JP2003317963A - Photoelectron element using polymer material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new photoelectron element using a conjugated polymer compound. <P>SOLUTION: This photoelectron element employs the polymer compound having a number average molecular weight in terms of polystyrene of 10<SP>3</SP>-10<SP>8</SP>and including a repetition unit expressed by following formula (1). [Wherein, R<SB>1</SB>and R<SB>2</SB>are each independently hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkenyl group, arylalkynyl group, substituted silyl group, alkylamino group, arylamino group, univalent heterocyclic group, carboxyl group, substituted carboxyl group, or cyano group. <P>COPYRIGHT: (C)2004,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a pyrimido [5,4]
-D] relates to a novel optoelectronic device using a polymer compound having a pyrimidine skeleton in the main chain.

[0002]

2. Description of the Related Art Conjugated polymer compounds have been applied to optoelectronic devices such as light emitting devices, switching devices and photoelectric conversion devices by utilizing their semiconductor properties. For example, an optoelectronic device using a conjugated polymer compound such as a polyphenylene vinylene derivative, a polyfluorene derivative, or a polyphenylene derivative is known.

[0003]

However, the above-mentioned optoelectronic element has not yet sufficiently exhibited the characteristics required for the optoelectronic element, and development of a novel optoelectronic element material and an optoelectronic element using the same is desired. It is rare. An object of the present invention is to provide a novel optoelectronic device using a conjugated polymer compound.

[0004]

The present invention relates to an optoelectronic device using a polymer compound having a polystyrene-equivalent number average molecular weight of 10 ³ to 10 ⁸ and containing a repeating unit represented by the following formula (1). Is. (1) [wherein R ₁ and R ₂ are each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, It represents an arylalkynyl group, a substituted silyl group, an alkylamino group, an arylamino group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group. ]

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The polymer compound used in the optoelectronic device of the present invention contains the repeating unit represented by the above general formula (1).

R ₁ and R ₂ in the general formula (1) are each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group,
An arylalkenyl group, an arylalkynyl group, a substituted silyl group, an alkylamino group, an arylamino group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group.

The alkyl group may be linear, branched or cyclic and has a carbon number of usually about 1 to 20. Specifically, a methyl group, an ethyl group, a propyl group, i
-Propyl group, butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group , A lauryl group and the like, and a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a decyl group and a 3,7-dimethyloctyl group are preferable.

The alkoxy group may be linear, branched or cyclic and has a carbon number of usually about 1 to 20. Specifically, methoxy group, ethoxy group, propyloxy group, i-propyloxy group, Butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group,
Examples thereof include an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group and a lauryloxy group, and a pentyloxy group, a hexyloxy group, an octyloxy group, 2
-Ethylhexyloxy group, decyloxy group, 3,7-
A dimethyloctyloxy group is preferred.

The alkylthio group may be linear, branched or cyclic, and the carbon number is usually about 1 to 20,
Specifically, methylthio group, ethylthio group, propylthio group, i-propylthio group, butylthio group, i-butylthio 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, laurylthio group and the like, pentylthio group,
Hexylthio group, octylthio group, 2-ethylhexylthio group, decylthio group and 3,7-dimethyloctylthio group are preferred.

The aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon. Here, the aromatic hydrocarbon includes those having a condensed aromatic polycycle, and those in which two or more independent benzene rings or condensed polycycles are bonded directly or through a group such as vinylene. The aryl group usually has about 6 to 60 carbon atoms, and specifically, a phenyl group and a C _{1 to} C ₁₂ alkoxyphenyl group (wherein C _{1 to} C ₁₂ have ₁ to ₁₂ carbon atoms). The same shall apply to the following.), A C ₁ -C ₁₂ alkylphenyl group, a 1-naphthyl group, a 2-naphthyl group and the like are exemplified, and a C ₁ -C ₁₂ alkoxyphenyl group and a C ₁ -C ₁₂ alkylphenyl group are preferable. .

The aryloxy group usually has 6 to 6 carbon atoms.
0, specifically, a phenoxy group, C _{1 to} C ₁₂
Examples thereof include an alkoxyphenoxy group, a C _{1 to} C ₁₂ alkylphenoxy group, a 1-naphthyloxy group and a 2-naphthyloxy group, and a C _{1 to} C ₁₂ alkoxyphenoxy group,
C ₁ -C ₁₂ alkylphenoxy group are preferable.

The arylalkyl group usually has 7 to 7 carbon atoms.
It is about 60, specifically, 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 are exemplified, and C ₁ -C
₁₂ alkoxyphenyl-C ₁ -C ₁₂ alkyl group, C ₁ -C
_{A 12} alkylphenyl-C ₁ -C ₁₂ alkyl group is preferred.

The arylalkoxy group usually has 7 carbon atoms.
To about 60, specifically, phenyl-C _{1 to} C ₁₂
Alkoxy group, C ₁ -C ₁₂ alkoxyphenyl-C ₁ -C
₁₂ alkoxy groups, C ₁ -C ₁₂ alkylphenyl-C ₁ -C
₁₂ alkoxy group, 1-naphthyl-C ₁ -C ₁₂ alkoxy group, 2-naphthyl-C ₁ -C ₁₂ alkoxy group and the like are exemplified, and C ₁ -C ₁₂ alkoxyphenyl-C ₁ -C ₁₂ alkoxy group, C ₁ ˜C ₁₂ alkylphenyl-C ₁ -C ₁₂ alkoxy groups are preferred.

The arylalkenyl group usually has about 8 to 60 carbon atoms, specifically, phenyl-C ₂
To C ₁₂ alkenyl group, C _{1 to} 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 groups and the like, C ₁ -C ₁₂ alkoxyphenyl -C ₂ -C ₁₂
Alkenyl group, C ₁ ~C _{1 2} alkylphenyl -C ₂ -C ₁₂
Alkenyl groups are preferred.

The arylalkynyl group usually has about 8 to 60 carbon atoms, specifically, phenyl-C ₂
To C ₁₂ alkynyl group, C _{1 to} 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, C ₁ -C ₁₂ alkoxyphenyl -C ₂ -C ₁₂
Alkynyl group, C ₂ ~C _{1 2} alkylphenyl -C ₁ -C ₁₂
Alkynyl groups are preferred.

