JP2009091559A - Composition containing metal complex and device using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a composition useful as a light emitting material having sufficient light emitting characteristics when used for producing an element such as a light emitting element. <P>SOLUTION: The composition includes a polymeric charge-transfer material and the metal complex represented by formula (1) (wherein X is a halogen atom; R1 to R15 are each a hydrogen atom or an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group or the like independently; M is an iridium atom, a platinum atom, an osmium atom, a ruthenium atom, a palladium atom, a rhodium atom, a rhenium atom or a cobalt atom; and n is 1 or 2). <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a composition containing a metal complex and a device using the same.

  Conventionally, various metal complex compounds have been used as light-emitting materials, charge transport materials, and the like for manufacturing light-emitting elements such as organic electroluminescence (EL) elements. As a light emitting material used for a light emitting layer of an organic EL element, an ortho metalated complex having iridium as a central metal (Non-patent Documents 1 and 2), a composition of a host compound such as polyvinyl carbazole and a phosphorescent metal complex (non- Patent Document 3) has been proposed.

APPLIED PHYSICS LETTERS, vol. 75, 4 (1999) APPLIED PHYSICS LETTERS, vol. 78, 1622 (2001) JOURNAL OF APPLIED PHYSICS, vol. 92, 87 (2002)

  However, these light-emitting materials do not provide sufficient light-emitting characteristics when used for manufacturing elements such as light-emitting elements.

  Therefore, an object of the present invention is to provide a composition useful as a light-emitting material or the like that can obtain sufficient light-emitting characteristics when used for manufacturing an element such as a light-emitting element.

（式中、Ｘはハロゲン原子を表す。Ｒ¹〜Ｒ¹⁵はそれぞれ独立に、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアルキルチオ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールオキシ基、ハロゲン原子で置換されていてもよいアリールチオ基、ハロゲン原子で置換されていてもよいアリールアルキル基、ハロゲン原子で置換されていてもよいアリールアルキルオキシ基、ハロゲン原子で置換されていてもよいアリールアルキルチオ基、ハロゲン原子で置換されていてもよいアリールアルケニル基、ハロゲン原子で置換されていてもよいアリールアルキニル基、ハロゲン原子で置換されていてもよい１価の複素環基、又はハロゲン原子を表す。Ｍは、イリジウム原子、白金原子、オスミウム原子、ルテニウム原子、パラジウム原子、ロジウム原子、レニウム原子、又はコバルト原子を表す。ｎは、１又は２である。Ｒ¹〜Ｒ¹⁰が複数存在する場合には、各々、同一であっても異なっていてもよい。）
本発明は第二に、さらに、溶媒を含有する前記組成物からなる液状組成物を提供する。
本発明は第三に、前記組成物を用いてなる薄膜、発光素子等の素子を提供する。
本発明は第四に、前記発光素子を備えた面状光源、表示装置及び照明を提供する。 The present invention first provides a composition comprising a metal complex represented by the following formula (1) and a polymer charge transport material.

(In the formula, X represents a halogen atom. R ^{1 to} R ¹⁵ are each independently a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or a halogen atom. An alkylthio group optionally substituted with, an aryl group optionally substituted with a halogen atom, an aryloxy group optionally substituted with a halogen atom, an arylthio group optionally substituted with a halogen atom, a halogen atom An optionally substituted arylalkyl group, an arylalkyloxy group optionally substituted with a halogen atom, an arylalkylthio group optionally substituted with a halogen atom, an arylalkenyl group optionally substituted with a halogen atom, An arylalkynyl group optionally substituted with a halogen atom, substituted with a halogen atom And M represents an iridium atom, a platinum atom, an osmium atom, a ruthenium atom, a palladium atom, a rhodium atom, a rhenium atom, or a cobalt atom, and n represents an optionally substituted monovalent heterocyclic group or a halogen atom. 1 or 2. When a plurality of R ^{1 to} R ¹⁰ are present, they may be the same or different.
The present invention secondly further provides a liquid composition comprising the composition containing a solvent.
Thirdly, the present invention provides an element such as a thin film and a light emitting element using the composition.
Fourthly, the present invention provides a planar light source, a display device, and illumination provided with the light emitting element.

  When the composition of the present invention is used for production of an element such as a light-emitting element, sufficient light-emitting characteristics can be obtained, and usually it has excellent solubility in a solvent. Therefore, the composition of this invention is useful for manufacture of light emitting elements, such as an organic EL element, a planar light source, a display apparatus, illumination, an organic transistor, etc.

Hereinafter, the present invention will be described in detail.
<Composition>
The composition of the present invention comprises a metal complex represented by the formula (1) and a polymer charge transport material.

-Metal complex-
In the formula (1), the metal atom represented by M is preferably an iridium atom or a platinum atom. N is 1 or 2, which is an integer obtained by subtracting 1 from the valence of the metal atom M represented by M.

  In the formula (1), examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom is preferable.

In the formula (1), the alkyl group represented by R ^{1 to} R ¹⁵ may be linear, branched or cyclic, and the carbon number is usually about 1 to 12, preferably 1 to 8. It is. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclohexyl group, a heptyl group, an octyl group, and a 2-ethylhexyl group. , Nonyl group, decyl group, 3,7-dimethyloctyl group, dodecyl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, and the like. An ethyl group, a t-butyl group, and a trifluoromethyl group are preferable.

In the formula (1), the alkoxy group represented by R ^{1 to} R ¹⁵ may be linear, branched or cyclic, and the carbon number is usually about 1 to 12, preferably 1 to 8. It is. Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyl Oxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, dodecyloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyl group, perfluoro Examples include an octyl group, a methoxymethyloxy group, a 2-methoxyethyloxy group, and the like, and a methoxy group, an ethoxy group, a t-butoxy group, and a trifluoromethoxy group are preferable.

In the formula (1), the alkylthio group represented by R ^{1 to} R ¹⁵ may be linear, branched or cyclic, and the carbon number is usually about 1 to 12, preferably 1 to 8. It is. Examples of the alkylthio group include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2 -Ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, dodecylthio group, trifluoromethylthio group and the like.

In the formula (1), the aryl group represented by R ^{1 to} R ¹⁵ is an aromatic hydrocarbon (having a condensed ring, two or more independent benzene rings or condensed rings are directly or via a group such as vinylene. From 1 to 4), and the number of carbon atoms is usually about 6 to 60, preferably 6 to 48. Examples of the aryl group include a phenyl group, C ₁ -C ₁₂ alkoxyphenyl group ( "C ₁ -C ₁₂ alkoxy". Hereinafter, the same indicating that the carbon atoms in the alkoxy moiety is 1 to 12 ), C ₁ -C ₁₂ alkylphenyl group (“C ₁ -C ₁₂ alkyl” indicates that the alkyl moiety has 1 to 12 carbon atoms, the same shall apply hereinafter), 1-naphthyl group, Examples include 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group, and the like, and phenyl group, methylphenyl group, and t-butylphenyl group are preferable.
The C ₁ -C ₁₂ alkoxyphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, isopropyloxyphenyl group, butoxyphenyl group, isobutoxyphenyl group, t-butoxyphenyl group, pentyloxyphenyl group, hexyl Oxyphenyl group, cyclohexyloxyphenyl group, heptyloxyphenyl group, octyloxyphenyl group, 2-ethylhexyloxyphenyl group, nonyloxyphenyl group, decyloxyphenyl group, 3,7-dimethyloctyloxyphenyl group, dodecyloxyphenyl group Etc.
Examples of the C ₁ -C ₁₂ alkylphenyl group include methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, t-butyl. Examples thereof include a phenyl group, a pentylphenyl group, an isoamylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, and a dodecylphenyl group.

In the formula (1), the aryloxy group represented by R ^{1 to} R ¹⁵ usually has about 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms. Examples of the aryloxy group include a phenoxy group, C ₁ -C ₁₂ alkoxy phenoxy group, C ₁ -C ₁₂ alkylphenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, a pentafluorophenyl group and the like.
Examples of the C _{1 to} C ₁₂ alkoxyphenoxy group include a methoxyphenoxy group, an ethoxyphenoxy group, a propyloxyphenoxy group, an isopropyloxyphenoxy group, a butoxyphenoxy group, an isobutoxyphenoxy group, a t-butoxyphenoxy group, and a pentyloxyphenoxy group. Hexyloxyphenoxy group, cyclohexyloxyphenoxy group, heptyloxyphenoxy group, octyloxyphenoxy group, 2-ethylhexyloxyphenoxy group, nonyloxyphenoxy group, decyloxyphenoxy group, 3,7-dimethyloctyloxyphenoxy group, dodecyloxy A phenoxy group etc. are mentioned, A phenoxy group, a methylphenoxy group, and t-butylphenoxy group are preferable.
Examples of the C _{1 to} C ₁₂ alkylphenoxy group include a methylphenoxy group, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxy group, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, an isopropylphenoxy group, and a butylphenoxy group. Group, isobutylphenoxy group, t-butylphenoxy group, pentylphenoxy group, isoamylphenoxy group, hexylphenoxy group, heptylphenoxy group, octylphenoxy group, nonylphenoxy group, decylphenoxy group, dodecylphenoxy group and the like.

In the formula (1), the arylthio group represented by R ^{1 to} R ¹⁵ usually has about 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms. As the arylthio group, for example, phenylthio group, C ₁ -C ₁₂ alkoxyphenyl-thio group, C ₁ -C ₁₂ alkyl phenylthio group, 1-naphthylthio group, 2-naphthylthio group, pentafluorophenylthio group and the like .

In the formula (1), the arylalkyl group represented by R ^{1 to} R ¹⁵ usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms. Examples of the arylalkyl group include a phenyl -C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkyl group 1-naphthyl-C ₁ -C ₁₂ alkyl group, 2-naphthyl-C ₁ -C ₁₂ alkyl group, etc., C ₁ -C ₁₂ alkoxyphenyl-C ₁ -C ₁₂ alkyl group, and C ₁ -C _{A 12} alkylphenyl-C ₁ -C ₁₂ alkyl group is preferred.

In the formula (1), the arylalkyloxy group represented by R ^{1 to} R ¹⁵ usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms. Examples of the arylalkyloxy group include phenyl-C ₁ -C ₁ such as phenylmethoxy group, phenylethoxy group, phenylbutoxy group, phenylpentyloxy group, phenylhexyloxy group, phenylheptyloxy group, and phenyloctyloxy group. ₁₂ alkoxy group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkoxy group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkoxy groups, 1-naphthyl -C ₁ -C ₁₂ alkoxy group, 2- naphthyl -C ₁ -C ₁₂ alkoxy groups and the like.

In the formula (1), the arylalkylthio group represented by R ^{1 to} R ¹⁵ usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms. Examples of the arylalkylthio group include a phenyl -C ₁ -C ₁₂ alkylthio group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkylthio group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkylthio group 1-naphthyl-C ₁ -C ₁₂ alkylthio group, 2-naphthyl-C ₁ -C ₁₂ alkylthio group and the like.

In the formula (1), the arylalkenyl group represented by R ^{1 to} R ¹⁵ usually has about 8 to 60 carbon atoms, preferably 8 to 48 carbon atoms. Examples of the arylalkenyl group include a phenyl -C ₂ -C ₁₂ alkenyl group, C ₁ -C ₁₂ alkoxyphenyl -C ₂ -C ₁₂ alkenyl group, C ₁ -C ₁₂ alkylphenyl -C ₂ -C ₁₂ alkenyl group 1-naphthyl-C ₂ -C ₁₂ alkenyl group, 2-naphthyl-C ₂ -C ₁₂ alkenyl group and the like.

