JP2012216817A - Organic electroluminescent element, and light-emitting device, display unit, luminaire using that element, and compound for that element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element having excellent durability in which chromaticity deviation is small during high-temperature storage.SOLUTION: The organic electroluminescent element comprises a substrate, a pair of electrodes including a positive electrode and a negative electrode arranged on the substrate, and an organic layer arranged between the electrodes and containing a phosphorescent material and a compound represented by a following formula (Xrepresents an oxygen atom or a sulfur atom, R-Rrepresents a hydrogen atom or a substituent group (excepting an alkyl radical and a cyano group), a plurality of R-Rmay be identical or different from each other. Lrepresents a single bond or an arylene group).

Description

  The present invention relates to an organic electroluminescent element, a light emitting device using the element, a display device, a lighting device, and a compound for the element.

  Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they emit light with high luminance when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.

  In recent years, the efficiency of organic electroluminescent devices has been increased by using phosphorescent materials. However, in practical use, improvements are required from the viewpoint of durability and the like. Patent Document 1 discloses the use of a dibenzothiophene-based charge transport material for further improving the light emission efficiency and device durability of the device. Further, Patent Document 2 discloses an organic electroluminescent device using a compound in which dibenzothiophene and triphenylene are linked by a phenyl group. Further, Patent Documents 3 and 4 describe organic electroluminescent devices using a compound in which dibenzothiophene is linked by a phenyl group.

  On the other hand, in recent years, various display devices including an organic electroluminescent element have been widely used, and are required to operate stably for a long time under various environments. For example, in-vehicle applications such as in-vehicle applications require a long life (so-called durability), and the interior of the vehicle becomes quite hot when running or parked during the day. There is also a need for no change. In addition, it is important that the organic electroluminescent element does not change its characteristics after being stored at such a high temperature from the viewpoint that it generates heat when driven to the same degree or more as a conventional light emitting device.

International Publication No. WO2007 / 069569 International Publication WO2009 / 021126 International Publication WO2009 / 085344 International Publication WO2009 / 073245

On the other hand, as a result of studying the characteristics of the organic electroluminescent elements described in Patent Documents 1 to 4, the present inventors are still unhappy with the durability of the conventional organic electroluminescent elements. It became clear that there was a problem that chromaticity changed when stored.
Thus, when the compound used in the organic layer was changed, it was found that the durability and chromaticity shift during high-temperature storage change to some extent. Therefore, further research was conducted on the compounds used in the organic layer, and it was found that simply increasing the molecular weight of the compound used in the organic layer does not necessarily improve the durability and chromaticity shift during high-temperature storage. It was. For example, compound 9S described in Patent Document 2 was found to be inferior in durability, although the chromaticity shift at the time of high-temperature storage was improved as compared with compound 2S having a molecular weight and a glass transition temperature lower than this compound. That is, it was found that it is difficult to improve both durability and chromaticity shift during high-temperature storage by changing the compound used in the organic layer.

  The problem to be solved by the present invention is to provide an organic electroluminescent device which is excellent in durability and has a small chromaticity shift during high-temperature storage.

  As a result of intensive studies by the present inventors, an organic electroluminescent device having excellent durability and small chromaticity shift during high-temperature storage is obtained by using a compound containing a dibenzothiophene structure or dibenzofuran structure and a p-terphenylene structure. I found out that it would be offered.

（一般式（１）中、Ｘ¹⁰¹は酸素原子または硫黄原子を表し、Ｒ¹⁰¹〜Ｒ¹¹⁰は水素原子又は置換基（但し、アルキル基とシアノ基を除く）を表し、複数のＲ¹⁰⁸〜Ｒ¹¹⁰は互いに同一でも異なっていてもよい。Ｌ¹⁰¹は単結合又はアリーレン基を表す。）
［２］ 前記一般式（１）で表される化合物の分子量が５５０以上であることを特徴とする［１］に記載の有機電界発光素子。
［３］ 前記一般式（１）における少なくとも１つのＲ¹¹⁰が縮合環である環員数１０〜３０のアリール基、縮合環である環員数８〜３０のヘテロアリール基、これらを置換基として有する炭素数６〜２５のアリール基又は環員数５〜２５のヘテロアリール基、あるいは、炭素数６〜２５の単環のアリール基を置換基として有する環員数５〜２５の単環のヘテロアリール基であることを特徴とする［１］又は［２］に記載の有機電界発光素子。
［４］ 前記一般式（１）で表される化合物が、下記一般式（２）又は（３）で表される化合物であることを特徴とする［１］〜［３］のいずれか一項に記載の有機電界発光素子。
一般式（２）

（一般式（２）中、Ｘ²⁰¹は酸素原子又は硫黄原子を表す。Ｒ²⁰¹〜Ｒ²¹²はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ²⁰⁸およびＲ²⁰⁹は互いに同一でも異なっていてもよい。Ｌ²⁰¹は単結合又はアリーレン基を表し、ｐ−ターフェニレン基ではない。Ａ²⁰¹およびＡ²⁰²の一方は縮合環である環員数１０〜３０のアリール基、縮合環である環員数８〜３０のヘテロアリール基、これらを置換基として有する炭素数６〜２５のアリール基又は環員数５〜２５のヘテロアリール基、あるいは、炭素数６〜２５の単環のアリール基を置換基として有する環員数５〜２５の単環のヘテロアリール基を表し、もう一方は水素原子、アリール基又はヘテロアリール基を表す。）
一般式（３）

（一般式（３）中、Ｘ³⁰¹は酸素原子又は硫黄原子を表す。Ｒ³⁰¹〜Ｒ³¹⁵はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ³⁰⁸〜Ｒ³¹²は互いに同一でも異なっていてもよい。Ｌ³⁰¹は単結合又はアリーレン基を表す。Ａ³⁰¹およびＡ³⁰²の一方は縮合環である環員数１０〜３０のアリール基、縮合環である環員数８〜３０のヘテロアリール基、これらを置換基として有する炭素数６〜２５のアリール基又は環員数５〜２５のヘテロアリール基、あるいは、炭素数６〜２５の単環のアリール基を置換基として有する環員数５〜２５の単環のヘテロアリール基を表し、もう一方は水素原子、アリール基又はヘテロアリール基を表す。）
［５］ 前記一般式（１）におけるＲ¹⁰⁸およびＲ¹⁰⁹がいずれも水素原子であることを特徴とする［１］〜［４］のいずれか一項に記載の有機電界発光素子。
［６］ 前記一般式（１）で表される化合物が、ガラス転移温度が１００℃以上の化合物であることを特徴とする［１］〜［５］のいずれか一項に記載の有機電界発光素子。
［７］ 前記一般式（１）で表される化合物が、下記一般式（４）〜（７）のいずれかで表される化合物である［１］〜［６］のいずれか一項に記載の有機電界発光素子。

（一般式（４）中、Ｘ⁴⁰¹およびＸ⁴⁰²はそれぞれ独立に酸素原子又は硫黄原子を表す。Ｒ⁴⁰¹〜Ｒ⁴¹⁷はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁴⁰⁸〜Ｒ⁴¹⁰は互いに同一でも異なっていてもよい。ｎ₄₀₁は０又は１を表す。）

（一般式（５）中、Ｘ⁵⁰¹は酸素原子又は硫黄原子を表す。Ｒ⁵⁰¹〜Ｒ⁵¹³はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁵⁰⁸〜Ｒ⁴¹³は互いに同一でも異なっていてもよい。ｎ₅₀₁は０又は１を表す。）

（一般式（６）中、Ｘ⁶⁰¹およびＸ⁶⁰²はそれぞれ独立に酸素原子又は硫黄原子を表す。Ｒ⁶⁰¹〜Ｒ⁶²¹はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁶⁰⁸〜Ｒ⁶¹³は互いに同一でも異なっていてもよい。）

（一般式（７）中、Ｘ⁷⁰¹は酸素原子又は硫黄原子を表す。Ｒ⁷⁰¹〜Ｒ⁷¹⁶はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁷⁰⁸〜Ｒ⁷¹⁶は互いに同一でも異なっていてもよい。）
［８］ 前記燐光発光材料が、下記一般式（Ｅ−１）で表されるイリジウム（Ｉｒ）錯体であることを特徴とする［１］〜［７］のいずれか一項に記載の有機電界発光素子。

（一般式（Ｅ−１）中、Ｚ¹及びＺ²はそれぞれ独立に、炭素原子又は窒素原子を表す。Ａ₁はＺ¹と窒素原子と共に５又は６員のヘテロ環を形成する原子群を表す。Ｂ₁はＺ²と炭素原子と共に５又は６員環を形成する原子群を表す。（Ｘ−Ｙ）はモノアニオン性の二座配位子を表す。ｎ_E1は１〜３の整数を表す。）
［９］ 前記一般式（Ｅ−１）で表されるイリジウム（Ｉｒ）錯体が下記一般式（Ｅ−２）で表されることを特徴とする［８］に記載の有機電界発光素子。

（一般式（Ｅ−２）中、Ａ^E1〜Ａ^E8はそれぞれ独立に、窒素原子、又は、Ｒ^Eで置換された炭素原子を表す。Ｒ^Eは水素原子又は置換基を表す。（Ｘ−Ｙ）はモノアニオン性の二座配位子を表す。ｎ_E2は１〜３の整数を表す。）
［１０］ 前記有機層が、前記燐光発光材料を含む発光層とその他の有機層を有し、前記発光層が前記一般式（１）で表される化合物を含有することを特徴とする［１］〜［９］のいずれか一項に記載の有機電界発光素子。
［１１］ 前記有機層が、前記燐光発光材料を含む発光層とその他の有機層を有し、該その他の有機層が、前記発光層と前記陰極との間に配置され、前記発光層に隣接し、かつ、前記一般式（１）で表される化合物を含有することを特徴とする［１］〜［１０］のいずれか一項に記載の有機電界発光素子。
［１２］ 前記一対の電極間に、前記陰極に隣接する電子輸送層を有し、さらに該電子輸送層の前記陰極の反対側に隣接する正孔ブロック層を任意に有し、前記電子輸送層又は前記正孔ブロック層が前記一般式（１）で表される化合物を含有することを特徴とする［１］〜［１１］のいずれか一項に記載の有機電界発光素子。
［１３］ 前記一対の電極間に配置された有機層が、少なくとも一層の前記一般式（１）で表される化合物を含む組成物の蒸着により形成された層を含むことを特徴とする［１］〜［１２］のいずれか一項に記載の有機電界発光素子。
［１４］ 発光ピーク波長が４９０〜５８０ｎｍであることを特徴とする［１］〜［１３］のいずれか一項に記載の有機電界発光素子。
［１５］ ［１］〜［１４］のいずれか一項に記載の有機電界発光素子を含むことを特徴とする発光装置、照明装置又は表示装置。
［１６］ 下記一般式（８）〜（１１）のいずれかで表されることを特徴とする化合物。

（一般式（８）〜（１１）中、Ｘ⁸⁰¹〜Ｘ⁸⁰⁶はそれぞれ独立に酸素原子又は硫黄原子を表し、Ｒ⁸⁰¹〜Ｒ⁸⁰⁶はそれぞれ独立に水素原子又は炭素数６〜１３のアリール基を表す。Ａ¹¹〜Ａ¹³はそれぞれ独立にＣＨ又は窒素原子を表し、少なくとも１つは窒素原子である。） That is, the present invention can be achieved by the following means.
[1] A substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer includes a phosphorescent material and the following general formula ( An organic electroluminescent device comprising the compound represented by 1).
General formula (1)

(In general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ^{101 to} R ¹¹⁰ represent a hydrogen atom or a substituent (excluding an alkyl group and a cyano group), and a plurality of R ^{108 to} R ¹¹⁰ may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.)
[2] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) has a molecular weight of 550 or more.
[3] In the general formula (1), at least one R ¹¹⁰ is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, and a carbon having these as a substituent. It is an aryl group having 6 to 25 rings, a heteroaryl group having 5 to 25 ring members, or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent. The organic electroluminescent element as described in [1] or [2], wherein
[4] The compound represented by the general formula (1) is a compound represented by the following general formula (2) or (3), any one of [1] to [3] The organic electroluminescent element of description.
General formula (2)

(In the general formula (2), X ²⁰¹ represents an oxygen atom or a .R ²⁰¹ to R ²¹² each independently represent a hydrogen atom a sulfur atom, an aryl group or a heteroaryl group, a plurality of R ²⁰⁸ and R ²⁰⁹ is each L ²⁰¹ represents a single bond or an arylene group and is not a p-terphenylene group, and one of A ²⁰¹ and A ²⁰² is a condensed ring aryl group having 10 to 30 ring members, a condensed ring A heteroaryl group having 8 to 30 ring members, a 6 to 25 carbon aryl group or a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent. A monocyclic heteroaryl group having 5 to 25 ring members as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.
General formula (3)

(In General Formula (3), X ³⁰¹ represents an oxygen atom or a sulfur atom. R ^{301 to} R ³¹⁵ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{308 to} R ³¹² are the same as each other. L ³⁰¹ represents a single bond or an arylene group, one of A ³⁰¹ and A ³⁰² is a condensed ring aryl group having 10 to 30 ring members, and a condensed ring hetero ring having 8 to 30 ring members. An aryl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent; 25 represents a monocyclic heteroaryl group, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.)
[5] The organic electroluminescent element as described in any one of [1] to [4], wherein R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1) are both hydrogen atoms.
[6] The organic electroluminescence according to any one of [1] to [5], wherein the compound represented by the general formula (1) is a compound having a glass transition temperature of 100 ° C. or higher. element.
[7] The compound represented by the general formula (1) is a compound represented by any one of the following general formulas (4) to (7), according to any one of [1] to [6]. Organic electroluminescent element.

