JP2014205641A - Condensed ring amine compound and organic electroluminescent element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a material having more highly luminous efficiency and an organic EL element using the same.SOLUTION: A condensed ring amine compound is represented by the formula (1) [where at least one of Arand Aris a group represented by the formula (2) (where X and Y are each independently O, S, SO, C(R), NRor Si(R))].

Description

  The present invention relates to a condensed ring amine compound and an organic electroluminescence device using the same.

The performance of organic EL elements has been gradually improved by recent improvements in light emitting materials for organic EL. In particular, improving the color purity of blue organic EL elements (shortening the emission wavelength) is an important technique that leads to improved color reproducibility of displays.
As an example of the material used for the light emitting layer, Patent Document 1 discloses a light emitting material having dibenzofuran, and blue light emission is obtained in an organic electroluminescent device to which the material is applied.

  Patent Document 2 discloses a diaminopyrene derivative having a pyrene ring at the center and having a dibenzofuran ring, a dibenzothiophene ring and the like bonded via an amino group at the 4-position, and an organic EL element to which the diaminopyrene derivative is applied Blue light emission was obtained.

  As described above, many materials such as condensed ring amine derivatives are known as fluorescent materials that emit blue light. However, there is a demand for a material for an organic electroluminescence element that has higher luminous efficiency and that emits light at a shorter wavelength than conventional materials.

WO2006 / 128800 pamphlet WO2010 / 122810 pamphlet

An object of this invention is to provide the material which has higher luminous efficiency, and an organic electroluminescent element using the same. Another object of the present invention is to provide a material that emits light having a shorter wavelength than conventional materials and an organic EL element using the material.
In order to achieve the above object, the present inventors have conducted intensive research and introduced a substituent having a non-conjugated tricyclic structure at the amine substituent end of the condensed ring amine compound, thereby achieving high luminous efficiency and the conventional technology. As a result, it was found that a material exhibiting light emission at a shorter wavelength was obtained, and the present invention was completed.

［式中、Ａｒは、置換若しくは無置換のピレン環、置換若しくは無置換のアントラセン環、置換若しくは無置換のクリセン環、置換若しくは無置換のペリレン環、置換若しくは無置換のフルオランテン環、置換若しくは無置換のベンゾフルオレン環、又は置換若しくは無置換のスピロフルオレン環のｎ価の残基を示す。
ｎは、１〜４の整数を示し、ｎが２以上のときは、複数の−［Ｌ］_ｍ−ＮＡｒ^１Ａｒ^２で示される構造は、互いに同一でも異なっていてもよい。
Ｌは、置換若しくは無置換の環形成炭素数６〜３０の芳香族炭化水素環、又は置換若しくは無置換の環形成原子数５〜３０の複素芳香族環の２価の残基を示す。
ｍは、０〜２の整数を示し、ｍが０のときは、Ａｒと窒素原子とが単結合により結合していることを示し、ｍが２のときは、２つのＬは互いに同一でも異なっていてもよく、２つのＬの置換基同士が結合して環を形成していてもよい。
Ａｒ^１及びＡｒ^２の少なくとも１つは下記式（２）で表される基であり、それ以外のＡｒ^１及びＡｒ^２は、それぞれ独立に置換若しくは無置換の環形成炭素数６〜３０のアリール基、又は置換若しくは無置換の環形成原子数５〜３０のヘテロアリール基である。同一の窒素原子に結合しているＡｒ^１とＡｒ^２の置換基同士が結合して環を形成してもよい。

（式中、Ｘ及びＹは、それぞれ独立にＯ、Ｓ、ＳＯ_２、Ｃ（Ｒ^１０）_２、ＮＲ^１０又はＳｉ（Ｒ^１０）_２を示す。
Ｒ^１１〜Ｒ^１８のいずれか１つは上記（１）式中の窒素原子との結合に用いられ、それ以外のＲ^１１〜Ｒ^１８、及びＲ^１０は、それぞれ独立に水素原子、ハロゲン原子、置換若しくは無置換の炭素数１〜２０のアルキル基、置換若しくは無置換の炭素数２〜２０のアルケニル基、置換若しくは無置換の炭素数２〜２０のアルキニル基、置換もしくは無置換の環形成炭素数３〜１０のシクロアルキル基、置換もしくは無置換の炭素数３〜３０のアルキルシリル基、置換若しくは無置換の環形成炭素数８〜３０のアリールシリル基、シアノ基、置換もしくは無置換の環形成炭素数６〜２０のアリール基、又は置換若しくは無置換の環形成原子数５〜２０のヘテロアリール基を示し、Ｒ^１１〜Ｒ^１８は隣接する置換基同士で飽和又は不飽和の環を形成してもよい。）］ According to one embodiment of the present invention, a condensed ring amine compound represented by the following formula (1) is provided.

[Wherein Ar represents a substituted or unsubstituted pyrene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted perylene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted An n-valent residue of a substituted benzofluorene ring or a substituted or unsubstituted spirofluorene ring is shown.
n represents an integer of 1 to 4, and when n is 2 or more, the structures represented by a plurality of — [L] _m —NAr ¹ Ar ² may be the same as or different from each other.
L represents a divalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms.
m represents an integer of 0 to 2, and when m is 0, it indicates that Ar and a nitrogen atom are bonded by a single bond. When m is 2, two Ls are the same or different from each other. Or two L substituents may be bonded to each other to form a ring.
At least one of Ar ¹ and Ar ² is a group represented by the following formula (2), Ar ¹ and Ar ² otherwise are independently a substituted or unsubstituted ring forming aryl having 6 to 30 carbon atoms Or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Ar ¹ and Ar ² substituents bonded to the same nitrogen atom may be bonded to form a ring.

(Wherein X and Y each independently represent O, S, SO ₂ , C (R ¹⁰ ) ₂ , NR ¹⁰ or Si (R ¹⁰ ) ₂ ).
Any one of R ^{11 to} R ¹⁸ is used for bonding to the nitrogen atom in the above formula (1), and other R ^{11 to} R ¹⁸ and R ¹⁰ are independently a hydrogen atom, a halogen atom, Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted ring-forming carbon A cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 carbon atoms, a cyano group, a substituted or unsubstituted ring forming an aryl group having 6 to 20 carbon atoms, or a substituted or indicates unsubstituted ring atoms 5-20 heteroaryl group, R ¹¹ to R ¹⁸ is a saturated or unsaturated adjacent substituents It may form a ring. ]]

  According to one aspect of the present invention, there is provided one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is a condensation represented by the above formula (1). An organic electroluminescence device containing at least one cyclic amine compound is provided.

  ADVANTAGE OF THE INVENTION According to this invention, the material for organic EL elements which shows high luminous efficiency is provided. Moreover, according to this invention, the material for organic EL elements which show light emission of a short wavelength compared with the past is provided.

In this specification, the number of ring-forming carbon atoms refers to a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among atoms constituting the ring itself. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” described below is the same unless otherwise specified.
The number of ring-forming atoms refers to the ring itself of a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of atoms to be played. An atom that does not constitute a ring (for example, a hydrogen atom that terminates the dangling bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is included in the number of ring-forming atoms Absent. The “number of ring-forming atoms” described below is the same unless otherwise specified.

  When adjacent substituents form a ring, the ring is separated at a position where the carbon number of one substituent is the smallest within the above range, and the carbon number of the other substituent is also within the above range. The inner structure is included. The carbon number of the substituent described below is the same unless otherwise specified.

  "Aromatic hydrocarbon ring" consists of only carbon and hydrogen atoms and has aromaticity (including single rings, condensed rings, and cases where these multiple rings are bonded via a single bond) The term “heteroaromatic ring” refers to a ring having a single aromatic bond (single ring, condensed ring or a plurality of these rings containing one or more heteroatoms in addition to a carbon atom and a hydrogen atom. "Heteroaliphatic ring" means a ring containing one or more heteroatoms in addition to carbon and hydrogen atoms and having no aromaticity (monocyclic, condensed) Ring, and a case where a plurality of these rings are bonded via a single bond).

  “Unsubstituted” in “substituted or unsubstituted...” Means that a hydrogen atom is substituted. In the present invention, “hydrogen atom” is an isotope having a different number of neutrons, that is, light hydrogen ( protium), deuterium, tritium.

(Fused ring amine compound)
The condensed ring amine compound which is one embodiment of the present invention is represented by the following formula (1).

In the formula (1), Ar represents a substituted or unsubstituted pyrene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted perylene ring, a substituted or unsubstituted fluoranthene ring, a substituted Or an n-valent residue of an unsubstituted benzofluorene ring or a substituted or unsubstituted spirofluorene ring.
n represents an integer of 1 to 4, and when n is 2 or more, the structures represented by a plurality of — [L] _m —NAr ¹ Ar ² may be the same as or different from each other.