In the formula (1), the arylalkynyl group represented by R ^{1 to} R ¹⁵ usually has about 8 to 60 carbon atoms, preferably 8 to 48 carbon atoms. As the arylalkynyl group, for example, a phenyl-C ₂ -C ₁₂ alkynyl group (“C ₂ -C ₁₂ alkynyl”) indicates that the alkynyl moiety has 2 to 12 carbon atoms. ), C ₁ -C ₁₂ alkoxyphenyl-C ₂ -C ₁₂ alkynyl group, C ₁ -C ₁₂ alkylphenyl-C ₂ -C ₁₂ alkynyl group, 1-naphthyl-C ₂ -C ₁₂ alkynyl group, 2-naphthyl- C ₂ -C ₁₂ alkynyl groups and the like.

In the formula (1), the monovalent heterocyclic group represented by R ^{1 to} R ¹⁵ means the remaining atomic group obtained by removing one hydrogen atom from the heterocyclic compound, and the carbon number thereof is usually 4 About 60, preferably 4-20. The carbon number of the heterocyclic group does not include the carbon number of the substituent. The heterocyclic compound is an organic compound having a cyclic structure in which not only carbon atoms but also heteroatoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms, and boron atoms are ring atoms. Means what is contained within. The monovalent heterocyclic group said, for example, thienyl group, C ₁ -C ₁₂ alkyl thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, C ₁ -C ₁₂ alkyl pyridyl group, piperidyl group, quinolyl group, isoquinolyl group Etc.

In the formula (1), the halogen atom represented by R ^{1 to} R ¹⁵ and the halogen atom that the above group represented by R ^{1 to} R ¹⁵ may have as a substituent are represented by X. This is the same as described and exemplified in the section of the halogen atom.

In Formula (1), R ^{1 to} R ¹⁵ may be a hydrogen atom, an alkyl group that may be substituted with a halogen atom, an alkoxy group that may be substituted with a halogen atom, or a substituent that is substituted with a halogen atom. Preferred aryl group, arylalkyl group optionally substituted with a halogen atom, halogen atom is preferred, hydrogen atom, alkyl group optionally substituted with halogen atom, alkoxy group, halogen atom is more preferred, hydrogen atom, halogen atom Alkyl groups that may be substituted with atoms are particularly preferred.

（式中、Ｘ及びＲ¹〜Ｒ¹⁵は、前記と同じ意味を有する。Ｒ¹〜Ｒ¹⁰が複数存在する場合には、それらは同一であっても異なっていてもよい。）

（式中、Ｘ’はハロゲン原子を表す。Ｒ^A〜Ｒ^Eはそれぞれ独立に、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールアルキル基、又はハロゲン原子を表す。） Among the metal complexes, from the viewpoint of ease of ligand synthesis, those represented by the following formulas (1a) and (1b) are preferable, and those represented by the following formulas (1c) and (1d) are more preferable. preferable.

(In the formula, X and R ^{1 to} R ¹⁵ have the same meaning as described above. When a plurality of R ^{1 to} R ¹⁰ are present, they may be the same or different.)

(In the formula, X ′ represents a halogen atom. R ^{A to} R ^E are each independently a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or a halogen. An aryl group that may be substituted with an atom, an arylalkyl group that may be substituted with a halogen atom, or a halogen atom.

In the formulas (1c) and (1d), the halogen atom represented by X ′ is the same as described and exemplified in the section of X, and is substituted with the halogen atom represented by R ^{A to} R ^E. An alkyl group which may be substituted, an alkoxy group which may be substituted with a halogen atom, an aryl group which may be substituted with a halogen atom, an arylalkyl group which may be substituted with a halogen atom, or a halogen atom, The groups represented by R ^{1 to} R ¹⁵ are the same as those described and exemplified in terms of atoms.

（式中、Ｘは前記と同じである。Ｒ’は、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールアルキル基、又はハロゲン原子を表す。複数存在するＲ’は、同一であっても異なっていてもよい。） Examples of the metal complex include the following.

(In the formula, X is the same as above. R ′ is a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or a halogen atom. An aryl group that may be substituted with a halogen atom, or a halogen atom, and R's that are present may be the same or different.

In the above formula, an alkyl group which may be substituted with a halogen atom represented by R ′, an alkoxy group which may be substituted with a halogen atom, an aryl group which may be substituted with a halogen atom, or a halogen atom The arylalkyl group or halogen atom which may be used is the same as described and exemplified in the section of groups and atoms represented by R ^{1 to} R ¹⁵ .

Specific examples of the metal complex are shown below.

  In the composition of the present invention, the metal complexes may be used alone or in combination of two or more.

  The metal complex of the present invention may be synthesized by any method. For example, Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 78 (4), 97-106 (1984).

  Specifically, a solvent is placed in a flask, and the mixture is stirred and bubbled with an inert gas such as nitrogen gas or argon gas, degassed, and then a metal complex (that is, a metal-containing compound) is distributed. Add a ligand compound. You may add a base and a silver salt compound as needed. While stirring the reaction solution thus obtained, stirring is continued under an inert gas atmosphere until ligand exchange is performed. You may heat as needed. The end point of the reaction can be determined by confirming that the reduction of the raw material has stopped or that one of the raw materials has disappeared using a TLC monitor or high performance liquid chromatography. The reaction time is usually about 30 minutes to 150 hours. The conditions for taking out and purifying the target product from the reaction mixture obtained after the completion of the reaction vary depending on the target metal complex.For example, the target product can be taken out by distilling off the reaction solvent or removing the precipitate generated by the reaction. What is necessary is just to perform by methods, such as filtration collection | recovery, and purification may be performed by methods, such as column chromatography, solvent washing | cleaning, sublimation, and recrystallization. The obtained metal complex can be identified and analyzed by CHN elemental analysis, mass spectrometry and NMR.

-Polymer charge transport material-
The polymer charge transport material is a high molecular weight charge transport material, and is classified into a conjugated polymer, a non-conjugated polymer, and the like.

  The conjugated polymer means a polymer compound in which 80 to 100%, particularly 85 to 100%, particularly 90 to 100% of all bonds in the main chain are conjugated, and includes an aromatic ring in the main chain. Conjugated polymers are preferred.

  Examples of the aromatic ring include benzene, fluorene, dibenzothiophene, dibenzofuran, dibenzosilole and the like.

  Examples of the conjugated polymer containing an aromatic ring in the main chain include a phenylene group which may have a substituent, a fluorenediyl group which may have a substituent, and a substituent. A high molecular weight compound containing a repeating unit such as a dibenzothiophene diyl group, an optionally substituted dibenzofurandiyl group, an optionally substituted dibenzosilolediyl group, etc. Copolymers having units and other repeating units; JP2003-231741, JP2004059899A, JP2004002654A, JP2004-292546A, US5708130, WO9954385, WO0046321 , WO02077060, "Organic EL display" Co-author, Ohm), 111 pages, monthly display, vol. 9, no. 9, polymer compounds described in pages 47-51, 2002, and the like.

（式中、Ｙは、−Ｏ−、−Ｓ−、−Ｓｅ−、−Ｂ（Ｒ¹⁸）−、−Ｓｉ（Ｒ¹⁹）（Ｒ²⁰）−、−Ｐ（Ｒ²¹）−、−Ｐ（Ｒ²²）（＝Ｏ）−、−Ｃ（Ｒ²³）（Ｒ²⁴）−、−Ｃ（Ｒ²⁵）（Ｒ²⁶）−Ｃ（Ｒ²⁷）（Ｒ²⁸）−、−Ｏ−Ｃ（Ｒ²⁹）（Ｒ³⁰）−、−Ｓ−Ｃ（Ｒ³¹）（Ｒ³²）−、−Ｎ（Ｒ³³）−Ｃ（Ｒ³⁴）（Ｒ³⁵）−、−Ｓｉ（Ｒ³⁶）（Ｒ³⁷）−Ｃ（Ｒ³⁸）（Ｒ³⁹）−、−Ｓｉ（Ｒ⁴⁰）（Ｒ⁴¹）−Ｓｉ（Ｒ⁴²）（Ｒ⁴³）−、−Ｃ（Ｒ⁴⁴）＝Ｃ（Ｒ⁴⁵）−、−Ｎ（Ｒ⁴⁶）−、−Ｎ＝Ｃ（Ｒ⁴⁷）−、又は−Ｓｉ（Ｒ⁴⁸）＝Ｃ（Ｒ⁴⁹）−を表す。Ｒ¹⁸〜Ｒ⁴⁹はそれぞれ独立に、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアルキルチオ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールオキシ基、ハロゲン原子で置換されていてもよいアリールチオ基、ハロゲン原子で置換されていてもよいアリールアルキル基、ハロゲン原子で置換されていてもよいアリールアルキルオキシ基、ハロゲン原子で置換されていてもよいアリールアルキルチオ基、ハロゲン原子で置換されていてもよいアリールアルケニル基、ハロゲン原子で置換されていてもよいアリールアルキニル基、ハロゲン原子で置換されていてもよい１価の複素環基又はハロゲン原子を表す。Ｒ¹⁶及びＲ¹⁷はそれぞれ独立に、水素原子、ハロゲン原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基又はハロゲン原子で置換されていてもよいアリール基を表す。複数存在するＲ¹⁶及びＲ¹⁷は、同一であっても異なっていてもよい。） Other examples of the conjugated polymer containing an aromatic ring in the main chain include a polymer compound having a repeating unit represented by the following formula (2).

(In the formula, Y represents —O—, —S—, —Se—, —B (R ¹⁸ ) —, —Si (R ¹⁹ ) (R ²⁰ ) —, —P (R ²¹ ) —, —P ( R ²² ) (═O) —, —C (R ²³ ) (R ²⁴ ) —, —C (R ²⁵ ) (R ²⁶ ) —C (R ²⁷ ) (R ²⁸ ) —, —O—C (R ²⁹⁾ ) (R ³⁰ ) —, —S—C (R ³¹ ) (R ³² ) —, —N (R ³³ ) —C (R ³⁴ ) (R ³⁵ ) —, —Si (R ³⁶ ) (R ³⁷ ) — C (R ³⁸ ) (R ³⁹ )-, -Si (R ⁴⁰ ) (R ⁴¹ ) -Si (R ⁴² ) (R ⁴³ )-, -C (R ⁴⁴ ) = C (R ⁴⁵ )-, -N ( R ⁴⁶ ) —, —N═C (R ⁴⁷ ) —, or —Si (R ⁴⁸ ) ═C (R ⁴⁹ ) —, wherein R ^{18 to} R ⁴⁹ are each independently substituted with a hydrogen atom or a halogen atom. An alkyl group which may be substituted, an alkoxy group which may be substituted with a halogen atom, or a substituent which may be substituted with a halogen atom An alkylthio group, an aryl group optionally substituted with a halogen atom, an aryloxy group optionally substituted with a halogen atom, an arylthio group optionally substituted with a halogen atom, an aryl optionally substituted with a halogen atom An alkyl group, an arylalkyloxy group optionally substituted with a halogen atom, an arylalkylthio group optionally substituted with a halogen atom, an arylalkenyl group optionally substituted with a halogen atom, and a halogen atom; R ¹⁶ and R ¹⁷ each independently represents a hydrogen atom, a halogen atom or a halogen atom, and may represent an arylalkynyl group, a monovalent heterocyclic group which may be substituted with a halogen atom, or a halogen atom. Alkyl group, alkoxy which may be substituted with a halogen atom Or optionally substituted with a halogen atom represents an even aryl group. R ¹⁶ and R ¹⁷ there are a plurality may be the same or different.)

