WO2011093056A1 - トリフェニルアミン構造を有する化合物および有機エレクトロルミネッセンス素子 - Google Patents
トリフェニルアミン構造を有する化合物および有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2011093056A1 WO2011093056A1 PCT/JP2011/000376 JP2011000376W WO2011093056A1 WO 2011093056 A1 WO2011093056 A1 WO 2011093056A1 JP 2011000376 W JP2011000376 W JP 2011000376W WO 2011093056 A1 WO2011093056 A1 WO 2011093056A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 125000006617 triphenylamine group Chemical group 0.000 title claims abstract description 25
- -1 arylamine compound Chemical class 0.000 claims abstract description 124
- 239000000463 material Substances 0.000 claims abstract description 63
- 238000002347 injection Methods 0.000 claims abstract description 28
- 239000007924 injection Substances 0.000 claims abstract description 28
- 239000012044 organic layer Substances 0.000 claims abstract description 24
- 239000000470 constituent Substances 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 133
- 125000004431 deuterium atom Chemical group 0.000 claims description 82
- 229910052805 deuterium Inorganic materials 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 230000005525 hole transport Effects 0.000 claims description 38
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 35
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 238000005401 electroluminescence Methods 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical group N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 238000003763 carbonization Methods 0.000 claims 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 16
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 8
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- 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 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 7
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- 239000006185 dispersion Substances 0.000 description 7
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 125000003226 pyrazolyl group Chemical group 0.000 description 7
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 6
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- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000005428 anthryl 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 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 5
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 5
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 1
- ZVSKZLHKADLHSD-OUHXUHDZSA-N n-(2,3,4,5,6-pentadeuteriophenyl)benzamide Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1NC(=O)C1=CC=CC=C1 ZVSKZLHKADLHSD-OUHXUHDZSA-N 0.000 description 1
- 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 1
- 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 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 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
- 150000003967 siloles Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 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 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
Images
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
Definitions
- the present invention relates to a compound suitable for an organic electroluminescence element (hereinafter abbreviated as an organic EL element) which is a self-luminous element suitable for various display devices, and the element, and more specifically, a triphenylamine structure. And an organic EL device using the compound.
- an organic electroluminescence element hereinafter abbreviated as an organic EL element
- organic EL elements are self-luminous elements, they have been actively researched because they are brighter and more visible than liquid crystal elements and are capable of clear display.
- the light emitting layer can also be prepared by doping a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
- a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
- the light injected from both electrodes is recombined in the light emitting layer to obtain light emission, but it is important how to efficiently transfer both holes and electrons to the light emitting layer, Improve the probability of recombination of holes and electrons by increasing the hole injection property and blocking the electrons injected from the cathode, and confine excitons generated in the light-emitting layer. Therefore, 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. There is also a need for a hole transport material that has a stable thin film and high heat resistance.
- JP-A-8-048656 Japanese Patent No. 3194657 Special table No. 2008-532998 JP 2009-231516 A JP-A-7-126615
- the object of the present invention is as a highly efficient and durable organic EL device material with excellent hole injection / transport performance, electron blocking ability, high stability in a thin film state, and heat resistance.
- An object of the present invention is to provide an organic compound having excellent characteristics, and to provide a highly efficient and highly durable organic EL device using this compound.
- the physical characteristics that the organic compound to be provided by the present invention should have include (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. It can be mentioned that the voltage is low.
- the present inventors have high hole injection / transport capability of the triphenylamine structure, and heat resistance and thin film stability due to substitution with deuterium atoms.
- the present invention is an arylamine compound having a structure in which two triphenylamine structures represented by the following general formula (1) are linked by a single bond or a divalent group not containing a hetero atom.
- R1 to R28 may be the same or different, and a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a nitro group, or a carbon atom which may have a substituent
- R29 to R32 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R33 to R42 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R43 to R50 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R51 to R55 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- the present invention is an arylamine compound having a structure in which four triphenylamine structures represented by the following general formula (2) are connected by a single bond or a divalent group not containing a hetero atom.
- R56 to R109 may be the same or different, and a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, nitro group, or optionally substituted carbon atom
- R29 to R32 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R33 to R42 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R43 to R50 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- R51 to R55 may be the same or different and each represents a hydrogen atom or a deuterium atom.
- the present invention provides an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the arylamine compound represented by the general formula (1) or the general formula (2) is at least It is an organic electroluminescent element characterized by being used as a constituent material of one organic layer.
- the “optionally substituted cycloalkyl group having 5 to 10 carbon atoms” or the “optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms” "C1-C6 linear or branched alkyl group", “C5-C10 cycloalkyl group” or "C2-C6 linear or branched alkenyl group”
- a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R1 to R28 or R56 to R109 in the general formulas (1) and (2), “having a substituent
- substituents in the “cycloalkyl group having 5 to 10 carbon atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, Trifluoromethyl group, 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, n-butyl group, isobutyl group, tert
- a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent represented by R1 to R28 or R56 to R109 in the general formulas (1) and (2)
- a linear or branched alkyloxy group having 1 to 6 carbon atoms in “optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms” or “5 to 5 carbon atoms”.
- cycloalkyloxy groups specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyl Oxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamanti Such oxy group and a 2-adamantyl group can be cited. These substituents may be bonded to each other to form a ring.
- a linear or branched alkyl group having 1 to 6 carbon atoms; 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, and a propyloxy group Linear or branched alkoxy groups; alkenyl groups such as allyl groups; aralkyl groups such as benzyl groups, naphthylmethyl groups and phenethyl groups; aryloxy groups such as phenoxy groups and tolyloxy groups; benzyloxy groups and phenethyloxy groups
- 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 R1 to R28 or R56 to R109 in the general formulas (1) and (2)
- substituted specifically, deuterium atom, cyano group, trifluoromethyl group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n- Linear or branched having 1 to 6 carbon atoms such as propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.
- Alkyl group cycloalkyl group having 5 to 10 carbon atoms such as cyclopentyl group and cyclohexyl group; vinyl group, allyl group, 2-butenyl group, 1-hexenyl group, etc.
- aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R1 to R28 or R56 to R109 in the general formulas (1) and (2) include a phenoxy group and a tolyloxy group. And biphenylyloxy group, terphenylyloxy group, naphthyloxy group, anthryloxy group, phenanthryloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, and the like. These substituents may be bonded to each other to form a ring.
- substituted aryloxy group represented by R1 to R28 or R56 to R109 in the general formulas (1) and (2)
- substituents in the “substituted aryloxy group” represented by R1 to R28 or R56 to R109 in the general formulas (1) and (2) include a deuterium atom, a cyano group, and trifluoromethyl.
- a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group or a propyloxy group; a cycloalkyl having 5 to 10 carbon atoms such as a cyclopentyloxy group or a cyclohexyloxy group Oxy group; aralkyl group such as benzyl group, naphthylmethyl group, phenethyl group; phenoxy group, tolyloxy group, biphenylyloxy group, terphenylyloxy group, naphthyloxy group, anthryloxy group, phenanthryloxy group, full Aryloxy group such as oleenyloxy group, indenyloxy group, pyrenyloxy group and perylenyloxy group; arylalkoxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naph
- the arylamine compound represented by the general formula (1) is preferably an arylamine compound represented by the following general formula (1 ′) or the following general formula (1 ′′) for use in an organic EL device.
- n1 to n4 may be the same or different and represent 0 or 5
- m1 and m2 may be the same or different and represent 0 or 4
- the arylamine compound represented by the general formula (2) is preferably an arylamine compound represented by the following general formula (2 ') for use in an organic EL device.
- At least one of R1 to R109 in the general formula (1) or (2) is preferably a deuterium atom or a substituent containing a deuterium atom, and contains a deuterium atom or a deuterium atom. More substituents are more preferable.
- all of R1 to R5, all of R6 to R10, all of R11 to R14, all of R15 to R18, all of R19 to R23, or all of R24 to R28 are deuterium atoms.
- the substituents R1 to R109 are all substituted with deuterium atoms except for the bonding position with the triphenylamine structure, aromatic hydrocarbon group, aromatic It is preferably a heterocyclic group, a condensed polycyclic aromatic group or an aryloxy group.
- A1 or A2 in the general formula (1) or (2) is represented by the structural formula (B), (C), (D) or (F), all of R29 to R32, R33 to R42 It is preferable that all of R43 to R46, all of R47 to R50, or all of R51 to R55 are substituted with deuterium atoms.
- the arylamine compound having a triphenylamine structure represented by the general formula (1) or (2) of the present invention is a novel compound, and has a thin film state stability and heat resistance equal to or higher than those of conventional hole transport materials. It has sex.
- the arylamine compound having a triphenylamine structure represented by the general formula (1) or (2) of the present invention is a constituent material of a hole injection layer and / or a hole transport layer and an electron blocking layer of an organic EL device.
- a compound having a substituted anthracene ring structure and a pyridoindole ring structure represented by the following general formula (3) is preferably used as a constituent material of the electron transport layer.
- Ar1 and Ar2 may be the same or different, and Ar1 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
- Ar2 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted condensed polycyclic aromatic group, and B and C may be the same or different, and may be a single bond, substituted or unsubstituted.
- Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic represented by Ar1 in general formula (3)
- aromatic hydrocarbon group “aromatic heterocyclic group” or “condensed polycyclic aromatic group” of the “group”
- phenyl group biphenylyl group, terphenylyl group, tetrakisphenyl group, styryl group, naphthyl group Group, anthryl group, acenaphthenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, pyridyl group, triazyl group, pyrimidyl group, furanyl group, pyronyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group,
- the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar1 in the general formula (3) is specifically Deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, hydroxyl group, nitro group, linear or branched alkyl group having 1 to 6 carbon atoms, cyclopentyl group, cyclohexyl group, carbon atom A linear or branched alkoxy group having 1 to 6 carbon atoms, a dialkylamino group substituted with a linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, anthryl group, fluorenyl group , A styryl group, a pyridyl group, a pyridoindolyl group, a quinolyl group, a benzothi
- Specific examples of the “polycyclic aromatic group” include groups such as a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, an indenyl group, and a pyrenyl group.
- substituted aromatic hydrocarbon group or “substituted condensed polycyclic aromatic group” represented by Ar 2 in the general formula (3), specifically, a deuterium atom, a fluorine atom, A chlorine atom, a cyano group, a trifluoromethyl group, a hydroxyl group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, a cyclopentyl group, a cyclohexyl group, a straight chain having 1 to 6 carbon atoms or Branched alkoxy group, dialkylamino group substituted with linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group, naphthyl group, anthryl group, fluorenyl group, styryl group, pyridyl group, pyridoin
- Examples thereof include a drill group, a quinolyl group, and a benzo
- substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R110 to R116 in the general formula (3)
- deuterium atom fluorine atom, chlorine atom, trifluoromethyl group, linear or branched alkyl group having 1 to 6 carbon atoms, phenyl group, biphenylyl group, terphenylyl group, tetrakisphenyl group, styryl
- examples thereof include a group such as a group, naphthyl group, fluorenyl group, phenanthryl group, indenyl group, pyrenyl group, and pyridoindolyl group, and these substituents may be further substituted.
- linear or branched alkyl group having 1 to 6 carbon atoms represented by R110 to R117 in the general formula (3) include a methyl group, an ethyl group, and an n-propyl group.
- the following groups can be mentioned.
- a divalent group of a substituted or unsubstituted aromatic hydrocarbon "a divalent group of a substituted or unsubstituted aromatic heterocyclic ring” or “substituted or As the “divalent group of aromatic hydrocarbon”, “divalent group of aromatic heterocycle” or “divalent group of condensed polycyclic aromatic” in the “unsubstituted fused polycyclic aromatic divalent group”, Specifically, phenylene group, biphenylylene group, terphenylylene group, tetrakisphenylene group, naphthylene group, anthrylene group, phenanthrylene group, fluorenylene group, phenanthrolylene group, indenylene group, pyrenylene group, pyridinylene group, pyrimidinylene group, quinolylene group, Isoquinolylene group, indolylene group, carbazolylene group, quinoxarylene group
- the arylamine compound having a triphenylamine structure represented by the general formula (1) or (2) of the present invention is useful as a constituent material of a hole injection layer, a hole transport layer, and an electron blocking layer of an organic EL device. It has a high hole injecting / transporting ability, excellent electron blocking ability, stable thin film state, and excellent heat resistance.
