JP4308663B2 - 新しい電子輸送用物質及びこれを利用した有機発光素子 - Google Patents
新しい電子輸送用物質及びこれを利用した有機発光素子 Download PDFInfo
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Description
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環より誘導された基であり、
R3は、水素原子、炭素数1乃至20のアルキル基もしくは脂肪族炭化水素、置換又は非置換のベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環の集合であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環より誘導された基である]
を提供する。
以下で本発明を詳細に説明するが、下記詳細な説明及び実施例は本発明による一つの実例であり、このような実施例は本発明の概念及び範囲内でこの分野の通常の知識を有する者によって多様に変更及び変形することができる。
図1は、本発明の有機電気発光素子に適用できる構造の一例を示す断面図であって、図面符号1は基板、2は陽極、3は正孔注入層、4は正孔輸送層、5は有機発光層、6は電子輸送層、7は陰極を各々示す。
である。
に置換できる。
(化学式aに示される出発物質の製造)
2,6−ジアミノアントラキノン(23.8g、100mmol)を48重量%濃度の臭化水素水溶液に分散させた後、20℃で亜硝酸ナトリウム(NaNO2;14.1g、204mmol)をゆっくり滴下した。気体発生が終わった後、48重量%濃度の臭化水素水溶液(63ml)に臭化銅(CuBr2;29.5g、206mmol)を溶かした溶液を少量のエタノール(50ml)と共にゆっくり滴下した。反応物の温度を常温まで徐々に上げた後、一時間ほど還流した。常温に冷却した後、水を加えて希釈し、生成した沈殿物を濾過して水で洗い、真空乾燥した。得られた固体をクロロホルムに溶解し、シリカゲルを通過させて濾過した後、減圧して溶媒を除去した。カラムクロマトグラフィで精製した後にクロロホルムより再結晶させて、淡い黄色の出発物質である化学式aの化合物(10g、収率27%)を得た。
この化合物の分析結果は次の通りである。
1H NMR (300 MHz, CDCl3), 8.44 (d, J = 2.1 Hz, 2H), 8.18 (d, J = 8.0 Hz, 2H), 7.95 (dd, J = 2.1, 8.0 Hz, 2H.)
(化学式bに示される出発物質の製造)
窒素雰囲気下で、2−ブロモビフェニル(8.83ml、51.2mmol)を乾燥したTHF(200ml)に溶解し、−78℃まで冷却した後、第3−ブチルリチウム(60ml、1.7Mのペンタン溶液)をゆっくり滴下した。同一温度で40分間攪拌した後、前記製造例1で製造された化学式aの化合物(7.50g、20.5mmol)を同一温度で加えた。冷却槽を除去した後、反応物を常温で15時間ほど攪拌した。反応溶液をジエチルエーテル(200ml)と2N塩酸溶液(200ml)の混合溶媒にゆっくり加え、40分間常温で攪拌した。生成した沈殿物を濾過した後、水とエチルエーテルで充分で洗浄した。この物質を真空乾燥して、化学式bに示される化合物(11.8g、収率85%)を得た。
(化学式cに示される出発物質の製造)
前記製造例2で製造された化学式bに示される化合物(4.00g、5.93mmol)、ヨウ化カリウム(9.85g、59.3mmol)と次亜リン酸ナトリウム水和物(10.4g、98.0mmol)の混合物をオルト−ジクロロベンゼン(600ml)と酢酸(80ml)の混合溶液で24時間ほど還流した。常温に冷却した後、混合物をクロロホルムで抽出し、硫酸マグネシウムで水分を除去した後に減圧して、溶媒を除去した。得られた固体をクロロホルムに溶解し、短いシリカゲルコラムを通過させた後に減圧して溶媒を除去した。これをn−ヘキサンに分散させて攪拌し、濾過した後に真空乾燥して、淡い黄色の化学式cに示される化合物(3.3g、収率87%)を得た。
この化合物の分析結果は次の通りである。
融点478.1℃;1H NMR (300 MHz, CDCl3) 7.92 (d, J = 7.6 Hz, 4H), 7.46 (t, J = 8.0 Hz, 4H), 7.33 (t, J = 7.4 Hz, 4H), 7.21 (d, J = 7.6 Hz, 4H), 6.88 (dd, J = 2.1, 8.6 Hz, 2H), 6.47 (d, J = 2.1 Hz, 2H), 6.22 (d, J = 8.6 Hz, 2H); MS (M+) 636; Anal. Calcd for C38H22Br2: C, 71.50; H, 3.47; Br, 25.03. Found: C, 71.90; H, 3.40; Br, 25.7.
