JP2009064968A - Organic electroluminescent element and display unit - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element having a larger luminescence intensity, a higher luminescence efficiency and a longer element life and being more easily produced than that using a polymer material without taking a material for an organic compound layer into consideration. <P>SOLUTION: This organic electroluminescent element is constituted of one or a plurality of organic compound layers pinched between a pair of electrodes composed of a positive electrode and a negative electrode at least one of which is transparent or translucent. In this case, at least one layer of organic compound layers contains one or more types of polyesters comprising a recurring unit containing as a partial structure, a structure represented by Formula (I-1) or Formula (I-2). In Formula (I-1) or Formula (I-2), Ar represents an unsubstituted or substituted phenyl group, an unsubstituted or substituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, an unsubstituted or substituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or an unsubstituted or substituted monovalent aromatic heterocyclic ring; R<SP>1</SP>to R<SP>6</SP>independently represent a hydrogen atom, an alkyl group, an alkoxyl group, an aralkyl group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or an unsubstituted or substituted monovalent aromatic heterocyclic ring; i and j represent 0 or 1; T represents a divalent straight chain hydrocarbon group having 1 to 6 carbon atoms or a divalent branched chain hydrocarbon group having 2 to 10 carbon atoms; and a, b and c independently represent an integer of 0 to 10, wherein a, b and c satisfy a+b+c≥1. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element and a display device.

  An electroluminescent element is a self-luminous all-solid-state element, has high visibility and is resistant to impact, and thus is widely expected to be applied. Currently, those using inorganic phosphors are the mainstream and widely used. However, since driving requires an AC voltage of 200 V or more, 50 Hz or more and 1000 Hz or less, the running cost is high and the luminance is insufficient. Have the following problems. On the other hand, research on electroluminescent devices using organic compounds first started with a single crystal such as anthracene, but the film thickness was as thick as about 1 mm and a driving voltage of 100 V or more was required. For this reason, attempts have been made to reduce the thickness by vapor deposition (see Non-Patent Document 1). The light emission of these elements is such that electrons are injected from one of the electrodes and holes are injected from the other electrode, so that the light emitting material in the element is excited to a high energy level, and the excited illuminant becomes the base. This is a phenomenon in which excess energy for returning to the state is emitted as light. However, the driving voltage is still as high as 30 V, the density of electron / hole carriers in the film is low, and the photon generation probability due to carrier recombination is low, so that sufficient luminance cannot be obtained, leading to practical use. There wasn't.

However, in 1987, Tang et al., A functionally separated organic electric field in which a hole transporting organic low molecular weight compound and a fluorescent organic low molecular weight compound having an electron transporting ability were sequentially stacked on a transparent substrate by a vacuum deposition method. As a light emitting device, a device capable of obtaining a high luminance of 1000 cd / m ² or more at a low voltage of about 10 V has been reported (see Non-Patent Document 2 and Patent Document 1). Since then, research and development of organic electroluminescent devices have been actively conducted. Has been done. These electroluminescent elements having a stacked structure are structures in which an organic light emitter and a charge transporting organic substance (charge transport material) are stacked on an electrode, and each hole and electron moves through the charge transport material and is regenerated. Emits light when bonded. As the organic light emitter, an organic dye emitting fluorescence such as 8-quinolinol aluminum complex or coumarin compound is used. Examples of the charge transport material include diamino compounds such as N, N-di (m-tolyl) N, N′-diphenylbenzidine and 1,1-bis [N, N-di (p-tolyl) aminophenyl] cyclohexane, 4- (N, N-diphenyl) aminobenzaldehyde-N, N-diphenylhydrazone compound and the like.

Organic electroluminescent devices using these organic compounds have high emission characteristics, but have problems in thermal stability and storage stability during light emission. A layer formed of an organic material of an electroluminescent element is very thin, tens to hundreds of nanometers, and a voltage applied per unit thickness is very high, and is driven at a high current density of several mA / cm ^2. Therefore, a large amount of Joule heat is generated. For this reason, hole transporting low molecular weight compounds and fluorescent organic low molecular weight compounds formed in an amorphous glass state by vapor deposition gradually crystallize as the temperature rises and finally melt, resulting in a decrease in luminance and dielectric breakdown. Many phenomena were observed, and as a result, the lifetime of the device was reduced. This low thermal stability is believed to be due to the low glass transition temperature of the material. That is, many low molecular weight compounds have low melting points and high symmetry. Therefore, in order to solve the problem relating to thermal stability, N, N-di (1-naphthyl) N, N′— introduced with an α-naphthyl group that improves the glass transition temperature and obtains a stable amorphous glass state is obtained. An organic electroluminescence device using diphenylbenzidine (see Non-Patent Document 3) and starburst amine (see Non-Patent Document 4) has been reported. However, since these materials alone have an energy barrier due to the ionization potential of the hole transport material, they do not satisfy the hole injection property from the anode or the hole injection property to the light emitting layer. Furthermore, in the two-layered element structure of the hole transport layer and the light emitting layer, an interdiffusion phenomenon occurs and the light emission efficiency is lowered. Also, during device fabrication, considerable heat is applied during fabrication processes such as vapor deposition, baking, annealing, wiring, and sealing, and thermal stability is ensured enough to withstand changes over time due to prolonged use. Therefore, improvement of the glass transition temperature in a further material is desired.

  On the other hand, research and development have also been conducted on electroluminescent devices using polymer materials instead of low molecular compounds, and conductive polymer devices such as poly (p-phenylene vinylene) (see Non-Patent Document 5 and Patent Document 2). , A polymer device in which triphenylamine is introduced into the side chain of polyphosphazene (see Non-Patent Document 6), an element in which an electron transport material and a fluorescent dye are mixed in a hole-transporting polyvinyl carbazole (see Non-Patent Document 7) Has been proposed. Although these have a relatively high glass transition point compared to low molecular weight compounds, poly (p-phenylene vinylene) is heat-treated after spin coating of a soluble precursor, so that defects occur in the main chain conjugated polymer. Easily reduces the light emission characteristics. Phosphazene has a problem that the ionization potential is high and the charge injection characteristic is lowered. Polyvinylcarbazole has a high glass transition point, but when trapped by impurities or when a low molecular weight compound is mixed into a polymer, the low molecular weight acts as a plasticizer, and the brightness and luminous efficiency are still low. It does not reach the laminated type field emission device using a compound.

In addition, as a manufacturing method, a coating method is desirable from the viewpoint of simplification of manufacturing, workability, large area, cost, and the like, and it has been reported that an element can be obtained by a casting method (Non-Patent Documents 8 and 9). reference). However, since the charge transport material has poor solubility and compatibility with solvents and resins, it is easy to crystallize and has defects in production or characteristics.
Thin Solid Films, 94, 171 (1982) Appl. Phys. Lett. , 51, 913 (1987) IEICE technical report, OME95-54 (1995) Proceedings of the 40th Joint Conference on Applied Physics 30a-SZK-14 (1993) Nature, 357, 477 (1992) 42nd Polymer Symposium Proceedings 20J21 (1993) Proceedings of the 38th Joint Conference on Applied Physics 31p-G-12 (1991) The 50th JSAP Scientific Lecture Proceedings, 29p-ZP-5 (1989)) Proceedings of the 51st Japan Society of Applied Physics, 28a-PB-7 (1990) JP 59-194393 Japanese Patent Laid-Open No. 10-92576 etc.

  An object of the present invention is to provide an organic electroluminescence device and a display device that have higher emission intensity, higher emission efficiency, and longer device lifetime than when a polymer material is used without considering the material of the organic compound layer. It is in.

The above problem is solved by the following means. That is, the present invention
The invention according to claim 1
In an electroluminescent element composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes consisting of an anode and a cathode, at least one of which is transparent or translucent,
At least one layer of the organic compound layer contains one or more polyesters composed of repeating units containing at least one selected from the structures represented by the following general formulas (I-1) and (I-2) as a partial structure. This is an organic electroluminescent element characterized by the above.

In the formula, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, and a substituted or unsubstituted aromatic ring having 2 to 10 monovalent monovalents. Or a substituted or unsubstituted monovalent aromatic heterocyclic ring, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, An alkyl group, an alkoxyl group, an aralkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, or a substituted or unsubstituted monovalent aromatic Represents a heterocycle. i, j represents 0 or 1, T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched hydrocarbon group having 2 to 10 carbon atoms, a , B, and c each independently represent an integer of 0 or more and 10 or less. Further, a + b + c ≧ 1.

The invention according to claim 2
The organic compound layer is composed of at least a light emitting layer and at least one of an electron transport layer and an electron injection layer, and the light emitting layer contains at least one kind of the polyester. It is an organic electroluminescent element as described in above.

The invention according to claim 3
The organic compound layer is composed of at least a light emitting layer and at least one layer of a hole transport layer and a hole injection layer, and the light emitting layer contains at least one kind of the polyester. Item 2. The organic electroluminescent device according to Item 1.

The invention according to claim 4
The organic compound layer is composed of at least a light emitting layer, at least one layer of a hole transport layer and a hole injection layer, and at least one layer of an electron transport layer and an electron injection layer, and the light emitting layer is the polyester. The organic electroluminescent element according to claim 1, comprising at least one of the above.

