JPWO2014132922A1 - 有機電界発光素子用ホウ素化合物及び有機電界発光素子 - Google Patents
有機電界発光素子用ホウ素化合物及び有機電界発光素子 Download PDFInfo
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- JPWO2014132922A1 JPWO2014132922A1 JP2015502911A JP2015502911A JPWO2014132922A1 JP WO2014132922 A1 JPWO2014132922 A1 JP WO2014132922A1 JP 2015502911 A JP2015502911 A JP 2015502911A JP 2015502911 A JP2015502911 A JP 2015502911A JP WO2014132922 A1 JPWO2014132922 A1 JP WO2014132922A1
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
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- 230000005525 hole transport Effects 0.000 claims abstract description 21
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 85
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
Description
Zは式(1a)で表されるホウ素含有基を示す。
Aは独立に、水素、重水素、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、炭素数2〜12のアルキニル基、炭素数1〜12のアルコキシル基、水酸基、塩素、臭素、フッ素、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、又は置換若しくは未置換の炭素数3〜17の芳香族複素環基を示し、Aが、アルキル基、アルケニル基、アルキニル基、アルコキシル基、芳香族炭化水素基、又は芳香族複素環基である場合は、隣接するこれらの基又はこれらの基が有する置換基が相互に結合して環を形成してもよく、これらの環はBを含む複素環であってもよく、縮合環であってもよい。
Yは独立に、下記式(1b)で表されるインドロカルバゾリル基を示す。
Zは、一般式(2)のZと同意であり、Zが複数存在する場合、それぞれ同一でも異なってもよい。
Rは、重水素、炭素数1〜12のアルキル基、炭素数7〜19のアラルキル基、炭素数2〜12のアルケニル基、炭素数2〜12のアルキニル基、シアノ基、炭素数2〜24のジアルキルアミノ基、炭素数6〜36のジアリールアミノ基、炭素数14〜38のジアラルキルアミノ基、アミノ基、ニトロ基、炭素数2〜12のアシル基、炭素数2〜12のアルコキシカルボニル基、カルボキシル基、炭素数1〜12のアルコキシル基、炭素数1〜12のアルキルスルホニル基、炭素数1〜12のハロアルキル基、水酸基、アミド基、フェノキシ基、炭素数1〜12のアルキルチオ基、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、置換若しくは未置換の炭素数3〜17の芳香族複素環基、又は式(1a)で表されるホウ素含有基を示す。
l及びmはそれぞれ独立に0〜4の整数を表し、nは0〜2の整数を表す。
また、a+c又はb+cが0である場合、少なくとも一つのRは式(1d)で表されるホウ素含有基を示す。l、m、n及びbが2以上の場合、複数のR及びZはそれぞれ同一でも異なってもよい。
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望ましい。
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。
電子阻止層は正孔を輸送しつつ、電子が正孔輸送層へ到達することを阻止する役割があり、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電子阻止材料から成り、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、本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。
APCI-TOFMS m/z 988 [M+1]、1H-NMR 測定結果(測定溶媒:C6D6)を図2に示す。
膜厚110 nmの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4.0×10-5 Paで積層させた。まず、ITO上に銅フタロシアニン(CuPC)を25 nmの厚さに形成した。次に、正孔輸送層として4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(NPB)を40 nmの厚さに形成した。次に、正孔輸送層上に、ホスト材料としての化合物(B14)と、燐光発光ドーパントとしてのトリス(2‐フェニルピリジン)イリジウム(III)(Ir(ppy)3)とを異なる蒸着源から、共蒸着し、40 nmの厚さに発光層を形成した。発光層中のIr(ppy)3の濃度は10.0 wt%であった。次に、電子輸送層としてトリス(8−ヒドロキシキノリナト)アルミニウム(III)(Alq3)を20 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1.0 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70 nmの厚さに形成し、有機EL素子を作製した。
合成例1と同様にして、化合物A8、A15、A24、B5、B6、B24、C8、D37、E25、F28及びF32を合成した。
実施例1の発光層のホスト材料として、化合物B14に代えて化合物A8、A15、A24、B5、B6、B24、C8、D37、E25、F28及びF32を用いた以外は実施例1と同様にして有機EL素子を作成した。各々の素子発光スペクトルの極大波長は520 nmであり、Ir(ppy)3からの発光が得られていることがわかった。各々の発光特性を表1に示す。
発光層のホスト材料として、CBPを用いた以外は実施例1と同様にして有機EL素子を作製した。
発光層のホスト材料として、下記化合物Ho−1を用いた以外は実施例1と同様にして有機EL素子を作製した。
Claims (7)
- 下記一般式(1)又は(2)で表される有機電界発光素子用ホウ素化合物。
L1は独立に、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、置換若しくは未置換の炭素数3〜17の芳香族複素環基、及び該置換若しくは未置換の芳香族炭化水素基及び芳香族複素環基の芳香族環が2〜6つ連結して構成される連結芳香族基から選ばれる2価又は3価の基を表し、連結芳香族基は直鎖状であっても分岐状であっても良く、連結する芳香族環は同一であっても異なっていてもよい。