(In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom or a sulfur atom. R ^{401 to} R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ to R ⁴¹⁰ is good .n ₄₀₁ be the same as or different from each other represents 0 or 1.)

(In General Formula (5), X ⁵⁰¹ represents an oxygen atom or a sulfur atom. R ^{501 to} R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{508 to} R ⁴¹³ are the same as each other. Or n ₅₀₁ represents 0 or 1.)

(In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent an oxygen atom or a sulfur atom. R ^{601 to} R ⁶²¹ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same or different from each other.)

(In General Formula (7), X ⁷⁰¹ represents an oxygen atom or a sulfur atom. R ^{701 to} R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{708 to} R ⁷¹⁶ are the same as each other. But it may be different.)
[8] The organic electric field according to any one of [1] to [7], wherein the phosphorescent material is an iridium (Ir) complex represented by the following general formula (E-1): Light emitting element.

(In General Formula (E-1), Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle together with Z ¹ and the nitrogen atom. B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 is an integer of 1 to 3. Represents.)
[9] The organic electroluminescent element as described in [8], wherein the iridium (Ir) complex represented by the general formula (E-1) is represented by the following general formula (E-2).

(In the formula (E-2), the A ^E1 to A ^E8 each independently a nitrogen atom, or, .R ^E representing a carbon atom substituted with R ^E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n _E2 represents an integer of 1 to 3.)
[10] The organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the light-emitting layer contains a compound represented by the general formula (1) [1] ] The organic electroluminescent element as described in any one of [9] to [9].
[11] The organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the other organic layer is disposed between the light-emitting layer and the cathode and adjacent to the light-emitting layer. And the organic electroluminescent element as described in any one of [1]-[10] characterized by containing the compound represented by the said General formula (1).
[12] An electron transport layer adjacent to the cathode is provided between the pair of electrodes, and a hole blocking layer adjacent to the opposite side of the electron transport layer to the cathode is optionally provided, and the electron transport layer Or the said hole block layer contains the compound represented by the said General formula (1), The organic electroluminescent element as described in any one of [1]-[11] characterized by the above-mentioned.
[13] The organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing a compound represented by the general formula (1) [1] ] The organic electroluminescent element as described in any one of [12].
[14] The organic electroluminescent element as described in any one of [1] to [13], wherein an emission peak wavelength is 490 to 580 nm.
[15] A light-emitting device, a lighting device, or a display device comprising the organic electroluminescent element according to any one of [1] to [14].
[16] A compound represented by any one of the following general formulas (8) to (11).

(In the general formulas (8) to (11), X ^{801 to} X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom, and R ^{801 to} R ⁸⁰⁶ each independently represents a hydrogen atom or an aryl group having 6 to 13 carbon atoms. represents .A ¹¹ to a ¹³ independently represents a CH or a nitrogen atom, at least one is a nitrogen atom.)

ADVANTAGE OF THE INVENTION According to this invention, it is excellent in durability and can provide the organic electroluminescent element with a small chromaticity shift | offset | difference at the time of high temperature storage.
In addition, according to the present invention, it is possible to provide a compound useful for an organic electroluminescent element as a charge transport material, a host material of a light emitting layer, and the like. Further, a light emitting device, a display device, and a display device using the organic electroluminescent element can be provided. A lighting device can be provided.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention. FIG. 2 is a ¹ H-NMR spectrum diagram of Compound 1B-2 of the present invention. FIG. 3 is a ¹ H-NMR spectrum of the compound 1B-3 of the present invention. FIG. 3 is a ¹ H-NMR spectrum of the compound 1B-4 of the present invention. FIG. 2 is a ¹ H-NMR spectrum diagram of Compound 1B-17 of the present invention. 1 is a ¹ H-NMR spectrum of a compound 1D-1 of the present invention. It is a < ¹ > H-NMR spectrum figure of compound 1D-3 of this invention.

  Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In the present specification, “to” is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.

（一般式（１）中、Ｘ¹⁰¹は酸素原子又は硫黄原子を表し、Ｒ¹⁰¹〜Ｒ¹¹⁰は水素原子又は置換基（但し、アルキル基とシアノ基を除く）を表し、複数のＲ¹⁰⁸〜Ｒ¹¹⁰は互いに同一でも異なっていてもよい。Ｌ¹⁰¹は単結合又はアリーレン基を表す。）。
有機電界発光素子では、陰極から電子が注入され、陽極から正孔が注入されて、これらが有機分子上を移動しながら、有機層（機能上、発光層と呼ばれることがある）でこれらが再結合する。その際に生じる励起エネルギーを利用して、発光材料が発光している。そこで、有機電界発光素子の寿命（耐久性）を考えた場合、材料の安定性が重要である。特に、材料上を電荷（電子又は正孔）が移動することから、材料の電荷に対する安定性（＝ラジカル状態での安定性）が非常に重要である。いかなる理論に拘泥するものでもないが、本発明では、ｐ−ターフェニル構造を導入した化合物を用いることで、ラジカル状態でのスピン密度分布を他のフェニル基やビフェニル基よりも一層広く非局在化できることを見出した。ここで、スピン密度分布が広がるほど、ラジカル種は熱力学的に安定化される。このため、ｐ−ターフェニル構造を備えたジベンゾチオフェン又はジベンゾフラン誘導体はラジカル状態での高い安定性を確保することができると考えられる。その結果、有機電界発光素子の耐久性を格段に向上させることができたと考えられる。さらに、ｐ−ターフェニル構造を導入した化合物は、可動性部位が例えばｍ−ターフェニル構造の場合に比べて少なく、高温時に有機層の膜質変化を防止できるため、有機電界発光素子の高温保管後の色度ずれも小さくすることができたと考えられる。 [Organic electroluminescence device]
The organic electroluminescent element of the present invention has a substrate, a pair of electrodes including an anode and a cathode disposed on the substrate, and an organic layer disposed between the electrodes, and the organic layer emits phosphorescence. A material and a compound represented by the following general formula (1) are included.
General formula (1)

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (excluding alkyl group and a cyano group), a plurality of R ¹⁰⁸ to R ¹¹⁰ may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.
In an organic electroluminescent device, electrons are injected from the cathode and holes are injected from the anode, and these move on the organic molecules and are regenerated in the organic layer (which may be called a light emitting layer functionally). Join. The light emitting material emits light using the excitation energy generated at that time. Therefore, when considering the lifetime (durability) of the organic electroluminescent element, the stability of the material is important. In particular, since charges (electrons or holes) move on the material, the stability of the material against the charge (= stability in the radical state) is very important. Although not bound by any theory, in the present invention, by using a compound having a p-terphenyl structure, the spin density distribution in the radical state is more broadly delocalized than other phenyl groups and biphenyl groups. I found out that Here, the radical species are thermodynamically stabilized as the spin density distribution increases. For this reason, it is considered that a dibenzothiophene or dibenzofuran derivative having a p-terphenyl structure can ensure high stability in a radical state. As a result, it is considered that the durability of the organic electroluminescent element could be remarkably improved. Furthermore, the compound having a p-terphenyl structure introduced is less mobile than the m-terphenyl structure, for example, and can prevent changes in the film quality of the organic layer at high temperatures. It is considered that the chromaticity shift of the image could be reduced.

The structure of the organic electroluminescent element of the present invention is not particularly limited. FIG. 1 shows an example of the configuration of the organic electroluminescent element of the present invention. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
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.
Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, light emission wavelength, and a use.

<Board>
The organic electroluminescent element of the present invention has a substrate.
The substrate used in the present invention 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.

<Electrode>
The organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
In view of the properties of the light-emitting element, at least one of the pair of electrodes, the anode and the cathode, is preferably transparent or translucent.

(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.

<Organic layer>
The organic electroluminescent element of the present invention has an organic layer disposed between the electrodes, and the organic layer includes a phosphorescent material and a compound represented by the general formula (1).
There is no restriction | limiting in particular in the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on the said transparent electrode or the said semi-transparent electrode. In this case, the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
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.
Hereinafter, in the organic electroluminescent element of the present invention, the configuration of the organic layer, the method for forming the organic layer, preferred embodiments of the layers constituting the organic layer, and materials used for the layers will be described in order.

(Organic layer structure)
In the organic electroluminescent element of the present invention, the organic layer preferably includes a charge transport layer. The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, a low-cost and highly efficient organic electroluminescent device can be produced.
The organic electroluminescent element of the present invention preferably has a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains the compound represented by the general formula (1). Furthermore, in the organic electroluminescent element of the present invention, it is more preferable that the organic layer has a light emitting layer containing the phosphorescent material and another organic layer. However, in the organic electroluminescent element of the present invention, even when the organic layer has a light emitting layer and other organic layers, the layers do not necessarily have to be clearly distinguished.

In the organic electroluminescent element of the present invention, the organic layer contains a phosphorescent material and a compound represented by the general formula (1). At this time, there is no particular limitation on the place where the phosphorescent material and the compound represented by the general formula (1) are included. In this invention, it is more preferable that the said organic layer has the light emitting layer containing the said phosphorescence-emitting material, and another organic layer, and the said light emitting layer contains the compound represented by the said General formula (1). At this time, it is preferable that the compound represented by the general formula (1) is used as a host compound of the light emitting layer.
Further, an electron transport layer adjacent to the cathode is provided between the pair of electrodes, and a hole blocking layer adjacent to the side opposite to the cathode of the electron transport layer is optionally included, and the electron transport layer or It is also preferable that the hole blocking layer contains a compound represented by the general formula (1).
A plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.

(Formation method of organic layer)
In the organic electroluminescence device of the present invention, each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
In the organic electroluminescent element of the present invention, the organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing the compound represented by the general formula (1). Is preferred.

(Light emitting layer)
The light emitting layer receives holes from an anode, a hole injection layer, or a hole transport layer, and receives electrons from a cathode, an electron injection layer, or an electron transport layer when an electric field is applied. It is a layer having a function of providing and emitting light. However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism. The light emitting layer in the organic electroluminescent element of the present invention preferably contains at least one kind of the phosphorescent material.

  The light emitting layer in the organic electroluminescence device of the present invention may be composed of only the phosphorescent material, or may be a mixed layer of a host material and the phosphorescent material. The phosphorescent material may be one kind or two or more kinds. 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.

  Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

  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.

In the organic electroluminescent element of the present invention, it is preferable that the light emitting layer contains a compound represented by the general formula (1), and the host material of the light emitting layer is represented by the general formula (1). It is a more preferable embodiment to use a compound. Here, in this specification, the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
Hereinafter, as the material of the light emitting layer, the host material other than the compound represented by the general formula (1), the phosphorescent light emitting material, and the compound represented by the general formula (1) will be described in order. In addition, the compound represented by the said General formula (1) may be used other than the said light emitting layer in the organic electroluminescent element of this invention.

(1) Compound Represented by General Formula (1) Hereinafter, the compound represented by the following general formula (1) will be described.

