JPWO2017056205A1 - Novel imidazole compounds, materials for electronic devices, light emitting elements and electronic devices - Google Patents
Novel imidazole compounds, materials for electronic devices, light emitting elements and electronic devices Download PDFInfo
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- JPWO2017056205A1 JPWO2017056205A1 JP2017542567A JP2017542567A JPWO2017056205A1 JP WO2017056205 A1 JPWO2017056205 A1 JP WO2017056205A1 JP 2017542567 A JP2017542567 A JP 2017542567A JP 2017542567 A JP2017542567 A JP 2017542567A JP WO2017056205 A1 JPWO2017056205 A1 JP WO2017056205A1
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- 239000000463 material Substances 0.000 title claims description 78
- 150000002460 imidazoles Chemical class 0.000 title 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 89
- -1 imidazole compound Chemical class 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 0 Cc1nc(C)nc(*)n1 Chemical compound Cc1nc(C)nc(*)n1 0.000 description 11
- 238000005401 electroluminescence Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
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- 238000010549 co-Evaporation Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 239000012299 nitrogen atmosphere Substances 0.000 description 4
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- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- MPVJHWOGTWPIIR-UHFFFAOYSA-N 2-(3-nitrophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MPVJHWOGTWPIIR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QPFMQLKDCFTFMY-UHFFFAOYSA-N 3-(4,6-diphenyl-1,3,5-triazin-2-yl)aniline Chemical compound NC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QPFMQLKDCFTFMY-UHFFFAOYSA-N 0.000 description 3
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- CYXOACUWOWUJNP-UHFFFAOYSA-N BrC=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC2=CC=CC=C2C=C1 Chemical compound BrC=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC2=CC=CC=C2C=C1 CYXOACUWOWUJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UBFXCKPOYBVZCM-UHFFFAOYSA-N BrC=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC=CC=C1 Chemical compound BrC=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC=CC=C1 UBFXCKPOYBVZCM-UHFFFAOYSA-N 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WPZDRZVULAPMOY-UHFFFAOYSA-N OB(C=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC2=CC=CC=C2C=C1)O Chemical compound OB(C=1C=C(C=CC=1)N1C(=NC2=C1C1=CC=CC=C1C=1C=CC=CC=12)C1=CC2=CC=CC=C2C=C1)O WPZDRZVULAPMOY-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Abstract
本発明は、電子デバイスの形成に用いた場合に、駆動電圧が低く、電流効率の高い電子デバイスを得ることができる新規イミダゾール化合物を提供することを目的とする。本発明のイミダゾール化合物は、下記一般式（１）で表されるものである。
【化１】
（式（１）中、Ｒ１及びＲ２はそれぞれ、明細書中に記載のものと同様である。）An object of the present invention is to provide a novel imidazole compound that can provide an electronic device with low driving voltage and high current efficiency when used for forming an electronic device. The imidazole compound of the present invention is represented by the following general formula (1).
[Chemical 1]
(In formula (1), R 1 and R 2 are the same as those described in the specification.)
Description
本発明は、新規イミダゾール化合物、電子デバイス用材料、発光素子及び電子デバイスに関し、とりわけ有機エレクトロルミネッセンス（ＥＬ）素子等の発光素子の発光層を構成するホスト材料として有用な新規イミダゾール化合物、これを含有する電子デバイス用材料、この電子デバイス用材料を含有する発光素子、その発光素子を含む電子デバイスに関する。 The present invention relates to a novel imidazole compound, a material for an electronic device, a light-emitting element, and an electronic device, and particularly includes a novel imidazole compound useful as a host material constituting a light-emitting layer of a light-emitting element such as an organic electroluminescence (EL) element. The present invention relates to an electronic device material, a light emitting element containing the electronic device material, and an electronic device including the light emitting element.
電子デバイス用材料、特に有機ＥＬ素子等の発光素子の発光層を構成する発光材料やホスト材料として、これまで様々な検討が行われてきている。
例えば、特許文献１には、２，４，５−トリアリール置換イミダゾール化合物及び１，２，４，５−テトラアリール置換イミダゾール化合物を青色蛍光発光材料に用いることが記載されている。
また、特許文献２には、フェニルピリジン誘導体を発光材料に用いること、２，４，５−トリス（６−ピリジルビフェニル）イミダゾール誘導体を燐光ホスト材料として用いることが記載されている。
さらに、特許文献３には、イミダゾールの少なくとも１位又は２位に電子受容性基を有し、他方が電子供与基である化合物をホスト材料として用いることが記載されている。
さらに、非特許文献１には、ＣＢＰ（４，４’−Ｎ，Ｎ’−ビス（カルバゾリル−９−イル）ビフェニル）やｍＣＰ（１，３−ジ（カルバゾリル−９−イル）ベンゼン）をホスト材料として用いることが記載されている。
また、非特許文献２には、ベンゾジフラン誘導体をバイポーラー性ホスト材料として用いることが記載されている。Various studies have been made so far as a light-emitting material or a host material constituting a light-emitting layer of a light-emitting element such as an electronic device material, particularly an organic EL element.
For example,
Furthermore, Patent Document 3 describes that a compound having an electron-accepting group at least at the 1-position or 2-position of imidazole and the other being an electron-donating group is used as a host material.
Further,
Non-Patent
燐光発光材料を発光材料（ドーパント）として用いた発光素子におけるホスト材料は、電子とホールの輸送能力を十分に持ち、且つ高い成膜性を有することが必要である。 A host material in a light-emitting element using a phosphorescent light-emitting material as a light-emitting material (dopant) needs to have a sufficient ability to transport electrons and holes and have high film-forming properties.
しかしながら、良く知られたホスト化合物であるＣＢＰは薄膜の安定性が不十分である。またｍＣＰは素子を形成した際の熱安定性が低いという問題があった。 However, CBP, which is a well-known host compound, has insufficient thin film stability. In addition, mCP has a problem of low thermal stability when an element is formed.
また、近年、高い発光効率を得るために、素子構造は非常に多くの層からなる多層構造になってきているので、素子構造の低層化による製造工程の簡略化、コストダウンが求められている。例えば非特許文献２に記載のベンゾジフラン誘導体を用いた発光素子においては、有機層の単層化ないし低層化を実現可能であるが、素子構成が特殊であり、製造が困難である。また、その成膜プロセスは真空蒸着法に限られるので、製造工程が煩雑であるという問題もある。すなわち、素子構成と製造プロセスをともに簡略化しうる電子デバイス用材料がこれまで見つかっていないのが現状である。
また、高い発光効率を得るには、使用するホスト材料が重要であり、該ホスト材料を含む発光層の安定性が低い場合は、実用化に向けて発光素子の駆動安定性に問題を抱えることとなる。In recent years, in order to obtain high luminous efficiency, the element structure has become a multi-layered structure composed of an extremely large number of layers. Therefore, it is required to simplify the manufacturing process and reduce the cost by lowering the element structure. . For example, in a light-emitting element using a benzodifuran derivative described in Non-Patent
In addition, in order to obtain high luminous efficiency, the host material to be used is important. When the stability of the light emitting layer containing the host material is low, there is a problem in the driving stability of the light emitting element for practical use. It becomes.
上述したような実状から、駆動電圧、電流効率、発光効率等に対して十分な性能を有する有機ＥＬ素子の開発が望まれており、該素子を得ることができる新たな化合物の開発が望まれている。
本発明は上記の事情に鑑みてなされたものであり、その目的は、電子デバイスの形成に用いた場合に、駆動電圧が低く、電流効率の高い電子デバイスを得ることができる新規イミダゾール化合物を提供することである。また、かかる新規イミダゾール化合物を含有する電子デバイス用材料、この電子デバイス用材料を含有する発光素子、その発光素子を含む電子デバイスを提供することである。From the actual situation as described above, it is desired to develop an organic EL element having sufficient performance with respect to driving voltage, current efficiency, light emission efficiency, etc., and development of a new compound capable of obtaining the element is desired. ing.
The present invention has been made in view of the above circumstances, and an object thereof is to provide a novel imidazole compound capable of obtaining an electronic device with low driving voltage and high current efficiency when used for forming an electronic device. It is to be. Moreover, it is providing the electronic device material containing this novel imidazole compound, the light emitting element containing this electronic device material, and the electronic device containing the light emitting element.
本発明者らは、上記課題を解決するために、鋭意検討を重ねた結果、フェナントロ［９，１０−ｄ］イミダゾール化合物が上記課題を解決しうることを見出した。 As a result of intensive studies to solve the above problems, the present inventors have found that a phenanthro [9,10-d] imidazole compound can solve the above problems.
すなわち、本発明の要旨は、以下の（１）〜（７）である。
（１）下記一般式（１）で表されるイミダゾール化合物。That is, the gist of the present invention is the following (1) to (7).
(1) An imidazole compound represented by the following general formula (1).
（式（１）中、Ｒ１は炭素数１〜２４のアルキル基、炭素数１〜２４の芳香族炭化水素基又は炭素数１〜２４の芳香族複素環基であり、Ｒ２は下記一般式（２）に示す基である。）(In the formula (1), R 1 is an alkyl group, an aromatic heterocyclic group of aromatic hydrocarbon group, or 1 to 24 carbon atoms having 1 to 24 carbon atoms having 1 to 24 carbon atoms, R 2 is represented by the following general (It is a group shown in Formula (2).)
（式（２）中、Ａｒ１は芳香族炭化水素鎖又は芳香族複素環鎖であり、Ａｒ２は下記一般式（３）、（４）、（５）、（６）又は（７）で表される基である。）(In the formula (2), Ar 1 is an aromatic hydrocarbon chain or an aromatic heterocyclic chain, and Ar 2 is the following general formula (3), (4), (5), (6) or (7). Group represented.)
（式（３）中、Ａｒ３及びＡｒ４はそれぞれ独立して、炭素数６〜２０の芳香族基又は炭素数５〜１８の芳香族複素環基であり、式（４）中、Ｘ１は、酸素原子、硫黄原子、或いは、アルキル基、芳香族炭化水素基又は芳香族複素環基が置換した窒素原子であり、式（４）及び（５）中、Ｘ２〜Ｘ５はそれぞれ独立して、窒素原子又は炭素原子であり、式（６）のＲ３及び（７）のＲ４はそれぞれ、炭素数１〜２４のアルキル基、炭素数６〜２４の芳香族炭化水素基又は炭素数１〜２４の芳香族複素環基である。）(In Formula (3), Ar 3 and Ar 4 are each independently an aromatic group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 5 to 18 carbon atoms. In Formula (4), X 1 Is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group, and in formulas (4) and (5), X 2 to X 5 are independent of each other. And R 3 in formula (6) and R 4 in (7) are each an alkyl group having 1 to 24 carbon atoms, an aromatic hydrocarbon group having 6 to 24 carbon atoms, or a carbon atom. (It is an aromatic heterocyclic group of formula 1-24.)
