JP4976288B2 - 有機金属錯体及びこれを用いた有機電界発光素子 - Google Patents
有機金属錯体及びこれを用いた有機電界発光素子 Download PDFInfo
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- JP4976288B2 JP4976288B2 JP2007520088A JP2007520088A JP4976288B2 JP 4976288 B2 JP4976288 B2 JP 4976288B2 JP 2007520088 A JP2007520088 A JP 2007520088A JP 2007520088 A JP2007520088 A JP 2007520088A JP 4976288 B2 JP4976288 B2 JP 4976288B2
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Description
(式中、環Aは置換基を有していてもよい含窒素複素環を示し、環Bは置換基を有していてもよい芳香族炭化水素環又は芳香族複素環を示し、環A及び環Bが各々の環において置換基を2以上有する場合は相互に結合して環を構成してもよい。Xは炭素原子又は窒素原子を示す。)
(式中、R1〜R8は、各々に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複素芳香族基を示す。)
(式中、R9〜R12は独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換基を有してもよい芳香族炭化水素基又は置換基を有してもよい複素芳香族基を示し、隣り合う置換基は相互に結合して環を構成してもよい。)
(式中、R13〜R17は、独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複素芳香族基を示し、隣り合う置換基は相互に結合して環を構成してもよい。)
脱気窒素置換した100ml三口フラスコにアルミニウムトリイソプロポキシド3.0g、2-(2‐ヒドロキシフェニル)ベンゾオキサゾール6.2gを加え、これに無水トルエン50mlを加えて溶解させた。その後60℃まで加熱し、30分攪拌した。これに4-ジフェニルアミノフェノール3.8gの溶けた無水トルエン50mlをゆっくり滴下して、そのまま60℃にて3時間攪拌した。室温まで冷却した後、生じた白色沈殿を濾取した後、ろ液を1/2量まで濃縮した。1/2量まで濃縮したろ液中に析出した結晶をろ別し、トルエンで洗浄した。これを、減圧乾燥して黄色粉末(化合物1;M=Al)9.0gを得た。この一部を昇華精製し、素子作成に用いた。
化合物1のEI−MS(M+1)は708、融点は274℃であった。
ガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物1とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %である薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物1の極大吸収波長であり、そのときに出てくる光を観察した。ホストからの発光ではなく、ドーパントからの発光が観測された。
薄膜主成分である化合物1をAlq3に変えて薄膜を作成した以外は、実施例2と同様に評価した。ホストからの発光が観測され、ドーパントからの発光は観測されなかった。
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物1とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
正孔輸送層としてHMTPDを、発光層の主成分としてTAZを用いた以外は実施例3と同様にして有機EL素子を作成した。
発光層の主成分として、TAZを用いた以外は実施例3と同様にして有機EL素子を作成した。
Claims (6)
- 下記一般式(I)で表される有機EL用有機金属錯体。
(式中、Ar1は置換基を有してもよいフェニレン基、ナフチレン基、又はピリジレン基を示す。Ar2、Ar3は置換基を有してもよいフェニル基、ナフチル基、ピリジル基、又はキノリル基を示すが、Ar2とAr3が結合して環を形成することはない。Mはアルミニウムを示し、Lは下記一般式(III)で表される配位子である。)
(式中、R 1 〜R 8 は水素原子、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシル基、又は炭素数1〜6のアルキル基が置換しても良いフェニル基を示し、隣り合う置換基は相互に結合して環を構成してもよい。Xは酸素原子又は硫黄原子を示す。) - Ar 2 、Ar 3 が下記一般式(X)で表される芳香族炭化水素基である請求項1〜3のいずれかに記載の有機EL用有機金属錯体。
(式中、R 13 〜R 17 は、独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複素芳香族基を示し、隣り合う置換基は相互に結合して環を構成してもよい。) - 請求項1〜4のいずれかに記載の有機EL用有機金属錯体を含む有機層を有する有機電界発光素子。
- 有機EL用有機金属錯体を含む有機層が、更に燐光発光ドーパントを含有する発光層である請求項5記載の有機電界発光素子。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007520088A JP4976288B2 (ja) | 2005-06-07 | 2006-06-05 | 有機金属錯体及びこれを用いた有機電界発光素子 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005166581 | 2005-06-07 | ||
| JP2005166581 | 2005-06-07 | ||
| PCT/JP2006/311203 WO2006132173A1 (ja) | 2005-06-07 | 2006-06-05 | 有機金属錯体及びこれを用いた有機電界発光素子 |
| JP2007520088A JP4976288B2 (ja) | 2005-06-07 | 2006-06-05 | 有機金属錯体及びこれを用いた有機電界発光素子 |
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| Publication Number | Publication Date |
|---|---|
| JPWO2006132173A1 JPWO2006132173A1 (ja) | 2009-01-08 |
| JP4976288B2 true JP4976288B2 (ja) | 2012-07-18 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2007520088A Expired - Fee Related JP4976288B2 (ja) | 2005-06-07 | 2006-06-05 | 有機金属錯体及びこれを用いた有機電界発光素子 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8709614B2 (ja) |
| JP (1) | JP4976288B2 (ja) |
| KR (1) | KR101010846B1 (ja) |
| CN (1) | CN101193875B (ja) |
| WO (1) | WO2006132173A1 (ja) |
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- 2006-06-05 KR KR1020087000400A patent/KR101010846B1/ko not_active Expired - Fee Related
- 2006-06-05 JP JP2007520088A patent/JP4976288B2/ja not_active Expired - Fee Related
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Also Published As
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| US20090026923A1 (en) | 2009-01-29 |
| JPWO2006132173A1 (ja) | 2009-01-08 |
| WO2006132173A1 (ja) | 2006-12-14 |
| CN101193875A (zh) | 2008-06-04 |
| CN101193875B (zh) | 2011-05-11 |
| KR101010846B1 (ko) | 2011-01-25 |
| US8709614B2 (en) | 2014-04-29 |
| KR20080021121A (ko) | 2008-03-06 |
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