(化学式dに示される出発物質の製造)
65℃で、アセトニトリル(250ml)に臭化銅(CuBr2;17.9g、80.0mmol)と第3−亜硝酸ブチル(12ml、101mmol)を分散させて攪拌した後、ここに2−アミノアントラキノン(15.0g、67.2mmol)を5分にかけてゆっくり滴下した。気体発生が終わった後、反応溶液を常温に冷却し、反応溶液を20%濃度の塩酸水溶液(1000ml)に加えてジクロロメタンで抽出した。有機層を硫酸マグネシウムで残留水分を除去した後に減圧して乾燥した。カラムクロマトグラフィで精製(ジクロロメタン/n−ヘキサン=4/1)し、淡い黄色の化学式dに示される化合物(14.5g、収率75%)を得た。
この化合物の分析結果は次の通りである。
融点207.5℃;1H NMR (500 MHz, CDCl3) 8.43 (d, J = 1.8 Hz, 1H), 8.30 (m, 2H), 8.17 (d, J = 8.3 Hz, 1H), 7.91 (dd, J = 1.8, 8.3 Hz, 1H), 7.82 (m, 2H); MS (M+) 286; Anal. Calcd for C14H7BrO2: C, 58.57; H, 2.46; Br, 27.83; O, 11.14. Found: C, 58.88; H, 2.39; Br, 27.80; O, 10.93.
(化学式eに示される出発物質の製造)
窒素雰囲気下で、乾燥されたテトラヒドロフラン(100ml)に2−ブロモビフェニル(9.0ml、52mmol)を溶解し、−78℃で第3−ブチルリチウム(40ml、1.7Mのペンタン溶液)をゆっくり滴下した。同一温度で一時間ほど攪拌した後、前記製造例4で製造された化学式dに示される化合物(4.9g、17mmol)を加えた。冷却槽を除去した後、常温で3時間ほど攪拌した。反応混合物に塩化アンモニウム水溶液を加えた後、ジクロロメタンで抽出した。有機層を硫酸マグネシウムで乾燥して溶媒を除去した。得られた固体をエタノールに分散させて一時間ほど攪拌した後、濾過し、エタノールで洗浄した。乾燥後、化学式eに示される化合物(9.50g、収率94%)を得た。
(化学式fに示される出発物質の製造)
窒素雰囲気下で、前記製造例5で製造された化学式eに示される化合物(6.0g、10.1mmol)を酢酸300mlに分散させた後、ヨウ化カリウム(16.8g、101mmol)、次亜リン酸ナトリウム水和物(17.7g、167mmol)を加えて3時間ほど沸騰させながら攪拌した。常温に冷却して濾過し、水とメタノールで洗浄した後に真空乾燥して、淡い黄色の化学式fに示される化合物(5.0g、収率88%)を得た。
(化学式gに示される出発物質の製造)
酢酸100mlに、前記製造例5で製造された化学式eに示される化合物(9.5g、16mmol)を分散させ、これに高濃度の硫酸5滴を加えて3時間ほど還流した。常温に冷却して生成された固体を濾過し、酢酸で洗った後、水とエタノールで順に洗浄した。乾燥した後に昇華法で精製して、白色の固体の化学式gに示される化合物(8.0g、収率89%)を得た。
(化学式hに示される出発物質の製造)
窒素雰囲気下で、150mlの乾燥したTHFに前記製造例7で製造された化学式gに示される化合物(10g、17.9mmol)を完全に溶解した後、−78℃で第3−ブチルリチウム(31.5ml、1.7Mのペンタン溶液)をゆっくり滴下した。同一温度で一時間ほど攪拌した後、ホウ酸トリメチル(8ml、71.5mmol)を加えた。冷却槽を除去して反応混合物を3時間ほど常温で攪拌した。反応混合物に2N塩酸水溶液(100ml)を加えて1.5時間ほど常温で攪拌した。生成した沈殿物を濾過し、水とエチルエーテルで順に洗浄した後に真空乾燥した。乾燥後、エチルエーテルに分散させて2時間ほど攪拌した後、濾過し乾燥して、白色の化学式hに示される化合物(7.6g、収率81%)を得た。
(化学式iに示される出発物質の製造)
