JP5946317B2 - ORGANIC ELECTROLUMINESCENT ELEMENT, COMPOUND USABLE FOR THE SAME, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE - Google Patents

Description

  The present invention relates to an organic electroluminescence device, a compound that can be used for the organic electroluminescence device, and a material for an organic electroluminescence device. The present invention also relates to a light emitting device, a display device or a lighting device using the organic electroluminescent element.

  Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they emit light with high luminance when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do. Organic electroluminescence devices can be provided as devices having various emission wavelengths, and are expected to be applied to a wide range of applications because of their high response speed and relatively thin and light weight. Yes. In particular, the development of an organic electroluminescent device having high blue purity and high luminous efficiency is important for application to full-color displays, and various development research results have been reported so far.

For example, Non-Patent Document 1 describes that pure blue light emission having a sharp spectrum can be obtained by a compound in which a diphenylamino group is substituted on a benzene ring at both ends of a mother nucleus in which five benzene rings are condensed. .
Patent Document 1 describes as a specific example a compound in which a diphenylamino group is substituted on the benzene ring at both ends of a mother nucleus in which an indene ring is condensed to a triphenylene skeleton, and two phenyl groups are substituted on the mother nucleus. . Thus, the compound having two phenyl groups in the mother nucleus has a broad spectrum, and in the example of Patent Document 1, although it is a mixture of isomers, the chromaticity is (0.41, 0.55) ( CIE1931 color system) and yellow to yellow-green light emission, and not pure blue light emission. In addition, Patent Document 1 [0019] describes, as a preferable example, that this compound is used for a light emitting material from yellow to white, and does not suggest use as a blue light emitting material.
Patent Document 2 describes a compound having a mother nucleus in which an indole ring is condensed on a triphenylene skeleton, and in the examples, only examples used as a host material for organic electroluminescence device emitting green phosphorescence are shown. There is no suggestion of using the above compound in an organic electroluminescence device emitting blue fluorescence.
Patent Document 3 discloses an example in which a tetrabenzo [a, cd, j, lm] perylene derivative is used as a green fluorescent material of an organic electroluminescence device.
Patent Document 4 discloses an example in which an acetonaphtho [1,2-k] benzo [e] acephenanthrene derivative is used as a blue fluorescent material of an organic electroluminescence device. From the examples of this document, it can be seen that the emission spectrum of the above compounds is indeed blue, but it has not reached the required pure blue.
Patent Document 5 describes a compound having a structure in which a triphenylene ring and a diphenylamino group are linked via a linking group such as a single bond, an arylene group, or a heteroarylene group, and is a host of an organic electroluminescence device that emits green phosphorescence. Examples used as materials are described. However, Patent Document 5 does not describe an example in which the above linking group forms a condensed ring with a triphenylene ring, and at least in the examples, the above compound is not used in an organic electroluminescence device emitting blue fluorescence. There wasn't.
Patent Document 6 discloses a compound having a structure similar to that of Patent Document 5, specifically, an example in which a triphenylene ring and a diphenylamino group are bonded only through an arylene group or a heteroarylene group. (No single bond is mentioned), and an example used for an organic electroluminescence device emitting blue fluorescence is described. However, the required pure blue color was not reached.

EP2308945 KR20111123106 JP 2002-319490 A JP 2010-270103 A International Publication WO2011 / 139129 JP 2009-292760 A

Balagopal Shainhama Shaibu et al. , J. et al. Org. Chem. , 2011, 76 (4), 1054-1061

However, as a result of investigations by the present inventors, it has been found that organic electroluminescent devices using the compounds described in Non-Patent Document 1 remain unsatisfactory in luminous efficiency. On the other hand, it was found that the organic electroluminescent elements using the compounds described in Patent Documents 1, 3, 4, and 6 did not reach the required pure blue color, and the blue purity remained unsatisfactory.
The problem to be solved by the present invention is to provide an organic electroluminescence device having high luminous efficiency, sharp spectrum and excellent blue purity.