The anthracene ring, pyrene ring, chrysene ring, perylene ring, fluoranthene ring, benzofluorene ring, and spirofluorene ring constituting the mother skeleton (ring excluding the substituent) of Ar are each represented by the following structural formula.

L represents a divalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms.
m represents an integer of 0 to 2, and when m is 0, it indicates that Ar and a nitrogen atom are bonded by a single bond. When m is 2, two Ls are the same or different from each other. Or two L substituents may be bonded to each other to form a ring.
m is preferably 0 or 1, and more preferably 0.

At least one of Ar ¹ and Ar ² is a group represented by the following formula (2), Ar ¹ and Ar ² otherwise are independently a substituted or unsubstituted ring forming aryl having 6 to 30 carbon atoms Or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Ar ¹ and Ar ² substituents bonded to the same nitrogen atom may be bonded to form a ring.

Ar ¹ and Ar ² other than the group represented by the formula (2) are preferably substituted or unsubstituted aryl groups having 6 to 20 ring carbon atoms.

Here, in the case where n is 2 or more, “at least one of Ar ¹ and Ar ² is a group represented by the following formula (2)” means that two or more Ar ¹ and Ar ² are respectively present. It means that one or more of may be a group represented by the following formula (2).

In formula (2), X and Y each independently represent O, S, SO ₂ , C (R ¹⁰ ) ₂ , NR ¹⁰ or Si (R ¹⁰ ) ₂ . X and Y are preferably each independently O, S, C (R ¹⁰ ) ² , NR ¹⁰ or Si (R ¹⁰ ) ₂ .

As a combination of X and Y, C (R ¹⁰ ) ₂ and C (R ¹⁰ ) ₂ , C (R ¹⁰ ) ₂ and O, C (R ¹⁰ ) ₂ and S, C (R ¹⁰ ) ₂ and NR ¹⁰ , O and O, O and NR ¹⁰ , O and S, S and S, S and NR ¹⁰ , O and Si (R ¹⁰ ) ₂ , NR ¹⁰ and Si (R ¹⁰ ) ₂ , NR ¹⁰ and NR ^{10 and the} like. , C (R ¹⁰ ) ₂ and C (R ¹⁰ ) ₂ , C (R ¹⁰ ) ₂ and O, C (R ¹⁰ ) ₂ and S, O and NR ¹⁰ , S and NR ¹⁰ , O and Si (R ¹⁰ ) ₂ , NR ¹⁰ and Si (R ¹⁰ ) ₂ are preferred.

Any one of R ^{11 to} R ¹⁸ is used for bonding to a nitrogen atom, and the other R ^{11 to} R ¹⁸ and R ¹⁰ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted carbon number. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms in a ring Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, cyano group, substituted or unsubstituted ring carbon atoms having 6 to 20 carbon atoms aryl group, or a substituted or indicates unsubstituted ring atoms 5-20 heteroaryl group, R ¹¹ to R ¹⁸ are also form a saturated or unsaturated substituents adjacent rings There.

R ¹⁰ is preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, and the like.

R ^{11 to} R ¹⁸ other than those used for bonding to the nitrogen atom are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring carbon number of 6 to 6 It is preferably 20 aryl groups.

  The condensed ring amine compound described using the above formula (1) is more preferably represented by the following formula (3).

In formula (3), L, Ar ¹ , Ar ² , m and n are as defined above.

Either the n R ²¹ to R ³⁰ is used for binding to the L or nitrogen atom, ^R 21 ^{to R 30} other than it are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C 1 -20 alkyl group, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, cyano group, substituted or unsubstituted aryl having 6 to 20 ring carbon atoms group, or a substituted or indicates unsubstituted ring atoms 5-20 heteroaryl group, R ²¹ to R ³⁰ may form a saturated or unsaturated substituents adjacent rings

In the above formula (3), when n is 2, the bonding position with the structure represented by-[L] _m -NAr ¹ Ar ² is preferably a combination of R ²¹ and R ²⁶ , R ²³ and R ²⁶ , and R A combination of ²¹ and R ²⁶ is more preferred.

  The condensed ring amine compound described using the above formula (3) is more preferably represented by the following formula (3-1).

In formula (3-1), L, Ar ¹ , Ar ² , m, R ^{22 to} R ²⁵ and R ^{27 to} R ³⁰ are as defined above.

  The condensed ring amine compound described using the above formula (1) is more preferably represented by the following formula (4).

In the formula (4), Ar, Ar ¹ , Ar ² , m and n are as defined above.
Any two of R ³¹ to R ^36, said each Ar, is used for binding to the nitrogen atom or adjacent phenylene group, ^R 31 ^{to R 36} other than it are each independently a hydrogen atom, a halogen atom, a substituted Or an unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted ring forming carbon number. A cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 carbon atoms, a cyano group, a substituted or unsubstituted ring formation An aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms is shown.

Here, “any two of R ^{31 to} R ³⁶ are each used for bonding to the Ar, nitrogen atom or adjacent phenylene group” means the following structure.
When m is 0, any two of R ^{31 to} R ³⁶ are bonded to the Ar and the nitrogen atom, respectively.
When m is 1, one of any two of R ^{31 to} R ³⁶ is bonded to the phenylene group adjacent to the Ar, and the other is bonded to the adjacent phenylene group and a nitrogen atom.

  The relationship of the bonding position between Ar and the nitrogen atom in the phenylene group may be any of ortho-position, meta-position and para-position. The para position is preferred.

The condensed ring amine compound described using the above formula (4) is more preferably represented by the following formula (4-1).

In formula (4-1), Ar, Ar ¹ , Ar ² , m, n, R ³² , R ³³ , R ³⁵ and R ³⁶ are as defined above.

式（２−１）及び（２−２）中、Ｘ、Ｙ、Ｒ^１１〜Ｒ^１８は、前記定義の通りである。
式（２−１）及び（−２）中の波線は、窒素原子との結合手であることを示す。 The group described using the formula (2) is more preferably a group represented by the following formula (2-1) or (2-2).

In formulas (2-1) and (2-2), X, Y, and R ^{11 to} R ¹⁸ are as defined above.
The wavy line in the formulas (2-1) and (-2) indicates a bond with a nitrogen atom.

式中、Ｒ^１１〜Ｒ^１８及び波線は、前記定義の通りである。 The groups described using the formulas (2-1) and (2-2) are more preferably groups represented by the following formulas (2-1-1) or (2-2-1), respectively.

In the formula, R ^{11 to} R ¹⁸ and the wavy line are as defined above.

  In addition, the substituents in “substituted or unsubstituted...” Include alkyl groups, alkylsilyl groups, arylsilyl groups, alkoxy groups, alkenyl groups, alkynyl groups, aryl groups, aryloxy groups, aralkyl groups as described later. Group, cycloalkyl group, heteroaryl group (heteroaromatic ring group), heteroaliphatic ring group, halogen atom, halogenated alkyl group, hydroxyl group, nitro group, cyano group, carboxy group and the like.

The above formulas (1), (2), (2-1), (2-2), (2-1-1), (2-2-1), (3), (3-1), (4 ) And (4-1), each group represented by Ar, L, Ar ¹ , Ar ² , R ^{10 to} R ¹⁸ and R ^{21 to} R ³⁶ , and a substituent in the above “substituted or unsubstituted...” Will be described in detail.

Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, An n-octyl group etc. are mentioned.
1-10 are preferable and, as for the said carbon number, 1-6 are more preferable. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl are preferred.

  Examples of the substituted silyl group include an alkylsilyl group having 3 to 30 carbon atoms, an arylsilyl group having 8 to 30 ring carbon atoms, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, and a vinyldimethylsilyl group. Group, propyldimethylsilyl group, triisopropylsilyl group, triphenylsilyl group and the like.

  The alkoxy group is represented as -OW, and examples of W include the above alkyl examples. The alkoxy group is, for example, a methoxy group or an ethoxy group.

  The alkenyl group is preferably a vinyl group, and the alkynyl group is preferably an ethynyl group.

  Examples of the aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, naphthacenyl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group 4-fluorenyl group, 9-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, terphenyl group, fluoranthenyl group, etc. Is mentioned.

  The aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12 carbon atoms, and among the aryl groups described above, a phenyl group, a biphenyl group, and a 1-naphthyl group are particularly preferable.

  Here, as the divalent residue of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms in L, a group having two bonds corresponding to the example of the aryl group (arylene) Group).

  The aryloxy group is represented as -OZ, and examples of Z include the above aryl groups, and examples of the monocyclic group and condensed ring group described above. The aryloxy group is, for example, a phenoxy group.

