JP2003123982A - Light emitting element and novel iridium complex - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a blue light emitting element and a multi-color light emitting element with satisfactory emitting characteristic containing a novel iridium complex or metal complex. SOLUTION: This light emitting element comprises two or more light emitting layers or organic compound layers containing the light emitting layers between electrodes, wherein a compound represented by the following formula is contained in the light emitting layers. (wherein R<11> represents a substituent, R<12> represents hydrogen atom or a substituent, Y<11> represents substituted or non-substituted nitrogen atom, or substituted or non-substituted carbon atom, Z<11> represents a connecting group, M<11> represents a transition metal ion, L<11> represents a ligand, and X<11> represents a paired ion. The bond between Y<11> and nitrogen atom represents a single bond or double bond. The bond between R<11> and nitrogen atom represents a single bond or double bond. n<11> and n<12> represent each 0 or 1, m<11> represents 1-3, m<12> represents 0-8, and m<13> represents 0-3. The compound represented by formula (1) has an electron attractive group in the compound).

Description

Detailed Description of the Invention

[0001]

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

[0002]

2. Description of the Related Art Today, research and development relating to various display elements are active, and among them, organic electroluminescence (EL) elements are attracting attention as promising display elements because they can emit light of high brightness at low voltage. ing. For example, a light emitting device in which an organic thin film is formed by vapor deposition of an organic compound is known (Applied Physics Letters, Vol. 51, 91).
3 pages, 1987). The light-emitting device described in this document uses tris (8-hydroxyquinolinato) aluminum complex (Alq) as an electron-transporting material and is laminated with a hole-transporting material (amine compound) to obtain a conventional single-layer device. Compared with this, the light emission characteristics are greatly improved.

In recent years, the application of organic EL elements to color displays and white light sources has been actively studied, but in order to develop high performance color displays and white light sources, blue, green and red light sources have been developed. It is necessary to improve the characteristics of the light emitting element.

As a means for improving the characteristics of the light emitting element, (Ir (pp
y) ₃ : Tris-Ortho-Metalated Complex of Iridium (II
I) with 2-Phenylpyridine; an orthometalated iridium complex) has been reported as a green light emitting device (Applied Physics Letters 75, 4 (199).
9)). This device has achieved an external quantum yield of 8%, which exceeds the external quantum yield of 5%, which was said to be the limit of conventional devices, but since it is limited to green emission, its application range as a display is limited. There was a demand for the development of light-emitting devices that are narrow, highly efficient, and of other colors.

Further, WO02 / 15645A1 discloses a light emitting device utilizing light emission from an organometallic compound.

[0006]

DISCLOSURE OF THE INVENTION The present invention provides a novel iridium complex and a blue light emitting device and a multicolor light emitting device containing a metal complex and having excellent light emitting characteristics.

[0007]

This problem has been achieved by the following means. That is, 1. A light emitting device having a light emitting layer or a plurality of organic compound layers including a light emitting layer formed between a pair of electrodes, wherein the light emitting layer contains at least one compound represented by the following general formula (1). Light emitting element.

General formula (1)

[Chemical 4]

(Where R is¹¹Represents a substituent, R¹²Is hydrogen
Represents an atom or a substituent, Y¹¹Is a substituted or non-substituted
Represents an elementary atom or a substituted or unsubstituted carbon atom,
Z¹¹Represents a linking group, M¹¹Represents a transition metal ion,
L¹¹Represents a ligand, X¹¹Represents a counter ion. Y¹¹When
The bond with the nitrogen atom represents a single bond or a double bond.
R ¹¹The bond between the nitrogen atom and the nitrogen atom is a single bond or a double bond.
Represent n¹¹Represents 0 or 1, and n¹²Represents 0 or 1,
m¹¹Represents an integer of 1 to 3, m¹²Represents an integer from 0 to 8
Then m¹³Represents an integer of 0 to 3. Represented by general formula (1)
Compound has at least one electron-withdrawing group in the compound.
To do. ) 2. The light emitting layer is represented by the general formula (1) with the host compound.
Compound and the lowest triplet excited state of the host compound
Energy level (T₁Level) is 62 kcal /
mol or more (259 kJ / mol or more), 85 kcal
/ Mol or less (355 kJ / mol or less)
2. The light emitting device as described in 1 above, which is characterized. 3. Minimum triple of compounds contained in the layer adjacent to the light emitting layer
Energy level of term excited state (T₁Level) is 62k
cal / mol or more (259 kJ / mol or more), 85
kcal / mol or less (355 kJ / mol or less)
3. The light emitting device as described in 1 or 2 above. 4. A plurality of light-emitting layers or a light-emitting layer between a pair of electrodes
A light-emitting device having an organic compound layer of
And at least one compound represented by the following general formula (5)
A light-emitting device characterized by containing. General formula (5)

[Chemical 5] (In the formula, R ⁵¹¹ represents a substituent, R ⁵¹² represents a hydrogen atom or a substituent, Y ⁵¹ represents a substituted or unsubstituted nitrogen atom, or a substituted or unsubstituted carbon atom, and Z ⁵¹ is a link. Represents a group, M ⁵¹ represents a transition metal ion, L ⁵¹ represents a ligand forming a non-carbon-metal bond, X ⁵¹ represents a counter ion, and the bond between Y ⁵¹ and a nitrogen atom is: Represents a single bond or a double bond, the bond between R ⁵¹¹ and a nitrogen atom represents a single bond or a double bond, n ⁵¹ represents 0 or 1, and n ⁵² represents 0.
Or 1, m ⁵¹ represents an integer of 1 to 3, m ⁵² represents 0
Represents an integer of 8 and m ⁵³ represents an integer of 0 to 3. ) 5. 5. The light emitting device as described in 4 above, wherein the general formula (5) is a compound represented by the following general formula (6). General formula (6)

