JP5194403B2 - Organic electroluminescence device - Google Patents

Description

  The present invention relates to an organic electroluminescent element (hereinafter referred to as “organic EL element”), and more particularly, to an organic EL element using a specific charge transporting polymer.

  An electroluminescent element (hereinafter referred to as an “EL element”) is a self-luminous all-solid-state element, and is highly visible and resistant to impacts. At present, those using inorganic phosphors are the mainstream. However, since an AC voltage of 200 V or more is required for driving, there are problems such as high manufacturing cost and insufficient brightness.

  On the other hand, research on EL devices using organic compounds first started with a single crystal such as anthracene, but in the case of a single crystal, a film thickness of about 1 mm and a driving voltage of 100 V or more were necessary. For this reason, attempts have been made to reduce the thickness by vapor deposition (see, for example, Non-Patent Document 1). However, the thin film obtained by this method still has a high driving voltage of 30 V, a low density of electron and hole carriers in the film, and a low probability of photon generation due to carrier recombination, resulting in sufficient luminance. I couldn't.

However, in recent years, in a function-separated EL device in which a thin film of a hole-transporting organic low-molecular compound and a fluorescent organic low-molecular compound having an electron-transporting capability are sequentially stacked by a vacuum deposition method, a 1000 cd / A device capable of obtaining high luminance of m ² or more has been reported (see, for example, Non-Patent Document 2), and research and development of stacked EL devices have been actively conducted since then. These stacked devices are injected into the light emitting layer made of a fluorescent organic compound while maintaining the carrier balance of holes and electrons from the electrode through the charge transporting layer made of the organic compound having a charge transporting property and confined in the light emitting layer. High-luminance light emission is realized by recombination of the generated holes and electrons.

However, in this type of EL element, the following problems are shown for realization.
(1) Since it is driven at a high current density of several mA, a large amount of Joule heat is generated. For this reason, there are many phenomena in which hole transporting low molecular weight compounds and fluorescent organic low molecular weight compounds formed in an amorphous glass state by vapor deposition are gradually crystallized and finally melted, resulting in a decrease in luminance and dielectric breakdown. As a result, there is a problem that the lifetime of the element is reduced.
(2) Since a low molecular weight organic compound is formed in a plurality of vapor deposition steps to a thickness of 0.1 μm or less, pinholes are likely to occur, and the film thickness is under strictly controlled conditions to obtain sufficient performance. It is necessary to perform control. Therefore, productivity is low and it is difficult to increase the area.

  In order to solve the problem shown in (1) above, a starburst amine capable of obtaining a stable amorphous glass state is used as a hole transport material, or a polymer in which triphenylamine is introduced into the side chain of polyphosphazene is used. There have been reports of EL devices that have been used (for example, see Non-Patent Documents 3 and 4). However, these alone do not satisfy the hole injection property from the anode or the hole injection property to the light emitting layer because there is an energy barrier due to the ionization potential of the hole transport material. In the case of the former starburst amine, since the solubility is small, it is difficult to purify and it is difficult to increase the purity, and in the case of the latter polymer, a high current density is not obtained and sufficient luminance is obtained. There are also problems such as not.

  Next, in order to solve the problem shown in (2), research and development of an organic EL element having a single-layer structure capable of shortening the process was advanced, and a conductive polymer such as poly (p-phenylene vinylene) was used. An element (for example, see Non-Patent Document 5) or an element in which an electron transport material and a fluorescent dye are mixed in a hole transporting polyvinyl carbazole (for example, see Non-Patent Document 6) has been proposed. Luminous efficiency is not as good as that of a stacked organic EL device using an organic low molecular weight compound.

Also, from the viewpoint of manufacturing methods, wet coating methods have been studied from the viewpoints of manufacturing simplification, workability, large area, cost, etc., and it has been reported that elements can also be obtained by casting methods ( For example, refer nonpatent literature 7 and 8.). However, the solubility and compatibility of the charge transport material with respect to the solvent and the resin are poor, so that there is a problem in production or characteristics because it is easily crystallized.
ThIn SolId FIms, Vol. 94, 171 (1982) ApplIed PhysIcs Letter, Vol. 51,913 (1987) Proceedings of the 40th Joint Conference on Applied Physics 30a-SZK-14 (1993) Proceedings of the 42nd Polymer Symposium, 20J21 (1993) Nature, Vol. 357, 477 (1992) Proceedings of the 38th Joint Conference on Applied Physics 31pg-12 (1991) Proceedings of the 50th Japan Society of Applied Physics, 29p-ZP-5 (1989) Proceedings of the 51st Japan Society of Applied Physics, 28a-PB-7 (1990)

  The present invention has been made in view of the above-mentioned problems of the prior art, and its purpose is an organic EL that has sufficient luminance, is excellent in stability and durability, has a large area, and is easy to manufacture. It is to provide an element.

  As a result of intensive studies to achieve the above object, the present inventors have found that the following general formulas (IA-1) and (IA-2) or general formulas (IB-1) and (IB-2) It has been found that a luminescent polyester containing at least one selected as a partial structure has suitable charge mobility and thin film forming ability as an organic EL device, and further contains at least one luminescent polyester in an organic compound layer Therefore, it has been found that it functions as an organic EL element having high efficiency, high luminance, and durability, and has completed the following present invention.

That is, the present invention
<1> In an electroluminescent device composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes, at least one of which is transparent or translucent,
At least one organic compound layer includes at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (IA-1) and (IA-2) as a partial structure. Contains,
The organic electroluminescent device is characterized in that the luminescent polyester is a luminescent polyester represented by the following general formula (III-1) or (III-2) .

In the general formulas (IA-1) and (IA-2), Ar represents a substituted or unsubstituted monovalent aromatic group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings. Substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or substituted or unsubstituted 1
Represents a valent aromatic heterocyclic ring, X represents a group represented by the general formula (IIA-1) or (IIA-2), and T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or A branched chain hydrocarbon group having 2 to 10 carbon atoms is represented. h represents an integer of 1; i and j each independently represents an integer of 0 or 1.

In general formulas (IIA-1) and (IIA-2), Ar ₁ represents a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent polynuclear aromatic carbon having 2 to 10 aromatic rings. Represents hydrogen, a substituted or unsubstituted divalent aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted divalent aromatic heterocyclic ring, k and l are each independently an integer of 1 to 10 Represents.

<2> The organic compound layer includes at least a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer is represented by the general formulas (IA-1) and (IA-2). <1> The organic electroluminescence device according to <1>, comprising at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures as a partial structure.

<3> The organic compound layer includes at least a hole transport layer and / or a hole injection layer, a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer has the general formula ( <1> Organic electroluminescence according to <1>, comprising at least one luminescent polyester comprising a repeating unit containing at least one selected from the structures represented by IA-1) and (IA-2) as a partial structure It is an element.

<4> The organic compound layer is composed of at least a hole transport layer and / or a hole injection layer and a light emitting layer, and at least the light emitting layer is represented by the general formulas (IA-1) and (IA-2). <1> The organic electroluminescent element according to <1>, comprising at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures shown as a partial structure.

<5> The organic compound layer is composed of only one light emitting layer having charge transporting ability, and the light emitting layer is at least selected from the structures represented by the general formulas (IA-1) and (IA-2) The organic electroluminescent element according to <1>, comprising at least one luminescent polyester composed of a repeating unit containing one type as a partial structure.

<6> The organic electroluminescent element according to any one of <2> to <5>, wherein the light emitting layer includes a charge transporting material.

  In general formulas (III-1) and (III-2), Y represents a divalent hydrocarbon group. Z represents a divalent hydrocarbon group. B and B ′ each represent —O— (Y—O) m—H or —O— (Y—O) m—CO—Z—CO—OR ′, wherein R and R ′ represent a hydrogen atom, an alkyl group, A substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group is represented. m represents an integer of 1 to 5. p represents an integer of 5 to 5,000. A represents at least one selected from the structures represented by the general formulas (IA-1) and (IA-2).

< 7 > In an electroluminescent device composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes, at least one of which is transparent or translucent,
At least one of the organic compound layers includes at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (IB-1) and (IB-2) as a partial structure. Contains,
The organic electroluminescent device is characterized in that the luminescent polyester is a luminescent polyester represented by the following general formula (III-1) or (III-2) .