（一般式（１）中、Ｘ¹⁰¹は酸素原子又は硫黄原子を表し、Ｒ¹⁰¹〜Ｒ¹¹⁰は水素原子又は置換基（但し、アルキル基とシアノ基を除く）を表し、複数のＲ¹⁰⁸〜Ｒ¹¹⁰は互いに同一でも異なっていてもよい。Ｌ¹⁰¹は単結合又はアリーレン基を表す。）
なお、本発明において、前記一般式（１）の説明における水素原子は同位体（重水素原子等）も含み、また更に置換基を構成する原子は、その同位体も含んでいることを表す。
本発明において、「置換基」というとき、その置換基は置換されていてもよい。例えば、本発明で「アルキル基」と言う時、フッ素原子で置換されたアルキル基（例えばトリフルオロメチル基）やアリール基で置換されたアルキル基（例えばトリフェニルメチル基）なども含むが、「炭素数１〜６のアルキル基」と言うとき、置換されたものも含めた全ての基として炭素数が１〜６であることを示す。 General formula (1)

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (excluding alkyl group and a cyano group), a plurality of R ¹⁰⁸ to R ¹¹⁰ may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.)
In the present invention, the hydrogen atom in the description of the general formula (1) includes an isotope (deuterium atom and the like), and the atoms constituting the substituent further include the isotope.
In the present invention, when referred to as “substituent”, the substituent may be substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that the number of carbon atoms is 1 to 6 as all groups including those substituted.

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom. A sulfur atom having a large van der Faals radius is preferred from the viewpoint of improving electron mobility.

In the general formula (1), the substituents represented by R ^{101 to} R ¹¹⁰ are substituents excluding an alkyl group and a cyano group, and can include the following substituent group A independently. Furthermore, you may have a substituent. Examples of the further substituent include a group selected from the substituent group A.

<< Substituent group A >>
An alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), Alkynyl group (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.), aryl group (preferably carbon It has 6 to 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthryl and the like, and an amino group (preferably having a carbon number). 0-30, more preferably 0-20 carbon atoms, particularly preferably 0-10 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, for example, methoxy , Ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, Phenyloxy, 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, pyrazinyloxy, pyrimidinyloxy, quinolyloxy, etc. ), An acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, pivaloyl, etc.), alkoxy A carbonyl 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, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably 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 2 to 30 carbon atoms, and more). Preferably it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms. Ruoxy and the like. ), An acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (Preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, and particularly preferably having 2 to 12 carbon atoms, such as methoxycarbonylamino), an aryloxycarbonylamino group (preferably having a carbon number) 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino, and the like, and sulfonylamino groups (preferably 1 to 30 carbon atoms, more preferably Has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms. And sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms, such as sulfamoyl and methylsulfamoyl). , Dimethylsulfamoyl, phenylsulfamoyl, 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, for example, carbamoyl , Methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, Ethylthio etc.), arylthio group (preferably Has 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 they are C1-C20, Most preferably, it is C1-C12, for example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio etc. are mentioned), sulfonyl. A group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), a sulfinyl group (preferably having 1 to 1 carbon atoms). 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl and the like. It is. ), 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), sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (heteroaryl group) Preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of heteroatoms include Nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl Quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.), silyl group ( Preferably, it has 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). Si 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.

R ^{101 to} R ¹¹⁰ are each independently preferably a hydrogen atom, an aryl group or a heteroaryl group.

The aryl group represented by R ^{101 to} R ¹¹⁰ preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 18 carbon atoms. For example, a phenyl group, a xylyl group, a biphenyl group, A phenyl group, a naphthyl group, an anthryl group, a triphenylenyl group, etc. are mentioned.
The heteroaryl group represented by R ^{101 to} R ¹¹⁰ preferably has 5 to 30 ring members, more preferably 5 to 20 ring members, and particularly preferably 5 to 15 ring members. For example, pyridyl group, pyrimidinyl group, triazinyl group Examples include a pyrazinyl group, a pyridazinyl group, a carbazolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, and the like.

R ^{101 to} R ¹⁰⁷ are more preferably each independently a hydrogen atom or an aryl group having 6 to 18 carbon atoms, particularly preferably a hydrogen atom or a phenyl group, and more preferably a hydrogen atom. However, an embodiment in which one or more of R ^{101 to} R ¹⁰⁷ is a phenyl group is also preferable, and an embodiment in which 1 or 2 is a phenyl group is also more preferable.

R ¹⁰⁸ and R ¹⁰⁹ are preferably a hydrogen atom, an aryl group having 6 to 18 carbon atoms or a heteroaryl group. In the organic electroluminescent device of the present invention, both R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1) are hydrogen. More preferably it is an atom.
When R ¹⁰⁸ and R ¹⁰⁹ have a further substituent, the substituent is preferably a substituted or unsubstituted aryl group or heteroaryl group, and more preferably a phenyl group.

Examples of R ¹¹⁰ include an aryl group having 10 to 30 ring members in which at least one R ¹¹⁰ is a condensed ring, a heteroaryl group having 8 to 30 ring members that is a condensed ring, and 6 to 25 carbon atoms having these as substituents. Or a heteroaryl group having 5 to 25 ring members, or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, and other R ¹¹⁰ is preferably a hydrogen atom, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 25 ring members.
Examples of R ¹¹⁰ include an aryl group having 12 to 18 ring members in which at least one R ¹¹⁰ is a condensed ring, a heteroaryl group having 9 to 13 ring members that is a condensed ring, or 6 to 18 carbon atoms having these as a substituent. Or a monocyclic heteroaryl group having 6 to 13 carbon atoms and a monocyclic aryl group having 6 to 13 carbon atoms as a substituent, and other R More preferably, ¹¹⁰ is a hydrogen atom. Further, the monocyclic heteroaryl group having 6 to 13 ring members having a monocyclic aryl group having 6 to 18 carbon atoms as a substituent is a ring having a monocyclic aryl group having 6 to 10 carbon atoms as a substituent. It is preferably a monocyclic heteroaryl group having 6 to 10 members, and the preferred number of monocyclic aryl groups having 6 to 10 carbon atoms is 1 or 2.
An aryl group having 10 to 30 ring members that is the condensed ring, an aryl group having 6 to 25 carbon atoms that has an aryl group having 8 to 30 ring members that is a condensed ring as a substituent, and 6 to 6 carbon atoms having these as a substituent R ¹¹⁰ which is a 25 aryl group or a 6 to 13 ring heteroaryl group, or a monocyclic heteroaryl group having 5 to 20 ring members having a monocyclic aryl group having 6 to 20 carbon atoms as a substituent. The position of the substituent may be any of the ortho, meta, and para positions relative to the substituent that forms the p-terphenylene skeleton of the benzene ring substituted by R ¹¹⁰ , and among these, the meta position Or it is preferable that it is para position from a viewpoint of suppressing the photocyclization reaction between this ^R110 and another substituent, or a viewpoint of a device drive voltage reduction. Moreover, when the luminescent color from an organic electroluminescent element is green (light emission peak wavelength is 490-580 nm), it is more preferable that it is a meta position from a viewpoint of luminous efficiency.

L ¹⁰¹ represents a single bond or an arylene group. The arylene group may be a condensed ring (for example, naphthyl group, anthryl group, etc.), but when the emission color from the organic electroluminescent element is green (emission peak wavelength is 490 to 580 nm), it is condensed from the viewpoint of luminous efficiency. An arylene group having no ring is preferable, and a phenylene group which may have a substituent or a structure in which a plurality of the phenylene groups are connected by a single bond is more preferable. Preferable examples of the arylene group represented by L ¹⁰¹ include a phenylene group, a biphenylene group, and a terphenylene group. Moreover, these connection modes are not particularly limited.
L ¹⁰¹ is preferably a single bond, a phenylene group, a biphenylene group or a terphenylene group, preferably a single bond or a terphenylene group (among them, a p-terphenylene group or an m-terphenylene group is more preferable, and a p-terphenylene group is more preferable. An unsubstituted p-terphenylene group is particularly preferred), and a single bond is more preferred.
In the present invention, p-terphenylene and m-terphenylene each represent the following structure (* represents a bond).

L ²⁰¹ is preferably unsubstituted, but may optionally have a substituent. Examples of the substituent in the case where L ²⁰¹ has a further substituent include the above-mentioned substituent group A, and a substituted or unsubstituted aryl group (phenyl group or biphenyl group) is preferable, and a phenyl group is preferable.

  In the organic electroluminescent element of the present invention, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (2) or (3).

General formula (2)

In general formula (2), ^X201 represents an oxygen atom or a sulfur atom. R ²⁰¹ to R ²¹² each independently represent a hydrogen atom, an aryl group or a heteroaryl group, a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same or different from each other. L ²⁰¹ represents a single bond or an arylene group, not a p- terphenylene group. One of A ²⁰¹ and A ²⁰² is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, an aryl group having 6 to 25 carbon atoms having these as a substituent, or Represents a heteroaryl group having 5 to 25 ring members or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, the other being a hydrogen atom, aryl Represents a group or a heteroaryl group.

A preferred range of X ²⁰¹ in formula (2) is the same as the preferred range of X ¹⁰¹ in formula (1).

The preferred range of R ^{201 to} R ²⁰⁹ in the general formula (2) is the same as the preferred range of R ^{101 to} R ¹⁰⁹ in the general formula (1).
R ^{210 to} R ²¹² in the general formula (2) are preferably a hydrogen atom or an aryl group having 6 to 20 carbon atoms, and more preferably a hydrogen atom.

The aryl group having 10 to 30 ring members which is a condensed ring represented by one of A ²⁰¹ and A ²⁰² in the general formula (2), the heteroaryl group having 8 to 30 ring members which is a condensed ring, and carbon having these as a substituent Preferred are an aryl group having 6 to 25 rings, a heteroaryl group having 5 to 25 ring members, or a monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent. The range is a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group, a carbazolyl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring members, or a carbon number of 6 to It is a monocyclic heteroaryl group having 5 to 25 ring members having 13 monocyclic aryl groups as substituents. Among them, a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group or a phenylene group having these substituents is more preferable, and a dibenzothiophenyl group, a dibenzofuranyl group or a triphenylenyl group is particularly preferable. A dibenzothiophenyl group or a triphenylenyl group is more particularly preferable, and a triphenylenyl group is more preferable. In addition, these condensed rings may have the above skeleton as a basic skeleton and further may be condensed with each other.
The other of A ²⁰¹ and A ²⁰² in the general formula (2) is preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring members, and preferably a hydrogen atom. More preferred.

L ²⁰¹ in the general formula (2) represents a single bond or an arylene group and is not a p-terphenylene group.
Arylene groups of the L ²⁰¹ represents the fused ring (e.g. naphthyl group, etc. anthryl group) may be any color of light emitted from the organic electroluminescent device green case (emission peak wavelength 490～580Nm) is the luminous efficiency From the viewpoint, it is preferably an arylene group having no condensed ring, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or a 3,5′-biphenylene group. It is particularly preferred.
L ²⁰¹ in the general formula (2) is preferably a single bond.

一般式（３）中、Ｘ³⁰¹は酸素原子又は硫黄原子を表す。Ｒ³⁰¹〜Ｒ³¹⁵はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ³⁰⁸〜Ｒ³¹²は互いに同一でも異なっていてもよい。Ｌ³⁰¹は単結合又はアリーレン基を表す。Ａ³⁰¹およびＡ³⁰²の一方は縮合環である環員数１０〜３０のアリール基、縮合環である環員数８〜３０のヘテロアリール基、これらを置換基として有する炭素数６〜２５のアリール基又は環員数５〜２５のヘテロアリール基、あるいは、炭素数６〜２５の単環のアリール基を置換基として有する環員数５〜２０の単環のヘテロアリール基を表し、もう一方は水素原子、アリール基又はヘテロアリール基を表す。 General formula (3)

In general formula (3), X ³⁰¹ represents an oxygen atom or a sulfur atom. R ^{301 to} R ³¹⁵ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and the plurality of R ^{308 to} R ³¹² may be the same as or different from each other. L ³⁰¹ represents a single bond or an arylene group. One of A ³⁰¹ and A ³⁰² is a condensed ring aryl group having 10 to 30 ring members, a condensed ring hetero ring group having 8 to 30 ring members, an aryl group having 6 to 25 carbon atoms having these as a substituent, or Represents a heteroaryl group having 5 to 25 ring members or a monocyclic heteroaryl group having 5 to 20 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, the other being a hydrogen atom, aryl Represents a group or a heteroaryl group.

The preferable range of X ³⁰¹ in the general formula (3) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

The preferable range of R ^{301 to} R ³¹² in the general formula (3) is the same as the preferable range of R ^{101 to} R ¹⁰⁹ in the general formula (1).
The preferred range of R ^{313 to} R ³¹⁵ in the general formula (3) is the same as the preferred range of R ^{210 to} R ²¹² in the general formula (2).

The preferred ranges of A ³⁰¹ and A ³⁰² in the general formula (3) are the same as the preferred ranges of A ²⁰¹ and A ²⁰² in the general formula (2).

