JP2010222383A - Aromatic compound, and electronic element using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound useful for manufacturing an organic electro-luminescence element excellent in brightness and light-emission efficiency. <P>SOLUTION: The aromatic compound includes three or more of the repetition units represented by formula (1) and one or more of the repetition unit represented by formula (2) and/or the repetition unit represented by formula (3) and does not includes a carbon-carbon triple bond, wherein Ar<SP>1</SP>is a (2+n) valent aromatic heterocyclic group, and M is a hydrogen atom, a metal atom, a metal ion or an ammonium ion. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an aromatic compound and an electronic device using the same.

で表される化合物の残基を側鎖に導入した高分子化合物が提案されている（特許文献１）。 In the field of electronic devices such as organic electroluminescent devices, electron injection materials are usually used to lower the barrier for electron injection from the cathode. As an electron injection material, the following formula:

A polymer compound in which a residue of a compound represented by the formula is introduced into a side chain has been proposed (Patent Document 1).

JP 2000-254514 A

However, an organic electroluminescence device using this polymer compound has a problem that luminance and luminous efficiency are low.
Then, an object of this invention is to provide a compound useful for manufacture of the organic electroluminescent element excellent in the brightness | luminance and luminous efficiency.

  As a result of intensive studies, the present inventors solved the above problem by using an aromatic compound having a specific substituent as an aromatic heterocyclic group in combination with the second repeating unit. As a result, the present invention has been completed.

（式中、Ａｒ¹は置換基を有していてもよい（２＋ｎ）価の芳香族複素環基である。Ｍは、水素原子、金属原子、金属イオン、アンモニウムイオン、１〜４個の炭化水素基で置換されたアンモニウムイオン、置換基を有してもよいベンジル基、又は置換基を有してもよい２個の炭化水素基で置換されたボリル基を表す。ｎは１以上の整数である。Ａｒ²、Ａｒ³及びＡｒ⁴は、同一又は異なり、直接結合、置換基を有していてもよい２価の芳香族炭化水素基、又は置換基を有していてもよい２価の芳香族複素環基を表す。Ｘは置換基を有していてもよいエテニレン基、又は置換基を有していてもよいイミノ基を表す。ｍは０〜２の整数である。但し、ｍが０である場合、Ａｒ²は直接結合ではない。Ｒは置換基を有していてもよい炭化水素基を表す。） In the present invention, firstly, three or more repeating units represented by the following formula (1), one repeating unit represented by the following formula (2) and / or one repeating unit represented by the following formula (3). The aromatic compound which contains the above and does not contain a carbon-carbon triple bond is provided.

(In the formula, Ar ¹ is a (2 + n) -valent aromatic heterocyclic group which may have a substituent. M is a hydrogen atom, a metal atom, a metal ion, an ammonium ion, or 1 to 4 carbon atoms. An ammonium ion substituted with a hydrogen group, a benzyl group which may have a substituent, or a boryl group substituted with two hydrocarbon groups which may have a substituent, where n is an integer of 1 or more Ar ² , Ar ³ and Ar ⁴ are the same or different and are a direct bond, a divalent aromatic hydrocarbon group which may have a substituent, or a divalent which may have a substituent. X represents an optionally substituted ethenylene group or an optionally substituted imino group, m is an integer of 0 to 2, provided that when m is 0, the Ar ² is directly not bind .R may have a substituent hydrocarbon group I am.)

  Secondly, the present invention provides a composition containing the aromatic compound.

  Thirdly, the present invention provides an electronic device using the aromatic compound.

  If the aromatic compound of this invention is applied, the organic electroluminescent element excellent in the brightness | luminance and luminous efficiency will be obtained. In addition, the aromatic compound of the present invention is useful as a material that can be used by a coating method in applications such as organic electroluminescence elements, organic transistors, and solar cells.

  The present invention will be described below.

<Aromatic compounds>
The aromatic compound of the present invention comprises 3 or more repeating units represented by the formula (1), a repeating unit represented by the formula (2) and / or a repeating unit 1 represented by the formula (3). An aromatic compound containing no carbon-carbon triple bond, preferably a repeating unit represented by the formula (1), a repeating unit represented by the formula (2), and the formula (3) ) Is an aromatic compound that is 60% or more (particularly 80 to 100%, especially 100%) of the total number of moles of all repeating units, and more preferably the above formula. The repeating unit represented by (1), the repeating unit represented by the formula (2) and / or the repeating unit represented by the formula (3) are contained in the main chain, and the formula ( 1) a repeating unit represented by the formula (2) An aromatic compound in which the total number of moles of the repeating unit represented by formula (3) is 60% or more (particularly 80 to 100%, especially 100%) of the total number of moles of all the repeating units. is there.

-Repeating unit represented by formula (1) In the above formula (1), the (2 + n) -valent aromatic heterocyclic group represented by Ar ¹ means (2 + n) hydrogen atoms from the aromatic heterocyclic ring. It means the remaining atomic group removed. Aromatic heterocycles include pyridine ring, 1,2-diazine ring, 1,3-diazine ring, 1,4-diazine ring, 1,3,5-triazine ring, furan ring, pyrrole ring, pyrazole ring, imidazole Monocyclic heterocycles such as rings, oxazole rings, oxadiazol rings, azadiazazole rings, thiophene rings and thiazole rings; condensed polycyclic heterocycles in which two or more rings selected from monocyclic aromatic rings are condensed A bridged polycyclic aromatic ring having a structure in which two heterocycles or one heterocycle and one aromatic ring are bridged by a divalent group such as a methylene group, an ethylene group or a carbonyl group Etc. The (2 + n) -valent aromatic heterocyclic group is preferably a group having 10 to 14 members.

Examples of the monocyclic heterocycle include rings represented by the following formulas 1-14.

Examples of the condensed polycyclic heterocycle include rings represented by the following formulas 15 to 31.

Examples of the bridged polycyclic heterocycle include rings represented by the following formulas 32-36.

  The aromatic heterocycle is preferably a ring represented by the above formulas 1 to 19 or 27 to 31 and more preferably a ring represented by the above formulas 15 or 27 from the viewpoint of ease of synthesis of the raw material monomer. Moreover, as an aromatic heterocyclic ring, from the viewpoint of the interaction strength with the group represented by M and an atom, the ring containing the imine nitrogen atom (the above formulas 1-5, 8-10, 12-19, 27 ~ 31, 36) are preferred.

  In the formula (1), the metal atom represented by M includes Li, Na, K, Cs, Be, Mg, Ca, Ba, Ag, Al, Bi, Cu, Fe, Ga, Mn, Pb, Sn , Ti, V, W, Y, Yb, Zn, Zr, preferably Li, Na, K, Cs, Al, more preferably Li, Na, Cs, Al, particularly preferably Li, Cs and Al.

In the formula (1), the (2 + n) -valent aromatic heterocyclic group represented by Ar ¹ may have a substituent. Examples of the substituent include a hydroxyl group, an aldehyde group, an amino group, a cyano group, a nitro group, a halogen atom, a hydrocarbon group that may have a substituent, a hydrocarbon oxy group that may have a substituent, A hydrocarbon carbonyl group which may have a substituent, a hydrocarbon oxycarbonyl group which may have a substituent, a hydrocarbon carbonyloxy group which may have a substituent, and a substituent. An optionally substituted sulfo group, an optionally substituted hydrocarbon azo group, an optionally substituted amino group substituted with one or two hydrocarbon groups, and a substituted group; An amide group substituted with one or two hydrocarbon groups which may be present, and an aromatic heterocyclic group optionally having a substituent, preferably a hydrocarbon group, a hydrocarbon oxy group, Aromatic heterocyclic group, more preferably hydrocarbon Group, a hydrocarbon oxy group, more preferably a hydrocarbon group. The same applies to “optionally substituted” and “having a substituent” in the present specification.

  Examples of the halogen atom that can be a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a fluorine atom, a chlorine atom, and a bromine atom, more preferably a fluorine atom and a chlorine atom, Particularly preferred is a fluorine atom.

  Examples of the hydrocarbon group that can be a substituent include an alkyl group, an aryl group, and an arylalkyl group.

  The alkyl group may be linear, branched or cyclic. As the alkyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group Decyl group, undecyl group, dodecyl group and the like. Carbon number of an alkyl group is 1-50 normally, Preferably it is 1-30, More preferably, it is 1-20, More preferably, it is 1-10.