[Chemical 6] (In the formula, Z ⁶¹ , n ⁶¹ , L ⁶¹ , Q ⁶¹ , m ⁶¹ , and m ⁶² have the same meanings as Z ⁵¹ , n ⁵¹ , and L ⁵¹ , respectively. Q ⁶¹ is necessary for forming a nitrogen-containing heterocycle. M ⁶¹ is 1 to 3
And an integer of 0 to 4 is represented by m ⁶² . ) 6. 6. The light emitting device according to 4 or 5, wherein L ⁵¹ is a ligand in which at least one atom selected from the group of nitrogen atom, oxygen atom, sulfur atom and phosphorus atom is coordinated with a metal atom. 7. L ⁵¹ is a bidentate ligand that coordinates to a metal with two nitrogen atoms, a bidentate ligand that coordinates to a metal with a nitrogen atom and an oxygen atom, or a bidentate that coordinates to a metal with two oxygen atoms. 6. The light emitting device according to 4 or 5 which is a ligand.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. In addition, in this specification, "-" shows the range which includes the numerical value described before and after that as a minimum value and a maximum value, respectively.

The general formula (1) will be described. R ¹¹ represents a substituent. As a substituent, for example, a group which is bonded to Y ¹¹ via a linking group to form a nitrogen-containing heterocycle (as the nitrogen-containing heterocycle to be formed, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a pyrazole ring, imidazole Ring, triazole ring, pyrrolidine ring, piperidine ring and the like), alkyl group (preferably having 1 to 3 carbon atoms).
0, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-
Examples include propyl, 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 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl. ), An alkynyl group (preferably having 2 carbon atoms)
To 30, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, for example, phenyl,
p-methylphenyl, naphthyl, anthranyl and the like can be mentioned. ), An amino group (preferably having a carbon number of 0 to 30,
It preferably has 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino and ditolylamino. ),

Alkoxy group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy. ),
Aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 1 carbon atoms)
2, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), A heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.) An acyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group. (Preferably has 2 to 30 carbon atoms, more preferably has 2 to 20 carbon atoms, and particularly preferably has 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl.),
Aryloxycarbonyl group (preferably having 7 to 3 carbon atoms)
It has 0, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl groups), a hydroxy group, a heterocyclic group. (Preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms.
As the hetero atom, for example, nitrogen atom, oxygen atom, sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, An azepinyl group etc. are mentioned. ), A silyl group (preferably having 3 to 40 carbon atoms,
It preferably has 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl. ), A silyloxy group (preferably having 3 to 40 carbon atoms, and more preferably having 3 to 3 carbon atoms).
0, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy. ), A group forming a carbon-nitrogen double bond with an adjacent nitrogen atom, and the like. These substituents may be further substituted with the substituents on the carbon atom in Y ¹¹ described below.

R ¹¹ is preferably a group which forms a nitrogen-containing heterocycle by being bonded to Y ¹¹ via a linking group, an alkyl group, an aryl group, a hydroxyl group or an alkoxy group, more preferably linked to Y ^11. A group which forms a aromatic nitrogen-containing heterocycle by bonding via a group, and more preferably a group which forms a pyridine ring by bonding to Y ¹¹ via a linking group.

The bond between Y ¹¹ and the nitrogen atom represents a single bond or a double bond. The bond between R ¹¹ and the nitrogen atom represents a single bond or a double bond. A bond between Y ¹¹ and the nitrogen atom,
And the bond between R ¹¹ and the nitrogen atom cannot be a double bond at the same time.

R ¹² represents a hydrogen atom or a substituent. Examples of the substituent include the groups described for R ¹¹ , and an alkyl group, an aryl group and a heterocyclic group are preferable, and an alkyl group is more preferable.

Y ¹¹ represents a substituted or unsubstituted nitrogen atom or a substituted or unsubstituted carbon atom, and is bonded to R ¹¹ via a linking group to form a nitrogen-containing heterocycle (as the nitrogen-containing heterocycle to be formed, Pyridine ring, pyrazine ring, pyrimidine ring, triazine ring, pyrazole ring, imidazole ring, triazole ring, pyrrolidine ring, piperidine ring and the like) may be formed. Examples of the substituent on the nitrogen atom for Y ¹¹ include the groups described for R ¹¹ .

The substituent on the carbon atom in Y ¹¹ is, for example, an alkyl group (preferably having 1 to 30 carbon atoms,
More preferably, it has 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, and for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl,
n-hexadecyl, cyclopropyl, cyclopentyl,
Examples include cyclohexyl. ), An alkenyl group (preferably having 2 to 30 carbon atoms, and more preferably having 2 carbon atoms).
To 20, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like. ), An alkynyl group (preferably having 2 to 2 carbon atoms).
30, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, for example, phenyl, p
-Methylphenyl, naphthyl, anthranil and the like. ), An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 carbon atoms).
10 to 10, and examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and the like. ),

Alkoxy group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy. ),
Aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 1 carbon atoms)
2, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), A heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.) An acyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group. (Preferably has 2 to 30 carbon atoms, more preferably has 2 to 20 carbon atoms, and particularly preferably has 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl.),
Aryloxycarbonyl group (preferably having 7 to 3 carbon atoms)
It has 0, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy). Acylamino group (preferably). 2 to 30 carbon atoms, more preferably 2 carbon atoms
To 20, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino. ), An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino).

Aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 2 carbon atoms)
0, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino. ), A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 1 carbon atoms).
2, and examples thereof include methanesulfonylamino and benzenesulfonylamino. ), A sulfamoyl group (preferably having a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, and particularly preferably a carbon number of 0 to 12), for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl. Etc.), a carbamoyl group (preferably having 1 to 30 carbon atoms,
It preferably has 1 to 20 carbon atoms, and 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 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio and ethylthio), and an arylthio group (preferably carbon). Number 6 to 30, more preferably carbon number 6 to 20,
Particularly preferably, it has 6 to 12 carbon atoms, and examples thereof include phenylthio. ), A heterocyclic thio 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 pyridylthio, 2-benzimizolylthio, and 2-benzoxazoli. Ruthio, 2-benzthiazolylthio, etc.), a sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 carbon atom).
To 12 and examples thereof include mesyl and tosyl. ), A sulfinyl group (preferably having 1 to 30 carbon atoms,
It preferably has 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), An ureido group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 2 carbon atoms).
0, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, phenylureido and the like. ),

Phosphoric acid amide group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include diethylphosphoric acid amide and phenylphosphoric acid amide. ), A hydroxy group, a mercapto group, a halogen atom (for example, a 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 1 to 1 carbon atoms
And the hetero atom is, for example, a nitrogen atom, an oxygen atom, a sulfur atom, specifically, for example, an imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group. , Azepinyl group and the like. ), A silyl group (preferably having 3 to 4 carbon atoms).
It has 0, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl. ), A silyloxy group (preferably having 3 to 40 carbon atoms, and more preferably having 3 carbon atoms).
To 30, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy and triphenylsilyloxy. ) And the like. These substituents may be substituted with the substituents on the carbon atom in Y ¹¹ described below.

[0021] Y ¹¹ is preferably a group forming a nitrogen-containing heterocycle linked via a linking group and R ^11, more preferably a group forming an aromatic nitrogen-containing heterocyclic bonded via a linking group and R ¹¹ , R ¹¹ which is bonded to R ¹¹ via a linking group to form a pyridine ring is more preferable.

Z ¹¹ represents a divalent linking group connecting the oxygen atom of the general formula (1) and Y ¹¹ . The linking group is not particularly limited, but for example, a carbonyl linking group (> C =
O), alkylene group, arylene group, heteroarylene group, nitrogen-containing heterocyclic linking group, oxygen atom linking group (-O
-), Nitrogen atom linking group (-NH-), thiocarbonyl linking group (> C = S), sulfoxide linking group (> S = O),
Examples thereof include a sulfonyl linking group (—SO ₂ —) and a linking group composed of a combination thereof. Z ¹¹ is preferably a carbonyl linking group or an alkylene linking group.

M ¹¹ represents a transition metal ion. The transition metal ion is not particularly limited, and iridium ion, platinum ion, rhenium ion, and ruthenium ion are preferable, iridium ion and platinum ion are more preferable, and iridium ion is particularly preferable.

L ¹¹ represents a ligand. Examples of the ligand include “Photochemistry and Photophysics of Coordin
ation Compounds "by Springer-Verlag H.Yersin 1
1987, "Organometallic Chemistry -Basics and Applications-" by Shokabosha, Akio Yamamoto, published in 1982, and the like. Preferred are halogen ligands (preferably chlorine ligands, chlorine ligands, Fluorine ligand), nitrogen-containing heterocyclic ligand (for example, bipyridyl, phenanthroline, phenylpyridine, pyrazolylpyridine, benzimidazolylpyridine, etc.), diketone ligand, nitrile ligand, CO ligand, isonitrile ligand , Phosphorus ligands (eg, phosphine derivatives, phosphite derivatives, phosphinine derivatives, etc.), carboxylic acid ligands (eg, acetic acid ligands, etc.), and more preferably bidentate nitrogen-containing heterocyclic coordination (Eg, bipyridyl, phenanthroline, phenylpyridine, pyrazolylpyridine, benzimidazolylpyridine, etc.).

X ¹¹ represents a counter ion. The counter ion is not particularly limited, preferably an alkali metal ion,
Alkaline earth metal ions, halogen ions, perchlorate ions, PF ₆ ions, ammonium ions (such as tetramethylammonium ion), borate ions and phosphonium ions, more preferably perchlorate ions and PF ₆ ions. n ¹¹ is 0 or 1
And 1 is preferred.

N¹²Represents 0 or 1. Y¹¹And nitrogen atom
The bond between is a single bond, and R ¹¹Between the nitrogen atom
N is a single bond¹²Is 1. Also Y¹¹And
Bond between elementary atoms, or R¹¹Between the and nitrogen atom
N if either is a double bond¹²Is 0.

M ¹¹ represents an integer of 1 to 3, preferably 1 or 2. m ¹² represents an integer of 0 to 8, preferably 0 to 3, and more preferably 1 or 2. m ¹³ represents an integer of 0 to 3, preferably 0 or 1, and more preferably 0. m ¹¹ , m
The combination of ¹² and m ¹³ is preferably a combination of the compound represented by the general formula (1) and a neutral complex.

The compound represented by the general formula (1) has at least one electron-withdrawing group in the compound. The electron-withdrawing group is preferably Hammett's σ value (σp value or σm
Values, reference: Chem. Rev. 1991,91,1
65. ) Is 0.1 or more, more preferably 0.3
That is all. As the electron-withdrawing group, a fluorine atom,
Trifluoromethyl group, acetyl group, methanesulfonyl group, trifluoroacetyl group, trifluoromethanesulfonyl group, cyano group are preferable, fluorine atom, trifluoromethyl group, trifluoroacetyl group, trifluoromethanesulfonyl group are more preferable, fluorine atom , Trifluoromethyl groups are more preferred, and fluorine atoms are particularly preferred.

