JP5782230B2 - Organic thin film and organic electroluminescent device - Google Patents

Description

  The present invention relates to an organic thin film and an organic electroluminescent element.

  In recent years, an organic electroluminescence element using an organic thin film that emits light by being excited by passing an electric current (hereinafter also referred to as “element” or “organic EL element”) can emit light with high luminance by being driven at a low voltage. There is active research and development. In general, an organic electroluminescent element is composed of an organic layer including a light emitting layer and a pair of electrodes sandwiching the layer, and electrons injected from the cathode and holes injected from the anode are recombined in the light emitting layer, The generated exciton energy is used for light emission.

  In recent years, the use of phosphorescent light emitting materials has led to higher efficiency of devices. For example, an organic electroluminescent element using a phosphorescent material and a platinum complex and having excellent luminous efficiency and durability has been studied. In addition, a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.

The organic EL element can be applied to a wide range of applications including, for example, a mobile phone display, a computer display, an automobile information display, a TV monitor, and general lighting, but it is a problem to express a wide range of emission colors with high efficiency depending on the application. It has become.
In Patent Documents 1 and 2, a monomer light-emitting material and an aggregate light-emitting material are used in combination, light emission from the aggregate light-emitting material has a longer wavelength than light emission from the monomer light-emitting material, and composite light emission from both light emitters is visible. An organic electroluminescent device that includes a spectrum and produces white light emission is described. Here, an iridium complex (for example, FIr (pic)) is used as the monomer luminescent material, and a platinum complex is used as the aggregate luminescent material.

JP 2005-514754 A JP 2007-73620 A

As described above, in Patent Documents 1 and 2, white light emission is obtained by an organic electroluminescence device using an iridium complex monomer luminescent material and a platinum complex aggregate luminescent material. However, as a result of investigations by the present inventors, it has been found that the organic electroluminescence device described in Patent Document 1 has low luminous efficiency and has a problem in color purity. In addition, the invention of Patent Document 2 aims to improve durability, and does not show any knowledge about a combination of a monomer light-emitting material and an aggregate light-emitting material that are preferable from the viewpoint of improving light emission efficiency.
The present invention has been made in order to solve the above-described problems, and has an object to provide an organic thin film and an organic electroluminescence device that have high luminous efficiency, high color purity, and a wide range of emission colors. To do.

［一般式（１）中、Ａ^１１は窒素原子又は炭素原子を表し、Ａ^１２はＮ又はＣＲ^１３を表す。Ｒ^１１〜Ｒ^１３は各々独立に水素原子又は置換基を表す。Ｑ^１１はＡ^１１及びＮとともに含窒素ヘテロ環を形成する原子群を表す。（Ｘ−Ｙ）は２座のモノアニオン性配位子を表す。ｎは１〜３の整数を表す。］
［４］
前記白金錯体が、下記一般式（２）で表されることを特徴とする［１］〜［３］のいずれか一項に記載の有機薄膜。

［一般式（２）中、Ａ^２１及びＡ^２２は各々独立に窒素原子又は炭素原子を表す。Ｑ^２１はＡ^２１及びＮとともに含窒素ヘテロ環を形成する原子群を表す。Ｑ^２２はＡ^２２及びＮとともに含窒素ヘテロ環を形成する原子群を表す。Ｌ^２１はＰｔ及びＡ^２１と結合する原子群を表し、Ｌ^２２はＰｔ及びＡ^２２と結合する原子群を表す。Ｌ^２３は連結基を表す。］
［５］
前記一般式（２）において、Ｑ^２１、Ａ^２１及びＮにより形成される含窒素ヘテロ環及びＱ^２２、Ａ^２２及びＮにより形成される含窒素ヘテロ環の少なくとも一方がピラゾール環であることを特徴とする［４］に記載の有機薄膜。
［６］
前記一般式（２）で表される白金錯体が、下記一般式（３）で表される白金錯体であることを特徴とする［５］に記載の有機薄膜。

［一般式（３）中、Ｒ^３０１〜Ｒ^３１２は各々独立に水素原子又は置換基を表す。Ｒ^３０１とＲ^３０２、Ｒ^３０３とＲ^３０４、Ｒ^３０５〜Ｒ^３０８の少なくとも２つ、及びＲ^３０９〜Ｒ^３１２の少なくとも２つは、それぞれ、互いに連結して環を形成してもよい。Ｌ^３１は連結基を表す。］
［７］
一対の電極間に、発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、前記発光層が［１］〜［６］のいずれか一項に記載の有機薄膜である有機電界発光素子。
［８］
［７］に記載の有機電界発光素子を用いた発光装置。
［９］
［７］に記載の有機電界発光素子を用いた照明装置。 The above problem is solved by the following means.
[1]
An organic thin film containing an iridium complex, a platinum complex and a host material,
In the organic thin film, the shortest emission maximum wavelength of the iridium complex is 430 nm or more and less than 480 nm, and the emission maximum wavelength of the platinum complex is 550 nm or more and less than 650 nm,
An organic thin film, wherein the shortest emission maximum wavelength of the platinum complex in the solution is shorter than the shortest emission maximum wavelength of the iridium complex in the solution.
[2]
The organic thin film as described in [1], wherein the shortest emission maximum wavelength of the iridium complex in the organic thin film is 430 nm or more and less than 470 nm.
[3]
The organic thin film according to [1] or [2], wherein the iridium complex is an iridium complex represented by the following general formula (1).

[In the general formula ^{(1), A 11} represents a nitrogen atom or a carbon ^{atom, A 12} represents N or ^{CR 13.} R ^{11 to} R ¹³ each independently represents a hydrogen atom or a substituent. Q ¹¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ¹¹ and N. (X—Y) represents a bidentate monoanionic ligand. n represents an integer of 1 to 3. ]
[4]
The said platinum complex is represented by following General formula (2), The organic thin film as described in any one of [1]-[3] characterized by the above-mentioned.

[In General Formula (2), A ²¹ and A ²² each independently represent a nitrogen atom or a carbon atom. Q ²¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ²¹ and N. Q ²² represents an atomic group that forms a nitrogen-containing heterocycle together with A ²² and N. L ²¹ represents an atomic group bonded to Pt and A ^21, and L ²² represents an atomic group bonded to Pt and A ²² . L ²³ represents a linking group. ]
[5]
In the general formula (2), at least one of the nitrogen-containing heterocycle formed by Q ²¹ , A ²¹ and N and the nitrogen-containing heterocycle formed by Q ²² , A ²² and N is a pyrazole ring. The organic thin film according to [4].
[6]
The organic thin film as described in [5], wherein the platinum complex represented by the general formula (2) is a platinum complex represented by the following general formula (3).

[In General Formula (3), R ^{301 to} R ³¹² each independently represents a hydrogen atom or a substituent. At least two of R ³⁰¹ and R ³⁰² , R ³⁰³ and R ³⁰⁴ , R ^{305 to} R ³⁰⁸ , and at least two of R ^{309 to} R ³¹² may be connected to each other to form a ring. L ³¹ represents a linking group. ]
[7]
An organic electroluminescent element having at least one organic layer including a light emitting layer between a pair of electrodes, wherein the light emitting layer is the organic thin film according to any one of [1] to [6]. Light emitting element.
[8]
[7] A light emitting device using the organic electroluminescent element as described in [7].
[9]
The illuminating device using the organic electroluminescent element as described in [7].