An aryl group is a remaining atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and has a condensed ring or two or more independent benzene rings or condensed rings bonded directly or via a vinylene group. Including things. Carbon number of an aryl group is 6-60 normally, Preferably it is 6-48. Examples of the aryl group include a phenyl group, C ₁ -C ₁₂ alkylphenyl group ( "C ₁ -C ₁₂ alkyl", carbon atoms in the alkyl moiety is meant to be 1-12. Hereinafter, the same.) 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group and the like. Among the aryl groups, a phenyl group, C ₁ -C preferably ₁₂ alkylphenyl group, C ₁ -C ₆ alkyl phenyl group is more preferable.
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. Phenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, undecylphenyl group, dodecylphenyl group and the like, preferably methylphenyl group , Ethylphenyl group, dimethylphenyl group, more preferably methylphenyl group, ethylphenyl group, and still more preferably methylphenyl group.

The arylalkyl group is a group in which the alkyl group is bonded to the aryl group. Carbon number of an arylalkyl group is 7-60 normally, Preferably it is 7-30. The aryl alkyl group, 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 and the like, preferably 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, more preferably phenyl -C ₁ -C ₁₂ alkyl group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkyl group, further Preferred are a phenyl-C ₁ -C ₆ alkyl group and a C ₁ -C ₆ alkoxyphenyl-C ₁ -C ₆ alkyl group.

  A hydrocarbon oxy group, a hydrocarbon carbonyl group, a hydrocarbon oxycarbonyl group, a hydrocarbon carbonyloxy group, and a hydrocarbon azo group, which can be substituted, are an oxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, an azo group, respectively. A group formed by bonding a group and the hydrocarbon group.

  An amino group substituted with one or two hydrocarbon groups and an amide group substituted with one or two hydrocarbon groups, which can serve as substituents, are respectively hydrogen atoms constituting the amino group and the amide group. 1 or 2 of these is a group substituted with the hydrocarbon group.

  The aromatic heterocyclic group that can be a substituent is a group formed by removing one hydrogen atom from the aromatic heterocyclic ring.

  In the formula (1), M preferably has a metal atom, a metal ion, an ammonium ion, an ammonium ion substituted with 1 to 4 hydrocarbon groups, or a substituent from the viewpoint of bond strength. A boryl group substituted with two hydrocarbon groups which may be substituted, more preferably a metal atom or a metal ion, and still more preferably a metal atom.

In the formula (1), examples of the metal ion represented by M include metal ions in which the metal atom is a cation, and preferably Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , Al ³⁺ , Zn ²⁺ , more preferably Li ⁺ , Cs ⁺ , and Al ³⁺ , and particularly preferably Li ⁺ and Cs ⁺ . The valence is 1-3 valence, Preferably it is 1-2 valence, More preferably, it is monovalence. When the valence is 2 or more, it preferably has a counter ion. Counter ions include F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , OH ⁻ , ClO ⁻ , ClO ₂ ⁻ , ClO ₃ ⁻ , ClO ₄ ⁻ , BF ₄ ⁻ , PF ₆ ⁻ , 8-quinolinolato anion, 2 -Methyl-8-quinolinolato anion and 2-phenyl-8-quinolinolato anion are mentioned, and 8-quinolinolato anion and 2-methyl-8-quinolinolato anion are preferable.

  In the formula (1), in the ammonium ion substituted with 1 to 4 hydrocarbon groups represented by M, 1 to 4 (preferably 4) of the hydrogen atoms constituting the ammonium ion are hydrocarbon groups. Is an ion substituted with

  In the formula (1), the boryl group substituted with two hydrocarbon groups represented by M is a group in which two hydrogen atoms constituting the boryl group are substituted with hydrocarbon groups.

  In said Formula (1), n becomes like this. Preferably it is an integer of 1-3, More preferably, it is 1, 2, More preferably, it is 1.

Examples of the condensed polycyclic aromatic ring include rings represented by the following formulas 32-34.

Examples of the bridged polycyclic aromatic ring include rings represented by the following formulas 35 to 39.

  The divalent aromatic hydrocarbon group is preferably a benzene ring or a ring represented by the above formulas 35 to 39 from the viewpoint of ease of synthesis of the raw material monomer, and is represented by a benzene ring or the above formulas 35 and 36. A ring is more preferred.

（式中、Ｒ’は、ヒドロキシル基、アルデヒド基、アミノ基、シアノ基、ニトロ基、ハロゲン原子、置換基を有していてもよい炭化水素基、置換基を有していてもよい炭化水素オキシ基、置換基を有していてもよい炭化水素カルボニル基、置換基を有していてもよい炭化水素オキシカルボニル基、置換基を有していてもよい炭化水素カルボニルオキシ基、置換基を有していてもよいスルホ基、置換基を有していてもよい炭化水素アゾ基、置換基を有していてもよい１個又は２個の炭化水素基で置換されたアミノ基、置換基を有していてもよい１個又は２個の炭化水素基で置換されたアミド基、又は置換基を有していてもよい１価の複素環基であるが、これらの基同士が環を形成してもよい。ｋは０〜４の整数である。Ｒ’が複数存在する場合には、複数のＲ’は同一であっても異なっていてもよい。Ｍ’は、水素原子、金属原子、金属イオン、アンモニウムイオン、１〜４個の炭化水素基で置換されたアンモニウムイオン、置換基を有してもよいベンジル基、又は置換基を有してもよい２個の炭化水素基で置換されたボリル基を表す。） The repeating unit represented by the formula (1) is preferably a repeating unit represented by the following formula (4) from the viewpoint of ease of synthesis of the aromatic compound.

(In the formula, R ′ is a hydroxyl group, an aldehyde group, an amino group, a cyano group, a nitro group, a halogen atom, a hydrocarbon group which may have a substituent, or a hydrocarbon which may have a substituent. An oxy group, a hydrocarbon carbonyl group which may have a substituent, a hydrocarbon oxycarbonyl group which may have a substituent, a hydrocarbon carbonyloxy group which may have a substituent, a substituent An optionally substituted sulfo group, an optionally substituted hydrocarbon azo group, an optionally substituted amino group substituted by one or two hydrocarbon groups, and a substituent An amide group substituted with one or two hydrocarbon groups which may have a monovalent heterocyclic group which may have a substituent. May be formed, k is an integer of 0 to 4. When a plurality of R's are present A plurality of R ′ may be the same or different, and M ′ is a hydrogen atom, a metal atom, a metal ion, an ammonium ion, an ammonium ion substituted with 1 to 4 hydrocarbon groups, or a substituent. And represents a boryl group substituted with two hydrocarbon groups which may have a substituent.

  In the formula (4), a halogen atom represented by R ′, a hydrocarbon group, a hydrocarbonoxy group, a hydrocarbon carbonyl group, a hydrocarbonoxycarbonyl group, a hydrocarbon carbonyloxy group, a hydrocarbon azo group, one or The amino group substituted with two hydrocarbon groups, the amide group substituted with one or two hydrocarbon groups, and the monovalent aromatic heterocyclic group are the same as those explained and exemplified above. is there.

  In the formula (4), R ′ is preferably a hydrocarbon group, a hydrocarbonoxy group, or an aromatic heterocyclic group, more preferably a hydrocarbon group or a hydrocarbonoxy group, and still more preferably, It is a hydrocarbon group.

  In said Formula (4), k becomes like this. Preferably it is an integer of 0-3, More preferably, it is 0 and 1, More preferably, it is 0.

  In said formula (4), it has a metal atom represented by M ′, a metal ion, an ammonium ion substituted with 1 to 4 hydrocarbon groups, a benzyl group which may have a substituent, and a substituent. The optionally substituted boryl group substituted by two hydrocarbon groups is the same as described and exemplified in the above M section.

（式中、Ｍ’は、前記と同じ意味を有する。Ｍｅは、メチル基を表す。） Examples of the repeating unit represented by the formula (4) include the following repeating units.

(In the formula, M ′ has the same meaning as described above. Me represents a methyl group.)

  In the aromatic compound of the present invention, the repeating unit represented by the formula (1) may be included alone or in combination of two or more.

