JP2002324677A - Light emitting element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light emitting element containing at least two kinds of aromatic condensed ring compounds in a light emitting layer with excellent light emitting characteristics and durability. SOLUTION: At least two kinds of compounds expressed in formula (1) are contained in the light emitting layer. In the formula, Ar<11> , Ar<21> , Ar<31> denote arylene groups and Ar<12> , Ar<22> , Ar<32> denote substituents or hydrogen atoms. At least one of Ar<11> , Ar<21> , Ar<31> , Ar<12> , Ar<22> and Ar<32> is either a condensed ring aryl structure or a condensed ring heteroaryl structure. Ar denotes an arylene group or a heteroarylene group.

Description

DETAILED DESCRIPTION OF THE INVENTION

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BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light-emitting element capable of emitting light by converting electric energy into light, and relates to a display element, a display, a backlight, an electrophotograph, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, The present invention relates to a light-emitting element that can be suitably used in fields such as signboards, interiors, and optical communication.

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2. Description of the Related Art At present, research and development on various display elements are active. Among them, an organic electroluminescence (EL) element has been attracting attention as a promising display element because it can emit light with high luminance at a low voltage. ing. For example, a light emitting device that forms an organic thin film by vapor deposition of an organic compound is known (Applied Physics Letters, Vol. 51, No. 91).
3, 1987). The light-emitting element described in this document uses a tris (8-hydroxyquinolinato) aluminum complex (Alq) as an electron transporting material and is laminated with a hole transporting material (amine compound) to form a conventional single-layered device. Compared with this, the light emission characteristics are greatly improved.

In recent years, the application of organic EL elements to full-color displays has been actively studied, but in order to develop high-performance full-color displays, blue, green, and
Red, it is necessary to improve the characteristics of each light emitting element.
For example, in the case of blue light-emitting devices, distyrylarylene compounds (DPVBi) described in “Organic EL Devices and the Forefront of Industrialization” (NTS Corp.) p. There are problems in durability, light emission luminance, and efficiency, and improvements have been desired.

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SUMMARY OF THE INVENTION An object of the present invention is to provide a light emitting device having good light emitting characteristics and durability.

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Means for Solving the Problems The present inventors have studied the above problems and as a result have reached the present invention by the following means. 1. A light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes, wherein the light-emitting layer contains at least two kinds of compounds represented by the following general formula (1). element.

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(Wherein, Ar ¹¹ , Ar ²¹ , and Ar ³¹ represent an arylene group, Ar ¹² , Ar ²² , and Ar ³² represent a substituent or a hydrogen atom. Ar ¹¹ , Ar ²¹ , Ar ³¹ , A
At least one of the ^{r 12, Ar 2 2, Ar} 32 is a condensed ring aryl structure or a condensed ring heteroaryl structure. Ar represents an arylene group or a heteroarylene group. ) 2. 2. The light-emitting device according to item 1, wherein at least one of the compounds represented by the general formula (1) is a compound represented by the following general formula (2).

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(In the formula, Ar ¹¹ , Ar ²¹ , and Ar ³¹ represent an arylene group, Ar ¹² , Ar ²² , and Ar ³² represent a substituent or a hydrogen atom. Ar ¹¹ , Ar ²¹ , Ar ³¹ , A
At least one of the ^{r 12, Ar 2 2, Ar} 32 is a condensed ring aryl structure or a condensed ring heteroaryl structure. R ¹ ,
R ² and R ³ represent a hydrogen atom or a substituent. ) 3. 2. The light-emitting device according to item 1, wherein at least one of the compounds represented by the general formula (1) is a compound represented by the following general formula (3).

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(Wherein, R ¹¹ , R ¹² and R ¹³ each represent a substituent. R ¹⁴ , R ¹⁵ and R ¹⁶ each represent a hydrogen atom or a substituent.
q ^11, q ^12, q ¹³ represents an integer of 0-9. )

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BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In this specification, “to” indicates a range including the numerical values described before and after it as the minimum value and the maximum value, respectively.

According to the present invention, in a light emitting device having a light emitting layer or a plurality of organic compound layers including the light emitting layer formed between a pair of electrodes, the light emitting layer contains at least two kinds of compounds represented by the general formula (1). The present invention relates to a light-emitting element characterized in that:
The light emitting layer may contain a compound other than the compound represented by the general formula (1). The light-emitting layer may be divided into two or more layers, and each layer may contain the compound represented by the general formula (1), or two or more compounds may be contained in the same light-emitting layer. A mode in which two or more compounds represented by the general formula (1) are contained in the same light emitting layer is more preferable.

When two or more compounds represented by the general formula (1) are contained in the same light emitting layer, the concentration of the compound represented by the general formula (1) in the light emitting layer is 5% by mass. It is preferably at least 95% by mass and more preferably at least 10% by mass and at most 90% by mass, and more preferably at least 30% by mass.
More preferably, it is at least 70% by mass.

In the light emitting device of the present invention, at least one of the compounds represented by the general formula (1) is preferably a compound represented by the general formula (2), and represented by the general formula (1). It is more preferable that at least one of the compounds is a compound represented by the general formula (3).

The general formula (1) will be described. Ar ¹¹ ,
Ar ²¹ and Ar ³¹ represent an arylene group. The carbon number of the arylene group is preferably from 6 to 30, more preferably from 6 to 20, and even more preferably from 6 to 16. Examples of the arylene group include, for example, a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a pyrenylene group, a perylenylene group, a fluorenylene group, a biphenylene group, a terphenylene group, a rubrenylene group, a chrysenylene group, a triphenylenylene group, and benzo. Examples include anthrylene group, benzophenanthrylene group, diphenylanthrylene group and the like, and these arylene groups may further have a substituent.