The arylene group represented by L ³⁰¹ in the general formula (3) may be a condensed ring (eg, naphthyl group, anthryl group, etc.), but the emission color from the organic electroluminescent element is green (emission peak wavelength is 490 to 580 nm). In some cases, an arylene group having no condensed ring is preferable from the viewpoint of luminous efficiency, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or 3, A 5′-biphenylene group is particularly preferred.
L ³⁰¹ in the general formula (3) is preferably a single bond.

  In the organic electroluminescent element of the present invention, the compound represented by the general formula (1) is a compound represented by any one of the following general formulas (4) to (7) and a general formula (11) described below. It is particularly preferable that the compound represented by the general formula (1) is more particularly preferably a compound represented by any one of the following general formulas (4) to (7).

In the general formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom or a sulfur atom. R ^{401 to} R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R ^{408 to} R ⁴¹⁰ may be the same as or different from each other. n ₄₀₁ represents 0 or 1;

The preferable range of X ⁴⁰¹ and X ⁴⁰² in the general formula (4) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

The preferable ranges of R ^{401 to} R ⁴⁰⁷ and R ^{411 to} R ⁴¹⁷ in the general formula (4) are the same as the preferable ranges of R ^{101 to} R ¹⁰⁷ in the general formula (1).
The preferable range of R ^{408 to} R ⁴¹⁰ in the general formula (4) is the same as the preferable range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).
In the general formula (4), n ₄₀₁ is preferably 0.

一般式（５）中、Ｘ⁵⁰¹は酸素原子又は硫黄原子を表す。Ｒ⁵⁰¹〜Ｒ⁵¹³はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁵⁰⁸〜Ｒ⁴¹³は互いに同一でも異なっていてもよい。ｎ₅₀₁は０又は１を表す。

In general formula (5), ^X501 represents an oxygen atom or a sulfur atom. R ^{501 to} R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R ^{508 to} R ⁴¹³ may be the same as or different from each other. n ₅₀₁ represents 0 or 1;

The preferable range of X ⁵⁰¹ in the general formula (5) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

The preferable range of R ^{501 to} R ⁵⁰⁷ in the general formula (5) is the same as the preferable range of R ^{101 to} R ¹⁰⁷ in the general formula (1).
The preferable range of R ^{508 to} R ⁵¹⁰ in the general formula (5) is the same as the preferable range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).
R ^{511 to} R ⁵¹³ in the general formula (5) are preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring members, and more preferably a hydrogen atom.

In the general formula (5), n ₅₀₁ is preferably 0.

In general formula (6), ^X601 and ^X602 each independently represent an oxygen atom or a sulfur atom. R ^{601 to} R ⁶²¹ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R ^{608 to} R ⁶¹³ may be the same as or different from each other.

The preferable range of X ⁶⁰¹ and X ⁶⁰² in the general formula (6) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

The preferred ranges of R ^{601 to} R ⁶⁰⁷ and R ^{614 to} R ⁶²⁰ in the general formula (6) are the same as the preferred ranges of R ^{101 to} R ¹⁰⁷ in the general formula (1).
The preferable range of R ^{608 to} R ⁶¹³ in the general formula (6) is the same as the preferable range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).

一般式（７）中、Ｘ⁷⁰¹は酸素原子又は硫黄原子を表す。Ｒ⁷⁰¹〜Ｒ⁷¹⁶はそれぞれ独立に水素原子、アリール基又はヘテロアリール基を表し、複数のＲ⁷⁰⁸〜Ｒ⁷¹⁶は互いに同一でも異なっていてもよい。

In general formula (7), ^X701 represents an oxygen atom or a sulfur atom. R ^{701 to} R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and the plurality of R ^{708 to} R ⁷¹⁶ may be the same as or different from each other.

The preferable range of X ⁷⁰¹ in the general formula (7) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

The preferred range of R ^{701 to} R ⁷⁰⁷ in the general formula (7) is the same as the preferred range of R ^{101 to} R ¹⁰⁷ in the general formula (1).
The preferable range of R ^{708 to} R ⁷¹³ in the general formula (7) is the same as the preferable range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).
The preferred range of R ^{714 to} R ⁷¹⁶ in the general formula (7) is the same as the preferred range of R ^{511 to} R ⁵¹³ in the general formula (5).

<< Compound of the Present Invention-Particularly Preferred Aspect of Compound Represented by Formula (1) >>
Among the compounds represented by the general formula (1), a compound represented by any one of the following general formulas (8) to (11) is particularly preferable in the present invention. The compound of the present invention represented by any one of the following general formulas (8) to (11) is an organic material such as an electrophotography, an organic transistor, an organic photoelectric conversion element (for energy conversion, sensor use, etc.), or an organic electroluminescence element. It can be preferably used for an electronic device, and is particularly preferably used for an organic electroluminescent device.

In the general formulas (8) to (11), X ^{801 to} X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom, and R ^{801 to} R ⁸⁰⁶ each independently represents a hydrogen atom or an aryl group having 6 to 13 carbon atoms. . A ^{11 to} A ¹³ each independently represent CH or a nitrogen atom, and at least one is a nitrogen atom.
In the general formulas (8) to (11), the preferable range of X ^{801 to} X ^{806 is} the same as the preferable range of X ¹⁰¹ in the general formula (1).

In the general formulas (8) to (11), R ^{801 to} R ⁸⁰⁶ are each independently preferably a hydrogen atom or a phenyl group, and more preferably a hydrogen atom.
In the general formula (11), A ^{11 to} A ¹³ each independently represent CH or a nitrogen atom, and at least one is a nitrogen atom. When the nitrogen atom contained in A ¹¹ to A ¹³ is one, it is preferred A ¹¹ or A ¹² is a nitrogen atom. When there are two nitrogen atoms contained in A ^{11 to} A ¹³ , it is preferable that A ¹² and A ¹³ are nitrogen atoms.
The compound represented by the general formula (11) has one nitrogen atom contained in A ^{11 to} A ¹³ and A ¹¹ or A ¹² is a nitrogen atom, or a nitrogen atom contained in A ^{11 to} A ¹³ More preferably, A ¹² and A ¹³ are two nitrogen atoms, or A ^{11 to} A ¹³ are all nitrogen atoms. Further among them, A ¹¹ and ~A nitrogen atoms contained in the ¹³ one A ¹² is a nitrogen atom compound, A ¹¹ ~A ¹³ nitrogen atoms contained in the 2 Tsude A ¹² and A ¹³ is a nitrogen atom Is particularly preferred.
The compound represented by the general formula (11) has a “nitrogen-containing heterocycle” that can deepen the LUMO, and is preferable from the viewpoint of reducing the device voltage. Moreover, it is also preferable from the viewpoint of small chromaticity deviation during high temperature storage.

  The molecular weight of the compound represented by the general formula (1) is usually 400 or more and 1500 or less, preferably 450 or more and 1200 or less, more preferably 500 or more and 1100 or less, and more preferably 550 or more and 1000 or less. Is more preferable. When the molecular weight is 450 or more, it is advantageous for forming a high-quality amorphous thin film, and when the molecular weight is 1200 or less, the solubility and sublimation property are improved, which is advantageous for improving the purity of the compound. In the organic electroluminescent element of the present invention, the molecular weight of the compound represented by the general formula (1) is preferably 550 or more from the viewpoint of reducing the chromaticity shift during high temperature storage. On the other hand, from the viewpoint of laminating a composition containing the compound represented by the general formula (1) by vapor deposition, the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less.

When the compound represented by the general formula (1) is used as a host material of a light emitting layer of an organic electroluminescence device or a charge transport material of a layer adjacent to the light emitting layer, an energy gap in a thin film state from the light emitting material (present invention) In the case where the light emitting material is a phosphorescent light emitting material such as the organic electroluminescent element, if the lowest excited triplet (T ₁ ) energy in the thin film state is large, the light emission is prevented from being quenched and the efficiency is improved. It is advantageous. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large.

The T ₁ energy in the film state of the compound represented by the general formula (1) is preferably 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less and preferably 2.39 eV (55 kcal). / Mol) and more preferably 3.25 eV (75 kcal / mol) or less. In the organic electroluminescent element of the present invention, it is preferable from the viewpoint of luminous efficiency that the T ₁ energy of the compound represented by the general formula (1) is higher than the T ₁ energy of the phosphorescent material described later. In particular, when the emission color from the organic electroluminescence device is green (emission peak wavelength is 490 to 580 nm), from the viewpoint of light emission efficiency, the T ₁ energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol). mol) or less.

The T ₁ energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a film thickness of about 50 nm by a vacuum deposition method, and the phosphorescence emission spectrum of the thin film is F-7000 Hitachi Spectrofluorimeter (Hitachi High-Technologies) under liquid nitrogen temperature. Use to measure. T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

  From the viewpoint of stably operating the organic electroluminescent element against heat generation during high temperature driving or during element driving, and from the viewpoint of reducing chromaticity deviation during high temperature storage, the organic electroluminescent element of the present invention has the general formula ( The compound represented by 1) is preferably a compound having a glass transition temperature of 100 ° C. or higher. The glass transition temperature (Tg) of the compound represented by the general formula (1) is more preferably from 100 ° C to 400 ° C, particularly preferably from 120 ° C to 400 ° C, and from 140 ° C to 400 ° C. More preferably, it is as follows.

  When the purity of the compound represented by the general formula (1) is low, impurities work as traps for charge transport or promote deterioration of the device. Therefore, the purity of the compound represented by the general formula (1) The higher the better. The purity can be measured by, for example, high performance liquid chromatography (HPLC), and the area ratio of the compound represented by the general formula (1) when detected with a light absorption intensity of 254 nm is preferably 95.0% or more, and more It is preferably 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more. Examples of a method for increasing the purity of the compound represented by the general formula (1) include sublimation purification.

  Specific examples of the compound represented by the general formula (1) are listed below, but the present invention is not limited thereto.

  The compound exemplified as the compound represented by the general formula (1) is a metal catalyst (for example, between a corresponding boronic acid or boronic ester or boronic ester salt and a corresponding halogen compound or triflate compound). It can be synthesized by a coupling reaction (for example, Suzuki-Miyaura coupling) using a ligand (such as Pd or Ni) and a ligand (such as triphenylphosphine or Buchwald ligand). For example, it can be synthesized by the method described in Patent Document 1 described above.

In the present invention, the compound represented by the general formula (1) is not limited in its use and may be contained in any layer in the organic layer. Examples of the introduction layer of the compound represented by the general formula (1) include the light emitting layer, a layer between the light emitting layer and the cathode (particularly a layer adjacent to the light emitting layer), and between the light emitting layer and the anode. It is preferably contained in any one of these layers, more preferably contained in any one or more of the light emitting layer, electron transport layer, electron injection layer, exciton block layer, hole block layer, electron block layer. Preferably, it is more preferably contained in any one of the light emitting layer, the electron transport layer, and the hole blocking layer, and particularly preferably contained in the light emitting layer or the electron transport layer. Moreover, you may use the compound represented by the said General formula (1) in said several layer. For example, you may use for both a light emitting layer and an electron carrying layer.
When the compound represented by the general formula (1) is contained in the light emitting layer, the compound represented by the general formula (1) is included in an amount of 0.1 to 99% by mass with respect to the total mass of the light emitting layer. It is preferable to include 1 to 97 mass%, and it is more preferable to include 10 to 96 mass%. When the compound represented by the general formula (1) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass with respect to the total mass of the layer other than the light emitting layer. More preferably, it is contained by mass%.

(Phosphorescent material)
In the present invention, it is preferable that the light emitting layer has at least one phosphorescent material. In the present invention, in addition to the phosphorescent light emitting material, a fluorescent light emitting material or a phosphorescent light emitting material different from the phosphorescent light emitting material contained in the light emitting layer can be used as the light emitting material.
Details of these fluorescent light-emitting materials and phosphorescent light-emitting materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.

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 the luminescent material include iridium (Ir) complex, platinum (Pt) complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu. Examples include phosphorescent metal complex compounds such as complexes, Tb complexes, Gd complexes, Dy complexes, and Ce complexes. Particularly preferred is an iridium (Ir) complex, a platinum (Pt) complex, or a Re complex. Among them, at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is used. An iridium (Ir) complex, a platinum (Pt) complex, or a Re complex is preferable. Furthermore, iridium (Ir) complex and platinum (Pt) complex are particularly preferable, and iridium (Ir) complex is most preferable from the viewpoint of luminous efficiency, driving durability, chromaticity and the like.
These phosphorescent metal complex compounds are preferably contained in the light emitting layer together with the compound represented by the general formula (1).

