JP2008280312A - ベンゾ[ghi]フルオランテン誘導体及びこれを用いた有機発光素子 - Google Patents
ベンゾ[ghi]フルオランテン誘導体及びこれを用いた有機発光素子 Download PDFInfo
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- JP2008280312A JP2008280312A JP2007127794A JP2007127794A JP2008280312A JP 2008280312 A JP2008280312 A JP 2008280312A JP 2007127794 A JP2007127794 A JP 2007127794A JP 2007127794 A JP2007127794 A JP 2007127794A JP 2008280312 A JP2008280312 A JP 2008280312A
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- 0 CC(C)(C)c(ccc(C)c1-c2c(C=*)cc3)c1-c1c2c3ccc1C(C)(C)C Chemical compound CC(C)(C)c(ccc(C)c1-c2c(C=*)cc3)c1-c1c2c3ccc1C(C)(C)C 0.000 description 3
- IXNYMFQBPGDEOP-UHFFFAOYSA-N CC(C)(C)C1=C(c2c3c(cc4)ccc2)c2c3c4ccc2CC1 Chemical compound CC(C)(C)C1=C(c2c3c(cc4)ccc2)c2c3c4ccc2CC1 IXNYMFQBPGDEOP-UHFFFAOYSA-N 0.000 description 1
- PXXUOXYPWFRJOR-UHFFFAOYSA-N Clc1ccc(-c2cccc(cc3)c22)c4c2c3ccc14 Chemical compound Clc1ccc(-c2cccc(cc3)c22)c4c2c3ccc14 PXXUOXYPWFRJOR-UHFFFAOYSA-N 0.000 description 1
- IOKFXCFIYCUWTK-UHFFFAOYSA-N c(cc1)ccc1-c1c(-c2c(c-3ccc4-c5ccc(-c6ccc7)c8c5ccc5c8c6c7cc5)c4ccc2)c-3c(-c2ccccc2)c2c1cccc2 Chemical compound c(cc1)ccc1-c1c(-c2c(c-3ccc4-c5ccc(-c6ccc7)c8c5ccc5c8c6c7cc5)c4ccc2)c-3c(-c2ccccc2)c2c1cccc2 IOKFXCFIYCUWTK-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(1)複数のベンゼン環が任意の位置で結合して構成されている置換基
(2)縮合多環芳香族基
(3)縮合多環芳香環に1以上のベンゼン環が任意の位置で結合して構成されている置換基
上記(1)の置換基の例としては、ビフェニル基、ターフェニル基等が挙げられる。
上記(2)の具体例の例としては、ナフチル基、ナフチル−d7基、アセナフチレニル基、アントリル基、アントリル−d9基、フェナントリル基、フェナントリル−d9基、ピレニル基、ピレニル−d9基、アセフェナントリレニル基、アセアントリレニル基、クリセニル基、ジベンゾクリセニル基、ベンゾアントリル基、ベンゾアントリル−d11基、ジベンゾアントリル基、ナフタセニル基、ピセニル基、ペンタセニル基、フルオレニル基、トリフェニレニル基、ペリレニル基、ペリレニル−d−11、フルオランテニル基、ベンゾ[k]フルオランテニル基等が挙げられるが、もちろんこれらに限定されるものではない。
上記(3)は、具体的には、上記(2)の具体例として挙げられる縮合多環芳香族基に、ベンゼン環又は上記(1)で挙げられる置換基が結合して構成される置換基をいう。
1.発光層内での電子・ホールの輸送。
2.ホストの励起子生成。
3.ホスト分子間の励起エネルギー伝達。
4.ホストからゲストへの励起エネルギー移動。
本発明の有機発光素子で使用されるtert−ブチル基4置換のベンゾ[ghi]フルオランテン誘導体及びtert−ブチル基5置換のベンゾ[ghi]フルオランテン誘導体は、例えば以下に説明するような方法により製造できる。
本発明の例示化合物216は、例えば以下に説明するような方法により製造できる。
2−クロロ−5−メトキシアニリンを出発原料として、下記反応式[1]で示される方法で、1−クロロ−2−ヨード−4−メトキシベンゼンを得た。このとき、Journal of Organic Chemistry 1983,48,4396に記載の合成法を参考にした。
上記反応式[3]で得られた中間体化合物1(5−クロロベンゾ[ghi]フルランテン)を出発原料として、下記反応式[4]で示される方法で例示化合物No.216の合成を行なった。このとき、Journal of American Chemical Society 2005,127,4685に記載の合成法を参考にした。
2−(7,12−ジフェニルベンゾ[k]フルオランテン−3−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン:185mg(0.345mmol)
ジシクロヘキシル(2’,6’−ジメトキシビフェニ−2−イル)フォスフィン:9.4mg(0.024mmol)
リン酸三カリウム:122mg(0.57mmol)
トルエン:20mL
水:2mL
酢酸パラジウム:2.6mg(0.012mmol)
(例示化合物134):4,4,5,5−テトラメチル−2−(9,9,9’,9’−テトラメチル−9H,9H’−2,2’−ビフルオレン−7−イル)―1,3,2,−ジオキサボロラン
(例示化合物201):4,4,5,5−テトラメチル−2−(ピレン−1−イル)−1,3,2,−ジオキサボロラン
(例示化合物203):2−(フルオランテン−3−イル)−4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン
(例示化合物205):2−(クリセン−6−イル)−4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン
(例示化合物207):2−(7−tert−ブチルピレン−2−イル)−4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン
(例示化合物208):2−(ベンゾ[ghi]−フルオランテン−5−イル)−4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン
下記式に示される化合物A−0について、実施例2と同様の方法で発光量子収率を求めた。結果を表2に示す。