As a substituent on the arylene group, for example, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms)
For example, methyl, ethyl, iso-propyl, t
tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An alkenyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl. ), An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, and particularly preferably having 2 carbon atoms.
To 10, for example, propargyl, 3-pentynyl and the like. ), An aryl group (preferably having 6 carbon atoms)
-30, more preferably 6-20 carbon atoms, particularly preferably 6-12 carbon atoms, for example, phenyl, p-methylphenyl, naphthyl, anthranyl and the like. ), An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 1 carbon atoms).
0, for example, amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and the like. ), An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, particularly preferably having 1 to 10 carbon atoms, and examples include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like. ), An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 2 carbon atoms)
0, particularly preferably 6 to 12 carbon atoms, for example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), A heteroaryloxy group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 2 carbon atoms)
0, particularly preferably 1 to 12 carbon atoms, for example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like. ),

An acyl group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, and particularly preferably having 1 carbon atom)
To 12, for example, acetyl, benzoyl, formyl, pivaloyl and the like. ), An alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 12 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl), and aryloxycarbonyl Group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 2 carbon atoms)
0, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 10 carbon atoms,
For example, acetoxy, benzoyloxy and the like can be mentioned. ), An acylamino group (preferably having 2 to 30 carbon atoms,
More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and includes, for example, acetylamino, benzoylamino and the like. ), An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino).
An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, particularly preferably having 7 to 12 carbon atoms, such as phenyloxycarbonylamino, etc.), and a sulfonylamino group ( It preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino.), A sulfamoyl group (preferably carbon number) 0-30, more preferably 0-20 carbon atoms, particularly preferably 0-12 carbon atoms, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl,
Phenylsulfamoyl and the like. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl). An alkylthio group (preferably having 1 to 30 carbon atoms,
More preferably, it has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio and ethylthio. ), An arylthio group (preferably having 6 carbon atoms)
-30, more preferably 6-20 carbon atoms, particularly preferably 6-12 carbon atoms, such as phenylthio. ),

A heteroarylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, pyridylthio, 2-
Benzimizolylthio, 2-benzoxazolylthio,
2-benzthiazolylthio and the like. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, particularly preferably having 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl and benzenesulfinyl, and a ureido group (preferably 1 to 30 carbon atoms) It preferably has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and includes, for example, ureide, methyl ureide, phenyl ureide and the like, and a phosphoric amide group (preferably 1 to 30 carbon atoms, more preferably It has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethylphosphoramide, phenylphosphoramide and the like. ), Hydroxy group, mercapto group, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino Group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl , Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms). , Particularly preferably 3 to 2 carbon atoms
4, for example, trimethylsilyl, triphenylsilyl and the like. ). These substituents may be further substituted.

Ar ¹¹ , Ar ²¹ , and Ar ³¹ are preferably a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, an arylene group having four or more rings (eg, a pyrenylene group, a peryleneylene group), More preferably, it is a phenylene group, a naphthylene group, a phenanthrene group, an arylene group having four or more rings, more preferably a phenylene group, a phenanthrylene group, or a pyrenylene group, and particularly preferably a pyrenylene group.

Ar ¹² , Ar ²² and Ar ³² represent a substituent or a hydrogen atom. Examples of the substituent include the groups described above for the substituent on Ar ¹¹ . Ar ¹² , Ar ²² , Ar ³²
Are preferably a hydrogen atom, an aryl group, a heteroaryl group, an alkyl group, and an alkenyl group, more preferably a hydrogen atom, an aryl group, and a heteroaryl group, and still more preferably a hydrogen atom and an aryl group. Represents a hydrogen atom or a pyrenyl group.

Ar ¹¹ , Ar ²¹ , Ar ³¹ , Ar ¹² , A
At least one of r ²² and Ar ³² has a condensed aryl structure or a condensed heteroaryl structure. Ar ¹¹ , Ar ²¹ ,
It is preferable that at least one of Ar ³¹ , Ar ¹² , Ar ²² and Ar ³² has a condensed aryl structure. As the condensed aryl structure, preferably, naphthalene structure, anthracene structure, phenanthrene structure, pyrene structure, perylene structure, more preferably naphthalene structure, anthracene structure, pyrene structure, phenanthrene structure, more preferably phenanthrene structure, It is an aryl structure having four or more rings, and particularly preferably a pyrene structure.

The fused heteroaryl structure is preferably a quinoline structure, a quinoxaline structure, a quinazoline structure, an acridine structure, a phenanthridine structure, a phthalazine structure, or a phenanthroline structure, and more preferably a quinoline structure, a quinoxaline structure, or a quinazoline structure. , A phthalazine structure and a phenanthroline structure.

Ar is an arylene group (preferably having 6 carbon atoms)
-30, more preferably 6-20, even more preferably 6-16 carbon atoms, such as phenylene, naphthylene, anthracenylene, phenanthrene, pyrenylene,
And a triphenylene group. ), A heteroarylene group (preferably a nitrogen atom, a sulfur atom, an oxygen atom as a hetero atom, more preferably a nitrogen atom, preferably 2 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and still more preferably 3 to 16 carbon atoms. For example, a pyridylene group, a pyrazylene group, a thiophenylene group, a quinolylene group, a quinoxalylene group, a triazylene group and the like), and these groups may have a substituent. Examples of the substituent include the groups described above for the substituent on Ar ¹¹ . Ar is preferably a phenylene group, a naphthylene group, an anthracenylene group, a pyrenylene group, a triphenylene group, more preferably a phenylene group, and an unsubstituted (Ar ¹¹ , Ar ²¹ and Ar ³¹ are substituted) phenylene group And an alkyl-substituted phenylene group.

