等,但并不限定于此。
作为上述金属配位化合物,有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但并不限定于此。
根据所使用的材料,根据本发明的有机发光器件可以为顶部发光型、底部发光型或双向发光型。
另外,由上述化学式1表示的化合物除了包含在有机发光器件中以外,还可以包含在有机太阳能电池或有机晶体管中。
下面,为了帮助理解本发明而更详细地进行说明。但,下述的实施例只用于例示本发明,本发明的内容并不限定于下述的实施例。
制造例1:化合物1-1的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-2-苯基-9H-咔唑(9-(2-bromophenyl)-2-phenyl-9H-carbazole)(6.52g,16.42mmol)、化合物a-1(7.97g,18.07mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.57g,0.49mmol)后,加热搅拌5小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用270ml的乙酸乙酯重结晶,从而制造了化合物1-1(7.26g,收率:62%)。
MS[M+H]+=715
制造例2:化合物1-2的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-苯基-9H-咔唑(9-(2-bromophenyl)-3-phenyl-9H-carbazole)(6.28g,15.82mmol)、化合物a-2(8.37g,17.40mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.55g,0.47mmol)后,加热搅拌2小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用320ml的乙酸乙酯重结晶,从而制造了化合物1-2(8.34g,收率:70%)。
MS[M+H]+=755
制造例3:化合物1-3的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-4-苯基-9H-咔唑(9-(2-bromophenyl)-4-phenyl-9H-carbazole)(6.38g,16.07mmol)、化合物a-3(9.58g,17.68mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.56g,0.48mmol)后,加热搅拌6小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用210ml的乙酸乙酯重结晶,从而制造了化合物1-3(7.16g,收率:55%)。
MS[M+H]+=816
制造例4:化合物1-4的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-1-苯基-9H-咔唑(9-(2-bromophenyl)-1-phenyl-9H-carbazole)(5.96g,15.01mmol)、化合物a-4(9.78g,16.51mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.52g,0.45mmol)后,加热搅拌7小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用420ml的乙酸乙酯重结晶,从而制造了化合物1-4(9.32g,收率:72%)。
MS[M+H]+=866
制造例5:化合物1-5的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-2-苯基-9H-咔唑(6.63g,16.70mmol)、化合物a-5(9.75g,18.37mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.58g,0.50mmol)后,加热搅拌4小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用240ml的乙酸乙酯重结晶,从而制造了化合物1-5(7.76g,收率:58%)。
MS[M+H]+=805
制造例6:化合物1-6的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-苯基-9H-咔唑(7.11g,17.91mmol)、化合物a-6(8.57g,19.70mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.62g,0.54mmol)后,加热搅拌7小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用240ml的乙酸乙酯重结晶,从而制造了化合物1-6(6.92g,收率:53%)。
MS[M+H]+=729
制造例7:化合物1-7的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-苯基-9H-咔唑(7.53g,18.97mmol)、化合物a-7(8.78g,20.86mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.66g,0.57mmol)后,加热搅拌5小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用250ml的乙酸乙酯重结晶,从而制造了化合物1-7(8.53g,收率:63%)。
MS[M+H]+=715
制造例8:化合物1-8的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-苯基-9H-咔唑(6.89g,17.36mmol)、化合物a-8(8.61g,19.09mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.60g,0.52mmol)后,加热搅拌6小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用310ml的乙酸乙酯重结晶,从而制造了化合物1-8(5.97g,收率:46%)。
MS[M+H]+=745
制造例9:化合物1-9的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-苯基-9H-咔唑(7.06g,17.78mmol)、化合物a-9(10.35g,19.56mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.62g,0.53mmol)后,加热搅拌3小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用250ml的乙酸乙酯重结晶,从而制造了化合物1-9(9.23g,收率:65%)。
