JP2002334785A - Luminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a luminescent element having an excellent light emission characteristic and high durability. SOLUTION: In this luminescent element, a luminescent layer or plural organic compound layers including the luminescent layer are formed between a pair of electrodes. The luminescent element is characterized by including, in the luminescent layer, at least one kind of a compound expressed by general formula (1), and at least one kind of styryl derivative comprising only carbon atoms, hydrogen atoms, oxygen atoms, sulfur atoms and halogen atoms. In general formula (1), Ar<11> , Ar<21> and Ar<31> each represent an arylene group, Ar<12> , Ar<22> and Ar<32> each represent a substituted group or a hydrogen atom, at least one of Ar<11> , Ar<21> , Ar<31> , Ar<12> , Ar<22> and Ar<32> is a condensed ring aryl structure or a condensed ring hetero-aryl structure, and Ar is an arylene group or a hetero-arylene group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent (EL) device capable of converting electric energy into light and emitting light.
The present invention relates to a light-emitting element that can be suitably used in fields such as 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, a sign, an interior, and an optical communication.

[0002]

2. Description of the Related Art At present, research and development on various display elements are active, and among them, an organic electroluminescent element has attracted attention as a promising display element because it can obtain high-luminance light emission at a low voltage. 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, p. 913, 19).
1987). The light emitting element described in this document is Tris (8
-Hydroxyquinolinato) aluminum complex (Alq)
Is used as an electron transporting material, and is laminated with a hole transporting material (amine compound), whereby the light emitting characteristics are greatly improved as compared with the conventional single-layer type device.

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.

[0004]

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

[0005]

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. In 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, at least one compound represented by the following general formula (1) is contained in the light-emitting layer, and a carbon atom and a hydrogen atom At least one styryl derivative composed of only oxygen, sulfur, and halogen atoms
And a seed.

[0006]

Embedded image

(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).

[0008]

Embedded image

(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).

[0010]

Embedded image

(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. ) 4. A styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a halogen atom has a general formula (S
T-1). The light-emitting device according to any one of 1 to 3 above,

[0012]

Embedded image

(In the general formula (ST-1), Ar ¹⁰¹ represents a substituted or unsubstituted arylene group having 12 to 50 carbon atoms. R ¹⁰¹ and R ¹⁰² represent a hydrogen atom, an alkyl group,
Represents an aryl group. R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ and R ¹⁰⁶ each represent a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. ) 5. 5. The light emitting device according to any one of the above items 1 to 4, wherein the glass transition point of the styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom and a halogen atom is 80 ° C. or higher.

[0014]

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.

The present invention provides a light-emitting element having a light-emitting layer or a plurality of organic compound layers including the light-emitting layer formed between a pair of electrodes, wherein the light-emitting layer contains at least one compound represented by the general formula (1). And a styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a halogen atom.

The concentration of the compound represented by the general formula (1) in the light-emitting layer is preferably 1% by mass to 99% by mass, more preferably 5% by mass to 90% by mass. More preferably, the content is 10% by mass or more and 80% by mass or less.

In the present invention, a carbon atom, a hydrogen atom, an oxygen atom,
The concentration of the styryl derivative composed of only a sulfur atom and a halogen atom in the light emitting layer is preferably 1% by mass to 99% by mass, and more preferably 5% by mass to 90% by mass.
The content is more preferably not more than 10% by mass and more preferably not more than 80% by mass.

The ratio of the compound represented by the general formula (1) to the styryl derivative composed of only carbon atom, hydrogen atom, oxygen atom, sulfur atom and halogen atom in the light emitting layer is 1: 1.
It is preferably 0 to 10: 1, more preferably 1: 5 to 5: 1, and still more preferably 1: 2 to 2: 1.

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 the 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 phenanthrenylene group, a biphenylene group, an arylene group having four or more rings (eg, a pyrenylene group, a peryleneylene group). And more preferably a phenylene group, a naphthylene group, a phenanthrene group, an arylene group having four or more rings, still more preferably a phenylene group, a phenanthrylene group or a pyrenylene group, and particularly preferably a pyrenylene group.

The above Ar¹², Ar^{twenty two}, Ar³² Is a substituent
Or represents a hydrogen atom. As the substituent, the aforementioned Ar¹¹Up
And the groups described for the substituent. Ar¹², Ar^{twenty two},
Ar ³² Is preferably a hydrogen atom, an aryl group,
Loaryl group, alkyl group, alkenyl group, and more
Preferably, a hydrogen atom, an aryl group, a heteroaryl group
And more preferably a hydrogen atom or an aryl group.
And particularly preferably a hydrogen atom and a pyrenyl group.