Preferred forms of the compound represented by the general formula (1) are a compound represented by the general formula (2) and a compound represented by the following general formula (6).
A compound represented by the following general formula (3), a compound represented by the following general formula (4), a compound represented by the following general formula (5), a compound represented by the following general formula (7), A compound represented by the formula (8), and a more preferred embodiment is a compound represented by the formula (3). Further, the compound of the present invention is preferably a compound composed of only carbon atoms and hydrogen atoms.

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The general formula (2) will be described. Ar ¹¹ , Ar ²¹ , Ar ³¹ , Ar ¹² , Ar ²² , A of the general formula (2)
r ³² is Ar ¹¹ , Ar ²¹ , Ar described in the general formula (1).
³¹ , Ar ¹² , Ar ²² , and Ar ³² have the same meanings,
The preferred range is also the same. R ¹ , R ² and R ³ represent a hydrogen atom or a substituent. Examples of the substituent include the groups described above for the substituent on Ar ¹¹ . R ¹ , R ² and R ³ are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group.

In the compounds represented by the general formulas (1) and (2), at least one of Ar ¹¹ , Ar ²¹ , Ar ³¹ , Ar ¹² , Ar ²² and Ar ³² has a phenanthrene structure and a condensed aryl structure having four or more rings. Alternatively, a compound having a condensed heteroaryl structure having three or more rings is preferable, and a phenanthrene structure and a pyrene structure are more preferable. In general formula (1), the compounds represented by (2) is preferably Ar ^12, Ar ^22, compound Ar ³² is a condensed aryl group or a hydrogen atom, Ar ^12, Ar
²² and Ar ³² are more preferably a condensed aryl group having three or more rings or a hydrogen atom, and Ar ¹² , Ar ²² and Ar ³² are preferred.
Is more preferably a phenanthrene structure, a condensed aryl structure having four or more rings, or a hydrogen atom. Compounds represented by the general formulas (1) and (2) are Ar ¹¹ , Ar ²¹ ,
Compounds in which Ar ³¹ is a phenanthrylene group or a condensed arylene group having four or more rings are preferred.

The compounds represented by the general formulas (1) and (2) are preferably compounds composed only of carbon atoms and hydrogen atoms.

The general formula (3) will be described. R ¹¹ , R
¹² and R ¹³ represent a substituent. As the substituent, the aforementioned Ar ¹¹
Examples include the groups described for the above substituents. R ¹¹ , R ¹² , R
¹³ is preferably an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, or an alkoxy group, more preferably an alkyl group or an aryl group, and further preferably an aryl group.

Q ¹¹ , q ¹² and q ^{13 each} represent an integer of 0-9. q ^11, q ^12, q ¹³ is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, more preferably 0, 1.

R ¹⁴ , R ¹⁵ and R ¹⁶ have the same meanings as R ¹ , and the preferred range is also the same.

The general formula (4) will be described. R ⁴¹ , R
⁴² and R ⁴³ have the same meanings as R ¹ described above, and the preferred ranges are also the same. R ⁴⁴ , R ⁴⁵ and R ⁴⁶ have the same meanings as R ¹¹ described above, and the preferred ranges are also the same. q ⁴¹ , q ⁴² and q ⁴³ are 0-9
And preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably 0 or 1.
It is.

The general formula (5) will be described. R⁵¹Is before
Note R¹¹And the preferred range is also the same.
R⁵⁴, R⁵⁵, R⁵⁶ Is R¹Is synonymous with
The box is the same. Ar⁵¹Is an anthryl group, phenantry
And a pyrenyl group; Ar⁵²Is a phenanthryl group,
Represents a pyrenyl group. Ar⁵¹Is a phenanthryl group, pyreni
And a pyrenyl group is more preferred. Ar⁵²Is
A pyrenyl group is preferred. q ⁵¹ Represents an integer of 0 to 9,
It is preferably an integer of 0 to 3, more preferably 0 to 2.
And more preferably 0 or 1.

The general formula (6) will be described. R ⁶¹ , R
⁶² has the same meaning as R ¹ , and the preferred range is also the same. Ar ⁶¹ , Ar ⁶² , Ar ⁶³ and Ar ⁶⁴ each represent a condensed aryl group, preferably a phenanthryl group, an aryl group having 4 or more rings, more preferably a phenanthryl group;
A pyrenyl group.

The general formula (7) will be described. R ⁷¹ , R
⁷² , R ⁷³ and R ⁷⁴ have the same meanings as R ¹¹ described above, and the preferred ranges are also the same. R ⁷⁵ and R ⁷⁶ are the same as R ¹ , and the preferred range is also the same. q ⁷¹ , q ⁷² , q ⁷³ , and q ⁷⁴ represent an integer of 0 to 9, preferably an integer of 0 to 3,
It is more preferably an integer of 0 to 2, and even more preferably 0 or 1.

The general formula (8) will be described. R ⁸¹ , R
⁸² , R ⁸³ and R ⁸⁴ have the same meanings as R ¹¹ described above, and the preferred ranges are also the same. R ⁸⁵ and R ⁸⁶ are the same as R ¹ , and the preferred range is also the same. q ⁸¹ , q ⁸² , q ⁸³ and q ^{84 each} represent an integer of 0 to 9, preferably 0 to 3;
It is more preferably an integer of 0 to 2, and even more preferably 0 or 1.