The invention according to claim 5
2. The organic electroluminescence according to claim 1, wherein the organic compound layer is composed of only a light emitting layer having a charge transport function, and the light emitting layer having the charge transport function contains one or more kinds of the polyester. It is an element.

The invention according to claim 6
The organic electroluminescent element according to claim 1, wherein the polyester is a polyester represented by the following general formula (II-1) or (II-2).

In the general formulas (II-1) and (II-2), A ¹ represents at least one selected from the structures represented by the general formulas (I-1) and (I-2), and Y ¹ represents Z ¹ represents a divalent carboxylic acid residue, m represents an integer of 1 to 5, and p represents an integer of 5 to 5000.

The invention according to claim 7 provides:
In a display device comprising one or more organic compound layers sandwiched between a pair of electrodes consisting of an anode and a cathode, at least one of which is transparent or translucent,
At least one layer of the organic compound layer includes at least one polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (I-1) and (I-2) as a partial structure. An organic electroluminescent device containing seeds and arranged in at least one of a matrix and a segment;
Drive means for driving the organic field effect elements arranged in at least one of a matrix and a segment;
It is provided with the following.

In the formula, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, and a substituted or unsubstituted aromatic ring having 2 to 10 monovalent monovalents. Or a substituted or unsubstituted monovalent aromatic heterocyclic ring, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, An alkyl group, an alkoxyl group, an aralkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, or a substituted or unsubstituted monovalent aromatic Represents a heterocycle. i, j represents 0 or 1, T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched hydrocarbon group having 2 to 10 carbon atoms, a , B, and c each independently represent an integer of 0 or more and 10 or less. Further, a + b + c ≧ 1.

  As described above, according to the present invention, an organic electroluminescent element and a display device having a large emission intensity, a high luminous efficiency, and a long element lifetime as compared with the case of using a polymer material without considering the material of the organic compound layer. There is an effect that it can be provided.

  The organic electroluminescent device of this embodiment is composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes consisting of an anode and a cathode, at least one of which is transparent or translucent, and at least one of the organic compound layers One layer contains 1 or more types of polyester which consists of a repeating unit which contains as a partial structure at least 1 type selected from the structure shown by the following general formula (I-1) and (I-2).

  This polyester is excellent in thermal stability during light emission, solubility in solvents and resins, and phase solubility. And since the organic electroluminescent element of this embodiment contains the organic compound layer containing the said polyester, luminous intensity is large, luminous efficiency is high, element lifetime is long, and manufacture is easy.

In the formula, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, and a substituted or unsubstituted aromatic ring having 2 to 10 monovalent monovalents. Or a substituted or unsubstituted monovalent aromatic heterocyclic ring, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently a hydrogen atom, An alkyl group, an alkoxyl group, an aralkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, or a substituted or unsubstituted monovalent aromatic Represents a heterocycle. i, j represents 0 or 1, T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched hydrocarbon group having 2 to 10 carbon atoms, a , B, and c each independently represent an integer of 0 or more and 10 or less. Further, a + b + c ≧ 1.

In general formulas (I-1) and (I-2), the number of aromatic rings of the polynuclear aromatic hydrocarbon and the condensed aromatic hydrocarbon selected as the structure representing Ar is 2 or more, but 10 or less. 5 or less is preferable.
In general formulas (I-1) and (I-2), the polynuclear aromatic hydrocarbon, the condensed aromatic hydrocarbon, and the aromatic heterocycle selected as the structure representing Ar are not particularly limited. In addition, the polynuclear aromatic hydrocarbon, the condensed aromatic hydrocarbon, and the aromatic heterocycle in the present embodiment mean specifically defined as follows.

  That is, the “polynuclear aromatic hydrocarbon” represents a hydrocarbon in which 2 to 10 aromatic rings composed of carbon and hydrogen are present and the rings are bonded to each other through a carbon-carbon bond. Specific examples include biphenyl and terphenyl. The “condensed aromatic hydrocarbon” represents a hydrocarbon in which two or more aromatic rings composed of carbon and hydrogen are present and the rings share a pair of carbon atoms. Specific examples include naphthalene, anthracene, phenanthrene and fluorene.

“Aromatic heterocycle” refers to an aromatic ring containing elements other than carbon and hydrogen. The aromatic heterocyclic ring includes both those in which an aromatic ring is substituted with a heterocyclic ring and those in which a heterocyclic ring is substituted with an aromatic ring.
In addition, for the heterocyclic ring, the number of atoms (Nr) constituting the ring skeleton is preferably Nr = 5 and / or 6. Further, the type and number of atoms (heterogeneous atoms) other than carbon atoms constituting the ring skeleton are not particularly limited. For example, a sulfur atom, a nitrogen atom, an oxygen atom and the like are preferably used, and two types are included in the ring skeleton. The above and / or two or more different atoms may be contained. In particular, as a heterocyclic ring having a 5-membered ring structure, thiophene, pyrrole and furan, or a heterocyclic ring in which the 3- and 4-position carbons of the compound are replaced with nitrogen are preferably used. Pyridine is preferably used.

In the general formulas (I-1) and (I-2), a, b, and c each independently represent an integer of 0 to 10, and any two or more of a, b, and c are It may be the same. Further, a + b + c ≧ 1.
Among these, 10 ≧ a + b + c ≧ 1 is preferable, and 5 ≧ a + b + c ≧ 1 is particularly preferable.

In the general formulas (I-1) and (I-2), the phenyl group, polynuclear aromatic hydrocarbon, condensed aromatic hydrocarbon, and aromatic heterocycle selected as the structure representing Ar have a substituent. Examples of the substituent include a hydrogen atom, an alkyl group, an alkoxyl group, an aryl group, an aralkyl group, a substituted amino group, and a halogen atom.
As an alkyl group, a C1-C10 thing is preferable, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group etc. are mentioned.
As the alkoxyl group, those having 1 to 10 carbon atoms are preferable, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
As the aryl group, those having 6 to 20 carbon atoms are preferable, and examples thereof include a phenyl group and a toluyl group.
As the aralkyl group, those having 7 to 20 carbon atoms are preferable, and examples thereof include a benzyl group and a phenethyl group.
Examples of the substituent of the substituted amino group include an alkyl group, an aryl group, an aralkyl group, and the like, and specific examples are as described above.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom is preferable.

In the general formulas (I-1) and (I-2), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are each independently a hydrogen atom, an alkyl group, an alkoxyl group, or an aralkyl. A substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, a substituted or unsubstituted monovalent aromatic heterocyclic ring, R ¹ , Any two or more of R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ may be the same.
As the alkyl group, alkoxyl group, and aralkyl group, the substitution that the benzene ring, polynuclear aromatic hydrocarbon or condensed aromatic hydrocarbon of Ar in the general formulas (I-1) and (I-2) described above may have Synonymous with group.
Examples of the substituted or unsubstituted phenyl group, the monovalent condensed aromatic hydrocarbon having 2 or more and 10 or less substituted or unsubstituted aromatic rings, and the substituted or unsubstituted monovalent aromatic heterocyclic ring include the above-described general formula ( It is synonymous with Ar in I-1) and (I-2).

  In the general formulas (I-1) and (I-2), T is a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched chain having 2 to 10 carbon atoms. Represents a hydrocarbon group, preferably selected from a divalent linear hydrocarbon group having 2 to 6 carbon atoms and a divalent branched hydrocarbon group having 3 to 7 carbon atoms. A specific structure is shown below.

In general formulas (I-1) and (I-2), Ar is preferably a phenyl group, a biphenyl group, a toluyl group, an ethylphenyl group, a fluorinated phenyl group, a carbazoyl group, a benzothienyl group, or triphenyl. Amino group, 4- (2-thienyl) phenyl group, 4- (5-hexyl-2-thienyl) phenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-dibutyl-2-fluorenyl group, diphenylstil A benin group, a naphthyl group, a spirofluorenyl group, a phenylsilole group, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are each independently a hydrogen atom, a methyl group, or a butyl group. I, j is 0 or 1, and T is an ethylene group, a propylene group, an isopropylene group, a 2,2′-dimethylbutylene group, a butylene group, or a pentylene group. A, b and c are each independently 0, 1 or 2, a + b + c is 1 or more and 5 or less, and the bonding position is 3, 4, or 3, 3 ′, 4, 4 ′ Is mentioned.

In general formulas (I-1) and (I-2), Ar is preferably a phenyl group, a biphenyl group, a 4- (5-hexyl-2-thienyl) phenyl group, a toluyl group, an ethylphenyl group, A triphenylamino group, a 9,9-dimethyl-2-fluorenyl group, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are each independently a hydrogen atom or a butyl group; i and j are 0 or 1, T is an ethylene group, butylene group or pentylene group, a, b and c are each independently 0 or 1 or 2, and a + b + c is 2 or more and 5 or less , The bonding position is 4, or 4,4 ′.

Specific examples (1-211) of the structure represented by the general formula (I-1) are shown below.
The central skeleton represents a skeleton including thiophene sandwiched between two nitrogen atoms in the structure represented by the general formula (I-1).

Specific examples (212 to 422) of the structure represented by the general formula (I-2) are shown below.
The central skeleton represents a skeleton including thiophene sandwiched between two nitrogen atoms in the structure represented by the general formula (I-2).