The above Ar ¹¹ , Ar ²¹ , Ar ³¹ , Ar ¹² , A
at least one of r ²² and Ar ³² is a condensed aryl structure;
Or a condensed heteroaryl structure. Ar ¹¹ , A
It is preferable that at least one of r ²¹ , Ar ³¹ , Ar ¹² , Ar ²² and Ar ³² has a condensed aryl structure.

The condensed aryl structure is preferably a naphthalene structure, an anthracene structure, a phenanthrene structure, a pyrene structure, a perylene structure, more preferably
It is a naphthalene structure, an anthracene structure, a pyrene structure, or a phenanthrene structure, more preferably a phenanthrene structure, an aryl structure having four or more rings, and particularly preferably a pyrene structure.

The condensed 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, more preferably a quinoline structure, a quinoxaline structure, They have a quinazoline structure, a phthalazine structure and a phenanthroline structure.

Ar is a trivalent arylene group (preferably having 6 to 30 carbon atoms, more preferably 6 to 2 carbon atoms).
0, more preferably 6 to 16 carbon atoms, for example, phenylene group, naphthylene group, anthracenylene group, phenanthrene group, pyrenylene group, triphenylene group and the like. ), 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 a trivalent group, each of which is a phenylene group (benzenetriyl), a naphthylene group (naphthalenetriyl), an anthracenylene group (anthracentriyl), a pyrenylene group (pyrentriyl),
It is preferably a triphenylene group, more preferably a phenylene group, and is unsubstituted (Ar ¹¹ , Ar ²¹ ,
Ar ³¹ is more preferably a phenylene group or an alkyl-substituted phenylene group.

Preferred forms of the compound represented by the general formula (1) are a compound represented by the following 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.

[0031]

Embedded image

[0032]

Embedded image

[0033]

Embedded image

[0034]

Embedded image

[0035]

Embedded image

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.

The compounds represented by the general formulas (1) and (2)
 Ar¹¹, Ar^{twenty one}, Ar³¹, Ar¹², Ar^{twenty two}, Ar³² of
At least one of which has a phenanthrene structure and four or more condensed rings
Aryl structure or condensed heteroaryl structure having three or more rings
Are preferable, and a phenanthrene structure and a pyrene structure
Is more preferred. Also, represented by general formulas (1) and (2)
Compound is Ar¹², Ar^{twenty two}, Ar³² Is a fused aryl group
Or a compound which is a hydrogen atom,¹², Ar
^{twenty two}, Ar ³² Is a fused aryl group having three or more rings or a hydrogen atom
And more preferably Ar,¹², Ar^{twenty two}, Ar³²
 Is a phenanthrene structure, a condensed aryl structure having four or more rings
And more preferably a hydrogen atom. Also, the general formula
The compound represented by (1) or (2) is Ar¹¹, Ar^{twenty one},
Ar³¹ Is a phenanthrylene group or a condensed ring of 4 or more rings
Compounds that are a arylene group are preferred.

The compounds represented by the general formulas (1) and (2) are preferably compounds composed of only 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 described above, and the preferred ranges are 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, at least one compound represented by the general formula (1) is contained in the light emitting layer, and at least one of them contains the compound represented by the general formula (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 compounds represented by the general formulas (1) to (8) of the present invention may be low molecular weight compounds, and oligomer compounds and polymer compounds (the weight average molecular weight (in terms of polystyrene) is preferably 1,000 to 5,000,000). , More preferably 2,000 to 1,000,000, and still 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 compounds represented by the general formulas (1) to (8) of the present invention preferably have a λmax (maximum emission wavelength) of the fluorescence spectrum of from 400 to 500 nm.
0 to 480 nm, more preferably 400 to 4 nm.
More preferably, it is 60 nm.

Next, examples of the compounds represented by formulas (1) to (8) of the present invention will be shown, but the present invention is not limited thereto.

[0052]

Embedded image

[0053]

Embedded image

[0054]

Embedded image

[0055]

Embedded image

[0056]

Embedded image

[0057]

Embedded image

[0058]

Embedded image

[0059]

Embedded image

[0060]

Embedded image

A styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom and a halogen atom contained in the light emitting device of the present invention will be described. The styryl derivative is a derivative having a styrene skeleton as a basic skeleton. As styryl derivatives, carbon atom, hydrogen atom,
There is no particular limitation as long as it is composed of only oxygen, sulfur and halogen atoms. For example, Japanese Patent Application Laid-Open Nos. Hei 7-147189, Hei 8-333283, Hei 10-261488 and U.S. Pat. ,
910 and the like, and a styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a halogen atom.

