JP2002329579A - Luminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a luminescent element with high luminescent characteristics and high durability. SOLUTION: In the luminescent element formed by interposing a luminescent layer or a plurality of organic compound layers containing a luminescent layer between a pair of electrodes, the luminescent element contains at least one kind of compounds represented by general formula 1 and at least one kind of organic silicon derivatives. (In the formula, Ar<11> , Ar<21> , Ar<31> represent an allylene group, Au<12> , Ar<22> , Ar<32> represent a substituent group or a hydrogen atom. At least one of Ar<11> , Ar<21> , Ar<31> , Ar<12> , Ar<22> , and Ar<32> is fused ring aryl structure or fused ring heteroaryl structure. Ar represents an allylene group, or a heteroallylene 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) and at least one organosilicon derivative are contained in the light-emitting layer. A light-emitting element comprising one kind.

[0006]

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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).

[0008]

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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).

[0010]

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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. ) 4. At least one kind of the organosilicon derivative is a compound represented by the following general formula (S-1), (S-2), (S-3), (S-4), or (S-5). 4. The light emitting device according to any one of the above 1 to 3, wherein

[0012]

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(In the general formula (S-1), R ¹ represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, and Ar ¹¹ , Ar ¹² and Ar ¹³ each represent a heteroaryl group. In the formula (S-2), R ² is an alkyl group,
It represents an aryl group, a heteroaryl group, or an alkynyl group, and Ar ²¹ , Ar ²² , and Ar ²³ each represent an arylene group. R ²¹ , R ²² and R ²³ each represent an aryl group or a heteroaryl group. In Formula (S-3), R ³ represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group, and Ar ³¹ , Ar ³² , and Ar ³³ each represent an arylene group. R ³¹ , R ³² and R ³³ each represent an alkenyl group or an alkynyl group. In Formula (S-4), R ⁴ represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group, and Ar ⁴¹ , Ar ⁴² , and Ar ⁴³ each represent an arylene group. R ⁴¹ , R ⁴² , and R ^{43 each} represent a —NR ⁴⁴ R ⁴⁵ group;
Represents an OR ⁴⁶ group or a —S—R ⁴⁷ group. R ⁴⁴ , R ⁴⁵ , R
⁴⁶ and R ⁴⁷ each represent a hydrogen atom or a substituent. In the general formula ^(S-5), R 5 represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group,, Ar ^51, Ar
⁵² and Ar ⁵³ each represent a condensed aromatic hydrocarbon group having three or more rings. ) 5. The light emitting device according to any one of the above items 1 to 3, wherein at least one kind of the organosilicon derivative is a compound represented by the following general formula (S-9), (S-10), or (S-11). .

[0014]

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(In the general formula (S-9), R¹, R^Two, R^Three
Represents a hydrogen atom or a substituent, respectively. Where R¹,
R^Two, R^ThreeIs not an alkenyl group. R^Four, R
^FiveRepresents a hydrogen atom or a substituent, respectively. Ar¹Is ant
A heteroaryl group, an alkenyl group. General
In the formula (S-10), R^{twenty one}, R^{twenty two}Is a hydrogen atom or a substituent
Represents R^{twenty three}, R^{twenty four}, R^{twenty five}, R²⁶Is a hydrogen atom or substitution
Represents a group. Ar^{twenty one}, Ar ^{twenty two}Is an aryl group, heteroaryl
And an alkenyl group. In the general formula (S-11), R
³⁰, R³¹, R³², R³³, R³⁴Is a hydrogen atom or a substituent
Represents Ar³¹Is an arylene group, a heteroarylene group,
Represents an alkenylene group. L¹Represents a divalent linking group. A
Represents a linking group. n¹Represents an integer of 2 or more. n¹Is 2
In the case of A, A may be a single bond. Multiple connected to A
Are the same as each other (the group having a vinylsilyl structure)
Or different. n^TwoRepresents 0 or 1. However,
A is an aryl linking group, a heteroaryl linking group or
A kenyl linking group, and n^ThreeN only when is 0^TwoIs 0
I can take it. n^ThreeRepresents an integer of 0 or more. ) 6. When the glass transition point of the organosilicon derivative is 80 ° C or higher
6. The light emitting device according to any one of the above 1 to 5, wherein

[0016]

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, there is provided 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, wherein at least one compound represented by the general formula (1) is contained in the light emitting layer. And a light-emitting device comprising at least one organic silicon derivative.

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.

The concentration of the organosilicon derivative of the present invention in the light emitting layer is preferably 1% by mass to 99% by mass, more preferably 5% by mass to 90% by mass, and more preferably 10% by mass. More preferably, it is at least 80% 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 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 (for example, 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 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.

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.

[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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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.

