JP6085985B2 - ORGANIC METAL COMPLEX, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, LIGHTING DEVICE AND DISPLAY DEVICE - Google Patents

Description

  The present invention relates to an organometallic complex, an organic electroluminescence element material, an organic electroluminescence element, an illumination device, and a display device. More specifically, the present invention relates to an organometallic complex with improved electron resistance, an organic electroluminescent element material and an organic electroluminescent element using the organometallic complex, and an illumination device and a display apparatus using the element.

  An organic electroluminescence element (hereinafter also referred to as an organic EL element) has a configuration in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. In addition, the organic EL element generates excitons by recombining holes injected from the anode and electrons injected from the cathode in the light emitting layer by applying an electric field. The organic EL element is a light-emitting element utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated. The organic EL element is an all-solid-state element composed of an organic material film having a thickness of only a submicron between the electrodes, and can emit light at a voltage of several V to several tens V. Therefore, it is expected to be used for next-generation flat display and lighting.

  As for the development of organic EL elements for practical application, Princeton University has reported on organic EL elements that use phosphorescence from excited triplets, and since then, research on materials that exhibit phosphorescence at room temperature has become active. (For example, see Patent Document 1).

  Furthermore, organic EL elements that utilize phosphorescence emission can in principle achieve a light emission efficiency that is approximately four times that of organic EL elements that utilize previous fluorescence emission. Research and development of device layer configurations and electrodes are performed all over the world. For example, many compounds have been studied focusing on heavy metal complexes such as iridium complexes.

As a typical blue phosphorescent compound, FIrpic (Bis [2- (4,6-difluorophenyl) pyridinato-C ² , N] (picolinato) iridium (III)) is known, and the main ligand is Shortening of the wavelength has been realized by replacing fluorine with phenylpyridine and using picolinic acid as a secondary ligand.
Not only FIrpic but also fluorine-substituted blue phosphorescent dopants are well known (see, for example, Patent Documents 2 to 4). The effect of fluorine substitution is that the wavelength of light emission is shortened, which is a useful substituent as a blue phosphorescent dopant. However, in our research, conventional fluorine-substituted dopants have poor carrier resistance, especially electron resistance, which indicates the stability of the anion radical state when electrons are received. It is known that it is causing deterioration.

US Pat. No. 6,097,147 International Publication No. 2007/097149 JP 2005-68110 A International Publication No. 2012/068736

  The present invention has been made in view of the above problems and situations. The problem to be solved is to provide an organometallic complex that is a fluorine-substituted blue dopant having excellent electron resistance. Another object of the present invention is to provide an organic electroluminescence element material and an organic electroluminescence element that have high luminous efficiency, long emission lifetime, and suppressed voltage increase during driving, and an illumination device and a display apparatus using the element.

As a result of examining the cause of the above-mentioned problem in order to solve the above-mentioned problems, the present inventor has an organometallic complex having a structure represented by the following general formula (1) having characteristics useful for solving the above-mentioned problems. And found the present invention.
That is, the said subject which concerns on this invention is solved by the following means.

（一般式（１）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１、Ｘ_２、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。ただし、Ｘ _１ 、Ｘ _２ 及びＸ _５ の全てが窒素原子を表す場合は除く。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。） 1. An organometallic complex having a structure represented by the following general formula (1).

(In General Formula (1), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, wherein X ₁ , X ₂ , X ₆ , X ₇ and X ₈ are Represents a carbon atom or a nitrogen atom, X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and X _{1 to} X ₅ may have a substituent. Except when X ₁ , X ₂ and X ₅ all represent a nitrogen atom, A ₁ and A ₂ are Each represents a residue necessary to form an aromatic hydrocarbon ring or an aromatic heterocycle, M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3. M represents an integer of 0 to 2 and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.)

（一般式（２）中、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１、Ｘ_２、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。） 2. 2. The organometallic complex according to item 1, which has a structure represented by the following general formula (2).

(In the general formula (2), R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent, where Ra is an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring; Represents a group or a non-aromatic heterocyclic group, X ₁ , X ₂ , X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom, and X ₃ , X ₄ and X ₅ represent a carbon atom or a nitrogen atom. Represents an oxygen atom or a sulfur atom, X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent, and A ₁ and A ₂ each represent an aromatic hydrocarbon ring or an aromatic group. Represents a residue necessary to form a group heterocycle, M represents iridium or platinum, and M represents iridium. In this case, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, and m represents 0 or 1. M + n is 2.)

3. 2. The organometallic complex according to item _1, wherein Y ₁ in the general formula (1) is N.

4). The organometallic complex according to any one of Items 1 to 3, wherein X _{1 to} X ₅ in the general formula (1) form an imidazole ring.

5. The organometallic complex according to any one of Items 1 to 3, wherein in the general formula (1), X _{1 to} X ₅ form a pyrazole ring.

6). The organometallic complex according to any one of Items 1 to 3, wherein X _{1 to} X ₅ in the general formula (1) form a triazole ring.

7). The organometallic complex according to any one of Items 1 to 3, wherein X _{1 to} X ₅ in the general formula (1) form a tetrazole ring.

（一般式（３）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_５及びＲ_６は、それぞれ独立にアルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。Ｒ_４及びＲ_７は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。ｎａは、１又は２を表し、ｎｂは１〜３の整数を表す。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。） 8). 2. The organometallic complex according to item 1, which has a structure represented by the following general formula (3).

(In General Formula (3), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, wherein R ₅ and R ₆ are each independently an alkyl group, aromatic It represents a hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent, and R ₄ and R ₇ are each independently hydrogen. Atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, Represents a silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group, and may further have a substituent, na represents 1 or 2 , Nb represents an integer of _{1 to 3.} X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom, and A ₁ and A ₂ each form an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. (When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.)

（一般式（４）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_８は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。ｎｃは、１又は２を表す。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。） 9. 2. The organometallic complex according to item 1, which has a structure represented by the following general formula (4).

(In General Formula (4), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and R ₈ each independently represents a hydrogen atom, a halogen atom, or a cyano group. Represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and further a substituent. good .nc have a represents 1 or 2 .X , .M X ₇ and X _8, which represents the atoms necessary to form a .A ₁ and A ₂ each, aromatic hydrocarbon ring or aromatic heterocyclic ring represents a carbon atom or a nitrogen atom, iridium Or M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2 M represents 0 or 1, and m + n is 2.)

（一般式（５）中、Ｒ _１ 、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_９はアルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_１０及びＲ_１１は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良く、Ｒ_１０とＲ_１１が縮合して環を形成しても良い。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。） 10. 2. The organometallic complex according to item 1, which has a structure represented by the following general formula (5).

(In General Formula (5) , R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic group. Represents a heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent, where Ra is an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring; R ₉ represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, R ₁₀ and R ₁₁ is independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon Represents a cyclic group or a non-aromatic heterocyclic group, In may have a substituent _{group, R 10} and _{R 11} is may be formed a fused ring _.X 6, _{X 7} and _{X 8,} .A ₁ and A represents a carbon atom or a nitrogen atom ₂ represents a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring, M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3. M represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

（式中、Ｖは３価の連結基を表し、Ｌ_１、Ｌ_２及びＬ_３と共有結合で連結している。Ｌ_１〜Ｌ_３は、下記一般式（７）又は一般式（８）で表され、少なくとも一つは一般式（７）である。Ｖが表す３価の連結基としては、分岐アルキル基、置換基を有する芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基である。）

（一般式（７）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１及びＸ_２は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。）

（一般式（８）中、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。） 11. 2. The organometallic complex according to item 1, which has a structure represented by the following general formula (6).

(In the formula, V represents a trivalent linking group and is covalently linked to L ₁ , L ₂ and L _3. L _{1 to} L ₃ are represented by the following general formula (7) or general formula (8). And at least one is represented by the general formula (7): The trivalent linking group represented by V includes a branched alkyl group, a substituted aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic group. An aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. )

(In General Formula (7), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and X ₁ and X _{2 each} represent a carbon atom or a nitrogen atom. X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent.

(In the general formula (8), X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ are each necessary to form an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Represents a residue.

12 The organometallic complex according to any one of Items 1 to 11, wherein R ₁ represents a cyano group.

13. The organometallic complex according to any one of Items 1 to 11, wherein R ₁ represents a —SiRa ₃ group.

14 The organometallic complex according to item 8, wherein R ₅ and R ₆ represent a branched alkyl group having 3 or more carbon atoms.

  15. The organometallic complex according to any one of Items 1 to 14, wherein M represents iridium.

  16. An organic electroluminescent element material comprising an organometallic complex having a structure represented by the general formula (1) described in item 1 as a component.

  17. The organic electroluminescent element material according to item 16, which contains as a component an organometallic complex having a structure represented by the general formula (2) described in item 2.

  18. The organic electroluminescent element material according to item 16, which contains as a component an organometallic complex having a structure represented by the general formula (3) described in item 8.

  19. Item 16. The organic electroluminescent device material according to item 16, which contains as a component an organometallic complex having a structure represented by the general formula (4) described in item 9.

  20. Item 16. An organic electroluminescent element material according to Item 16, comprising an organometallic complex having a structure represented by Formula (5) according to Item 10 as a component.

  21. Item 16. An organic electroluminescent element material according to item 16, which contains as a component an organometallic complex having a structure represented by the general formula (6) according to item 11.

22. An organic electroluminescence device in which an organic layer including a light emitting layer is sandwiched between an anode and a cathode,
The said organic layer contains the organometallic complex which has a structure represented by General formula (1) of 1st term | claim, The organic electroluminescent element characterized by the above-mentioned.

  23. 23. The organic electroluminescent element according to item 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (2) described in item 2.

  24. 23. The organic electroluminescent element according to item 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (3) described in item 8.

  25. Item 23. The organic electroluminescent element according to Item 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (4) described in Item 9.

  26. 23. The organic electroluminescent element according to item 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (5) described in item 10.

  27. 23. The organic electroluminescent element according to item 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (6) described in item 11.

  28. Item 28. The organic electroluminescence device according to any one of Items 22 to 27, wherein the emission color is white.

  29. An organic electroluminescence device according to any one of items 22 to 27 is provided.

  30. A display device comprising the organic electroluminescence element according to any one of items 22 to 27.

By the above means of the present invention, an organometallic complex that is a fluorine-substituted blue dopant having excellent electron resistance can be provided. In addition, it is possible to provide an organic electroluminescence element material and an organic electroluminescence element that have high luminous efficiency, have a long emission lifetime, and suppress a voltage increase during driving, and a lighting device and a display apparatus using the element.
The expression mechanism and action mechanism of the effects of the present invention are not clear, but are presumed as follows.

In the organometallic complex used for the conventional organic EL element, it has been found that having a fluorine atom at the position of R _{2 in} the general formula (1) leads to a decrease in electron resistance. Therefore, in the present invention, a fluorine atom is present at a specific position in the general formula (1) (ortho position as seen from the carbon bonded to the 5-membered ring), and Y ₁ represents C—R ₁ or N. Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group or a non-aromatic hydrocarbon. It is considered that the electron resistance can be improved by using a cyclic group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ as a substituent.

Schematic diagram showing an example of a display device composed of organic EL elements Schematic diagram of an active matrix display device Schematic showing the pixel circuit Schematic diagram of a passive matrix display device Schematic of lighting device Schematic diagram of lighting device

  The organometallic complex of the present invention has a structure represented by the general formula (1). This feature is a technical feature common to the inventions according to claims 1 to 30.

