JP2007123863A - Material for light emitting element, and organic electroluminescent element using it - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a material for an organic electroluminescent element with sufficient performance, such as emission efficiency, current efficiency, an element lifetime and external quantum efficiency, etc. <P>SOLUTION: The material for the organic electroluminescent element includes at least one kind of a compound expressed by a general formula (1). Here, in the formula, R<SP>10</SP>and R<SP>11</SP>are each hydrogen, alkyl, aryl, hetero aryl, etc., and R<SP>20</SP>-R<SP>29</SP>are each hydrogen, alkyl, etc., and R<SP>10</SP>, R<SP>11</SP>, R<SP>20</SP>-R<SP>29</SP>may form each a ring by adjoining adjacent substituents. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a light emitting device material and an organic electroluminescent device using the same.

  The organic electroluminescent element is a self-luminous light emitting element and is expected as a light emitting element for display or illumination. As an organic electroluminescent element, for example, a fluorescent light emitting element using fluorescent light emission, or an organic electroluminescent phosphor element using phosphorescent light emission (hereinafter sometimes referred to as a phosphorescent light emitting element) is known (for example, the United States). (Japanese Patent No. 6097147: Patent Document 1). In the case of emitting light using only fluorescence as in a fluorescent light emitting element, an excited singlet state is used. On the other hand, in the phosphorescent light emitting element, the excitation energy in the triplet state contributes to light emission.

  An organic electroluminescent element has a structure composed of a pair of electrodes composed of an anode and a cathode and one or a plurality of layers disposed between the pair of electrodes and containing an organic compound. Materials have been developed (for example, JP 2003-109763 A, JP 2003-109764 A, JP 2000-150167 A, JP 11-35532 A, JP 7-90257 A, No. 7-90258, JP-A-5-302081, and US Pat. No. 6,428,912: see Patent Documents 2-9).

US Pat. No. 6,097,147 JP 2003-109763 A JP 2003-109764 A JP 2000-150167 A JP-A-11-35532 JP-A-7-90257 Japanese Patent Laid-Open No. 7-90258 JP-A-5-302081 US Pat. No. 6,428,912

  However, even with the organic materials described above, an organic electroluminescent device having sufficient performance with respect to luminous efficiency, current efficiency, device lifetime, external quantum efficiency, and the like has not been obtained yet. Under such circumstances, it is desired to develop an organic electroluminescence device having better performance in terms of luminous efficiency, current efficiency, device lifetime, external quantum efficiency, and the like.

  As a result of intensive studies to solve the above problems, the present inventors have found that the phenalene compound represented by the following general formula (1) has excellent characteristics as a light emitting device material. In addition, an organic electroluminescent device improved in light emission efficiency, current efficiency, device lifetime, external quantum efficiency, and the like by arranging the layer containing the phenalene compound between a pair of electrodes to constitute an organic electroluminescent device. As a result, the present invention was completed.

  That is, this invention provides the organic electroluminescent element using the layer for light emitting elements which consists of the following phenalene compounds, and the layer containing this phenalene compound.

（式中、
Ｒ¹⁰およびＲ¹¹は、それぞれ独立して、水素、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいシクロアルキルまたは置換されていてもよいアラルキルであり、
Ｒ²⁰、Ｒ²¹、Ｒ²²、Ｒ²³、Ｒ²⁴、Ｒ²⁵、Ｒ²⁶、Ｒ²⁷、Ｒ²⁸およびＲ²⁹は、それぞれ独立して、水素、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいシクロアルキル、置換されていてもよいアルコキシ、置換されていてもよいアリールオキシ、置換されていてもよいアルキルチオ、置換されていてもよいアリールチオ、置換されていてもよいアリールアルキル、置換されていてもよいアラルキル、ハロゲン、置換されていてもよいアミノ、置換されていてもよいボリル、シアノ、ニトロ、ヒドロキシルまたは置換されていてもよいシリルであり、そして、
Ｒ¹⁰、Ｒ¹¹、Ｒ²⁰、Ｒ²¹、Ｒ²²、Ｒ²³、Ｒ²⁴、Ｒ²⁵、Ｒ²⁶、Ｒ²⁷、Ｒ²⁸およびＲ²⁹の少なくとも１つの隣接する置換基同士は互いに結合又は縮合して炭素からなる環を形成してもよく、また、形成された環は置換されていてもよい。） [1] A light emitting device material containing at least one compound represented by the following general formula (1).

(Where
R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, substituted Heteroaryl, optionally substituted cycloalkyl or optionally substituted aralkyl,
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted alkyl, substituted May be alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkoxy, substituted May be aryloxy, optionally substituted alkylthio, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aralkyl, halogen, optionally substituted amino, substituted Optionally substituted boryl, cyano, nitro, hydroxyl or optionally substituted silyl, and
At least one adjacent substituent of R ¹⁰ , R ¹¹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ is bonded or condensed with each other. To form a ring made of carbon, and the formed ring may be substituted. )

[2] R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, optionally substituted alkenyl having 2 to 20 carbon atoms, or optionally substituted. Good alkynyl having 2 to 20 carbon atoms, optionally substituted aryl having 5 to 30 carbon atoms, optionally substituted heteroaryl having 2 to 30 carbon atoms, optionally substituted 3 to 10 carbon atoms A cycloalkyl or an optionally substituted aralkyl having 7 to 20 carbon atoms,
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted 1 to 20 carbon atoms. Alkyl, optionally substituted alkenyl having 2 to 20 carbon atoms, optionally substituted alkynyl having 2 to 20 carbon atoms, optionally substituted aryl having 5 to 30 carbon atoms, optionally substituted C2-C30 heteroaryl, C3-C10 cycloalkyl which may be substituted, C1-C20 alkoxy which may be substituted, C6-C20 which may be substituted Aryloxy, optionally substituted alkylthio having 1 to 20 carbon atoms, optionally substituted arylthio having 6 to 30 carbon atoms, optionally substituted arylalkyl having 6 to 30 carbon atoms, substituted Good carbon Aralkyl of 7 to 20, a halogen, an aromatic amino optionally substituted, an optionally substituted aromatic boryl, cyano, nitro, hydroxyl or optionally substituted silyl, and,
R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁷ and R ²⁸ , R ²⁸ and R ^29, and R ¹⁰ and R ¹¹ One adjacent substituent may be bonded to each other or condensed to form a carbon ring, and the formed ring is a condensed ring composed of 1 to 6 rings, and constitutes this condensed ring. Each ring is a 5-membered ring or a 6-membered ring, respectively, and the formed condensed ring may be substituted with aryl, alkoxy or substituted amino.
The material for a light-emitting element described in [1] above.

[3] R ¹⁰ and R ¹¹ are each independently methyl, ethyl, propyl, butyl, hexyl, octyl, phenyl or naphthyl;
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently methyl, ethyl, propyl, butyl, hexyl, octyl, phenyl, Naphthyl, thiophenyl, carbazolyl, diazolyl, triazolyl, pyridyl, methoxy, ethoxy, phenoxy, F, Cl, Br, I, dialkylamino, diarylamino, diarylboryl, cyano, trialkylsilyl, anthryl, phenanthryl, biphenyl, terphenyl, Furanyl or fluorenyl, and
R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ or R ¹⁰ and R ¹¹ One adjacent substituent may be bonded to each other or condensed to form a carbon ring, and this formed ring is a condensed ring composed of 2 or 3 rings, and constitutes this condensed ring. Each ring is a 5-membered or 6-membered ring, respectively, and the formed condensed ring may be substituted with phenyl, naphthyl, methoxy, ethoxy or diarylamino.
The material for a light-emitting element described in [1] above.

（式中、
Ｒ¹⁰およびＲ¹¹は、それぞれ独立して、水素、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいシクロアルキルまたは置換されていてもよいアラルキルであり、
Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｒ¹²およびＲ¹³は、それぞれ独立して、水素、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいシクロアルキル、置換されていてもよいアルコキシ、置換されていてもよいアリールオキシ、置換されていてもよいアルキルチオ、置換されていてもよいアリールチオ、置換されていてもよいアリールアルキル、置換されていてもよいアラルキル、ハロゲン、置換されていてもよいアミノ、置換されていてもよいボリル、シアノ、ニトロ、ヒドロキシルまたは置換されていてもよいシリルであり、そして、
Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴およびＸ⁵は、それぞれの環にそれぞれ独立して複数個結合していてもよい。） [4] A light-emitting element material containing at least one compound represented by the following general formula (2), (3), (4) or (5).