  Examples of polyesters composed of repeating units having at least one selected from the structures represented by formulas (I-1) and (I-2) as partial structures in the present embodiment include the following formulas (II-1) and (II). -2) is preferably used.

In the general formulas (II-1) and (II-2), A ¹ represents at least one selected from the structures represented by the general formulas (I-1) and (I-2), and one polymer Two or more types of structures A may be included therein.

In general formulas (II-1) and (II-2), Y ¹ represents a divalent alcohol residue, Z ¹ represents a divalent carboxylic acid residue, and m represents an integer of 1 to 5. , P represents an integer of 5 or more and 5000 or less. Specific examples of Y ¹ and Z ¹ include groups selected from the following formulas (1) to (6).

Wherein R ³ and R ⁴ are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, or Represents a halogen atom, d and e each represents an integer of 1 to 10, f and g each represents an integer of 0, 1 or 2, h and i each represents 0 or 1, and V represents It has the same meaning as described above.

The weight average molecular weight Mw of the polyester composed of repeating units with at least one selected from the structures represented by the general formulas (I-1) and (I-2) used in the present embodiment as a partial structure is 5000 or more and 300,000 or less. Those in the range are preferred.
Hereinafter, although the specific example of said polyester shown by general formula (II-1) and (II-2) is shown, this embodiment is not limited to these specific examples. The numbers in the monomer column in the table correspond to the structure numbers which are specific examples of the structures represented by the general formulas (I-1) and (I-2). Moreover, m means m in general formula (II-1) and (II-2). Hereinafter, specific examples (compounds) assigned with respective numbers, for example, specific examples assigned number 15 are referred to as exemplary compounds (15).

A method for synthesizing monomers used in this embodiment will be described below. The synthesis method in the present embodiment is not limited to these.
Palladium coupling reaction of a dihalogen compound having a central thiophene skeleton represented by general formulas (I-1) and (I-2) with a diarylamine compound or a center represented by general formulas (I-1) and (I-2) It can be synthesized through a copper-catalyzed coupling reaction between a boron compound such as diboronic acid or dipinacol ester having a thiophene skeleton and the diarylamine compound.

  The method for synthesizing the polyester used in the present embodiment can be used by combining known methods depending on the desired structure, and is not particularly limited, but as a specific example, the general formula (I-1) And a polyester comprising a repeating unit containing at least one selected from the structure represented by (I-2) as a partial structure is a polyester represented by the general formula (II-1) or (II-2). Some cases will be described in detail below.

  When the polyester used in the present embodiment is a polyester represented by the general formula (II-1) or (II-2), a monomer represented by the following general formula (I-3) is, for example, It can be synthesized by polymerization by a known method described in the 4th edition, Experimental Chemistry Course Vol. 28 (Maruzen, 1992).

In General Formula (I-3), A ¹ represents at least one selected from the structures represented by General Formulas (I-1) and (I-2), and A ′ represents a hydroxyl group or a halogen atom. Or the group —O—R ⁶ , where R ⁶ represents an alkyl group, a substituted or unsubstituted aryl group, or an aralkyl group.

  That is, the polyesters represented by the general formulas (I-1) and (I-2) can be synthesized as follows.

1) When A ′ is a hydroxyl group, the monomer is HO— (Y ¹ —O) _m —H (Y ¹ represents a divalent alcohol residue, and m represents an integer of 1 or more and 5 or less). The indicated dihydric alcohols are mixed in an approximately equivalent amount and polymerized using an acid catalyst. As the acid catalyst, those used for usual esterification reaction such as sulfuric acid, toluenesulfonic acid, trifluoroacetic acid and the like can be used. It is preferably used in the range of 1/1000 to 1/50 parts by weight. In order to remove water generated during the polymerization, it is preferable to use a solvent azeotropic with water, and toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and 1 part by weight with respect to 1 part by weight of the monomer. The amount is 100 parts by weight or less, preferably 2 parts by weight or more and 50 parts by weight or less. The reaction temperature can be arbitrarily set, but it is preferable to carry out the reaction at the boiling point of the solvent in order to remove water generated during the polymerization.

  When the solvent is not used after completion of the reaction, it is dissolved in a soluble solvent. When a solvent is used, the reaction solution is dropped as it is in a poor solvent in which alcohols such as methanol and ethanol and polymers such as acetone are difficult to dissolve, to precipitate the polyester, and after separating the polyester, Wash thoroughly with organic solvent and dry. Further, if necessary, the reprecipitation treatment in which the polyester is precipitated by dissolving in an appropriate organic solvent and dropping in a poor solvent may be repeated. The reprecipitation treatment is preferably carried out with efficient stirring with a mechanical stirrer or the like. The solvent for dissolving the polyester in the reprecipitation treatment is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight, based on 1 part by weight of the polyester. The poor solvent is used in an amount of 1 to 1,000 parts by weight, preferably 10 to 500 parts by weight, based on 1 part by weight of the polyester.

2) When A ′ is halogen, the monomer is HO— (Y ¹ —O) _m —H (Y ¹ represents a divalent alcohol residue, and m represents an integer of 1 to 5). The indicated dihydric alcohols are mixed in an approximately equivalent amount and polymerized using an organic basic catalyst such as pyridine or triethylamine. The organic basic catalyst is used in the range of 1 equivalent to 10 equivalents, preferably 2 equivalents to 5 equivalents, relative to 1 equivalent of the monomer. As the solvent, methylene chloride, tetrahydrofuran (THF), toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and are 1 to 100 parts by weight, preferably 2 to 50 parts by weight with respect to 1 part by weight of the monomer. It is used in the range of parts by weight or less. The reaction temperature can be arbitrarily set. After the polymerization, reprecipitation treatment is performed as described above, and purification is performed.

  In the case of dihydric alcohols with high acidity such as bisphenol, an interfacial polymerization method can also be used. That is, it can polymerize by adding a dihydric alcohol to water, adding an equivalent base and dissolving it, and then adding a monomer solution equivalent to the dihydric alcohol with vigorous stirring. In this case, water is used in an amount of 1 to 1,000 parts by weight, preferably 2 to 500 parts by weight, per 1 part by weight of the dihydric alcohol. As the solvent for dissolving the monomer, methylene chloride, dichloroethane, trichloroethane, toluene, chlorobenzene, 1-chloronaphthalene and the like are effective. The reaction temperature can be arbitrarily set, and in order to promote the reaction, it is effective to use a phase transfer catalyst such as an ammonium salt or a sulfonium salt. The phase transfer catalyst is used in the range of 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, based on 1 part by weight of the monomer.

3) When A ′ is —O—R ⁶ , the monomer contains HO— (Y ¹ —O) _m —H (Y ¹ represents a divalent alcohol residue, and m is an integer of 1 or more and 5 or less. In addition, an excess of a dihydric alcohol represented by (2) is used, and inorganic acids such as sulfuric acid and phosphoric acid, titanium alkoxides, acetates or carbonates such as calcium and cobalt, and oxides of zinc and lead are used as catalysts. It can be synthesized by heating and transesterification. The dihydric alcohol is used in a range of 2 equivalents to 100 equivalents, preferably 3 equivalents to 50 equivalents, relative to 1 equivalent of the monomer. The catalyst is used in the range of 1 / 10,000 parts by weight to 1 part by weight, preferably 1 / 1,000 parts by weight to 1/2 part by weight, based on 1 part by weight of the monomer. The reaction is carried out at a reaction temperature of 200 ° C. or more and 300 ° C. or less, and after completion of the ester exchange from the group —O—R ⁶ to the group —O— (Y ¹ —O) _m —H, HO— (Y—O) _m In order to promote polymerization due to elimination of -H, it is preferable to carry out the reaction under reduced pressure. Also, HO- (Y ¹ -O) _m —H is removed azeotropically under normal pressure using a high boiling point solvent such as 1-chloronaphthalene that can be azeotroped with HO— (Y ¹ —O) _m —H. Can also be reacted.

  Further, polyester can be synthesized as follows. In each of the above cases, a compound represented by the following general formula (I-4) was produced by adding an excess of a dihydric alcohol and reacting, and then the compound was represented by the above general formula (I-3). What is necessary is just to make it react with a bivalent carboxylic acid or a bivalent carboxylic acid halide etc. by the method similar to the above using it instead of a monomer, and, thereby, polyester can be obtained.

However, in the general formula (I-4), ^{A 1} represents or at least one selected from structures represented by the general formula (I-1) and (I-2), ^{Y 1} is a divalent alcohol Represents a residue, and m represents an integer of 1 or more and 5 or less.

  Further, an arbitrary molecule may be introduced into the terminal of the polyester. In that case, the following method is mentioned. That is, when A 'is a hydroxyl group, it can be introduced by copolymerizing a monocarboxylic acid as a terminal-introducing compound or by charging and reacting a monocarboxylic acid with an electron transporting compound after the polymerization reaction of the polymer.

When A ′ is halogen, the monoacid chloride of the terminally introduced compound can be copolymerized, or after the polymerization reaction of the polymer, the monoacid chloride of the terminally introduced compound can be charged and reacted for introduction. When A ′ is —O—R ⁶ , it is possible to copolymerize the monoester of the terminally introduced compound, or after the polymerization reaction of the polymer, charge and introduce the monoester of the terminally introduced compound.