  Therefore, the present inventor has intensively studied for the purpose of providing an organic electroluminescence device having high luminous efficiency, sharp spectrum and excellent blue purity. As a result, the inventors have found that the above problems can be solved by using a compound having a specific structure, and have provided the present invention described below.

[1] A substrate, a pair of electrodes formed on the substrate and including an anode and a cathode, and at least one organic layer including a light emitting layer disposed between the electrodes, and the at least one organic layer An organic electroluminescent device comprising a compound represented by the following general formula (1) in any of the above:
(In the general formula (1), R ^{1 to} R ¹² each independently represents a hydrogen atom or a substituent. R ¹⁰ and R ¹¹ may form a ring together, but R ¹¹ and R ¹² are And one pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ together represents any one of the divalent substituents represented by the following general formulas a to e, However, the combination of R ⁴ and R ⁵ and R ⁸ and R ⁹ does not form a ring, and R ⁴ and R ⁵ together form the following general formula a. R ³ and R ⁹ each represent a substituent other than an unsubstituted phenyl group or a hydrogen atom, and R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a hetero group. X ^{1 to} X ¹² each independently represents a carbon atom or a nitrogen atom, and when X ^{1 to} X ¹² represent a nitrogen atom, they are bonded to the nitrogen atom. R ^{1 to} R ¹² are not present.)
(In general formulas a to e, * represents a bonding site between X ⁴ and X ⁵ or a bonding site between X ⁸ and X ^9. R ^{105 to} R ¹⁰⁹ are each independently an alkyl group, an aryl group, or Represents a heteroaryl group.)
[2] In the organic electroluminescent element according to [1], it is preferable that in the general formula (1), X ^{1 to} X ¹² are all carbon atoms.
[3] In the organic electroluminescent element according to [1] or [2], the compound represented by the general formula (1) is preferably a compound represented by the following general formula (2).
(In General Formula (2), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom or a substituent. One group of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the general formulas a to e and forms a ring, provided that both R ⁴ and R ⁵ and R ⁸ and R ⁹ are combined. In addition, when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula a, R ³ and R ⁹ are other than an unsubstituted phenyl group. In addition, when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula c, R ¹⁵ is other than an aryl group, heteroaryl group, or arylamino group. R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group or a heteroaryl group, X ^{1 to} X ⁹ And X ^{12 to} X ¹⁶ each independently represent a carbon atom or a nitrogen atom, and when X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ represent a nitrogen atom, R ^{1 to} R ⁹ and R ¹² bonded to the nitrogen atom ~R ¹⁶ does not exist.)
[4] In the organic electroluminescent element according to [3], it is preferable that in the general formula (2), X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ are all carbon atoms.
[5] In the organic electroluminescent element according to any one of [1] to [4], the compound represented by the general formula (1) is a compound represented by the following general formula (3). Is preferred.
(In General Formula (3), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom, an alkyl group or a fluorine atom. One set of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the above general formulas a to e to form a ring, provided that R ⁴ and R ⁵ , and both R ⁸ and R ⁹ are combined. And R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group.)
[6] In the organic electroluminescent element according to any one of [1] to [5], the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less.
[7] In the organic electroluminescent element according to any one of [1] to [6], at least one organic layer containing the compound represented by the general formula (1) is the light emitting layer. preferable.
[8] In the organic electroluminescent element according to any one of [1] to [7], the compound represented by the general formula (1) is preferably a luminescent material.
[9] The organic electroluminescent element according to any one of [1] to [8] preferably includes a compound represented by the following general formula (An-1) in at least one layer of the organic layer.
(In the general formula (An-1), Ar ¹ and Ar ² each independently represent an aryl group or a heteroaryl group, and R ^{301 to} R ³⁰⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ^307, and R ³⁰⁷ and R ³⁰⁸ may be bonded to each other to form a ring.
[10] In the organic electroluminescent element according to [9], the compound represented by the general formula (An-1) is preferably a compound represented by the following general formula (An-2).
(In General Formula (An-2), R ^{301 to} R ³¹⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ R ³⁰⁶ and R ³⁰⁷ , R ³⁰⁷ and R ³⁰⁸ , R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , R ³¹¹ and R ³¹² , R ³¹² and R ³¹³ , R ³¹⁴ and R ³¹⁵ , R ³¹⁵ and R ³¹⁶ , R ³¹⁶ and R ³¹⁷ and R ³¹⁷ and R ³¹⁸ may be bonded to each other to form a ring.)
[11] In the organic electroluminescent element according to [9] or [10], it is preferable that at least one organic layer containing the compound represented by the general formula (An-1) is the light emitting layer.
[12] A light-emitting device using the organic electroluminescent element according to any one of [1] to [11].
[13] A display device using the organic electroluminescent element according to any one of [1] to [11].
[14] An illumination device using the organic electroluminescent element according to any one of [1] to [11].
[15] A compound represented by the following general formula (3):
(In General Formula (3), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom, an alkyl group or a fluorine atom. One set of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the following general formulas a to e to form a ring, provided that both R ⁴ and R ⁵ , and both R ⁸ and R ⁹ are combined. And R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group.)
(In general formulas a to e, * represents a bonding site between X ⁴ and X ⁵ or a bonding site between X ⁸ and X ^9. R ^{105 to} R ¹⁰⁹ are each independently an alkyl group, an aryl group, or Represents a heteroaryl group.)
[16] A material for an organic electroluminescence device comprising the compound according to [15].
[17] The material for an organic electroluminescent element according to [16] is preferably a luminescent material.

