WO2017073594A1 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2017073594A1 WO2017073594A1 PCT/JP2016/081685 JP2016081685W WO2017073594A1 WO 2017073594 A1 WO2017073594 A1 WO 2017073594A1 JP 2016081685 W JP2016081685 W JP 2016081685W WO 2017073594 A1 WO2017073594 A1 WO 2017073594A1
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- -1 arylamine compound Chemical class 0.000 claims abstract description 97
- 239000000463 material Substances 0.000 claims abstract description 82
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 230000005525 hole transport Effects 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 53
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 50
- 125000006617 triphenylamine group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000004431 deuterium atom Chemical group 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 238000005401 electroluminescence Methods 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 150000001454 anthracenes Chemical class 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 claims 1
- 125000005581 pyrene group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 34
- 239000007924 injection Substances 0.000 abstract description 34
- 239000010409 thin film Substances 0.000 abstract description 26
- 239000000243 solution Substances 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 174
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
- 238000000034 method Methods 0.000 description 28
- 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 25
- 239000000843 powder Substances 0.000 description 19
- 238000005259 measurement Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 15
- 125000001624 naphthyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 12
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 12
- 125000001725 pyrenyl group Chemical group 0.000 description 12
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 238000007740 vapor deposition Methods 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000001041 indolyl group Chemical group 0.000 description 9
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 9
- 125000005493 quinolyl group Chemical group 0.000 description 9
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 9
- 239000002356 single layer Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 8
- 125000005956 isoquinolyl group Chemical group 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- UUOYDHJVGOATFJ-UHFFFAOYSA-N [4-(n-(4-phenylphenyl)anilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 UUOYDHJVGOATFJ-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 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 7
- 238000000746 purification Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 125000004306 triazinyl group Chemical group 0.000 description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
- 125000004623 carbolinyl group Chemical group 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 125000000168 pyrrolyl group Chemical group 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 5
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 5
- 150000003220 pyrenes Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 0 *c1ccccc1 Chemical compound *c1ccccc1 0.000 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 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004322 quinolinols Chemical class 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 description 3
- 125000005346 substituted cycloalkyl group Chemical group 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
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- OKPXOQSNTNQGFG-UHFFFAOYSA-N 2-phenyl-3-[4-(N-(4-phenylphenyl)anilino)phenyl]aniline Chemical group NC=1C(=C(C=CC=1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1 OKPXOQSNTNQGFG-UHFFFAOYSA-N 0.000 description 2
- SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ISXSUKUXUPLGTD-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(5-oxopyrrolidin-2-yl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2NC(CC2)=O)C=CC=1 ISXSUKUXUPLGTD-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- YKKPYMXANSSQCA-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3-pyrazol-1-ylazetidin-1-yl)methanone Chemical compound N1(N=CC=C1)C1CN(C1)C(=O)C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F YKKPYMXANSSQCA-UHFFFAOYSA-N 0.000 description 2
- JOSCNYCOYXTLTN-GFCCVEGCSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)CO JOSCNYCOYXTLTN-GFCCVEGCSA-N 0.000 description 2
- JWSIZPAOIFLWKM-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[3-(dimethylamino)-4-hydroxypyrrolidin-1-yl]methanone Chemical compound CN(C)C1CN(CC1O)C(=O)c1cccc(Oc2cc(CN)cc(n2)C(F)(F)F)c1 JWSIZPAOIFLWKM-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen 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
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
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Images
Classifications
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Definitions
- the present invention relates to an organic electroluminescence element which is a self-luminous element suitable for various display devices, and more specifically, a specific arylamine compound and the compound (and a compound having a pyrimidine ring structure having a specific structure).
- the present invention relates to the used organic electroluminescence element (hereinafter abbreviated as an organic EL element).
- the organic EL element is a self-luminous element, it has been actively researched because it is brighter and more visible than a liquid crystal element and can be clearly displayed.
- Non-Patent Document 2 An element utilizing light emission by thermally activated delayed fluorescence (TADF) has also been developed.
- TADF thermally activated delayed fluorescence
- the light emitting layer can be prepared by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound or a material emitting delayed fluorescence.
- a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound or a material emitting delayed fluorescence.
- selection of an organic material in the organic EL element greatly affects various characteristics such as efficiency and durability of the element (for example, see Non-patent document 2).
- the light injected from both electrodes is recombined in the light emitting layer to obtain light emission, but it is important how efficiently both holes and electrons are transferred to the light emitting layer. It is necessary to make the device excellent in carrier balance.
- the probability of recombination of holes and electrons is improved by improving the hole injection property and blocking the electrons injected from the cathode, and further excitons generated in the light emitting layer. By confining, high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
- the heat resistance and amorphous nature of the material are important for the lifetime of the element.
- thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated.
- the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
- NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine (NPD) and various aromatic amine derivatives are known as hole transport materials that have been used in organic EL devices so far.
- NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-patent document 4).
- Tg glass transition point
- arylamine compounds having a substituted carbazole structure have been proposed as compounds with improved characteristics such as heat resistance and hole injection properties (see, for example, Patent Document 4 and Patent Document 5), these compounds are injected with holes.
- the elements used for the layer or the hole transport layer have been improved in heat resistance, luminous efficiency, etc., they are still not sufficient, and further lower driving voltage and higher luminous efficiency are required. .
- JP-A-8-048656 Japanese Patent No. 3194657 Japanese Patent No. 4943840 JP 2006-151979 A International Publication No. 2008/62636 International Publication No. 2011/059000 International Publication No. 2003/060956 JP-A-7-126615 JP 2005-108804 A
- the object of the present invention is as a material for an organic EL device having high efficiency and high durability, and for an organic EL device excellent in hole injection / transport performance, electron blocking capability, stability in a thin film state, and durability.
- the materials and various materials for organic EL elements having excellent hole and electron injection / transport performance, electron blocking ability, stability in a thin film state, and durability It is an object of the present invention to provide an organic EL element with high efficiency, low driving voltage, and long life by combining them so that the characteristics of these materials can be effectively expressed.
- the physical characteristics of the organic compound to be provided by the present invention are as follows: (1) good hole injection characteristics; (2) high hole mobility; and (3) electron blocking ability. (4) the thin film state is stable, and (5) the heat resistance is excellent. Further, the physical characteristics to be provided by the organic EL element to be provided by the present invention are (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical driving. Low voltage and (4) long life can be mentioned.
- the present inventors focused on the fact that arylamine-based materials are excellent in hole injection and transport capability, thin film stability and durability, and synthesized various compounds. As a result of diligent evaluation, it was found that an arylamine compound having a specific position substituted with an aryl group can efficiently inject and transport holes to the light emitting layer.