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 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 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 compounds, and oligomer compounds and polymer compounds (preferably having a weight average molecular weight (in terms of polystyrene) of 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 the general formulas (1) to (8) of the present invention are shown, but the present invention is not limited thereto.

[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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The organic silicon derivative contained in the light emitting device of the present invention will be described. Examples of the organosilicon derivative include, for example, alkylsilane, vinylsilane, arylsilane, heteroarylsilane, aminosilane, alkoxysilane, and derivatives thereof, and vinylsilane, arylsilane, heteroarylsilane, and derivatives thereof are more preferred. preferable. Preferred specific examples of the organosilicon derivative are described in JP-A-12-21575 and JP-A-12-351966.

As the organosilicon derivative contained in the light emitting device of the present invention, preferably, at least one of the organosilicon derivatives has the following general formula (S-1), (S-2) or (S-
3) The compound represented by (S-4) or (S-5).

[0064]

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The general formula (S-1) will be described. R ¹
Represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, and Ar ¹¹ , Ar ¹² and Ar ¹³ each represent a heteroaryl group.

R ¹ is an alkyl group (preferably having 1 to carbon atoms)
20, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-
Propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 carbon atoms)
-20, particularly preferably 6-12 carbon atoms, for example, phenyl, p-methylphenyl, naphthyl and the like. ), A heteroaryl group (preferably an oxygen atom,
It contains any one of a sulfur atom and a nitrogen atom, preferably has 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 12 carbon atoms. For example, imidazolyl, pyridyl, furyl, piperidyl, benzoxa Zolyl, thienyl, triazolyl group, carbazolyl group and the like. ), Alkynyl group (preferably having 2 to 20 carbon atoms,
More preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl. ). These groups may be further substituted.

R ¹ is preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an aryl group or a heteroaryl group, still more preferably a heteroaryl group, and particularly preferably a —Ar ¹⁴ group (Ar ¹⁴
Is a group having the same meaning as the following Ar ¹¹ ).

Ar ¹¹ , Ar ¹² and Ar ¹³ represent a heteroaryl group. When the heteroaryl group is composed of a plurality of condensed rings (in the case of a condensed heteroaryl group), it is preferable that a silicon atom is substituted on a ring containing a hetero atom. Ar ¹¹ , Ar ¹² , and Ar ¹³ are preferably a pyridyl group, a pyrazyl group, an oxadiazolyl group, a triazolyl group, a thiadiazolyl group, a thienyl group, a carbazolyl group, a quinolino group, a benzazolyl group (eg, a benzoxazolyl group, a benzimidazolyl group, A benzothiazolyl group, preferably a benzoxazolyl group, a benzimidazolyl group, more preferably a benzimidazolyl group), a carbazolyl group, more preferably a pyridyl group, a pyrazyl group, an oxadiazolyl group, a triazolyl group, a quinolino group, a benzozolyl group, A carbazolyl group, more preferably a pyridyl group, a pyrazyl group, a benzoazolyl group, or a carbazolyl group; and particularly preferably a pyridyl group, a benzozolyl group, or a carbazolyl group. Examples of the substituent on the heteroaryl group include R ¹ described above and R described below.
^21, those described in R ^31, R ^41, and include a cyano group, hereinafter R ²¹ group, R ³¹ group, R ⁴¹ groups are preferred.

The general formula (S-2) will be described. R ²
Is an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, ter
t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl), and hetero. An aryl group (preferably containing any of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 2 carbon atoms;
12, for example, imidazolyl, pyridyl, furyl,
Examples include piperidyl, benzoxazolyl, thienyl, triazolyl group, carbazolyl group and the like. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl). These groups may be further substituted.

R ² is preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an aryl group or a heteroaryl group, further preferably an aryl group, particularly preferably an —Ar ²⁴ —R ²⁴ group. (A
r ²⁴ and R ²⁴ are the same groups as Ar ²¹ and R ²¹ below, respectively. Ar ²¹ , Ar ²² and Ar ²³ represent an arylene group (preferably having 6 to 40 carbon atoms, more preferably having 6 to 30 carbon atoms, and still more preferably having 6 to 12 carbon atoms). Ar ²¹ , Ar
²² , Ar ²³ is preferably a phenylene group, a naphthylene group,
Anthracenylene group, pyrenylene group and rubrenylene group, more preferably phenylene group, naphthylene group and anthracenylene group, further preferably phenylene group, particularly preferably unsubstituted p-phenylene group.

