JP7469152B6 - 有機エレクトロルミネセント化合物及びそれを含む有機エレクトロルミネセントデバイス - Google Patents
有機エレクトロルミネセント化合物及びそれを含む有機エレクトロルミネセントデバイス Download PDFInfo
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- JP7469152B6 JP7469152B6 JP2020106209A JP2020106209A JP7469152B6 JP 7469152 B6 JP7469152 B6 JP 7469152B6 JP 2020106209 A JP2020106209 A JP 2020106209A JP 2020106209 A JP2020106209 A JP 2020106209A JP 7469152 B6 JP7469152 B6 JP 7469152B6
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- substituted
- unsubstituted
- organic electroluminescent
- aryl
- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims description 101
- -1 cyano, carboxyl Chemical group 0.000 claims description 214
- 239000000463 material Substances 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 57
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 34
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000010410 layer Substances 0.000 description 126
- 238000002347 injection Methods 0.000 description 31
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- 230000005525 hole transport Effects 0.000 description 21
- 239000002019 doping agent Substances 0.000 description 19
- 230000000903 blocking effect Effects 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
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- 238000001771 vacuum deposition Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
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- 235000010290 biphenyl Nutrition 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 150000001555 benzenes Chemical class 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
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- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
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- 125000003003 spiro group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
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- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 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 1
- YAVCXSHORWKJQQ-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YAVCXSHORWKJQQ-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
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- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
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- 238000007341 Heck reaction Methods 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