In general formulas (IB-1) and (IB-2), Ar represents a substituted or unsubstituted monovalent aromatic group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings. Represents a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, and X represents a group represented by the general formula (IIB) T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a branched hydrocarbon group having 2 to 10 carbon atoms. h represents an integer of 1; i and j each independently represents an integer of 0 or 1.

In general formula (IIB), Ar ₁ represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cyclohexa ring, a substituted or unsubstituted aromatic polynuclear aromatic having 2 to 10 aromatics. Hydrocarbon, substituted or unsubstituted aromatic 2-10 condensed polycyclic aromatic hydrocarbon, substituted or unsubstituted aromatic heterocycle, carbon number 1 substituted with a substituent containing at least one aromatic heterocycle Represents a cyclohexacycle substituted with an alkylene group of ˜5 or a substituent containing at least one aromatic heterocycle, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, a cyano group, A halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group is represented. Q is an integer of 1 to 10, r and s are integers of 0 to 10 (where r and s are not 0), and u is 0 or 1.

< 8 > The organic compound layer includes at least a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer is represented by the general formulas (IB-1) and (IB-2). < 7 > The organic electroluminescence device according to < 7 >, comprising at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures as a partial structure.

< 9 > The organic compound layer includes at least a hole transport layer and / or a hole injection layer, a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer has the general formula ( < 7 > Organic electroluminescence according to < 7 >, comprising at least one luminescent polyester comprising a repeating unit containing at least one selected from the structures represented by IB-1) and (IB-2) as a partial structure It is an element.

< 10 > The organic compound layer includes at least a hole transport layer and / or a hole injection layer, and a light emitting layer, and at least the light emitting layer is represented by the general formulas (IB-1) and (IB-2). < 7 > The organic electroluminescence device according to < 7 >, comprising at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures shown as a partial structure.

< 11 > The organic compound layer is composed of only one light emitting layer having charge transporting ability, and the light emitting layer is at least selected from the structures represented by the general formulas (IB-1) and (IB-2). < 7 > The organic electroluminescent element according to < 7 >, comprising at least one luminescent polyester composed of a repeating unit containing one type as a partial structure.

< 12 > The organic electroluminescent element according to any one of < 8 > to < 11 >, wherein the light emitting layer includes a charge transporting material.

  In general formulas (III-1) and (III-2), Y represents a divalent hydrocarbon group. Z represents a divalent hydrocarbon group. B and B ′ each represent —O— (Y—O) m—H or —O— (Y—O) m—CO—Z—CO—OR ′, wherein R and R ′ represent a hydrogen atom, an alkyl group, A substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group is represented. m represents an integer of 1 to 5. p represents an integer of 5 to 5,000. A represents at least one selected from the structures represented by the general formulas (IB-1) and (IB-2).

  ADVANTAGE OF THE INVENTION According to this invention, it has sufficient brightness | luminance, is excellent in stability and durability, can provide an organic EL element which can be enlarged and can be manufactured easily.

Hereinafter, the present invention will be described in detail.
The first organic EL element of the present invention (hereinafter referred to as “first present invention”) includes at least one organic compound layer sandwiched between a pair of electrodes that are transparent or translucent. In the organic electroluminescent device constituted by the above, at least one of the organic compound layers includes at least one selected from the structures represented by the following general formulas (IA-1) and (IA-2) as a partial structure. It is characterized by containing one or more luminescent polyesters composed of repeating units. However, in 1st this invention, polyester in which h represents the integer of 1 in general formula (IA-1) and (IA-2) is applied.

In general formulas (IA-1) and (IA-2), Ar represents a substituted or unsubstituted monovalent phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, Represents a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, and X represents a compound represented by the general formula (IIA-1) or (IIA-2) And T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a branched hydrocarbon group having 2 to 10 carbon atoms. h, i, and j each independently represents an integer of 0 or 1.

In the general formulas (IIA-1) and (IIA-2), Ar ₁ represents a substituted or unsubstituted divalent phenylene group, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings. Represents a substituted or unsubstituted divalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted divalent aromatic heterocyclic ring, k and l each independently represents an integer of 1 to 10; Represent.

The second organic EL element of the present invention (hereinafter referred to as “second present invention”) includes at least one organic compound layer sandwiched between a pair of electrodes that are transparent or translucent. In the organic electroluminescent device constituted by the above, at least one of the organic compound layers includes at least one selected from the structures represented by the following general formulas (IB-1) and (IB-2) as a partial structure. It contains at least one luminescent polyester composed of repeating units.
However, in 2nd this invention, polyester in which h represents the integer of 1 in general formula (IB-1) and (IB-2) is applied.

  In the general formulas (IB-1) and (IB-2), Ar represents a substituted or unsubstituted monovalent phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, A substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, and X represents a group represented by the general formula (IIB) , T represents a C1-C6 divalent linear hydrocarbon group or a C2-C10 branched hydrocarbon group. h, i, and j each independently represents an integer of 0 or 1.

In general formula (IIB), Ar ₁ represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cyclohexa ring, a substituted or unsubstituted aromatic polynuclear aromatic having 2 to 10 aromatics. Hydrocarbon, substituted or unsubstituted aromatic 2-10 condensed polycyclic aromatic hydrocarbon, substituted or unsubstituted aromatic heterocycle, carbon number 1 substituted with a substituent containing at least one aromatic heterocycle Represents a cyclohexacycle substituted with an alkylene group of ˜5 or a substituent containing at least one aromatic heterocycle, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, a cyano group, A halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group is represented. Q is an integer of 1 to 10, r and s are integers of 0 to 10 (where r and s are not 0), and u is 0 or 1.

  The organic EL device of the present invention has sufficient brightness and stability and durability because at least one of the organic compound layers has a layer containing the charge transporting polyester. Furthermore, by using the luminescent polyester, it is possible to increase the area and to manufacture easily. In addition, the luminescent polyester can control the luminescent color by appropriately selecting the structure to be described later, and can also provide hole and / or electron charge transport ability. For this reason, it can be used as a light emitting layer having both electron transport properties according to the purpose.

  In addition, since the light-emitting polyester in the present invention has a so-called bipolar transport ability having a hole and electron charge transport function, the light-emitting layer is not only a single-layer structure having only a light-emitting layer but also a light-emitting layer for a laminated structure. Not only can it be applied as a material, but it has the ability to transport both holes and electrons, so that the carrier balance in the light-emitting layer is maintained appropriately, and as a result, it is possible to obtain the effect of improving device characteristics such as light emission efficiency. .

  Since the first invention and the second invention have many common parts, they will be described below together. Accordingly, the contents of the description apply to both inventions unless otherwise specified.

  First, in the general formulas (IA-1) and (IA-2) or the general formulas (IB-1) and (IB-2), Ar represents a substituted or unsubstituted monovalent aromatic group. Specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 10 aromatic rings, or a substituted or unsubstituted monovalent aromatic ring having 2 to 10 aromatic rings. Or a substituted or unsubstituted monovalent aromatic heterocyclic ring, or a substituted or unsubstituted monovalent aromatic group containing at least one aromatic heterocyclic ring.

  Here, the number of aromatic rings constituting the polynuclear aromatic hydrocarbon and condensed aromatic hydrocarbon selected as the structure representing Ar is not particularly limited, but those having 2 to 5 aromatic rings are preferable, and condensed rings In the aromatic hydrocarbon, a fully condensed ring aromatic hydrocarbon is preferable. In the present invention, the polynuclear aromatic hydrocarbon and condensed aromatic hydrocarbon specifically mean polycyclic aromatics defined below.

  That is, the “polynuclear aromatic hydrocarbon” represents a hydrocarbon compound in which two or more aromatic rings composed of carbon and hydrogen are present and these aromatic rings are bonded to each other through a carbon-carbon bond. Specific examples include biphenyl, terphenyl, stilbene and the like. In addition, “condensed aromatic hydrocarbon” refers to a carbon atom in which two or more aromatic rings composed of carbon and hydrogen exist, and these aromatic rings share a pair of adjacent bonded carbon atoms. Represents a hydrogen compound. Specific examples include naphthalene, anthracene, phenanthrene, pyrene, perylene, and fluorene.