In the formula (2), the groups and atoms represented by R ¹⁶ and R ¹⁷ and R ^{18 to} R ⁴⁹ are the same as those described and exemplified in the groups and atoms represented by the R ^{1 to} R ^15. It is.

（式中、Ｒ^*は、水素原子、ハロゲン原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基又はハロゲン原子で置換されていてもよいアリール基を表す。Ｒ^**は、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアルキルチオ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールオキシ基、ハロゲン原子で置換されていてもよいアリールチオ基、ハロゲン原子で置換されていてもよいアリールアルキル基、ハロゲン原子で置換されていてもよいアリールアルキルオキシ基、ハロゲン原子で置換されていてもよいアリールアルキルチオ基、ハロゲン原子で置換されていてもよいアリールアルケニル基、ハロゲン原子で置換されていてもよいアリールアルキニル基、ハロゲン原子で置換されていてもよい１価の複素環基又はハロゲン原子を表す。複数存在するＲ^*は、同一であっても異なっていてもよい。Ｒ^**が複数存在する場合には、それらは同一であっても異なっていてもよい。） Examples of the repeating unit represented by the formula (2) include those having the following structure.

(In the formula, R ^* represents a hydrogen atom, a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or an aryl group optionally substituted with a halogen atom. R ^** represents a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, an alkylthio group optionally substituted with a halogen atom, or a halogen atom. Aryl group which may be substituted, aryloxy group which may be substituted with halogen atom, arylthio group which may be substituted with halogen atom, arylalkyl group which may be substituted with halogen atom, substituted with halogen atom Arylalkyloxy group which may be substituted, arylalkylthio which may be substituted with halogen atom Represents an arylalkenyl group optionally substituted with a halogen atom, an arylalkynyl group optionally substituted with a halogen atom, a monovalent heterocyclic group optionally substituted with a halogen atom, or a halogen atom. The R ^{* s} may be the same or different, and when there are a plurality of R ^** , they may be the same or different.)

In the above formula, the group and atom represented by R ^* are the same as the group and atom represented by R ¹⁶ and R ¹⁷ , but a hydrogen atom is preferred.

In the above formula, the group and atom represented by R ^** are the same as the group and atom represented by R ^{18 to} R ⁴⁹ , but an alkyl group which may be substituted with a halogen atom is preferred and unsubstituted. The alkyl group is more preferable.

（式中、Ｒ^*及びＲ^**は、前記と同じ意味を有する。複数存在するＲ^*及びＲ^**は、各々、同一であっても異なっていてもよい。） As the repeating unit represented by the formula (2), the followings are preferable from the viewpoint of device lifetime and device characteristics.

(In the formula, R ^* and R ^** have the same meaning as described above. A plurality of R ^* and R ^** may be the same or different.)

（式中、Ａｒ¹、Ａｒ²、Ａｒ³及びＡｒ⁴はそれぞれ独立に、アリーレン基又は２価の複素環基を表す。Ａｒ⁵、Ａｒ⁶及びＡｒ⁷はそれぞれ独立に、アリール基又は１価の複素環基を表す。Ａｒ¹〜Ａｒ⁷は置換基を有していてもよい。ｘ及びｙはそれぞれ独立に、０又は１を示し、０≦ｘ＋ｙ≦１である。） The conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the formula (2) and a repeating unit represented by the following formula (3) from the viewpoint of emission intensity. There may be.

(In the formula, Ar ¹ , Ar ² , Ar ³ and Ar ⁴ each independently represent an arylene group or a divalent heterocyclic group. Ar ⁵ , Ar ⁶ and Ar ⁷ each independently represent an aryl group or a monovalent group. Ar ^{1 to} Ar ⁷ may have a substituent, and x and y each independently represent 0 or 1, and 0 ≦ x + y ≦ 1.

（式中、Ｒ^***は、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアルキルチオ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールオキシ基、ハロゲン原子で置換されていてもよいアリールチオ基、ハロゲン原子で置換されていてもよいアリールアルキル基、ハロゲン原子で置換されていてもよいアリールアルキルオキシ基、ハロゲン原子で置換されていてもよいアリールアルキルチオ基、ハロゲン原子で置換されていてもよいアリールアルケニル基、ハロゲン原子で置換されていてもよいアリールアルキニル基、ハロゲン原子で置換されていてもよい１価の複素環基又はハロゲン原子を表す。複数存在するＲ^***は、同一であっても異なっていてもよい。） In the formula (3), the arylene group represented by Ar ¹ , Ar ² , Ar ³ and Ar ⁴ means an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and usually has 6 carbon atoms. About 60, preferably 6-20. The aromatic hydrocarbon includes those having a condensed ring and those in which two or more independent benzene rings or condensed rings are bonded directly or via a group such as vinylene. Examples of the arylene group include those having the following structure.

(In the formula, R ^*** represents a hydrogen atom, an alkyl group which may be substituted with a halogen atom, an alkoxy group which may be substituted with a halogen atom, an alkylthio group which may be substituted with a halogen atom, a halogen atom, An aryl group optionally substituted by an atom, an aryloxy group optionally substituted by a halogen atom, an arylthio group optionally substituted by a halogen atom, an arylalkyl group optionally substituted by a halogen atom, a halogen An arylalkyloxy group optionally substituted with an atom, an arylalkylthio group optionally substituted with a halogen atom, an arylalkenyl group optionally substituted with a halogen atom, an arylalkynyl optionally substituted with a halogen atom Group, a monovalent heterocyclic group which may be substituted with a halogen atom, or a halogen atom A plurality of R ^*** may be the same or different.)

（式中、Ｒは、水素原子、ハロゲン原子で置換されていてもよいアルキル基、ハロゲン原子で置換されていてもよいアルコキシ基、ハロゲン原子で置換されていてもよいアルキルチオ基、ハロゲン原子で置換されていてもよいアリール基、ハロゲン原子で置換されていてもよいアリールオキシ基、ハロゲン原子で置換されていてもよいアリールチオ基、ハロゲン原子で置換されていてもよいアリールアルキル基、ハロゲン原子で置換されていてもよいアリールアルキルオキシ基、ハロゲン原子で置換されていてもよいアリールアルキルチオ基、ハロゲン原子で置換されていてもよいアリールアルケニル基、ハロゲン原子で置換されていてもよいアリールアルキニル基、又はハロゲン原子を表す。複数存在するＲは、同一であっても異なっていてもよい。） In the formula (3), the divalent heterocyclic group represented by Ar ¹ , Ar ² , Ar ³ and Ar ⁴ means an atomic group obtained by removing two hydrogen atoms from a heterocyclic compound. Examples of the divalent heterocyclic group include the following.
Divalent heterocyclic group containing a nitrogen atom as a hetero atom; pyridinediyl group (formula 45 to 50), diazaphenylene group (formula 51 to 54), quinolinediyl group (formula 55 to 69), quinoxalinediyl Groups (the following formulas 70 to 74), acridinediyl groups (the following formulas 75 to 78), bipyridyldiyl groups (the following formulas 79 to 84), and phenanthroline diyl groups (the following formulas 82 to 84).
A group having a fluorene structure containing a silicon atom, a nitrogen atom, a sulfur atom, a selenium atom or the like as a hetero atom (the following formulas 85 to 96).
5-membered ring heterocyclic groups containing silicon atom, nitrogen atom, sulfur atom, selenium atom and the like as a hetero atom: (the following formulas 97 to 101).
5-membered ring condensed hetero groups containing a silicon atom, a nitrogen atom, a sulfur atom, a selenium atom and the like as a hetero atom: (the following formulas 102 to 111).
A 5-membered ring heterocyclic group containing a silicon atom, a nitrogen atom, a sulfur atom, a selenium atom, etc. as a hetero atom, and bonded to the α-position of the hetero atom to form a dimer or oligomer: (Formula 112 ~ 115).
A 5-membered ring heterocyclic group containing a silicon atom, a nitrogen atom, a sulfur atom, a selenium atom or the like as a hetero atom, and a group bonded to the phenyl group at the α-position of the hetero atom (the following formulas 116 to 122).
Groups in which a 5-membered condensed heterocyclic group containing an oxygen atom, a nitrogen atom, a sulfur atom or the like as a hetero atom is substituted with a phenyl group, a furyl group, or a thienyl group: (the following formulas 123 to 128).

(In the formula, R is a hydrogen atom, an alkyl group which may be substituted with a halogen atom, an alkoxy group which may be substituted with a halogen atom, an alkylthio group which may be substituted with a halogen atom, or a halogen atom. Aryl group which may be substituted, aryloxy group which may be substituted with halogen atom, arylthio group which may be substituted with halogen atom, arylalkyl group which may be substituted with halogen atom, substituted with halogen atom An arylalkyloxy group that may be substituted, an arylalkylthio group that may be substituted with a halogen atom, an arylalkenyl group that may be substituted with a halogen atom, an arylalkynyl group that may be substituted with a halogen atom, or Represents a halogen atom, and a plurality of R may be the same or different. It may be.)

The group and atom represented by R are the same as the group and atom described in the section of R ^{1 to} R ¹⁵ .

In the above formula, the group and atom represented by R ^*** are the same as the group and atom represented by R ^{1 to} R ¹⁵ , but a hydrogen atom is preferred.

（式中、Ｒ^***は、前記と同じ意味を有する。複数存在するＲ^***は、同一であっても異なっていてもよい。）
で表される基がより好ましい。 In the above formula (3), Ar ¹ , Ar ² , Ar ³ and Ar ⁴ are preferably arylene groups, represented by the following formula:

(In the formula, R ^*** has the same meaning as described above. A plurality of R ^*** may be the same or different.)
Is more preferable.

In the formula (3), the aryl group represented by Ar ⁵ , Ar ⁶ and Ar ⁷ is preferably an aryl group substituted with an alkyl group. Aryl group in an aryl group substituted with the alkyl group are those having a carbon number of usually 6 to 60, specifically, a phenyl group, C ₁ -C ₁₂ alkoxyphenyl group, C ₁ -C ₁₂ alkylphenyl Group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group and the like, and phenyl group is preferable.
The alkyl group in the aryl group substituted with the alkyl group may be linear, branched or cyclic, and the carbon number thereof is usually about 1 to 12, specifically, methyl group, ethyl Group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyl An octyl group, a dodecyl group, etc. are mentioned.

In the formula (3), the monovalent heterocyclic group represented by Ar ⁵ , Ar ⁶ and Ar ⁷ is the same as the monovalent heterocyclic group represented by R ^{1 to} R ¹⁵ .

  In the formula (3), x and y are each preferably 0 from the viewpoint of ease of synthesis.

（式中、Ｒ^****は、ハロゲン原子で置換されていてもよいアルキル基を表す。）
で表されるものが好ましく、下記式：

で表されるものがより好ましい。 As the repeating unit represented by the formula (3), the following formula:

(In the formula, R ^**** represents an alkyl group which may be substituted with a halogen atom.)
Are preferably represented by the following formula:

Is more preferable.

The alkyl group which may be substituted with a halogen atom represented by R ^**** is the same as the alkyl group which may be substituted with a halogen atom represented by R ^{1 to} R ¹⁵ .