-Repeating unit represented by formula (2) In the above formula (2), the divalent aromatic hydrocarbon group represented by Ar ² is the remainder of the aromatic hydrocarbon ring after removing two hydrogen atoms. It means atomic group. Examples of the aromatic hydrocarbon ring include monocyclic aromatic rings such as benzene rings; condensed polycyclic aromatic rings in which two or more monocyclic aromatic rings are condensed; monocyclic aromatic rings and condensed polycyclic aromatic rings Examples thereof include a bridged polycyclic aromatic ring in which two or more selected from the group consisting of the above groups are bridged by a divalent group such as a methylene group, an ethylene group, or a carbonyl group.

In the formula (2), the divalent aromatic heterocyclic group represented by Ar ² is a group formed by removing two hydrogen atoms from the aromatic heterocyclic ring.

  In the formula (2), the imino group represented by X means a bifunctional group having a C═N structure. The imino group is preferably a —CH═N— group.

  In the formula (2), X is preferably an optionally substituted ethenylene group, and more preferably an unsubstituted ethenylene group.

In the formula (2), m is preferably 0 or 2, more preferably 0. However, when m is 0, Ar ² is not a direct bond.

The divalent aromatic hydrocarbon group represented by Ar ² in the formula (2) and the divalent aromatic heterocyclic group include, as a substituent, groups and atoms exemplified as the substituent, -COOM (wherein M has the same meaning as described above) may be included.

（式中、Ａｒ⁵は置換基を有していてもよい２価の芳香族炭化水素基、又は置換基を有していてもよい２価の芳香族複素環基を表す。） The repeating unit represented by the formula (2) is preferably a repeating unit represented by the following formula (2 ′) from the viewpoint of ease of synthesis of the aromatic compound.

(In the formula, Ar ⁵ represents a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent.)

In the formula (2 ′), the divalent aromatic hydrocarbon group represented by Ar ⁵ and the divalent aromatic heterocyclic group are the divalent aromatic hydrocarbon groups described and exemplified in the section for Ar ^2. The same as the divalent aromatic heterocyclic group.

In the formula (2 ′), the substituent that Ar ⁵ may have is the same as the substituent that Ar ¹ may have.

（式中、Ｍは前記と同じ意味を有する。Ｍｅはメチル基を表す。） Examples of the repeating unit represented by the formula (2 ′) include the following repeating units.

(In the formula, M has the same meaning as described above. Me represents a methyl group.)

  In the aromatic compound of the present invention, the repeating unit represented by the formula (2) may be included alone or in combination of two or more.

-Repeating unit represented by formula (3) In the above formula (3), the divalent aromatic hydrocarbon group represented by Ar ³ and Ar ⁴ is a term of Ar ² . This is the same as the divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group described and exemplified in the above.

  In the formula (3), the hydrocarbon group represented by R is the same as described and exemplified as the hydrocarbon group.

The divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group represented by Ar ³ and Ar ⁴ in the formula (3) are the groups and atoms exemplified as the substituent. In addition, -COOM (wherein M has the same meaning as described above) may be included.

（式中、Ａｒ⁶は、直接結合、置換基を有していてもよい２価の芳香族炭化水素基、又は置換基を有していてもよい２価の芳香族複素環基を表す。Ｒ’’及びＲ’’’は、同一又は異なり、置換基を有していてもよい炭化水素基を表す。複数存在するＲ’’’は、同一であっても異なっていてもよい。） The repeating unit represented by the formula (3) is preferably a repeating unit represented by the following formula (3 ′) from the viewpoint of ease of synthesis of the aromatic compound.

(In the formula, Ar ⁶ represents a direct bond, a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent. R ″ and R ′ ″ are the same or different and each represents a hydrocarbon group which may have a substituent. A plurality of R ′ ″ may be the same or different.)

In the formula (3 ′), the divalent aromatic hydrocarbon group represented by Ar ⁶ and the divalent aromatic heterocyclic group are the divalent aromatic hydrocarbon groups explained and exemplified in the section of Ar ^2. The same as the divalent aromatic heterocyclic group.

  In the formula (3 ′), the hydrocarbon groups represented by R ″ and R ″ ″ are the same as those described and exemplified as the hydrocarbon group.

（式中、Ｍｅはメチル基を表す。） Examples of the repeating unit represented by the formula (3 ′) include the following repeating units.

(In the formula, Me represents a methyl group.)

  In the aromatic compound of the present invention, the repeating unit represented by the formula (3) may be included alone or in combination of two or more.

The weight average molecular weight of - General aromatic compound of the present invention is usually ^{3 × 10 3 ~1 × 10 8} , preferably ^{5 × 10 3 ~1 × 10 7} , is 5 × 10 ³ ~1 × 10 ⁶ More preferred. The weight average molecular weight can be determined by gel permeation chromatography (GPC) or light scattering method.

  The aromatic compound of the present invention may have the repeating unit represented by the formulas (1) to (3) in any of the main chain, side chain, and terminal of the polymer. From the viewpoint of ease of synthesis, it is preferable to have the polymer main chain. The polymer main chain means the longest chain in the aromatic compound of the present invention.

  In the aromatic compound of the present invention, the total of the repeating unit represented by the formula (2) and the repeating unit represented by the formula (3) with respect to 1 mol of the repeating unit represented by the formula (1). Is usually 1 to 1000 mol, preferably 3 to 1000 mol, more preferably 10 to 100 mol.

  Moreover, the aromatic compound of this invention may contain repeating units other than said Formula (1)-(3) in the range which does not impair the effect of this invention.

Examples of the aromatic compound of the present invention include aromatic compounds composed of combinations of repeating units represented by the following formulas.

  When the aromatic compound of the present invention is used as an electron injection layer of an organic electroluminescence device, an organic electroluminescence device excellent in luminance and luminous efficiency can be obtained.

（式中、Ａｒ¹、Ａｒ²、Ａｒ³、Ａｒ⁴、Ｍ、Ｘ、Ｒ、ｎ及びｍは、前記と同じ意味を有する。Ｙ¹、Ｙ²、Ｙ³、Ｙ⁴、Ｙ⁵及びＹ⁶はそれぞれ独立に、縮合重合に関与する基を表す。） -Manufacturing method Next, the manufacturing method of the aromatic compound of this invention is demonstrated.
The aromatic compound of the present invention requires, for example, a compound represented by the following formula (1a), a compound represented by the following formula (2a) and / or a compound represented by the following formula (3a). Accordingly, it can be synthesized by dissolving or dispersing in an organic solvent and performing condensation polymerization in the presence of an alkali and / or an appropriate catalyst. In addition, when using an organic solvent, it is preferable that reaction temperature shall be more than melting | fusing point and below boiling point of the organic solvent.

(In the formula, Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , M, X, R, n and m have the same meaning as described above. Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ each independently represents a group involved in condensation polymerization.)

Examples of groups involved in condensation polymerization include halogen atoms, boric acid ester residues, -B (OH) ₂ groups, phosphonium methyl groups, phosphonic acid ester methyl groups, aldehyde groups, monohalogenated methyl groups, alkyltin groups, and the like. It is done.

  Examples of the halogen atom that can be a group involved in the condensation polymerization include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the boric acid ester residue that can be a group involved in condensation polymerization include groups represented by the following formulae.

Examples of the phosphonium salt methyl group that can be a group involved in condensation polymerization include —CH ₂ Ph ₃ PCl (where Ph represents a phenyl group, the same shall apply hereinafter), —CH ₂ Ph ₃ PBr, CH _2. Ph ₃ PI and the like can be mentioned.

Examples of the phosphonate methyl group that can be a group involved in condensation polymerization include groups represented by the following formulae.

  Examples of the halogenated methyl group that can be a group involved in condensation polymerization include a methyl chloride group, a methyl bromide group, and a methyl iodide group.

  Examples of the alkyltin group that can be a group involved in condensation polymerization include a trimethyltin group, a triethyltin group, a tripropyltin group, and a tri (n-butyl) tin group.

  As a method of condensation polymerization, “Organic Reactions”, Vol. 14, pp. 270-490, John Wiley & Sons, Inc., 1965, “Organic Synthesis” Collective Volume VI, 407-411, John Wiley & Sons, Inc., 1988, Chemical Review (Chem. Rev.), 95, 2457 (1995). , Journal of Organometallic Chemistry (J. Organomet. Chem.), 576, 147 (1999), Macromolecular Chemistry. A publicly known method described in, for example, a macro-molecular symposium (Macromol. Chem., Macromol. Symp.), Vol. 12, page 229 (1987) may be employed.