  The aralkyl group is represented as -W-Z, and examples of W include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples. The aralkyl group has 7 to 50 carbon atoms (the aryl moiety has 6 to 49 carbon atoms (preferably 6 to 30, more preferably 6 to 20, particularly preferably 6 to 12), and the alkyl moiety has 1 to 44 carbon atoms. (Preferably 1-30, more preferably 1-20, still more preferably 1-10, particularly preferably 1-6)), for example, benzyl group, phenylethyl group, 2-phenylpropane-2- It is an yl group.

  Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, and a norbornyl group. The ring forming carbon number is preferably 3 to 10, more preferably 3 to 8 ring forming carbon atoms, and particularly preferably 3 to 6 ring forming carbon atoms.

When the cycloalkyl group is a substituent of the aryl group, the cycloalkyl group may be condensed with the aryl group. Examples of such a condensing group include the following groups.

  Examples of the heteroaryl group include pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, imidazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, 1-dibenzofuranyl group, and 2-dibenzofuranyl group. Group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, quinolyl group, isoquinolyl group, Quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, Phenoxazinyl group, oxazolyl group, oxadi Zoriru group, furazanyl group, a thienyl group, benzothiophenyl group and the like.

5-20 are preferable and, as for the number of ring formation atoms of the said heteroaryl group, 5-14 are more preferable.
Preferably, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group Group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group.

  Here, as the divalent residue of the substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms in L, the bond corresponding to the example of the above heteroaryl group has two groups (heteroarylene). Group).

Examples of the halogen atom include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
Examples of the halogenated alkyl group include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group, and a trifluoromethyl group is preferable.

  Examples of the heteroaliphatic cyclic group include piperidinyl group, piperazinyl group, morpholinyl group, quinuclidinyl group, pyridinyl group, oxetanyl group and the like.

In the R ^{11 to} R ¹⁸ and R ^{21 to} R ³⁰ ,
The halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and selected from the group consisting of n-octyl,
The substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is vinyl;
The substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is ethynyl;
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl and norbornyl;
The substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, or the substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms is trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, Selected from the group consisting of propyldimethylsilyl, triisopropylsilyl and triphenylsilyl;
The substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3- Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, Selected from the group consisting of benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl;
The substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms includes pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, imidazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, 1 -Dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4- Dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, phenanthridinyl group, acridinyl group, phenant Lorinyl group, phenazinyl group, phenothiazinyl group, phenoxadi Group, oxazolyl group, oxadiazolyl group, furazanyl group, is preferably selected from a thienyl group, and the group consisting of benzothiophenyl group.

In the R ^{11 to} R ¹⁸ and R ^{21 to} R ³⁰ ,
The halogen atom is fluorine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl. And
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-methylcyclohexyl;
The substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is more preferably selected from the group consisting of phenyl, biphenyl, tolyl, xylyl and 1-naphthyl.

R ^{11 to} R ¹⁸ and R ^{21 to} R ³⁰ are each independently a hydrogen atom, or phenyl substituted with a methyl, ethyl, propyl, isopropyl, n-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methyl group. More preferably, it is a group selected from the group consisting of 1-naphthyl.

  The condensed ring amine compound which is one embodiment of the present invention can be generally synthesized by the following method, but is not limited to the following synthesis method. Moreover, in the following scheme, the substituents of the starting material 1, the intermediate 2, the intermediate 3 and the final body 4 are omitted for the sake of simplicity.

Ar ¹ is a group represented by the formula (2), m is 0, that is, the condensed ring amine compound represented by the formula (1) when L is not present can be synthesized, for example, by the following method.

In the formula, X, Y, Ar, L, n and Ar ² are the same as those in the formula (1). Hal represents a halogen atom.

  Step 1 is a step of obtaining intermediate 2 by halogenating starting material 1 corresponding to the structure represented by formula (2). A base such as n-BuLi or t-BuLi and a halogen source such as bromine, N-bromosuccinimide, or N-iodosuccinimide can be used. These reagents may be used independently or in combination.

In step 2, intermediate 2 is coupled with amine derivative (Ar ² —NH ₂ ) to obtain intermediate 3, and Buchwald-Hartwig cross-coupling reaction, Ullmann reaction, or the like can be used.

  Step 3 is a step of coupling the intermediate 3 and the condensed aromatic hydrocarbon corresponding to Ar in the formula (1) to obtain the final product 4 (the condensed ring amine compound of the formula (1)), Buchwald-Hartwig cross-coupling reaction, Ullmann reaction, etc. can be used.

The condensed ring amine compound represented by the formula (1) when Ar ¹ is a group represented by the formula (2) and m is 1 or 2 can be synthesized, for example, by the following method.

In the formula, X, Y, Ar, L, m, n and Ar ² are the same as those in the formula (1). Hal, Hal ¹ and Hal ² each represent a halogen atom.

Process 4 is a process of obtaining Ar- [L] _m -Hal ² by linking ArHal ¹ and Hal ^2- [L] -M. Suzuki-Miyaura coupling, Stille coupling, Kumada coupling, Negishi cup A ring or the like can be used. Here, M represents an organometallic species such as B (OH) ₂ , SnBu ₃ , MgBr, ZnBr. In order to prevent scrambling, it is desirable that Hal ¹ and Hal ² are different halogen atoms.

  Step 5 is a step of linking the product of Step 4 and the intermediate 3 obtained in Step 2 above to obtain the final product 5 (the condensed ring amine compound of the above formula (1)), and the Buchwald-Hartwig cross-cup. Ring reaction, Ullmann reaction, etc. can be used.

  Details of the method for synthesizing the condensed ring amine compound which is one embodiment of the present invention will be described in Synthesis Examples described later. In addition, condensed ring amine compounds not described in the synthesis examples can be synthesized according to the synthesis examples.

In the condensed ring amine compound having a structure represented by the formula (1), Ar in the case of n = 2, Ar in the case of n = 1, and Ar ¹ (referred to as a group represented by the formula (2)) Specific examples of Ar ² and L are shown in Tables 1-1 to 1-4.
The wavy line in the table below indicates a bond (bonding position) to an adjacent group.

Specific examples of the condensed ring amine compound represented by the formula (1) are shown below.

The condensed ring amine compound can be used as a material for an organic EL device, particularly preferably used as a material for a light emitting layer, and particularly preferably used as a doping material for a light emitting layer.
When the condensed ring amine compound is used as a doping material for a fluorescent light emitting layer, an element that emits light of a blue color (that is, light emission with a small CIEy value) is obtained as compared with the case where a known doping material is used. be able to.

This is because the condensed ring amine compound has a structure represented by the above formula (2) at the end of the amine side chain, so that the mother skeleton represented by Ar and the structure represented by (2) It is considered that it is difficult to take a planar structure, and the light emission becomes shorter (more blue color) by increasing the energy gap (Eg) by reducing the conjugation contribution. Also, depending on the substituent, it can be considered that the wavelength of light emission becomes shorter (becomes a blue color) by acting as an electron withdrawing group.
Moreover, since the compound with these structures has a high fluorescence quantum yield, it is thought that luminous efficiency is also improved.

(Organic electroluminescence device)
An organic electroluminescence device which is one embodiment of the present invention has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is the above condensed ring amine compound It contains 1 or more types.
It is preferable that the light emitting layer contains the condensed ring amine compound. The light emitting layer can be composed of only the above condensed ring amine compound, or can be included as a host material or a doping material, but is preferably included as a doping material.

At least one of the organic thin film layers is at least one of a condensed ring amine compound represented by the formula (1) and an anthracene derivative represented by the following formula (5) or a pyrene derivative represented by the following formula (6). It is preferable to contain.
Moreover, it is preferable that a light emitting layer contains the said condensed ring amine compound as a dopant and an anthracene derivative as a host. In particular, when an anthracene derivative represented by the following formula (5) is used as a host material, high emission efficiency and light emission with a blue color can be obtained.

（式（５）中、Ａｒ^１１及びＡｒ^１２は、それぞれ独立に、置換若しくは無置換の環形成原子数５〜５０の単環基又は置換若しくは無置換の環形成原子数１０〜５０の縮合環基であり、Ｒ^１０１〜Ｒ^１０８は、それぞれ独立に、水素原子、置換若しくは無置換の環形成原子数５〜５０の単環基、置換若しくは無置換の環形成原子数１０〜５０の縮合環基、置換若しくは無置換の炭素数１〜５０のアルキル基、置換若しくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換若しくは無置換の炭素数１〜５０のアルコキシ基、置換若しくは無置換の炭素数７〜５０のアラルキル基、置換若しくは無置換の環形成炭素数６〜５０のアリールオキシ基、置換若しくは無置換の炭素数１〜２０のアルキルシリル基、置換若しくは無置換の環形成炭素数６〜３０のアリールシリル基、ハロゲン原子又はシアノ基である。） (Anthracene derivative)
The anthracene derivative represented by the formula (5) is the following compound.