The styryl derivative composed of only carbon, hydrogen, oxygen, sulfur and halogen atoms is preferably a styryl derivative composed of only carbon and hydrogen.

As a styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom and a halogen atom contained in the light emitting device of the present invention, more preferably a compound represented by the following general formula (ST-1) It is.

[0064]

Embedded image

The general formula (ST-1) will be described. A
r ¹⁰¹ represents a substituted or unsubstituted arylene group having 12 to 50 carbon atoms. Examples of the arylene group of Ar ¹⁰¹ include divalent groups derived from benzene, biphenyl, naphthalene, phenanthrene, anthracene, pyrene, perylene, and derivatives thereof. Further, the substituents of the aryl group may be bonded to each other to form a substituted or unsubstituted saturated 5-membered ring or a substituted or unsubstituted saturated 6-membered ring.

The carbon number of Ar ¹⁰¹ is preferably from 12 to 50, more preferably from 14 to 40, even more preferably from 18 to 36. Ar ¹⁰¹ is preferably a group having three or more benzene rings (eg, a terphenylene group, an anthrylene group, a diphenylanthrylene group, and the like). The substituent on Ar ¹⁰¹ is preferably an alkyl group, an aryl group, a styrene group, a substituted alkyl group, a substituted aryl group, or a substituted styrene group.
Examples of the substituent include R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R
^This is the same as the specific examples of the substituent of the aryl group and the alkyl group of ¹⁰⁶ .

Here, Ar in the general formula (ST-1)
^Examples of the arylene group ¹⁰¹ include the following groups.

[0068]

Embedded image

R ¹⁰¹ and R ¹⁰² each represent a hydrogen atom, an alkyl group or an aryl group, and a hydrogen atom is preferable.
R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , and R ¹⁰⁶ each represent a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group is preferable.

Specific examples of the substituent of the aryl group and the alkyl group of R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , and R ¹⁰⁶ include an alkyl group having 1 to 6 carbon atoms (a methyl group, an ethyl group, an n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, isopentyl group, tert-pentyl group, neopentyl group, isohexyl group), alkoxy group having 1 to 6 carbon atoms (methoxy) Group, ethoxy group, propoxy group, i-propoxy group, butyloxy group, i-butyloxy group, sec-butyloxy group, t
-Butyloxy group, isopentyloxy group, t-pentyloxy group), an aryloxy group, an arylthio group, a phenyl group, and a halogen atom, and the substituent may be singular or plural.

The glass transition point of the styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom and a halogen atom contained in the light emitting device of the present invention is preferably 8
0 ° C. or higher, more preferably 100 ° C. or higher,
More preferably, it is 120 ° C. or higher.

The following are specific examples of styryl derivatives comprising only carbon, hydrogen, oxygen, sulfur and halogen atoms contained in the light emitting device of the present invention, but the present invention is not limited to these. Not done.

[0073]

Embedded image

[0074]

Embedded image

A method for producing the compound of the present invention (compounds represented by formulas (1) to (8)) will be described. The compound of the present invention can be synthesized using various known aromatic carbon-carbon bond formation reactions.
synthesis Reaction Guide (J
ohn Wiley & Sons, Inc. Company) p. 6
17 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.

Examples of the boric acid derivative include substituted or unsubstituted arylboric acid derivatives (for example, 1,4-phenyldiboric acid, 4,4'-biphenyldiboric acid, pyreneboric acid derivatives, phenanthreneboric acid derivatives and the like). And heteroarylboric acid derivatives (for example, pyridyldiboric acid and the like).

The halogen atom of the aryl halide derivative is preferably a chlorine atom, a bromine atom and an iodine atom, more preferably a bromine atom and an 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.

This reaction preferably uses 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. Organic EL as a typical light emitting element
(Electroluminescence) elements.

The method of 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,
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 washed or otherwise treated to lower the driving voltage of the element and 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 and the like. The cathode has good adhesion and ionization potential between the negative electrode such as the electron injecting layer, the electron transporting layer and the light emitting layer. 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.

The cathode is manufactured by a method such as an electron beam method, a sputtering method, a resistance heating evaporation method, a coating method and the like. The metal can be evaporated alone or two or more components can be evaporated simultaneously. 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 the anode, the hole injection layer, and the hole transport layer and applying electrons from the cathode, the electron injection layer, and the 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.), and ink jet method. , A printing method, an LB method, a transfer method, and the like, and preferably a resistance heating evaporation and a coating method.

The material of the hole injection layer and the hole transport layer has one of a function of injecting holes from the anode, a function of transporting holes, and 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.

