JPWO2008146839A1 - 有機電界発光素子用化合物及び有機電界発光素子 - Google Patents
有機電界発光素子用化合物及び有機電界発光素子 Download PDFInfo
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- JPWO2008146839A1 JPWO2008146839A1 JP2009516335A JP2009516335A JPWO2008146839A1 JP WO2008146839 A1 JPWO2008146839 A1 JP WO2008146839A1 JP 2009516335 A JP2009516335 A JP 2009516335A JP 2009516335 A JP2009516335 A JP 2009516335A JP WO2008146839 A1 JPWO2008146839 A1 JP WO2008146839A1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
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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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
Description
また、特許文献7では、適度な電子輸送能力を有する上記BAlqを燐光有機EL素子のホスト材料として用いることが提案されている。本文献によれば、層構成を複雑にすることなく長寿命な燐光有機EL素子が実現できるとされているが、実用上十分なものとはいえない。
環aは、2つの隣接環と縮合する式(a1)又は(a2)で表される芳香環又は複素環を示し、環a'は、3つの隣接環と縮合する式(a1)で表される芳香環又は複素環を示し、Xは、CH又はNを示す。環bは、2つの隣接環と縮合する式(b1)で表される複素環を示す。
Ar1は、芳香族複素環基からなるm+n価の基を示す。
Lは独立に、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、少なくとも一つは縮環構造を有する。
Rは独立に、水素、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、又は置換若しくは未置換の芳香族炭化水素基若しくは芳香族複素環基を示す。
mは1を示し、nは1又は2を示す。
L、R及びAr3は、一般式(V)のL、R及びAr3と同じ意味を有する。
環b'は独立に、2つの隣接環と縮合する式(b1)で表される複素環を示す。
(化合物21の合成)
脱気窒素置換した200ml三口フラスコに1,2-シクロヘキサンジオン33.3g(0.297mol)、フェニルヒドラジン塩酸塩86.0g(0.595mol)を加え、これにエタノール1000mlを加えて攪拌させた。その後、同フラスコ内に濃硫酸3.0g(0.03mol)を5分間かけ滴下した。その後65℃まで加熱し、4時間攪拌した。室温まで冷却した後、生じた紫茶色結晶を濾取した後、濾取した結晶をエタノール500mlで二回、リスラリー洗浄をおこなった。これを、減圧乾燥して紫茶色粉末80.0g(0.286mol、収率96.3%)を得た。
例示化合物21のEI−MS(M+1)は868、融点は398℃であった。
正孔注入層に銅フタロシアニン(CuPC)を用い、正孔輸送層にα-NPD及び電子輸送層にAlq3を用いた。膜厚150nm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5.0×10-4 Paで積層させた。まず、ITO上に正孔注入層としてCuPCを3.0Å/秒で25 nmの膜厚で成膜した。次いで、正孔注入層上に、正孔輸送層としてα-NPDを蒸着速度3.0Å/秒にて55nmの厚さに形成した。
次に、電子輸送層としてAlq3を蒸着速度3.0Å/秒にて30nmの厚さに形成した。更に、電子輸送層上に、電子注入層としフッ化リチウム(LiF)を蒸着速度0.1Å/秒にて1nm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)を蒸着速度10Å/秒にて200nmの厚さに形成し、有機EL素子を作成した。
(化合物4の合成)
窒素置換した200ml三口フラスコに実施例1で得られた白色粉末A10.0g(0.036mol)、炭酸カリウム12.9g(0.093mol)、銅粉5.7g(0.090mol)、テトラグライム50.0gを加え、窒素気流下で攪拌した。同フラスコ内に2-ブロモナフタレン9.87g(0.047mol)をテトラグライム10.0gに溶解させた溶液を10分間かけ滴下した。滴下終了後、195℃で1時間攪拌を継続した。その後、室温まで冷却し、不溶物を濾取した。濾液にメタノール30gおよび水150gを加え、2時間攪拌した。その後、析出物を濾取し、これを水100gで2回、更に、メタノール100gで1回リスラリー洗浄した。減圧乾燥後、カラムクロマトグラフィーで精製して白色粉末D 13.0g(0.034mol、収率94.7%)を得た。
例示化合物4のAPCI−MSはm/Z 614[M+H]+、融点は317℃であった。
発光層のホスト材料として例示化合物21に代えて例示化合物4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。
(化合物5の合成例)
窒素置換した500ml三口フラスコに、マグネシウム3.65g(0.150mol)、脱水THF 10.0g、ヨウ素0.01gを加え、窒素気流下で攪拌した。60℃まで昇温した後、2-ブロモナフタレン32.1g(0.155mol)の脱水THF( 100.0ml)溶液を1時間かけ滴下した。その後、加熱還流下、2時間攪拌を続けた。室温まで冷却をした後、更に氷浴にて3℃まで冷却した。これに、塩化シアヌル9.21g(0.050mol)の脱水THF (50.0ml)溶解を、氷浴にて10℃以下に保ちながら30分間かけて滴下し、滴下終了後、更に室温で5時間攪拌した。その後、同フラスコを氷浴に浸し、15℃以下に保ちながら10%塩酸50.0gを30分間で滴下した。氷浴を外し、トルエン150.0mlを加え、500 ml分液ロートにて、有機層と水層に分画した。有機層を50mlの水で三回洗浄し、有機層を硫酸マグネシウムで脱水し、一旦、硫酸マグネシウムを濾別した後、溶媒を減圧留去することにより濃縮物33.6gを得た。得られた濃縮物を75.0gのTHFに溶解させ、攪拌しながらメタノール200.0gを徐々に加えた。析出した結晶を濾別しし、これをヘキサンにて再結晶し、7.6g(0.021mol、収率41.3%)の白色粉末Fを得た。