Zは式(1a)で表されるホウ素含有基を示す。
Aは独立に、水素、重水素、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、炭素数2〜12のアルキニル基、炭素数1〜12のアルコキシル基、水酸基、塩素、臭素、フッ素、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、又は置換若しくは未置換の炭素数3〜17の芳香族複素環基を示し、Aが、アルキル基、アルケニル基、アルキニル基、アルコキシル基、芳香族炭化水素基、又は芳香族複素環基である場合は、隣接するこれらの基又はこれらの基が有する置換基が相互に結合して環を形成してもよく、これらの環はBを含む複素環であってもよく、縮合環であってもよい。
Yは独立に、下記式(1b)で表されるインドロカルバゾリル基を示す。
環Iは隣接環と任意の位置で縮合する式(1c)で表される芳香族炭化水素環を示し、環IIは隣接環と任意の位置で縮合する式(1d)で表される複素環を表す。L2は上記L1と同意であるが、c+1価の基である。
Zは、一般式(2)のZと同意であり、Zが複数存在する場合、それぞれ同一でも異なってもよい。
Rは、重水素、炭素数1〜12のアルキル基、炭素数7〜19のアラルキル基、炭素数2〜12のアルケニル基、炭素数2〜12のアルキニル基、シアノ基、炭素数2〜24のジアルキルアミノ基、炭素数6〜36のジアリールアミノ基、炭素数14〜38のジアラルキルアミノ基、アミノ基、ニトロ基、炭素数2〜12のアシル基、炭素数2〜12のアルコキシカルボニル基、カルボキシル基、炭素数1〜12のアルコキシル基、炭素数1〜12のアルキルスルホニル基、炭素数1〜12のハロアルキル基、水酸基、アミド基、フェノキシ基、炭素数1〜12のアルキルチオ基、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、置換若しくは未置換の炭素数3〜17の芳香族複素環基、又は式(1a)で表されるホウ素含有基を示す。
l及びmはそれぞれ独立に0〜4の整数を表し、nは0〜2の整数を表す。
a及びbは0又は1の整数を表し、cは0〜5の整数を表す。但し、一般式(1)においては、l+m+n+a+c≧1であり、一般式(2)においては、l+m+n+b+c≧1であり、a+c又はb+cが0である場合、少なくとも一つのRは式(1a)で表されるホウ素含有基を示す。また、l、m、n、b及びcが2以上の場合、複数のR及びZはそれぞれ同一でも異なってもよい。 - Aがそれぞれ独立に、炭素数1〜12のアルキル基、置換若しくは未置換の炭素数6〜18の芳香族炭化水素基、又は置換若しくは未置換の炭素数3〜17の芳香族複素環基である請求項1に記載の有機電界発光素子用ホウ素化合物。
- L1及びL2の少なくとも一方が縮環構造を有する基である請求項1に記載の有機電界発光素子用ホウ素化合物。
- 請求項1〜4のいずれかに記載の有機電界発光素子用ホウ素化合物を含む有機層を有する有機電界発光素子。
- 有機電界発光素子用ホウ素化合物を含む有機層が、発光層、正孔輸送層、正孔注入層、電子輸送層及び電子注入層から選ばれる少なくとも一つの層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。
- 有機電界発光素子用ホウ素化合物を含む有機層が発光層であり、該発光層が燐光発光性ドーパントと該有機電界発光素子用化合物をホスト材料として含有する請求項5に記載の有機電界発光素子。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149691A1 (ja) * | 2007-05-30 | 2008-12-11 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
KR20110011578A (ko) * | 2009-07-27 | 2011-02-08 | 에스에프씨 주식회사 | 인돌로카바졸 유도체 및 이를 이용한 유기전계발광소자 |
JP2011071460A (ja) * | 2009-08-31 | 2011-04-07 | Fujifilm Corp | 有機電界発光素子 |
CN102827196A (zh) * | 2012-09-12 | 2012-12-19 | 山西大学 | 一种含硼吲哚[3,2-b]咔唑衍生物及其制备方法和应用 |
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US5942340A (en) | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
US5952115A (en) | 1997-10-02 | 1999-09-14 | Xerox Corporation | Electroluminescent devices |
ATE511222T1 (de) | 1999-12-01 | 2011-06-15 | Univ Princeton | Komplex der formel l2irx |
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 |
CN101321755B (zh) | 2005-12-01 | 2012-04-18 | 新日铁化学株式会社 | 有机电致发光元件用化合物及有机电致发光元件 |
JP5457907B2 (ja) | 2009-08-31 | 2014-04-02 | 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 |
KR20110132721A (ko) | 2010-06-03 | 2011-12-09 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
CN102372718B (zh) * | 2010-08-20 | 2014-12-17 | 清华大学 | 一种含有吡啶基团的并咔唑类化合物及其应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008149691A1 (ja) * | 2007-05-30 | 2008-12-11 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
KR20110011578A (ko) * | 2009-07-27 | 2011-02-08 | 에스에프씨 주식회사 | 인돌로카바졸 유도체 및 이를 이용한 유기전계발광소자 |
JP2011071460A (ja) * | 2009-08-31 | 2011-04-07 | Fujifilm Corp | 有機電界発光素子 |
CN102827196A (zh) * | 2012-09-12 | 2012-12-19 | 山西大学 | 一种含硼吲哚[3,2-b]咔唑衍生物及其制备方法和应用 |
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