  As the phosphorescent material contained in the light emitting layer, it is preferable to use an iridium (Ir) complex represented by the following general formula (E-1). Hereinafter, the iridium (Ir) complex represented by the general formula (E-1) will be described.

In general formula (E-1), Z < ¹ > and Z < ² > represent a carbon atom or a nitrogen atom each independently.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of ₁ to 3.

n _E1 represents an integer of 1 to 3, and is preferably 2 or 3. When n _E1 is 2 or 3, a plurality of ligands may be the same as or different from each other.
Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom. The 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom includes a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the 5- or 6-membered hetero ring formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole. A ring, more preferably a pyridine ring, an imidazole ring and a pyrazine ring, still more preferably a pyridine ring and an imidazole ring, and most preferably a pyridine ring.

The 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent, and the substituent group A can be applied as the substituent. The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, a heteroaryl group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group or a perfluoroalkyl group is preferably selected. For the purpose of adjusting the intermolecular interaction, an alkyl group, a cycloalkyl group, an aryl group or the like is preferably selected.

  The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.

B ₁ represents a 5- or 6-membered ring containing Z ² and a carbon atom. Examples of the 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole is preferable as the 5- or 6-membered ring formed by B ₁ , Z ² and carbon atom. A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.

The 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as the substituent on the carbon atom. The following substituent group B can be applied.
The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

<< Substituent group B >>
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, including phenyl, p-methylphenyl, naphthyl, anthryl, etc.), cyano group, heterocyclic group (including heteroaryl group, preferably carbon The hetero atom is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl. , Pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, Benzimidazo , Benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and further substituents are groups selected from the substituent group B described above. Can be mentioned.

  The substituent on the carbon is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group , Aryl groups, heteroaryl groups and the like are selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected. For the purpose of adjusting the intermolecular interaction, an alkyl group, a cycloalkyl group, an aryl group or the like is preferably selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
The 5- or 6-membered heterocyclic substituent formed by A ₁ , Z ¹ and a nitrogen atom is linked to the 5- or 6-membered substituent formed by B ₁ , Z ² and a carbon atom. Then, the same condensed ring as described above may be formed.

(XY) represents a bidentate monoanionic ligand. Examples of bidentate monoanionic ligands are described on pages 89-90 of Lamansky et al., WO 02/15645.
The bidentate monoanionic ligand represented by (XY) is preferably a bidentate monoanionic ligand represented by the following general formula (L-1).

In General Formula (L-1), R ^L1 and R ^L2 each independently represent an alkyl group, an aryl group, or a heteroaryl group.
R ^L3 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.

The alkyl group represented by R ^{L1 to} R ^L3 may have a substituent and may be saturated or unsaturated. Examples of the substituent in the case of having a substituent include the following substituent Z ′, and preferred substituent Z ′ includes a phenyl group, a heteroaryl group, a fluorine atom, a silyl group, an amino group, a cyano group, or a combination thereof. And a phenyl group, a fluorine atom, and a cyano group are more preferable. The alkyl group represented by R ^{L1 to} R ^L3 is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.

<< Substituent Z '>>
An alkyl group (preferably having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, such as methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n- Butyl, neopentyl, n-pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl and the like), an alkenyl group (preferably having 2 to 8 carbon atoms, more preferably 2 to 5 carbon atoms, such as vinyl) And aryl groups (having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, such as phenyl group, naphthyl group, anthracenyl group, tetracenyl group, pyrenyl group, perylenyl group, triphenylenyl group, and chrysenyl group). Heteroaryl group (preferably having 4 to 30 carbon atoms, more preferably carbon 4 to 20, for example, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiophene, furan, oxazole, thiazole, imidazole, pyrazole, triazole, oxadiazole, thiadiazole, etc.), alkoxy group (preferably having 1 carbon atom) To 8, more preferably 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, an n-propyloxy group, and an iso-propyloxy group), a phenoxy group, a halogen atom (preferably a fluorine atom), A silyl group (preferably having 4 to 30 carbon atoms, more preferably 4 to 20 carbon atoms, such as trimethylsilyl group, triethylsilyl group, triphenylsilyl group), amino group (preferably having 2 to 60 carbon atoms, More preferably, it has 2 to 40 carbon atoms, and dimethyl Amino group, a diethylamino group, and a diphenylamino group), a cyano group or a group formed by combining these groups, a plurality of substituents Z 'may form an aryl ring bonded to each other. Examples of the aryl ring formed by bonding a plurality of substituents Z ′ to each other include a phenyl ring and a pyridine ring, and a phenyl ring is preferable.

The aryl group represented by R ^{L1 to} R ^L3 may be condensed or may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z ′. The substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group. The aryl group represented by R ^{L1 to} R ^L3 is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 18 carbon atoms.

The heteroaryl group represented by R ^{L1 to} R ^L3 may be condensed or may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z ′. The substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group. The heteroaryl group represented by R ^{L1 to} R ^L3 is preferably a heteroaryl group having 4 to 12 carbon atoms, and more preferably a heteroaryl group having 4 to 10 carbon atoms.

R ^L1 and R ^L2 are preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and particularly preferably an alkyl group.
The alkyl group represented by R ^L1 and R ^L2 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, such as a methyl group or an ethyl group. N-propyl group, iso-propyl group, iso-butyl group, t-butyl group, n-butyl group, cyclohexyl group and the like, and methyl group, ethyl group, iso-butyl group, or t-butyl group A methyl group is preferable, and a methyl group is particularly preferable.

R ^L3 is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

A preferred embodiment of the iridium (Ir) complex represented by the general formula (E-1) is an iridium (Ir) complex material represented by the following general formula (E-2).
Next, general formula (E-2) is demonstrated.

In formula (E-2), A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E2 represents an integer of 1 to 3.

A ^{E1 to} A ^E8 each independently represent a nitrogen atom or C—R ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. Examples of the ring formed include the same condensed rings described in the general formula (E-1). As the substituent represented by R ^E , those exemplified as the substituent group A can be applied.
A ^E1 is preferably a to A ^E4 is C-R ^E, if A ^E1 to A ^E4 is C-R ^E, preferably a hydrogen atom R ^E of A ^E3, alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. R ^E in A ^E1 , A ^E2 and A ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.

A ^{E5 to} A ^E8 are preferably C-R ^E , and when A ^{E5 to} A ^E8 are C-R ^E , R ^E is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, heteroaryl Group, dialkylamino group, diarylamino group, alkyloxy group, cyano group, or fluorine atom, more preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, or fluorine atom. And more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. When the emission wavelength is shifted to the short wavelength side, A ^E6 is preferably a nitrogen atom.
(X-Y), and n _E2 of the general formula in (E1) (X-Y) , and has the same meaning as n _E1 preferable ranges are also the same.

  A more preferable form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

In the general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, perfluoroalkyl group, trifluorovinyl _{group, -CO 2 R, -C (O} ) R, -NR 2, -NO 2, -OR, halogen atom, an aryl group or a heteroaryl group, a substituent Z may be included. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
A represents CR ′ or a nitrogen atom, and R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O ) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^{T1 to} R ^T7 and R ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl. The condensed 4- to 7-membered ring may further have a substituent Z. Of these, the case where R ^T1 and R ^T7 , or R ^T5 and R ^T6 are condensed to form a benzene ring is preferred, and the case where R ^T5 and R ^T6 are condensed to form a benzene ring is particularly preferred.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or -SO ₃ R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(X—Y) represents a monoanionic bidentate ligand. n _E3 represents an integer of 1 to 3.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The alkyl group represented by R ^{T1 to} R ^T7 and R ′ is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The cycloalkyl group represented by R ^{T1 to} R ^T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total. A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
The alkenyl group represented by R ^{T1 to} R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, and 3-pentenyl.
The alkynyl group represented by R ^{T1 to} R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include ethynyl and propargyl. , 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^{T1 to} R ^T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^{T1 to} R ^T7 and R ′ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, or a naphthyl group.

The heteroaryl group represented by R ^{T1 to} R ^T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group. Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group Benz Sookisazoriru group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, such as 7 pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^{T1 to} R ^T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

Any one of R ^{T1 to} R ^T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent Z. The definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R ^{T1 to} R ^T7 and R ′.
Further, it is particularly preferable that A represents CR ′, and among R ^{T1 to} R ^T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R ^{T1 to} R ^T7 , And R ′ are particularly preferably 0 to 2 alkyl groups and the rest are all hydrogen atoms.

n _E3 is preferably 2 or 3. When n _E3 is 2 or 3, the plurality of ligands may be the same or different. The type of ligand in the complex is preferably composed of 1 to 2 types.
(XY) is synonymous with (XY) in general formula (E-1), and its preferable range is also the same.

  One of the preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

R ^{T1 to} R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are R ^{T1 to} R ^T4 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and optionally having a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any _{one of} R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or -SO ₃ R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
Moreover, the preferable range in R < ₁ >'-R< ₅ >' is the same as R ^{< T1} > -R <^T7> , R 'in general formula (E-3). Further, it is particularly preferable that A represents CR ′, and among R ^{T1 to} R ^T4 , R ′, and R ₁ ′ to R ₅ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^{T1 to} R ^T4 , R ′, and R ₁ ′ to R ₅ ′, 0 to 2 are more preferably alkyl groups and the rest are all hydrogen atoms.

  Although the preferable specific example of a compound represented by the said general formula (E-1) is enumerated below, it is not limited to the following.

  The compounds exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP2009-99783A or various methods described in US Pat. No. 7,279,232. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

  The phosphorescent light emitting material is preferably contained in the light emitting layer, but its use is not limited and may be further contained in any layer in the organic layer.

  The phosphorescent light-emitting material in the light-emitting layer is preferably contained in the light-emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total compound mass that generally forms the light-emitting layer. From the viewpoint of external quantum efficiency, the content is more preferably 1% by mass to 50% by mass, and particularly preferably 2% by mass to 40% by mass.

  Use the compound represented by any one of the general formulas (1) to (7) and the compound represented by any one of the general formulas (E-1) to (E-4) in combination in the light emitting layer. Is particularly preferred in the present invention.

(3) Other host materials Examples of other host materials that can be used for the light emitting layer other than the compound represented by the general formula (1) include compounds having the following structure as a partial structure. it can.
Aromatic hydrocarbon, pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styryl Conductivity of anthracene, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, polythiophene, etc. Polymer oligomer, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorine Olenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine, 8- Various metal complexes typified by metal complexes of quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazol ligands and their derivatives (may have substituents and condensed rings) And the like.

(Other layers)
The organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
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,
Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The organic electroluminescent element of the present invention preferably comprises (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
The organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
Specifically, an example of a preferable embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
Hereinafter, other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.

(A) Organic layer preferably disposed between the anode and the light emitting layer First, (A) the organic layer preferably disposed between the anode and the light emitting layer will be described.

(A-1) 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.
Regarding the hole injection layer and the hole transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By containing an electron-accepting dopant in the hole injection layer, hole injection properties are improved, driving voltage is reduced, and efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations. For example, tetracyanoquinodimethane ( TCNQ), tetrafluorotetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide and the like.

  The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total compound mass forming the hole injection layer. % Content is more preferable, and 0.2% by mass to 30% by mass is more preferable.

(A-2) Electron Blocking 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.
The T ₁ energy in the film state of the organic compound composing the electron blocking layer must be higher than the T ₁ energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. Is preferred.
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.

(A-3) Material [compound represented by general formula (M-1)] particularly preferably used for the organic layer preferably disposed between the anode and the light emitting layer
The organic electroluminescent device of the present invention is represented by at least one of the following general formula (M-1) as a material particularly preferably used for the organic layer preferably disposed between the (A) anode and the light emitting layer. Can be mentioned.

The compound represented by the general formula (M-1) is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited, and the organic layer It may be further contained in any of the layers. As the introduction layer of the compound represented by the general formula (M-1), any of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge blocking layer, or a plurality of layers can be used. Can be contained.
The organic layer adjacent to the light emitting layer between the light emitting layer and the anode, containing the compound represented by the general formula (M-1), is more preferably an electron block layer or a hole transport layer.

In the general formula (M-1), Ar ₁ and Ar ₂ are each independently one or more selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S Represents a 5- or 6-membered heterocycloalkyl or cycloalkyl containing a heteroatom, and may further have a substituent Z. Ar ₁ and Ar ₂ may be bonded to each other by a single bond, alkylene, or alkenylene (with or without a condensed ring) to form a condensed 5- to 9-membered ring.
Ar ₃ represents P-valent alkyl, aryl, heteroaryl, or arylamino, and may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or -SO ₃ R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
p is an integer of 1 to 4, and when p is 2 or more, Ar ₁ and Ar ₂ may be the same or different.