The substituted silyl group means a silyl group substituted with 1, 2 or 3 groups selected from an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, and usually has a carbon number of 1 to 1. It is about 60. The alkyl group, aryl group, arylalkyl group or monovalent heterocyclic group may have a substituent. Examples of the substituted silyl group include an alkylsilyl group and an (alkyl) (aryl) silyl group. The alkylsilyl group may be linear, branched or cyclic, and the carbon number thereof is usually about 1 to 60, and specifically, methylsilyl group, ethylsilyl group, propylsilyl group, i-propylsilyl group, butylsilyl group. , I-butylsilyl group, t-butylsilyl group, pentylsilyl group, hexylsilyl group, cyclohexylsilyl group, heptylsilyl group, octylsilyl group,
2-ethylhexylsilyl group, nonylsilyl group, decylsilyl group, 3,7-dimethyloctylsilyl group, laurylsilyl group, trimethylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, i-propyldimethylsilyl group, butyldimethylsilyl group, t-butyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyl Octyl-dimethylsilyl group,
Examples include lauryldimethylsilyl group, pentylsilyl group, hexylsilyl group, octylsilyl group, 2-ethylhexylsilyl group, decylsilyl group, 3,7-dimethyloctylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, octyl Dimethylsilyl group,
A 2-ethylhexyl-dimethylsilyl group, a decyldimethylsilyl group and a 3,7-dimethyloctyl-dimethylsilyl group are preferable. The (alkyl) (aryl) silyl group is a phenyl-C ₁ -C ₁₂ alkylsilyl group, C ₁ -C ₁₂
Alkoxyphenyl -C ₁ -C ₁₂ alkylsilyl group, C ₁
To C ₁₂ alkylphenyl C _{1 to} C ₁₂ alkylsilyl group,
1-naphthyl-C ₁ -C ₁₂ alkylsilyl group, 2-naphthyl-C ₁ -C ₁₂ alkylsilyl group, phenyl-C ₁ -C
₁₂ alkyl dimethyl silyl group, triphenyl silyl group,
Tri-p-xylylsilyl group, tribenzylsilyl group,
Examples thereof include a diphenylmethylsilyl group, a t-butyldiphenylsilyl group and a dimethylphenylsilyl group.

The alkylamino group may be linear, branched or cyclic and may be a monoalkylamino group or a dialkylamino group, and usually has about 1 to 40 carbon atoms. These alkyl groups may be the same or different. Specifically, methylamino group, ethylamino group, propylamino group, i-propylamino group, butylamino group, i-butylamino group, t-butylamino group, pentylamino group, hexylamino group, cyclohexylamino group , Heptylamino group, octylamino group, 2-ethylhexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, laurylamino group and the like. In these embodiments, all di-forms are also included. Among these, pentylamino group,
Hexylamino group, octylamino group, 2-ethylhexylamino group, decylamino group and 3,7-dimethyloctylamino group are preferred.

The arylamino group usually has 6 to 6 carbon atoms.
It has an aryl group of about 0, and may be a mono-form or a di-form, and in the case of the di-form, it may be the same group or different groups. More specifically, a phenylamino group, a C ₁ -C ₁₂ alkoxyphenylamino group, a C ₁ -C ₁₂ alkylphenylamino group, a 1-naphthylamino group, a 2-naphthylamino group, etc. are exemplified, and a C ₁ -C ₁₂ Alkylphenylamino group, C ₁
The -C ₁₂ alkoxyphenylamino group is preferred. These examples include di body

The monovalent heterocyclic group usually has 4 to 60 carbon atoms.
And specifically, a thienyl group, a C ₁ -C ₁₂ alkyl thienyl group, a pyrrolyl group, a furyl group, a pyridyl group,
C ₁ -C ₁₂ is like the illustration alkylpyridyl group, a thienyl group, C ₁ -C ₁₂ alkyl thienyl group, a pyridyl group, C ₁
~ C ₁₂ alkylpyridyl groups are preferred. The monovalent heterocyclic group means an atomic group remaining after removing one hydrogen atom from the heterocyclic compound.

The substituted carboxyl group usually has 2 to 6 carbon atoms.
It is about 0 and refers to a carboxyl group substituted with an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, and is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an i-propoxycarbonyl group or a butoxycarbonyl group. Group, i-butoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, cyclohexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, nonyloxycarbonyl group Group, decyloxycarbonyl group, 3,7-dimethyloctyloxycarbonyl group, dodecyloxycarbonyl group, trifluoromethoxycarbonyl group, pentafluoroethoxycarbonyl group, perfluorobut Aryloxycarbonyl group, perfluorohexyloxy carbonyl group, perfluorooctyloxy carbonyl group, phenoxycarbonyl group, naphthoxycarbonyl group, and pyridyl oxycarbonyl group. The alkyl group, aryl group, arylalkyl group or monovalent heterocyclic group may have a substituent. The carbon number of the substituted carboxyl group does not include the carbon number of the substituent.

Among the examples of the substituent described above, in the substituent containing an alkyl chain, they may be linear, branched or cyclic, or a combination thereof, and when they are not linear, For example, isoamyl group, 2
Examples include -ethylhexyl group, 3,7-dimethyloctyl group, cyclohexyl group, 4-C ₁ -C ₁₂ alkylcyclohexyl group and the like. Furthermore, when an aryl group or a heterocyclic group is included in a part of the examples of the substituents, they may further have one or more substituents.

When the group other than hydrogen atom is a long-chain substituent, from the viewpoint of good solubility, C (carbon), N
The total number of (nitrogen), O (oxygen) and S (sulfur) atoms is preferably 4 or more, more preferably 4 or more carbon atoms and nitrogen atoms.

Of these groups, an alkyl group, an aryl group, an alkylamino group and an arylamino group are preferable,
More preferred are alkylamino group and arylamino group.

The polymer compound of the present invention may contain a repeating unit other than the repeating unit represented by the formula (1). The total of the repeating units represented by the formula (1) is usually 1 mol% or more and 100 mol% or less, preferably 10 mol% or more and 90 mol% or less, and more preferably 30 mol% or more and 80 mol% or less of all the repeating units. % Or less.

