JP2013530936A - Oledのための、ビカルバゾール含有化合物 - Google Patents
Oledのための、ビカルバゾール含有化合物 Download PDFInfo
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- JP2013530936A JP2013530936A JP2013508128A JP2013508128A JP2013530936A JP 2013530936 A JP2013530936 A JP 2013530936A JP 2013508128 A JP2013508128 A JP 2013508128A JP 2013508128 A JP2013508128 A JP 2013508128A JP 2013530936 A JP2013530936 A JP 2013530936A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 239000010410 layer Substances 0.000 claims description 81
- 239000000463 material Substances 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 230000000903 blocking effect Effects 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002019 doping agent Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- -1 azadibenzofuran Chemical compound 0.000 abstract description 26
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 10
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 10
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 abstract description 6
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002894 organic compounds Chemical class 0.000 abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- 239000003446 ligand Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000007924 injection Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- PUMOFXXLEABBTC-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9h-carbazole Chemical group C1=CC=C2C3=CC(C4=CC=C5NC=6C(C5=C4)=CC=CC=6)=CC=C3NC2=C1 PUMOFXXLEABBTC-UHFFFAOYSA-N 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
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- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- 0 BC(*)(CCC1)CC(*2)=C1C1(C)C2CC(C)(*)CCC1 Chemical compound BC(*)(CCC1)CC(*2)=C1C1(C)C2CC(C)(*)CCC1 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 3
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- YMUPVHDJENQJSL-UHFFFAOYSA-N 1-chloro-[1]benzofuro[2,3-c]pyridine Chemical compound C12=CC=CC=C2OC2=C1C=CN=C2Cl YMUPVHDJENQJSL-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
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- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
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- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [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
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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Abstract
Description
本明細書は、そのすべての開示物が参照により本明細書で明確に組み込まれている、2010年4月26日に出願された、米国特許出願第12/767,433号明細書の優先権を主張する。
本発明中で使用されるべき空孔注入/輸送物質は特に限定はされず、その化合物が典型的に、空孔注入/輸送物質として使用される限り、任意の化合物を使用してよい。物質の例には、フタロシアニンまたはポリフィリン誘導体、芳香族アミン誘導体、インドロカルバゾール誘導体、フルオロ炭化水素を含むポリマー、伝導性ドーパントを添加したポリマー、PEDOT/PSSのような伝導ポリマー、リン酸およびシラン誘導体のような化合物から由来する自己アセンブリモノマー、MoOxのような酸化金属誘導体、1,4,5,8,9,12−ヘキサアザトリフェニレンヘキサカルボニトリルのようなp型半導体有機化合物、金属錯体および架橋可能化合物が含まれるが、これらに限定はされない。
本発明の有機ELデバイスの光発光層は好ましくは、光放射物質として、少なくとも1つの金属錯体を持ち、ドーパント化合物として、金属錯体を用いるホスト化合物を含んでよい。ホスト物質の例は、とくに限定はされず、ホストの三重エネルギーが、ドーパントのものよりも大きい限り、任意の金属錯体または有機化合物を使用してよい。
空孔ブロッキング層(HBL)を、発光層を離れる空孔および/またはエキシトンの数を減少させるために使用してよい。デバイス中のそのようなブロッキング層の存在により、結果として、ブロッキング層を欠く同様のデバイスと比較して、本質的により効率が高くなる。また、ブロッキング層を、OLEDの望む領域に発光を限定するために使用してよい。
電子輸送層(ETL)には、電子を輸送可能な物質が含まれうる。電子輸送層は、内因性(ドープされていない)か、またはドープされていてよい。ドープ化を、伝導性を増強するために使用してよい。ETL物質の例は特に限定はされないが、電子を輸送するために典型的に使用される限り、任意の金属錯体または有機化合物が使用されてよい。
化合物実施例
実施例1 化合物1の合成
化合物2の合成
化合物3の合成
化合物4の合成
化合物5の合成
化合物9の合成
すべてのデバイス実施例を、高真空(<10−7Torr)温度蒸発によって加工した。陽極電極は、800Åの酸化インジウムスズ(ITO)である。陰極は、10ÅのLiFとそれに続く1000ÅのAlからなる。すべてのデバイスを、加工の直後、窒素グローブボックス(<1ppmのH2OとO2)中エポキシ樹脂で密封したガラス蓋でカプセル封入し、湿気吸収物をパッケージ内に組み込んだ。
Claims (23)
- ビカルバゾールを含む化合物であって、式
式中Ra、Rb、Rc、Rd、R1およびR2は、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アリールおよびヘテロアリールからなる群より独立して選択され、
式中R1およびR2のうち少なくとも1つは、式
式中AおよびBは、独立して5または6員炭素環状またはヘテロ環状環であり、
式中RAおよびRBは、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アリールおよびヘテロアリールからなる群より独立して選択され、
式中XはS、OまたはSeである、化合物。 - R1およびR2が、アリールおよびヘテロアリールから独立して選択される、請求項1に記載の化合物。
- AおよびBが、フェニルおよびピリジンから独立して選択される、請求項1に記載の化合物。
- さらに、
陽極、
陰極、および
陽極と陰極の間に配置される有機層
を含む有機発光デバイスを含む第一デバイスであって、
前記有機層がビカルバゾールを含む化合物を含み、前記化合物が、式
式中Ra、Rb、Rc、Rd、R1およびR2は、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アリールおよびヘテロアリールからなる群より独立して選択され、
式中R1およびR2のうちの少なくとも1つが、式
式中AおよびBは、独立して5または6員炭素環状またはヘテロ環状環であり、