- the organic EL device of the present invention has high luminous efficiency and high power efficiency, which can reduce the practical driving voltage of the device. Furthermore, the light emission starting voltage can be lowered and the durability can be improved. And the element lifetime of an organic EL element can be improved dramatically. Further, as a constituent material of the electron transport layer, a substituted compound represented by the general formula (3) was used.
- FIG. 1 is a 1H-NMR chart of the compound of Example 1 of the present invention (Compound 5).
- FIG. 3 is a 1H-NMR chart of the compound of Example 2 of the present invention (Compound 49).
- FIG. 3 is a 1H-NMR chart of the compound of Example 3 of the present invention (Compound 18).
- FIG. 3 is a 1H-NMR chart of the compound of Example 4 of the present invention (Compound 19).
- FIG. 6 is a 1H-NMR chart of the compound of Example 5 of the present invention (Compound 20).
- FIG. 6 is a 1H-NMR chart of the compound of Example 6 of the present invention (Compound 21).
- FIG. 6 is a 1H-NMR chart of the compound of Example 7 of the present invention (Compound 40).
- FIG. 6 is a diagram showing EL element configurations of Examples 11 to 14 and Comparative Example 2.
- FIG. 6 is a diagram showing EL device configurations of Examples 15 to 18 and Comparative Example 3.
- the arylamine compound having a triphenylamine structure of the present invention is a novel compound and can be synthesized by a known method (for example, see Patent Documents 1 and 5) using a deuterated raw material.
- Tg glass transition point
- work function index of hole transportability
- the glass transition point (Tg) was determined with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
- the work function was measured using an atmospheric photoelectron spectrometer AC-2 manufactured by Riken Keiki Co., Ltd. after a 100 nm thin film was formed on the ITO substrate.
- the structure of the organic EL device of the present invention includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and between the anode and the hole transport layer. And those having an electron injection layer between the electron transport layer and the cathode.
- these multilayer structures several organic layers can be omitted.
- a structure having an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on a substrate can be used. .
- an electrode material having a large work function such as ITO or gold is used.
- a hole injection layer of the organic EL device of the present invention in addition to the arylamine compound having a triphenylamine structure represented by the general formula (1) or (2) of the present invention, a porphyrin compound represented by copper phthalocyanine, Materials such as starburst type triphenylamine derivatives and various triphenylamine tetramers, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating type polymer materials 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.
- N, N′-diphenyl-N, N'-di (m-tolyl) benzidine hereinafter abbreviated as TPD
- NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) benzidine
- NPD N, N , N ′, N′-tetrabiphenylylbenzidine and other benzidine derivatives
- 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane hereinafter abbreviated as TAPC
- various amounts of triphenylamine Bodies, tetramers and the like can be used.
- PEDOT poly (3,4-ethylenedioxythiophene)
- PSS poly (styrene sulfonate)
- a material that is usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the like, or a TPD structure having a partial structure. Molecular compounds and the like can be used.
- TCTA N-carbazolyl triphenylamine
- Ad-Cz 1,3-bis (carbazol-9-yl) benzene
- Ad-Cz Carbazole derivatives such as 2,2-bis (4-carbazol-9-ylphenyl) adamantane
- Phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene a compound having a triphenylsilyl group and a triarylamine structure. It may be a compound having the electron blocking action. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with 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.
- 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 such as Alq 3 Can be used.
- the light emitting layer may be composed of a host material and a dopant material, and in addition to the light emitting material, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used as the host material.
- quinacridone coumarin, rubrene, perylene, and derivatives thereof
- benzopyran derivatives rhodamine derivatives, aminostyryl derivatives, and the like
- These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
- a phosphorescent light emitting material can be used as the light emitting material.
- 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, and red phosphorescent emitters
- Btp 2 Ir (acac) are used as the host material.
- carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, and the like can be used.
- p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) represented by the following formula -Tris (1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like can be used.
- 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.
- 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.
- phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
- BCP bathocuproine
- BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
- BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
- various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
- These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with 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.
- various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, in addition to metal complexes of quinolinol derivatives including Alq 3 and BAlq.
- Derivatives, phenanthroline derivatives, silole derivatives and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with 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.
- 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.
- Tetrakis (triphenylphosphine) palladium 2.28 g was added and heated, followed by stirring under reflux for 7.5 hours. After allowing to cool to room temperature, a liquid separation operation was performed to collect the organic layer. The organic layer was dried over magnesium sulfate and then concentrated to obtain 22.27 g of a black crude product.
- the crude product was purified by column chromatography (carrier: silica gel, eluent: n-hexane) by performing afforded white crystals 14.07g biphenyl -d 10 (86% yield).
- the mixture was stirred at 210 ° C. for 26.5 hours. After cooling to 100 ° C. and adding 70 ml of toluene, the mixture was further cooled to room temperature, and the precipitated solid was collected by filtration. After dispersion washing by adding 200 ml of water and 20 ml of methanol, 3.2 L of o-dichlorobenzene was added and heated to 100 ° C. to dissolve. The insoluble material was removed by filtration, the filtrate was concentrated, and recrystallization with o-dichlorobenzene was repeated 4 times. Further, 300 ml of methanol was added and stirred for 1 hour while heating to reflux.
- N-[(4′-iodo) biphenyl-4-yl] -N- (phenyl-d 5 ) -benzamide 33.43 g, diphenylamine 14.13 g, copper powder 0.45 g, potassium carbonate 14.43 g, Sodium hydrogen sulfite 1.08 g and dodecylbenzene 56 ml were added to a nitrogen-substituted reaction vessel and heated. The mixture was stirred at 210 ° C. for 7.5 hours while adding 0.45 g of copper powder and 0.96 g of potassium carbonate, respectively. After cooling to 80 ° C. and adding 500 ml of toluene, the mixture was further cooled to 60 ° C.