窒素雰囲気下で、乾燥されたテトラヒドロフラン(100ml)に2−ブロモナフタレン(11g、53.1mmol)を溶解し、−78℃で第3−ブチルリチウム(47ml、1.7Mのペンタン溶液)をゆっくり滴下した。同一温度で一時間ほど攪拌した後、前記製造例4で製造された化学式dに示される化合物(6.31g、22mmol)を加えた。冷却槽を除去した後、常温で3時間ほど攪拌した。反応混合物に塩化アンモニウム水溶液を加えた後、ジクロロメタンで抽出した。有機層を硫酸マグネシウムで乾燥して溶媒を除去した。得られた混合物をジエチルエーテル少量で溶解した後に石油エーテルを加え、数時間ほど攪拌して固体化合物を得た。濾過した後に真空乾燥して、ジナフチルジアルコール(11.2g、収率94%)を得た。窒素雰囲気下でジナフチルジアルコール(11.2g、20.6mmol)を酢酸600mlに分散させ、ヨウ化カリウム(34.2g、206mmol)、次亜リン酸ナトリウム水和物(36g、340mmol)を加えた後、3時間ほど沸騰させながら攪拌した。常温に冷却して濾過し、水とメタノールで洗浄した後に真空乾燥して、淡い黄色の化学式iに示される化合物(10.1g、収率96%)を得た。
(化学式2−2に示される化合物の製造)
4−ブロモフェニルアルデヒド(41.6g、225mmol)と1,3−プロパンジオール(16.3ml、225mmol)をトルエン500mlに溶解した後、パラ−トルエンスルホン酸1gを入れ、水を除去しながら2日間還流した。反応物にジエーテル100mlを加えて希釈した後、水100mlを注いで抽出した。これを硫酸マグネシウム上で乾燥し、有機溶媒を除去して得た液体をカラムクロマトグラフィで精製し、得られた液体を石油エーテルで結晶形成させて、白色の固体の4−ブロモフェニルアセタールを得た(45g、収率82%)。
この化合物の分析結果は次の通りである。
融点395.0℃;1H NMR (300 MHz, CDCl3) 7.88(2H), 7.62(2H), 7.66-7.60 (10H), 7.55-7.44(15H), 7.40(2H), 7.38-30(9H), 6.95(6H), 6.83(4H); MS [M+H] 1019.
(化学式1−2に示される化合物の製造)
前記製造例6で製造された化学式fに示される化合物(1.00g、1.80mmol)と4−ホルミルフェニルボロン酸(0.74g、4.93mmol)を2N炭酸カリウム水溶液20mlとトルエン40mlの溶液に入れて攪拌しながらPd(PPh3)4(0.20g、0.17mmol)を入れ、3日間還流した。トルエン層を抽出した後に水で洗浄し、無水硫酸マグネシウムで乾燥させた後、シリカゲル層を通過させて溶媒を除去して固体化合物を得た。エタノール100mlで洗浄した後に濾過し、エチルアセテートより再結晶させて、アントラセンフェニルアルデヒド(330mg、収率31%)を得た。
この化合物の分析結果は次の通りである。
1H NMR (300 MHz, CDCl3) 7.89(1H), 7.75(1H), 7.62-7.29 (24H), 6.98-6.76(12H); MS [M+H] 751.
(化学式1−4に示される化合物の製造)
前記製造例9で製造された化学式iに示される化合物(4.0g、7.85mmol)と4−ホルミルフェニルボロン酸(3.53g、23.5mmol)を2N炭酸カリウム水溶液20mlとトルエン60mlの溶液に入れて攪拌しながらPd(PPh3)4(0.27g、0.23mmol)を入れ、3日間還流した。トルエン層を抽出した後に水で洗浄し、無水硫酸マグネシウムで乾燥させた後、シリカゲル層を通過させて溶媒を除去して固体化合物を得た。エタノール100mlで洗浄した後に濾過し、エチルアセテートより再結晶させて、アントラセンフェニルアルデヒド(2g、収率47.6%)を得た。
融点352.0℃;1H NMR (300 MHz, CDCl3) 8.28(s, 2H), 8.14(d, 2H), 7.99(t, 4H), 7.81(t, 4H), 7.62(m, 4H), 7.53(d, 2H), 7.45(m, 4H), 7.32-7.26(m, 6H), 7.22(s, 6H); MS [M+H] 699.
