JP2007299980A - Organic electroluminescence device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescence device which is excellent in performance such as light emission and current efficiency. <P>SOLUTION: The organic electroluminescence device has such a configuration that a pair of electrodes of an anode and a cathode are provided, and a light emitting layer containing a host and a dopant is arranged between the electrodes, wherein the dopant contains, at least, a kind of a fused polycyclic compound. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element and a display device and a lighting device using the same.

  2. Description of the Related Art Conventionally, display devices using light emitting elements that emit electroluminescence have been studied variously because they can be reduced in power and thinned. Further, organic electroluminescent elements made of organic materials can be easily reduced in weight and size. Therefore, it has been actively studied. In particular, the development of organic materials with light emission characteristics such as blue, which is one of the three primary colors of light, and organic materials that have charge transporting ability (such as semiconductors and superconductors) such as holes and electrons The development of materials has been actively studied so far, regardless of whether it is a high molecular compound or a low molecular compound.

  For example, an organic electroluminescent device using a distyrylbenzene derivative as a light emitting layer has been reported (Japanese Patent Laid-Open No. 1-245087 (Patent Document 1), Appl. Phys. Lett., 56, 799, 1990 (non-patent). Reference 1)). However, since these distyrylbenzene derivatives are easily crystallized, the stability of the thin film is low, and the pi conjugation is relatively small, so that the light emission efficiency of the organic electroluminescence device using them is low, which is not practical.

  As a material design capable of exhibiting high luminous efficiency and high charge transporting ability, it is possible to construct a molecule having a pi-conjugated skeleton with high planarity. One example is a distyrylbenzene derivative crosslinked with silicon and carbon as an example of a distyrylbenzene derivative in which pi conjugation is effectively expanded (Japanese Patent Laid-Open No. 2005-154410 (Patent Document 2), J. Am. Chem. Soc., 2005, 127, 1638-1639 (non-patent document 2)). In these documents, optical properties in a solution are reported, but examples in which these are used as a light emitting material for an organic EL device are not disclosed.

  Examples using an anthracene derivative in the light emitting layer of an organic electroluminescent device (Japanese Patent Laid-Open No. 2006-45503 (Patent Document 3), Japanese Patent Laid-Open No. 11-3782 (Patent Document 4), Appl. Phys. Lett., 56, 799, 1990 (Non-Patent Document 1), JP-A-11-312588 (Patent Document 5), JP-A-11-323323 (Patent Document 6), JP-A-11-329732 (Patent Document 7) JP-A-8-12600 (Patent Document 8), JP-A-11-111458 (Patent Document 9), JP-A 2000-344691 (Patent Document 10) and JP-A-2002-154993 (Patent Document). 11)) has been reported.

  In order to obtain an organic EL element with higher efficiency and longer life, a method of doping a light emitting layer with a small amount of fluorescent dye has been proposed. As an example of this, an organic EL device using an anthracene derivative as a host material and a perylene derivative as a dopant material is disclosed (Appl. Phys. Lett., 80, 3201, 2002 (Non-patent Document 3), JP-A 2006- No. 45503 (Patent Document 3)). In addition, an organic EL element using an anthracene derivative as a host material and an amine-containing styryl derivative as a dopant is disclosed (Japanese Patent Laid-Open No. 2006-45503 (Patent Document 3), International Publication No. 01/21729 (Patent Document). Reference 12)).

JP-A-1-245087 JP 2005-154410 A JP 2006-45503 A Japanese Patent Laid-Open No. 11-3782 Japanese Patent Laid-Open No. 11-312588 JP-A-11-323323 JP 11-329732 A JP-A-8-12600 JP-A-11-111458 Japanese Patent Laid-Open No. 2000-344691 Japanese Patent Laid-Open No. 2002-154993 International Publication No. 01/21729 Specification Appl. Phys. Lett., 56, 799, 1990 J. Am. Chem. Soc., 2005, 127, 1638-1639 Appl. Phys. Lett., 80, 3201, 2002

  However, even if the organic material described above is used alone as the light emitting material, sufficient characteristics may not be obtained in terms of color purity, light emission efficiency, carrier mobility, carrier injection, and device lifetime. is there. The same applies to the doping method described above. Therefore, it is desired to develop an organic electroluminescent device having a light emitting layer satisfying these characteristics by examining various combinations of organic materials.

  As a result of intensive studies to solve the above problems, the inventors of the present invention have an organic electric field including a light emitting layer containing at least one compound represented by the following general formula (1) or (2) as a dopant material in the light emitting layer. It has been found that an organic electroluminescent device excellent in luminous efficiency, current efficiency, etc. can be obtained by using a light emitting device, and the present invention has been completed. Further, it has been found that an organic electroluminescent device having better performance can be obtained by containing at least one compound containing at least one anthracene ring in the molecular structure as a host material.

  That is, this invention provides the following organic electroluminescent elements and a display apparatus and an illuminating device using the same.

（一般式（１）又は（２）において、
Ｒ¹及びＲ²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ルコキシ、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、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リールアルコキシ、置換されていてもよいアリールアルキルチオ、置換されていてもよいアリールアルケニル、置換されていてもよいアリールアルキニル、置換されていてもよいアミノ、置換されていてもよいシリル、置換されていてもよいシリルオキシ、置換されていてもよいアリールスルフォニルオキシ、置換されていてもよいアルキルスルフォニルオキシ又は置換されていてもよいヘテロアリールであり、
Ｒ³及びＲ⁴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ルコキシ、置換されていてもよいアリール、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リールアルキル、置換されていてもよいアリールアルコキシ、置換されていてもよいアリールアルケニル、置換されていてもよいアリールアルキニル又は置換されていてもよいヘテロアリールであり、また、Ｒ³及びＲ⁴は互いに結合して環を形成してもよく、
Ｒ⁵及びＲ⁶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ルコキシ、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、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リールアルコキシ、置換されていてもよいアリールアルキルチオ、置換されていてもよいアリールアルケニル、置換されていてもよいアリールアルキニル、置換されていてもよいボリル、置換されていてもよいアミノ、置換されていてもよいシリル、置換されていてもよいシリルオキシ、置換されていてもよいアリールスルフォニルオキシ、置換されていてもよいアルキルスルフォニルオキシ、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、ハロゲン、シアノ、ニトロ又はヒドロキシルであり、そして、
ｍは０，１又は２であり、ｎは、それぞれ独立して、０，１，２，３又は４である。） [1] A light emitting layer containing a pair of electrodes composed of an anode and a cathode and a host and a dopant disposed between the pair of electrodes, and represented by the following general formula (1) or (2) as the dopant An organic electroluminescent device containing at least one compound.

(In general formula (1) or (2),
R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Alkylthio, which may be substituted, aryl which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, arylalkyl which may be substituted, arylalkoxy which may be substituted, substituted Arylalkylthio which may be substituted, arylalkenyl which may be substituted, arylalkynyl which may be substituted, amino which may be substituted, silyl which may be substituted, silyloxy which may be substituted, substituted Arylsulfonyloxy which may be substituted, alkyls which may be substituted Sulfonyloxy or optionally substituted heteroaryl;
R ³ and R ⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl, optionally substituted arylalkoxy, optionally substituted arylalkenyl, optionally substituted arylalkynyl or substituted And R ³ and R ⁴ may be bonded to each other to form a ring,
R ⁵ and R ⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Alkylthio, which may be substituted, aryl which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, arylalkyl which may be substituted, arylalkoxy which may be substituted, substituted Optionally substituted arylalkylthio, optionally substituted arylalkenyl, optionally substituted arylalkynyl, optionally substituted boryl, optionally substituted amino, optionally substituted silyl, substituted Optionally substituted silyloxy, optionally substituted arylsulfonyloxy, Optionally substituted alkylsulfonyloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, halogen, cyano, nitro or hydroxyl, and
m is 0, 1 or 2, and n is independently 0, 1, 2, 3 or 4. )

[2] R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl, substituted Arylalkyl which may be substituted or heteroaryl which may be substituted,
R ³ and R ⁴ are each independently hydrogen, optionally substituted aryl, or optionally substituted heteroaryl,
In the case where R ³ and R ⁴ may be substituted aryl, they may be bonded to each other and optionally substituted divalent biaryl.
R ⁵ and R ⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl, An optionally substituted arylalkyl, an optionally substituted arylalkoxy, an optionally substituted boryl, an optionally substituted amino, an optionally substituted silyl, an optionally substituted heteroaryl or halogen. And
m is 0, 1 or 2, and n is independently 0, 1, 2, 3 or 4,
The organic electroluminescent element as described in [1].

[3] R ¹ and R ² 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 C1-C20 alkoxy, C6-C30 aryl which may be substituted, C7-C30 arylalkyl which may be substituted, or C2-C30 which may be substituted Is heteroaryl,
R ³ and R ⁴ are each independently hydrogen, optionally substituted aryl having 6 to 30 carbon atoms or optionally substituted heteroaryl having 2 to 30 carbon atoms,
In the case where R ³ and R ⁴ are optionally substituted aryl having 6 to 30 carbon atoms, they may be bonded to each other and optionally substituted divalent biaryl having 12 to 60 carbon atoms,
R ⁵ and R ⁶ 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. 1-20 alkoxy, optionally substituted aryl having 6-30 carbon atoms, optionally substituted arylalkyl having 7-30 carbon atoms, optionally substituted arylalkoxy having 7-30 carbon atoms, An optionally substituted aromatic boryl, an optionally substituted aromatic amino, an optionally substituted silyl, an optionally substituted heteroaryl having 2 to 30 carbon atoms or halogen;
The substituents in R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl. Phenanthrolinyl or thienyl, and
m is 0, 1 or 2, and n is independently 0, 1, 2 or 3,
The organic electroluminescent element as described in [1].

[4] R ¹ and R ² are each independently alkyl having 1 to 12 carbons, aryl having 6 to 25 carbons, or heteroaryl having 2 to 25 carbons,
R ³ and R ⁴ are each independently hydrogen, aryl having 6 to 25 carbon atoms or heteroaryl having 2 to 25 carbon atoms,
Further, when R ³ and R ⁴ are aryl having 6 to 25 carbon atoms, they may be bonded to each other to be bivalent biaryl having 12 to 50 carbon atoms,
R ⁵ and R ⁶ are each independently hydrogen, C 1-12 alkyl, C 1-12 alkoxy, C 6-25 aryl, aromatic boryl, aromatic amino, C 2 25 heteroaryls or halogens, and
m is 0, 1 or 2, and n is independently 0, 1 or 2,
The organic electroluminescent element as described in [1].

[5] R ¹ and R ² are each independently methyl, ethyl, propyl, butyl, hexyl, octyl or phenyl;
R ³ and R ⁴ are each independently phenyl, biphenyl, naphthyl or pyridyl;
Further, when R ³ and R ⁴ are phenyl, they may be bonded to each other to be divalent biphenyl,
R ⁵ and R ⁶ are each independently hydrogen, methoxy or F, and
m is 0 or 1, and n is independently 0 or 1,
The organic electroluminescent element as described in [1].

[6] The compound represented by the general formula (1) or (2) is a compound represented by the following formula (1-1), (1-2), (2-1) or (2-2). The organic electroluminescent element as described in [1].

[7] The organic electroluminescence device according to any one of [1] to [6], wherein the host contains at least one compound containing at least one anthracene ring in the molecular structure.

（一般式（３）において、
Ｒ¹⁰，Ｒ¹¹，Ｒ¹²，Ｒ¹³，Ｒ¹⁴，Ｒ¹⁵，Ｒ¹⁶及びＲ¹⁷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ルコキシ、置換されていてもよいアリール、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リールアルキル、置換されていてもよいアリールアルケニル、置換されていてもよいヘテロアリール又は置換されていてもよいシクロアルキルであり、そして、
Ｒ¹⁸及びＲ¹⁹は、それぞれ独立して、置換されていてもよいアリール、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リールアルキル、置換されていてもよいアリールアルコキシ、置換されていてもよいアリールアルケニル、置換されていてもよいアリールアルキニル又は置換されていてもよいヘテロアリールである。） [8] The organic electroluminescent element according to any one of [1] to [7], wherein the host contains at least one compound represented by the following general formula (3).

(In general formula (3),
R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl, optionally substituted arylalkenyl, substituted Optionally substituted heteroaryl or optionally substituted cycloalkyl, and
R ¹⁸ and R ¹⁹ are each independently an optionally substituted aryl, an optionally substituted aryloxy, an optionally substituted arylalkyl, an optionally substituted arylalkoxy, a substituted An optionally substituted arylalkenyl, an optionally substituted arylalkynyl or an optionally substituted heteroaryl. )

[9] R ¹⁰ , R ¹¹ , R ¹² and R ¹³ each independently represent hydrogen, optionally substituted alkyl having 1 to 25 carbon atoms, or optionally substituted alkenyl having 2 to 25 carbon atoms. , An optionally substituted alkoxy having 1 to 25 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms,
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, alkyl having 1 to 25 carbons or alkoxy having 1 to 25 carbons;
R ¹⁸ and R ¹⁹ are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and
The substituents in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl, phenanthrolinyl or Is thienyl,
The organic electroluminescent element as described in [8].

