JPWO2018207135A1 - 有機化合物、発光素子、発光装置、電子機器、表示装置及び照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器、表示装置及び照明装置 Download PDFInfo
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- JPWO2018207135A1 JPWO2018207135A1 JP2019516739A JP2019516739A JPWO2018207135A1 JP WO2018207135 A1 JPWO2018207135 A1 JP WO2018207135A1 JP 2019516739 A JP2019516739 A JP 2019516739A JP 2019516739 A JP2019516739 A JP 2019516739A JP WO2018207135 A1 JPWO2018207135 A1 JP WO2018207135A1
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Abstract
Description
本発明の一態様の有機化合物は、下記一般式(G1)で表される有機化合物である。
本発明の一態様である発光素子の例について図1(A)を用いて以下、詳細に説明する。
本実施の形態では、実施の形態1に記載の発光素子を用いた発光装置について説明する。
本発明の一態様である照明装置を図8を参照しながら説明する。図8(B)は照明装置の上面図、図8(A)は図8(B)におけるe−f断面図である。
本発明の一態様である電子機器の例について説明する。電子機器として、例えば、テレビジョン装置(テレビ、またはテレビジョン受信機ともいう)、コンピュータ用などのモニタ、デジタルカメラ、デジタルビデオカメラ、デジタルフォトフレーム、携帯電話機(携帯電話、携帯電話装置ともいう)、携帯型ゲーム機、携帯情報端末、音響再生装置、パチンコ機などの大型ゲーム機などが挙げられる。これらの電子機器の具体例を以下に示す。
本合成例では、実施の形態1で構造式(102)として示したN,N’−ビス(3−メチルフェニル)−N,N’−ビス[3−(9−フェニル−9H−フルオレン−9−イル)フェニル]−ナフト[2,3−b;6,7−b’]ビスベンゾフラン−3,10−ジアミン(略称:3,10mMemFLPA2Nbf(IV))の合成方法について詳細に説明する。3,10mMemFLPA2Nbf(IV)の構造式を以下に示す。
500mL三口フラスコに11g(24mmol)の3,7−ジヨード−2,6−ジメトキシナフタレンと、14g(78mmol)の4−クロロ−2−フルオロフェニルボロン酸と、22g(0.16mol)の炭酸カリウムと、0.74g(2.4mmol)のトリス(2−メチルフェニル)ホスフィンを入れた。この混合物に、120mLのトルエンを加えた。この混合物を減圧しながら攪拌することで脱気した。この混合物に0.11g(0.49mmol)の酢酸パラジウム(II)を加え、窒素気流下、110℃で50.5時間攪拌した。
1H NMR(CDCl3,300MHz):δ=3.88(s,6H),7.18−7.24(m,6H),7.37(t,J1=7.2Hz,2H),7.65(s,2H).
200mL三口フラスコに5.7g(13mmol)の3,7−ビス(4−クロロ−2−フルオロフェニル)−2,6−ジメトキシナフタレンを入れ、フラスコ内を窒素置換した。このフラスコに32mLのジクロロメタンを加えた。この溶液に28mL(28mmol)の三臭化ホウ素(約1.0mol/Lジクロロメタン溶液)と20mLのジクロロメタンを滴下した。滴下終了後、この溶液を室温で攪拌した。
1H NMR(DMSO−d6,300MHz):δ=7.20(s,2H),7.37(dd,J1=8.4Hz,J2=1.8Hz,2H),7.46−7.52(m,4H),7.59(s,2H),9.71(s,2H).
200mLの三口フラスコに5.4g(13mmol)の3,7−ビス(4−クロロ−2−フルオロフェニル)−2,6−ジヒドロキシナフタレンと7.1g(52mmol)の炭酸カリウムを入れた。この混合物に、N−メチル−2−ピロリドン130mLを加え、この混合物を減圧しながら攪拌することで脱気した。脱気後、この混合物を、窒素気流下、120℃で7時間攪拌した。撹拌後、この混合物に水を加え、析出した固体を濾取した。この固体を水、エタノールで洗浄した。得られた固体にエタノールを加え、加熱撹拌後、濾過し固体を得た。得られた固体に酢酸エチルを加え、加熱撹拌後、濾過して淡黄色固体を4.5g、収率92%で得た。ステップ3の合成スキームを以下に示す。
1H NMR(1,1,2,2−Tetrachloroethane−D2,300MHz):δ=7.44(dd,J1=8.1Hz,J2=1.5Hz,2H),7.65(d,J1=1.8Hz,2H),8.05(d,J1=8.4Hz,2H),8.14(s,2H),8.52(s,2H).