- a compound having a pyrimidine ring structure is excellent in electron injection and transport capability, and stability and durability of a thin film
- an arylamine compound in which a specific position is substituted with an aryl group and a pyrimidine having a specific structure Various organic EL devices that combine a hole transport material and an electron transport material so that a carrier can be balanced by selecting a compound having a ring structure so that holes and electrons can be efficiently injected and transported to the light emitting layer. The device was intensively evaluated for device characteristics.
- the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and two specific types of triphenylamine derivatives are selected to efficiently inject holes into the light emitting layer.
- select the material of the first hole transport layer and the material of the second hole transport layer so that they can be transported, and make various organic EL devices with elaborate combinations that can achieve carrier balance, and evaluate the device characteristics. I went diligently. As a result, the present invention has been completed.
- the following organic EL elements are provided.
- the hole transport layer contains an arylamine compound represented by the following general formula (1).
- An organic EL element characterized by the above.
- Ar 1 to Ar 5 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring
- Ar 6 to Ar 8 may be the same as or different from each other, and represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted group.
- Ar 1 to Ar 5 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring
- Ar 6 to Ar 8 may be the same as or different from each other, and represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted group.
- Ar 9 represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group
- Ar 10 and Ar 11 may be the same or different, and each represents a hydrogen atom.
- Ar 12 represents a substituted or unsubstituted aromatic heterocyclic group
- R 1 to R 4 represent , Which may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, linear or branched alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Ar 10 and Ar 11 are not hydrogen atoms at the same time And)
- the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer contains the arylamine compound.
- the organic EL device according to any one of 1) to 3) above.
- the first hole transport layer contains a triphenylamine derivative different from the arylamine compound contained in the second hole transport layer, and the triphenylamine derivative contains two triphenylamines.
- Organic EL element wherein the amine skeleton has a molecular structure linked by a single bond or a divalent hydrocarbon group, and has 2 to 6 triphenylamine skeletons as a whole molecule.
- R 5 to R 10 are a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent.
- 5, r 6, r 9, r 10 represents 0 to 5 r 7, if r 8 .r 5, r 6, r 9, r 10 which represents 0-4 is 2-5, or,
- a plurality of r 5 to r 10 bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom Alternatively, they may be bonded to each other via a sulfur atom to form a ring, and L 1 represents a divalent group represented by the following structural formulas (C) to (G) or a single bond.
- R 11 to R 22 are a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent.
- R 11, r 12, r 15, r 18, r 21, r 22 represents 0 ⁇ 5, r 13, r 14, r 16, r 17, r 19, r 20 represents 0 ⁇ 4 .
- r 11 , r 12 , r 15 , r 18 , r 21 , r 22 are 2 to 5 or r 13 , r 14 , r 16 , r 17 , r 19 , r 20 are 2 to 4
- R 11 to R 22 bonded to the same benzene ring may be the same or different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- L 2 , L 3 and L 4 may be the same or different and represent a divalent group represented by the following structural formulas (B) to (G) or a single bond.
- Ar 1 to Ar 5 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring
- Ar 6 to Ar 8 may be the same as or different from each other, and represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted group.
- Ar 1 to Ar 5 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring
- Ar 6 to Ar 8 may be the same as or different from each other, and represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted group.
- the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “unsubstituted fused polycyclic aromatic group” specifically includes a phenyl group, a biphenylyl group, a terphenylyl group.
- substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)
- substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)
- substituents include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group
- a linear or branched alkyl group having 1 to 6 carbon atoms such as n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group,
- An aromatic vinyl group such as a styryl group and a naphthyl vinyl group; and a group such as an acyl group such as an acetyl group and a benzoyl group. May be substituted. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- Specific examples of the ⁇ hydrocarbon group '' or ⁇ fused polycyclic aromatic group '' include phenyl group, biphenylyl group, terphenylyl group, quarterphenyl group, styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, and fluorenyl group.
- groups such as indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, and triphenylenyl group.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 12 in the general formula (2), specifically, a triazinyl group, a pyridyl group, a pyrimidinyl group, Furyl, pyrrolyl, thienyl, quinolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl And a group such as a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- linear or branched alkyl group having 1 to 6 carbon atoms represented by R 1 to R 4 in the general formula (2)
- R 1 to R 4 in the general formula (2)
- Specific examples of the “linear or branched alkyl group having 1 to 6 carbon atoms” represented by R 1 to R 4 in the general formula (2) include a methyl group, an ethyl group, n- Propyl, i-propyl, n-butyl, 2-methylpropyl, t-butyl, n-pentyl, 3-methylbutyl, tert-pentyl, n-hexyl, iso-hexyl and tert -A hexyl group can be mentioned.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) or general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) or general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- n1 represents 0 or an integer of 1 to 2. When n1 is 0, a benzene ring substituted with two diarylamino groups is directly (with a single bond).
- n1 1, it indicates that the benzene ring substituted with two diarylamino groups is bonded via one phenylene group, and when n1 is 2, It shows that a benzene ring substituted with two diarylamino groups is bonded via two phenylene groups (biphenylene groups).
- Ar 9 in the general formula (2) includes a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, an acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, and a triphenylenyl group.
- a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable.
- the phenyl group preferably has a substituted or unsubstituted condensed polycyclic aromatic group as a substituent, and is selected from a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluoranthenyl group, and triphenylenyl group. It is more preferable to have a substituent.
- Ar 10 in the general formula (2) is preferably a phenyl group having a substituent.
- substituents include an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, and an anthracenyl group.
- Ar 11 in the general formula (2) is preferably a phenyl group having a substituent.
- examples of the substituent include an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, and an anthracenyl group.
- an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, and an anthracenyl group.
- Group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other condensed polycyclic aromatic groups are preferable, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, A pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are
- Ar 9 and Ar 10 are not the same from the viewpoint of the stability of the thin film.
- Ar 9 and Ar 10 may be different substituents or different substitution positions.
- Ar 10 and Ar 11 may be the same group, but may be easily crystallized by improving the symmetry of the whole molecule.
- Ar 10 And Ar 11 are preferably different groups, and Ar 10 and Ar 11 are not simultaneously hydrogen atoms.
- Ar 12 in the general formula (2) is a triazinyl group, pyridyl group, pyrimidinyl group, pyrrolyl group, quinolyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group , Pyrazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, carbolinyl group and other nitrogen-containing heterocyclic groups are preferable, triazinyl group, pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, benzoimidazolyl group Group, naphthyridinyl group, phenanthrolinyl group, and acridinyl group are more preferable.