（２）前記Ｒ１が、炭素数６〜２４の芳香族炭化水素基である前記（１）に記載のイミダゾール化合物。
（３）前記Ａｒ２が、前記一般式（３）又は（４）である前記（１）又は（２）に記載のイミダゾール化合物。
（４）前記（１）〜（３）のいずれか１つに記載のイミダゾール化合物を含有する電子デバイス用材料。
（５）前記（４）に記載の電子デバイス用材料を含有する発光素子。
（６）前記（４）に記載の電子デバイス用材料をホスト材料として含有する発光素子。
（７）前記（４）に記載の電子デバイス用材料を正孔阻止材料として含有する発光素子。
（８）前記（４）に記載の電子デバイス用材料を電子輸送材料として含有する発光素子。
（９）前記（５）〜（８）のいずれか１つに記載の発光素子を含む電子デバイス。(2) The imidazole compound according to (1), wherein R 1 is an aromatic hydrocarbon group having 6 to 24 carbon atoms.
(3) The imidazole compound according to (1) or (2), wherein Ar 2 is the general formula (3) or (4).
(4) An electronic device material containing the imidazole compound according to any one of (1) to (3).
(5) A light emitting device containing the electronic device material according to (4).
(6) A light-emitting element containing the electronic device material according to (4) as a host material.
(7) A light-emitting device containing the electronic device material according to (4) as a hole blocking material.
(8) A light-emitting device containing the electronic device material according to (4) as an electron transport material.
(9) An electronic device comprising the light emitting element according to any one of (5) to (8).
本発明の新規イミダゾール化合物は、材料の安定性や成膜した際の薄膜の安定性が高い。したがって、本発明の新規イミダゾール化合物を含有する電子デバイス用材料を用いて、例えば発光素子に適用した場合、発光効率が向上し、発光素子が長寿命化され、かかる発光素子を含む、ディスプレイ装置等の電子デバイスの駆動電圧と電流効率が良好となり、該電子デバイスが長寿命化されるという効果が得られる。
また、本発明のイミダゾール化合物をホスト材料として用いることによって、低電圧駆動特性に優れ、安定で高い量子効率の発光素子を得ることができる。The novel imidazole compound of the present invention has high material stability and thin film stability when deposited. Therefore, when the electronic device material containing the novel imidazole compound of the present invention is used, for example, when applied to a light emitting element, the light emitting efficiency is improved, the life of the light emitting element is extended, and a display device including such a light emitting element, etc. As a result, the driving voltage and current efficiency of the electronic device can be improved, and the life of the electronic device can be extended.
In addition, by using the imidazole compound of the present invention as a host material, it is possible to obtain a light-emitting element that is excellent in low-voltage driving characteristics, stable and has high quantum efficiency.
以下に、本発明を詳細に述べる。
本発明のイミダゾール化合物は、下記一般式（１）で示されるものである。The present invention is described in detail below.
The imidazole compound of the present invention is represented by the following general formula (1).
（式（１）中、Ｒ１は炭素数１〜２４のアルキル基、炭素数６〜２４の芳香族炭化水素基又は炭素数１〜２４の芳香族複素環基であり、Ｒ２は下記一般式（２）に示す基である。）(In the formula (1), R 1 is an alkyl group having 1 to 24 carbon atoms, an aromatic hydrocarbon group having 6 to 24 carbon atoms or an aromatic heterocyclic group having 1 to 24 carbon atoms, and R 2 is the following general formula. (It is a group shown in Formula (2).)
（式（２）中、Ａｒ１は芳香族炭化水素鎖又は芳香族複素環鎖であり、Ａｒ２は下記一般式（３）、（４）、（５）、（６）又は（７）で表される基である。）(In the formula (2), Ar 1 is an aromatic hydrocarbon chain or an aromatic heterocyclic chain, and Ar 2 is the following general formula (3), (4), (5), (6) or (7). Group represented.)
（式（３）中、Ａｒ３及びＡｒ４はそれぞれ独立して、炭素数６〜２０の芳香族基又は炭素数５〜１８の芳香族複素環基であり、式（４）中、Ｘ１は、酸素原子、硫黄原子、或いは、アルキル基、芳香族炭化水素基又は芳香族複素環基が置換した窒素原子であり、式（４）及び（５）中、Ｘ２〜Ｘ５はそれぞれ独立して、窒素原子又は炭素原子であり、式（６）のＲ３及び（７）のＲ４はそれぞれ、炭素数１〜２４のアルキル基、炭素数１〜２４の芳香族炭化水素基又は炭素数１〜２４の芳香族複素環基である。）(In Formula (3), Ar 3 and Ar 4 are each independently an aromatic group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 5 to 18 carbon atoms. In Formula (4), X 1 Is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group, and in formulas (4) and (5), X 2 to X 5 are independent of each other. And R 3 in formula (6) and R 4 in (7) are each an alkyl group having 1 to 24 carbon atoms, an aromatic hydrocarbon group having 1 to 24 carbon atoms, or a carbon atom. (It is an aromatic heterocyclic group of formula 1-24.)
一般式（１）において、Ｒ１の炭素数１〜２４のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、アミル基、イソアミル基、ｔｅｒｔ−アミル基、ネオペンチル基、ｎ−ヘキシル基等が挙げられ、中でも炭素数１〜１２のアルキル基が好ましく、炭素数１〜６のアルキル基がより好ましい。In the general formula (1), examples of the alkyl group having 1 to 24 carbon atoms of R 1 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. A butyl group, an n-pentyl group, an amyl group, an isoamyl group, a tert-amyl group, a neopentyl group, an n-hexyl group and the like can be mentioned. Among them, an alkyl group having 1 to 12 carbon atoms is preferable, and an alkyl having 1 to 6 carbon atoms Groups are more preferred.
一般式（１）において、Ｒ１の炭素数６〜２４の芳香族炭化水素基としては、フェニル基、トリル等の単環芳香族炭化水素基、フェナントリル基、ナフチル基、アントリル基、フルオレニル基、ピレニル基、ペリレニル基等の縮合多環芳香族炭化水素基、ビフェニル基、ターフェニル基等の環連結芳香族炭化水素基等が挙げられ、中でも炭素数６〜２０の芳香族炭化水素基が好ましく、炭素数６〜１４の芳香族炭化水素基がより好ましい。In the general formula (1), examples of the aromatic hydrocarbon group having 6 to 24 carbon atoms represented by R 1 include a monocyclic aromatic hydrocarbon group such as phenyl group and tolyl, phenanthryl group, naphthyl group, anthryl group, fluorenyl group, Examples thereof include condensed polycyclic aromatic hydrocarbon groups such as pyrenyl group and perylenyl group, ring-linked aromatic hydrocarbon groups such as biphenyl group and terphenyl group, among which aromatic hydrocarbon groups having 6 to 20 carbon atoms are preferable. An aromatic hydrocarbon group having 6 to 14 carbon atoms is more preferable.
一般式（１）において、Ｒ１の炭素数１〜２４の芳香族複素環基としては、例えば、ピリジル基、チエニル基、フリル基、オキサゾリル基、チアゾリル基、オキサジアゾリル基、ベンゾチエニル基、ジベンゾフリル基、ジベンゾチエニル基、ピラジニル基、ピリミジニル基、ピラゾリル基、イミダゾリル基、フェニルカルバゾリル基等が挙げられ、中でも炭素数２〜２０の芳香族複素環基が好ましく、炭素数３〜１５の芳香族複素環基がより好ましい。In the general formula (1), examples of the aromatic heterocyclic group having 1 to 24 carbon atoms represented by R 1 include a pyridyl group, a thienyl group, a furyl group, an oxazolyl group, a thiazolyl group, an oxadiazolyl group, a benzothienyl group, and a dibenzofuryl group. Group, dibenzothienyl group, pyrazinyl group, pyrimidinyl group, pyrazolyl group, imidazolyl group, phenylcarbazolyl group, etc. Among them, an aromatic heterocyclic group having 2 to 20 carbon atoms is preferable, and an aromatic group having 3 to 15 carbon atoms is preferred. A group heterocyclic group is more preferred.
本発明において、Ｒ１は電荷受容性の観点から、芳香族炭化水素基又は芳香族複素環基であることが好ましく、炭素数６〜１４の芳香族炭化水素基又は炭素数３〜１５の芳香族複素環基がより好ましい。In the present invention, R 1 is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group from the viewpoint of charge acceptance, and an aromatic hydrocarbon group having 6 to 14 carbon atoms or an aromatic group having 3 to 15 carbon atoms. A group heterocyclic group is more preferred.
一般式（１）において、Ｒ２は上記一般式（２）に示す基である。一般式（２）において、Ａｒ１の芳香族炭化水素鎖としては、例えば、ベンゼンから誘導される２価鎖（フェニル鎖）、多環芳香族炭化水素から誘導される２価鎖（多環芳香族炭化水素鎖）、４，４’−ビフェニリレン等のビフェニルから誘導される２価鎖（ビフェニル鎖）等が挙げられる。芳香族炭化水素鎖の炭素数は６〜２０が好ましく、より好ましくは６〜１８であり、特に好ましくは６〜１４である。
Ａｒ１の芳香族複素環鎖としては、例えば、イミダゾール、フラン、チオフェン、ピロール、ピリジン等から誘導される２価鎖が挙げられる。
中でも、Ａｒ１は、フェニル鎖、多環芳香族炭化水素鎖が好ましく、フェニル鎖がより好ましい。In the general formula (1), R 2 is a group represented by the general formula (2). In the general formula (2), examples of the aromatic hydrocarbon chain of Ar 1 include a divalent chain derived from benzene (phenyl chain) and a divalent chain derived from polycyclic aromatic hydrocarbon (polycyclic aromatic). Group hydrocarbon chain), and bivalent chains (biphenyl chains) derived from biphenyl such as 4,4′-biphenylylene. 6-20 are preferable, as for carbon number of an aromatic hydrocarbon chain, More preferably, it is 6-18, Especially preferably, it is 6-14.
Examples of the aromatic heterocyclic chain of Ar 1 include a divalent chain derived from imidazole, furan, thiophene, pyrrole, pyridine and the like.
Among these, Ar 1 is preferably a phenyl chain or a polycyclic aromatic hydrocarbon chain, and more preferably a phenyl chain.
一般式（２）において、Ａｒ２は上記一般式（３）〜（７）に示す基である。In the general formula (2), Ar 2 is a group represented by the general formulas (3) to (7).