(In the formula (5), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted condensed ring having 10 to 50 ring atoms. R ^{101 to} R ¹⁰⁸ are each independently a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted condensed ring having 10 to 50 ring atoms. Group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted Substituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring Forming carbon atoms of 6 to 30 aryl silyl group, a halogen atom or a cyano group.)

In formula (5), the monocyclic group is a group composed only of a ring structure having no condensed structure.
Specific examples of the monocyclic group having 5 to 50 ring atoms (preferably 5 to 30 ring atoms, more preferably 5 to 20 ring atoms) include phenyl, biphenyl, terphenyl, and quarter An aromatic group such as a phenyl group and a heterocyclic group such as a pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group, and thienyl group are preferable.
Of these, a phenyl group, a biphenyl group, and a terphenyl group are preferable.

In the formula (5), the condensed ring group is a group in which two or more ring structures are condensed.
Specific examples of the condensed ring group having 10 to 50 ring atoms (preferably 10 to 30 ring atoms, more preferably 10 to 20 ring atoms) include a naphthyl group, a phenanthryl group, an anthryl group, and a chrysenyl group. Group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzocrisenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl Groups, condensed aromatic ring groups such as benzofluoranthenyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, quinolyl group, phenanthrolinyl group, etc. A fused heterocyclic group is preferred.
Among these, naphthyl group, phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzoanthryl group, dibenzothiophenyl group, dibenzofuranyl group, and carbazolyl group are preferable.

  Specific examples of the alkyl group, silyl group, alkoxy group, aryloxy group, aralkyl group, cycloalkyl group and halogen atom in the formula (5) are the groups in the above formulas (1) to (4) and “substitution” Or, it is the same as the specific example of the substituent in “Unsubstituted ...”. Below, only the preferable specific example in Formula (5) is given.

As preferred substituents of “substituted or unsubstituted” in Ar ¹¹ , Ar ¹² , R ^{101 to} R ¹⁰⁸ , monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups, alkoxy groups, cyano groups, halogens Atoms (especially fluorine) are preferable, particularly preferably a monocyclic group or a condensed ring group, and preferable specific substituents are the groups in the above formula (5) and the above formulas (1) to (4). It is the same as each group.

In Formula (5), Ar ¹¹ is preferably an unsubstituted phenyl group, and Ar ¹² is preferably a substituted or unsubstituted condensed ring group having 10 to 50 ring atoms.

  The anthracene derivative represented by the formula (5) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected depending on the configuration of the organic EL element to be applied and the required characteristics. .

(Anthracene derivative (A))
In the anthracene derivative, Ar ¹¹ and Ar ¹² in Formula (5) are each independently a substituted or unsubstituted condensed ring group having 10 to 50 ring atoms. The anthracene derivative can be classified into a case where Ar ¹¹ and Ar ¹² are the same substituted or unsubstituted condensed ring group and a case where they are different substituted or unsubstituted condensed ring groups.

Anthracene derivatives which are substituted or unsubstituted condensed ring groups in which Ar ¹¹ and Ar ¹² in formula (5) are different (including differences in substitution position) are particularly preferred, and preferred specific examples of the condensed ring are as described above. Of these, a naphthyl group, a phenanthryl group, a benzanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group are preferable.

(Anthracene derivative (B))
In the anthracene derivative, one of Ar ¹¹ and Ar ¹² in formula (5) is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other is a substituted or unsubstituted ring atom having 10 to 10 ring atoms. 50 condensed ring groups.
As a preferred form, Ar ¹² is a naphthyl group, phenanthryl group, benzoanthryl group, 9,9-dimethylfluorenyl group, dibenzofuranyl group, and Ar ¹¹ is a phenyl substituted with a monocyclic group or a condensed ring group It is a group.
Specific groups of preferred monocyclic groups and condensed ring groups are as described above.
In another preferred embodiment, Ar ¹² is a condensed ring group, and Ar ¹¹ is an unsubstituted phenyl group. In this case, as the condensed ring group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, and a benzoanthryl group are particularly preferable.

(Anthracene derivative (C))
In the anthracene derivative, Ar ¹¹ and Ar ¹² in Formula (5) are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.
As a preferred form, both Ar ¹¹ and Ar ¹² are substituted or unsubstituted phenyl groups.
In a more preferred embodiment, Ar ¹¹ is an unsubstituted phenyl group, Ar ¹² is a monocyclic group, a phenyl group having a condensed ring group as a substituent, and Ar ¹¹ and Ar ¹² are each independently a monocyclic group. In some cases, it may be a phenyl group having a condensed ring group as a substituent.
Specific examples of the preferred monocyclic group and condensed ring group as the substituent are as described above. More preferably, a monocyclic group as a substituent is a phenyl group, a biphenyl group, and a condensed ring group is a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a benzoanthryl group. .

  Specific examples of the anthracene derivative represented by the formula (5) include the following.

式（６）中、Ａｒ^１１１及びＡｒ^２２２は、それぞれ独立に、置換もしくは無置換の環形成炭素数６〜３０のアリール基である。
Ｌ^１及びＬ^２は、それぞれ独立に、置換もしくは無置換の環形成炭素数６〜３０の２価のアリール基又は複素環基を示す。
ｍは０〜１の整数、ｎは１〜４の整数、ｓは０〜１の整数、ｔは０〜３の整数である。
また、Ｌ^１又はＡｒ^１１１はピレンの１〜５位のいずれかに結合し、Ｌ^２又はＡｒ^２２２はピレンの６〜１０位のいずれかに結合する。 As another form, at least one layer of the organic thin film layer is an organic electroluminescence device containing a condensed ring amine compound represented by the formula (1) and a pyrene derivative represented by the following formula (6). Also good. More preferably, the light emitting layer contains the condensed ring amine compound as a dopant and a pyrene derivative as a host.

In formula (6), Ar ¹¹¹ and Ar ²²² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
L ¹ and L ² each independently represent a substituted or unsubstituted divalent aryl group or heterocyclic group having 6 to 30 ring carbon atoms.
m is an integer of 0 to 1, n is an integer of 1 to 4, s is an integer of 0 to 1, and t is an integer of 0 to 3.
L ¹ or Ar ¹¹¹ is bonded to any one of positions 1 to 5 of pyrene, and L ² or Ar ²²² is bonded to any of positions 6 to 10 of pyrene.

L ¹ and L ² in the general formula (6) are preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group and a substituted or unsubstituted It is a divalent aryl group composed of an unsubstituted fluorenylene group and a combination of these substituents.
Moreover, as this substituent, it is the same as that of the substituent in "substituted or unsubstituted ..." in said (1)-(4). The substituent for L ¹ and L ² is preferably an alkyl group having 1 to 20 carbon atoms.

M in the general formula (6) is preferably an integer of 0 to 1. N in the general formula (6) is preferably an integer of 1 to 2. S in the general formula (6) is preferably an integer of 0 to 1.
T in General formula (6) becomes like this. Preferably it is an integer of 0-2.
The aryl groups of Ar ¹¹¹ and Ar ²²² are the same as the groups in the above (1) to (4).
Preferably, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms, and preferred specific examples of the aryl group include a phenyl group. Naphthyl group, phenanthryl group, fluorenyl group, biphenyl group, anthryl group, pyrenyl group.

  When a condensed ring amine compound is included as a dopant, it is preferably 0.1 to 20% by mass, and more preferably 1 to 10% by mass.

  The condensed ring amine compound and the anthracene derivative or pyrene derivative can be used for a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer in addition to the light emitting layer.

  In the present embodiment, organic EL elements having a plurality of organic thin film layers include (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / positive). And a layer laminated with a structure such as (hole injection layer / light emitting layer / electron injection layer / cathode), (anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode).

  The organic EL element can prevent the brightness | luminance and lifetime fall by quenching by making the said organic thin film layer into a multilayer structure. If necessary, a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. In addition, depending on the doping material, light emission luminance and light emission efficiency may be improved. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer for injecting electrons from an electrode is called an electron injection layer, and a layer for receiving electrons from the electron injection layer and transporting electrons to a light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.

  Examples of materials other than the above formula (5) that can be used in the light emitting layer together with the condensed ring amine compound that is one embodiment of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, Condensed polycyclic aromatic compounds such as tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, triarylamine derivatives, styrylamine derivatives, stilbene Derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole Conductor, acridone derivatives, quinacridone derivatives, and the like, but is not limited thereto.

  As a hole injection material, a compound having the ability to transport holes, the hole injection effect from the anode, the hole injection effect excellent for the light emitting layer or the light emitting material, and the thin film forming ability Is preferred. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine type triphenylamine, diamine type triphenylamine, hexacyanohexaazatriphenylene and the like, and derivatives thereof, such as polyvinylcarbazole, polysilane, conductive polymer, etc. Examples include, but are not limited to, polymer materials.