- the Ar 12 bond position in the benzene ring is preferably a meta position with respect to the bond position with the pyrimidine ring from the viewpoint of thin film stability.
- Examples of the compound having a pyrimidine ring structure represented by the general formula (2) include compounds having a pyrimidine ring structure represented by the following general formula (2a) and general formula (2b), which have different bonding modes of substituents. .
- the organic EL element of the present invention in this case has a configuration including at least an anode, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, and a cathode in this order.
- the second hole transport layer contains an arylamine compound represented by the general formula (1) or the general formula (1a), and the first hole transport layer further includes the first hole transport layer.
- triphenylamine derivative different from the arylamine compound contained in the two-hole transport layer, and the triphenylamine derivative is composed of two triphenylamine skeletons having a single bond or a divalent hydrocarbon group.
- An embodiment having a linked molecular structure and a compound having 2 to 6 triphenylamine skeletons as a whole molecule is more preferable.
- the phenylamine derivative is represented by the following general formula (3), the triphenylamine derivative having two triphenylamine skeletons as a whole molecule, or the whole molecule represented by the following general formula (4)
- the triphenylamine derivative having four triphenylamine skeletons is preferable.
- R 5 to R 10 are a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent.
- 5, r 6, r 9, r 10 represents 0 to 5 r 7, if r 8 .r 5, r 6, r 9, r 10 which represents 0-4 is 2-5, or,
- a plurality of r 5 to r 10 bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom Alternatively, they may be bonded to each other via a sulfur atom to form a ring, and L 1 represents a divalent group represented by the following structural formulas (C) to (G) or a single bond.
- R 11 to R 22 are a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl having 1 to 6 carbon atoms which may have a substituent.
- R 11, r 12, r 15, r 18, r 21, r 22 represents 0 ⁇ 5, r 13, r 14, r 16, r 17, r 19, r 20 represents 0 ⁇ 4 .
- r 11 , r 12 , r 15 , r 18 , r 21 , r 22 are 2 to 5 or r 13 , r 14 , r 16 , r 17 , r 19 , r 20 are 2 to 4
- R 11 to R 22 bonded to the same benzene ring may be the same or different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- L 2 , L 3 and L 4 may be the same or different and represent a divalent group represented by the following structural formulas (B) to (G) or a single bond.
- a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 5 to R 10 in the general formula (3), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
- Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclyl A hexyl group, a 1-adamantyl group, a 2-adamantyl group, a vinyl group, an allyl group, an isopropenyl group, a 2-butenyl group, etc., and these groups are a single bond, a substituted or unsubstituted methylene group, A ring may be formed by bonding to each other via an
- a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 5 to R 10 in the general formula (3), “5 to 10 carbon atoms having a substituent”
- Specific examples of the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, a cyano group, and a nitro group; Halogen atoms such as fluorine, chlorine, bromine and iodine; linear or branched alkyloxy having 1 to 6 carbon atoms such as methyloxy, ethyloxy and propyloxy; vinyl and allyl Alkenyl groups such as phenyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; Group, biphenylyl
- These groups to each other is a single bond, a substituted or unsubstituted methylene group, via an oxygen atom or a sulfur atom may bond to each other to form a ring.
- these groups may have a substituent, and the substituent is represented by R 5 to R 10 in the general formula (3), which is a straight chain having 1 to 6 carbon atoms having a substituent.
- R 5 to R 10 in the general formula (3), which is a straight chain having 1 to 6 carbon atoms having a substituent.
- Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 5 to R 10 in the general formula (3), or “substituted or unsubstituted condensed hydrocarbon group”
- the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” includes Ar 1 to Ar in the general formula (1) and general formula (1a).
- Aromatic carbonization in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by Ar 8 Examples thereof include the same as those shown for the “hydrogen group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group”, and these groups are a single bond, a substituted or unsubstituted methylene group, Bonded to each other through oxygen or sulfur atoms to form a ring It may form.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 5 to R 10 in the general formula (3) include a phenyloxy group, a biphenylyloxy group, a terphenyl group.
- Examples include ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, and the like. They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- R 5 to R 10 may be the same or different, r 5 , r 6 , r 9 and r 10 represent 0 to 5, and r 7 and r 8 represent 0 to 4.
- a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 11 to R 22 in the general formula (4), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
- the “6 linear or branched alkyl group”, “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group” includes the above general formula “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R 5 to R 10 in (3), “having a substituent; A cycloalkyl group having 5 to 10 carbon atoms Or the same as those described for the “optionally substituted straight-chain or branched alkenyl group having 2 to 6 carbon atoms”, and possible embodiments are also the same. Can give.
- these groups may have a substituent, and the substituent is represented by R 5 to R 10 in the general formula (3), which is a straight chain having 1 to 6 carbon atoms having a substituent.
- R 5 to R 10 in the general formula (3), which is a straight chain having 1 to 6 carbon atoms having a substituent.
- the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” includes Ar 1 to Ar in the general formula (1) and general formula (1a).
- Aromatic carbonization in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by Ar 8 Examples thereof include the same as those shown for the “hydrogen group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group”, and these groups are a single bond, a substituted or unsubstituted methylene group, Bonded to each other through oxygen or sulfur atoms It may be formed.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 11 to R 22 in the general formula (4) is represented by R 5 to R 10 in the general formula (3).
- lifted These groups are a single bond, a substituted or unsubstituted methylene group, oxygen atom Alternatively, they may be bonded to each other via a sulfur atom to form a ring.
- these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- a “substituted aromatic hydrocarbon group represented by Ar 1 to Ar 8 in the general formula (1) and general formula (1a)” may be used.
- “Substituted aromatic heterocyclic group ”or“ Substituted condensed polycyclic aromatic group ” can be the same as those shown for“ Substituent ”, and possible embodiments are also the same. Can do.
- r 11 to r 22 may be the same or different, and r 11 , r 12 , r 15 , r 18 , r 21 , r 22 represent 0 to 5, and r 13 , r 14 , r 16 , r 17 , r 19 and r 20 each represents 0-4.
- n2 represents 1 to 3.
- the arylamine compound represented by the general formula (1) or general formula (1a) that is preferably used in the organic EL device of the present invention is a hole injection layer, an electron blocking layer, or a hole transport layer of the organic EL device. It can be used as a constituent material. It is a compound that has a high hole mobility and is preferable as a material for the hole injection layer or the hole transport layer. In addition, it has a high electron blocking performance and is a preferred compound as a material for the electron blocking layer.