一般式（３）において、Ａｒ３及びＡｒ４の炭素数６〜２０の芳香族基としては、例えば、フェニル基、トリル等の単環芳香族炭化水素基、フェナントリル基、ナフチル基、アントリル基、フルオレニル基、ピレニル基、ペリレニル基等の縮合多環芳香族炭化水素基、ビフェニル基、ターフェニル基等の環連結芳香族炭化水素基等が挙げられ、中でも、炭素数６〜２０の芳香族炭化水素基が好ましく、炭素数３〜１５の芳香族複素環基がより好ましい。
Ａｒ３及びＡｒ４の炭素数５〜１８の芳香族複素環基としては、例えば、ピリジル基、チエニル基、フリル基、オキサゾリル基、チアゾリル基、オキサジアゾリル基、ベンゾチエニル基、ジベンゾフリル基、ジベンゾチエニル基、ピラジニル基、ピリミジニル基、ピラゾリル基、イミダゾリル基、フェニルカルバゾリル基等が挙げられ、中でも、炭素数２〜２０の芳香族複素環基が好ましく、炭素数３〜１５の芳香族複素環基がより好ましい。
式（３）中、Ａｒ３とＡｒ４は、同一であっても異なっていてもよい。In the general formula (3), examples of the aromatic group having 6 to 20 carbon atoms of Ar 3 and Ar 4 include a monocyclic aromatic hydrocarbon group such as phenyl group and tolyl, phenanthryl group, naphthyl group, anthryl group, Examples thereof include condensed polycyclic aromatic hydrocarbon groups such as fluorenyl group, pyrenyl group and perylenyl group, and ring-linked aromatic hydrocarbon groups such as biphenyl group and terphenyl group, among which aromatic carbon atoms having 6 to 20 carbon atoms. A hydrogen group is preferable, and an aromatic heterocyclic group having 3 to 15 carbon atoms is more preferable.
Examples of the aromatic heterocyclic group having 5 to 18 carbon atoms of Ar 3 and Ar 4 include a pyridyl group, a thienyl group, a furyl group, an oxazolyl group, a thiazolyl group, an oxadiazolyl group, a benzothienyl group, a dibenzofuryl group, and a dibenzothienyl group. Group, pyrazinyl group, pyrimidinyl group, pyrazolyl group, imidazolyl group, phenylcarbazolyl group and the like. Among them, an aromatic heterocyclic group having 2 to 20 carbon atoms is preferable, and an aromatic heterocyclic ring having 3 to 15 carbon atoms is preferable. Groups are more preferred.
In formula (3), Ar 3 and Ar 4 may be the same or different.
一般式（３）で表される基としては、具体的に以下に列挙する基が挙げられる。 Specific examples of the group represented by the general formula (3) include the groups listed below.
一般式（４）において、Ｘ１は、酸素原子、硫黄原子、或いは、アルキル基、芳香族炭化水素基又は芳香族複素環基が置換した窒素原子である。
前記アルキル基としては、上記した炭素数１〜２４のアルキル基が挙げられ、前記芳香族炭化水素基としては、上記した炭素数１〜２４の芳香族炭化水素基が挙げられ、前記芳香族複素環基としては、上記した炭素数１〜２４の芳香族複素環基が挙げられ、好ましい基も同様である。
Ｘ１は、酸素原子、硫黄原子、又は、芳香族炭化水素基が置換した窒素原子が好ましい。In the general formula (4), X 1 is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.
Examples of the alkyl group include the above-described alkyl group having 1 to 24 carbon atoms, and examples of the aromatic hydrocarbon group include the above-described aromatic hydrocarbon group having 1 to 24 carbon atoms. Examples of the cyclic group include the above-described aromatic heterocyclic groups having 1 to 24 carbon atoms, and preferred groups are also the same.
X 1 is preferably an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an aromatic hydrocarbon group.
一般式（４）において、Ｘ２〜Ｘ５は窒素原子又は炭素原子であり、式（４）中、Ｘ２〜Ｘ５は同一であっても異なっていてもよい。中でも、Ｘ２〜Ｘ５は全て炭素原子、又は、１つが窒素原子であることがより好ましい。In the general formula (4), X 2 to X 5 are nitrogen atoms or carbon atoms, and in the formula (4), X 2 to X 5 may be the same or different. Among these, it is more preferable that all of X 2 to X 5 are carbon atoms or one is a nitrogen atom.
一般式（４）で表される基としては、具体的に以下に列挙する基が挙げられる。 Specific examples of the group represented by the general formula (4) include the groups listed below.
一般式（５）において、Ｘ２〜Ｘ５は上記一般式（４）と同様である。
一般式（５）で表される基としては、具体的に以下に列挙する基が挙げられる。In the general formula (5), X 2 to X 5 are the same as those in the general formula (4).
Specific examples of the group represented by the general formula (5) include the groups listed below.
一般式（６）において、Ｒ３の炭素数１〜２４のアルキル基、炭素数１〜２４の芳香族炭化水素基及び炭素数１〜２４の芳香族複素環基としては、上記一般式（１）で挙げたものと同様の基が挙げられ、好ましい基も同様である。In the general formula (6), the alkyl group having 1 to 24 carbon atoms, the aromatic hydrocarbon group having 1 to 24 carbon atoms, and the aromatic heterocyclic group having 1 to 24 carbon atoms in R 3 include the above general formula (1 ) And the same groups as mentioned above, and preferred groups are also the same.
一般式（６）で表される基としては、具体的に以下に列挙する基が挙げられる。 Specific examples of the group represented by the general formula (6) include the groups listed below.
一般式（７）において、Ｒ４の炭素数１〜２４のアルキル基、炭素数１〜２４の芳香族炭化水素基及び炭素数１〜２４の芳香族複素環基としては、上記一般式（１）で挙げたものと同様の基が挙げられ、好ましい基も同様である。In the general formula (7), as the alkyl group having 1 to 24 carbon atoms, the aromatic hydrocarbon group having 1 to 24 carbon atoms, and the aromatic heterocyclic group having 1 to 24 carbon atoms in R 4 , the above general formula (1 ) And the same groups as mentioned above, and preferred groups are also the same.
一般式（７）で表される基としては、具体的に以下に列挙する基が挙げられる。 Specific examples of the group represented by the general formula (7) include the groups listed below.
上記一般式（１）で示されるイミダゾール化合物の具体例としては、例えば、以下に列挙する化合物が挙げられる。 Specific examples of the imidazole compound represented by the general formula (1) include the compounds listed below.
一般式（１）で示されるイミダゾール化合物は、例えば、Ｊ．Ｏｒｇ．Ｃｈｅｍ，１９３７，２，３１９等に記載の公知一般の方法により製造することができる。さらに、イミダゾール化合物の置換基については、鈴木カップリング、薗頭カップリング等、公知の反応方法を用いて導入することが可能である。 Examples of the imidazole compound represented by the general formula (1) include J.M. Org. Chem, 1937, 2, 319 and the like can be produced by a known general method. Furthermore, the substituent of the imidazole compound can be introduced using a known reaction method such as Suzuki coupling or Sonogashira coupling.
本発明のイミダゾール化合物は、電子デバイス用材料として発光素子や有機薄膜太陽電池等に好適に用いることができる。詳細には、例えば、有機ＥＬディスプレイや有機ＥＬ照明等に用いる発光ダイオード等の発光素子の発光層に含有されるホスト材料として好適に用いることができる。 The imidazole compound of this invention can be used suitably for a light emitting element, an organic thin-film solar cell, etc. as an electronic device material. Specifically, for example, it can be suitably used as a host material contained in a light emitting layer of a light emitting element such as a light emitting diode used for an organic EL display, organic EL illumination, or the like.
本発明の電子デバイス用材料は、本発明のイミダゾール化合物を通常１〜１００重量％にて含むものである。目的とする用途により、公知の溶媒、他の発光材料、他のホスト材料、添加剤等を０〜９９重量％の範囲で含有していてもよい。 The electronic device material of the present invention contains the imidazole compound of the present invention in an amount of usually 1 to 100% by weight. Depending on the intended use, a known solvent, other light emitting materials, other host materials, additives and the like may be contained in the range of 0 to 99% by weight.
本発明の電子デバイスは、発光素子を含み、例えば、陰極及び陽極と、これら各極間に介在する発光層とを有する発光素子を含む。かかる発光素子としては、例えば、有機ＥＬ素子が挙げられる。有機ＥＬ素子では、陽極から正孔が、陰極から電子が発光層に注入され、それらが発光層中で再結合することにより励起子が生成し、これが失活する際に発光する。この有機ＥＬ素子は、発光光源、照明装置、表示デバイス等の電子デバイスに応用できる。
なお、有機ＥＬ素子の陰極、陽極、及び発光層を構成するその他の材料等は、公知のものから適宜選択して用いることができる。また、上記素子は、陰極と発光層との間に電子輸送材料を含む電子輸送層を備えていてもよく、陽極と有機薄膜層との間に正孔輸送材料を含む正孔輸送層を備えていてもよい。これらの電子輸送材料や正孔輸送材料も公知の材料を適宜用いることができる。The electronic device of the present invention includes a light emitting element, for example, a light emitting element having a cathode and an anode, and a light emitting layer interposed between these electrodes. Examples of such light emitting elements include organic EL elements. In the organic EL element, holes from the anode and electrons from the cathode are injected into the light emitting layer, and they recombine in the light emitting layer to generate excitons, which emit light when they are deactivated. This organic EL element can be applied to electronic devices such as a light emitting light source, a lighting device, and a display device.
The cathode, anode, and other materials constituting the light emitting layer of the organic EL element can be appropriately selected from known materials and used. The element may include an electron transport layer including an electron transport material between the cathode and the light emitting layer, and a hole transport layer including a hole transport material between the anode and the organic thin film layer. It may be. As these electron transporting material and hole transporting material, known materials can be appropriately used.
本発明のイミダゾール化合物は、電子デバイス用材料として発光層に含有される発光材料（ドーパント材料）やホスト材料として好適に用いることができる。
２種以上の化合物で構成される発光層中において、混合比（質量比）の最も低い化合物が発光材料であり、混合比（質量比）の最も高い化合物がホスト材料である。例えば、発光層が化合物Ａ、化合物Ｂの２種から構成され、その混合比がＡ：Ｂ＝１０：９０であれば、化合物Ａが発光材料化合物であり、化合物Ｂがホスト化合物である。さらに、発光層が化合物Ａ、化合物Ｂ、化合物Ｃの３種から構成され、その混合比がＡ：Ｂ：Ｃ＝５：１０：８５であれば、化合物Ａが発光材料化合物であり、化合物Ｃがホスト化合物である。
本発明のイミダゾール化合物を発光材料に用いる場合、キャリア輸送、注入材料、キャリアブロック材料として正孔輸送材料や電子輸送材料に適用することも可能である。The imidazole compound of the present invention can be suitably used as a light emitting material (dopant material) or a host material contained in the light emitting layer as a material for electronic devices.