The compound represented by the general formula (1) preferably has at least one fluorine atom in the compound, and preferably has at least two fluorine atoms in the compound. The fluorine atom is Z ¹¹ , X ¹¹ , R ¹¹ , or L.
Preferably have within the groups represented by ^11, and more preferably has in the group represented by L ^11.

In the present invention, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (2),
The compound represented by the following general formula (3) is more preferable, and the compound represented by the general formula (4) is further preferable.

[0031]

[Chemical 7]

[0032]

[Chemical 8]

[0033]

[Chemical 9]

The general formula (2) will be described. Z ²¹ , n
²¹ and L ²¹ have the same meanings as Z ¹¹ , n ¹¹ and L ¹¹ , respectively, and their preferable ranges are also the same. m ²¹ represents an integer of 1 to 3, preferably 1 or 2. m ²² represents an integer of 0 to 4, and preferably 1 or 2.

Q ²¹ represents an atomic group necessary for forming a nitrogen-containing heterocycle. The nitrogen-containing heterocycle formed by Q ²¹ is not particularly limited, but is preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring,
An oxazole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxadiazole ring, and a condensed ring containing them (for example, a quinoline ring, a benzoxazole ring, a benzimidazole ring, etc.), more preferably a pyridine ring, a pyrazole A ring, an imidazole ring and an oxazole ring, more preferably a pyridine ring, a pyrazole ring and an imidazole ring, and further preferably a pyridine ring.

The compound represented by the general formula (2) has at least one fluorine atom in the compound. It is preferable that the compound has at least two fluorine atoms. The fluorine atom is preferably contained in the group represented by Q ²¹ or L ²¹ , and more preferably contained in the group represented by L ²¹ .

The general formula (3) will be described. Z³¹, N
³¹, Q³¹Are each Z^{twenty one}, N^{twenty one}, Q^{twenty one}Synonymous with
The preferred range is also the same. R³¹, R³², R³³, R
³⁴, R ³⁵, R³⁶, R³⁷, R³⁸Represents a hydrogen atom or a substituent
You As the substituent, Y of the general formula (1) is used.¹¹Charcoal in
The groups described as the substituent on the elementary atom can be mentioned.

R ³¹ and R ³³ are preferably a hydrogen atom, an alkyl group or a fluorine atom, and more preferably a hydrogen atom or a fluorine atom. R ³² and R ³⁴ are preferably a hydrogen atom, an alkyl group or a fluorine atom, more preferably a fluorine atom.

R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are preferably a hydrogen atom, an alkyl group, an alkoxy group or a substituted amino group. The substituent of the substituted amino group is represented by Y in the general formula (1).
^The groups described as the substituent on the carbon atom in ¹¹ can be mentioned.

The compound represented by the general formula (3) has at least one fluorine atom in the compound. It is preferable that the compound has at least two fluorine atoms. The fluorine atom is Q ³¹ , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ ,
Preferably have within the groups represented by R ^36, R ³⁷ or R ^38, more preferably have in the groups represented by R ³² or R ^34, R ³² or R ³⁴ is a fluorine atom It is more preferable that both R ³² and R ³⁴ be a fluorine atom.

The general formula (4) will be described. R ⁴¹ ,
^{R 42, R 43, R 44} , R 45, R 46, R 4 7, R 48 wherein R ^{31 each, R 32, R 33, R} 34, R 35, R 36, R 37, R
^It is synonymous with ³⁸ and the preferred range is also the same. R ⁴¹ , R
^At least one of ⁴² , R ⁴³ and R ⁴⁴ is a fluorine atom.

R ⁴⁹ , R ⁵⁰ , R ⁵¹ , and R ⁵² represent a hydrogen atom or a substituent, and a hydrogen atom, an alkyl group, an alkoxy group,
A substituted amino group and a fluorine atom are preferable. Examples of the substituent of the substituted amino group include the groups described as the substituent on the carbon atom in Y ¹¹ in the general formula (1).

In the present invention, the compound of the general formula (5) can be applied to the light emitting device as in the case of the general formula (1). General formula (5)

[0044]

[Chemical 10]

In the general formula (5), R ⁵¹¹ represents a substituent,
R ⁵¹² represents a hydrogen atom or a substituent, Y ⁵¹ represents a substituted or unsubstituted nitrogen atom, or a substituted or unsubstituted carbon atom, Z ⁵¹ represents a linking group, and M ⁵¹ represents a transition metal ion. , L ⁵¹ represents a ligand forming a non-carbon-metal bond, and X ⁵¹ represents a counter ion. The bond between Y ⁵¹ and the nitrogen atom represents a single bond or a double bond. The bond between R ⁵¹¹ and the nitrogen atom represents a single bond or a double bond. n ⁵¹ represents 0 or 1, n ⁵² represents 0 or 1, m ⁵¹ is 1 to 3
Represents an integer of 0, m ⁵² represents an integer of 0 to 8, and m ⁵³ represents 0.
Represents an integer of 3.

In the general formula (5), R ⁵¹¹ , R ⁵¹² , Y ⁵¹ and Z
⁵¹ , M ⁵¹ , X ⁵¹ , n ⁵¹ , n ⁵² , m ⁵¹ , m ⁵² , and m ⁵³ are R ¹¹ , R ¹² , Y ¹¹ , Z ¹¹ , M ¹¹ , X ¹¹ , n ¹¹ , n ¹² , and
It has the same meaning as m ¹¹ , m ¹² , and m ¹³ , respectively, and the preferred range is also the same.