- the compound having a pyrimidine ring structure represented by the general formula (2) that is preferably used in the organic EL device of the present invention can be used as a constituent material of the electron transport layer of the organic EL device.
- the compound having a pyrimidine ring structure represented by the general formula (2) is excellent in electron injection and transport ability, and further excellent in stability and durability of a thin film, and is a preferable compound as a material for an electron transport layer. .
- a triphenylamine derivative having two triphenylamine skeletons as a whole molecule represented by the general formula (3), and a trimethylamine as a whole molecule represented by the general formula (4).
- a triphenylamine derivative having four phenylamine skeletons is a preferable compound as a constituent material of a hole injection layer or a hole transport layer of an organic EL device.
- the second hole transport layer in the case where the hole transport layer has a structure in which two layers of the first hole transport layer and the second hole transport layer are laminated, which is a preferred embodiment in the organic EL device of the present invention, It is preferable to contain the arylamine compound represented by the general formula (1) or the general formula (1a).
- the organic EL element of the present invention combines materials for organic EL elements that are excellent in hole / electron injection / transport performance, thin film stability and durability in consideration of carrier balance. Compared to EL devices, the hole transport efficiency from the hole transport layer to the light-emitting layer is improved, and the electron transport efficiency from the electron transport layer to the light-emitting layer is also improved. In the case of a two-layer structure of a layer and a second hole transport layer, two types of triphenylamine derivatives having a specific structure are combined in consideration of carrier balance and material characteristics) As a result, the driving voltage is lowered and the durability of the organic EL element can be improved. It has become possible to realize organic EL elements with high efficiency, low drive voltage, and long life.
- a specific arylamine compound that is excellent in hole and electron injection / transport performance, thin film stability and durability, and capable of effectively expressing the role of hole injection / transport was selected. Accordingly, holes can be efficiently injected and transported to the light emitting layer, and an organic EL element with high efficiency, low driving voltage, and long life can be realized.
- a specific arylamine compound is selected and combined with a specific electron transport material so that carrier balance can be achieved, thereby realizing an organic EL element with high efficiency, low driving voltage, and long life.
- the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer
- two types of triphenylamine derivatives having a specific structure can be used for carrier balance and material properties.
- FIG. 3 is a diagram showing organic EL element configurations of Examples 12 to 17 and Comparative Examples 1 and 2.
- the compound having the pyrimidine ring structure described above can be synthesized according to a method known per se (see, for example, Patent Documents 6 to 7).
- the hole transport layer is preferably used for the first hole transport layer in the case where the first hole transport layer and the second hole transport layer are laminated.
- Specific examples of preferable compounds among the triphenylamine derivatives represented by the general formula (3) having two triphenylamine skeletons as a whole molecule are shown below, but are limited to these compounds. It is not something.
- the hole transport layer is preferably used for the first hole transport layer in the case where the first hole transport layer and the second hole transport layer are laminated.
- Specific examples of preferable compounds among the triphenylamine derivatives represented by the general formula (4) having four triphenylamine skeletons as a whole molecule are shown below, but are limited to these compounds. It is not something.
- Triphenylamine derivatives having four skeletons can be synthesized according to a method known per se (see, for example, Patent Documents 1 and 8 to 9).
- Purification of the arylamine compounds represented by the general formulas (1) and (1a) is performed by purification using column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, sublimation purification, etc. went.
- the compound was identified by NMR analysis.
- melting point, glass transition point (Tg) and work function were measured.
- the melting point is an index of vapor deposition
- the glass transition point (Tg) is an index of stability in a thin film state
- the work function is an index of hole transportability and hole blocking property.
- the compound used in the organic EL device of the present invention is purified by column chromatography, purification by adsorption using silica gel, activated carbon, activated clay, etc., recrystallization using a solvent, crystallization method, sublimation purification method, etc. Finally, the product purified by the sublimation purification method was used.
- Tg Melting point and glass transition point (Tg) were measured with a high sensitivity differential scanning calorimeter (Bruker AXS, DSC3100SA) using powder.
- the work function was determined using an ionization potential measurement device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) after forming a 100 nm thin film on the ITO substrate.
- PYS-202 manufactured by Sumitomo Heavy Industries, Ltd.
- the substrate is composed of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode sequentially on the substrate. And those having a hole blocking layer between the light emitting layer and the electron transport layer, and those having an electron injection layer between the electron transport layer and the cathode.
- a structure that serves as a hole injection layer and a hole transport layer and a structure that serves as an electron injection layer and an electron transport layer. And so on.
- the hole transport layer has a structure in which two layers of a first hole transport layer and a second hole transport layer are laminated.
- an electrode material having a large work function such as ITO or gold is used.
- the hole injection layer of the organic EL device of the present invention in addition to the arylamine compound represented by the general formula (1), materials such as starburst type triphenylamine derivatives and various triphenylamine tetramers; A porphyrin compound typified by copper phthalocyanine; an acceptor heterocyclic compound such as hexacyanoazatriphenylene, a coating-type polymer material, or the like can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- the arylamine compound represented by the general formula (1) is used as the hole transport layer of the organic EL device of the present invention. These may be formed alone, or may be used as a single layer formed by mixing with other hole transporting materials, or may be formed by mixing layers formed alone. A layered structure of layers formed by mixing layers with each other or a layer formed by itself may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method. As a hole transporting material that can be mixed with or simultaneously used with the arylamine compound represented by the general formula (1), N, N′-diphenyl-N, N′-di (m-tolyl) benzidine (TPD) is used.
- TPD N, N′-diphenyl-N, N′-di (m-tolyl) benzidine
- N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine NPD
- benzidine derivatives such as N, N, N ′, N′-tetrabiphenylylbenzidine, 1,1-bis [ 4- (di-4-tolylamino) phenyl] cyclohexane (TAPC)
- TAPC 1,1-bis [ 4- (di-4-tolylamino) phenyl] cyclohexane
- TAPC 1,1-bis [ 4- (di-4-tolylamino) phenyl] cyclohexane
- Triphenylamine derivatives having four triphenylamine skeletons as the entire molecule represented triphenylamine derivatives having three triphenylamine skeletons as various molecules You can raise your body.
- P-doping with trisbromophenylamine hexachloroantimony, a radicalene derivative (for example, see International Publication No. 2014/009310), etc. for the materials usually used for the layer.
- a high molecular compound having a partial structure of a benzidine derivative such as TPD.
- the first hole transport layer on the anode side has two triphenylamine skeletons as a whole molecule represented by the general formula (3).
- the triphenylamine derivative having four triphenylamine skeletons as the whole molecule represented by the general formula (4) is preferably used.