- the insoluble material was removed by filtration, then concentrated and added to another reaction vessel.
- Potassium hydroxide (9.76 g), water (11 ml) and isoamyl alcohol (49 ml) were added, and the mixture was stirred for 3 hours while heating. After allowing to cool to room temperature, 500 ml of toluene and 500 ml of water were added and stirred, and a liquid separation operation was performed to collect the organic layer. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. A crude product was obtained by adding 400 ml of hexane and collecting the precipitated solid by filtration.
- Example 8 About the comparative compounds 50, 51, and 52 which are not substituted by the corresponding deuterium atom with the compound of this invention, the glass transition point was calculated
- the compound of the present invention has a glass transition point of 90 ° C. or higher, which indicates that the thin film state is stable in the compound of the present invention.
- the compounds of Examples 1 and 2 of the present invention have almost the same glass transition point as that of the comparative compound 50 that is not substituted with the corresponding deuterium atom.
- the compounds of Examples 3 to 6 of the present invention have almost the same glass transition point as that of the comparative compound 51 which is not substituted with the corresponding deuterium atom.
- the compound of Inventive Example 7 has almost the same glass transition point as that of the comparative compound 52 not substituted with the corresponding deuterium atom.
- Example 9 Using the compound of the present invention, a deposited film having a thickness of 100 nm was formed on an ITO substrate, and the work function was measured with an atmospheric photoelectron spectrometer (AC-2 type, manufactured by Riken Keiki Co., Ltd.). Work function Compound of Example 1 of the present invention 5.47 eV Inventive Example 2 compound 5.51 eV Comparative compound 50 5.46 eV Inventive Example 3 Compound 5.43 eV Inventive Example 4 Compound 5.44 eV Inventive Example 5 compound 5.43 eV Inventive Example 6 Compound 5.42 eV Comparative compound 51 5.45 eV Inventive Example 7 Compound 5.43 eV Comparative Compound 52 5.44 eV
- the compound of the present invention exhibits a suitable energy level as compared with the work function 5.4 eV of general hole transport materials such as NPD and TPD, and has a good hole transport capability.
- the compounds of Examples 1 and 2 of the present invention have substantially the same energy level as that of the comparative compound 50 not substituted with the corresponding deuterium atom.
- the compounds of Examples 3 to 6 of the present invention have almost the same energy level as that of the comparative compound 51 that is not substituted with the corresponding deuterium atom.
- the compound of Inventive Example 7 has almost the same energy level as that of the comparative compound 52 not substituted with the corresponding deuterium atom.
- the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2 as shown in FIG. 7, an electron injection layer 8 and a cathode (aluminum electrode) 9 were deposited in this order.
- the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, the compound 52 having the above structural formula was formed to a thickness of 20 nm as the hole injection layer 3 so as to cover the transparent anode 2. On this hole injection layer 3, the compound (compound 5) of Example 1 of the present invention was formed as a hole transport layer 4 so as to have a film thickness of 40 nm.
- a film thickness of 30 nm On this emitting layer 5 was formed to have the Alq 3 film thickness 30nm as the electron transport layer 7.
- lithium fluoride was formed as the electron injection layer 8 so as to have a film thickness of 0.5 nm.
- aluminum was deposited to a thickness of 150 nm to form the cathode 9.
- the characteristic measurement was performed at normal temperature in air
- Example 10 For comparison, in Example 10, except that the comparative compound 50 was formed so as to have a film thickness of 40 nm instead of the compound of Example 1 of the present invention (Compound 5) as the material of the hole transport layer 4.
- the organic EL element was produced under the conditions described above. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- the driving voltage when a current having a current density of 10 mA / cm 2 was passed was 4.97 V of Comparative Compound 50, while that of Compound (Compound 5) of Example 1 of the present invention was 5. Although it is almost the same value as 02V, the luminous efficiency is greatly improved to 9.00 cd / A in the compound of Example 1 (Compound 5) of 8.53 cd / A in Comparative Compound 50. The power efficiency was also improved to 5.60 lm / W in the compound of Example 1 (Compound 5) of 5.40 lm / W of Comparative Compound 50.
- the organic EL device using the arylamine compound having the triphenylamine structure of the present invention is compared with the organic EL device using the comparative compound 50 not substituted with a known deuterium atom. Even so, it has been found that the luminous efficiency and power efficiency can be improved.
- the organic EL element has a hole transport layer 4, a light emitting layer 5, an electron transport layer 7 and an electron injection layer 8 on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
- the cathode (aluminum electrode) 9 was deposited in this order.
- the compound of Example 1 of the present invention (Compound 5) was formed to a film thickness of 60 nm as the hole transport layer 4 so as to cover the transparent electrode 2.
- the compound 55 of the following structural formula was formed as the electron carrying layer 7 so that it might become a film thickness of 30 nm.
- the electron transport layer 7 lithium fluoride was formed as the electron injection layer 8 so as to have a film thickness of 0.5 nm.
- aluminum was deposited to a thickness of 150 nm to form the cathode 9.
- the characteristic measurement was performed at normal temperature in air
- Table 2 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the organic EL device produced using the compound of Example 1 (Compound 5) of the present invention.
- Example 12 In Example 11, the compound (Compound 19) of Example 4 of the present invention was formed so as to have a film thickness of 60 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material for the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 13 In Example 11, the compound (Compound 21) of Example 6 of the present invention was formed so as to have a film thickness of 60 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material for the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 14 In Example 11, except that the compound (Compound 40) of Example 7 of the present invention was formed to a film thickness of 60 nm in place of the compound (Compound 5) of Example 1 of the present invention as the material for the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 11 For comparison, in Example 11 except that the comparative compound 50 was formed so as to have a film thickness of 60 nm instead of the compound of Example 1 of the present invention (Compound 5) as the material of the hole transport layer 4.
- the organic EL element was produced under the conditions described above. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- the organic EL device using the compound of the example of the present invention is a comparative compound 50 in any of driving voltage, light emission efficiency, and power efficiency when a current density of 10 mA / cm 2 is passed. It can be seen that the performance is equivalent to or better than that of an organic EL device using the above.