  ADVANTAGE OF THE INVENTION According to this invention, the organic thin film and organic electroluminescent element which can obtain a wide luminescent color with high luminous efficiency and high color purity can be provided.

2 is a graph showing an emission spectrum of an organic thin film obtained in Example 1. FIG. 6 is a graph showing an emission spectrum of an organic thin film obtained in Example 2. FIG. It is a figure which shows the emission spectrum of the organic thin film obtained in Example 5. FIG. It is a figure which shows the emission spectrum of the organic thin film obtained in Example 6. It is a figure which shows the emission spectrum of the organic thin film (ratio is 10:90 (mass%)) which consists of an iridium complex and host material used in Example 1. It is a figure which shows the emission spectrum of the organic thin film (ratio is 10:90 (mass%)) which consists of an iridium complex and host material used in Example 2. It is a figure which shows the emission spectrum of the organic thin film (ratio is 10:90 (mass%)) which consists of the platinum complex and host material which were used in Example 2. It is a figure which shows the emission spectrum of the organic thin film (ratio is 10:90 (mass%)) which consists of the platinum complex and host material which were used in Example 3. It is the schematic which shows an example (1st Embodiment) of the layer structure of the organic EL element which concerns on this invention. It is the schematic which shows an example (2nd Embodiment) of the light-emitting device which concerns on this invention. It is the schematic which shows an example (3rd Embodiment) of the illuminating device which concerns on this invention.

The hydrogen atom in the description of the general formula according to the present invention includes isotopes (deuterium atoms and the like), and further, the atoms constituting the substituents also include the isotopes.
In the present invention, the “carbon number” of a substituent such as an alkyl group includes the case where a substituent such as an alkyl group may be substituted by another substituent, and also includes the carbon number of the other substituent. Used in meaning.

(Substituent group A)
Moreover, in this specification, the substituent group A represents the following substituents.
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), amino group (preferably 0 to 30 carbon atoms, more preferably 0 carbon atoms). -20, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms). More preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably 6 to 6 carbon atoms). 30 and more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. Nyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, acetyl , Benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonyl, ethoxy Carbonyl, etc.), an aryloxycarbonyl group (preferably It has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid. An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( An aromatic heterocyclic group is also included, preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like. A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). Ryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

Hereinafter, the present invention will be described in detail.
[Organic thin film]
The organic thin film of the present invention is an organic thin film containing an iridium complex, a platinum complex and a host material,
In the organic thin film, the shortest emission maximum wavelength of the iridium complex is 430 nm or more and less than 480 nm, and the emission maximum wavelength of the platinum complex is 550 nm or more and less than 650 nm,
The shortest emission maximum wavelength of the platinum complex in the solution is shorter than the shortest emission maximum wavelength of the iridium complex in the solution.

In the iridium complex and platinum complex used in the present invention, the shortest emission maximum wavelength of the platinum complex is shorter than that of the iridium complex in the solution, and the shortest emission maximum wavelength of the iridium complex is the emission maximum wavelength of the platinum complex in the organic thin film. The wavelength becomes shorter. That is, the platinum complex according to the present invention is a complex in which the emission maximum shifts to the long wavelength side in the organic thin film relative to the solution. This means that two or more molecules of the platinum complex are associated in the ground state or excited state in the organic thin film, and emit light in the associated state. Since the compound of the present invention does not show a large difference between the absorption spectrum and the excitation spectrum of the organic thin film, it is considered that the compound emits light mainly derived from an excitation aggregate (excimer).
In the organic thin film of the present invention, a platinum complex having an emission maximum wavelength of 550 nm to less than 650 nm and an iridium complex having a shortest emission maximum wavelength of 430 nm to less than 480 nm from the associated state (hereinafter also referred to as “associative emission”) By using together, it is possible to obtain a wide emission color (white and blue-white to orange emission color) with high color purity.
Furthermore, since the shortest emission maximum wavelength in the solution of the platinum complex is shorter than the shortest emission maximum wavelength of the iridium complex in the solution, the light emission efficiency is improved and the emission color with higher color purity is obtained. be able to. If the shortest emission maximum wavelength in the solution is in such a relationship, it is estimated that energy transfer from the iridium complex to the platinum complex hardly occurs and the iridium complex can emit light efficiently.
In the present invention, the emission maximum wavelength of the complex in the solution can be measured, for example, by the following method. That is, the complex is dissolved or dispersed in a dichloromethane solution (depending on the type of complex, for example, the complex concentration in the solution is 0.01 to 0.1 g / ml%), and a spectrofluorometer RF-5300PC manufactured by SHIMADU. Can be measured.
Further, the emission maximum wavelength of the complex in the organic thin film can be measured by depositing each material on a glass substrate and, for example, using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics.
In the present invention, the “shortest emission maximum wavelength” means the wavelength of the emission maximum on the shortest wavelength side among the emission maximums.

(Iridium complex)
The iridium complex according to the present invention is a complex having a shortest emission maximum wavelength in an organic thin film of 430 nm or more and less than 480 nm. The shortest emission maximum wavelength is preferably 430 nm or more and less than 470 nm, more preferably 440 nm or more and less than 460 nm, and still more preferably 440 nm or more and less than 455 nm. If the shortest emission maximum wavelength in the organic thin film is in this range, the emission of the iridium complex becomes blue emission with high color purity, so the range of colors that can be expressed by combining with the association emission of the platinum complex is widened, and white In this case, the color purity can be improved.
From the viewpoint of color purity, the half width at the shortest emission maximum wavelength in the organic thin film of the iridium complex according to the present invention is preferably 10 to 100 nm, and more preferably 20 to 80 nm. Furthermore, the iridium complex according to the present invention may have a light emission maximum on the longer wavelength side than the shortest light emission maximum wavelength in the organic thin film, and in the case of having such a light emission maximum, the light emission from the viewpoint of color purity. The maximum is preferably 430 nm or more and 490 nm or less, and more preferably 440 nm or more and 480 nm or less.
The shortest emission maximum wavelength in the solution of the iridium complex according to the present invention is not particularly limited as long as it is longer than the shortest emission maximum wavelength in the solution of the platinum complex according to the present invention, but is not less than 440 nm and not more than 470 nm. Is preferable, and it is more preferable that it is 440 nm or more and 465 nm or less.

  The iridium complex according to the present invention is preferably an iridium complex represented by the following general formula (1).

