JP4980938B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP4980938B2 JP4980938B2 JP2008009909A JP2008009909A JP4980938B2 JP 4980938 B2 JP4980938 B2 JP 4980938B2 JP 2008009909 A JP2008009909 A JP 2008009909A JP 2008009909 A JP2008009909 A JP 2008009909A JP 4980938 B2 JP4980938 B2 JP 4980938B2
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- organic electroluminescent
- light emitting
- general formula
- Prior art date
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- 238000002347 injection Methods 0.000 claims description 64
- 239000007924 injection Substances 0.000 claims description 64
- 239000000463 material Substances 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000002346 layers by function Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
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Description
Appl.Phys.Lett.,51,913(1987) J.Appl.Phys.,65,3610(1989) Appl.Phys.Lett.,70,1665(1997) Jpn.J.Appl.Phys.,34,L824(1995) Appl.Phys.Lett.,74,442(1999) Appl.Phys.Lett.,75,4(1999)
[1]一対の電極間に、発光層を含む機能層を挟持してなる有機電界発光素子であって、
前記発光層は燐光発光材料を含有し、
前記機能層のいずれかの層は、一般式(1)で表されるフルオレン化合物の少なくとも1種を含有する、有機電界発光素子。
R1〜R6は、それぞれ独立に置換基を表し、R1〜R6はそれぞれ隣接する基と共に、環を形成していてもよく、
n1〜n6は0または1〜3の整数を表し、
AおよびBは、直鎖、分岐鎖または環状のアルキル基、置換または未置換のアリール基あるいは置換または未置換のアラルキル基を表すが、AとBは互いに同一の基ではなく
nは1または2を表す。
ただし、AおよびBがいずれもアリール基である場合は除かれる。
また、発光層に含まれる化合物の正孔注入機能や正孔輸送機能が十分でない場合には、発光層の陽極側に正孔注入輸送層を設けた二層型の素子とすることが好ましい。一方、発光層に含まれる化合物の電子注入機能や電子輸送機能が十分でない場合には、発光層の陰極側に電子注入輸送層を設けた二層型の素子とすることができる。もちろん、発光層を、正孔注入輸送層と電子注入輸送層で挟み込んだ三層型の素子とすることもできる。
図1には、基板1/陽極2/正孔注入輸送層3/発光層4/電子注入輸送層5/陰極6と、電源7を含む素子(EL−1)が;図2には、基板1/陽極2/正孔注入輸送層3/発光層4/陰極6と、電源7を含む素子(EL−2)が;図3には、基板1/陽極2/発光層4/電子注入輸送層5/陰極6と、電源7を含む素子(EL−3)が;図4には、基板1/陽極2/発光層4/陰極型6と、電源7を含む素子(EL−4)が示される。
本発明の有機発光素子の発光層は、燐光発光材料を含む。燐光発光材料は、発光層においてドーパント材料(またはゲスト材料)として作用することが好ましい。発光層に含有される燐光発光材料は、一種単独でも、二種以上の組合せでもよい。燐光発光材料は、特に限定されないが、遷移金属錯体であることが好ましい。遷移金属錯体の例には、下記一般式(a−1)または一般式(a−2)で表される化合物が含まれる。
本発明の有機電界発光素子は、一対の電極に狭持される機能層の、少なくともいずれかの一層に、一般式(1)で表される化合物を含む。一般式(1)で表される化合物は、正孔注入輸送層および/または発光層に含まれることが好ましく、発光層に含まれることがより好ましい。発光層に含まれる一般式(1)で表される化合物は、ホスト材料として作用することが好ましい。