- Table 3 summarizes the results of measuring element lifetime using the same organic EL elements as in Example 11 and Comparative Example 2.
- the lifetime of the element is measured by measuring the time when the luminance is attenuated to 97 when the initial luminance is 100 with respect to the emission luminance when the current amount (W) when emitting light at 350 cd / m 2 is constant. Asked.
- the device lifetime of the organic EL device using the compound of Example 1 of the present invention is that of the organic EL device using the comparative compound 50 not substituted with deuterium atoms.
- the life has been significantly extended.
- Table 4 summarizes the results of measuring the element lifetime using the same organic EL elements as in Examples 11 to 14 and Comparative Example 2.
- the element lifetime is the time when the luminance is attenuated to 50 when the initial luminance is 100 with respect to the emission luminance when the current amount (W) when emitting light at a luminance of 5000 cd / m 2 is constant (luminance half-life). ) was measured.
- the device lifetime of the organic EL device using the compound of the example of the present invention is longer than that of the organic EL device using the comparative compound 50 not substituted with deuterium atoms.
- the organic EL element has a hole transport layer 4, a light emitting layer 5, a hole blocking layer 6, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2. 7, an electron injection layer 8 and a cathode (aluminum electrode) 9 were deposited in this order.
- the film was formed to a thickness of 20 nm.
- BCP was formed as a hole blocking layer 6 so as to have a film thickness of 10 nm.
- Alq 3 was formed as an electron transport layer 7 so as to have a film thickness of 30 nm.
- lithium fluoride was formed as the electron injection layer 8 so as to have a film thickness of 0.5 nm.
- aluminum was deposited to a thickness of 150 nm to form the cathode 9.
- the characteristic measurement was performed at normal temperature in air
- Example 16 In Example 15, except that instead of the compound (Compound 5) of Example 1 of the present invention as the material for the hole transport layer 4, the compound (Compound 19) of Example 4 of the present invention was formed to a film thickness of 50 nm. An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 17 In Example 15, except that the compound (Compound 21) of Example 6 of the present invention was formed to have a film thickness of 50 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material of the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 18 In Example 15, except that the compound (Compound 40) of Example 7 of the present invention was formed so as to have a film thickness of 50 nm instead of the compound (Compound 5) of Example 1 of the present invention as the material of the hole transport layer 4.
- An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- Example 15 For comparison, in Example 15, except that the comparative compound 50 was formed so as to have a film thickness of 50 nm instead of the compound of Example 1 of the present invention (Compound 5) as the material of the hole transport layer 4.
- the organic EL element was produced under the conditions described above. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
- the organic EL device using the compound of the example of the present invention has the comparative compound 50 in any of the driving voltage, the light emission efficiency, and the power efficiency when a current density of 10 mA / cm 2 is passed. It can be seen that the performance is equal to or better than the organic EL element used.
- the organic EL device using the compound of the example of the present invention has a current density of 10 mA / in comparison with the organic EL device using the comparative compound 50 not substituted with deuterium atoms. It was found that the driving voltage, the light emission efficiency, and the current efficiency when a current of cm 2 was passed showed the same or better performance.
- the organic EL device using the arylamine compound having the triphenylamine structure of the present invention is compared with the organic EL device using the comparative compound 50 not substituted with a known deuterium atom.