[In the general formula ^{(1), A 11} represents a nitrogen atom or a carbon ^{atom, A 12} represents N or ^{CR 13.} R ^{11 to} R ¹³ each independently represents a hydrogen atom or a substituent. Q ¹¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ¹¹ and N. (X—Y) represents a bidentate monoanionic ligand. n represents an integer of 1 to 3. ]

The general formula (1) will be described.
A ¹¹ represents a nitrogen atom or a carbon atom, and is preferably a carbon atom.
Q ¹¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ¹¹ and N. The nitrogen-containing heterocycle is not particularly limited, but is preferably a nitrogen-containing heteroaromatic 6-membered ring or a nitrogen-containing heteroaromatic 5-membered ring. Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazole ring, pyrazole ring and imidazole ring are preferable, pyridine ring, pyrazole ring and imidazole ring are more preferable, pyridine ring and imidazole ring are further preferable, and pyridine ring is particularly preferable. preferable. In the case of a pyrimidine ring, a pyrazine ring, a triazole ring, a pyrazole ring and an imidazole ring, A ¹¹ is preferably a carbon atom.
The nitrogen-containing heterocycle may have a substituent. Although it does not specifically limit as this substituent, The substituent of the said substituent group A is mentioned. A halogen atom, an alkyl group, an aryl group, and a cyano group are preferable, an alkyl group and an aryl group are more preferable, and a methyl group and a phenyl group are more preferable. Moreover, the substituent which a nitrogen-containing heterocycle has may connect with the other substituent which this nitrogen-containing heterocycle or R < ¹¹ > -R < ¹³ > may form a ring, and as a ring, a benzene ring, heteroaryl is included. Groups. These substituents and rings may further have a substituent, and the further substituent is preferably an alkyl group or an aryl group, and more preferably a methyl group or a phenyl group.

R ¹¹ and R ¹² each independently represents a hydrogen atom or a substituent. Although it does not specifically limit as a substituent, The substituent of the substituent group A is mentioned. R ¹¹ and R ¹² are preferably a cyano group, a halogenated alkyl group (for example, a fluorinated alkyl group such as a trifluoromethyl group), an aryl group, a heteroaryl group, or a fluorine atom. The group is more preferably a fluorine atom, and still more preferably a fluorine atom.

A ¹² represents N or CR ¹³ and is preferably N.
When A ¹² is CR ¹³ , R ¹³ represents a hydrogen atom or a substituent. Although it does not specifically limit as a substituent, The substituent of the substituent group A is mentioned. R ¹³ is preferably a cyano group, a trifluoromethyl group, an aryl group, a heteroaryl group, or a fluorine atom, more preferably a cyano group or an aryl group, and even more preferably a cyano group. R ¹³ may be linked to and bonded to R ¹¹ or R ¹² . In that case, the ring formed may have a substituent and may be further condensed.

  (X—Y) represents a bidentate monoanionic ligand. These ligands are believed not to contribute directly to the luminescent properties, but to control the luminescent properties of the molecules. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Examples include the ligands described in Yersin's 1987 issue, “Organometallic Chemistry: Fundamentals and Applications”, Akebono Yamamoto, Akio Yamamoto, 1982 issue, etc. For example, a phosphine ligand, a nitrogen-containing heteroaryl ligand (for example, picolinic acid, bipyridyl, phenanthroline, etc.), a diketonato ligand (for example, acetylacetone, etc.) can be mentioned. Preferred are diketones (acetylacetonato (acac)) or picolinic acid derivatives. A picolinic acid derivative is more preferable from the viewpoint of color purity, and a diketone ligand is more preferable from the viewpoint of durability.

  Specific examples of the bidentate ligand formed by (XY) are given below, but the present invention is not limited thereto.

In general formulas (I-1) to (I-14), Rx, Ry, and Rz each independently represent a hydrogen atom or a substituent.

Examples of the substituent represented by Rx, Ry, and Rz include those in the aforementioned substituent group A. An alkyl group having 3 or less carbon atoms or a hydrogen atom is preferable.
Of the bidentate ligands (XY) formed by (X—Y), those represented by the general formulas (1-1) or (1-4) are preferred. .

  In general formula (1), n represents an integer of 1 to 3, and is preferably 2 or 3. 2 is preferable from the viewpoint of ease of synthesis, and 3 is preferable from the viewpoint of stability of the compound in the organic EL device.

  Specific examples of the general formula (1) include the following compounds. However, the present invention is not limited to these compounds.

  The compound represented by the general formula (1) can be synthesized, for example, by the method described in JP-A-2005-220136.

  In the present invention, the compound represented by the general formula (1) is also preferably a compound represented by the following general formula (A1) or (A3).

(In the general formulas (A1) and (A3), E _{1a to} E _1k each independently represents a carbon atom or a hetero atom. R _{1a to} R _1i each independently represents a hydrogen atom or a substituent (XY). ) Is an auxiliary ligand and represents a bidentate monoanionic ligand, n represents an integer of 1 to 3, and is represented by the compound represented by the general formula (A1) and the general formula (A3). Each compound has a total of 18π electronic structure.)

The compound represented by the general formula (A1) or (A3) has a monoanionic bidentate ligand represented by the following general formula (A1 ′) or (A3 ′) as a main ligand. ing. In the general formula of the ligand in the present invention, * is a coordination site to iridium, the bond between E _1a and iridium, and the bond between the carbon atom of the benzene ring having R _{1g to} R _1i and iridium These may be independently a covalent bond or a coordinate bond.

(In the general formulas (A1 ′) and (A3 ′), E _{1a to} E _1k each independently represents a carbon atom or a hetero atom, and R _{1a to} R _1i each independently represents a hydrogen atom or a substituent. (The bidentate ligand represented by (A1 ′) and the bidentate ligand represented by formula (A3 ′) each have a total of 18π electronic structure.)

  The bidentate ligand represented by the general formula (A1 ′) or (A3 ′) binds to another ligand to form a tridentate, tetradentate, pentadentate or hexadentate ligand. Can do.

In the general formulas (A1), (A3), (A1 ′) and (A3 ′), E _{1a to} E _1k are selected from a carbon atom or a hetero atom, and preferably selected from a carbon atom or a nitrogen atom. The metal complex preferably has an 18π electronic structure.
The ring formed from E _{1a to} E _1e represents a 5-membered heterocycle, and specific examples include oxazole, thiazole, isoxazole, isothiazole, pyrrole, imidazole, pyrazole, triazole, and tetrazole. Preferred is imidazole or pyrazole, and more preferred is imidazole.
The rings formed from E _{1f to} E _1k are each independently selected from 6-membered aromatic hydrocarbon rings, 5-membered or 6-membered heterocycles, such as benzene, oxazole, thiazole, isoxazole, isothiazole, oxadiazole. , Thiadiazole, furan, thiophene, pyrrole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine and the like.
R _{1a to} R _1i are each independently selected from the aforementioned substituent group A, preferably a hydrogen atom, a hydrocarbon substituent, a cyano group, a fluoro group, OR _2a , SR _2a , NR _2a R _2b , BR _2a R _2b. Or SiR _2a R _2b R _2c . R _{2a to} R _2c are each independently a hydrocarbon substituent or a hydrocarbon substituent substituted with a hetero atom, and two of R _{1a to} R _1i and R _{2a to} R _2c are bonded to each other, saturated or An unsaturated aromatic ring or non-aromatic ring may be formed. When bonded to a nitrogen atom, R _{1a to} R _1i are not hydrogen atoms.

  A hetero atom refers to an atom other than a carbon atom or a hydrogen atom. Examples of heteroatoms include, for example, oxygen, nitrogen, phosphorus, sulfur, selenium, arsenic, chlorine, bromine, silicon, or fluorine.