Next, the layer configuration of the organic electroluminescent element according to the present embodiment will be described in detail.
The organic electroluminescent device according to the present embodiment is an electrode composed of a pair of anode and cathode, at least one of which is transparent or translucent, and one or a plurality of organic compound layers sandwiched between the pair of electrodes, It has a layer structure including Moreover, at least one layer of the organic compound layer contains at least one kind of the polyester.

  In addition, the film thickness of the organic compound layer positioned closest to the anode among the organic compound layers containing the polyester is in the range of 20 nm to 100 nm (desirably, 20 nm to 80 nm, more desirably 20 nm. And within 50 nm or less). This organic compound layer is a light-emitting layer having charge transport capability when the organic compound layer is a single layer type, and preferably a hole transport layer when the organic compound layer is a function separation type (stacked type).

  In the organic electroluminescent device according to the present embodiment, when the organic compound layer is composed of only the buffer layer and the light emitting layer, this light emitting layer means a light emitting layer having charge transporting ability, and this charge transporting ability The light emitting layer which has this contains the said polyester.

  When the organic compound layer has one or more other layers in addition to the light emitting layer (in the case of a function separation type of three or more layers), the other layers excluding the light emitting layer are carrier transport layers, , A hole transport layer, an electron transport layer, or a layer composed of a hole transport layer and an electron transport layer, and the polyester is contained in at least one of these layers.

  Specifically, the organic compound layer includes, for example, (1) a configuration including at least a light emitting layer and at least one of an electron transport layer and an electron injection layer, and (2) at least an issue layer, a hole transport layer, and a hole. (3) a configuration including at least a light emitting layer, at least one of an electron transport layer and an electron injection layer, and at least one of a hole transport layer and a hole injection layer. May be. In this case, it is desirable that the polyester is contained in at least one of these layers (hole transport layer, electron transport layer, light emitting layer), but preferably the polyester is contained as a hole transport material. Is desirable. In particular, it is preferable that at least one of the light emitting layer, the hole transport layer, and the hole injection layer contains the polyester.

  Here, in the configuration including the light-emitting layer and at least one of the electron transport layer and the electron injection layer, both manufacturability and luminous efficiency can be achieved as compared with other layer configurations. This is because the number of layers is smaller than that of a layer structure in which all functions are separated, but in general, the electron injection efficiency, which is lower in mobility than holes, is compensated for and the charge in the light emitting layer is balanced. Conceivable.

  In a configuration including a light emitting layer, at least one of a hole transport layer and a hole injection layer, and at least one of an electron transport layer and an electron transport layer, the light emitting layer is superior in luminous efficiency and low in comparison with other layers. Voltage drive is possible. This is presumably because the functional separation results in the highest charge injection efficiency compared to other layer configurations, and charges can be recombined in the light emitting layer.

  In the configuration including the light emitting layer and at least one of the hole transport layer and the hole injection layer, both manufacturability and durability can be achieved as compared with other configurations. This is thought to be because the number of layers is smaller than that of the layer structure in which all functions are separated, but the efficiency of hole injection into the light emitting layer is improved and excessive electron injection is suppressed in the light emitting layer.

  In the case of being composed only of the light emitting layer, it is easy to increase the area and manufacture of the element as compared with other layer configurations. This is because the number of layers is small and can be produced by wet coating, for example.

  Furthermore, in the organic electroluminescent element according to the present embodiment, the light emitting layer may contain a charge transporting material (a hole transporting material other than the polyester, an electron transporting material). Details of the transportable material will be described later.

Hereinafter, the organic electroluminescence device according to the present embodiment will be described in more detail with reference to the drawings, but is not limited thereto.
The organic electroluminescent elements of FIGS. 1 to 3 are examples when the organic compound layer has a three-layer or four-layer structure, and the organic electroluminescent elements of FIG. 4 are examples when the organic compound layer has a two-layer structure. Show. In FIG. 1 to FIG. 4, components having similar functions are described with the same reference numerals.

An organic electroluminescent element 10 shown in FIG. 1 is formed by sequentially laminating a transparent electrode 2, a light emitting layer 4, an electron transport layer 5 and a back electrode 7 on a transparent insulator substrate 1.
An organic electroluminescent element 10 shown in FIG. 2 is formed by sequentially laminating a transparent electrode 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5 and a back electrode 7 on a transparent insulator substrate 1.
The organic electroluminescent element 10 shown in FIG. 3 is formed by sequentially laminating a transparent electrode 2, a hole transport layer 3, a light emitting layer 6 having a charge transport capability, and a back electrode 7 on a transparent insulator substrate 1.
An organic electroluminescent element 10 shown in FIG. 4 is formed by sequentially laminating a transparent electrode 2, a light emitting layer 6 having a charge transport capability, and a back electrode 7 on a transparent insulator substrate 1.

  1-4, the transparent electrode 2 means an anode, and the back electrode 7 means a cathode. Each will be described in detail below.

  Further, depending on the structure of the layer containing the polyester, in the case of the layer configuration of the organic electroluminescent device 10 shown in FIG. 1, both the light emitting layer 4 and the electron transporting layer 5 can act. In the case of the layer configuration of the organic electroluminescent element 10 shown in FIG. 3, both the hole transport layer 3 and the electron transport layer 5 can act. In the case of the layer configuration of the organic electroluminescent element 10 shown in FIG. Both the hole transport layer 3 and the light emitting layer 6 having charge transporting ability can act, and in the case of the layer configuration of the organic electroluminescent element 10 shown in FIG. 4, it acts as the light emitting layer 6 having charge transporting ability. Can do. In particular, it can preferably act as a hole transport material.

  In the case of the layer configuration of the organic electroluminescent element shown in FIGS. 1 to 4, the transparent insulator substrate 1 is preferably transparent in order to extract emitted light, and glass, plastic film or the like is used. The term “transparent” means that the light transmittance in the visible region is 10% or more, and the transmittance is preferably 75% or more. The transparent electrode 2 is transparent in order to extract emitted light in the same manner as the transparent insulator substrate, and has a high work function for injecting holes, and preferably has a work function of 4 eV or more.

  As specific examples, oxide films such as indium tin oxide (ITO), tin oxide (NESA), indium oxide, zinc oxide, and indium zinc oxide, and gold, platinum, palladium, or the like deposited or sputtered are used. The sheet resistance of the electrode is desirably as low as possible, preferably several hundred Ω / □ or less, and more preferably 100 Ω / □ or less. Further, like the transparent insulator substrate, it is preferable that the light transmittance in the visible region is 10% or more, and the transmittance is 75% or more.

  In the present embodiment, the buffer layer may be formed so as to be in contact with the anode (transparent electrode 2). The buffer layer preferably contains one or more charge injection materials. Then, the charge injection material is formed using the charge injection material having the substituted silicon group. Specifically, for example, the buffer layer includes a three-dimensional cross-linked product formed of the charge injection material having the substituted silicon group.

  The charge injection material is a layer provided in contact with the surface of the buffer layer opposite to the side on which the anode is provided (that is, the light emitting layer 4 in FIG. 1, the hole transport layer 3 in FIGS. 4, the ionization potential is preferably 5.2 eV or less, and more preferably 5.1 eV or less, in order to improve the charge injection property into the light emitting layer 6) having a charge transporting ability. The number of buffer layers 3 is not particularly limited, but is preferably one or two layers, and more preferably one layer.

  In addition to the above materials, other materials that do not have charge injection properties such as a binder resin can be used as necessary for the material constituting the buffer layer.

  The electron transport layer 5 may be formed of the polyester alone provided with a function (electron transport ability) according to the purpose, but the electron mobility is adjusted for the purpose of further improving electrical characteristics. Therefore, it may be formed by mixing and dispersing an electron transport material other than the polyester in the range of 1 wt% to 50 wt%.

  Preferred examples of such an electron transport material include oxadiazole derivatives, triazole derivatives, phenylquinoxaline derivatives, nitro-substituted fluorenone derivatives, diphenoquinone derivatives, thiopyrandioxide derivatives, fluorenylidenemethane derivatives, and the like. Preferable specific examples include the following compounds (III-1) to (III-3), but are not limited thereto. In addition, when forming the electron transport layer 6 without using the said polyester, the electron transport layer 6 is formed using these electron transport materials.

  For the purpose of improving the electron injection property from the cathode, the material for forming the electron injection layer between the electron transport layer 5 and the back electrode 7 has a function of injecting electrons from the cathode. Any material that is the same as the electron transporting material can be used.

  The hole transport layer 3 may be formed of a polyester having a function (hole transport ability) according to the purpose, but a hole transport material other than polyester may be used to adjust the hole mobility. It may be formed by mixing and dispersing in the range of 1% by weight to 50% by weight.

  Examples of the hole transport material include tetraphenylenediamine derivatives, triphenylamine derivatives, carbazole derivatives, stilbene derivatives, arylhydrazone derivatives, porphyrin-based compounds, and the like, and particularly preferable specific examples include the following compounds (IV-1) to (IV- 7), and a tetraphenylenediamine derivative is desirable because of its good compatibility with the polyester. Moreover, you may mix and use with other general purpose resin etc. In addition, when forming the hole transport layer 4 without using the said polyester, the hole transport layer 4 is formed by using these hole transportable materials. In compound (IV-7), n (integer value) is preferably in the range of 10 to 100,000, and more preferably in the range of 1,000 to 50,000.