- improvement in device performance such as drive voltage, light emission efficiency, and power efficiency can be expected, and that further improvement in device life can be achieved.
- the arylamine compound having a triphenylamine structure of the present invention is excellent as a compound for an organic EL device because it has a high hole injection / transport capability, an electron blocking capability, and a stable thin film state.
- an organic EL device using the compound, high light emission efficiency and power efficiency can be obtained, and the device life can be significantly extended. For example, it has become possible to develop home appliances and lighting.
Abstract
Description
また、発光効率のさらなる向上を目的として三重項励起子の利用が試みられ、燐光発光体の利用が検討されている(例えば、非特許文献3参照)。
また、薄膜が安定で耐熱性が高い正孔輸送材料が求められている。
これは、重水素原子で置換された場合、励起子の形成が容易になることによって発光効率が高くなるということを応用したものである。しかしながら、このことは、発光層の材料に対してはいえるが、正孔輸送層の材料に対しては当てはまらず、したがって正孔輸送層の材料に応用した例は知られていなかった。
尚、下記構造式では、水素原子は省略して記載している。
<4,4’-ビス〔(ビフェニル-4-イル)-(フェニル-d5)-アミノ〕ビフェニル(化合物5)の合成>
窒素置換した反応容器に、アニリン-2,3,4,5,6-d530.00g、酢酸50mlを加え、攪拌しながら70℃まで加熱した後、無水酢酸34.7mlを滴下し、さらに70℃で4時間撹拌した。室温まで冷却した後、反応液を氷水に注加し、析出した結晶をろ別することによって、淡褐色結晶48.71gを得た。一方、ろ液を分液ロートに移し、トルエン1000mlを加えて抽出操作を行い、抽出液を濃縮、乾固することによって褐色結晶4.05gを得た。これらの結晶を合わせ、減圧下で乾燥させてアセトアニリド-2,3,4,5,6-d5の褐色結晶41.33g(収率96.5%)を得た。
ろ液を濃縮した後、窒素置換した反応容器に加え、さらに水酸化カリウム30g、水40ml、イソアミルアルコール61ml加えて加熱し、撹拌しながら、3時間還流した。冷却して析出する粗結晶を、メタノール100mlを用いて洗浄した後、メタノール/水の混合溶媒を加えて加熱し、78℃で1時間撹拌した。析出する結晶をろ過によって採取した後、さらにトルエン/n-ヘキサンを用いた再結晶を行うことによって精製し、(ビフェニル-4-イル)-(フェニル-d5)-アミンの褐色結晶35.78g(収率68.7%)を得た。
<4,4’-ビス{(ビフェニル-d9-4-イル)-フェニルアミノ}ビフェニル(化合物49)の合成>
窒素置換した反応容器に、ブロモベンゼン-d516.08g、(フェニル-d5)ボロン酸13.79g、炭酸カリウム20.46g、水74ml、トルエン160ml、エタノール40mlを加え、超音波を照射しながら30分間窒素ガスを通気した。テトラキス(トリフェニルホスフィン)パラジウム2.28gを加えて加熱し、還流下7.5時間撹拌した。室温まで放冷した後、分液操作を行って有機層を採取し、有機層を硫酸マグネシウムで乾燥した後、濃縮することによって黒色の粗製物22.27gを得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:n-ヘキサン)による精製を行うことによって、ビフェニル-d10の白色結晶14.07g(収率86%)を得た。
<4,4’-ビス{(ビフェニル-4-イル)-[(ビフェニル-2,3,5,6-d4)-4-イル]アミノ}ビフェニル(化合物18)の合成>
窒素置換した反応容器に、(ビフェニル-4-イル)-(フェニル-d5)アミン20.0g、DMF400mlを加えて溶解させた後、氷冷下にて、N-ブロモコハク酸イミド4.7gを加えた。N-ブロモコハク酸イミド9.4gを2回に分けて追加しながら、反応温度を室温まで上げた。3時間撹拌した後、反応溶液を水2000mlに滴下し、析出する固体をろ過によって採取した。得られた固体にトルエン1000mlを加えて溶解した後、硫酸マグネシウムで乾燥し、ろ過操作を行った後に、ろ液を濃縮した。得られた濃縮物にn-ヘキサン200mlを加えて分散洗浄を行い、減圧下、一晩乾燥させることによって、(ビフェニル-4-イル)-4-ブロモ(フェニル-2,3,5,6-d4)アミンの小豆色の固体23.4g(収率89.0%)を得た。
<4,4’-ビス{(ビフェニル-4-イル)-[(ビフェニル-1’,2’,3’,5’,6’-d5)-4-イル]アミノ}ビフェニル(化合物19)の合成>
窒素置換した反応容器に、(ビフェニル-4-イル)-フェニルアミン35.0g、DMF700mlを加えて溶解させた後、氷冷下にて、N-ブロモコハク酸イミド8.5gを加えた。N-ブロモコハク酸イミド17.0gを2回に分けて追加しながら、反応温度を室温まで上げた。25.5時間撹拌した後、反応溶液を水3500mlに滴下し、析出する固体をろ過によって採取した。得られた固体にトルエン2500mlを加えて溶解した後、硫酸マグネシウムで乾燥し、ろ過操作を行った後に、ろ液を濃縮した。得られた濃縮物にn-ヘキサン500mlを加えて分散洗浄を行い、減圧下、一晩乾燥させることによって、(ビフェニル-4-イル)-(4-ブロモフェニル)アミンの小豆色の固体44.1g(収率95.4%)を得た。
<4,4’-ビス{ビス[(ビフェニル-1’,2’,3’,5’,6’-d5)-4-イル]アミノ}ビフェニル(化合物20)の合成>
窒素置換した反応容器に、ビス(4-ブロモフェニル)アミン20.7g、(フェニル-d5)ボロン酸17.0g、リン酸三カリウム53.5g、THF340mlを加え、超音波を照射しながら30分間窒素ガスを通気した。酢酸パラジウム0.7g、トリ(tert-ブチル)ホスフィン1.9gを加え、酢酸パラジウム1.8g、トリ(tert-ブチル)ホスフィン3.8g、リン酸三カリウム53.5gをそれぞれ追加しながら加熱し、60℃で16.5時間攪拌した。室温まで放冷し、不溶物をろ過によって除いた後、濃縮し、トルエンから再結晶することによって固体を得た。減圧下一晩乾燥させることによって、ビス[(ビフェニル-1’,2’,3’,5’,6’-d5)-4-イル]アミンの黒黄色固体8.0g(収率37.7%)を得た。
<4,4’-ビス[ビス(ビフェニル-4-イル)アミノ]ビフェニル-2,3,5,6,2’,3’,5’,6’-d8(化合物21)の合成>
窒素置換した反応容器に、ビス(ビフェニル-4-イル)アミン20.0g、ブロモベンゼン-d510.2g、tert-ブトキシナトリウム9.0g、トルエン150mlを加え、超音波を照射しながら30分間窒素ガスを通気した。酢酸パラジウム0.2g、トリ(tert-ブチル)ホスフィン0.5gを加えて加熱し、90℃で2時間攪拌した。室温まで放冷し、メタノール100mlを加えて分散洗浄を行った後、トルエン102mlを加えて溶解させた。シリカゲル20gを用いた吸着精製を行った後、濃縮した。メタノール100mlを加えて分散洗浄を行った後、減圧下一晩乾燥することによって、N-(フェニル-d5)-ビス(ビフェニル-4-イル)アミンの白色固体20.1g(収率80.1%)を得た。
<4,4’-ビス{[(4’-ジフェニルアミノ)ビフェニル-4-イル]-(フェニル-d5)アミノ}ビフェニル(化合物40)の合成>
窒素置換した反応容器に、N-(フェニル-d5)-ベンズアミド36.00g、4,4’-ジヨードビフェニル144.54g、銅粉2.26g、炭酸カリウム29.52g、亜硫酸水素ナトリウム3.70g、キシレン180ml、ドデシルベンゼン90mlを加えた後、キシレン150mlを留去しながら加熱し、銅粉2.26g、炭酸カリウム4.92gをそれぞれ2回に分けて追加しながら、200℃で16.5時間攪拌した。80℃まで冷却した後、トルエン1000mlを加え、さらに50℃まで冷却した。不溶物をろ過によって除いた後、濃縮し、ヘキサン800mlを加えて、シリカゲルを用いた吸着精製を行った。さらに、NHシリカゲルを用いた吸着精製を行った後、濃縮することによって、N-[(4’-ヨード)ビフェニル-4-イル]-N-(フェニル-d5)-ベンズアミドの白色粉体35.58g(収率41%)を得た。
本発明の化合物と対応する重水素原子で置換されていない比較化合物50、51、52について、高感度示差走査熱量計(ブルカー・エイエックスエス製、DSC3100S)によってガラス転移点を求めた。
ガラス転移点
本発明実施例1の化合物 100℃
本発明実施例2の化合物 101℃
比較化合物50 101℃
本発明実施例3の化合物 134℃
本発明実施例4の化合物 133℃
本発明実施例5の化合物 134℃
本発明実施例6の化合物 133℃
比較化合物51 132℃
本発明実施例7の化合物 144℃
比較化合物52 144℃
本発明の化合物を用いて、ITO基板の上に膜厚100nmの蒸着膜を作製して、大気中光電子分光装置(理研計器製、AC-2型)で仕事関数を測定した。
仕事関数
本発明実施例1の化合物 5.47eV