As an embodiment of the present invention, from the viewpoint of expression of the effect of the present invention, in the general formula (1), X _{1 to} X ₅ may form an imidazole ring, a pyrazole ring, a triazole ring, or a tetrazole ring. Depending on the structure of the substituent, the emission color can be finely adjusted, which is preferable.

  Moreover, in the organometallic complex which has a structure represented by the said General formula (1) of this invention, it represents with the said General formula (2), (3), (4), (5) or (6). It is preferable to have a structure in order to make the effect of the present invention remarkable.

In addition, it is preferable that R ₁ represents a cyano group or a —SiRa ₃ group because the emission color can be finely adjusted.

It is preferable for R ₅ and R ₆ to represent a branched alkyl group having 3 or more carbon atoms in order to make the effect of the present invention remarkable.

  It is preferable that M represents iridium from the viewpoints of luminous efficiency and luminous lifetime.

The organometallic complex of the present invention can be suitably used as an organic electroluminescence element material. In addition, when using as an organic electroluminescent element material, the organometallic complex of this invention may be used independently, or may be used as a material which contains a several compound together.
Moreover, the organic electroluminescent element using the said organic electroluminescent element material can be used conveniently for an illuminating device or a display apparatus.

  Hereinafter, the present invention, its components, and modes and modes for carrying out the present invention will be described in detail. In addition, in this application, "-" is used in the meaning which includes the numerical value described before and behind that as a lower limit and an upper limit.

一般式（１）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１、Ｘ_２、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。 <Organic metal complex>
<Organic metal complex having a structure represented by the general formula (1)>
The organometallic complex of the present invention has a structure represented by the following general formula (1).

In General Formula (1), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R _2, and R ₃ each independently represent a hydrogen atom, an alkyl group, An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ may be further substituted. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. X ₁ , X ₂ , X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom. X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum. When M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

In the general formula (1), examples of the alkyl group represented by R ₁ , R ₂ and R ₃ include a methyl group, an ethyl group, a trifluoromethyl group, an isopropyl group, an n-butyl group, a t-butyl group, Examples include n-hexyl group, 2-methylhexyl group, pentyl group, adamantyl group, n-decyl group and n-dodecyl group.

Examples of the aromatic hydrocarbon ring represented by R ₁ , R ₂ and R ₃ include a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene Ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene And a ring, a pyranthrene ring and an anthraanthrene ring.

In the general formula (1), examples of the aromatic heterocycle represented by R ₁ , R ₂ and R ₃ include a silole ring, a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, and a pyrimidine. Ring, pyrazine ring, triazine ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzthiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, thieno Thiophene ring, carbazole ring, azacarbazole ring (representing any one or more of the carbon atoms constituting the carbazole ring replaced by a nitrogen atom), dibenzosilole ring, dibenzofuran ring, dibenzothiophene ring, benzothiophene ring, dibenzofuran Of the carbon atoms that make up the ring Rings in which any one or more are replaced by nitrogen atoms, benzodifuran rings, benzodithiophene rings, acridine rings, benzoquinoline rings, phenazine rings, phenanthridine rings, phenanthroline rings, cyclazine rings, quindrine rings, tepenidine rings, quinindrin rings , Triphenodithiazine ring, triphenodioxazine ring, phenanthrazine ring, anthrazine ring, perimidine ring, naphthofuran ring, naphthothiophene ring, naphthodifuran ring, naphthodithiophene ring, anthrafuran ring, anthradifuran ring, anthrathiophene ring , Anthradithiophene ring, thianthrene ring, phenoxathiin ring, dibenzocarbazole ring, indolocarbazole ring and dithienobenzene ring.

In the general formula (1), examples of the non-aromatic hydrocarbon ring represented by R ₁ , R ₂ and R ₃ include a cycloalkane (for example, a cyclopentane ring or a cyclohexane ring), a cycloalkoxy group (for example, A cyclopentyloxy group or a cyclohexyloxy group), a cycloalkylthio group (for example, a cyclopentylthio group or a cyclohexylthio group), a cyclohexylaminosulfonyl group, a tetrahydronaphthalene ring, a 9,10-dihydroanthracene ring and a biphenylene ring.

In the general formula (1), examples of the non-aromatic heterocyclic ring represented by R ₁ , R ₂ and R ₃ include, for example, an epoxy ring, an aziridine ring, a thiirane ring, an oxetane ring, an azetidine ring, a thietane ring, a tetrahydrofuran ring, Dioxolane ring, pyrrolidine ring, pyrazolidine ring, imidazolidine ring, oxazolidine ring, tetrahydrothiophene ring, sulfolane ring, thiazolidine ring, ε-caprolactone ring, ε-caprolactam ring, piperidine ring, hexahydropyrimazine ring, hexahydropyrimidine ring, piperazine Ring, morpholine ring, tetrahydropyran ring, 1,3-dioxane ring, 1,4-dioxane ring, trioxane ring, tetrahydrothiopyran ring, thiomorpholine ring, thiomorpholine-1,1-dioxide ring, pyranose ring, diazabicyclo [ 2,2,2] -Oct Down ring, phenoxazine ring, a phenothiazine ring, Okisantoren rings include thioxanthene ring and a phenoxathiin ring.

Further, in the general formula (1), when R ₁ represents a cyano group or a —SiRa ₃ group, the emission color can be finely adjusted, which is preferable.

X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent. Specifically, X _{1 to} X _{5 each} represents a carbon atom, CRb, nitrogen atom, NRc, oxygen atom or sulfur atom, and at least one of them preferably represents a nitrogen atom.
Rb and Rc represent a hydrogen atom or a substituent. Examples of the substituent include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group, or a pentadecyl group). A cycloalkyl group (for example, a cyclopentyl group or a cyclohexyl group), an alkenyl group (for example, a vinyl group or an allyl group), an alkynyl group (for example, an ethynyl group or a propargyl group), an aromatic hydrocarbon group (an aromatic hydrocarbon) Also referred to as a cyclic group, aromatic carbocyclic group or aryl group, for example, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group, azulenyl group, acenaphthenyl group, fluorenyl group, phenanthryl Group, indenyl group, pyrenyl group or biphenylyl group, etc. An aromatic heterocyclic group (for example, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, pyrazinyl group or triazolyl group (for example, 1,2,4-triazol-1-yl group) Or 1,2,3-triazol-1-yl group), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group, thienyl group, quinolyl group, benzofuryl group, dibenzofuryl group, Benzothienyl group, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (indicating that one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom), quinoxalinyl group , Pyridazinyl group, triazinyl group, key Zolinyl group or phthalazinyl group), heterocyclic group (for example, pyrrolidyl group, imidazolidyl group, morpholyl group or oxazolidyl group), alkoxy group (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group) Octyloxy group or dodecyloxy group), cycloalkoxy group (for example, cyclopentyloxy group or cyclohexyloxy group), aryloxy group (for example, phenoxy group, naphthyloxy group, etc.), alkylthio group (for example, methylthio group, An ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group or a dodecylthio group), a cycloalkylthio group (for example, a cyclopentylthio group or a cyclohexylthio group), an arylthio group (for example, a phenylthio group, Naphthylthio group etc.), alkoxycarbonyl group (eg methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group or dodecyloxycarbonyl group etc.), aryloxycarbonyl group (eg phenyloxycarbonyl group or Naphthyloxycarbonyl group, etc.), sulfamoyl group (for example, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group) , Phenylaminosulfonyl group, naphthylaminosulfonyl group or 2-pyridylaminosulfonyl group), acyl group (for example, acetyl group, ethyl group) Bonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group or pyridylcarbonyl group), acyloxy group (for example, acetyloxy) Group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group or phenylcarbonyloxy group), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propyl) Carbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino , Dodecylcarbonylamino group, phenylcarbonylamino group or naphthylcarbonylamino group), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl) Group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group or 2-pyridylaminocarbonyl group), ureido group (for example, methylureido group, ethylureido group, Pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, or 2-pyridylami Noureido group, etc.), sulfinyl group (for example, methylsulfinyl group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group or 2-pyridylsulfinyl group) ), Alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group or heteroarylsulfonyl group (for example, phenylsulfonyl group) Naphthylsulfonyl group or 2-pyridylsulfonyl group), amino group (for example, amino group, ethylamino group, dimethylamino group, diphenyla) Group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group or 2-pyridylamino group), halogen atom (for example, fluorine atom, chlorine atom or bromine atom) , Fluorinated hydrocarbon group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group or pentafluorophenyl group), cyano group, nitro group, hydroxy group, mercapto group, silyl group (for example, trimethylsilyl group, A triisopropylsilyl group, a triphenylsilyl group or a phenyldiethylsilyl group) and a phosphono group. Preferably, an alkyl group, an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkoxy group, an amino group, and a cyano group are exemplified.
Moreover, these substituents may be further substituted with the above substituents.
Further, these substituents may be bonded together to form a ring.
An aromatic nitrogen-containing heterocycle is formed by the five atoms X _{1 to} X ₅ . Examples of the aromatic nitrogen-containing heterocycle include, for example, a pyrrole ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, and a carbene-containing ring. Examples include thiadiazole rings. Among these, a ring including a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, and a carbene is preferable.

  The organometallic complex according to the present invention is also referred to as a light-emitting dopant (phosphorescent dopant (“phosphorescent dopant”, “phosphorescent dopant group”) of an organic electroluminescence element (hereinafter also referred to as an organic EL element). .), Fluorescent dopants, etc.).

  Next, the organometallic complex represented by the general formulas (2) to (6) in which the structure of the general formula (1) is limited will be described.

一般式（２）中、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１、Ｘ_２、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。 <Organic metal complex having a structure represented by the general formula (2)>
The organometallic complex according to the present invention preferably has a structure represented by the following general formula (2).

In general formula (2), R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. It represents a heterocyclic group, a cyano group or —SiRa ₃ and may further have a substituent. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. X ₁ , X ₂ , X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom. X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum. When M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

In the general formula _(2), the substituent represented by R 1, _{R 2} and _{R 3,} can be used a _{substituent R} 1 in the general formula (1), _{R 2} and _{R 3} represents.

In the general formula _(2), for the atom represented by X 1 to X _5, it is possible to use a general formula (1) _X 1 to X ₅ represents atoms in.

一般式（３）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_５及びＲ_６は、それぞれ独立にアルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。Ｒ_４及びＲ_７は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。ｎａは、１又は２を表し、ｎｂは１〜３の整数を表す。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２は、それぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。 <Organic metal complex having a structure represented by the general formula (3)>
The organometallic complex according to the present invention preferably has a structure represented by the following general formula (3).

In General Formula (3), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ may be further substituted. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. R ₅ and R ₆ each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and further has a substituent. May be. R ₄ and R ₇ are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic Represents a hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent. na represents 1 or 2, and nb represents an integer of 1 to 3. X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum. When M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

In general formula (3), the alkyl group, aromatic hydrocarbon ring group, aromatic heterocyclic group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group represented by R ₅ and R ₆ is represented by the general formula ( Specific examples are given as the alkyl group, aromatic hydrocarbon ring group, aromatic heterocyclic group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group represented by R ₁ , R ₂ and R _{3 in} 1). Things can be used.

In general formula (3), examples of the alkyl group represented by R ₄ and R ₇ include a methyl group, an ethyl group, a trifluoromethyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, Examples include 2-methylhexyl group, pentyl group, adamantyl group, n-decyl group, and n-dodecyl group, but are not limited thereto.

In general formula (3), R ₅ and R ₆ are preferably branched alkyl groups having 3 or more carbon atoms.

In the general formula (3), examples of the alkenyl group represented by R ₄ and R ₇ include a vinyl group and an allyl group. Examples of the alkynyl group represented by R ₄ and R ₇ include an ethynyl group and a propargyl group.