(Where
R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, substituted Heteroaryl, optionally substituted cycloalkyl or optionally substituted aralkyl,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted Good alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, substituted Alkylthio, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aralkyl, halogen, optionally substituted amino, optionally substituted boryl, cyano, nitro , Hydroxyl or optionally substituted silyl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring. )

[5] R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, optionally substituted alkenyl having 2 to 20 carbon atoms, or optionally substituted. Good alkynyl having 2 to 20 carbon atoms, optionally substituted aryl having 5 to 30 carbon atoms, optionally substituted heteroaryl having 2 to 30 carbon atoms, optionally substituted 3 to 10 carbon atoms A cycloalkyl or an optionally substituted aralkyl having 7 to 20 carbon atoms,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted C 1-20 alkyl, or optionally substituted carbon. Alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms that may be substituted, aryl having 5 to 30 carbon atoms that may be substituted, heteroaryl having 2 to 30 carbon atoms that may be substituted, An optionally substituted cycloalkyl having 3 to 10 carbon atoms, an optionally substituted alkoxy having 1 to 20 carbon atoms, an optionally substituted aryloxy having 6 to 20 carbon atoms, and optionally substituted. Alkylthio having 1 to 20 carbon atoms, arylthio having 6 to 30 carbon atoms which may be substituted, arylalkyl having 6 to 30 carbon atoms which may be substituted, aralkyl having 7 to 20 carbon atoms which may be substituted , Androgenic, aromatic amino optionally substituted, an optionally substituted aromatic boryl, cyano, nitro, hydroxyl or a silyl substituted, and,
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[6] R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, optionally substituted alkenyl having 2 to 20 carbon atoms, or optionally substituted. Good alkynyl having 2 to 20 carbon atoms, optionally substituted aryl having 5 to 30 carbon atoms,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ each independently represent hydrogen, optionally substituted aryl having 5 to 30 carbon atoms, or optionally substituted carbon. A heteroaryl having 2 to 30 carbon atoms, an alkoxy having 1 to 15 carbon atoms which may be substituted, an aromatic amino which may be substituted or an aromatic boryl which may be substituted; and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[7] R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl, naphthyl, thiophenyl, carbazolyl, diazolyl, triazolyl, pyridyl, methoxy, ethoxy, diarylamino or diarylboryl, and X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ is hydrogen or phenyl, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The material for a light emitting device according to the above [4].

[8] The light emitting element material is a material for a hole transport layer or a hole injection layer,
In the compound represented by the general formula (2),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² and X ³ are each independently hydrogen or optionally substituted aromatic amino, and
A plurality of X ¹ , X ² and X ³ may be bonded to each ring independently.
The material for a light emitting device according to the above [4].

[9] The light emitting element material is a material for a hole transport layer or a hole injection layer,
In the compound represented by the general formula (2),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are diarylamino, X ³ is hydrogen, and
X ¹ , X ² and X ³ are bonded to each ring,
The material for a light emitting device according to the above [4].

[10] The light emitting device material is a material for an electron transport layer or an electron injection layer,
In the compound represented by the general formula (2), (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen or optionally substituted heteroaryl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[11] The light emitting element material is a material for an electron transport layer or an electron injection layer,
In the compound represented by the general formula (2), (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenanthrolinyl, carbazolyl, diazolyl, triazolyl or pyridyl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The material for a light emitting device according to the above [4].

[12] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen or optionally substituted aryl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[13] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl or naphthyl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The material for a light emitting device according to the above [4].

[14] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, an optionally substituted aromatic amino or an optionally substituted aromatic boryl. And
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[15] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently diarylamino or diarylboryl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The material for a light emitting device according to the above [4].

[16] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 6 carbons or aryl having 5 to 20 carbons;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, aryl having 5 to 20 carbon atoms, alkoxy having 1 to 10 carbon atoms or aromatic amino; and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The material for a light emitting device according to the above [4].

[17] The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl, naphthyl, methoxy, ethoxy, diphenylamino or dinaphthylamino, X ³ , X ⁴ and X ⁵ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The material for a light emitting device according to the above [4].

[18] A pair of electrodes consisting of an anode and a cathode;
It is disposed between the pair of electrodes, and has a single layer or a plurality of layers including the light emitting element material described in any one of [1] to [17].
Organic electroluminescent device.

[19] A display device comprising the organic electroluminescent element as described in [18] above.

[20] A lighting device comprising the organic electroluminescent element as described in [18] above.

  According to a preferred embodiment of the present invention, an organic electroluminescence device improved in light emission efficiency, current efficiency, device lifetime, external quantum efficiency, and the like can be provided. In addition, since it can be applied to a plurality of organic layers constituting an organic electroluminescent device by changing some condensation structures and substituents of the phenalene compound which is the main skeleton, it can be used for a highly versatile organic electroluminescent device. Material can be provided. Furthermore, it is possible to provide a display device, a lighting device, and the like provided with this effective organic electroluminescent element.

The light emitting device material of the present invention will be described in detail.
The light emitting device material according to the present invention is a material containing at least one compound represented by the general formula (1).

1. Compound represented by general formula (1) First, the compound represented by the general formula (1) will be described.

The “alkyl” of “optionally substituted alkyl” in R ¹⁰ and R ¹¹ of the general formula (1) may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 20 carbon atoms. Or a C3-C20 branched alkyl is mention | raise | lifted. Preferred “alkyl” is alkyl having 1 to 12 carbons. More preferable “alkyl” is alkyl having 1 to 6 carbon atoms. Particularly preferred “alkyl” is alkyl having 1 to 4 carbon atoms. Specific examples of “alkyl” include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, heptyl, octyl and the like.

“Alkenyl” of “optionally substituted alkenyl” in R ¹⁰ and R ¹¹ of the general formula (1) may be linear or branched, for example, linear or branched having 2 to 20 carbon atoms. Examples thereof include chain alkenyl. Preferred “alkenyl” is alkenyl having 2 to 12 carbon atoms. More preferable “alkenyl” is alkenyl having 2 to 6 carbon atoms. Particularly preferred “alkenyl” is alkenyl having 2 to 4 carbon atoms. Specific examples include vinyl, propenyl, isopropenyl, allyl, butenyl, pentenyl, geranyl, farnesyl and the like.

“Alkynyl” of “optionally substituted alkynyl” in R ¹⁰ and R ¹¹ of the general formula (1) may be linear or branched, for example, linear or branched having 2 to 20 carbon atoms. Examples thereof include chain alkynyl. Preferred “alkynyl” is alkynyl having 2 to 12 carbon atoms. More preferable “alkynyl” is alkynyl having 2 to 6 carbon atoms. Particularly preferred “alkynyl” is alkynyl having 2 to 4 carbon atoms. Specific examples include ethynyl, propynyl, butynyl and the like.

Examples of “aryl” in “optionally substituted aryl” in R ¹⁰ and R ¹¹ of the general formula (1) include aryl having 5 to 30 carbon atoms. Preferred “aryl” is aryl having 5 to 25 carbon atoms. More preferable “aryl” is aryl having 5 to 20 carbon atoms. Particularly preferred “aryl” is phenyl or naphthyl. Specific examples of “aryl” include phenyl, tolyl, xylyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, terphenylyl, fluorenyl, pyrenyl, and a spiro structure in which aryl of R ¹⁰ and R ¹¹ are bonded.

Examples of “heteroaryl” of “optionally substituted heteroaryl” in R ¹⁰ and R ¹¹ of the general formula (1) include heteroaryl having 2 to 30 carbon atoms. Preferred “heteroaryl” is heteroaryl having 2 to 25 carbon atoms. More preferred “heteroaryl” is heteroaryl having 2 to 20 carbon atoms.

  “Heteroaryl” includes, for example, a heterocyclic group containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms. And heterocyclic groups.

  Examples of the “heterocyclic group” include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenodiazinyl, indodinyl Among them, imidazolyl, pyridyl, carbazolyl and the like are preferable.

  Examples of the `` aromatic heterocyclic group '' include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, Benzofuranyl, isobenzofuranyl, benzo [b] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, Naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phena Cycloalkenyl, phenoxathiinyl, thianthrenyl, etc. indolizinyl, and the like, thienyl, imidazolyl, pyridyl, such as carbazolyl are preferable.

Examples of “cycloalkyl” of “optionally substituted cycloalkyl” in R ¹⁰ and R ¹¹ of the general formula (1) include cycloalkyl having 3 to 10 carbon atoms. Preferred “cycloalkyl” is cycloalkyl having 3 to 8 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 3 to 5 carbon atoms. Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, cycloheptyl, and cyclooctyl.

