JP5366505B2 - インデノピレン化合物及びこれを用いた有機発光素子 - Google Patents
インデノピレン化合物及びこれを用いた有機発光素子 Download PDFInfo
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- JP5366505B2 JP5366505B2 JP2008285376A JP2008285376A JP5366505B2 JP 5366505 B2 JP5366505 B2 JP 5366505B2 JP 2008285376 A JP2008285376 A JP 2008285376A JP 2008285376 A JP2008285376 A JP 2008285376A JP 5366505 B2 JP5366505 B2 JP 5366505B2
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- -1 Indenopyrene compound Chemical class 0.000 title claims abstract description 100
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
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- 239000012044 organic layer Substances 0.000 abstract description 6
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- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 9
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 7
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- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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Images
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Description
(a)R1、R3乃至R5、R9、R11、R13及びR14が水素原子
(b)R2、R6、R7、R8及びR12が水素原子又は置換あるいは無置換のアルキル基
(c)R10が水素原子、置換あるいは無置換のアルキル基、ハロゲン原子又は置換あるいは無置換のアミノ基
この第一の好適例の具体例を以下に示す。ただし本発明はこれに限定されない。
(b)R2、R6、R7及びR8が水素原子又は置換あるいは無置換のアルキル基
(c)R10が水素原子、置換あるいは無置換の芳香族基又は置換あるいは無置換の縮合多環芳香族基
(b)R2、R7及びR8が水素原子又は置換あるいは無置換のアルキル基
(c)R10が置換あるいは無置換の縮合多環芳香族基又は置換あるいは無置換のアミノ基
この第三の好適例の具体例を以下に示す。ただし本発明はこれに限定されない。
1.発光層内での電子・正孔の輸送。
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。
非特許文献2に記載の合成方法を参考にして、2−ブロモ−5−クロロ安息香酸を出発原料として、中間体[1−1](2−ブロモ−5−クロロ安息香酸メチル)を合成した。
(2)中間体[1−2](2−(7−tert−ブチルピレン−1−イル)−5−クロロ安息香酸メチル)の合成
非特許文献3に記載の合成方法を参考にして、中間体[1−1](2−ブロモ−5−クロロ安息香酸メチル)を出発原料として、中間体[1−2](2−(7−tert−ブチルピレン−1−イル)−5−クロロ安息香酸メチル)を合成した。
(3)中間体[1−3](2−(2−(7−ターシャリーブチルピレン−1−イル)−5−クロロフェニル)プロパン−2−オール)の合成
中間体[1−2](2−(7−tert−ブチルピレン−1−イル)−5−クロロ安息香酸メチル)を出発原料として、中間体[1−3](2−(2−(7−tert−ブチルピレン−1−イル)−5−クロロフェニル)プロパン−2−オール)を得た。合成にあたっては、非特許文献4に記載の合成方法を参考にした。
(4)例示化合物3の合成
反応容器内を窒素雰囲気にした後、以下に示す試薬、溶媒を仕込んだ。
中間体[1−3]:3.710g
ジクロロメタン:100mL
フッ化ホウ素エテラート:0.2ml
1H−NMR(CDCl3):δ(ppm)=8.87(1H,d,J=9.16Hz),8.42(1H,d,J=8.47Hz),8.25(2H,d,J=1.98Hz),8.22(1H,d,J=9.39Hz),8.18(1H,s),8.07(2H,d,J=1.37Hz),7.56(1H,d,J=2.06Hz),7.48(1H,dd,J1=8.47,J2=2.06Hz).
2−(7−tert−ブチルピレン−1−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボランに代えて2−ピレニル−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。また2−ブロモ−5−クロロ安息香酸に代えて2−ブロモ安息香酸を使用する。こうすることで例示化合物1を合成することができる。
2−(7−tert−ブチルピレン−1−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−(7−tert−ブチル−3−メチルピレン−1−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランにする。こうすることで例示化合物2を合成することができる。
2−(7−tert−ブチルピレン−1−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−(7−tert−ブチル−3−メチルピレ−1−ニル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。また2−ブロモ−5−クロロ安息香酸に代えて2−ブロモ−5−メチル安息香酸を使用する。こうすることで例示化合物6を合成することができる。
2−ブロモ−5−クロロ安息香酸に代えて2−ブロモ−5−アミノ安息香酸を使用する。こうすることで例示化合物7を合成することができる。
2−ブロモ−5−クロロ安息香酸に代えて2−ブロモ−3−メチル安息香酸を使用する。こうすることで例示化合物10を合成することができる。
反応容器内を窒素雰囲気にした後、以下に示す試薬、溶媒を仕込んだ。
例示化合物2:119mg
2−(2,7−ジ−tert−ブチル−9,9−ジメチル−9H−フルオレン−4−イル−)4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン:144mg(0.33mmol)
酢酸パラジウム:15mg
ジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)フォスフィン:48mg
リン酸カリウム:357mg
トルエン:80mL
水:10mL
1H−NMR(CDCl3):δ(ppm)=9.07(1H,d,J=9.39Hz),8.65(1H,d,J=8.01Hz),8.37(1H,d,J=9.16Hz),8.23(2H,s),8.17(1H,d,J=9.16Hz),8.12(1H,d,J=9.16Hz),7.78(1H,d,J=1.60Hz),7.64(1H,d,J=7.79Hz),7.48(1H,d,J=1.83Hz),7.43(1H,d,J=1.60Hz),7.33(1H,d,J=1.83Hz),7.09(1H,d,J=8.24Hz),7.03−7.00(1H,M),3.20(3H,s),1.61(9H,s),1.517(3H,s),1.514(6H,s),1.511(3H,s),1.45(9H,s),1.30(9H,s).