  The organic electroluminescent device of the present invention has high luminous efficiency, sharp spectrum and excellent blue purity. Moreover, if the compound of this invention is used, such an outstanding organic electroluminescent element can be manufactured easily. Furthermore, the light emitting device, the display device, and the lighting device of the present invention have advantageous effects of low power consumption and excellent blue purity.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention.

  Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In the present specification, a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.

[Organic electroluminescence device]
The organic electroluminescent element of the present invention comprises a substrate, a pair of electrodes formed on the substrate and comprising an anode and a cathode, and at least one organic layer including a light emitting layer disposed between the electrodes, Any of the at least one organic layer contains a compound represented by the following general formula (1).
(In the general formula (1), R ^{1 to} R ¹² each independently represents a hydrogen atom or a substituent. R ¹⁰ and R ¹¹ may form a ring together, but R ¹¹ and R ¹² are And one pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ together represents any one of the divalent substituents represented by the following general formulas a to e, However, the combination of R ⁴ and R ⁵ and R ⁸ and R ⁹ does not form a ring, and R ⁴ and R ⁵ together form the following general formula a. R ³ and R ⁹ each represent a substituent other than an unsubstituted phenyl group or a hydrogen atom, and R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a hetero group. X ^{1 to} X ¹² each independently represents a carbon atom or a nitrogen atom, and when X ^{1 to} X ¹² represent a nitrogen atom, they are bonded to the nitrogen atom. R ^{1 to} R ¹² are not present.)
(In general formulas a to e, * represents a bonding site between X ⁴ and X ⁵ or a bonding site between X ⁸ and X ^9. R ^{105 to} R ¹⁰⁹ are each independently an alkyl group, an aryl group, or Represents a heteroaryl group.)