In the general formula (3), examples of the alkoxy group represented by R ₄ and R ₇ include a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, and a dodecyloxy group. Can be mentioned.

In the general formula (3), examples of the amino group represented by R ₄ and R ₇ include an amino group, an ethylamino group, a dimethylamino group, a butylamino group, a cyclopentylamino group, a 2-ethylhexylamino group, and a dodecylamino group. Groups, anilino groups, naphthylamino groups, 2-pyridylamino groups, piperidyl groups (also referred to as piperidinyl groups), 2,2,6,6-tetramethylpiperidinyl groups, and the like.

In the general formula (3), examples of the silyl group represented by R ₄ and R ₇ include a trimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group, and a phenyldiethylsilyl group.

In the general formula (3), examples of the arylalkyl group represented by R ₄ and R ₇ include a benzyl group, a naphthylmethyl group, and a diphenylmethyl group.

In the general formula (3), the aromatic hydrocarbon ring group represented by R ₄ and R ₇ includes a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, chrysene ring, naphthacene ring, triphenylene Ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene And groups derived from a ring, a pyranthrene ring, an anthraanthrene ring, and the like.

In the general formula (3), examples of the aromatic heterocyclic group represented by R ₄ and R ₇ include a silole ring, a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring. , Triazine ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzthiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, thienothiophene ring, carbazole A ring, an azacarbazole ring (representing any one or more of the carbon atoms constituting the carbazole ring replaced by a nitrogen atom), a dibenzosilole ring, a dibenzofuran ring, a dibenzothiophene ring, a benzothiophene ring or a dibenzofuran ring Any one of carbon atoms Ring substituted with nitrogen atom, benzodifuran ring, benzodithiophene ring, acridine ring, benzoquinoline ring, phenazine ring, phenanthridine ring, phenanthroline ring, cyclazine ring, quindrine ring, tepenidine ring, quinindrin ring, triphenodithia Gin ring, triphenodioxazine ring, phenanthrazine ring, anthrazine ring, perimidine ring, naphthofuran ring, naphthothiophene ring, naphthodifuran ring, naphthodithiophene ring, anthrafuran ring, anthradifuran ring, anthrathiophene ring, anthradithiophene And groups derived from a ring, a thianthrene ring, a phenoxathiin ring, a dibenzocarbazole ring, an indolocarbazole ring, a dithienobenzene ring, an indoloindole ring, and the like.

In the general formula (3), examples of the non-aromatic hydrocarbon ring group represented by R ₄ and R ₇ include a cycloalkyl group (for example, a cyclopentyl group or a cyclohexyl group) and a cycloalkoxy group (for example, a cyclopentyloxy group or Cyclohexyloxy group, etc.), cycloalkylthio group (for example, cyclopentylthio group or cyclohexylthio group), cyclohexylaminosulfonyl group, or groups derived from tetrahydronaphthalene ring, 9,10-dihydroanthracene ring, biphenylene ring, etc. Can be mentioned.

In the general formula (3), examples of the non-aromatic heterocyclic group represented by R ₄ and R ₇ include an epoxy ring, an aziridine ring, a thiirane ring, an oxetane ring, an azetidine ring, a thietane ring, a tetrahydrofuran ring, and a dioxolane ring. Pyrrolidine ring, pyrazolidine ring, imidazolidine ring, oxazolidine ring, tetrahydrothiophene ring, sulfolane ring, thiazolidine ring, ε-caprolactone ring, ε-caprolactam ring, piperidine ring, hexahydropyridazine ring, hexahydropyrimidine ring, piperazine ring, Morpholine ring, tetrahydropyran ring, 1,3-dioxane ring, 1,4-dioxane ring, trioxane ring, tetrahydrothiopyran ring, thiomorpholine ring, thiomorpholine-1,1-dioxide ring, pyranose ring, diazabicyclo [2, 2,2] -octane , Phenoxazine ring, a phenothiazine ring, Okisantoren ring, and a group derived from thioxanthene ring and a phenoxathiin ring, and the like.

一般式（４）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_８は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良い。ｎｃは、１又は２を表す。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。 <Organic metal complex having a structure represented by the general formula (4)>
The organometallic complex according to the present invention preferably has a structure represented by the following general formula (4).

In General Formula (4), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ may be further substituted. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. R ₈ is independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon It represents a cyclic group or a non-aromatic heterocyclic group, and may further have a substituent. nc represents 1 or 2. X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum. When M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

In the general formula _(4), the substituent represented by R 1, _{R 2} and _{R 3,} can be used a _{substituent R} 1 in the general formula (1), _{R 2} and _{R 3} represents.

In the general formula (4), the halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic carbonization represented by R ₈ For the hydrogen ring group or the non-aromatic heterocyclic group, the halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group represented by R ₄ and R ₇ in the general formula (3) , Arylalkyl groups, aryl groups, heteroaryl groups, non-aromatic hydrocarbon ring groups, or non-aromatic heterocyclic groups can be used as specific examples.

一般式（５）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_９はアルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｒ_１０及びＲ_１１は、それぞれ独立に水素原子、ハロゲン原子、シアノ基、アルキル基、アルケニル基、アルキニル基、アルコキシ基、アミノ基、シリル基、アリールアルキル基、アリール基、ヘテロアリール基、非芳香族炭化水素環基又は非芳香族複素環基を表し、更に置換基を有していても良く、Ｒ_１０とＲ_１１が縮合して環を形成しても良い。Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。Ｍは、イリジウム又は白金を表す。Ｍがイリジウムを表す場合、ｎは１〜３の整数を表し、ｍは０〜２の整数を表し、ｍ＋ｎは３である。Ｍが白金を表す場合、ｎは１又は２を表し、ｍは０又は１を表し、ｍ＋ｎは２である。 <Organic metal complex having a structure represented by the general formula (5)>
The organometallic complex according to the present invention preferably has a structure represented by the following general formula (5).

In General Formula (5), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ may be further substituted. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. R ₉ represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. R ₁₀ and R ₁₁ are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic Represents a hydrocarbon ring group or a non-aromatic heterocyclic group, may further have a substituent, and R ₁₀ and R ₁₁ may be condensed to form a ring. X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum. When M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.

In the general formula _(5), the substituent represented by R 1, _{R 2} and _{R 3,} can be used a _{substituent R} 1 in the general formula (1), _{R 2} and _{R 3} represents.

In general formula (5), for the alkyl group, aromatic hydrocarbon ring group, aromatic heterocyclic group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group represented by R ₉ in general formula (1), Use of alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups or non-aromatic heterocyclic groups represented by R ₁ , R ₂ and R ₃ as specific examples Can do.

In the general formula (5), a halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-represented by R ₁₀ and R ₁₁ As an aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group represented by R ₄ and R ₇ in the general formula (2) Specific examples of the silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group can be used.

式中、Ｖは３価の連結基を表し、Ｌ_１、Ｌ_２及びＬ_３と共有結合で連結している。Ｌ_１〜Ｌ_３は、下記一般式（７）又は一般式（８）で表され、少なくとも一つは一般式（７）である。

一般式（７）中、Ｙ_１はＣ−Ｒ_１又はＮを表し、Ｙ_２はＣ−Ｒ_３又はＮを表し、Ｒ_１、Ｒ_２及びＲ_３は、それぞれ独立に水素原子、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基、非芳香族複素環基、シアノ基又は−ＳｉＲａ_３を表し、更に置換基を有していても良い。Ｒａは、アルキル基、芳香族炭化水素環基、芳香族複素環基、非芳香族炭化水素環基又は非芳香族複素環基を表す。Ｘ_１及びＸ_２は、炭素原子又は窒素原子を表す。Ｘ_３、Ｘ_４及びＸ_５は、炭素原子、窒素原子、酸素原子又は硫黄原子を表す。Ｘ_１〜Ｘ_５は、置換基を有してもよい５員の複素環基を形成する。

一般式（８）中、Ｘ_６、Ｘ_７及びＸ_８は、炭素原子又は窒素原子を表す。Ａ_１及びＡ_２はそれぞれ、芳香族炭化水素環又は芳香族複素環を形成するのに必要な残基を表す。 <Organic metal complex having a structure represented by the general formula (6)>
The organometallic complex according to the present invention preferably has a structure represented by the following general formula (6).

In the formula, V represents a trivalent linking group and is linked to L ₁ , L ₂ and L ₃ by a covalent bond. L _{1 to} L ₃ are represented by the following general formula (7) or general formula (8), and at least one of them is general formula (7).

In General Formula (7), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group, An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group, or —SiRa ₃ may be further substituted. Ra represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group. X ₁ and X ₂ represent a carbon atom or a nitrogen atom. X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom. X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent.

In General Formula (8), X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ each represent a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

In the general formula _(6), the substituent represented by R 1, _{R 2} and _{R 3,} can be used a _{substituent R} 1 in the general formula (1), _{R 2} and _{R 3} represents.

  In the general formula (6), examples of the trivalent linking group represented by V include a branched alkyl group, a substituted aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic hydrocarbon ring group, and a non-aromatic hydrocarbon ring group. Aromatic heterocyclic groups can be used.

  As specific examples of the compounds represented by the general formulas (1) to (6), BD-1 to BD-120 are shown below.

<Method of synthesizing organometallic complex>
Although the synthesis example of the compound represented by General formula (1)-(6) below is demonstrated, this invention is not limited to this. Of the specific examples described above, a synthesis method of BD-1, BD-4, BD5, BD-27, and BD-69 will be described below as an example.

[Method for synthesizing BD-1]
BD-1 can be synthesized according to the following steps.

(Step 1-1)
In a three-necked flask, 17.3 g of intermediate A, 30 g of intermediate B, 3.2 g of Pd (dba) ₂ (dba = dibenzylideneacetone), 3.2 g of dppf (1,1′-Bis (diphenylphosphino) ferrocene) Then, 23.4 g of potassium carbonate was added, 500 ml of dimethoxyethane and 160 ml of water were added, and the mixture was refluxed and stirred for 14 hours under a nitrogen atmosphere.
After completion of the reaction, the reaction solution was cooled to room temperature, transferred to a separatory funnel, 1 L of ethyl acetate was added, and the aqueous layer was removed. Thereafter, the organic layer was washed three times with a saturated saline solution, and further the organic layer was dried over magnesium sulfate, and then the organic layer was removed with an evaporator. This residue was purified by column chromatography (hexane / ethyl acetate = 1/4) to obtain 13.5 g of Intermediate C.

(Step 1-2)
A three-necked flask was charged with 10 g of Intermediate C, 4.2 g of iridium chloride, 100 ml of ethoxyethanol, and 30 ml of water, and the mixture was heated and stirred at 100 ° C. for 4 hours in a nitrogen atmosphere.
The precipitated crystals were collected by filtration, and the collected crystals were washed with methanol to obtain 7.6 g of Intermediate D.

(Step 1-3)
In a three-necked flask, 4.0 g of Intermediate D obtained in Step 1-2, 2.5 g of acetylacetone, 7 g of potassium carbonate, and 100 ml of ethoxyethanol were placed and stirred with heating at 80 ° C. for 5 hours in a nitrogen atmosphere. .
The precipitated crystals were collected by filtration, and the collected crystals were washed with methanol and then washed with water to obtain 2.3 g of Intermediate E.

(Step 1-4)
In a three-necked flask, 1.4 g of Intermediate E obtained in Step 1-3, 0.7 g of Intermediate C and 50 ml of ethylene glycol were placed, and the mixture was heated and stirred at 150 ° C. for 7 hours in a nitrogen atmosphere.
The precipitated crystals were collected by filtration, washed with methanol, and then separated and purified by silica gel chromatography to obtain 0.7 g of BD-1.