In the light emitting layer composed of two or more compounds, the compound having the lowest mixing ratio (mass ratio) is the light emitting material, and the compound having the highest mixing ratio (mass ratio) is the host material. For example, when the light emitting layer is composed of two types of compound A and compound B and the mixing ratio is A: B = 10: 90, compound A is a light emitting material compound and compound B is a host compound. Further, when the light emitting layer is composed of three types of compound A, compound B, and compound C and the mixing ratio is A: B: C = 5: 10: 85, compound A is a light emitting material compound, and compound C Is a host compound.
When the imidazole compound of the present invention is used as a light emitting material, it can be applied to a hole transport material or an electron transport material as a carrier transport, injection material, or carrier block material.
また、かかる電子デバイス用材料は、本発明の新規イミダゾール化合物を含有するので、溶液塗布法、溶融塗布等の塗布法や蒸着法により基板上に薄膜を成膜し発光素子を製造することが可能である。
例えば、本発明の電子デバイス用材料を用いて発光素子の発光層を成膜する方法としては、該電子デバイス用材料の溶液を基板上に塗布する方法、該電子デバイス用材料を基板上に蒸着する方法、該電子デバイス用材料を溶融させて基板上に塗布する方法が挙げられる。In addition, since the electronic device material contains the novel imidazole compound of the present invention, it is possible to produce a light-emitting element by forming a thin film on a substrate by a coating method such as a solution coating method, a melt coating method, or a vapor deposition method. It is.
For example, as a method of forming a light-emitting layer of a light-emitting element using the electronic device material of the present invention, a method of applying a solution of the electronic device material on a substrate, and depositing the electronic device material on the substrate And a method in which the electronic device material is melted and applied onto a substrate.
かかる基板としては、一般的に電子デバイスに用いられる公知の基板が挙げられ、ガラス、水晶、サファイア、シリコン、炭化ケイ素、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリエーテルスルフォン、ポリイミド、ポリアラミド、シクロオレフィン系ポリマー及びポリカーボネイト等が挙げられる。
かかる基板は、ＩＴＯ等の透明導電層を有していてもよい。Examples of such a substrate include known substrates generally used for electronic devices, such as glass, quartz, sapphire, silicon, silicon carbide, polyethylene terephthalate, polyethylene naphthalate, polyether sulfone, polyimide, polyaramid, and cycloolefin polymers. And polycarbonate.
Such a substrate may have a transparent conductive layer such as ITO.
本発明の電子デバイス用材料の溶液を基板上に塗布する方法としては、スピンコート法、キャスト法、インクジェット法、印刷法等が挙げられる。電子デバイス用材料の溶液に用いられる溶剤としては、例えば、トルエン、キシレン等の芳香族化合物、１，２−ジクロロエタン、クロロベンゼン等の含ハロゲン溶剤、エチレングリコールジメチルエーテル等のエーテル系溶剤、酢酸エチル等の脂肪族エステル、アセトン、メチルエチルケトン等のケトン系溶剤、Ｎ，Ｎ−ジメチルホルムアミド等のアミド系溶剤、ジメチルスルホキシド等が挙げられる。これらは１種を単独で用いてもよく、２種以上を併用してもよい。
電子デバイス用材料の溶液を基板や他の層の上に塗布した後、必要に応じて、加熱乾燥や減圧乾燥等を行って溶剤を除去することによって、発光層が成膜される。Examples of the method for applying the solution of the electronic device material of the present invention on the substrate include a spin coating method, a casting method, an ink jet method, and a printing method. Examples of the solvent used in the solution of the electronic device material include aromatic compounds such as toluene and xylene, halogen-containing solvents such as 1,2-dichloroethane and chlorobenzene, ether solvents such as ethylene glycol dimethyl ether, and ethyl acetate. Examples include aliphatic esters, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, and dimethyl sulfoxide. These may be used alone or in combination of two or more.
After the solution of the electronic device material is applied on the substrate or other layers, the light emitting layer is formed by removing the solvent by performing drying by heating, drying under reduced pressure, or the like as necessary.
本発明の電子デバイス用材料を基板上に蒸着する方法としては、例えばシグマアルドリッチ「材料科学の基礎」Ｖｏｌ．１，Ｎｏ．１記載の公知の蒸着法を適用することができる。
また、本発明の電子デバイス用材料を基板上に溶融塗布する方法としては、一般的な溶融コーティング法等の溶融塗布法を適用することができる。As a method for depositing the electronic device material of the present invention on a substrate, for example, Sigma-Aldrich “Basics of Material Science” Vol. 1, No. 1 The well-known vapor deposition method of 1 is applicable.
Moreover, as a method of melt-coating the material for an electronic device of the present invention on a substrate, a melt coating method such as a general melt coating method can be applied.
以下、実施例を挙げて本発明を更に具体的に説明するが、本発明はその趣旨を超えない限り、以下の実施例に限定されるものではない。
実施例で得られた化合物は、それぞれ融点（ｍｐ）、赤外分光法（ＩＲ）、核磁気共鳴法（１Ｈ ＮＭＲ、１３Ｃ ＮＭＲ）、マトリックス支援レーザー脱離イオン化法（ＭＡＬＤＩ）と飛行時間型（ＴＯＦ）重量分析計（ＭＳ）を用いて同定した。
実施例にて採用した分析条件等を実施例中に記載した。EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated more specifically, this invention is not limited to a following example, unless the meaning is exceeded.
The compounds obtained in the examples have melting point (mp), infrared spectroscopy (IR), nuclear magnetic resonance ( 1 H NMR, 13 C NMR), matrix-assisted laser desorption / ionization (MALDI) and time of flight, respectively. Identified using a mold (TOF) gravimetric analyzer (MS).
Analysis conditions and the like employed in the examples are described in the examples.
〔参考例１〕
１−（３−ブロモフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
ベンズアルデヒド（３２．０ｇ）と３−ブロモアニリン（５１．８ｇ）に酢酸（３００ｍＬ）を加えて１時間加熱還流後、９，１０−フェナントレンキノン（６２．７ｇ）と酢酸アンモニウム（２３．３ｇ）を加えて更に３時間加熱還流した。反応混合物を室温まで放冷後、メタノール（３Ｌ）を加えて氷浴で冷却し、２時間静置した。析出した茶色固体を濾取、メタノール（２００ｍＬ）で洗浄し、茶色固体として１−（３−ブロモフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（８２．０ｇ、収率６１％）を得た。[Reference Example 1]
Synthesis of 1- (3-bromophenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole Acetic acid (300 mL) was added to benzaldehyde (32.0 g) and 3-bromoaniline (51.8 g). After heating to reflux for 1 hour, 9,10-phenanthrenequinone (62.7 g) and ammonium acetate (23.3 g) were added, and the mixture was further heated to reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, methanol (3 L) was added, cooled in an ice bath, and allowed to stand for 2 hours. The precipitated brown solid was collected by filtration, washed with methanol (200 mL), and 1- (3-bromophenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (82.0 g, yield) as a brown solid. 61%).
〔参考例２〕
１−（３−ブロモフェニル）−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
２−ナフチルアルデヒド（４．５ｇ）と３−ブロモアニリン（５．０ｇ）に酢酸（３０ｍＬ）を加えて２時間加熱還流後、９，１０−フェナントレンキノン（６．０ｇ）と酢酸アンモニウム（２．２ｇ）を加えて更に６時間加熱還流した。反応混合物を室温まで放冷後、メタノール（３００ｍＬ）を加えて氷浴で冷却し、２時間静置した。析出した固体を濾取、メタノールで洗浄し、茶色固体として１−（３−ブロモフェニル）−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（１０．０ｇ、収率６９％）を得た。[Reference Example 2]
Synthesis of 1- (3-bromophenyl) -2- (2-naphthyl) -1H-phenanthro [9,10-d] imidazole To 2-naphthylaldehyde (4.5 g) and 3-bromoaniline (5.0 g) Acetic acid (30 mL) was added, and the mixture was heated to reflux for 2 hours. 9,10-phenanthrenequinone (6.0 g) and ammonium acetate (2.2 g) were added, and the mixture was further heated to reflux for 6 hours. The reaction mixture was allowed to cool to room temperature, methanol (300 mL) was added, cooled in an ice bath, and allowed to stand for 2 hours. The precipitated solid was collected by filtration, washed with methanol, and 1- (3-bromophenyl) -2- (2-naphthyl) -1H-phenanthro [9,10-d] imidazole (10.0 g, yield) as a brown solid. 69%).
〔参考例３〕
２−（３−ニトロフェニル）−４，６−ジフェニル−１，３，５−トリアジンの合成
窒素雰囲気下、２−クロロ−４，６−ジフェニル−１，３，５−トリアジン（１２．２ｇ）、３−ニトロフェニルボロン酸（４．０ｇ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（０．５６ｇ）に脱気したトルエン（８０ｍＬ）、エタノール（４０ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（８０ｍＬ）を加え、４時間加熱還流した。反応混合物を室温まで放冷し、析出した固体を濾取し、メタノールで洗浄し、白色固体として２−（３−ニトロフェニル）−４，６−ジフェニル−１，３，５−トリアジン（７．６ｇ、収率８８％）を得た。[Reference Example 3]
Synthesis of 2- (3-nitrophenyl) -4,6-diphenyl-1,3,5-triazine Under nitrogen atmosphere, 2-chloro-4,6-diphenyl-1,3,5-triazine (12.2 g) , 3-nitrophenylboronic acid (4.0 g), and toluene (80 mL) degassed to tetrakis (triphenylphosphine) palladium (0) (0.56 g), ethanol (40 mL), and 2M aqueous sodium carbonate (80 mL) ) And heated to reflux for 4 hours. The reaction mixture is allowed to cool to room temperature, and the precipitated solid is collected by filtration, washed with methanol, and 2- (3-nitrophenyl) -4,6-diphenyl-1,3,5-triazine (7. 6 g, yield 88%).
