JP2018536626A - 新規化合物およびこれを含む有機発光素子 - Google Patents
新規化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2018536626A JP2018536626A JP2018515481A JP2018515481A JP2018536626A JP 2018536626 A JP2018536626 A JP 2018536626A JP 2018515481 A JP2018515481 A JP 2018515481A JP 2018515481 A JP2018515481 A JP 2018515481A JP 2018536626 A JP2018536626 A JP 2018536626A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- 239000010410 layer Substances 0.000 claims description 216
- 238000002347 injection Methods 0.000 claims description 65
- 239000007924 injection Substances 0.000 claims description 65
- 230000005525 hole transport Effects 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000011368 organic material Substances 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000005264 aryl amine group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 150000003974 aralkylamines Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 3
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000151 deposition Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000872 buffer Substances 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- 230000001629 suppression Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 150000002220 fluorenes Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal 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
- 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
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 5
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 3
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 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 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000005266 diarylamine group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- 229940125898 compound 5 Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- FFYZMBQLAYDJIG-UHFFFAOYSA-N dibenzofuran-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3OC2=C1 FFYZMBQLAYDJIG-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 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 2
- 150000002736 metal compounds Chemical class 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 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
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- 229930192474 thiophene Natural products 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-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
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- ZZLQHXCRRMUGQJ-UHFFFAOYSA-N 2'-Hydroxyflavone Natural products OC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 ZZLQHXCRRMUGQJ-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
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- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
[化学式1]
L1〜L3は、直接結合;または2価の連結基であり、