Further, the hydrocarbon substituent is a monovalent or divalent, linear, branched or cyclic substituent, which is composed of only carbon atoms and hydrogen atoms. Examples of monovalent hydrocarbon substituents include, for example, an alkyl group having 1 to 20 carbon atoms (one or more groups selected from alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 8 carbon atoms, and aryl groups). C1-C20 alkyl group substituted by A cycloalkyl group having 3 to 8 carbon atoms (a cycloalkyl group having 3 to 8 carbon atoms substituted by one or more groups selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, and an aryl group). Alkyl group), an aryl group having 6 to 18 carbon atoms (an aryl group substituted with one or more groups selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, and an aryl group), etc. Is mentioned.
Examples of the divalent hydrocarbon group include, for example, —CH ₂ —, —CH ₂ CH ₂ —, —CH ₂ CH _2.
CH ₂ —, 1,2-phenylene group and the like can be mentioned.

At least one of R _{1a to} R _1i is preferably an aryl group having a dihedral angle of 70 degrees or more with respect to the mother skeleton, more preferably a substituent represented by the following general formula ss-1. , 6-disubstituted aryl groups are more preferred, and R _1b is most preferably a 2,6-disubstituted aryl group.

(In general formula ss-1, Ra, Rb, and Rc each independently represent a hydrogen atom, an alkyl group, or an aryl group.)

  The alkyl group represented by Ra, Rb and Rc preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. For example, methyl, ethyl, n-propyl, iso -Propyl, n-butyl, tert-butyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-octadecyl, n-hexadecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, 1-adamantyl , Trifluoromethyl and the like, and a methyl group or an isopropyl group is preferable.

  The aryl group represented by Ra, Rb, and Rc preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. For example, phenyl, o-methylphenyl, m- Examples thereof include methylphenyl, p-methylphenyl, 2,6-xylyl, p-cumenyl, mesityl, naphthyl, anthranyl, and the like, and a phenyl group is preferable.

At least one of Ra and Rb is selected from an alkyl group or an aryl group, and at least one of Ra and Rb is preferably selected from an alkyl group, and both Ra and Rb are preferably alkyl groups, and Ra, Rb Are most preferably a methyl group or an isopropyl group.
The 2,6-disubstituted aryl group is preferably 2,6-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 2, 6-dimethyl-4-phenylphenyl group, 2,6-dimethyl-4- (2,6-dimethylpyridin-4-yl) phenyl group, 2,6-diphenylphenyl group, 2,6-diphenyl-4-isopropyl Phenyl group, 2,4,6-triphenylphenyl group, 2,6-diisopropyl-4- (4-isopropylphenyl) phenyl group, 2,6-diisopropyl-4- (3,5-dimethylphenyl) phenyl group, 2,6-diisopropyl-4- (pyridin-4-yl) phenyl group or 2,6-di- (3,5-dimethylphenyl) phenyl group.

At least one of R _{1a to} R _1i is preferably an alkyl group, and R _1e is more preferably an alkyl group. The alkyl group is preferably an alkyl group branched at a site away from the benzyl position consisting of 4 or more carbon atoms.

In the general formulas (A1) and (A3), examples of the auxiliary ligand represented by (XY) include those exemplified as specific examples of (XY) in the general formula (1). The thing is the same.
In general formula (A1) and (A3), n represents the integer of 1-3 and it is preferable that it is 2 or 3. 2 is preferable from the viewpoint of ease of synthesis, and 3 is preferable from the viewpoint of stability of the compound in the organic EL device.

  In the present invention, the metal complex is constituted by a combination of a main ligand or a tautomer thereof and an auxiliary ligand or a tautomer thereof, or all of the ligands of the metal complex are a main ligand. Or you may be comprised only by the partial structure represented by the tautomer.

  Further, as a so-called ligand used for forming a conventionally known metal complex, the trader may have a known ligand (also referred to as a coordination compound) as an auxiliary ligand, if necessary.

  From the viewpoint of preferably obtaining the effects described in the present invention, the type of ligand in the complex is preferably composed of 1 to 2 types, and more preferably 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.

  The compound represented by the general formula (A1) or (A3) is preferably a compound represented by the following general formula (A1-1) or (A3-1).

(In General Formulas (A1-1) and (A3-1), E _{1f to} E _1k each independently represents a carbon atom or a hetero atom. R _{1a to} R _1i each independently represents a hydrogen atom or a substituent. (X—Y) is an auxiliary ligand and represents a bidentate monoanionic ligand, n represents an integer of 1 to 3. Compounds represented by formula (A1-1) and formula (The compounds represented by (A3-1) each have a total of 18π electronic structure.)

In formula (A1-1) and _{(A3-1), E} 1f _{~E 1k} is and definition of _R 1a _{to R 1i} is, _E 1f _{to E} in the general formula (A1) and (A3) _1k is and _{R 1a} It is the same as _-R1i , and a preferable thing is also the same.

  The compound represented by the general formula (A1) or (A3) is also preferably a compound represented by the following general formula (A1-2) or (A3-2).

(In General Formulas (A1-2) and (A3-2), E _{1f to} E _1k each independently represents a carbon atom or a hetero atom. R _{1a to} R _1i each independently represents a hydrogen atom or a substituent. (X—Y) is an auxiliary ligand, which represents a bidentate monoanionic ligand, n represents an integer of 1 to 3. Compounds represented by formula (A1-2) and formula The compounds represented by (A3-2) each have a total of 18π electronic structure.)

In formula (A1-2) and _{(A3-2), E} 1f ~E _1k and the definition of _R 1a _{to R 1i} is, (A1-1) and _E 1f _{to E 1k} and _{R 1a} in (A3-1) It is the same as _-R1i , and a preferable thing is also the same.

  In the present invention, the general formula (A1-2) is more preferable, and the general formula (A1-2) is more preferably a compound represented by the following general formula (A1-3).

(In the general formula (A1-3), R _{1a to} R _1i each independently represents a hydrogen atom or a substituent. (XY) is an auxiliary ligand, and a bidentate monoanionic ligand is represented by N represents an integer of 1 to 3. The compound represented by the general formula (A1-3) has an 18π electronic structure.

In formula _(A1-3), the definition of R 1a _{to R 1i} are the same as _R 1a _{to R 1i} in (A1), preferable ones are also same.

  Preferred specific examples of the general formulas (A1 ′) and (A3 ′) are shown below. Of these, (X-63), (X-64), and (X-67) are most preferable.

R ^{1a to} R ¹ⁱ have the same meaning as in the general formula (A1), and preferably all are hydrogen atoms.

The compound represented by the general formula (A1) or (A3) can be synthesized by various methods such as the methods described in US2007 / 0190359 and US2008 / 0297033.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic or organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective). Specifically, XM-64 can be synthesized by a synthesis method described in [0132] to [0134] of US2007 / 0190359 using 7-methylimidazophenanthridine as a starting material. XM-63 can be synthesized by the synthesis method described in [0281] to [0287] of US2008 / 0297033.

  Of the compounds represented by the general formula (A1-3), compounds represented by the following compounds (1-25) to (1-30) are particularly preferable.