〔参考例４〕
３−（４，６−ジフェニル−１，３，５−トリアジン−２−イル）アニリンの合成
オートクレーブに２−（３−ニトロフェニル）−４，６−ジフェニル−１，３，５−トリアジン（８．０ｇ）、５％パラジウム担持−活性炭素（５０％含水）（５．１ｇ）、およびＴＨＦ（２４０ｍＬ）を加えて、初期水素圧１ＭＰａ、２５℃で４時間水素添加反応を行った。得られた反応液を濾過し、ろ液を濃縮乾固することで、黄色固体として３−（４，６−ジフェニル−１，３，５−トリアジン−２−イル）アニリン（７．３ｇ、収率９９％）を得た。[Reference Example 4]
Synthesis of 3- (4,6-diphenyl-1,3,5-triazin-2-yl) aniline In an autoclave, 2- (3-nitrophenyl) -4,6-diphenyl-1,3,5-triazine (8 0.0 g), 5% palladium-supported activated carbon (containing 50% water) (5.1 g), and THF (240 mL) were added, and a hydrogenation reaction was performed at 25 ° C. for 4 hours at an initial hydrogen pressure of 1 MPa. The resulting reaction solution was filtered, and the filtrate was concentrated to dryness to give 3- (4,6-diphenyl-1,3,5-triazin-2-yl) aniline (7.3 g, yield) as a yellow solid. 99%).
〔実施例１〕
１−（４−ジベンゾチオフェン−３−イルフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（２０．０ｇ）、４−ジベンゾチオフェンボロン酸（１１．２ｇ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（１．０ｇ）に脱気したトルエン（１６０ｍＬ）、エタノール（８０ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（１６０ｍＬ）を加え、６時間加熱還流した。反応混合物を室温まで放冷し、析出した固体を濾取した。トルエンで再結晶を行い、白色固体として１−（４−ジベンゾチオフェン−３−イルフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（１０．５ｇ、収率４３％）を得た。[Example 1]
1- (4-Dibenzothiophen-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (20.0 g), 4-dibenzothiopheneboronic acid (11.2 g), and tetrakis ( Toluene (160 mL), ethanol (80 mL), and 2M aqueous sodium carbonate solution (160 mL) were added to triphenylphosphine) palladium (0) (1.0 g), and the mixture was heated to reflux for 6 hours. The reaction mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration. Recrystallization from toluene gave 1- (4-dibenzothiophen-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (10.5 g, 43% yield) as a white solid. Obtained.
Ｃｏｌｏｒｌｅｓｓ ｐｏｗｄｅｒ；ｍ．ｐ．２３８℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．３６（ｄｄ，Ｊ＝８．２，１．０Ｈｚ，１Ｈ），７．４１−７．４５（ｍ，４Ｈ），７．５０−７．５２（ｍ，２Ｈ），７．５７−７．６２（ｍ，３Ｈ），７．６８−７．７２（ｍ，３Ｈ），７．７７−７．９４（ｍ，４Ｈ），８．０２−８．０５（ｍ，２Ｈ），８．３６−８．３９（ｍ，２Ｈ），８．７２（ｄｄ，Ｊ＝９．２，１．２Ｈｚ，１Ｈ），８．８９（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ），８．９５（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ）．
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３）δ１２０．９，１２２．２，１２２．５，１２２．８，１２３．０，１２３．２，１２４．２，１２５．０，１２５．４，１２５．８，１２６．１，１２６．２，１２７．２，１２７．６，１２７．８，１２８．０，１２８．２，１２８．２，１２８．８，１２９．０，１２９．３，１２９．６，１２９．９，１３０．２，１３０．８，１３１．５，１３５．１，１３５．６，１３６．４，１３７．１，１３８．０，１３８．８，１３９．１，１４２．２，１５１．３．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ３９Ｈ２４Ｎ２Ｓ；５５２（Ｍ＋），ｆｏｕｎｄ：５５３（［Ｍ＋Ｈ］＋）Colorless powder; m. p. 238 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.36 (dd, J = 8.2, 1.0 Hz, 1H), 7.41-7.45 (m, 4H), 7.50-7.52 (M, 2H), 7.57-7.62 (m, 3H), 7.68-7.72 (m, 3H), 7.77-7.94 (m, 4H), 8.02-8 .05 (m, 2H), 8.36-8.39 (m, 2H), 8.72 (dd, J = 9.2, 1.2 Hz, 1H), 8.89 (d, J = 8. 4 Hz, 1H), 8.95 (d, J = 8.4 Hz, 1H).
13 C NMR (100 MHz, CDCl 3 ) δ 120.9, 122.2, 122.5, 122.8, 123.0, 123.2, 124.2, 125.0, 125.4, 125.8, 126 1,126.2,127.2,127.6,127.8,128.0,128.2,128.2,128.8,129.0,129.3,129.6,129.9 , 130.2, 130.8, 131.5, 135.1, 135.6, 136.4, 137.1, 138.0, 138.8, 139.1, 142.2, 151.3.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 39 H 24 N 2 S; 552 (M + ), found: 553 ([M + H] + )
〔実施例２〕
１−（９−フェニルカルバゾール−３−イルフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
窒素雰囲気下、参考例１で得た１−（３−ブロモフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（２０．０ｇ）、９−フェニルカルバゾール−３−ボロン酸（１４．０ｇ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（１．１ｇ）に脱気したトルエン（１４０ｍＬ）、エタノール（７０ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（１４０ｍＬ）を加え、６時間加熱還流した。反応混合物を室温まで放冷し、析出した固体を濾取した。得られた固体をＴＨＦ（３００ｍＬ）で加熱溶解させた後、氷冷しながらメタノール（３００ｍＬ）を加えた。析出した結晶を濾取し、白色固体として１−（９−フェニルカルバゾール−３−イルフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（１２．１ｇ、収率４４％）を得た。[Example 2]
Synthesis of 1- (9-phenylcarbazol-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole 1- (3-Bromophenyl)-obtained in Reference Example 1 under nitrogen atmosphere 2-phenyl-1H-phenanthro [9,10-d] imidazole (20.0 g), 9-phenylcarbazole-3-boronic acid (14.0 g), and tetrakis (triphenylphosphine) palladium (0) (1. 1 g) was added with degassed toluene (140 mL), ethanol (70 mL), and 2M aqueous sodium carbonate solution (140 mL), and the mixture was heated to reflux for 6 hours. The reaction mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration. The obtained solid was dissolved by heating in THF (300 mL), and methanol (300 mL) was added while cooling with ice. The precipitated crystals were collected by filtration, and 1- (9-phenylcarbazol-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (12.1 g, yield 44%) as a white solid. Got.
Ｃｏｌｏｒｌｅｓｓ ｐｏｗｄｅｒ；ｍ．ｐ．３０１℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．２７−７．４４（ｍ，９Ｈ），７．５４−７．５７（ｍ，２Ｈ），７．６２−７．７３（ｍ，８Ｈ），７．７８−７．８２（ｍ，２Ｈ），７．８５（ｄｄ，Ｊ＝８．６，１．６Ｈｚ，１Ｈ），８．１９（ｄ，Ｊ＝８．０Ｈｚ，１Ｈ），８．２１（ｄ，Ｊ＝１．６Ｈｚ，１Ｈ），８．３１（ｄ，Ｊ＝８．０Ｈｚ，１Ｈ），８．７２−８．７４（ｍ，２Ｈ），８．９０（ｄ，Ｊ＝８．８Ｈｚ，１Ｈ），８．９５（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ）．
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３）δ１１０．２，１１０．６，１１９．４，１２０．８，１２０．８，１２１．４，１２２．５，１２３．１，１２３．３，１２４．０，１２４．２，１２５．０，１２５．６，１２５．７，１２６．２，１２７．１，１２７．２，１２７．２，１２７．３，１２７．６，１２８．０，１２８．２，１２８．３，１２８．３，１２８．３，１２８．７，１２９．０，１２９．５，１２９．７，１３０．７，１３０．８，１３０．８，１３１．３，１３７．０，１３０．８，１３０．８，１３１．３，１３７．０，１３７．１，１３９．４，１４０．５，１４１．１，１４２．９，１５１．１．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ４５Ｈ２９Ｎ３；６１１（Ｍ＋），ｆｏｕｎｄ：６１２（［Ｍ＋Ｈ］＋）Colorless powder; m. p. 301 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.27-7.44 (m, 9H), 7.54-7.57 (m, 2H), 7.62-7.73 (m, 8H), 7.78-7.82 (m, 2H), 7.85 (dd, J = 8.6, 1.6 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 8.21 (D, J = 1.6 Hz, 1H), 8.31 (d, J = 8.0 Hz, 1H), 8.72-8.74 (m, 2H), 8.90 (d, J = 8. 8 Hz, 1H), 8.95 (d, J = 8.4 Hz, 1H).
13 C NMR (100 MHz, CDCl 3 ) δ 110.2, 110.6, 119.4, 120.8, 120.8, 121.4, 122.5, 123.1, 123.3, 124.0, 124 2, 125.0, 125.6, 125.7, 126.2, 127.1, 127.2, 127.2, 127.3, 127.6, 128.0, 128.2, 128.3 , 128.3, 128.3, 128.7, 129.0, 129.5, 129.7, 130.7, 130.8, 130.8, 131.3, 137.0, 130.8, 130 8, 131.3, 137.0, 137.1, 139.4, 140.5, 141.1, 142.9, 151.1.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 45 H 29 N 3 ; 611 (M + ), found: 612 ([M + H] + )
〔実施例３〕
２−フェニル−１−（３−ピリド［２，３−ｂ］インドール−９−イル−フェニル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
１−（３−ブロモフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（２２．８ｇ）、α−カルボリン（９．４ｇ）、ヨウ化銅（Ｉ）（９．７ｇ）、及び炭酸カリウム（２８．１ｇ）にジメチルアセトアミド（４００ｍＬ）を加え、４８時間加熱還流した。水（２Ｌ）を加えて３０分撹拌した。析出した粉末を濾取し、メタノールで洗浄した。得られた固体をＴＨＦで再結晶し、白色固体として２−フェニル−１−（３−ピリド［２，３−ｂ］インドール−９−イル−フェニル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（４．６ｇ、収率１７％）を得た。Example 3
Synthesis of 2-phenyl-1- (3-pyrido [2,3-b] indol-9-yl-phenyl) -1H-phenanthro [9,10-d] imidazole 1- (3-Bromophenyl) -2- Phenyl-1H-phenanthro [9,10-d] imidazole (22.8 g), α-carboline (9.4 g), copper (I) iodide (9.7 g), and potassium carbonate (28.1 g) with dimethyl Acetamide (400 mL) was added and heated to reflux for 48 hours. Water (2 L) was added and stirred for 30 minutes. The precipitated powder was collected by filtration and washed with methanol. The resulting solid was recrystallized from THF and 2-phenyl-1- (3-pyrido [2,3-b] indol-9-yl-phenyl) -1H-phenanthro [9,10-d] as a white solid. Imidazole (4.6 g, 17% yield) was obtained.