The organic electroluminescent element of the present invention is characterized in that the emission spectrum is sharpened and the blue purity is improved by containing the compound represented by the general formula (1) in at least one organic layer. In order to improve the blue purity, it is known that shortening the emission wavelength is also useful. However, when the emission wavelength of the light emitting material is shortened, the S ₁ (minimum excited singlet energy level) of the light emitting material increases, so that the difference between S ₁ of the light emitting material and S ₁ of the host material decreases, or S ₁ of the host material than S ₁ of the light emitting material is increased. For this reason, the luminous efficiency is lowered, and there is a problem that the blue purity is lowered due to a mixture of the sub-light emission of the host material. On the other hand, if the compound represented by the general formula (1) is used according to the present invention, the spectrum can be sharpened while realizing high luminous efficiency, and the blue purity can be improved.
The reason why the spectrum can be sharpened is not well understood, but it is thought as follows. By making the mother nucleus part into a condensed ring structure, the part where the molecule can rotate is restricted by the fact that the structure is rigid, and as a result, this is considered to be due to the fact that subtransitions are suppressed.
The reason why the luminous efficiency is excellent is not well understood, but it is considered as follows. For example, J. et al. Org. Chem. , 2011, 76 (4), 1054-1061, the HOMO and LUMO distribution modes mainly involved in the transition are not on the same atom but different from each other. It is considered that the light emission efficiency was lowered because the transition dipole was reduced and, as a result, the oscillator strength was reduced. On the other hand, in the compound represented by the general formula (1) of the present invention, the HOMO and LUMO distribution modes mainly involved in the transition are mainly on the same atom of the phenylene moiety sandwiched between the two amino groups. It is considered that the luminous efficiency has been improved by increasing the dipole and, as a result, increasing the oscillator strength.

<< Compound Represented by Formula (1) >>
In the following, first, the compound represented by the general formula (1) will be described in detail.
In the present invention, the hydrogen atom in the description of the general formula (1) includes an isotope (deuterium atom and the like), and the atoms constituting the substituent further include the isotope.
In the present invention, when the term “substituent” is used, the substituent may be further substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that the number of carbon atoms is 1 to 6 as all groups including those substituted.

General formula (1)

In the general formula (1), R ^{1 to} R ¹² each independently represents a hydrogen atom or a substituent. R ¹⁰ and R ¹¹ may form a ring together, but R ¹¹ and R ¹² do not form a ring together. One pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ jointly represents any one of the divalent substituents represented by the following general formulas a to e to form a ring.
However, the combination of R ⁴ and R ⁵ , and R ⁸ and R ⁹ together does not form a ring. When R ⁴ and R ⁵ together represent a divalent substituent represented by the following general formula a, R ³ and R ⁹ represent a substituent other than an unsubstituted phenyl group or a hydrogen atom.

First, one group of R ⁴ and R ⁵ or R ⁸ and R ⁹ jointly describes a divalent substituent represented by the following general formulas a to e.

In the general formulas a to e, * represents a binding site between X ⁴ and X ⁵ or a binding site between X ⁸ and X ⁹ . R ^{105 to} R ¹⁰⁹ each independently represents an alkyl group, an aryl group or a heteroaryl group.
The general formulas a to e will be described in order from the general formula a.

In the general formula a, examples of R ¹⁰⁵ or R ¹⁰⁶ (substituent on the carbon atom) include substituents included in the following substituent group A.
However, when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula a, R ³ and R ⁹ are substituents other than an unsubstituted phenyl group from the viewpoint of spectrum sharpening. It is necessary to represent a group (preferably a substituent other than a phenyl group, more preferably a substituent other than an aryl group) or a hydrogen atom. In the case where R ⁸ and R ⁹ together represent a divalent substituent represented by the general formula a, there is no such limitation.