  The organic solvent varies depending on the compound used and the reaction, but it is preferable to use an organic solvent that has been sufficiently deoxygenated to suppress side reactions. The reaction is preferably allowed to proceed under an inert atmosphere using an organic solvent.

  Organic solvents include saturated hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane, unsaturated hydrocarbons such as benzene, toluene, ethylbenzene and xylene, carbon tetrachloride, chloroform, dichloromethane, chlorobutane, bromobutane, chloropentane and bromo. Halogenated saturated hydrocarbons such as pentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane, halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene, methanol, ethanol, propanol, isopropanol, butanol, t-butyl Alcohols such as alcohol, carboxylic acids such as formic acid, acetic acid and propionic acid, dimethyl ether, diethyl ether, methyl-t-butyl ether, tetrahydro , Ethers such as tetrahydropyran and dioxane, amines such as trimethylamine, triethylamine, N, N, N ′, N′-tetramethylethylenediamine and pyridine, N, N-dimethylformamide, N, N-dimethylacetamide, N , N-diethylacetamide, amides such as N-methylmorpholine oxide, and the like. These organic solvents may be used alone or in combination of two or more.

As the alkali and catalyst, those which are sufficiently dissolved in the solvent used in the reaction are preferable.
Examples of the alkali include sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, cesium hydroxide, thallium hydroxide, triethylamine, potassium phosphate, sodium ethoxide, tetraethylammonium hydroxy Do.

  Examples of the catalyst include tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium, palladium acetate, and palladium black.

  In addition, alkali or catalyst is dissolved in an organic solvent to prepare a solution, and the solution is slowly added to the reaction solution while stirring the reaction solution in an inert atmosphere such as argon or nitrogen. Conversely, the reaction solution may be slowly added to the solution.

<Composition>
The aromatic compound of the present invention may be used as it is, but may be used as a composition in combination with other components. Examples of other components include a light emitting material, a hole transport material, and an electron transport material, which will be described later. Each of these components may be used alone or in combination of two or more. Moreover, the composition of this invention is good also as a state of a solution by containing the organic solvent.

<Electronic element>
The electronic device of the present invention includes the aromatic compound of the present invention. Hereinafter, a light-emitting element which is a typical electronic element will be described as an example.

  A light-emitting device using the aromatic compound of the present invention (hereinafter referred to as “the light-emitting device of the present invention”) includes an electrode composed of an anode and a cathode, and the aromatic compound of the present invention provided between the electrodes. An organic layer. The light emitting device of the present invention may further include a substrate, a hole injection layer, an electron injection layer, a hole transport layer, an electron transport layer, an interlayer layer, a light emitting layer, and the like.

  The organic layer is preferably at least one layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and an interlayer layer, and the organic layer is More preferably, it is a light emitting layer.

  The light emitting layer means a layer having a function of emitting light. The hole transport layer means a layer having a function of transporting holes. The electron transport layer means a layer having a function of transporting electrons. The interlayer layer is adjacent to the light emitting layer between the light emitting layer and the anode, and is a layer having a role of separating the light emitting layer and the anode or the light emitting layer from the hole injection layer or the hole transport layer. That is. The electron transport layer and the hole transport layer are collectively referred to as a charge transport layer. The electron injection layer and the hole injection layer are collectively referred to as a charge injection layer. Each of the light emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer, and the interlayer layer may be composed of only one layer or two or more layers.

  When the organic layer is a light emitting layer, the light emitting layer further comprises at least one selected from the group consisting of a hole transport material, an electron transport material, a light emitting material, and an additive that increases the luminance half life of the light emitting element. May be included. Here, the light emitting material means a material exhibiting fluorescence and / or phosphorescence (however, excluding the aromatic compound of the present invention). As the hole transport material, the electron transport material, and the light emitting material, known low molecular weight compounds, triplet light emitting complexes, and high molecular weight compounds can be used.

  Examples of the high molecular weight compound include polymers and copolymers having a fluorenediyl group as a repeating unit (hereinafter referred to as “(co) polymer”), (co) polymers having an arylene group as a repeating unit, Examples thereof include (co) polymers having an arylene vinylene group as a repeating unit, and (co) polymers having a divalent aromatic amine group as a repeating unit.

  Examples of the low molecular weight compounds include naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, polymethine series, xanthene series, coumarin series, cyanine series pigments, 8-hydroxyquinoline and derivative metal complexes, aromatic Examples include amines, tetraphenylcyclopentadiene and derivatives thereof, and tetraphenylbutadiene and derivatives thereof.

Examples of the triplet light-emitting complex include Ir (ppy) ₃ , Btp ₂ Ir (acac) having iridium as a central metal, ADS066GE (trade name) commercially available from American Dye Source, Inc., platinum PtOEP having a central metal and Eu (TTA) ₃ phen having europium as a central metal.

  Examples of the additive include bipyridyl such as 2,2′-bipyridyl, 3,3′-bipyridyl, 4,4′-bipyridyl, 4-methyl-2,2′-bipyridyl, 5-methyl-2,2′- Bipyridyl derivatives such as bipyridyl and 5,5′-dimethyl-2,2′-bipyridyl are exemplified.

  The film thickness of the light-emitting layer varies depending on the material used, and may be selected so that the driving voltage and the light emission efficiency are appropriate. Usually, the film thickness is 1 nm to 1 μm, preferably 2 nm to 500 nm. More preferably, it is 5 nm-200 nm, More preferably, it is 50 nm-150 nm.

  Examples of the method for forming the light emitting layer include a method of forming a film from a solution. For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

  The light-emitting device of the present invention includes a device in which a light-emitting layer is provided between the anode and the cathode, a light-emitting device in which an electron transport layer is provided between the cathode and the light-emitting layer, and hole transport between the anode and the light-emitting layer. And a light emitting device in which an electron transport layer is provided between the cathode and the light emitting layer and a hole transport layer is provided between the anode and the light emitting layer.

Examples of the structure of such a light emitting device include the following structures a) to d).
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.)

For each of these structures, an interlayer layer may be provided adjacent to the light emitting layer between the light emitting layer and the anode. Examples of the structure of such a light emitting device include the following structures a ′) to d ′).
a ′) Anode / interlayer layer / light emitting layer / cathode b ′) Anode / hole transport layer / interlayer layer / light emitting layer / cathode c ′) Anode / interlayer layer / light emitting layer / electron transport layer / cathode d ′ ) Anode / hole transport layer / interlayer layer / light emitting layer / electron transport layer / cathode

  When the light-emitting element of the present invention has a hole transport layer, the hole transport layer usually contains the hole transport material (a high molecular weight compound, a low molecular weight compound). Examples of the hole transport material include polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having aromatic amines in the side chain or main chain, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyaniline And derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, and the like.

  Among these, high molecular weight compounds include polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having an aromatic amine compound group in the side chain or main chain, polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (P-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, etc. are preferred, polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, poly having aromatic amine in the side chain or main chain Siloxane derivatives are more preferred.

  Among these, examples of the low molecular weight compound include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, and triphenyldiamine derivatives. These low molecular weight compounds are preferably used by being dispersed in a polymer binder.

  The polymer binder is preferably one that does not extremely inhibit charge transport and does not strongly absorb visible light. Examples of the polymer binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, Examples include polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, and polysiloxane.

  Polyvinylcarbazole and derivatives thereof are obtained, for example, from a vinyl monomer by cation polymerization or radical polymerization.

  Examples of the polysilane and derivatives thereof include compounds described in Chem. Rev. 89, 1359 (1989) and GB 2300196 published specification. As the synthesis method, the methods described in these can be used, but the Kipping method is particularly preferably used.

  Since the polysiloxane and derivatives thereof have almost no hole transporting property in the siloxane skeleton structure, those having the structure of the low molecular weight hole transporting material in the side chain or main chain are preferable, and the hole transporting aromatic group is preferable. What has an amine in a side chain or a principal chain is more preferable.

  As a film formation method of the hole transport layer, when a low molecular weight compound is used, a method by film formation from a mixed solution with a polymer binder is exemplified, and when a high molecular weight compound is used, a solution is formed. The method by film formation from is illustrated.