Ｃｏｌｏｒｌｅｓｓ ｓｏｌｉｄ；ｍ．ｐ．２７３℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．２３−７．２９（ｍ，３Ｈ），７．３２−７．３９（ｍ，５Ｈ），７．５１（ｔｄ，Ｊ＝７．８，１．２Ｈｚ，１Ｈ），７．６０（ｔｄ，Ｊ＝７．８，１．２Ｈｚ，１Ｈ），７．６６−７．７０（ｍ，３Ｈ），７．７９−７．８１（ｍ，２Ｈ），７．８６（ｔ，８．０Ｈｚ，１Ｈ），８．０９−８．１５（ｍ，３Ｈ），８．４１（ｄｄ，Ｊ＝４．８，２．０Ｈｚ，１Ｈ），８．４５（ｄｄ，Ｊ＝７．６，１．６Ｈｚ，１Ｈ），８．７７（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ），８．８１（ｄｄ，Ｊ＝８．０，１．２Ｈｚ，１Ｈ），８．８５（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ）．
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＴＨＦ−ｄ８）δ１１１．０，１１７．３，１１７．５，１２１．９，１２２．１，１２２．２，１２３．５，１２４．０，１２４．１，１２５．０，１２５．６，１２６．２，１２７．１，１２７．７，１２７．９，１２８．５，１２８．６，１２８．９，１２９．０，１２９．２，１２９．３，１２９．４，１３０．２，１３１．６，１３２．１，１３８．６，１３９．１，１４０．３，１４０．９，１４７．２，１５１．７，１５２．６．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ３８Ｈ２４Ｎ４；５３６（Ｍ＋），ｆｏｕｎｄ：５３７（［Ｍ＋Ｈ］＋）Colorless solid; m. p. 273 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.23-7.29 (m, 3H), 7.32-7.39 (m, 5H), 7.51 (td, J = 7.8, 1 .2 Hz, 1H), 7.60 (td, J = 7.8, 1.2 Hz, 1H), 7.66-7.70 (m, 3H), 7.79-7.81 (m, 2H) 7.86 (t, 8.0 Hz, 1H), 8.09-8.15 (m, 3H), 8.41 (dd, J = 4.8, 2.0 Hz, 1H), 8.45 ( dd, J = 7.6, 1.6 Hz, 1H), 8.77 (d, J = 8.4 Hz, 1H), 8.81 (dd, J = 8.0, 1.2 Hz, 1H), 8 .85 (d, J = 8.4 Hz, 1H).
13 C NMR (100 MHz, THF-d 8 ) δ 111.0, 117.3, 117.5, 121.9, 122.1, 122.2, 123.5, 124.0, 124.1, 125.0 , 125.6, 126.2, 127.1, 127.7, 127.9, 128.5, 128.6, 128.9, 129.0, 129.2, 129.3, 129.4, 130 2, 131.6, 132.1, 138.6, 139.1, 140.3, 140.9, 147.2, 151.7, 152.6.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 38 H 24 N 4 ; 536 (M + ), found: 537 ([M + H] + )
〔実施例４〕
１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
アルゴン雰囲気下、−７０℃にて、参考例１で得た１−（３−ブロモフェニル）−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（４０．０ｇ）の乾燥ＴＨＦ（４００ｍＬ）溶液に１．６Ｍブチルリチウムヘキサン溶液（６７．０ｍＬ）を２０分かけて滴下した。反応液を−７０℃で３０分攪拌後、ホウ酸トリメチル（６０．０ｍＬ）を１０分かけて滴下した。反応液を室温まで昇温し２時間撹拌した後、５％塩酸（１．３Ｌ）と酢酸エチル（１．３Ｌ）を加えて３０分攪拌した。有機層を硫酸マグネシウムで乾燥したのち濃縮乾固し、１−［３−（ジヒドロキシボリル）フェニル］−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの粗生成物（４４．４ｇ）を得た。
次いで、窒素雰囲気下、１−［３−（ジヒドロキシボリル）フェニル］−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（４４．４ｇ）、２−クロロ−４，６−ジフェニル−１，３，５−トリアジン（５４．５ｇ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（２．５ｇ）に脱気したトルエン（４００ｍＬ）、エタノール（２００ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（４００ｍＬ）を加え、３時間加熱還流した。反応混合物を室温まで放冷し、有機層を硫酸マグネシウムで乾燥の後、濃縮乾固した。ＴＨＦで再結晶を行い、黄色固体として１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−フェニル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（１０．８ｇ、収率２０％）を得た。Example 4
Synthesis of 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2-phenyl-1H-phenanthro [9,10-d] imidazole To a solution of 1- (3-bromophenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (40.0 g) obtained in Reference Example 1 in dry THF (400 mL) at 70 ° C. A 6M butyllithium hexane solution (67.0 mL) was added dropwise over 20 minutes. The reaction solution was stirred at −70 ° C. for 30 minutes, and trimethyl borate (60.0 mL) was added dropwise over 10 minutes. The reaction solution was warmed to room temperature and stirred for 2 hours, and then 5% hydrochloric acid (1.3 L) and ethyl acetate (1.3 L) were added and stirred for 30 minutes. The organic layer was dried over magnesium sulfate and concentrated to dryness to give a crude product of 1- [3- (dihydroxyboryl) phenyl] -2-phenyl-1H-phenanthro [9,10-d] imidazole (44.4 g). Got.
Then, under a nitrogen atmosphere, 1- [3- (dihydroxyboryl) phenyl] -2-phenyl-1H-phenanthro [9,10-d] imidazole (44.4 g), 2-chloro-4,6-diphenyl-1 , 3,5-triazine (54.5 g) and tetrakis (triphenylphosphine) palladium (0) (2.5 g) degassed toluene (400 mL), ethanol (200 mL), and 2M aqueous sodium carbonate solution (400 mL) And heated to reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, and the organic layer was dried over magnesium sulfate and concentrated to dryness. Recrystallization from THF gave 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2-phenyl-1H-phenanthro [9,10- as a yellow solid. d] Imidazole (10.8 g, 20% yield) was obtained.
Ｙｅｌｌｏｗ ｐｏｗｄｅｒ；ｍ．ｐ．２９９℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．２０（ｄｄ，Ｊ＝８．４，１．２Ｈｚ，１Ｈ），７．３２−７．３８（ｍ，５Ｈ），７．５３−７．６３（ｍ，５Ｈ），７．６７−７．７２（ｍ，５Ｈ），７．８２（ｔ，Ｊ＝７．６Ｈｚ，１Ｈ），８．００（ｔ，Ｊ＝７．８Ｈｚ，１Ｈ），８．１２−８．１５（ｍ，１Ｈ），８．７１−８．７６（ｍ，５Ｈ），８．９１（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ），８．９６（ｄ，Ｊ＝８．０Ｈｚ，１Ｈ），９．０１（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），９．１０（ｄｔ，Ｊ＝８．０，１．２Ｈｚ，１Ｈ）．
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３）δ１２０．７，１２２．５，１２３．０，１２４．２，１２５．１，１２５．８，１２６．３，１２７．２，１２７．３，１２８．０，１２８．２，１２８．４，１２８．８，１２９．０，１２９．３，１２９．５，１２９．６，１２９．８，１３０．７，１３０．８，１３１．６，１３３．７，１３４．２，１３５．６，１３７．０，１３８．１，１３９．６，１５１．１，１７０．４，１７１．４．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ４２Ｈ２７Ｎ５；６０１（Ｍ＋），ｆｏｕｎｄ：６０２（［Ｍ＋Ｈ］＋）Yellow powder; m. p. 299 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.20 (dd, J = 8.4, 1.2 Hz, 1H), 7.32-7.38 (m, 5H), 7.53-7.63 (M, 5H), 7.67-7.72 (m, 5H), 7.82 (t, J = 7.6 Hz, 1H), 8.00 (t, J = 7.8 Hz, 1H), 8 .12-8.15 (m, 1H), 8.71-8.76 (m, 5H), 8.91 (d, J = 8.4 Hz, 1H), 8.96 (d, J = 8. 0 Hz, 1H), 9.01 (t, J = 1.8 Hz, 1H), 9.10 (dt, J = 8.0, 1.2 Hz, 1H).
13 C NMR (100 MHz, CDCl 3 ) δ 120.7, 122.5, 123.0, 124.2, 125.1, 125.8, 126.3, 127.2, 127.3, 128.0, 128 .2,128.4,128.8,129.0,129.3,129.5,129.6,129.8,130.7,130.8,131.6,133.7,134.2 135.6, 137.0, 138.1, 139.6, 151.1, 170.4, 171.4.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 42 H 27 N 5 ; 601 (M + ), found: 602 ([M + H] + )
〔実施例５〕
１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］の合成
アルゴン雰囲気下、−７０℃にて、参考例２で得た１−（３−ブロモフェニル）−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（３５．０ｇ）の乾燥ＴＨＦ（３５０ｍＬ）溶液に１．６Ｍブチルリチウムヘキサン溶液（５０．０ｍＬ）を２０分かけて滴下した。反応液を−７０℃にて３０分攪拌後、ホウ酸トリメチル（４５ｍＬ）を１０分かけて滴下した。反応液を室温まで昇温し２時間撹拌した後、５％塩酸（１．０Ｌ）と酢酸エチル（１．０Ｌ）を加えて３０分攪拌した。有機層を硫酸マグネシウムで乾燥したのち濃縮乾固し、１−［３−（ジヒドロキシボリル）フェニル］−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの粗生成物（３８．６ｇ）を得た。
次いで、窒素雰囲気下、１−［３−（ジヒドロキシボリル）フェニル］−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（３８．６ｇ）、２−クロロ−４，６−ジフェニル−１，３，５−トリアジン（４２．０ｇ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０）（１．９ｇ）に脱気したトルエン（３６０ｍＬ）、エタノール（１８０ｍＬ）、及び２Ｍ炭酸ナトリウム水溶液（３６０ｍＬ）を加え、６間加熱還流した。反応混合物を室温まで放冷し、析出した固体を濾取した。得られた固体をＴＨＦで再結晶し、黄色固体として１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−（２−ナフチル）−１Ｈ−フェナントロ［９，１０−ｄ］（１４．０ｇ、収率２６％）を得た。Example 5
Synthesis of 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2- (2-naphthyl) -1H-phenanthro [9,10-d] Argon atmosphere Below, dry THF of 1- (3-bromophenyl) -2- (2-naphthyl) -1H-phenanthro [9,10-d] imidazole (35.0 g) obtained in Reference Example 2 at −70 ° C. To the (350 mL) solution, 1.6 M butyl lithium hexane solution (50.0 mL) was added dropwise over 20 minutes. The reaction solution was stirred at −70 ° C. for 30 minutes, and trimethyl borate (45 mL) was added dropwise over 10 minutes. The reaction solution was warmed to room temperature and stirred for 2 hours, and then 5% hydrochloric acid (1.0 L) and ethyl acetate (1.0 L) were added and stirred for 30 minutes. The organic layer was dried over magnesium sulfate and concentrated to dryness to give a crude product of 1- [3- (dihydroxyboryl) phenyl] -2- (2-naphthyl) -1H-phenanthro [9,10-d] imidazole ( 38.6 g) was obtained.