（式中、Ｒ^*、Ｒ^**及びＲ^****は、前記と同じ意味を有する。複数存在するＲ^*及びＲ^**は、各々、同一であっても異なっていてもよい。） When the conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the formula (2) and a repeating unit represented by the formula (3), the polymer Examples of the compound include a polymer compound having a repeating unit represented by the following formula (2a) and a repeating unit represented by the following formula (3a).

(In the formula, R ^* , R ^** and R ^**** have the same meaning as described above. A plurality of R ^* and R ^** may be the same or different.)

  When the conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the formula (2) and a repeating unit represented by the formula (3), the polymer The repeating unit represented by the formula (2) in the compound: The repeating unit represented by the formula (3) is preferably 98: 2 to 60:40 in terms of molar ratio, and 95: 5 to 70: More preferably, it is 30.

  The non-conjugated polymer means a polymer compound other than the conjugated polymer. Examples of the non-conjugated polymer include polyvinyl carbazole and derivatives thereof. This polyvinyl carbazole and derivatives thereof are obtained, for example, from a vinyl monomer by cation polymerization or radical polymerization.

  As the polymer charge transport material, one of the conjugated polymer and the non-conjugated polymer may be used alone, or two or more of them may be used in combination, or both may be used alone or in combination. You may use together each above.

The number average molecular weight in terms of polystyrene of the polymer charge transport material is preferably 1 × 10 ³ to 1 × 10 ^8, more preferably 1 × 10 ⁴ to 1 × 10 ⁶ , and the weight average molecular weight in terms of polystyrene is 1 ×. 10 ³ to 1 × 10 ⁸ are preferable, and 5 × 10 ^{3 to} 5 × 10 ⁶ are more preferable.

  The amount of the metal complex in the composition of the present invention is usually 0.001 to 70 parts by weight, preferably 0.01 to 50 parts by weight, more preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the polymer charge transport material. Parts by weight.

-Other ingredients-
The composition of the present invention may contain other components as needed in addition to the metal complex and the polymer charge transport material. Examples of the other component include at least one selected from the group consisting of a low molecular hole transport material, a low molecular electron transport material, and a light emitting material.

  Examples of the low molecular hole transport material include TAPC (1,1-bis [4- (di-p-tolyl) aminophenyl] cyclohexane), TPD (N, N′-dimethyl-N, N ′-(3- Methylphenyl) -1,1'-biphenyl-4,4'-diamine), α-NPD (4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl), m-MTDATA ( 4,4 ', 4' '-tris (3-methylphenylphenylamino) triphenylamine), TCTA (4,4-tri (N-carbazolyl) triphenylamine), 2-TNATA (4,4', 4 '' -Tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine) and the like.

Examples of the low molecular electron transport material include Alq ₃ (tris (8-quinolinol) aluminum), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), oxadiazole derivative tBu-PBD ( 2- (4′-t-butylphenyl) -5- (4 ″ -biphenylyl) -1,3,4-oxadiazole) and the like.

  As the light emitting material, known materials can be used. For example, naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, polymethine, xanthene, coumarin, and cyanine dyes, 8-hydroxyquinoline and the like. Metal complexes of derivatives, aromatic amines, tetraphenylcyclopentadiene and derivatives thereof, tetraphenylbutadiene and derivatives thereof, metal complexes of 2-phenyl-pyridine and derivatives thereof, metal complexes of 2-phenyl-benzothiazole and derivatives thereof, 2 -Metal complexes of phenyl-benzoxazole and its derivatives, metal complexes of porphyrin and its derivatives, and the like.

  When the composition of the present invention contains other components, the ratio of the total amount of the metal complex and the polymer charge transport material in the composition of the present invention (components other than the solvent in this paragraph) is usually 30. It is ˜99.9% by weight, preferably 50 to 99.9% by weight.

<Liquid composition>
The composition of the present invention is particularly useful as a liquid composition for the production of light-emitting elements and organic transistors. The liquid composition is such that the composition of the present invention further contains a solvent. In the present specification, the “liquid composition” means a liquid composition at the time of device fabrication. The liquid composition typically means a liquid at normal pressure (ie, 1 atm) and 25 ° C., and may be called ink, ink composition, solution, or the like.

When forming a film using this liquid composition (for example, a composition in a solution state) at the time of producing a light emitting device, it is only necessary to remove the solvent by drying after applying the liquid composition. Very advantageous. In addition, in the case of drying, you may dry in the state heated at about 50-150 degreeC, and may be dried by reducing pressure to about 10 ^<-3 > Pa.

  For film formation using a liquid composition, spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing A coating method such as a method, a flexographic printing method, an offset printing method, an ink jet printing method, a nozzle coating method, or a capillary coating method can be used.

  The proportion of the solvent in the liquid composition is usually 1% by weight to 99.9% by weight, preferably 60% by weight to 99.9% by weight, based on the total weight of the liquid composition. Preferably it is 90 weight%-99.8 weight%. The viscosity at 25 ° C. of the liquid composition varies depending on the printing method, but is preferably in the range of 0.5 to 500 mPa · s. When the liquid composition such as the ink jet printing method passes through a discharge device, In order to prevent clogging and flight bending, the viscosity is preferably in the range of 0.5 to 20 mPa · s.

  As the solvent contained in the liquid composition, those capable of dissolving or dispersing components other than the solvent in the liquid composition are preferable. Examples of the solvent include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene, and trimethyl. Aromatic hydrocarbon solvents such as benzene and mesitylene, aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, ester solvents such as ethyl acetate, butyl acetate, methyl benzoate, ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether Polyethylene alcohol and its derivatives such as ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, 1,2-hexanediol, methanol, ethanol, propanol, isopropanol, cyclohexanol, etc. Examples thereof include alcohol-based solvents, sulfoxide-based solvents such as dimethyl sulfoxide, and amide-based solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination. Among the solvents, it is preferable from the viewpoint of viscosity, film formability, and the like to include an organic solvent having a structure containing a benzene ring and having a melting point of 0 ° C. or lower and a boiling point of 100 ° C. or higher.

  The solvent is an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, an ester from the viewpoints of solubility in organic solvent of components other than the solvent in the liquid composition, uniformity during film formation, viscosity characteristics, and the like. Solvents and ketone solvents are preferable, and toluene, xylene, ethylbenzene, diethylbenzene, trimethylbenzene, mesitylene, n-propylbenzene, i-propylbenzene, n-butylbenzene, i-butylbenzene, s-butylbenzene, anisole, ethoxy Benzene, 1-methylnaphthalene, cyclohexane, cyclohexanone, cyclohexylbenzene, bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane, n-hexylcyclohexane, methylbenzoate, 2-propylcyclohexanone, 2-heptanone, 3-heptan Non, 4-heptanone, 2-octanone, 2-nonanone, 2-decanone, dicyclohexyl ketone are preferred, xylene, anisole, mesitylene, cyclohexylbenzene and bicyclohexyl methyl benzoate preferred.

  The type of solvent contained in the liquid composition is preferably two or more, more preferably two to three, and more preferably two from the viewpoints of film forming properties and device characteristics. Further preferred.

  When two kinds of solvents are contained in the liquid composition, one of the solvents may be in a solid state at 25 ° C. From the viewpoint of film formability, it is preferable that one type of solvent has a boiling point of 180 ° C. or higher, and the other one type of solvent preferably has a boiling point of less than 180 ° C. One type of solvent has a boiling point of 200 ° C. More preferably, the solvent has a boiling point of less than 180 ° C. Further, from the viewpoint of viscosity, at 60 ° C., it is preferable that 0.2% by weight or more of the component excluding the solvent from the liquid composition is dissolved in the solvent, and one of the two solvents has 25 ° C. It is preferable that 0.2% by weight or more of the component excluding the solvent from the liquid composition dissolves.

  When the liquid composition contains three kinds of solvents, one or two kinds of the solvents may be in a solid state at 25 ° C. From the viewpoint of film formability, at least one of the three solvents is preferably a solvent having a boiling point of 180 ° C. or higher, and at least one solvent is preferably a solvent having a boiling point of less than 180 ° C. At least one of the types of solvents is a solvent having a boiling point of 200 ° C. or more and 300 ° C. or less, and at least one of the solvents is more preferably a solvent having a boiling point of less than 180 ° C. From the viewpoint of viscosity, it is preferable that two of the three types of solvents have 0.2% by weight or more of the component obtained by removing the solvent from the liquid composition at 60 ° C. Of these solvents, it is preferable that 0.2% by weight or more of the component obtained by removing the solvent from the liquid composition is dissolved in the solvent at 25 ° C.

  When two or more kinds of solvents are contained in the liquid composition, the solvent having the highest boiling point is 40 to 90% by weight of the total solvent contained in the liquid composition from the viewpoint of viscosity and film formability. Preferably, it is 50 to 90% by weight, more preferably 65 to 85% by weight.

  As the solvent contained in the liquid composition, from the viewpoints of viscosity and film formability, a combination of anisole and bicyclohexyl, a combination of anisole and cyclohexylbenzene, a combination of xylene and bicyclohexyl, a combination of xylene and cyclohexylbenzene, mesitylene and methyl A combination of benzoates is preferred.

  From the viewpoint of solubility of components other than the solvent contained in the liquid composition in the solvent, the difference between the solubility parameter of the solvent and the solubility parameter of the component other than the solvent contained in the liquid composition is 10 or less. Is more preferable, and it is more preferable that it is 7 or less. These solubility parameters can be obtained by the method described in “Solvent Handbook (published by Kodansha, 1976)”.

<Thin film>
The thin film of the present invention uses the composition or the liquid composition (hereinafter, the composition and the liquid composition are collectively referred to as “composition”). Examples of the thin film include a light-emitting thin film, a conductive thin film, and an organic semiconductor thin film.

  The light-emitting thin film preferably has a high quantum yield of light emission from the viewpoint of the brightness of the element, the light emission voltage, and the like.

  The conductive thin film preferably has a surface resistance of 1 KΩ / □ or less. The electrical conductivity can be increased by doping the thin film with a Lewis acid, an ionic compound or the like. The surface resistance is more preferably 100Ω / □ or less, and further preferably 10Ω / □ or less.

The organic semiconductor thin film has a higher electron mobility or hole mobility, preferably 10 ⁻⁵ cm ² / V / second or more, more preferably 10 ⁻³ cm ² / V / second or more, More preferably, it is 10 ^-1 cm ² / V / second or more. In addition, an organic transistor can be manufactured using an organic semiconductor thin film. Specifically, an organic transistor can be formed by forming an organic semiconductor thin film on a Si substrate on which an insulating film such as SiO ₂ and a gate electrode are formed, and forming a source electrode and a drain electrode with Au or the like. .

<Element>
The element of the present invention has a composition using the composition, for example, an electrode composed of an anode and a cathode, and a layer formed between the electrodes and composed of the composition. This element can be used as, for example, a light emitting element, a switching element, or a photoelectric conversion element.
-Light emitting device-
Hereinafter, a light emitting element which is a typical application will be described as an example.
The light-emitting device of the present invention has, for example, an electrode composed of an anode and a cathode, and a layer (light-emitting layer) provided between the electrodes and using the composition, and further includes a charge transport layer (hole A transport layer, an electron transport layer), a charge blocking layer (a hole blocking layer, an electron blocking layer), and the like.