Ar1およびAr2は、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;置換もしくは非置換のアミン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;置換もしくは非置換のフルオレン基および置換もしくは非置換のヘテロ環基からなる群より選択されるいずれか1つであり、
前記L1〜L3、Ar1およびAr2は、隣接する基と互いに結合して置換もしくは非置換の環を形成してもよいし、
nおよびmはそれぞれ、0〜6の整数であり、
o+sは、1〜4の整数であり、
s、pおよびqは、1〜4の整数である。
aは、1〜10の整数であり、
b〜eはそれぞれ、1〜8の整数である。
Ar3は、前記Ar1またはAr2であり、
fは、1〜9の整数であり、
g〜jはそれぞれ、1〜7の整数である。
また、本明細書の一実施態様によれば、R10〜R15は、それぞれ独立に、置換もしくは非置換のアルキル基;および置換もしくは非置換のアリール基からなる群より選択される。
さらに、本明細書の一実施態様によれば、R10〜R15は、それぞれ独立に、アルキル基;およびアリール基からなる群より選択される。
本明細書の一実施態様によれば、前記化学式1において、nおよびmはそれぞれ、0〜6の整数であり、o+sは、1〜4の整数であり、sは、1〜4の整数である。
nまたはmが0の場合には、R1またはR2の置換基は存在せず、水素でのみ置換されたことを意味する。また、コア構造の右側下端のベンゼン環には、R3とLが置換されていてもよいが、これらの置換基の個数が4を超えることができない。さらに、Lは、少なくとも1つ以上が置換されるものを意味し、sが4の場合には、置換基が位置し得るすべての位置にLが置換されたものあり、R3は存在しないことを意味する。
(1)第1電極/正孔輸送層/発光層/第2電極
(2)第1電極/正孔注入層/正孔輸送層/発光層/第2電極
(3)第1電極/正孔注入層/正孔バッファ層/正孔輸送層/発光層/第2電極
(4)第1電極/正孔輸送層/発光層/電子輸送層/第2電極
(5)第1電極/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極
(6)第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/第2電極
(7)第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極
(8)第1電極/正孔注入層/正孔バッファ層/正孔輸送層/発光層/電子輸送層/第2電極
(9)第1電極/正孔注入層/正孔バッファ層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極
(10)第1電極/正孔輸送層/電子抑制層/発光層/電子輸送層/第2電極
(11)第1電極/正孔輸送層/電子抑制層/発光層/電子輸送層/電子注入層/第2電極
(12)第1電極/正孔注入層/正孔輸送層/電子抑制層/発光層/電子輸送層/第2電極
(13)第1電極/正孔注入層/正孔輸送層/電子抑制層/発光層/電子輸送層/電子注入層/第2電極
(14)第1電極/正孔輸送層/発光層/正孔抑制層/電子輸送層/第2電極
(15)第1電極/正孔輸送層/発光層/正孔抑制層/電子輸送層/電子注入層/第2電極
(16)第1電極/正孔注入層/正孔輸送層/発光層/正孔抑制層/電子輸送層/第2電極
(17)第1電極/正孔注入層/正孔輸送層/発光層/正孔抑制層/電子輸送層/電子注入層/第2電極
1−ナフトール(22.26g、154.4mmol)と2−ブロモフルオレン(20g、77.2mmol)を1,2−ジクロロベンゼン(300ml)に添加した後、メタンスルホン酸(10ml)を添加し、160℃で24時間加熱撹拌した。常温に温度を下げて反応を終了した後、クロロホルムと水で抽出した後、テトラヒドロフランとエチルアセテートで再結晶して、前記化合物A1(31.6g、収率80%)を製造した。
MS[M+H]+=512.42
A1(10g、19.55mmol)と、ジ([1,1'−ビフェニル]−4−イル)アミン(6.47g、20.14mmol)、ソジウム−t−ブトキシド(2.6g、27.4mmol)をトルエンに入れて加熱撹拌した後、還流させ、[ビス(トリ−t−ブチルホスフィン)]パラジウム(200mg、2mmol%)を入れる。常温に温度を下げて反応を終了した後、クロロホルムとエチルアセテートを用いて再結晶して、化合物1を製造した。
MS[M+H]+=752.94
前記化合物1の合成において、ジ([1,1'−ビフェニル]−4−イル)アミンの代わりにN−([1,1'−ジフェニル]−4−イル)−9,9−ジメチル−9H−フルオレン−2−アミンを用いたことを除けば同様の方法で合成して、化合物2を製造した。
MS[M+H]+=793.00
前記化合物1の合成において、ジ([1,1'−ビフェニル]−4−イル)アミンの代わりにN−([1,1'−ジフェニル]−4−イル)−[1,1':2',1"−ターフェニル]−4−アミンを用いたことを除けば同様の方法で合成して、化合物3を製造した。
MS[M+H]+=824.03
前記A1の合成において、化合物2−ブロモフルオレンの代わりに3−ブロモフルオレンを用いたことを除けば同様の方法で合成して、化合物A2を製造した。
MS[M+H]+=512.42
A2(10g、19.55mmol)と、N−([1,1'−ジフェニル]−4−イル)ジベンゾ[b,d]フラン−2−アミン(6.75g、20.14mmol)、ソジウム−t−ブトキシド(2.6g、27.4mmol)をトルエンに入れて加熱撹拌した後、還流させ、[ビス(トリ−t−ブチルホスフィン)]パラジウム(200mg、2mmol%)を入れる。常温に温度を下げて反応を終了した後、クロロホルムとエチルアセテートを用いて再結晶して、化合物4を製造した。
MS[M+H]+=766.91
前記化合物4の合成において、N−([1,1'−ジフェニル]−4−イル)ジベンゾ[b,d]フラン−2−アミンの代わりにN−フェニル−[1,1,4',1"−ターフェニル]−4−アミンを用いたことを除けば同様の方法で合成して、化合物5を製造した。
MS[M+H]+=752.93
前記A1の合成において、化合物2−ブロモフルオレンの代わりに4−ブロモフルオレンを用いたことを除けば同様の方法で合成して、化合物A3を製造した。
MS[M+H]+=512.42
