JPWO2009136595A1 - 有機電界発光素子用化合物及び有機電界発光素子 - Google Patents
有機電界発光素子用化合物及び有機電界発光素子 Download PDFInfo
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- JAFUSJHYVMLOMY-YIOKEUICSA-N C/C=C\C=C/C(N(c(cc1c2ccc(c(cc(cc3)N(c4ccccc4)c4ccccc4)c3[n]3-c4ccccc4)c3c22)ccc1[n]2-c1cc(cccc2)c2nc1)C1=CCCC=C1)=C Chemical compound C/C=C\C=C/C(N(c(cc1c2ccc(c(cc(cc3)N(c4ccccc4)c4ccccc4)c3[n]3-c4ccccc4)c3c22)ccc1[n]2-c1cc(cccc2)c2nc1)C1=CCCC=C1)=C JAFUSJHYVMLOMY-YIOKEUICSA-N 0.000 description 1
- WNODWFGZDRCDMI-QHCPKHFHSA-N C[C@@H]1c(nc(cc2)-[n]3c(c(c4c5cccc4)c(cc4)[n]5-c5nc6ccccc6cc5)c4c4ccccc34)c2C=CC1 Chemical compound C[C@@H]1c(nc(cc2)-[n]3c(c(c4c5cccc4)c(cc4)[n]5-c5nc6ccccc6cc5)c4c4ccccc34)c2C=CC1 WNODWFGZDRCDMI-QHCPKHFHSA-N 0.000 description 1
- ASEYPSUBYGGZOI-CPSFFCFKSA-N Cc1c(/C=C\C=C)c(c2c(cc3)c4ccccc4[n]2-c2cc(cccc4)c4cc2)c3[n]1-c1cncc2ccccc12 Chemical compound Cc1c(/C=C\C=C)c(c2c(cc3)c4ccccc4[n]2-c2cc(cccc4)c4cc2)c3[n]1-c1cncc2ccccc12 ASEYPSUBYGGZOI-CPSFFCFKSA-N 0.000 description 1
- QGDNOFKZPQITED-UHFFFAOYSA-N c(cc1)cc(c(c2c3c4c5cccc4)ccc3[n]5-c3c4ncccc4ccc3)c1[n]2-c1c2ncccc2ccc1 Chemical compound c(cc1)cc(c(c2c3c4c5cccc4)ccc3[n]5-c3c4ncccc4ccc3)c1[n]2-c1c2ncccc2ccc1 QGDNOFKZPQITED-UHFFFAOYSA-N 0.000 description 1
- DLNOUHYYKKGXQM-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c(cccc2)c2[n]1-c1c2ncccc2ccc1 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c(cccc2)c2[n]1-c1c2ncccc2ccc1 DLNOUHYYKKGXQM-UHFFFAOYSA-N 0.000 description 1
- MWYYWXOOXSRGAL-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc1c1cnc2c3c4cccc3)c1c2[n]4-c1nc(cccc2)c2cc1 Chemical compound c(cc1)ccc1-[n](c1ccccc1c1cnc2c3c4cccc3)c1c2[n]4-c1nc(cccc2)c2cc1 MWYYWXOOXSRGAL-UHFFFAOYSA-N 0.000 description 1
- QTJPUTYNKBMLRF-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(c2c(cc3)c4ccccc4[n]2-c(cc2)nc(cc4)c2nc4-[n]2c4ccccc4c4ccccc24)c3c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(c2c(cc3)c4ccccc4[n]2-c(cc2)nc(cc4)c2nc4-[n]2c4ccccc4c4ccccc24)c3c2c1cccc2 QTJPUTYNKBMLRF-UHFFFAOYSA-N 0.000 description 1
- KYEHPXWKJYUSTH-UHFFFAOYSA-N c(cc1c(c2c3)cc4c3c3ccccc3[n]4-c3cccc4c3nccc4)ccc1[n]2-c1c2ncccc2ccc1 Chemical compound c(cc1c(c2c3)cc4c3c3ccccc3[n]4-c3cccc4c3nccc4)ccc1[n]2-c1c2ncccc2ccc1 KYEHPXWKJYUSTH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
R1〜R7のうち二つが隣接する場合、互いに結合して縮環を形成してもよい。例えば、二つのビニル基が隣接する場合、互いに結合し、ビニル基がそれぞれ結合しているインドロカルバゾール骨格中の二つの炭素と共に六員環を形成し、含窒素縮合六環となる。また、二つの隣接する置換基が二組ある場合、含窒素縮合七環を形成することもできる。
次に、1000ml三口フラスコに上記紫茶色粉末72.0g(261.5mmol)を加え、これに酢酸720g、トリフルオロ酢酸72.0gを加えて攪拌した。その後100℃まで加熱し、15時間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取し、得られた結晶を酢酸200 mlでリンス洗浄した後、ヘキサン200mlでリンス洗浄した。これを、減圧乾燥して白色粉末A’30.0g(117.1mmol、収率44.8%)を得た。得られた白色粉末A’は、インドロ[2,3-a]カルバゾールである。
APCI-MS, m/z 460 [M+H]+
図1において、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 上に正孔注入層として、銅フタロシアニン(CuPC) を 20 nm の厚さに形成した。次に、正孔輸送層として NPB を 40 nm の厚さに形成した。次に、正孔輸送層上に、発光層のホスト材料として化合物3と、ドーパントとしてのIr(ppy)3とを異なる蒸着源から、共蒸着し、35nmの厚さに発光層を形成した。この時、Ir(ppy)3の濃度は7.0 wt%であった。次に、電子輸送層としてAlq3を40nm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。