R ²¹ , R ²² and R ²³ are an aryl group (preferably a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, more preferably a phenyl group, a naphthyl group, further preferably a phenyl group), a heteroaryl group (preferably a phenyl group). Is a pyridyl group, a pyrazyl group, an oxadiazolyl group, a triazolyl group, a thiadiazolyl group, a thienyl group, a carbazolyl group, a quinolino group, a benzoazolyl group (for example, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a carbazolyl group; Zolyl group, benzimidazolyl group, carbazolyl group, more preferably benzimidazolyl group), more preferably
Pyridyl group, pyrazyl group, oxadiazolyl group, triazolyl group, benzoazolyl group, carbazolyl group,
More preferred are a pyridyl group, a pyrazyl group, a benzazolyl group and a carbazolyl group, and particularly preferred are a pyridyl group, a benzazolyl group and a carbazolyl group. ). R ²¹ , R ²² , and R ²³ are preferably a heteroaryl group, an aromatic condensed hydrocarbon ring group having three or more rings (for example, a group described later for Ar ⁵¹ , and a preferable range is also the same), and more preferably 3 It is a condensed aromatic hydrocarbon ring group having a ring or more.

The general formula (S-3) will be described. R ³
Is an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, ter
t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl), and hetero. An aryl group (preferably containing any of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 2 carbon atoms;
12, for example, imidazolyl, pyridyl, furyl,
Examples include piperidyl, benzoxazolyl, thienyl, triazolyl group, carbazolyl group and the like. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl). These groups may be further substituted.

R ³ is preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an aryl group or a heteroaryl group, further preferably an aryl group, and particularly preferably an —Ar ³⁴ —R ³⁴ group. (A
r ³⁴ and R ³⁴ are the same groups as Ar ³¹ and R ³¹ below, respectively. Ar ³¹ , Ar ³² , and Ar ³³ are groups having the same meaning as Ar ²¹ . R ³¹ , R ³² and R ³³ represent an alkenyl group or an alkynyl group, and an alkenyl group is preferable. The substituent on the alkenyl is preferably an aryl group or a heteroaryl group, more preferably a heteroaryl group.

The general formula (S-4) will be described. R ⁴
Is an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, ter
t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl), and hetero. An aryl group (preferably containing any of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 2 carbon atoms;
12, for example, imidazolyl, pyridyl, furyl,
Examples include piperidyl, benzoxazolyl, thienyl, triazolyl group, carbazolyl group and the like. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl). These groups may be further substituted.

R ⁴ is preferably an alkyl group, an aryl group, or a heteroaryl group, more preferably an aryl group or a heteroaryl group, further preferably an aryl group, and particularly preferably an —Ar ⁴⁴ —R ⁴⁸ group. (A
r ⁴⁴ and R ⁴⁸ are the same groups as Ar ⁴¹ and R ⁴¹ below, respectively. Ar ⁴¹ , Ar ⁴² and Ar ⁴³ are groups having the same meaning as Ar ²¹ .

R ⁴¹ , R ⁴² , and R ⁴³ represent —NR ⁴⁴ R ⁴⁵ groups, —O
R ⁴⁶ represents a —S—R ⁴⁷ group. ^R44 , ^R45 , ^R46 , ^R47
Represents a hydrogen atom or a substituent. R ⁴⁴ and R ⁴⁵ may combine to form a ring structure (for example, a carbazole ring or a benzazepine ring). R ⁴⁴ and R ⁴⁵ are preferably an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 1 carbon atoms).
2, particularly preferably 1 to 8 carbon atoms, aryl group (preferably 6 to 30 carbon atoms, more preferably 6 to 2 carbon atoms)
0, particularly preferably 6 to 12 carbon atoms, a heteroaryl group (preferably containing any of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, Particularly preferably, it has 2 to 12 carbon atoms),
And more preferably an aryl group, still more preferably a phenyl group, a naphthyl group, a group forming a carbazole ring by bonding, a group forming a benzoazepine ring by bonding, and particularly preferably It is a group that forms an azepine ring. R ⁴⁶ and R ⁴⁷ are preferably an alkyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 carbon atom).
To 12, particularly preferably 1 to 8 carbon atoms, and an aryl group (preferably 6 to 30 carbon atoms, more preferably 6 carbon atoms).
-20, particularly preferably 6-12), more preferably an alkyl group. R ⁴¹ , R ⁴² and R ⁴³ are -N
R ⁴⁴ R ⁴⁵ groups and —OR ⁴⁶ groups are preferred, and more preferably —
NR ⁴⁴ R ⁴⁵ groups.

The general formula (S-5) will be described. R ⁵
Is an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, ter
t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl), and hetero. An aryl group (preferably containing any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably 2 to 1 carbon atoms;
2, for example, imidazolyl, pyridyl, furyl, piperidyl, benzoxazolyl, thienyl, triazolyl group, carbazolyl group and the like. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl).
Represents These groups may be further substituted.