A3(10g、19.55mmol)と、ジ([1,1'−ビフェニル]−4−イル)アミン(6.47g、20.14mmol)、ソジウム−t−ブトキシド(2.6g、27.4mmol)をトルエンに入れて加熱撹拌した後、還流させ、[ビス(トリ−t−ブチルホスフィン)]パラジウム(200mg、2mmol%)を入れる。常温に温度を下げて反応を終了した後、クロロホルムとエチルアセテートを用いて再結晶して、化合物6を製造した。
MS[M+H]+=752.94
前記化合物5の合成において、ジ([1,1'−ビフェニル]−4−イル)アミンの代わりにN−([1,1'−ジフェニル]−4−イル)−9,9−ジメチル−9H−フルオレン−2−アミンを用いたことを除けば同様の方法で合成して、化合物7を製造した。
MS[M+H]+=793.00
前記化合物5の合成において、ジ([1,1'−ビフェニル]−4−イル)アミンの代わりにN−([1,1'−ジフェニル]−4−イル)ナフタレン−2−アミンを用いたことを除けば同様の方法で合成して、化合物8を製造した。
MS[M+H]+=726.89
ITO(インジウムスズ酸化物)が1,000Åの厚さに薄膜コーティングされたガラス基板(corning 7059 glass)を、分散剤を溶かした蒸留水に入れて超音波洗浄した。洗剤はFischer Co.の製品を使用し、蒸留水はMillipore Co.製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノール溶剤の順に超音波洗浄をし乾燥させた。
[ヘキサニトリルヘキサアザトリフェニレン基] [HT1]
前記実施例1において、正孔輸送層として化合物1の代わりに化合物2を用いたことを除けば、同様に実験した。
前記実施例1において、正孔輸送層として化合物1の代わりに化合物3を用いたことを除けば、同様に実験した。
前記実施例1において、正孔輸送層として化合物1の代わりに化合物4を用いたことを除けば、同様に実験した。
前記実施例1において、正孔輸送層として化合物1の代わりに化合物5を用いたことを除けば、同様に実験した。
前記実施例1において、正孔輸送層として化合物1の代わりにHT1を用いたことを除けば、同様に実験した。
ITO(インジウムスズ酸化物)が1,000Åの厚さに薄膜コーティングされたガラス基板(corning 7059 glass)を、分散剤を溶かした蒸留水に入れて超音波洗浄した。洗剤はFischer Co.の製品を使用し、蒸留水はMillipore Co.製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノール溶剤の順に超音波洗浄をし乾燥させた。
[ヘキサニトリルヘキサアザトリフェニレン基] [HT1]
前記実施例6において、正孔調節層として化合物6の代わりに化合物7を用いたことを除けば、同様に実験した。
前記実施例6において、正孔調節層として化合物6の代わりに化合物8を用いたことを除けば、同様に実験した。
前記実施例6において、正孔調節層として化合物6の代わりに前記[HT2]を用いたことを除けば、同様に実験した。
Claims (13)
- 下記化学式1で表される化合物:
[化学式1]
L1〜L3は、直接結合;または2価の連結基であり、
Ar1およびAr2は、それぞれ独立に、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;置換もしくは非置換のアミン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;置換もしくは非置換のフルオレン基および置換もしくは非置換のヘテロ環基からなる群より選択されるいずれか1つであり、
前記L1〜L3、Ar1およびAr2は、隣接する基と互いに結合して置換もしくは非置換の環を形成してもよいし、
nおよびmはそれぞれ、0〜6の整数であり、
o+sは、1〜4の整数であり、
s、pおよびqは、1〜4の整数である。 - 前記L1〜L3は、直接結合;置換もしくは非置換のアルキレン基;置換もしくは非置換のシクロアルキレン基;置換もしくは非置換のアルケニレン基;置換もしくは非置換のアルアルキレン基;置換もしくは非置換のアルアルケニレン基;置換もしくは非置換のアルキルアリーレン基;置換もしくは非置換の2価のアミン基;置換もしくは非置換の2価のアラルキルアミン基;置換もしくは非置換の2価のアリールアミン基;置換もしくは非置換のアリーレン基;および置換もしくは非置換のヘテロ環基からなる群より選択されるいずれか1つである、
請求項1に記載の化合物。 - 前記L1〜L3は、下記化学式のうちのいずれか1つである、
請求項1に記載の化合物:
- 前記Ar1およびAr2は、それぞれ独立に、置換もしくは非置換のアリール基;置換もしくは非置換のフルオレン基;および置換もしくは非置換のヘテロ環基からなる群より選択されるいずれか1つである、
請求項1から3のいずれか1項に記載の化合物。 - 前記Ar1およびAr2が互いに結合して形成する置換もしくは非置換の環は、下記化学式のうちのいずれか1つである、
請求項1から3のいずれか1項に記載の化合物:
aは、1〜10の整数であり、
b〜eはそれぞれ、1〜8の整数である。 - 前記L1〜L3および、Ar1またはAr2が互いに結合して形成する置換もしくは非置換の環は、下記化学式のうちのいずれか1つである、
請求項1に記載の化合物:
Ar3は、前記Ar1またはAr2であり、
fは、1〜9の整数であり、
g〜jはそれぞれ、1〜7の整数である。 - 前記化合物は、下記化学式のうちのいずれか1つである、
請求項1に記載の化合物:
- 第1電極と、
前記第1電極に対向して備えられた第2電極と、
前記第1電極と前記第2電極との間に備えられた1層以上の有機物層と
を含む有機発光素子であって、
前記有機物層のうちの1層以上は、請求項1〜7のいずれか1項に記載の化合物を含むものである
有機発光素子。 - 前記有機物層は、前記化合物単独からなるか、または前記化合物がドーピングされてなるものである、
請求項8に記載の有機発光素子。 - 前記有機物層は、正孔注入層、正孔輸送層、電子輸送層、または電子注入層である、
請求項8または9に記載の有機発光素子。 - 前記有機物層は、正孔注入および正孔輸送を同時に行う層である、
請求項8から10のいずれか1項に記載の有機発光素子。 - 前記有機物層は、電子輸送および電子注入を同時に行う層である、
請求項8から11のいずれか1項に記載の有機発光素子。 - 前記有機物層は、発光層である、
請求項8から12のいずれか1項に記載の有機発光素子。
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