  As a solvent used for film formation from a solution, a solvent capable of dissolving or uniformly dispersing the hole transport material is 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 the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether , Propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, polyhydric alcohols such as 1,2-hexanediol and derivatives thereof, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples thereof include sulfoxide solvents such as sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

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

  When the light-emitting device of the present invention has an electron transport layer, the electron transport layer usually contains the electron transport material (a high molecular weight compound, a low molecular weight compound). As the electron transport material, known materials can be used, such as oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and Examples thereof include 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, and polyfluorene and derivatives thereof.

  As a method for forming the electron transport layer, when a low molecular weight compound is used, a vacuum deposition method from powder or a method by film formation from a solution or a molten state is exemplified, and when a high molecular weight compound is used. Examples of the method include film formation from a solution or a molten state. In the method of film formation from a solution or a molten state, the polymer binder may be used in combination.

  The solvent used for film formation from a solution is preferably a solvent capable of dissolving or uniformly dispersing the electron transport material and / or the polymer binder. 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 the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether , Propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, polyhydric alcohols such as 1,2-hexanediol and derivatives thereof, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples thereof include sulfoxide solvents such as sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution or molten state, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing Coating methods such as a method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

  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 appropriate values. If it is thick, the driving 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 to 500 nm.

  The hole injection layer and the electron injection layer have the function of improving the charge injection efficiency from the electrode among the charge transport layers provided adjacent to the electrode, and have the effect of lowering the driving voltage of the light emitting device. is there.

  In order to improve adhesion to the electrode and charge injection from the electrode, the charge injection layer or insulating layer adjacent to the electrode (usually 0.5 to 4.0 nm in average film thickness, hereinafter the same) 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 the adhesion at the interface or prevent mixing.

  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, as a light emitting device provided with a charge injection layer (electron injection layer, hole injection layer), a light emitting device provided with a charge injection layer adjacent to the cathode, and a charge injection layer provided adjacent to the anode. A light emitting element is mentioned. Examples of the structure of such a light emitting device include the following structures e) to p).
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 / electron 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 / electron 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

  For each of these structures, a structure in which an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. In this case, the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.

  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 electric conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ to 1 × 10 ³ S / cm.

  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 and tetrabutylammonium ion.

  The material used for the charge injection layer may be appropriately selected in relation to the electrode and the material of the adjacent layer. Polyaniline and its derivatives, polythiophene and its derivatives, polypyrrole and its derivatives, polyphenylene vinylene and its derivatives, polythienylene Examples include vinylene and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain, metal phthalocyanines (such as copper phthalocyanine), and carbon. .

  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 the 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.

Examples of the structure of such a light emitting element 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 For each of the structures, a structure in which an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. In this case, the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.

  Regarding the structure in which the interlayer layer is applied to the structures a) to ab), the interlayer layer is provided between the anode and the light emitting layer, and the anode, the hole injection layer or the hole transport layer, and the light emitting layer. It is preferable that it is comprised with the material which has an ionization potential intermediate | middle with the aromatic compound which comprises.

  Examples of materials used for the interlayer layer include aromatic compounds containing aromatic amines such as polyvinyl carbazole and derivatives thereof, polyarylene derivatives having aromatic amines in the side chain or main chain, arylamine derivatives, and triphenyldiamine derivatives. The

  As a method for forming the interlayer layer, when a high molecular weight material is used, a method of forming a film from a solution can be used.

  As a solvent used for film formation from a solution, a solvent capable of dissolving or uniformly dispersing a material used for an interlayer layer is 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 the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether , Propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, polyhydric alcohols such as 1,2-hexanediol and derivatives thereof, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples include sulfoxide solvents such as sulfoxide and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

  The film thickness of the interlayer layer varies depending on the material used, and may be selected so that the driving voltage and the light emission efficiency are appropriate values, and is usually 1 nm to 1 μm, preferably 2 to 500 nm.

  When the interlayer is provided adjacent to the light-emitting layer, particularly when both layers are formed by a coating method, the two layers of materials may be mixed to adversely affect the characteristics of the device. . When the light emitting layer is formed by the coating method after the interlayer layer is formed by the coating method, as a method for reducing the mixing of the two layers of materials, the interlayer layer is formed by the coating method, and the interlayer layer is heated. A method of forming a light emitting layer after insolubilizing in an organic solvent used for preparing the light emitting layer is mentioned. The heating temperature is usually 150 to 300 ° C. The heating time is usually 1 minute to 1 hour.

  The substrate on which the light emitting element of the present invention is formed may be any substrate that does not change when an electrode is formed and an organic layer is formed, and examples thereof include materials made of materials such as glass, plastic, polymer film, and silicon. The In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent.

  At least one of the anode and the cathode included in the light emitting device of the present invention is usually transparent or translucent, but the anode side is preferably transparent or translucent.

  Examples of the material of the anode include a conductive metal oxide film, a translucent metal thin film, and the like. Specifically, indium oxide, zinc oxide, tin oxide, and a composite thereof such as indium / tin / A film (NESA or the like) manufactured using a conductive compound made of oxide (ITO), indium / zinc / oxide, or the like, gold, platinum, silver, copper, or the like is used.

  Examples of a method for producing the anode include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method. As the anode, an organic transparent conductive film such as polyaniline and a derivative thereof, polythiophene and a derivative thereof may be used. The anode may have a laminated structure of two or more layers.

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

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

  The material of the cathode is preferably a material having a low work function, lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium. , Europium, terbium, ytterbium, etc., or two or more alloys thereof, or one or more of them, and among gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin One or more alloys, graphite, graphite intercalation compounds, and the like 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 cathode may have a laminated structure of two or more layers.

  The film thickness of the cathode may be appropriately adjusted in consideration of electric conductivity and durability, and is usually 10 nm to 10 μm, preferably 20 nm to 1 μm.

  As a method for manufacturing 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. Further, a layer made of a conductive polymer, or a metal oxide, a metal fluoride, an organic insulating material, or the like between the cathode and the organic layer (that is, any layer containing the aromatic compound of the present invention). A layer may be provided, and a protective layer for protecting the light-emitting element may be attached after the cathode is manufactured.

  A display device can be manufactured using the light-emitting element of the present invention. The display device includes a light emitting element as a pixel unit. The arrangement in units of pixels can be an arrangement normally employed in a display device such as a television, and can be an aspect in which a large number of pixels are arranged on a common substrate. In the display device, the pixels arranged on the substrate may be formed in a pixel region defined by the bank.

  The aromatic compound of the present invention can be used for any of a hole injection layer, a hole transport layer, an interlayer layer, a light emitting layer, an electron transport layer, and an electron injection layer, but a light emitting layer, an electron transport layer, and an electron injection layer. It is preferably used for the electron injecting layer.

  The aromatic compound of the present invention is useful not only for light emitting devices (organic electroluminescence devices) but also for organic transistors and solar cells.

  Examples are given below to illustrate the present invention in more detail.

<Synthesis Example 1> (Synthesis of 5,7-dibromo-8-benzyloxyquinoline)
Under an argon atmosphere, 5 g of 5,7-dibromo-8-quinolinol, 2.28 g of potassium carbonate, and 0.27 g of potassium iodide were charged into a 300 ml four-necked flask and dissolved by adding 85 ml of acetone. To the obtained solution, 15 ml of an acetone solution of 2.3 g of benzyl chloride was added dropwise and then heated to 65 ° C. 40 ml of acetone was added to the resulting reaction solution and refluxed for 10 hours. The obtained reaction solution was cooled to room temperature and poured into water at 0 ° C. to obtain a yellow solid. This yellow solid was washed with water and recrystallized from ethanol to obtain 5.4 g of 5,7-dibromo-8-benzyloxyquinoline.
¹ H-NMR (300 MHz / CDCl ₃ ):
δ (ppm) = 7.37 [q, 1H], 7.55 [1, 1H], 7.62 [d, 1H], 7.99 [s, 1H], 8.49 [d, 1H], 8.99 [d, 1H]

