JP2010140976A - 有機エレクトロルミネッセンス素子用材料およびそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料およびそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP2010140976A JP2010140976A JP2008313814A JP2008313814A JP2010140976A JP 2010140976 A JP2010140976 A JP 2010140976A JP 2008313814 A JP2008313814 A JP 2008313814A JP 2008313814 A JP2008313814 A JP 2008313814A JP 2010140976 A JP2010140976 A JP 2010140976A
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- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
窒素複素環誘導体を有機化合物層の少なくとも1 層に用いることにより、低駆動電圧化、高輝度化、高発光効率化、長寿命化が達成できる有機E L 素子を提供することを目的とする。
分子量よりも、使用する溶媒に対する溶解性と塗布膜のアモルファス性が重要となるので、
非対称構造がより好ましい。
注入機能;電界印加時に陽極または正孔注入層より正孔を注入することができ、陰極または電子注入層より電子を注入することができる機能
輸送機能;注入した電荷(電子と正孔)を電界の力で移動させる機能
発光機能;電子と正孔の再結合の場を提供し、これを発光につなげる機能
ただし、正孔の注入されやすさと電子の注入されやすさには、違いがあってもよく、また正孔と電子の移動度で表される輸送能に大小があってもよい。
洗浄したITO電極付きガラス板上に、表3のHTM8を蒸着して膜厚25nmの正孔注入層を形成した。次に、表1の化合物(1)と下記化合物(A)とを100:3の組成比で共蒸着して膜厚45nmの発光層を形成した。さらに、下記化合物(B)を蒸着して膜厚20nmの正孔ブロッキング層を形成した。その上に、さらに、トリス(8−ヒドロキシキノリノ)アルミニウム錯体(Alq3)を真空蒸着して膜厚30nmの電子注入型発光層を作成し、その上に、まずフッ化リチウム(LiF)を1nm、次いでアルミニウム(Al)を200nm蒸着して電極を形成して、有機EL素子を得た。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命は、500時間以上あった。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表7に示す。
化合物(1)のかわりに表7に示す化合物を用いて発光層を作成した以外は実施例1と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表7に示す。
化合物(1)のかわりに、下記化合物(C)を用いて発光層を作成した以外は実施例1と同様に素子を作成した。この素子は、緑色発光を示した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表7に示す。
ITO電極付きガラス板上に、表2のHIM4を真空蒸着して膜厚40nmの正孔注入層を得た。次に、表1の化合物(1)を真空蒸着して膜厚20nmの正孔注入層を得た。ついで下記化合物(D)と化合物(A)とを100:5の組成比で共蒸着して膜厚45nmの発光層を形成した。さらに下記化合物(E)を蒸着して膜厚20nmの電子注入層を形成した。その上に、LiFを1nm、さらにAlを100nm蒸着によって陰極を形成して有機EL素子を得た。この素子は、直流電圧10Vでの外部量子効率が3.4%を示した。また、発光輝度500(cd/m2)で定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表8に示す。
化合物(1)の代わりに表8中の化合物を用いた以外は、実施例21と同様に素子を作成した。これらの素子は、直流電圧10Vでの外部量子効率がいずれも3%以上を示した。また、発光輝度500(cd/m2)で定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表8に示す。
化合物(1)のかわりに、化合物(C)を用いた以外は実施例21と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表8に示す。
ITO電極付きガラス板上に、表2のHIM6を真空蒸着して膜厚30nmの正孔注入層を得た。次に、α−NPDを真空蒸着して膜厚30nmの正孔注入層を得た。ついで、下記化合物(F)と化合物(A)とを100:5の組成比で共蒸着して膜厚45nmの発光層を形成した。さらに表1中の化合物(7)を蒸着して膜厚10nmの正孔ブロッキング層を形成し、次に、下記化合物(G)を真空蒸着して、膜厚30nmの電子注入層を形成した。その上に、Li2Oを1nm、さらにAlを100nm蒸着によって陰極を形成して有機EL素子を得た。この素子は、直流電圧10Vでの外部量子効率は3.4%を示した。また、発光輝度500(cd/m2)で定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表9に示す。
化合物(1)の代わりに表8中の化合物を用いた以外は、実施例31と同様に素子を作成した。これらの素子は、直流電圧10Vでの外部量子効率がいずれも3%以上を示した。また、発光輝度500(cd/m2)で定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表9に示す。
化合物(1)のかわりに、化合物(C)を用いた以外は実施例31と同様に素子を作成した。この素子を発光輝度500(cd/m2)で室温にて定電流駆動したときの輝度半減寿命を測定した。また、電流密度10mA/cm2で駆動させた時の初期輝度、および80℃の環境で100時間連続駆動させた後の輝度を測定した。結果を表9に示す。
Claims (5)
- 下記一般式[1]で表される有機エレクトロルミネッセンス素子用材料。
一般式[1]
(式中、R1〜R16は、それぞれ独立に、水素原子、ハロゲン原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基、シアノ基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリ−ルオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリ−ルチオ基、置換アミノ基、置換もしくは未置換のアシル基、置換もしくは未置換のアルキルカルボニル基、置換もしくは未置換のアリ−ルカルボニル基、置換もしくは未置換のアルキルスルホニル基、または、置換もしくは未置換のアリ−ルスルホニル基を表す。) - R1およびR12が、下記一般式[2]で表される置換もしくは未置換のフェニル基である請求項1記載の有機エレクトロルミネッセンス素子用材料。
一般式[2]
(式中、R17〜R21は、それぞれ独立に、水素原子、ハロゲン原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基、シアノ基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリ−ルオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリ−ルチオ基、置換アミノ基、置換もしくは未置換のアシル基、置換もしくは未置換のアルキルカルボニル基、置換もしくは未置換のアリ−ルカルボニル基、置換もしくは未置換のアルキルスルホニル基、または、置換もしくは未置換のアリ−ルスルホニル基を表し、R17〜R21は、それぞれ隣り合う置換基同士で環を形成しても良い。) - 陽極と陰極からなる一対の電極間に、少なくとも、発光層を含む有機薄膜層を有する有機エレクトロルミネッセンス素子であって、
発光層が、リン光発光材料と請求項1または2記載の有機エレクトロルミネッセンス素子用材料とを含んでなる有機エレクトロルミネッセンス素子。 - 陽極と陰極からなる一対の電極間に、少なくとも、発光層と、電子注入層および/または
電子輸送層とを含む有機薄膜層を有する有機エレクトロルミネッセンス素子であって、
電子注入層および/または電子輸送層が、請求項1または2記載の有機エレクトロルミネ
ッセンス素子用材料を含んでなる有機エレクトロルミネッセンス素子。 - 陽極と陰極からなる一対の電極間に、少なくとも、発光層と、正孔阻止層とを含む有機薄
膜層を有する有機エレクトロルミネッセンス素子であって、
正孔阻止層が、請求項1または2記載の有機エレクトロルミネッセンス素子用材料を含む
有機エレクトロルミネッセンス素子。
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