Then, under nitrogen atmosphere, 1- [3- (dihydroxyboryl) phenyl] -2- (2-naphthyl) -1H-phenanthro [9,10-d] imidazole (38.6 g), 2-chloro-4,6 -Toluene (360 mL), ethanol (180 mL), and 2M sodium carbonate degassed to diphenyl-1,3,5-triazine (42.0 g) and tetrakis (triphenylphosphine) palladium (0) (1.9 g) An aqueous solution (360 mL) was added, and the mixture was heated to reflux for 6 minutes. The reaction mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration. The obtained solid was recrystallized from THF, and 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2- (2-naphthyl)-was obtained as a yellow solid. 1H-phenanthro [9,10-d] (14.0 g, 26% yield) was obtained.
Ｙｅｌｌｏｗ ｐｏｗｄｅｒ；ｍ．ｐ．２８２℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．０９−７．１３（ｍ，１Ｈ），７．２２−７．２９（ｍ，３Ｈ），７．３１−７．３９（ｍ，５Ｈ），７．４１−７．４５（ｍ，２Ｈ），７．４９−７．５３（ｍ，２Ｈ），７．５９−７．６６（ｍ，３Ｈ），７．７９（ｔ，Ｊ＝７．６Ｈｚ，１Ｈ），７．８２−７．８５（ｍ，１Ｈ），７．８５（ｄｄ，Ｊ＝９．０，１．８Ｈｚ，１Ｈ），７．９９（ｓ，１Ｈ），８．６１−８．６３（ｍ，４Ｈ），８．６６（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ），８．７２（ｄ，Ｊ＝８．０Ｈｚ，１Ｈ），８．７９（ｄｄ，Ｊ＝８．０，１．２Ｈｚ，１Ｈ），９．０４（ｄｔ，Ｊ＝７．６，１．６Ｈｚ，１Ｈ），９．０８（ｔ，Ｊ＝１．６Ｈｚ，１Ｈ）
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３）δ１２０．７，１２２．６，１２３．１，１２３．２，１２４．１，１２４．７，１２５．３，１２６．１，１２６．２，１２６．５，１２６．９，１２７．４，１２７．５，１２７．６，１２８．３，１２８．４，１２８．５，１２８．６，１２８．９，１２９．３，１２９．４，１３０．１，１３０．７，１３２．６，１３３．０，１３３．２，１３３．４，１３５．９，１３７．８，１３８．７，１４０．２，１５０．４，１７０４，１７０１．９．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ４６Ｈ２９Ｎ５；６５１（Ｍ＋），ｆｏｕｎｄ：６５２（［Ｍ＋Ｈ］＋）Yellow powder; m. p. 282 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.09-7.13 (m, 1H), 7.22-7.29 (m, 3H), 7.31-7.39 (m, 5H), 7.41-7.45 (m, 2H), 7.49-7.53 (m, 2H), 7.59-7.66 (m, 3H), 7.79 (t, J = 7.6 Hz) , 1H), 7.82-7.85 (m, 1H), 7.85 (dd, J = 9.0, 1.8 Hz, 1H), 7.99 (s, 1H), 8.61-8 .63 (m, 4H), 8.66 (d, J = 8.4 Hz, 1H), 8.72 (d, J = 8.0 Hz, 1H), 8.79 (dd, J = 8.0, 1.2 Hz, 1H), 9.04 (dt, J = 7.6, 1.6 Hz, 1H), 9.08 (t, J = 1.6 Hz, 1H)
13 C NMR (100 MHz, CDCl 3 ) δ 120.7, 122.6, 123.1, 123.2, 124.1, 124.7, 125.3, 126.1, 126.2, 126.5, 126 .9, 127.4, 127.5, 127.6, 128.3, 128.4, 128.5, 128.6, 128.9, 129.3, 129.4, 130.1, 130.7 132.6, 133.0, 133.2, 133.4, 135.9, 137.8, 138.7, 140.2, 150.4, 1704, 1701.9.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 46 H 29 N 5 ; 651 (M + ), found: 652 ([M + H] + )
〔実施例６〕
１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−ピリジン−４−イル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾールの合成
４−ピリジンカルボキシアルデヒド（２．２ｇ）と３−（４，６−ジフェニル−１，３，５−トリアジン−２−イル）アニリン（６．８ｇ）に酢酸（７０ｍＬ）を加えて４０℃で１時間撹拌後、９，１０−フェナントレンキノン（４．３ｇ）と酢酸アンモニウム（１．６ｇ）を加えて７０℃で５時間撹拌した。反応混合物を室温まで放冷後、メタノール（３００ｍＬ）を加えて氷浴で冷却し、２時間静置した。析出した固体を濾取し、メタノールで洗浄した。得られた固体をＴＨＦで再結晶し、淡黄色固体として１−［３−（４，６−ジフェニル−［１，３，５］トリアジン−２−イル）フェニル］−２−ピリジン−４−イル−１Ｈ−フェナントロ［９，１０−ｄ］イミダゾール（７．５ｇ、収率６０％）を得た。Example 6
Synthesis of 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2-pyridin-4-yl-1H-phenanthro [9,10-d]
Ｐａｌｅ ｙｅｌｌｏｗ ｐｏｗｄｅｒ；ｍ．ｐ．３１６℃
１Ｈ ＮＭＲ（４００ＭＨｚ，ＴＨＦ−ｄ８）δ７．３８（ｔｄ，Ｊ＝７．８，１．２Ｈｚ，１Ｈ），７．４８（ｄｄ，Ｊ＝８．４，１．２Ｈｚ，１Ｈ），７．６１−７．６８（ｍ，５Ｈ），７．７１−７．７５（ｍ，４Ｈ），７．８０（ｔｄ，Ｊ＝７．８，１．６Ｈｚ，１Ｈ），７．８８（ｔｄ，Ｊ＝７．７，１Ｈｚ，１Ｈ），８．１１−８．１２（ｍ，２Ｈ），８．６１−８．６２（ｍ，２Ｈ），８．９０−８．９４（ｍ，５Ｈ），９．０１（ｔ，Ｊ＝７．８Ｈｚ，２Ｈ），９．３２−９．３８（ｍ，２Ｈ）．
１３Ｃ ＮＭＲ（１００ＭＨｚ，ＴＨＦ−ｄ８）δ１２０．８，１２２．３，１２２．５，１２２．９，１２３．２，１２４．２，１２５．２，１２５．７，１２６．４，１２７．１，１２７．４，１２８．５，１２８．９，１２９．０，１２９．１，１２９．７，１３０．５，１３１．０，１３２．７，１３３．１，１３５．８，１３７．６，１３７．８，１３９．０，１３９．６，１４７．６，１４９．８．
ＭＡＬＤＩ−ＴＯＦ−ＭＳ（ｐｏｓｉｔｉｖｅ，Ｄｉｔｈｒａｎｏｌ）ｍ／ｚ：ｃａｌｃｄ．ｆｏｒ Ｃ４１Ｈ２６Ｎ６；６０２（Ｍ＋），ｆｏｕｎｄ：６０２（Ｍ＋）Pale yellow powder; m. p. 316 ° C
1 H NMR (400 MHz, THF-d 8 ) δ 7.38 (td, J = 7.8, 1.2 Hz, 1H), 7.48 (dd, J = 8.4, 1.2 Hz, 1H), 7 .61-7.68 (m, 5H), 7.71-7.75 (m, 4H), 7.80 (td, J = 7.8, 1.6 Hz, 1H), 7.88 (td, J = 7.7, 1 Hz, 1H), 8.11-8.12 (m, 2H), 8.61-8.62 (m, 2H), 8.90-8.94 (m, 5H), 9.01 (t, J = 7.8 Hz, 2H), 9.32-9.38 (m, 2H).
13 C NMR (100 MHz, THF-d 8 ) δ 120.8, 122.3, 122.5, 122.9, 123.2, 124.2, 125.2, 125.7, 126.4, 127.1 , 127.4, 128.5, 128.9, 129.0, 129.1, 129.7, 130.5, 131.0, 132.7, 133.1, 135.8, 137.6, 137 .8, 139.0, 139.6, 147.6, 149.8.
MALDI-TOF-MS (positive, Dithanol) m / z: calcd. for C 41 H 26 N 6 ; 602 (M + ), found: 602 (M + )
〔実施例７〕
＜発光素子の評価＞
パターニングを施した洗浄済みＩＴＯ基板（膜厚１１０ｎｍ）に真空蒸着にてＴＡＰＣ（下記化学式参照）（４０ｎｍ）を製膜し、ホール輸送層を形成した。これにＩｒ（ｐｐｙ）３（下記化学式参照）と実施例１のイミダゾール化合物を膜厚比２０：１になるように共蒸着により製膜し発光層（２０ｎｍ）を形成した。次いでＴｐＰｙＰＢ（下記化学式参照）（５０ｎｍ）を製膜し、電子輸送層を製膜した後、フッ化リチウム（０．５ｎｍ）とアルミニウム（１００ｎｍ）を成膜して陰極を形成し、キャップガラスによる封止を行い、２ｍｍ角の発光素子を作成した。
この発光素子に電圧を印加することで緑色発光が確認された。得られた発光素子の素子特性（駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ））をＩ−Ｖ−Ｌ測定装置（コニカミノルタセンシング株式会社製「ＣＳ−２０００」）により測定した。Example 7
<Evaluation of light emitting element>
TAPC (see the following chemical formula) (40 nm) was formed by vacuum deposition on a patterned ITO substrate (film thickness 110 nm) subjected to patterning to form a hole transport layer. Ir (ppy) 3 (refer to the following chemical formula) and the imidazole compound of Example 1 were formed on this by co-evaporation so as to have a film thickness ratio of 20: 1 to form a light emitting layer (20 nm). Next, TpPyPB (refer to the following chemical formula) (50 nm) is formed, an electron transport layer is formed, lithium fluoride (0.5 nm) and aluminum (100 nm) are formed, a cathode is formed, and the cap glass is used. Sealing was performed to produce a 2 mm square light emitting device.