  Another preferable embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-2).

In the general formula (M-2), R ^M1 represents an alkyl group, an aryl group, or a heteroaryl group.
R ^{M2 to} R ^M23 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, a cyano group, a nitro group, or a fluorine atom.

In the general formula (M-2), R ^M1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z. R ^M1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. Preferred substituents when the aryl group of R ^M1 has a substituent include an alkyl group, a halogen atom, a cyano group, an aryl group, and an alkoxy group, and an alkyl group, a halogen atom, a cyano group, and an aryl group are more preferable. An alkyl group, a cyano group, or an aryl group is more preferable. The aryl group of R ^M1 is preferably a phenyl group that may have a substituent Z, and more preferably a phenyl group that may have an alkyl group or a cyano group.

R ^{M2 to} R ^M23 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to 12 carbon atoms), Alkoxy group (preferably having 1 to 8 carbon atoms), aryloxy group (preferably having 6 to 30 carbon atoms), amino group (preferably having 0 to 24 carbon atoms), silyl group (preferably having 0 to 18 carbon atoms), cyano Represents a group, a nitro group, or a fluorine atom, and these may have the substituent Z described above.

R ^M2 , R ^M7 , R ^M8 , R ^M15 , R ^M16 and R ^M23 are preferably a hydrogen atom or an alkyl group or an aryl group which may have a substituent Z, more preferably a hydrogen atom. .
R ^M4 , R ^M5 , R ^M11 , R ^M12 , R ^M19 and R ^M20 are preferably a hydrogen atom, an alkyl or aryl group which may have a substituent Z, or a fluorine atom, more preferably a hydrogen atom. Is an atom.
R ^M3 , R ^M6 , R ^M9 , R ^M14 , R ^M17 and R ^M22 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, a fluorine atom, or a cyano group, and more A hydrogen atom or an alkyl group which may have a substituent Z is preferable, and a hydrogen atom is more preferable.
R ^M10 , R ^M13 , R ^M18 and R ^M21 are preferably a hydrogen atom, an alkyl group optionally having a substituent Z, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom, or a cyano group. More preferably a hydrogen atom, an alkyl or aryl group optionally having a substituent Z, a nitro group, a fluorine atom, or a cyano group, still more preferably a hydrogen atom or a substituent Z. It is an alkyl group that may be present. When the alkyl group has a substituent, the substituent is preferably a fluorine atom, and the alkyl group which may have the substituent Z preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. is there.

  Another preferable embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-3).

In the general formula (M-3), R ^{S1 to} R ^S5 are each independently an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, — C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group, or a heteroaryl group may be represented, and may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. When a plurality of R ^{S1 to} R ^S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
a represents an integer of 0 to 4, and when a plurality of R ^S1 are present, they may be the same or different and may be bonded to each other to form a ring. b to e each independently represent an integer of 0 to 5, and when there are a plurality of R ^{S2 to} R ^S5 , they may be the same or different, and any two may be bonded to form a ring. Good.
q is an integer of 1 to 5, and when q is 2 or more, a plurality of R ^S1 may be the same or different, and may be bonded to each other to form a ring.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The alkyl group represented by R ^{S1 to} R ^S5 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as a methyl group or an ethyl group. I-propyl group, cyclohexyl group, t-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The cycloalkyl group represented by R ^{S1 to} R ^S5 is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, such as a cyclopentyl group or cyclohexyl group. Groups and the like.
The alkenyl group represented by R ^{S1 to} R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like can be mentioned.
The alkynyl group represented by R ^{S1 to} R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl, 1-propynyl , 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^{S1 to} R ^S5 include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^{S1 to} R ^S5 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a biphenyl group, and a terphenyl group.

The heteroaryl group represented by R ^{S1 to} R ^S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group, For example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group, furyl group, benzofuryl group, thienyl group, Benzothienyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxa Examples include zolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thiazolinyl group, sulfolanyl group, carbazolyl group, dibenzofuryl group, dibenzothienyl group, pyridoindolyl group and the like. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^{S1 to} R ^S5 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom or an alkyl group. Group, cyano group, trifluoromethyl group, fluoro group and aryl group, more preferably a hydrogen atom, an alkyl group and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom and an alkyl group are more preferable.

Any two of R ^{S1 to} R ^S5 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The 7-membered ring may further have a substituent Z. The definition and preferred range of cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R ^{S1 to} R ^S5 .

When the compound represented by the general formula (M-1) is used in the hole transport layer, the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100% by mass, It is preferable that 80-100 mass% is contained, and it is especially preferable that 95-100 mass% is contained.
Moreover, when using the compound represented by the said general formula (M-1) for a some organic layer, it is preferable to contain in said range in each layer.

  The compound represented by the general formula (M-1) may contain only one kind in any of the organic layers, and the compound represented by the plurality of general formulas (M-1) may be arbitrarily selected. You may contain combining in a ratio.

  The thickness of the hole transport layer containing the compound represented by the general formula (M-1) is preferably 1 nm to 500 nm, more preferably 3 nm to 200 nm, and 5 nm to 100 nm. Is more preferable. The hole transport layer is preferably provided in contact with the light emitting layer.

The lowest excited triplet (T ₁ ) energy in the film state of the compound represented by the general formula (M-1) is 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less. Is preferably 2.39 eV (55 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less. In the organic electroluminescent element of the present invention, it is preferable from the viewpoint of luminous efficiency that the T ₁ energy of the compound represented by the general formula (M-1) is higher than the T ₁ energy of the phosphorescent material. . In particular, when the emission color from the organic electroluminescence device is green (emission peak wavelength is 490 to 580 nm), from the viewpoint of light emission efficiency, the T ₁ energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol). mol) or less.

  The hydrogen atoms constituting the general formula (M-1) include hydrogen isotopes (deuterium atoms and the like). In this case, all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used.

  The compound represented by the general formula (M-1) can be synthesized by combining various known synthesis methods. Most commonly, carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo). Regarding the coupling reaction of the obtained carbazole compound and halogenated aryl compound using a palladium catalyst, Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like. The reaction temperature and reaction time are not particularly limited, and the conditions described in the above literature can be applied.

  The compound represented by the general formula (M-1) preferably forms a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be suitably used. The molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Particularly preferred.

  Specific examples of the compound represented by the general formula (M-1) are shown below, but the present invention is not limited thereto.

(B) Organic layer preferably disposed between the cathode and the light emitting layer Next, the (B) organic layer preferably disposed between the cathode and the light emitting layer will be described.

(B-1) Electron injection layer and 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. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, the compound represented by the general formula (1) can be used. Other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane. Derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivatives Represented by metal complexes, metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole ligands, and siloles Organosilane derivatives, a layer containing such is preferable.

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

  The electron injection layer preferably contains an electron donating dopant. By including an electron donating dopant in the electron injection layer, the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) , Tetrathianaphthacene (TTT), dihydroimidazole compounds such as bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

  The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass, based on the total mass of the compound forming the electron injection layer. It is more preferable that 0.5% by mass to 30% by mass is contained.

(B-2) 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.
The T ₁ energy in the film state of the organic compound constituting the hole blocking layer is higher than the T ₁ energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
As an example of the organic compound constituting the hole blocking layer, the compound represented by the general formula (1) can be used.
Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like. In the present invention, the hole blocking layer is not limited to the function of actually blocking holes, and the exciton of the light emitting layer may not diffuse into the electron transport layer, or may have a function of blocking energy transfer quenching. . The compound of the present invention can also be preferably applied as a hole blocking layer.
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.

(B-3) Material particularly preferably used for the organic layer preferably disposed between the cathode and the light emitting layer The organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer. As a material particularly preferably used for the material of the organic layer, the compound represented by the general formula (1), the aromatic hydrocarbon compound (particularly, the following general formula (Tp-1)) and the following general formula (O— The compound represented by 1) can be mentioned.
Hereinafter, the aromatic hydrocarbon compound and the compound represented by the general formula (O-1) will be described.

[Aromatic hydrocarbon compounds]
The aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but its use is not limited, and any layer in the organic layer may be included. Further, it may be contained. The introduction layer of the aromatic hydrocarbon compound is contained in one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer. be able to.
The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode and containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transport layer, and more preferably an electron transport layer.

The aromatic hydrocarbon compound preferably comprises only carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.
When the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, more preferably 85 to 100% by mass. When the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably included in an amount of 0.1 to 99% by mass, more preferably 1 to 95% by mass, and more preferably 10 to 95%, based on the total mass of the light emitting layer. It is more preferable to include the mass%.
As the aromatic hydrocarbon compound, it is preferable to use a hydrocarbon compound having only a carbon atom and a hydrogen atom, having a molecular weight in the range of 400 to 1200 and having a condensed polycyclic skeleton having a total carbon number of 13 to 22. Examples of the condensed polycyclic skeleton carbon atoms in total 13 to 22, fluorene fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, is preferably one of triphenylene, in view of T _1, triphenylene, phenanthrene Is more preferable, and triphenylene is more preferable from the viewpoint of stability of the compound and charge injection / transport properties, and a compound represented by the following general formula (Tp-1) is particularly preferable.

  The hydrocarbon compound represented by the general formula (Tp-1) preferably has a molecular weight in the range of 400 to 1200, more preferably 400 to 1000, and still more preferably 400 to 800. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.

  The application of the hydrocarbon compound represented by the general formula (Tp-1) is not limited, and may be further contained in any layer within the organic layer as well as the organic layer adjacent to the light emitting layer. .

In the general formula (Tp-1), R ^{12 to} R ²³ are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, A fluorenyl group, a naphthyl group, or a triphenylenyl group is represented. However, R ^{12 to} R ²³ are not all hydrogen atoms.

Examples of the alkyl group represented by R ^{12 to} R ²³ include a substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group and the like can be mentioned, preferably methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, more preferably methyl group, ethyl group, or A tert-butyl group.

R ^{12 to} R ²³ are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, and a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
A benzene ring that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (which may be further substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group); It is particularly preferred.

  The total number of aryl rings in the general formula (Tp-1) is preferably 2 to 8, and preferably 3 to 5. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

R ^{12 to} R ²³ each independently preferably has a total carbon number of 20 to 50, and more preferably a total carbon number of 20 to 36. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

  The hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-2).

In General Formula (Tp-2), a plurality of Ar ¹ are the same, and a phenyl group, a fluorenyl group, a naphthyl group, or a group optionally substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, or Represents a triphenylenyl group.

The alkyl group and alkyl group represented by Ar ¹ , a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group that may be substituted with a triphenylenyl group include R ^{12 to} R ²³ . It is synonymous with what was mentioned, and a preferable thing is also the same.

  The hydrocarbon compound represented by the general formula (Tp-1) is also preferably a hydrocarbon compound represented by the following general formula (Tp-3).

  In general formula (Tp-3), L is a phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof, which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group. An n-valent linking group is represented. n represents an integer of 1 to 6.

The alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group that forms the n-valent linking group represented by L has the same meaning as that described for R ^{12 to} R ²³ .
L is preferably an alkyl group or an n-valent linking group formed by combining a benzene ring, a fluorene ring, or a combination thereof, which may be substituted with a benzene ring.
Although the preferable specific example of L is given to the following, it is not limited to these. In the specific examples, it is bonded to the triphenylene ring by *.

  n is preferably 1 to 5, and more preferably 1 to 4.

When the hydrocarbon compound represented by the general formula (Tp-1) is used as a host material of a light emitting layer of an organic electroluminescent element or a charge transport material of a layer adjacent to the light emitting layer, it is in a thin film state than the light emitting material. When the energy gap (low emission triplet (T ₁ ) energy in a thin film state when the light emitting material is a phosphorescent light emitting material) is large, the light emission is prevented from quenching, which is advantageous in improving efficiency. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large. The T ₁ energy in the film state of the hydrocarbon compound represented by the general formula (Tp-1) is preferably 1.77 eV (40 kcal / mol) or more and 3.51 eV (81 kcal / mol) or less. It is more preferable that it is 39 eV (55 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less. In the organic electroluminescent element of the present invention, it is preferable from the viewpoint of luminous efficiency that the T ₁ energy of the compound represented by the general formula (Tp-1) is higher than the T ₁ energy of the phosphorescent material. . In particular, when the emission color from the organic electroluminescence device is green (emission peak wavelength is 490 to 580 nm), from the viewpoint of light emission efficiency, the T ₁ energy is 2.39 eV (55 kcal / mol) or more and 2.82 eV (65 kcal / mol). mol) or less.