  Among the hole injection materials that can be used in the organic EL device which is one embodiment of the present invention, a more effective hole injection material is a phthalocyanine derivative.

Examples of the phthalocyanine (Pc) derivatives include H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, and OPP Although there exist phthalocyanine derivatives and naphthalocyanine derivatives, such as MoOPc and GaPc-O-GaPc, it is not limited to these.
In addition, carriers can be sensitized by adding an electron acceptor such as a TCNQ derivative to the hole injection material.

A preferred hole transport material that can be used in the organic EL device which is one embodiment of the present invention is an aromatic tertiary amine derivative.
Examples of aromatic tertiary amine derivatives include N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra. Biphenyl-1,1′-biphenyl-4,4′-diamine or the like, or an oligomer or polymer having an aromatic tertiary amine skeleton is not limited thereto.

  As the electron injecting material, a compound having an ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable.

In the organic EL element which is one embodiment of the present invention, more effective electron injection materials are a metal complex compound and a nitrogen-containing heterocyclic derivative.
Examples of the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, and bis. (10-Hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, and the like may be mentioned, but are not limited thereto.

As the nitrogen-containing heterocyclic derivative, for example, oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine and the like are preferable, and among them, benzimidazole derivative, phenanthroline derivative, imidazopyridine Derivatives are preferred.
As a preferred mode, these electron injection materials further contain a dopant, and more preferably, a dopant typified by an alkali metal is doped in the vicinity of the cathode interface of the second organic layer in order to facilitate the reception of electrons from the cathode. .
Examples of the dopant include a donor metal, a donor metal compound, and a donor metal complex. These reducing dopants may be used singly or in combination of two or more.

  In the organic EL device which is one embodiment of the present invention, in the light emitting layer, in addition to at least one selected from the condensed ring amine compounds represented by the formula (1), a light emitting material, a doping material, a hole injection material, At least one of the hole transport material and the electron injection material may be contained in the same layer. In addition, in order to improve the stability of the organic EL element with respect to temperature, humidity, atmosphere, etc., it is possible to provide a protective layer on the surface of the element, or to protect the entire element with silicon oil, resin or the like.

  As the conductive material used for the anode of the organic EL element which is one embodiment of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver Gold, platinum, palladium and the like and alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.

  In the organic EL element which is one embodiment of the present invention, in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the element. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.

  The formation of each layer of the organic EL element which is one embodiment of the present invention may be performed by any of dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dipping, and flow coating. Can be applied. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.

In the case of the wet film forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
As a solution suitable for such a wet film formation method, an organic EL material-containing solution containing a condensed ring amine compound which is one embodiment of the present invention and a solvent can be used as the organic EL material.

  The organic EL material includes a host material and a dopant material, the dopant material is a condensed ring amine compound which is one embodiment of the present invention, and the host material is selected from compounds represented by formula (5) It is preferable that it is at least one kind.

  In any organic thin film layer, an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.

The organic EL element which is one embodiment of the present invention can be used for various electronic devices and lighting fixtures. For example, it can be used as a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or an instrument, a display board, a marker lamp, and the like.
The condensed ring amine compound which is one embodiment of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photoreceptor, a photoelectric conversion device, a solar cell, and an image sensor.

  EXAMPLES Hereinafter, although an Example is given and the aspect of this invention is demonstrated more concretely, this invention is not limited at all by these Examples.

<Example of compound synthesis>
Synthesis of Compound A:

(1) Synthesis of intermediate A1

9,9,10,10-Tetramethyl-9,10-dihydroanthracene (25.0 g, 140 mmol) was weighed into a 1 L three-necked flask and dissolved in acetic anhydride (150 mL). This solution was slowly added dropwise to nitric acid (150 mL) at −10 ° C., and the temperature was kept at 5 to 10 ° C., followed by stirring for 1 hour. The reaction solution was added to ice water, extracted with ethyl acetate, and the organic layer was dehydrated with magnesium sulfate. After filtration, the crude product obtained by concentrating this solution was purified by column chromatography to obtain Intermediate A1 (35.5 g, 126 mmol, yield 90%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate A2

Intermediate A1 (19.0 g, 67.6 mmol) was weighed into a 1 L eggplant-shaped flask, and palladium-carbon (2 g) and toluene (300 mL) were added. The system was placed in a hydrogen atmosphere and then heated to reflux for 8 hours. The mixture was allowed to cool to room temperature, purged with nitrogen, and filtered through celite. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate A2 (16.5 g, 65.6 mmol, yield 97%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of intermediate A3

In a 1 L three-necked flask, intermediate A2 (16.0 g, 63.7 mmol), bromobenzene (10.0 g, 63.7 mmol, 1.0 eq.), Tris (dibenzylideneacetone) palladium (880 mg, 1.0 mmol, 1.5 mol%), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (1.19 g, 1.9 mmol, 3.0 mol%), tertiary butoxy sodium (6.74 g, 70. 1 mmol, 1.1 eq.) Was weighed and dehydrated toluene (300 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate A3 (14.4 g, 44.0 mmol, yield 69%).
It was confirmed that the product was obtained by FD-MS.

(4) Synthesis of Compound A

In a 500 mL four-necked flask, 1,6-dibromopyrene (3.0 g, 8.3 mmol), intermediate A3 (5.5 g, 17 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0.46 g, 0.50 mmol, 6.0 mol%) and tertiary butoxy sodium (1.8 g, 18 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (100 mL), tri A 8.23 M toluene solution (49 μL, 0.40 mmol, 4.8 mol%) of (butylene) phosphine was added, and the mixture was heated and stirred for 12 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound A (3.6 g, 4.3 mmol, yield 51%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound B:
Compound B was synthesized in the same manner as Compound A except that p-bromocumene was used instead of bromobenzene in the synthesis of Intermediate A3.

Synthesis of Compound C:
Compound C was synthesized in the same manner as Compound A except that 1,6-diisopropyl-3,8-dibromopyrene was used instead of 1,6-dibromopyrene in the synthesis of Intermediate A.

Synthesis of Compound D:

(1) Synthesis of intermediate D1

Diethylene glycol dimethyl ether (52 mL) was added to a 500 mL four-necked flask and cooled on ice. Lithium aluminum hydride (4.64 g, 122 mmol, 2.6 eq.) Was slowly added and stirred for 15 minutes. 1-Chloroanthracene (10.0 g, 47.0 mmol) was added, and the system was heated and stirred under a nitrogen atmosphere for 6 hours. The reaction solution was ice-cooled, and 1N hydrochloric acid was added to stop the reaction. The resulting precipitate was filtered to obtain Intermediate D1 (6.24 g, 23 mmol, yield 49%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate D2

In a 1 L three-necked flask, intermediate B1 (6.1 g, 23 mmol), tris (dibenzylideneacetone) palladium (0.62 g, 0.68 mmol, 1.5 mol%), tertiary butoxy sodium (2.5 g, 25 mmol, 1.1 eq.), Weighed, dehydrated toluene (300 mL), aniline (2.1 g, 23 mmol, 1.0 eq.), Tritertiary butylphosphine in 8.23 M toluene solution (66 μL, 0.54 mmol, 2 .4 mol%) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate D2 (4.7 g, 14 mmol, yield 63%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of compound D

In a 500 mL four-necked flask, 1,6-dibromopyrene (3.0 g, 8.3 mmol), intermediate D2 (5.5 g, 17 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0.46 g, 0.50 mmol, 6.0 mol%) and tertiary butoxy sodium (1.8 g, 18 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (100 mL), tri A 8.23 M toluene solution (49 μL, 0.40 mmol, 4.8 mol%) of (butylene) phosphine was added, and the mixture was heated and stirred for 12 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound D (4.8 g, 5.6 mmol, 67% yield).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound E:
Compound E was synthesized in the same manner as Compound D except that p-bromocumene was used instead of bromobenzene in the synthesis of Intermediate D2.

Synthesis of Compound F:
Compound F was synthesized in the same manner as the synthesis of Compound D except that 1,6-diisopropyl-3,8-dibromopyrene was used in place of 1,6-dibromopyrene in the synthesis of Intermediate D.