Specifically, the following structures a) to d) are exemplified.
a) Anode / light emitting layer / cathode b) Anode / hole transport layer / light emitting layer / cathode c) Anode / light emitting layer / electron transport layer / cathode d) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (Here, / indicates that each layer is laminated adjacently. The same shall apply hereinafter.)
The light emitting layer is a layer having a light emitting function, the hole transporting layer is a layer having a function of transporting holes, and the electron transporting layer is a layer having a function of transporting electrons. Note that two or more light emitting layers, hole transport layers, and electron transport layers may be used.
Among the charge transport layers provided adjacent to the electrode, those having the function of improving the charge injection efficiency from the electrode and having the effect of lowering the driving voltage of the element are particularly charge injection layers (hole injection layer, electron (Injection layer).

In order to improve adhesion with the electrode and charge injection from the electrode, the charge injection layer or the insulating layer (average film thickness is usually 0.5 to 4 nm) may be provided adjacent to the electrode. In addition, a thin buffer layer may be inserted at the interface between the charge transport layer and the light emitting layer in order to improve adhesion at the interface or prevent mixing. Further, a hole blocking layer may be inserted at the interface with the light emitting layer in order to transport electrons and confine holes.
The order and number of layers to be stacked, and the thickness of each layer may be adjusted in consideration of light emission efficiency and element lifetime.

In the present invention, examples of the light emitting element provided with the charge injection layer include a light emitting element provided with the charge injection layer adjacent to the cathode and a light emitting element provided with the charge injection layer adjacent to the anode.
For example, the following structures e) to p) are specifically mentioned.
e) Anode / charge injection layer / light emitting layer / cathode f) Anode / light emitting layer / charge injection layer / cathode g) Anode / charge injection layer / light emitting layer / charge injection layer / cathode h) Anode / charge injection layer / hole Transport layer / light emitting layer / cathode i) anode / hole transport layer / light emitting layer / charge injection layer / cathode j) anode / charge injection layer / hole transport layer / light emitting layer / charge injection layer / cathode k) anode / charge Injection layer / light emitting layer / charge transport layer / cathode l) anode / light emitting layer / electron transport layer / charge injection layer / cathode m) anode / charge injection layer / light emitting layer / electron transport layer / charge injection layer / cathode n) anode / Charge injection layer / hole transport layer / light emitting layer / charge transport layer / cathode o) anode / hole transport layer / light emitting layer / electron transport layer / charge injection layer / cathode p) anode / charge injection layer / hole transport Layer / light emitting layer / electron transport layer / charge injection layer / cathode

  The charge injection layer is a layer containing a conductive polymer, provided between the anode and the hole transport layer, and has an ionization potential of an intermediate value between the anode material and the hole transport material contained in the hole transport layer. Examples thereof include a layer including a material having a material, a layer including a material provided between the cathode and the electron transport layer, and having a material having an intermediate electron affinity between the cathode material and the electron transport material included in the electron transport layer.

When the charge injection layer is a layer containing a conductive polymer, the electrical conductivity of the conductive polymer is preferably 10 ⁻⁵ to 10 ³ S / cm, and the leakage current between the light emitting pixels is reduced. Therefore, 10 ⁻⁵ to 10 ² S / cm is more preferable, and 10 ⁻⁵ to 10 ¹ S / cm is further preferable. Usually, in order to set the electric conductivity of the conductive polymer to 10 ⁻⁵ to 10 ³ S / cm, the conductive polymer is doped with an appropriate amount of ions.

  The type of ions to be doped is an anion for the hole injection layer and a cation for the electron injection layer. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, camphor sulfonate ion, and the like, and examples of the cation include lithium ion, sodium ion, potassium ion, tetrabutylammonium ion, and the like.

  The material of the charge injection layer may be appropriately selected in relation to the electrode and the material of the adjacent layer. Polyaniline and derivatives thereof, polyaminophen and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, polythienylene vinylene And derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain, metal phthalocyanine (copper phthalocyanine, etc.), carbon, etc. . The thickness of the charge injection layer is usually 1 nm to 100 nm, preferably 2 nm to 50 nm.

  Examples of the material for the insulating layer include metal fluorides, metal oxides, and organic insulating materials. Examples of the light emitting element provided with an insulating layer include a light emitting element provided with an insulating layer adjacent to the cathode and a light emitting element provided with an insulating layer adjacent to the anode.

Specific examples include the following structures q) to ab).
q) anode / insulating layer / light emitting layer / cathode r) anode / light emitting layer / insulating layer / cathode s) anode / insulating layer / light emitting layer / insulating layer / cathode t) anode / insulating layer / hole transport layer / light emitting layer / Cathode u) anode / hole transport layer / light emitting layer / insulating layer / cathode v) anode / insulating layer / hole transport layer / light emitting layer / insulating layer / cathode w) anode / insulating layer / light emitting layer / electron transport layer / Cathode x) anode / light emitting layer / electron transport layer / insulating layer / cathode y) anode / insulating layer / light emitting layer / electron transport layer / insulating layer / cathode z) anode / insulating layer / hole transport layer / light emitting layer / Electron transport layer / cathode aa) anode / hole transport layer / light emitting layer / electron transport layer / insulating layer / cathode ab) anode / insulating layer / hole transport layer / light emitting layer / electron transport layer / insulating layer / cathode

  The material of the hole blocking layer is made of a material having an ionization potential larger than that of the material of the light emitting layer, such as a metal complex of bathocuproine, 8-hydroxyquinoline or a derivative thereof. The film thickness of the hole blocking layer is usually 1 nm to 100 nm, preferably 2 nm to 50 nm.

Specifically, for example, the following structures ac) to an) are mentioned.
ac) anode / charge injection layer / light emitting layer / hole blocking layer / cathode ad) anode / light emitting layer / hole blocking layer / charge injection layer / cathode ae) anode / charge injection layer / light emitting layer / hole blocking layer / Charge injection layer / cathode af) anode / charge injection layer / hole transport layer / light emitting layer / hole blocking layer / cathode ag) anode / hole transport layer / light emitting layer / hole blocking layer / charge injection layer / cathode ah ) Anode / charge injection layer / hole transport layer / light emitting layer / hole blocking layer / charge injection layer / cathode ai) anode / charge injection layer / light emitting layer / hole blocking layer / charge transport layer / cathode aj) anode / Light emitting layer / hole blocking layer / electron transport layer / charge injection layer / cathode ak) anode / charge injection layer / light emitting layer / hole blocking layer / electron transport layer / charge injection layer / cathode al) anode / charge injection layer / Hole transport layer / light emitting layer / hole blocking layer / charge transport layer / cathode am) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer Charge injection layer / cathode an) anode / charge injection layer / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / charge injection layer / cathode

  When the light emitting layer of the present invention is formed, when the light emitting layer is formed from a solution, it is only necessary to remove the solvent by drying after applying the solution, and also charge transport materials and light emitting materials (specifically, The same method can be applied to the case of mixing as described above, which is very advantageous in production.

  When forming a film from a solution, spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, nozzle coating, Coating methods such as a capillary coating method, a screen printing method, a flexographic printing method, an offset printing method, and an ink jet printing method can be used. These methods can also be applied to film formation of a hole transport layer, an electron transport layer, and the like described later.

  When the light emitting device of the present invention has a hole transport layer, examples of the hole transport material used include polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, and polysiloxane having an aromatic amine in the side chain or main chain. Derivatives, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyaniline and derivatives thereof, polyaminophen and derivatives thereof, polypyrrole and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5- Thienylene vinylene) and derivatives thereof, such as polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having aromatic amine compound groups in the side chain or main chain, polyaniline and derivatives thereof, polyaminophen and derivatives thereof. High molecular weight hole transport materials such as poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, side A polysiloxane derivative having an aromatic amine in the chain or main chain is more preferable. In the case of a low molecular weight hole transport material, it is preferably used by being dispersed in a polymer binder.

  As a method for forming a hole transport layer, a method of forming a film from a mixed solution with a polymer binder is used for a low molecular weight hole transport material, and a method of forming a film from a solution for a high molecular weight hole transport material. Is used.

  Solvents used for film formation from solutions include those that dissolve hole transport materials, for example, chlorinated solvents such as chloroform, methylene chloride, and dichloroethane, ether solvents such as tetrahydrofuran, and aromatic carbonization such as toluene and xylene. Examples thereof include hydrogen solvents, ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.

  The film thickness of the hole transport layer differs depending on the material used and may be selected so that the drive voltage and the light emission efficiency are appropriate, but at least a thickness that does not cause pinholes is required. If the thickness is too thick, the driving voltage of the element increases, which is not preferable. Accordingly, the thickness of the hole transport layer is usually 1 nm to 1 μm, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.

  When the light-emitting device of the present invention has an electron transport layer, examples of the electron transport material used include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinones and derivatives thereof. Derivatives, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and Derivatives thereof, aminoxadiazole derivatives, benzoquinone and derivatives thereof, anthraquinone and derivatives thereof, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof. , Polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof are preferred, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum and polyquinoline are more preferable.

  In the case of an electron transport material having a low molecular weight, the electron transport layer may be formed from a vacuum deposition method using a powder, a solution or a molten state. In the case of a high molecular weight electron transport material, the film may be formed from a solution or a molten state. A film may be used. When forming a film from a solution or a molten state, a polymer binder may be used in combination.

  Solvents used for film formation from solution include those that dissolve electron transport materials and / or polymer binders, for example, chlorine-based solvents such as chloroform, methylene chloride, dichloroethane, ether-based solvents such as tetrahydrofuran, toluene, xylene And aromatic hydrocarbon solvents such as acetone, ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.

  The film thickness of the electron transport layer varies depending on the material used, and may be selected so that the drive voltage and the light emission efficiency are moderate values, but at least a thickness that does not cause pinholes is required. If the thickness is too thick, the drive voltage of the element becomes high, which is not preferable. Therefore, the film thickness of the electron transport layer is usually 1 nm to 1 μm, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.

  The light emitting device of the present invention is usually formed on a substrate. The substrate is not particularly limited as long as it forms an electrode and does not change when forming each layer of the light emitting element, and examples thereof include substrates such as glass, plastic, polymer film, and silicon. In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent.

  Usually, it is preferable that at least one of the electrodes composed of the anode and the cathode is transparent or translucent, and the anode side is transparent or translucent. Each of the anode and the cathode may be a single layer or a laminated structure of two or more layers.

  As the material for the anode, a conductive metal oxide film, a translucent metal thin film, or the like is used. Specifically, indium oxide, zinc oxide, tin oxide, and a composite film made of conductive glass made of indium / tin / oxide (ITO), indium / zinc / oxide, etc. (NESA) Etc.), gold, platinum, silver, copper and the like are used, and ITO, indium / zinc / oxide, and tin oxide are preferable. Examples of the production method include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like. Moreover, you may use organic transparent conductive films, such as polyaniline and its derivative (s), polyaminophen, and its derivative (s) as this anode.

  The thickness of the anode can be appropriately selected in consideration of light transmittance and electric conductivity, but is usually 10 nm to 10 μm, preferably 20 nm to 1 μm, more preferably 50 nm to 500 nm. It is.

  In addition, a layer made of a phthalocyanine derivative, a conductive polymer, carbon, or the like, or an insulating layer made of a metal oxide, a metal fluoride, an organic insulating material, or the like may be provided on the anode to facilitate charge injection. Good.

  The cathode material preferably has a low work function. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, or the like Two or more of these alloys, or one or more of them and an alloy of one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, or graphite or graphite intercalation compound Etc. are used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy and the like.

  The thickness of the cathode can be appropriately selected in consideration of electric conductivity and durability, but is usually 10 nm to 10 μm, preferably 20 nm to 1 μm, and more preferably 50 nm to 500 nm.