例示化合物5のAPCI−MSはm/Z 664[M+H]+、融点は355℃であった。
発光層のホスト材料として例示化合物21に代えて例示化合物5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。
発光層のホスト材料として例示化合物21に代えてBAlq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 (6)
- 下記一般式(I)で表される有機電界発光素子用化合物。
ここで、
環aは、2つの隣接環と縮合する式(a1)又は(a2)で表される芳香環又は複素環を示し、環a'は、3つの隣接環と縮合する式(a1)で表される芳香環又は複素環を示し、Xは、CH又はNを示す。環bは、2つの隣接環と縮合する式(b1)で表される複素環を示し、
Ar1は、芳香族複素環基からなるm+n価の基を示し、
Lは独立に、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を示し、少なくとも一つは縮環構造を有し、
Rは独立に、水素、アルキル基、アラルキル基、アルケニル基、アルキニル基、シアノ基、ジアルキルアミノ基、ジアリールアミノ基、ジアラルキルアミノ基、アミノ基、ニトロ基、アシル基、アルコキシカルボニル基、カルボキシル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基、又は置換若しくは未置換の芳香族炭化水素基若しくは芳香族複素環基を示し、
mは1を示し、nは1又は2を示す。 - 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと請求項1〜3のいずれかに記載の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ことを特徴とする有機電界発光素子。
- 陽極と発光層の間に正孔注入輸送層を有し、陰極と発光層の間に電子注入輸送層を有してなる請求項4記載の有機電界発光素子。
- 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項5記載の有機電界発光素子。
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2008
- 2008-05-27 TW TW97119549A patent/TWI468489B/zh not_active IP Right Cessation
- 2008-05-28 KR KR1020097025724A patent/KR101041642B1/ko active IP Right Grant
- 2008-05-28 JP JP2009516335A patent/JP4550160B2/ja active Active
- 2008-05-28 US US12/600,773 patent/US8008657B2/en active Active
- 2008-05-28 EP EP14161321.6A patent/EP2759545B1/en active Active
- 2008-05-28 WO PCT/JP2008/059807 patent/WO2008146839A1/ja active Application Filing
- 2008-05-28 CN CN200880015477XA patent/CN101679438B/zh active Active
- 2008-05-28 EP EP08776922.0A patent/EP2166011B1/en active Active
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JPH11162650A (ja) * | 1997-10-02 | 1999-06-18 | Xerox Corp | エレクトロルミネセントデバイス |
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JP2004204234A (ja) * | 2002-12-24 | 2004-07-22 | Samsung Sdi Co Ltd | 青色発光高分子及びこれを採用した有機el素子 |
Also Published As
Publication number | Publication date |
---|---|
TWI468489B (zh) | 2015-01-11 |
JP4550160B2 (ja) | 2010-09-22 |
EP2166011B1 (en) | 2016-03-30 |
US8008657B2 (en) | 2011-08-30 |
EP2166011A1 (en) | 2010-03-24 |
US20100148161A1 (en) | 2010-06-17 |
EP2759545B1 (en) | 2018-07-04 |
EP2166011A4 (en) | 2011-08-17 |
TW200914577A (en) | 2009-04-01 |
EP2759545A1 (en) | 2014-07-30 |
WO2008146839A1 (ja) | 2008-12-04 |
KR20100017737A (ko) | 2010-02-16 |
CN101679438B (zh) | 2012-10-10 |
CN101679438A (zh) | 2010-03-24 |
KR101041642B1 (ko) | 2011-06-14 |
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