[10] R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, optionally substituted alkyl having 1 to 25 carbon atoms, or optionally substituted alkenyl having 2 to 25 carbon atoms. , An optionally substituted alkoxy having 1 to 25 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms,
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, alkyl having 1 to 25 carbons or alkoxy having 1 to 25 carbons;
R ¹⁸ and R ¹⁹ are each independently an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted anthryl, an optionally substituted phenanthryl, and
The substituents in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl, phenanthrolinyl or Is thienyl,
The organic electroluminescent element as described in [8].

（一般式（３’）において、
Ｒ¹⁰，Ｒ¹¹，Ｒ¹²及びＲ¹³は、それぞれ独立して、水素、炭素数１〜２４のアルキル又は炭素数１〜２４のアルコキシであり、
Ａ¹，Ａ²，Ａ³，Ａ⁴及びＡ⁵は、それぞれ独立して、水素、炭素数１〜２４のアルキル又は炭素数３〜２４のシクロアルキルであり、
Ｂ¹及びＢ²は、それぞれ独立して、水素、炭素数６〜２５のアリール、炭素数１〜２４のアルキル又は炭素数３〜２４のシクロアルキルであり、この炭素数６〜２５のアリールにおける任意の水素は炭素数１〜１２のアルキル、炭素数３〜１２のシクロアルキル又は炭素数６〜１２のアリールで置換されていてもよく、この炭素数１〜２４のアルキルにおける任意の−ＣＨ₂−は、−Ｏ−で置換されていてもよく、この炭素数１〜２４のアルキルにおけるナフタレン環に直結している−ＣＨ₂−を除く任意の−ＣＨ₂−は、炭素数６〜２４のアリーレンで置換されていてもよく、この炭素数３〜２４のシクロアルキルにおける任意の水素は炭素数１〜２４のアルキル又は炭素数６〜２５のアリールで置換されていてもよく、そして、
Ｘ¹，Ｘ²，Ｘ³，Ｘ⁴及びＸ⁵は、それぞれ独立して、水素、炭素数１〜２４のアルキル又は炭素数３〜２４のシクロアルキルであり、この炭素数１〜２４のアルキルにおける任意の−ＣＨ₂−は、−Ｏ−で置換されていてもよく、この炭素数１〜２４のアルキルにおけるフェニル基に直結している−ＣＨ₂−を除く任意の−ＣＨ₂−は、炭素数６〜２４のアリーレンで置換されていてもよく、この炭素数３〜２４のシクロアルキルにおける任意の水素は炭素数１〜２４のアルキル又は炭素数６〜１２のアリールで置換されていてもよい。） [11] The organic electroluminescence device according to [8], wherein the compound represented by the general formula (3) is a compound represented by the following general formula (3 ′).

(In general formula (3 ′),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 24 carbons or alkoxy having 1 to 24 carbons;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are each independently hydrogen, alkyl having 1 to 24 carbons or cycloalkyl having 3 to 24 carbons;
B ¹ and B ² are each independently hydrogen, aryl having 6 to 25 carbon atoms, alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, and in the aryl having 6 to 25 carbon atoms, Arbitrary hydrogen may be substituted by alkyl having 1 to 12 carbons, cycloalkyl having 3 to 12 carbons or aryl having 6 to 12 carbons, and any —CH ₂ in the alkyl having 1 to 24 carbons. — May be substituted with —O—, and any —CH ₂ — other than —CH ₂ — directly bonded to the naphthalene ring in the alkyl having 1 to 24 carbon atoms may have 6 to 24 carbon atoms. Optionally substituted with arylene, any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 6 to 25 carbon atoms, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, alkyl having 1 to 24 carbons or cycloalkyl having 3 to 24 carbons, and the alkyl having 1 to 24 carbons Any —CH ₂ — in the above may be substituted with —O—, and any —CH ₂ — except for —CH ₂ — directly bonded to the phenyl group in the alkyl having 1 to 24 carbon atoms is Arylene having 6 to 24 carbon atoms may be substituted, and any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 6 to 12 carbon atoms. Good. )

[12] R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen or alkyl having 1 to 12 carbons;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are each independently hydrogen, alkyl having 1 to 12 carbons or cyclohexyl,
B ¹ and B ² are each independently hydrogen, methyl, t-butyl, or any hydrogen atom having 1 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 12 carbon atoms. Phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, which may be substituted with
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, alkyl having 1 to 12 carbons or cycloalkyl having 3 to 12 carbons,
The organic electroluminescent element as described in [8].

[13] R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, methyl or t-butyl;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are hydrogen, methyl, t-butyl or cyclohexyl,
B ¹ and B ² are each independently hydrogen, phenyl, 2-biphenylyl, 3-biphenylyl, m-terphenyl-5′-yl, m-terphenyl-3-yl, 1-naphthyl, 2-naphthyl. 2- (2-naphthyl) phenyl, 3,5-di (1-naphthyl) phenyl, 3,5-di (2-naphthyl) phenyl, p-terphenyl-2′-yl, m-terphenyl-2 -Yl, o-terphenyl-2-yl, p-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, m -Quaterphenyl-2-yl, m-quaterphenyl-3-yl, 6- (m-terphenyl-5'-yl) -2-naphthyl or 4- (m-terphenyl-5'-yl) -1-naphthyl, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, methyl, t-butyl or cyclohexyl.
The organic electroluminescent element as described in [8].

[14] The organic electroluminescence device according to [8], wherein the compound represented by the general formula (3) is a compound represented by the following formula (3-1).

（一般式（４）において、
Ｒ²¹，Ｒ²²，Ｒ²³，Ｒ²⁴，Ｒ²⁵及びＲ²⁶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コキシ、置換されていてもよいアリール、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リールアルケニル、置換されていてもよいボリル、置換されていてもよいアミノ、置換されていてもよいシリル、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、ハロゲン、シアノ、ニトロ又はヒドロキシルであり、
Ｍは、Ａｌ、Ｇａ、Ｍｇ、Ｂｅ又はＺｎであり、そして、
ｎは、２又は３である。） [15] [1] to [14] having an electron transport layer and / or an electron injection layer containing at least one compound represented by the following general formula (4) between the cathode and the light emitting layer. An organic electroluminescent device according to any one of the above.

(In general formula (4),
R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, Optionally substituted aryl, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted boryl, optionally substituted amino, optionally substituted silyl, Optionally substituted heteroaryl, optionally substituted cycloalkyl, halogen, cyano, nitro or hydroxyl;
M is Al, Ga, Mg, Be or Zn, and
n is 2 or 3. )

[16] R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted. Good alkoxy, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, halogen or cyano,
M is Al, Ga, Mg, Be or Zn, and
n is 2 or 3;
The organic electroluminescent element as described in [15].

[17] R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, or optionally substituted carbon. Alkenyl having 2 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms which may be substituted, aryl having 6 to 30 carbon atoms which may be substituted, arylalkyl having 7 to 30 carbon atoms which may be substituted, Optionally substituted heteroaryl having 2 to 30 carbon atoms, halogen or cyano,
The substituents in R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl or pyrimidinyl. ,
M is Al, Mg or Zn, and
n is 2 or 3;
The organic electroluminescent element as described in [15].

[18] R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or 1 to 15 carbons. Alkoxy, aryl having 6 to 25 carbon atoms, arylalkyl having 7 to 25 carbon atoms, heteroaryl having 2 to 25 carbon atoms, halogen or cyano,
M is Al, Mg or Zn, and
n is 2 or 3;
The organic electroluminescent element as described in [15].

[19] R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, methyl, ethyl, propyl, isopropyl, butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, Halogen or cyano,
M is Al and
n is 3.
The organic electroluminescent element as described in [15].

[20] The organic electroluminescence device according to [15], wherein the compound represented by the general formula (4) is a compound represented by the following formula (4-1).

（一般式（５）において、
Ｇは、単なる結合手又はｎ価の連結基を表し、
ｎは、２，３，４，５，６，７又は８であり、
Ｒ³¹，Ｒ³²，Ｒ³³，Ｒ³⁴，Ｒ³⁵，Ｒ³⁶，Ｒ³⁷及びＲ³⁸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リール、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リールアルケニル、置換されていてもよいボリル、置換されていてもよいシリル、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又はシアノであり、隣接する基は互いに結合して縮合環を形成してもよく、Ｒ³¹，Ｒ³²，Ｒ³³，Ｒ³⁴，Ｒ³⁵，Ｒ³⁶，Ｒ³⁷及びＲ³⁸のうち少なくとも１つはＧを表し、そして、
Ｒ³¹，Ｒ³²，Ｒ³³，Ｒ³⁴，Ｒ³⁵，Ｒ³⁶，Ｒ³⁷及びＲ³⁸と２，２’−ビピリジル核とで形成されるｎ個の２，２’−ビピリジル残基は、それぞれ同じか又は異なっていてもよい。） [21] [1] to [14] having an electron transport layer and / or an electron injection layer containing at least one compound represented by the following general formula (5) between the cathode and the light emitting layer. The organic electroluminescent element as described in any of the above.

(In general formula (5),
G represents a simple bond or an n-valent linking group,
n is 2, 3, 4, 5, 6, 7 or 8;
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally substituted aryl, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted boryl, optionally substituted silyl, optionally substituted heteroaryl, substituted Cycloalkyl or cyano which may be substituted, adjacent groups may be bonded to each other to form a condensed ring, and R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and At least one of R ³⁸ represents G, and
N 2,2′-bipyridyl residues formed by R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ and the 2,2′-bipyridyl nucleus are respectively They may be the same or different. )

[22] G represents an optionally substituted n-valent aromatic group or heteroaromatic group composed of one or more 5-membered or 6-membered rings,
n is 2, 3, 4, 5 or 6;
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, or substituted. May be an alkenyl having 2 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms which may be substituted, an arylalkyl having 7 to 30 carbon atoms which may be substituted, and an 8 to 30 carbon atoms which may be substituted. Arylalkenyl, arylboryl, alkylsilyl, optionally substituted heteroaryl having 2 to 30 carbon atoms, optionally substituted cycloalkyl having 3 to 10 carbon atoms, or cyano, and
The substituents for G, R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl. , Naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, oxadiazolyl, quinolyl, phenanthrolinyl, benzoxazolyl, benzothiazolyl, benzothienyl or carbazolyl Is,
The organic electroluminescent element as described in [21].

[23] G represents an optionally substituted n-valent aromatic group or heteroaromatic group composed of one or a plurality of 5-membered or 6-membered rings. 4 alkyls, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, oxadiazolyl, quinolyl, phenanthrolinyl, Optionally substituted with benzoxazolyl, benzothiazolyl, benzothienyl or carbazolyl,
n is 2, 3 or 4 and
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number. 6-25 aryl, C7-25 arylalkyl, diarylboryl, trialkylsilyl, C3-8 cycloalkyl or cyano.
The organic electroluminescent element as described in [21].

[24] G is an n-valent benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, terphenyl ring, biphenyl ring, thiophene ring, pyridine ring, pyrazine ring, pyrimidine ring, phenalene ring, silole ring or Pyridazine rings, which are alkyls having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl , Triazolyl, quinolyl, phenanthrolinyl, benzothiazolyl, benzothienyl or carbazolyl,
n is 2 or 3, and
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 6 carbons, alkenyl having 2 to 6 carbons or carbon number. 6-20 aryls,
The organic electroluminescent element as described in [21].

[25] G is an n-valent benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, thiophene ring, pyridine ring, phenalene ring or silole ring, and these rings have 1 to 4 carbon atoms. Optionally substituted with alkyl, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl or pyridyl;
n is 2 or 3,
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 4 carbons, phenyl, tolyl or xylyl.
The organic electroluminescent element as described in [21].

[26] The organic electroluminescence device according to [21], wherein the compound represented by the general formula (5) is a compound represented by the following formula (5-1).

[27] A display device comprising the organic electroluminescent element according to any one of [1] to [26].

[28] A lighting device comprising the organic electroluminescent element according to any one of [1] to [26].

  According to a preferred embodiment of the present invention, for example, an organic electroluminescence device having excellent characteristics in terms of color purity, light emission efficiency, carrier mobility and carrier injection, and device life can be obtained. . Moreover, the compound used as a host in the present invention has high fluorescence quantum yield and heat resistance. In addition, the compound used as a dopant in the present invention has a structure in which a distyrylbenzene skeleton is cross-linked, has high planarity, and effectively expands pi conjugation, so that the fluorescence quantum yield is high. Therefore, an organic electroluminescence device having high luminous efficiency, low driving voltage, excellent heat resistance, and long life can be obtained by using a light emitting layer containing such a host material and a dopant material. Furthermore, by using this organic electroluminescent element, a high-performance display device such as a full color display can be obtained.