The light-emitting device of the present invention preferably has a form having a compound represented by the general formula (1) having a phenanthrene structure and a compound represented by the general formula (1) having a pyrene structure. The species is more preferably a form containing the compound represented by the general formula (3) and the compound represented by the general formula (4).

In the present invention, the light emitting layer contains at least two compounds represented by the general formula (1), and at least one of them contains the compounds represented by the general formulas (2) to (8). May do it. The concentration of the compound represented by any one of formulas (2) to (8) in the light-emitting layer is preferably from 1% by mass to 99% by mass, more preferably from 3% by mass to 97% by mass. More preferably, the content is 5% by mass or more and 95% by mass or less.

The compound of the present invention may be a low molecular weight compound, and an oligomer compound or a polymer compound (having a weight average molecular weight (in terms of polystyrene) of preferably 1000 to 1000)
5,000,000, more preferably 2,000 to 10,000
00, more preferably 3,000 to 100,000. ). In the case of a polymer compound, the structures represented by the general formulas (1) to (8) may be contained in the polymer main chain, or may be contained in the polymer side chain. In the case of a polymer compound, it may be a homopolymer compound or a copolymer. The compound of the present invention is preferably a low molecular compound.

The λmax (maximum emission wavelength) of the fluorescence spectrum of the compound of the present invention is preferably from 400 to 500 nm, more preferably from 400 to 480 nm, and still more preferably from 400 to 460 nm.

Next, examples of compounds of the present invention will be shown.
The present invention is not limited to this.

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Next, a method for producing the compound of the present invention (the compound represented by the general formula (1)) will be described. The compound of the present invention can be synthesized using various known aromatic carbon-carbon bond forming reactions, and for example, Organic Sy.
nthesis Reaction Guide (Jo
hn Wiley & Sons, Inc. Company) p. 61
7 to p. 643 and Comprehensive
Organic Transformation (VC
H) p. 5-p. 103 can be synthesized. A synthesis method of generating a carbon-carbon bond in the presence of a palladium catalyst is preferable, and a method of synthesizing a boric acid derivative and an aryl halide derivative in the presence of a palladium catalyst is more preferable.

As the boric acid derivative, a substituted or unsubstituted aryl boric acid derivative (for example, 1,4-phenyldiboric acid, 4,4'-biphenyldiboric acid, pyrene boric acid derivative, phenanthrene boric acid derivative, etc.) And heteroarylboric acid derivatives (for example, pyridyldiboric acid and the like).

The halogen atom in the aryl halide derivative is preferably a chlorine, bromine or iodine atom, and particularly preferably a bromine atom.

The palladium catalyst is not particularly restricted but includes, for example, palladium tetrakistriphenylphosphine, palladium carbon, palladium acetate, palladium dichloride (dppf) (dppf: 1,1'-bisdiphenylphosphinoferrocene) and the like. . A ligand such as triphenylphosphine may be added at the same time.

In this reaction, it is preferable to use a base. The type of the base used is not particularly limited, and examples thereof include sodium carbonate, sodium acetate, and triethylamine. The amount of the base used is not particularly limited, but is preferably 0.1 to 20 equivalents, particularly preferably 1 to 10 equivalents, to the boric acid (ester) site.

In this reaction, it is preferable to use a solvent. The solvent used is not particularly limited, for example, ethanol, water,
Ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, toluene, tetrahydrofuran, and a mixed solvent thereof can be used.

Next, a light emitting device containing the compound of the present invention will be described. The light emitting device of the present invention is not particularly limited as long as it is a device using the compound of the present invention, such as a system, a driving method, and a use form. The thing used as is preferred.

The method for forming the organic layer of the light emitting device containing the compound of the present invention is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, and the like.
Methods such as a coating method, an ink jet method, and a printing method are used, and resistance heating evaporation, a coating method, and a transfer method are preferable in terms of characteristics and production.

The light-emitting device of the present invention is a device in which a light-emitting layer or a plurality of organic compound layers including the light-emitting layer are formed between a pair of anode and cathode electrodes. , An electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers may have another function. Various appropriate materials can be used for forming each layer.

The anode supplies holes to the hole injection layer, the hole transport layer, the light emitting layer, etc., and may be made of a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof. It is possible to use a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO), or metals such as gold, silver, chromium, and nickel, and those metals and conductive metal oxides. Mixtures or laminates, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO, and the like. Oxides,
In particular, ITO is preferable in terms of productivity, high conductivity, transparency, and the like. The thickness of the anode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm to 500 nm.

As the anode, a layer formed on a soda lime glass, an alkali-free glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass in order to reduce ions eluted from the glass. Further, when soda lime glass is used, it is preferable to use a glass coated with a barrier coat such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength. When glass is used, the thickness is usually 0.2 mm or more, preferably 0.7 mm or more. Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (such as a sol-gel method), and a coating of a dispersion of indium tin oxide are used. The film is formed by the method described above. The anode can be cleaned or otherwise treated to lower the device's drive voltage,
It is also possible to increase the luminous efficiency. For example, in the case of ITO, UV-ozone treatment, plasma treatment and the like are effective.