“Aralkyl” of “optionally substituted aralkyl” in R ¹⁰ and R ¹¹ of the general formula (1) includes aralkyl having 7 to 20 carbon atoms. Preferred “aralkyl” is aralkyl having 7 to 15 carbon atoms. More preferable “aralkyl” is aralkyl having 7 to 10 carbon atoms. Specific examples of “aralkyl” include benzyl, phenylethyl, methylbenzyl (tolubenzyl), and naphthylmethyl (mennaphthyl).

Examples of the “substituent” in R ¹⁰ and R ¹¹ of the general formula (1) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl. Alkyl such as cycloheptyl, octyl, cyclooctyl and trifluoromethyl; aryl such as phenyl, naphthyl, anthracenyl and phenanthryl; methylphenyl, ethylphenyl, s-butylphenyl, t-butylphenyl, 1-methylnaphthyl, 2- Alkylaryl such as methylnaphthyl, 4-methylnaphthyl, 1,6-dimethylnaphthyl, 4-t-butylnaphthyl; pyridyl, quinazolinyl, quinolyl, pyrimidinyl, furyl, thienyl, pyrrolyl, imidazolyl, tetrazolyl, phenayl Heterocycles, such as Tororiniru; and cyano. The number of substituents is, for example, the maximum possible number of substitution, preferably 1 to 3, more preferably 1 to 2.

“Substituted in R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ (hereinafter referred to as R ^{20 to} R ²⁹ ) in the general formula (1) Optionally substituted alkyl ”,“ optionally substituted alkenyl ”,“ optionally substituted alkynyl ”,“ optionally substituted aryl ”,“ optionally substituted heteroaryl ”,“ substituted ” As the “optionally substituted cycloalkyl” and “optionally substituted aralkyl”, the same as those described for R ¹⁰ and R ¹¹ in formula (1) can be used.

Examples of “alkoxy” of “optionally substituted alkoxy” in R ^{20 to} R ²⁹ of the general formula (1) include alkoxy having 1 to 20 carbon atoms. Preferred “alkoxy” is alkoxy having 1 to 15 carbon atoms. More preferred “alkoxy” is alkoxy having 1 to 10 carbon atoms. Specific examples of “alkoxy” include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy, cyclopentoxy, hexyloxy, cyclohexyloxy, heptyloxy, cycloheptyloxy, octyl And oxy, cyclooctyloxy, phenoxy and the like.

Examples of “aryloxy” of “optionally substituted aryloxy” in R ^{20 to} R ²⁹ of the general formula (1) include aryloxy having 6 to 20 carbon atoms. Preferred “aryloxy” is aryloxy having 6 to 16 carbon atoms. More preferable “aryloxy” is aryloxy having 6 to 13 carbon atoms. Specific examples of “aryloxy” include phenyloxy, naphthyloxy, anthracenyloxy, phenanthryloxy and the like.

“Alkylthio” of “optionally substituted alkylthio” in R ^{20 to} R ²⁹ of the general formula (1) includes alkylthio having 1 to 20 carbon atoms. Preferred “alkylthio” is alkylthio having 1 to 15 carbon atoms. More preferable “alkylthio” is alkylthio having 1 to 10 carbon atoms. Specific examples of “alkylthio” include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, t-butylthio, t-butylthio, pentylthio, cyclopentylthio, hexylthio, cyclohexylthio, heptylthio, cycloheptylthio, octylthio, cyclo Examples include octylthio.

“Arylthio” of “optionally substituted arylthio” in R ^{20 to} R ²⁹ of the general formula (1) includes arylthio having 6 to 30 carbon atoms. Preferred “arylthio” is arylthio having 6 to 25 carbon atoms. More preferable “arylthio” is arylthio having 6 to 20 carbon atoms. Specific “arylthio” includes phenylthio, naphthylthio, anthracenylthio, phenanthrylthio and the like.

“Arylalkyl” of “optionally substituted arylalkyl” in R ^{20 to} R ²⁹ of the general formula (1) includes arylalkyl having 6 to 30 carbon atoms. Preferred “arylalkyl” is arylalkyl having 6 to 25 carbon atoms. More preferred “arylalkyl” is arylalkyl having 6 to 20 carbon atoms. Specific examples of “arylalkyl” include arylmethyl, arylethyl and the like, and “aryl” is the same as the above-mentioned aryl.

Examples of “halogen” in R ^{20 to} R ²⁹ of the general formula (1) include F, Cl, Br, I and the like.

Specific examples of the “optionally substituted amino” in R ^{20 to} R ²⁹ of the general formula (1) include amino; alkylamino such as methylamino, ethylamino, cyclohexylamino, and acetylamino; dimethylamino, And dialkylamino such as diethylamino and dibutylamino; diarylamino such as diphenylamino and the like.

Specific examples of the “optionally substituted boryl” in R ^{20 to} R ²⁹ of the general formula (1) include diarylboryl such as diphenylboryl, ditolylboryl, dimesitylboryl, dianthrylboryl, anthrylmesitylboryl, etc. Is given. Examples of the “substituent” of substituted boryl include ortho-disubstituted phenyl. Specific “substituents” include xylyl, mesityl, diisopropylphenyl, triisopropylphenyl, terphenyl and the like.

Specific examples of the “optionally substituted silyl” in R ^{20 to} R ²⁹ of the general formula (1) include trialkylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, triphenylsilyl and the like. Examples thereof include alkoxysilyl groups such as silyl, trimethoxysilyl group, triethoxysilyl group and tributoxysilyl group.

Examples of the “substituent” in R ^{20 to} R ²⁹ of the general formula (1) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl. Alkyl such as cycloheptyl, octyl, cyclooctyl and trifluoromethyl; aryl such as phenyl, naphthyl, anthracenyl and phenanthryl; methylphenyl, ethylphenyl, s-butylphenyl, t-butylphenyl, 1-methylnaphthyl, 2- Alkylaryl such as methylnaphthyl, 4-methylnaphthyl, 1,6-dimethylnaphthyl, 4-t-butylnaphthyl; pyridyl, quinazolinyl, quinolyl, pyrimidinyl, furyl, thienyl, pyrrolyl, imidazolyl, tetrazolyl, phenanthate Heterocycle such as rolinyl; cyano and the like. The number of substituents is, for example, the maximum possible number of substitution, preferably 1 to 3, more preferably 1 to 2.

なお、形成された環は置換されていてもよく、この置換基としては、上記一般式（１）におけるＲ¹⁰およびＲ¹¹の説明、及びＲ²⁰〜Ｒ²⁹の説明で記載したものと同様ものもがあげられる。好ましい置換基としては、アリール、アルコキシ又は置換アミノがあげられ、より好ましい置換基としては、フェニル、ナフチル、メトキシ、エトキシ又はジアリールアミノがあげられる。 As a form in the case where at least one adjacent substituent of R ¹⁰ , R ¹¹ , R ^{20 to} R ^{29 in} the general formula (1) is bonded or condensed to each other to form a carbon ring, R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁷ and R ²⁸ , R ²⁸ and R ^29, and R ¹⁰ and R ¹¹ are adjacent to each other. Substituents may be bonded to each other or condensed to form a carbon ring. The formed ring is a condensed ring composed of 1 to 6 rings, and each ring constituting the condensed ring is preferably a 5-membered ring or a 6-membered ring. Further, the formed ring is a condensed ring composed of 2 or 3 rings, and each ring constituting the condensed ring is preferably a 5-membered ring or a 6-membered ring, respectively. Specific examples include the following ring structures (illustrated including the main skeleton).

In addition, the formed ring may be substituted, and the substituent is the same as that described in the description of R ¹⁰ and R ^{11 and} the description of R ^{20 to} R ^{29 in} the general formula (1). I can give it. Preferred substituents include aryl, alkoxy or substituted amino, and more preferred substituents include phenyl, naphthyl, methoxy, ethoxy or diarylamino.

2. Compounds represented by the general formulas (2) to (5) As further specific examples of the compound represented by the general formula (1), for example, the general formulas (2), (3), (4) And compounds represented by (5).
In these formulas, R ¹⁰ and R ¹¹ each independently represent hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, or an optionally substituted aryl. , Optionally substituted heteroaryl, optionally substituted cycloalkyl or optionally substituted aralkyl. Specifically, it is the same as that described in the description of R ¹⁰ and R ¹¹ in the general formula (1).
In the formula, X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, Optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy , Optionally substituted alkylthio, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aralkyl, halogen, optionally substituted amino, optionally substituted Boryl, cyano, nitro, hydroxyl or optionally substituted silyl, and X ¹ , X ² , X ³ , X ⁴ and X ⁵ are A plurality of each ring may be independently bonded. Specifically, it is the same as that described in the description of R ¹⁰ and R ^{11 and} the description of R ^{20 to} R ^{29 in} the general formula (1).

