JP2017043596A - 有機電子素子用化合物、これを用いた有機電子素子及びその電子装置 - Google Patents
有機電子素子用化合物、これを用いた有機電子素子及びその電子装置 Download PDFInfo
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Abstract
【解決手段】式1で表される化合物と、第1電極、第2電極及び前記第1電極と前記第2電極との間の有機物層を含む有機電子素子、及び前記有機電子素子を含む電子装置が開示される。
【選択図】図1
Description
110 基板
120 第1電極
130 正孔注入層
140 正孔輸送層
141 バッファ層
150 発光層
151 発光補助層
160 電子輸送層
170 電子注入層
180 第2電極
Claims (19)
- 下記式1で表される化合物:
前記式1において、
Z環はC10−C20のアリール基であり、XはO又はSであり、
L1は単結合;C6−C60のアリーレン基;フルオレニレン基;O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基;及びC3−C60の脂肪族環とC6−C60の芳香族環との縮合環基;からなる群より選ばれ、
Ar1はC6−C60のアリール基;O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基;フルオレニル基;及びC3−C60の脂肪族環とC6−C60の芳香族環との縮合環基;からなる群より選ばれ、
m、n及びoはそれぞれ0〜4の整数であり、
R1、R2及びR3は互いに独立に、重水素;ハロゲン;C6−C60のアリール基;フルオレニル基;O、N、S、Si及びPのうち、少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基;C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基;C1−C50のアルキル基;C2−C20のアルケニル基;C2−C20のアルキニル基;C1−C30のアルコキシ基;C6−C30のアリールオキシル基;及び−L’−N(Ra)(Rb)からなる群より選ばれ、隣接するR1同士、隣接するR2同士及び隣接するR3同士のうち、少なくとも1組が互いに結合して環を形成することができ、
L’は単結合;C6−C60のアリーレン基;フルオレニレン基;C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基;及びC2−C60のヘテロ環基;からなる群より選ばれ、
Ra及びRbは互いに独立に、C6−C60のアリール基;フルオレニル基;C3−C60の脂肪族環とC6−C60の芳香族環との縮合環基;及びO、N、S、Si及びPのうち、少なくとも1つのヘテロ原子を含むC2−C60のヘテロ環基からなる群より選ばれ、
前記アリール基、ヘテロ環基、フルオレニル基、縮合環基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アリールオキシル基、アリーレン基及びフルオレニレン基は重水素;ハロゲン;シラン基;シロキサン基;ホウ素基;ゲルマニウム基;シアノ基;ニトロ基;C1−C20のアルキルチオ基;C1−C20のアルコキシ基;C1−C20のアルキル基;C2−C20のアルケニル基;C2−C20のアルキニル基;C6−C20のアリール基;重水素で置換されたC6−C20のアリール基;フルオレニル基;O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C20のヘテロ環基;C3−C20のシクロアルキル基;C7−C20のアリールアルキル基;及びC8−C20のアリールアルケニル基;からなる群より選ばれた1つ以上の置換基で更に置換することができる。 - 前記式1は下記式2〜4のうちのいずれか1つに表される、請求項1に記載の化合物:
前記式2〜4において、Ar1、L1、R1〜R3、m、n、o及びXは請求項1における定義と同様である。 - 前記Z環はナフタレン又はフェナントレンであり、請求項1に記載の化合物。
- 前記式1は下記化合物のうちの1つである、請求項1に記載の化合物:
- 第1電極;第2電極;及び前記第1電極と第2電極との間に位置する有機物層;を含む有機電子素子において、
前記有機物層は請求項1〜請求項4のうち、いずれか1つの請求項の化学物を含有することを特徴とする有機電子素子。 - 前記化合物は前記有機物層の発光層に含有されていることを特徴とする請求項5に記載の有機電子素子。
- 前記化合物は前記発光層の燐光レッドホスト材料として用いられることを特徴とする請求項6に記載の有機電子素子。
- 前記発光層のホスト材料は前記化合物を含み、前記発光層のドーパント材料は下記式6で表される化合物を含むことを特徴とする請求項6に記載の有機電子素子:
前記式6において、
A環及びB環は互いに独立に、C4−C20のシクロアルキル;C2−C20のヘテロシクロアルキル;C6−C60のアリール;フルオレン;O、N、S、Si及びPからなる群より選ばれた少なくとも1つのヘテロ原子を含むC2−C60のヘテロアリール;及びC3−C60の脂肪族環とC6−C60の芳香族環との縮合環;からなる群より選ばれ、
X21〜X24は互いに独立に、炭素原子又は窒素原子であり、