The cathode supplies electrons to the electron injecting layer, the electron transporting layer, the light emitting layer, etc., and provides the adhesion between the negative electrode and the adjacent layer, such as the electron injecting layer, the electron transporting layer, the light emitting layer, the ionization potential, and the like. It is selected in consideration of stability and the like. As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples thereof include an alkali metal (for example, L
i, Na, K, etc.) and their fluorides or oxides, alkaline earth metals (eg, Mg, Ca, etc.) and their fluorides or oxides, gold, silver, lead, aluminum, sodium-potassium alloys or mixtures thereof Metal, a lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof, indium, rare earth metals such as ytterbium and the like, preferably a material having a work function of 4 eV or less, more preferably aluminum , A lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof or the like. The cathode can have not only a single-layer structure of the compound and the mixture, but also a stacked structure including the compound and the mixture. For example, a laminated structure of aluminum / lithium fluoride and aluminum / lithium oxide is preferable. The thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and further preferably 100 nm.
nm to 1 μm. A method such as an electron beam method, a sputtering method, a resistance heating evaporation method, or a coating method is used for manufacturing the cathode, and a metal can be evaporated alone or two or more components can be simultaneously evaporated. Further, an alloy electrode can be formed by depositing a plurality of metals at the same time, or an alloy prepared in advance may be deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

The material of the light emitting layer is capable of injecting holes from an anode, a hole injection layer, or a hole transport layer and applying electrons from a cathode, an electron injection layer, or an electron transport layer when an electric field is applied. Any function can be used as long as it can form a layer having a function of transferring injected charges, providing a field for recombination of holes and electrons and emitting light, and a singlet exciton. Or a substance that emits light from any of triplet excitons. For example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives, oxadiazole derivatives, aldazine derivatives , Metal complexes and rare earth complexes of pyrrolidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives Polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene, such as various metal complexes, Machine silane derivatives, the compounds of the present invention, and the like. The thickness of the light emitting layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 1 μm.
500 nm. The method for forming the light-emitting layer is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip coating, etc.), inkjet, and printing. LB method, transfer method and the like are used, and preferably, resistance heating evaporation and coating method.

The material of the hole injection layer and the hole transport layer has a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode. Should be fine. Specific examples thereof include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, and styryl anthracene derivatives , Fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds,
Examples thereof include poly (N-vinylcarbazole) derivatives, aniline-based copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silane derivatives, carbon films, and the compounds of the present invention. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually 1
It is preferably in the range of nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 50 μm.
0 nm. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. Examples of the method for forming the hole injection layer and the hole transport layer include a vacuum deposition method, an LB method, and a method in which the hole injection and transport material is dissolved or dispersed in a solvent and coated (spin coating method, casting method, dip coating method). Such),
An ink jet method, a printing method, and a transfer method are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane,
Melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, and the like.

The material of the electron injecting layer and the electron transporting layer is not limited as long as it has a function of injecting electrons from the cathode, a function of transporting electrons, or a function of blocking holes injected from the anode. Good. Specific examples thereof include triazole derivatives, oxazole derivatives, oxadiazole derivatives,
Aromatic tetracarboxylic anhydrides such as imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalenes and perylenes Phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole as ligands, organic silane derivatives,
Examples include the compounds of the present invention. The thickness of the electron injection layer and the electron transport layer is not particularly limited, but is usually 1 nm.
~ 5 μm, more preferably 5n
m to 1 μm, more preferably 10 nm to 500 n
m. The electron injection layer and the electron transport layer are made of one of the materials described above.
It may be a single layer structure composed of two or more kinds,
It may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. Examples of the method for forming the electron injecting layer and the electron transporting layer include a vacuum deposition method, an LB method, a method in which the electron injecting and transporting material is dissolved or dispersed in a solvent and coated (eg, a spin coating method, a casting method, a dip coating method), An ink jet method, a printing method, a transfer method, and the like are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.

As the material of the protective layer, any material may be used as long as it has a function of preventing a substance that promotes element deterioration such as moisture and oxygen from entering the element. As a specific example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO ₂ , Al ₂ O ₃ , G
eO, NiO, CaO, BaO, Fe 2 O 3, Y 2 O 3, T
metal oxides such as iO ₂ , MgF ₂ , LiF, AlF ₃ , C
metal fluorides such as aF ₂ , SiO _x N _y , polyethylene,
Polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer A copolymer obtained by copolymerizing a monomer mixture containing, a fluorine-containing copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, and a moisture-proof property having a water absorption of 0.1% or less Substances and the like.
There is no particular limitation on the method of forming the protective layer. For example, a vacuum deposition method, a sputtering method, a reactive sputtering method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, a plasma polymerization method (high-frequency excitation ion Plating method), plasma CV
D method, laser CVD method, thermal CVD method, gas source CV
D method, coating method, printing method and transfer method can be applied.

In the light emitting device containing the compound of the present invention, a blue light emitting device having high efficiency and high durability can be manufactured. In addition, orange to red luminescent dyes (for example, DCM (7,4-
(Dicyanomethlene) -2-methyl-6- (4-dimethylaminostyry
l) -4H-pyran), a pyran derivative represented by Ir (ac
ac) (phq) ₂ (acac = acetylacetone, p
hq = phenylquinoline) in a light-emitting layer, whereby a highly efficient and highly durable white light-emitting element can be manufactured.

[0073]

EXAMPLES Examples of the present invention will be described below.
Embodiments of the present invention are not limited to these.