  As a method for producing the cathode, a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression bonded, or the like is used. In addition, a protective layer for protecting the light emitting element may be attached after the cathode is manufactured. In order to use the light emitting element stably for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the element from the outside.

  As the protective layer, a polymer compound, metal oxide, metal fluoride, metal boride and the like can be used. Further, as the protective cover, a glass plate, a plastic plate having a low water permeability treatment on the surface, or the like can be used, and a method of sealing the cover by bonding it to the element substrate with a thermosetting resin or a photocurable resin is preferable. Used for. If the space is maintained by using the spacer, it is easy to prevent the element from being damaged. If an inert gas such as nitrogen or argon is sealed in the space, oxidation of the cathode can be prevented, and the moisture adsorbed in the manufacturing process can be prevented by installing a desiccant such as barium oxide in the space. It becomes easy to suppress damage to the element. Among these, it is preferable to take one or more measures.

  The light-emitting element of the present invention can be used for a planar light source, a display device (segment display device, dot matrix display device, liquid crystal display device), its backlight, illumination, and the like.

  In order to obtain planar light emission using the light emitting element of the present invention, the planar anode and cathode may be arranged so as to overlap each other. In addition, in order to obtain pattern-like light emission, a method of installing a mask provided with a pattern-like window on the surface of the planar light-emitting element, an organic material layer of a non-light-emitting portion is formed extremely thick and substantially non- There are a method of emitting light and a method of forming either one of the anode or the cathode or both electrodes in a pattern. By forming a pattern by any one of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display element capable of displaying numbers, letters, simple symbols and the like can be obtained. Further, in order to obtain a dot matrix element, both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by a method of separately applying a plurality of types of light emitting materials having different emission colors or a method using a color filter or a light emission conversion filter. The dot matrix element can be driven passively or may be active driven in combination with a TFT or the like. These display elements can be used as display devices for computers, televisions, mobile terminals, mobile phones, car navigation systems, video camera viewfinders, and the like.

-Photoelectric conversion element-
Next, a photoelectric conversion element is demonstrated as a use of the composition of this invention.
As a photoelectric conversion element, for example, an element in which a layer formed by using the composition of the present invention is sandwiched between two pairs of electrodes, at least one of which is transparent or translucent, or the composition of the present invention formed on a substrate An element having a comb-shaped electrode formed on a layer made of In order to improve the characteristics, fullerene, carbon nanotube, or the like may be mixed.

  As a manufacturing method of a photoelectric conversion element, the method described in Japanese Patent No. 3146296 is exemplified. Specifically, a method of forming a thin film using the composition of the present invention on a substrate having a first electrode and forming a second electrode thereon, a set of combs formed on the substrate The method of forming the thin film which uses the composition of this invention on an electrode is illustrated. One of the first and second electrodes is transparent or translucent. As the method for forming the thin film and the method for mixing fullerene and carbon nanotube, those exemplified for the light emitting device can be suitably used.

  Examples will be shown below for illustrating the present invention in more detail, but the present invention is not limited to these examples.

で表される構造を添え字のモル比率で有する高分子化合物（Ｈ−１）を370mg得た。この高分子化合物（Ｈ−１）のポリスチレン換算の重量平均分子量Ｍｗは46,000であり、ポリスチレン換算の数平均分子量Ｍｎは16,000であった。 <Example 1>
-Synthesis of polymer compound (H-1)-
Under an inert atmosphere, 2,7-dibromo-9,9-dioctylfluorene (252 mg, 0.460 mmol), 9,9-dioctylfluorene-2,7-bis (ethylene boronate) (305 mg, 0.575 mmol), And N-4-s-butyl-N, N-4,4-bromophenylamine (52.8 mg, 0.115 mmol) were dissolved in toluene (5.2 g), and tetrakis (triphenylphosphine) palladium (1.99 mg, 0.00173 mmol) was added and stirred at room temperature for 10 minutes. Subsequently, 2 ml of a 20% by weight aqueous solution of tetraethylammonium hydroxide was added and stirred at room temperature for 20 minutes. The resulting solution was then warmed and heated to reflux for 18 hours, then 90 mg of bromobenzene was added for 2 hours, and 70 mg of phenylboronic acid was added and heated to reflux for 2 hours. After completion of heating, the resulting solution was cooled to room temperature. The obtained reaction mixture was added dropwise to 50 ml of methanol, and the deposited precipitate was separated by filtration. After drying this precipitate under reduced pressure, the obtained solid was dissolved in 15 ml of toluene, added to 50 ml of methanol and stirred. The deposited precipitate is separated by filtration, washed with methanol, and dried under reduced pressure to obtain the following formula:

370 mg of the polymer compound (H-1) having the structure represented by The polymer compound (H-1) had a polystyrene equivalent weight average molecular weight Mw of 46,000 and a polystyrene equivalent number average molecular weight Mn of 16,000.

で表される金属錯体(Ir-dimer-1)2.96gを得た。 -Synthesis of metal complex (Ir-dimer-1)-
In a reaction vessel, weigh 1-phenylisoquinoline (2.46 g, 12 mmol), iridium chloride trihydrate (1.93 g, 5.5 mmol), 2-ethoxyethanol (24 mL), and water (8 mL) under a nitrogen stream, Heated at 140 ° C. for 9 hours. After air cooling, the obtained reaction product was filtered off, washed with water, methanol and hexane in this order and dried to obtain the following formula:

As a result, 2.96 g of a metal complex (Ir-dimer-1) represented by the following formula was obtained.

で表される金属錯体（１−１）97mgを得た。
¹H-NMR(400.4MHz、CDCl₃)：9.95(d , 1H, J = 6.4 Hz)、9.18-8.75(br , 2H )、9.00-8.98(m , 1H )、8.86(d , 1H, J = 8.4 Hz)、8.17(d , 1H, J = 8.0 Hz)、8.13(d , 1H, J = 8.0 Hz)、8.01(d , 1H, J = 6.0 Hz)、7.94-7.88(m, 2H)、7.72-7.61(m, 5H)、7.53(d , 1H, J = 6.4 Hz), 7.35(d , 1H, J = 6.4 Hz)、7.18(t , 2H, J = 6.4 Hz)、6.94(t , 1H, J = 7.6 Hz)、6.88(t , 1H, J = 7.6 Hz)、6.75(t , 1H, J = 7.4 Hz)、6.69(t , 1H, J = 7.2 Hz)、6.42(d , 1H, J = 7.6 Hz), 6.26(d , 1H, J = 7.6 Hz) -Synthesis of metal complex (1-1)-
In a reaction vessel, pyridine (0.034 g, 0.4 mmol), dichloromethane (10 ml), and metal complex (Ir-dimer-1) (0.127 g, 0.1 mmol) were weighed and stirred at room temperature for 16 hours under an argon gas atmosphere. . The resulting solution was concentrated to about 1/3 volume and hexane was added dropwise to precipitate. The precipitate was filtered off, washed with hexane and dried under reduced pressure. Furthermore, by recrystallizing this precipitate several times using dichloromethane and hexane, the following formula:

97 mg of a metal complex (1-1) represented by
¹ H-NMR (400.4 MHz, CDCl ₃ ): 9.95 (d, 1H, J = 6.4 Hz), 9.18-8.75 (br, 2H), 9.00-8.98 (m, 1H), 8.86 (d, 1H, J = 8.4 Hz), 8.17 (d, 1H, J = 8.0 Hz), 8.13 (d, 1H, J = 8.0 Hz), 8.01 (d, 1H, J = 6.0 Hz), 7.94-7.88 (m, 2H), 7.72 -7.61 (m, 5H), 7.53 (d, 1H, J = 6.4 Hz), 7.35 (d, 1H, J = 6.4 Hz), 7.18 (t, 2H, J = 6.4 Hz), 6.94 (t, 1H, J = 7.6 Hz), 6.88 (t, 1H, J = 7.6 Hz), 6.75 (t, 1H, J = 7.4 Hz), 6.69 (t, 1H, J = 7.2 Hz), 6.42 (d, 1H, J = 7.6 Hz), 6.26 (d, 1H, J = 7.6 Hz)

-Preparation of Composition 1-
A 0.5 wt% chloroform solution (that is, composition 1) of a mixture obtained by adding 5 parts by weight of the metal complex (1-1) to 95 parts by weight of the compound (H-1) was prepared.

-Production of organic EL elements-
Using a solution of poly (ethylenedioxythiophene) / polystyrene sulfonic acid (Bayer, trade name: BaytronP) on a glass substrate on which an ITO film having a thickness of 150 nm is formed by sputtering, the film is spin-coated to a thickness of 50 nm. The solution was applied to form a film, and dried on a hot plate at 200 ° C. for 10 minutes. Next, a film (film thickness: mixture of the metal complex (1-1) and the polymer compound (H-1) at a rotational speed of 3200 rpm by spin coating using the chloroform solution (composition 1) prepared above. About 90 nm). The obtained film was dried in a nitrogen atmosphere at 60 ° C. for 20 minutes, and then, as a cathode, barium was deposited at about 5 nm, and then aluminum was deposited at about 80 nm to produce an organic EL device. Note that, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started. By applying a voltage to the obtained organic EL element, EL light emission having a peak at 620 nm was obtained. This organic EL element started to emit light at about 5.3 V, and emitted 1000 cd / m ² at about 7.7 V.

<Example 2>
-Preparation of composition 2-
A 0.4 wt% chloroform solution (that is, composition 2) of a mixture obtained by adding 10 parts by weight of the metal complex (1-1) to 90 parts by weight of the polymer compound (H-1) was prepared.

-EL emission characteristics of Composition 2-
In Example 1, the composition 2 was used in place of the composition 1, and an organic EL device was prepared and measured in the same manner as in Example 1 except that the spin coat was applied at a rotational speed of 4000 rpm. By applying a voltage to the obtained organic EL element, EL light emission having a peak at 625 nm was obtained. This organic EL element started to emit light at about 6.4 V, and emitted 1000 cd / m ² at about 9.6 V.