Ar ⁵¹ , Ar ⁵² and Ar ⁵³ each represent a condensed aromatic hydrocarbon group having three or more rings. Examples of the three or more aromatic condensed hydrocarbon ring structure constituting the three or more aromatic condensed hydrocarbon ring group include, for example, Aldrich Structure Inde
x (Aldrich 1996-1997 edition, e.g. p177-178),
Library of Rare Chemicals Structure Index (Sigma-A
ldrich 1993 edition, for example, pages 165 to 168), and the structures described in Organic Chemistry and Biochemical Nomenclature, Vol. 21 to 28 (translated by Nanao-do Hirayama, published in 1988), and the like. Structure, pyrene structure, triphenylene structure, perylene structure, fluoranthene structure, indacene structure, acenaphthylene structure, fluorene structure, tetraphenylene structure, and structures further condensed to these structures (for example, benzanthracene structure, benzopyrene structure, pentacene structure, Coronene structure, chrysene structure, etc.).

Ar ⁵¹ , Ar ⁵² and Ar ⁵³ are preferably anthracenyl group, phenanthrenyl group, pyrenyl group and perylenyl group, more preferably pyrenyl group.

The formulas (S-1), (S-2) and (S
Of the compounds represented by (-3), (S-4) or (S-5), the compound represented by formula (S-4) or (S-5) is more preferable. Further, the preferable range of the general formula (S-4) is the following general formula (S-6) and the following general formula (S-8)
And the more preferable range is the general formula (S-6).
A preferred range of the general formula (S-5) is as follows.
-7).

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The general formula (S-6) will be described.
R ⁶¹ and R ⁶² represent a substituent, l ¹ represents an integer of 0 to 4, and l ² represents an integer of 0 to 12. As the substituent, for example, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 1 carbon atoms)
0, for example methyl, ethyl, iso-propyl,
tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), Alkenyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms,
Particularly preferably, it has 2 to 10 carbon atoms, for example, vinyl,
Allyl, 2-butenyl, 3-pentenyl and the like can be mentioned. ), 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 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, acetyl,
Benzoyl, formyl, pivaloyl and the like can be mentioned. ), An alkoxycarbonyl group (preferably having 2 carbon atoms)
-30, more preferably 2-20 carbon atoms, particularly preferably 2-12 carbon atoms, for example, methoxycarbonyl,
Ethoxycarbonyl and the like. ), An aryloxycarbonyl group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, and particularly preferably having 7 to 1 carbon atoms.
2, for example, phenyloxycarbonyl and the like. ), An acyloxy group (preferably having 2 to 3 carbon atoms)
It has 0, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy. ), An acylamino group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 10 carbon atoms, such as acetylamino and benzoylamino), and an alkoxycarbonylamino group. (Preferably having 2 to 30 carbon atoms,
More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino. ), An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably having 7 carbon atoms)
20 to 20, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino. ), A sulfonylamino group (preferably having 1 to 3 carbon atoms)
0, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino,
Benzenesulfonylamino and the like. ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methylsulfamoyl,
Dimethylsulfamoyl, phenylsulfamoyl and the like can be mentioned. ), 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 having 1 to 2 carbon atoms)
0, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio and the like. ), An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, such as phenylthio, etc.), and a heteroarylthio group (preferably having 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, pyridylthio, 2-benzimidisolylthio,
2-benzoxazolylthio, 2-benzothiazolylthio and the like can be mentioned. ), 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. Is.), Hydroxy group, a mercapto group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, iodine atom), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, sulfino group, hydrazino group,
An imino group, a 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 and the like; a silyl group (preferably having 3 to 40 carbon atoms, more preferably having 3 to 30 carbon atoms, particularly preferably Has 3 to 24 carbon atoms and includes, for example, trimethylsilyl, triphenylsilyl and the like.) And the like. These substituents may be further substituted, and the substituents may combine with each other to form a ring structure.

R ⁶¹ and R ⁶² are preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an alkyl group or an aryl group. l ¹ is preferably 0 to 2, more preferably 0 or 1. l ² is preferably 0 to 4, more preferably 0 or 1.

The general formula (S-7) will be described. R ⁷¹
Represents a substituent, l ³ is an integer of 0-9. Examples of the substituent include the groups described in the R ^61. R ⁷¹ is preferably an alkyl group, an aryl group, or a heteroaryl group, and more preferably an alkyl group or an aryl group.
l ³ is preferably 0 to 2, more preferably 0, 1
It is.

The general formula (S-8) will be described.
R ⁸¹ and R ⁸² represent a substituent, l ⁴ represents an integer of 0 to 4, and l ⁵ represents an integer of 0 to 8. Examples of the substituent include the groups described in the R ^61. R ⁸¹ and R ⁸² are preferably an alkyl group, an aryl group, a heteroaryl group,
More preferred are an alkyl group and an aryl group. l ⁴ is preferably 0 to 2, more preferably 0 or 1. l ⁵ is preferably 0-2, more preferably 0,1.