Synthesis of (1-1) Pyrene borate ester (a) 1.0 g, 1,3
0.29 g of 5-tribromobenzene, sodium carbonate
To 0.6 g, 0.05 g of triphenylphosphine and 0.05 g of palladium carbon, 20 ml of diethylene glycol dimethyl ether and 20 ml of water were added, and the mixture was stirred under reflux. Six hours later, 200 ml of chloroform was added to the reaction solution,
The mixture was diluted with 200 ml of water and filtered through Celite (Wako Pure Chemical Industries). The organic layer was washed twice with 100 ml of water, dried over sodium sulfate, and concentrated. After purification by column chromatography (chloroform), purification by recrystallization (chloroform / methanol) (1-1) 0.5 g
I got A vapor-deposited film (film thickness: 100 nm) of (1-1) was prepared and its film fluorescence was measured.
ax was 480 nm. The measured glass transition point (Tg) of the compound was 164 ° C.

[0075]

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Synthesis of (1-2) Phenanthrene borate 1.5 g, 1,3,5
0.47 g of tribromobenzene, sodium carbonate
To 1.6 g, 0.07 g of triphenylphosphine and 0.07 g of palladium carbon, 30 ml of diethylene glycol dimethyl ether and 30 ml of water were added, and the mixture was stirred under reflux. After 6 hours, the reaction solution was chloroform 200m
The mixture was diluted with 200 ml of 1M aqueous hydrochloric acid and filtered through celite. The organic layer was washed twice with 100 ml of water, dried over sodium sulfate, and concentrated. After purifying by column chromatography (hexane / ethyl acetate system), purifying by recrystallization (chloroform / methanol) (1-2)
1.0 g was obtained. The MS spectrum was measured and (1-
The structure of 2) was confirmed. (1-2) producing a deposited film,
When the membrane fluorescence was measured, the maximum wavelength of the membrane fluorescence was λmax.
Was 380 nm.

[0077]

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Synthesis of (1-39) Pyrene borate ester 1.0 g, 1,2,4,5-tetrabromobenzene 0.28 g, sodium carbonate 0.1 g
To 88 g, 0.05 g of triphenylphosphine and 0.05 g of palladium carbon, 30 ml of diethylene glycol dimethyl ether and 30 ml of water were added and stirred under reflux. Six hours later, 200 ml of chloroform was added to the reaction solution,
The mixture was diluted with 200 ml of 1M hydrochloric acid and filtered through celite. The organic layer was washed twice with 100 ml of water, dried over sodium sulfate, and concentrated. After purification by column chromatography (chloroform), purification was performed by recrystallization (chloroform / methanol) to obtain 0.4 g of (1-39). The MS spectrum was measured to confirm the structure of (1-39).

[0079]

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Synthesis of (1-40) Phenanthrene borate 1.15 g, 1,2,2
0.35 g of 4,5-tetrabromobenzene, 0.96 g of sodium carbonate, 0.07 of triphenylphosphine
g, 0.07 g of palladium carbon, 30 ml of diethylene glycol dimethyl ether and 30 ml of water were added, and the mixture was stirred under reflux. After 6 hours, the mixture was cooled to room temperature and filtered through celite. The filtered solid was dissolved in chloroform and filtered through celite to remove palladium carbon. After purification by column chromatography (chloroform), purification by recrystallization (chloroform / methanol) (1-40)
0.5 g was obtained. According to MS spectrum measurement, (1-4
The structure of 0) was confirmed. When the deposited film of (1-40) was prepared and the film fluorescence was measured, the film fluorescence maximum wavelength λm
ax was 440 nm.

[0081]

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Synthesis of (1-35) To 25 g of 1,3,5-tribromobenzene was added 250 ml of diethyl ether, and the mixture was cooled to −78 ° C. under a nitrogen stream. n-butyllithium (1.6 M hexane solution) 5
2 ml was added dropwise, and the temperature was raised to room temperature. Anthrone 15.4
g was added in portions, and the mixture was stirred for 3 hours while heating under reflux. 500 ml of ethyl acetate and 300 ml of 1M aqueous hydrochloric acid were added to the solution cooled to room temperature.
ml was added, and the organic layer was separated. Organic layer was washed with saturated saline 3
After washing with 00 ml, it was concentrated. Purification by column chromatography (chloroform) gave 1.5 g of compound A. 0.84 g of pyrene borate, compound A
0.5 g, sodium carbonate 0.51 g, triphenylphosphine 0.05 g, palladium carbon 0.05
g to diethylene glycol dimethyl ether 30m
1 and 30 ml of water were added and stirred under reflux. After 6 hours, the mixture was cooled to room temperature and filtered through celite. The filtered solid was dissolved in chloroform and filtered through celite to remove palladium carbon. Column chromatography (chloroform)
After purification by recrystallization, purification was performed by recrystallization (chloroform / methanol) to obtain 0.3 g of (1-35). The structure of (1-35) was confirmed by MS spectrum measurement. (1-3
5) A vapor-deposited film was prepared and the film fluorescence was measured.
The membrane fluorescence maximum wavelength λmax was 470 nm.