で表されるイリジウム錯体（Ａ−１）は、Eur. J. Inorg. Chem. ２５６９,（２００２）.に記載の方法で合成した。
反応容器に、１−フェニルイソキノリン(0.25 g,1.2mmol)、イリジウム錯体（Ａ−１）(0.15g,0.20mmol)、2-エトキシエタノール(2mL)を量り取り、窒素気流下、１４時間還流した。空冷後、得られた褐色反応物を濾別し、水、メタノール、ヘキサンの順で洗浄、乾燥させることにより、下記式：

で表される金属錯体(Ir-dimer-2) 0.16gを得た。
¹H NMR (400 MHz, CDCl₃): δ 9.35 (d, 6.4 Hz, 4H), 8.95 (d, 8.8 Hz, 4H), 8.10 (d, 7.6 Hz, 4H), 7.96 (d, 8.0 Hz, 4H), 7.84 (t, 7.4 Hz, 4H), 7.75 (t, 7.8 Hz, 4H), 6.83-6.79 (m, 8H), 6.52 (t, 7.4 Hz, 4H), 6.01 ppm (d, 8.0 Hz, 4H); (400 MHz, DMSO-d₆): δ 9.77-9..73 (m, 2H), 8.90-8.84 (m, 2H), 8.25-8.12 (m, 4H), 8.02-7.81 (m, 6H), 7.02 (t, 8.2 Hz, 1H), 6.89 (t, 7.4 Hz, 1H), 6.79 (t, 7.0 Hz, 1H), 6.63 (t, 7.4 Hz, 1H), 6.21 (d, 7.2 Hz, 1H), 5.57 ppm (d, 7.6 Hz, 1H). <Example 3>
-Synthesis of metal complex (Ir-dimer-2)-
Following formula:

The iridium complex (A-1) represented by this was synthesized by the method described in Eur. J. Inorg. Chem. 2569, (2002).
In a reaction vessel, 1-phenylisoquinoline (0.25 g, 1.2 mmol), iridium complex (A-1) (0.15 g, 0.20 mmol) and 2-ethoxyethanol (2 mL) were weighed and refluxed for 14 hours under a nitrogen stream. . After cooling with air, the resulting brown reaction product was filtered off, washed with water, methanol, and hexane in this order, and dried to obtain the following formula:

As a result, 0.16 g of a metal complex (Ir-dimer-2) represented by the following formula was obtained.
¹ H NMR (400 MHz, CDCl ₃ ): δ 9.35 (d, 6.4 Hz, 4H), 8.95 (d, 8.8 Hz, 4H), 8.10 (d, 7.6 Hz, 4H), 7.96 (d, 8.0 Hz, 4H ), 7.84 (t, 7.4 Hz, 4H), 7.75 (t, 7.8 Hz, 4H), 6.83-6.79 (m, 8H), 6.52 (t, 7.4 Hz, 4H), 6.01 ppm (d, 8.0 Hz, 4H ); (400 MHz, DMSO-d ₆ ): δ 9.77-9..73 (m, 2H), 8.90-8.84 (m, 2H), 8.25-8.12 (m, 4H), 8.02-7.81 (m, 6H ), 7.02 (t, 8.2 Hz, 1H), 6.89 (t, 7.4 Hz, 1H), 6.79 (t, 7.0 Hz, 1H), 6.63 (t, 7.4 Hz, 1H), 6.21 (d, 7.2 Hz, 1H) ), 5.57 ppm (d, 7.6 Hz, 1H).

で表される金属錯体（１−２）２６mgを得た。
¹H NMR(400 MHz, CDCl₃): δ 10.15(d, 1H, J = 6.0 Hz), 9.20-8.90(br, 2H ), 9.00-8.98(m, 1H ), 8.81(d, 1H, J = 8.4 Hz), 8.18(d, 1H, J = 8.4Hz), 8.09-8.07(m, 2H), 7.95-7.89(m, 2H), 7.73-7.61(m, 5H), 7.53(d, 1H, J = 6.4 Hz), 7.36(d, 1H, J = 6.4 Hz), 7.16(t, 2H, J = 6.4 Hz), 6.93(t, 1H, J = 7.6 Hz), 6.88(t, 1H, J = 7.6 Hz), 6.76(t, 1H, J = 7.4 Hz), 6.70(t, 1H, J = 7.2 Hz), 6.32(t, 2H, J = 8.4 Hz). -Synthesis of metal complex (1-2)-
In a reaction vessel, pyridine (3 mL) and metal complex (Ir-dimer-2) (0.030 g, 0.022 mmol) were weighed and heated and stirred at 100 ° C. for 15 hours in an argon gas atmosphere. After air cooling, the obtained solution was dropped into hexane to cause precipitation. This red-orange precipitate was filtered off, washed with hexane, and then dried under reduced pressure to obtain the following formula:

26 mg of a metal complex (1-2) represented by
¹ H NMR (400 MHz, CDCl ₃ ): δ 10.15 (d, 1H, J = 6.0 Hz), 9.20-8.90 (br, 2H), 9.00-8.98 (m, 1H), 8.81 (d, 1H, J = 8.4 Hz), 8.18 (d, 1H, J = 8.4 Hz), 8.09-8.07 (m, 2H), 7.95-7.89 (m, 2H), 7.73-7.61 (m, 5H), 7.53 (d, 1H, J = 6.4 Hz), 7.36 (d, 1H, J = 6.4 Hz), 7.16 (t, 2H, J = 6.4 Hz), 6.93 (t, 1H, J = 7.6 Hz), 6.88 (t, 1H, J = 7.6 Hz), 6.76 (t, 1H, J = 7.4 Hz), 6.70 (t, 1H, J = 7.2 Hz), 6.32 (t, 2H, J = 8.4 Hz).

-Preparation of Composition 3-
A 0.4 wt% chloroform solution (that is, composition 3) of a mixture obtained by adding 10 parts by weight of the metal complex (1-2) to 90 parts by weight of the polymer compound (H-1) was prepared.

-EL emission characteristics of Composition 3-
In Example 2, an organic EL device was produced and measured in the same manner as in Example 2 except that the composition 3 was used instead of the composition 2. By applying a voltage to the obtained organic EL element, EL light emission having a peak at 620 nm was obtained. This organic EL device started to emit light at about 6.9 V, and emitted 1000 cd / m ² at about 11.0 V.

<Example 4>
-Preparation of composition 4-
A 0.4 wt% chloroform solution (that is, composition 4) of a mixture obtained by adding 5 parts by weight of metal complex (1-2) to 95 parts by weight of polymer compound (H-1) was prepared.

-EL emission characteristics of Composition 4-
An organic EL device was produced and measured in the same manner as in Example 2 except that the composition 4 was used instead of the composition 2. By applying a voltage to the obtained organic EL element, EL light emission having a peak at 615 nm was obtained. The organic EL device started to emit light at about 4.8V and emitted 1000 cd / m ² at about 6.9V.

で表されるイリジウム錯体（Ａ−２）は、Z. Naturforsch. 1986, 41b, 76.に記載の方法で合成した。
反応容器に、１−フェニルイソキノリン(0.25 g, 1.2 mmol)、イリジウム錯体（Ａ−２）(0.17 g, 0.20 mmol)、2-エトキシエタノール(2mL)を量り取り、窒素気流下、１６時間還流した。空冷後、得られた明橙色反応物を濾別し、水、メタノール、ヘキサンの順で洗浄、乾燥させることにより、粗生成物０．２６ｇを得た。これをジクロロメタンで抽出し、溶媒を除去することにより、下記式：

で表される金属錯体(Ir-dimer-3)４３ｍｇを得た。
¹H NMR (400 MHz, CDCl₃): δ 9.84 (d, 6.0 Hz, 4H), 8.91 (d, 8.8 Hz, 4H), 8.09-8.06 (m, 8H), 7.84 (t, 7.6 Hz, 4H), 7.74 (t, 7.8 Hz, 4H), 7.16 (d, 6.4 Hz, 4H), 6.80 (t, 7.6 Hz, 4H), 6.53 (t, 7.6 Hz, 4H), 6.01 ppm (d, 7.6 Hz, 4H); (400 MHz, DMSO-d₆): δ 9.95 (d, 6.0 Hz, 1H), 9.79 (d, 6.8 Hz, 1H), 8.85 (d, 8.4 Hz, 2H), 8.24-8.13 (m, 4H), 7.97-7.80 (m, 6H), 7.03 (t, 7.0 Hz, 1H), 6.87 (t, 7.6 Hz, 1H), 6.81 (t, 7.6 Hz, 1H), 6.63 (t, 6.8 Hz, 1H), 6.05 (d, 7.6 Hz, 1H), 5.61 ppm (d, 7.2 Hz, 1H). <Example 5>
-Synthesis of metal complex (Ir-dimer-3)-
The following formula (A-2):

The iridium complex (A-2) represented by this was synthesized by the method described in Z. Naturforsch. 1986, 41b, 76.
In a reaction vessel, 1-phenylisoquinoline (0.25 g, 1.2 mmol), iridium complex (A-2) (0.17 g, 0.20 mmol) and 2-ethoxyethanol (2 mL) were weighed and refluxed for 16 hours under a nitrogen stream. . After air cooling, the obtained bright orange reaction product was filtered off, washed with water, methanol and hexane in this order and dried to obtain 0.26 g of a crude product. By extracting this with dichloromethane and removing the solvent, the following formula:

43 mg of a metal complex (Ir-dimer-3) represented by
¹ H NMR (400 MHz, CDCl ₃ ): δ 9.84 (d, 6.0 Hz, 4H), 8.91 (d, 8.8 Hz, 4H), 8.09-8.06 (m, 8H), 7.84 (t, 7.6 Hz, 4H) , 7.74 (t, 7.8 Hz, 4H), 7.16 (d, 6.4 Hz, 4H), 6.80 (t, 7.6 Hz, 4H), 6.53 (t, 7.6 Hz, 4H), 6.01 ppm (d, 7.6 Hz, 4H ); (400 MHz, DMSO-d ₆ ): δ 9.95 (d, 6.0 Hz, 1H), 9.79 (d, 6.8 Hz, 1H), 8.85 (d, 8.4 Hz, 2H), 8.24-8.13 (m, 4H ), 7.97-7.80 (m, 6H), 7.03 (t, 7.0 Hz, 1H), 6.87 (t, 7.6 Hz, 1H), 6.81 (t, 7.6 Hz, 1H), 6.63 (t, 6.8 Hz, 1H) , 6.05 (d, 7.6 Hz, 1H), 5.61 ppm (d, 7.2 Hz, 1H).

で表される金属錯体（１−３）２６mgを得た。
¹H NMR(400 MHz、CDCl₃): δ 10.42(d, 1H, J = 6.4 Hz), 9.25-8.95(br, 2H ), 9.00-8.98(m, 1H ), 8.75(d, 1H, J = 8.4 Hz), 8.22-8.18(m, 2H), 7.99(d, 1H, J = 8.0 Hz), 7.95-7.90(m, 2H), 7.74-7.60(m, 5H), 7.51(d, 1H, J = 6.8 Hz), 7.36(d, 1H, J = 6.4 Hz), 7.14-7.11(m, 2H), 6.92(t, 1H, J = 7.0 Hz), 6.86(t, 1H, J = 6.8 Hz), 6.77(t, 1H, J = 7.4 Hz), 6.71(t , 1H, J = 7.4 Hz), 6.38(d, 1H, J = 7.6 Hz), 6.17(d, 1H, J = 6.4 Hz). -Synthesis of metal complex (1-3)-
In a reaction vessel, pyridine (3 mL) and metal complex (Ir-dimer-3) (0.030 g, 0.020 mmol) were weighed and heated and stirred at 100 ° C. for 15 hours in an argon gas atmosphere. After air cooling, the obtained solution was dropped into hexane to cause precipitation. The red-orange precipitate was filtered off, washed with hexane, and then dried under reduced pressure to obtain the following formula (1-3):

26 mg of a metal complex (1-3) represented by
¹ H NMR (400 MHz, CDCl ₃ ): δ 10.42 (d, 1H, J = 6.4 Hz), 9.25-8.95 (br, 2H), 9.00-8.98 (m, 1H), 8.75 (d, 1H, J = 8.4 Hz), 8.22-8.18 (m, 2H), 7.99 (d, 1H, J = 8.0 Hz), 7.95-7.90 (m, 2H), 7.74-7.60 (m, 5H), 7.51 (d, 1H, J = 6.8 Hz), 7.36 (d, 1H, J = 6.4 Hz), 7.14-7.11 (m, 2H), 6.92 (t, 1H, J = 7.0 Hz), 6.86 (t, 1H, J = 6.8 Hz), 6.77 (t, 1H, J = 7.4 Hz), 6.71 (t, 1H, J = 7.4 Hz), 6.38 (d, 1H, J = 7.6 Hz), 6.17 (d, 1H, J = 6.4 Hz).