- a material etc. can be used.
- the arylamine compound represented by the general formula (1) is preferably used, but the above-described hole transport material can be used.
- These may be formed singly, but may be used as a single layer formed by mixing with other materials, or may be used as a single layer, mixed layers, or singly
- a layered structure of layers formed by mixing with the layers formed in (1) may be used.
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to the vapor deposition method.
- the light emitting layer of the organic EL device of the present invention various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc., in addition to metal complexes of quinolinol derivatives including Alq 3 Can be used.
- the light emitting layer may be composed of a host material and a dopant material, and an anthracene derivative is preferably used as the host material.
- a heterocyclic compound having an indole ring as a partial structure of a condensed ring A heterocyclic compound having a carbazole ring as a partial structure of a condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used.
- a dopant material a pyrene derivative is preferably used.
- Derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used. These may be formed singly, but may be used as a single layer formed by mixing with other materials, or may be used as a single layer, mixed layers, or singly
- a layered structure of layers formed by mixing with the layers formed in (1) may be used.
- a phosphorescent emitter As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used. Green phosphorescent emitters such as Ir (ppy) 3 , blue phosphorescent emitters such as FIrpic and FIr6, red phosphorescent emitters such as Btp 2 Ir (acac), and the like are used as the host material. As the hole injecting / transporting host material, carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (CBP), TCTA, and mCP can be used.
- CBP 4,4′-di (N-carbazolyl) biphenyl
- CBP 4,4′-di (N-carbazolyl) biphenyl
- TCTA TCTA
- mCP mCP
- p-bis (triphenylsilyl) benzene (UGH2) and 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl-1H-benzimidazole) ) (TPBI) or the like, and a high-performance organic EL element can be manufactured.
- the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
- Non-Patent Document 3 a material that emits delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN as the light emitting material (see, for example, Non-Patent Document 3).
- CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- a phenanthroline derivative such as bathocuproine (BCP) or aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter abbreviated as BAlq).
- BCP bathocuproine
- BAlq aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
- compounds having a hole blocking action such as various rare earth complexes, triazole derivatives, triazine derivatives, and oxadiazole derivatives can be used. These materials may also serve as the material for the electron transport layer.
- These may be formed singly, but may be used as a single layer formed by mixing with other materials, or may be used as a single layer, mixed layers, or singly
- a layered structure of layers formed by mixing with the layers formed in (1) may be used.
- These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- a compound having a pyrimidine ring structure represented by the general formula (2) is preferably used. These may be formed alone, or may be used as a single layer formed by mixing with other electron transporting materials, or may be used as a single layer formed by mixing layers formed separately. Alternatively, a stacked structure of layers formed by mixing with each other or a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
- Examples of the electron transporting material that can be mixed or simultaneously used with the compound having a pyrimidine ring structure represented by the general formula (2) include metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, and triazoles. Derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives, and the like.
- an alkali metal salt such as lithium fluoride and cesium fluoride
- an alkaline earth metal salt such as magnesium fluoride
- a metal oxide such as aluminum oxide
- an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
- the arylamine compound represented by the general formula (1) has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable.
- a deposited film having a film thickness of 100 nm was prepared on the ITO substrate, and an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) was used. The work function was measured. Work function Compound of Example 1 5.79 eV Compound of Example 2 5.74 eV Compound of Example 3 5.67 eV Compound of Example 4 5.70 eV Compound of Example 5 5.62 eV Compound of Example 6 5.60 eV Compound of Example 7 5.65 eV Compound of Example 8 5.63 eV Compound of Example 9 5.57 eV
- the arylamine compound represented by the general formula (1) exhibits a suitable energy level as compared with a work function of 5.4 eV possessed by a general hole transport material such as NPD or TPD. It can be seen that it has a hole transport capability.
- the organic EL element has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
- the layer 5, the light emitting layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were deposited in this order.
- the glass substrate 1 formed with ITO having a film thickness of 150 nm was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 200 ° C. for 10 minutes. Then, after performing UV ozone treatment for 15 minutes, this glass substrate with ITO was attached in a vacuum evaporation machine, and pressure was reduced to 0.001 Pa or less. Subsequently, a compound (HIM-1) having the following structural formula was formed to a thickness of 5 nm as a hole injection layer 3 so as to cover the transparent anode 2.
- a triphenylamine derivative (3-1) having two triphenylamine skeletons as a whole molecule of the following structural formula as the first hole transport layer 4 was formed with a film thickness of 60 nm. It formed so that it might become.
- the compound (1-12) of Example 1 was formed as a second hole transport layer 5 to a thickness of 5 nm.
- a pyrene derivative (EMD-1) having the following structural formula and an anthracene derivative (EMH-1) having the following structural formula are formed as the light emitting layer 6, and the deposition rate ratio is EMD-1: EMH.
- a compound (2-125) having a pyrimidine ring structure of the following structural formula and a compound (ETM-1) of the following structural formula as the electron transporting layer 7 are deposited at a deposition rate ratio of 2-125: ETM.
- lithium fluoride was formed as the electron injection layer 8 to a thickness of 1 nm.
- aluminum was deposited to 100 nm to form the cathode 9.
- the characteristic measurement was performed at normal temperature in air
- Example 12 the compound (1-9) of Example 2 was used instead of the compound (1-12) of Example 1 as a material for the second hole transport layer 5, and the film was formed to a thickness of 5 nm.
- An organic EL element was produced under the same conditions except that. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 10 the compound (1-1) of Example 4 was used instead of the compound (1-12) of Example 1 as a material for the second hole transport layer 5, and the film thickness was 5 nm.
- An organic EL element was produced under the same conditions except that. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 12 the compound (1-26) of Example 6 was used instead of the compound (1-12) of Example 1 above as the material of the second hole transport layer 5, and the film was formed to a thickness of 5 nm.
- An organic EL element was produced under the same conditions except that. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 12 the compound (1-27) of Example 7 was used instead of the compound (1-12) of Example 1 as a material for the second hole transport layer 5, and the film was formed to a thickness of 5 nm.
- An organic EL element was produced under the same conditions except that. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 12 the compound (1-29) of Example 8 was used instead of the compound (1-12) of Example 1 above as the material of the second hole transport layer 5, and the film was formed to a thickness of 5 nm.
- An organic EL element was produced under the same conditions except that. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 12 For comparison, in Example 12, instead of the compound (1-12) of Example 1 as the material of the second hole transport layer 5, the entire molecule of the structural formula has two triphenylamine skeletons.