<< Substituent group A >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl group, etc.), alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms). For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms). For example, propargyl, 3-pentynyl, etc.), an aryl group (preferably having 6 to 3 carbon atoms) More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, naphthyl, anthranyl. , Triphenylenyl, etc.), an amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino) , Dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms such as methoxy, And ethoxy, butoxy, 2-ethylhexyloxy, etc.), aryl Oxy group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.) A heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.). An acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group ( Preferably it has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms. Examples thereof include methoxycarbonyl and ethoxycarbonyl. ), An aryloxycarbonyl group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, such as phenyloxycarbonyl), an acyloxy group (preferably Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.), An acylamino group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, more preferably carbon atoms). 2 to 20, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino). A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), a sulfamoyl group (Preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms. Examples thereof include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably A prime number of 1-20, particularly preferably a carbon number of 1-12, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc., an alkylthio group (preferably having a carbon number of 1-30, more preferably a carbon number). 1 to 20, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio, etc.), arylthio groups (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably carbon atoms). And a heterocyclic thio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). Pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio Etc. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as mesyl and tosyl), a sulfinyl group (preferably carbon). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably 1 to 30 carbon atoms, more Preferably it is C1-C20, Most preferably, it is C1-C12, for example, ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide group (preferably C1-C30, more preferably It has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms. Examples thereof include diethyl phosphoric acid amide and phenyl phosphoric acid amide. Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group Group, heterocyclic group (including aromatic heterocyclic group, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, phosphorus Atoms, silicon atoms, selenium atoms, tellurium atoms, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, Tellurophenyl, piperidyl, piperidino Morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, dibenzothiophenyl group, dibenzofuranyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms) , More preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenylsilyl, etc.), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably carbon atoms). 3 to 30, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy and triphenylsilyloxy), and phosphoryl groups (such as diphenylphosphoryl and dimethylphosphoryl groups). . These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

In the general formula a, R ¹⁰⁵ or R ¹⁰⁶ each independently preferably represents an aryl group or an alkyl group, preferably a phenyl group or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms. Particularly preferred is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, and particularly preferred is a methyl group.
From the viewpoint of ease of synthesis, R ¹⁰⁵ and R ¹⁰⁶ are preferably the same substituent.

In the general formula b, examples and preferred ranges of R ¹⁰⁷ or R ¹⁰⁸ (substituent on silicon atom) are the same as examples and preferred ranges of R ¹⁰⁵ or R ¹⁰⁶ (substituent on carbon atom).

In the general formula c, examples of the R ¹⁰⁹ (substituent on the nitrogen atom) include the substituent group A.

In the general formula c, R ¹⁰⁹ preferably represents an aryl group, and is a phenyl group, m-methylphenyl group, p-methylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group. A naphthyl group is more preferable, and a phenyl group is particularly preferable.

From the viewpoint of sharpening the spectrum, it is preferable that one pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ collectively represents a divalent substituent represented by the general formulas a to d. From the viewpoint, it is more preferable to represent a divalent substituent represented by the general formulas a, c and d.

In the general formula (1), any combination of R ⁴ and R ⁵ or R ⁸ and R ⁹ represents any one of the divalent substituents represented by the general formulas a to e, and the ring Form.
Among them, R ⁴ and R ⁵ jointly represent any one of the divalent substituents represented by the general formulas a to e, and R ⁸ and R ⁹ jointly form a ring. From the viewpoint of luminous efficiency, it is preferable to form a ring.

Next, in R ^{1 to} R ¹² in the general formula (1), a group of substituents that do not form a ring together among R ⁴ and R ⁵ and R ⁸ and R ⁹ , and R ^{1 to} R ³ , R ⁶ , R ⁷ and R ^{10 to} R ¹² will be described. Hereinafter, these groups are referred to as “groups other than the divalent substituents represented by the general formulas a to e in R ^{1 to} R ¹² ”.
In the general formula (1), groups other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² represent a hydrogen atom or a substituent.
Examples of the substituent represented by the group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² include the substituents included in the substituent group A.

As the substituent represented by the group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ^12, among the substituent group A, an alkyl group, an aryl group, a heteroaryl group, A halogen atom, a cyano group and a silyl group are preferred, and an alkyl group, an aryl group and a halogen atom are more preferred.