(Platinum complex)
The platinum complex according to the present invention is a complex that emits associated light in an organic thin film and has an emission maximum wavelength of 550 nm or more and less than 650 nm. The emission maximum wavelength is preferably 555 nm or more and 630 nm or less, and more preferably 560 nm or more and 600 nm or less. When the shortest emission maximum wavelength in the organic thin film is within this range, the range of colors that can be expressed by combining with the emission of the iridium complex is expanded, and the color purity when white is achieved can also be improved.
Furthermore, when the emission intensity at the shortest emission maximum wavelength of the iridium complex in the organic thin film is 1.0, the emission intensity at the emission maximum wavelength of 550 nm to 650 nm of the platinum complex in the organic thin film is It is preferably 0.3 to 1.5, more preferably 0.4 to 1.3, and still more preferably 0.5 to 1.2.
The shortest emission maximum wavelength in the solution of the platinum complex according to the present invention is not particularly limited as long as it is shorter than the shortest emission maximum wavelength in the solution of the iridium complex according to the present invention, but from the viewpoint of luminous efficiency or color purity. Therefore, it is preferably 420 nm or more and 470 nm or less, more preferably 430 nm or more and 460 nm or less, further preferably 435 nm or more and 455 nm or less, and particularly preferably 435 nm or more and 450 nm or less.

  The platinum complex according to the present invention is preferably a platinum complex represented by the following general formula (2) from the viewpoint of luminous efficiency.

[In General Formula (2), A ²¹ and A ²² each independently represent a nitrogen atom or a carbon atom. Q ²¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ²¹ and N. Q ²² represents an atomic group that forms a nitrogen-containing heterocycle together with A ²² and N. L ²¹ represents an atomic group bonded to Pt and A ^21, and L ²² represents an atomic group bonded to Pt and A ²² . L ²³ represents a linking group. ]

The general formula (2) will be described.
A ²¹ and A ²² each independently represent a nitrogen atom or a carbon atom, preferably a carbon atom.
Q ²¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ²¹ and N. Q ²² represents an atomic group that forms a nitrogen-containing heterocycle together with A ²² and N. The nitrogen-containing heterocycle is not particularly limited, but is preferably a nitrogen-containing heteroaromatic 6-membered ring or a nitrogen-containing heteroaromatic 5-membered ring. Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazole ring, pyrazole ring and imidazole ring are preferable, pyridine ring, pyrazole ring and imidazole ring are more preferable, pyridine ring and pyrazole ring are more preferable, and pyrazole ring is particularly preferable. preferable. When the nitrogen-containing heterocycle formed by Q ²¹ , A ²¹ and N is a pyrimidine ring, pyrazine ring, triazole ring, pyrazole ring or imidazole ring, A ²¹ is preferably a carbon atom. Similarly, when the nitrogen-containing heterocycle formed by Q ²² , A ²² and N is a pyrimidine ring, a pyrazine ring, a triazole ring, a pyrazole ring or an imidazole ring, A ²² is preferably a carbon atom. The nitrogen-containing heterocycle formed by Q ²¹ , A ²¹ and N and the nitrogen-containing heterocycle formed by Q ²² , A ²² and N may be the same or different, but from the viewpoint of color purity or luminous efficiency At least one of the nitrogen-containing heterocycles is preferably a pyrazole ring.
The nitrogen-containing heterocycle may have a substituent. Although it does not specifically limit as this substituent, The substituent of the said substituent group A is mentioned. Preferred are an alkyl group, an alkoxy group, an alkylthio group, a cyano group, an aryl group and an amino group, more preferred are an alkyl group and an aryl group, and further preferred are an n-butyl group and a phenyl group. In addition, substituents of the nitrogen-containing heterocycle may be linked to form a ring. These substituents and rings may further have a substituent, and examples of the further substituent include the substituents of the substituent group A.

L ²³ represents a linking group. The linking group is not particularly limited, but a divalent linking group containing a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a germanium atom, or a phosphorus atom is particularly preferable, and is selected from the following linking group group A: Particularly preferred are the groups
(Linking group A)

In the above linking group A, R ₂₅ , R ₂₆ , R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₂ , R ₃₃ , R ₃₄ , R ₃₅ and R ₃₆ are each independently a hydrogen atom or a substituent. Represents a group. When R _{25 to} R ₃₆ represent a substituent, examples of the substituent include a substituent selected from the following substituent group B. When R _{25 to} R ₃₆ can be substituted, they may further have a substituent selected from the substituent group B, and R ₂₅ and R ₂₆ , R ₂₇ and R ₂₈ , R ₂₉ and R ₃₀ , R ₂₇ and R ₂₉ , R ₂₇ and R ₃₀ , R ₂₈ and R ₃₀ , R ₂₈ and R ₂₉ , R ₃₁ and R ₃₂ or R ₃₃ and R ₃₄ may be bonded to each other to form a ring.

(Substituent group B)
Substituent group B is an alkyl group, a cycloalkyl group, an aryl group, a halogen atom, an amino group, an alkylthio group, an arylthio group, an alkyloxy group, an aryloxy group, more preferably an alkyl group, still more preferably. A methyl group, an ethyl group, an n-propyl group, and an n-butyl group are preferable, and a methyl group is particularly preferable.

L ²³ includes -C (R ₂₅ ) (R ₂₆ )-, -C (R ₂₇ ) (R ₂₈ ) C (R ₂₉ ) (R ₃₀ )-, -Si (R ₃₁ ) (R ₃₂ )-, —N (R ₃₅ ) —, —O—, —S—, —SO—, —SO ₂ — or —CO— is preferred, and —C (R ₂₅ ) (R ₂₆ ) —, —C (R ₂₇ ) ( R ₂₈ ) C (R ₂₉ ) (R ₃₀ ) —, —Si (R ₃₁ ) (R ₃₂ ) —, —O—, or —S— is more preferred, —C (R ₂₅ ) (R ₂₆ ) —, or _{-C (R 27) (R 28} ) C (R 29) (R 30) - it is further preferable.

In the -C (R ₂₅ ) (R ₂₆ )-, R ₂₅ and R ₂₆ are preferably a hydrogen atom or a substituent selected from the substituent group B.
The _{-C (R 27) (R 28} ) C (R 29) (R 30) - _{In, R 27, R 28, R} 29 and _{R 30} substituents preferably selected from a hydrogen atom or a substituent group B It is.
In the —Si (R ₃₁ ) (R ₃₂ ) —, R ₃₁ and R ₃₂ are preferably a hydrogen atom or the substituent selected from the substituent group B.
In the -Ge (R ₃₃ ) (R ₃₄ )-, R ₃₃ and R ₃₄ are preferably a hydrogen atom or the substituent selected from the substituent group B.
In the —N (R ₃₅ ) —, R ₃₅ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group.
In the above -P (R ₃₆ )-, R ₃₆ has the same _{meaning as} the preferred range of R ₃₅ .

In the general formula (2), L ²¹ represents an atomic group bonded to Pt and A ^21, and L ²² represents an atomic group bonded to Pt and A ²² .
L ²¹ and L ²² preferably represent an aromatic ring or an aromatic heterocycle. The aromatic ring and aromatic heterocycle are preferably 5-membered or 6-membered rings, including benzene rings (including condensed ring structures such as naphthalene, dibenzofuran, dibenzothiophene, and carbazole), pyridine rings, pyrazine rings, and pyridazine rings. , A pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, a pyrrole ring, a thiophene ring, a furan ring, and the like, more preferably a benzene ring and a pyridine ring, and still more preferably a benzene ring. The aromatic ring or aromatic heterocycle may have a substituent. Although it does not specifically limit as this substituent, The substituent represented by the substituent group A is mentioned, Preferably the alkyl group, cyano group, and aryl group which may have a halogen atom and a substituent are mentioned, Furthermore, A trifluoromethyl group, a perfluorobutyl group, and a cyano group are preferable. In addition, substituents may be connected to form a ring.