Green light emission was confirmed by applying a voltage to the light emitting element. The element characteristics (driving voltage (V) and current efficiency (cd / A)) of the obtained light-emitting element were measured with an I-V-L measuring device (“CS-2000” manufactured by Konica Minolta Sensing Co., Ltd.).
〔実施例８〕
実施例７において用いた実施例１のイミダゾール化合物を実施例２で合成したイミダゾール化合物に替えた以外は同様に発光素子を作成した。
この発光素子に電圧を印加することで緑色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。Example 8
A light emitting device was similarly produced except that the imidazole compound of Example 1 used in Example 7 was replaced with the imidazole compound synthesized in Example 2.
Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
〔比較例１〕
実施例７において用いた実施例１のイミダゾール化合物を一般的なホスト化合物であるＣＢＰ（下記化学式参照）に替えた以外は同様に発光素子を作成した。
この発光素子に電圧を印加することで緑色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。[Comparative Example 1]
A light emitting device was similarly produced except that the imidazole compound of Example 1 used in Example 7 was replaced with CBP (see the following chemical formula) which is a general host compound.
Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
上記の実施例７，８及び比較例１で製造された発光素子の１，０００ｃｄ／ｍ２における駆動電圧及び電流効率を表１に示す。これらの発光素子の発光輝度−電圧特性、及び電流効率−電流密度の比較を図１、図２に示す。Table 1 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Examples 7 and 8 and Comparative Example 1 described above. A comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements is shown in FIGS.
〔実施例９〕
パターニングを施した洗浄済みＩＴＯ基板（膜厚１１０ｎｍ）に真空蒸着にてＨＡＴ−ＣＮ（下記化学式参照）（１ｎｍ）、次いでＨＴ１（下記化学式参照）（４０ｎｍ）を成膜し、正孔注入層と正孔輸送層を形成した。これにＩｒ（ｐｐｙ）３と実施例４のイミダゾール化合物を膜厚比１：２０になるように共蒸着により製膜し発光層（２０ｎｍ）を形成した。次いでＥＴ１とＬｉｑ（下記化学式参照）を膜厚比１：１になるように共蒸着により成膜し、電子輸送層（５０ｎｍ）を製膜した後、フッ化リチウム（０．５ｎｍ）とアルミニウム（１００ｎｍ）を成膜して陰極を形成し、キャップガラスによる封止を行い、２ｍｍ角の発光素子を作成した。
この発光素子に電圧を印加することで緑色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。Example 9
HAT-CN (refer to the following chemical formula) (1 nm) and then HT1 (refer to the following chemical formula) (40 nm) are formed on the cleaned ITO substrate (film thickness 110 nm) subjected to patterning by vacuum deposition, A hole transport layer was formed. Ir (ppy) 3 and the imidazole compound of Example 4 were formed into a film by co-evaporation so that the film thickness ratio was 1:20, thereby forming a light emitting layer (20 nm). Next, ET1 and Liq (see the following chemical formula) were formed by co-evaporation so that the film thickness ratio was 1: 1, and after forming an electron transport layer (50 nm), lithium fluoride (0.5 nm) and aluminum ( 100 nm) was formed to form a cathode and sealed with cap glass to produce a 2 mm square light emitting device.
Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
〔比較例２〕
実施例９において用いた実施例４のイミダゾール化合物を一般的なホスト化合物であるＣＢＰに替えた以外は同様に発光素子を作成した。
この発光素子に電圧を印加することで緑色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。[Comparative Example 2]
A light emitting device was similarly produced except that the imidazole compound of Example 4 used in Example 9 was replaced with CBP which is a general host compound.
Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
上記の実施例９及び比較例２で製造された発光素子の１，０００ｃｄ／ｍ２における駆動電圧及び電流効率を表２に示す。これらの発光素子の発光輝度−電圧特性、及び電流効率−電流密度の比較を図３、図４に示す。Table 2 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Example 9 and Comparative Example 2 described above. Comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements is shown in FIGS.
〔実施例１０〕
パターニングを施した洗浄済みＩＴＯ基板（膜厚１５０ｎｍ）に真空蒸着にてＨＡＴ−ＣＮ（１ｎｍ）、次いでＨＴ１（４０ｎｍ）を成膜し、正孔注入層と正孔輸送層を形成した。これにＩｒ（ｐｉｃ）３（下記化学式参照）と実施例５のイミダゾール化合物を膜厚比１：２０になるように共蒸着により製膜し発光層（２０ｎｍ）を形成した。次いでＥＴ１とＬｉｑを膜厚比１：１になるように共蒸着により成膜し、電子輸送層（５０ｎｍ）を製膜した後、フッ化リチウム（０．５ｎｍ）とアルミニウム（１００ｎｍ）を成膜して陰極を形成し、キャップガラスによる封止を行い、２ｍｍ角の発光素子を作成した。
この発光素子に電圧を印加することで赤色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。Example 10
HAT-CN (1 nm) and then HT1 (40 nm) were formed by vacuum deposition on a patterned ITO substrate (thickness 150 nm) subjected to patterning to form a hole injection layer and a hole transport layer. Ir (pic) 3 (refer to the following chemical formula) and the imidazole compound of Example 5 were formed on this by co-evaporation so as to have a film thickness ratio of 1:20 to form a light emitting layer (20 nm). Next, ET1 and Liq were formed by co-evaporation so as to have a film thickness ratio of 1: 1, an electron transport layer (50 nm) was formed, and then lithium fluoride (0.5 nm) and aluminum (100 nm) were formed. Then, a cathode was formed and sealed with a cap glass to produce a 2 mm square light emitting device.
Red light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
〔比較例３〕
実施例１０において用いた実施例５のイミダゾール化合物を一般的なホスト化合物であるＣＢＰに替えた以外は同様に発光素子を作成した。
この発光素子に電圧を印加することで赤色発光が確認された。得られた発光素子の駆動電圧（Ｖ）と電流効率（ｃｄ／Ａ）を、実施例７と同様に測定した。[Comparative Example 3]
A light emitting device was similarly produced except that the imidazole compound of Example 5 used in Example 10 was replaced with CBP which is a general host compound.
Red light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
上記の実施例１０及び比較例３で製造された発光素子の１，０００ｃｄ／ｍ２における駆動電圧及び電流効率を表３に示す。これらの発光素子の発光輝度−電圧特性、及び電流効率−電流密度の比較を図５、図６に示す。Table 3 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Example 10 and Comparative Example 3 above. Comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements is shown in FIGS.
表１〜３及び図１〜６の結果より、本発明のイミダゾール化合物を用いた発光素子（実施例７〜１０）は、ＣＢＰを用いた発光素子（比較例１〜３）と比較し、駆動電圧も低く、電流効率も高いことがわかった。この結果から、本発明のイミダゾール化合物を用いることにより、低電圧での駆動特性に優れ、安定で高い量子効率の発光素子を得ることができることがわかる。 From the results of Tables 1 to 3 and FIGS. 1 to 6, the light emitting devices using the imidazole compound of the present invention (Examples 7 to 10) are driven in comparison with the light emitting devices using CBP (Comparative Examples 1 to 3). It was found that the voltage was low and the current efficiency was high. From this result, it can be seen that by using the imidazole compound of the present invention, it is possible to obtain a light emitting element which is excellent in driving characteristics at a low voltage, stable and has high quantum efficiency.
本発明の新規イミダゾール化合物を含有する電子デバイス用材料は、発光素子や有機薄膜太陽電池等の様々な電子デバイスに利用することができる。例えば、有機ＥＬ素子等の発光素子を含む様々な電子デバイス、より具体的には、フラットパネル・ディスプレイ（例えば、コンピュータ用ディスプレイや壁掛けテレビ）や面発光体光源（例えば、照明、複写機用光源、液晶ディスプレイ用バックライト光源、計器類のバックライト光源）、表示板、標識灯等の電子デバイスにおいて、好適に利用することができる。 The electronic device material containing the novel imidazole compound of the present invention can be used in various electronic devices such as light-emitting elements and organic thin-film solar cells. For example, various electronic devices including light-emitting elements such as organic EL elements, more specifically, flat panel displays (for example, computer displays and wall-mounted televisions) and surface-emitting body light sources (for example, lighting, light sources for copying machines) , Liquid crystal display backlight light source, instrument backlight light source), display boards, beacon lamps and other electronic devices.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090114008A (en) * | 2008-04-29 | 2009-11-03 | 주식회사 엘지화학 | New imidazole derivatives and organic electronic device using the same |
| KR20120096383A (en) * | 2011-02-22 | 2012-08-30 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| JP2014105209A (en) * | 2012-11-26 | 2014-06-09 | Universal Display Corp | Organic luminescent compound with delayed fluorescence |
| KR20140094408A (en) * | 2013-01-22 | 2014-07-30 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN104447566A (en) * | 2013-09-13 | 2015-03-25 | 沈阳工业大学 | N1 biphenyl linked phenanthroimidazole compound, preparation method and application thereof |
| CN104672244A (en) * | 2015-02-14 | 2015-06-03 | 上海道亦化工科技有限公司 | Compound based on carbazole derivative |
-
2015
- 2015-09-29 JP JP2017542567A patent/JPWO2017056205A1/en active Pending
- 2015-09-29 WO PCT/JP2015/077632 patent/WO2017056205A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090114008A (en) * | 2008-04-29 | 2009-11-03 | 주식회사 엘지화학 | New imidazole derivatives and organic electronic device using the same |
| KR20120096383A (en) * | 2011-02-22 | 2012-08-30 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| JP2014105209A (en) * | 2012-11-26 | 2014-06-09 | Universal Display Corp | Organic luminescent compound with delayed fluorescence |
| KR20140094408A (en) * | 2013-01-22 | 2014-07-30 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN104447566A (en) * | 2013-09-13 | 2015-03-25 | 沈阳工业大学 | N1 biphenyl linked phenanthroimidazole compound, preparation method and application thereof |
| CN104672244A (en) * | 2015-02-14 | 2015-06-03 | 上海道亦化工科技有限公司 | Compound based on carbazole derivative |
Non-Patent Citations (2)
| Title |
|---|
| HUANG, HONG ET AL.: "Controllably tunable phenanthroimidazole-carbazole hybrid bipolar host materials for efficient green", JOURNAL OF MATERIALS CHEMISTRY C, vol. Volume 1 Issue 37, JPN6015048802, 2013, pages 5899 - 5908, ISSN: 0004159095 * |
| HUANG, HONG ET AL.: "Simple Phenanthroimidazole/Carbazole Hybrid Bipolar Host Materials for Highly Efficient Green and Ye", THE JOURNAL OF PHYSICAL CHEMISTRY C, vol. Volume 116 Issue 36, JPN6015048801, 2012, pages 19458 - 19466, ISSN: 0004159094 * |
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