  The aromatic heterocycle selected as one of the structures representing Ar represents an aromatic ring including elements other than carbon and hydrogen. Nr = 5 and / or 6 is preferably used as the number of atoms (Nr) constituting the ring skeleton. Further, the type and number of atoms (heterogeneous atoms) other than carbon atoms constituting the ring skeleton are not limited, but for example, a sulfur atom, a nitrogen atom, an oxygen atom, etc. are preferably used. / Or two or more hetero atoms may be contained. In particular, as a heterocyclic ring having a 5-membered ring structure, thiophene, thiophine, pyrrole, furan, or a heterocyclic ring in which the 3- and 4-position carbons thereof are further substituted with nitrogen is preferably used. A pyridine ring is preferably used as the ring.

  Furthermore, the aromatic group containing an aromatic heterocyclic ring selected as one of the structures representing Ar represents a linking group containing at least one kind of the aromatic heterocyclic ring in an atomic group forming a skeleton. These may be either all composed of a conjugated system or partly composed of a conjugated system, but those composed entirely of a conjugated system are preferred in terms of charge transportability and light emission efficiency.

  In the general formulas (IA-1) and (IA-2) or the general formulas (IB-1) and (IB-2), examples of the substituent for the monovalent aromatic group represented by Ar include a hydrogen atom, Examples thereof include an alkyl group, an alkoxy group, a phenoxy group, an aryl group, an aralkyl group, a substituted amino group, and a halogen atom. As said 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 said alkoxy group, a C1-C10 thing is preferable, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group etc. are mentioned. As said aryl group, a C6-C20 thing is preferable, for example, a phenyl group, a toluyl group, etc. are mentioned. As said aralkyl group, a C7-C20 thing is preferable, for example, a benzyl group, a phenethyl group, etc. are mentioned. Examples of the substituent of the substituted amino group include an alkyl group, an aryl group, and an aralkyl group, and specific examples are as described above.

In the general formulas (IA-1) and (IA-2) or the general formulas (IB-1) and (IB-2), T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms, or the number of carbon atoms. Represents a divalent branched hydrocarbon group having 2 to 10 carbon atoms, preferably a divalent linear hydrocarbon group having 2 to 6 carbon atoms, and a divalent branched chain group having 3 to 7 carbon atoms Selected from hydrocarbon groups.
The specific structure of T is shown below.

  In general formulas (IA-1) and (IA-2) or general formulas (IB-1) and (IB-2), h, i, and j each independently represent an integer of 0 or 1.

In the first present invention, in the general formulas (IA-1) and (IA-2), X represents a group represented by (IIA-1) or (IIA-2).

In general formulas (IIA-1) and (IIA-2), Ar ₁ represents a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent polynuclear aromatic carbon having 2 to 10 aromatic rings. Represents hydrogen, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, k and l are each independently an integer of 1 to 10 Represents.

Specifically, Ar ₁ represents a substituted or unsubstituted divalent phenylene group, and the like, and “polynuclear aromatic hydrocarbon”, “condensed aromatic hydrocarbon”, “aromatic heterocycle”, “aromatic heterocycle” The “aromatic group containing” is as described above.

Specific examples of the structure represented by the general formula (IA-1) in the first present invention are shown in Tables 1 to 1 below.
Table 14 to Table 30 show specific examples of the structure shown in FIG. 3 and represented by the general formula (IA-2).
However, specific examples of the structure represented by the general formula (IA-1) and the general formula (IA-2) in the first invention are (1-15) to (1-91), (1-115) to (1-210)

  In the second present invention, in the general formulas (IB-1) and (IB-2), X represents a group represented by the general formula (IIB).

In general formula (IIB), Ar ₁ represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cyclohexa ring, a substituted or unsubstituted aromatic polynuclear aromatic having 2 to 10 aromatics. Hydrocarbon, substituted or unsubstituted aromatic 2-10 condensed polycyclic aromatic hydrocarbon, substituted or unsubstituted aromatic heterocycle, carbon number 1 substituted with a substituent containing at least one aromatic heterocycle Represents a cyclohexacycle substituted with an alkylene group of ˜5 or a substituent containing at least one aromatic heterocycle, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, a cyano group, A halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group is represented. Q is an integer of 1 to 10, r and s are integers of 0 to 10 (where r and s are not 0), and u is 0 or 1.
The “polynuclear aromatic hydrocarbon”, “condensed aromatic hydrocarbon”, “aromatic heterocycle”, and “aromatic group containing an aromatic heterocycle” are also as described above.

  Hereinafter, specific examples of the structure represented by the general formula (IB-1) in the second invention are shown in Tables 31 to 55, and specific examples of the structure represented by the general formula (IB-2) are shown in Tables 56 to 55. 80. In the structural formula, “Et” represents an ethyl group.

Further, light emission comprising a repeating unit containing at least one selected from the structures represented by the general formulas (IA-1) and (IA-2) or the general formulas (IB-1) and (IB-2) as a partial structure Examples of the reactive polyester are those represented by the following general formulas (III-1) and (III-2) .

  In general formulas (III-1) and (III-2), Y represents a divalent hydrocarbon group. Z represents a divalent hydrocarbon group. B and B ′ each independently represent —O— (YO) m—H, or —O— (YO) m—CO—Z—CO—OR ′, wherein R ′ represents a hydrogen atom or an alkyl group. Represents a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group. m represents an integer of 1 to 5. p represents an integer of 5 to 5,000.

  In the general formulas (III-1) and (III-2), A is at least one selected from the structures represented by the general formulas (IA-1) and (IA-2), or the general formula (IB) -1) represents at least one selected from the structures represented by (IB-2), and two or more structures A may be contained in one polymer.

  In general formulas (III-1) and (III-2), R represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group. The aryl group preferably has 6 to 20 carbon atoms, 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 for the substituted aryl or substituted aralkyl group include a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, and a halogen atom.

  In general formulas (III-1) and (III-2), Y represents a divalent alcohol residue, and Z represents a divalent carboxylic acid residue. Specific examples of Y and Z include groups selected from the following formulas (1) to (7).

In formulas (1) to (7), R ₄ and R ₅ 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, and a substituted group. Or an unsubstituted aralkyl group or a halogen atom, a to c each represent an integer of 1 to 10, d and e each represent an integer of 0, 1 or 2, f represents 0 or 1, and V represents The group selected from following formula (8)-(18) is represented.

  In formulas (8) to (18), g represents an integer of 1 to 10, and h represents an integer of 0 to 10.

  In general formulas (III-1) and (III-2), B and B ′ are each independently —O— (Y′—O) m′—R ′ or —O— (Y′—O) m ′. —CO—Z′—CO—O—R ″ is represented. Here, R ′, Y ′, and Z ′ are the same as R, Y, and Z, and R ″ represents an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, m ′ represents an integer of 1 to 5.

In general formulas (III-1) and (III-2), m represents 0 or 1, and p represents an integer of 5 to 5,000, preferably 10 to 1,000. The weight average molecular weight Mw of the luminescent polyester in the present invention is in the range of 5,000 to 1,000,000, but is preferably in the range of 10,000 to 300,000.
Furthermore, it is preferable that the glass transition point (Tg) of the luminescent polyester in this invention is 100 degreeC or more.

Hereinafter, specific examples of the luminescent polyesters represented by the general formulas (III-1) and (III-2) will be shown. It is not necessarily limited to these specific examples.
Tables 81 to 85 show specific examples in the first invention, and Tables 86 to 89 show specific examples in the second invention. In the table, the numbers in the column A of the monomer column are the structure numbers (specific examples of the structures represented by the general formulas (IA-1) and (IA-2) in the case of Tables 81 to 85) ( Tables 1 to 30) and Tables 86 to 89 are specific examples of structures represented by the general formulas (IB-1) and (IB-2) (structures shown in Tables 31 to 80). ) Corresponding to the structure number. In addition, those in which the column of “-” is “−” indicate specific examples of the luminescent polyester represented by the general formula (III-1), and the others indicate specific examples of the luminescent polyester represented by (III-2). . Hereinafter, the specific example which attached | subjected each number, for example, the specific example which attached | subjected the number of 15, is called illustration compound (15).

  The luminescent polyesters represented by the general formulas (III-1) and (III-2) are luminescent monomers represented by the following structural formulas (V-1) and (V-2). It can be synthesized by polymerization by a known method described in Lecture 28 (Edited by Chemical Society of Japan, Maruzen, 1992).