-Preparation of Composition 5-
A 0.4 wt% chloroform solution (that is, composition 5) of a mixture obtained by adding 5 parts by weight of metal complex (1-3) to 95 parts by weight of polymer compound (H-1) was prepared.

-EL emission characteristics of Composition 5-
In Example 2, an organic EL device was produced and measured in the same manner as in Example 2 except that the composition 5 was used instead of the composition 2. By applying a voltage to the obtained organic EL element, EL light emission having a peak at 620 nm was obtained. The organic EL device started to emit light at about 5.3 V, and emitted 1000 cd / m ² at about 8.0 V.

で表される金属錯体（Ｐｔ−１）は、J.Organomet.Chem. ６９０，４０９０−４０９３,２００５.に記載の方法で合成した。反応容器に、ピリジン４ｍＬ及び金属錯体(Ｐｔ−１)0.13 g（0.20 mmol）を量り取り、アルゴンガス雰囲気下、１００℃で３０分間加熱撹拌した。空冷後、得られた溶液をヘキサンに滴下して沈殿させた。この橙黄色沈殿を濾別し、ヘキサンで洗浄した後、減圧下で乾燥することにより、下記式：

で表される金属錯体（２−１）０．１１ｇを得た。
¹H NMR (400 MHz, CD₂Cl₂): δ 9.60 (d with satellites, 6.4 Hz, 1H), 9.00 (d with satellites, 6.8 Hz, 2H), 8.85 (d, 8.4 Hz, 1H), 8.08 (d, 8.0 Hz, 1H), 7.95 (t, 7.6 Hz, 1H), 7.92 (d, 8.4 Hz, 1H), 7.81 (t, 7.4 Hz, 1H), 7.72 (t, 7.6 Hz, 1H), 7.53 (d, 6.4 Hz, 1H), 7.48 (t, 6.4 Hz, 2H), 7.19 (t, 7.6 Hz, 1H), 7.02 (t, 7.4 Hz, 1H), 6.49 (d with satellites, 7.6 Hz, 1H). <Example 6>
-Synthesis of metal complex (2-1)-
Following formula:

The metal complex (Pt-1) represented by these was synthesize | combined by the method of J.Organomet.Chem.690, 4090-4093,2005. In a reaction vessel, 4 mL of pyridine and 0.13 g (0.20 mmol) of metal complex (Pt-1) were weighed and heated and stirred at 100 ° C. for 30 minutes in an argon gas atmosphere. After air cooling, the obtained solution was dropped into hexane to cause precipitation. The orange-yellow precipitate was filtered off, washed with hexane, and then dried under reduced pressure to obtain the following formula:

0.11 g of a metal complex (2-1) represented by
¹ H NMR (400 MHz, CD ₂ Cl ₂ ): δ 9.60 (d with satellites, 6.4 Hz, 1H), 9.00 (d with satellites, 6.8 Hz, 2H), 8.85 (d, 8.4 Hz, 1H), 8.08 ( d, 8.0 Hz, 1H), 7.95 (t, 7.6 Hz, 1H), 7.92 (d, 8.4 Hz, 1H), 7.81 (t, 7.4 Hz, 1H), 7.72 (t, 7.6 Hz, 1H), 7.53 ( d, 6.4 Hz, 1H), 7.48 (t, 6.4 Hz, 2H), 7.19 (t, 7.6 Hz, 1H), 7.02 (t, 7.4 Hz, 1H), 6.49 (d with satellites, 7.6 Hz, 1H).

-Preparation of Composition 6-
A 0.4 wt% chloroform solution (that is, composition 6) of a mixture obtained by adding 10 parts by weight of the metal complex (2-1) to 90 parts by weight of the polymer compound (H-1) was prepared.

-EL emission characteristics of composition 6-
In Example 2, except that the composition 6 is used in place of the composition 2, it can be confirmed that an organic EL device is produced and measured in the same manner as in Example 2 and exhibits excellent light emission characteristics.

で表される金属錯体（Ｂ）１０重量部を添加してなる混合物の０．４重量％クロロホルム溶液（即ち、組成物Ｃ１）を調製したが、金属錯体（Ｂ）が十分に溶解せず溶け残りが生じた。実施例２において、組成物２の代わりに組成物Ｃ１を用いた以外は実施例２と同様にして有機ＥＬ素子の作製を試みたが、膜が不均一のため測定に適した素子を得ることができなかった。 <Comparative Example 1>
-EL emission characteristic of composition C1-
The following formula (B) with respect to 90 parts by weight of the polymer compound (H-1):

A 0.4 wt% chloroform solution (that is, composition C1) of a mixture obtained by adding 10 parts by weight of the metal complex (B) represented by formula (1) was prepared, but the metal complex (B) was not sufficiently dissolved but dissolved. The rest has occurred. In Example 2, an attempt was made to produce an organic EL device in the same manner as in Example 2 except that the composition C1 was used instead of the composition 2, but an element suitable for measurement was obtained because the film was non-uniform. I could not.

Claims (20)

A composition comprising a metal complex represented by the following formula (1) and a polymer charge transport material.

(In the formula, X represents a halogen atom. R ^{1 to} R ¹⁵ are each independently a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or a halogen atom. An alkylthio group optionally substituted with, an aryl group optionally substituted with a halogen atom, an aryloxy group optionally substituted with a halogen atom, an arylthio group optionally substituted with a halogen atom, a halogen atom An optionally substituted arylalkyl group, an arylalkyloxy group optionally substituted with a halogen atom, an arylalkylthio group optionally substituted with a halogen atom, an arylalkenyl group optionally substituted with a halogen atom, An arylalkynyl group optionally substituted with a halogen atom, substituted with a halogen atom And M represents an iridium atom, a platinum atom, an osmium atom, a ruthenium atom, a palladium atom, a rhodium atom, a rhenium atom, or a cobalt atom, and n represents an optionally substituted monovalent heterocyclic group or a halogen atom. 1 or 2. When a plurality of R ^{1 to} R ¹⁰ are present, they may be the same or different. The composition according to claim 1, wherein the metal complex represented by the formula (1) is represented by the following formula (1a) or (1b).

(In the formula, X and R ^{1 to} R ¹⁵ have the same meaning as described above. When a plurality of R ^{1 to} R ¹⁰ are present, they may be the same or different.) The composition according to claim 2, wherein the metal complex represented by the formula (1a) is represented by the following formula (1c).

(In the formula, X ′ represents a halogen atom. R ^{A to} R ^E are each independently a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or a halogen. An aryl group that may be substituted with an atom, an arylalkyl group that may be substituted with a halogen atom, or a halogen atom. The composition according to claim 2, wherein the metal complex represented by the formula (1b) is represented by the following formula (1d).

(In the formula, X ′ and R ^{A to} R ^E have the same meaning as described above.)   The composition according to any one of claims 1 to 4, wherein the polymer charge transport material is a conjugated polymer or a non-conjugated polymer.   The composition according to claim 5, wherein the conjugated polymer is a conjugated polymer containing an aromatic ring in the main chain. The composition according to claim 6, wherein the conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the following formula (2).

(In the formula, Y represents —O—, —S—, —Se—, —B (R ¹⁸ ) —, —Si (R ¹⁹ ) (R ²⁰ ) —, —P (R ²¹ ) —, —P ( R ²² ) (═O) —, —C (R ²³ ) (R ²⁴ ) —, —C (R ²⁵ ) (R ²⁶ ) —C (R ²⁷ ) (R ²⁸ ) —, —O—C (R ²⁹⁾ ) (R ³⁰ ) —, —S—C (R ³¹ ) (R ³² ) —, —N (R ³³ ) —C (R ³⁴ ) (R ³⁵ ) —, —Si (R ³⁶ ) (R ³⁷ ) — C (R ³⁸ ) (R ³⁹ )-, -Si (R ⁴⁰ ) (R ⁴¹ ) -Si (R ⁴² ) (R ⁴³ )-, -C (R ⁴⁴ ) = C (R ⁴⁵ )-, -N ( R ⁴⁶ ) —, —N═C (R ⁴⁷ ) —, or —Si (R ⁴⁸ ) ═C (R ⁴⁹ ) —, wherein R ^{18 to} R ⁴⁹ are each independently substituted with a hydrogen atom or a halogen atom. An alkyl group which may be substituted, an alkoxy group which may be substituted with a halogen atom, or a substituent which may be substituted with a halogen atom An alkylthio group, an aryl group optionally substituted with a halogen atom, an aryloxy group optionally substituted with a halogen atom, an arylthio group optionally substituted with a halogen atom, an aryl optionally substituted with a halogen atom An alkyl group, an arylalkyloxy group optionally substituted with a halogen atom, an arylalkylthio group optionally substituted with a halogen atom, an arylalkenyl group optionally substituted with a halogen atom, and a halogen atom; R ¹⁶ and R ¹⁷ each independently represents a hydrogen atom, a halogen atom or a halogen atom, and may represent an arylalkynyl group, a monovalent heterocyclic group which may be substituted with a halogen atom, or a halogen atom. Alkyl group, alkoxy which may be substituted with a halogen atom Or optionally substituted with a halogen atom represents an even aryl group. R ¹⁶ and R ¹⁷ there are a plurality may be the same or different.) The conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the formula (2) and a repeating unit represented by the following formula (3). Composition.

(In the formula, Ar ¹ , Ar ² , Ar ³ and Ar ⁴ each independently represent an arylene group or a divalent heterocyclic group. Ar ⁵ , Ar ⁶ and Ar ⁷ each independently represent an aryl group or a monovalent group. Ar ^{1 to} Ar ⁷ may have a substituent, and x and y each independently represent 0 or 1, and 0 ≦ x + y ≦ 1. The conjugated polymer containing an aromatic ring in the main chain is a polymer compound having a repeating unit represented by the following formula (2a) and a repeating unit represented by the following formula (3a). Composition.

(In the formula, R ^* represents a hydrogen atom, a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, or an aryl group optionally substituted with a halogen atom. R ^** represents a hydrogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, an alkylthio group optionally substituted with a halogen atom, or a halogen atom. Aryl group which may be substituted, aryloxy group which may be substituted with halogen atom, arylthio group which may be substituted with halogen atom, arylalkyl group which may be substituted with halogen atom, substituted with halogen atom Arylalkyloxy group which may be substituted, arylalkylthio which may be substituted with halogen atom , Which may be substituted with a halogen atom arylalkenyl group, a halogen atom which may be substituted arylalkynyl group, substituted 1 may be monovalent heterocyclic group, or a halogen atom with a halogen atom .R ^{* ***} represents an alkyl group which may be substituted with a halogen atom, and a plurality of R ^* and R ^** may be the same or different.   The composition according to claim 5, wherein the non-conjugated polymer is polyvinyl carbazole or a derivative thereof.   Furthermore, the composition as described in any one of Claims 1-10 containing at least 1 sort (s) chosen from the group which consists of a low molecular hole transport material, a low molecular electron transport material, and a luminescent material.   Furthermore, the liquid composition which consists of a composition of Claims 1-11 containing a solvent.   The liquid composition according to claim 12, which has a viscosity at 25 ° C of 0.5 to 500 mPa · s.   The thin film formed using the composition as described in any one of Claims 1-11.   The organic transistor which uses the composition as described in any one of Claims 1-11.   The element formed using the composition as described in any one of Claims 1-11.   A light emitting device comprising the device according to claim 16.   A planar light source comprising the light emitting device according to claim 17.   A display device comprising the light emitting device according to claim 17.   The illumination provided with the light emitting element of Claim 17.