L ⁵¹ is preferably a ligand which forms a non-carbon-metal bond (a ligand which does not form a carbon-metal bond), and more preferably a bidentate ligand which forms a non-carbon-metal bond.
The ligand that forms a non-carbon-metal bond is preferably a ligand that coordinates to a metal atom with a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom. More preferred ligands are bidentate ligands that coordinate to a metal at two different nitrogen atoms (eg, bipyridyl, phenanthroline, pyrazolylpyridine, benzimidazolylpyridine, pyrromethene, etc.), nitrogen atoms and oxygen atoms coordinate to the metal. A bidentate ligand (eg, picolinic acid, 2-hydroxymethylpyridine, etc.) or a bidentate ligand (acetylacetone, acetyl, etc.) that coordinates with a metal at two different oxygen atoms. Further preferred ligands are bidentate ligands which coordinate to the metal at two different nitrogen atoms.

The compound represented by the general formula (5) is preferably the compound represented by the general formula (6), and more preferably the compound represented by the general formula (7).

General formula (6)

[Chemical 11]

General formula (7)

[Chemical 12]

The general formula (6) will be described. Where Z
⁶¹, N⁶¹, L⁶¹, Q⁶¹, M⁶¹, M⁶²Are the above
Z⁵¹, N⁵¹, L⁵¹Is synonymous with. Q⁶¹Is a nitrogen-containing heterocycle
Represents an atomic group necessary for forming. m⁶¹Is an integer from 1 to 3
Represents m⁶²Represents an integer of 0 to 4. Z⁶¹, N⁶¹,
L⁶¹, Q⁶¹, M⁶¹, M⁶²Are each Z⁵¹, N⁵¹, L
⁵¹, Q ^{twenty one}, M^{twenty one}, M^{twenty two}Is synonymous with
It is the same.

The general formula (7) will be described. R ⁷⁰ , R
⁷¹ , R ⁷² , R ⁷⁹ , L ⁷¹ , m ⁷¹ and m ⁷² have the same meanings as R ⁵⁰ , R ⁵¹ , R ⁵² , R ⁴⁹ , L ⁵¹ , m ⁶¹ and m ⁶² , respectively, and the preferred ranges are also the same. .

The compound of the present invention may be a low molecular weight compound, and an oligomer compound and a polymer compound (the weight average molecular weight (in terms of polystyrene) thereof is preferably 1000).
~ 5,000,000, more preferably 2000-1000
000, and more preferably 3000 to 100,000. ) May be sufficient. When the compound of the present invention is a polymer compound, the structures represented by the general formulas (1) to (7) may be contained in the polymer main chain and / or the polymer side chain. When the compound of the present invention is a polymer compound, it may be a homopolymer compound or a copolymer. The compound of the present invention is preferably a low molecular weight compound.

Specific examples (exemplary compounds) of the compounds represented by the general formulas (1) to (7) of the present invention (hereinafter referred to as the compounds of the present invention) are shown below, but the present invention is not limited thereto.

[0055]

[Chemical 13]

[0056]

[Chemical 14]

[0057]

[Chemical 15]

[0058]

[Chemical 16]

[0059]

[Chemical 17]

The compound of the present invention can be synthesized by various known methods. For example, the ligand or its dissociation product and the transition metal compound can be used as a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, water, etc.). Can be synthesized in the presence. In the absence of a solvent, in the presence of a base (inorganic or organic various bases such as sodium methoxide, potassium t-butoxide, triethylamine, potassium carbonate, etc.), or in the absence of a base, at room temperature or lower. It can be obtained by reaction or heating (in addition to ordinary heating, a method of heating by microwave is also effective).

The compound of the present invention is also applicable to medical applications, fluorescent whitening agents, photographic materials, UV absorbing materials, laser dyes, dyes for color filters, color conversion filters and the like.

The 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 in terms of system, driving method, usage form, etc., as long as it is a device containing the compound, but it is preferable to use the compound as a light emitting material. The light emitting material means a compound which is contained in the light emitting layer of the light emitting element or the organic compound layer including the light emitting layer and emits light by itself. An organic EL (electroluminescence) element can be mentioned as a typical light emitting element.

In the light emitting device of the present invention, the light emitting layer is composed of the host compound and the compound represented by the general formula (1), and the energy level (T ₁ level) of the lowest triplet excited state of the host compound is 62 kcal / mol or more (259k
J / mol or more), 85 kcal / mol or less (355
kJ / mol or less), the light emitting layer is composed of the host compound and the compound represented by the general formula (1), and the T ₁ level of the host compound is 65 kcal /
mol or more (272 kJ / mol or more), 80 kca
It is more preferably 1 / mol or less (334 kJ / mol or less).

As the host compound of the light emitting device of the present invention satisfying the above physical property values, the host compounds described in Japanese Patent Application Nos. 2001-197135 and 2001-76704 are preferable, and the host compounds described in Japanese Patent Application No. 2001-197135 are more preferable. . The preferred range of the host compound described in Japanese Patent Application No. 2001-197135 is as described in the specification.

In the light emitting device of the present invention, the compound contained in the layer adjacent to the light emitting layer has a T ₁ level of 62 kcal / mol.
Above (259 kJ / mol or above), 85 kcal / mo
1 or less (355 kJ / mol or less), preferably 65 kcal / mol or more (272 kJ / mol or more), 80 kcal / mol or less (334 kJ / mol)
The following is more preferable.

The compounds contained in the layer adjacent to the light emitting layer satisfying the above physical properties are described in Japanese Patent Application No. 2001-197135.
The hole transport material and the electron transport material described in 1) are preferable. The preferable ranges of the hole transport material and the electron transport material described in Japanese Patent Application No. 2001-197135 are as described in the same specification.