An organic electroluminescence device according to an embodiment of the present invention will be described in detail.
The organic electroluminescent element according to the present embodiment has a pair of electrodes composed of an anode and a cathode, and a light emitting layer that is disposed between the pair of electrodes and contains a host and a dopant. ) Or an organic electroluminescence device containing at least one compound represented by (2).
The host preferably contains at least one compound containing at least one anthracene ring in the molecular structure. Furthermore, the compound containing this anthracene ring in the molecular structure is preferably a compound represented by the above general formula (3).

  A light emitting layer is formed by containing at least one compound containing at least one anthracene ring in the molecular structure as a host material and containing at least one compound represented by the general formula (1) or (2) as a dopant material. Accordingly, the overlap between the absorption wavelength of the dopant material and the fluorescence wavelength of the host material can be increased, and excitation energy generated on the host material by charge recombination can be transferred to the dopant material with high efficiency. That is, by making the combination of the host material and the dopant material high in energy transfer efficiency, the dopant material can be used at the same efficiency as or higher than that using a dopant material having a high fluorescence quantum yield to increase the light emission efficiency. Can be excited and emitted with high efficiency, and a light emitting layer with improved luminous efficiency can be obtained.

  In addition, an electron transport layer and / or an electron injection layer containing at least one compound represented by the general formula (4) or the general formula (5) may be provided between the cathode and the light emitting layer. preferable. By providing such an electron transport layer and / or an electron injection layer, the characteristics of the organic electroluminescence device can be further improved.

1. Description of Compounds Hereinafter, the compound represented by the above general formula (1) or (2), the compound represented by the above general formula (3), the compound represented by the above general formula (4), and the above general formula (5) ) Will be described in detail.

1-1. The compound represented by the general formula (1) or (2) The compound represented by the general formula (1) or (2) will be described.
The “alkyl” of “optionally substituted alkyl” in R ¹ and R ² of the general formula (1) or (2) may be linear, branched, or cyclic. -20 linear or branched alkyls or cyclic alkyls. 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, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, cyclooctyl and the like. .

The “alkenyl” of “optionally substituted alkenyl” in R ¹ and R ² of the general formula (1) or (2) may be linear or branched, for example, straight chain having 2 to 20 carbon atoms. Examples thereof include chain or branched 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.

The “alkynyl” of the “optionally substituted alkynyl” in R ¹ and R ² of the general formula (1) or (2) may be linear or branched, for example, a straight chain having 2 to 20 carbon atoms. Examples thereof include chain or branched 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 “alkoxy” of “optionally substituted alkoxy” in R ¹ and R ² of the general formula (1) or (2) 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, pentyloxy, cyclopentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, cycloheptyloxy, octyl Examples include oxy, cyclooctyloxy, phenoxy and the like.

“Alkylthio” of “optionally substituted alkylthio” in R ¹ and R ² of formula (1) or (2) 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.

Examples of “aryl” in “optionally substituted aryl” in R ¹ and R ² of the general formula (1) or (2) include aryl having 6 to 30 carbon atoms. Preferred “aryl” is aryl having 6 to 25 carbon atoms. More preferable “aryl” is aryl having 6 to 20 carbon atoms. Specific examples of “aryl” include phenyl, tolyl, xylyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, terphenylyl, fluorenyl, pyrenyl and the like. Particularly preferred “aryl” is phenyl or naphthyl.

“Aryloxy” of “optionally substituted aryloxy” in R ¹ and R ² of the general formula (1) or (2) includes 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. The “aryl” in “aryloxy” includes the aryl described above.

“Arylthio” of “optionally substituted arylthio” in R ¹ and R ² of the general formula (1) or (2) 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. The “aryl” in “arylthio” includes the aryl described above.

Examples of the “arylalkyl (aralkyl)” of the “optionally substituted arylalkyl” in R ¹ and R ² of the general formula (1) or (2) include arylalkyl having 7 to 30 carbon atoms. Preferred “arylalkyl” is arylalkyl having 7 to 25 carbon atoms. More preferable “arylalkyl” is arylalkyl having 7 to 20 carbon atoms. Specific examples of “arylalkyl” include benzyl (phenylmethyl), p-methylbenzyl, o-methoxybenzyl, 3,5-dichlorobenzyl, diphenylmethyl, trityl (triphenylmethyl), mennaphthyl (naphthylmethyl), Phenethyl (phenylethyl), 2,4-dimethylphenethyl, p-methoxyphenethyl, phenylpropyl, 3-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-3-phenylpropyl, phenylbutyl, phenylpentyl, Examples thereof include phenylhexyl, phenylheptyl, phenyloctyl, phenylnonyl, cinnamyl (3-phenylallyl) and styryl (2-phenylvinyl). The “aryl” in “arylalkyl” includes the aryl described above. The “alkyl” in “arylalkyl” includes the above-mentioned alkyl.

“Arylalkoxy” of “optionally substituted arylalkoxy” in R ¹ and R ² of the general formula (1) or (2) includes arylalkoxy having 7 to 30 carbon atoms. Preferred “arylalkoxy” is arylalkoxy having 7 to 25 carbon atoms. More preferred “arylalkoxy” is arylalkoxy having 7 to 20 carbon atoms. Specific examples of “arylalkoxy” include arylmethoxy and arylethoxy. The “aryl” in “arylalkoxy” includes the aryl described above. The “alkoxy” in “arylalkoxy” includes the alkoxy described above.

Examples of “arylalkylthio” of “optionally substituted arylalkylthio” in R ¹ and R ² of general formula (1) or (2) include arylalkylthio having 7 to 30 carbon atoms. Preferred “arylalkylthio” is arylalkylthio having 7 to 25 carbon atoms. More preferred “arylalkylthio” is arylalkylthio having 7 to 20 carbon atoms. Specific “arylalkylthio” includes arylmethoxy, arylethoxy and the like. The “aryl” in “arylalkylthio” includes the aryl described above. The “alkylthio” of “arylalkylthio” includes the alkylthio described above.

Examples of the “arylalkenyl” of the “optionally substituted arylalkenyl” in R ¹ and R ² of the general formula (1) or (2) include arylalkenyl having 8 to 30 carbon atoms. Preferred “arylalkenyl” is arylalkenyl having 8 to 25 carbon atoms. More preferable “arylalkenyl” is arylalkenyl having 8 to 20 carbon atoms. Specific “arylalkenyl” includes arylvinyl, arylpropenyl, arylisopropenyl and the like. The “aryl” in “arylalkenyl” includes the aryl described above. The “alkenyl” in “arylalkenyl” includes the above-mentioned alkenyl.

“Arylalkynyl” of “optionally substituted arylalkynyl” in R ¹ and R ² of the general formula (1) or (2) includes arylalkynyl having 8 to 30 carbon atoms. Preferred “arylalkynyl” is arylalkynyl having 8 to 25 carbon atoms. More preferred “arylalkynyl” is arylalkynyl having 8 to 20 carbon atoms. Specific examples of “arylalkynyl” include arylethynyl, arylpropynyl and the like. The “aryl” in “arylalkynyl” includes the aryl described above. The “alkynyl” of “arylalkynyl” includes the above-mentioned alkynyl.

Specific examples of the “optionally substituted amino” in R ¹ and R ² of the general formula (1) or (2) include amino; alkylamino such as methylamino, ethylamino, cyclohexylamino, and acetylamino. Dialkylamino such as dimethylamino, diethylamino and dibutylamino; diarylamino such as diphenylamino;

Specific examples of the “optionally substituted silyl” in R ¹ and R ² of the general formula (1) or (2) include trimethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and triphenylsilyl. And trioxysilyl such as trimethoxysilyl, triethoxysilyl, and tributoxysilyl.

Examples of “optionally substituted silyloxy” in R ¹ and R ² of the general formula (1) or (2) include trialkylsilyloxy, trialkylarylsilyloxy and the like. Examples of the trialkylsilyloxy include trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, diethylisopropylsilyloxy, dimethylisopropylsilyloxy, di-t-butylmethylsilyloxy, isopropyldimethylsilyloxy, and t-butyldimethylsilyl. Examples thereof include oxy and texyldimethylsilyloxy. Examples of the trialkylarylsilyloxy include diphenylmethylsilyloxy, t-butyldiphenylsilyloxy, t-butyldimethoxyphenylsilyloxy, triphenylsilyloxy, and the like.

Examples of “optionally substituted arylsulfonyloxy” in R ¹ and R ² of the general formula (1) or (2) include benzenesulfonyloxy, p-toluenesulfonyloxy, mesitylenesulfonyloxy, naphthalenesulfonyloxy and the like. It is done. The “aryl” in “arylsulfonyloxy” includes the aryl described above.

Examples of the “optionally substituted alkylsulfonyloxy” in R ¹ and R ² of the general formula (1) or (2) include methanesulfonyloxy, ethanesulfonyloxy, butanesulfonyloxy, octanessulfonyloxy, trifluoromethanesulfonyloxy. Etc. The “alkyl” in “alkylsulfonyloxy” includes the above-mentioned alkyl.

Examples of the “heteroaryl” of the “optionally substituted heteroaryl” in R ¹ and R ² of the general formula (1) or (2) include, for example, an oxygen atom, a sulfur atom, and a nitrogen other than a carbon atom as a ring atom And heterocyclic groups containing 1 to 5 heteroatoms selected from atoms. Focusing on carbon atoms that are constituent atoms other than heteroatoms, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms Is given. For example, 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, phenazinyl, phenoxathinyl, Antoreniru, indolizinyl, phenanthridine, etc. Lori sulfonyl and the like, such as thienyl, oxadiazolyl, pyridyl, benzo [b] thienyl, quinolyl, such as carbazolyl are preferable.

Further, in R ³ and R ⁴ in the general formula (1) or (2), an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted alkoxy An optionally substituted aryl, an optionally substituted aryloxy, an optionally substituted arylalkyl, an optionally substituted arylalkoxy, an optionally substituted arylalkenyl, an optionally substituted Examples of the preferable arylalkynyl or optionally substituted heteroaryl include those described in the description of R ¹ and R ² in the general formula (1) or (2), and the same is preferable. R ³ and R ⁴ may be bonded to each other to form a ring. In particular, when R ³ and R ⁴ are aryls that may be substituted, they may be bonded to each other to be substituted. Biaryls of Examples of “divalent biaryl” of “optionally substituted divalent biaryl” include divalent biaryl having 12 to 60 carbon atoms. Preferred divalent biaryl is divalent biaryl having 12 to 50 carbon atoms. More preferred divalent biaryl is divalent biaryl having 12 to 40 carbon atoms. Specific bivalent biaryls include biphenyl-2,2′-diyl, 1,1′-binaphthyl-2,2′-diyl, 2,2′-binaphthyl-3,3′-diyl and the like. For example, biphenyl-2,2′-diyl is preferred.

Further, in R ⁵ and R ⁶ of the general formula (1) or (2), an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted alkoxy , Optionally substituted alkylthio, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted aryl Alkoxy, optionally substituted arylalkylthio, optionally substituted arylalkenyl, optionally substituted arylalkynyl, optionally substituted amino, optionally substituted silyl, optionally substituted Good silyloxy, optionally substituted arylsulfonyloxy, optionally substituted Examples of the alkylsulfonyloxy and optionally substituted heteroaryl include the same as those described in the description of R ¹ and R ² in the general formula (1) or (2), and the same is preferable. .
In addition, although two R < ⁵ > has couple | bonded with General formula (1) or (2), it is preferable that two R < ⁵ > is the same.

Specific examples of the “optionally substituted boryl” in R ⁵ and R ⁶ of the general formula (1) or (2) include diphenylboryl, ditolylboryl, dimesityrylboryl, dianthrylboryl, anthrylmesitylboryl and the like. And diarylboryl. Examples of the “substituent” of substituted boryl include ortho-disubstituted phenyl. Specific “substituents” include xylyl, mesityl, diisopropylphenyl, triisopropylphenyl, terphenyl and the like.

Examples of “cycloalkyl” of “optionally substituted cycloalkyl” in R ⁵ and R ⁶ of the general formula (1) or (2) 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.

Examples of “halogen” in R ⁵ and R ⁶ of the general formula (1) or (2) include F, Cl, Br, I and the like. Preferred halogen is F.

Examples of the “substituent” in R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the general formula (1) or (2) include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s -Alkyl such as butyl, t-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, cyclooctyl, trifluoromethyl; aryl such as phenyl, naphthyl, anthracenyl, phenanthryl; methylphenyl, ethylphenyl, s Alkylaryl such as -butylphenyl, t-butylphenyl, 1-methylnaphthyl, 2-methylnaphthyl, 4-methylnaphthyl, 1,6-dimethylnaphthyl, 4-t-butylnaphthyl; pyridyl, quinazolinyl, quinolyl, pyrimidinyl, Furyl, thienyl, pyrrolyl, imi Heterocycles such as dazolyl, tetrazolyl, phenanthrolinyl; 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, and still more preferably 1.