式(1)におけるAおよびBは、直鎖、分岐または環状のアルキル基、置換または未置換のアリール基あるいは置換または未置換のアラルキル基を表す。ただし、AとBは互いに同一の基ではない。さらに、AとBのいずれもが、アリール基である場合は除かれる。
式(1)におけるnは、1または2を表す。
R1〜R6が表す置換基は、水素原子;ハロゲン原子;シアノ基;ニトロ基;置換または未置換のアミノ基;エステル基;炭素数1〜10の直鎖、分岐または環状のアルキル基;炭素数1〜10の直鎖、分岐または環状のアルコキシ基;炭素数7〜20の置換または未置換のアラルキル基;炭素数7〜20の置換または未置換のアラルキルオキシ基;炭素数4〜20の置換または未置換のアリール基;または炭素数4〜20の置換または未置換のアリールオキシ基であることが好ましい。
R1〜R6が表す置換基は、水素原子;ハロゲン原子;シアノ基;ニトロ基;置換または未置換のアミノ基;炭素数1〜8の直鎖、分岐または環状のアルキル基;炭素数1〜8の直鎖、分岐または環状のアルコキシ基;炭素数7〜16の置換または未置換のアラルキル基;炭素数7〜16の置換または未置換のアラルキルオキシ基;炭素数4〜16の置換または未置換のアリール基;または炭素数4〜16の置換または未置換のアリールオキシ基であることがより好ましい。
1.Aが直鎖、分岐または環状のアルキル基、BがAとは異なる直鎖、分岐または環状のアルキル基の組合せ
1−1.Aが直鎖または分岐のアルキル基、Bが環状のアルキル基の組合せ
1−2.Aが環状のアルキル基、Bが直鎖または分岐のアルキル基の組合せ
1−3.Aが直鎖のアルキル基、Bが分岐のアルキル基の組合せ
1−4.Aが分岐のアルキル基、Bが直鎖のアルキル基の組合せ
2.Aが直鎖、分岐または環状のアルキル基、Bが置換または未置換のアリール基の組合せ
3 Aが置換または未置換のアリール基、Bが直鎖、分岐または環状のアルキル基の組合せ
4.Aが直鎖、分岐または環状のアルキル基、Bが置換または未置換のアラルキル基の組合せ
5.Aが置換または未置換のアラルキル基、Bが直鎖、分岐または環状のアルキル基の組合せ
6.Aが置換または未置換のアラルキル基、Bが置換または未置換のアリール基の組合せ
7.Aが置換または未置換のアリール基、Bが置換または未置換のアラルキル基の組合せ
8.Aが置換または未置換のアラルキル基、BがAとは異なる置換または未置換のアラルキル基の組合せ
(式(a)におけるQは、置換または未置換の8-キノリノラート配位子を表す)
(Q)2−Al−O−L’ ・・・(b)
(式(b)におけるQは、置換または未置換の8-キノリノラート配位子を表し、O−L’はフェノラート配位子を表し、L’はフェニル基を有する炭素数6〜24の炭化水素基を表す)
(Q)2−Al−O−Al−(Q)2 ・・・(c)
(式(c)におけるQは、置換または未置換の8-キノリノラート配位子を表す)
バインダー樹脂を使用する場合、塗布液におけるその含有量は特に限定されない。正孔注入輸送層、発光層、電子注入輸送層等の各層を形成する成分の合計に対するバインダー樹脂の含有率は、通常は5〜99.9重量%であり、好ましくは10〜99重量%である。
厚さ150nmのITO透明電極(陽極)を有するガラス基板を、中性洗剤、セミコクリーン(フルウチ化学製)、超純水、アセトン、イソプロパノールを用いて超音波洗浄した。この基板を窒素ガスにより乾燥し、さらにUV/オゾン洗浄した後、蒸着装置の基板ホルダーに固定し、蒸着槽を1×10−5Paに減圧した。
実施例1において、発光層の形成に際して例示化合物A−4の化合物を使用する代わりに、下記の化合物(CBP)を使用した以外は、実施例1に記載の操作に従い、有機電界発光素子を作製した。
実施例1において、例示化合物A−4の化合物を使用する変わりに、例示化合物A−9の化合物を使用した以外は、実施例1に記載の操作に従い、有機電界発光素子を作製した。
実施例1において、発光層の形成に際して例示化合物A−4の化合物を使用する代わりに、下記の4,4'−ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(α−NPD)を使用した以外は、実施例1に記載の操作に従い、有機電界発光素子を作製した。
実施例1において、例示化合物A−4の化合物を使用する変わりに、例示化合物A−21の化合物を使用した以外は、実施例1に記載の操作に従い、有機電界発光素子を作製した。
実施例1において、例示化合物A−4の化合物を使用する変わりに、例示化合物A−26の化合物を使用した以外は、実施例1に記載の操作に従い、有機電界発光素子を作製した。
厚さ150nmのITO透明電極(陽極)を有するガラス基板を、中性洗剤、セミコクリーン(フルウチ化学製)、超純水、アセトン、イソプロパノールを用いて超音波洗浄した。この基板を窒素ガスにより乾燥し、さらにUV/オゾン洗浄した後、蒸着装置の基板ホルダーに固定し、蒸着槽を1×10−5Paに減圧した。