[0083]

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Synthesis of (1-37) To 10 g of 1,3,5-tribromobenzene was added 150 ml of diethyl ether, and the mixture was cooled to −78 ° C. under a nitrogen stream. n-butyllithium (1.6 M hexane solution) 4
1.7 ml was added dropwise, and the temperature was raised to room temperature. Anthrone 1
3.0 g was added in portions, and the mixture was stirred for 3 hours while heating under reflux. Diethyl ether was removed by distillation, 200 ml of toluene and 0.1 g of paratoluenesulfonic acid were added, and the mixture was stirred with heating under reflux for 3 hours. Chloroform 300 is added to the solution cooled to room temperature.
ml and 300 ml of water were added, and the organic layer was separated and concentrated.
After purification by column chromatography (chloroform), crystallization (chloroform / hexane) was carried out to give Compound B
2.0 g were obtained. 0.27 g of pyrene borate,
Compound B 0.4 g, sodium carbonate 0.17 g, triphenylphosphine 0.05 g, palladium carbon
0.05 g to diethylene glycol dimethyl ether
30 ml and 30 ml of water were added and the mixture was stirred under reflux. After 6 hours, the mixture was cooled to room temperature and filtered through celite. The filtered solid was dissolved in chloroform and filtered through celite to remove palladium carbon. The residue was purified by column chromatography (eluted with hexane / ethyl acetate, then eluted with chloroform) and then recrystallized to obtain 0.1 g of (chloroform / methanol) (1-37). MS
The structure (1-37) was confirmed by spectrum measurement.
When a vapor-deposited film of (1-37) was prepared and the film fluorescence was measured, the film fluorescence maximum wavelength λmax was 467 nm.

[0085]

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Comparative Example 1 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was evaporated to a thickness of 40 nm, a distyryl compound b was evaporated to a thickness of 20 nm, and an azole compound c was evaporated to a thickness of 40 nm. A mask (a mask having a light-emitting area of 4 mm × 5 mm) patterned on the organic thin film is provided, and magnesium: silver = 10:
1 was co-evaporated to 50 nm, and then 50 nm of silver was evaporated to produce a device. Toyo Technica Source Measure Unit 2
Using a 400 type, a DC constant voltage is applied to the EL element to emit light, and the luminance is measured by a luminance meter BM-8 manufactured by Topcon Corporation, and the emission wavelength is measured by a spectrum analyzer PM manufactured by Hamamatsu Photonics.
It measured using A-11. As a result, the chromaticity value (0.1
5,0.20) blue-green emission with maximum brightness of 1130 cd
/ M ² . When left in a nitrogen atmosphere for one day, cloudiness of the film surface was observed.

Comparative Example 2 A device was prepared and evaluated in the same manner as in Comparative Example 1, except that the compound (1-1) of the present invention was used instead of the compound b. as a result,
(0.17, 0.31) blue-green emission with maximum brightness of 1
It was 2740 cd / m ² . The external quantum efficiency of the device (φ
Was calculated _EL) (emission luminance, emission spectrum, current density, calculated from the relative luminous efficiency curve) was φ _EL = 1.8%. When left in a nitrogen atmosphere for one day, the film surface was transparent. In addition, when light was continuously emitted at 100 cd / m ² for 2 hours, the driving voltage increased by 1.0 V.

[0088]

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Example 1 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N'-diphenyl-N, N'-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and the compound (1-1) and the compound (1-2) were further deposited thereon at a ratio of 1: 1. And the azole compound c was deposited thereon by 40 nm.
As a result of performing cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.
15, 0.15) blue light emission, maximum luminance 4200 cd
/ M ² . When the external quantum efficiency of the device was calculated, φ _EL = 2.2%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100 cd / m
^{After 2} hours of continuous light emission at 2, the driving voltage was 0.2 V
Rose.

Example 2 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and the compound (1-1) and the compound (1-2) were further deposited thereon at a ratio of 1: 3. And the azole compound c was deposited thereon by 40 nm.
As a result of performing cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.
15, 0.15) blue light emission with a maximum luminance of 3300c
d / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.8%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100 cd / m
^{After 2} hours of continuous light emission at 2, the driving voltage was 0.2 V
Rose.

Example 3 A cleaned ITO substrate was put into a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and a compound (1-1) and a compound (1-2) were added thereon in a ratio of 1:10. And the azole compound c was deposited thereon by 40 nm. As a result of cathode deposition and device evaluation as in Comparative Example 1,
(0.16, 0.10) blue light emission with a maximum luminance of 13
40 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.0%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100 cd
/ M ² for 2 hours, the driving voltage was 0.1.
It increased by 3V.

Example 4 A cleaned ITO substrate was put into a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and a compound (1-1) and a compound (1-27) having a ratio of 1: 1 were formed thereon. And the azole compound c was deposited thereon by 40 nm. As a result of cathode deposition and device evaluation as in Comparative Example 1,
A blue-green emission of (0.16, 0.26) was obtained, and a maximum luminance of 13,200 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 2.0%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 1
When the light was continuously emitted at 00 cd / m ² for 2 hours, the driving voltage increased by 0.2 V.

Example 5 A cleaned ITO substrate was put into a vapor deposition apparatus, and α-NPD
(N, N'-diphenyl-N, N'-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and a compound (1-1) and a compound (1-36) were added thereon in a ratio of 1: 1. And the azole compound c was deposited thereon by 40 nm. As a result of cathode deposition and device evaluation as in Comparative Example 1,
Blue light emission of (0.15, 0.15) was obtained, and a maximum luminance of 3200 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.8%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100
When light was continuously emitted at cd / m ² for 2 hours, the driving voltage increased by 0.3 V.

Example 6 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthy
) -Benzidine) is evaporated to a thickness of 40 nm, and the compound is
(1-1) and compound (1-37) at a ratio of 1: 1
And an azole compound c is deposited thereon to a thickness of 40 nm.
Was. As a result of cathode deposition and device evaluation as in Comparative Example 1,
Blue-green light emission of (0.15, 0.20) was obtained,
4700 cd / m ^TwoI got Calculate the external quantum efficiency of the device
When I put it out, φ_EL= 1.9%. Nitrogen atmosphere
When left for one day, the film surface was transparent. Also, 10
0 cd / m^Two Flash for 2 hours,
The pressure rose 0.3V.