The T ₁ energy of the hydrocarbon compound represented by the general formula (Tp-1) can be obtained by a method similar to the method in the description of the general formula (1).

  The glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is 80 ° C. or more and 400 ° C. or less from the viewpoint of stably operating the organic electroluminescence device against heat generation during high temperature driving or during device driving. The temperature is preferably 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.

  Hereinafter, specific examples of the hydrocarbon compound represented by the general formula (Tp-1)) will be exemplified, but the hydrocarbon compound used in the present invention is not limited thereto. Absent.

The compounds exemplified as the hydrocarbon compound represented by the general formula (Tp-1) include WO05 / 013388 pamphlet, WO06 / 130598 pamphlet, WO09 / 021107 pamphlet, US2009 / 0009065, WO09 / 008311 pamphlet and WO04 / 018587 pamphlet.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

[Compound represented by formula (O-1)]
As a material particularly preferably used for the material of the organic layer that is preferably arranged between the (B) cathode and the light emitting layer, it is possible to use a compound represented by the following general formula (O-1) as an organic electroluminescence. It is preferable from the viewpoint of element efficiency and driving voltage. Below, general formula (O-1) is demonstrated.

In general formula (O-1), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. A ^{O1 to} A ^O4 each independently represent C—R ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different. L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring or a heteroaryl ring. n ^O1 represents an integer of 2 to 6.

R ^O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these are the aforementioned substituents. You may have the group A. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. A preferable substituent when the aryl group of R ^O1 has a substituent includes an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, and even more preferably an unsubstituted group. A phenyl group or a 2-phenylphenyl group.

A ^{O1 to} A ^O4 each independently represent C—R ^A or a nitrogen atom. Of A ^{O1 to} A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. It is preferred that all of A ^{O1 to} A ^O4 are C—R ^A , or A ^O1 is a nitrogen atom and A ^{O2 to} A ^O4 are C—R ^A , A ^O1 is a nitrogen atom, and A ^O2 to More preferably, A ^O4 is C—R ^A , A ^O1 is a nitrogen atom, A ^{O2 to} A ^O4 are C—R ^A , and all R ^A are hydrogen atoms.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent Z ′. The plurality of R ^A may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group. L ^O1 may have the above-described substituent Z ′, and when it has a substituent, the substituent is preferably an alkyl group, an aryl group, or a cyano group. Specific examples of L ^O1 include the following.

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, and more preferably 2 or 3. n ^O1 is most preferably 3 from the viewpoint of the efficiency of the organic electroluminescent element, and most preferably 2 from the viewpoint of the durability of the organic electroluminescent element.
The compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

In general formula (O-2), R ^O1 independently represents an alkyl group, an aryl group, or a heteroaryl group. R ^{O2 to} R ^O4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^{O1 to} A ^O4 each independently represent C—R ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different.

R ^O1 and A ^O1 to A ^O4, the general formula (O1) in the same meaning as R ^O1 and A ^O1 to A ^O4 of, also the same preferable ranges thereof.
R ^{02 to} R ⁰⁴ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have the substituent group A described above. R ^{02 to} R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

  The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stability at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably ˜400 ° C., more preferably 120 ° C. to 400 ° C., and still more preferably 140 ° C. to 400 ° C.

  Specific examples of the compound represented by the general formula (O-1) are shown below, but the compound used in the present invention is not limited thereto.

  The compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

  In the organic electroluminescent device of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the layer on the cathode side adjacent to the light emitting layer. It is more preferable that it is contained.

<Protective layer>
In the present invention, the entire organic electroluminescent 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. The material for the protective layer may be inorganic or organic.

<Sealing container>
The organic electroluminescent element of the present invention may be sealed entirely 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.

<Driving method>
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. Obtainable.
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 external quantum efficiency of the organic electroluminescent device of the present invention is preferably 7% or more, and more preferably 10% 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 around 300 to 400 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 substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

<Emission wavelength>
There is no restriction | limiting in the light emission wavelength of the organic electroluminescent element of this invention. For example, among the three primary colors of light, it may be used for red light emission, green light emission, or blue light emission. Among them, the organic electroluminescence device of the present invention has an emission peak wavelength of 490 to 580 nm, considering the lowest excited triplet (T ₁ ) energy of the compound represented by the general formula (1). From the viewpoint of
Specifically, in the organic electroluminescence device of the present invention, when the compound represented by the general formula (1) is used as a host material for the light emitting layer, an electron transport layer or an electron transport material for the hole blocking layer, light emission The peak wavelength is preferably 490 to 580 nm, more preferably 490 to 550 nm, and particularly preferably 500 to 535 nm.

<Use of the organic electroluminescent device of the present invention>
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for a device that is driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.

[Light emitting device]
The light emitting device of the present invention includes the organic electroluminescent element of the present invention.
Next, the light emitting device of the present invention will be described with reference to FIG.
FIG. 2 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. 2 includes a transparent substrate (supporting substrate) 2, an organic electroluminescent element 10, a sealing container 16, 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]
The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.
Next, the illumination device of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention. As shown in FIG. 3, the illumination device 40 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. 3, 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.

[Display device]
The display device of the present invention includes the organic electroluminescent element of the present invention.
Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.

  The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.

[Examples 1 to 6]
1. Synthesis of compound represented by general formula (1) (synthesis of compound 1B-2)

  According to the above scheme, Compound 1B-2 was synthesized by repeating Suzuki-Miyaura coupling.

Compounds 1B-3, 1B-4, 1B-17, 1D-1, and 1D-3, which are compounds represented by the general formula (1), are converted into the same Suzuki-Miyaura cup as in the synthesis of Compound 1B-2. The ring was synthesized.
¹ H-NMR data of the following compounds 1B-2, 1B-3, 1B-4, 1B-17, 1D- ^{1, and} 1D-3 synthesized in Examples 1 to 6 are shown in FIGS. 4 to 9, respectively.

Details of ¹ H-NMR data of compounds 1B-2, 1B-3, 1B-4, 1B-17, 1D- ^{1, and} 1D-3 read from FIGS. 4 to 9 are shown below.

Compound 1B-2
1H-NMR (solvent): heavy DMSO, standard: tetramethylsilane) δ (ppm)
7.53-7.58 (4H, m), 7.67-7.73 (6H, m), 7.78 (2H, d), 7.88 (2H, d), 7.94 (4H, s), 8.02-8.06 (2H, m)), 8.13 (2H, s), 8.44 (4H, dd)

Compound 1B-3
1H-NMR (solvent): heavy CDCl ₃ , standard: tetramethylsilane) δ (ppm)
7.38-7.42 (2H, m), 7.46-7.52 (6H, m), 7.54-7.62 (8H, m), 7.68-7.74 (12H, m) ), 7.94 (2H, s), 8.20-8.23 (4H, m)

Compound 1B-4
1H-NMR (solvent): heavy CDCl ₃ , standard: tetramethylsilane) δ (ppm)
7.46-7.52 (2H, m), 7.57-7.78 (11H, m), 7.80-7.88 (6H, m), 7.98 (1H, dd), 8. 08-8.09 (2H, m), 8.19-8.23 (2H, m), 8.68-8.72 (3H, m), 8.75-8.79 (2H, m), 8.93 (1H, s)

Compound 1B-17
1H-NMR (solvent): heavy CDCl ₃ , standard: tetramethylsilane) δ (ppm)
7.44-7.52 (4H, m), 7.56-7.69 (12H, m), 7.73-7.76 (4H, m), 7.78-7.83 (8H, m) ), 7.84-7.87 (2H, m), 7.94 (2H, s), 8.07 (2H, s), 8.18-8.23 (4H, m)

Compound 1D-1
1H-NMR (solvent): heavy CDCl ₃ , standard: tetramethylsilane) δ (ppm)
7.44-7.66 (12H, m), 7.74-7.87 (9H, m), 7.96 (2H, s), 8.01 (1H, s), 8.08 (1H, s) 8.19-8.24 (6H, m)

Compound 1D-3
1H-NMR (solvent): heavy CDCl ₃ , standard: tetramethylsilane) δ (ppm)
7.46-7.69 (12H, m), 7.75-7.77 (2H, m), 7.83-7.88 (6H, m), 8.10 (2H, s), 8. 19-8.23 (2H, m) 8.27-8.34 (3H, m), 8.56 (1H, s), 8.75 (2H, dd)

  Thereafter, the compound represented by the general formula (1) used for the preparation of the organic electroluminescence device described later and the comparative compounds 1 to 4 having a part of the structure similar to them are the same as the compound 1B-2. And synthesized.

2. Fabrication and Evaluation of Organic Electroluminescence Device (2-A) Fabrication of Green Phosphorescent Organic Electroluminescence Device-1
All materials used for the production of the organic electroluminescent element were subjected to sublimation purification in advance.

[Comparative Example 1]
(Preparation of anode)
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat 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.
This was used as an anode (ITO film, transparent anode).

(Lamination of organic layers)
On the anode, the first to fifth organic layers were sequentially deposited using the following compounds by vacuum deposition. In addition, the structure of the compound used for each layer is shown.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Comparative compound 1 (host material) and green phosphorescent material GD-1 (guest material) (mass ratio 90:10): film thickness 30 nm
Fourth layer: TpH-17: film thickness 10 nm
Fifth layer: Alq: film thickness 40 nm

(Preparation of cathode)
On top of this, 0.1 nm of lithium fluoride and 200 nm of metallic aluminum were deposited in this order to form a cathode.

(Production of organic electroluminescence)
The laminated body having five organic layers between the cathode and the anode is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV) And an organic electroluminescent element of Comparative Example 1 was obtained.

(Evaluation of organic electroluminescence device)
(A) The organic electroluminescent device of durability Comparative Example 1, at room temperature brightness continues to emit light by applying a DC voltage to be 5000 cd / m ^2, the time which the luminance is completed to reach a 4000 cd / m ² Was measured. This time was used as an index of durability of the organic electroluminescent element.
In each example and comparative example described later, in Table 1 described below, the durability when the organic electroluminescent element of Comparative Example 1 was used was set to 100, and the relative value of durability was less than 100. X: 100 or more and less than 150: ◯, 150 or more: ◎.
Here, durability is so preferable that a number is large.

(B) Chromaticity shift after high-temperature storage For the organic electroluminescent element of Comparative Example 1 after high-temperature storage (48 hours at 100 ° C.) and before storage, a DC voltage was applied so that the luminance was 1000 cd / m ² . An emission spectrum was measured by an emission spectrum measurement system (ELS 1500) manufactured by Shimadzu Corporation, and chromaticity (CIE chromaticity) was calculated.
The chromaticity after storage at high temperature (48 hours at 100 ° C.) in which the x-coordinate or y-coordinate of the CIE (x, y) coordinate deviates by 0.01 or more from that before storage is x, both of which are 0 A value of 0.005 or more and less than 0.01 was rated as ◯, and a value of less than 0.005 was rated as ◎.

(C) Glass transition temperature The glass transition temperature of the comparative compound 1 used as the host material in the third layer of the organic layer was measured by differential scanning calorimetry (DSC).
The results are shown in Table 1 below, where the glass transition temperature Tg is less than 100 ° C., x is 100 ° C. or more and less than 120 ° C., and ◯ is 120 ° C. or more.

[Examples A1 to A9 and Comparative Examples 2 to 4]
Comparative Example 1 except that the compound represented by the general formula (1) shown in Table 1 below or Comparative Compounds 2 to 4 shown in Table 1 below was used in place of Comparative Compound 1 as the material for the third layer of the organic layer in Comparative Example 1. In the same manner as in Example 1, organic electroluminescent elements of Examples A1 to A9 and Comparative Examples 2 to 4 were obtained.
Comparative compound 1 is compound compound 2S described in International Publication WO2009 / 073245, Comparative Compound 3 is compound compound 2S described in International Publication WO2009 / 021126, and Comparative Compound 4 is International Publication WO2009 / Compound compound 9S described in No. 021126.

  These organic electroluminescent elements were evaluated in the same manner as in Comparative Compound 1 above. The results are shown in Table 1 below.

From Table 1 above, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of Examples A1 to A9 as the host compound of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good. Moreover, the compound represented by General formula (1) of these Examples A1 to A9 had a high glass transition temperature and was good.
On the other hand, the organic electroluminescent elements of Comparative Examples 1, 2, and 4 were those using Comparative Compounds 1, 2, and 4 as the host compound of the light emitting layer, and were found to have poor durability. The organic electroluminescent element of Comparative Example 3 was obtained by using Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor. Further, Comparative Compounds 1 to 3 used in Comparative Examples 1 to 3 had a low glass transition temperature.
In addition, the emission peak wavelength of the organic electroluminescent element produced in Examples A1 to A9 was 515 to 535 nm.