発光層のホスト材料として、化合物2を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物9を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物18を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物20を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物23を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物26を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物29を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物31を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物33を用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物35を用いた以外は実施例2と同様にして有機EL素子を作成した。
正孔輸送層としてHMTPDを用い、発光層のホスト材料としてTAZを用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、TAZを用いた以外は実施例2と同様にして有機EL素子を作成した。
発光層のホスト材料として、化合物35を用いた以外は実施例2と同様にして有機EL素子を作成した。
Claims (7)
- 下記一般式(1)で示される有機電界発光素子用化合物。
ここで、環aは、2つの隣接環と縮合する式(a1)又は(a2)で表される芳香環又は複素環を示し、環a'は、3つの隣接環と縮合する式(a1)で表される芳香環又は複素環を示す。環bは、2つの隣接環と縮合する式(b1)で表される複素環を示す。Xは、CR又はNを示す。Lは縮環構造を有するn+1価の芳香族複素環基を示す。Ar1〜Ar3は独立に、アルキル基、アラルキル基、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示すが、Ar2、Ar3は含窒素六員環であることはない。R、R1〜R7は独立に、水素、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、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、そのうちの二つが隣接する場合、互いに結合して環を形成してもよい。nは0〜5の整数を表す。 - 一般式(1)〜(3)において、Lがn+1価の炭素数6〜20の縮環構造を有する芳香族複素環基である請求項1〜3のいずれかに記載の有機電界発光素子用化合物。
- 請求項1〜3のいずれかに記載の有機電界発光素子用化合物を含む有機層を有することを特徴とする有機電界発光素子。
- 有機電界発光素子用化合物を含む有機層が、発光層、正孔輸送層、正孔注入層、電子輸送層、電子注入層及び正孔阻止素子層から選ばれる少なくとも一つの層である請求項5に記載の有機電界発光素子。
- 有機電界発光素子用化合物を含む有機層が発光層であり、該発光層が燐光発光性ドーパントと該有機電界発光素子用化合物をホスト材料として含有する請求項5に記載の有機電界発光素子。
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US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
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TWI468489B (zh) * | 2007-05-29 | 2015-01-11 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent element compounds and organic electroluminescent elements |
US8049411B2 (en) | 2008-06-05 | 2011-11-01 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
WO2009148016A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
CN102056911B (zh) * | 2008-06-05 | 2015-07-22 | 出光兴产株式会社 | 卤素化合物、多环系化合物及使用其的有机电致发光元件 |
DE102009005289B4 (de) * | 2009-01-20 | 2023-06-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung und elektronische Vorrichtungen, enthaltend diese |
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EP2284920B1 (en) | 2015-07-29 |
TW201006908A (en) | 2010-02-16 |
KR101082144B1 (ko) | 2011-11-09 |
JP4819181B2 (ja) | 2011-11-24 |
EP2284920A4 (en) | 2012-08-22 |
EP2284920A1 (en) | 2011-02-16 |
US8795848B2 (en) | 2014-08-05 |
KR20110010750A (ko) | 2011-02-07 |
WO2009136595A1 (ja) | 2009-11-12 |
TWI452114B (zh) | 2014-09-11 |
CN102017220B (zh) | 2012-11-07 |
CN102017220A (zh) | 2011-04-13 |
US20110062429A1 (en) | 2011-03-17 |
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