本発明実施例2の化合物 5.51eV
比較化合物50 5.46eV
本発明実施例3の化合物 5.43eV
本発明実施例4の化合物 5.44eV
本発明実施例5の化合物 5.43eV
本発明実施例6の化合物 5.42eV
比較化合物51 5.45eV
本発明実施例7の化合物 5.43eV
比較化合物52 5.44eV
有機EL素子は、図8に示すような、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔注入層3、正孔輸送層4、発光層5、電子輸送層7、電子注入層8、陰極(アルミニウム電極)9の順に蒸着して作製した。
比較のために、実施例10において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて前記比較化合物50を膜厚40nm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なった。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。
有機EL素子 化合物 発光開始電圧[V]
実施例10 化合物5 2.7
比較例1 比較化合物50 2.8
その結果、重水素原子で置換されていない比較化合物50を使用した比較例1に対し、本発明の実施例1の化合物(化合物5)を使用した実施例10ではほぼ同程度の発光開始電圧であることが分かる。
有機EL素子は、図9に示すような、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔輸送層4、発光層5、電子輸送層7、電子注入層8、陰極(アルミニウム電極)9の順に蒸着して作製した。
実施例11において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例4の化合物(化合物19)を膜厚60nm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2にまとめて示した。
実施例11において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例6の化合物(化合物21)を膜厚60nm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2にまとめて示した。
実施例11において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例7の化合物(化合物40)を膜厚60nm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2にまとめて示した。
比較のために、実施例11において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて前記比較化合物50を膜厚60nm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なった。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2にまとめて示した。
有機EL素子は、図10に示すような、ガラス基板1上に透明陽極2としてITO電極をあらかじめ形成したものの上に、正孔輸送層4、発光層5、正孔阻止層6、電子輸送層7、電子注入層8、陰極(アルミニウム電極)9の順に蒸着して作製した。
実施例15において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例4の化合物(化合物19)を膜厚50nm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5にまとめて示した。
実施例15において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例6の化合物(化合物21)を膜厚50nm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5にまとめて示した。
実施例15において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて本発明実施例7の化合物(化合物40)を膜厚50nm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5にまとめて示した。
比較のために、実施例15において、正孔輸送層4の材料として本発明実施例1の化合物(化合物5)に代えて前記比較化合物50を膜厚50nm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5にまとめて示した。
2 透明陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 正孔阻止層
7 電子輸送層
8 電子注入層
9 陰極
Claims (26)
- 下記一般式(1)で表される、分子中にトリフェニルアミン構造を2個、単結合またはヘテロ原子を含まない2価基で連結した構造を有するアリールアミン化合物。
(式中、R1~R28は同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基であって、互いに結合して環を形成していてもよい。但し、R1~R28の少なくともひとつは重水素原子、もしくは重水素原子を含む置換基であるものとする。A1は下記構造式(B)~(F)で示される2価基、または単結合を表す。)
(式中、R29~R32は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R33~R42は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R43~R50は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R51~R55は同一でも異なってもよく、水素原子または重水素原子を表す。) - 下記一般式(2)で表される、分子中にトリフェニルアミン構造を4個、単結合またはヘテロ原子を含まない2価基で連結した構造を有するアリールアミン化合物。
(式中、R56~R109は同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、ニトロ基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキル基、置換基を有していてもよい炭素原子数2ないし6の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数5ないし10のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基であって、互いに結合して環を形成していてもよい。但し、R56~R109の少なくともひとつは重水素原子、もしくは重水素原子を含む置換基であるものとする。A2は下記構造式(B)~(F)で示される2価基、または単結合を表す。)
(式中、R29~R32は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R33~R42は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R43~R50は同一でも異なってもよく、水素原子または重水素原子を表す。)
(式中、R51~R55は同一でも異なってもよく、水素原子または重水素原子を表す。) - 前記一般式(1)において、R1~R10またはR19~R28の少なくともひとつが、トリフェニルアミン構造との結合位置以外の全てが重水素原子で置換されている、芳香族炭化水素基、芳香族複素環基、縮合多環芳香族基またはアリールオキシ基である、請求項1記載のアリールアミン化合物。
- 前記一般式(1)において、R1~R10またはR19~R28の少なくともふたつが、トリフェニルアミン構造との結合位置以外の全てが重水素原子で置換されている、芳香族炭化水素基、芳香族複素環基、縮合多環芳香族基またはアリールオキシ基である、請求項1または請求項3記載のアリールアミン化合物。
- 前記一般式(1)において、R1~R5の全てが重水素原子である、請求項1記載のアリールアミン化合物。
- 前記一般式(1)において、R1~R5およびR19~R23の全てが重水素原子である、請求項1または請求項5記載のアリールアミン化合物。
- 前記一般式(1)において、R11~R18の全てが重水素原子である、請求項1記載のアリールアミン化合物。
- 前記一般式(1)において、R1~R5から選ばれる4個およびR19~R23から選ばれる4個の全てが重水素原子である、請求項1記載のアリールアミン化合物。
- 前記一般式(2)において、R56~R60、R69~R78、R87~R91またはR100~R109の少なくともひとつが、トリフェニルアミン構造との結合位置以外の全てが重水素原子で置換されている、芳香族炭化水素基、芳香族複素環基、縮合多環芳香族基またはアリールオキシ基である、請求項2記載のアリールアミン化合物。
- 前記一般式(2)において、R56~R60、R69~R78、R87~R91またはR100~R109の少なくともふたつが、トリフェニルアミン構造との結合位置以外の全てが重水素原子で置換されている、芳香族炭化水素基、芳香族複素環基、縮合多環芳香族基またはアリールオキシ基である、請求項2または請求項9記載のアリールアミン化合物。
- 前記一般式(2)において、R56~R60の全てが重水素原子である、請求項2記載のアリールアミン化合物。
- 前記一般式(2)において、R56~R60およびR87~R91の全てが重水素原子である、請求項2または請求項11記載のアリールアミン化合物。
- 前記一般式(2)において、R79~R86の全てが重水素原子である、請求項2記載のアリールアミン化合物。
