JP5572806B2 - オリゴフェニレン骨格を含む有機材料及びそれを用いた発光素子 - Google Patents
オリゴフェニレン骨格を含む有機材料及びそれを用いた発光素子 Download PDFInfo
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- NCGNDVHEWTVPOJ-UHFFFAOYSA-N CC1(C)OB(c2cc(-c3ccccc3C)c(B3OC(C)(C)C(C)(C)O3)cc2-c2ccccc2C)OC1(C)C Chemical compound CC1(C)OB(c2cc(-c3ccccc3C)c(B3OC(C)(C)C(C)(C)O3)cc2-c2ccccc2C)OC1(C)C NCGNDVHEWTVPOJ-UHFFFAOYSA-N 0.000 description 1
- 0 CC=*C1=CN1 Chemical compound CC=*C1=CN1 0.000 description 1
- AFINNPRPCFDDMV-UHFFFAOYSA-N Cc(cc(C)c(-c(c(-c1ccccc1)c1)cc(-c2ccccc2)c1-c1c(C)c(-c2cccnc2)c(C)cc1C)c1C)c1-c1cnccc1 Chemical compound Cc(cc(C)c(-c(c(-c1ccccc1)c1)cc(-c2ccccc2)c1-c1c(C)c(-c2cccnc2)c(C)cc1C)c1C)c1-c1cnccc1 AFINNPRPCFDDMV-UHFFFAOYSA-N 0.000 description 1
- XAZAGCFQWUYUTB-UHFFFAOYSA-N Cc1ccccc1-c1cc([Br]=C)cc(-c2c(C)cccc2)c1 Chemical compound Cc1ccccc1-c1cc([Br]=C)cc(-c2c(C)cccc2)c1 XAZAGCFQWUYUTB-UHFFFAOYSA-N 0.000 description 1
- YZMLMXTXUKFCDX-UHFFFAOYSA-N Cc1ccccc1C(CC(c1ccccc1C)=C1)C=C1c(c(-c1ccccc1C)c1)cc(-c2ccccc2C)c1-c1cc(-c2c(C)cccc2)cc(-c2ccccc2C)c1 Chemical compound Cc1ccccc1C(CC(c1ccccc1C)=C1)C=C1c(c(-c1ccccc1C)c1)cc(-c2ccccc2C)c1-c1cc(-c2c(C)cccc2)cc(-c2ccccc2C)c1 YZMLMXTXUKFCDX-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1cc(-[n]2c3ccccc3c3c2cccc3)ccc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1cc(-[n]2c3ccccc3c3c2cccc3)ccc1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
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Description
J. Appl. Phys.,第90巻,(2001年)、第5048頁 Appl. Phys. Lett.,第79巻(2001年)、第156頁 Appl.Phys.Lett.,第79巻(2001年),第2082頁 Appl.Phys.Lett.,第82巻(2003年),第2422頁 Appl.Phys.Lett.,第83巻(2003年),第569頁
であり、nは0または1である。R1はそれぞれ独立に、炭素数1〜6のアルキル基、炭素数1〜6のフルオロアルキル基、またはハロゲン原子であり、aはそれぞれ独立に0〜5の整数である]
を含有することを特徴とする、新規の有機電界発光素子を見出した。このオリゴフェニレン誘導体は、その基本骨格は炭素原子及び水素原子のみからなり、当該基本骨格に、さらに窒素原子、ハロゲン原子が加わることもある、新規の化合物であり、公知の化合物を原料とし、カップリング反応等の手法を組み合わせて、効率的に合成できることを見出した。
(a)ねじれた分子構造による分子の柔軟性(アモルファス性)が向上し、それにより発光層全体の耐久性が向上したこと
(b)分子構造の非平面性により、π共役が弱くなり、それにより効果的にバンドギャップが広がったこと
等の効果が、複合した結果と考えられる。
で表されるターフェニル誘導体。
で表されるターフェニル誘導体。
であり、R1はそれぞれ独立に、炭素数1〜6のアルキル基、炭素数1〜6のフルオロアルキル基、またはハロゲン原子であり、aはそれぞれ独立に0〜5の整数、nは0または1である。]
を含有することを特徴とする、有機電界発光素子。
で表されるターフェニル誘導体であることを特徴とする、発明5乃至発明7の何れかに記載の有機電界素子。
で表されるターフェニル誘導体を含有することを特徴とする、有機電界発光素子。
で表されるターフェニル誘導体であることを特徴とする、発明8に記載の有機電界発光素子。
有機電界発光素子が、さらに正孔輸送層、励起子ブロック層、電子輸送層および正孔ブロック層を含み、
前記有機発光層にはホスト材料および青色燐光ドーパント材料を含み、
該ホスト材料が、下記式(3)で表される化合物
であり、
該青色燐光ドーパントが、下記式で表されるFIrpic
有機電界発光素子が、さらに正孔輸送層、励起子ブロック層、電子輸送層および正孔ブロック層を含み、