The light emitting device of the present invention is a device in which a light emitting layer or a plurality of organic compound layers (organic layers) including a light emitting layer are formed between a pair of electrodes of an anode and a cathode, and in addition to the light emitting layer, a hole injection layer, It may have a hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers may have other functions. Various materials can be used for forming each layer.

A light emitting device containing the compound of the present invention is prepared by adding the compound to a light emitting layer or an organic compound layer containing the light emitting layer.
It is preferable to contain 0.1% by mass to 100% by mass, 1
The content is more preferably 50% by mass to 50% by mass, and particularly preferably 1% by mass to 20% by mass.

In the light emitting device of the present invention, it is preferable to use a layer containing a compound having an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the cathode and the light emitting layer, and the layer having an ionization potential of 5.9 eV or more is used. It is more preferable to use an electron transport layer.

The method for forming the organic layer of the light emitting device containing the compound of the present invention is not particularly limited, but resistance heating vapor deposition, electron beam, sputtering, molecular lamination method,
Coating method, ink jet method, printing method, transfer method, etc. are used.
A coating method and a transfer method are preferable.

The anode supplies holes to the hole injecting layer, the hole transporting layer, the light emitting layer and the like, and may be a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof. A material having a work function of 4 eV or more is preferable. 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.
Furthermore, a mixture or a laminate of these metals and a conductive metal oxide, an inorganic conductive substance such as copper iodide and copper sulfide, an organic conductive material such as polyaniline, polythiophene, polypyrrole, and a laminate of these and ITO. And the like. Among them, a conductive metal oxide is preferable, and ITO is particularly preferable in terms of productivity, high conductivity, transparency and the like.

The film 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,
The thickness is more preferably 50 nm to 1 μm, and further preferably 100 nm to 500 nm.

As the anode, a layer formed on soda lime glass, non-alkali glass, transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass as the material in order to reduce the amount of ions eluted from the glass. Further, when soda lime glass is used, it is preferable to use a glass coated with a barrier such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, it 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, electron beam method, sputtering method, resistance heating vapor deposition method, chemical reaction method (sol-gel method, etc.), indium tin oxide dispersion material is used. A film is formed by a method such as coating.

It is also possible to lower the driving voltage of the element and enhance the luminous efficiency by washing the anode and other treatments. For example, in the case of ITO, UV-ozone treatment and plasma treatment are effective.

The cathode supplies electrons to the electron injecting layer, the electron transporting layer, the light emitting layer, etc., and the adhesion between the negative electrode such as the electron injecting layer, the electron transporting layer, the light emitting layer and the adjacent layer and the ionization potential, 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 of the cathode include alkali metals (eg, Li, Na, K, etc.) and fluorides or oxides thereof, alkaline earth metals (eg, Mg, Ca, etc.) and fluorides or oxides thereof, gold, silver. , Lead, aluminum, sodium-potassium alloy or mixed metal thereof, lithium-aluminum alloy or mixed metal thereof, magnesium-silver alloy or mixed metal thereof, indium, rare earth metals such as ytterbium, and the like, preferably work. A material having a 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 may have not only a single layer structure of the above compound and mixture but also a laminated structure including the above compound and mixture. For example, a laminated structure of aluminum / lithium fluoride and aluminum / lithium oxide is preferable.

The film thickness of the cathode can be appropriately selected depending on the material, but it is usually preferably in the range of 10 nm to 5 μm,
The thickness is more preferably 50 nm to 1 μm, still more preferably 100 nm to 1 μm.

Electrodes, sputtering, resistance heating vapor deposition, coating, transfer and other methods are used for producing the cathode, and metal may be vapor-deposited alone or two or more components may be vapor-deposited simultaneously. it can. Further, it is possible to simultaneously deposit a plurality of metals to form an alloy electrode, and an alloy prepared in advance may be deposited. The sheet resistance of the anode and cathode is preferably low, several hundred Ω / □
The following are preferred.

As a material for the light emitting layer, holes can be injected from the anode or the hole injection layer or the hole transport layer when an electric field is applied, and electrons can be injected from the cathode or the electron injection layer or the electron transport layer. Any compound can be used as long as it can form a layer having a function, a function of moving injected charges, and a function of providing a field for recombination of holes and electrons to emit light. , For example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin,
Perylene, perinone, oxadiazole, aldazine,
Pyrrolidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, aromatic dimethylidyne compounds, various metal complexes represented by 8-quinolinol metal complex and rare earth complex, polythiophene, polyphenylene Polymer compounds such as polyphenylene vinylene, organic silanes, transition metal complexes represented by iridium trisphenylpyridine complexes, and platinum porphyrin complexes, and derivatives thereof.

The thickness of the light emitting layer is not particularly limited, but is preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and further preferably 1 nm.
It is 0 nm to 500 nm.

The method for forming the light emitting layer is not particularly limited, but resistance heating vapor deposition, electron beam, sputtering, molecular lamination method, coating method (spin coating method, casting method, dip coating method, etc.), ink jet method. The printing method, the LB method, the transfer method and the like are used, and the resistance heating vapor deposition and the coating method are preferable.

The light emitting layer may be formed of a single compound or a plurality of compounds. Further, the number of light emitting layers may be one or more, and each layer may emit light of different emission colors, for example, white light may be emitted. White light may be emitted from a single light emitting layer. When there are a plurality of light emitting layers, each light emitting layer may be formed of a single material, or may be formed of a plurality of compounds.

The material for the hole injecting layer and the hole transporting layer has any of the function of injecting holes from the anode, the function of transporting holes, and the function of blocking the electrons injected from the cathode. If Specific examples thereof include carbazole,
Triazole, oxazole, oxadiazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound , Aromatic dimethylidyne compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, conductive polymer oligomer such as polythiophene, organic silane, carbon film, Examples thereof include compounds and their derivatives.

