JP5173836B2 - 有機エレクトロルミネッセンス化合物およびエレクトロルミネッセンス物質としてそれを使用したディスプレイデバイス - Google Patents
有機エレクトロルミネッセンス化合物およびエレクトロルミネッセンス物質としてそれを使用したディスプレイデバイス Download PDFInfo
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- JP5173836B2 JP5173836B2 JP2008552233A JP2008552233A JP5173836B2 JP 5173836 B2 JP5173836 B2 JP 5173836B2 JP 2008552233 A JP2008552233 A JP 2008552233A JP 2008552233 A JP2008552233 A JP 2008552233A JP 5173836 B2 JP5173836 B2 JP 5173836B2
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- 150000001875 compounds Chemical class 0.000 title claims description 54
- 239000000463 material Substances 0.000 title claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052790 beryllium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims 3
- 230000003796 beauty Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 32
- -1 compound compound Chemical class 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 12
- 0 C*c(cccc1)c1-c1ccc(cccc2)c2*1I Chemical compound C*c(cccc1)c1-c1ccc(cccc2)c2*1I 0.000 description 9
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 8
- GHGZVWOTJDLREY-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2O1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 8
- PMVRBPKKJNHTLA-UHFFFAOYSA-N 2-(1-phenylbenzimidazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 PMVRBPKKJNHTLA-UHFFFAOYSA-N 0.000 description 8
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 8
- 239000004246 zinc acetate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 6
- HPDNGBIRSIWOST-UHFFFAOYSA-N 2-pyridin-2-ylphenol Chemical compound OC1=CC=CC=C1C1=CC=CC=N1 HPDNGBIRSIWOST-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DIMYTQPLZWDZFE-UHFFFAOYSA-L beryllium sulfate tetrahydrate Chemical compound [Be+2].O.O.O.O.[O-]S([O-])(=O)=O DIMYTQPLZWDZFE-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- KQHXBDOEECKORE-UHFFFAOYSA-L beryllium sulfate Chemical compound [Be+2].[O-]S([O-])(=O)=O KQHXBDOEECKORE-UHFFFAOYSA-L 0.000 description 4
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- G08G1/00—Traffic control systems for road vehicles
- G08G1/07—Controlling traffic signals
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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- Electroluminescent Light Sources (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
L1L2M 〔化学式1〕
50mLのメタノール中に、2−ピリジン−2−イル−フェノール(1.0g、5.84mmol)を溶解させ、それに10mLの1M水酸化ナトリウム水溶液を加えた。この溶液を混合したものに、10mLのメタノール水溶液(メタノール7mL:水3mL)中の硫酸ベリリウム四水和物(1.05g、5.93mmol)の溶液を滴下し、得られた混合物を周囲温度で2時間撹拌した。撹拌終了後、50mLのメタノール中に溶解させた2−ヒドロキシ−フェニルベンゾオキサゾール(1.54g、7.30mmol)をゆっくりと加えた。その反応溶液を次に周囲温度で2時間撹拌した。溶液の温度を50℃まで上昇させ、その溶液を10時間撹拌した。
MS/FAB:391(測定値)、391.43(計算値)
EA:C 73.55%、H 4.59%、N 7.05%、O 12.41%
50mLのメタノール中に、2−ピリジン−2−イル−フェノール(1.0g、5.84mmol)を溶解させ、それに10mLの1M水酸化ナトリウム水溶液を加えた。この溶液を混合したものに、メタノール(10mL)中に溶解させた酢酸亜鉛(0.95g、5.18mmol)を滴下し、得られた混合物を周囲温度で2時間撹拌した。撹拌終了後、50mLのメタノール中に溶解させた2−ヒドロキシ−フェニルベンゾオキサゾール(1.50g、7.10mmol)をゆっくりと加えた。その反応混合物を次に周囲温度で10時間撹拌した。
MS/FAB: 447(測定値)、447.79(計算値)
