JP2021014444A - アミン類誘導体及びその有機電界発光素子 - Google Patents
アミン類誘導体及びその有機電界発光素子 Download PDFInfo
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- 150000001412 amines Chemical class 0.000 title claims abstract description 45
- 125000001424 substituent group Chemical group 0.000 claims abstract description 42
- -1 benzoimidazolyl group Chemical group 0.000 claims abstract description 33
- 239000010410 layer Substances 0.000 claims description 143
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 238000000605 extraction Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000005549 heteroarylene group Chemical group 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 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 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 85
- 238000000034 method Methods 0.000 abstract description 19
- 239000011368 organic material Substances 0.000 abstract description 13
- 230000009477 glass transition Effects 0.000 abstract description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 38
- 239000007787 solid Substances 0.000 description 37
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000010586 diagram Methods 0.000 description 20
- 238000004949 mass spectrometry Methods 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 239000007983 Tris buffer Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000006870 function Effects 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000002356 single layer Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 230000005684 electric field Effects 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- IOQORVDNYPOZPL-VQTJNVASSA-N (5S,6R)-5-(4-chlorophenyl)-6-cyclopropyl-3-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-5,6-dihydro-2H-1,2,4-oxadiazine Chemical compound ClC1=CC=C(C=C1)[C@@H]1NC(=NO[C@@H]1C1CC1)C1=NC(=C(C=C1)N1C=NC(=C1)C)OC IOQORVDNYPOZPL-VQTJNVASSA-N 0.000 description 5
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 5
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 5
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 5
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 5
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 5
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 5
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 5
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229940126208 compound 22 Drugs 0.000 description 5
- 229940126540 compound 41 Drugs 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 5
- 150000002825 nitriles Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 3