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- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 230000006798 recombination Effects 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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Description
Ar1は、置換若しくは非置換(C6~C30)アリール、又は置換若しくは非置換(5~30員)ヘテロアリールを表し;
R5及びR6は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1~C30)アルキル、置換若しくは非置換(C6~C30)アリール、又は置換若しくは非置換(5~30員)ヘテロアリールを表し;
Ar2は、
ここで、Ar2は、位置R1~R4の1つで
a及びdは、それぞれ独立して、1~3の整数を表し、b、c、e及びfは、それぞれ独立して、1~4の整数を表し;
式中、a~fが2以上の整数である場合、各R1~各R6は、互いに同じものであっても、異なってもよい。
本開示による有機エレクトロルミネセント化合物を使用することによって、改善された駆動電圧及び/又は電流効率特性を有する有機エレクトロルミネセントデバイスを製造することが可能である。
R1~R6、Ar1、及びa~fは、式1において定義された通りである、但し、dは、式1-1において1又は2であり、bは、式1-2において1、2又は3である)
で表され得る。
Ar41は、置換若しくは非置換(C6~C50)アリール又はスチリルを表し;Laは、単結合、置換若しくは非置換(C6~C30)アリーレン、又は置換若しくは非置換(3~30員)ヘテロアリーレンを表し;Ar42及びAr43は、それぞれ独立して、水素、重水素、ハロゲン、置換若しくは非置換(C1~C30)アルキル、置換若しくは非置換(C6~C30)アリール、又は置換若しくは非置換(3~30員)ヘテロアリールを表すか;或いは隣接置換基と結合して(3~30員)の単環式若しくは多環式の脂環式、芳香族又はそれらの組み合わせの環を形成し得、ここで、形成された脂環式、芳香族又はそれらの組み合わせの炭素原子は、N、O、及びSから選択される1つ以上のヘテロ原子で置き換えられ得;jjは、1又は2であり、jjが2である場合、各
化合物9-ブロモアントラセン(20g、0.077mol)、化合物B-4(25.1g、0.085mol)、Pd(PPh3)4(4.5g、0.003mol)、K2CO3(32g、0.23mol)、97mLのエタノール、97mLの蒸留水、及び390mLのトルエンをフラスコに添加し100℃で撹拌した。12時間後に、混合物を室温に冷却し、ジクロロメタンで抽出し、有機層を蒸留水で洗浄した。得られた有機層を減圧下に蒸留し、カラムクロマトグラフィーによって分離して化合物B-3(25.8g、96.6%)を得た。
化合物B-3(25.8g、0.074mol)をフラスコに添加し、374mLのジメチルホルムアミド(DMF)に溶解させ、N-ブロムスクシンイミド(13.3g、0.074mol)をそれに添加した。混合物を室温で18時間撹拌し、ジクロロメタンで抽出し、有機層を蒸留水で洗浄した。得られた有機層を減圧下に蒸留し、カラムクロマトグラフィーによって分離して化合物B-2(30g、94.6%)を得た。
化合物B-2(30g、0.070mol)をフラスコに添加し、700mLのテトラヒドロフランをそれに添加した。n-BuLi(37mL、2.5M、0.092mol)を-78℃でゆっくり添加した。10分後に、トリメチルボレート(10.3mL、0.092mol)をそれに添加した。混合物を12時間撹拌した後、蒸留水をそれに添加した。有機層を酢酸エチルで抽出し、残りの水分を硫酸マグネシウムで除去した。有機層を減圧下に蒸留し、ヘキサンを添加することによって固化させて化合物B-1(16g、58.8%)を得た。
化合物A-1(6g、0.016mol)、化合物B-1(8.4g、0.021mol)、Pd(PPh3)4(0.97g、0.00084mol)、K2CO3(6.9g、0.050mol)、20mLのエタノール、20mLの蒸留水、及び84mLのトルエンをフラスコに添加し、混合物を130℃で撹拌した。16時間後に、混合物を室温に冷却し、酢酸エチルで抽出し、有機層を蒸留水で洗浄した。得られた有機層を減圧下に蒸留し、カラムクロマトグラフィーによって分離して化合物C-35(5.5g、52.7%)を得た。
本開示による有機エレクトロルミネセント化合物を使用するOLEDを以下の通り製造した:OLED用のガラス基板上の透明電極酸化インジウムスズ(ITO)薄膜(10Ω/sq)(ジオマテック株式会社、日本)を、順次、アセトン、エタノール、及び蒸留水での超音波洗浄にかけ、その後イソプロパノール中に保存した。ITO基板を真空蒸着装置の基板ホルダーに装着した。化合物HI-1を真空蒸着装置のセルに導入し、装置のチャンバー中の圧力を10-6トールに制御した。その後、セルに電流を流して上記導入された物質を蒸発させ、それによってITO基板上に60nmの厚さを有する第1正孔注入層を形成した。次に、化合物HI-2を真空蒸着装置の別のセルに導入し、セルに電流を流すことによって蒸発させ、それによって第1正孔注入層上に5nmの厚さを有する第2正孔注入層を形成した。