  In the general formulas (V-1) and (V-2), Ar, X, T, h, i, and j are the general formulas (IA-1) and (IA-2) or the general formula (IB-1) and The same as Ar, X, Th, i, j in (IB-2). A ′ represents a hydroxyl group, a halogen atom, or an alkoxy group —O—R (wherein R represents an alkyl group, a substituted or unsubstituted aryl group, or an aralkyl group).

That is, the luminescent polyester represented by the general formulas (III-1) and (III-2) can be synthesized, for example, as follows.
When A ′ is a hydroxyl group, HO— (YO) m—H (where Y and m are the same as Y and m represented by the general formulas (III-1) and (III-2)). A dihydric alcohol represented by the same formula below is mixed in an 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, and 1 / 10,000 to 1/10 parts by weight, preferably 1 with respect to 1 part by weight of monomers. / 1,000 to 1/50 parts by mass. In order to remove water generated during the synthesis, it is preferable to use a solvent which can be azeotroped with water, and toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and 1 to 100 parts by weight per 1 part by weight of the monomer. It is used in the range of part by mass, preferably 2-50 parts by mass. 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 into a poor solvent in which a polymer such as methanol or ethanol or a polymer such as acetone is difficult to dissolve, the polymer is precipitated, and after separating the polymer, Wash thoroughly with organic solvent and dry. Further, if necessary, the reprecipitation treatment in which the polymer 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 polymer in the reprecipitation treatment is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight, with respect to 1 part by weight of the polymer. On the other hand, it is used in the range of 1 to 1,000 parts by mass, preferably 10 to 500 parts by mass.

  When A 'is halogen, a dihydric alcohol represented by HO- (YO) m-H is mixed in an approximately equivalent amount and polymerized using an organic basic catalyst such as pyridine or triethylamine. An organic basic catalyst is used in 1-10 equivalent with respect to 1 mass part of monomers, Preferably it is 2-5 equivalent. As the solvent, methylene chloride, tetrahydrofuran (THF), toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight with respect to 1 part by weight of the monomer. Used. 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 divalent alcohols with high acidity such as bisphenol, an interfacial polymerization method can also be used. That is, polymerization can be carried out by adding water to a dihydric alcohol, adding an equivalent base and dissolving it, and then adding a monomer solution equivalent to the divalent alcohol with vigorous stirring. At this time, water is used in an amount of 1 to 1,000 parts by mass, preferably 2 to 500 parts by mass, with respect to 1 part by mass 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 an amount 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.

  When A ′ is an alkoxyl group, dihydric alcohols represented by HO— (YO) m—H are added in excess, inorganic acid such as sulfuric acid and phosphoric acid, acetic acid such as titanium alkoxide, calcium and cobalt. It can be synthesized by transesterification by heating using a salt, carbonate or oxide of zinc as a catalyst. The dihydric alcohol is used in the range of 2 to 100 equivalents, preferably 3 to 50 equivalents, with respect to 1 equivalent of the monomer. The catalyst is used in the range of 1/1000 to 1 part by mass, preferably 1/100 to 1/2 part by mass, with respect to 1 part by mass of the monomer. The reaction is carried out at a reaction temperature of 200 to 300 ° C. After the transesterification from the group —O—R to the group HO— (YO) m—H is completed, the group HO— (Y—O) m—H is eliminated. In order to promote the polymerization reaction due to, it is preferable to carry out the reaction under reduced pressure. Also, using a high-boiling solvent such as 1-chloronaphthalene that can be azeotroped with the group HO- (YO) m-H, the group HO- (YO) m-H is removed azeotropically under reduced pressure. Can also be reacted.

  Moreover, the luminescent polyester shown by general formula (III-1) and (III-2) is compoundable as follows. In each of the above cases, a compound represented by the following structural formulas (VI-1) and (VI-2) is produced by adding an excess of dihydric alcohols and reacting them, and then using this as a luminescent monomer. The polymer may be obtained by reacting with a divalent carboxylic acid or a divalent carboxylic acid halide in the same manner as described above.

  In the general formulas (VI-1) and (VI-2), Ar, X, T, h, i, and j are the general formulas (IA-1) and (IA-2) or the general formula (IB-1) and Ar, X, T, h, i, j in (IB-2) are the same, and Y, m are synonymous with Y, m in (III-1) and (III-2).

Next, the layer structure of the organic EL element of the present invention will be described in detail.
The organic EL device of the present invention comprises a pair of electrodes, at least one of which is transparent or translucent, and one or a plurality of organic compound layers including a light emitting layer sandwiched between the electrodes. The layer structure is not particularly limited as long as at least one light-emitting polyester as described above is contained in at least the light-emitting layer.

  In the organic EL device of the present invention, when there is one organic compound layer, the organic compound layer means a light emitting layer having charge transporting ability, and the light emitting layer contains the light emitting polyester. On the other hand, when there are a plurality of organic compound layers (that is, in the case of a function separation type in which each layer has a different function), at least one of the layers is a light emitting layer, and this light emitting layer is a light emitting layer having a charge transporting ability. Also good.

In this case, as a specific example of the layer structure composed of the light emitting layer or the light emitting layer having the charge transporting capability and other layers,
(1) A layer configuration comprising a light emitting layer, an electron transport layer and / or an electron injection layer,
(2) A layer configuration including a hole transport layer and / or a hole injection layer, a light emitting layer, an electron transport layer and / or an electron injection layer,
(3) Layer structure formed from a hole transport layer and / or a hole injection layer, and a light emitting layer,
The layers other than the light-emitting layer having the layer constitutions (1) to (3) and the light-emitting layer having charge transport ability have a function as a charge transport layer or a charge injection layer.

  In any one of the layer configurations (1) to (3), it is sufficient that the luminescent polyester is contained in any one layer. In any layer configuration, the luminescent polyester is included in the luminescent layer. Is preferably contained.

  In the organic EL device of the present invention, the light emitting layer having a charge transport function, the hole transport layer, the hole injection layer, the electron transport layer, and the electron injection layer are formed of a charge transport compound other than the light emitting polyester (positive (A hole transport material, an electron transport material). Details of such a charge transporting compound will be described later.

Hereinafter, although it demonstrates in detail, referring drawings, it is not necessarily limited to these.
1 to 4 are schematic cross-sectional views for explaining the layer structure of the organic EL device of the present invention. In the case of FIG. 1, FIG. 2, and FIG. 3, an example in which there are a plurality of organic compound layers is shown. FIG. 4 shows an example in the case of one organic compound layer. In FIG. 1 to FIG. 4, components having similar functions are described with the same reference numerals.

The organic EL element shown in FIG. 1 is formed by sequentially laminating a transparent electrode 2, a light emitting layer 4, an electron transport layer and / or an electron injection layer 5, and a back electrode 7 on a transparent insulator substrate 1. This corresponds to 1). However, when the layer denoted by reference numeral 5 is composed of an electron transport layer and an electron injection layer, the electron transport layer, the electron injection layer, and the back electrode 7 are laminated in this order on the back electrode 7 side of the light emitting layer 4. .
2 includes a transparent electrode 2, a hole transport layer and / or a hole injection layer 3, a light emitting layer 4, an electron transport layer and / or an electron injection layer 5, and a back surface. The electrodes 7 are sequentially stacked and correspond to the layer configuration (2). However, when the layer denoted by reference numeral 3 is composed of a hole transport layer and a hole injection layer, the hole injection layer, the hole transport layer, and the light emitting layer 4 are provided on the back electrode 7 side of the transparent electrode 2. Laminated sequentially.

The organic EL element shown in FIG. 3 is obtained by sequentially laminating a transparent electrode 2, a hole transport layer and / or a hole injection layer 3, a light emitting layer 4 and a back electrode 7 on a transparent insulator substrate 1. This corresponds to the configuration (3). However, when the layer denoted by reference numeral 3 is composed of a hole transport layer and a hole injection layer, the hole injection layer, the hole transport layer, and the light emitting layer 4 are provided on the back electrode 7 side of the transparent electrode 2. Laminated sequentially.
The organic EL element shown in FIG. 4 is obtained by sequentially laminating a transparent electrode 2, a light emitting layer 6 having a charge transporting capability, and a back electrode 7 on a transparent insulator substrate 1.