前記有機発光層にはホスト材料および青色燐光ドーパント材料を含み、
該ホスト材料が、下記式(4)で表される化合物
であり、
該青色燐光ドーパントが、下記式で表されるFIrpic
有機電界発光素子が、さらに正孔輸送層、励起子ブロック層、電子輸送層および正孔ブロック層を含み、
前記有機発光層にはホスト材料および青色燐光ドーパント材料を含み、
該ホスト材料が、下記式(5)で表される化合物
であり、
該青色燐光ドーパントが、下記式で表されるFIrpic
有機電界発光素子が、さらに正孔輸送層、励起子ブロック層、電子輸送層および正孔ブロック層を含み、
前記有機発光層にはホスト材料および青色燐光ドーパント材料を含み、
該ホスト材料が、下記式(6)で表される化合物
であり、
該青色燐光ドーパントが、下記式で表されるFIrpic
を含有することを特徴とするものである。
ここで、式中のAr1はそれぞれ独立に、式(1a)で表されるオリゴフェニル基
で表される、ターフェニル誘導体や、式(4)
で表されるターフェニル誘導体や、式(5)
で表されるターフェニル誘導体や、式(6)
(a)ねじれた分子構造による分子の柔軟性(アモルファス性)が向上し、それにより発光層全体の耐久性が向上したこと
(b)分子構造の非平面性により、π共役が弱くなり、それにより効果的にバンドギャップが広がったこと、
の各効果が相乗した結果である。
次に、本発明のオリゴフェニレン誘導体の合成について説明する。まず、公知の手法で得ることができる1,4−ジブロモ−2,5−ジヨードベンゼンとフェニル金属試薬との反応などを用いることにより下記一般式(5)に示すオリゴフェニレン誘導体を得ることができる。
であり、M’’は金属基、またはハロゲン原子を示す]
を反応させ、Ar1基を導入することができる。このためには、次の各種の方法のうち、何れを採用してもよい。
2)一般式(5)で示されるオリゴフェニレン誘導体をアルキルリチウムによるリチオ化や遷移金属触媒によるカップリング反応等を用いて、アルキルグリニヤール試薬、アルキルマグネシウムアミド、などの有機マグネシウム試薬、あるいは亜鉛試薬、すず試薬、ほう酸エステル等の金属交換試薬へと変換したのち、ついでパラジウムなどの遷移金属触媒の存在下で、一般式(6)の化合物をクロスカップリング反応させる方法。
次に、本発明の実施形態1に係るオリゴフェニレン誘導体を使用した有機電界発光素子の実施形態について説明する。
該青色燐光ドーパントが、下記式で表されるFIrpic
以下、実施例および比較例を挙げ、本発明をより具体的に詳細に説明するが、本発明は以下の実施例に限定されるものではない。
<オリゴフェニレン誘導体の合成>
[比較例1]
公知材料であるCBPはガラス転移点をもたず、薄膜状態の安定性に乏しく結晶化しやすい性質であることを示した。また、励起三重項エネルギーは2.6eVであった。
ホスト材料をCBPに代えた以外は、実施例13と同様にして有機電界発光素子を構成した。 この素子の外部量子効率は5.7%であり、実施例13乃至21より劣るものであった。
比較例2の有機電界発光素子に100mA/cm2の負荷をかけて駆動させたところ、外部量子効率は3.0%となり、実施例22乃至24よりも劣るものであった。
(a)ねじれた分子構造による分子の柔軟性(アモルファス性)が向上し、それにより発光層全体の耐久性が向上したこと
(b)分子構造の非平面性により、π共役が弱くなり、それにより効果的にバンドギャップが広がったこと、
の各効果が相乗した結果、青色燐光発光用にも十分なバンドギャップを持ち、なおかつ、エネルギー遷移が効率的に起こる発光素子が得られたことを示している。
Claims (16)
- 一般式(3)
で表されるターフェニル誘導体。 - 一般式(4)
で表されるターフェニル誘導体。 - 一対の電極間に、少なくとも一層の有機発光層を有する有機電界発光素子であって、該有機発光層が、一般式(1)で表されるオリゴフェニレン誘導体
であり、R1はそれぞれ独立に、炭素数1〜6のアルキル基、炭素数1〜6のフルオロアルキル基、またはハロゲン原子であり、aはそれぞれ独立に0〜5の整数、nは0または1である。]
を含有することを特徴とする、有機電界発光素子。 - 請求項5において、前記有機発光層にはホスト材料および青色燐光ドーパント材料を含み、該ホスト材料が、請求項5に記載のオリゴフェニレン誘導体である、青色燐光発光を用いた有機電界発光素子。
- 前記有機電界発光素子が、さらに正孔輸送層、励起子ブロック層、電子輸送層を含む、請求項6に記載の有機電界発光素子。
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PCT/JP2008/073222 WO2009081873A1 (ja) | 2007-12-25 | 2008-12-19 | オリゴフェニレン骨格を含む有機材料及びそれを用いた発光素子 |
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US20100326526A1 (en) | 2009-06-29 | 2010-12-30 | Nitto Denko Corporation | Emissive aryl-heteroaryl compounds |
JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