The film thickness of the hole injecting layer and the hole transporting 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.
More preferably, it is 10 nm to 500 nm. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-mentioned materials, or may have a multi-layer structure composed of a plurality of layers having the same composition or different compositions.

The hole injecting layer and the hole transporting layer are formed by a vacuum vapor deposition method, an LB method, a method in which the hole injecting and transporting material is dissolved or dispersed in a solvent and coated (spin coating method, casting method, The dip coating method, etc.), the inkjet method, the printing method, and the transfer method are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, 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 and the like.

The material for the electron injecting layer and the electron transporting layer may be any one having a function of injecting electrons from the cathode, a function of transporting electrons, or a function of blocking holes injected from the anode. Good. Specific examples thereof include triazole,
Oxazole, oxadiazole, imidazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide,
Aromatic ring tetracarboxylic acid anhydrides such as fluorenylidenemethane, distyrylpyrazine, naphthalene, and perylene, phthalocyanines, metal complexes of 8-quinolinol, metal phthalocyanines, and metal complexes having benzoxazole and benzothiazole as ligands are typical. And various metal complexes, organic silanes, and derivatives thereof.

The thickness of the electron injection layer and the electron transport layer is not particularly limited, but it is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm,
More preferably, it is 10 nm to 500 nm. The electron injection layer and the electron transport layer may have a single-layer structure composed of one or more of the above-mentioned materials, or 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 are formed by a vacuum vapor deposition method, an LB method, a method in which the electron injecting and transporting material is dissolved or dispersed in a solvent and coated (spin coating method, casting method, dip coating method). Etc.), an inkjet method, a printing method, a transfer method and the like are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component, and as the resin component, for example, those exemplified in the case of the hole injecting and transporting layer can be applied.

The material of the protective layer is an element such as water or oxygen.
Function to prevent substances that promote deterioration from entering the device
As long as it has As a concrete example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO₂, Al₂O₃, G
eO, NiO, CaO, BaO, Fe₂O₃, Y₂O₃, T
iO₂Metal oxides such as MgF₂, LiF, AlF ₃, C
aF₂Metal fluorides such as SiN_x, SiO_xN_y Such as
Nitride, polyethylene, polypropylene, polymethylmeth
Tacrylate, polyimide, polyurea, polytetraf
Luoroethylene, polychlorotrifluoroethylene, polyethylene
Lydichlorodifluoroethylene, chlorotrifluoroe
A copolymer of ethylene and dichlorodifluoroethylene,
With trafluoroethylene and at least one comonomer
Copolymerization obtained by copolymerizing a monomer mixture containing
Body, a fluorinated copolymer having a cyclic structure in the copolymer main chain,
Water-absorbing substances with a water absorption rate of 1% or more, and water-absorbing substances with a water absorption rate of 0.1% or less
Examples include moist substances.

The method for forming the protective layer is not particularly limited, and examples thereof include vacuum deposition method, sputtering method, reactive sputtering method, MBE (molecular beam epitaxy) method, cluster ion beam method, ion plating method and plasma polymerization method ( A high frequency excitation ion plating method), a plasma CVD method, a laser CVD method, a thermal CVD method, a gas source CVD method, a coating method, a printing method, and a transfer method can be applied.

The light emitting device of the present invention includes a display device, a display, a back light, an electrophotography, an illumination light source, a recording light source,
It can be suitably used in the fields of exposure light source, reading light source, sign, signboard, interior, optical communication and the like.

[0093]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited thereto.

(Synthesis of Compound 1) To 3,45 g of 2,4-difluorophenylboric acid and 25 g of 2-bromopyridine, 200 ml of diethylene glycol dimethyl ether and 100 ml of water were added, and 33.5 g of sodium carbonate was added thereto.
g, palladium carbon (Pd content 10% by mass), and 0.1 g of triphenylphosphine were added, and the mixture was stirred under reflux for 5 hours. After cooling the solution to room temperature, ethyl acetate 500m
1 and 300 ml of water were added, and the mixture was filtered through Celite (manufactured by Wako Pure Chemical Industries). The organic layer was washed twice with 100 ml of water and then dried over sodium sulfate, and the organic layer was concentrated. Purification by column chromatography (developing with chloroform, then developing with chloroform / methanol = 5/1 (volume ratio)) gave 15 g of a single yellow liquid. 3.75 g of the obtained single yellow liquid
50 ml of 2-methoxyethanol, 30 ml of water, K ₃
5.0 g of IrCl ₆ was added, and the mixture was stirred under reflux for 4 hours.
After cooling to room temperature, the precipitated solid was filtered off to obtain 4 g of yellow solid compound 1. (Synthesis of Exemplified Compound 1-2) To 0.2 g of Compound 1 and 1.88 g of sodium picolinate, 10 ml of chloroform was added, and the mixture was stirred under reflux for 3 hours. Cool the reaction to room temperature,
Column chromatography (after developing with dichloromethane,
Purification with dichloromethane / methanol = 10/1) gave 0.15 g of Exemplified compound 1-2 as a yellow solid. The structure of (1-2) was confirmed by mass spectrum measurement. (1-2) emitted blue phosphorescence.