Specific examples of the repeating unit other than the repeating unit represented by the general formula (1) include WO99 /
13692 publication specification, WO99 / 48160 publication specification, GB2340304A, WO00 / 53656 publication specification, WO01 / 19834 publication specification, WO00.
/ 55927 Published Specification, GB2348316, WO0
0/46321 publication specification, WO00 / 06665 publication specification, WO99 / 54943 publication specification, WO99 /
54385 published specification, US 5777070, WO98.
/ 067773 publication specification, WO97 / 05184 publication specification, WO00 / 35987 publication specification, WO00 / 5
3655 publication specification, WO01 / 34722 publication specification, WO99 / 24526 publication specification, WO00 / 22
027 published specification, WO00 / 22026 published specification,
WO98 / 27136 published specification, US573636,
WO98 / 21262 publication specification, US574192
1, WO97 / 09394 published specification, WO96 / 29
356 published specification, WO96 / 10617 published specification,
EP0707020, WO95 / 07955 published specification, JP 2001-181618 A, JP 2001
-123156, JP 2001-3045 A, JP 2000-351967 A, JP 2000
-303066, JP 2000-299189, JP 2000-252065, and JP 200
0-136379, JP-A 2000-104057.
JP-A-2000-80167, JP-A-10
-324870, JP-A-10-114891, JP-A-9-111233, and JP-A-9-454.
(Co) of polyfluorene, its derivatives and copolymers, polyarylene, its derivatives and copolymers, polyarylene vinylene, its derivatives and copolymers, aromatic amines and its derivatives disclosed in Japanese Patent Publication No. 78 The repeating unit contained in the polymer is exemplified.

The polystyrene-reduced number average molecular weight of the polymer compound used in the present invention is usually 10 ³ to 10 ⁸ .

The method for producing the polymer compound used in the present invention is not particularly limited, but it can be produced, for example, by a polymerization reaction of a monomer compound represented by the following formula (2). (2) Here, R ₁ and R ₂ are the same as above. X ₁ and X ₂ each independently represent a polymerizable group.

Examples of the polymerizable group include halogen atom, hydrogen atom, hydroxyl group, acyloxy group, boric acid group, boric acid ester group, halogenated methyl group, sulfonium group, aldehyde group, phosphonium group and the like. .

When the polymer compound used in the present invention does not have a vinylene group or a triple bond in a repeating unit other than the repeating unit represented by the general formula (1), it is polymerized from the corresponding monomer by Suzuki coupling reaction. Method, polymerization by Grignard reaction, polymerization by Ni (0) catalyst, polymerization by an oxidizing agent such as FeCl ₃ , electrochemical oxidation polymerization, or a method for producing an intermediate having a suitable leaving group. Examples thereof include a method using molecular decomposition.

More specifically, when the polymerizable group is a halogen atom, it can be produced by a dehalogenation polymerization reaction of a monomer compound represented by the formula (2) with a zero-valent nickel complex. In this polymerization reaction,
It is considered that it is preferable to use a 0.1- to 3-fold molar quantity of 0-valent nickel (Ni (0)) complex with respect to the monomer compound, and to carry out using a solvent. The zero-valent nickel (Ni (0)) complex can be used in the form of, for example, a mixture of bis (1,5-cyclooctadiene) nickel and 2,2′-bipyridyl.

The polymerization can be carried out using an organic solvent such as a nitrile solvent such as DMF (dimethylformamide), dimethylsulfoxide, tetrahydrofuran or acetonitrile, preferably at a temperature of about 20 to 80 ° C. The zero-valent nickel complex may be prepared by reacting zinc with a divalent nickel complex in the reaction system. In this case, since the nickel complex can be repeatedly used with zinc or the like in the reaction system, the use ratio of the nickel complex with respect to the raw material monomer compound may be in the range of about 0.01 to 0.5.

The halogenated pyrimidine compound serving as a repeating unit having an amino group as a raw material monomer compound is described in, for example, the literature; Fischer, FG, Roch, J. &amp;
Neumann, WPChlor-, Hydroxy- und Amino-Derivate
des Pyrimido [5,4-d] pyrimidins. Ann. Chem. 631, 147
-162 (1960). It can be synthesized by incorporating the method described.

When the repeating unit other than the repeating unit represented by the general formula (1) has a vinylene group, for example, the method described in JP-A-5-202355 can be mentioned. That is, polymerization of a compound having an aldehyde group and a compound having a phosphonium base, or a compound having an aldehyde group and a phosphonium base by Wittig reaction, a compound having a vinyl group and a compound having a halogen group, or a vinyl group Polymerization by Heck reaction of a compound having a halogen group, Horner-Wadsworth of a compound having an aldehyde group and a compound having an alkylphosphonate group, or a compound having an aldehyde group and an alkylphosphonate group
-Polymerization by Emmons method, 2 halogenated methyl groups
Polycondensation of one or two or more compounds by dehydrohalogenation method, polycondensation of two or more compounds of sulfonium base by sulfonium salt decomposition method,
Method such as polymerization of a compound having an aldehyde group and a compound having an acetonitrile group or a compound having an aldehyde group and an acetonitrile group by Knoevenagel reaction, polymerization of a compound having two or more aldehyde groups by McMurry reaction, etc. Is exemplified. When the polymer compound has a triple bond in the main chain, for example, the Heck reaction can be used.