(化学式2−4に示される化合物の製造)
窒素雰囲気下で、2−ブロモナフタレン(5.78g、28.0mmol)を乾燥したTHF(40ml)に溶解して−78℃まで冷却した後、第3−ブチルリチウム(21ml、1.7Mのペンタン溶液)をゆっくり滴下した。同一温度で40分間攪拌した後、前記製造例1で製造された化学式aに示される化合物(2.93g、8.00mmol)を同一温度で加えた。冷却槽を除去した後、反応物を常温で3時間ほど攪拌した。反応溶液にアンモニウムクロライド溶液(40ml)をゆっくり加えて40分間常温で攪拌した。生成した沈殿物を濾過した後、水と石油エーテルで充分洗浄した。この物質を真空乾燥してジアルコール(4.10g、収率82%)を得た。
(化学式3−2に示される化合物の製造)
9,10−ジオキソ−9,10−ジヒドロ−アントラセン−2−カルバアルデヒド(1.63g、6.9mmol)にN−フェニル−1,2−フェニレンジアミン(1.27g、6.90mmol)を加え、トルエン80mlと酢酸10mlを入れて12時間ほど還流した。溶媒を除去してエタノールを注いで結晶化させた後に濾過して、ベンゾイミダゾール化合物(2−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−アントラキノン、1.14g、収率41%)を得た。
この化合物の分析結果は次の通りである。
融点270。0℃;1H NMR (300 MHz, CDCl3) 7.86(d, 1H), 7.75(dd, 1H), 7.70(s, 1H), 7.63-7.48(m, 8H), 7.42-7.0(m, 12H), 6.92-6.81(m, 9H), 6.63(d, 2H); MS [M+H] 675.
(有機発光素子の製造)
ITO(indium tin oxide)が1500Åの厚さで薄膜コーティングされたガラス基板を、洗剤を溶解した蒸溜水に入れて超音波で洗浄した。洗剤は、フィッシャー(Fischer Co.)社の製品を用い、ミリポア(Millipore Co.)社製造のフィルターに2回濾過された蒸溜水を用いた。ITOを30分間洗浄した後、蒸溜水で2回繰り返して超音波洗浄を10分間進行した。蒸溜水洗浄が終わったら、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄を行って乾燥させた後、プラズマ洗浄機に移送した。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を移送した。
(有機発光素子の製造)
前記実施例6と同様に用意されたITO透明電極上に、ヘキサニトリルヘキサアザトリフェニレンを500Åの厚さで熱真空蒸着して正孔注入層を形成した。その上に正孔を移送する物質であるNPB(600Å)を真空蒸着した後、発光層及び電子輸送層の役割を果たすAlq3を500Åの厚さで真空蒸着した。前記Alq3発光層上に、順に5Åの厚さでフッ化リチウム(LiF)と2500Åの厚さのアルミニウムを蒸着して陰極を形成した。前記過程において、有機物の蒸着速度は1Å/secを維持し、フッ化リチウムは0.2Å/sec、アルミニウムは3〜7Å/secの蒸着速度を維持した。
(有機発光素子の製造)
本実施例では本発明の化合物が正孔と電子とが再結合して光を発光する発光層として使用するための安定性テストを行った。前記発光層にp−型発光物質(正孔移動度>電子移動度)又は適切な量のp−型ドーパントが用いられる場合、正孔が電子輸送層へ移送される。したがって、電子輸送層を構成する物質が正孔に対して不安定な場合には素子が容易に壊れるようになるが、これは前記発光物質の不安定さのためでなく電子輸送物質が原因である。
(有機発光素子の製造)
発光物質として化学式1−4の化合物の代わりにTPBIを用いたことを除いては、前記実施例6と同様な方法で有機発光素子を製造した。
前記製造された素子に6.9Vの順方向電界を加えた結果、50mA/cm2の電流密度で、354nit明るさ(440nmで最大ピーク)の青色スペクトルが観察された。
前記素子の寿命は50mA/cm2のDC電流を印加して測定しており、この時、本発明の有機物質の効率を確認できる輝度と駆動電圧との関係を測定した。図6を参照すれば、駆動の20時間後に前記素子の輝度が20%減少し、前記駆動電圧は8.2V増加したが、これは、図7を参照すれば初期駆動電圧の124%の増加に該当する。このような結果は、本発明による物質が正孔を安定化して有機電気発光素子の青色発光層として用いられ、寿命を増加させることを示す。
(有機発光素子の製造)
前記実施例7と同様に用意されたITO透明電極上に、ヘキサニトリルヘキサアザトリフェニレンを500Åの厚さで熱真空蒸着して正孔注入層を形成した。その上に正孔を移送する物質であるNPB(600Å)を真空蒸着した後、発光層の役割をする前記化学式jに示される化合物を100Åの厚さで真空蒸着した。発光層上に電子の注入及び移送の役割をする前記化学式1−2に示される化合物を200Åの厚さで真空蒸着して、有機物層の薄膜形成を完了した。前記電子注入及び輸送層上に、順に5Åの厚さでフッ化リチウム(LiF)と2500Åの厚さのアルミニウムを蒸着して陰極を形成した。前記過程において、有機物の蒸着速度は1Å/secを維持し、フッ化リチウムは0.2Å/sec、アルミニウムは3〜7Å/secの蒸着速度を維持した。