[Method for synthesizing BD-4]
BD-4 can be synthesized according to the following steps.

(Step 4-1)
3 g of BD-1 was placed in a three-necked flask and dissolved in 20 ml of DMF. While stirring at room temperature, 1.5 g of NBS (N-Bromosuccinimide) was added little by little. After stirring for 1 hour, crystals were precipitated, which were collected by filtration with a Kiriyama funnel, and further washed with MeOH to obtain 2 g of Intermediate F.

(Step 4-2)
Three-necked flask, intermediate F 1 g, Zn (CN) ₂ and 0.5 g, Pd and (dba) ₂ 0.03 g, was placed 0.02g of Zn (zinc), followed by the addition of 10 ml of DMF. Furthermore, 0.5 ml of P (t-Bu) ₃ (50% by mass toluene solution) was added under a nitrogen atmosphere, and the mixture was stirred at 130 ° C. for 4 hours.
After completion of the reaction, the reaction solution was cooled to room temperature, transferred to a separatory funnel, 1 L of ethyl acetate was added, and the aqueous layer was removed. Thereafter, the organic layer was washed three times with a saturated saline solution, and further the organic layer was dried over magnesium sulfate, and then the organic layer was removed with an evaporator. The residue was purified by column chromatography (hexane / THF = 1/1) to obtain 0.4 g of BD-4.

[Method for synthesizing BD-5]
BD-5 can be synthesized according to the following steps.

(Process 5)
In a three-necked flask, 1 g of intermediate F, 0.8 g of intermediate G and 0.09 g of Pd (dba) ₂ were added, and then 10 ml of NMP (N-methylpyrrolidone) was added. Further, 1.0 ml of P (t-Bu) ₃ (50% by mass toluene solution) was added under a nitrogen atmosphere. Furthermore, 1.0 g of potassium phosphate was added and stirred at 110 ° C. for 5 hours.
After completion of the reaction, the reaction solution was cooled to room temperature, transferred to a separatory funnel, 1 L of ethyl acetate was added, and the aqueous layer was removed. Thereafter, the organic layer was washed three times with a saturated saline solution, and further the organic layer was dried over magnesium sulfate, and then the organic layer was removed with an evaporator. This residue was purified by column chromatography (hexane / THF = 4/1) to obtain 0.55 g of BD-5.

[Synthesis Method of BD-27]
BD-27 can be synthesized according to the following steps.

(Step 27-1)
In a three-necked flask, 29 g of intermediate H, 15 g of intermediate I, 15 g of Cu (copper), 35 g of potassium carbonate, and 500 ml of DMF were added, and then stirred at 160 ° C. in a nitrogen atmosphere.
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel, 1 L of ethyl acetate was added, and the aqueous layer was removed. Thereafter, the organic layer was washed three times with a saturated saline solution, further dried over magnesium sulfate, and then the organic layer was removed by an evaporator. This residue was purified by column chromatography (hexane / ethyl acetate = 1/4) to obtain 27.5 g of Intermediate J.

(Step 27-2)
A three-necked flask was charged with 10 g of intermediate J, 4.8 g of iridium chloride, 100 ml of ethoxyethanol, and 30 ml of water, and the mixture was heated and stirred at 100 ° C. for 4 hours in a nitrogen atmosphere.
The precipitated crystals were collected by filtration, and the collected crystals were washed with methanol to obtain 8.5 g of Intermediate K.

(Step 27-3)
In a three-necked flask, 4.0 g of Intermediate K obtained in Step 27-2, 2.8 g of acetylacetone, 8 g of potassium carbonate, and 100 ml of ethoxyethanol were placed, and the mixture was heated and stirred at 80 ° C. for 5 hours in a nitrogen atmosphere. .
The precipitated crystals were collected by filtration, and the collected crystals were washed with methanol and then washed with water to obtain 2.7 g of Intermediate L.

(Step 27-4)
In a three-necked flask, 1.4 g of intermediate L obtained in step 27-3, 0.85 g of intermediate J and 50 ml of ethylene glycol were placed, and the mixture was heated and stirred at 150 ° C. for 7 hours under a nitrogen atmosphere.
The precipitated crystals were collected by filtration, washed with methanol, and then separated and purified by silica gel chromatography to obtain 0.6 g of BD-27.

[Synthesis Method of BD-69]
BD-69 can be synthesized according to the following steps.

(Step 69)
A three-necked flask was charged with 5 g of Intermediate M, 2.6 g of Ir (acac) 3 and 50 ml of ethylene glycol, and heated and stirred at 200 ° C. for 24 hours under a nitrogen atmosphere.
The precipitated crystals were collected by filtration, and the collected crystals were washed with methanol to obtain 1.2 g of BD-69.

  In addition, about synthetic methods, such as BD-42-48, 61, 62, 72, 73, 91-94 represented by General formula (5), international publication 2011/051404 and international publication 2009/050281. Etc. were synthesized with reference to the above.

<< Constitutional layer of organic EL element >>
In the organic EL device of the present invention, preferred specific examples of the layer structure of various organic layers sandwiched between the anode and the cathode are shown below, but the present invention is not limited thereto.

(I) Anode / light emitting layer unit / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer unit / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer unit / hole blocking Layer / electron transport layer / cathode (iv) anode / hole transport layer / light emitting layer unit / hole blocking layer / electron transport layer / cathode buffer layer / cathode (v) anode / anode buffer layer / hole transport layer / light emission Layer unit / hole blocking layer / electron transport layer / cathode buffer layer / cathode

Furthermore, the light emitting layer unit may have a non-light emitting intermediate layer between a plurality of light emitting layers, and may have a multi-photon unit configuration in which the intermediate layer is a charge generation layer. In this case, as the charge generation layer, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO ₂ , TiN, ZrN, HfN, TiO _x , VO _x , CuI, InN, GaN, CuAlO _{2 are used.} , CuGaO ₂ , SrCu ₂ O ₂ , LaB ₆ , RuO _{2 and} other conductive inorganic compound layers, Au / Bi ₂ O _{3 and} other bilayer films, SnO ₂ / Ag / SnO ₂ , ZnO / Ag / ZnO, Bi ₂ O ₃ / Au / Bi ₂ O ₃ , TiO ₂ / TiN / TiO ₂ and multilayer films such as TiO ₂ / ZrN / TiO ₂ , fullerenes such as C ₆₀ , conductive organic layer such as oligothiophene, metal phthalocyanine And conductive organic compound layers such as metal-free phthalocyanines, metalloporphyrins and metal-free porphyrins.

  The light emitting layer in the organic EL device of the present invention is preferably a white light emitting layer, and an illumination device using these is preferable.

  Each layer which comprises the organic EL element of this invention is demonstrated below.

<Light emitting layer>
The light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode or the electron transport layer and the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.

  The total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the driving current. Preferably, it is adjusted to the range of 2 nm to 5 μm, more preferably adjusted to the range of 2 to 200 nm, and particularly preferably adjusted to the range of 5 to 100 nm.

  For the production of the light emitting layer, a light emitting dopant or a host compound described later is used, for example, a vacuum deposition method or a wet method (also referred to as a wet process, such as a spin coating method, a casting method, a die coating method, a blade coating method, a roll). Examples thereof include a coating method, an inkjet method, a printing method, a spray coating method, a curtain coating method, and an LB method (Langmuir Brodgett method). In addition, when using the hexadentate ortho metal iridium complex based on this invention as a material of a light emitting layer, it is preferable to form into a film by a wet process.

  In the light emitting layer of the organic EL device of the present invention, a light emitting dopant (a phosphorescent dopant (also referred to as a phosphorescent dopant or a phosphorescent dopant group) or a fluorescent dopant) compound and a light emitting host compound are contained. It is preferable to contain.

(1) Luminescent dopant As the luminescent dopant ("luminescent dopant", "dopant compound", also simply referred to as "dopant"), fluorescent dopant (also referred to as fluorescent compound), phosphorescent dopant (phosphor phosphor) , Phosphorescent compounds, phosphorescent compounds, etc.), specifically, organometallic complexes represented by the aforementioned general formulas (1) to (6) can be used. .

(1.1) Phosphorescent dopant The phosphorescent dopant according to the present invention (also referred to as “phosphorescent dopant” or “phosphorescent dopant”) is a compound in which light emission from an excited triplet is observed, Specifically, it is a compound that emits phosphorescence at room temperature (25 ° C.), and is defined as a compound having a phosphorescence quantum yield of 0.01 or more at 25 ° C. 1 or more.

  The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.

  There are two types of light emission principles of the phosphorescent dopant. First, recombination of carriers occurs on the host compound to which carriers are transported to generate an excited state of the luminescent host compound, and this energy is transferred to the phosphorescent dopant to obtain light emission from the phosphorescent dopant. It is an energy transfer type. The other is a carrier trap type in which the phosphorescent dopant serves as a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the luminescent host compound.

(1.2) Fluorescent dopants Fluorescent dopants (also referred to as “fluorescent compounds”) include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, and fluorescein dyes. Examples include dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, rare earth complex phosphors, and compounds having high fluorescence quantum yields typified by laser dyes.

(1.3) Combined use with conventionally known dopants In addition, the luminescent dopant according to the present invention may be used in combination of a plurality of types of compounds, a combination of phosphorescent dopants having different structures, or a phosphorescent dopant. And a fluorescent dopant may be used in combination.

  Here, as a luminescent dopant, D-1 to D-47 are given as specific examples of conventionally known luminescent dopants that may be used in combination with the organometallic complex represented by the general formula (1) according to the present invention. The present invention is not limited to these examples.

(2) Luminescent Host Compound In the present invention, the luminescent host compound (also referred to as “luminescent host”, “luminescent host”, or “host compound”) is a compound contained in the luminescent layer. Is defined as a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.1 at room temperature (25 ° C.). The phosphorescence quantum yield is preferably less than 0.01. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.

  There is no restriction | limiting in particular as a luminescent host which can be used for this invention, The compound conventionally used with an organic EL element can be used. Typically, carbazole derivatives, triarylamine derivatives, aromatic derivatives, nitrogen-containing heterocyclic compounds, thiophene derivatives, furan derivatives, oligoarylene compounds and other basic skeletons, carboline derivatives and diazacarbazole derivatives (where, Examples of the diazacarbazole derivative include those in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom.

  Known light-emitting host compounds that can be used in the present invention include compounds that have a hole transporting ability or an electron transporting ability, prevent the emission of longer wavelengths, and have a high Tg (glass transition temperature). preferable.

  In the present invention, conventionally known luminescent host compounds may be used alone or in combination of two or more. By using a plurality of types of luminescent host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. Further, by using a plurality of kinds of the organometallic complex of the present invention and / or a conventionally known compound used as the phosphorescent dopant, it becomes possible to mix different emission colors, thereby obtaining an arbitrary emission color. .

  The luminescent host compound used in the present invention may be a low molecular compound or a high molecular compound having a repeating unit, and a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (polymerizable luminescent host). ), Or one or more of such compounds may be used.

  Specific examples of known luminescent host compounds include the compounds described in the following documents. For example, Japanese Patent Application Laid-Open Nos. 2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, 2002-8860 Gazette, 2002-334787 gazette, 2002-15871 gazette, 2002-334788 gazette, 2002-43056 gazette, 2002-334789 gazette, 2002-75645 gazette, 2002-338579 gazette. No. 2002-105445, No. 2002-343568, No. 2002-141173, No. 2002-352957, No. 2002-203683, No. 2002-363227, No. 2002-231453. No. 2003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-286061, No. 2002-280183, No. 2002-299060. , 2002-302516, 2002-305083, 2002-305084, 2002-308837, and the like.