As the organosilicon derivative contained in the light emitting device of the present invention, preferably, at least one of the organosilicon derivatives is represented by the following formula (S-9), (S-10) or (S-11). Compound.

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The general formula (S-9) will be described in detail.
You. R¹, R^Two, R^ThreeRepresents a hydrogen atom or a substituent.
Where R¹, R^Two, R^ThreeIs not an alkenyl group
No. R ¹, R^Two, R^ThreeExamples of the substituent of
Group (preferably having 1 to 30 carbon atoms, more preferably
1 to 12, more preferably 1 to 6 carbon atoms, e.g.
Tyl group, t-butyl group, hexyl group, cyclohexyl group
Alkynyl group (preferably having carbon atoms)
2 to 30, more preferably 2 to 12 carbon atoms, even more preferably
Or C2-C6, for example, an ethynyl group, etc.
), An aryl group (preferably having 6 to 40 carbon atoms,
Preferably C6-20, more preferably C6
To 12, for example, phenyl group, naphthyl group, anthracene
A heteroaryl group (preferable).
Containing oxygen, sulfur, or nitrogen atoms
And preferably has 1 to 40 carbon atoms, more preferably
Examples having 2 to 20 carbon atoms, more preferably 3 to 12 carbon atoms
For example, pyridyl group, thienyl group, carbazolyl group, etc.
And an alkoxy group (preferably having 1 to 3 carbon atoms).
0, more preferably 1 to 12 carbon atoms, still more preferably
1-6 carbon atoms, for example, methoxy group, isopropoxy group, etc.
And an aryloxy group (preferably having carbon atoms)
6 to 40, more preferably 6 to 20 carbon atoms, still more preferably
Or C6-C12, for example, phenoxy group, naphtho
Xy group, pyrenyloxy group, etc.), hetero
Ring group (preferably an oxygen atom or a sulfur atom or a nitrogen atom
Containing atoms, preferably having 1 to 40 carbon atoms,
More preferably, it has 2 to 20 carbon atoms, and more preferably, it has 2 carbon atoms.
3 to 12, for example, piperidyl group, morpholino group and the like.
Group), a silyl group (preferably having 1 to 30 carbon atoms,
Preferably has 3 to 20 carbon atoms, more preferably has
3-12, for example, trimethylsilyl group, t-butyldim
Tylsilyl group, triphenylsilyl group and the like.
). These substituents are further substituted
May be provided.

R ¹ , R ² , and R ³ are preferably an alkyl group, an aryl group, a heteroaryl group, or an alkoxy group, more preferably an alkyl group, an aryl group, or a heteroaryl group. An aryl group and a heteroaryl group, particularly preferably an aryl group.

R ⁴ and R ⁵ represent a hydrogen atom or a substituent. Examples of the substituent include an alkyl group, an aryl group,
Examples include a heteroaryl group, a heterocyclic group, and a cyano group. R ⁴ and R ⁵ are preferably an alkyl group, an aryl group, a heteroaryl group, a cyano group, or a hydrogen atom. More preferred are a hydrogen atom, an alkyl group and an aryl group, still more preferred are a hydrogen atom and an aryl group, and particularly preferred are a hydrogen atom.

Ar ¹ is an aryl group, a heteroaryl group,
Represents an alkenyl group. An aryl group and a heteroaryl group are preferred, and an aryl group is more preferred.

A preferred form of the compound represented by formula (S-9) is a compound represented by formula (S-11).

The general formula (S-11) will be described. R
³⁰ , R ³¹ , and R ³² each represent R ^{1 in the} general formula (S-9).
Is synonymous with R ³³ and R ³⁴ are each represented by the general formula (S-
9) the same meaning as R ⁴ in. n ¹ represents an integer of 2 or more.
When n ¹ is 2, A may be a single bond. A plurality of substituents (groups having a vinylsilyl structure) linked to A may be the same or different. n ¹ is preferably 2 to 4
And more preferably 2, 3, and even more preferably 2.

Ar ³¹ is an arylene group (preferably having 6 to 40 carbon atoms, more preferably having 6 to 20 carbon atoms, still more preferably having 6 to 12 carbon atoms, and examples thereof include a phenylene group, a naphthylene group, and an anthracenylene group) A heteroarylene group (preferably containing an oxygen atom, a sulfur atom, or a nitrogen atom,
-40, more preferably 2-20 carbon atoms, still more preferably 3-12 carbon atoms, for example, a pyridylene group, a thienylene group, a carbazolylen group, etc.), an alkenylene group (preferably 2-20 carbon atoms, more preferably Has 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms,
For example, vinylene, allylene, 2-butenylene, 3-pentenylene and the like can be mentioned. These linking groups may further have a substituent.

Ar ³¹ is preferably an arylene group or a heteroarylene group, more preferably an arylene group, further preferably a phenylene group, and particularly preferably an unsubstituted phenylene group.