Among these, polymerization by Wittig reaction, polymerization by Heck reaction, Horner-Wad
Polymerization by the swath-Emmons method, Knoev
Polymerization by the enagel reaction, polymerization by the Suzuki coupling reaction, polymerization by the Grignard reaction, and polymerization by the Ni (0) catalyst are preferable because the structure can be easily controlled. More preferably, a method of polymerizing by Suzuki coupling reaction, a method of polymerizing by Grignard reaction, Ni
(0) A method of polymerizing with a catalyst

Specifically, if necessary, a compound having a plurality of reactive substituents serving as a monomer is dissolved in an organic solvent, and, for example, an alkali or a suitable catalyst is used, and the temperature is not lower than the melting point and not higher than the boiling point of the organic solvent. Can be reacted. For example,
"Organic Reactions (Organic R
actions) ", Vol. 14, 270-490,
John Wiley and Sons (John Wile
y & Sons, Inc. ), 1965, "Organic Reactions (Organic Reactio
ns) ”, vol. 27, pp. 345-390, John Wiley & Sons (John Wiley & Sons).
s, Inc. ), 1982, "Organic Syntheses", Collective Volume 6 (Collective Volume).
VI), pages 407-411, John Wiley & Sons, In.
c. ), 1988, Chemical Review (Chem.
Rev. ), 95, 2457 (1995), Journal of Organometallic Chemistry (J. Organomet. Chem.), 576.
Vol., 147 (1999), Journal of Practical Chemistry (J. Prakt. Che.
m. ), 336, 247 (1994), Macromolecular Chemistry Macromolecular Symposium (Makromol. Chem., Macr.
omol. Symp. ), Vol. 12, p. 229 (198
Known methods described in (7 years) and the like can be used.

Although the organic solvent varies depending on the compound and reaction used, it is generally preferable that the solvent used is sufficiently deoxidized and the reaction proceeds in an inert atmosphere in order to suppress side reactions. In addition, it is preferable to perform dehydration treatment in the same manner. However, this is not the case in the case of a reaction in a two-phase system with water, such as the Suzuki coupling reaction.

For the reaction, an alkali or a suitable catalyst is added. These may be selected according to the reaction used. The alkali or catalyst is preferably one that is sufficiently dissolved in the solvent used for the reaction. The method for mixing the alkali or the catalyst is to slowly add the solution of the alkali or the catalyst while stirring the reaction solution under an inert atmosphere such as argon or nitrogen, or, conversely, slowly add the reaction solution to the solution of the alkali or the catalyst. The method of adding is illustrated.

When the polymer compound is used in an optoelectronic device,
Since the purity affects the performance of the device, it is preferable to purify the monomer before polymerization by a method such as distillation, sublimation purification, and recrystallization, and then polymerize it. After polymerization, reprecipitation purification,
Purification such as fractionation by chromatography is preferred.

The optoelectronic device of the present invention has a layer containing a polymer compound containing a repeating unit represented by the general formula (1). The content of the polymer compound containing the repeating unit represented by the general formula (1) in the layer is preferably about 1 to 99% by weight. Examples of the optoelectronic element of the present invention include a light emitting element, a switching element, a photoelectric conversion element, a solar cell, and an optical sensor utilizing photoelectric characteristics.

A light emitting device according to one embodiment of the present invention will be described. The light emitting device of the present invention has a light emitting layer between electrodes composed of an anode and a cathode. The light emitting device of the present invention may have a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer in addition to the light emitting layer. Here, the hole transport layer is
The layer having a function of transporting holes is referred to, and the electron transport layer is a layer having a function of transporting electrons. The electron transport layer and the hole transport layer are collectively referred to as a charge transport layer. Further, the light emitting layer, the hole transporting layer, and the electron transporting layer may be two or more layers independently of each other. Here, the hole transport layer and / or the electron transport layer may be two or more layers.

That is, as the light emitting device of the present invention, a device having a hole injecting layer in contact with the anode between electrodes composed of an anode and a cathode, and further having a light emitting layer (for example, a below))
In addition to the above, for example, a light emitting element in which a hole transport layer is provided between the hole injection layer and the light emitting layer and adjacent to the light emitting layer (for example, b) below); between the cathode and the light emitting layer. A light emitting device having an electron transport layer provided adjacent to the light emitting layer (for example, the following c)); an electron transport layer provided adjacent to the light emitting layer between the cathode and the light emitting layer; And a light emitting layer, a light emitting device element in which a hole transporting layer is provided adjacent to the light emitting layer (for example, d below));
Etc.

A) anode / hole injection layer / light emitting layer / cathode b) anode / hole injection layer / hole transport layer / light emitting layer / cathode c) anode / hole injection layer / light emitting layer / electron transport layer / Cathode d) Anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / cathode (here, / indicates that each layer is laminated adjacently. The same applies hereinafter.)

In the case of a light emitting device, a polymer compound containing the repeating unit of the formula (1) can be used in the light emitting layer, the charge transport layer and the charge injection layer. In this case, the polymer compound may be used alone, or one or more kinds of light emitting materials, charge transport materials, and charge injection materials other than the polymer compound may be mixed and used in each layer. When the polymer compound is used in the light emitting layer, the light emitting layer further contains, in addition to the polymer compound, at least one material selected from a hole transporting material, an electron transporting material, and a light emitting material other than the polymer compound. You can leave.

The thickness of the light emitting layer of the light emitting device of the present invention has an optimum value depending on the material used for the light emitting layer, and may be selected so that the driving voltage and the light emitting efficiency have appropriate values. It is necessary to have a thickness that does not cause pinholes, and if it is too thick, the driving voltage of the element becomes high, which is not preferable. Therefore, the thickness of the light emitting layer is, for example, 1 nm to 1 μm, and preferably 10 nm.
To 300 nm, more preferably 20 nm to 15 nm
It is 0 nm.

When the low molecular weight fluorescent substance is used as the light emitting material, the light emitting layer can be formed by, for example, vacuum deposition or film formation from a mixed solution with a polymer binder.

When a polymer compound having a repeating unit represented by the general formula (1) is used as a light emitting material, a film can be formed from a solution containing the compound.
When forming a film from a solution, a film forming method similar to that of the above hole injection layer is adopted. In addition to the polymer compound having the repeating unit represented by the general formula (1), another polymer compound may be contained, and the other polymer compound is not particularly limited, but has, for example, a fluorene skeleton. Conjugated polymers such as polymers are preferred.
As a solvent used when forming a film of a luminescent material from a solution,
There is no particular limitation as long as it dissolves a polymer compound having a repeating unit represented by the general formula (1) or a polymer binder. Specifically, chlorine-based solvents such as chloroform, methylene chloride and dichloroethane, ether-based solvents such as tetrahydrofuran, and aromatics such as toluene, xylene, mesitylene, 1,2,3,4-tetramethylbenzene and n-butylbenzene. A compound solvent or the like is more preferably used. As a light emitting material

When the light-emitting device of the present invention has a hole-transporting layer, the film thickness of the hole-transporting layer varies depending on the material used, and is selected so that the driving voltage and the luminous efficiency are appropriate values. However, if the thickness is too large, the driving voltage of the element becomes high, which is not preferable. Therefore, the film thickness of the hole transport layer is, for example, 1 nm to 1 μm, preferably 2 nm to 300 nm, and more preferably 5 nm.
nm to 200 nm.