  Hereinafter, although the specific example (OC-1 to OC-32) used as a luminescent host compound of the light emitting layer of the organic EL element of this invention is given, this invention is not limited to these.

  Furthermore, a compound represented by the following general formula (A) or general formula (B) is particularly preferable as the light-emitting host compound of the light-emitting layer of the organic EL device of the present invention.

  In the general formulas (A) and (B), Xa represents an oxygen atom or a sulfur atom. Xb, Xc, Xd and Xe each represent a hydrogen atom, a substituent or a group represented by the following general formula (C). At least one of Xb, Xc, Xd, and Xe represents a group represented by the following general formula (C), and at least one of the groups represented by the following general formula (C) represents Ar as a carbazolyl group. .

In general formula (C), L ₄ represents a divalent linking group derived from an aromatic hydrocarbon ring or an aromatic heterocyclic ring. n represents an integer of 0 to 3, and when n is 2 or more, the plurality of L ₄ may be the same or different. * Represents a linking site with the general formula (A) or (B). In the compound represented by the general formula (A), preferably at least two of Xb, Xc, Xd and Xe are represented by the general formula (C), and more preferably Xc is represented by the general formula (C). In addition, Ar in the general formula (C) represents a carbazolyl group represented by the following general formula (D).

In general formula (D), Xf represents N (R ″), an oxygen atom or a sulfur atom, E _{1 to} E ₈ represent C (R ″ ₁ ) or N, R ″ and R ″ ₁ are hydrogen atoms, It represents a substituent or a linking site with L ₄ in formula (C). * Represents a linking site with L ₄ in the general formula (C).

  Hereinafter, H-1 to H-56 are given as specific examples of the compound represented by the general formula (A) preferably used as a host compound (also referred to as a light emitting host) of the light emitting layer of the organic EL device of the present invention. However, the present invention is not limited to these.

  In addition, a compound represented by the following general formula (A ′) is also particularly preferably used as a light-emitting host of the light-emitting layer of the organic EL device of the present invention.

In the general formula (A ′), Xa represents an oxygen atom or a sulfur atom, and Xb and Xc each represents a substituent or a group represented by the general formula (C).
At least one of Xb and Xc represents a group represented by the general formula (C), and at least one of the groups represented by the general formula (C) represents Ar as a carbazolyl group.

In the compound represented by the general formula (A ′), Ar in the general formula (C) preferably represents a carbazolyl group which may have a substituent, and more preferably, in the general formula (C). Ar may have a substituent and represents a carbazolyl group linked to L ₄ in formula (C) at the N-position.

  The compound represented by the general formula (A ′) that is preferably used as a host compound (also referred to as a light-emitting host) of the light-emitting layer of the organic EL device of the present invention is specifically a specific example previously used as a light-emitting host. OC-9, OC-11, OC-12, OC-14, OC-18, OC-18, OC-29, OC-30, OC-31 and OC-32 mentioned as, but the present invention is not limited to these. Not.

《Electron transport layer》
The electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. The electron transport layer can be provided with a single layer or a plurality of layers.

  The electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and as a constituent material of the electron transport layer, any one of conventionally known compounds may be selected and used in combination. Is also possible.

Examples of conventionally known materials used for the electron transport layer (hereinafter referred to as electron transport materials) include polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, At least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the ring tetracarboxylic anhydride, carbodiimide, fluorenylidenemethane derivative, anthraquinodimethane and anthrone derivative, oxadiazole derivative, carboline derivative, carboline derivative is nitrogen Derivatives having a ring structure substituted with an atom, hexaazatriphenylene derivatives and the like.
Furthermore, in the oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as an electron transport material.
A polymer material in which these materials are introduced into a polymer chain, or a polymer material having these materials as a polymer main chain can also be used.

  In addition, organometallic complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) Aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metals of these organometallic complexes are indium, magnesium Organometallic complexes replaced with copper, calcium, tin, gallium or lead can also be used as the electron transporting material.

In addition, metal-free or metal phthalocyanine, or those having a terminal substituted with an alkyl group or a sulfonic acid group can be used as the electron transport material.
In addition, inorganic semiconductors such as n-type-Si and n-type-SiC can also be used as the electron transport material.

  The electron transport layer is formed of an electron transport material, for example, a vacuum deposition method or a wet method (also referred to as a wet process, for example, a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, an ink jet method, a printing method, a spray method). The film is preferably formed by thinning by a coating method, a curtain coating method, an LB method (such as Langmuir Brodgett method)).

  Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, about 5-5000 nm, Preferably it is 5-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.

  The electron transport layer may be doped with an n-type dopant such as an organometallic complex or a metal halide.

  Specific examples of known electron transport materials include compounds described in the following documents. For example, ET-1 to ET-39 described in [0096] to [0104] of JP2012-169325A and E1-1 to ET1 to [0082] of JP2012-104536A are disclosed. And compounds such as E5-6.

"cathode"
As the cathode, a material having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) Mixtures, indium, lithium / aluminum mixtures and rare earth metals. Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, A magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al ₂ O ₃ ) mixture, a lithium / aluminum mixture, aluminum or the like is preferred.

  The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm.

In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the emission luminance is advantageously improved.
In addition, a transparent or translucent cathode can be produced by producing a conductive transparent material mentioned in the explanation of the anode described later on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.

<< Injection layer: electron injection layer (cathode buffer layer), hole injection layer >>
The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. You may let them.

  An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance. “Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166), and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).

  The details of the anode buffer layer (hole injection layer) are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like. As a specific example, copper phthalocyanine is used. Representative phthalocyanine buffer layer, hexaazatriphenylene derivative buffer layer, oxide buffer layer typified by vanadium oxide, amorphous carbon as described in JP-T-2003-519432 and JP-A-2006-135145 Examples thereof include a buffer layer, a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) and polythiophene, and an orthometalated complex layer represented by tris (2-phenylpyridine) iridium complex.

  The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc. Metal buffer layer typified by, alkali metal compound buffer layer typified by lithium fluoride and potassium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride and cesium fluoride, typified by aluminum oxide Examples thereof include an oxide buffer layer. The buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 μm although it depends on the material.

<Blocking layer: hole blocking layer, electron blocking layer>
The blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258, 11-204359, and “Organic EL elements and their forefront of industrialization” (issued by NTT, Inc. on November 30, 1998). There is a hole blocking (hole blocking) layer.

  In a broad sense, the hole blocking layer has a function of an electron transport layer and is composed of a hole blocking material having a function of transporting electrons and having a remarkably small ability to transport holes, while transporting electrons. By blocking holes, the recombination probability of electrons and holes can be improved.

  Moreover, the structure of the electron carrying layer mentioned above can be used as a hole-blocking layer concerning this invention as needed.

  The hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.

  The hole blocking layer includes a carbazole derivative, a carboline derivative, a diazacarbazole derivative (herein, a diazacarbazole derivative refers to any one of the carbon atoms constituting the carboline ring). It is preferable to contain a compound that is replaced with a nitrogen atom.

  In the present invention, when a plurality of light emitting layers having different light emission colors are provided, the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers. In this case, it is preferable to additionally provide a hole blocking layer between the shortest wave layer and the light emitting layer next to the anode next to the anode. Furthermore, it is preferable that 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.

The ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied orbital) level of the compound to the vacuum level, and can be determined by the following method, for example.
(1) Wave motion using Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), molecular orbital calculation software manufactured by Gaussian, USA. It can be obtained as a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G * as a function keyword (calculation method and basis function). This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
(2) The ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a method known as ultraviolet photoelectron spectroscopy can be suitably used by using a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd.

  On the other hand, the electron blocking layer, in a broad sense, has a function of a hole transport layer, and is made of a material having a function of transporting holes while having a remarkably small ability to transport electrons, while transporting holes. By blocking electrons, the probability of recombination of electrons and holes can be improved.

  Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed. The film thickness of the hole blocking layer and the electron transporting layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.

《Hole transport layer》
The hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.

The hole transport material has any of hole injection or transport and electron barrier properties, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, or conductive polymer oligomers, particularly thiophene oligomers.
Further, azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as a hole transport material.

  Although the above-mentioned thing can be used as a positive hole transport material, It is preferable to use a porphyrin compound, an aromatic tertiary amine compound, and a styryl amine compound, especially an aromatic tertiary amine compound.

  Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl; N, N'-diphenyl-N, N'- Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N ' − (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylaminostilbene; N-phenylcarbazole, and also two fused aromatic rings described in US Pat. No. 5,061,569. What is contained in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), Japanese Patent Laid-Open No. 4-308688 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA), etc., in which three triphenylamine units described in 1 are linked in a starburst type Is mentioned.

Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.

  JP-A-11-251067, J. Org. Huang et. al. A so-called p-type hole transport material as described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used. In the present invention, these materials are preferably used because a light-emitting element with higher efficiency can be obtained.

The hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The hole transport layer may have a single layer structure composed of one or more of the above materials.

Alternatively, a hole transport layer having a high p property doped with impurities can be used. Examples thereof include JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
In the present invention, it is preferable to use a hole transport layer having such a high p property because a device with lower power consumption can be produced.

"anode"
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ , and ZnO.

Alternatively, an amorphous material such as IDIXO (In ₂ O ₃ —ZnO) capable of forming a transparent conductive film may be used. The anode may be formed by depositing a thin film of these electrode materials by vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or when pattern accuracy is not so high (about 100 μm or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.

  Or when using the substance which can be apply | coated like an organic electroconductivity compound, wet film-forming methods, such as a printing system and a coating system, can also be used. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.

《Support substrate》
The support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is transparent. Or opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.

  Examples of the resin film include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate (TAC), cellulose acetate butyrate, cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones, Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by Mitsui Chemicals) Can be mentioned.

An inorganic film, an organic film, or a hybrid film of both may be formed on the surface of the resin film, and the water vapor permeability (25 ± 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ± 2)% RH) is preferably 1 × 10 ⁻² g / m ² · 24 h or less barrier film, and further measured by a method according to JIS K 7126-1987. A high barrier film having an oxygen permeability of 1 × 10 ⁻³ ml / m ² · 24 h · atm or less and a water vapor permeability of 1 × 10 ⁻⁵ g / m ² · 24 h or less is preferable.

  As a material for forming the barrier film, any material may be used as long as it has a function of suppressing entry of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like can be used. Further, in order to improve the brittleness of the film, it is more preferable to have a laminated structure of these inorganic layers and organic material layers. Although there is no restriction | limiting in particular about the lamination | stacking order of an inorganic layer and an organic layer, It is preferable to laminate | stack both alternately several times.

  The method for forming the barrier film is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma polymerization A plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.

  Examples of the opaque support substrate include a metal plate such as aluminum and stainless steel, a film, an opaque resin substrate, a ceramic substrate, and the like.

  The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, and more preferably 5% or more.

  Here, external extraction quantum efficiency (%) = number of photons emitted to the outside of the organic EL element / number of electrons flowed to the organic EL element × 100.

  In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination. In the case of using a color conversion filter, the λmax of light emission of the organic EL element is preferably 480 nm or less.

<< Method for producing organic EL element >>
As an example of a method for producing an organic EL device, a device comprising an anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer (electron injection layer) / cathode Will be described.

  First, a desired electrode material, for example, a thin film made of an anode material is formed on a suitable substrate so as to have a thickness of 1 μm or less, preferably 10 to 200 nm, and an anode is manufactured.