The hole injecting layer and the hole transporting layer may be formed by a vacuum deposition method, an LB method, or a method in which the hole injecting and transporting material is dissolved or dispersed in a solvent and coated (spin coating, casting, Dip coating method), an ink jet method, a printing method, and a transfer method. 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,
Poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. .

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, and 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.

The electron injecting layer and the electron transporting layer may be formed by a vacuum deposition method, an LB method, or a method in which the electron injecting and transporting material is dissolved or dispersed in a solvent and coated (spin coating, casting, dip coating, etc.). Etc.), an ink jet method, a printing method, a transfer method, and the like. 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 such as moisture or oxygen which promotes element deterioration 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.

The method for forming the protective layer is not particularly limited. For example, a vacuum evaporation 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), plasma CVD, laser CVD, thermal CVD, gas source CVD, coating, printing, and transfer are applicable.

[0096]

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.

[0098]

Embedded image

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.

[0100]

Embedded image

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).

[0102]

Embedded image

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.

[0104]

Embedded image

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.

[0106]

Embedded image

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.

[0108]

Embedded image

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 was obtained, and the maximum luminance was 113.
A luminance of 0 cd / m ² was obtained. 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,
A blue-green emission of (0.17, 0.31) was obtained, and the maximum luminance was 1
2740 cd / m ² were obtained. When the external quantum efficiency of the device was calculated (calculated from the light emission luminance, light emission spectrum, current density, and relative luminous efficiency curve), 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.

[0111]

Embedded image

Example 1 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 the compound (1-1) and the compound (2-1) 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.
16,0.20) blue light emission, maximum brightness 3700cd
/ M ² . 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 0.5 V.

Example 2 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 compound (1-1) and (2-5) were added thereon in a ratio of 1: 1. Co-deposition was performed, and an azole compound c was deposited thereon by 40 nm. As a result of cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.16
0.19) blue light emission, maximum luminance 4900 cd / m ²
I got When the external quantum efficiency of the device was calculated, φ _EL =
It was 1.8%. When left in a nitrogen atmosphere for one day, the film surface was transparent. When light emission was performed continuously at 100 cd / m ² for 2 hours, the driving voltage increased by 0.3 V.

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 (2-8) 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.
16,0.20) blue-green light emission, maximum brightness 3800c
d / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 1.9%. When left in a nitrogen atmosphere for one day, the film surface was transparent. 100 cd / m ²
When the light emission was continued for 2 hours, the driving voltage increased by 0.2 V.

Example 4 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 (2-15) 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 cathode deposition and device evaluation as in Comparative Example 1,
(0.16, 0.22) blue-green light emission, maximum brightness 33
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. 100 cd /
When light was continuously emitted for 2 hours at m ² , the driving voltage was 0.2
V rose.

Example 5 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 (1-2) and a compound (2-8) 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.
16,0.15) blue light emission, maximum brightness 2700cd
/ M ² . When the external quantum efficiency of the device was calculated,
φ _EL = 1.9%. When left in a nitrogen atmosphere for one day, the film surface was transparent. It is ² at 100 cd / m 2
When the light was continuously emitted for a time, the driving voltage increased by 0.4 V.

Example 6 40 mg of polyvinylcarbazole, 2- (4-t-butylphenyl) -5- (4-biphenyl) -1,3,4
-Oxadiazole 12 mg, (1-1) 1 mg,
(2-2) 1 mg was dissolved in 2.5 ml of dichloroethane and spin-coated on a washed ITO substrate (15).
00 rpm, 20 sec). The thickness of the organic layer is 120 nm
Met. As a result of cathode deposition and device evaluation in the same manner as in Comparative Example 1, (0.16, 0.20) blue light emission and a maximum luminance of 2 were obtained.
200 cd / m ² was obtained.

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

[0119]

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 (5)

[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,
The light-emitting layer contains at least one compound represented by the following general formula (1) and at least one styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a halogen atom. A light emitting element characterized by the above-mentioned. 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. ) 4. A styryl derivative composed of only a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a halogen atom is represented by the general formula (ST-1).
The light-emitting device according to item 1. Embedded image (In the formula (ST-1), Ar ¹⁰¹ represents a substituted or unsubstituted arylene group having 12 to 50 carbon atoms.
R ¹⁰¹ and R ¹⁰² represent a hydrogen atom, an alkyl group, and an aryl group, respectively. R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ and R ¹⁰⁶ each represent a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. ) 5. The light emission according to claim 1, wherein a glass transition point of a styryl derivative composed of only carbon atom, hydrogen atom, oxygen atom, sulfur atom, and halogen atom is 80 ° C. or higher. element.