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- WKRCOZSCENDENK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=CC=C2S1 WKRCOZSCENDENK-UHFFFAOYSA-N 0.000 description 3
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 3
- 0 IC(*1)=Nc2c1cccc2 Chemical compound IC(*1)=Nc2c1cccc2 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940125851 compound 27 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
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- 238000001953 recrystallisation Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 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
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000005580 triphenylene group Chemical group 0.000 description 3
- 239000011701 zinc Substances 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 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 2
- 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
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 1
- KEQRPCPOINRCDB-UHFFFAOYSA-N iridium(3+);pentane-2,4-dione;1-phenylisoquinoline Chemical compound [Ir+3].CC(=O)CC(C)=O.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 KEQRPCPOINRCDB-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
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- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 125000005562 phenanthrylene group Chemical group 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- FOGKDYADEBOSPL-UHFFFAOYSA-M rubidium(1+);acetate Chemical compound [Rb+].CC([O-])=O FOGKDYADEBOSPL-UHFFFAOYSA-M 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- FXFWLXFJBVILBE-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C FXFWLXFJBVILBE-UHFFFAOYSA-N 0.000 description 1
- SXXNJJQVBPWGTP-UHFFFAOYSA-K tris[(4-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-] SXXNJJQVBPWGTP-UHFFFAOYSA-K 0.000 description 1
- 108010086502 tumor-derived adhesion factor Proteins 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Abstract
Description
前記Ar3、Ar4は、独立して、置換もしくは未置換のC6〜C30のアリール基、置換もしくは未置換のC3〜C30のヘテロアリール基から選択される1種であり、
前記Lは、下記に示す基から選択される1種であり、
前記L11、L12は、独立して、単結合、置換もしくは未置換のC6〜C18のアリーレン基、置換もしくは未置換のC3〜C18のヘテロアリーレン基から選択される1種である。
本発明に係るアミン類誘導体のガラス転移温度が高く、良好な熱安定性を有するため、本発明に係るアミン類誘導体は、より安定した光学材料であり、それを有機電界発光素子の光取り出し材料として用いた場合、有機電界発光素子は、より長い使用寿命を示す。
前記Ar3、Ar4は、独立して、置換もしくは未置換のC6〜C30のアリール基、置換もしくは未置換のC3〜C30のヘテロアリール基から選択される1種であり、
前記Lは、下記に示す基から選択される1種であり、
前記L11、L12は、独立して、単結合、置換もしくは未置換のC6〜C18のアリーレン基、置換もしくは未置換のC3〜C18のヘテロアリーレン基から選択される1種である。
前記cは、0〜4から選択される整数であり、前記R3は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、cが1を超えると、それぞれのR3は、同じか又は異なる。
前記Ar3、Ar4は、独立して、置換もしくは未置換のC6〜C30のアリール基、置換もしくは未置換のC3〜C30のヘテロアリール基から選択される1種である。