次いで、化合物HT-1を真空蒸着装置の別のセルに導入し、セルに電流を流すことによって蒸発させ、それによって第2正孔注入層上に20nmの厚さを有する第1正孔輸送層を形成した。次いで、化合物HT-2を真空蒸着装置の別のセルに導入し、セルに電流を流すことによって蒸発させ、それによって第1正孔輸送層上に5nmの厚さを有する第2正孔輸送層を形成した。正孔注入層及び正孔輸送層を形成した後、発光層をその上に以下の通り形成した:化合物C-1を発光層のホストとして真空蒸着装置の1つのセルに導入し、化合物BDを別のセルに導入した。2つの物質を異なる速度で蒸発させ、ドーパントを、ホストとドーパントの総量を基準として2重量%のドープ量で蒸着させて、第2正孔輸送上に20nmの厚さを有する発光層を形成した。次に、化合物ET-1及び化合物EI-1を、2つの他のセルにおいて、それぞれ、50重量%の量で1:1の速度で蒸発させて発光層上に35nmの厚さを有する電子輸送層を蒸着させた。電子輸送層上に2nmの厚さを有する電子注入層として化合物EI-1を蒸着させた後、別の真空蒸着装置によって電子注入層上に80nmの厚さを有するAlカソードを蒸着させた。このようにして、OLEDを製造した。
発光層のホスト材料として化合物C-1の代わりに化合物C-35を使用したことを除いて、デバイスの実施例1におけるのと同じ方法でOLEDを製造した。
発光層のホスト材料として化合物C-1の代わりに化合物BH-1を使用したことを除いて、デバイス実施例1におけるのと同じ方法でOLEDを製造した。
Claims (9)
- 次式1:
Ar1は、置換若しくは非置換(C6~C30)アリール、又は置換若しくは非置換(5~30員)ヘテロアリールを表し;
R5及びR6は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1~C30)アルキル、置換若しくは非置換(C6~C30)アリール、又は置換若しくは非置換(5~30員)ヘテロアリールを表し;
Ar2は、
ここで、Ar2は、位置R1~R4の1つで
a及びdは、それぞれ独立して、1~3の整数を表し、b、c、e、及びfは、それぞれ独立して、1~4の整数を表し、
式中、a~fが2以上の整数である場合、各R1~各R6は、互いに同じものであっても、異なってもよい]
で表される有機エレクトロルミネセント化合物。 - R1~R6、及びAr1における前記置換アルキル、前記置換アリール、及び前記置換ヘテロアリールの置換基が、それぞれ独立して、重水素;ハロゲン;シアノ;カルボキシル;ニトロ;ヒドロキシル;(C1~C30)アルキル;ハロ(C1~C30)アルキル;(C2~C30)アルケニル;(C2~C30)アルキニル;(C1~C30)アルコキシ;(C1~C30)アルキルチオ;(C3~C30)シクロアルキル;(C3~C30)シクロアルケニル;(3~7員)ヘテロシクロアルキル;(C6~C30)アリールオキシ;(C6~C30)アリールチオ;非置換の若しくは(C6~C30)アリールで置換された(3~30員)ヘテロアリール;非置換の若しくは重水素、(C1~C30)アルキル及び(3~30員)ヘテロアリールの少なくとも1つで置換された(C6~C30)アリール;トリ(C1~C30)アルキルシリル;トリ(C6~C30)アリールシリル;ジ(C1~C30)アルキル(C6~C30)アリールシリル;(C1~C30)アルキルジ(C6~C30)アリールシリル;アミノ;モノ若しくはジ(C1~C30)アルキルアミノ;モノ若しくはジ(C6~C30)アリールアミノ;(C1~C30)アルキル(C6~C30)アリールアミノ;(C1~C30)アルキルカルボニル;(C1~C30)アルコキシカルボニル;(C6~C30)アリールカルボニル;ジ(C6~C30)アリールボロニル;ジ(C1~C30)アルキルボロニル;(C1~C30)アルキル(C6~C30)アリールボロニル;(C6~C30)アリール(C1~C30)アルキル;及び(C1~C30)アルキル(C6~C30)アリールからなる群から選択される少なくとも1つである、請求項1に記載の有機エレクトロルミネセント化合物。
- Ar1が、非置換の若しくは重水素、(C1~C6)アルキル、(C6~C12)アリール、重水素で置換された(C6~C12)アリール、及び(5~15員)ヘテロアリールから選択される1つ以上で置換された(C6~C24)アリール;又は非置換の若しくは重水素、(C6~C12)アリール、及び重水素で置換された(C6~C12)アリールから選択される1つ以上で置換された(5~20員)ヘテロアリールであり;
R5及びR6が、それぞれ独立して、水素又は重水素である、
請求項1に記載の有機エレクトロルミネセント化合物。 - 請求項1に記載の有機エレクトロルミネセント化合物を含む有機エレクトロルミネセント材料。
- 請求項1に記載の有機エレクトロルミネセント化合物を含む有機エレクトロルミネセントデバイス。
- 前記有機エレクトロルミネセント化合物が発光層に含まれる、請求項8に記載の有機エレクトロルミネセントデバイス。
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JP2019057711A (ja) | 2012-07-20 | 2019-04-11 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | ホスト化合物およびドーパント化合物の新規組み合わせおよびそれを含む有機エレクトロルミネセンスデバイス |
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