N ² represents 0 or 1. However, n ² can take 0 only when A is an aryl linking group, a heteroaryl linking group or an alkenyl linking group and n ³ is 0. n ² is preferably 1.

L ¹ represents a divalent linking group, and n ³ represents an integer of 0 or more. When n ³ is 2 or more, each L ¹ may be the same or different. The number of carbon atoms of the — (L ¹ ) n ³ — group is preferably 0 to 40, more preferably 0.
To 24, and particularly preferably 0 to 12. Examples of the divalent linking group include a substituted or unsubstituted alkylene group (eg, a methylene group, an ethylene group, a cyclohexylene group, etc.), an alkenylene group (eg, a vinylene group, a methylvinylene group, etc.), an alkynylene group (eg, an ethynylene group), Arylene group (for example, phenylene group, naphthylene group, anthracenylene group, etc.), silylene group (for example,
Dimethylsilylene group, diphenylsilylene group, etc.),-
O-group, -S-group, -C (= O)-group, -N (R)-group (R represents a group capable of being substituted on nitrogen), heteroarylene group (for example, pyridylene group, thienylene group ).

L ¹ is preferably a substituted or unsubstituted alkylene group, an arylene group, a heteroarylene group,
Alkenylene group, silylene group, more preferably,
It is a substituted or unsubstituted arylene group, alkenylene group or heteroarylene group, more preferably an arylene group or an alkenylene group, particularly preferably a phenylene group or a vinylene group. n ³ is preferably 0 to 5, more preferably 0 or 1, and particularly preferably 0.
It is.

A represents a linking group. Only when n ¹ is 2,
A can take a single bond. Valency of the linking group will vary depending on the number of n ^1, preferably 2 to 4, more preferably 2,
3, particularly preferably 2. The linking group, for example a divalent linking group described in the L ^1, and, like linking group which changes its valence. A is preferably a single bond, an alkyl linking group, an aryl linking group, or a heteroaryl linking group, more preferably a single bond, an aryl linking group, or a heteroaryl linking group, and further preferably,
It is a single bond or an aryl group, particularly preferably a single bond.

The general formula (S-10) will be described. R
²¹ and R ²² represent a hydrogen atom or a substituent. As the substituent, for example, an alkyl group (preferably having 1 to 20 carbon atoms,
More preferably, it has 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n
-Hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 1 carbon atoms)
2, particularly preferably having 2 to 8 carbon atoms, for example, vinyl, allyl, 2-butenyl, 3-pentenyl and the like. ), Alkynyl group (preferably having 2 to 2 carbon atoms)
It has 0, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl). A carbonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl ), An amino group (preferably having 0 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 1 carbon atoms).
2, for example, dimethylamino, methylcarbonylamino, ethylsulfonylamino, dimethylaminocarbonylamino group, phthalimide group and the like. ), A sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, and particularly preferably having 1 carbon atoms.
To 12, for example, mesyl, tosyl and the like. ), A sulfo group, a carboxyl group, and a heterocyclic group (aliphatic heterocyclic group and aromatic heterocyclic group.
It contains any of an oxygen atom, a sulfur atom and a nitrogen atom, and preferably has 1 to 50 carbon atoms, more preferably 1 to 3 carbon atoms.
0, particularly preferably 2 to 12 carbon atoms, for example, imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl group and the like. ), A hydroxy group, an alkoxy group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include a methoxy group and a benzyloxy group). Aryloxy group (preferably having 6 to 20 carbon atoms, more preferably having 6 carbon atoms)
To 16, particularly preferably 6 to 12 carbon atoms, such as a phenoxy group and a naphthyloxy group. ), A halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a thiol group, an alkylthio group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 16 carbon atoms, and particularly preferably having 1 carbon atom. To 12, and examples thereof include a methylthio group and the like) and an arylthio group (preferably having 6 to 20 carbon atoms, more preferably having 6 carbon atoms).
To 16, particularly preferably having 6 to 12 carbon atoms, such as a phenylthio group), and a cyano group. These substituents may be further substituted.

R ²¹ and R ²² are preferably an aryl group, a heteroaryl group, an alkenyl group, an alkynyl group,
More preferably an aryl group, a heteroaryl group,
An aryl group is more preferred, and an unsubstituted phenyl group is particularly preferred.

R ²³ , R ²⁴ , R ²⁵ and R ²⁶ represent a hydrogen atom or a substituent. Examples of the substituent and the preferred range are the same as those of R ^{4 in} formula (S-9).

Ar ²¹ and Ar ²² represent an aryl group, a heteroaryl group or an alkenyl group. The preferred range is the same as that of Ar ^{1 in} formula (S-9).