- An organic EL device was produced under the same conditions except that the triphenylamine derivative (3-1) used was formed to a thickness of 5 nm.
- the characteristic measurement was performed at normal temperature in air
- Example 12 For comparison, in Example 12, instead of the compound (1-12) of Example 1 as the material of the second hole transport layer 5, the compound (1-12) of Example 1 having the following structural formula:
- An organic EL device was produced under the same conditions except that an arylamine compound (HTM-1) in which the 3-position was not substituted with a phenyl group was formed to a thickness of 5 nm.
- HTM-1 arylamine compound
- Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.
- Table 1 summarizes the results of measuring the element lifetime using the organic EL elements prepared in Examples 12 to 17 and Comparative Examples 1 and 2.
- the element lifetime corresponds to 95% of the emission brightness of 1900 cd / m 2 (when the initial brightness is 100%) when the constant current drive is performed with the emission brightness (initial brightness) at the start of light emission being 2000 cd / m 2 : It was measured as the time to decay to 95% decay.
- the luminous efficiency when a current density of 10 mA / cm 2 was passed was 7.82 to 8.69 cd / A of the organic EL elements of Comparative Examples 1 and 2, and Examples 12 to The 17 organic EL devices had high efficiency of 8.64 to 9.05 cd / A.
- the organic EL elements of Examples 12 to 17 were as high as 7.21 to 7.54 lm / W compared to 6.54 to 7.13 lm / W of the organic EL elements of Comparative Examples 1 and 2. It was efficiency.
- the organic EL elements of Examples 12 to 17 are 171 to 228 hours longer than the 136 to 162 hours of the organic EL elements of Comparative Examples 1 and 2, which greatly increases the life. I understand that.
- the organic EL device of the present invention improves the carrier balance inside the organic EL device by combining an arylamine compound in which a specific position is substituted with an aryl group in the hole transport layer, compared with the conventional organic EL device. It was found that an organic EL device with high luminous efficiency and long life can be realized.
- the organic EL device of the present invention which combines an arylamine compound in which a specific position is substituted with an aryl group in the hole transport layer, can improve the light emission efficiency and improve the durability of the organic EL device. It has become possible to expand into home appliances and lighting applications.
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Abstract
Description
そして、熱活性化遅延蛍光(TADF)による発光を利用する素子も開発されている。2011年に九州大学の安達らは、熱活性化遅延蛍光材料を用いた素子によって5.3%の外部量子効率を実現させた(例えば、非特許文献3参照)。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)において、Ar1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
一般式(1)、一般式(1a)において、n1は0または1~2の整数を表すが、n1が0の時は、2つのジアリールアミノ基で置換されたベンゼン環が直接(単結合で)結合していることを示し、n1が1の時は、2つのジアリールアミノ基で置換されたベンゼン環が1個のフェニレン基を介して結合していることを示し、n1が2の時は、2つのジアリールアミノ基で置換されたベンゼン環が2個のフェニレン基(ビフェニレン基)を介して結合していることを示す。
一般式(2)中のAr10としては、置換基を有するフェニル基が好ましく、この場合の置換基としては、フェニル基、ビフェニリル基、ターフェニル基などの芳香族炭化水素基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの縮合多環芳香族基が好ましく、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基がより好ましい。
一般式(2)中のAr11としては、置換基を有するフェニル基が好ましく、この場合の置換基としては、フェニル基、ビフェニリル基、ターフェニル基などの芳香族炭化水素基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの縮合多環芳香族基が好ましく、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基がより好ましい。
一般式(2)において、Ar9とAr10が同一ではないことが、薄膜の安定性の観点から好ましい。ここで、Ar9とAr10が同一の基である場合、異なる置換基であってもよいし、あるいは、異なる置換位置であってもよい。
一般式(2)において、Ar10とAr11は同一の基であってもよいが、分子全体の対称性がよくなることによって結晶化し易くなる恐れがあり、薄膜の安定性の観点から、Ar10とAr11は異なる基であることが好ましく、Ar10とAr11が同時に水素原子とはなることはないものとする。
一般式(2)において、Ar10とAr11の一方が水素原子であることが好ましい。
一般式(2)において、ベンゼン環におけるAr12の結合位置は、ピリミジン環との結合位置に対し、メタ位であることが、薄膜の安定性の観点から好ましい。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(3)中のR5~R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数5ないし10のシクロアルキル基」または「置換基を有する炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(3)中のR5~R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数5ないし10のシクロアルキル基」または「置換基を有する炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(3)中のR5~R10で表される「置換基を有する炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数5ないし10のシクロアルキル基」または「置換基を有する炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