Example 7 A cleaned ITO substrate was put in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and a compound (1-1) and a compound (1-8) were added thereon in a ratio of 1: 1. And the azole compound c was deposited thereon by 40 nm.
As a result of performing cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.
15, 0.17) and a maximum luminance of 310.
0 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.7%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100 cd /
When light was continuously emitted at m ² for 2 hours, the driving voltage was 0.6
V rose.

Example 8 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited in a thickness of 40 nm, and the compound (1-1) and the compound (1-4) were further deposited thereon at a ratio of 5: 1. And the azole compound c was deposited thereon by 40 nm.
As a result of performing cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.
17, 0.29) blue-green emission was obtained, and the maximum luminance was 78.
00 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.7%. When left in a nitrogen atmosphere for one day, the film surface was transparent. Also, 100 cd
/ M ² for 2 hours, the driving voltage was 0.1.
It rose by 6V.

Example 9 A cleaned ITO substrate was put into a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthy
) -Benzidine) is evaporated to a thickness of 40 nm, and the compound is
(1-1) and compound (1-48) are co-evaporated at a ratio of 5: 1.
And an azole compound c is deposited thereon to a thickness of 40 nm.
Was. As a result of cathode deposition and device evaluation as in Comparative Example 1,
Blue-green light emission of (0.17, 0.25) was obtained,
6200 cd / m ^TwoI got Calculate the external quantum efficiency of the device
When I put it out, φ_EL= 1.7%. Nitrogen atmosphere
When left for one day, the film surface was transparent. Also, 10
0 cd / m^Two Flash for 2 hours,
The pressure rose 0.8V.

Example 10 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N'-diphenyl-N, N'-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, compound (1-1) was deposited thereon to a thickness of 10 nm, and compound (1-
2) was deposited to a thickness of 10 nm, and an azole compound c was deposited thereon to a thickness of 40 nm. As a result of cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.17, 0.27) blue-green light was obtained, and a maximum luminance of 12,000 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.8%. When left in a nitrogen atmosphere for one day, the film surface was transparent. In addition, when light was continuously emitted at 100 cd / m ² for 2 hours, the driving voltage increased by 0.8 V.

Example 11 40 mg of polyvinylcarbazole, 2- (4-t-butylphenyl) -5- (4-biphenyl) -1,3,4
-Oxadiazole 12 mg, (1-1) 1 mg,
(1-39) 1 mg was dissolved in dichloroethane 2.5 ml, and spin-coated on a washed ITO substrate (1).
500 rpm, 20 sec). The thickness of the organic layer is 120 n
m. As a result of performing cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.16, 0.15) blue light emission was obtained, and a maximum luminance of 2200 cd / m ² was obtained.

Example 12 A cleaned ITO substrate was placed in a vapor deposition apparatus, and α-NPD
(N, N′-diphenyl-N, N′-di (α-naphthyl) -benzidine) was deposited to a thickness of 40 nm, and a compound (1-1) and a compound (1-2) were added thereon in a ratio of 1: 100. And the azole compound c was deposited thereon by 40 nm. Cathode vapor deposition and device evaluation were performed in the same manner as in Comparative Example 1. As a result, blue light emission of (0.16, 0.09) and a maximum luminance of 12
It was 80 cd / m ² . When the external quantum efficiency of the device was calculated, φ _EL = 1.0%. Under nitrogen atmosphere 1
After standing for a day, the film surface was transparent. Also, 100 c
When the light was continuously emitted at d / m ² for 2 hours, the driving voltage increased by 0.4 V.

[0101]

Light-emitting element of the present invention exhibits emission characteristics (color purity, external quantum efficiency (phi _EL)), no clouding durability (film surface,
Excellent in display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signs, interiors, optical communications, etc. it can.

Claims (3)

[Claims] 1. A light-emitting element in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of electrodes,
A light-emitting element comprising at least two compounds represented by the following general formula (1) in a light-emitting layer. Embedded image ^{(Wherein, Ar 11, Ar 21, Ar} 31 represents an arylene ^{group, Ar 12, Ar 22, Ar} 32 .Ar 11 that represents a substituent group or a hydrogen ^{atom, Ar 21, Ar 31, Ar} 12, Ar 2 2 , A
At least one of r ³² has a condensed aryl structure or a condensed heteroaryl structure. Ar represents an arylene group or a heteroarylene group. ) 2. The light emitting device according to claim 1, wherein at least one of the compounds represented by the general formula (1) is a compound represented by the following general formula (2). Embedded image ^{(Wherein, Ar 11, Ar 21, Ar} 31 represents an arylene ^{group, Ar 12, Ar 22, Ar} 32 .Ar 11 that represents a substituent group or a hydrogen ^{atom, Ar 21, Ar 31, Ar} 12, Ar 2 2 , A
At least one of r ³² has a condensed aryl structure or a condensed heteroaryl structure. R ¹ , R ² and R ³ represent a hydrogen atom or a substituent. ) 3. The light emitting device according to claim 1, wherein at least one of the compounds represented by the general formula (1) is a compound represented by the following general formula (3). Embedded image ^{(Wherein, R 11, R 12, R} 13 represents a substituent .R ^14,
R ¹⁵ and R ¹⁶ represent a hydrogen atom or a substituent. q ¹¹ ,
q ^12, q ¹³ represents an integer of 0-9. )