  Next, a thin film containing organic compounds such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and a cathode buffer layer, which are element materials, is formed thereon.

As a method for forming a thin film, for example, a thin film can be formed by a vacuum deposition method, a wet method (also referred to as a wet process), or the like.
Wet methods include spin coating, casting, die coating, blade coating, roll coating, ink jet, printing, spray coating, curtain coating, and LB, but precise thin films can be formed. From the viewpoint of high productivity, a method having high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method or a spray coating method is preferable. Different film formation methods may be applied for each layer.

Examples of the liquid medium for dissolving or dispersing the organic EL material according to the present invention include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene. Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin and dodecane, or organic solvents such as DMF (N, N′-dimethylformamide) and DMSO (Dimethyl sulfoxide) can be used.
Moreover, as a dispersion method, it can disperse | distribute by dispersion methods, such as an ultrasonic wave, high shear force dispersion | distribution, and media dispersion | distribution.

  After the formation of these layers, a thin film made of a cathode material is formed thereon so as to have a thickness of 1 μm or less, preferably in the range of 50 to 200 nm, and a desired organic EL device can be obtained by providing a cathode. .

  Further, the order can be reversed, and the cathode, cathode buffer layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be formed in this order.

  The organic EL device of the present invention is preferably produced from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is preferable to perform the work in a dry inert gas atmosphere.

<Sealing>
As a sealing means used for this invention, the method of adhere | attaching a sealing member, an electrode, a sealing member, and a support substrate with an adhesive agent can be mentioned, for example.

  The sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.

Specific examples include a glass plate, a polymer plate / film, and a metal plate / film. Examples of the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
Examples of the polymer plate include those formed from polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone, and the like.
Examples of the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.

In the present invention, a polymer film or a metal film can be preferably used because the element can be thinned.
Furthermore, the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 × 10 ⁻³ ml / m ² · 24 h · atm or less, and measured by a method according to JIS K 7129-1992. The water vapor permeability (25 ± 0.5 ° C., relative humidity (90 ± 2)% RH) is preferably 1 × 10 ⁻³ g / m ² · 24 h or less.

  For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.

  Specific examples of the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to. Moreover, heat | fever and chemical curing types (two-component mixing), such as an epoxy type, can be mentioned. Moreover, hot-melt type polyamide, polyester, and polyolefin can be mentioned. Moreover, a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.

  In addition, since an organic EL element may deteriorate by heat processing, what can be adhesive-hardened from room temperature to 80 degreeC is preferable. A desiccant may be dispersed in the adhesive. Application | coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.

In addition, it is also preferable that the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film. . In this case, the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, or silicon nitride may be used. it can.
Further, in order to improve the brittleness of the film, it is preferable to have a laminated structure of these inorganic layers and layers made of organic materials. The method for forming these films is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.

  In the gap between the sealing member and the display area of the organic EL element, an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase. preferable. A vacuum is also possible. Moreover, a hygroscopic compound can also be enclosed inside.

  Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide and magnesium iodide) and perchloric acids (eg perchloric acid) Barium and magnesium perchlorate), and the like, and anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.

《Protective film, protective plate》
In order to increase the mechanical strength of the element, a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film. In particular, when the sealing is performed by the sealing film, the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate. As a material that can be used for this, the same glass plate, polymer plate / film and metal plate / film as those used for the sealing can be used. Is preferably used.

《Light extraction》
The organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle θ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.

  As a technique for improving the light extraction efficiency, for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435), condensing on the substrate. A method of improving the efficiency by imparting the property (Japanese Patent Laid-Open No. Sho 63-314795), a method of forming a reflective surface on the side surface of the element (Japanese Patent Laid-Open No. 1-220394), and between the substrate and the light emitter A method of introducing an antireflection film by introducing a flat layer having an intermediate refractive index (Japanese Patent Laid-Open No. 62-172691), and introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter. A method (Japanese Patent Laid-Open No. 2001-202827), a method of forming a diffraction grating between any one of the substrate, the transparent electrode layer and the light emitting layer (including between the substrate and the outside) (Japanese Patent Laid-Open No. 11-283951), and the like. is there.

  In the present invention, these methods can be used in combination with the organic EL device of the present invention. However, a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.

  In the present invention, by combining these means, it is possible to obtain an element having higher luminance or durability.

  When a medium with a low refractive index is formed between the transparent electrode and the transparent substrate with a thickness longer than the wavelength of light, the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower. .

  Examples of the low refractive index layer include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.

  Further, the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.

  The method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency. This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction. Of these, light that cannot go out due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (inside a transparent substrate or transparent electrode). I want to take it out.

  The introduced diffraction grating desirably has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.

  However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and light extraction efficiency is increased.

  As described above, the position where the diffraction grating is introduced may be in any one of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.

  At this time, the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.

  The arrangement of the diffraction grating is preferably two-dimensionally repeated, such as a square lattice, a triangular lattice, or a honeycomb lattice.

《Condensing sheet》
The organic EL element of the present invention can be processed on a light extraction side of a substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, for example in a specific direction, for example, with respect to the element light emitting surface. By condensing in the front direction, the luminance in a specific direction can be increased.

  As an example of the microlens array, quadrangular pyramids having a side of 30 μm and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate. One side is preferably 10 to 100 μm. If it becomes smaller than this, the effect of diffraction will generate | occur | produce and color, and if too large, thickness will become thick and is not preferable.

As the condensing sheet, for example, a sheet that is put into practical use in an LED backlight of a liquid crystal display device can be used. As such a sheet, for example, a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
As the shape of the prism sheet, for example, the base material may be formed by forming a △ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 μm, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.

  Moreover, in order to control the light emission angle from a light emitting element, you may use together a light diffusing plate and a film with a condensing sheet. For example, a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.

<Application>
The organic EL element of the present invention can be used as a display device, a display, and various light sources. Examples of light sources include lighting devices (home lighting, interior lighting), clocks and backlights for liquid crystals, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, and light. Examples include a light source of a sensor. Although it does not limit to these, it can be effectively used especially for the use as a backlight of a liquid crystal display device and a light source for illumination.

  In the organic EL element of the present invention, patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned. In the fabrication of the element, a conventionally known method is used. Can do.

  The light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total CS-1000 (manufactured by Konica Minolta Optics Co., Ltd.) is applied to the CIE chromaticity coordinates.

When the organic EL element of the present invention is a white element, white means that the chromaticity in the CIE1931 color system at 1000 cd / m ² is X when the 2 ° viewing angle front luminance is measured by the above method. = 0.33 ± 0.07 and Y = 0.33 ± 0.1.

<Display device>
The display device of the present invention will be described. The display device of the present invention comprises the organic EL element of the present invention. Although the display device of the present invention may be single color or multicolor, the multicolor display device will be described here.

In the case of a multicolor display device, a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.
In the case of patterning only the light emitting layer, there is no limitation on the method, but a vapor deposition method, an inkjet method, a spin coating method, and a printing method are preferable.

  The configuration of the organic EL element provided in the display device is selected from the above-described configuration examples of the organic EL element as necessary.

  Moreover, the manufacturing method of an organic EL element is as having shown to the one aspect | mode of manufacture of the organic EL element of said invention.

  When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state. The alternating current waveform to be applied may be arbitrary.

  The multicolor display device can be used as a display device, a display, or various light emission sources. In a display device or display, full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.

  Examples of the display device or display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in an automobile. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.

  Light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc. The present invention is not limited to these examples.

Hereinafter, an example of a display device having the organic EL element of the present invention will be described with reference to the drawings.
FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.

The display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, a wiring unit C that electrically connects the display unit A and the control unit B, and the like.
The control unit B is electrically connected to the display unit A via the wiring unit C, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.

FIG. 2 is a schematic diagram of a display device using an active matrix method.
The display unit A includes a wiring unit C including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate. The main members of the display unit A will be described below.
FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).

The scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated). Not)
When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data.
Full-color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.

Next, the light emission process of the pixel will be described. FIG. 3 is a schematic diagram showing a pixel circuit.
The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. A full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.

  In FIG. 3, an image data signal is applied from the control unit B to the drain of the switching transistor 11 through the data line 6. When a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.

  By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.

When the scanning signal is moved to the next scanning line 5 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, since the capacitor 13 holds the charged potential of the image data signal even if the driving of the switching transistor 11 is turned off, the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues. When the scanning signal is next applied by sequential scanning, the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
That is, the light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels, and the light emission of the organic EL element 10 of each of the plurality of pixels 3. It is carried out. Such a light emitting method is called an active matrix method.

Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good. The potential of the capacitor 13 may be held continuously until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
In the present invention, not only the active matrix method described above, but also a passive matrix light emission drive in which the organic EL element emits light according to the data signal only when the scanning signal is scanned.

FIG. 4 is a schematic view of a passive matrix display device. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
In the passive matrix system, the pixel 3 has no active element, and the manufacturing cost can be reduced.

《Lighting device》
The lighting device of the present invention will be described. The illuminating device of this invention has the said organic EL element.
The organic EL element of the present invention may be used as an organic EL element having a resonator structure. Examples of the purpose of use of the organic EL element having such a resonator structure include a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processing machine, and a light source of an optical sensor. It is not limited. Moreover, you may use for the said use by making a laser oscillation.
Further, the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a type for directly viewing a still image or a moving image. It may be used as a display device (display).
The driving method when used as a display device for reproducing a moving image may be either a passive matrix method or an active matrix method. Alternatively, it is possible to produce a full-color display device by using two or more organic EL elements of the present invention having different emission colors.

The organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials and mixed to obtain white light emission. The combination of a plurality of emission colors may include three emission maximum wavelengths of three primary colors of red, green, and blue, or two of the complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.
In addition, a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those in combination with a dye material that emits light as a light source, but in the white organic EL device according to the present invention, it is only necessary to combine and mix a plurality of light-emitting dopants.

In addition, the organic EL element material forming method of the present invention may be simply arranged by providing a mask only when forming a light emitting layer, a hole transport layer, an electron transport layer, or the like, and separately coating with the mask. Since the other layers are common, patterning of a mask or the like is unnecessary, and for example, an electrode film can be formed on one surface by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is improved.
According to this method, unlike a white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.
There is no restriction | limiting in particular as a luminescent material used for a light emitting layer, For example, if it is a backlight in a liquid crystal display element, the organometallic complex which concerns on this invention so that it may adapt to the wavelength range corresponding to CF (color filter) characteristic, or Any one of known luminescent materials may be selected and combined to whiten.

<< One Embodiment of Lighting Device of the Present Invention >>
One aspect of the lighting device of the present invention that includes the organic EL element of the present invention will be described.
The non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a 300 μm thick glass substrate is used as a sealing substrate, and an epoxy photocurable adhesive (LUX Track LC0629B) was applied. This is stacked on the cathode and brought into close contact with the transparent support substrate, UV light is irradiated from the glass substrate side, cured, and sealed to form an illumination device as shown in FIGS. Can do.

  FIG. 5 shows a schematic diagram of the illumination device. The organic EL element 101 of the present invention is covered with a glass cover 102 (note that the sealing operation with the glass cover is a glove box under a nitrogen atmosphere (purity 99.75%) without bringing the organic EL element 101 into contact with the atmosphere. In an atmosphere of high-purity nitrogen gas of 999% or more).

  FIG. 6 shows a cross-sectional view of the lighting device. In FIG. 6, 105 is a cathode, 106 is an organic EL layer, and 107 is a glass substrate with a transparent electrode. The glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.