EA:C 64.22%、H 4.01%、N 6.05%、O 10.95%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、10−ヒドロキシベンゾ[h]キノリン(1.48g、7.58mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して、表題化合物の化合物(1−3)(0.35g、0.84mmol、収率:14%)を得た。
MS/FAB:415(測定値)、415.46(計算値)
EA:C 75.02%、H 4.27%、N 6.64%、O 11.65%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、10−ヒドロキシベンゾ[h]キノリン(1.48g、7.58mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して、表題化合物の化合物(1−4)(0.52g、1.10mmol、収率:19%)を得た。
MS/FAB: 471(測定値)、471.81(計算値)
EA:C 66.08%、H 3.79%、N 5.84%、O 10.30%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、2−ヒドロキシ−フェニルベンゾチアゾール(1.72g、7.57mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−5)(0.96g、2.15mmol、収率:37%)を得た。
MS/FAB:447(測定値)、447.52(計算値)
EA:C 69.68%、H 4.01%、N 6.16%、O 10.85% S 7.05%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、2−ヒドロキシ−フェニルベンゾチアゾール(1.72g、7.57mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−6)(1.36g、2.70mmol、収率:46%)を得た。
MS/FAB:503(測定値)、503.88(計算値)
EA:C 61.88%、H 3.54%、N 5.46%、O 9.73%、S 6.26%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、2−ピリジン−2−イル−フェノール(1.30g、7.59mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−7)(0.59g、1.45mmol、収率:25%)を得た。
MS/FAB:407(測定値)、407.50(計算値)
EA:C 70.64%、H 4.35%、N 6.76%、O 7.96%、S 7.75%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、2−ピリジン−2−イル−フェノール(1.30g、7.59mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−8)(0.83g、1.79mmol、収率:31%)を得た。
MS/FAB:463(測定値)、463.86(計算値)
EA:C 62.04%、H 3.82%、N 5.98%、O 7.02%、S 6.83%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、2−ヒドロキシ−フェニルベンゾオキサゾールの代わりの10−ヒドロキシベンゾ[h]キノリン(1.48g、7.58mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−9)(0.98g、2.27mmol、収率:39%)を得た。
MS/FAB:431(測定値)、431.52(計算値)
EA:C 72.22%、H 4.10%、N 6.40%、O 7.62%、S 7.33%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、10−ヒドロキシベンゾ[h]キノリン(1.48g、7.58mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例4と同じ手順を実施して表題化合物の化合物(1−10)(1.22g、2.50mmol、収率:43%)を得た。
MS/FAB:487(測定値)、487.88(計算値)
EA:C 63.93%、H 3.65%、N 5.64%、O 6.70%、S 6.44%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェノール(2.17g、7.58mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−11)(0.56g、1.11mmol、収率:19%)を得た。
MS/FAB:506(測定値)、506.57(計算値)
EA:C 75.67%、H 4.50%、N 8.20%、O 9.68%
2−ヒドロキシ−フェニルベンゾオキサゾール(1.23g、5.82mmol)、2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェノール(2.17g、7.58mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−12)(0.72g、1.28mmol、収率:22%)を得た。
MS/FAB:562(測定値)、562.93(計算値)
EA:C 68.16%、H 4.05%、N 7.36%、O 8.68%
2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)フェノール(1.67g、5.83mmol)、2−ピリジン−2−イル−フェノール(1.30g、7.59mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−13)(0.84g、1.80mmol、収率:31%)を得た。
MS/FAB:466(測定値)、466.55(計算値)
EA:C 77.08%、H 4.87%、N 8.90%、O 6.98%
2−(1−フェニル−1H−ベンズイミダゾール−2−イル)−フェノール(1.67g、5.83mmol)、2−ピリジン−2−イル−フェノール(1.30g、7.59mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−14)(0.88g、1.68mmol、収率:29%)を得た。
MS/FAB:522(測定値)、522.91(計算値)