  Examples of m in the general formula (1) or (2) include 0 to 2, preferably 0 or 1, and more preferably 0.

  N in the general formula (1) or (2) includes 0 to 4, preferably 0 to 3, more preferably 0 to 2, still more preferably 0 or 1, and most preferably. Is 0.

  Specific examples of the compound represented by the general formula (1) or (2) include, for example, the above formulas (1-1), (1-2), (2-1), and (2-2) The compound represented by these can be mention | raise | lifted.

Further, specific examples of the compound represented by the general formula (1) or (2) are represented by the above formulas (1-1), (1-2), (2-1) and (2-2). In addition to the above compounds, for example, the compounds represented by the general formula (1) exemplified in Table 1 below are represented by the compounds of Specific Examples 1-3 to 1-18 and General Formula (2). With respect to the compounds, the compounds of Specific Examples 2-3 to 2-18 can be mentioned.

1-2. Compound represented by formula (3) The compound represented by formula (3) will be described.
In R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ in the general formula (3), optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl, optionally substituted arylalkenyl, substituted Optionally substituted heteroaryl, optionally substituted cycloalkyl, and halogen as described in the description of R ¹ and R ^{2 and} the description of R ⁵ and R ^{6 in} the general formula (1) or (2) The same thing is mention | raise | lifted and the same thing is preferable.

In R ¹⁸ and R ¹⁹ in the general formula (3), aryl which may be substituted, aryloxy which may be substituted, arylalkyl which may be substituted, arylalkoxy which may be substituted, substituted Examples of the optionally substituted arylalkenyl, optionally substituted arylalkynyl, or optionally substituted heteroaryl include, for example, the description of R ¹ and R ² and R ⁵ and R ^{5 in} formula (1) or (2) Examples thereof are the same as those described in the description of R ⁶ .
Other preferred examples of R ¹⁸ and R ¹⁹ are each independently an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted anthryl, an optionally substituted phenanthryl. is there.

The R ^10, R ¹¹ in the general formula ^{(3), R 12, R} 13, R 14, R 15, definitive R ¹⁶ and R ¹⁷ 'substituent ", R ¹ and in the general formula (1) or (2) Examples thereof are the same as those described in the description of R ² . Preferred substituents include methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl, phenanthrolinyl or thienyl.
Examples of the “substituent” in R ¹⁸ and R ¹⁹ in the general formula (3) include those similar to those described in the description of R ¹ and R ² in the general formula (1) or (2). It is done. In particular, when one of R ¹⁸ and R ¹⁹ is a phenyl group and the other is a naphthyl group, the phenyl group may be substituted with alkyl or cycloalkyl, and the naphthyl group is aryl, alkyl or cycloalkyl. May be substituted.

  Among the compounds represented by the general formula (3), a particularly preferred structure is, for example, a compound represented by the general formula (3 ′).

Examples of the “alkyl having 1 to 24 carbon atoms” in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ of the general formula (3 ′) include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s -Butyl, t-butyl, n-pentyl, isopentyl, t-pentyl, neopentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl , 5-methylhexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.

Examples of the “C1-C24 alkoxy” in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ in the general formula (3 ′) include, for example, methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, s-butyloxy, t-butyloxy, n-pentyloxy, isopentyloxy, t-pentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, n-hexyl Examples include oxy. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.

R ¹⁰ , R ¹¹ , R ¹² and R ¹³ in the general formula (3 ′) are preferably hydrogen or alkyl having 1 to 12 carbons, more preferably hydrogen, methyl or t-butyl, and still more preferably Is hydrogen.

Examples of the “alkyl having 1 to 24 carbon atoms” in A ¹ , A ² , A ³ , A ⁴ and A ⁵ in the general formula (3 ′) include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, t-pentyl, neopentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, n-hexyl, isohexyl, 1-methylpentyl, 2 -Methylpentyl, 5-methylhexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.

Examples of the “cycloalkyl having 3 to 24 carbon atoms” in A ¹ , A ² , A ³ , A ⁴ and A ⁵ in the general formula (3 ′) include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.

A ¹ , A ² , A ³ , A ⁴ and A ^{5 in the} general formula (3 ′) are preferably hydrogen, alkyl having 1 to 12 carbons or cyclohexyl, and more preferably hydrogen, methyl, t-butyl. Or it is a cyclohexyl, More preferably, it is hydrogen.

B ¹ and B ² in formula (3 ′) are each independently hydrogen, aryl having 5 to 25 carbon atoms, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms. These groups are described in detail below.

First, as “aryl having 5 to 25 carbon atoms”, for example, phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, m-terphenyl-2-yl, m-terphenyl-3-yl, m -Terphenyl-4-yl, m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-2-yl, o-ter Phenyl-3-yl, o-terphenyl-4-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2-yl, p-terphenyl-3 -Yl, p-terphenyl-4-yl, p-terphenyl-2'-yl, m-quaterphenyl-2-yl, m-quaterphenyl-3-yl, m-quaterphenyl-4- Il, o-quaterphenyl-2-yl o-quaterphenyl-3-yl, o-quaterphenyl-4-yl, p-quaterphenyl-2-yl, p-quaterphenyl-3-yl, p-quaterphenyl-4-yl, 1-naphthyl, 2-naphthyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 5-chrysenyl, 6-chrenyl, 1- Examples include triphenylenyl and 2-triphenylenyl. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.
Arbitrary hydrogen in this C5-C25 aryl may be substituted by C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl.

  Examples of “aryl having 5 to 25 carbon atoms in which arbitrary hydrogen is substituted with alkyl having 1 to 12 carbon atoms” include, for example, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, 2, 6-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-t-butylphenyl, 2,4-di-t-butylphenyl, 2,4,6-tri-t-butyl Phenyl, 2-methyl-4-biphenylyl, 2-methyl-3-biphenylyl, 2-methyl-2-biphenyl, 3,5-di (2′-methylphenyl) phenyl, 3,5-di (3′-methyl) Phenyl) phenyl, 3,5-di (4′-methylphenyl) phenyl, 3,5-di (4′-tert-butylphenyl) phenyl, 3,5-bis (2 ′, 4′-dimethylphenyl) phenyl 3,5-bi (3 ′, 5′-dimethylphenyl) phenyl, 4-methyl-1-naphthyl, 4-t-butyl-1-naphthyl, 6-methyl-2-naphthyl, 6-t-butyl-2-naphthyl and the like It is done.

  Examples of “aryl having 5 to 25 carbon atoms in which arbitrary hydrogen is substituted with cycloalkyl having 3 to 12 carbon atoms” include, for example, 2-cyclohexylphenyl, 3-cyclohexylphenyl, 4-cyclohexylphenyl, and 2,4-dicyclohexyl. Examples include phenyl, 3,5-dicyclohexylphenyl, 4-cyclohexyl-1-naphthyl, 6-cyclohexyl-2-naphthyl and the like.

  Examples of “aryl having 5 to 25 carbon atoms in which arbitrary hydrogen is substituted with aryl having 6 to 12 carbon atoms” include, for example, 2- (1-naphthyl) phenyl, 3- (1-naphthyl) phenyl, 4- ( 1-naphthyl) phenyl, 2- (2-naphthyl) phenyl, 3- (2-naphthyl) phenyl, 4- (2-naphthyl) phenyl, 3,5-di (1-naphthyl) -phenyl, 3,5- Di (2-naphthyl) -phenyl, 2,4-di (1-naphthyl) -phenyl, 2,4-di (2-naphthyl) -phenyl, 5- (1-naphthyl) -3-biphenylyl, 5- ( 2-naphthyl) -3-biphenylyl, 3,5-bis (2-biphenylyl) phenyl, 3,5-bis (3-biphenylyl) phenyl, 3,5-bis (4-biphenylyl) phenyl, 5′-phenyl- m-Terphenyl- -Yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, 5 '-(1-naphthyl) -m-terphenyl-2-yl, 5 '-(1-naphthyl) -m-terphenyl-3-yl, 5'-(1-naphthyl) -m-terphenyl-4-yl, 5 '-(2-naphthyl) -m-terphenyl-2 -Yl, 5 '-(2-naphthyl) -m-terphenyl-3-yl, 5'-(2-naphthyl) -m-terphenyl-4-yl, 4-phenyl-1-naphthyl, 6-phenyl 2-naphthyl, 2,2′-binaphthyl-6-yl, 1,2′-binaphthyl-6′-yl, 1,2′-binaphthyl-4-yl, 1,1′-binaphthyl-4-yl, 4- (2-biphenylyl) -1-naphthyl, 4- (3-biphenylyl) -1- Butyl, 4- (4-biphenylyl) -1-naphthyl, 4- (m-terphenyl-5′-yl) -1-naphthyl, 6- (2-biphenylyl) -2-naphthyl, 6- (3-biphenylyl) ) -2-naphthyl, 6- (4-biphenylyl) -2-naphthyl, 6- (m-terphenyl-5′-yl) -2-naphthyl and the like.

Secondly, as "alkyl having 1 to 24 carbon atoms", for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, t-pentyl , Neopentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 5-methylhexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.
Arbitrary —CH ₂ — in the alkyl having 1 to 24 carbon atoms may be substituted with —O—. Further, any —CH ₂ — except for —CH ₂ — directly bonded to the naphthalene ring in the alkyl having 1 to 24 carbon atoms may be substituted with arylene having 6 to 24 carbon atoms. Examples of the arylene having 6 to 24 carbon atoms include 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, naphthalene 1,4-diyl, naphthalene-2,6-diyl, and the like.

Examples of the “alkyl having 1 to 24 carbon atoms in which any —CH ₂ — is substituted with —O—” include, for example, methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, s-butyloxy, t -Butyloxy, n-pentyloxy, isopentyloxy, t-pentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, n-hexyloxy, etc. .

The "- - arbitrary -CH ₂ except -CH ₂ connected directly to the naphthalene ring alkyl of 1 to 24 carbon atoms which is substituted by arylene of 6 to 24 carbon atoms", for example, 2-phenylethyl, 2- (4-methylphenyl) ethyl, 1-methyl-1-phenylethyl, 1,1-dimethyl-2-phenylethyl, trityl, 2- (4-biphenylyl) ethyl, 2- (4′-methyl-biphenylyl) ) Ethyl, 2- (4-methyl-1-naphthyl) ethyl, 2- (6-methyl-2-naphthyl) ethyl and the like.

"Arbitrary -CH ₂ - is replaced by -O-, and -CH ₂ connected directly to the naphthalene ring - arbitrary -CH ₂ except - 1 carbon atoms which is substituted by an arylene having 6 to 24 carbon atoms Examples of ˜24 alkyl ”include phenoxy, o-tolyloxy, m-tolyloxy, p-tolyloxy, 1-naphthoxy, 2-naphthoxy, 2,4-dimethylphenoxy, 2,6-dimethylphenoxy, 2,4, 6-trimethylphenoxy, 4-t-butylphenoxy, 2,4-di-t-butylphenoxy, 2,4,6-tri-t-butylphenoxy, 2-phenylethoxy, 2- (4-methylphenyl) ethoxy Etc.

Thirdly, examples of “cycloalkyl having 3 to 24 carbon atoms” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.
Any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 5 to 25 carbon atoms.

  Examples of the “cycloalkyl having 3 to 24 carbon atoms in which arbitrary hydrogen is substituted with alkyl having 1 to 24 carbon atoms” include, for example, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 4, 6 -Trimethylcyclohexyl, 2-t-butylcyclohexyl, 3-t-butylcyclohexyl, 4-t-butylcyclohexyl, 2,4,6-tri-t-butylcyclohexyl and the like.

  Examples of the “cycloalkyl having 3 to 12 carbon atoms in which arbitrary hydrogen is substituted with aryl having 6 to 24 carbon atoms” include 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenylcyclohexyl, and 2,4-diphenyl. Examples include cyclohexyl and 3,5-diphenylcyclohexyl.

Preferred examples of B ¹ and B ² are hydrogen, methyl, t-butyl, phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, m-terphenyl-4′-yl, m-terphenyl-5′-. Yl, p-terphenyl-2'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, o-terphenyl-2-yl, o- Terphenyl-3-yl, 3,5-di (2-naphthyl) phenyl, 3,5-di (1-naphthyl) phenyl, 1-naphthyl, 2-naphthyl, 4-phenyl-1-naphthyl, 6-phenyl 2-naphthyl, 1,2'-binaphthyl-4-yl, 2,2'-binaphthyl-6-yl, 9-phenanthryl, 2-triphenylenyl, 2- (2-naphthyl) phenyl, 5'-phenyl-m -Terphenyl-2 -Yl, 5'-phenyl-m-terphenyl-3-yl, m-quaterphenylyl-2-yl, m-quaterphenylyl-3-yl, 6- (m-terphenyl-5'- Yl) -2-naphthyl, 4- (m-terphenyl-5′-yl) -1-naphthyl and the like. Particularly preferred examples are 2-biphenylyl, 3-biphenylyl, m-terphenyl-5′-yl, m-terphenyl-3-yl, 1-naphthyl, 2-naphthyl and the like.

