JP6563943B2 - 有機電界発光素子用材料及びこれを用いた有機電界発光素子 - Google Patents
有機電界発光素子用材料及びこれを用いた有機電界発光素子 Download PDFInfo
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- JP6563943B2 JP6563943B2 JP2016551624A JP2016551624A JP6563943B2 JP 6563943 B2 JP6563943 B2 JP 6563943B2 JP 2016551624 A JP2016551624 A JP 2016551624A JP 2016551624 A JP2016551624 A JP 2016551624A JP 6563943 B2 JP6563943 B2 JP 6563943B2
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- light emitting
- organic electroluminescent
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 19
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 3
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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Description
また、この有機電界発光素子用材料は、良好なアモルファス特性ならびに高い熱安定性および電気的安定性を示すことから、これを用いた有機EL素子は駆動寿命が長く、実用レベルの耐久性を有する。
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm〜5μm、好ましくは50〜200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。
発光層は、陽極及び陰極のそれぞれから注入された正孔及び電子が再結合することにより励起子が生成した後、発光する層であり、発光層には有機発光材料とホスト材料を含むことがよい。有機発光材料(発光ドーパント)としては、蛍光発光材料(蛍光発光ドーパント)、燐光発光材料(燐光発光ドーパント)及び遅延蛍光発光材料(遅延蛍光発光ドーパント)が挙げられる。
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。
正孔阻止層とは、広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
電子阻止層とは、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料から成り、正孔を輸送しつつ電子を阻止することで電子と正孔が再結合する確率を向上させることができる。
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、励起子阻止層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。
正孔輸送層とは、正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。
電子輸送層とは、電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。
膜厚 150nm の 酸化インジウムスズ(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2.0×10-5 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α-NPD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の化合物(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、35 nm の厚さに発光層を形成した。Ir(ppy)3の濃度は 7.0 %であった。次に、電子輸送層としてAlq3を40 nm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0.5 nm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170 nmの厚さに形成し、有機EL素子を作製した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(4)、(5)、(10)、(13)又は(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。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(3)とCBPを30対70の比率(重量比)で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(3)とCBPを40対60の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(18)と化合物(5)を40対60の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(18)と化合物(5)を50対50の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として化合物(3)に代えて、CBP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。
実施例2における発光層のホスト材料として化合物(3)に代えて、複素環化合物(H−1)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。
実施例2における発光層のホスト材料として化合物(3)に代えて、複素環化合物(H−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。
Claims (12)
- 一般式(1)で表される複素環化合物からなることを特徴とする有機電界発光素子用材料。
ここで、R1は炭素数1〜12のアルキル基、炭素数1〜12のアルコキシ基、置換若しくは未置換の炭素数6〜30の芳香族炭化水素基、置換若しくは未置換の炭素数3〜22の芳香族複素環基、又はこれらの芳香族環が2〜6個連結してなる置換若しくは未置換の連結芳香族基を表す。
R2〜R5は独立に、炭素数1〜12のアルキル基、炭素数1〜12のアルコキシ基、置換若しくは未置換の炭素数6〜30の芳香族炭化水素基、ヘテロ原子として酸素又は硫黄のみを含む置換若しくは未置換の炭素数3〜22の芳香族複素環基、又はこれらの芳香族環が2〜6連結してなる置換若しくは未置換の連結芳香族基を表す。
a、b、c、dは独立に、0〜2の整数を表す。 - 基板上に、陽極、有機層及び陰極が積層されてなる有機電界発光素子において、該有機層の少なくとも1層が請求項1に記載の有機電界発光素子用材料を含む有機層であ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材料を含む有機層が、発光層、電子輸送層、及び正孔阻止層からなる群れから選ばれる少なくとも一つの層である請求項2に記載の有機電界発光素子。
- 有機電界発光素子用材料を含む有機層が、発光層であることを特徴とする請求項2に記載の有機電界発光素子。
- 発光層が、発光ドーパントとホスト材料を含むことを特徴とする請求項4に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして燐光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして蛍光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして遅延蛍光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして遅延蛍光発光ドーパントを含み、前記有機電界発光素子用材料が遅延蛍光発光ドーパントであることを特徴とする請求項5記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして蛍光発光ドーパントを含み、前記有機電界発光素子用材料が蛍光発光ドーパントであることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層が2種類以上のホスト材料と1種類以上の発光ドーパントを含み、少なくとも1種のホスト材料が前記有機電界発光素子用材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層が2種類以上のホスト材料と1種類以上の発光ドーパントを含み、少なくとも1種の発光ドーパントが前記有機電界発光素子用材料であることを特徴とする請求項5に記載の有機電界発光素子。
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JP3924869B2 (ja) * | 1997-11-05 | 2007-06-06 | 東レ株式会社 | 有機積層薄膜発光素子 |
EP2270895A3 (en) | 1999-12-01 | 2011-03-30 | The Trustees of Princeton University | Complexes for OLEDs |
JP2001313178A (ja) | 2000-04-28 | 2001-11-09 | Pioneer Electronic Corp | 有機エレクトロルミネッセンス素子 |
JP2005310742A (ja) * | 2004-03-25 | 2005-11-04 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセンス素子 |
JP5284677B2 (ja) * | 2008-04-25 | 2013-09-11 | 山本化成株式会社 | 有機トランジスタ |
JP5498681B2 (ja) | 2008-10-02 | 2014-05-21 | 山本化成株式会社 | 有機トランジスタ |
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US8946688B2 (en) * | 2009-12-14 | 2015-02-03 | Idemitsu Kosan Co., Ltd. | Polycyclic ring-fused compound and organic thin film transistor utilizing the same |
KR20120129889A (ko) * | 2009-12-25 | 2012-11-28 | 고쿠리츠다이가쿠호진 히로시마다이가쿠 | 고분자 화합물, 이것을 포함하는 박막 및 잉크 조성물 |
JP2012017272A (ja) * | 2010-07-06 | 2012-01-26 | Canon Inc | 新規有機化合物およびそれを有する有機発光素子 |
JPWO2012090462A1 (ja) * | 2010-12-28 | 2014-06-05 | 出光興産株式会社 | 有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ |
JP6100476B2 (ja) * | 2012-04-27 | 2017-03-22 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用材料並びに該有機電界発光素子を用いた発光装置、表示装置及び照明装置 |
JP2013234151A (ja) * | 2012-05-09 | 2013-11-21 | Idemitsu Kosan Co Ltd | 縮合多環芳香族化合物及びそれを用いた有機薄膜トランジスタ |
CN105073754B (zh) * | 2013-03-29 | 2018-07-06 | 新日铁住金化学株式会社 | 芳香族杂环化合物、其制造方法、及其应用 |
KR102313358B1 (ko) * | 2014-07-10 | 2021-10-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102304718B1 (ko) * | 2014-07-10 | 2021-09-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
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US10629820B2 (en) * | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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KR102398991B1 (ko) | 2022-05-17 |
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CN106716667A (zh) | 2017-05-24 |
TWI656125B (zh) | 2019-04-11 |
US20180233687A1 (en) | 2018-08-16 |
WO2016051977A1 (ja) | 2016-04-07 |
CN106716667B (zh) | 2019-02-22 |
JPWO2016051977A1 (ja) | 2017-08-31 |
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