  The platinum complex represented by the general formula (2) is preferably a platinum complex represented by the following general formula (3).

[In General Formula (3), R ^{301 to} R ³¹² each independently represents a hydrogen atom or a substituent. At least two of R ³⁰¹ and R ³⁰² , R ³⁰³ and R ³⁰⁴ , R ^{305 to} R ³⁰⁸ , and at least two of R ^{309 to} R ³¹² may be connected to each other to form a ring. L ³¹ represents a linking group. ]

The general formula (3) will be described.
L ³¹ has the same meaning as ^{L 23} in the general formula (2), and the preferred range is also the same.
R ^{301 to} R ³¹² each independently represent a hydrogen atom or a substituent. Although it does not specifically limit as this substituent, The substituent represented by the substituent group A is mentioned, Preferably the halogen group, the alkyl group which may have a substituent, a cyano group, an aryl group, an alkoxy group, aryl An oxy group, an alkylamino group, an arylamino group, etc. are mentioned, More preferably, they are a trifluoromethyl group, a perfluorobutyl group, and a cyano group. At least two of R ³⁰¹ and R ³⁰² , R ³⁰³ and R ³⁰⁴ , R ^{305 to} R ³⁰⁸ , and at least two of R ^{309 to} R ³¹² may be connected to each other to form a ring.

  Specific examples of the general formula (2) include the following compounds. However, the present invention is not limited to these compounds.

  The compound represented by the general formula (2) can be synthesized, for example, by the following scheme.

  In the above scheme, R and R ′ represent a hydrogen atom or a substituent.

(Host material)
The organic thin film of the present invention contains a host material in addition to an iridium complex and a platinum complex.
Although it does not specifically limit as host material, A carbazole derivative, an arylamine derivative, a benzene derivative (a condensed ring structure is included) etc. are mentioned. From the viewpoint of luminous efficiency, carbazole derivatives and arylamine derivatives are preferable, and carbazole derivatives are more preferable.

  Examples of the carbazole derivative include the following compounds. However, it is not necessarily limited to these compounds.

  Examples of the arylamine derivative include the following compounds. However, it is not necessarily limited to these compounds.

Examples of other host materials include the following compounds. However, it is not necessarily limited to these compounds.

The organic thin film of the present invention can be suitably formed by any of dry film forming methods such as vapor deposition and sputtering, wet film forming methods such as solution coating, transfer methods, and printing methods.
The content of the iridium complex in the organic thin film of the present invention is preferably 1% by mass to 30% by mass, more preferably 5% by mass to 20% by mass, and still more preferably 8% by mass to 15% by mass. The content of the platinum complex is preferably 1% by mass to 20% by mass, more preferably 2% by mass to 15% by mass, and particularly preferably 4% by mass to 12% by mass. From the viewpoint of obtaining a wide range of emission colors, the mass ratio of the iridium complex to the platinum complex in the organic thin film (iridium complex: platinum complex) is preferably 10: 1 to 1:10, and more preferably 5: 1 to 1: 5. 5: 2 to 2: 5 are particularly preferable.
The content of the host material in the organic thin film of the present invention is preferably 15% by mass to 95% by mass, more preferably 30% by mass to 90% by mass, and 60% by mass to 90% by mass. More preferably, 70 mass%-90 mass% is especially preferable.

  The thickness of the organic thin film is not particularly limited, but from the viewpoint of film forming properties, it is preferably 1 nm or more and 1000 nm or less, more preferably 3 nm or more and 500 nm or less, and further preferably 5 nm or more and 300 nm or less, It is particularly preferably 10 nm or more and 100 nm or less. In addition, when the film is formed, the surface may become rough. In that case, the film thickness is an average film thickness. The film thickness was measured using a stylus thickness meter (Dektak 3ST manufactured by Sloan) A. It can be measured with a spectroscopic ellipsometry M-2000 manufactured by Woollam.

[Organic electroluminescence device]
The organic electroluminescent element of the present invention has at least one organic layer including a light emitting layer between a pair of electrodes, and at least one light emitting layer is the organic thin film of the present invention.
In the organic electroluminescent element of the present invention, the light emitting layer is an organic layer, but may further have a plurality of organic layers.
In view of the properties of the light-emitting element, at least one of the anode and the cathode is preferably transparent or translucent.
FIG. 9 shows an example of the configuration of the organic electroluminescent element according to the present invention. An organic electroluminescent element 10 according to the present invention shown in FIG. 9 has a pair of electrodes (anode 3 and cathode 9) on a substrate 12, and a light emitting layer 6 between the pair of electrodes. Specifically, a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7, and an electron transport layer 8 are provided in this order between the anode 3 and the cathode 9.

<Structure of organic layer>
There is no restriction | limiting in particular as a layer structure of the said organic layer, According to the use and objective of an organic electroluminescent element, it can select suitably. It is preferably formed on the anode or the cathode. In this case, the organic layer is formed on the whole surface or a part on the anode or the cathode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.

Specific examples of the layer structure of the organic layer between the cathode and the anode include the following, but the present invention is not limited to these structures.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.

<Board>
The substrate is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
<Anode>
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.
<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.
Regarding the substrate, anode, and cathode, the matters described in paragraphs [0070] to [0089] of JP-A-2008-270736 can be applied to the present invention.

<Organic layer>
The organic layer will be described.
-Formation of organic layer-
In the organic electroluminescent element, each organic layer can be suitably formed by any of dry film forming methods such as vapor deposition and sputtering, wet film forming methods such as solution coating, transfer methods, and printing methods.

(Light emitting layer)
<Light emitting material>
The light emitting material in the light emitting layer of the organic electroluminescent element of the present invention is preferably a phosphorescent light emitting material, and is preferably the iridium complex or platinum complex.

The light emitting material in the light emitting layer is preferably contained in an amount of 0.1% by mass to 50% by mass with respect to the mass of all the compounds that generally form the light emitting layer in the light emitting layer. In view of the above, the content is more preferably 1% by mass to 50% by mass, and further preferably 2% by mass to 40% by mass.
The phosphorescent light emitting material in the light emitting layer is preferably contained in the light emitting layer in an amount of 1% by mass to 30% by mass, and more preferably 2% by mass to 20% by mass, from the viewpoint of durability and emission hue.

  Although the thickness of the light emitting layer is not particularly limited, it is usually preferably 2 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.

The light emitting layer may have other materials (light emitting material or host material) as long as it is a mixed layer of an iridium complex, a platinum complex and a host material. Other light-emitting materials that may be included may be fluorescent light-emitting materials or phosphorescent light-emitting materials.
The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
Moreover, the light emitting layer may consist of a plurality of layers, in which case at least one layer is the organic thin film of the present invention. When the light emitting layer is composed of a plurality of layers, the respective emission colors may be the same or different.