  For the purpose of improving the hole injection property from the anode, the material for forming the hole injection layer between the transparent electrode 2 and the hole transport layer 3 injects holes from the anode. Any material may be used as long as it has a function, and the same material as the hole transporting material can be used. As a particularly preferable specific example, the following exemplified compound (V-1) or (V-2) can be used. Can be mentioned. Here, in (V-2), n represents an integer of 1 or more.

  For the light-emitting layer 4, a compound that exhibits a high fluorescence quantum yield in a solid state as compared with other types is used as the light-emitting material. In the case where the light emitting material is an organic low molecule, it is a condition that a good thin film can be formed by applying and drying a solution or dispersion containing a low molecular weight and a binder resin. In the case of a polymer, it is a condition that a good thin film can be formed by applying and drying a solution or dispersion containing itself.

  Preferably, in the case of small organic molecules, chelate-type organometallic complexes, polynuclear or condensed aromatic ring compounds, perylene derivatives, coumarin derivatives, styrylarylene derivatives, silole derivatives, oxazole derivatives, oxathiazole derivatives, oxadiazole derivatives, etc. In the case of a polymer, examples include polyparaphenylene derivatives, polyparaphenylene vinylene derivatives, polythiophene derivatives, polyacetylene derivatives, polyfluorene derivatives, and the like. As preferred specific examples, the following compounds (VI-1) to (VI-17) are used, but are not limited thereto.

In the structural formulas (VI-1) to (VI-17) below, Ar is a monovalent group or a divalent group having the same structure as Ar shown in the general formulas (I-1) and (I-2). Means group.
X represents a substituted or unsubstituted divalent aromatic group. Specifically, X is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having 2 to 10 aromatics, or a substituted or unsubstituted aromatic number 2 or more. A divalent condensed ring aromatic hydrocarbon having 10 or less, a substituted or unsubstituted divalent aromatic heterocyclic ring, or a substituted or unsubstituted divalent aromatic group containing at least one aromatic heterocyclic ring; To express. n and x represent an integer of 1 or more, and y represents 0 or 1.

  In addition, for the purpose of improving the durability of the organic electroluminescent device or improving the light emission efficiency, the light emitting material may be doped with a dye compound different from the light emitting material as a guest material. When the light emitting layer is formed by vacuum deposition, doping is performed by co-evaporation, and when the light emitting layer is formed by applying and drying a solution or dispersion, doping is performed by mixing in the solution or dispersion. The doping ratio of the dye compound in the light emitting layer is about 0.001 to 40% by weight, preferably about 0.01 to 10% by weight.

  As the coloring compound used for this doping, an organic compound that has good compatibility with the light emitting material and does not prevent the formation of a good thin film of the light emitting layer is used, and preferably a DCM derivative, a quinacridone derivative, a rubrene derivative, a porphyrin System compounds and the like. As preferred specific examples, the following compounds (VII-1) to (VII-4) are used, but are not limited thereto.

  In addition, for the purpose of improving the durability of the organic electroluminescent device or improving the light emission efficiency, 0.1% of a hole transport material other than the polyester for adjusting the hole mobility with respect to the polyester used in the present embodiment is used. It may be formed by mixing and dispersing in the range of wt% to 50 wt%. Examples of such hole transporting materials include tetraphenylenediamine derivatives, triphenylamine derivatives, carbazole derivatives, stilbene derivatives, aryl hydrazone derivatives, and porphyrin compounds. Tetraphenylene has good compatibility with polyesters. Diamine derivatives and triphenylamine derivatives are preferred.

  Similarly, when adjusting the electron mobility, the electron transport material may be mixed and dispersed in the range of 0.1% by weight to 50% by weight with respect to the polyester. Such electron transport materials include oxadiazole derivatives, nitro-substituted fluorenone derivatives, diphenoquinone derivatives, thiopyran dioxide derivatives, silole derivatives, chelate-type organometallic complexes, polynuclear or condensed aromatic ring compounds, perylene derivatives, triazole derivatives, full Examples include olenylidene methane derivatives.

Further, when both the hole mobility and the electron mobility need to be adjusted, both the hole transport material and the electron transport material may be mixed together in the polyester.
Furthermore, an appropriate resin (polymer) or an additive may be added to improve film formability and prevent pinholes. Specific resins include polycarbonate resin, polyester resin, methacrylic resin, acrylic resin, polyvinyl chloride resin, cellulose resin, urethane resin, epoxy resin, polystyrene styrene resin, polyvinyl acetate resin, styrene butadiene copolymer, vinyl chloride- An acrylonitrile copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicon resin, poly-N-vinylcarbazole resin, polysilane resin, polythiophene, polypyrrole, or other conductive resin can be used. Moreover, as an additive, a well-known antioxidant, a ultraviolet absorber, a plasticizer, etc. can be used.

In order to improve the charge injection property, a hole injection layer and / or an electron injection layer may be used. As the hole injection material, a phenylenediamine derivative, a phthalocyanine derivative, an indanthrene derivative, a polyalkylene diester, An oxythiophene derivative or the like is used. These may be mixed with a Lewis acid, a sulfonic acid, or the like. As the electron injection material, metals such as Li, Ca, and Sr, metal fluorides such as LiF and MgF, and metal oxides such as MgO, Al ₂ O ₃ , and LiO are used.

  When the polyester is used for a function other than the light emitting function, a light emitting compound is used as a light emitting material. As the light-emitting material, a compound that exhibits high emission quantum efficiency in a solid state is used. The light-emitting material may be either a low molecular compound or a high molecular compound. Suitable examples of organic low molecular compounds include chelate-type organometallic complexes, polynuclear or condensed aromatic ring compounds, perylene derivatives, coumarin derivatives, and styrylarylene derivatives. In the case where a silole derivative, an oxazole derivative, an oxathiazole derivative, an oxadiazole derivative or the like is a polymer, a polyparaphenylene derivative, a polyparaphenylene vinylene derivative, a polythiophene derivative, a polyacetylene derivative, or the like is used. As preferable specific examples, the following light emitting materials (VIII-1) to (VIII-17) are used, but the invention is not limited thereto. In the light emitting materials (VIII-13) to (VIII-17), V represents the functional group shown above, and n and g each represents an integer of 1 or more.

  Further, for the purpose of improving the durability of the device or improving the light emission efficiency, a dye compound different from the light emitting material may be doped as a guest material in the light emitting material or the polyester. The doping ratio of the dye compound is about 0.001 to 40% by weight, preferably about 0.001 to 10% by weight. As the coloring compound used for such doping, an organic compound that has good compatibility with the light emitting material and the polyester and does not prevent the formation of a good thin film of the light emitting layer is used, and preferably a coumarin derivative, a DCM derivative, Quinacridone derivatives, rubrene derivatives, porphyrin derivatives, metal complex compounds such as Ir, Eu, and Pt are used. Preferable specific examples include the following dye compounds (IX-1) to (IX-6), but are not limited thereto.

  The light emitting layer 4 may be formed of the light emitting material alone, but the polyester is added to the light emitting material in the range of 1% by weight to 50% by weight for the purpose of further improving electrical characteristics and light emitting characteristics. It may be formed by mixing and dispersing, or a charge transporting material other than the polyester may be mixed and dispersed in the light-emitting polymer in the range of 1 to 50% by weight.

  The light emitting layer 6 having a charge transporting ability is, for example, the light emitting material (VI-1) to (VI) as a light emitting material in the polyester given a function (hole transport ability or electron transport ability) according to the purpose. It is desirable to include a material in which VI-17) is dispersed in an amount of 50% by weight or less. In this case, in order to adjust the balance between holes and electrons injected into the organic electroluminescent device, a charge transport material other than the polyester may be dispersed in an amount of 10 wt% to 50 wt%.

  As the charge transport material, when adjusting the electron mobility, the electron transport material preferably includes an oxadiazole derivative, a nitro-substituted fluorenone derivative, a diphenoquinone derivative, a thiopyrandioxide derivative, a fluorenylidenemethane derivative, and the like. . Preferable specific examples include the compounds (III-1) to (III-3). In addition, it is desirable to use an organic compound that does not exhibit strong electron interaction with the polyester, and more desirably, the following compound (X) is used, but is not limited thereto.

  Similarly, when adjusting the hole mobility, particularly preferable examples of the hole transporting material include tetraphenylenediamine derivatives, triphenylamine derivatives, carbazole derivatives, stilbene derivatives, arylhydrazone derivatives, porphyrin compounds, and the like. Although the said compound (VIII-1)-(VIII-7) is mentioned, Since the compatibility with polyester is good, a tetraphenylenediamine derivative is desirable.

  The back electrode 7 is made of a metal element that can be vacuum-deposited and has a small work function for electron injection, but is particularly preferably magnesium, aluminum, silver, indium and alloys thereof, lithium fluoride, and oxide. Examples thereof include metal halogen compounds such as lithium and metal oxides.

Further, a protective layer may be provided on the back electrode 7 in order to prevent the element from being deteriorated by moisture or oxygen. Specific materials for the protective layer include metals such as In, Sn, Pb, Au, Cu, Ag, and Al, metal oxides such as MgO, SiO ₂ , and TiO ₂ , polyethylene resin, polyurea resin, and polyimide resin. Resin. For forming the protective layer, a vacuum deposition method, a sputtering method, a plasma polymerization method, a CVD method, a coating method, or the like can be applied.