EP2354207B1 (en) | 2010-01-20 | 2016-10-12 | Hitachi, Ltd. | Organic luminescent materials, coating solution using same for organic emitting layer, organic light emitting device using coating solution and light source device using organic light emitting device |
TW201211004A (en) | 2010-03-16 | 2012-03-16 | Tosoh Corp | 1,2,4,5-substituted phenyl derivative and production method thereof, and organic electroluminescent element using the same derivative as constituent |
JP2012140414A (ja) * | 2010-12-16 | 2012-07-26 | Tosoh Corp | 1,2,4,5−置換フェニル誘導体とその製造方法、及びそれらを構成成分とする有機電界発光素子 |
WO2012081541A1 (ja) * | 2010-12-17 | 2012-06-21 | 東ソー株式会社 | 1,2,4,5-置換フェニル誘導体とその製造方法、及び有機電界発光素子 |
KR101396552B1 (ko) | 2012-08-30 | 2014-05-20 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
CN104781368B (zh) * | 2012-10-12 | 2018-05-01 | 默克专利有限公司 | 具有芳族单元的发光体和主体 |
JP6048823B2 (ja) * | 2012-12-19 | 2016-12-21 | 国立研究開発法人物質・材料研究機構 | 蛍光プローブ、および、セシウム含有物質を検出する方法 |
CN103044421B (zh) * | 2012-12-26 | 2015-06-17 | 浙江大学 | 钯催化的苯并咪唑并异喹啉的制备方法 |
US9224958B2 (en) | 2013-07-19 | 2015-12-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP5998235B2 (ja) * | 2015-02-20 | 2016-09-28 | 株式会社日立製作所 | 有機発光素子の製造方法 |
CN106450017B (zh) * | 2016-10-21 | 2018-04-20 | 京东方科技集团股份有限公司 | 一种oled器件及oled显示装置 |
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JPH07157473A (ja) | 1993-12-06 | 1995-06-20 | Chisso Corp | トリアジン誘導体、その製造法及びそれを用いた電界発光素子 |
JP4514841B2 (ja) * | 1998-02-17 | 2010-07-28 | 淳二 城戸 | 有機エレクトロルミネッセント素子 |
JPH11283746A (ja) | 1998-03-27 | 1999-10-15 | Fuji Photo Film Co Ltd | ビスベンゾアゾール化合物を用いたエレクトロルミネッセンス素子およびビスベンゾアゾール化合物の製造方法 |
US6645645B1 (en) * | 2000-05-30 | 2003-11-11 | The Trustees Of Princeton University | Phosphorescent organic light emitting devices |
JP2002212181A (ja) | 2001-01-23 | 2002-07-31 | Mitsubishi Chemicals Corp | ベンゾアゾール基含有トリアジン系化合物の製造方法 |
US6998487B2 (en) * | 2001-04-27 | 2006-02-14 | Lg Chem, Ltd. | Double-spiro organic compounds and organic electroluminescent devices using the same |
JP4377198B2 (ja) | 2003-10-22 | 2009-12-02 | 富士フイルム株式会社 | 有機電界発光素子 |
EP1903020B1 (en) * | 2005-07-14 | 2014-03-19 | Idemitsu Kosan Co., Ltd. | Biphenyl derivatives, organic electroluminescent materials, and organic electroluminescent devices made by using the same |
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WO2009081873A1 (ja) | 2009-07-02 |
EP2236485A1 (en) | 2010-10-06 |
US20100308313A1 (en) | 2010-12-09 |
CN101910095A (zh) | 2010-12-08 |
JPWO2009081873A1 (ja) | 2011-05-06 |
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