（式中、Ｅｔはエチル基、Ｂｎはベンジル基を表す。）
で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物１」と言う。）を１．８ｇ得た。芳香族化合物１のポリスチレン換算の数平均分子量は４３０００であり、ポリスチレン換算の重量平均分子量は１１００００であった。なお、これらの分子量は、テトラヒドロフランを溶媒として、ゲルパーミエーションクロマトグラフィ（ＧＰＣ）により求めた。 <Example 1> (Synthesis of aromatic compound 1)
In a flask under an argon atmosphere, 393 mg of 5,7-dibromo-8-benzyloxyquinoline, 820 mg of 2,7-dibromo-9,9-bis (4′-hexyloxy-3-ethoxycarbonylphenyl) -fluorene, 2, 7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,9-bis (4′-hexyloxy-3-ethoxycarbonylphenyl) -fluorene 1830 mg, Methyl trioctyl ammonium chloride (trade name: Aliquat 336, manufactured by Aldrich) (hereinafter referred to as “Aliquat 336”) 81 mg, tetrakis triphenylphosphine palladium 116 mg, and toluene 40 ml were mixed, and 2 M Na ₂ CO was added to the resulting solution. ₃ Aqueous solution (20 ml) was added dropwise at 100 ° C Refluxed with heating for 10 hours. Then, after cooling the obtained reaction solution to room temperature, when this reaction solution was dripped at 300 ml of methanol and stirred for 1 hour, solid precipitated. The solid is filtered and dried to give the following formula:

(In the formula, Et represents an ethyl group, and Bn represents a benzyl group.)
As a result, 1.8 g of an aromatic compound (hereinafter referred to as “aromatic compound 1”) having a ratio of 1: 3 (molar ratio; theoretical value from charged raw materials) in order was obtained. The aromatic compound 1 had a polystyrene-equivalent number average molecular weight of 43,000 and a polystyrene-equivalent weight average molecular weight of 110,000. These molecular weights were determined by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent.

（式中、Ｅｔはエチル基を表す。）
で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物２」と言う。）を４２５ｍｇ得た。 <Example 2> (Synthesis of aromatic compound 2)
Aromatic compound 1 (500 mg) was charged into a flask under an argon atmosphere and dissolved in 7 ml of tetrahydrofuran and 1 ml of ethanol. To the obtained solution, 250 mg of palladium / carbon (Pd 10%) and 0.21 ml of 1,4-cyclohexadiene were added and stirred while heating at 55 ° C. for 6 hours. To the resulting reaction solution, 0.21 ml of 1,4-cyclohexadiene was added and stirred while heating at 55 ° C. for 5 hours. The resulting reaction solution was cooled to room temperature and then filtered using celite. When the obtained filtrate was added dropwise to 300 ml of methanol and stirred for 1 hour, a solid was precipitated. The solid is filtered and dried to give the following formula:

(In the formula, Et represents an ethyl group.)
425 mg of an aromatic compound (hereinafter referred to as “aromatic compound 2”) having the two types of repeating units represented by the formula in the order of 1: 3 (molar ratio; theoretical value from the charged raw materials) was obtained.

で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物３」と言う。）を９７ｍｇ得た。 <Example 3> (Synthesis of aromatic compound 3)
Aromatic compound 2 (106 mg) was charged into a flask under an argon atmosphere and dissolved in 20 ml of tetrahydrofuran and 2 ml of ethanol. 3 ml of an aqueous solution of 24 mg of lithium hydroxide was added to the resulting solution, and the mixture was stirred at 55 ° C. for 1 hour. To the resulting reaction solution was added 5 ml of tetrahydrofuran, and the mixture was further stirred at 60 ° C. for 5 hours. 5 ml of methanol was added to the obtained reaction solution, and the mixture was stirred while heating at 60 ° C. for 3 hours. Thereto, 3 ml of an aqueous solution of 24 mg of lithium hydroxide was added and refluxed while heating at 65 ° C. for 2 hours. When the solvent of the obtained reaction solution was distilled off, a solid was obtained. The solid was washed with water. The solid after washing is filtered and dried to obtain the following formula:

97 mg of an aromatic compound (hereinafter referred to as “aromatic compound 3”) having the two types of repeating units represented by the formula in order at 1: 3 (molar ratio; theoretical value from the charged raw materials) was obtained.

（式中、Ｂｎはベンジル基、Ｅｔはエチル基を表す。）
で表される２種の繰り返し単位を順に１：９（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物４」と言う。）を１．４ｇ得た。芳香族化合物４のポリスチレン換算の数平均分子量は３４０００であり、ポリスチレン換算の重量平均分子量は７４０００であった。 <Example 4> (Synthesis of aromatic compound 4)
In a flask under an argon atmosphere, 98 mg of 5,7-dibromo-8-benzyloxyquinoline, 821 mg of 2,7-dibromo-9,9-bis (4′-hexyloxy-3-ethoxycarbonylphenyl) -fluorene, 2, 1143 mg of 7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,9-bis (4′-hexyloxy-3-ethoxycarbonylphenyl) -fluorene, Aliquat 336 (81 mg), tetrakistriphenylphosphine palladium 116 mg, and toluene 40 ml were mixed to prepare a solution. To this solution, 2M Na ₂ CO ₃ aqueous solution (20 ml) was added dropwise and refluxed while heating at 100 ° C. for 10 hours. After cooling the obtained reaction solution to room temperature, it was dripped at 300 ml of methanol, and when it stirred for 1 hour, solid precipitated. This solid is filtered off and dried to give the following formula:

(In the formula, Bn represents a benzyl group and Et represents an ethyl group.)
1.4 g of an aromatic compound (hereinafter referred to as “aromatic compound 4”) having two repeating units represented by the formula in the order of 1: 9 (molar ratio; theoretical value from charged raw materials) was obtained. The aromatic compound 4 had a polystyrene-equivalent number average molecular weight of 34,000 and a polystyrene-equivalent weight average molecular weight of 74,000.

（式中、Ｅｔはエチル基を表す。）
で表される２種の繰り返し単位を順に１：９（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物５」と言う。）を３４０ｍｇ得た。 <Example 5> (Synthesis of aromatic compound 5)
Aromatic compound 4 (500 mg) was charged into a flask under an argon atmosphere and dissolved in 4 ml of tetrahydrofuran and 0.5 ml of methanol. To the obtained solution, 500 mg of palladium / carbon (Pd 10%) and 0.21 ml of 1,4-cyclohexadiene were added and stirred while heating at 55 ° C. for 6 hours. To the resulting reaction solution, 0.21 ml of 1,4-cyclohexadiene was added and stirred while heating at 55 ° C. for 5 hours. The resulting reaction solution was cooled to room temperature and then filtered using celite. When the obtained filtrate was added dropwise to 300 ml of methanol and stirred for 1 hour, a solid was precipitated. This solid is filtered off and dried to give the following formula:

(In the formula, Et represents an ethyl group.)
340 mg of an aromatic compound (hereinafter referred to as “aromatic compound 5”) having the two types of repeating units represented by the formula in the order of 1: 9 (molar ratio; theoretical value from the charged raw materials) was obtained.

で表される２種の繰り返し単位を順に１：９（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物６」と言う。）を７２ｍｇ得た。 <Example 6> (Synthesis of aromatic compound 6)
Aromatic compound 5 (100 mg) was charged into a flask under an argon atmosphere and dissolved in 20 ml of tetrahydrofuran and 2 ml of ethanol. 3 ml of an aqueous solution of 24 mg of lithium hydroxide was added to the resulting solution, and the mixture was stirred at 55 ° C. for 1 hour. To the resulting reaction solution was added 5 ml of tetrahydrofuran, and the mixture was further stirred at 60 ° C. for 5 hours. Next, 5 ml of methanol was added thereto and stirred while heating at 60 ° C. for 3 hours, and then 3 ml of an aqueous solution of 24 mg of lithium hydroxide was added and refluxed with heating at 65 ° C. for 2 hours. When the solvent of the obtained reaction solution was distilled off, a solid was deposited. This solid was washed with water. The washed solid is collected by filtration and dried to obtain the following formula:

In this way, 72 mg of an aromatic compound (hereinafter referred to as “aromatic compound 6”) having two repeating units represented by the formula (1) (molar ratio; theoretical value from charged raw materials) was obtained.