前記eは、0〜4から選択される整数であり、前記R5は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、eが1を超えると、それぞれのR5は、同じか又は異なり、
前記fは、0〜4から選択される整数であり、前記R6は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、fが1を超えると、それぞれのR6は、同じか又は異なり、
前記gは、0〜5から選択される整数であり、前記R7は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、gが1を超えると、それぞれのR7は、同じか又は異なり、
前記R0は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、
前記L2は、単結合、置換もしくは未置換のC6〜C18のアリーレン基、置換もしくは未置換のC3〜C18のヘテロアリーレン基から選択される1種である。
前記R5は、メチル基、エチル基、プロピル基、ブチル基から選択される1種であり、且つそれぞれのR5は、同じか又は異なり、
前記R7は、メチル基、エチル基、プロピル基、ブチル基、フェニル基、トリル基、エチルフェニル基から選択される1種であり、且つそれぞれのR7は、同じか又は異なる。
前記R2は、メチル基、エチル基、プロピル基、ブチル基から選択される1種であり、且つそれぞれのR2は、同じか又は異なり、
前記R3は、メチル基、エチル基、プロピル基、ブチル基から選択される1種である。
基板/陽極/正孔輸送層/発光層/電子輸送層/金属陰極/光取り出し層、又は、
基板/陽極/正孔輸送層/発光層/電子輸送層/電子注入層/金属陰極/光取り出し層、又は、
基板/陽極/正孔輸送層/発光層/正孔ブロッキング層/電子輸送層/金属陰極/光取り出し層、又は、
基板/陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/金属陰極/光取り出し層、又は、
基板/陽極/正孔注入層/正孔輸送層/発光層/正孔ブロッキング層/電子輸送層/電子注入層/金属陰極/光取り出し層である。
1.
原料、試薬及び分析用デバイスの説明
本発明で使用される原料及び試薬はすべて純粋な試薬であった。
質量分析は、島津集団英国のKratos Analytical社製のAXIMA−CFR plusマトリックス支援レーザー脱離イオン化飛行質量分析計を使用し、クロロホルムを溶媒とした。
元素分析は、ドイツのElementar社製のVario EL cube型有機元素分析計を使用し、サンプル質量は5〜10mgでした。
核磁気共鳴(1H NMR)は、600MHzのBruker−510型核磁気共鳴スペクトロメーター(ドイツのBruker社製)を使用し、CDCl3を溶媒とし、TMSを内部標準とした。
1Lの反応フラスコに脱気したトルエン溶媒(400mL)を加えた後、原料の4−(2−ベンゾオキサゾール)アニリン(37.8g、0.18mol)、ブロモベンゼン(19.0ml、0.18mol)及びナトリウム−tert−ブトキシド(22.8g、0.234mol)を順次に加えた。窒素置換を3回行った後、酢酸パラジウム(0.4g、0.0018mol)を加えた。窒素置換を更に3回行った後、トリ−t−ブチル−ホスフィン(7.2mLの1.0Mのトルエン溶液、0.0072mol)を加えた。窒素置換ステップを更に3回繰り返した後、当該混合物を窒素雰囲気下で2時間還流した。反応停止後、混合物を室温まで冷却し、珪藻土でろ過してろ液を得た。ろ液を濃縮し、少量のメタノールを加えた後、静置して再結晶し、一定時間後に固体が生成し、その固体を吸引ろ過してメタノールでリンスし、再結晶固体である中間体I−1(46.3g、収率約90%)を得て、HPLCにて固体純度≧98.1%を検出した。
250mLの反応フラスコに脱気したトルエン溶媒(100mL)を加えた後、原料の中間体I−1(17.6g、0.062mol)、2,7−ジブロモ−9,9−ジメチルフルオレン(9.8g、0.028mol)及びナトリウム−tert−ブトキシド(8.0g、0.084mol)を順次に加えた。窒素置換を3回行った後、酢酸パラジウム(0.12g、0.00056mol)を加えた。窒素置換を更に3回行った後、トリ−t−ブチル−ホスフィン(2.24mLの1.0Mのトルエン溶液、0.00224mol)を加えた。窒素置換ステップを更に3回繰り返した後、当該混合物を窒素雰囲気下で2時間還流した。反応停止後、混合物を室温まで冷却し、珪藻土でろ過してろ液を得た。ろ液を濃縮して60℃まで加熱した後、少量のエタノールを加え、室温まで静置して再結晶し、一定時間後,固体が生成し、その固体を吸引ろ過してエタノールでリンスし、再結晶固体である淡黄色の固体化合物1(18.1g、収率約85%)を得て、HPLCにて固体純度≧99.9%を検出した。
1Lの反応フラスコに固体原料の2−ブロモ−7−ヨードフルオレン(37.1g、0.1mol)、4−ブロモフェニルボロン酸(22.1g、0.11mol)を順次に加えた後、超音波で脱気したトルエン(250mL)、エタノール(100mL)及び150mLの炭酸カリウム(41.4g、0.3mol)の水溶液を加えた。真空にして窒素を3回充填し、窒素雰囲気下で触媒のテトラキス(トリフェニルホスフィン)パラジウム(1.15g、0.001mol)を加え、真空にして窒素を3回充填し続け、80℃で還流撹拌して4時間反応させてから加熱停止し、混合物に150mLの水を加え、30分間撹拌し、約40℃まで冷却し、減圧ろ過し、熱水(100mL)及びアセトン(150mL)を順次に用いてろ過ケーキを洗浄し、ろ液のpH値が約7になるように確保した。ろ過ケーキを1Lのクロロホルムに溶解し、溶液をシリカゲル漏斗に通し、ろ液を500mLまで濃縮してから少量のメタノール(約25mL)を加えて再結晶し、減圧ろ過して固体(36.0g、収率約90%)を得て、HPLCにて固体純度≧98.6%を検出した。