実施例5において、例示化合物B−9の化合物を使用する変わりに、例示化合物B−31の化合物を使用した以外は、実施例5に記載の操作に従い、有機電界発光素子を作製した。
実施例5において、例示化合物B−9の化合物を使用する変わりに、例示化合物A−61の化合物を使用した以外は、実施例5に記載の操作に従い、有機電界発光素子を作製した。
実施例5において、例示化合物B−9の化合物を使用する変わりに、例示化合物A−36の化合物を使用した以外は、実施例5に記載の操作に従い、有機電界発光素子を作製した。
実施例5において、例示化合物B−9の化合物を使用する変わりに、例示化合物A−2の化合物を使用した以外は、実施例5に記載の操作に従い、有機電界発光素子を作製した。
厚さ110nmのITO透明電極(陽極)を有するガラス基板を、中性洗剤、セミコクリーン(フルウチ化学製)、超純水、アセトン、イソプロパノールを用いて超音波洗浄した。この基板を窒素ガスにより乾燥し、さらにUV/オゾン洗浄した後、蒸着装置の基板ホルダーに固定し、蒸着槽を1×10−5Paに減圧した。
比較例1の有機電界発光素子と比較して本発明の化合物を正孔阻止層に使用することで、駆動電圧が低電圧化し、発光輝度が向上し、輝度の半減期も永くなることが分かる。
実施例10において、正孔阻止層(電子輸送層)の形成にあたり、例示化合物A−61の化合物を使用する変わりに、例示化合物B−31の化合物を使用した以外は、実施例10に記載の操作に従い、有機電界発光素子を作製した。
厚さ110nmのITO透明電極(陽極)を有するガラス基板を、中性洗剤、セミコクリーン(フルウチ化学製)、超純水、アセトン、イソプロパノールを用いて超音波洗浄した。この基板を窒素ガスにより乾燥し、さらにUV/オゾン洗浄した後、蒸着装置の基板ホルダーに固定し、蒸着槽を1×10−5Paに減圧した。
比較例1の有機電界発光素子と比較して本発明の化合物を正孔輸送層に使用することで、駆動電圧が低電圧化し、発光輝度が向上し、輝度の半減期も永くなることが分かる。
2 陽極
3 正孔注入輸送層
3’ 正孔注入層
3” 正孔輸送層
3a 正孔注入輸送成分
4 発光層
4a 発光成分
5 電子注入輸送層
5’ 正孔阻止層(電子輸送層)
5a 電子注入輸送成分
6 陰極
7 電源
Claims (9)
- 一対の電極間に、発光層、正孔注入輸送層、及び電子注入輸送層を含む機能層を挟持してなる有機電界発光素子であって、
前記発光層は下記一般式(a−1)で表される燐光発光材料を含有し、
前記発光層、前記正孔注入輸送層、及び前記電子注入輸送層からなる群から選ばれるいずれかの層に、下記一般式(1)で表されるフルオレン化合物の少なくとも1種を含有する、有機電界発光素子。
M1は、m価の金属原子を表し、
A1は、5員または6員の含窒素複素環を形成するための原子群を表し、
A2は、5員または6員の環状構造を形成するための原子群を表し、
LおよびL’はM1に配位可能な原子を表し、LおよびL’を繋ぐ点線は結合を形成していても、分離していてもよいことを表し、
ndは1〜mの整数を表す。〕
R1〜R6は、それぞれ独立に置換基を表し、R1〜R6はそれぞれ隣接する基と共に、環を形成していてもよく、
n1〜n6は0または1〜3の整数を表し、
AおよびBは、直鎖、分岐鎖または環状のアルキル基、置換または未置換のアリール基あるいは置換または未置換のアラルキル基を表すが、AとBは互いに同一の基ではなく
nは1または2を表す(ただし、AおよびBがいずれもアリール基である場合を除く)。〕 - 前記式(a−1)中のM1で表される金属原子が、イリジウムまたは白金である、請求項1に記載の有機電界発光素子。
- 一般式(1)において、AおよびBの一方が、直鎖、分岐または環状のアルキル基であり、かつ他方が、置換または未置換のアラルキル基である、請求項1に記載の有機電界発光素子。
- 一般式(1)において、AおよびBの一方が、直鎖または分岐のアルキル基であり、他方が、環状のアルキル基である、請求項1に記載の有機電界発光素子。
- 一般式(1)で表されるフルオレン化合物を含有する層が発光層である、請求項1〜4のいずれか一項に記載の有機電界発光素子。
- 一般式(1)で表されるフルオレン化合物を含有する層が正孔注入輸送層である、請求項1〜4のいずれか一項に記載の有機電界発光素子。
- 一般式(1)で表されるフルオレン化合物を含有する層が電子注入輸送層である、請求項1〜4のいずれか一項に記載の有機電界発光素子。
- 前記一対の電極間に挟持される機能層は、正孔注入輸送層をさらに有する、請求項1〜7のいずれか一項に記載の有機電界発光素子。
- 前記一対の電極間に挟持される機能層は、電子注入輸送層をさらに有する、請求項1〜8のいずれか一項に記載の有機電界発光素子。
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