Each will be described in detail below.
Depending on the structure of the organic compound layer containing the light-emitting polyester in the present invention, both the light-emitting layer 4 and the electron transport layer 5 function in the case of the organic EL element layer configuration shown in FIG. In the case of the layer structure of the organic EL element shown in FIG. 2, any of the hole transport layer 3, the light emitting layer 4, and the electron transport layer 5 can function, and the organic EL shown in FIG. In the case of the layer structure of the element, both can act as the hole transport layer 3 and the light emitting layer 4, and in the case of the layer structure of the organic EL element shown in FIG. be able to.

  In the case of the layer structure of the organic EL 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, etc. are used, but are not limited thereto. . Further, the transparent electrode 2 is preferably transparent to extract emitted light in the same manner as the transparent insulator substrate, and preferably has a high work function for injecting holes. Indium tin oxide (ITO), tin oxide (NESA) ), Oxide films such as indium oxide and zinc oxide, and vapor deposited or sputtered gold, platinum, palladium and the like are used, but not limited thereto.

  In the case of the layer configuration of the organic EL element shown in FIGS. 1 and 2, the electron transport layer 5 is formed of an electron transport material having a function (electron transport ability) according to the purpose. As such an electron transporting material, an oxadiazole derivative, a nitro-substituted fluorenone derivative, a diphenoquinone derivative, a thiopyrandioxide derivative, a fluorenylidenemethane derivative, and the like are preferable. Preferable specific examples include the following exemplary compounds (VII-1) to (VII-3), but are not limited thereto. Moreover, you may combine with several electron transport material instead of single.

  In the case of the layer configuration of the organic EL element shown in FIGS. 2 and 3, the hole transport layer 3 is composed of a hole transport material provided with a function (hole transport ability) according to the purpose. Examples of such hole transporting materials include tetraphenylenediamine derivatives, triphenylamine derivatives, carbazole derivatives, stilbene derivatives, aryl hydrazone derivatives, porphyrin compounds, and the following exemplified compounds (VIII-1) to ( VIII-9), but is not limited thereto. Moreover, you may combine not with single but with several hole transportable material. In the following, n and x represent an integer of 1 or more.

In the case of the layer structure of the organic EL device shown in FIGS. 1 to 4, the light emitting layer 4 and the light emitting layer 6 having charge transporting ability are represented by the general formulas (IA-1) and (IA-2) or It contains at least one luminescent polyester composed of repeating units containing at least one selected from the structures represented by formulas (IB-1) and (IB-2) as a partial structure.
In the present invention, the light emitting layer 4 is a hole transport for adjusting the hole mobility with respect to the light emitting polyester used in the present invention for the purpose of improving the durability of the organic electroluminescent device or improving the light emitting efficiency. The material may be formed by mixing and dispersing the material in the range of 0.1% by mass to 50% by mass. In addition, the light emitting layer 6 having a charge transporting ability is formed by mixing and dispersing a hole transporting material for adjusting hole mobility in a range of 0.1 mass% to 50 mass%. Examples of such hole transporting materials include tetraphenylenediamine derivatives, triphenylamine derivatives, carbazole derivatives, stilbene derivatives, aryl hydrazone derivatives, and porphyrin compounds, but are compatible with the luminescent polyester. , Tetraphenylenediamine derivatives and triphenylamine derivatives are preferred.

In addition, the light emitting layer 4 has an electron transport material for adjusting the electron mobility of 0.1 mass with respect to the light emitting polyester used in the present invention for the same purpose when mixing and dispersing the hole transport material. It may be formed by mixing and dispersing in the range of% to 50% by mass. The light emitting layer 6 having charge transporting ability is formed by mixing and dispersing an electron transporting material for adjusting electron mobility in a range of 0.1 mass% to 50 mass%. Examples of such electron transport materials include oxadiazole derivatives, nitro-substituted fluorenone derivatives, diphenoquinone derivatives, thiopyran dioxide oxide derivatives, fluorenylidenemethane derivatives, and the like.
In addition, 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 luminescent polyester.

In addition, the light emitting layer 4 and the light emitting layer 6 having charge transporting ability may be doped with a different dye compound as a guest material for improving the light emission intensity, adjusting the color purity, and the light emission spectrum. The dye compound to be doped may be an organic low molecule or an organic polymer.
Preferable examples when the dye compound to be doped is a low-molecular organic molecule include chelate-type organometallic complexes, polynuclear or condensed aromatic ring compounds, perylene derivatives, coumarin derivatives, styrylarylene derivatives, silole derivatives, oxazole derivatives, oxathiazoles Preferable examples in the case where the derivative, the oxadiazole derivative, or the like is a polymer include polyparaphenylene derivatives, polyparaphenylene vinylene derivatives, polythiophene derivatives, polyacetylene derivatives, and the like. As preferred specific examples, the following compounds (IX-1) to (IX-17) are used as preferred specific examples, but are not limited thereto.

  In Structural Formulas (IX-1) to (IX-17), n and x represent an integer of 1 or more, and y represents 0 or 1. In Structural Formulas (IX-16) and (IX-17), Ar represents a substituted or unsubstituted monovalent or divalent aromatic group. In Structural Formula (IX-17), X represents substituted or unsubstituted. Represents a substituted divalent aromatic group.

  In practice, doping is performed by mixing in a luminescent polyester solution or dispersion. The doping ratio of the dye compound in the light emitting layer is about 0.001% by mass to 40% by mass, preferably about 0.01% by mass to 10% by mass. As the coloring compound used for such doping, an organic compound that is compatible with the light emitting material and does not interfere with the formation of a good thin film of the light emitting layer is used, preferably a DCM derivative, a quinacridone derivative, a rubrene derivative. And porphyrin-based compounds. As preferred specific examples, the following compounds (X-1) to (X-4) are used, but are not limited thereto.

In the case of the layer structure of the organic EL element shown in FIGS. 1 to 4, the back electrode 7 is made of a metal that can be vacuum-deposited and has a low work function for performing electron injection. Silver, indium and alloys thereof, metal halide compounds such as lithium fluoride and lithium oxide, 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, or a coating method can be applied.

  The organic electroluminescent elements shown in FIGS. 1 to 4 are manufactured by sequentially forming individual layers on the transparent electrode 2 according to the layer structure of each organic electroluminescent element. Note that the hole transport layer and / or hole injection layer 3, the light-emitting layer 4, the electron transport layer and / or the electron injection layer 5, or the light-emitting layer 6 having a charge transport function is obtained by using the above-described materials by vacuum deposition, Or it melt | dissolves or disperses | distributes in a suitable organic solvent, and it forms with the spin coating method, the casting method, the dip method etc. on the said transparent electrode using the obtained coating liquid.

  The film thicknesses of the hole transport layer and / or hole injection layer 3, the light-emitting layer 4, the electron transport layer and / or the electron injection layer 5, and the light-emitting layer 6 having a charge transport function are each 10 μm or less, particularly A range of 0.001 to 5 μm is preferred. The dispersion state of each of the above materials (light emitting polyester, light emitting material, etc.) may be a molecular dispersion state or a fine particle state such as a microcrystal. In the case of a film forming method using a coating solution, it is necessary to select a dispersion solvent in consideration of the dispersibility and solubility of each material in order to obtain a molecular dispersion state. In order to disperse into fine particles, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer, an ultrasonic method, or the like can be used.

  Finally, in the case of the organic electroluminescence device shown in FIGS. 1 and 2, the back electrode 7 is formed on the electron transport layer and / or the electron injection layer 5 by vacuum deposition, sputtering, or the like. The organic electroluminescent element of the present invention is completed. In the case of the organic electroluminescent element shown in FIG. 3, the back electrode 7 is provided on the light emitting layer 4, and in the case of the organic electroluminescent element shown in FIG. 4, on the light emitting layer 6 having a charge transport function. By forming the back electrode 7 by a vacuum deposition method, a sputtering method or the like, the organic electroluminescence device of the present invention is completed.

The organic EL element of the present invention can emit light by applying a direct current voltage of 1 to 200 mA / cm ² at a current density of, for example, 4 to 20 V between a pair of electrodes.

EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not restrict | limited to these Examples.
<Examples relating to the first invention>
First, the luminescent polyester used in the examples was synthesized, for example, as follows.
(Synthesis Example 1-1)
1.0 g of diamine [the following exemplified compound (XII)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 7 hours in a nitrogen stream. After confirming that the raw material diamine was consumed by TLC, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Then, it is cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter is filtered through a 0.5 μm polytetrafluoroethylene (PTFE) filter, and the filtrate is dropped into 500 ml of methanol while stirring to form a polymer. Was precipitated. The obtained polymer was filtered, washed thoroughly with methanol, and then dried to obtain 1.0 g of luminescent polyester (A-1). When the molecular weight of this luminescent polyester (A-1) was measured by GPC gel permeation chromatography (GPC), Mw was 1.01 × 10 ⁵ (in terms of styrene), and Mn / Mw was 2.60. The degree of polymerization p determined from the molecular weight of the monomer was about 105.

(Synthesis Example 1-2)
1.0 g of diamine [the following exemplified compound (XIII)], 8.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 6.5 hours under a nitrogen stream. After confirming that the raw material diamine was consumed by TLC, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 5 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.9 g of luminescent polyester (A-2). When the molecular weight was measured by GPC, Mw was 9.63 × 10 ⁴ (styrene conversion), Mw / Mn was 3.04, and p determined from the molecular weight of the monomer was about 85.

(Synthesis Example 1-3)
1.0 g of diamine [the following example compound (XIV)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 7 hours in a nitrogen stream. After confirming that the raw material diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 200 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, washed thoroughly with methanol, and then dried to obtain 0.9 g of a light-emitting polyester (A-3). When the molecular weight was measured by GPC, Mw was 1.20 × 10 ⁵ (in terms of styrene), Mw / Mn was 2.56, and p determined from the molecular weight of the monomer was about 115.

(Synthesis Example 1-4)
1.0 g of diamine [the following example compound (XV)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 5 hours in a nitrogen stream. After confirming that the diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, washed thoroughly with methanol, and then dried to obtain 0.9 g of a light-emitting polyester (A-4). When the molecular weight was measured by GPC, Mw was 6.26 × 10 ⁴ (in terms of styrene), Mw / Mn was 3.60, and p determined from the molecular weight of the monomer was about 85.

(Synthesis Example 1-5)
1.0 g of diamine [Example compound (XVI) below], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask, and the mixture was heated and stirred at 200 ° C. for 5 hours in a nitrogen stream. After confirming that the diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.8 g of luminescent polyester (A-5). When the molecular weight was measured by GPC, Mw was 5.84 × 10 ⁴ (styrene conversion), Mw / Mn was 3.20, and p obtained from the molecular weight of the monomer was about 66.

(Synthesis Example 1-6)
1.0 g of diamine [the following example compound (XVII)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 5 hours in a nitrogen stream. After confirming that the diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.8 g of luminescent polyester (A-6). When the molecular weight was measured by GPC, Mw was 5.74 × 10 ⁴ (in terms of styrene), Mw / Mn was 3.60, and p determined from the molecular weight of the monomer was about 51.

(Example 1-1)
A luminescent polyester (A-1) was prepared as a 5% by mass dichloroethane solution as a material for the luminescent layer and filtered through a 0.1 μm polytetrafluoroethylene (PTFE) filter.
Using this solution, a 2 mm-wide strip-shaped ITO electrode, which had been washed and dried, was applied on a glass substrate formed by etching to form a light-emitting layer having a thickness of 0.05 μm by spin coating. After sufficiently drying, 5% by mass of dichloroethane as an electron transporting material was charged with a charge transporting polyester [the following exemplified compound (XVIII)] (Mw = 8.08 × 10 ⁴ (in terms of styrene), Mn / Mw = 2.21). The solution was prepared as a solution, filtered through a PTFE filter having an aperture of 0.1 μm, and then applied onto the light emitting layer by a spin coating method to form an electron transport layer having a thickness of 0.03 μm. Finally, 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 .

(Example 1-2)
Charge transporting polyester [Exemplary Compound (VIII-9)] (Mw = 1.04 × 10 ⁵ (in terms of styrene), Mn / Mw = 1.87) prepared as a 5% by mass chlorobenzene solution as a material for the hole transport layer And filtered through a 0.1 μm PTFE filter. Using this solution, a 2 mm wide strip-shaped ITO electrode that had been washed and dried was applied by spin coating on a glass substrate formed by etching to form a hole transport layer having a thickness of 0.03 μm.
After sufficiently drying, the light-emitting polyester (A-2) is prepared as a 5% by mass dichloroethane solution as a material for the light-emitting layer, filtered through a PTFE filter having an aperture of 0.1 μm, and then spin coated on the hole transport layer. Was applied to form a light emitting layer having a thickness of 0.03 μm. Further, after sufficiently drying, a charge transporting polyester [Exemplary Compound (XVIII)] as an electron transporting material is prepared as a 5% by mass dichloroethane solution, filtered through a PTFE filter having an opening of 0.1 μm, and then spinned onto the light emitting layer. Application was performed by a coating method to form an electron transport layer having a thickness of 0.03 μm. Finally, 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 .

(Example 1-3)
A charge transporting polyester [Exemplary Compound (VIII-9)] was prepared as a 5% by mass chlorobenzene solution as a material for the hole transport layer, and filtered through a 0.1 μm PTFE filter. Using this solution, a 2 mm wide strip-shaped ITO electrode that had been washed and dried was applied by spin coating on a glass substrate formed by etching to form a hole transport layer having a thickness of 0.03 μm. After sufficiently drying, the light-emitting polyester (A-3) is prepared as a 5% by mass dichloroethane solution as a material for the light-emitting layer, filtered through a PTFE filter having an opening of 0.1 μm, and then spin coated on the hole transport layer. Was applied to form a light emitting layer having a thickness of 0.05 μm. Finally, 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 .

(Example 1-4)
0.5 parts by mass of charge transporting polyester [Exemplary Compound (VIII-9)] as a hole transporting material and 0.1 parts by mass of luminescent polyester (A-4) as a luminescent material are mixed to provide a 5% by mass chlorobenzene solution. Was filtered through a polytetrafluoroethylene (PTFE) filter having an opening of 0.1 μm. Using this solution, a 2 mm wide strip-shaped ITO electrode, which has been washed and dried, is applied by spin coating on a glass substrate formed by etching to form a light emitting layer having a thickness of 0.05 μm and having a charge transport capability. Finally, 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 .

(Example 1-5)
An organic EL device was produced in the same manner as in Example 1-4 except that the luminescent polyester (A-5) was used instead of the luminescent polyester (A-4).

(Example 1-6)
An organic EL device was produced in the same manner as in Example 1-4 except that the luminescent polyester (A-6) was used instead of the luminescent polyester (A-4).

<Examples relating to the second invention>
The luminescent polyester used in the examples was synthesized as follows, for example.
(Synthesis Example 2-1)
1.0 g of diamine [the following exemplified compound (XIX)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask, and the mixture was heated and stirred at 200 ° C. for 7 hours in a nitrogen stream. After confirming that the raw material diamine was consumed by TLC, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Then, it is cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter is filtered through a 0.5 μm polytetrafluoroethylene (PTFE) filter, and the filtrate is dropped into 500 ml of methanol while stirring to form a polymer. Was precipitated. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 1.0 g of luminescent polyester (B-1). When the molecular weight of this luminescent polyester (B-1) was measured by GPC gel permeation chromatography (GPC), Mw was 1.10 × 10 ⁵ (in terms of styrene) and Mn / Mw was 2.78. The degree of polymerization p determined from the molecular weight of the monomer was about 101.

(Synthesis Example 2-2)
1.0 g of diamine [the following exemplified compound (XX)], 8.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask, and the mixture was heated and stirred at 200 ° C. for 6.5 hours in a nitrogen stream. After confirming that the raw material diamine was consumed by TLC, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 5 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.9 g of luminescent polyester (B-2). When the molecular weight was measured by GPC, Mw was 8.75 × 10 ⁴ (styrene conversion), Mw / Mn was 3.23, and p determined from the molecular weight of the monomer was about 75.