The organosilicon derivative of the present invention has the general formula (S-
A so-called low molecular weight compound containing only one repeating unit of the skeleton of 1) to (S-11) may be used, or the skeleton of general formulas (S-1) to (S-11) may be used as a side chain. Having a high molecular weight compound (polymer, oligomer) (preferably a weight average molecular weight of 1,000 to 5,000,000, more preferably 2,000 to 1,000,000, and still more preferably 3,000
-50,000) or the general formulas (S-1) to (S-1)
A high molecular weight compound having a skeleton of 1) in the main chain (preferably, a weight average molecular weight of 1,000 to 5,000,000, particularly preferably 2,000 to 1,000,000, more preferably 300
0 to 500,000). In the case of a high molecular weight compound, it may be a homopolymer or a copolymer with another monomer. The compound of the present invention is preferably a low-molecular-weight compound, represented by any one of formulas (S-1) to (S-1).
It is a high molecular weight compound having the skeleton of 1) in the main chain, and more preferably a low molecular weight compound.

The glass transition point of the organosilicon derivative contained in the light emitting device of the present invention is preferably 80 ° C. or higher,
It is more preferably at least 100 ° C, and even more preferably at least 120 ° C.

Examples of the compounds of the organosilicon derivatives represented by formulas (S-1) to (S-11) are shown below, but the invention is not limited thereto.

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[0119]

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[0122]

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[0123]

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[0127]

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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.

Examples of the palladium catalyst include, but are not particularly limited to, 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.

A method for producing the organosilicon derivative of the present invention will be described. From the viewpoint of ease of synthesis, the compound of the present invention does not preferably have a spiro structure centered on a silicon atom. The compound of the present invention can be synthesized by various known methods, and can be obtained, for example, by reacting a lithioaryl derivative (eg, phenyllithium) with a silicon halide compound. The Ar ² —R ²² , Ar ³ —R ³² , and Ar ⁴ —R ⁴² bond formation reaction of the compound of the present invention is performed by the following formulas: —Ar ² —X, —Ar ³ —X, —Ar ⁴ —X
(X = Cl, Br, I , -OSO 2 CH 3, -OSO 2
It is preferable to use CF _3, preferably Br, I) as a precursor to form a bond using a metal catalyst (for example, Suzuki coupling using an alkyl boric acid derivative, Heck reaction using an alkene derivative, Ullmann-type reaction using an amine derivative) , A still reaction using an organic tin compound). The metal catalyst is not particularly limited,
Copper and palladium derivatives are preferred, and palladium derivatives are more preferred. The palladium catalyst is not particularly limited, such as valence and ligand. For example, palladium tetrakistriphenylphosphine, palladium carbon, palladium dichloride (dppf) (dppf: 1,1′-)
Bis (diphenylphosphinoferrocene), palladium acetate and the like.

In the reaction using the palladium catalyst, it is preferable to use a base. The type of base used is not particularly limited, and examples thereof include sodium carbonate, sodium acetate, rubidium carbonate, and triethylamine. The amount of the base used is not particularly limited, but is preferably 0.1 to 20 equivalents to the halide, particularly preferably 1 to 1 equivalent.
It is 0 equivalent.

The reaction using the above-mentioned palladium catalyst 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,
Acetone 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 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 a light-emitting layer is 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 injecting layer, the hole transporting layer, the light emitting layer, and the like. A metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof is used. 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, one having 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, and a coating method. A 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.

As the material of the light emitting layer, holes can be injected from the anode, the hole injection layer, and the hole transport layer when an electric field is applied, and electrons can be injected from the cathode, the electron injection layer, and the electron transport layer. 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 of 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-jetting. , 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 injection layer and the electron transport 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 evaporation method, an LB method, or a method of coating by dissolving or dispersing the electron injecting and transporting material in a solvent (spin coating method, casting method, dip coating method). 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 method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, and transfer method can be applied.

[0152]

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.

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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.

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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).

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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.

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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.

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Synthesis of (1-37) 150 ml of diethyl ether was added to 10 g of 1,3,5-tribromobenzene, 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.

[0164]

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Comparative Example 1 A cleaned ITO substrate was put 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.

[0167]

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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 a compound (1-1) and a compound (2-4) 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, 0.15) blue light emission, maximum luminance 4200 cd
/ M ² . 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. In addition, when light was continuously emitted at 100 cd / m ² for 2 hours, the driving voltage increased by 0.3 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 vapor-deposited to a thickness of 40 nm, and compound (1-1) and (2-4) were further added thereon at a ratio of 1:10. Co-deposit,
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, (0.1
5,0.16) with blue light emission and a maximum luminance of 8200 cd /
It was obtained m ^2. When the external quantum efficiency of the device was calculated, φ
_EL = 2.5%. 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 period of time, the driving voltage increased by 0.3 V.