When the light emitting device of the present invention has an electron transporting layer, the film thickness of the electron transporting layer varies depending on the material used, and is selected so that the driving voltage and the light emitting efficiency have appropriate values. It is good, but at least a thickness that does not cause pinholes is necessary. If it is too thick, the driving voltage of the element becomes high, which is not preferable. Therefore, the film thickness of the electron transport layer is, for example, 1 nm to 1 μm, preferably 2 nm to 300 nm, and more preferably 5 nm.
nm to 200 nm.

As the hole transporting material and electron transporting material used in the light emitting device of the present invention, known low molecular weight compounds and high molecular weight compounds can be used, but it is preferable to use high molecular weight compounds. As specific examples of the hole transporting material and the electron transporting material, WO 99/1369 is given as a polymer compound.
No. 2, published specification, WO99 / 48160 published specification, G
B2340304A, WO00 / 53656 publication specification, WO01 / 19834 publication specification, WO00 / 55
927 published specification, GB2348316, WO00 / 4
6321 publication specification, WO00 / 06665 publication specification, WO99 / 54943 publication specification, WO99 / 54
385 Published Specification, US5777070, WO98 / 0
6773 publication specification, WO 97/05184 publication specification, WO 00/35987 publication specification, WO 00/53
655 specification, WO 01/34722 specification,
WO99 / 24526 publication specification, WO00 / 2202
7 Published specification, WO00 / 22026 Published specification, WO
98/27136 published specification, US573636, WO
98/21262 Published Specification, US5741921, W
O97 / 09394 published specification, WO96 / 29356
Open specification, WO96 / 10617 Open specification, EP0
707020, WO95 / 07955 published specification, JP 2001-181618 A, JP 2001-123.
156, JP 2001-3045 A, JP 2
000-351967, JP 2000-3030A.
No. 66, No. 2000-299189, No. 2000-252065, No. 2000-136.
379, JP-A 2000-104057, JP-A 2000-80167, and JP-A 10-3248.
70, JP-A-10-114891, JP-A-9-111233, JP-A-9-45478, and the like, polyfluorene, derivatives and copolymers thereof, polyarylene, derivatives and copolymers thereof. Examples thereof include polymers, polyarylene vinylene, derivatives and copolymers thereof, and (co) polymers of aromatic amines and derivatives thereof.

As the hole transporting material of the polymer compound,
Those described in the above-mentioned documents are more preferably used, but other polymer compounds such as polyvinylcarbazole or its derivative, polysilane or its derivative, and polysiloxane having an aromatic amine in its side chain or main chain. A derivative, polyaniline or a derivative thereof, polythiophene or a derivative thereof, polypyrrole or a derivative thereof, or poly (2,5-thienylenevinylene) or a derivative thereof can be used.
Further, as a hole transporting material of a low molecular weight compound, a pyrazoline derivative, an arylamine derivative, a stilbene derivative,
An example is a triphenyldiamine derivative.

As the electron transporting material of the polymer compound,
In addition to those described in the above-mentioned documents, polyquinoline or its derivative, polyquinoxaline or its derivative may be used. Further, as the electron transporting material of low molecular weight compounds, oxadiazole derivatives, anthraquinodimethane or its derivatives, benzoquinone or its derivatives, naphthoquinone or its derivatives, anthraquinone or its derivatives, tetracyanoanthraquinodimethane or its derivatives , Fluorenone derivatives,
Examples include metals such as diphenyldicyanoethylene or its derivative, diphenoquinone derivative, or 8-hydroxyquinoline or its derivative. JP-A-63-7
No. 0257, No. 63-175860, No. 2-135359, No. 2-135361.
No. 2-209988, No. 3-37992,
A hole transporting material, an electron transporting material and the like described in JP-A-3-152184 can be preferably used.

The hole transport layer and the electron transport layer are formed by using a hole transport material and an electron transport material, respectively. When the hole transporting material or the electron transporting material is a low molecular compound, vacuum deposition or film formation from a mixed solution with a polymer binder is exemplified, and in the case of a polymer compound, it is prepared from a solution or a molten state. Can be membrane.

When forming a film of a polymer compound or a hole transporting material from a solution, the solvent used in the solution is not particularly limited as long as it can dissolve the material. Specifically, chlorinated solvents such as chloroform, methylene chloride and dichloroethane, toluene, xylene, mesitylene, 1,
Aromatic compound solvents such as 2,3,4-tetramethylbenzene and n-butylbenzene are preferably used. The solvent used when forming the hole transport layer from a solution is not particularly limited as long as it dissolves the hole transport material and the polymer binder used as necessary. As the solvent, chlorine-based solvents such as chloroform, methylene chloride and dichloroethane, ether-based solvents such as tetrahydrofuran, aromatic hydrocarbon-based solvents such as toluene and xylene, ketone-based solvents such as acetone and methyl ethyl ketone,
Examples thereof include ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate.

The method for forming the electron transport layer is not particularly limited, but for the low molecular weight electron transporting material, the vacuum deposition method from powder, or the method by film formation from a solution or a molten state is used as a polymer electron. For the transportable material, a method of forming a film from a solution or a molten state is exemplified. When forming a film from a solution or a molten state, a polymer binder may be used together.

As the polymer binder to be mixed with the hole transporting material or the electron transporting material as needed, those which do not extremely disturb the charge transportation are preferable, and those which do not have strong absorption of visible light are suitably used. To be As the polymer binder, poly (N-vinylcarbazole), polyaniline or its derivative, polythiophene or its derivative, poly (p-phenylene vinylene) or its derivative, poly (2,5-thienylene vinylene) or its derivative, polycarbonate , Polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane, and the like.