The alkyl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is preferably an alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, n -Propyl group, i-propyl group, tert-butyl group, pentyl group, cyclohexyl group are more preferable,
A methyl group and a tert-butyl group are particularly preferred. The alkyl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² may further have a substituent, and examples of the substituent include the substituent group described above. The substituent contained in A can be mentioned, Among these, a halogen atom is preferable and a fluorine atom is more preferable.

The aryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is preferably an aryl group having 6 to 15 carbon atoms, and more preferably a phenyl group. The aryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² may further have a substituent, and the substituent includes the substituent group. The substituent contained in A can be mentioned, Among these, an alkyl group, an aryl group, an amino group, and a fluorine atom are preferable, a methyl group, a phenyl group, and a fluorine atom are more preferable, and a methyl group and a fluorine atom are especially preferable. There are no particular restrictions on the position of the substituent substituted on the aryl group.
The aryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² may have an amino group, but the emission spectrum is sharpened and colored. From the viewpoint of increasing the purity, the aryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is unsubstituted or substituted with an alkyl group or a fluorine atom. Is preferred.

The heteroaryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is preferably a heteroaryl group having 5 to 10 ring members, and the number of ring members More preferably, it is a 5 or 6 heteroaryl group. The hetero atom constituting the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. The number of heteroatoms contained in the heteroaryl group is preferably 1 to 3, more preferably 1. The heteroaryl group represented by a group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is particularly preferably a pyridyl group or a thiophenyl group, and more preferably a 2-pyridyl group.

The halogen atom represented by the group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is preferably a fluorine atom.

The silyl group represented by the group other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is preferably a trimethylsilyl group or a triphenylsilyl group, and more preferably a trimethylsilyl group.

In the compound of the present invention, in the general formula (1), the substituents represented by R ^{1 to} R ¹² are represented by the general formulas a to e represented by one of R ⁴ and R ⁵ or R ⁸ and R ⁹ together. 2 to 6 including the divalent substituent represented by (corresponding to 2) is preferable, 2 to 4 is more preferable, and 2 is particularly preferable.
In R ^{1 to} R ¹² of the general formula (1), the position that may have a substituent other than the divalent substituent represented by the general formulas a to e in R ^{1 to} R ¹² is particularly limit is not, is preferably ^{R 6, R 7, R 10} , R 11, and more preferably R ^10, R ^11.

In the general formula (1), R ¹⁰ and R ¹¹ may or may not form a ring together, but preferably form a ring together.
In the general formula (1), the ring that R ¹⁰ and R ¹¹ may form together is preferably a 5- or 6-membered ring, and preferably a 6-membered ring. The ring formed by R ¹⁰ and R ¹¹ together is preferably an aromatic ring, and more preferably a hydrocarbon aromatic ring.

R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group.
R ¹⁰¹ and R ¹⁰² , or R ¹⁰³ and R ¹⁰⁴ may form a ring together.

The alkyl group represented by R ^{101 to} R ¹⁰⁴ is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms. Methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, and methyl group. A group, an ethyl group, and an n-propyl group are more particularly preferable.
The alkyl group represented by R ^{101 to} R ¹⁰⁴ may further have a substituent, and examples of the substituent include substituents included in the substituent group A. Among them, an aryl group is preferable, and phenyl Groups are more preferred.

When R ^{101 to} R ¹⁰⁴ represent an alkyl group, it is also preferable that R ¹⁰¹ and R ¹⁰² , or R ¹⁰³ and R ¹⁰⁴ jointly form a ring, and the ring formed in this case is a 5- or 6-membered ring It is preferably a ring, more preferably a 6-membered ring, and particularly preferably a piperidine ring.