  The organic electroluminescent elements shown in FIGS. 1 to 4 are produced by the following procedure. First, the buffer layer 3 is formed on the transparent electrode 2 formed in advance on the transparent insulator substrate 1, and the coating solution obtained by dissolving or dispersing in the solvent is used for spin coating or dip coating on the transparent electrode 2. The film can be formed using a method or the like, and can be cured by heating or the like as necessary. Next, the hole transport layer 4, the light emitting layer 5, the electron transport layer 6, and the light emitting layer 7 having charge transporting ability are formed on the buffer layer 3 in accordance with the layer configuration of each organic electroluminescent element. Furthermore, on each of these layers, each layer is sequentially laminated according to the layer configuration of each organic electroluminescent element.

  Moreover, the hole transport layer 3, the light emitting layer 4, the electron transport layer 5, and the light emitting layer 6 having charge transporting ability are formed by using the materials constituting these layers by vacuum deposition as described above. Or it forms by forming into a film using a spin coating method, a dip method, etc. using the coating liquid obtained by melt | dissolving or disperse | distributing this material in an organic solvent.

  When a polymer is used as the charge transport material and the light emitting material, each layer is preferably formed by a film forming method using a coating solution, but may be formed by film forming using an ink jet method.

  Further, the thickness of the formed buffer layer is preferably in the range of 1 nm to 200 nm, particularly in the range of 10 nm to 150 nm.

  The film thicknesses of the hole transport layer 3, the light emitting layer 4, and the electron transport layer 5 are each preferably 20 nm or more and 100 nm or less, and particularly preferably 30 nm or more and 80 nm or less. The film thickness of the light emitting layer 6 having charge transporting ability is preferably 20 nm to 200 nm and preferably about 30 nm to 200 nm.

  The dispersion state of each of the materials (the polyester, the light emitting material, etc.) may be a molecular dispersion state or a particle dispersion state. In the case of a film forming method using a coating solution, it is necessary to use a common solvent for each of the above materials as a dispersion solvent in order to obtain a molecular dispersion state. It is necessary to select in consideration of solubility and solubility. In order to disperse into particles, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer, an ultrasonic method, or the like can be used.

  And finally, the organic electroluminescent element shown in FIGS. 1-4 is obtained by forming the back electrode 7 by the vacuum evaporation method on the light emitting layer 4, the electron carrying layer 5, or the light emitting layer 6 which has charge transport ability. Can do.

-Display device-
Next, the configuration of the display device according to the present embodiment will be described in detail.
The display device according to the present embodiment includes the organic electroluminescent element according to the present embodiment and driving means for driving the organic electroluminescent element.
Specifically, as a display device, for example, as shown in FIGS. 1 to 4, the display device is connected to a pair of electrodes (transparent electrode 2, back electrode 7) of an organic electroluminescent element, and a DC voltage is applied between the pair of electrodes. For example, a device provided with the voltage applying device 9 for driving as a driving means can be used.
As a driving method of the organic electroluminescent element using the voltage application device 9, for example, a DC voltage of 4 mA to 20 V and a current density of 1 mA / cm ^{2 to} 200 mA / cm ² is applied between a pair of electrodes. The organic electroluminescence device is caused to emit light.

In addition, the organic electroluminescence element of the present embodiment has been described with respect to the configuration of the minimum unit (one pixel unit). For example, the one pixel unit (organic electroluminescence element) is arranged in at least one of a matrix shape and a segment shape. Applied to the display device. When the organic electroluminescent elements are arranged in a matrix, only the electrodes may be arranged in a matrix, or both the electrodes and the organic compound layer may be arranged in a matrix. Further, in the present embodiment, when the organic electroluminescent elements are arranged in a segment shape, the electrode may be arranged in a segment shape, or both the electrode and the organic compound may be arranged in a segment shape. Also good. Note that the matrix-like or segment-like organic compound layer can be easily formed by using the above-described inkjet method.
As a driving method of the display device, a conventionally known technique, for example, a plurality of row electrodes and column electrodes are arranged, and the column electrodes are collectively processed according to image information corresponding to each row electrode while scanning the row electrodes. Simple matrix driving to be driven, active matrix driving by pixel electrodes arranged for each pixel, and the like are used.

  Hereinafter, the present embodiment will be described more specifically with reference to examples. However, these examples do not limit the present embodiment.

Example 1
-Synthesis Example 1
500 ml of acetanilide (25.0 g), methyl 4-iodophenylpropionate (64.4 g), potassium carbonate (38.3 g), copper sulfate pentahydrate (2.3 g), n-tridecane (50 ml) The flask was placed in a flask and heated and stirred at 230 ° C. for 20 hours under a nitrogen stream. After completion of the reaction, potassium hydroxide (15.6 g) dissolved in ethylene glycol (300 ml) was added, heated under reflux for 3.5 hours under a nitrogen stream, cooled to room temperature, and the reaction solution was diluted with 1 L of distilled water. And neutralized with hydrochloric acid to precipitate crystals. The crystals were collected by suction filtration, washed thoroughly with water, and transferred to a 1 L flask. Toluene (500 ml) was added thereto, heated to reflux, water was removed by azeotropy, then a solution of concentrated sulfuric acid (1.5 ml) in methanol (300 ml) was added, and the mixture was heated to reflux for 5 hours under a nitrogen stream. After the reaction, extraction with toluene was performed, and the organic layer was washed thoroughly with distilled water. Subsequently, after drying with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 36.5 g of DAA-1 was obtained by recrystallization from hexane.

  DAA-1 (8.0 g), 5,5′-dibromo-2,2′-bithiophene (4.9 g), palladium acetate (II) was added to a 200 ml three-necked flask equipped with a thermometer, a condenser and a magnetic stirrer. ) (170 mg) and rubidium carbonate (21 g) were added and dissolved in 50 ml of xylene. Tri-tertiary-butylphosphine (1.2 g) was quickly added, and the mixture was heated and refluxed magnetically stirred for 9 hours under a nitrogen atmosphere. After confirming the disappearance of the spot of [Intermediate 1] by TLC (hexane / ethyl acetate = 3/1), the mixture was cooled to room temperature. After removing inorganic substances by Celite suction filtration, washing was carried out in the order of dilute hydrochloric acid 100 ml, water 200 ml × 3, and saturated saline 200 ml × 1 in this order. After drying over anhydrous sodium sulfate, purification is performed by silica gel column chromatography (hexane / ethyl acetate = 3/1), followed by vacuum drying at 70 ° C. for 15 hours. Specific Example 18 of the above general formula (I-1) 18 Was obtained in a yield of 57%.

1.5 g of a monomer containing the above-mentioned specific example 18 of the general formula (I-1) as a partial structure, 10 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium are placed in a 50 ml three-necked eggplant flask, and 5% at 200 ° C. in a nitrogen atmosphere Stir for hours. After confirming the disappearance of the raw material 1 by TLC, the pressure was reduced to 40 Pa and the mixture was heated to 200 ° C. while distilling off ethylene glycol, and the reaction was continued for 7 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of tetrahydrofuran, insoluble matter was filtered through a 0.5 μl polytetrafluoroethylene (PTFE) filter, the filtrate was distilled off under reduced pressure, and then dissolved in 300 ml of monochlorobenzene. Washing was performed in the order of 300 ml of 1N HCl and 500 ml of water × 3. The monochlorobenzene solution was distilled off under reduced pressure to 30 ml and dropped into ethyl acetate / methanol = 1/5: 800 ml to reprecipitate the polymer. The obtained polymer was filtered, thoroughly washed with methanol, and then vacuum-dried at 70 ° C. for 16 hours to obtain 0.9 g of a polymer [Exemplary Compound: (9)]. When the molecular weight of this polymer was measured by gel permeation chromatography (GPC) (manufactured by Tosoh Corporation, HLC-8120GPC), Mw = 9.1 × 10 ⁴ (in terms of styrene) and Mw / Mn = 1.22. The degree of polymerization p determined from the molecular weight of the monomer was about 130.

ITO (manufactured by Sanyo Vacuum Co., Ltd.) formed on the transparent insulating substrate was patterned by photolithography using a strip-shaped photomask, and further etched to form a strip-shaped ITO electrode (width 2 mm). Next, the ITO glass substrate was washed with neutral detergent, pure water, acetone (for electronics industry, manufactured by Kanto Chemical) and isopropanol (for electronics industry, manufactured by Kanto Chemical) for 5 minutes each, and then spinned. It was dried with a coater. Polyester [Exemplary Compound (9)] is prepared as a hole transporting layer on the substrate in a 5 wt% monochlorobenzene solution, filtered through a 0.1 μm PTFE filter, and then a thin film having a thickness of 0.050 μm by dipping. Formed. The compound (IV-1) was deposited as a light emitting material to form a light emitting layer having a thickness of 0.055 μm. Subsequently, using a metallic mask provided with a strip-shaped hole, this mask is finally installed, and a Mg-Ag alloy is vapor-deposited by co-evaporation to form a back electrode having a width of 2 mm and a thickness of 0.15 μm by ITO. It formed so that it might cross | intersect an electrode. The effective area of the formed organic electroluminescent element was 0.04 cm ² .