Both B ¹ and B ² may be the above groups, or one of them may be the above group and the other may be hydrogen. When B ¹ or B ² is a bulky group, the emission wavelength is shifted to the lower wavelength side due to the steric hindrance of the group, so that it is preferable as a host. Further, when B ¹ or B ² is a bulky group, since the glass transition temperature of the compound obtained is high, preferred. When an organic electroluminescent device is produced, crystallization progresses with time if the glass transition temperature is low, and the light emission efficiency and stability may change. Change is smaller. However, when both B ¹ and B ² are too bulky groups, the synthesis may be difficult due to steric hindrance caused by these groups.

Depending on whether the above group is introduced at B ¹ or B ² , the properties of the obtained compound do not change so much. However, the introduction to B ¹ is easier than the introduction to B ² and is advantageous in terms of cost.

X ¹ , X ² , X ³ , X ⁴ and X ⁵ in the general formula (3 ′) are each independently hydrogen, alkyl having 1 to 24 carbons or cycloalkyl having 3 to 24 carbons. These groups are described in detail below.

First, as "alkyl having 1 to 24 carbon atoms", for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, t-pentyl , Neopentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 5-methylhexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.
Arbitrary —CH ₂ — in the alkyl having 1 to 24 carbon atoms may be substituted with —O—. Further, any —CH ₂ — except for —CH ₂ — directly bonded to the naphthalene ring in the alkyl having 1 to 24 carbon atoms may be substituted with arylene having 6 to 24 carbon atoms. Examples of arylene having 6 to 24 carbon atoms are the same as those described in the description of B ¹ and B ² .

Examples of the “alkyl having 1 to 24 carbon atoms in which any —CH ₂ — is substituted with —O—” include, for example, methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, s-butyloxy, t -Butyloxy, n-pentyloxy, isopentyloxy, t-pentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, n-hexyloxy, etc. .

The "- - arbitrary -CH ₂ except -CH ₂ connected directly to the naphthalene ring alkyl of 1 to 24 carbon atoms which is substituted by arylene of 6 to 24 carbon atoms", for example, 2-phenylethyl, 2- (4-methylphenyl) ethyl, 1-methyl-1-phenylethyl, 1,1-dimethyl-2-phenylethyl, trityl, 2- (4-biphenylyl) ethyl, 2- (4′-methyl-biphenylyl) ) Ethyl, 2- (4-methyl-1-naphthyl) ethyl, 2- (6-methyl-2-naphthyl) ethyl and the like.

"Arbitrary -CH ₂ - is replaced by -O-, and -CH ₂ connected directly to the naphthalene ring - arbitrary -CH ₂ except - 1 carbon atoms which is substituted by an arylene having 6 to 24 carbon atoms Examples of ˜24 alkyl ”include phenoxy, o-tolyloxy, m-tolyloxy, p-tolyloxy, 1-naphthoxy, 2-naphthoxy, 2,4-dimethylphenoxy, 2,6-dimethylphenoxy, 2,4, 6-trimethylphenoxy, 4-t-butylphenoxy, 2,4-di-t-butylphenoxy, 2,4,6-tri-t-butylphenoxy, 2-phenylethoxy, 2- (4-methylphenyl) ethoxy Etc.

Secondly, examples of “cycloalkyl having 3 to 24 carbon atoms” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Moreover, what was described by description of general formula (1) or (2) is mention | raise | lifted.
Any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 6 to 12 carbon atoms.

Examples of the “cycloalkyl having 3 to 24 carbon atoms in which arbitrary hydrogen is substituted with alkyl having 1 to 24 carbon atoms” include, for example, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 4, 6 -Trimethylcyclohexyl, 2-t-butylcyclohexyl, 3-t-butylcyclohexyl, 4-t-butylcyclohexyl, 2,4,6-tri-t-butylcyclohexyl and the like.
Examples of the “cycloalkyl having 3 to 12 carbon atoms in which arbitrary hydrogen is substituted with aryl having 6 to 12 carbon atoms” include 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenylcyclohexyl and 2,4-diphenyl. Examples include cyclohexyl and 3,5-diphenylcyclohexyl.

Preferred examples of X ¹ , X ² , X ³ , X ⁴ and X ⁵ are hydrogen, alkyl having 1 to 12 carbons or cycloalkyl having 3 to 12 carbons, and more preferred examples are hydrogen, methyl, t- Butyl and cyclohexyl, and more preferred examples are hydrogen, methyl and t-butyl. The most preferred example is shown below in terms of the structure of the phenyl group.

  Furthermore, specific examples of the compound represented by the general formula (3) include compounds represented by the following formulas (3-2) to (3-103). The following formula (3-32) is the same as the compound represented by the above formula (3-1).

  Among the above specific examples, the compounds (3-20), (3-29), (3-30), (3-31), (3-32), (3-33), (3-34), ( 3-37), (3-38), (3-39), (3-40), (3-41), (3-43), (3-44), (3-45), (3- 47), (3-48), (3-55), (3-56), (3-64), (3-69), (3-70), (3-71) and (3-75) Is preferred.

  Specific examples of the compound represented by the general formula (3) include compounds represented by the following formulas (3-104) to (3-127).

1-3. The compound represented by the general formula (4) The compound represented by the general formula (4) will be described.
R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ in formula (4) may be substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, substituted. Aryl which may be substituted, arylalkyl which may be substituted, arylalkenyl which may be substituted, boryl which may be substituted, amino which may be substituted, silyl which may be substituted, substituted Optionally substituted heteroaryl, optionally substituted cycloalkyl, and halogen are those described in the description of R ¹ and R ^{2 and} the description of R ⁵ and R ⁶ in formula (1) or (2) The same thing is mention | raise | lifted and the same thing is preferable.

The “substituent” in R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ in the general formula (4) is described in the description of R ¹ and R ² in the general formula (1) or (2). The thing similar to what was mentioned is mention | raise | lifted, and the same thing is preferable.

  Examples of M in the general formula (4) include Al, Ga, Mg, Be, and Zn, preferably Al, Mg, and Zn, and more preferably Al.

  In the general formula (4), n is 2 or 3, preferably 3.

  As a further specific example of the compound represented by the general formula (4), for example, a compound represented by the above formula (4-1) can be exemplified.

1-4. The compound represented by the general formula (5) The compound represented by the general formula (5) will be described.
G in the general formula (5) represents a mere bond or an n-valent linking group, for example, an n-valent aromatic group which may be substituted and composed of one or more 5-membered or 6-membered rings. Represents a group or a heteroaromatic group. The n-valent aromatic group or heteroaromatic group is a residue obtained by removing n hydrogen atoms or substituents from an arbitrary aromatic hydrocarbon compound or aromatic heterocyclic compound and a combination thereof, Specifically, it is an n-valent linking group in which n bonds are out of the aromatic ring.

  As the aromatic ring, for example, benzene ring, naphthalene ring, anthracene ring, fluorene ring, biphenyl ring, terphenyl ring, azulene ring, phenanthrene ring, triphenylene ring, pyrene ring, chrysene ring, naphthacene ring, perylene ring, pentacene ring, Hexacene ring, coronene ring, trinaphthylene ring, furan ring, thiophene ring, pyrrole ring, imidazole ring, pyrazole ring, 1,2,4-triazole ring, 1,2,3-triazole ring, oxazole ring, thiazole ring, isoxazole Ring, isothiazole ring, furazane ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, indolizine ring, quinoline ring, isoindole ring, indole ring, isoquinoline ring, phthalazine ring, purine ring, naphthyridine ring, quinoxaline ring, Quinazoline ring Norin ring, pteridine ring, carbazole ring, acridine ring, perimidine ring, phenanthroline ring, phenazine ring, phenalene ring, silole ring, and the like. In addition, they may each independently have a plurality of arbitrary substituents, and the plurality of substituents may be condensed with each other to further form a ring.

  More preferably, a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, terphenyl ring, biphenyl ring, thiophene ring, pyridine ring, pyrazine ring, pyrimidine ring, phenalene ring, silole ring, or pyridazine ring, These rings may be substituted. More preferably, they are a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a thiophene ring, a pyridine ring, a phenalene ring, or a silole ring, and these rings may be substituted.

  Examples of the “substituent” of “optionally having a plurality of arbitrary substituents” include aliphatic carbonization such as methyl, ethyl, propyl, isopropyl, s-butyl, t-butyl and pentyl. Hydrogen groups, cycloaliphatic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, mesityl, o-cumenyl, m-cumenyl, p -Aromatic hydrocarbon groups such as cumenyl, naphthyl, anthracenyl, phenanthryl, biphenylyl, methylphenyl, ethylphenyl, butylphenyl, methylnaphthyl, dimethylnaphthyl, ethylnaphthyl, diethylnaphthyl and butylnaphthyl, pyridyl, quinazolinyl, quinolyl, pyrimidinyl, Pyrazinyl, pi Heterocyclic groups such as dazinyl, furyl, thienyl, pyrrolyl, imidazolyl, tetrazolyl, thiazolyl, triazolyl, oxazolyl, oxadiazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, carbazolyl, phenanthrolinyl, methoxy, ethoxy, propoxy , Alkoxyl groups such as phenoxy and benzyloxy.

  More preferred “substituents” are alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl , Oxazolyl, oxadiazolyl, quinolyl, phenanthryl, benzoxazolyl, benzothiazolyl, benzothienyl or carbazolyl. More preferable “substituents” are alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl. Quinolyl, phenanthrolinyl, benzothiazolyl, benzothienyl or carbazolyl. The most preferred “substituent” is alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl or pyridyl.

Moreover, as G of General formula (2), the following are mentioned, for example. In the structural formula, each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl or 2-naphthyl.

  As n in General formula (5), 2-8 are mentioned, Preferably it is 2-6, More preferably, it is 2-4, More preferably, it is 2 or 3, Most preferably, it is 2.

In R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ in the general formula (5), optionally substituted alkyl, optionally substituted alkenyl, substituted Examples of the optionally substituted aryl, the optionally substituted arylalkyl, the optionally substituted arylalkenyl, the optionally substituted boryl, the optionally substituted silyl, and the optionally substituted cycloalkyl include The thing similar to what was described by description of R < ¹ > and R < ² > and description of R < ⁵ > and R < ⁶ > in General formula (1) or (2) is mention | raise | lifted, and the same thing is preferable. In addition, R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ may be bonded to each other to form a condensed ring. Here, examples of the condensed ring formed include a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a benzoisoquinoline ring, and a phenanthroline ring.

“Heteroaryl” of “optionally substituted heteroaryl” in R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ in the general formula (5) is, for example, a ring Examples of the constituent atom include a heterocyclic group containing 1 to 5 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom in addition to carbon atom. Focusing on carbon atoms that are constituent atoms other than heteroatoms, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms Is given. For example, 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, phenazinyl, phenoxathinyl, Antoreniru, indolizinyl, phenanthridine, etc. Lori sulfonyl and the like, for example triazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, benzo [b] thienyl, benzimidazolyl, quinolyl, isoquinolyl, carbazolyl, etc. phenanthrolinyl are preferred.

As the "substituent" in ^{R 31, R 32, R 33} , R 34, R 35, R 36, R 37 and R ³⁸ in general formula (5), R ¹ and in the general formula (1) or (2) Examples thereof are the same as those described in the description of R ² . Preferred “substituents” are alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, Quinolyl, phenanthrolinyl, benzothiazolyl, benzothienyl or carbazolyl.

  Specific examples of the compound represented by the general formula (5) include a compound represented by the above formula (5-1). Moreover, as description regarding the compound represented by the said General formula (5), the description described in Unexamined-Japanese-Patent No. 2003-123983 can be used, for example.

2. Next, a method for producing the compound represented by the general formula (1), (2), (3), (3 ′), (4) or (5) will be described.

2-1. Production method of compound represented by general formula (1) or (2) The compound represented by general formula (1) or (2) is disclosed in, for example, JP-A-2005-154410 and J. Am. Chem. , 2005, 127, 1638-1639. For reference, the manufacturing method described in JP-A-2005-154410 will be described below.

  The compound represented by the general formula (1) is produced through an intermediate represented by the following formula (1b). Moreover, the compound represented by General formula (2) is manufactured through the intermediate body represented by following formula (2b). First, a method for producing each intermediate represented by the following formula (1b) or (2b) will be described below.

Each raw material represented by the formula (1a) or (2a) is dimetalated by a halogen-metal exchange reaction using an organometallic base, and then an organosilicon reagent represented by the general formula of R ¹ R ² SiXY Each of the intermediates represented by the formula (1b) or (2b) can be produced by capturing at In addition, each raw material represented by Formula (1a) and (2a) is a well-known compound, and is generally available.