(有機発光素子の製造)
前記実施例7と同様に用意されたITO透明電極上に、ヘキサニトリルヘキサアザトリフェニレンを500Åの厚さで熱真空蒸着して正孔注入層を形成した。その上に正孔を移送する物質であるNPB(600Å)を真空蒸着した後、発光層の役割をする前記化学式iに示される化合物を200Åの厚さで真空蒸着した。発光層上に電子の注入及び移送の役割をする前記化学式2−2に示される化合物を200Åの厚さで真空蒸着して、有機物層の薄膜形成を完了した。前記電子注入及び輸送層上に、順に5Åの厚さでフッ化リチウム(LiF)と2500Åの厚さのアルミニウムを蒸着して陰極を形成した。前記過程において、有機物の蒸着速度は1Å/secを維持し、フッ化リチウムは0.2Å/sec、アルミニウムは3〜7Å/secの蒸着速度を維持した。
(有機発光素子の製造)
前記実施例6と同様に用意されたITO透明電極上に、ヘキサニトリルヘキサアザトリフェニレンを500Åの厚さで熱真空蒸着して正孔注入層を形成した。その上に正孔を移送する物質であるNPB(600Å)を真空蒸着した後、発光層の役割をする前記化学式kに示される化合物を200Åの厚さで真空蒸着した。発光層上に電子の注入及び移送の役割をする前記化学式3−2に示される化合物を200Åの厚さで真空蒸着して、有機物層の薄膜形成を完了した。前記電子注入及び輸送層上に、順に5Åの厚さでフッ化リチウム(LiF)と2500Åの厚さのアルミニウムを蒸着して陰極を形成した。前記過程において、有機物の蒸着速度は1Å/secを維持し、フッ化リチウムは0.2Å/sec、アルミニウムは3〜7Å/secの蒸着速度を維持した。
Claims (25)
- 下記の化学式1:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、
R3は、水素原子、炭素数1乃至20のアルキル基もしくは脂肪族炭化水素、置換又は非置換のベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である]
に示される化合物。 - 下記の化学式2:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である] に示される化合物。 - 下記の化学式3:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
R3は、水素原子、炭素数1乃至20のアルキル基もしくは脂肪族炭化水素、置換又は非置換のベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である]
に示される化合物。 - 下記の化学式5:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である]
に示される化合物。 - 下記の化学式1に示される化合物、化学式2に示される化合物、化学式3に示される化合物、化学式4に示される化合物、及び化学式5に示される化合物からなる群より1種以上選択される有機化合物:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、
R3は、水素原子、炭素数1乃至20のアルキル基もしくは脂肪族炭化水素、置換又は非置換のベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である]
を含有する少なくとも一つの有機化合物層を含む有機発光素子。 - 前記有機化合物層が、正孔を注入する陽極と電子を注入する陰極との間に少なくとも一つが位置する、請求項6に記載の有機発光素子。
- 少なくとも一つの前記有機化合物層が、電子注入及び輸送機能を有する電子注入及び輸送層である、請求項6に記載の有機発光素子。
- 少なくとも一つの前記有機化合物層が、電子注入及び発光機能を有する電子注入及び発光層である、請求項6に記載の有機発光素子。
- 少なくとも一つの前記有機化合物層が発光機能を有する発光層である、請求項6に記載の有機発光素子。
- 少なくとも一つの前記有機化合物層が、電子輸送及び発光機能を有する電子輸送及び発光層である、請求項6に記載の有機発光素子。
- 前記有機発光素子が、下から基板、陽極、正孔注入層、正孔輸送層、有機発光層、電子輸送層、及び陰極を含み、前記有機化合物層が前記有機発光層に含まれている、請求項6に記載の有機発光素子。
- 前記有機発光素子が、下から基板、陽極、正孔注入層、正孔輸送層、有機発光層、電子輸送層、及び陰極を含み、前記有機化合物層が前記電子注入/輸送層に含まれている、請求項6に記載の有機発光素子。
- 前記有機化合物層が下記の化学式1又は化学式3の化合物:
R1及びR2は、各々独立的に又は同時に、水素原子、炭素数1乃至20の脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、R1及びR2が同時に水素原子であることはできず、