Other specific examples of the compound represented by the general formula (1) include, for example, the following compounds. It should be noted that the substituents in the following compounds, although not shown in detail, is similar to those described in the description of description of R ¹⁰ and R ^11, and R ²⁰ to R ²⁹ in formula (1).

3. Method for producing compound
3-1. Manufacturing method of phenalene compound represented by General formula (1) The phenalene compound represented by General formula (1) can be manufactured by a well-known synthesis method using a well-known compound.
For example, the following general formula (a) is reacted with a corresponding organometallic reagent such as an organolithium reagent or Grignard reagent to introduce R ¹⁰ , and then Friedel-Crafts using an acid such as CF ₃ SO ₃ H as a promoter. It can be synthesized by introducing R ¹¹ in the reaction. The compound represented by the formula (a) may be a known compound, or may be produced by a known synthesis method using a known compound.

Further, when R ²³ is other than hydrogen, it can be produced using the method of scheme (2). That is, general formula (b) and general formula (c) are reacted using Suzuki-Miyaura coupling reaction, and then reacted with an organometallic reagent such as an organolithium compound or a Grignard reagent to introduce R ¹⁰ . Or may be reduced to alcohol using Dibal.
At this time, Z ¹ and Z ² are halogen, triflate, boronic acid and boronic acid ester, and when either Z ¹ or Z ² is halogen or triflate, either one becomes boronic acid or boronic acid ester, Y is an alkyl group such as methyl, ethyl, or butyl.
Further, the general formula (1) can be produced by treatment with an acid. The acid used in this step is an inorganic salt such as sulfuric acid or hydrochloric acid, an organic acid such as p-toluenesulfonic acid, or a Lewis acid such as BF ₃ · OEt ₂ , BAr ₃ , AlCl ₃ , AlBr ₃ , EtAlCl ₂ or Et ₂ AlCl. be able to. As the reaction solvent, acetic acid, methylene chloride, toluene and the like can be used. Moreover, when an acid is a liquid, an acid can be used as a solvent. The reaction temperature varies depending on the raw materials and acids used in the reaction, but is preferably 0 ° C to 120 ° C.

3-2. Production method of phenalene compound represented by general formula (2) The phenalene compound represented by general formula (2) can be produced by applying the synthesis method of general formula (1).

3-3. Manufacturing method of phenalene compound represented by general formula (3) The phenalene compound represented by general formula (3) can be manufactured using the method of the following scheme (3).

3-4. Manufacturing method of phenalene compound represented by General formula (4) The phenalene compound represented by General formula (4) can be manufactured using the method of the following scheme (4).

3-5. Manufacturing method of phenalene compound represented by General formula (5) The phenalene compound represented by General formula (5) can be manufactured using the method of the following scheme (5).

4). Organic electroluminescent device The organic electroluminescent device according to the present invention comprises a pair of electrodes composed of an anode and a cathode, and a light emission containing at least one of the compounds represented by the general formula (1) disposed between the pair of electrodes. An organic electroluminescent device having one or more layers containing a device material.
The organic electroluminescent element according to this embodiment will be described in detail based on the drawings. FIG. 1 is a schematic cross-sectional view showing an organic electroluminescent element according to this embodiment.

<Structure of organic electroluminescence device>
An organic electroluminescent device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103. A hole transport layer 104 provided on the hole transport layer 104, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, and an electron transport layer 106. And the cathode 108 provided on the electron injection layer 107.

  The organic electroluminescent element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer. An electron transport layer 106 provided on 107, a light-emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light-emitting layer 105, and a hole transport layer 104 A structure including the hole injection layer 103 provided above and the anode 102 provided on the hole injection layer 103 may be employed.

  Not all of the above layers are necessary, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection are included. The layer 107 is an arbitrarily provided layer. Moreover, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

  As an aspect of the layer constituting the organic electroluminescence device, in addition to the above-described configuration aspect of “substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode”, "Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode ”,“ substrate ” / Anode / light emitting layer / electron transport layer / electron injection layer / cathode ”,“ substrate / anode / hole transport layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole transport layer / light emitting layer / “Electron transport layer / cathode”, “substrate / anode / hole injection layer / light emitting layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / light emitting layer / electron transport” Layer / cathode ”,“ substrate / anode / hole injection layer / hole transport layer / light emitting layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / cathode ”,“ substrate / anode / hole transport ” Layer / light emitting layer / cathode ”,“ substrate / anode / light emitting layer / electron transport layer / cathode ”,“ substrate / anode / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / light emitting layer / cathode ” An aspect may be sufficient.

<Substrate in organic electroluminescence device>
The substrate 101 serves as a support for the organic electroluminescent device 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable. In the case of a glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness only needs to be sufficient to maintain the mechanical strength. The upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, non-alkali glass is preferred because it is better that there are fewer ions eluted from the glass, but soda-lime glass with a barrier coat such as SiO ₂ is also available on the market. it can. Further, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one surface in order to improve the gas barrier property, and a synthetic resin plate, film or sheet having a low gas barrier property is used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescence device>
The anode 102 serves to inject holes into the light emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .

  Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), etc.), halogenated compounds. Examples thereof include metals (such as copper iodide), copper sulfide, carbon black, ITO glass, and nesa glass. Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole and polyaniline, and the like. In addition, it can select suitably from the substances currently used as an anode of an organic electroluminescent element, and can use it.

The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the light emitting element can be supplied. For example, an ITO substrate of 300 Ω / cm ² or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 Ω / cm ² , for example, 100 to 5 Ω / cm ² , preferably It is particularly desirable to use a low resistance product of 50-5 Ω / cm ² . The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescence device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one kind or two or more kinds of hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder. Is done. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

  As a hole injection / transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. The hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do. For this purpose, it is preferable to use a substance that has a low ionization potential, a high hole mobility, excellent stability, and is less likely to generate trapping impurities during production and use.

As a material for forming the hole injection layer 103 and the hole transport layer 104, a material for a light-emitting element in which X ¹ and X ² are aromatic amino in the phenalene compound of the general formula (2) is particularly preferable. The content of the phenalene compound represented by the general formula (2) in the hole injection layer 103 or the hole transport layer 104 is 1 to 100% by weight, more preferably 10 to 100% by weight, particularly 50 to 100% by weight, 80 to 100% by weight is preferred.

  Further, as other materials for forming the hole injection layer 103 and the hole transport layer 104, compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, organic electroluminescent elements are used. Any of known materials used for the hole injection layer and the hole transport layer can be selected and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-allylcarbazole) or bis (N-alkylcarbazole), triarylamine derivatives (aromatic tertiary class). Polymer having amine in main chain or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N′-diphenyl-N, N′-di (3-methylphenyl) -4 , 4′-diaminobiphenyl, N, N′-diphenyl-N, N′-dinaphthyl-4,4′-diaminobiphenyl, N, N′-diphenyl-N, N′-di (3-methylphenyl) -4 , 4′-diphenyl-1,1′-diamine, N, N′-dinaphthyl-N, N′-diphenyl-4,4′-diphenyl-1,1 -Triphenylamine derivatives such as diamine, 4,4 ', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine, starburst amine derivatives, stilbene derivatives, phthalocyanine derivatives (metal free, copper phthalocyanine, etc.) ), Pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, heterocyclic compounds such as oxadiazole derivatives, porphyrin derivatives, polysilanes, etc. In polymer systems, polycarbonates and styrene derivatives having the above monomers in the side chain, Polyvinyl carbazole and polysilane are preferable, but the compound is not particularly limited as long as it is a compound that forms a thin film necessary for manufacturing a light-emitting element, can inject holes from the anode, and can further transport holes.

  It is also known that the conductivity of organic semiconductors is strongly influenced by the doping. Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping of electron donor materials. (For example, the document “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998)”) and the document “J. Blochwitz, M Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)). M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998). And J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998). These generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. Known matrix substances having hole transporting properties include, for example, benzidine derivatives (TPD and the like), starburst amine derivatives (TDATA and the like), and specific metal phthalocyanines (particularly zinc phthalocyanine ZnPc and the like). 2005-167175).

<Light emitting layer in organic electroluminescent element>
The light emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light emitting layer 105 may be a compound that emits light when excited by recombination of holes and electrons (light emitting compound), can form a stable thin film shape, and is in a solid state And a compound exhibiting a strong light emission (fluorescence and / or phosphorescence) efficiency.