  In this case, as the organometallic base to be used, organolithium reagents such as n-BuLi, s-BuLi and t-BuLi, organomagnesium reagents such as alkyl Grignard reagents and alkylmagnesium amides, or alkylzinc reagents can be used. Among these, the yield is the best when metalation is performed in THF using t-BuLi.

  The solvent used in the reaction is not particularly limited as long as it is inert to these organometallic bases, and ether solvents such as THF, diethyl ether and 1,2-dimethoxyethane, aromatic solvents such as benzene and toluene, An aliphatic solvent such as pentane or hexane can be used. The reaction temperature can be −150 ° C. to 150 ° C., preferably −100 ° C. to 100 ° C.

In the organosilicon reagent R ¹ R ² SiXY, X and Y are independently hydrogen, halogen, alkoxy, alkylthio, aryloxy, arylthio, silyl, substituted silyl, silyloxy, substituted silyloxy, arylsulfonyloxy, alkylsulfonyloxy , Stannyl or substituted stannyl.

In formula (1b) or (2b), as X, hydrogen or alkoxy is particularly useful. For the production of a compound having hydrogen as X, for example, R ¹ R ² SiH ₂ , R ¹ R ² SiHCl or the like can be used as the organosilicon reagent R ¹ R ² SiXY.

For the production of a compound having alkoxy as X, R ¹ R ² Si (OR) ₂ or R ¹ R ² SiCl (NR ₂ ) can be used as the organosilicon reagent R ¹ R ² SiXY. In the latter case, after reacting with R ¹ R ² SiCl (NR ₂ ), the desired product can be obtained by alcoholysis in the presence of an acid catalyst such as ammonium chloride without isolation.

  Next, the intramolecular reductive cyclization reaction will be described based on the above reaction formulas. First, each compound represented by the formula (1b) or (2b) is reacted with a metal reducing agent (reductant), whereby an intramolecular reductive cyclization reaction proceeds to produce a dianion intermediate. By further capturing the intermediate with an electrophile, a polycyclic fused-ring π-conjugated organic material which is a cyclization product represented by the formula (1c) or (2c) can be obtained.

  Examples of the metal reducing agent include lithium, lithium naphthalenide, lithium biphenylide, lithium (4,4′-di-t-butylbiphenylide), lithium [8- (N, N-dimethylamino) naphthalenide], Lithium / liquefied ammonia, sodium, sodium naphthalenide, sodium biphenylide, sodium (4,4′-di-t-butylbiphenylide), sodium [8- (N, N-dimethylamino) naphthalenide], sodium / liquefaction Ammonia, potassium, potassium graphite and the like can be mentioned.

  As a solvent used for the reaction, ether solvents such as diethyl ether, dimethyl ether, and 1,2-dimethoxyethane can be used in addition to THF. The reaction temperature can be −78 ° C. to 50 ° C., preferably −20 ° C. to 30 ° C.

A feature of this reaction is that the intermediate produced is a dianion species, and various substituents ^Ra can be introduced by using various electrophiles. As electrophiles, in addition to conventional carbon electrophiles such as alkyl halides and carbonyl compounds, ICH ₂ CH ₂ I, I ₂ , Br ₂ , ICl, NIS, NBS, BrCH ₂ CH ₂ Br, BrCl ₂ CCCl Electrophilic halogenating agents such as ₂ Br or BrF ₂ CCF ₂ Br, or Me ₃ SnCl, Bu ₃ SnCl, Ph ₃ SnCl, R ₃ SiCl, R ₂ Si (OR) Cl, RSi (OR) ₂ Cl, Si (OR) ₃ Cl, R ₂ SiF ₂ , RSiF ₃ , B (OR) ₃ , (iPrO) B (—OCMe ₂ CMe ₂ O—), ClB (NR ₂ ) ₂ , MgCl ₂ , MgBr ₂ , MgI ₂ , Representative examples include electrophilic metallating agents such as ZnCl ₂ , ZnBr ₂ , ZnI ₂ or ZnCl ₂ (tmen) (where R is an alkyl group or an aryl group). In addition, by using a fluorine compound such as aryl fluoride, an aryl group, a heterocyclic group, or a fluorine-substituted alkyl group can be directly introduced.

As shown in each of the following reaction formulas, the conversion from formula (1d) to general formula (1) or from formula (2d) to general formula (2) is performed using BF ₃ .OEt ₂ , BAr ₃ , AlCl, respectively. ₃ , AlBr ₃ , EtAlCl ₂ , Et ₂ AlCl and other common Lewis acids can be used.

  In addition, the production | generation reaction of the compound represented by Formula (1b) or (2b), the production | generation reaction of the compound represented by Formula (1c) or (2c), and the compound represented by General formula (1) or (2) It is preferable to perform the three reactions of the production reaction in an inert gas, and nitrogen, argon, etc. can be used as the inert gas. There is no restriction | limiting in particular in reaction time, What is necessary is just to stop reaction when reaction has fully progressed. The reaction may be traced by a general analytical means such as NMR or chromatography, and the end point of the reaction may be determined at an optimal time.

2-2. Manufacturing method of compound represented by general formula (3) and (3 ') The compound represented by general formula (3) can be manufactured by a well-known synthesis method using a well-known compound. As an example of the manufacturing method, known documents (for example, Patent Document 4, Non-Patent Document 1, Patent Document 5, Patent Document 6, Patent Document 7, Patent Document 8, Patent Document 9, Patent Document 10, and Patent Document 11) It can be synthesized by the method described in 1.
In addition, the compound represented by the general formula (3 ′) can be synthesized, for example, by the method described in JP-A-2004-203268. For reference, the manufacturing method described in JP-A-2004-203268 will be described below.

The compound represented by the general formula (3 ′) can be synthesized using a known synthesis method such as a Suzuki coupling reaction. The Suzuki coupling reaction is a method of coupling an aromatic halide and an aromatic boronic acid using a palladium catalyst in the presence of a base. Specific examples of the reaction route for obtaining the compound represented by the general formula (3 ′) by this method are as follows. In the formula, R ^{10 to} R ¹³ , X ^{1 to} X ⁵ , A ^{1 to} A ⁵ , B ¹ and B ² are as described above.

Specific examples of the palladium catalyst used in this reaction are Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) ₂ , tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone). ) Dipalladium chloroform complex (0) and the like.

  In order to accelerate the reaction, a phosphine compound may optionally be added to these palladium compounds. Specific examples of the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N-dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1′-bis (di-t -Butylphosphino) ferrocene, 2,2'-bis (di-t-butylphosphino) -1,1'-binaphthyl, 2-methoxy-2 '-(di-t-butylphosphino) -1,1 '-Binaphthyl and the like.

  Specific examples of the base used in this reaction are sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid. Tripotassium, potassium fluoride and the like.

  Furthermore, specific examples of the solvent used in this reaction are benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butylmethyl ether, 1,4-dioxane, methanol, ethanol, Isopropyl alcohol and the like. These solvents can be appropriately selected depending on the structures of the aromatic halide and aromatic boronic acid to be reacted. A solvent may be used independently and may be used as a mixed solvent.

  The reaction temperature can be −150 ° C. to 150 ° C., preferably −100 ° C. to 100 ° C. There is no restriction | limiting in particular in reaction time, What is necessary is just to stop reaction when reaction has fully progressed. The reaction may be traced by a general analytical means such as NMR or chromatography, and the end point of the reaction may be determined at an optimal time.

2-3. Production method of compound represented by general formula (4) The compound represented by general formula (4) can be produced by a known synthesis method using a known compound. As an example of the production method, it can be synthesized by a method described in known literature (for example, Jpn. J. Appl. Phys., 32, L514, 1993, etc.). . Moreover, you may use the quinolinol type metal complex marketed.

2-4. The compound represented by the manufacturing method formula of the compound represented by the general formula (5) (5), using known compounds, can be prepared by known synthetic methods. As an example of the production method, publicly known documents (for example, “Metal-Catalyzed Cross-Coupling Reactions-Second, Completely Revised and Enlarged Edition”, “J. Am. Chem. Soc. (1996), 118, 11974”, etc.) ) And the methods described in the examples of the present specification.

3. Organic Electroluminescent Device The organic electroluminescent device 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 it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10Ω / □, for example, 100-5Ω / □, preferably 50-5Ω. It is particularly desirable to use a low resistance product of / □. 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, in a photoconductive material, a compound conventionally used as a charge transport material for holes, a p-type semiconductor, and a hole injection of an organic electroluminescent element are used. Any known material used for the 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, and each is formed of a light emitting material (host material, dopant material). As a material for forming the host in at least one light emitting layer, the compound represented by the general formula (3) is used. Moreover, as a material which forms a dopant, the compound represented by the said General formula (1) or (2) is used.

  The total content of the compounds represented by the general formula (1) or (2) and (3) in the light emitting layer is 1 to 100% by mass, more preferably 10 to 100% by mass, particularly 50 to 100% by mass, especially 80-100 mass% is preferable. 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 0.1 to 50% by mass, more preferably 0.5 to 20% by mass with respect to 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.

  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.

  Moreover, it does not specifically limit as another dopant material, A known compound can be used and it can select from various materials according to a desired luminescent 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, 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 the 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., and longer wavelengths such as aryl groups, heteroaryl groups, arylvinyl groups, amino groups, and cyano groups can be added to the compounds exemplified above as blue to blue-green and green to yellow dopant materials. 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.

  As a material for forming the electron transport layer 106 or the electron injection layer 107, a compound represented by the general formula (4) or (5) can be used. The content of the compound represented by the general formula (4) or (5) in the electron transport layer 106 or the electron injection layer 107 is 1 to 100% by mass, further 10 to 100% by mass, particularly 50 to 100% by mass, 80-100 mass% is especially preferable.

  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 hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials. Among them, anthracene derivatives such as 9,10-bis (2-naphthyl) anthracene, styryl aromatic ring derivatives such as 4,4′-bis (diphenylethenyl) biphenyl, 4,4′-bis (N-carbazolyl) biphenyl A carbazole derivative such as 1,3,5-tris (N-carbazolyl) benzene is 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 terpyridine, naphthyridine derivatives, aldazine derivatives, bisstyryl Conductor, and the like.

<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.

  Hereinafter, each example will be shown to describe the present invention in more detail, but the present invention is not limited thereto.

<Production Example of Compound Represented by Formula (1-1)>
Production examples of the compound represented by the above formula (1-1) will be described.

Reaction (1): Synthesis of Compound (1-1 ′) In a argon atmosphere, a mixture of lithium (130 mg) and naphthalene (2.40 g) was stirred in THF (18 mL) at room temperature for 4 hours to obtain a lithium naphthalenide solution. Prepared. To this solution was added about 1/4 molar amount of Compound (1-1 ") (1.85 g) in THF (12 mL) to the above solution at room temperature. After stirring at room temperature for 5 minutes, benzophenone (3.42) was added. g) was added at room temperature, and the mixture was stirred for 10 minutes, and then a saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ether, and the resulting organic layer was washed with saturated brine, dried over anhydrous MgSO ₄ and filtered. Thereafter, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (toluene / ethyl acetate = 10/1) to give 2.77 g of the objective compound (1-1 ′) as a white solid. Obtained in 78% yield.

Reaction (2): Under argon atmosphere, the compound represented by the above formula (1-1), the compound (1-1 ') in CH ₂ Cl ₂ (350 mL) solution of (2.72 g) BF ₃ · OEt ₂ ( 0.99 mL) was added at room temperature and stirred for 15 minutes. Water was added to the reaction mixture, and the organic layer was extracted with ether. The obtained organic layer was washed with saturated brine, dried over anhydrous MgSO ₄ , filtered, and the solvent was evaporated under reduced pressure. The obtained mixture was purified by silica gel column chromatography (toluene) and recrystallization to obtain 0.48 g of the compound represented by the above formula (1-1) as a yellow solid in a yield of 18%.

The physical properties of the compound represented by the formula (1-1) thus obtained were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 0.34 (s, 12H), 7.06-7.10 (m, 2H), 7.16-7.25 (m, 16H), 7.30-7.33 (m, 12H)
¹³ C-NMR (100.4 MHz, CDCl ₃ ): −4.28, 67.20, 121.86, 124.39, 125.58, 126.68, 127.08, 127.11, 128.07, 128.97, 142.41, 142.53, 143.75, 144.89, 157.49, 171.10
Melting point: 407 ° C, glass transition temperature (Tg): 133 ° C [measuring instrument: Diamond DSC (manufactured by PERKIN-ELMER); measurement conditions: cooling rate 200 ° C / min, heating rate 10 ° C / min]

<Production Example of Compound Represented by Formula (2-1)>
Production examples of the compound represented by the above formula (2-1) will be described.