MS[M+H]+=804
制造例10:化合物1-10的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-(萘-1-基)-9H-咔唑(9-(2-bromophenyl)-3-(naphthalen-1-yl)-9H-carbazole)(8.26g,18.48mmol)、化合物a-10(8.96g,20.33mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.64g,0.55mmol)后,加热搅拌4小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用320ml的乙酸乙酯重结晶,从而制造了化合物1-10(7.55g,收率:53%)。
MS[M+H]+=765
制造例11:化合物1-11的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-3-(萘-2-基)-9H-咔唑(9-(2-bromophenyl)-3-(naphthalen-2-yl)-9H-carbazole)(7.77g,17.38mmol)、化合物a-11(9.22g,19.12mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.60g,0.52mmol)后,加热搅拌2小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用260ml的乙酸乙酯重结晶,从而制造了化合物1-11(6.85g,收率:49%)。
MS[M+H]+=806
制造例12:化合物1-12的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物2-([1,1'-联苯]-4-基)-9-(2-溴苯基)-9H-咔唑(2-([1,1'-biphenyl]-4-yl)-9-(2-bromophenyl)-9H-carb azole)(6.96g,14.68mmol)、化合物a-12(7.51g,16.15mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.51g,0.44mmol)后,加热搅拌5小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用270ml的乙酸乙酯重结晶,从而制造了化合物1-12(5.73g,收率:48%)。
MS[M+H]+=816
制造例13:化合物1-13的制造
在氮气氛下,在500ml的圆底烧瓶中,将化合物9-(2-溴苯基)-2-苯基-9H-咔唑(6.87g,14.49mmol)、化合物a-13(5.58g,15.94mmol)完全溶解于240ml的四氢呋喃后,添加2M的碳酸钾水溶液(120ml),加入四(三苯基膦)钯(0.50g,0.43mmol)后,加热搅拌3小时。将温度降低至常温,去除水层,用无水硫酸镁干燥后,进行减压浓缩,用260ml的乙酸乙酯重结晶,从而制造了化合物1-13(7.44g,收率:72%)。
MS[M+H]+=715
实施例1-1
将ITO(氧化铟锡,indium tin oxide)以的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中,利用超声波进行洗涤。这时,洗涤剂使用菲希尔公司(Fischer Co.)制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后,用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后,用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后,输送至等离子体清洗机。此外,利用氧等离子体,将上述基板清洗5分钟后,将基板输送至真空蒸镀机。
在这样准备的作为阳极的ITO透明电极上,将下述化合物HI1和下述化合物HI2的化合物以成为98:2(摩尔比)的比的方式、以的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上,将下述化合物HT1进行真空蒸镀而形成空穴传输层。接着,在上述空穴传输层上,以膜厚度将上述制造的化合物1进行真空蒸镀而形成电子抑制层。接着,在上述电子抑制层上,以膜厚度将下述化合物BH和下述化合物BD以25:1的重量比进行真空蒸镀而形成发光层。在上述发光层上,以膜厚度将下述化合物HB1进行真空蒸镀而形成空穴阻挡层。接着,在上述空穴阻挡层上,将下述化合物ET1和下述化合物LiQ以1:1的重量比进行真空蒸镀,从而以的厚度形成电子注入和传输层。在上述电子注入和传输层上,依次将氟化锂(LiF)以的厚度、将铝以的厚度进行蒸镀,从而形成阴极。
实施例1-2至实施例1-13
使用下述表1中记载的化合物代替制造例1的化合物,除此以外,通过与上述实施例1-1相同的方法制造了有机发光器件。
比较例1-1至1-4
使用下述表1中记载的化合物代替制造例1的化合物,除此以外,通过与上述实施例1-1相同的方法制造了有机发光器件。下述表1中使用的化合物EB2、EB3、EB4和EB5如下所示。
实验例
对上述实施例和比较例中制造的有机发光器件施加10mA/cm2的电流时,测定了电压、效率、色坐标和寿命,将其结果示于下述表1。T95是指亮度从初始亮度(1600尼特)减少至95%所需的时间。
[表1]
如上述表1所示,将本发明的化合物用作电子抑制层的有机发光器件在有机发光器件的效率、驱动电压和稳定性方面显示出优异的特性。
可知,在实施例1-1至1-13中,将在亚联苯基连接基团的特定位置各自取代有咔唑核和胺取代基且咔唑核包含芳基取代基的物质用作电子抑制层时,显示出低电压、高效率、长寿命的特性。
符号说明
1:基板2:阳极
3:电子抑制层4:发光层
5:阴极6:空穴注入层
7:空穴传输层8:空穴阻挡层
9:电子传输层10:电子注入层。
Claims (7)
3.根据权利要求1所述的化合物,其中,Ar1和Ar2各自独立地为苯基、联苯基、三联苯基、被5个氘取代的联苯基、萘基、萘基苯基、二甲基芴基、二苯基芴基、三亚苯基、菲基苯基、萘基联苯基、苯基二甲基芴基、二苯并呋喃基或二苯并噻吩基。
5.根据权利要求1所述的化合物,其中,R1至R4各自独立地为氢、苯基、联苯基、萘基、菲基、或者被1个叔丁基取代的苯基,R1至R4中的至少一个为苯基、联苯基、萘基、菲基、或者被1个叔丁基取代的苯基。
7.一种有机发光器件,其中,包括:第一电极;与所述第一电极对置而具备的第二电极;以及具备在所述第一电极与所述第二电极之间的1层以上的有机物层,所述有机物层中的1层以上包含权利要求1至6中任一项所述的化合物。
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