また、これらの基は置換基を有していてもよく、置換基として、前記一般式(1)、一般式(1a)中のAr1~Ar8で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
構造式(B)において、n2は1~3を表す。
前記一般式(2)で表される、ピリミジン環構造を有する化合物は、電子注入および輸送能力に優れており、さらに薄膜の安定性や耐久性に優れ、電子輸送層の材料として好ましい化合物である。
本発明の有機EL素子における好適な態様である、正孔輸送層が第一正孔輸送層および第二正孔輸送層の2層が積層した構造である場合の第二正孔輸送層は、前記一般式(1)、または一般式(1a)で表されるアリールアミン化合物を含有することが好ましい。
高効率、低駆動電圧、長寿命の有機EL素子を実現することが可能となった。
その他、本発明の有機EL素子に用いられる化合物は、カラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土などによる吸着精製、溶媒による再結晶や晶析法、昇華精製法などによって精製を行った後、最後に昇華精製法によって精製したものを用いた。
前記一般式(1)で表されるアリールアミン化合物と混合もしくは同時に使用できる、正孔輸送性の材料としては、N,N’-ジフェニル-N,N’-ジ(m-トリル)ベンジジン(TPD)、N,N’-ジフェニル-N,N’-ジ(α-ナフチル)ベンジジン(NPD)、N,N,N’,N’-テトラビフェニリルベンジジンなどのベンジジン誘導体、1,1-ビス[4-(ジ-4-トリルアミノ)フェニル]シクロヘキサン(TAPC)、一般式(3)で表される分子全体としてトリフェニルアミン骨格を2個有しているトリフェニルアミン誘導体、一般式(4)で表される分子全体としてトリフェニルアミン骨格を4個有しているトリフェニルアミン誘導体、種々の分子全体としてトリフェニルアミン骨格を3個有しているトリフェニルアミン誘導体などをあげることができる。
また、第二正孔輸送層としては、一般式(1)で表されるアリールアミン化合物が好ましく用いられるが、その他、前記した正孔輸送性の材料などを用いることができる。
前記一般式(2)で表されるピリミジン環構造を有する化合物と混合もしくは同時に使用できる、電子輸送性の材料としては、Alq3、BAlqをはじめとするキノリノール誘導体の金属錯体、各種金属錯体、トリアゾール誘導体、トリアジン誘導体、オキサジアゾール誘導体、ピリジン誘導体、ピリミジン誘導体、ベンズイミダゾール誘導体、チアジアゾール誘導体、アントラセン誘導体、カルボジイミド誘導体、キノキサリン誘導体、ピリドインドール誘導体、フェナントロリン誘導体、シロール誘導体などをあげることができる。
窒素置換した反応容器に、4-{(ビフェニル-4-イル)-フェニルアミノ}-4’’-{(ビフェニル-4-イル)-アミノ}-3-フェニル-1,1’;3’,1’’-ターフェニル17.0g、ブロモベンゼン4.12g、酢酸パラジウム0.13g、トリ-tert-ブチルホスフィンの50%(w/v)トルエン溶液0.33ml、tert-ブトキシナトリウム2.73g、トルエン190mlを加えて加熱し、80℃で3時間撹拌した。冷却し、ろ過によって不溶物を除いた後濃縮し、カラムクロマトグラフ(担体:シリカゲル、溶離液:トルエン/n-ヘキサン)によって精製した。アセトンを加えることによって析出する固体を集めることによって、4,4’’-ビス{(ビフェニル-4-イル)-フェニルアミノ}-3-フェニル-1,1’;3’,1’’-ターフェニル(化合物1-12)の白色粉体13.29g(収率71%)を得た。
1H-NMR(CDCl3)で以下の44個の水素のシグナルを検出した。
δ(ppm)=7.62-7.58(4H)、7.55-7.49(4H)、7.48-7.38(6H)、7.37-7.05(30H)。
窒素置換した反応容器に、4,4’’-ビス{(ビフェニル-4-イル)-アミノ}-3、3’’-ジフェニル-1,1’;4’,1’’-ターフェニル16.3g、ヨードベンゼン18.6g、銅粉0.29g、炭酸カリウム9.61g、3,5-ジ-tert-ブチルサリチル酸1.85g、亜硫酸水素ナトリウム0.47g、ドデシルベンゼン20mlを加えて加熱し、190~200℃で17時間撹拌した。冷却し、トルエン1500ml、シリカゲル40g、活性白土20gを添加した後、撹拌した。ろ過によって不溶物を除いた後濃縮し、クロロベンゼンを用いた再結晶を繰り返すことによって、4,4’’-ビス{(ビフェニル-4-イル)-フェニルアミノ}-3、3’’-ジフェニル-1,1’;4’,1’’-ターフェニル(化合物1-9)の白色粉体9.65g(収率49%)を得た。
1H-NMR(CDCl3)で以下の48個の水素のシグナルを検出した。
δ(ppm)=7.62(4H)、7.52(4H)、7.45(4H)、7.36-7.04(32H)、6.99(4H)。
窒素置換した反応容器に、4-ビス(ビフェニル-4-イル)アミノ-2,6-ジフェニル-ブロモベンゼン16.0g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸10.2g、テトラキストリフェニルホスフィンパラジウム0.60g、炭酸カリウム4.62g、水60ml、トルエン320ml、エタノール60mlを加えて加熱し、還流下18時間撹拌した。冷却し、水200mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理、シリカゲル40gを用いた吸着精製を行った後、濃縮し、メタノールを用いた分散洗浄を行うことによって粗製物を得た。
粗製物にトルエン/エタノールを用いた再結晶、酢酸エチルを用いた再結晶を繰り返すことによって、4-ビス(ビフェニル-4-イル)アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-2,6-ジフェニル-ビフェニル(化合物1-23)の白色粉体12.7g(収率57%)を得た。
1H-NMR(CDCl3)で以下の48個の水素のシグナルを検出した。
δ(ppm)=7.65-7.53(8H)、7.48-6.97(36H)、6.79-6.73(4H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-(1,1’-ビフェニル-4-イル)フェニルアミン 18.0g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸10.2g、(1,1’-ビフェニル-4-イル)フェニルアミノ(1,1’-ビフェニル-4’-イル)ボロン酸ピナコラートエステル 21.8g、テトラキストリフェニルホスフィンパラジウム0.87g、炭酸カリウム6.3g、水46ml、トルエン144ml、エタノール36mlを加えて加熱し、還流下18時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行った後に濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4,4’’-ビス{(ビフェニル-4-イル)-フェニルアミノ}-2-フェニル-1,1’;4’,1’’-ターフェニル(化合物1-1)の白色粉体12.9g(収率43%)を得た。
1H-NMR(CDCl3)で以下の44個の水素のシグナルを検出した。
δ(ppm)=7.65-7.61(4H)、7.57-7.07(40H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-ビス(ビフェニル-4-イル)アミン 10.0g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸7.9g、テトラキストリフェニルホスフィンパラジウム0.60g、炭酸カリウム5.0g、水30ml、トルエン80ml、エタノール40mlを加えて加熱し、還流下16時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行い、濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4-ビス(ビフェニル-4-イル)アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-2-フェニル-1,1’-ビフェニル(化合物1-24)の白色粉体5.3g(収率37%)を得た。
1H-NMR(CDCl3)で以下の44個の水素のシグナルを検出した。
δ(ppm)=7.65-7.56(8H)、7.52-7.14(28H)、7.08-6.99(8H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-{(ナフタレン-1-イル)フェニル-4-イル}(ビフェニル-4-イル)アミン 10.0g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸7.3g、テトラキストリフェニルホスフィンパラジウム0.60g、炭酸カリウム4.6g、水30ml、トルエン80ml、エタノール40mlを加えて加熱し、還流下16時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行い、濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4-{(ナフタレン-1-イル)フェニル-4-イル}(ビフェニル-4-イル)アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-2-フェニル-1,1’-ビフェニル(化合物1-26)の白色粉体9.7g(収率69%)を得た。