式中RAおよびRBは、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アリールおよびヘテロアリールからなる群より独立して選択され、
式中XはS、OまたはSeである、第一デバイス。 - R1およびR2が、アリールおよびヘテロアリールから独立して選択される、請求項10に記載のデバイス。
- AおよびBが、フェニルおよびピリジンから独立して選択される、請求項10に記載の第一デバイス。
- 前記有機層が、ブロッキング層であり、式Iを持つ前記化合物がブロッキング物質である、請求項10に記載の第一デバイス。
- 前記有機層が発光層であり、式Iを持つ前記化合物がホストである、請求項10に記載の第一デバイス。
- 前記第一デバイスが、民生用製品である、請求項10に記載の第一デバイス。
- 前記第一デバイスが、有機発光デバイスである、請求項10に記載の第一デバイス。
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US12/767,433 US8227801B2 (en) | 2010-04-26 | 2010-04-26 | Bicarbzole containing compounds for OLEDs |
PCT/US2011/033782 WO2011137072A1 (en) | 2010-04-26 | 2011-04-25 | Bicarbazole containing compounds for oleds |
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---|---|---|---|---|
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WO2015036080A1 (de) * | 2013-09-11 | 2015-03-19 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
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EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
CN103601668A (zh) * | 2013-11-26 | 2014-02-26 | 大连联化化学有限公司 | 一种n-苯基-3-溴咔唑的制备方法 |
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US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106414452B (zh) * | 2014-03-10 | 2019-10-11 | 三星Sdi株式会社 | 缩合环状化合物和含有其的有机发光装置 |
WO2015137630A1 (ko) * | 2014-03-10 | 2015-09-17 | 삼성에스디아이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
WO2015137472A1 (ja) * | 2014-03-12 | 2015-09-17 | 出光興産株式会社 | 組成物、化合物、有機エレクトロルミネッセンス素子用材料、インク組成物、有機エレクトロルミネッセンス素子、及び電子機器 |
KR102288347B1 (ko) | 2014-05-02 | 2021-08-11 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102255197B1 (ko) | 2014-05-02 | 2021-05-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102293727B1 (ko) | 2014-05-02 | 2021-08-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102208859B1 (ko) * | 2014-05-21 | 2021-01-28 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20150135123A (ko) * | 2014-05-23 | 2015-12-02 | 롬엔드하스전자재료코리아유한회사 | 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
KR102308903B1 (ko) * | 2014-06-17 | 2021-10-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US10297762B2 (en) | 2014-07-09 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3174885B1 (en) | 2014-07-28 | 2019-10-02 | Idemitsu Kosan Co., Ltd. | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
KR102256932B1 (ko) | 2014-09-18 | 2021-05-28 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
KR101818581B1 (ko) * | 2014-10-31 | 2018-01-15 | 삼성에스디아이 주식회사 | 유기 광전자 소자 및 표시 장치 |
KR102285386B1 (ko) * | 2014-11-03 | 2021-08-04 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
KR102384649B1 (ko) | 2014-11-10 | 2022-04-11 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
KR102385230B1 (ko) | 2014-11-19 | 2022-04-12 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102364220B1 (ko) | 2014-12-03 | 2022-02-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
KR102363260B1 (ko) | 2014-12-19 | 2022-02-16 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
WO2016193243A1 (en) | 2015-06-03 | 2016-12-08 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
KR101805686B1 (ko) * | 2015-07-27 | 2017-12-07 | 희성소재(주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11522140B2 (en) | 2015-08-17 | 2022-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2017056055A1 (en) | 2015-10-01 | 2017-04-06 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3356368B1 (en) | 2015-10-01 | 2021-07-21 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
US20180319813A1 (en) | 2015-11-04 | 2018-11-08 | Idemitsu Kosan Co., Ltd | Benzimidazole fused heteroaryls |
WO2017093958A1 (en) | 2015-12-04 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
WO2017109722A1 (en) | 2015-12-21 | 2017-06-29 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing heterocyclic compounds and organic electroluminescence devices containing them |
CN105820105A (zh) * | 2016-03-31 | 2016-08-03 | 齐鲁工业大学 | 一种n-苯基咔唑二聚物的简化合成方法 |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
KR102061246B1 (ko) | 2016-09-28 | 2020-02-20 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
KR101885898B1 (ko) * | 2016-11-16 | 2018-08-06 | 주식회사 엘지화학 | 유기 발광 소자 |
US11264576B2 (en) | 2016-12-19 | 2022-03-01 | Idemitsu Kosan Co., Ltd. | Specifically substituted ladder type compounds for organic light emitting devices |