The aryl group represented by R ^{101 to} R ¹⁰⁴ is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms (for example, a phenyl group, a naphthyl group, an anthranyl group, a phenanthrenyl group). And triphenylenyl group), particularly preferably an aryl group having 6 to 15 carbon atoms, more particularly preferably a phenyl group, a 1-naphthyl group and a 2-naphthyl group, and still more particularly preferably a phenyl group and 2 -A naphthyl group.
The aryl group represented by R ^{101 to} R ¹⁰⁴ may further have a substituent, and examples of the substituent include the substituents included in the substituent group A, and among them, an alkyl group (having 1 carbon atom). To 5 alkyl groups are preferred, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, tert-butyl groups are more preferred, methyl groups are particularly preferred, and aryl groups (C6-C10 aryl groups are preferred). The aryl group may further have a substituent, and is preferably an alkyl group, a halogen atom, an aryl group or a silyl group (preferably a trimethylsilyl group or a triphenylsilyl group), and an alkyl group. An aryl group and a fluorine atom are more preferred.

When R ^{101 to} R ¹⁰⁴ represent an aryl group, it is also preferred that R ¹⁰¹ and R ¹⁰² , or R ¹⁰³ and R ¹⁰⁴ together form a ring, and in this case, the ring formed is 5 or 6 A member ring is preferred. When R ¹⁰¹ and R ¹⁰² jointly form a ring (the relationship in which R ¹⁰¹ and R ¹⁰² together form a ring is the same as the relationship where R ¹⁰³ and R ¹⁰⁴ jointly form a ring) In other ^words , when R ¹⁰¹ and R ¹⁰² form a ring via a single bond, when R ¹⁰¹ further forms a ring and R ¹⁰² forms a ring, R ¹⁰² further has a substituent and R ¹⁰¹ The case where a ring is formed and the case where a substituent further possessed by R ¹⁰¹ and a substituent further possessed by R ¹⁰² form a ring are included. Otherwise the R ¹⁰¹ and R ¹⁰² form a ring via a single bond, R ¹⁰¹ and R ¹⁰² is preferably bonded through a linking group L. As the linking group L, CR ¹¹² R ¹¹³ , NR ¹¹⁴ , Si ¹¹⁵ R ¹¹⁶ (R ¹¹² , R ¹¹³ , R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ each independently represents a substituent, fluorine atom, alkyl group, aryl Preferably represents a group or a heteroaryl group), O atom or S atom, preferably CR ¹¹² R ¹¹³ , NR ¹¹⁴ , O atom or S atom, CR ¹¹² R ¹¹³ , Particular preference is given to NR ¹¹⁴ or O atoms. Examples of R ¹¹² , R ¹¹³ , R ^115, and R ¹¹⁶ (substituents on carbon atoms and substituents on silicon atoms) can include the substituent group A, and the preferred ranges thereof are those of R ¹⁰⁵ and R ¹⁰⁶ . This is the same as the preferred range.

Examples of R ¹¹⁴ (substituent on the nitrogen atom) include the substituent group B, and a preferred range is the same as the preferred range of R ¹⁰⁹ .

The heteroaryl group represented by R ^{101 to} R ¹⁰⁴ is preferably a heteroaryl group having 5 to 30 ring members, more preferably a heteroaryl group having 5 to 10 ring members, and particularly preferably 5 or 6 ring members. Of the heteroaryl group. The hetero atom constituting the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. The number of heteroatoms contained in the heteroaryl group is preferably 1 to 3, more preferably 1. The heteroaryl group represented by R ^{101 to} R ¹⁰⁴ is particularly preferably a pyridyl group, a furanyl group, or a thiophenyl group, and more preferably a 2-pyridyl group, a 2-furanyl group, or a 2-thiophenyl group.
The heteroaryl group represented by R ^{101 to} R ¹⁰⁴ may further have a substituent, and examples of the substituent include substituents included in the substituent group A, and among them, an alkyl group is preferable. An alkyl group having 1 to 3 carbon atoms is more preferable, and a methyl group is particularly preferable.