Reaction (1): Synthesis of Compound (2-1 ′) In a argon atmosphere, a mixture of lithium (22.7 mg) and naphthalene (0.417 g) was stirred in THF (2.5 mL) at room temperature for 4 hours to obtain lithium naphthalenide. A solution was prepared. To this solution was added a THF solution (2 mL) of about 1/4 molar amount of compound (2-1 ") (0.300 g) of the above mixture at room temperature. After stirring at room temperature for 5 minutes, benzophenone (0.595 g) was added at room temperature and stirred for 10 minutes, and then the reaction mixture was added with saturated ammonium chloride solution and extracted with ether, and the resulting organic layer was washed with saturated brine, dried over anhydrous MgSO ₄ and filtered. Thereafter, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel column chromatography to obtain 0.487 g of the objective compound (2-1 ′) as a white solid in a yield of 84%.

Reaction (2): Synthesis of Compound Represented by Formula (2-1) In an argon atmosphere, a solution of compound (1-1 ′) (0.248 g) in CH ₂ Cl ₂ (35 mL) was added to BF ₃ .OEt ₂ ( 0.09 mL) was added at room temperature and stirred for 15 minutes. Water was added to the reaction mixture, and the organic layer was extracted with ether. The obtained organic layer was washed with saturated brine, dried over anhydrous MgSO ₄ , filtered, and the solvent was evaporated under reduced pressure. The obtained mixture was washed with hexane and dried under reduced pressure to obtain 0.226 g of the compound represented by the above formula (2-1) as a yellow solid in a yield of 96%.

The physical properties of the compound represented by the formula (2-1) thus obtained were as follows.
¹ H-NMR (270 MHz, CDCl ₃ ): δ 0.38 (s, 12H), 6.98-7.06 (m, 8H), 7.14-7.24 (m, 12H), 7.30-7.35 (m, 8H), 7.44 (m, 2H)
¹³ C-NMR (67.8 MHz, CDCl ₃ ): −3.83, 66.65, 118.13, 123.27, 125.94, 126.57, 128.10, 129.11, 129.20, 131.10, 142.05, 142.37, 142.42, 144.55, 145.72, 157.18, 170.25
Melting point: 397 ° C, glass transition temperature (Tg): 151 ° C [measuring instrument: Diamond DSC (manufactured by PERKIN-ELMER); measurement conditions: cooling rate 200 ° C / min, temperature rising rate 10 ° C / min]

<Production Example of Compound Represented by Formula (3-1)>
Production examples of the compound represented by the above formula (3-1) will be described.
Under a nitrogen atmosphere, 9-bromo-10-phenylanthracene (3.33 g), 6- (m-terphenyl-5′-yl) naphthylene-2-boronic acid (4.8 g) was mixed with toluene and ethanol (100 mL). Dissolved in (toluene / ethanol = 4/1), added tetrakis (triphenylphosphine) palladium (0) (0.58 g), stirred for 5 minutes, then added 2M aqueous sodium carbonate (10 mL) and refluxed for 8 hours. . After completion of the heating, the reaction solution was cooled, the organic layer was separated, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solid obtained by removing the desiccant and evaporating the solvent under reduced pressure was subjected to column purification with silica gel (solvent: heptane / toluene = 3/1), followed by sublimation purification, and the above formula (3-1 ) Was obtained.

The physical properties of the compound represented by the formula (3-1) thus obtained were as follows.
Melting point: 280 ° C., glass transition temperature (Tg): 143 ° C. [measuring instrument: Diamond DSC (manufactured by PERKIN-ELMER); measurement conditions: cooling rate 200 ° C./min, heating rate 10 ° C./min]

<Compound represented by the above formula (4-1)>
As the compound represented by the above formula (4-1), a reagent manufactured by Tokyo Chemical Industry was used.

<Production Example of Compound Represented by Formula (5-1)>
Production examples of the compound represented by the above formula (5-1) will be described.
A tetrahydrofuran solution (70 ml) containing lithium (0.55 g) and naphthalene (10 g) was stirred in a stream of argon at room temperature for 15 hours to produce lithium naphthalinide. The solution was cooled to −20 ° C., and a tetrahydrofuran solution (30 ml) containing dimethyl-bis- (2,4,6-trimethyl-phenylethynyl) -silane (6.9 g) was added dropwise. Further, tertbutyl bromide (4.6 ml) was added dropwise, and zinc chloride tetramethylethylenediamine (12.6 g) was added. Subsequently, the solution was stirred at room temperature for 30 minutes, 6-bromo-2,2′-bipyridine (11.2 g) and PdCl ₂ (PPh ₃ ) ₂ (1.4 g) were added, and the mixture was stirred at reflux temperature for 4.5 hours. did. After completion of the reaction, the solution was cooled to room temperature and concentrated with an evaporator. The concentrate was purified by column chromatography and recrystallization to obtain 9.2 g of the target compound.

The physical properties of the compound represented by the formula (5-1) thus obtained were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 0.9 (s, 6H), 2.0 (s, 12H), 2.2 (s, 6H), 6.4 (s, 2H), 6.7 (s, 4H), 7.3 (m , 2H), 7.4 (t, 2H), 7.9 (t, 2H), 8.1 (d, 2H), 8.5 (d, 2H), 8.7 (d, 2H)
Melting point: 221 ° C., glass transition temperature (Tg): 97 ° C. [Measuring instrument: Diamond DSC (manufactured by PERKIN-ELMER); measurement conditions: cooling rate 200 ° C./min, heating rate 10 ° C./min]

<Spectral data of the compounds represented by the above formulas (1-1), (2-1) and (3-1)>
For the compounds represented by the above formulas (1-1), (2-1) and (3-1), vapor-deposited thin films were prepared on glass substrates, respectively. An absorption spectrum or a fluorescence spectrum of the prepared thin film was measured using a spectrophotometer (V-560 manufactured by JASCO) or a fluorimeter (FP-777W manufactured by JASCO). FIG. 2 shows the normalized absorption spectrum of the compound represented by the above formula (1-1) or (2-1) and the fluorescence spectrum of the compound represented by the above formula (3-1). As shown in FIG. 2, there is a large overlap between the fluorescence spectrum of the compound represented by the above formula (3-1) and the absorption spectrum of the compound represented by the above formula (1-1) or (2-1). I understand.

<Examples of organic electroluminescence device using the above compound>
The electroluminescent elements according to Examples 1, 2, and 3 and the electroluminescent elements according to Comparative Examples 1 and 2 were produced, and the device characteristics at a luminance of 1000 cd / m ² were respectively expressed as voltage (V) and current density (mA / cm ² ), luminous efficiency (lm / W), current efficiency (cd / A), emission wavelength (nm), and CIE chromaticity (x, y) measurement, and a lifetime that reduces the initial luminance of 1000 cd / m ² by half. A certain luminance half-life (time) was measured. Hereinafter, examples and comparative examples will be described in detail.

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

In Table 1, “Host 1” is a compound represented by the above formula (3-1), “Dopant 1” is a compound represented by the above formula (1-1), and “Dopant 2” is the above It is a compound represented by Formula (2-1). “Alq3” is a compound represented by the above formula (4-1), and “ET” is a compound represented by the above formula (5-1).
In Table 1, “CuPc” is copper phthalocyanine, and “NPD” is N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine, each having the following chemical structural formula.

<Example 1>
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 containing “host 1”. Boat, molybdenum deposition boat with "Dopant 1", molybdenum deposition boat with "ET", molybdenum deposition boat with lithium fluoride, and tungsten deposition boat with aluminum Attached.

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 “host 1” and the vapor deposition boat containing “dopant 1” were heated at the same time to form a light emitting layer by vapor deposition to a film thickness of 30 nm. The deposition rate was adjusted so that the mass ratio of “Host 1” and “Dopant 1” was 99: 1. Next, the evaporation boat containing “ET” was heated and evaporated to a thickness of 20 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 organic electroluminescent element according to Example 1 was obtained by forming a cathode by vapor deposition at a vapor deposition rate of 0.1 to 1 nm / second so that the film thickness was 100 nm.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the device characteristics at a luminance of 1000 cd / m ² were measured. The voltage was 3.8 V, the current density was 11 mA / cm ² , and the luminous efficiency was 7.5 (lm / W). The current efficiency was 9.1 cd / A, the emission wavelengths were 469 nm and 498 nm, and the luminance half-life was 170 hours.

<Example 2>
Except for adjusting the deposition rate of “Host 1” and “Dopant 1” so that the mass ratio of “Host 1” and “Dopant 1” is 95: 5 and setting the material of the electron transport layer to “Alq3”, An electroluminescent device was obtained in exactly the same manner as in Example 1.
Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the device characteristics at a luminance of 1000 cd / m ² were measured. The voltage was 6.6 V, the current density was 14 mA / cm ² , and the luminous efficiency was 3.4 (lm / W). The current efficiency was 7.1 cd / A, the emission wavelengths were 471 nm and 499 nm, and the luminance half-life was 2300 hours.

<Example 3>
An electroluminescent device was obtained in exactly the same manner as in Example 1, except that the dopant material was “Dopant 2” and the material of the electron transport layer was “Alq3”.
Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the device characteristics at a luminance of 1000 cd / m ² were measured. The voltage was 6.6 V, the current density was 27 mA / cm ² , and the luminous efficiency was 1.8 (lm / W). The current efficiency was 3.7 cd / A, the emission wavelengths were 449 nm and 473 nm, and the luminance half-life was 890 hours.

<Comparative Example 1>
An electroluminescent device was obtained in exactly the same manner as in Example 1 except that the light emitting layer was formed only from the host material without adding the dopant material.
Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the device characteristics at a luminance of 1000 cd / m ² were measured. The voltage was 5.1 V, the current density was 46 mA / cm ² , and the luminous efficiency was 1.3 (lm / W). The current efficiency was 2.2 cd / A, the emission wavelength was 442 nm, and the luminance half life was 40 hours.

<Comparative example 2>
An electroluminescent device was obtained in exactly the same manner as in Example 1 except that the light emitting layer was formed only from the host material without adding the dopant material, and the material of the electron transport layer was changed to “Alq3”.
Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the device characteristics at a luminance of 1000 cd / m ² were measured. The voltage was 7.3 V, the current density was 62 mA / cm ² , and the luminous efficiency was 0.69 (lm / W). The current efficiency was 1.6 cd / A, the emission wavelength was 438 nm, and the luminance half-life was 120 hours.

Table 3 below shows the results of the element characteristics of the electroluminescent elements according to Examples 1, 2, and 3 and the electroluminescent elements according to Comparative Examples 1 and 2.

  According to a preferred aspect of the present invention, it is possible to provide an organic electroluminescent element having better performance in light emission efficiency and current efficiency, a display device including the same, a lighting device including the same, and the like.

It is a schematic sectional drawing which shows the organic electroluminescent element which concerns on this embodiment. 2 is an absorption spectrum of a compound represented by formula (1-1) or (2-1) and a fluorescence spectrum of a compound represented by formula (3-1).

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 (28)

A compound having a light emitting layer containing a host and a dopant disposed between a pair of electrodes composed of an anode and a cathode and the host and a dopant, and a compound represented by the following general formula (1) or (2) as the dopant An organic electroluminescent device containing at least one kind.

