JP2003086379A5 - - Google Patents

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JP2003086379A5
JP2003086379A5 JP2002150546A JP2002150546A JP2003086379A5 JP 2003086379 A5 JP2003086379 A5 JP 2003086379A5 JP 2002150546 A JP2002150546 A JP 2002150546A JP 2002150546 A JP2002150546 A JP 2002150546A JP 2003086379 A5 JP2003086379 A5 JP 2003086379A5
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陽極と陰極の間に発光物質として少なくとも発光材料、正孔輸送材料および電子輸送材料が存在し、電気エネルギーにより発光する素子であって、該素子は発光ピーク波長が580nm以上720nm以下で発光し、発光材料に少なくとも下記一般式(1)に示すジケトピロロ[3,4−c]ピロール誘導体と蛍光ピーク波長が580nm以上720nm以下の有機蛍光物質を含み、電子輸送材料のイオン化ポテンシャルが5.9eV以上であることを特徴とする発光素子。
Figure 2003086379
{RおよびRは同じでも異なっていてもよく、炭素数1〜25のアルキル基または、下記一般式(2)の中から選ばれ、
Figure 2003086379
(RおよびRは同じでも異なっていてもよく、炭素数1〜4のアルキル基、無知間または炭素数1〜3のアルキル基が置換されたフェニル基から選ばれ、Arはアルキル基、アルコキシ基、ハロゲン、フェニル基の中から選ばれた置換基を有するフェニル基、無置換もしくは置換基を有するナフチル基の中から選ばれる。mは0〜4の整数を表す。)
ArおよびArは同じでも異なっていてもよく、無置換または置換基を有するフェニル基、ナフチル基、スチリル基、カルバゾリル基から選ばれる。}
An element that includes at least a light-emitting material, a hole transport material, and an electron transport material as a light- emitting substance between an anode and a cathode and emits light by electric energy, the element emits light at an emission peak wavelength of 580 nm to 720 nm, At least the following general formula diketopyrrolo [3,4-c] pyrrole derivative and the fluorescence peak wavelength shown in (1) is seen containing a 720nm following organic fluorescent substance or 580 nm, ionization potential of the electron transporting material is more than 5.9eV the luminescent material emitting element characterized in that it.
Figure 2003086379
{R 1 and R 2 may be the same or different and are selected from alkyl groups having 1 to 25 carbon atoms or the following general formula (2);
Figure 2003086379
(R 3 and R 4 may be the same or different, and are selected from alkyl groups having 1 to 4 carbon atoms, ignorant or phenyl groups substituted with 1 to 3 carbon atoms, and Ar 3 is an alkyl group. And a phenyl group having a substituent selected from an alkoxy group, a halogen, and a phenyl group, an unsubstituted or substituted naphthyl group, and m represents an integer of 0 to 4.)
Ar 1 and Ar 2 may be the same or different and are selected from an unsubstituted or substituted phenyl group, naphthyl group, styryl group, and carbazolyl group. }
前記有機蛍光物質が下記一般式(3)に示すピロメテン骨格を有する化合物もしくはその金属錯体であることを特徴とする請求項1記載の発光素子。
Figure 2003086379
(ここで、R〜R11のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合環を形成し、残りは水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アルキルセレノ基、アリールエーテル基、アリールチオエーテル基、アリールセレノエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。Xは炭素または窒素であるが、窒素の場合には上記R11は存在しない。金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金から選ばれる少なくとも一種である。)
The light-emitting element according to claim 1, wherein the organic fluorescent material is a compound having a pyromethene skeleton represented by the following general formula (3) or a metal complex thereof.
Figure 2003086379
(Here, at least one of R 5 to R 11 contains an aromatic ring or forms a condensed ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group. , Cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, alkylseleno group, arylether group, arylthioether group, arylselenoether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne , A cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxanyl group, and a condensed ring and an aliphatic ring formed between adjacent substituents X is carbon or nitrogen, but in the case of nitrogen, the above R 11 (The metal of the metal complex is at least one selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum.)
前記金属錯体が下記一般式(4)で表されることを特徴とする請求項記載の発光素子。
Figure 2003086379
(ここで、R12〜R18のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合芳香環を形成し、残りは水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アルキルセレノ基、アリールエーテル基、アリールチオエーテル基、アリールセレノエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。R19およびR20は同じでも異なっていてもよく、ハロゲン、水素、アルキル、アリール、複素環基から選ばれる。Xは炭素または窒素であるが、窒素の場合には上記R18は存在しない。)
The light emitting device according to claim 2, wherein the metal complex is represented by the following general formula (4).
Figure 2003086379
(At least one of R 12 to R 18 contains an aromatic ring or forms a condensed aromatic ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl. Group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, alkylseleno group, arylether group, arylthioether group, arylselenoether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, Haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, in condensed and aliphatic rings formed between adjacent substituents .R 19 and R 20 is selected from the be the same or different , Halogen, hydrogen, alkyl, aryl, .X selected from heterocyclic group is a carbon or nitrogen, in the case of nitrogen above R 18 is absent.)
前記電子輸送材料のイオン化ポテンシャルが5.9eV以上であり、かつ分子量が400以上であることを特徴とする請求項記載の発光素子。The electron ionization potential of transporting material is not less than 5.9 eV, and the light-emitting element according to claim 1, wherein the molecular weight is equal to or 400 or more. 前記電子輸送材料のガラス転移温度が90℃以上であることを特徴とする請求項記載の発光素子。Emitting device of claim 1, wherein the glass transition temperature of the electron transporting material is characterized in that at 90 ° C. or higher. 陽極、正孔輸送層、発光層、電子輸送層、陰極を順次積層することを特徴とする請求項記載の発光素子。Anode, a hole transport layer, light emitting layer, electron transporting layer, the light emitting device of claim 1, wherein the sequentially stacking a cathode.
JP2002150546A 2001-05-28 2002-05-24 Light emitting element Expired - Fee Related JP4061969B2 (en)

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KR20070097494A (en) * 2004-12-09 2007-10-04 시바 스페셜티 케미칼스 홀딩 인크. Fluorescent diketopyrolopyroles
US8278819B2 (en) 2007-03-09 2012-10-02 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and display
KR100901887B1 (en) * 2008-03-14 2009-06-09 (주)그라쎌 Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010084852A1 (en) 2009-01-23 2010-07-29 東レ株式会社 Light-emitting element material and light-emitting element
JP6465350B2 (en) * 2015-03-09 2019-02-06 公立大学法人首都大学東京 Novel organic compounds and their use

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