1H-NMR(CDCl3)で以下の46個の水素のシグナルを検出した。
δ(ppm)=8.08-8.07(1H)、7.95-7.87(2H)、7.66-6.99(43H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-{(ナフタレン-2-イル)フェニル-4-イル}(ビフェニル-4-イル)アミン 7.5g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸5.5g、テトラキストリフェニルホスフィンパラジウム0.40g、炭酸カリウム3.4g、水23ml、トルエン60ml、エタノール30mlを加えて加熱し、還流下16時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行い、濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4-{(ナフタレン-2-イル)フェニル-4-イル}(ビフェニル-4-イル)アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-2-フェニル-1,1’-ビフェニル(化合物1-27)の白色粉体6.1g(収率58%)を得た。
1H-NMR(CDCl3)で以下の46個の水素のシグナルを検出した。
δ(ppm)=8.07(1H)、7.95-7.76(4H)、7.68-6.98(41H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-ビス{(ナフタレン-1-イル)フェニル-4-イル}アミン10.0g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸6.7g、テトラキストリフェニルホスフィンパラジウム0.50g、炭酸カリウム4.2g、水30ml、トルエン80ml、エタノール40mlを加えて加熱し、還流下16時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行い、濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4-ビス{(ナフタレン-1-イル)フェニル-4-イル}アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-2-フェニル-ビフェニル(化合物1-29)の白色粉体10g(収率73%)を得た。
1H-NMR(CDCl3)で以下の48個の水素のシグナルを検出した。
δ(ppm)=8.12-8.10(2H)、7.97-7.88(4H)、7.63-7.01(42H)。
窒素置換した反応容器に、(6-ブロモ-1,1’-ビフェニル-3-イル)-{(9,9-ジメチルフルオレン-2-イル)フェニル-4-イル}(ビフェニル-4-イル)アミン 12.1g、4-{N-(ビフェニル-4-イル)-N-フェニルアミノ}フェニルボロン酸8.9g、テトラキストリフェニルホスフィンパラジウム0.70g、炭酸カリウム5.6g、水40ml、トルエン100ml、エタノール50mlを加えて加熱し、還流下16時間撹拌した。冷却し、水100mlを加えた後、分液操作によって有機層を採取した。有機層に無水硫酸マグネシウムを用いた脱水処理を行い、濃縮し、残渣をカラムクロマトグラフィーで精製を行い、4-{(9,9-ジメチルフルオレン-2-イル)フェニル-4-イル}(ビフェニル-4-イル)アミノ-4’-{(ビフェニル-4-イル)-フェニルアミノ}-3-フェニル-1,1’-ビフェニル(化合物1-30)の白色粉体8.3g(収率49%)を得た。
1H-NMR(CDCl3)で以下の48個の水素のシグナルを検出した。
δ(ppm)=7.71-7.15(34H)、7.09-6.99(8H)、1.51(6H)。
融点 ガラス転移点
実施例1の化合物 観測されず 116℃
実施例2の化合物 263℃ 124℃
実施例3の化合物 238℃ 126℃
実施例4の化合物 観測されず 120℃
実施例5の化合物 観測されず 118℃
実施例6の化合物 観測されず 121℃
実施例7の化合物 観測されず 121℃
実施例8の化合物 観測されず 125℃
実施例9の化合物 観測されず 125℃
仕事関数
実施例1の化合物 5.79eV
実施例2の化合物 5.74eV
実施例3の化合物 5.67eV
実施例4の化合物 5.70eV
実施例5の化合物 5.62eV
実施例6の化合物 5.60eV
実施例7の化合物 5.65eV
実施例8の化合物 5.63eV
実施例9の化合物 5.57eV
比較のために、実施例12において、第二正孔輸送層5の材料として実施例1の化合物(1-12)に代えて前記構造式の分子全体としてトリフェニルアミン骨格を2個有しているトリフェニルアミン誘導体(3-1)を膜厚5nmとなるように形成した以外は、同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行った。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例12において、第二正孔輸送層5の材料として実施例1の化合物(1-12)に代えて下記構造式の、実施例1の化合物(1-12)において、3位がフェニル基で置換されていないアリールアミン化合物(HTM-1)を膜厚5nmとなるように形成した以外は、同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行った。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
さらに、素子寿命(95%減衰)においては、比較例1~2の有機EL素子の136~162時間に対し、実施例12~17の有機EL素子では171~228時間と、大きく長寿命化していることが分かる。
2 透明陽極
3 正孔注入層
4 第一正孔輸送層
5 第二正孔輸送層
6 発光層
7 電子輸送層
8 電子注入層
9 陰極
Claims (13)
- 少なくとも陽極、正孔輸送層、発光層、電子輸送層及び陰極をこの順に有する有機エレクトロルミネッセンス素子において、前記正孔輸送層が下記一般式(1)で表されるアリールアミン化合物を含有することを特徴とする有機エレクトロルミネッセンス素子。
- 前記電子輸送層が、下記一般式(2)で表されるピリミジン環構造を有する化合物を含有することを特徴とする請求項1~2のいずれか一項に記載の有機エレクトロルミネッセンス素子。
- 前記正孔輸送層が、第一正孔輸送層および第二正孔輸送層の2層構造であって、該第二正孔輸送層が、前記アリールアミン化合物を含有することを特徴とする請求項1~3のいずれか一項に記載の有機エレクトロルミネッセンス素子。
- 前記第一正孔輸送層が、前記第二正孔輸送層に含まれているアリールアミン化合物とは異なるトリフェニルアミン誘導体を含有しており、該トリフェニルアミン誘導体は、2つのトリフェニルアミン骨格が単結合または2価の炭化水素基で連結された分子構造を有しており且つ分子全体としてトリフェニルアミン骨格を2個~6個有している誘導体である請求項4に記載の有機エレクトロルミネッセンス素子。
- 前記第一正孔輸送層に含まれているトリフェニルアミン誘導体が、下記一般式(3)で表される誘導体である請求項5記載の有機エレクトロルミネッセンス素子。
- 前記第一正孔輸送層に含まれているトリフェニルアミン誘導体が、下記一般式(4)で表される誘導体である請求項5記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、青色発光性ドーパントを含有することを特徴とする請求項1~7のいずれか一項に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、ピレン誘導体である青色発光性ドーパントを含有することを特徴とする請求項8記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、アントラセン誘導体を含有することを特徴とする請求項1~9のいずれか一項に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、アントラセン誘導体であるホスト材料を含有することを特徴とする請求項10記載の有機エレクトロルミネッセンス素子。
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EP3370272A1 (en) | 2018-09-05 |
JPWO2017073594A1 (ja) | 2018-08-16 |
US11594683B2 (en) | 2023-02-28 |
JP6815326B2 (ja) | 2021-01-20 |
CN108352454B (zh) | 2020-02-28 |
TW201727965A (zh) | 2017-08-01 |
TWI720044B (zh) | 2021-03-01 |
KR20180075559A (ko) | 2018-07-04 |
US20180331298A1 (en) | 2018-11-15 |
CN108352454A (zh) | 2018-07-31 |
EP3370272A4 (en) | 2019-07-10 |
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