(Example 2)
-Synthesis Example 2-
1.7 g of polyester [Exemplary Compound (17)] was obtained in the same manner as in Synthesis Example 1.
When the molecular weight of this polymer was measured by GPC, it was Mw = 9.1 × 10 ⁴ (styrene conversion), Mw / Mn = 1.15, and the degree of polymerization p determined from the molecular weight of the monomer was about 98.

Example 1 1 part by weight of the polyester [Exemplary Compound (17)] used in Example 1, 4 parts by weight of poly (N-vinylcarbazole), and the compound (VIII-1) were etched and washed in the same manner as in Example 1. A 10 wt% dichloroethane solution was prepared and filtered through a 0.1 μm PTFE filter. Using this solution, a thin film having a thickness of about 0.15 μm was formed by spin coating on a glass substrate on which a 2 mm wide strip-shaped ITO electrode was formed by etching. After sufficiently drying, a Mg—Ag alloy was vapor-deposited by co-evaporation to form a back electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross the ITO electrode. The effective area of the formed organic electroluminescent element was 0.04 cm ² .

-Synthesis Example 3-
In the same manner as in Synthesis Example 1, 1.6 g of polyester [Exemplary Compound (34)] was obtained.
When the molecular weight of this polymer was measured by GPC, it was Mw = 6.7 × 10 ⁴ (in terms of styrene), Mw / Mn = 1.09, and the degree of polymerization p determined from the molecular weight of the monomer was about 86.

(Example 3)
Polyester [Exemplary Compound (34)] having a thickness of 0.050 μm was formed on the ITO glass substrate etched and washed as in Example 1 as a hole transport layer as in Example 1. The compound (VIII-1) and the compound (IX-1) were formed with a thickness of 0.065 μm as the light emitting layer, and the compound (VIII-9) was formed with a thickness of 0.030 μm as the electron transport layer. Subsequently, a Mg—Ag alloy was deposited by co-evaporation to form a back electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross the ITO electrode. The effective area of the formed organic electroluminescent element was 0.04 cm ² .

-Synthesis Example 4-
In the same manner as in Synthesis Example 1, 2.2 g of polyester [Exemplary Compound (66)] was obtained.
When the molecular weight of this polymer was measured by GPC, Mw = 5.8 × 10 ⁴ (in terms of styrene) and Mw / Mn = 1.12. The degree of polymerization p determined from the molecular weight of the monomer was about 59.

Example 4
A polyester [Exemplary Compound (10)] having a thickness of 0.050 μm was formed on the ITO glass substrate etched and washed in the same manner as in Example 1 as a hole transport layer in the same manner as in Example 1 by an inkjet method. The compound (VIII-17) and the compound (IX-5) were formed as a light emitting layer with a thickness of 0.065 μm by a spin coater method. After sufficiently drying, a back electrode having a width of 2 mm and a total thickness of 0.23 μm was formed so as to intersect the ITO electrode by vapor-depositing Ca to a thickness of 0.08 μm and Al to a thickness of 0.15 μm. The effective area of the formed organic electroluminescent element was 0.04 cm ² .

(Example 5)
-Synthesis Example 5-
In the same manner as in Synthesis Example 1, 1.5 g of polyester [Exemplary Compound (81)] was obtained.
When the molecular weight of this polymer was measured by GPC, it was Mw = 8.7 × 10 ⁴ (styrene conversion), Mw / Mn = 1.34, and the degree of polymerization p determined from the molecular weight of the monomer was about 64.

  An organic electroluminescent device was produced in the same manner as in Example 2 except that the exemplified compound (81) was used instead of the exemplified compound (9) used in Example 1.

(Example 6)
-Synthesis Example 6
In the same manner as in Synthesis Example 1, 2.3 g of polyester [Exemplary Compound (82)] was obtained.
When the molecular weight of this polymer was measured by GPC, it was Mw = 7.4 × 10 ⁴ (styrene conversion), Mw / Mn = 1.17, and the degree of polymerization p determined from the molecular weight of the monomer was about 74.
An organic electroluminescent device was produced in the same manner as in Example 3 except that the exemplified compound (82) was used instead of the exemplified compound (9) used in Example 1.

(Example 7)
A 1.5 weight part dichloroethane solution of the polyester [Exemplary Compound (9)] used in Example 1 was prepared on an ITO glass substrate etched and washed in the same manner as in Example 1, and filtered through a 0.1 μm PTFE filter. Using this solution, a thin film having a thickness of about 0.05 μm was formed by an inkjet method on a glass substrate on which a 2 mm wide strip-shaped ITO electrode was formed by etching. A light emitting layer having a thickness of 0.050 μm was formed from the compound (VIII-14) as a light emitting material by an ink jet method. After sufficiently drying, a back electrode having a width of 2 mm and a total thickness of 0.23 μm was formed so as to intersect the ITO electrode by vapor-depositing Ca to a thickness of 0.08 μm and Al to a thickness of 0.15 μm. The effective area of the formed organic electroluminescent element was 0.04 cm ² .

(Example 8)
-Synthesis Example 8-
A mixed solution of 21.4 g of 5-phenylpentanoic acid, 12.1 g of iodine and 4.6 g of periodic acid dihydrate in a 300 ml three-necked flask (2 ml of sulfuric acid, 80 ml of acetic acid, 15 ml of water) was added. After stirring at 80 ° C. for 2 hours, it was poured into 500 ml of 1 l beaker pure water. The precipitated crystals were collected by suction filtration. It was washed twice with 500 ml of 10% aqueous sodium thiosulfate solution, and further washed with pure water until neutral. Vacuum drying at 50 ° C. for 15 hours gave 30 g of 5- (4-iodophenyl) pentanoic acid.
The obtained crystals were placed in a 300 ml three-necked flask, and 100 ml of toluene was added. (Methanol 20 ml, sulfuric acid 2 ml) was added and stirred at reflux for 1 hour. 500 ml of pure water obtained by distilling off methanol from the water removal tube was added for liquid separation. The toluene layer was washed with pure water until neutral, and then dried over sodium sulfate. After drying, toluene was distilled off under reduced pressure to obtain colorless crystals. The obtained crystal was recrystallized from toluene / hexane to obtain 25 g of Intermediate 8-1.

Under a nitrogen atmosphere, 5.8 g of tetrakis (triphenylphosphine) palladium (0) and 100 ml of THF were dissolved in a 500 ml three-necked flask. 4-bromoaniline 18.9 _g, was added in this order _{2MNa 2 CO 3 100ml, 5- (} 2- hexylthiophene) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 28.0 g. After stirring at reflux for 5 hours, concentrated hydrochloric acid was added until acidic and extracted with 200 ml of ethyl acetate. The ethyl acetate layer was washed with pure water until neutral. The ethyl acetate layer was dried over sodium sulfate, and then toluene was distilled off under reduced pressure to obtain 18.1 g of an amine intermediate.
18.1 g of the amine intermediate was placed in a 500 ml three-necked flask, dissolved in 100 ml of toluene, 15 ml of acetic anhydride, 8.6 g of sodium acetate / 50 ml of pure water were added, and the mixture was stirred at 25 ° C. for 1 hour. The toluene layer was washed with pure water until neutral and then dried over sodium sulfate. Toluene was distilled off under reduced pressure, and then recrystallized from ethyl acetate / hexane to obtain 19.0 g of Intermediate 8-3.

  In the same manner as in Example 1, 10 g of Intermediate 8-4 was obtained.

  10.0 g of α-quarterthiophene was placed in a 300 ml three-necked flask and dissolved in 100 ml of DMF. Under magnetic stirring at 25 ° C., 10.8 g of N-bromosuccinimide (NBS) was added and stirred at 25 ° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into 500 ml of pure water and stirred for 1 hour, and the precipitated yellow crystals were collected by filtration. It was washed with 500 ml of pure water and 100 ml of methanol in this order to obtain 13.0 g of yellow crystals (intermediate 8-5).

  In the same manner as in Example 1, 3.0 g of a monomer including the specific example 153 of the general formula (I-1) described above as a partial structure was obtained.

  3.0 g of polyester [Exemplary Compound 49] was obtained in the same manner as in Synthesis Example 1 except that hexylene glycol was used instead of ethylene glycol.

When the molecular weight of this polymer was measured by GPC, it was Mw = 9.2 × 10 ⁴ (styrene conversion), Mw / Mn = 1.12, and the degree of polymerization p determined from the molecular weight of the monomer was about 69.

  An organic electroluminescent device was produced in the same manner as in Example 4 except that the exemplified compound (49) was used instead of the exemplified compound (9) used in Example 1.

Example 9
-Synthesis Example 9-
10.7 g of magnesium and 200 ml of THF were placed in a 500 ml three-necked flask. After stirring at 40 ° C. for 30 minutes, the mixture was refluxed for 1 hour to prepare a Grignard reagent.
Into a 1000 ml three-necked flask, 48 g of 3,4-dibromothiophene and 4.0 g of [1,1′-Bis (diphenylphosphino) feroccine nickel (II) Dichloride Dichloromethane Complex (1: 1) were added and dissolved in 400 ml of THF. The Grignard reagent was added dropwise at 25 ° C. over 30 minutes. Thereafter, the mixture was stirred at reflux for 1 hour to complete the reaction. Treated with 500 ml of 1N HCl and extracted with ethyl acetate. The ethyl acetate layer was washed to neutrality and dried with sodium sulfate. Vacuum distillation yielded 30 g of 3,4-dibutylthiophene.
This was brominated using the same method as the synthesis of Example 8, Intermediate 8-5 to obtain 30 g of 2,5-dibromo-3,4-dibutylthiophene.