  The light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting material (host material, dopant material), which may be a mixture of a host material and a dopant material or a host material alone. Or either. That is, in each layer of the light emitting layer, only the host material or the dopant material may emit light, or both the host material and the dopant material may emit light. Each of the host material and the dopant material may be one kind or a plurality of combinations. The dopant material may be included in the host material as a whole, or may be included partially. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that it is preferably used in an amount of 10 to 1% by weight, more preferably 5 to 2% by weight, based on the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited.

  In addition, the light emitting material of the light emitting element according to this embodiment may be either fluorescent or phosphorescent.

As the host material, a light-emitting element material in which X ¹ and X ² are aryl in the phenalene compound represented by the general formula (3), (4), or (5) is particularly preferable. The content of the phenalene compound represented by the general formula (3), (4) or (5) in the light emitting layer 105 as a host material is 1 to 100% by weight, more preferably 10 to 100% by weight, particularly 50 to 100%. % By weight, especially 80 to 100% by weight is preferred.

  Other host materials include, but are not limited to, metal chelated oxinoid compounds such as fused ring derivatives such as anthracene and pyrene, tris (8-quinolinolato) aluminum, which have been known as light emitters. Bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, For pyrrolopyrrole derivatives and polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives are preferably used.

  In addition, as a host material, it can select and use suitably from the compound etc. which were described in the chemical industry June, 2004 issue page 13, and the reference cited up.

Examples of the blue dopant material include materials for light-emitting elements in which X ¹ and X ² are aryl, aromatic amino, or aromatic boryl in the phenalene compound represented by the general formula (3), (4), or (5). Particularly preferred. The content of the phenalene compound represented by the general formula (3), (4) or (5) in the light emitting layer 105 as a dopant material is 1 to 100% by weight, more preferably 10 to 100% by weight, particularly 50 to 100%. % By weight, especially 80 to 100% by weight is preferred.

  The other dopant material is not particularly limited, and a known compound can be used, and can be selected from various materials according to a desired emission color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene and rubrene, benzoxazole derivatives, benzthiazole derivatives, benzimidazole derivatives, benztriazole derivatives, oxazole derivatives, Bisstyryl derivatives such as oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives Kaihei 1-245087), bisstyrylarylene derivatives (Japanese Patent Laid-Open No. 2-247278) Isobenzofuran derivatives such as diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) isobenzofuran, di (2-trifluoromethylphenyl) isobenzofuran, phenylisobenzofuran, Dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzthiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives Derivatives, coumarin derivatives such as 3-benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives , Oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2, 5-thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, diazaflavin derivatives, and the like.

  Illustratively for each color light, blue to blue-green dopant materials include naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene and other aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, silole, Aromatic heterocyclic compounds such as 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene And its derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thiadiazole, cal Azole derivatives such as sol, oxazole, oxadiazole, triazole and metal complexes thereof, and N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′- Examples thereof include aromatic amine derivatives represented by diamine.

  Examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene, and the above blue A compound in which a substituent capable of increasing the wavelength such as an aryl group, a heteroaryl group, an arylvinyl group, an amino group, or a cyano group is introduced into the compound exemplified as a blue-green dopant material is also a suitable example.

  Further, examples of the orange to red dopant material include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazones Conductors and thiadiazolopyrene derivatives, etc. can be used. In addition, the compounds exemplified above as blue to blue-green and green to yellow dopant materials can increase the wavelength of aryl groups, heteroaryl groups, arylvinyl groups, amino groups, cyano groups, etc. A compound into which a substituent is introduced is also a suitable example. Furthermore, a phosphorescent metal complex having iridium represented by tris (2-phenylpyridine) iridium (III) or platinum as a central metal is also a suitable example.

  In addition, as a dopant, it can select and use suitably from the compound etc. which were described in the chemical industry June, 2004 issue page 13, and the reference cited up.

<Electron injection layer and electron transport layer in organic electroluminescence device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport / injection materials, or a mixture of the electron transport / injection material and a polymer binder.

  The electron injecting / transporting layer is a layer that administers electrons injected from the cathode and further transports electrons. It is desirable that the electron injecting electrons have high efficiency and efficiently transport the injected electrons. For this purpose, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is unlikely to generate trapping impurities during production and use. However, considering the transport balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is much higher. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron injection / transport layer in this embodiment may include a function of a layer that can efficiently block the movement of holes.

In addition, as a material for forming the electron transport layer 106 and the electron injection layer 107, in the phenalene compound represented by the general formula (2), (3), (4), or (5), X ¹ and X ² may be heterocycles ( A light emitting device material such as heteroaryl is particularly preferable. The content of the phenalene compound represented by the general formula (2), (3), (4) or (5) in the electron transport layer 106 or the electron injection layer 107 is 1 to 100% by weight, and further 10 to 100% by weight. %, In particular 50 to 100% by weight, in particular 80 to 100% by weight.

  Other materials for forming the electron transport layer and the electron injection layer include compounds conventionally used as electron transport compounds in photoconductive materials, and known materials used for the electron injection layer and the electron transport layer of organic electroluminescent devices. Any of these compounds can be selected and used.

  As a material used for the electron transport layer and the electron injection layer, a compound comprising an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, a pyrrole derivative And at least one selected from the condensed ring derivatives thereof and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinones And quinone derivatives such as diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include quinolinol complexes such as tris (8-quinolinolato) aluminum, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Etc. These materials can be used alone or in combination with different materials. Among them, quinolinol complexes such as tris (8-quinolinolato) aluminum, anthracene derivatives such as 9,10-bis (2-naphthyl) anthracene, styryl aromatic ring derivatives such as 4,4′-bis (diphenylethenyl) biphenyl, Carbazole derivatives such as 4,4′-bis (N-carbazolyl) biphenyl and 1,3,5-tris (N-carbazolyl) benzene are preferably used from the viewpoint of durability.

  Specific examples of other electron transfer compounds include pyridine derivatives, phenanthroline derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, Quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benz Thiazole derivatives, quinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, naphthyridine derivatives, aldazine derivatives, Such as Susuchiriru derivatives.

Among them, pyridine derivatives (for example, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1,1-dimethyl-3,4-diphenylsilole (hereinafter abbreviated as PyPySPyPy), 9,10 -Di (2 ', 2 "-bipyridyl) anthracene, 2,5-di (2', 2" -bipyridyl) thiophene, 2,5-di (3 ', 2 "-bipyridyl) thiophene, 6'6"- Di (2-pyridyl) 2,2 ′: 4 ′, 3 ″: 2 ″, 2 ″ -quaterpyridine, etc.), phenanthroline derivatives (for example, 4,7-diphenyl-1,10-phenanthroline, 2,9- Dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, , 3, -Tri (1,10-phenanthroline-5-yl) benzene, 9,9'-difluoro-bis (1,10-phenanthroline-5-yl), bathocuproine or 1,3-bis (2-phenyl-1,10 -Phenanthroline-9-yl) benzene), quinolinol-based metal complexes (for example, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq3), bis (10-hydroxybenzo [h] quinoline) beryllium, tris Imidazoles such as (4-methyl-8-hydroxyquinoline) aluminum, bis (2-methyl-8-hydroxyquinoline)-(4-phenylphenol) aluminum), tris (N-phenylbenzimidazol-2-yl) benzene Derivative 1,3-bis [(4-tert-butylphenyl) 1,3,4- Oxadiazole derivatives such as oxadiazolyl] phenylene, triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, 2,2′-bis (benzo [h] quinolin-2-yl)- Benzoquinoline derivatives such as 9,9′-spirobifluorene, terpyridine derivatives such as 1,3-bis (4 ′-(2,2 ′: 6′2 ″ -terpyridinyl)) benzene, bis (1-naphthyl)- Naphthyridine derivatives such as 4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferred.
In particular, when a pyridine derivative or a phenanthroline derivative is used for the electron transport layer or the electron injection layer, low voltage and high efficiency can be realized.

  A case where an organic phosphor having a phenanthroline skeleton is used for the electron transport layer will be described. In order to obtain stable light emission over a long period of time, a material excellent in thermal stability and thin film formation is desired, and among organic phosphors having a phenanthroline skeleton, the substituent itself has a three-dimensional structure, Those having a three-dimensional structure by steric repulsion with a phenanthroline skeleton or adjacent substituents, or those having a plurality of phenanthroline skeletons linked to each other are preferred. Furthermore, when linking a plurality of phenanthroline skeletons, a compound containing a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, or a substituted or unsubstituted aromatic heterocycle in the linking unit is more preferable.