US11594685B2 (en) | 2017-03-30 | 2023-02-28 | Lg Chem, Ltd. | Organic light emitting device |
US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
CN110759930B (zh) * | 2018-12-06 | 2022-04-05 | 广州华睿光电材料有限公司 | 螺环化合物及其用途 |
KR102290359B1 (ko) * | 2018-12-11 | 2021-08-19 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물 |
CN111384299B (zh) * | 2018-12-29 | 2024-02-09 | 固安鼎材科技有限公司 | 一种有机发光二极管及其制备方法 |
CN109912610B (zh) * | 2019-04-04 | 2020-06-23 | 石家庄诚志永华显示材料有限公司 | 有机化合物及其在制备有机电致发光元件中的应用 |
KR102446400B1 (ko) * | 2019-08-09 | 2022-09-22 | 주식회사 엘지화학 | 유기 발광 소자 |
CN111039962B (zh) * | 2019-12-30 | 2020-11-27 | 陕西莱特光电材料股份有限公司 | 一种含氮化合物和应用以及使用其的有机电致发光器件 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060046172A1 (en) * | 2004-08-30 | 2006-03-02 | Violeta Vaitkeviciene | Polymeric charge transport materials having carbazolyl repeating units |
JP2008523049A (ja) * | 2004-12-08 | 2008-07-03 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | りん光エミッターのためのホストマトリックスとして半導体材料で用いるための9,9’−及び2,2’−置換3,3’−ビカルバゾリル誘導体 |
US20090153034A1 (en) * | 2007-12-13 | 2009-06-18 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emittinig diodes |
WO2011122132A1 (ja) * | 2010-03-31 | 2011-10-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US8148891B2 (en) * | 2005-10-04 | 2012-04-03 | Universal Display Corporation | Electron impeding layer for high efficiency phosphorescent OLEDs |
JP5556012B2 (ja) * | 2006-03-17 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5011908B2 (ja) * | 2006-09-26 | 2012-08-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US7745990B2 (en) * | 2007-03-29 | 2010-06-29 | Konica Minolta Holdings, Inc. | White light emitting organic electroluminescent element and lighting device |
WO2009060742A1 (ja) * | 2007-11-08 | 2009-05-14 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
EP2453496B1 (en) * | 2009-07-07 | 2018-11-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, novel compound, lighting device and display device |
-
2010
- 2010-04-26 US US12/767,433 patent/US8227801B2/en active Active
-
2011
- 2011-04-25 JP JP2013508128A patent/JP5878519B2/ja active Active
- 2011-04-25 CN CN201180020940.1A patent/CN102869659B/zh active Active
- 2011-04-25 WO PCT/US2011/033782 patent/WO2011137072A1/en active Application Filing
- 2011-04-25 DE DE112011101447T patent/DE112011101447T5/de active Pending
- 2011-04-25 KR KR1020127030236A patent/KR101843211B1/ko active IP Right Grant
- 2011-04-25 CN CN201410575147.3A patent/CN104478864B/zh active Active
- 2011-04-26 TW TW100114551A patent/TWI558700B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060046172A1 (en) * | 2004-08-30 | 2006-03-02 | Violeta Vaitkeviciene | Polymeric charge transport materials having carbazolyl repeating units |
JP2008523049A (ja) * | 2004-12-08 | 2008-07-03 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | りん光エミッターのためのホストマトリックスとして半導体材料で用いるための9,9’−及び2,2’−置換3,3’−ビカルバゾリル誘導体 |
US20090153034A1 (en) * | 2007-12-13 | 2009-06-18 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emittinig diodes |
WO2011122132A1 (ja) * | 2010-03-31 | 2011-10-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2011125680A1 (ja) * | 2010-03-31 | 2011-10-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9876178B2 (en) | 2014-09-05 | 2018-01-23 | Samsung Display Co., Ltd. | Organic light emitting device and display device including the same |
JP2016076700A (ja) * | 2014-10-06 | 2016-05-12 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネッセンス材料及びデバイス |
JP2016147851A (ja) * | 2015-02-13 | 2016-08-18 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 有機光電子素子用化合物、有機光電子素子および表示装置 |
JP2017222636A (ja) * | 2016-05-11 | 2017-12-21 | ヒソン・マテリアル・リミテッドHeesung Material Ltd. | ヘテロ環化合物およびこれを用いた有機発光素子 |
JP2019196323A (ja) * | 2018-05-09 | 2019-11-14 | 公益財団法人相模中央化学研究所 | 9−(1−ナフチル)−9h−カルバゾール誘導体の製造方法 |
JP7023176B2 (ja) | 2018-05-09 | 2022-02-21 | 公益財団法人相模中央化学研究所 | 9-(1-ナフチル)-9h-カルバゾール誘導体の製造方法 |
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TWI558700B (zh) | 2016-11-21 |
CN104478864A (zh) | 2015-04-01 |
WO2011137072A1 (en) | 2011-11-03 |
KR101843211B1 (ko) | 2018-03-28 |
CN102869659A (zh) | 2013-01-09 |
US20110260138A1 (en) | 2011-10-27 |
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