The light emitting device of the present invention may have layers other than the anode, the cathode, the light emitting layer, the hole injection layer, the hole transport layer and the electron transport layer. Examples of such a layer include an electron injection layer and an insulating layer having a film thickness of 10 nm or less (a thin buffer layer provided at the interface between the charge transport layer and the light emitting layer for improving the adhesiveness at the interface and preventing mixing). To be Here, a layer provided adjacent to the cathode, which has a function of improving electron injection efficiency from the cathode and has an effect of lowering the driving voltage of the element, is referred to as an electron injection layer. The order and number of layers to be laminated, and the thickness of each layer can be appropriately used in consideration of luminous efficiency and device life.

Specific examples of the electron injection layer include a work function of the cathode material and an electron affinity of the light emitting material contained in the light emitting layer or an electron transporting layer provided between the cathode and the light emitting layer or the electron transporting layer. A layer containing a material having an electron affinity of an intermediate value with the contained electron transporting material is preferably used.

When the electron injection layer is a layer containing a conductive polymer, the layer is provided between the cathode and the light emitting layer and adjacent to the electrode. The electric conductivity of the conductive polymer is 10 ⁻⁷ S /
cm or more and 10 ³ S / cm or less, and in order to reduce the leak current between the light emitting pixels, 10 ⁻⁵ S
/ Cm to 10 more preferably ² S / cm, 10 ^{- 5}
S / cm or more and 10 ¹ S / cm or less are more preferable. Usually, in order to make the electric conductivity of the conductive polymer 10 ⁻⁵ S / cm or more and 10 ³ S / cm or less, the conductive polymer is doped with an appropriate amount of ions. The types of ions to be doped are
It is a cation, and examples thereof include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion. The thickness of the electron injection layer is, for example, 1 nm to 150 nm, and 2 nm to 10 nm.
0 nm is preferred.

As a film forming method of the electron injection layer, film formation from a solution is exemplified, and it is sufficient to remove the solvent by coating this solution and then drying, which is very advantageous in manufacturing.
As a film forming method from a solution, a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, A coating method such as a flexographic printing method, an offset printing method or an inkjet printing method can be used. Further, as the electron injecting material, an emulsion that is dispersed in water or alcohol can be formed into a film by a method similar to that of the solution.

Examples of the insulating layer having a thickness of 10 nm or less provided in contact with the cathode include metal fluorides, metal oxides, and organic insulating materials. Metal fluorides or metal oxides such as alkali metals or alkaline earth metals are used. preferable. A vacuum deposition method is exemplified as a method for forming the inorganic compound used for the insulating layer.

The substrate on which the light emitting device of the present invention is formed may be any one that does not change when forming the electrodes and each layer of the device, such as glass, plastic, polymer film,
A silicon substrate etc. are illustrated. In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent.

It is preferable that at least one of the electrodes comprising an anode and a cathode of the light emitting device of the present invention is usually transparent or semitransparent, and the anode side is transparent or semitransparent. The material of the anode is a conductive metal oxide,
A semitransparent metal or the like is used. Specifically, conductive glass (NES, which is made of indium oxide, zinc oxide, tin oxide, and indium-tin-oxide (ITO), indium-zinc-oxide, or the like, which is a composite thereof, (NES
A, etc.), gold, platinum, silver, copper, etc. are used, and ITO,
Indium / zinc / oxide and tin oxide are preferable.
Further, as the anode, an organic transparent conductive film such as polyaniline or a derivative thereof and polythiophene or a derivative thereof may be used.

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

Examples of the method for producing the anode include a vacuum vapor deposition method, a sputtering method, an ion plating method and a plating method.

As a material of the cathode used in the light emitting device of the present invention, a material having a small work function is preferable. For example, lithium, sodium, potassium, rubidium, cesium,
Beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and two or more alloys thereof, or one of them Alloys of one or more with one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, graphite intercalation compounds, and the like are used. Examples of alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys,
Examples thereof include 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 can be appropriately selected in consideration of electric conductivity and durability, but is, for example, 10 nm to 10 μm, preferably 20 nm to 1 μm, and more preferably 50 nm to 500 nm. is there.

As a method for producing the cathode, a vacuum vapor deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression bonded and the like are used.

After forming the cathode, a protective layer for protecting the light emitting device may be attached. In order to stably use the light emitting device for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the device from the outside.

As the protective layer, polymer compounds, metal oxides, metal nitrides, metal oxynitrides, metal fluorides, metal borides and the like can be used. Further, as the protective cover, a glass plate, a plastic plate whose surface has been subjected to low water permeability treatment, or the like can be used, and a method in which the cover is adhered to the element substrate with a thermosetting resin or a photocurable resin and sealed is preferable. Used for. If the space is maintained by using the spacer, it is easy to prevent the element from being damaged. If the space is filled with an inert gas such as nitrogen or argon, oxidation of the cathode can be prevented, and a desiccant such as barium oxide or calcium oxide can be placed in the space to improve the manufacturing process. It becomes easy to prevent the adsorbed water from deteriorating the performance of the device. It is preferable to take any one or more of these measures.

The light emitting device of the present invention can be used as a surface light source, a segment display device, a dot matrix display device, a backlight of a liquid crystal display device and the like.

In order to obtain planar light emission using the light emitting device of the present invention, the planar anode and cathode may be arranged so as to overlap each other. In addition, in order to obtain a patterned light emission,
A method of installing a mask provided with a patterned window on the surface of the planar light-emitting device, a method of forming an organic material layer of a non-light emitting portion to be extremely thick and substantially non-light emitting, either one of an anode and a cathode. Alternatively, there is a method of forming both electrodes in a pattern. By forming a pattern by any of these methods and arranging some electrodes so that they can be turned on / off independently, a segment type display element capable of displaying numbers, letters, simple symbols, etc. can be obtained. Further, in order to form a dot matrix device, both the anode and the cathode may be formed in stripes and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymers having different emission colors or a method of using a color filter or a fluorescence conversion filter. The dot matrix element may be passively driven or may be actively driven in combination with a thin film transistor using amorphous silicon or low temperature polysilicon. 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. Further, the planar light emitting element is a self-luminous thin type and can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. Further, if a flexible substrate is used, it can be used as a curved light source or a display device.