<Cathode in organic electroluminescence device>
The cathode 108 serves to inject electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

  The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that for forming the anode 102 can be used. Among them, metals such as tin, magnesium, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, tin, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium- Silver alloys, magnesium-indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum) are preferred. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium, cesium, or magnesium (1 nm or less in vacuum vapor deposition thickness gauge display). Although a method using a highly stable electrode can be given as a preferred example, it is particularly limited to these because inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. It is not something.

  Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.

<Binder that may be used in each layer>
The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, Polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, vinyl acetate, ABS resin, Disperse in solvent-soluble resins such as polyurethane resin, curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. Possible it is.

<Method for producing organic electroluminescent element>
Each layer constituting the organic electroluminescent element is formed by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or casting method, coating method, etc. It can be formed by using a thin film. The thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When a thin film is formed using a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the intended crystal structure and association structure of the film, and the like. Deposition conditions generally include boat heating temperature of 50 to 400 ° C., vacuum degree of 10 ⁻⁶ to 10 ⁻³ Pa, deposition rate of 0.01 to 50 nm / second, substrate temperature of −150 to + 300 ° C., and film thickness of 2 nm to 5 μm. It is preferable to set appropriately within the range.

  Next, as an example of a method for producing an organic electroluminescent device, an organic electric field composed of an anode / hole injection layer / hole transport layer / a light emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode. A method for manufacturing a light-emitting element will be described. A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-evaporated on this to form a thin film to form a light emitting layer. An electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by vapor deposition. By forming it as a cathode, a desired organic electroluminescent element can be obtained. In the preparation of the above-described organic electroluminescence device, the order of preparation may be reversed, and the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode may be fabricated in this order. Is possible.

  When a DC voltage is applied to the organic electroluminescent device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, the organic electroluminescent device is transparent or translucent. Luminescence can be observed from the electrode side (anode or cathode, and both). The organic electroluminescence device emits light when a pulse current or an alternating current is applied. The alternating current waveform to be applied may be arbitrary.

<Application examples of organic electroluminescent devices>
The present invention can also be applied to a display device provided with an organic electroluminescent element or a lighting device provided with an organic electroluminescent element.
A display device or an illuminating device including an organic electroluminescent element can be manufactured by a known method such as connecting the organic electroluminescent element according to the present embodiment and a known driving device, such as direct current driving, pulse driving, or alternating current. It can be driven by appropriately using a known driving method such as driving.

  Examples of the display device include a panel display such as a color flat panel display, and a flexible display such as a flexible color organic electroluminescence (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). Gazette, Japanese Patent Application Laid-Open No. 2004-281086, etc.). Examples of the display method of the display include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.

  A matrix means a pixel in which pixels for display are two-dimensionally arranged such as a lattice or a mosaic, and displays a character or an image with a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.

  In the segment method (type), a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned.

  Examples of the illuminating device include an illuminating device such as indoor lighting, a backlight of a liquid crystal display device, and the like (for example, Japanese Patent Application Laid-Open Nos. 2003-257621, 2003-277741, and 2004-119211). Etc.) The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, as a backlight for liquid crystal display devices, especially personal computers for which thinning is an issue, considering that conventional methods are made of fluorescent lamps and light guide plates, it is difficult to reduce the thickness. The backlight using the light emitting element according to the embodiment is thin and lightweight.

<Synthesis example of phenanthrene compound>
Next, Table 1 shows some physical property values of the synthesized phenalene compounds. The measuring method of each physical property value is as follows. About NMR measurement, the reference | standard was measured as TMS using JNM-made JNM-GSX. For UV absorbance measurement, the excitation wavelength was measured at 254 nm using a JASCO V-560 spectrophotometer. About melting | fusing point measurement, it measured using Diamond DSC made from PerkinElmer.

  Hereinafter, synthesis examples of compounds 1 to 5 will be described.

<Synthesis Example of Compound 1>
After dissolving 0.9 g (1.2 mmol) of dimethyl 2- (4-diphenylamino-1-phenyl) -5- (4-diphenylamino-1-naphthyl) -terephthalate in 50 ml of THF, the mixture was cooled to −75 ° C. Then, 2.2 equivalents of PhLi / dibutyl ether solution was added to the carboxylic acid ester group, the temperature was raised to room temperature, and the mixture was stirred for 2 hours and then quenched by adding saturated aqueous ammonium chloride solution to form a diol form. . The aqueous layer was separated, the solvent was removed under reduced pressure, and the residue washed with ethanol was added with 50 ml of acetic acid and several drops of concentrated sulfuric acid, and stirred at 100 ° C. for 3 hours. After the reaction, 50 ml of water was added and the precipitate was filtered. The precipitate was further washed with water and methanol. The precipitate was extracted with ethyl acetate, and then ethyl acetate was distilled off under reduced pressure. The residue was developed with silica gel chromatography using toluene-hexane (1: 1) to obtain 852 mg (0.9 mmol) of Compound 1 in a yield of 98%.

<Synthesis Example of Compound 2>
After dissolving 1.0 g (1.3 mmol) of dimethyl 2,5-bis (4-diphenylamino-1-naphthyl) -terephthalate in 150 ml of THF, the solution was cooled to −75 ° C. .2 equivalents of PhLi / dibutyl ether solution was added, the temperature was raised to room temperature, and after stirring for 2 hours, a saturated aqueous solution of ammonium chloride was added to quench the reaction to produce a diol. The aqueous layer was separated, the solvent was removed under reduced pressure, and the residue washed with ethanol was added with 50 ml of acetic acid and several drops of concentrated sulfuric acid, and stirred at 100 ° C. for 3 hours. After the reaction, 50 ml of water was added and the precipitate was filtered. The precipitate was further washed with water and methanol. The precipitate was extracted with ethyl acetate, and then ethyl acetate was distilled off under reduced pressure. The residue was developed with silica gel chromatography using toluene-hexane (1: 1) to obtain 328 mg (0.33 mmol) of Compound 2 in a yield of 25%.

<Synthesis Example of Compound 3>
After dissolving 3.8 g (5.4 mmol) of 1,4-bis (4-methoxy-2-carboxylate methyl-1-phenyl) -naphthalene in 200 ml of THF, the solution was cooled to −75 ° C. to form a carboxylate group. On the other hand, 2.2 equivalents of PhLi / dibutyl ether solution was added, the temperature was raised to room temperature, and the mixture was stirred for 2 hours, and then quenched by adding saturated aqueous ammonium chloride solution to produce a diol form. The aqueous layer was separated, the solvent was removed under reduced pressure, and the residue washed with ethanol was added with 200 ml of acetic acid and several drops of concentrated sulfuric acid, and stirred at 100 ° C. for 3 hours. After the reaction, 100 ml of water was added and the precipitate was filtered. The precipitate was further washed with water and methanol. The precipitate was extracted with ethyl acetate, and then ethyl acetate was distilled off under reduced pressure. The residue was developed with silica gel chromatography using toluene-hexane (1: 1) to obtain 2.65 g (4.0 mmol) of Compound 3 in a yield of 73%.

<Synthesis Example of Compound 4>
After 2.9 g (4.5 mmol) of dimethyl 2- (1,4-biphenyl) -5- (4-diphenylamino-1-naphthyl) -terephthalate was dissolved in 80 ml of THF, the solution was cooled to −75 ° C. and carboxylic acid To the ester group, 2.2 equivalent of PhLi / dibutyl ether solution was added, the temperature was raised to room temperature, and after stirring for 2 hours, a saturated aqueous solution of ammonium chloride was added to quench the reaction to produce a diol form. The aqueous layer was separated, the solvent was removed under reduced pressure, 30 ml of acetic acid and several drops of concentrated sulfuric acid were added to 1.0 g (1.1 mmol) of the residue washed with ethanol, and the mixture was stirred at 80 ° C. for 3 hours. After the reaction, 50 ml of water was added and the precipitate was filtered. The precipitate was further washed with water and methanol. The precipitate was extracted with ethyl acetate, and then ethyl acetate was distilled off under reduced pressure. The residue was developed by silica gel chromatography using ethyl acetate-heptane (1:30) to obtain 0.52 mg (0.61 mmol) of Compound 4. in a yield of 55% (based on the diol form).