例示化合物2に代えて例示化合物3を使用する。また2−〔2,7−ジ−tert−ブチル−9,9−ジメチル−9H−フルオレン−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−〔ビフェニル−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。こうすることで例示化合物13を合成することができる。
2−〔2,7−ジ−tert−9,9−ジメチル−9H−フルオレン−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−〔4−〔9,9−ジメチル−9H−フルオレン−2−イル〕フェニル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。こうすることで例示化合物14を合成することができる。
例示化合物2に代えて例示化合物3を使用する。また2−〔2,7−ジ−tert−ブチル−9,9−ジメチル−9H−フルオレン−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−〔ピレン−1−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。こうすることで例示化合物17を合成することができる。
例示化合物2に代えて例示化合物3を使用する。また2−〔2,7−ジ−tert−ブチル−9,9−ジメチル−9H−フルオレン−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランに代えて2−〔クリセン−6−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを使用する。こうすることで例示化合物27を合成することができる。
例示化合物2に代えて例示化合物3を使用する。2−〔2,7−ジ−tert−ブチル−9,9−ジメチル−9H−フルオレン−4−イル〕−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランから2−〔4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル〕キノリンに代える。こうすることで例示化合物32を合成することができる。
例示化合物3を出発原料として、中間体[1−4](2−(2−tert−ブチル−7,7−ジメチル−7H−インデノ〔1,2−a〕ピレン−9−イル)−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン)を合成した。合成にあたっては、非特許文献5に記載の方法を参考にした。
反応容器内を窒素雰囲気にした後、以下の試薬、溶媒を仕込んだ。
中間体[1−5]:1300mg
4,4’−ジヨードビフェニル:380mg
テトラキストリフェニルホスフィンパラジウム:50mg
炭酸ナトリウム:500mg
トルエン:40mL
エタノール:10mL
水:25mL
1H−NMR(ODB):δ(ppm)=8.27(4H,s),8.24(4H,s),8.23(2H,s),8.04(4H,d,J=5.95Hz),7.98(2H,s),7.90(4H,d,J=8.01Hz),7.83(4H,d,J=8.47Hz),7.19(4H,d,J=6.64Hz),1.77(12H,s),1.58(18H,s).
〔E〕−1,2−ジヨードエチレンを使用することにより例示化合物42を合成することができる。
3,8−ジブロモフルオランテンを使用することにより例示化合物46を合成することができる。
6,12−ジブロモクリセンを使用することにより例示化合物47を合成することができる。
下記に示されるピレン(化合物A−0)について、まず約10-7mol/lトルエン溶液を調製し、分光光度計(U−3310、(株)日立製作所社製)を用い、波長332nmでの当該溶液の吸光度を測定した。次に、蛍光分光光度(F−4500、(株)日立製作所社製)を用い、波長332nmを励起波長としたときの当該溶液の発光スペクトルを測定した。発光スペクトルのピーク面積及び吸光度から発光量子収率の相対値を求めた。このとき実施例1における例示化合物3の発光量子収率を0.55とした。結果を表1に示す。
図4に示される構造の有機発光素子を以下に示す方法で作製した。
実施例4において、発光層5のゲストとして例示化合物48に代えて例示化合物26を使用した。これ以外は実施例4と同様の方法により有機発光素子を作製した。この素子について実施例4と同様に電圧を印加すると青色の発光が観測された。
2 陽極
3 発光層
4 陰極
5 正孔輸送層
6 電子輸送層
7 正孔注入層
8 正孔/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)
- 陽極と陰極と、
該陽極と該陰極との間に挟持される有機化合物層と、から構成され、
該陽極及び該陰極のいずれかが透明電極又は半透明電極であり、
該有機化合物層のうち少なくとも一層に請求項1または2に記載のインデノピレン化合物が少なくとも一種類含まれることを特徴とする、有機発光素子。 - 前記インデノピレン化合物が発光層に含まれることを特徴とする、請求項3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4に記載の有機発光素子。
- 前記インデノピレン化合物が前記ゲストであ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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