2,2−(9,9’−ジメチル−9H−フルオレン−2,7−ジイル)−ビス(4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン):257mg(0.57mmol)
テトラキストリフェニルフォスフィンパラジウム:66mg(0.06mmol)
(例示化合物No.401):1,4−ビフェニルボロン酸
(例示化合物No.407):ビフェニル−4,4’−ジイルボロン酸
(例示化合物No.504):2,7−ビス(4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン−2−イル)ナフタレン
(例示化合物No.506):2,6−ビス(4,4,5,5−テトラメチル−1,3,2,−ジオキサボロラン−2−イル)ナフタレン
(例示化合物No.505):ナフタレン−1,4−ジボロン酸
(例示化合物No.507):ナフタレン−1,5−ジボロン酸
(例示化合物No.508):アントラセン−9,10−ジボロン酸
(例示化合物No.510):クリセン−6,12−ジボロン酸
図2に示す構造の有機発光素子を以下に示す方法で作製した。
図4に示す構造の有機発光素子を以下に示す方法で作製した。
2 陽極
3 発光層
4 陰極
5 ホール輸送層
6 電子輸送層
7 ホール注入層
8 ホール/エキシトンブロッキング層
10,20,30,40,50 有機発光素子
Claims (6)
- 前記R5及び前記R10のいずれかが二環以上からなる置換あるいは無置換のアリール基及び置換あるいは無置換の縮合多環複素環基から選ばれる置換基であることを特徴とする、請求項1に記載のベンゾ[ghi]フルオランテン誘導体。
- 下記一般式[2]で示されることを特徴とする、請求項1に記載のベンゾ[ghi]フルオランテン誘導体。
- 陽極及び陰極からなる一対の電極と、該一対の電極間に挟持される少なくとも一層の有機化合物を含む層とからなり、該陽極及び該陰極のいずれかが透明又は半透明である有機発光素子において、該有機化合物を含む層のうち少なくとも一層が請求項1乃至3のいずれか1項に記載のベンゾ[ghi]フルオランテン誘導体を少なくとも一種類含有することを特徴とする、有機発光素子。
- 前記ベンゾ[ghi]フルオランテン誘導体を含有する層が発光層であることを特徴とする、請求項4に記載の有機発光素子。
- 前記発光層が、ホストとゲストとから構成されることを特徴とする請求項5に記載の有機発光素子。
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JP2007127794A JP5159164B2 (ja) | 2007-05-14 | 2007-05-14 | ベンゾ[ghi]フルオランテン誘導体及びこれを用いた有機発光素子 |
US12/118,227 US8021766B2 (en) | 2007-05-14 | 2008-05-09 | Benzo(GHI)fluoranthene derivative and organic light emitting device using the same |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008255099A (ja) * | 2007-03-12 | 2008-10-23 | Canon Inc | ナフタレン化合物及びこれを用いた有機発光素子 |
WO2010076878A1 (ja) * | 2009-01-05 | 2010-07-08 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2017183723A (ja) * | 2016-03-29 | 2017-10-05 | 住友化学株式会社 | 発光素子 |
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4819655B2 (ja) * | 2006-04-27 | 2011-11-24 | キヤノン株式会社 | 4−アリールフルオレン化合物及びそれを用いた有機発光素子 |
JP5089235B2 (ja) * | 2006-08-04 | 2012-12-05 | キヤノン株式会社 | 縮合複素環化合物および有機発光素子 |
JP5241256B2 (ja) * | 2007-03-09 | 2013-07-17 | キヤノン株式会社 | 縮合環芳香族化合物及びこれを用いた有機発光素子 |
JP5414190B2 (ja) * | 2007-04-02 | 2014-02-12 | キヤノン株式会社 | 有機発光素子 |
JP5441348B2 (ja) | 2007-05-16 | 2014-03-12 | キヤノン株式会社 | ベンゾ[a]フルオランテン化合物及びそれを用いた有機発光素子 |
JP5361237B2 (ja) * | 2007-05-16 | 2013-12-04 | キヤノン株式会社 | ベンゾ[a]フルオランテン化合物及びそれを用いた有機発光素子 |
JP5361238B2 (ja) * | 2007-05-16 | 2013-12-04 | キヤノン株式会社 | ベンゾ[a]フルオランテン化合物及びそれを用いた有機発光素子 |
JP5142589B2 (ja) * | 2007-05-28 | 2013-02-13 | キヤノン株式会社 | インデノクリセン誘導体及びそれを用いた有機発光素子 |
JP5777408B2 (ja) | 2011-05-30 | 2015-09-09 | キヤノン株式会社 | 縮合多環化合物及びこれを用いた有機発光素子 |
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JP2008255099A (ja) * | 2007-03-12 | 2008-10-23 | Canon Inc | ナフタレン化合物及びこれを用いた有機発光素子 |
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JP2017183723A (ja) * | 2016-03-29 | 2017-10-05 | 住友化学株式会社 | 発光素子 |
JP7033397B2 (ja) | 2016-03-29 | 2022-03-10 | 住友化学株式会社 | 発光素子 |
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
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JP5159164B2 (ja) | 2013-03-06 |
US20080286611A1 (en) | 2008-11-20 |
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