EXAMPLES Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited to these. In Example 1, an electron single charge device (hereinafter also referred to as “electron-only device”) through which only electrons flow was manufactured. In Examples 2 to 5, organic EL elements were produced.
Moreover, the structure of the compound used in the Example demonstrated below is shown below.

[Example 1]
<< Production of Electron Only Element 1-1 >>
A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NA45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ITO (indium tin oxide) film was formed as an anode on a 100 mm × 100 mm × 1.1 mm glass substrate The supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.

  This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of Ca (calcium) is put into a molybdenum resistance heating boat, and 100 mg of Comparative 1 as a dopant compound is put into another molybdenum resistance heating boat, 200 mg of OC-11 as a luminescent host compound was put in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.

Then, after reducing the vacuum chamber to 4 × 10 ⁻⁴ Pa, the heating boat containing Ca (calcium) is heated by heating, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second. A 10 nm hole blocking layer was provided.

  Furthermore, the hole blocking layer is heated at a deposition rate of 0.006 nm / second and 0.1 nm / second, respectively, by heating the heating boat containing Comparative 1 as the luminescent dopant and OC-11 as the luminescent host compound. A light emitting layer having a thickness of 80 nm was provided by co-evaporation.

The heating boat containing Ca was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second.
In addition, the substrate temperature at the time of vapor deposition was room temperature (25 degreeC).

  Subsequently, aluminum was deposited to form a cathode having a film thickness of 110 nm, and an electron-only device 1-1 was produced.

<< Production of Electron Only Elements 1-2 to 1-28 >>
In the production of the electron-only device 1-1, the dopant compounds in the light-emitting layer were changed to the compounds shown in Table 1, and other than that, electron-only devices 1-2 to 1-28 were produced in the same manner.

<< Evaluation of Electron Only Elements 1-1 to 1-28 >>
When evaluating the obtained electron-only devices 1-1 to 1-28, the non-light-emitting surface of each electron-only device after production was covered with a glass case, and a glass substrate having a thickness of 300 μm was used as a sealing substrate. In addition, an epoxy-based photo-curing adhesive (Lux Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealing material around the periphery, and this is placed on the cathode so as to be in close contact with the transparent support substrate and irradiated with UV light from the glass substrate side. Then, it was cured and sealed, and a lighting device as shown in FIGS. 5 and 6 was produced and evaluated.
The following evaluation was performed for each sample thus prepared. The evaluation results are shown in Table 1.

(1) Voltage rise at the time of driving The organic EL element was energized for 100 hours under a constant current condition of room temperature (25 ° C.) and 2.5 mA / cm ² , and the voltage when driven was measured. Table 1 shows the results obtained by the calculation formula shown.
The value is expressed as a relative value where the electron-only device 1-1 is 100.
Voltage rise during driving (relative value) = driving voltage at half brightness-initial driving voltage A smaller value indicates a smaller voltage rise during driving for comparison.

(2) Summary Durability test at the time of electron energization by electron-only device driving was conducted, and as shown in Table 1, the compound of the present invention has less voltage increase at the time of driving and the stability at the time of electron energization compared to the comparative compound. It was found that (electron resistance) was improved. Also, an organic EL element 1-8 using BD-23 whose central metal is iridium, and an organic EL element 1 using BD-89 whose central metal is platinum and containing the same ligand as BD-8. 23, it was found that the organic EL element 1-8 using BD-23 whose central metal is iridium is superior in the stability (electron resistance) during energization of electrons.

[Example 2]
<< Preparation of Organic EL Element 2-1 >>
A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NA45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ITO (indium tin oxide) film was formed as an anode on a 100 mm × 100 mm × 1.1 mm glass substrate The supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.

  On this transparent support substrate, poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, manufactured by HC Starck Co., Ltd., CLEVIO P VP AI 4083) was diluted to 70% by mass with pure water. Using the solution, a thin film was formed by spin coating at 3000 rpm for 30 seconds, and then dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 20 nm.

  This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of α-NPD is added as a hole transport material to a resistance heating boat made of molybdenum, and compared with another molybdenum resistance heating boat as a luminescent dopant. 100 mg of 1 was added, 200 mg of OC-30 as a luminescent host compound was placed in another resistance heating boat made of molybdenum, 200 mg of ET-1 was placed as an electron transport material in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus. .

Next, the pressure in the vacuum chamber was reduced to 4 × 10 ⁻⁴ Pa, and the heating boat containing α-NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second. The second hole transport layer was provided.

  Furthermore, the second hole is heated at a deposition rate of 0.006 nm / second and 0.1 nm / second respectively by heating the heating boat containing Comparative 1 as a luminescent dopant and OC-30 as a luminescent host compound. A light emitting layer having a thickness of 40 nm was provided by co-evaporation on the transport layer.

Furthermore, the heating boat containing ET-1 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
In addition, the substrate temperature at the time of vapor deposition was room temperature (25 degreeC).

  Subsequently, lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm. Thus, an organic EL element 2-1 was produced.

<< Production of Organic EL Elements 2-2 to 2-26 >>
In the production of the organic EL element 2-1, the luminescent dopant and the luminescent host compound in the luminescent layer were changed to the compounds shown in Table 2.
Other than that produced the organic EL element 2-2 to 2-26 similarly.

<< Evaluation of Organic EL Elements 2-1 to 2-26 >>
When evaluating the obtained organic EL elements 2-1 to 2-26, the non-light-emitting surface of each organic EL element after production was covered with a glass case, and a glass substrate having a thickness of 300 μm was used as a sealing substrate. In addition, an epoxy-based photo-curing adhesive (Lux Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealing material around the periphery, and this is placed on the cathode so as to be in close contact with the transparent support substrate and irradiated with UV light from the glass substrate side. Then, it was cured and sealed, and a lighting device as shown in FIGS. 5 and 6 was produced and evaluated.
The following evaluation was performed for each sample thus prepared. The evaluation results are shown in Table 2.

(1) External extraction quantum efficiency (also simply referred to as efficiency)
The organic EL device is turned on at room temperature (25 ° C.) under a constant current condition of ^2.5 mA / cm ² and the emission luminance (L) [cd / m ² ] immediately after the start of lighting is measured. Efficiency (η) was calculated.
Here, the measurement of emission luminance was performed using CS-1000 (manufactured by Konica Minolta Optics, Inc.), and the external extraction quantum efficiency was expressed as a relative value with the organic EL element 2-1 being 100.

(2) Half-life The half-life was evaluated according to the measurement method shown below.
Each organic EL device driven with a constant current at a current giving an initial luminance 1000 cd / ^{m 2,} obtains the time to be 1/2 (500cd / ^{m 2)} of the initial luminance, which was used as a measure of the half-life.
The half life was expressed as a relative value where the organic EL element 2-1 was 100.

(3) Voltage rise at the time of driving The voltage when the organic EL element was driven at room temperature (25 ° C.) and a constant current condition of ^2.5 mA / cm ² was measured, respectively, and the measurement result was calculated by the calculation formula shown below. The results obtained are shown in Table 2.
It represents with the relative value which sets the organic EL element 2-1 to 100.
Voltage rise during driving (relative value) = driving voltage at half brightness-initial driving voltage A smaller value indicates a smaller voltage rise during driving for comparison.

(4) Summary From Table 2, the organic EL elements 2-3 to 2-26 of the present invention show high luminous efficiency and long life with respect to the organic EL elements 2-1 and 2-2 of the comparative examples, It has been found that the characteristics as an element have been improved, such as suppressing a voltage rise during driving.

[Example 3]
<< Production of Organic EL Element 3-1 >>
A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NA45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ITO (indium tin oxide) film was formed as an anode on a 100 mm × 100 mm × 1.1 mm glass substrate The supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.

  This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of α-NPD is added as a hole transport material to a resistance heating boat made of molybdenum, and compared with another molybdenum resistance heating boat as a luminescent dopant. 100 mg of 1 and 200 mg of OC-11 as a luminescent host compound in another molybdenum resistance heating boat, 200 mg of ET-2 as an electron transport material in another molybdenum resistance heating boat, another molybdenum resistance heating 100 mg of D-10 as a luminescent dopant was put into a boat and attached to a vacuum deposition apparatus.

Next, after reducing the vacuum tank to 4 × 10 ⁻⁴ Pa, each of the heating boats containing α-NPD was separately energized and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second. A first hole transport layer was provided.

  Further, the heating boat containing Comparative 1 and D-10 as the luminescent dopant and OC-11 as the luminescent host compound was energized, and the deposition rate of OC-11, Comparative 1, and D-10 was 100: 5: The light emitting layer was provided by adjusting the thickness to 0.6 and depositing the film to a thickness of 30 nm.

Further, the heating boat containing ET-2 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
In addition, the substrate temperature at the time of vapor deposition was room temperature.

  Subsequently, lithium fluoride was vapor-deposited to form a cathode buffer layer having a thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a thickness of 110 nm. Thus, an organic EL element 3-1 was produced.

  When the produced organic EL element 3-1 was energized, almost white light was obtained, and it was found that it could be used as a lighting device. In addition, it turned out that white light emission is obtained similarly even if it replaces with the other compound of illustration.

<< Production of Organic EL Elements 3-2 to 3-14 >>
In the production of the organic EL element 3-1, the luminescent dopant and the luminescent host compound in the luminescent layer were changed to the compounds shown in Table 3.
Other than that produced the organic EL element 3-2 to 3-14 similarly.

<< Evaluation of Organic EL Elements 3-1 to 3-14 >>
When evaluating the obtained organic EL elements 3-1 to 3-14, the organic EL elements were sealed in the same manner as the organic EL elements 2-1 to 2-26 of Example 2, and FIGS. A lighting device as shown in FIG.
Each sample thus produced was evaluated for external extraction quantum efficiency, half life, voltage increase during driving, and thermal stability in the same manner as in Example 2. The evaluation results are shown in Table 3. In addition, the measurement result of the external extraction quantum efficiency in Table 3, the light emission lifetime, and the voltage rise at the time of a drive was represented by the relative value which sets the measured value of the organic EL element 3-1 to 100.

  From Table 3, the organic EL elements 3-3 to 3-14 of the present invention show higher luminous efficiency and longer life than the organic EL elements 3-1 and 3-2 of the comparative example, and the voltage rise during driving It was found that the characteristics as an element were improved.

[Example 4]
<< Preparation of Organic EL Element 4-1 >>
Patterning was performed on a substrate (NA-45, manufactured by AvanState Co., Ltd.) on which a 100 nm ITO (indium tin oxide) film was formed as an anode on a 100 mm × 100 mm × 1.1 mm glass substrate. Thereafter, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.

  On this transparent support substrate, a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, manufactured by Bayer, Baytron P Al 4083) diluted to 70% by mass with pure water was used, After forming a thin film by spin coating, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.

  On the first hole transport layer, a hole transport material Poly (N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.

  On this second hole transport layer, a thin film was formed by spin coating using Comparative 1 as a dopant compound and a butyl acetate solution of OC-11 as a host compound, and dried by heating at 120 ° C. for 1 hour. A light emitting layer having a thickness of 30 nm was provided.

  On this light emitting layer, a 1-butanol solution of ET-2 as an electron transport material was used to form a thin film by a spin coating method, and an electron transport layer having a thickness of 20 nm was provided.

This substrate was attached to a vacuum deposition apparatus, and the vacuum chamber was decompressed to 4 × 10 ⁻⁴ Pa. Subsequently, lithium fluoride was vapor-deposited to form an electron injection layer having a thickness of 1.0 nm, aluminum was vapor-deposited to form a cathode having a thickness of 110 nm, and an organic EL element 4-1 was produced.