Next, a switching element will be described as another aspect of the optoelectronic element of the present invention. As the switching element, the formula (1) is used for the source and drain electrodes.
, A field effect transistor having a thin film containing a polymer compound containing repeating units and having an insulating film facing the film and a gate electrode provided on the side of the insulating film opposite to the polymer compound thin film, or a source electrode and a drain. An example is a static induction type transistor in which a thin film containing the above-mentioned polymer compound sandwiched between electrodes is formed and a gate electrode is embedded in the thin film. As a method of making these switching elements, a method similar to that described in Japanese Patent No. 2609366 is exemplified. Specifically, a method of forming a thin film of a polymer compound on a substrate having a source electrode and a drain electrode and then forming an insulating film and a gate electrode, or a substrate having a gate electrode and an insulating film so as to cover the gate electrode. An example is a method of forming a source electrode and a drain electrode after forming a polymer thin film on. Further, in the electrostatic induction transistor, a first polymer thin film is formed on a substrate having a source electrode, a gate electrode is formed on the first polymer thin film, and then a second polymer thin film is formed, and then, A method of forming the drain electrode is exemplified. In this case, the first polymer thin film and the second polymer thin film may be the same polymer compound,
Different polymer compounds may be used. Furthermore, the polymer compound of the present invention may be contained in at least one of the two polymer thin films. These polymer thin films may be further laminated with one or more layers, they may be laminated with layers containing the same polymer compound, or may be laminated with layers containing different materials. The method for forming the polymer thin film is not particularly limited, but those exemplified for the light emitting device can be preferably used. An active matrix drive circuit can be constructed using the switching element of the present invention. The circuit can be used in liquid crystal or light emitting display devices.

Next, as another aspect of the present invention, a photoelectric conversion element will be described. One formed on a polymer compound layer formed on a device or a substrate in which a layer of a polymer compound containing a repeating unit of the formula (1) is sandwiched between two sets of electrodes, at least one of which is transparent or semitransparent. A device having a pair of comb-shaped electrodes is exemplified. In order to improve the characteristics, fullerenes, carbon nanotubes, etc. may be mixed. A method described in Japanese Patent No. 3146296 is exemplified as a method for manufacturing the photoelectric conversion element. Specifically, a method of forming a polymer thin film on a substrate having a first electrode and then forming a second electrode on the substrate, forming a polymer thin film on the substrate, and Examples include a method of forming a comb-shaped electrode and a method of forming a polymer thin film on a pair of comb-shaped electrodes formed on a substrate. One of the first and second electrodes is transparent or semi-transparent. The method for forming the polymer thin film and the method for mixing the fullerene and the carbon nanotube are not particularly limited, but those exemplified for the light emitting device can be preferably used.

A solar cell or a photosensor utilizing photoconductivity is a specific application example of such a photoelectric conversion element.

[0075]

EXAMPLES Examples will be shown below to explain the present invention in more detail, but the present invention is not limited to these. Here, regarding the weight average molecular weight and the number average molecular weight, the polystyrene equivalent average molecular weight was determined by gel permeation chromatography (GPC) using chloroform as a solvent.

Reference Example 1 <Synthesis of Polymer Compound 1> 2,6-dichloro-4,8-di (N, N-dihexylamino) pyrimido [wherein R ₁ and R ₂ are N, N-dihexylamino groups] 5,4-d]
The polymerization reaction was carried out in the presence of a zero-valent nickel complex as a mixture of bis (1,5-cyclooctadiene) nickel and 2,2'-bipyridyl using pyrimidine as a raw material monomer. The reaction was carried out using DMF as a solvent at a temperature of 60 ° C for 4 hours.
It went for 8 hours.

80% of poly [4,8-di (N, N-dihexylamino) pyrimido [5,4-d] pyrimidine-2,6-diyl] was obtained by this dehalogenation polymerization reaction.
Obtained in high yield. The number average molecular weight of this product by GPC (polystyrene conversion) was Mn = 19000, and the weight average molecular weight was Mw = 92000.

The absorption peak of 890 cm ^-1 based on the C-Cl bond of the monomer compound was not observed at all in the infrared absorption spectrum of the polymer.

[0079] In analogy to the above polymerization reaction <Synthesis of Polymer Compound 2, 3, 4>, R ₁ and R ₂ are, N, a polymer compound is N- didecylamino group, R ₁ and R ₂ are,
A polymer compound 3 having an N, N-di-2-ethylhexylamino group and a polymer compound 4 having R ₁ and R _{2 each} being an N-octylamino group were synthesized.

<Synthesis of Polymer Compound 5> 2,7-Dibromo-9,9-dioctylfluorene (26.32 g,
0.0480 mol), 2,7-dibromo-9,9-diisopentylfluorene (5.6 g, 0.0121 mo)
1) and 2,2′-bipyridyl (22 g, 0.141
(mol) was dissolved in 1600 mL of dehydrated tetrahydrofuran, and then the inside of the system was replaced with nitrogen by bubbling with nitrogen. Under a nitrogen atmosphere, bis (1,5
-Cyclooctadiene) nickel (0) {Ni (CO
D) ₂ } (40.01 g, 0.145 mol) added, 6
The temperature was raised to 0 ° C. and the reaction was carried out for 8 hours. After the reaction, the reaction solution was cooled to room temperature (about 25 ° C.), and 25% ammonia water 200 mL / methanol 1200 mL / ion-exchanged water 1
After dripping into a 200 mL mixed solution and stirring for 30 minutes,
The deposited precipitate was filtered and air dried. Then toluene 1
It was dissolved in 100 mL and then filtered, and the filtrate was added dropwise to 3300 mL of methanol and stirred for 30 minutes. The deposited precipitate was filtered, washed with 1000 mL of methanol, and dried under reduced pressure for 5 hours. The yield of the obtained polymer is 2
It was 0.47 g. The obtained polymer is used as a polymer compound 5
Call. The polystyrene-converted average molecular weight of the polymer is
Mn = 6.0 × 10 ⁴ , Mw = 1.5 × 10 ⁵ .
Copolymer 2 was easily soluble in solvents such as toluene and chloroform.