(In general formula (1) or (2),
R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Alkylthio, which may be substituted, aryl which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, arylalkyl which may be substituted, arylalkoxy which may be substituted, substituted Arylalkylthio which may be substituted, arylalkenyl which may be substituted, arylalkynyl which may be substituted, amino which may be substituted, silyl which may be substituted, silyloxy which may be substituted, substituted Arylsulfonyloxy which may be substituted, alkyls which may be substituted Sulfonyloxy or optionally substituted heteroaryl;
R ³ and R ⁴ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl, optionally substituted arylalkoxy, optionally substituted arylalkenyl, optionally substituted arylalkynyl or substituted And R ³ and R ⁴ may be bonded to each other to form a ring,
R ⁵ and R ⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, substituted Alkylthio, which may be substituted, aryl which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, arylalkyl which may be substituted, arylalkoxy which may be substituted, substituted Optionally substituted arylalkylthio, optionally substituted arylalkenyl, optionally substituted arylalkynyl, optionally substituted boryl, optionally substituted amino, optionally substituted silyl, substituted Optionally substituted silyloxy, optionally substituted arylsulfonyloxy, Optionally substituted alkylsulfonyloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, halogen, cyano, nitro or hydroxyl, and
m is 0, 1 or 2, and n is independently 0, 1, 2, 3 or 4. ) R ¹ and R ² are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl, substituted Arylalkyl or optionally substituted heteroaryl,
R ³ and R ⁴ are each independently hydrogen, optionally substituted aryl, or optionally substituted heteroaryl,
In the case where R ³ and R ⁴ may be substituted aryl, they may be bonded to each other and optionally substituted divalent biaryl.
R ⁵ and R ⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl, An optionally substituted arylalkyl, an optionally substituted arylalkoxy, an optionally substituted boryl, an optionally substituted amino, an optionally substituted silyl, an optionally substituted heteroaryl or halogen. And
m is 0, 1 or 2, and n is independently 0, 1, 2, 3 or 4,
The organic electroluminescent element according to claim 1. R ¹ and R ² 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. 1 to 20 alkoxy, optionally substituted aryl having 6 to 30 carbon atoms, optionally substituted aryl alkyl having 7 to 30 carbon atoms, or optionally substituted heteroaryl having 2 to 30 carbon atoms Yes,
R ³ and R ⁴ are each independently hydrogen, optionally substituted aryl having 6 to 30 carbon atoms or optionally substituted heteroaryl having 2 to 30 carbon atoms,
In the case where R ³ and R ⁴ are optionally substituted aryl having 6 to 30 carbon atoms, they may be bonded to each other and optionally substituted divalent biaryl having 12 to 60 carbon atoms,
R ⁵ and R ⁶ 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. 1-20 alkoxy, optionally substituted aryl having 6-30 carbon atoms, optionally substituted arylalkyl having 7-30 carbon atoms, optionally substituted arylalkoxy having 7-30 carbon atoms, An optionally substituted aromatic boryl, an optionally substituted aromatic amino, an optionally substituted silyl, an optionally substituted heteroaryl having 2 to 30 carbon atoms or halogen;
The substituents in R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl. Phenanthrolinyl or thienyl, and
m is 0, 1 or 2, and n is independently 0, 1, 2 or 3,
The organic electroluminescent element according to claim 1. R ¹ and R ² are each independently alkyl having 1 to 12 carbons, aryl having 6 to 25 carbons or heteroaryl having 2 to 25 carbons;
R ³ and R ⁴ are each independently hydrogen, aryl having 6 to 25 carbon atoms or heteroaryl having 2 to 25 carbon atoms,
Further, when R ³ and R ⁴ are aryl having 6 to 25 carbon atoms, they may be bonded to each other to be bivalent biaryl having 12 to 50 carbon atoms,
R ⁵ and R ⁶ are each independently hydrogen, C 1-12 alkyl, C 1-12 alkoxy, C 6-25 aryl, aromatic boryl, aromatic amino, C 2 25 heteroaryls or halogens, and
m is 0, 1 or 2, and n is independently 0, 1 or 2,
The organic electroluminescent element according to claim 1. R ¹ and R ² are each independently methyl, ethyl, propyl, butyl, hexyl, octyl or phenyl;
R ³ and R ⁴ are each independently phenyl, biphenyl, naphthyl or pyridyl;
Further, when R ³ and R ⁴ are phenyl, they may be bonded to each other to be divalent biphenyl,
R ⁵ and R ⁶ are each independently hydrogen, methoxy or F, and
m is 0 or 1, and n is independently 0 or 1,
The organic electroluminescent element according to claim 1. The compound represented by the general formula (1) or (2) is a compound represented by the following formula (1-1), (1-2), (2-1) or (2-2), Item 2. The organic electroluminescent device according to Item 1.

  The organic electroluminescence device according to any one of claims 1 to 6, wherein the host contains at least one compound containing at least one anthracene ring in the molecular structure. The organic electroluminescent element according to claim 1, wherein the host contains at least one compound represented by the following general formula (3).

(In general formula (3),
R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylalkyl, optionally substituted arylalkenyl, substituted Optionally substituted heteroaryl or optionally substituted cycloalkyl, and
R ¹⁸ and R ¹⁹ are each independently an optionally substituted aryl, an optionally substituted aryloxy, an optionally substituted arylalkyl, an optionally substituted arylalkoxy, a substituted An optionally substituted arylalkenyl, an optionally substituted arylalkynyl or an optionally substituted heteroaryl. ) R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 25 carbon atoms which may be substituted, alkenyl having 2 to 25 carbon atoms which may be substituted, substituted Or an optionally substituted alkoxy having 1 to 25 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms,
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, alkyl having 1 to 25 carbons or alkoxy having 1 to 25 carbons;
R ¹⁸ and R ¹⁹ are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and
The substituents in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl, phenanthrolinyl or Is thienyl,
The organic electroluminescent element according to claim 8. R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 25 carbon atoms which may be substituted, alkenyl having 2 to 25 carbon atoms which may be substituted, substituted Or an optionally substituted alkoxy having 1 to 25 carbon atoms or an optionally substituted aryl having 6 to 30 carbon atoms,
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each independently hydrogen, alkyl having 1 to 25 carbons or alkoxy having 1 to 25 carbons;
R ¹⁸ and R ¹⁹ are each independently an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted anthryl, an optionally substituted phenanthryl, and
The substituents in R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl, pyrimidinyl, quinolyl, phenanthrolinyl or Is thienyl,
The organic electroluminescent element according to claim 8. The organic electroluminescent element according to claim 8, wherein the compound represented by the general formula (3) is a compound represented by the following general formula (3 ').

(In general formula (3 ′),
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, alkyl having 1 to 24 carbons or alkoxy having 1 to 24 carbons;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are each independently hydrogen, alkyl having 1 to 24 carbons or cycloalkyl having 3 to 24 carbons;
B ¹ and B ² are each independently hydrogen, aryl having 6 to 25 carbon atoms, alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, and in the aryl having 6 to 25 carbon atoms, Arbitrary hydrogen may be substituted by alkyl having 1 to 12 carbons, cycloalkyl having 3 to 12 carbons or aryl having 6 to 12 carbons, and any —CH ₂ in the alkyl having 1 to 24 carbons. — May be substituted with —O—, and any —CH ₂ — other than —CH ₂ — directly bonded to the naphthalene ring in the alkyl having 1 to 24 carbon atoms may have 6 to 24 carbon atoms. Optionally substituted with arylene, any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 6 to 25 carbon atoms, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, alkyl having 1 to 24 carbons or cycloalkyl having 3 to 24 carbons, and the alkyl having 1 to 24 carbons Any —CH ₂ — in the above may be substituted with —O—, and any —CH ₂ — except for —CH ₂ — directly bonded to the phenyl group in the alkyl having 1 to 24 carbon atoms is Arylene having 6 to 24 carbon atoms may be substituted, and any hydrogen in the cycloalkyl having 3 to 24 carbon atoms may be substituted with alkyl having 1 to 24 carbon atoms or aryl having 6 to 12 carbon atoms. Good. ) R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen or alkyl having 1 to 12 carbons;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are each independently hydrogen, alkyl having 1 to 12 carbons or cyclohexyl,
B ¹ and B ² are each independently hydrogen, methyl, t-butyl, or any hydrogen atom having 1 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 12 carbon atoms. Phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, which may be substituted with
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, alkyl having 1 to 12 carbons or cycloalkyl having 3 to 12 carbons,
The organic electroluminescent element according to claim 8. R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently hydrogen, methyl or t-butyl;
A ¹ , A ² , A ³ , A ⁴ and A ⁵ are hydrogen, methyl, t-butyl or cyclohexyl,
B ¹ and B ² are each independently hydrogen, phenyl, 2-biphenylyl, 3-biphenylyl, m-terphenyl-5′-yl, m-terphenyl-3-yl, 1-naphthyl, 2-naphthyl. 2- (2-naphthyl) phenyl, 3,5-di (1-naphthyl) phenyl, 3,5-di (2-naphthyl) phenyl, p-terphenyl-2′-yl, m-terphenyl-2 -Yl, o-terphenyl-2-yl, p-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, m -Quaterphenyl-2-yl, m-quaterphenyl-3-yl, 6- (m-terphenyl-5'-yl) -2-naphthyl or 4- (m-terphenyl-5'-yl) -1-naphthyl, and
X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently hydrogen, methyl, t-butyl or cyclohexyl.
The organic electroluminescent element according to claim 8. The organic electroluminescent element according to claim 8, wherein the compound represented by the general formula (3) is a compound represented by the following formula (3-1).

The electron transport layer and / or the electron injection layer containing at least one kind of the compound represented by the following general formula (4) are provided between the cathode and the light emitting layer. Organic electroluminescent device.

(In general formula (4),
R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, Optionally substituted aryl, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted boryl, optionally substituted amino, optionally substituted silyl, Optionally substituted heteroaryl, optionally substituted cycloalkyl, halogen, cyano, nitro or hydroxyl;
M is Al, Ga, Mg, Be or Zn, and
n is 2 or 3. ) R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, Optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, halogen or cyano;
M is Al, Ga, Mg, Be or Zn, and
n is 2 or 3;
The organic electroluminescent element according to claim 15. R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, alkyl having 1 to 20 carbon atoms which may be substituted, or carbon atoms having 2 to 2 carbon atoms which may be substituted. 20 alkenyl, optionally substituted alkoxy having 1 to 20 carbon atoms, optionally substituted aryl having 6 to 30 carbon atoms, optionally substituted aryl alkyl having 7 to 30 carbon atoms, substituted May be a heteroaryl of 2 to 30 carbon atoms, halogen or cyano,
The substituents in R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently methyl, ethyl, propyl, isopropyl, phenyl, naphthyl, methylphenyl, methylnaphthyl, pyridyl or pyrimidinyl. ,
M is Al, Mg or Zn, and
n is 2 or 3;
The organic electroluminescent element according to claim 15. R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 15 carbons, Aryl having 6 to 25 carbon atoms, arylalkyl having 7 to 25 carbon atoms, heteroaryl having 2 to 25 carbon atoms, halogen or cyano;
M is Al, Mg or Zn, and
n is 2 or 3;
The organic electroluminescent element according to claim 15. R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ are each independently hydrogen, methyl, ethyl, propyl, isopropyl, butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, halogen or cyano. And
M is Al and
n is 3.
The organic electroluminescent element according to claim 15. The organic electroluminescent element according to claim 15, wherein the compound represented by the general formula (4) is a compound represented by the following formula (4-1).

The electron transport layer and / or the electron injection layer containing at least one kind of the compound represented by the following general formula (5) are provided between the cathode and the light emitting layer. Organic electroluminescent device.

(In general formula (5),
G represents a simple bond or an n-valent linking group,
n is 2, 3, 4, 5, 6, 7 or 8;
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, substituted Optionally substituted aryl, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted boryl, optionally substituted silyl, optionally substituted heteroaryl, substituted Cycloalkyl or cyano which may be substituted, adjacent groups may be bonded to each other to form a condensed ring, and R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and At least one of R ³⁸ represents G, and
N 2,2′-bipyridyl residues formed by R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ and the 2,2′-bipyridyl nucleus are respectively They may be the same or different. ) G represents an optionally substituted n-valent aromatic group or heteroaromatic group composed of one or more 5-membered or 6-membered rings,
n is 2, 3, 4, 5 or 6;
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, optionally substituted alkyl having 1 to 20 carbon atoms, or substituted. May be an alkenyl having 2 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms which may be substituted, an arylalkyl having 7 to 30 carbon atoms which may be substituted, and an 8 to 30 carbon atoms which may be substituted. Arylalkenyl, arylboryl, alkylsilyl, optionally substituted heteroaryl having 2 to 30 carbon atoms, optionally substituted cycloalkyl having 3 to 10 carbon atoms, or cyano, and
The substituents for G, R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl. , Naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, oxadiazolyl, quinolyl, phenanthrolinyl, benzoxazolyl, benzothiazolyl, benzothienyl or carbazolyl Is,
The organic electroluminescent element according to claim 21. G represents an optionally substituted n-valent aromatic group or heteroaromatic group composed of one or a plurality of 5-membered or 6-membered rings, which is an alkyl having 1 to 4 carbon atoms , Phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, oxadiazolyl, quinolyl, phenanthrolinyl, benzoxazolyl Optionally substituted with benzoyl, benzothiazolyl, benzothienyl or carbazolyl,
n is 2, 3 or 4 and
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or carbon number. 6-25 aryl, C7-25 arylalkyl, diarylboryl, trialkylsilyl, C3-8 cycloalkyl or cyano.
The organic electroluminescent element according to claim 21. G is an n-valent benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, terphenyl ring, biphenyl ring, thiophene ring, pyridine ring, pyrazine ring, pyrimidine ring, phenalene ring, silole ring or pyridazine ring. And these rings are alkyl having 1 to 4 carbon atoms, phenyl, tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, imidazolyl, thiazolyl, triazolyl, Optionally substituted with quinolyl, phenanthrolinyl, benzothiazolyl, benzothienyl or carbazolyl,
n is 2 or 3, and
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 6 carbons, alkenyl having 2 to 6 carbons or carbon number. 6-20 aryls,
The organic electroluminescent element according to claim 21. G is an n-valent benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, thiophene ring, pyridine ring, phenalene ring or silole ring, and these rings are alkyl having 1 to 4 carbon atoms, phenyl , Tolyl, xylyl, mesityl, naphthyl, ethylphenyl, methylnaphthyl, ethylnaphthyl or pyridyl,
n is 2 or 3,
R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ are each independently hydrogen, alkyl having 1 to 4 carbons, phenyl, tolyl or xylyl.
The organic electroluminescent element according to claim 21. The organic electroluminescent element according to claim 21, wherein the compound represented by the general formula (5) is a compound represented by the following formula (5-1).

  A display device comprising the organic electroluminescent element according to claim 1.   A lighting device comprising the organic electroluminescent element according to any one of claims 1 to 26.

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