<< Production of Organic EL Elements 4-2 to 4-14 >>
In the production of the organic EL element 2-1, the luminescent dopant and the luminescent host compound in the luminescent layer were changed to the compounds shown in Table 2.
Other than that produced the organic EL element 4-2 to 4-14 similarly.

<< Evaluation of Organic EL Elements 4-1 to 4-14 >>
When evaluating the obtained organic EL elements 4-1 to 4-14, the organic EL elements were sealed in the same manner as the organic EL elements 2-1 to 2-26 of Example 2, and FIGS. A lighting device as shown in FIG.
Each sample thus produced was evaluated for external extraction quantum efficiency, half life, and voltage increase during driving in the same manner as in Example 2. The evaluation results are shown in Table 4. In addition, the measurement result of the external extraction quantum efficiency in Table 4, a half life, and the voltage rise at the time of a drive was represented by the relative value which sets the measured value of the organic EL element 4-1 to 100.

  From Table 4, the organic EL elements 4-3 to 4-14 of the present invention show higher luminous efficiency and longer life than the organic EL elements 4-1 and 4-2 of the comparative example, and the voltage rise during driving. It was found that the characteristics of the device were improved, such as suppressing

[Example 5]
Similarly to the element 2-1 of Example 2, 5-1 and 5-2 were produced.
(1) Thermal stability evaluation About the organic EL elements 5-1 and 5-2, the same vapor deposition boat (molybdenum resistance heating boat) was used, and the element of the same structure was produced 5 elements each (for example, organic EL element 5) -1a, 5-1b, 5-1c, 5-1d and 5-1e and organic EL elements 5-2a, 5-2b, 5-2c, 5-2d and 5-2e).
Specifically, a predetermined amount of 100 mg of an organometallic complex is placed in a vapor deposition boat, 200 mg of OC-11 is charged as a host compound, and a deposition rate of 0.006 nm / second, 0.1 nm / second is applied to each substrate. In a second, vapor deposition with a film thickness of 40 nm was performed five times, thereby producing five elements each having the same configuration.
Each of the first fabricated elements (for example, the organic EL element 5-1a), the third fabricated element (for example, the organic EL element 5-1c), and the fifth fabricated element (for example, the organic EL element 5-1e). ) Was measured for the half-life by the same method as above. The half-life of each element was expressed as a relative value with 100 as the organic EL element 5-1a produced for the first time. Thereby, the thermal stability of the organometallic complex heated by the vapor deposition boat can be evaluated.

  The organic EL device 5-1 of the comparative example has a half-life that gradually decreases from that of the first device 5-1a, the third device 5-1c, and the fifth device 5-1e. On the other hand, the organic EL device 5-2 of the present invention has the first device 5-2a manufactured, the third device 5-2c, and the fifth device 5-2e. And the half-life has hardly decreased. Thereby, the compound of BD-5 which is the luminescent dopant used for the organic EL element 5-2 is more thermally stable than the compound of Comparative 3 which is the luminescent dopant used for the organic EL element 5-1. I found it excellent.

As described above, the present inventors have conducted extensive research to achieve the object of the present invention. As a result, the organometallic complex represented by the general formula (1) is made to emit light in the organic layer of the organic EL element. By including as a dopant, the electronic resistance of the organic EL element could be improved. We have found that having a fluorine atom at the R ₂ position deteriorates the electron resistance, and improved it. That is, F is present at a specific position in the general formula (1) (ortho position as seen from the carbon bonded to the 5-membered ring), Y ₁ represents C—R ₁ or N, and Y ₂ represents C—R. ₃ or N, and R ₁ , R ₂ and R ₃ are hydrogen atoms, alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups, non-aromatic heterocyclic groups, cyano It has been found that the electron resistance is improved by using a group or —SiRa ₃ as a substituent.
In addition, by having fluorine at a specific position in the general formula (1) (ortho position as seen from the carbon bonded to the 5-membered ring), the interaction between the organometallic complexes is relaxed and the sublimation property is improved. Furthermore, the thermal stability of the organometallic complex was improved. As a result, when the organic metal complex is formed as a luminescent dopant by vapor deposition to form an organic layer, continuous repeated vapor deposition becomes possible.

  Therefore, the organic EL element of the present invention is constituted by containing an organic metal complex represented by the general formula (1) as an organic EL element material in at least one organic layer. Preferably, the organic EL device of the present invention is configured such that an organic metal complex represented by the general formula (1) is contained as an organic EL device material in a light emitting layer of an organic layer. .

DESCRIPTION OF SYMBOLS 1 Display 3 Pixel 5 Scan line 6 Data line 7 Power supply line 10 Organic EL element 11 Switching transistor 12 Drive transistor 13 Capacitor 101 Organic EL element 102 Glass cover 105 Cathode 106 Organic EL layer 107 Glass substrate 108 with a transparent electrode Nitrogen gas 109 Water capturing Agent A Display unit B Control unit C Wiring unit

Claims (30)

An organometallic complex having a structure represented by the following general formula (1).

(In General Formula (1), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, wherein X ₁ , X ₂ , X ₆ , X ₇ and X ₈ are Represents a carbon atom or a nitrogen atom, X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and X _{1 to} X ₅ may have a substituent. form a heterocyclic group. _However, .A ₁ and _{a 2,} excluding the case where all of X 1, _{X 2} and _{X 5} represents a nitrogen atom, it And represents a residue necessary to form an aromatic hydrocarbon ring or an aromatic heterocycle, M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.) The organometallic complex according to claim 1, which has a structure represented by the following general formula (2).

(In the general formula (2), R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent, where Ra is an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring; Represents a group or a non-aromatic heterocyclic group, X ₁ , X ₂ , X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom, and X ₃ , X ₄ and X ₅ represent a carbon atom or a nitrogen atom. Represents an oxygen atom or a sulfur atom, X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent, and A ₁ and A ₂ each represent an aromatic hydrocarbon ring or an aromatic group. Represents a residue necessary to form a group heterocycle, M represents iridium or platinum, and M represents iridium. In this case, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, and m represents 0 or 1. M + n is 2.) The organometallic complex according to claim 1, wherein Y ₁ in the general formula (1) is N. The organometallic complex according to any one of claims 1 to 3, wherein in the general formula (1), X _{1 to} X ₅ form an imidazole ring. The organometallic complex according to any one of claims 1 to 3, wherein in the general formula (1), X _{1 to} X ₅ form a pyrazole ring. The organometallic complex according to any one of claims 1 to 3, wherein in the general formula (1), X _{1 to} X ₅ form a triazole ring. The organometallic complex according to any one of claims 1 to 3, wherein in the general formula (1), X _{1 to} X ₅ form a tetrazole ring. The organometallic complex according to claim 1, which has a structure represented by the following general formula (3).

(In General Formula (3), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, wherein R ₅ and R ₆ are each independently an alkyl group, aromatic It represents a hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent, and R ₄ and R ₇ are each independently hydrogen. Atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, Represents a silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group, and may further have a substituent, na represents 1 or 2 , Nb represents an integer of _{1 to 3.} X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom, and A ₁ and A ₂ each form an aromatic hydrocarbon ring or an aromatic heterocyclic ring. M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. (When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2.) The organometallic complex according to claim 1, which has a structure represented by the following general formula (4).

(In General Formula (4), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and R ₈ each independently represents a hydrogen atom, a halogen atom, or a cyano group. Represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and further a substituent. good .nc have a represents 1 or 2 .X , .M X ₇ and X _8, which represents the atoms necessary to form a .A ₁ and A ₂ each, aromatic hydrocarbon ring or aromatic heterocyclic ring represents a carbon atom or a nitrogen atom, iridium Or M represents iridium, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2 M represents 0 or 1, and m + n is 2.) The organometallic complex according to claim 1, which has a structure represented by the following general formula (5).

(In General Formula (5) , R ₁ , R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic group. Represents a heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent, where Ra is an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring; R ₉ represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, R ₁₀ and R ₁₁ is independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, non-aromatic hydrocarbon Represents a cyclic group or a non-aromatic heterocyclic group, In may have a substituent _{group, R 10} and _{R 11} is may be formed a fused ring _.X 6, _{X 7} and _{X 8,} .A ₁ and A represents a carbon atom or a nitrogen atom ₂ represents a residue necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring, M represents iridium or platinum, and when M represents iridium, n represents an integer of 1 to 3. M represents an integer of 0 to 2, and m + n is 3. When M represents platinum, n represents 1 or 2, m represents 0 or 1, and m + n is 2. It has a structure represented by following General formula (6), The organometallic complex of Claim 1 characterized by the above-mentioned.

(In the formula, V represents a trivalent linking group and is covalently linked to L ₁ , L ₂ and L _3. L _{1 to} L ₃ are represented by the following general formula (7) or general formula (8). And at least one is represented by the general formula (7): The trivalent linking group represented by V includes a branched alkyl group, a substituted aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic group. An aromatic hydrocarbon ring group and a non-aromatic heterocyclic group.)

(In General Formula (7), Y ₁ represents C—R ₁ or N, Y ₂ represents C—R ₃ or N, and R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom or an alkyl group. Represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, a non-aromatic heterocyclic group, a cyano group or —SiRa ₃ , and may further have a substituent. Represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and X ₁ and X _{2 each} represent a carbon atom or a nitrogen atom. X ₃ , X ₄ and X ₅ represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and X _{1 to} X ₅ form a 5-membered heterocyclic group which may have a substituent.

(In the general formula (8), X ₆ , X ₇ and X ₈ represent a carbon atom or a nitrogen atom. A ₁ and A ₂ are each necessary to form an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Represents a residue. The organometallic complex according to any one of claims 1 to 11, wherein R ₁ represents a cyano group. The organometallic complex according to claim 1, wherein R ₁ represents a —SiRa ₃ group. The organometallic complex according to claim 8, wherein R ₅ and R ₆ represent a branched alkyl group having 3 or more carbon atoms.   The organometallic complex according to claim 1, wherein M represents iridium.   An organic electroluminescence element material comprising an organometallic complex having a structure represented by the general formula (1) according to claim 1 as a component.   The organic electroluminescent element material according to claim 16, comprising an organometallic complex having a structure represented by the general formula (2) according to claim 2 as a component.   The organic electroluminescent element material according to claim 16, comprising an organometallic complex having a structure represented by the general formula (3) according to claim 8 as a component.   The organic electroluminescent element material according to claim 16, comprising an organometallic complex having a structure represented by the general formula (4) according to claim 9 as a component.   The organic electroluminescent element material according to claim 16, comprising an organometallic complex having a structure represented by the general formula (5) according to claim 10 as a component.   The organic electroluminescent element material according to claim 16, comprising an organometallic complex having a structure represented by the general formula (6) according to claim 11 as a component. An organic electroluminescence device in which an organic layer including a light emitting layer is sandwiched between an anode and a cathode,
The organic electroluminescent element characterized in that the organic layer contains an organometallic complex having a structure represented by the general formula (1) according to claim 1.   The organic electroluminescence device according to claim 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (2) according to claim 2.   The organic electroluminescence device according to claim 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (3) according to claim 8.   The organic electroluminescence device according to claim 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (4) according to claim 9.   The organic electroluminescence device according to claim 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (5) according to claim 10.   The organic electroluminescence device according to claim 22, wherein the organic layer contains an organometallic complex having a structure represented by the general formula (6) according to claim 11.   28. The organic electroluminescent element according to claim 22, wherein the luminescent color is white.   An illuminating device comprising the organic electroluminescent element according to any one of claims 22 to 27.   A display device comprising the organic electroluminescence element according to any one of claims 22 to 27.

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