R21及びR22は互いに独立に、重水素;ハロゲン原子;ヒドロキシル基;シアノ基;ニトロ基;アミノ基;アミジノ基;ヒドラジン;ヒドラゾン;カルボキシル基若しくはこの塩;スルホン酸基若しくはこの塩;リン酸若しくはこの塩;−C(=O)Q1(ここで、Q1はC1−C10のアルキル基、C6−C10のアリール基又はC6−C60のアリールオキシル基);置換又は非置換されたC1−C60のアルキル基;置換又は非置換されたC2−C60のアルケニル基;置換又は非置換されたC2−C60のアルキニル基;置換又は非置換されたC1−C60のアルコキシ基;置換又は非置換されたC3−C60のシクロアルキル基;置換又は非置換されたC2−C60のヘテロシクロアルキル基;置換又は非置換されたC3−C60のシクロアルケニル基;置換又は非置換されたC2−C60のヘテロシクロアルケニル基;置換又は非置換されたC6−C−60のアリール基;置換又は非置換されたC6−C60のアリールオキシル基;置換又は非置換されたC6−C60のアリールチオ基;及び置換又は非置換されたC2−C60のヘテロアリール基;からなる群より選ばれ、a1及びa2は互いに独立に、0〜8の整数であり、
Mは原子量40以上の遷移金属であり、
Lは一座配位(monodentate)有機配位子、二座配位(bidentate)有機配位子、三座配位(tridentate)有機配位子又は四座配位(tetradentate)有機配位子であり、mは0〜4の整数であり、
nは1〜3の整数である。 - 前記式6において、Mがイリジウム(Ir)、プラチナ(Pt)、オスミウム(Os)及びルテニウム(Ru)の中から選択された、請求項8に記載の有機電子素子。
- 前記式6において、X21〜X24のうち、少なくとも1つが窒素原子である、請求項8に記載の有機電子素子。
- 前記式6において、A環及びB環は互いに独立に、シクロペンテン、シクロヘキセン、ベンゼン、ナフタレン、インデン、フルオレン、ピロール、イミダゾール、ピラゾール、ピリジン、ピラジン、ピリミジン、ピリダジン、インドール、キノリン、イソキノリン、ベンゾイミダゾール、フラン、ベンゾフラン、チオフェン、ベンゾチオフェン、チアゾール、イソチアゾール、オキサゾール、イソオキサゾール、ベンゾチアゾール及びベンゾオキサゾールからなる群より選ばれた、請求項8に記載の有機電子素子。
- 前記式6において、R21及びR22は互いに独立に、重水素、−F、−Cl、シアノ基、ニトロ基、−C(=O)Q1(ここで、Q1はメチル基又はフェニル基)、メチル基、エチル基、tert−ブチル基、メトキシ基、tert−ブトキシ基及び フェニル基からなる群より選ばれ、
前記メチル基、エチル基及びtert−ブチル基はそれぞれ重水素、−F、−Cl、シアノ基及びニトロ基のうち、少なくとも1つで置換されていてもよく、
前記フェニル基は重水素、−F、−Cl、シアノ基、ニトロ基、−C(=O)Q1(ここで、Q1はメチル基又はフェニル基)、メチル基、tert−ブチル基、メトキシ基及びtert−ブトキシ基のうち、少なくとも1つで置換された、請求項8に記載の有機電子素子。 - 前記式6において、Lは下記式のうちの1つである、請求項8に記載の有機電子素子:
前記式において、Z11〜Z17は互いに独立に、水素、重水素、ハロゲン原子、ヒドロキシル基、シアノ基、ニトロ基、C1−C60のアルキル基、C1−C60のアルコキシ基、C6−C60のアリール基及びC2−C60のヘテロアリール基;からなる群より選ばれ、
前記C1−C60のアルキル基及びC1−C60のアルコキシ基は重水素、ハロゲン原子、ヒドロキシル基、シアノ基及びニトロ基のうち、少なくとも1つで置換されていてもよく、
前記C6−C60のアリール基及びC2−C60のヘテロアリール基は重水素、ハロゲン原子、ヒドロキシル基、シアノ基、ニトロ基、C1−C60のアルキル基及びC1−C60のアルコキシ基のうち、少なくとも1つで置換されていてもよく、d1〜d4は1〜4の整数である。 - 前記式6は下記式のうちの1つである、請求項8に記載の有機電子素子:
前記式6−1及び6−2において、
A環及びB環は互いに独立に、シクロペンテン、ベンゼン、ナフタレン、フルオレン、ピリジン、ピリダジン、キノリン、イソキノリン、ベンゾフラン、ベンゾチオフェン、チアゾール、イソチアゾール、オキサゾール、イソオキサゾール、ベンゾチアゾール及びベンゾオキサゾールのうちから選択され、
R21及びR22は互いに独立に、重水素、−F、−Cl、シアノ基、ニトロ基、−C(=O)Q1(ここで、Q1はメチル基又はフェニル基)、メチル基、エチル基、tert−ブチル基、メトキシ基、tert−ブトキシ基及びフェニル基からなる群より選ばれ、
前記メチル基、エチル基及びtert−ブチル基はそれぞれ重水素、−F、−Cl、シアノ基及びニトロ基のうち、少なくとも1つで置換されていてもよく、
前記フェニル基は重水素、−F、−Cl、シアノ基、ニトロ基、−C(=O)Q1(ここで、Q1はメチル基又はフェニル基)、メチル基、tert−ブチル基、メトキシ基及びtert−ブトキシ基のうち、少なくとも1つで置換されていてもよく、
a1及びa2はそれぞれ0〜2の整数であり、 Z11〜Z13は互いに独立に、水素、重水素、メチル基、エチル基及びtert−ブチル基からなる群より選ばれ、前記メチル基、エチル基及びtert−ブチル基はそれぞれ重水素、−F、シアノ基及びニトロ基のうち、少なくとも1つで置換することができる。 - 前記式6で表される化合物は下記化合物のうちの1つである、請求項8に記載の有機電子素子:
- 前記第1電極の一面と第2電極の一面のうち、前記有機物層と反対される、少なくとも一面に形成される光効率改善層を更に含む、請求項5に記載の有機電子素子。
- 前記有機物層はスピンコーティング工程、ノズルプリンティング工程、インクジェットプリンティング工程、スロットコーティング工程、ディップコーティング工程又はロールツーロール工程 によって形成されることを特徴とする請求項5に記載の有機電子素子。
- 請求項5に記載の有機電子素子を含むディスプレイ装置;及び
前記ディスプレイ装置を駆動する制御部;を含む電子装置。 - 前記有機電子素子は、有機電子発光素子、有機太陽電池、有機感光体、有機トランジスタ、及び単色又は白色照明用素子のうちの少なくとも1つであることを特徴とする請求項18に記載の電子装置。
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