で表される２種の繰り返し単位を順に１：９（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物７」と言う。）を９１ｍｇ得た。 <Example 7> (Synthesis of aromatic compound 7)
Aromatic compound 6 (100 mg) was charged into a flask under an argon atmosphere and dissolved in 20 ml of tetrahydrofuran and 2 ml of ethanol. To the obtained solution was added 3 ml of an aqueous solution of 334 mg of cesium hydroxide, and the mixture was stirred at 55 ° C. for 1 hour. To the resulting reaction solution was added 5 ml of tetrahydrofuran, and the mixture was further stirred at 60 ° C. for 5 hours. Next, 5 ml of methanol was added thereto and stirred while heating at 60 ° C. for 3 hours. Then, 3 ml of an aqueous solution of 334 mg of cesium hydroxide was added and refluxed with heating at 65 ° C. for 2 hours. When the solvent of the obtained reaction solution was distilled off, a solid was deposited. This solid was washed with water. The washed solid is collected by filtration and dried to obtain the following formula:

91 mg of an aromatic compound (hereinafter, referred to as “aromatic compound 7”) having the two types of repeating units represented by the formula in the order of 1: 9 (molar ratio; theoretical value from the charged raw materials) was obtained.

（式中、Ｂｎはベンジル基を表す。）
で表される２種の繰り返し単位を順に１：１（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物８」と言う。）を５６８ｍｇ得た。芳香族化合物８のポリスチレン換算の数平均分子量は１１０００であり、ポリスチレン換算の重量平均分子量は１９５００であった。 <Example 8> (Synthesis of aromatic compound 8)
In a flask under an argon atmosphere, 393 mg of 5,7-dibromo-8-benzyloxyquinoline, 530 mg of 9,9-dioctylfluorene-2,7-diboronic acid bis (1,2-ethanediol) ester, Aliquat 336 (40 mg), A solution was prepared by mixing 58 mg of tetrakistriphenylphosphine palladium and 10 ml of toluene. To this solution, 2M Na ₂ CO ₃ aqueous solution (10 ml) was added dropwise and refluxed while heating at 100 ° C. for 6 hours. After cooling the obtained reaction solution to room temperature, it was dripped at 300 ml of methanol, and when it stirred for 1 hour, solid precipitated. This solid is filtered off and dried to give the following formula:

(In the formula, Bn represents a benzyl group.)
As a result, 568 mg of an aromatic compound (hereinafter referred to as “aromatic compound 8”) having 1: 1 (molar ratio; theoretical value from charged raw materials) in the order of 2 types of repeating units represented by the formula (1) was obtained. The aromatic compound 8 had a polystyrene-equivalent number average molecular weight of 11,000 and a polystyrene-equivalent weight average molecular weight of 19,500.

（式中、Ｂｎはベンジル基を表す。）
で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物９」と言う。）を１．２６ｇ得た。芳香族化合物９のポリスチレン換算の数平均分子量は１７０００であり、ポリスチレン換算の重量平均分子量は３５０００であった。 <Example 9> (Synthesis of aromatic compound 9)
In a flask under an argon atmosphere, 393 mg of 5,7-dibromo-8-benzyloxyquinoline, 548 mg of 2,7-dibromo-9,9-dioctylfluorene, 548 mg of 9,9-dioctylfluorene-2,7-diboronic acid (1 , 2-ethanediol) ester 1060 mg, Aliquat 336 (40 mg), tetrakistriphenylphosphine palladium 116 mg, and toluene 40 ml were mixed to prepare a solution. To this solution, 2M Na ₂ CO ₃ aqueous solution (20 ml) was added dropwise and refluxed while heating at 100 ° C. for 9 hours. After cooling the obtained reaction solution to room temperature, it was dripped at 300 ml of methanol, and when it stirred for 1 hour, solid precipitated. This solid is filtered off and dried to give the following formula:

(In the formula, Bn represents a benzyl group.)
1.26 g of an aromatic compound (hereinafter, referred to as “aromatic compound 9”) having two types of repeating units represented by the formula in order of 1: 3 (molar ratio; theoretical value from charged raw materials) was obtained. The aromatic compound 9 had a polystyrene-equivalent number average molecular weight of 17,000 and a polystyrene-equivalent weight average molecular weight of 35,000.

で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物１０」と言う。）を４４１ｍｇ得た。 <Example 10> (Synthesis of aromatic compound 10)
Aromatic compound 9 (500 mg) was charged into a flask under an argon atmosphere and dissolved in 7 ml of tetrahydrofuran and 1 ml of ethanol. To the obtained solution were added 250 mg of palladium / carbon (Pd 10%) and 0.33 ml of 1,4-cyclohexadiene, and the mixture was refluxed with heating at 65 ° C. for 13 hours. The resulting reaction solution was cooled to room temperature and then filtered using celite. When the obtained filtrate was added dropwise to 300 ml of methanol and stirred for 1 hour, a solid was precipitated. This solid is filtered off and dried to give the following formula:

As a result, 441 mg of an aromatic compound (hereinafter referred to as “aromatic compound 10”) having two types of repeating units represented by the following formulas in the order of 1: 3 (molar ratio; theoretical value from charged raw materials) was obtained.

で表される２種の繰り返し単位を順に１：３（モル比；仕込み原料からの理論値）で有する芳香族化合物（以下、「芳香族化合物１１」と言う。）を９０ｍｇ得た。 <Example 11> (Synthesis of aromatic compound 11)
Aromatic compound 10 (100 mg) was charged into a flask under an argon atmosphere and dissolved in 20 ml of tetrahydrofuran and 2 ml of ethanol. To the resulting solution was added 3 ml of an aqueous solution of 24 mg of lithium hydroxide and stirred at room temperature for 3 and a half hours. Then, 5 ml of tetrahydrofuran was added and further stirred at room temperature for 5 and a half hours. When the solvent of the obtained reaction solution was distilled off, a solid was deposited. This solid was washed with water. The washed solid is collected by filtration and dried to obtain the following formula:

90 mg of an aromatic compound (hereinafter referred to as “aromatic compound 11”) having the two types of repeating units represented by the following formulas in the order of 1: 3 (molar ratio; theoretical value from the charged raw materials) was obtained.

<Example 12> (Preparation of electroluminescent element 1)
Poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (manufactured by HCStarck, PEDOT: PSS solution, product name) as a hole injection material solution on ITO on a glass substrate on which ITO is formed as an anode CLEVIOS (registered trademark) PVPAl 4083) 0.5 ml was applied, and a hole injection material layer was formed by spin coating so that the film thickness became 70 nm. The glass substrate with the hole injection material layer thus formed was heated in air at 200 ° C. for 10 minutes to insolubilize the hole injection layer, and then the substrate was naturally cooled to room temperature. The formed glass substrate A was obtained.

Further, 5.2 mg of a hole transport material and 1 ml of xylene were mixed to prepare a composition for a hole transport layer having a hole transport material content of 0.6% by weight. The hole transport material was synthesized by the following method.
To a 1 liter three-necked round bottom flask equipped with a reflux condenser and an overhead stirrer was added 2,7-bis (1,3,2-dioxyborol) -9,9-di (1-octyl) fluorene (3.863 g). 7.283 mmol), N, N-di (p-bromophenyl) -N- (4- (butan-2-yl) phenyl) amine (3.177 g, 6.919 mmol) and di (4-bromophenyl) Benzocyclobutanamine (156.3 mg, 0.364 mmol) was added. Subsequently, methyl trioctyl ammonium chloride (manufactured by Aldrich, trade name: Aliquat 336 (registered trademark)) (2.29 g), and then 50 mL of toluene were added. After adding PdCl ₂ (PPh ₃ ) ₂ catalyst (4.9 mg), the resulting mixture was stirred in an oil bath at 105 ° C. for 15 minutes. A sodium carbonate aqueous solution (2.0 M, 14 mL) was added thereto, and the obtained reaction product was stirred in an oil bath at 105 ° C. for 16.5 hours. Phenylboronic acid (0.5 g) was then added and the resulting reaction was stirred for 7 hours. The aqueous layer was removed and the organic layer was washed with 50 mL of water. The organic layer was returned to the reaction flask, to which 0.75 g of sodium diethyldithiocarbamate and 50 mL of water were added. The resulting reaction was stirred in an 85 ° C. oil bath for 16 hours. The aqueous layer was removed, and the organic layer was washed 3 times with 100 mL of water and then passed through a column of silica gel and basic alumina. Next, the operation of precipitating the toluene solution containing the target hole transport material in methanol is repeated twice, and the resulting precipitate is vacuum dried at 60 ° C. 2 g was obtained. The polystyrene-equivalent weight average molecular weight of the hole transport material was 124,000, and the dispersion (Mw / Mn) was 2.8.
Next, the composition for a hole transport layer was applied onto the glass substrate A on which the hole injection layer was formed by a spin coating method to form a coating film having a film thickness of 25 nm. The glass substrate on which the coating film is formed is heated at 200 ° C. for 20 minutes in a nitrogen atmosphere to insolubilize the coating film, and then naturally cooled to room temperature, thereby forming a glass substrate on which a hole transport layer is formed. B was obtained.