(Synthesis Example 2-3)
1.0 g of diamine [the following example compound (XXI)], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask and heated and stirred at 200 ° C. for 7 hours in a nitrogen stream. After confirming that the raw material diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 200 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.9 g of luminescent polyester (B-3). When the molecular weight was measured by GPC, Mw was 6.84 × 10 ⁴ (in terms of styrene), Mw / Mn was 3.31, and p determined from the molecular weight of the monomer was about 56.

(Synthesis Example 2-4)
1.0 g of diamine [Example compound (XXII) below], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask, and the mixture was heated and stirred at 200 ° C. for 5 hours in a nitrogen stream. After confirming that the diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, washed thoroughly with methanol, and then dried to obtain 0.9 g of luminescent polyester (B-4). When the molecular weight was measured by GPC, Mw was 4.82 × 10 ⁴ (in terms of styrene), Mw / Mn was 3.52, and p determined from the molecular weight of the monomer was about 38.

(Synthesis Example 2-5)
1.0 g of diamine [Example compound (XXIII) below], 10.0 ml of ethylene glycol and 0.02 g of tetrabutoxytitanium were placed in a 50 ml three-necked eggplant flask, and the mixture was heated and stirred at 200 ° C. for 5 hours in a nitrogen stream. After confirming that the diamine was consumed, the pressure was reduced to 6.66 Pa and the mixture was heated to 210 ° C. while distilling off ethylene glycol, and the reaction was continued for 4 hours. Thereafter, the mixture was cooled to room temperature, dissolved in 50 ml of monochlorobenzene, the insoluble matter was filtered through a 0.5 μm PTFE filter, and the filtrate was dropped into 500 ml of methanol while stirring to precipitate a polymer. The obtained polymer was filtered, sufficiently washed with methanol, and then dried to obtain 0.8 g of luminescent polyester (B-5). When the molecular weight was measured by GPC, Mw was 5.92 × 10 ⁴ (in terms of styrene), Mw / Mn was 3.20, and p determined from the molecular weight of the monomer was about 47.

(Example 2-1)
A luminescent polyester (B-1) was prepared as a 5% by mass dichloroethane solution as a material for the luminescent layer, and filtered through a 0.1 μm polytetrafluoroethylene (PTFE) filter.
Using this solution, a 2 mm-wide strip-shaped ITO electrode, which had been washed and dried, was applied on a glass substrate formed by etching to form a light-emitting layer having a thickness of 0.05 μm by spin coating. After sufficiently drying, 5% by mass of dichloroethane as an electron transporting material was charged with a charge transporting polyester [Exemplary Compound (XVIII)] (Mw = 8.08 × 10 ⁴ (in terms of styrene), Mn / Mw = 2.21). The solution was prepared as a solution, filtered through a PTFE filter having an aperture of 0.1 μm, and then applied onto the light emitting layer by a spin coating method to form an electron transport layer having a thickness of 0.03 μm. Finally, 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 .

(Example 2-2)
Charge transporting polyester [Exemplary Compound (VIII-9)] (Mw = 1.04 × 10 ⁵ (in terms of styrene), Mn / Mw = 1.87) prepared as a 5% by mass chlorobenzene solution as a material for the hole transport layer And filtered through a 0.1 μm PTFE filter. Using this solution, a 2 mm wide strip-shaped ITO electrode that had been washed and dried was applied by spin coating on a glass substrate formed by etching to form a hole transport layer having a thickness of 0.03 μm.
After sufficiently drying, the light-emitting polyester (B-2) is prepared as a 5% by mass dichloroethane solution as a material for the light-emitting layer, filtered through a PTFE filter having a mesh size of 0.1 μm, and then spin coated onto the hole transport layer. Was applied to form a light emitting layer having a thickness of 0.03 μm. Further, after sufficiently drying, a charge transporting polyester [Exemplary Compound (XVIII)] as an electron transporting material is prepared as a 5% by mass dichloroethane solution, filtered through a PTFE filter having an opening of 0.1 μm, and then spinned onto the light emitting layer. Application was performed by a coating method to form an electron transport layer having a thickness of 0.03 μm. Finally, 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 .

(Example 2-3)
A charge transporting polyester [Exemplary Compound (VIII-9)] was prepared as a 5% by mass chlorobenzene solution as a material for the hole transport layer, and filtered through a 0.1 μm PTFE filter. Using this solution, a 2 mm wide strip-shaped ITO electrode that had been washed and dried was applied by spin coating on a glass substrate formed by etching to form a hole transport layer having a thickness of 0.03 μm. After sufficiently drying, the light-emitting polyester (B-3) is prepared as a 5% by mass dichloroethane solution as the material for the light-emitting layer, filtered through a PTFE filter having an opening of 0.1 μm, and then spin coated onto the hole transport layer. Was applied to form a light emitting layer having a thickness of 0.05 μm. Finally, 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 .

(Example 2-4)
0.5 parts by mass of charge transporting polyester [Exemplary Compound (VIII-9)] as a hole transporting material and 0.1 parts by mass of luminescent polyester (B-4) as a luminescent material are mixed to form a 5% by mass chlorobenzene solution. Was filtered through a polytetrafluoroethylene (PTFE) filter having an opening of 0.1 μm. Using this solution, a 2 mm wide strip-shaped ITO electrode, which has been washed and dried, is applied by spin coating on a glass substrate formed by etching to form a light emitting layer having a thickness of 0.05 μm and having a charge transport capability. Finally, 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 .

(Example 2-5)
A luminescent polyester (B-5) was prepared as a 5% by mass dichloroethane solution as a material for the luminescent layer, and filtered through a 0.1 μm polytetrafluoroethylene (PTFE) filter.
Using this solution, a 2 mm-wide strip-shaped ITO electrode, which had been washed and dried, was applied on a glass substrate formed by etching to form a light-emitting layer having a thickness of 0.05 μm by spin coating. After sufficiently drying, 5% by mass of dichloroethane as an electron transporting material was charged with a charge transporting polyester [Exemplary Compound (XVIII)] (Mw = 8.08 × 10 ⁴ (in terms of styrene), Mn / Mw = 2.21). The solution was prepared as a solution, filtered through a PTFE filter having an aperture of 0.1 μm, and then applied onto the light emitting layer by a spin coating method to form an electron transport layer having a thickness of 0.03 μm. Finally, 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 .

(Comparative Example 1)
Except that a light emitting polymer [the following exemplified compound (XXIV), polyfluorene type] (Mw = 7.64 × 10 ⁴ (styrene conversion), Mn / Mw = 2.34) was used as the material for the light emitting layer. A device was fabricated in the same manner as in Example 1-1.

(Comparative Example 2)
Except for using a light-emitting polymer [the following exemplified compound (XXV), PPV type] (Mw = 8.03 × 10 ⁴ (in terms of styrene), Mn / Mw = 2.11) as a material for the light-emitting layer. A device was fabricated in the same manner as in 1-2.

(Comparative Example 3)
Example 1 except that a light-emitting polymer [Exemplary compound (XXV), PPV system] (Mw = 8.03 × 10 ⁴ (in terms of styrene), Mn / Mw = 2.11) was used as the material for the light-emitting layer. A device was produced in the same manner as in -3.

(Comparative Example 4)
Sublimation-purified Alq3 [Exemplary Compound (IX-1)] as a light emitting layer material was put on a tungsten board and deposited by a vacuum vapor deposition method to form a light emitting layer having a thickness of 0.05 μm on the hole transport layer. Were fabricated in the same manner as in Example 1-3. (The degree of vacuum at the time of deposition was 10 ⁻⁵ Torr, and the boat temperature was 300 ° C.)

(Comparative Example 5)
A device was fabricated in the same manner as in Example 1-4, except that a light-emitting polymer [Exemplary Compound (XXV), PPV type] was used as the light-emitting material.

(Comparative Example 6)
Sublimation-purified oligothiophene compound [Exemplary Compound (XXVI)] as a light emitting layer material was placed in a tungsten boat and evaporated by a vacuum vapor deposition method to form a light emitting layer having a thickness of 0.05 μm on the hole transport layer. Except for the above, an element was fabricated in the same manner as in Example 1-3 (the degree of vacuum during vapor deposition was 10 ⁻⁵ Torr, and the boat temperature was 300 ° C.).