- 前記一般式(2)において、R61~R68およびR92~R99の全てが重水素原子である、請求項2記載のアリールアミン化合物。
- 一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、前記請求項1~17に記載のアリールアミン化合物が、少なくとも1つの有機層の構成材料として用いられてい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。
- 前記した有機層が正孔輸送層である請求項18記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が正孔注入層である請求項18記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が電子阻止層である請求項18記載の有機エレクトロルミネッセンス素子。
- 一対の電極とその間に挟まれた、発光層、正孔輸送層と電子輸送層を含む、複数層の有機層を有する有機EL素子において、前記請求項1~17に記載のアリールアミン化合物が、該正孔輸送層の構成材料として用いられ、下記一般式(3)で表される、置換されたアントラセン環構造とピリドインドール環構造を有する化合物が、該電子輸送層の構成材料として用いられていることを特徴とする請求項18記載の有機エレクトロルミネッセンス素子。
(式中、Ar1、Ar2は同一でも異なってもよく、Ar1は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ar2は置換もしくは無置換の芳香族炭化水素基または置換もしくは無置換の縮合多環芳香族基を表し、B、Cは同一でも異なってもよく、単結合、あるいは置換もしくは無置換の芳香族炭化水素の2価基、置換もしくは無置換の芳香族複素環の2価基または置換もしくは無置換の縮合多環芳香族の2価基を表し、R110~R116は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、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、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、R117は重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、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を表し、r117は0または1~8の整数を表し、r117が2以上のとき複数のR117は互いに同一でも異なってもよく、r117が0である場合はR117で置換されていないことを表す。W、X、Y、Zは炭素原子または窒素原子を表す。ここでW、X、Y、Zはそのいずれか1つのみが窒素原子であるものとし、この場合の窒素原子はR110~R113の水素原子もしくは置換基を有さないものとする。) - 一対の電極とその間に挟まれた、燐光性の発光材料を含有する発光層と複数層の有機層を有する有機EL素子において、前記請求項1~17に記載のアリールアミン化合物が、少なくとも一層の有機層の構成材料として用いられていることを特徴とする請求項18記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が正孔注入層である請求項23記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が電子阻止層である請求項23記載の有機エレクトロルミネッセンス素子。
- 前記した燐光性の発光材料がイリジウムまたは白金を含む金属錯体である請求項23~25のいずれか1項に記載の有機エレクトロルミネッセンス素子。
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EP11736773.0A EP2530069B1 (en) | 2010-01-26 | 2011-01-25 | Compound with triphenylamine structure, and organic electroluminescent element |
CN201180007234.3A CN102781906B (zh) | 2010-01-26 | 2011-01-25 | 具有三苯胺结构的化合物及有机电致发光器件 |
US13/574,923 US9196839B2 (en) | 2010-01-26 | 2011-01-25 | Compound having triphenylamine structure, and organic electroluminescent device |
JP2011551756A JP5335103B2 (ja) | 2010-01-26 | 2011-01-25 | トリフェニルアミン構造を有する化合物および有機エレクトロルミネッセンス素子 |
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US (1) | US9196839B2 (ja) |
EP (1) | EP2530069B1 (ja) |
JP (2) | JP5335103B2 (ja) |
KR (1) | KR20120112672A (ja) |
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JPWO2013038627A1 (ja) * | 2011-09-12 | 2015-03-23 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
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WO2012117973A1 (ja) * | 2011-02-28 | 2012-09-07 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
JP5977227B2 (ja) * | 2011-02-28 | 2016-08-24 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
US9444055B2 (en) | 2011-02-28 | 2016-09-13 | Hodogaya Chemical Co., Ltd. | Organic electroluminescent device |
JP2014527021A (ja) * | 2011-04-01 | 2014-10-09 | ドクサン ハイ メタル カンパニー リミテッド | 化合物及びこれを用いた有機電気素子、その電子装置 |
US9691990B2 (en) | 2011-04-01 | 2017-06-27 | Duk San Neolux Co., Ltd. | Compound, organic electronic element using same, and electronic device using the latter |
JPWO2013038627A1 (ja) * | 2011-09-12 | 2015-03-23 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
JP2018110121A (ja) * | 2011-09-12 | 2018-07-12 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
TWI471308B (zh) * | 2012-11-13 | 2015-02-01 | Ind Tech Res Inst | 有機化合物及包含其之有機電激發光裝置 |
US11575087B1 (en) | 2020-12-25 | 2023-02-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device, light emitting device, organic electroluminescence display device and electronic device |
KR20230126721A (ko) | 2020-12-25 | 2023-08-30 | 이데미쓰 고산 가부시키가이샤 | 유기 일렉트로루미네센스 소자, 발광 장치, 유기 일렉트로루미네센스표시 장치 및 전자 기기 |
KR20230131254A (ko) | 2021-01-13 | 2023-09-12 | 이데미쓰 고산 가부시키가이샤 | 유기 일렉트로루미네센스 소자, 유기 일렉트로루미네센스표시 장치 및 전자 기기 |
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US20120292609A1 (en) | 2012-11-22 |
TWI508933B (zh) | 2015-11-21 |
CN102781906A (zh) | 2012-11-14 |
JP2013216667A (ja) | 2013-10-24 |
US9196839B2 (en) | 2015-11-24 |
CN102781906B (zh) | 2014-06-04 |
EP2530069A1 (en) | 2012-12-05 |
EP2530069A4 (en) | 2013-10-30 |
EP2530069B1 (en) | 2016-09-14 |
KR20120112672A (ko) | 2012-10-11 |
JP5335103B2 (ja) | 2013-11-06 |
TW201202177A (en) | 2012-01-16 |
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