<Synthesis Example of Compound 5>
After 4.0 g (6.2 mmol) of Compound 3 was dissolved in 150 ml of methylene chloride, the mixture was cooled to −30 ° C., a BBr ₃ / methylene chloride solution was added, and the mixture was stirred overnight at room temperature. After neutralizing with an aqueous sodium hydrogen carbonate solution and washing with water, the organic layer was concentrated, and the residue was developed with silica gel chromatography using ethyl acetate-heptane (1:30) to produce a diol form. 4.0 g (6.2 mmol) of the diol was dissolved in methylene chloride, 5.6 g (19 mmol) of trifluoromethanesulfonic anhydride was added, and the mixture was stirred at room temperature for 5 hours. After the reaction, the mixture was neutralized with an aqueous sodium hydrogen carbonate solution, and the organic layer was washed with water. The organic layer was concentrated and ethanol was added to purify the precipitate, followed by filtration to obtain a triflate as a white solid. 2.2 g (2.4 mmol) of this white solid, 0.95 g (5.5 mmol) of 2-naphthylboronic acid, 0.15 g (0.13 mmol) of tetrakis (triphenylphosphine) palladium and 3.0 g of potassium phosphate ( 14 mmol) was stirred at 70 ° C. for 5 hours under an argon atmosphere using 50 ml of THF / 2-propanol as a solvent. After cooling, water was added to the reaction solution, and the organic layer was washed with water. After the aqueous layer was separated, the organic layer was collected and the solvent was removed under reduced pressure. This residue was developed with silica gel chromatography using ethyl acetate-heptane (1:30) to obtain 1.3 g (1.5 mmol) of compound 5 in a yield of 63% (based on triflate form).

<Example>
The electroluminescent elements according to Examples 1, 2, 3, and 4 and the electroluminescent elements according to Comparative Examples 1 and 2 were prepared, and voltage (V) and current density (mA), which are characteristics at the time of 100 cd / m ² emission, respectively. / Cm ² ), luminous efficiency (Lm / W), current efficiency (cd / A), emission wavelength (nm) and chromaticity (x, y) measurement, external quantum efficiency (%) measurement, 20 mA / cm ² The luminance half-life (time), which is the element life characteristic when the constant current drive was performed, was measured. However, with respect to Example 4 and Comparative Example 2, instead of measuring the element lifetime characteristics at 20 mA / cm ² constant current driving, the luminance half-life, which is the element lifetime characteristics at 1000 cd / m ² constant current driving, is used. (Time) was measured. Hereinafter, each example and comparative example will be described in detail.

Table 2 below shows the material configuration of each layer in the electroluminescent devices according to Examples 1, 2, 3, and 4 and the electroluminescent devices according to Comparative Examples 1 and 2.

  In Table 2, compounds 1, 2, 4 and 5 represent compounds 1, 2, 4 and 5 in Table 1, respectively. In Table 2, “CuPc” is copper phthalocyanine, “NPD” is N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine, and “BH1” is 9-phenyl-10- [6- ([1,1 ′: 3,1 ″] terphenyl-5′-yl) -naphthalen-2-yl] anthracene, “BD1” is N, N, N ′, N′-tetra (4-biphenylyl) -4,4-diaminostilbene, "ETM1" is tris (8-quinolinolato) aluminum and "ETM2" is 2,5-bis (6 '-(2'2 "-bipyridyl) -1,1-dimethyl-3, 4-Dimesitylsilol, each having the following chemical structural formula.

  A transparent support substrate was obtained by depositing ITO on a glass substrate to a thickness of 150 nm. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus, a molybdenum vapor deposition boat containing “CuPc”, a molybdenum vapor deposition boat containing “NPD”, and a molybdenum vapor deposition vessel containing “BH1” A molybdenum vapor deposition boat containing “Compound 1”, a molybdenum vapor deposition boat containing “ETM1”, a molybdenum vapor deposition boat containing lithium fluoride, and a tungsten vapor deposition boat containing aluminum. Installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 1 × 10 ⁻³ Pa, and first, a vapor deposition boat containing “CuPc” is heated and vapor-deposited to a thickness of 20 nm to form a hole injection layer. The evaporation boat containing “is heated and evaporated to a film thickness of 30 nm to form a hole transport layer. Next, the vapor deposition boat containing “BH1” and the vapor deposition boat containing “Compound 1” were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 35 nm. The deposition rate was adjusted so that the weight ratio of “BH1” to “Compound 1” was approximately 95 to 5. Next, the evaporation boat containing “ETM1” was heated and evaporated to a film thickness of 15 nm to form an electron transport layer. The deposition rate of each layer was 0.001 to 3.0 nm / sec.

  Thereafter, the evaporation boat containing lithium fluoride is heated to deposit at a deposition rate of 0.003 to 0.01 nm / second so that the film thickness becomes 0.5 nm, and then the evaporation boat containing aluminum is heated. The cathode was formed by vapor deposition at a vapor deposition rate of 0.1 to 1 nm / second so that the film thickness was 100 nm, and an electroluminescent element was obtained.

The ITO electrode as the anode, a cathode and a lithium fluoride / aluminum electrode, when measuring the characteristics at the time of 100 cd / m ² light emission, voltage 5.4 (V), current density 1.9 (mA / cm ^2), luminous efficiency 3 0.0 (Lm / W), current efficiency 5.2 (cd / A), emission wavelength 465 (nm), and chromaticity (0.14, 0.23). The external quantum efficiency was 5.0 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 20 mA / cm ² constant current driving was performed was measured, the luminance half time was 700 (hours).

  An electroluminescent device was obtained in exactly the same manner as in Example 1 except that Compound 2 was used instead of Compound 1 as the dopant used in Example 1.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 4.7 (V), the current density was 1.3 (mA / cm ² ), and the emission efficiency was 5 0.3 (Lm / W), current efficiency 7.9 (cd / A), emission wavelength 485 (nm), and chromaticity (0.16, 0.42). The external quantum efficiency was 4.6 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 20 mA / cm ² constant current driving was performed was measured, the luminance half time was 1000 (hours).

  An electroluminescent device was obtained in exactly the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 as the dopant used in Example 1.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 5.7 (V), the current density was 2.0 (mA / cm ² ), and the luminous efficiency was 2 0.7 (Lm / W), current efficiency 4.9 (cd / A), emission wavelength 468 (nm), and chromaticity (0.14, 0.24). The external quantum efficiency was 3.7 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 20 mA / cm ² constant current driving was performed was measured, the luminance half time was 1000 (hours).
[Comparative Example 1]

  An electroluminescent device was obtained in exactly the same manner as in Example 1 except that BD1 was used instead of Compound 1 as the dopant used in Example 1.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 4.5 (V), the current density was 2.4 (mA / cm ² ), and the luminous efficiency was 3 0.0 (Lm / W), current efficiency 4.3 (cd / A), emission wavelength 455 (nm), and chromaticity (0.16, 0.20). The external quantum efficiency was 3.7 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 20 mA / cm ² constant current driving was performed was measured, the luminance half time was 1000 (hours).

  An electroluminescent device was obtained in exactly the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 which was the dopant used in Example 1, and ETM2 was used instead of ETM1 which was the electron transport material. .

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 3.4 (V), the current density was 1.7 (mA / cm ² ), and the emission efficiency was 5 0.6 (Lm / W), current efficiency 6.1 (cd / A), emission wavelength 450 (nm), and chromaticity (0.15, 0.14). The external quantum efficiency was 5.7 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 1000 cd / m ² constant current driving was performed was measured, the luminance half time was 180 (hours).
[Comparative Example 2]

  An electroluminescent device was obtained in exactly the same manner as in Example 1, except that BD1 was used instead of Compound 1 which is the dopant used in Example 1, and ETM2 was used instead of ETM1 which was the electron transport material.

The ITO electrode as the anode, a cathode and a lithium fluoride / aluminum electrode, when measuring the characteristics at the time of 100 cd / m ² light emission, voltage 3.2 (V), current density 1.7 (mA / cm ^2), luminous efficiency 6 0.0 (Lm / W), current efficiency 6.1 (cd / A), emission wavelength 455 (nm), and chromaticity (0.15, 0.19). The external quantum efficiency was 5.3 (%), and the current density at that time was 10 (mA / cm ² ). In addition, when the device lifetime characteristic when the 1000 cd / m ² constant current driving was performed was measured, the luminance half time was 120 (hours).

Table 3 below summarizes the performance evaluation of the electroluminescent elements according to Examples 1, 2, 3 and 4 and the electroluminescent elements according to Comparative Examples 1 and 2.

  According to a preferred aspect of the present invention, an organic electroluminescent element having better performance in any of luminous efficiency, current efficiency, element lifetime, external quantum efficiency, and the like, a display device including the same, and a lighting device including the same Can be provided.

It is a schematic sectional drawing which shows the organic electroluminescent element which concerns on this embodiment.