Next, BP361 (manufactured by Summation Co., Ltd.) (11.3 mg) as a light emitting material and 1 ml of xylene were mixed to prepare a composition for a light emitting layer in which the light emitting material was 1.3 wt%.
This composition for light emitting layer was apply | coated on the glass substrate B in which the positive hole transport layer was formed by the spin coat method, and the coating film with a film thickness of 80 nm was formed. The substrate on which this coating film was formed was heated at 130 ° C. for 15 minutes in a nitrogen atmosphere to evaporate the solvent, and then naturally cooled to room temperature to obtain a glass substrate C on which a light emitting layer was formed. .

Next, 1 ml of a solvent in which methanol and tetrahydrofuran were mixed at a volume ratio of 9: 1 and aromatic compound 3 (2 mg) were mixed to prepare a composition containing 0.2% by weight of aromatic compound 3.
This composition was applied on a glass substrate C on which a light emitting layer was formed by a spin coating method to form a coating film having a thickness of 10 nm. The glass substrate on which this coating film was formed was heated at 130 ° C. for 15 minutes in a nitrogen atmosphere to evaporate the solvent, and then naturally cooled to room temperature, whereby a layer made of the aromatic compound 3 was formed. A glass substrate D was obtained.

  The glass substrate D on which the layer made of the aromatic compound 3 is formed is inserted into a small vacuum deposition apparatus (trade name: VPC-260F, manufactured by ULVAC Kiko Co., Ltd.), and aluminum is deposited to a thickness of 100 nm by a vacuum deposition method. Thereby, the glass substrate E in which the cathode was formed was obtained. The glass substrate E on which the cathode was formed was taken out from the vacuum apparatus, and sealed with sealing glass and a two-component mixed epoxy resin in a nitrogen atmosphere, whereby the electroluminescent element 1 was produced.

  A forward voltage of 12 V was applied to the electroluminescent element 1, and the luminance and luminous efficiency were measured. The obtained results are shown in Table 1.

<Example 13> (Preparation of electroluminescent element 2)
In Example 12, the electroluminescent element 2 was produced in the same manner as in Example 12 except that the aromatic compound 6 was used instead of the aromatic compound 3. A forward voltage of 12 V was applied to the electroluminescent element 2, and luminance and luminous efficiency were measured. The obtained results are shown in Table 1.

<Example 14> (Preparation of electroluminescent element 3)
In Example 12, the electroluminescent element 3 was produced in the same manner as in Example 12 except that the aromatic compound 7 was used instead of the aromatic compound 3. A forward voltage of 12 V was applied to the electroluminescent element 3, and the luminance and luminous efficiency were measured. The obtained results are shown in Table 1.

<Example 15> (Preparation of electroluminescent element 4)
In Example 12, the electroluminescent element 4 is produced in the same manner as in Example 12 except that the aromatic compound 11 is used instead of the aromatic compound 3. When a forward voltage of 12 V is applied to the electroluminescent element 4, excellent luminance and luminous efficiency are exhibited.

<Comparative example 2> (Preparation of electroluminescent element C1)
In Example 12, the electroluminescent element C1 was produced in the same manner as in Example 12 except that the layer made of the aromatic compound 3 was not formed. A forward voltage of 12 V was applied to the electroluminescent element C1, and luminance and luminous efficiency were measured. The obtained results are shown in Table 1.

<Evaluation>
As can be seen from Table 1, the electroluminescent device using the aromatic compound of the present invention is superior in luminance and luminous efficiency as compared to the electroluminescent device not using the aromatic compound of the present invention.

Claims (12)

Including three or more repeating units represented by the following formula (1), one or more repeating units represented by the following formula (2) and / or one represented by the following formula (3), Aromatic compounds containing no carbon triple bonds.

(In the formula, Ar ¹ is a (2 + n) -valent aromatic heterocyclic group which may have a substituent. M is a hydrogen atom, a metal atom, a metal ion, an ammonium ion, or 1 to 4 carbon atoms. An ammonium ion substituted with a hydrogen group, a benzyl group which may have a substituent, or a boryl group substituted with two hydrocarbon groups which may have a substituent, where n is an integer of 1 or more Ar ² , Ar ³ and Ar ⁴ are the same or different and are a direct bond, a divalent aromatic hydrocarbon group which may have a substituent, or a divalent which may have a substituent. X represents an optionally substituted ethenylene group or an optionally substituted imino group, m is an integer of 0 to 2, provided that when m is 0, the Ar ² is directly not bind .R may have a substituent hydrocarbon group I am.)   M in the formula (1) is a metal atom, a metal ion, an ammonium ion, an ammonium ion substituted with 1 to 4 hydrocarbon groups, or two hydrocarbon groups which may have a substituent. The aromatic compound according to claim 1, which is a substituted boryl group. The aromatic compound according to claim 1 or 2, wherein Ar ¹ in the formula (1) is an (2 + n) -valent aromatic heterocyclic group which has an imine nitrogen atom and may have a substituent. The (2 + n) -valent aromatic heterocyclic group which may have a substituent represented by Ar ¹ in the formula (1) is 10 to 14 members. The aromatic compound described in 1. The aromatic compound according to any one of claims 1 to 4, wherein the repeating unit represented by the formula (1) is a repeating unit represented by the following formula (4).

(In the formula, R ′ is a hydroxyl group, an aldehyde group, an amino group, a cyano group, a nitro group, a halogen atom, a hydrocarbon group which may have a substituent, or a hydrocarbon which may have a substituent. An oxy group, a hydrocarbon carbonyl group which may have a substituent, a hydrocarbon oxycarbonyl group which may have a substituent, a hydrocarbon carbonyloxy group which may have a substituent, a substituent An optionally substituted sulfo group, an optionally substituted hydrocarbon azo group, an optionally substituted amino group substituted by one or two hydrocarbon groups, and a substituent An amide group substituted with one or two hydrocarbon groups which may have a monovalent heterocyclic group which may have a substituent. May be formed, k is an integer of 0 to 4. When a plurality of R's are present A plurality of R ′ may be the same or different, and M ′ is a hydrogen atom, a metal atom, a metal ion, an ammonium ion, an ammonium ion substituted with 1 to 4 hydrocarbon groups, or a substituent. And represents a boryl group substituted with two hydrocarbon groups which may have a substituent. The aromatic compound according to any one of claims 1 to 5, wherein the repeating unit represented by the formula (2) is a repeating unit represented by the following formula (2 ').

(In the formula, Ar ⁵ represents a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent.) The aromatic compound according to any one of claims 1 to 6, wherein the repeating unit represented by the formula (3) is a repeating unit represented by the following formula (3 ').

(In the formula, Ar ⁶ represents a direct bond, a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent. R ″ and R ′ ″ are the same or different and each represents a hydrocarbon group which may have a substituent. A plurality of R ′ ″ may be the same or different.) The aromatic compound according to any one of claims 1 to 7, which has a weight average molecular weight of 3 x 10 ³ to 1 x 10 ⁸ .   The total number of moles of the repeating unit represented by the formula (1), the repeating unit represented by the formula (2) and the repeating unit represented by the formula (3) is 60 of the total number of moles of all repeating units. The aromatic compound according to claim 8, which is at least%.   The repeating unit represented by the formula (1), the repeating unit represented by the formula (2) and / or the repeating unit represented by the formula (3) are included in the main chain, and The total number of moles of the repeating unit represented by formula (1), the repeating unit represented by formula (2) and the repeating unit represented by formula (3) is 60% of the total number of moles of all repeating units. It is the above, The aromatic compound of Claim 8.   The composition containing the aromatic compound as described in any one of Claims 1-10.   The electronic device formed using the aromatic compound as described in any one of Claims 1-10.