200mL三口フラスコに0.82g(2.2mmol)の3,10−ジクロロナフト[2,3−b;6,7−b’]ビスベンゾフランと、2.8g(6.5mmol)のN−(3−メチルフェニル)−3−(9−フェニル−9H−フルオレン−9−イル)フェニルアミンと、78mg(0.22mmol)のジ(1−アダマンチル)−n−ブチルホスフィンと、1.3g(13mmol)のナトリウムtert−ブトキシドを入れた。この混合物に、25mLのキシレンを加えた。この混合物を減圧しながら攪拌することで脱気した。この混合物に25mg(43μmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、窒素気流下、150℃で9.5時間攪拌した。
1H NMR(1,1,2,2−Tetrachloroethane−D2,300MHz):δ=2.30(s,6H),6.74(d,J1=7.8Hz,2H),6.90−7.00(m,8H),7.05−7.32(m,24H),7.36−7.41(m,8H),7.76−7.79(m,4H),7.85(d,J1=8.1Hz,2H),8.02(s,2H),8.37(s,2H).
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子1は、発光素子1における発光層113に用いた3,10mMemFLPA2Nbf(IV)を上記構造式(v)で表される3,10−ビス(ジフェニルアミノ)ナフト[2,3−b;6,7−b’]ビスベンゾフラン(略称:3,10DPhA2Nbf(IV))に変えて発光層113を形成し、また、電子輸送層114に用いたNBPhenを上記構造式(vi)で表されるバソフェナントロリン(略称:BPhen)に変えて電子輸送層114を形成することによって作製した。比較発光素子1で用いた3,10DPhA2Nbf(IV)と、発光素子1で用いた3,10mMemFLPA2Nbf(IV)は、主骨格であるナフトビスベンゾフランの構造は同一であるが、結合するアミンの構造が異なる物質である。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
本合成例では、N,N’−ジフェニル−N,N’−ビス[3−(9−フェニル−9H−フルオレン−9−イル)フェニル]−ナフト[2,3−b;6,7−b’]ビスベンゾフラン−3,10−ジアミン(略称:3,10mFLPA2Nbf(IV))の合成方法について詳細に説明する。3,10mFLPA2Nbf(IV)の構造式を以下に示す。
実施例1の合成例1におけるステップ1と同様に合成した。
実施例1の合成例1におけるステップ2と同様に合成した。
実施例1の合成例1におけるステップ3と同様に合成した。
200mL三口フラスコに、0.84g(2.2mmol)の3,10−ジクロロナフト[2,3−b;6,7−b’]ビスベンゾフランと、2.7g(6.7mmol)の3−(9−フェニル−9H−フルオレン−9−イル)ジフェニルアミンと、80mg(0.22mmol)のジ(1−アダマンチル)−n−ブチルホスフィンと、1.3g(13mmol)のナトリウム tert−ブトキシドを入れた。この混合物に、25mLのキシレンを加えた。この混合物を減圧しながら攪拌することで脱気した。この混合物に26mg(45μmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、窒素気流下、150℃で7時間攪拌した。
1H NMR(1,1,2,2−Tetrachloroethane−D2,300MHz):δ=6.76(d,J1=8.1Hz,2H),6.98−7.33(m,32H),7.36−7.40(m,8H),7.76−7.79(m,4H),7.85(d,J1=8.4Hz,2H),8.02(s,2H),8.38(s,2H).
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
Claims (20)
- 下記一般式(G1)で表される有機化合物。
- 請求項1において、前記Ar2が炭素数6乃至12の芳香族炭化水素基である有機化合物。
- 請求項1または請求項2において、前記pが0である有機化合物。
- 請求項1または請求項2において、前記pが1であり、前記α4がフェニレン基である有機化合物。
- 請求項1または請求項2において、前記l、前記mおよび前記nがそれぞれ独立に0または1であり、前記α1乃至α3がフェニレン基である有機化合物。
- 請求項1または請求項2において、前記lが0である有機化合物。
- 請求項7において、前記一般式(B1)におけるR11、R12、R17およびR18のいずれか1または2が前記一般式(g1)で表される基を表す有機化合物。
- 請求項9において、前記一般式(B2)におけるR31、R32、R37およびR38のいずれか1または2が前記一般式(g1)で表される基を表す有機化合物。
- 請求項11において、前記一般式(B3)におけるR51、R52、R57およびR58のいずれか1または2が前記一般式(g1)で表される基を表す有機化合物。
- 請求項7、請求項9および請求項11のいずれか一項において、前記X2およびX3が酸素原子である有機化合物。
- 請求項1、請求項7、請求項9および請求項11のいずれか一項において、分子量が1300以下である有機化合物。
- 請求項1、請求項7、請求項9および請求項11のいずれか一項において、分子量が1200以下である有機化合物。
- 請求項1、請求項7、請求項9および請求項11のいずれか一項に記載の有機化合物を含む発光素子。
- 請求項16に記載の発光素子と、トランジスタ、または、基板と、を有する発光装置。
- 請求項17に記載の発光装置と、センサ、操作ボタン、スピーカ、または、マイクと、を有する電子機器。
- 請求項17に記載の発光装置と、筐体と、を有する照明装置。
- 請求項1、請求項7、請求項9および請求項11のいずれか一項に記載の有機化合物を含む電子デバイス。
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