Explanation of symbols

DESCRIPTION OF SYMBOLS 100 Organic electroluminescent element 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (20)

The material for light emitting elements containing at least 1 type of the compound represented by following General formula (1).

(Where
R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, substituted Heteroaryl, optionally substituted cycloalkyl or optionally substituted aralkyl,
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted alkyl, substituted May be alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkoxy, substituted May be aryloxy, optionally substituted alkylthio, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aralkyl, halogen, optionally substituted amino, substituted Optionally substituted boryl, cyano, nitro, hydroxyl or optionally substituted silyl, and
At least one adjacent substituent of R ¹⁰ , R ¹¹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ is bonded or condensed with each other. To form a ring made of carbon, and the formed ring may be substituted. ) R ¹⁰ and R ¹¹ are each independently hydrogen, an optionally substituted alkyl having 1 to 20 carbon atoms, an optionally substituted alkenyl having 2 to 20 carbon atoms, or an optionally substituted carbon number. 2-20 alkynyl, optionally substituted aryl having 5-30 carbon atoms, optionally substituted heteroaryl having 2-30 carbon atoms, optionally substituted cycloalkyl having 3-10 carbon atoms, or An optionally substituted aralkyl having 7 to 20 carbon atoms,
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently hydrogen, optionally substituted 1 to 20 carbon atoms. Alkyl, optionally substituted alkenyl having 2 to 20 carbon atoms, optionally substituted alkynyl having 2 to 20 carbon atoms, optionally substituted aryl having 5 to 30 carbon atoms, optionally substituted C2-C30 heteroaryl, C3-C10 cycloalkyl which may be substituted, C1-C20 alkoxy which may be substituted, C6-C20 which may be substituted Aryloxy, optionally substituted alkylthio having 1 to 20 carbon atoms, optionally substituted arylthio having 6 to 30 carbon atoms, optionally substituted arylalkyl having 6 to 30 carbon atoms, substituted Good carbon Aralkyl of 7 to 20, a halogen, an aromatic amino optionally substituted, an optionally substituted aromatic boryl, cyano, nitro, hydroxyl or optionally substituted silyl, and,
R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁷ and R ²⁸ , R ²⁸ and R ^29, and R ¹⁰ and R ¹¹ One adjacent substituent may be bonded to each other or condensed to form a carbon ring, and the formed ring is a condensed ring composed of 1 to 6 rings, and constitutes this condensed ring. Each ring is a 5-membered ring or a 6-membered ring, respectively, and the formed condensed ring may be substituted with aryl, alkoxy or substituted amino.
The light emitting device material according to claim 1. R ¹⁰ and R ¹¹ are each independently methyl, ethyl, propyl, butyl, hexyl, octyl, phenyl or naphthyl;
R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently methyl, ethyl, propyl, butyl, hexyl, octyl, phenyl, Naphthyl, thiophenyl, carbazolyl, diazolyl, triazolyl, pyridyl, methoxy, ethoxy, phenoxy, F, Cl, Br, I, dialkylamino, diarylamino, diarylboryl, cyano, trialkylsilyl, anthryl, phenanthryl, biphenyl, terphenyl, Furanyl or fluorenyl, and
R ²⁰ and R ²¹ , R ²¹ and R ²² , R ²² and R ²³ , R ²⁴ and R ²⁵ , R ²⁵ and R ²⁶ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ or R ¹⁰ and R ¹¹ One adjacent substituent may be bonded to each other or condensed to form a carbon ring, and this formed ring is a condensed ring composed of 2 or 3 rings, and constitutes this condensed ring. Each ring is a 5-membered or 6-membered ring, respectively, and the formed condensed ring may be substituted with phenyl, naphthyl, methoxy, ethoxy or diarylamino.
The light emitting device material according to claim 1. A light emitting device material containing at least one compound represented by the following general formula (2), (3), (4) or (5).

(Where
R ¹⁰ and R ¹¹ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, substituted Heteroaryl, optionally substituted cycloalkyl or optionally substituted aralkyl,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted Good alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, substituted Alkylthio, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aralkyl, halogen, optionally substituted amino, optionally substituted boryl, cyano, nitro , Hydroxyl or optionally substituted silyl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring. ) R ¹⁰ and R ¹¹ are each independently hydrogen, an optionally substituted alkyl having 1 to 20 carbon atoms, an optionally substituted alkenyl having 2 to 20 carbon atoms, or an optionally substituted carbon number. 2-20 alkynyl, optionally substituted aryl having 5-30 carbon atoms, optionally substituted heteroaryl having 2-30 carbon atoms, optionally substituted cycloalkyl having 3-10 carbon atoms, or An optionally substituted aralkyl having 7 to 20 carbon atoms,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted C 1-20 alkyl, or optionally substituted carbon. Alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms that may be substituted, aryl having 5 to 30 carbon atoms that may be substituted, heteroaryl having 2 to 30 carbon atoms that may be substituted, An optionally substituted cycloalkyl having 3 to 10 carbon atoms, an optionally substituted alkoxy having 1 to 20 carbon atoms, an optionally substituted aryloxy having 6 to 20 carbon atoms, and optionally substituted. Alkylthio having 1 to 20 carbon atoms, arylthio having 6 to 30 carbon atoms which may be substituted, arylalkyl having 6 to 30 carbon atoms which may be substituted, aralkyl having 7 to 20 carbon atoms which may be substituted , Androgenic, aromatic amino optionally substituted, an optionally substituted aromatic boryl, cyano, nitro, hydroxyl or a silyl substituted, and,
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. R ¹⁰ and R ¹¹ are each independently hydrogen, an optionally substituted alkyl having 1 to 20 carbon atoms, an optionally substituted alkenyl having 2 to 20 carbon atoms, or an optionally substituted carbon number. 2 to 20 alkynyl, optionally substituted aryl having 5 to 30 carbon atoms,
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ each independently represent hydrogen, optionally substituted aryl having 5 to 30 carbon atoms, or optionally substituted carbon. A heteroaryl having 2 to 30 carbon atoms, an alkoxy having 1 to 15 carbon atoms which may be substituted, an aromatic amino which may be substituted or an aromatic boryl which may be substituted; and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl, naphthyl, thiophenyl, carbazolyl, diazolyl, triazolyl, pyridyl, methoxy, ethoxy, diarylamino or diarylboryl, and X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ is hydrogen or phenyl, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The light emitting device material according to claim 4. The light emitting device material is a material for a hole transport layer or a hole injection layer,
In the compound represented by the general formula (2),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² and X ³ are each independently hydrogen or optionally substituted aromatic amino, and
A plurality of X ¹ , X ² and X ³ may be bonded to each ring independently.
The light emitting device material according to claim 4. The light emitting device material is a material for a hole transport layer or a hole injection layer,
In the compound represented by the general formula (2),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are diarylamino, X ³ is hydrogen, and
X ¹ , X ² and X ³ are bonded to each ring,
The light emitting device material according to claim 4. The light emitting element material is a material for an electron transport layer or an electron injection layer,
In the compound represented by the general formula (2), (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen or optionally substituted heteroaryl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. The light emitting element material is a material for an electron transport layer or an electron injection layer,
In the compound represented by the general formula (2), (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenanthrolinyl, carbazolyl, diazolyl, triazolyl or pyridyl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen or optionally substituted aryl, and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl or naphthyl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted aryl;
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are each independently hydrogen, an optionally substituted aromatic amino or an optionally substituted aromatic boryl. And
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ and R ¹¹ are each independently methyl or phenyl;
X ¹ and X ² are each independently diarylamino or diarylboryl, X ³ , X ⁴ , X ⁵ , R ¹² and R ¹³ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 6 carbons or aryl having 5 to 20 carbons;
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, aryl having 5 to 20 carbon atoms, alkoxy having 1 to 10 carbon atoms or aromatic amino; and
A plurality of X ¹ , X ² , X ³ , X ⁴ and X ⁵ may be independently bonded to each ring;
The light emitting device material according to claim 4. The light emitting element material is a material for a light emitting layer,
In the compound represented by the general formula (3), (4) or (5),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl or phenyl;
X ¹ and X ² are each independently phenyl, naphthyl, methoxy, ethoxy, diphenylamino or dinaphthylamino, X ³ , X ⁴ and X ⁵ are hydrogen, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each bonded to each ring,
The light emitting device material according to claim 4. A pair of electrodes consisting of an anode and a cathode;
It is disposed between the pair of electrodes, and has one or a plurality of layers containing the light emitting element material according to any one of claims 1 to 17.
Organic electroluminescent device.   A display device comprising the organic electroluminescent element according to claim 18.   The illuminating device provided with the organic electroluminescent element of Claim 18.

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