  Under a nitrogen atmosphere, into a 300 ml three-necked flask, 2.9 g of triphenylphosphine palladium (0), 17.7 g of 2,5-dibromo-3,4-dibutylthiophene, 100 ml of 2M aqueous sodium hydrogen carbonate solution, 2,2′-bithiophene-5 21 g of boronic acid was added and dissolved in 200 ml of THF. After stirring at reflux for 5 hours, the completion of the reaction was confirmed by TLC. 600 ml of 1N HCl was added and the reaction was extracted with toluene. It was washed with pure water to neutrality and dried with sodium sulfate. The solvent was distilled off under reduced pressure and recrystallized from toluene to obtain 20.5 g of intermediate 9-1.

  This was brominated using the same method as the synthesis of intermediate 8-5 in Example 8 to obtain 10.5 g of intermediate 9-2.

  30 g of intermediate 9-3 was obtained in the same manner as in Example 1.

  Ullmann reaction was carried out in the same manner as in Example 1 to obtain 3.5 g of Intermediate 9-4. In addition, Intermediate 9-5 was obtained in the same manner as in Example 1.

  In the same manner as in Example 8, 2.0 g of the polyester [Exemplary Compound 57] in the general formula (I-1) was obtained.

When the molecular weight of this polymer was measured by GPC, it was Mw = 1.0 × 10 ⁵ (in terms of styrene), Mw / Mn = 1.22, and the degree of polymerization p determined from the molecular weight of the monomer was about 82.

  An organic electroluminescent device was produced in the same manner as in Example 5 except that the exemplified compound (57) was used instead of the exemplified compound (9) used in Example 1.

(Example 10)
-Synthesis Example 10-
In the same manner as in Example 1, 3.5 g of intermediate 10-1 was obtained.

  In the same manner as in Example 1, 1.8 g of [Exemplary Compound 59] represented by General Formula (I-2) was obtained.

When the molecular weight of this polymer was measured by GPC, Mw = 5.7 × 10 ⁴ (in terms of styrene) and Mw / Mn = 1.33, and the degree of polymerization p determined from the molecular weight of the monomer was about 69.
An organic electroluminescent element was produced in the same manner as in Example 6 except that the exemplified compound (59) was used instead of the exemplified compound (9) used in Example 1.

(Example 11)
-Synthesis Example 11-
In the same manner as in Example 9, 2.5 g of Intermediate 11-1 was obtained.

  2.3 g of [Exemplary Compound 97] represented by formula (I-2) was obtained in the same manner as in Example 9.

When the molecular weight of this polymer was measured by GPC, it was Mw = 8.0 × 10 ⁴ (styrene conversion), Mw / Mn = 1.49, and the degree of polymerization p determined from the molecular weight of the monomer was about 58.
An organic electroluminescent device was produced in the same manner as in Example 7 except that the exemplified compound (97) was used instead of the exemplified compound (9) used in Example 1.

(Comparative Example 1)
A device was fabricated in the same manner as in Example 1 except that the compound represented by the following structural formula (VI) was used instead of the exemplified compound (9) used in Example 1.

(Comparative Example 2)
2 parts by weight of polyvinyl carbazole (PVK) as a charge transporting polymer, 0.1 part by weight of the compound (V-1) as a light emitting material, and 1 part by weight of the compound (IV-9) as an electron transporting material are mixed. A weight% dichloroethane solution was prepared and filtered through a 0.1 μm PTFE filter. Using this solution, a hole transport layer having a film thickness of 0.15 μm was formed on a glass substrate formed by etching a 2 mm wide strip-shaped ITO electrode by dipping. After sufficiently drying, a Mg—Ag alloy was vapor-deposited by co-evaporation to form a back electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross the ITO electrode. The effective area of the formed organic EL element was 0.04 cm ² .

(Evaluation)
The organic EL device produced as described above was sealed with glass with an adhesive in dry nitrogen, and the measurement was performed with the ITO electrode side as plus and the Mg-Ag back electrode as minus.
The light emission characteristics (maximum luminance) were compared based on the driving current density when the initial luminance was 400 cd / m ^{2 in} the direct current driving method (DC driving). In addition, the evaluation of the light emission lifetime is based on the drive time when the luminance (initial luminance L ₀ : 400 cd / m ² ) of the element of Comparative Example 1 becomes luminance L / initial luminance L ₀ = 0.5 at room temperature. _0.0 , and the relative time when the brightness was set to ₀ , and the voltage increase (= voltage / initial driving voltage) when the luminance of the element became luminance L / initial luminance L ₀ = 0.5 were evaluated. The results are shown in Table 1.

  As described above, the organic electroluminescent device of this example uses polyester that is superior in thermal durability, solubility in solvents and resins, and compatibility compared with the organic electroluminescent device of the comparative example, and has a small voltage increase. It is possible to provide an organic electroluminescent element that can emit light with less power, that is, has high luminance, high efficiency, and a long element lifetime. In addition, when the obtained element was observed, in this example, an organic electroluminescent element with fewer defects such as pinholes and easy to increase in area than the comparative example can be provided.

It is a schematic block diagram which shows the display apparatus of embodiment. It is a schematic block diagram which shows the display apparatus of other embodiment. It is a schematic block diagram which shows the display apparatus of other embodiment. It is a schematic block diagram which shows the display apparatus of other embodiment.

Explanation of symbols

1 transparent insulator substrate,
2 transparent electrodes,
3 hole transport layer,
4 Light emitting layer,
DESCRIPTION OF SYMBOLS 5 Electron transport layer 6 Light emitting layer 7 which has charge transport ability Back electrode 9 Voltage application apparatus 10 Organic electroluminescent element

Claims (7)

In an electroluminescent element composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes consisting of an anode and a cathode, at least one of which is transparent or translucent,
At least one layer of the organic compound layer contains one or more polyesters composed of repeating units containing at least one selected from the structures represented by the following general formulas (I-1) and (I-2) as a partial structure. An organic electroluminescent device characterized by that.

[In the formula, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, and a substituted or unsubstituted aromatic ring having 1 to 10 aromatic rings. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ each independently represent a hydrogen atom, which represents a condensed condensed aromatic hydrocarbon or a substituted or unsubstituted monovalent aromatic heterocyclic ring , Alkyl group, alkoxyl group, aralkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, or substituted or unsubstituted monovalent aromatic Represents a family heterocycle. i, j represents 0 or 1, T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched hydrocarbon group having 2 to 10 carbon atoms, a , B, and c each independently represent an integer of 0 or more and 10 or less. Further, a + b + c ≧ 1. ]   The organic compound layer is composed of at least a light emitting layer and at least one of an electron transport layer and an electron injection layer, and the light emitting layer contains at least one kind of the polyester. The organic electroluminescent element of description.   The organic compound layer is composed of at least a light emitting layer and at least one layer of a hole transport layer and a hole injection layer, and the light emitting layer contains at least one kind of the polyester. Item 2. The organic electroluminescent device according to Item 1.   The organic compound layer is composed of at least a light emitting layer, at least one layer of a hole transport layer and a hole injection layer, and at least one layer of an electron transport layer and an electron injection layer, and the light emitting layer is the polyester. The organic electroluminescent element according to claim 1, comprising at least one of the above.   2. The organic electroluminescence according to claim 1, wherein the organic compound layer is composed of only a light emitting layer having a charge transport function, and the light emitting layer having the charge transport function contains one or more kinds of the polyester. element. The organic electroluminescent element according to claim 1, wherein the polyester is a polyester represented by the following general formula (II-1) or (II-2).

[In General Formulas (II-1) and (II-2), A ¹ represents at least one selected from the structures represented by General Formulas (I-1) and (I-2), and Y ¹ Represents a divalent alcohol residue, Z ¹ represents a divalent carboxylic acid residue, m represents an integer of 1 to 5, and p represents an integer of 5 to 5000. ] In a display device comprising one or more organic compound layers sandwiched between a pair of electrodes consisting of an anode and a cathode, at least one of which is transparent or translucent,
At least one layer of the organic compound layer includes at least one polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (I-1) and (I-2) as a partial structure. An organic electroluminescent device containing seeds and arranged in at least one of a matrix and a segment;
Drive means for driving the organic field effect elements arranged in at least one of a matrix and a segment;
A display device comprising:

[In the formula, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, and a substituted or unsubstituted aromatic ring having 1 to 10 aromatic rings. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ each independently represent a hydrogen atom, which represents a condensed condensed aromatic hydrocarbon or a substituted or unsubstituted monovalent aromatic heterocyclic ring , Alkyl group, alkoxyl group, aralkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings, or substituted or unsubstituted monovalent aromatic Represents a family heterocycle. i, j represents 0 or 1, T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a divalent branched hydrocarbon group having 2 to 10 carbon atoms, a , B, and c each independently represent an integer of 0 or more and 10 or less. Further, a + b + c ≧ 1. ]

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