Synthesis of Compound G:

(1) Synthesis of intermediate G1

9,9-dimethylxanthene (5.14 g, 24.4 mmol) was weighed in a 300 mL four-necked flask, and the system was placed in a nitrogen atmosphere, and then dissolved in anhydrous dichloromethane (63 mL). After this solution was cooled to 0 ° C., a dichloromethane solution (26 mL) of bromine (1.26 mL, 24.7 mmol, 1.0 eq.) Was slowly added dropwise and stirred at 0 to 5 ° C. for 3 hours. Bromine (0.26 mL, 2.47 mmol, 0.1 eq.) In dichloromethane (7.5 mL) was added and stirred for 1 hour, and bromine (0.26 mL, 2.47 mmol, 0.1 eq.) In dichloromethane was added. (7.5 mL) was added and stirred for 1 hour. The reaction was stopped by adding water, and the organic layer was extracted with toluene and dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate G1 (5.69 g, 19.7 mmol, yield 80%; including dibromo compound, HPLC purity 91.9%). .
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate G2

In a 1 L three-necked flask, intermediate G1 (4.69 g, ca. 16.2 mmol), aniline (1.51 g, 16.5 mmol, 1.0 eq.), Tris (dibenzylideneacetone) palladium (223 mg, 0.244 mmol). , 1.5 mol%), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (303 mg, 0.487 mmol, 3.0 mol%), tertiary butoxy sodium (1.71 g, 17.8 mmol) , 1.1 eq.) Was weighed and dehydrated toluene (65 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 7 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate G2 (3.38 g, ca. 10.8 mmol, yield 67%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of Compound G

In a 500 mL four-necked flask, 1,6-dibromopyrene (1.94 g, 5.38 mmol), intermediate G2 (3.38 g, ca.10.8 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium ( 296 mg, 0.323 mmol, 6.0 mol%) and tertiary butoxy sodium (1.14 g, 11.9 mmol, 2.2 eq.) Were weighed and the system was placed under a nitrogen atmosphere, and then dehydrated toluene (40 mL) , Tri (tertiary butyl) phosphine in 8.23M toluene solution (31.4 μL, 0.258 mmol, 4.8 mol%) was added, and the mixture was stirred with heating for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound G (1.65 g, 2.06 mmol, yield 38%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound H:
Compound H was synthesized in the same manner as Compound G except that p-isopropylaniline was used instead of aniline in the synthesis of Intermediate G2.

Synthesis of Compound I:
Compound I was synthesized in the same manner as the synthesis of Compound G, except that 1,6-diisopropyl-3,8-dibromopyrene was used instead of 1,6-dibromopyrene in the synthesis of Compound G.

Synthesis of Compound J:

(1) Synthesis of intermediate J1

9,9-dimethylxanthene (10.1 g, 48.0 mmol) was weighed in a 300 mL four-necked flask, and the system was put under a nitrogen atmosphere, and then dissolved in dehydrated THF (96 mL). The reaction solution was cooled to −78 ° C. in a dry ice / methanol bath, and then a 1.64 M hexane solution (29.3 mL, 48.0 mmol, 1.0 eq.) Of n-butyllithium was added, and the mixture was gradually brought to room temperature. The mixture was warmed and stirred for 5 hours. The reaction solution was cooled again to −78 ° C., 1,2-dibromoethane (8.3 mL, 96.3 mmol, 2.0 eq.) Was added, and the mixture was gradually warmed to room temperature and stirred for 2 hours. The reaction was stopped by adding water, and the organic layer was extracted with toluene and dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate J1 (9.50 g, 31.6 mmol, yield 66%; including dibromo compound).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate J2

A 300 mL four-necked flask was charged with intermediate J1 (7.25 g, ca. 25.1 mmol), tris (dibenzylideneacetone) palladium (344 mg, 0.376 mmol, 1.5 mol%), 2,2′-bis (diphenylphosphine). Fino) -1,1′-binaphthyl (468 mg, 0.752 mmol, 3.0 mol%) and tertiary butoxy sodium (2.65 g, 27.6 mmol, 1.1 eq.) Were weighed and dehydrated toluene (100 mL) , Aniline (2.33 g, 25.5 mmol, 1.0 eq.) Was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 7 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate J2 (8.04 g,> quant.).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of Compound J

In a 500 mL four-necked flask, 1,6-dibromopyrene (4.51 g, 25.1 mmol), intermediate J2 (8.04 g, ca. 25.1 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium ( 459 mg, 0.501 mmol, 2.0 mol%), tri (tertiarybutyl) phosphine tetrafluoroborate (582 mg, 2.01 mmol, 8.0 mol%), tertiary butoxy sodium (3.37 g, 35.1 mmol, 1.4 eq.) Was weighed and the system was placed in a nitrogen atmosphere, dehydrated toluene (100 mL) was added, and the mixture was heated and stirred for 7 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude purified product obtained by concentration under reduced pressure was recrystallized to obtain Compound J (4.14 g, 5.18 mmol, yield 21%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound K:
Compound K was synthesized in the same manner as Compound J except that p-isopropylaniline was used instead of aniline in the synthesis of Intermediate J2.

Synthesis of Compound L:
Compound L was synthesized in the same manner as the synthesis of Compound J, except that 1,6-diisopropyl-3,8-dibromopyrene was used instead of 1,6-dibromopyrene in the synthesis of Compound J.

Synthesis of Compound M:
Compound M was synthesized in the same manner as Compound G except that 9,9-dimethylthioxanthene was used instead of 9,9-dimethylxanthene in the synthesis of Compound G.

Synthesis of Compound N:
Compound N was synthesized in the same manner as Compound J except that 9,9-dimethylthioxanthene was used instead of 9,9-dimethylxanthene in the synthesis of Compound J.

Synthesis of Compound O:

(1) Synthesis of intermediate O1

10-Phenylphenoxazine (10.0 g, 39 mmol) was weighed into a 500 mL four-necked flask, and the system was placed in a nitrogen atmosphere, and then dissolved in dehydrated THF (200 mL). The solution was cooled to −78 ° C. in a dry ice / methanol bath, 1.6M hexane solution of n-butyllithium (27 mL, 43 mmol, 1.1 eq.) Was added, and the temperature was gradually raised to room temperature. Stir for hours. The reaction solution was again cooled to −78 ° C., 1,2-dibromoethane (6.6 mL, 77 mmol) was added, and the mixture was gradually warmed to room temperature and stirred for 6 hours. The reaction was stopped by adding water, and the organic layer was extracted with toluene and dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate O1 (6.9 g, 20 mmol, yield 53%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate O2

In a 300 mL three-necked flask, intermediate O1 (6.9 g, 20 mmol), aniline (1.9 g, 20 mmol, 1.0 eq.), Tris (dibenzylideneacetone) palladium 0.28 g, 0.31 mmol, 1.5 mol% ), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.98 g, 0.61 mmol, 3.0 mol%), tertiary butoxy sodium (2.2 g, 22 mmol, 1.1 eq.). ) Was weighed and dehydrated toluene (100 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate O2 (5.9 g, 17 mmol, yield 82%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of compound O

In a 500 mL four-necked flask, 1,6-dibromopyrene (3.0 g, 8.3 mmol), intermediate O 2 (5.8 g, 17 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0.46 g, 0.50 mmol, 6.0 mol%) and tertiary butoxy sodium (1.8 g, 18 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (100 mL), tri A 8.23 M toluene solution (49 μL, 0.40 mmol, 4.8 mol%) of (butylene) phosphine was added, and the mixture was heated and stirred for 12 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound O (3.9 g, 4.6 mmol, yield 55%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound P:

(1) Synthesis of intermediate P1

In a 300 mL three-necked flask, 3-bromo-10- (4-tertiarybutylphenyl) phenoxazine (3.0 g, 7.6 mmol), aniline (0.71 g, 7.6 mmol, 1.0 eq.), Tris ( Dibenzylideneacetone) palladium (0.10 g, 0.11 mmol, 1.5 mol%), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.37 g, 0.23 mmol, 3.0 mol) %), Tertiary butoxy sodium (0.80 g, 8.4 mmol, 1.1 eq.) Was weighed and dehydrated toluene (80 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 8 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate P1 (2.2 g, 5.5 mmol, yield 72%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of compound P

In a 500 mL four-necked flask, 1,6-dibromopyrene (0.9 g, 2.5 mmol), intermediate P1 (2.0 g, 5.0 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0. 14 g, 0.15 mmol, 6.0 mol%) and tertiary butoxy sodium (0.53 g, 5.5 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (20 mL) , Tri (tertiary butyl) phosphine in 8.23 M toluene solution (15 μL, 0.12 mmol, 4.8 mol%) was added, and the mixture was stirred with heating for 13 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound P (1.7 g, 1.7 mmol, 66% yield).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound Q:
Compound Q was synthesized using the same method as the synthesis of Compound O except that 10-phenylphenoxazine was replaced with 10-phenylphenothiazine in the synthesis of Compound O.

Synthesis of Compound R:
Compound R was synthesized using the same method as the synthesis of Compound P except that 3-bromo-10-phenylphenoxazine was replaced with 3-bromo-10-phenylphenothiazine in the synthesis of Compound P.