Example 3 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 the compound (1-1) and the compound (2-4) were overlaid thereon at a ratio of 10: 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, 0.27) blue-green light emission, maximum brightness 10
300 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 2.1%. Under nitrogen atmosphere 1
After standing for a day, the film surface was transparent. Also 100 cd
/ M ² for 2 hours, the driving voltage was 0.1.
It rose by 4V.

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 (2-72) were added thereon in a ratio of 1: 1. , And an 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, 0.18) blue-green light emission, maximum brightness 76
00 cd / m ² was obtained. When the external quantum efficiency of the device was calculated, φ _EL = 2.3%. 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 in a thickness of 40 nm, and the compound (1-1) and the compound (2-82) were added 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,
(0.16, 0.15) blue light emission, maximum brightness 410
0 cd / 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
Drive for 2 hours, drive voltage is 0.3V
Rose.

Example 6 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 (2-4) 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) blue light emission and the highest luminance of 8220 cd
/ M ² . When the external quantum efficiency of the device was calculated,
φ _EL = 2.9%. 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 0.2 V.

Example 7 40 mg of polyvinyl carbazole, 2- (4-t-butylphenyl) -5- (4-biphenyl) -1,3,4
-Oxadiazole 12 mg, (1-1) 1 mg,
(2-47) 1 mg was dissolved in 2.5 ml of dichloroethane, 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 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 2100 cd / m ² were 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.

[0176]

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 (6)

[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 a light-emitting layer containing at least one compound represented by the following general formula (1) and at least one organic silicon derivative. 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. The method according to claim 1, wherein at least one of the organosilicon derivatives has the following general formula (S-1), (S-2), (S-3) or (S-
4) or the compound represented by (S-5). Embedded image (In the formula (S-1), R ¹ represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group;
r ¹¹ , Ar ¹² and Ar ¹³ each represent a heteroaryl group.
In the general formula (S-2), R ² is an alkyl group, an aryl group,
Represents a heteroaryl group or an alkynyl group,
r ²¹ , Ar ²² and Ar ²³ each represent an arylene group.
R ²¹ , R ²² and R ²³ each represent an aryl group or a heteroaryl group. In Formula (S-3), R ³ represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group, and Ar ³¹ , Ar ³² , and Ar ³³ each represent an arylene group. R ³¹ , R ³² and R ³³ each represent an alkenyl group or an alkynyl group. In Formula (S-4), R ⁴ represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group, and Ar ⁴¹ , Ar ⁴² , and Ar ⁴³ each represent an arylene group. R ⁴¹ , R ⁴² and R ⁴³ represent —NR ⁴⁴ R ⁴⁵ groups, —O
Represents an R ⁴⁶ group or a —S—R ⁴⁷ group. R ⁴⁴ , R ⁴⁵ ,
R ⁴⁶ and R ⁴⁷ each represent a hydrogen atom or a substituent. In the general formula ^(S-5), R 5 represents an alkyl group, an aryl group, a heteroaryl group, or an alkynyl group,, Ar ^51, A
r ⁵² and Ar ⁵³ each represent a condensed aromatic hydrocarbon group having three or more rings. ) 5. The method according to claim 1, wherein at least one of the organosilicon derivatives is
The general formula (S-9), (S-10), or (S-1)
2. A compound represented by the formula (1):
4. The light emitting device according to any one of items 1 to 3. Embedded image(In the general formula (S-9), R¹, R^Two, R^ThreeIs water
Represents an atom or a substituent. Where R¹, R^Two, R^ThreeBut
It is not an alkenyl group. R^Four, R^FiveAre each
Represents a hydrogen atom or a substituent. Ar¹Is an aryl group,
Represents a loaryl group or an alkenyl group. General formula (S-1
0) Medium, R^{twenty one}, R^{twenty two}Represents a hydrogen atom or a substituent. R
^{twenty three}, R^{twenty four}, R^{twenty five}, R²⁶Represents a hydrogen atom or a substituent.
Ar^{twenty one}, Ar ^{twenty two}Is an aryl group, a heteroaryl group,
Represents a phenyl group. In the general formula (S-11), R³⁰, R³¹,
R³², R³³, R³⁴Represents a hydrogen atom or a substituent. A
r³¹Is an arylene group, a heteroarylene group, an alkenylene
Represents a group. L¹Represents a divalent linking group. A represents a linking group
Represent. n¹Represents an integer of 2 or more. n¹A is 2
May be a single bond. A plurality of substituents linked to A
(Groups having vinylsilyl structure)
May be. n^TwoRepresents 0 or 1. However, A is ant
Linking group, heteroaryl linking group or alkenyl linking group
A group and n^ThreeN only when is 0^TwoCan take 0
You. n^ThreeRepresents an integer of 0 or more. ) 6. The organic silicon derivative has a glass transition point of 80.
The light emitting device according to claim 1, wherein the temperature is not less than ° C. 7.