Arは、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環であり、
R3は、水素原子、炭素数1乃至20のアルキル基もしくは脂肪族炭化水素、置換又は非置換のベンゼン、ナフタレン、ビフェニル、アントラセン、又は芳香族複素環もしくは芳香族環の集合であり、
R4は、水素原子、炭素数1乃至12のアルキル基もしくは脂肪族炭化水素、ベンゼン、ナフタレン、ビフェニル、アントラセン、又は置換又は非置換の芳香族複素環もしくは置換又は非置換の芳香族環である]
を含有する、請求項6に記載の有機発光素子。
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- 2003-01-17 CN CN038001551A patent/CN1625552B/zh not_active Expired - Lifetime
- 2003-01-17 WO PCT/KR2003/000112 patent/WO2003060956A2/en active Application Filing
- 2003-01-17 JP JP2003560958A patent/JP4308663B2/ja not_active Expired - Lifetime
- 2003-01-17 AU AU2003215914A patent/AU2003215914A1/en not_active Abandoned
- 2003-01-17 EP EP03729561.5A patent/EP1465874B1/en not_active Expired - Lifetime
- 2003-08-05 TW TW092121428A patent/TWI227655B/zh not_active IP Right Cessation
Cited By (8)
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KR20130097715A (ko) | 2010-07-09 | 2013-09-03 | 유디씨 아일랜드 리미티드 | 유기 전계 발광 소자 |
US10431749B2 (en) | 2010-07-09 | 2019-10-01 | Udc Ireland Limited | Organic electroluminescent element |
CN105074948A (zh) * | 2013-02-22 | 2015-11-18 | 保土谷化学工业株式会社 | 有机电致发光器件 |
CN105074948B (zh) * | 2013-02-22 | 2017-12-26 | 保土谷化学工业株式会社 | 有机电致发光器件 |
US9853223B2 (en) | 2015-05-28 | 2017-12-26 | Kabushiki Kaisha Toshiba | Compound, organic photoelectric conversion device and solid-state imaging device |
US11581487B2 (en) | 2017-04-26 | 2023-02-14 | Oti Lumionics Inc. | Patterned conductive coating for surface of an opto-electronic device |
US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11730012B2 (en) | 2019-03-07 | 2023-08-15 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
Also Published As
Publication number | Publication date |
---|---|
EP1465874A2 (en) | 2004-10-13 |
US6878469B2 (en) | 2005-04-12 |
KR100691543B1 (ko) | 2007-03-09 |
EP1465874B1 (en) | 2013-06-19 |
AU2003215914A1 (en) | 2003-07-30 |
TW200507696A (en) | 2005-02-16 |
TWI227655B (en) | 2005-02-01 |
CN1625552B (zh) | 2011-09-28 |
KR20030067773A (ko) | 2003-08-19 |
WO2003060956A2 (en) | 2003-07-24 |
JP2005515233A (ja) | 2005-05-26 |
CN1625552A (zh) | 2005-06-08 |
AU2003215914A8 (en) | 2003-07-30 |
US20030165715A1 (en) | 2003-09-04 |
WO2003060956A3 (en) | 2003-11-13 |
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