<Host material>
The host material used in the present invention may contain the following compounds. For example, pyrrole, indole, carbazole (eg, CBP (4,4′-di (9-carbazoyl) biphenyl)), azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, Pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinyl) Carbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazo , Pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds , Metal complexes of heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine, 8-quinolinol derivatives and metal complexes represented by metal phthalocyanine, benzoxazole and benzothiazole ligands And derivatives thereof (which may have a substituent or a condensed ring).

In the light emitting layer, the triplet minimum excitation energy (T ₁ energy) of the host material is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability.

  Although content of a host compound is not specifically limited, From a viewpoint of luminous efficiency and a drive voltage, it is preferable that it is 15 to 95 mass% with respect to the total compound mass which forms a light emitting layer.

(Fluorescent material)
Examples of fluorescent light-emitting materials that can be used in the present invention include, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives. , Condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Complexes of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives and pyromethene derivatives Various complexes represented, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds include compounds such as organic silane derivatives.

(Phosphorescent material)
Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, EP 121157, JP -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-17367. , JP 2002-203678, JP 2002-203679, JP 2004-357799, JP 2006-256999, JP 2007-19462, JP 2007-84635, JP 2007-96259, and the like. Examples of such a luminescent dopant include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, among others. Gd complex, Dy complex, and Ce complex are mentioned. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity, etc., an Ir complex, a Pt complex, or a Re complex containing a tridentate or higher polydentate ligand is particularly preferable.

-Hole injection layer, hole transport layer-
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
In the present invention, the organic layer preferably includes a hole injection layer or a hole transport layer containing an electron-accepting dopant.

-Electron injection layer, electron transport layer-
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.

  Regarding the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention. .

-Hole blocking layer-
The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
As an example of the organic compound constituting the hole blocking layer, aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as BAlq), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-Dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP)) and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.

-Electronic block layer-
The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

<Protective layer>
In the present invention, the entire organic EL element may be protected by a protective layer.
Regarding the protective layer, the matters described in paragraph numbers [0169] to [0170] of JP-A-2008-270736 can be applied to the present invention.

<Sealing container>
The element of this invention may seal the whole element using a sealing container.
Regarding the sealing container, the matters described in paragraph No. [0171] of JP-A-2008-270736 can be applied to the present invention.

(Drive)
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Can be obtained.
The driving method of the organic electroluminescent device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

  The light-emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, by processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate / ITO layer / organic layer, controlling the film thickness of the substrate / ITO layer / organic layer, etc. It is possible to improve light extraction efficiency and external quantum efficiency.

  The light emitting element of the present invention may be a so-called top emission method in which light emission is extracted from the anode side.

The organic EL element in the present invention may have a resonator structure. For example, a multilayer mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate. The light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
In another preferred embodiment, a transparent or translucent electrode and a metal electrode each function as a reflecting plate on a transparent substrate, and light generated in the light emitting layer repeats reflection and resonates between them.
In order to form a resonant structure, the optical path length determined from the effective refractive index of the two reflectors and the refractive index and thickness of each layer between the reflectors is adjusted to an optimum value to obtain the desired resonant wavelength. Is done. The calculation formula in the case of the first embodiment is described in JP-A-9-180883. The calculation formula in the case of the second aspect is described in Japanese Patent Application Laid-Open No. 2004-127795.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 7% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m ² when the device is driven at 20 ° C. Can do.

  The internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%. However, the shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, the refractive index of the inorganic layer, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

(Use of the organic electroluminescence device of the present invention)
The organic electroluminescent element of the present invention is suitable for light emitting devices, pixels, display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, etc. Available. In particular, it is preferably used for a device driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.
Since the organic electroluminescent element of the present invention has the organic thin film of the present invention as a light emitting layer, it is suitable for a light emitting device such as a display that expresses blue from a white light source through a color filter. By using the organic electroluminescent element of the present invention in a light emitting device as a white light source, blue light emission with good color purity and good luminous efficiency can be obtained.

Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 10 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
The light-emitting device 20 in FIG. 10 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 11, and the like.

The organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. A protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween. In addition, a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

  The use of the light-emitting device of the present invention is not particularly limited, and for example, in addition to a lighting device, a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.

(Lighting device)
Next, an illumination device according to an embodiment of the present invention will be described with reference to FIG.
FIG. 11 is a cross-sectional view schematically illustrating an example of a lighting device according to an embodiment of the present invention.
As shown in FIG. 11, the lighting device 40 according to the embodiment of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 11, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.

    EXAMPLES The present invention will be described more specifically with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

(Synthesis example)
Synthesis of Compound (2-1) A synthesis scheme of the compound (2-1) is shown below.

1.76 g of compound (G-1), 10.88 g of compound (G-11), 0.14 g of copper (I) oxide, 0.56 g of compound (G-4), 16 g of cesium carbonate, 1,3-dimethyl-2 -30 ml of imidazolidinone was placed in a three-necked flask and allowed to react overnight at 175 ° C under a nitrogen atmosphere. The temperature was returned to room temperature, 300 ml of ethyl acetate was added, celite filtration was performed, and a liquid separation operation was performed with ethyl acetate / brine. Purification by silica gel column chromatography using ethyl acetate / hexane as an eluent gave 2.71 g of compound (G-2).
2.46 g of compound (G-2), 1.41 g of platinum chloride and 30 ml of m-tolunitrile were placed in a three-necked flask and reacted at 178 ° C. for 7 hours in a nitrogen atmosphere. The mixture was returned to room temperature and purified by silica gel column chromatography using chloroform as an eluent, recrystallization using benzonitrile, and heat washing using ethyl acetate to obtain 570 mg of compound (2-1). The obtained compound was identified by ¹ H-NMR. 400 MHz 1H-NMR (dmso-d6) δ: 8.93 (d, 2H), 8.05 (t, 2H), 7.91 (d, 2H), 7.57 (d, 2H), 7.17 (d, 2H)

Example 1
-Preparation of organic thin film-
The compound (1-1) as the iridium complex, the compound (2-1) as the platinum complex, and the compound (H-1) as the host material were co-deposited on the glass substrate so as to have the ratio (mass%) shown in Table 1. An organic thin film having a thickness of 50 nm was prepared.

The emission spectrum of the produced organic thin film was measured with a quantum yield measuring device manufactured by Hamamatsu Photonics. The obtained emission spectrum is shown in FIG. The CIExy coordinates were (0.34, 0.37).
The emission quantum yield was measured as follows as the emission maximum wavelength of the iridium complex and the platinum complex in the organic thin film and in the solution, and as an index of the emission efficiency.
(Measurement of light emission maximum wavelength)
The organic thin film made of an iridium complex and a host material and the organic thin film made of a platinum complex and a host material were produced without changing the contents of the produced organic thin film and the complex, respectively, and a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics Co., Ltd. was used. The maximum wavelength of light emission in the organic thin film of each complex was determined. Each complex was dissolved in a dichloromethane solution (complex concentration: 0.01 mg / ml), and the emission maximum wavelength in the solution of each complex was determined with a spectrofluorophotometer RF-5300PC manufactured by SHIMADU.
(Measurement of luminescence quantum yield Φ)
The produced organic thin film was measured with a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics using an integrating sphere at an excitation wavelength of 310 nm (“Φ of organic thin film” in Table 1).
Next, without changing the content of the complex, an organic thin film composed of an iridium complex and a host material and an organic thin film composed of a platinum complex and a host material were prepared and measured by the same method as above (in Table 1). "Ir complex Φ", "Pt complex Φ").
The higher the emission quantum yield, the higher the emission efficiency. In the present invention, the evaluation was performed according to the following criteria.
○: Φ is 0.7 or more Δ: Φ is 0.5 or more and less than 0.7 ×: Φ is less than 0.5 Table 1 shows the measurement results of the emission maximum wavelength and the emission quantum yield Φ. Moreover, the organic thin film (ratio 10:90 (mass%)) which consists of an iridium complex and host material used in Example 1 was produced similarly to Example 1, and the emission spectrum was measured. FIG. 5 shows the emission spectrum.