Synthesis of Compound S:

(1) Synthesis of intermediate S1

To a 1 L three-necked flask, N, N, N ′, N′-tetramethyl-1,2-ethanediamine (13.1 g, 113 mmol, 2.0 eq.) And dehydrated diethyl ether (500 mL) were added. Under a nitrogen atmosphere. After cooling this solution to −78 ° C. using a dry ice / methanol bath, a 1.0M solution of secondary butyl lithium in cyclohexane (113 mL, 113 mmol) was slowly added followed by 2,8,10,10-tetramethyl. A diethyl ether solution (100 mL) of benzo [b] [1,4] benzosaliline (14.3 g, 56.3 mmol) was slowly added, the temperature was raised to −40 ° C., and the mixture was stirred for 3 hours. The reaction solution was cooled again to −78 ° C., 1,2-dibromoethane (21.2 g, 113 mmol, 2.0 eq.) Was added, the temperature was gradually raised to room temperature, and the mixture was stirred for 7 hours. After completion of the reaction, methanol and water were added to stop the reaction and diluted with toluene. The organic layer was extracted with toluene and dried over sodium sulfate. After filtration, the crude product obtained by concentration under reduced pressure was purified by column chromatography using basic silica gel to obtain Intermediate S1 (3.74 g, 11.3 mmol, yield 20%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate S2

In a 300 mL three-necked flask, intermediate S1 (3.5 g, 11 mmol), aniline (0.98 g, 11 mmol, 1.0 eq.), Tris (dibenzylideneacetone) palladium (0.14 g, 0.16 mmol, 1.5 mol) %), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.51 g, 0.32 mmol, 3.0 mol%), tertiary butoxy sodium (1.1 g, 12 mmol, 1.1 eq) .) Was weighed and dehydrated toluene (100 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 8 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate S2 (1.7 g, 5.3 mmol, yield 50%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of compound S

In a 500 mL four-necked flask, 1,6-dibromopyrene (0.9 g, 2.5 mmol), intermediate S2 (1.6 g, 5.0 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0. 14 g, 0.15 mmol, 6.0 mol%) and tertiary butoxy sodium (0.53 g, 5.5 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (20 mL) , Tri (tertiary butyl) phosphine in 8.23 M toluene solution (15 μL, 0.12 mmol, 4.8 mol%) was added, and the mixture was stirred with heating for 13 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound S (1.0 g, 1.2 mmol, yield 47%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound T:

(1) Synthesis of intermediate T1

In a 1 L eggplant-shaped flask, 10,10-dimethyl-2-nitro-benzo [b] [1,4] benzoxacillin (4.0 g, 14.8 mmol) was weighed, palladium-carbon (0.5 g), Toluene (100 mL) was added. The system was placed in a hydrogen atmosphere and then heated to reflux for 7 hours. The mixture was allowed to cool to room temperature, purged with nitrogen, and filtered through celite. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate T1 (3.2 g, 13.3 mmol, yield 90%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of intermediate T2

In a 1 L three-necked flask, intermediate T1 (3.0 g, 12 mmol), bromobenzene (2.0 g, 12 mmol, 1.0 eq.), Tris (dibenzylideneacetone) palladium (0.17 g, 0.19 mmol, 1. 5 mol%), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.23 g, 0.37 mmol, 3.0 mol%), tertiary butoxy sodium (1.3 g, 14 mmol, 1. 1 eq.) Was weighed and dehydrated toluene (100 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain intermediate T2 (2.7 g, 8.6 mmol, yield 66%).
It was confirmed that the product was obtained by FD-MS.

(3) Synthesis of compound T

In a 500 mL four-necked flask, 1,6-dibromopyrene (1.5 g, 4.2 mmol), intermediate T2 (2.6 g, 8.3 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0. 23 g, 0.25 mmol, 6.0 mol%) and tertiary butoxy sodium (0.88 g, 9.2 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (40 mL) , Tri (tertiarybutyl) phosphine in 8.23 M toluene solution (24 μL, 0.20 mmol, 4.8 mol%) was added, and the mixture was stirred with heating for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound T (1.5 g, 1.8 mmol, yield 44%).
It was confirmed that the product was obtained by FD-MS.

Synthesis of Compound U:

(1) Synthesis of intermediate U1

In a 500 mL three-necked flask, 2-bromo-5,8,10,10-tetramethyl-benzo [b] [1,4] benzazacillin (5.0 g, 15 mmol), aniline (1.4 g, 15 mmol, 1.0 eq) .), Tris (dibenzylideneacetone) palladium (0.21 g, 0.23 mmol, 1.5 mol%), 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.73 g, 0. 45 mmol, 3.0 mol%) and tertiary butoxy sodium (1.6 g, 17 mmol, 1.1 eq.) Were weighed and dehydrated toluene (150 mL) was added. After substituting the system with nitrogen, the reaction solution was heated and stirred for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Intermediate U1 (3.4 g, 9.8 mmol, yield 65%).
It was confirmed that the product was obtained by FD-MS.

(2) Synthesis of compound U

In a 500 mL four-necked flask, 1,6-dibromopyrene (1.5 g, 4.2 mmol), intermediate U1 (2.9 g, 8.3 mmol, 2.0 eq.), Tris (dibenzylideneacetone) palladium (0. 23 g, 0.25 mmol, 6.0 mol%) and tertiary butoxy sodium (0.88 g, 9.2 mmol, 2.2 eq.) Were weighed and the system was placed in a nitrogen atmosphere, and then dehydrated toluene (40 mL) , Tri (tertiarybutyl) phosphine in 8.23 M toluene solution (24 μL, 0.20 mmol, 4.8 mol%) was added, and the mixture was stirred with heating for 10 hours. After cooling to room temperature, water was added, extracted with toluene, and the organic layer was dried over sodium sulfate. The crude product obtained by concentration under reduced pressure was purified by column chromatography to obtain Compound U (1.7 g, 1.9 mmol, yield 45%).
It was confirmed that the product was obtained by FD-MS.
Other exemplary compounds and compounds within the scope of the claims can also be synthesized in accordance with the above synthesis method by using raw materials suited to the object.

The condensed ring amine compound which is one embodiment of the present invention is useful as a material for an organic EL device, particularly as a doping material for a light emitting layer.
The organic EL element which is another aspect of the present invention can be used for various electronic devices and lighting equipment. For example, it can be used for display devices such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and electronic devices such as light emitting devices for lighting or vehicular lamps.

Claims (29)

A condensed ring amine compound represented by the following formula (1).

[Wherein Ar represents a substituted or unsubstituted pyrene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted perylene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted An n-valent residue of a substituted benzofluorene ring or a substituted or unsubstituted spirofluorene ring is shown.
n represents an integer of 1 to 4, and when n is 2 or more, the structures represented by a plurality of — [L] _m —NAr ¹ Ar ² may be the same as or different from each other.
L represents a divalent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms.
m represents an integer of 0 to 2, and when m is 0, it indicates that Ar and a nitrogen atom are bonded by a single bond. When m is 2, two Ls are the same or different from each other. Or two L substituents may be bonded to each other to form a ring.
At least one of Ar ¹ and Ar ² is a group represented by the following formula (2), Ar ¹ and Ar ² otherwise are independently a substituted or unsubstituted ring forming aryl having 6 to 30 carbon atoms Or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Ar ¹ and Ar ² substituents bonded to the same nitrogen atom may be bonded to form a ring.

(Wherein X and Y each independently represent O, S, SO ₂ , C (R ¹⁰ ) ₂ , NR ¹⁰ or Si (R ¹⁰ ) ₂ ).
Any one of R ^{11 to} R ¹⁸ is used for bonding to the nitrogen atom in the above formula (1), and other R ^{11 to} R ¹⁸ and R ¹⁰ are independently a hydrogen atom, a halogen atom, Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted ring-forming carbon A cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 carbon atoms, a cyano group, a substituted or unsubstituted ring forming an aryl group having 6 to 20 carbon atoms, or a substituted or indicates unsubstituted ring atoms 5-20 heteroaryl group, R ¹¹ to R ¹⁸ is a saturated or unsaturated adjacent substituents It may form a ring. ]] The condensed ring amine compound of Claim 1 represented by following formula (3).

(Wherein L, Ar ¹ , Ar ² , m and n are as defined above).
Either the n R ²¹ to R ³⁰ is used for binding to the L or nitrogen atom, ^R 21 ^{to R 30} other than it are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C 1 -20 alkyl group, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, cyano group, substituted or unsubstituted aryl having 6 to 20 ring carbon atoms group, or a substituted or indicates unsubstituted ring atoms 5-20 heteroaryl group, R ²¹ to R ³⁰ may form a saturated or unsaturated substituents adjacent rings ) The condensed ring amine compound of Claim 2 represented by a following formula (3-1).

(In the formula, L, Ar ¹ , Ar ² , m, R ^{22 to} R ²⁵ and R ^{27 to} R ³⁰ are as defined above.) The condensed ring amine compound in any one of Claims 1-3 represented by following formula (4).