(2-B) Preparation of organic electroluminescent element emitting green phosphorescence-2
[Comparative Example 5]
About the organic layer of the organic electroluminescent element of Comparative Example 1, the same as Comparative Example 1 except that NPD used for the second layer was replaced with HTL-1, and GD-1 used for the third layer was replaced with GD-2. Thus, an organic electroluminescent element of Comparative Example 5 was obtained. The structure of the organic layer in Comparative Example 5 is shown below.
First layer: LG101: film thickness 10 nm
Second layer: HTL-1: film thickness 30 nm
Third layer: Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
Fourth layer: TpH-17: film thickness 10 nm
Fifth layer: Alq: film thickness 40 nm

[Examples B1 to B4, Comparative Example 6]
In Comparative Example 5, the same procedure as in Comparative Example 5 was performed except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material of the third layer of the organic layer. Organic electroluminescent elements of Examples B1 to B4 and Comparative Example 6 were obtained.
The organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. The durability when the organic electroluminescence device of Comparative Example 5 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescence devices of other Examples and Comparative Examples were less than 100. The product was evaluated as x, 100 or more and less than 150 as 、, and 150 or more as ◎.
The results are shown in Table 2 below.

From Table 2 above, the organic electroluminescent elements of the examples using the compounds represented by the general formula (1) of Examples B1 to B6 as the host compounds of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
On the other hand, the organic electroluminescent element of Comparative Example 5 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability. The organic electroluminescent element of Comparative Example 6 uses Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after storage at high temperature was poor.
In addition, the light emission wavelength of the organic electroluminescent element produced in Examples B1 to B6 was 510 to 525 nm.

(2-C) Preparation of organic electroluminescent element emitting red phosphorescence [Comparative Example 7]
For the organic layer of the organic electroluminescent element of Comparative Example 1, LG101 used for the first layer was replaced with GD-1, GD-1 used for the third layer was replaced with red phosphorescent material RD-1, and the fourth layer An organic electroluminescent element of Comparative Example 7 was produced in the same manner as Comparative Example 1 except that TpH-17 used in the above was changed to Alq. The structure of the organic layer in Comparative Example 7 is shown below.
First layer: GD-1: Film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Comparative compound 1 (host material) and red phosphorescent material RD-1 (guest material) (mass ratio 90:10): film thickness 30 nm
Fourth layer: Alq: film thickness 10 nm
Fifth layer: Alq: film thickness 40 nm

[Examples C1 to C3, Comparative Example 8]
In the same manner as in Comparative Example 7, except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material for the third layer of the organic layer in the comparative example 7. Organic electroluminescent elements of Examples C1 to C6 and Comparative Example 8 were obtained.
The organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. The durability when the organic electroluminescent element of Comparative Example 7 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100. The product was evaluated as x, 100 or more and less than 150 as 、, and 150 or more as ◎.
The results are shown in Table 3 below.

From Table 3 above, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of Examples C1 to C3 as the host compound of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
On the other hand, the organic electroluminescent element of Comparative Example 7 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability. The organic electroluminescent element of Comparative Example 8 was obtained by using Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor.
In addition, the light emission wavelength of the organic electroluminescent element produced in Examples C1 to C3 was 615 to 630 nm.

(2-D) Preparation of Green Phosphorescent Organic Electroluminescent Device-3
[Comparative Example 9]
The device of Comparative Example 9 is the same as Comparative Example 5 except that TpH-17 used for the fourth layer of the device of Comparative Example 5 is changed to OM-8 and Alq used for the fifth layer is changed to OM-8. Produced. The structure of the organic layer in Comparative Example 9 is shown below.
First layer: LG101: film thickness 10 nm
Second layer: HTL-1: film thickness 30 nm
Third layer: Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
Fourth layer: OM-8: film thickness 10 nm
Fifth layer: OM-8: film thickness 40 nm

[Examples D1 to D5, Comparative Example 10]
In the same manner as in Comparative Example 9, except that the compound represented by the general formula (1) and the comparative compound 3 were used in place of the comparative compound 1 as the material of the third layer of the organic layer in the comparative example 9. Organic electroluminescent elements of Examples D1 to D5 and Comparative Example 10 were obtained.
These elements were evaluated in the same manner as in Comparative Example 1. The organic electroluminescent elements in these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. The durability when the organic electroluminescent element of Comparative Example 9 was used as an evaluation criterion for durability was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100. The product was evaluated as x, 100 or more and less than 150 as 、, and 150 or more as ◎.
The results are shown in Table 4 below.

From Table 4 above, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of Examples D1 to D5 as the host compounds of the light emitting layer are all durable and the color after high temperature storage. It was found that the degree deviation was good.
On the other hand, the organic electroluminescent element of Comparative Example 9 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer, and was found to have poor durability. The organic electroluminescent element of Comparative Example 10 uses Comparative Compound 3 as the host compound of the light emitting layer, and it was found that the chromaticity shift after high temperature storage was poor.
In addition, the light emission wavelength of the organic electroluminescent element produced in Examples D1 to D5 was 510 to 525 nm.

(2-E) Production of Green Phosphorescent Organic Electroluminescent Device-4
(Comparative Example 11)
The device of Comparative Example 11 was prepared in the same manner as Comparative Example 4 except that TpH-17 used for the fourth layer of Comparative Example 5 was replaced with Comparative Compound 1 and Alq used for the fifth layer was replaced with OM-8. Produced. The structure of the organic layer in Comparative Example 11 is shown below.
First layer: LG101: film thickness 10 nm
Second layer: HTL-1: film thickness 30 nm
Third layer: Comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90:10): film thickness 30 nm
Fourth layer: Comparative compound 1: film thickness 10 nm
Fifth layer: OM-8: film thickness 40 nm

[Examples E1 to E3, Comparative Example 12]
In Comparative Example 11, the compound represented by the general formula (1) or the comparative compound 3 is used instead of the comparative compound 1 as the material of the third layer of the organic layer, and the comparative compound 1 is used as the material of the fourth layer of the organic layer. Organic electroluminescent elements of Examples E1 to E3 and Comparative Example 12 were obtained in the same manner as in Comparative Example 11 except that the compound represented by the general formula (1) or the comparative compound 3 was used instead of.
The organic electroluminescent elements of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. The durability when the organic electroluminescent element of Comparative Example 11 was used as a durability evaluation standard was set to 100, and the relative values of the durability of the organic electroluminescent elements of other Examples and Comparative Examples were less than 100. The product was evaluated as x, 100 or more and less than 150 as 、, and 150 or more as ◎.
The results are shown in Table 5 below.

From Table 5 above, the organic electroluminescent elements of the respective examples using the compounds represented by the general formula (1) of Examples E1 to E3 as the host compound of the light emitting layer and the fourth layer of the organic layer are all durable. It was also found that the chromaticity deviation after storage at high temperature was good.
On the other hand, the organic electroluminescent element of Comparative Example 11 was obtained by using Comparative Compound 1 as the host compound of the light emitting layer and the fourth organic layer, and was found to have poor durability. The organic electroluminescent element of Comparative Example 12 uses Comparative Compound 3 as the host compound of the light emitting layer and the fourth layer of the organic layer, and it was found that the chromaticity shift after high temperature storage was poor.
In addition, the light emission wavelength of the organic electroluminescent element produced in Examples E1 to E3 was 510 to 525 nm.

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 Outgoing surface 31 ... Transparent substrate 32 ... Fine particles 40 ... Illumination device

Claims (16)

A substrate,
A pair of electrodes disposed on the substrate, including an anode and a cathode;
An organic layer disposed between the electrodes,
The organic electroluminescent device, wherein the organic layer contains a phosphorescent material and a compound represented by the following general formula (1).
General formula (1)

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (excluding alkyl group and a cyano group), a plurality of R ¹⁰⁸ to R ¹¹⁰ may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.)   The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) has a molecular weight of 550 or more. In the general formula (1), at least one R ¹¹⁰ is an aryl group having 10 to 30 ring members that is a condensed ring, a heteroaryl group having 8 to 30 ring members that is a condensed ring, and 6 to 6 carbon atoms having these as a substituent. 25 aryl group or heteroaryl group having 5 to 25 ring members, or monocyclic heteroaryl group having 5 to 25 ring members having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent. The organic electroluminescent element according to claim 1 or 2. The organic electric field according to any one of claims 1 to 3, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2) or (3). Light emitting element.
General formula (2)

(In the general formula (2), X ²⁰¹ represents an oxygen atom or a .R ²⁰¹ to R ²¹² each independently represent a hydrogen atom a sulfur atom, an aryl group or a heteroaryl group, a plurality of R ²⁰⁸ and R ²⁰⁹ is each L ²⁰¹ represents a single bond or an arylene group and is not a p-terphenylene group, and one of A ²⁰¹ and A ²⁰² is a condensed ring aryl group having 10 to 30 ring members, a condensed ring A heteroaryl group having 8 to 30 ring members, a 6 to 25 carbon aryl group or a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent. A monocyclic heteroaryl group having 5 to 25 ring members as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.
General formula (3)

(In General Formula (3), X ³⁰¹ represents an oxygen atom or a sulfur atom. R ^{301 to} R ³¹⁵ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{308 to} R ³¹² are the same as each other. L ³⁰¹ represents a single bond or an arylene group, one of A ³⁰¹ and A ³⁰² is a condensed ring aryl group having 10 to 30 ring members, and a condensed ring hetero ring having 8 to 30 ring members. An aryl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring members, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent; 25 represents a monocyclic heteroaryl group, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.) 5. The organic electroluminescent element according to claim 1, wherein R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1) are both hydrogen atoms.   The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is a compound having a glass transition temperature of 100 ° C. or higher. The organic electroluminescence device according to any one of claims 1 to 6, wherein the compound represented by the general formula (1) is a compound represented by any one of the following general formulas (4) to (7). .

(In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom or a sulfur atom. R ^{401 to} R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ to R ⁴¹⁰ is good .n ₄₀₁ be the same as or different from each other represents 0 or 1.)

(In General Formula (5), X ⁵⁰¹ represents an oxygen atom or a sulfur atom. R ^{501 to} R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{508 to} R ⁴¹³ are the same as each other. Or n ₅₀₁ represents 0 or 1.)

(In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent an oxygen atom or a sulfur atom. R ^{601 to} R ⁶²¹ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same or different from each other.)

(In General Formula (7), X ⁷⁰¹ represents an oxygen atom or a sulfur atom. R ^{701 to} R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ^{708 to} R ⁷¹⁶ are the same as each other. But it may be different.) The organic electroluminescent element according to claim 1, wherein the phosphorescent material is an iridium (Ir) complex represented by the following general formula (E-1).

(In General Formula (E-1), Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle together with Z ¹ and the nitrogen atom. B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 is an integer of 1 to 3. Represents.) The organic electroluminescent device according to claim 8, wherein the iridium (Ir) complex represented by the general formula (E-1) is represented by the following general formula (E-2).

(In the formula (E-2), the A ^E1 to A ^E8 each independently a nitrogen atom, or, .R ^E representing a carbon atom substituted with R ^E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n _E2 represents an integer of 1 to 3.) The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The said light emitting layer contains the compound represented by the said General formula (1), The organic electroluminescent element as described in any one of Claims 1-9 characterized by the above-mentioned. The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The other organic layer is disposed between the light emitting layer and the cathode, is adjacent to the light emitting layer, and contains a compound represented by the general formula (1). The organic electroluminescent element as described in any one of 1-10. Having an electron transport layer adjacent to the cathode between the pair of electrodes;
Furthermore, optionally having a hole blocking layer adjacent to the opposite side of the cathode of the electron transport layer,
The organic electroluminescent element according to claim 1, wherein the electron transport layer or the hole blocking layer contains a compound represented by the general formula (1).   The organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing a compound represented by the general formula (1). Organic electroluminescent element as described in any one of these.   The organic electroluminescent element according to claim 1, wherein an emission peak wavelength is 490 to 580 nm.   A light emitting device, a lighting device, or a display device comprising the organic electroluminescent element according to claim 1. A compound represented by any one of the following general formulas (8) to (11).

(In the general formulas (8) to (11), X ^{801 to} X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom, and R ^{801 to} R ⁸⁰⁶ each independently represents a hydrogen atom or an aryl group having 6 to 13 carbon atoms. represents .A ¹¹ to a ¹³ independently represents a CH or a nitrogen atom, at least one is a nitrogen atom.)

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