[0095]

[Chemical 18]

(Evaluation of Light Emitting Properties as Light Emitting Element) (Comparative Example 1) The cleaned ITO substrate was put in a vapor deposition apparatus and T
PD (N, N'-diphenyl-N, N'-di (m-tolyl) -benzidine) was vapor-deposited at 50 nm, and compound A and compound B were co-evaporated at a ratio of 1 to 17 (mass ratio) to 36 nm. Then, the azole compound C was vapor-deposited thereon to a thickness of 36 nm. A patterned mask (a mask having a light emitting area of 4 mm × 5 mm) is placed on the organic thin film, and lithium fluoride is vapor-deposited in a vapor deposition apparatus to a thickness of 3 nm.
nm was vapor-deposited to produce a device. Using a Toyo Technica source measure unit Model 2400, E
The light was applied to the L element to emit light, and the luminance was measured using a luminance meter BM-8 manufactured by Topcon and the emission wavelength was measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. As a result, green emission with ELmax (maximum emission wavelength) = 518 nm and chromaticity values (0.31, 0.61) was obtained, and the external quantum efficiency (emission luminance, emission spectrum, current density, specific luminous efficiency curve of the device was obtained. (Calculated) was 7.2%.

Comparative Example 2 A device was prepared and evaluated in the same manner as in Comparative Example 1 using Compound D instead of Compound A. As a result, green light emission was obtained.

[0098]

[Chemical 19]

Example 1 A device was prepared and evaluated in the same manner as in Comparative Example 1 except that the compound (1-2) of the present invention was used instead of the compound A. As a result, blue light emission with ELmax = 472 nm and a chromaticity value (0.18, 0.38) was obtained, and the external quantum efficiency of the device (emission brightness, emission spectrum, current density, and relative luminous efficiency curve) was 9. It was 0.4%.

A blue light emitting device can be similarly prepared by using other compounds of the present invention. In addition, a white light emitting element can be manufactured by using a red light emitting material in combination.

[0101]

The light emitting device of the present invention is capable of emitting blue light, has a small chromaticity value and is excellent in external quantum efficiency.

Claims (7)

[Claims] 1. A light emitting device having a light emitting layer or a plurality of organic compound layers including a light emitting layer formed between a pair of electrodes,
A light emitting device comprising a light emitting layer containing at least one compound represented by the following general formula (1). General formula (1) (In the formula, R ¹¹ represents a substituent, R ¹² represents a hydrogen atom or a substituent, Y ¹¹ represents a substituted or unsubstituted nitrogen atom, or a substituted or unsubstituted carbon atom, and Z ¹¹ is a link. Represents a group, M ¹¹ represents a transition metal ion, L ¹¹ represents a ligand, X ¹¹ represents a counter ion, and the bond between Y ¹¹ and a nitrogen atom represents a single bond or a double bond. The bond between R ¹¹ and the nitrogen atom represents a single bond or a double bond, and n ¹¹ is 0.
Or 1, n ¹² represents 0 or 1, m ¹¹ represents an integer of 1 to 3, m ¹² represents an integer of 0 to 8 and m ¹³ represents 0 to 3
Represents the integer. The compound represented by the general formula (1) has at least one electron-withdrawing group in the compound. ) 2. The light emitting layer contains a host compound and a compound represented by the general formula (1), and the energy level (T ₁ level) of the lowest triplet excited state of the host compound is 62 k.
cal / mol or more (259 kJ / mol or more), 85
It is kcal / mol or less (355 kJ / mol or less), The light emitting element of Claim 1 characterized by the above-mentioned. 3. The lowest triplet excited state energy level (T ₁ level) of the compound contained in the layer adjacent to the light emitting layer.
Is 62 kcal / mol or more (259 kJ / mol or more), 85 kcal / mol or less (355 kJ / mol)
The following), The light emitting element according to claim 1 or 2. 4. A light emitting device having a light emitting layer or a plurality of organic compound layers including a light emitting layer formed between a pair of electrodes,
A light emitting device comprising a light emitting layer containing at least one compound represented by the following general formula (5). General formula (5) (In the formula, R ⁵¹¹ represents a substituent, R ⁵¹² represents a hydrogen atom or a substituent, Y ⁵¹ represents a substituted or unsubstituted nitrogen atom, or a substituted or unsubstituted carbon atom, and Z ⁵¹ is a link. Represents a group, M ⁵¹ represents a transition metal ion, L ⁵¹ represents a ligand forming a non-carbon-metal bond, X ⁵¹ represents a counter ion, and the bond between Y ⁵¹ and a nitrogen atom is: Represents a single bond or a double bond, the bond between R ⁵¹¹ and a nitrogen atom represents a single bond or a double bond, n ⁵¹ represents 0 or 1, n ⁵² represents 0 or 1, m ⁵¹ Represents an integer of 1 to 3, m ⁵² is 0
Represents an integer of 8 and m ⁵³ represents an integer of 0 to 3. ) 5. The light emitting device according to claim 4, wherein the general formula (5) is a compound represented by the following general formula (6). General formula (6) (In the formula, Z ⁶¹ , n ⁶¹ , L ⁶¹ , Q ⁶¹ , m ⁶¹ , and m ⁶² have the same meanings as Z ⁵¹ , n ⁵¹ , and L ⁵¹ , respectively. Q ⁶¹ is necessary for forming a nitrogen-containing heterocycle. M ⁶¹ is 1 to 3
And an integer of 0 to 4 is represented by m ⁶² . ) 6. The ligand according to claim 4, wherein L ⁵¹ is a ligand in which at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom and a phosphorus atom is coordinated with a metal atom. Light emitting element. 7. L ⁵¹ is a bidentate ligand which coordinates to a metal with two nitrogen atoms, and 2 which coordinates to a metal with a nitrogen atom and an oxygen atom.
The light-emitting device according to claim 4, which is a bidentate ligand or a bidentate ligand that coordinates to a metal with two oxygen atoms.