Wherein Ar, Ar ¹ , Ar ² , m and n are as defined above.
Any two of R ³¹ to R ^36, said each Ar, is used for binding to the nitrogen atom or adjacent phenylene group, ^R 31 ^{to R 36} other than it are each independently a hydrogen atom, a halogen atom, a substituted Or an unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted ring forming carbon number. A cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 carbon atoms, a cyano group, a substituted or unsubstituted ring formation An aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms is shown. ) The condensed ring amine compound of Claim 4 represented by a following formula (4-1).

(In the formula, Ar, Ar ¹ , Ar ² , m, n, R ³² , R ³³ , R ³⁵ and R ³⁶ are as defined above.) In R ^{11 to} R ¹⁸ other than those used for bonding to the nitrogen atom,
The halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and selected from the group consisting of n-octyl,
The substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is vinyl;
The substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is ethynyl;
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl and norbornyl;
The substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, or the substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms is trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, Selected from the group consisting of propyldimethylsilyl, triisopropylsilyl and triphenylsilyl;
The substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3- Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, Selected from the group consisting of benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl;
The substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms includes pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, imidazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, 1 -Dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4- Dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, phenanthridinyl group, acridinyl group, phenant Lorinyl group, phenazinyl group, phenothiazinyl group, phenoxadi Group, oxazolyl group, oxadiazolyl group, furazanyl group, condensed ring amine compound of Claim 1 which is selected from a thienyl group, and the group consisting of benzothiophenyl group. In R ^{11 to} R ¹⁸ other than those used for bonding to the nitrogen atom,
The halogen atom is fluorine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl. And
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-methylcyclohexyl;
The condensed ring amine compound according to claim 1 or 6, wherein the substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is selected from the group consisting of phenyl, biphenyl, tolyl, xylyl, and 1-naphthyl. R ^{11 to} R ¹⁸ other than those used for bonding to the nitrogen atom are each independently substituted with a hydrogen atom or a methyl, ethyl, propyl, isopropyl, n-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methyl group. The condensed ring amine compound according to claim 1, 6 or 7, which is a group selected from the group consisting of phenyl and 1-naphthyl. In R ^{21 to} R ³⁰ ,
The halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and selected from the group consisting of n-octyl,
The substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is vinyl;
The substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is ethynyl;
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl and norbornyl;
The substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, or the substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms is trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, Selected from the group consisting of propyldimethylsilyl, triisopropylsilyl and triphenylsilyl;
The substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3- Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, Selected from the group consisting of benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl;
The substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms includes pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, imidazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, 1 -Dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4- Dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, phenanthridinyl group, acridinyl group, phenant Lorinyl group, phenazinyl group, phenothiazinyl group, phenoxadi Group, oxazolyl group, oxadiazolyl group, furazanyl group, condensed ring amine compound of claim 2 which is selected from a thienyl group, and the group consisting of benzothiophenyl group. In R ^{21 to} R ³⁰ ,
The halogen atom is fluorine;
The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl. And
The substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-methylcyclohexyl;
The condensed ring amine compound according to claim 2 or 9, wherein the substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms is selected from the group consisting of phenyl, biphenyl, tolyl, xylyl, and 1-naphthyl. R ^{21 to} R ³⁰ are each independently a hydrogen atom, or a group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl substituted with a methyl group, and 1-naphthyl. The condensed ring amine compound according to claim 2, 9 or 10, which is a group selected from: The condensed ring amine compound according to any one of claims 1 to 11, wherein the group represented by the formula (2) is a group represented by the following formula (2-1) or (2-2).

(In the formula, X, Y and R ^{11 to} R ¹⁸ are as defined above.
The wavy line in the above formulas (2-1) and (-2) indicates a bond with a nitrogen atom. ) The group represented by the formulas (2-1) and (2-2) is a group represented by the following formula (2-1-1) or (2-2-1), respectively. Of the fused ring amine compound.

(Wherein R ^{11 to} R ¹⁸ and the wavy line are as defined above.) The fused ring amine according to any one of claims 1 to 13, wherein Ar ¹ and Ar ² other than the group represented by the formula (2) are substituted or unsubstituted aryl groups having 6 to 20 ring carbon atoms. Compound.   Formulas (1), (2), (2-1), (2-2), (2-1-1), (2-2-1), (3), (3-1), (4 ) And (4-1) “Substituted or unsubstituted...” Is independently substituted with an alkyl group, an alkylsilyl group, an arylsilyl group, an alkoxy group, an alkenyl group, an alkynyl group, an aryl group. Group, aryloxy group, aralkyl group, cycloalkyl group, heteroaryl group (heteroaromatic ring group), heteroaliphatic ring group, halogen atom, halogenated alkyl group, hydroxyl group, nitro group, cyano group and carboxy group The condensed ring amine compound according to any one of claims 1 to 14, which is selected from the group consisting of: Formulas (1), (2), (2-1), (2-2), (2-1-1), (2-2-1), (3), (3-1), (4 ) And (4-1) “Substituted or unsubstituted...” In each group independently represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group. , Isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl Group, triisopropylsilyl group, triphenylsilyl group,
Methoxy group, ethoxy group, vinyl group, ethynyl group,
Phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9- Phenanthryl group, naphthacenyl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrycenyl group, triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9 -Fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, terphenyl group, fluoranthenyl group,
Phenoxy group,
Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, adamantyl group, norbornyl group,

Pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, imidazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group , Furazanyl group, thienyl , Benzothiophenyl group,
Fluorine, chlorine, bromine, iodine,
Fluoromethyl group, difluoromethyl group, trifluoromethyl group, fluoroethyl group, trifluoromethylmethyl group,
The condensed ring amine compound according to claim 15, selected from the group consisting of a piperidinyl group, a piperazinyl group, a morpholinyl group, a quinuclidinyl group, a pyridinyl group, and an oxetanyl group. Formulas (1), (2), (2-1), (2-2), (2-1-1), (2-2-1), (3), (3-1), (4 ) And (4-1) “Substituted or unsubstituted...” In each group independently represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group. , Isobutyl group, t-butyl group, n-pentyl group, n-hexyl group,
Phenyl group, biphenyl group, tolyl group, xylyl group, 1-naphthyl group,
Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group,
Benzyl group, phenylethyl group, 2-phenylpropan-2-yl group,
1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4 -Dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group,
Fluorine atom, trifluoromethyl group,
The fused ring amine compound according to claim 16, which is selected from the group consisting of:   It has one or more organic thin film layers containing a light emitting layer between a cathode and an anode, and at least 1 layer of the said organic thin film layer is 1 or more types of the condensed ring amine compounds in any one of Claims 1-17. An organic electroluminescence element to be contained.   The organic electroluminescence device according to claim 18, wherein the light emitting layer contains the condensed ring amine compound. The organic electroluminescence device according to claim 18 or 19, wherein the light emitting layer contains an anthracene derivative represented by the following formula (5).

(In Formula (5), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, or a condensed ring having 10 to 50 substituted or unsubstituted ring atoms. A cyclic group,
R ^{101 to} R ¹⁰⁸ each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted condensed ring group having 10 to 50 ring atoms, substituted or unsubstituted, An unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 7 to 50 aralkyl groups, substituted or unsubstituted aryloxy having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms An arylsilyl group, a halogen atom or a cyano group. ) 21. The organic electroluminescence device according to claim 20, wherein in the formula (5), Ar ¹¹ and Ar ¹² are each a substituted or unsubstituted condensed ring group having 10 to 50 ring carbon atoms. In the formula (5), one of Ar ¹¹ and Ar ¹² is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other is a substituted or unsubstituted condensed ring having 10 to 50 ring atoms. The organic electroluminescence device according to claim 20, which is a cyclic group. In the formula (5), Ar ¹¹ is an unsubstituted phenyl group, or a phenyl group substituted with a monocyclic group or a condensed ring group, and Ar ¹² is a naphthyl group, a phenanthryl group, a benzoanthryl group, or dibenzofuranyl. The organic electroluminescence device according to claim 22, which is a group. 21. The organic electroluminescence device according to claim 20, wherein in the formula (5), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms. 25. The organic electroluminescence device according to claim 24, wherein in the formula (5), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted phenyl group. 26. The organic electroluminescence device according to claim 25, wherein in the formula (5), Ar ¹¹ is an unsubstituted phenyl group, and Ar ¹² is a phenyl group having a monocyclic group or a condensed ring group as a substituent. 26. The organic electroluminescence device according to claim 25, wherein in the formula (5), Ar ¹¹ and Ar ¹² are each independently a phenyl group having a monocyclic group or a condensed ring group as a substituent.   Electronic equipment provided with the organic electroluminescent element in any one of Claims 18-27. A lighting fixture comprising the organic electroluminescence element according to any one of claims 18 to 27.