EA:C 68.81 %、H 4.33%、N 7.92%、O 6.32%
2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェノール(1.67g、5.83mmol)、10−ヒドロキシベンゾ[h]キノリン(1.50g、7.68mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−15)(0.26g、0.53mmol、収率:9%)を得た。
MS/FAB:490(測定値)、490.57(計算値)
EA:C 78.20%、H 4.68%、N 8.42%、O 6.70%
2−(1−フェニル−1H−ベンズイミダゾール−2−イル)−フェノール(1.67g、5.83mmol)、10−ヒドロキシベンゾ[h]キノリン(1.50g、7.68mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−16)(0.42g、0.77mmol、収率:13%)を得た。
MS/FAB:546(測定値)、546.93(計算値)
EA:C 70.13%、H 4.16%、N 7.58%、O 5.98%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェノール(2.17g、7.58mmol)、および硫酸ベリリウム四水和物(1.05g、5.93mmol)を使用することによって調製実施例1と同じ手順を実施して表題化合物の化合物(1−17)(0.64g、1.22mmol、収率:21%)を得た。
MS/FAB:522(測定値)、522.64(計算値)
EA:C 73.42%、H 4.34%、N 7.97%、O 6.25%、S 6.04%
2−ヒドロキシ−フェニルベンゾチアゾール(1.32g、5.80mmol)、2−(1−フェニル−1H−ベンズイミダゾール−2−イル)−フェノール(2.17g、7.58mmol)、および酢酸亜鉛(0.95g、5.18mmol)を使用することによって調製実施例2と同じ手順を実施して表題化合物の化合物(1−18)(0.94g、1.62mmol、収率:28%)を得た。
MS/FAB:578(測定値)、578.99(計算値)
EA:C 66.22%、H 3.94%、N 7.16%、O 5.70%、S 5.49%
発明による化合物を使用することによるOLEDデバイスの製造
本発明による主材料を使用した構造を有するOLEDデバイスを製造した。
ビス(2−メチル−8−キノリナト)(p−フェニルフェノラト)アルミニウム(III)(BAlq)を真空蒸着装置中の別のセルに発光主材料として投入し、(NPy)2Ir(acac)を発光材料としてさらに別のセルに投入し、これら2つの材料を、4〜10mol%のドーピングが得られるように異なる速度で蒸発させて、上記正孔輸送層上に厚さ30nmを有する発光層を蒸着したことを除けば、実施例1に記載の手順と同じ手順によりOLEDを作製した。
OLED特性の確認
実施例1〜18の中の1つから調製した本発明によるエレクトロルミネッセンス化合物および比較例1で調製した従来のエレクトロルミネッセンス化合物を含有する各OLEDデバイスの発光効率および電力効率を1,000cd/m2において測定し、それらの結果を表1に示している。
電力効率(lm/W)=(π×輝度)/(電流密度×電圧) (1)
Claims (7)
- 化学式1によって表されるエレクトロルミネッセンス化合物。
〔化学式1〕
L1L2M
(式中、L1およびL2は互いに異なり、および以下の構造式によって表されるものから選択される:
- Mが、Be、Zn、Mg、Cu、およびNiから選択される、請求項1記載のエレクトロルミネッセンス化合物。
- 請求項1から5のいずれか1項記載のエレクトロルミネッセンス化合物を含むエレクトロルミネッセンスデバイス。
- 前記エレクトロルミネッセンス化合物が発光層中の主材料として使用される、請求項6記載のエレクトロルミネッセンスデバイス。
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PCT/KR2007/000423 WO2007086682A1 (en) | 2006-01-24 | 2007-01-24 | Organic electroluminescent compounds and display device using the same as an electrolu¬ minescent material |
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JP (1) | JP5173836B2 (ja) |
KR (1) | KR100684109B1 (ja) |
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KR100850886B1 (ko) * | 2007-09-07 | 2008-08-07 | (주)그라쎌 | 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고있는 표시소자 |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
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KR100970713B1 (ko) * | 2007-12-31 | 2010-07-16 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광소자 |
KR100966885B1 (ko) | 2008-02-29 | 2010-06-30 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자 |
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JP2003192691A (ja) * | 2001-12-26 | 2003-07-09 | Mitsubishi Chemicals Corp | 有機イリジウム錯体及び有機電界発光素子 |
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WO2007086682A1 (en) | 2007-08-02 |
CN101517033A (zh) | 2009-08-26 |
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JP2009524650A (ja) | 2009-07-02 |
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