合成例1における2,7−ジブロモ−9,9−ジメチルフルオレンを等モル量の中間体aで置き換え、他のステップは同様にして、淡黄色の固体化合物73(18.3g、収率約78%)を得た。質量分析m/z:839.29(計算値:839.01)。理論元素含有量(%)C59H42N4O2:C, 84.46; H, 5.05; N, 6.68; O, 3.81 実測元素含有量(%):C, 84.54; H, 5.05; N, 6.66; O, 3.75。1H NMR (600 MHz, CDCl3) (δ, ppm): 8.19−8.05 (m, 4H), 7.74 (ddd, J=14.1, 8.0, 4.9 Hz, 3H), 7.67 (d, J=8.1 Hz, 1H), 7.63 (dd, J=5.0, 3.5 Hz, 3H), 7.60−7.52 (m, 3H), 7.39−7.29 (m, 8H), 7.29−7.26 (m, 2H), 7.26−7.21 (m, 5H), 7.21−7.10 (m, 7H), 1.49 (s, 6H)。上記結果から、得られた生成物がターゲット製品であることを確認した。
化合物のガラス転移温度(Tg)の測定:測定装置は米国TA社製のDSC25型示差走査熱量計、テスト雰囲気は窒素雰囲気、窒素の流速は50ml/min、昇温速度は10℃/min、温度範囲は50〜350℃、化合物サンプルの質量は1〜6mg、坩堝タイプは、アルミニウム製坩堝であった。測定されたガラス転移温度(Tg)を、表1に示す。
本発明において、有機材料はいずれも昇華したものであり、純度はすべて99.99%以上であった。実験で使用されたITOガラス基板は、深セン南玻表示デバイス科技有限公司から購入した。ITOガラス基板は、5%のガラス清浄液によって毎回20分間で2回超音波清浄してから、脱イオン水によって毎回10分間で2回超音波清浄し、アセトン及びイソプロピルケトンを順次に用いて20分間超音波清浄し、120℃で乾燥させた。
ガラス基板上にITO/Ag/ITOを陽極とし、陽極上にHIM−1を真空蒸着して第1の正孔注入層とし、蒸着厚さは60nmであり、第1の正孔注入層上にHAT−CNを真空蒸着して第2の正孔注入層とし、蒸着厚さは5nmであり、第2の正孔注入層上にNPBを真空蒸着して正孔輸送層とし、蒸着厚さは60nmであり、正孔輸送層上にBH−1と3%のBD−1を真空蒸着して発光層とし、蒸着厚さは25nmであり、発光層上にAlq3:Liq(1:1)を真空蒸着して電子輸送層とし、蒸着厚さは30nmであり、電子輸送層上にLiFを真空蒸着して電子注入層とし、蒸着厚さは1nmであり、電子注入層上にMg/Ag(9:1)を真空蒸着して陰極とし、蒸着厚さは15nmであり、陰極上に本発明に係る化合物1を真空蒸着して光取り出し層とし、蒸着厚さは60nmであった。
Claims (10)
- 式Iで示され、
前記Ar3、Ar4は、独立して、置換もしくは未置換のC6〜C30のアリール基、置換もしくは未置換のC3〜C30のヘテロアリール基から選択される1種であり、
前記Lは、下記に示す基から選択される1種であり、
前記L11、L12は、独立して、単結合、置換もしくは未置換のC6〜C18のアリーレン基、置換もしくは未置換のC3〜C18のヘテロアリーレン基から選択される1種である、ことを特徴とするアミン類誘導体。 - 前記Ar2、Ar4は、同じ置換基から選択される、ことを特徴とする請求項3に記載のアミン類誘導体。
- 前記Ar3、Ar4は、独立して、下記に示す基から選択される1種であり、
前記eは、0〜4から選択される整数であり、前記R5は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、eが1を超えると、それぞれのR5は、同じか又は異なり、
前記fは、0〜4から選択される整数であり、前記R6は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、fが1を超えると、それぞれのR6は、同じか又は異なり、
前記gは、0〜5から選択される整数であり、前記R7は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、gが1を超えると、それぞれのR7は、同じか又は異なり、
前記R0は、置換もしくは未置換のC1〜C10のアルキル基、置換もしくは未置換のC6〜C18のアリール基から選択される1種であり、
前記L2は、単結合、置換もしくは未置換のC6〜C18のアリーレン基、置換もしくは未置換のC3〜C18のヘテロアリーレン基から選択される1種である、ことを特徴とする請求項1〜5のいずれか一項に記載のアミン類誘導体。 - 陽極と、有機物層と、陰極と、光取り出し層とを含み、前記有機物層は、陽極と陰極との間に位置し、前記有機物層は、正孔輸送層と、発光層と、電子輸送層とを含み、前記正孔輸送層は、陽極と発光層との間に位置し、前記電子輸送層は、発光層と陰極との間に位置し、前記光取り出し層は、陽極から離れる陰極の側に位置し、前記光取り出し層は、請求項1〜9のいずれか一項に記載のアミン類誘導体を含む、ことを特徴とする有機電界発光素子。
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KR102429199B1 (ko) | 2022-08-04 |
EP3763707B1 (en) | 2023-05-03 |
US20210009574A1 (en) | 2021-01-14 |
US11725003B2 (en) | 2023-08-15 |
KR20210007817A (ko) | 2021-01-20 |
ES2949041T3 (es) | 2023-09-25 |
CN110256358B (zh) | 2020-03-17 |
PL3763707T3 (pl) | 2023-10-09 |
CN110256358A (zh) | 2019-09-20 |
JP6972226B2 (ja) | 2021-11-24 |
EP3763707A1 (en) | 2021-01-13 |
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