Example 1 A glass substrate having an ITO film with a thickness of 150 nm formed by a sputtering method was coated with poly (ethylenedioxythiophene) /
Polystyrene sulfonic acid solution (Bayer, Bayt
ronP) to form a film with a thickness of 50 nm by spin coating, and dried at 200 ° C. for 10 minutes on a hot plate. Next, the polymer material 1 obtained above was spin-coated at a rotation speed of 1800 rpm using a chloroform solution prepared to have a concentration of 1.6 wt%. Further, this was dried under reduced pressure at 80 ° C. for 1 hour, and then, as a cathode, calcium was deposited by about 20 nm, and then aluminum was deposited by about 50 nm to prepare an EL device. After the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, vapor deposition of metal was started. By applying a voltage to the obtained device,
EL having peak at 504 nm from polymer compound 1
Luminescence was obtained. The intensity of EL light emission was almost proportional to the current density. The device has 0.24 cd / m at about 24.6V.
^It exhibited a luminescence of ² .

Example 2 A device was obtained in the same manner as in Example 1 except that the polymer compound 1 and the polymer compound 5 were mixed instead of the polymer compound 1. At this time, the mixing amount of the polymer compound 1 was 27.4 based on the total amount of the polymer compound 1 and the polymer compound 5.
It was wt%. EL light emission having a peak at 504 nm was obtained from this device. The intensity of EL light emission was almost proportional to the current density. The device has a brightness of about 13V and a brightness of 1c.
The brightness exceeded 3.1 d / m ² and exhibited a brightness of 3.1 cd / m ² at 16.3V.

Example 3 A device was obtained in the same manner as in Example 1 except that the polymer compound 2 was used instead of the polymer compound 1 of Example 1. EL light emission having a peak at 486 nm was obtained from this device. The intensity of EL light emission was almost proportional to the current density. The device has a brightness of more than 1 cd / m ² at 19 V and 0.1 c
The efficiency of d / A was shown.

Example 4 A device was prepared in the same manner as in Example 2 except that the polymer compound 2 was used in place of the polymer compound 1 of Example 2, and the polymer compound 2 and the polymer compound 5 were mixed. An EL device using the film was obtained. At this time, the mixing ratio of the polymer compound 2 was 21.5% by weight based on the total weight of the polymer compound 2 and the polymer compound 5. EL light emission having a peak of 452 nm was obtained from this device. The intensity of EL light emission was almost proportional to the current density. The device has a brightness of about 14V and a brightness of 1 cd.
/ M ² exceeded.

Example 5 A device was prepared in the same manner as in Example 2 except that the polymer compound 3 was used in place of the polymer compound 2 of Example 4, and the polymer compound 3 and the polymer compound 5 were mixed. An EL device using the film was obtained. The mixing ratio of the polymer compound 3 at this time was 25.4% by weight with respect to the total of the polymer compound 3 and the polymer compound 5. 476nm and 508nm from this device
EL light emission having a peak of was obtained. The intensity of EL light emission was almost proportional to the current density. The device showed an efficiency of 0.24 cd / A with a brightness of more than 1 cd / m ² at about 14V.

Example 6 A device was prepared in the same manner as in Example 2 except that the polymer compound 4 was used instead of the polymer compound 1 of Example 2, and the polymer compound 4 and the polymer compound 5 were mixed. An EL device using the film was obtained. The mixing ratio of the polymer compound 4 at this time is 2 with respect to the total of the polymer compound 4 and the polymer compound 5.
It was 9.4% by weight. 424 nm from this element, 4
EL emission having peaks at 72 nm and 504 nm was obtained. The intensity of EL light emission was almost proportional to the current density.
The device has a brightness of about 1 cd / m ² at about 26 V,
The efficiency was 0.15 cd / A.

[0087]

According to the present invention, pyrimido [5,4-d]
It was possible to provide a novel optoelectronic device using a polymer compound having a pyrimidine skeleton in the main chain. The light emitting element or the switching element which is the optoelectronic element can be preferably used for a device such as a curved or flat light source for a backlight or illumination of a liquid crystal display, a segment type display element, a dot matrix flat panel display and the like. Furthermore, it can be preferably used as a solar cell or an optical sensor.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) H01L 31/04 H05B 33/22 D H05B 33/22 H01L 27/14 E 31/04 D (72) Inventor Toshihiro Ohnishi 6 Kitahara, Tsukuba-shi, Ibaraki Sumitomo Chemical Co., Ltd. Internal F-term (reference) 2H091 FA41Z FA44Z GA01 GA02 GA09 GA11 LA30 3K007 AB02 AB03 DB03 4J032 BA12 BB01 BC03 BC05 BD02 4M118 AA10 AB10 CA14 CB20 5F051 AA11 FA14 CB03

Claims (12)

[Claims] 1. A polystyrene-equivalent number average molecular weight of 10 ³
A 10 ^8, optoelectronic element characterized by using a polymer compound containing a repeating unit represented by the following formula (1). (1) [wherein R ₁ and R ₂ are each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, It represents an arylalkynyl group, a substituted silyl group, an alkylamino group, an arylamino group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group. ] 2. An optoelectronic device according to claim 1, which has a layer containing a polymer compound containing a repeating unit represented by the formula (1). 3. The optoelectronic device according to claim 1, wherein the optoelectronic device is a light emitting device. 4. The optoelectronic device according to claim 1, wherein the optoelectronic device is a switching device. 5. The optoelectronic device according to claim 1, wherein the optoelectronic device is a photoelectric conversion device. 6. The optoelectronic device according to claim 1, wherein the optoelectronic device is a solar cell. 7. The optoelectronic element according to claim 1, wherein the optoelectronic element is an optical sensor utilizing photoconductivity. 8. A planar light source using the light emitting device according to claim 3. 9. A segment display device using the light emitting device according to claim 3. 10. A dot matrix display device comprising the light emitting device according to claim 3. 11. A liquid crystal display device comprising the light emitting device according to claim 3 as a backlight. 12. A liquid crystal or light emitting display device having an active matrix drive circuit mainly constructed from the switching element according to claim 4.