(Examples 2-15, Comparative Examples 1-2)
As shown in Table 1, an organic thin film was prepared in the same manner as in Example 1 except that the types and ratios of the iridium complex, platinum complex and host material were changed, and the emission maximum wavelength and the emission quantum yield Φ were measured.
Moreover, about the organic thin film of Example 2, 5 and 6, the emission spectrum was measured by the method similar to Example 1. FIG. The obtained emission spectra are shown in FIGS. The CIExy coordinates of light emission from the organic thin film of Example 2 were (0.34, 0.38).
Furthermore, for the iridium complex used in Example 2 and the platinum complex used in Examples 2 and 3, an organic thin film composed of each complex and the host material used in each Example (ratio is 10:90 (mass%)) ) And an emission spectrum was measured in the same manner as in Example 1. The obtained emission spectra are shown in FIGS.

  In Table 1 below, the emission color from each organic thin film is also described. In Table 1, the reason why the emission maximum wavelength of the platinum complex in the organic thin film is described in the range is that a slight deviation is likely to occur every time the thin film is produced. This is because the amount of associated molecules can change depending on how close the Pt complexes are in the thin film, or the amount of overlap between the Ir complex and the Pt complex overlaps the emission spectrum of the partner. This is probably because the maximum wavelength can change.

  From the results of Table 1, it can be seen that the organic thin film of the present invention can produce white light emission with high luminous efficiency and high color purity.

(Examples 16, 17, 18, 19)
In Example 9, the organic thin film of Example 16 was produced like Example 9 except having used compound (2-2) as a platinum complex. Moreover, in Example 9, the organic thin film of Example 17 was produced like Example 9 except having used the compound (2-7) as a platinum complex. Moreover, the organic thin film of Example 18 was produced like Example 9 except having used the compound (2-10) as a platinum complex in Example 9. In Example 1, the organic thin film of Example 19 was prepared in the same manner as in Example 1 in which the compound (1-27) was to be used as the iridium complex.
In Examples 16, 17, 18, and 19, light blue to white light emission was obtained.

  From the results of Examples 1 and 2, it can be seen that the organic thin film of the present invention can emit light with high white color purity. Moreover, it turns out that the wide light emission color is obtained from the result of Examples 1-15.

(Example 20)
A glass substrate having an ITO film of 0.5 mm thickness and 2.5 cm square (manufactured by Geomatek Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic layers (organic compound layers) were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
The vapor deposition rate in the examples of the present specification is 0.2 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The film thicknesses described below were also measured using a crystal resonator.

The cleaned ITO substrate was put into a vapor deposition apparatus, and 4,4 ′, 4 ″ -tris (2-naphthylphenylamino) triphenylamine (2-TNATA), 2,3,5,6-tetrafluoro-7,7 , 8,8-Tetracyanoquinodimethane (F ₄ -TCNQ) is co-evaporated at a mass ratio of 99.7: 0.3 with a thickness of 120 nm, and α-NPD is further evaporated thereon with a thickness of 7 nm. (H-12) was deposited by 3 nm. On top of this, the compound (1-1) as an iridium complex, the compound (2-1) as a platinum complex, and the compound (H-14) as a host material were co-deposited at 30 nm in the same proportion as the organic thin film of Example 2 (luminescence) Layer), and further, BAlq was deposited thereon by 30 nm.
A patterned mask (with a light emitting area of 4 mm × 5 mm) was placed on the organic thin film obtained, and 1 nm of lithium fluoride was deposited, and then 100 nm of aluminum was deposited. Without exposing it to the atmosphere, put it in a glove box substituted with argon gas, and seal it with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba). The organic electroluminescent element of Example 20 was produced.
About the obtained organic electroluminescent element, when white voltage was applied to the element using a source measure unit 2400 manufactured by Toyo Technica to emit light, strong white light emission was observed.

  From the results of Example 2 and Example 20, it is considered that the light emission color similar to that of the organic thin film can be obtained also in the organic electroluminescent element including the organic thin film of Example 1 and Examples 3 to 19.

  The compounds used in Examples and Comparative Examples are shown below.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ...・ Cathode 10: Organic electroluminescent device (organic EL device)
DESCRIPTION OF SYMBOLS 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 30A ... Light incident surface 30B ... Light Emitting surface 32... Fine particle 40.

Claims (9)

An organic thin film containing an iridium complex, a platinum complex and a host material,
In the organic thin film, the shortest emission maximum wavelength of the iridium complex is 430 nm or more and less than 480 nm, and the emission maximum wavelength of the platinum complex is 550 nm or more and less than 650 nm,
Shortest emission maximum wavelength of the platinum complex in dichloromethane, Ri shorter wavelength der than the shortest emission maximum wavelength before Symbol iridium complex in dichloromethane,
The iridium complex is an iridium complex represented by the following general formula (1):
The organic thin film characterized in that the platinum complex is a platinum complex represented by the following general formula (3).

[In General Formula (1), A ¹¹ represents a nitrogen atom or a carbon atom, and A ¹² represents N or CR ¹³ . R ^{11 to} R ¹³ each independently represents a hydrogen atom or a substituent. Q ¹¹ represents an atomic group that forms a nitrogen-containing heterocycle together with A ¹¹ and N. (X—Y) represents a bidentate monoanionic ligand. n represents an integer of 1 to 3. ]

[In General Formula (3), R ^{301 to} R ³¹² each independently represents a hydrogen atom or a substituent. At least two of R ³⁰¹ and R ³⁰² , R ³⁰³ and R ³⁰⁴ , R ^{305 to} R ³⁰⁸ , and at least two of R ^{309 to} R ³¹² may be connected to each other to form a ring. L ³¹ represents a linking group. ]   The organic thin film according to claim 1, wherein the shortest emission maximum wavelength of the iridium complex in the organic thin film is 430 nm or more and less than 470 nm. A in the general formula (1) ¹² The organic thin film according to claim 1, wherein N is N. The organic thin film according to any one of claims 1 to 3, wherein XY in the general formula (1) is any one of the following bidentate ligands.

The organic thin film according to any one of claims 1 to 4, wherein the host material is a carbazole derivative, an arylamine derivative, or a benzene derivative. The organic thin film according to any one of claims 1 to 4, wherein the host material is any of the following.

  It is an organic electroluminescent element which has an at least 1 layer of organic layer containing a light emitting layer between a pair of electrodes, Comprising: The said light emitting layer is an organic electroluminescent element which is an organic thin film as described in any one of Claims 1-6. .   The light-emitting device using the organic electroluminescent element of Claim 7. The illuminating device using the organic electroluminescent element of Claim 7.

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