(Evaluation)
The organic EL device produced as described above was applied with a DC voltage in vacuum (133.3 × 10 ⁻³ Pa (10 ⁻⁵ Torr)) with the ITO electrode side plus and the Mg—Ag back electrode minus, The emission was measured, and the rising voltage, maximum luminance, and driving voltage at the maximum luminance were evaluated. The results are shown in Table 90. Moreover, the light emission lifetime of the organic EL element was measured in dry nitrogen. In the evaluation of the light emission lifetime, the current value was set so that the initial luminance was 50 cd / m ^2, and the time until the luminance was reduced by half from the initial value by constant current driving was defined as the element lifetime. The device lifetime at this time is also shown in Table 90.

  From the examples and comparative examples, at least one selected from the structures represented by the general formulas (IA-1) and (IA-2) or the general formulas (IB-1) and (IB-2) as a partial structure The light-emitting polyester composed of repeating structural units contains suitable light-emitting characteristics, ionization potential, and charge mobility for organic EL elements, and can form a good thin film using a spin coating method, a dip method, or the like. I understand that. In addition, it exhibits stable, high brightness and high efficiency characteristics. Therefore, the organic EL device of the present invention has few defects such as pinholes, can be easily increased in area, and has excellent durability and light emission characteristics.

It is the schematic block diagram which showed an example of the laminated constitution of the organic electroluminescent element of this invention. It is the schematic block diagram which showed an example of the laminated constitution of the organic electroluminescent element of this invention. It is the schematic block diagram which showed an example of the laminated constitution of the organic electroluminescent element of this invention. It is the schematic block diagram which showed an example of the laminated constitution of the organic electroluminescent element of this invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Transparent insulator board | substrate 2 Transparent electrode 3 Hole transport layer and / or hole injection layer 4 Light emitting layer 5 Electron transport layer and / or electron injection layer 6 Light emitting layer 7 which has a charge transport function 7 Back electrode

Claims (12)

In an electroluminescent element composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes, at least one of which is transparent or translucent,
At least one organic compound layer includes at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (IA-1) and (IA-2) as a partial structure. Contains,
The organic electroluminescent element is characterized in that the luminescent polyester is a luminescent polyester represented by the following general formula (III-1) or (III-2).


(In the general formulas (IA-1) and (IA-2), Ar represents a substituted or unsubstituted monovalent aromatic group, a substituted or unsubstituted monovalent polynuclear aromatic carbon having 2 to 10 aromatic rings. Represents hydrogen, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, and X represents a compound represented by the general formula (IIA-1) or (IIA) -2), T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a branched hydrocarbon group having 2 to 10 carbon atoms, and h is an integer of 1. the expressed. i, j represent each independently 0 or 1 integer.)


(In the general formulas (IIA-1) and (IIA-2), Ar ₁ represents a substituted or unsubstituted divalent aromatic group, a substituted or unsubstituted divalent polynuclear aromatic having 2 to 10 aromatic rings. Represents a hydrocarbon, a divalent condensed aromatic hydrocarbon having 2 to 10 substituted or unsubstituted aromatic rings or a substituted or unsubstituted divalent aromatic heterocyclic ring, k and l are each independently 1 to 10 Represents an integer.)


(In General Formulas (III-1) and (III-2), Y represents a divalent hydrocarbon group. Z represents a divalent hydrocarbon group. B and B ′ represent —O— (Y—O). ) M—H, or —O— (Y—O) m—CO—Z—CO—OR ′, wherein R and R ′ are hydrogen atoms, alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted M represents an integer of 1 to 5. p represents an integer of 5 to 5,000, and A is selected from the structures represented by the general formulas (IA-1) and (IA-2). Represents at least one selected from   The organic compound layer is composed of at least a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer is selected from the structures represented by the general formulas (IA-1) and (IA-2) The organic electroluminescent device according to claim 1, comprising at least one luminescent polyester composed of a repeating unit containing at least one selected as a partial structure.   The organic compound layer is composed of at least a hole transport layer and / or a hole injection layer, a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer has the general formula (IA-1). And at least one light-emitting polyester comprising a repeating unit containing at least one selected from the structures represented by (IA-2) and (IA-2) as a partial structure. Electroluminescent device.   The organic compound layer is composed of at least a hole transport layer and / or a hole injection layer and a light emitting layer, and at least the light emitting layer has a structure represented by the general formulas (IA-1) and (IA-2) 2. The organic electroluminescent device according to claim 1, comprising at least one luminescent polyester comprising a repeating unit containing at least one selected from the above as a partial structure.   The organic compound layer is composed of only one light emitting layer having a charge transporting ability, and the light emitting layer includes at least one selected from the structures represented by the general formulas (IA-1) and (IA-2). 2. The organic electroluminescent element according to claim 1, comprising at least one luminescent polyester composed of repeating units contained as a partial structure.   The organic electroluminescent element according to claim 2, wherein the light emitting layer contains a charge transporting material. In an electroluminescent element composed of one or a plurality of organic compound layers sandwiched between a pair of electrodes, at least one of which is transparent or translucent,
At least one of the organic compound layers includes at least one luminescent polyester composed of a repeating unit containing at least one selected from the structures represented by the following general formulas (IB-1) and (IB-2) as a partial structure. Contains,
The organic electroluminescent element is characterized in that the luminescent polyester is a luminescent polyester represented by the following general formula (III-1) or (III-2).


(In the general formulas (IB-1) and (IB-2), Ar represents a substituted or unsubstituted monovalent aromatic group, a substituted or unsubstituted monovalent polynuclear aromatic carbon having 2 to 10 aromatic rings. Represents hydrogen, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 10 aromatic rings or a substituted or unsubstituted monovalent aromatic heterocyclic ring, and X represents a group represented by the general formula (IIB) T represents a divalent linear hydrocarbon group having 1 to 6 carbon atoms or a branched hydrocarbon group having 2 to 10 carbon atoms, h represents an integer of 1. i and j are respectively Independently represents an integer of 0 or 1.)


(In the general formula (IIB), Ar ₁ represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cyclohexa ring, a substituted or unsubstituted polynuclear aromatic having 2 to 10 aromatics. Carbon number substituted with a substituent containing aromatic hydrocarbon, substituted or unsubstituted aromatic 2-10 condensed polycyclic aromatic hydrocarbon, substituted or unsubstituted aromatic heterocycle, at least one aromatic heterocycle 1 to 5 alkylene groups, or a cyclohexa ring substituted with a substituent containing at least one aromatic heterocycle, wherein R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group or a cyano group Represents a halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, q is an integer of 1 to 10, and r and s are integers of 0 to 10. (However r, s are not both 0 and becomes possible), u represents 0 or 1.)


(In General Formulas (III-1) and (III-2), Y represents a divalent hydrocarbon group. Z represents a divalent hydrocarbon group. B and B ′ represent —O— (Y—O). ) M—H, or —O— (Y—O) m—CO—Z—CO—OR ′, wherein R and R ′ are hydrogen atoms, alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted M represents an integer of 1 to 5. p represents an integer of 5 to 5,000, and A is selected from the structures represented by the above general formulas (IB-1) and (IB-2). Represents at least one selected from   The organic compound layer is composed of at least a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer is selected from the structures represented by the general formulas (IB-1) and (IB-2) 8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent device comprises at least one luminescent polyester comprising a repeating unit containing at least one selected from the above as a partial structure.   The organic compound layer is composed of at least a hole transport layer and / or a hole injection layer, a light emitting layer, an electron transport layer and / or an electron injection layer, and at least the light emitting layer has the general formula (IB-1). ) And at least one luminescent polyester comprising a repeating unit containing at least one selected from the structures represented by (IB-2) as a partial structure. Electroluminescent device.   The organic compound layer is composed of at least a hole transport layer and / or a hole injection layer and a light emitting layer, and at least the light emitting layer has a structure represented by the general formulas (IB-1) and (IB-2). 8. The organic electroluminescent device according to claim 7, comprising at least one luminescent polyester comprising a repeating unit containing at least one selected from the above as a partial structure.   The organic compound layer is composed of only one light emitting layer having charge transporting ability, and the light emitting layer comprises at least one selected from the structures represented by the general formulas (IB-1) and (IB-2). 8. The organic electroluminescent element according to claim 7, wherein the organic electroluminescent element comprises at least one luminescent polyester composed of repeating units contained as a partial structure.   The organic light-emitting device according to claim 8, wherein the light-emitting layer includes a charge transporting material.