The compounds of the present invention, in the general formula (1), R ¹⁰¹ ~R ¹⁰⁴ each preferably from the viewpoint of the emission efficiency represent an aryl group or a heteroaryl group independently, both R ¹⁰¹ to R ¹⁰⁴ is an aryl group It is preferably any one of an unsubstituted phenyl group, 1-naphthyl group, 2-naphthyl group, biphenyl group (preferably p-phenylphenyl group) and methylphenyl group (preferably p-methylphenyl group). It is more preferable from the viewpoint of luminous efficiency.
When R ^{101 to} R ¹⁰⁴ are all aryl groups, the combination of R ^{101 to} R ¹⁰⁴ is not particularly limited.

In the compound of the present invention, the combination of the group represented by —NR ¹⁰¹ R ¹⁰² and the group represented by —NR ¹⁰³ R ¹⁰⁴ in the general formula (1) is not particularly limited, but is the same as each other. Is preferable from the viewpoint of the shape of the emission spectrum and the ease of synthesis.

In the compound of the present invention, in the general formula (1), X ^{1 to} X ¹² each independently represent a carbon atom or a nitrogen atom. Of X ^{1 to} X ¹² , at least X ¹⁰ and X ¹¹ are preferably carbon atoms.
In the general formula (1), 9 or more of X ^{1 to} X ¹² are preferably carbon atoms, more preferably 11 or more are carbon atoms, and X ^{1 to} X ¹² are all carbon atoms. Particularly preferred is an atom.

  In the compound of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (2).

In general formula (2), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom or a substituent. One pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ jointly represents any one of the divalent substituents represented by the general formulas a to e, and forms a ring. However, the combination of R ⁴ and R ⁵ , and R ⁸ and R ⁹ together does not form a ring. When R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula a, R ³ and R ⁹ represent a substituent other than an unsubstituted phenyl group or a hydrogen atom. Further, when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula c, R ¹⁵ represents a substituent other than an aryl group, a heteroaryl group or an arylamino group, or a hydrogen atom. . R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group or a heteroaryl group. X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ each independently represent a carbon atom or a nitrogen atom, and when X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ represent a nitrogen atom, R ¹ to R ¹ bonded to the nitrogen atom R ⁹ and R ^{12 to} R ¹⁶ are not present.

The explanation and preferred range of R ^{1 to} R ⁹ and R ¹² in the general formula (2) are the same as the explanation and preferred range of R ^{1 to} R ⁹ and R ¹² in the general formula (1). However, in the general formula (2), when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula c, R ¹⁵ described later is an aryl group, a heteroaryl group, an arylamino group Represents a substituent other than or a hydrogen atom.

The preferred range of the substituent represented by R ^{13 to} R ¹⁶ in the general formula (2) is a divalent substituent represented by the general formula a to e in R ^{1 to} R ¹² in the general formula (1). It is the same as the preferable range of groups other than.
In R ^{13 to} R ¹⁶ in the general formula (2), 0 to 4 substituents are preferable, 0 to 3 are more preferable, 0 to 2 are particularly preferable, and 0 Or, it is more particularly preferably 1, and even more preferably 0.

The explanation and preferred range of R ^{101 to} R ¹⁰⁴ in the general formula (2) are the same as the explanation and preferred range of R ^{101 to} R ¹⁰⁴ in the general formula (1).

The explanation and preferred range of X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ in the general formula (2) are the same as the explanation and preferred range of X ^{1 to} X ¹² in the general formula (1).

In the compound of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (3).
In General Formula (3), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom, an alkyl group, or a fluorine atom. One pair of R ⁴ and R ⁵ or R ⁸ and R ⁹ jointly represents any one of the divalent substituents represented by the general formulas a to e, and forms a ring. However, the combination of R ⁴ and R ⁵ , and R ⁸ and R ⁹ together does not form a ring. R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group or a heteroaryl group.

R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ in the general formula (3) each independently represent a hydrogen atom, an alkyl group, or a fluorine atom. The explanation and preferred range when R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ are alkyl groups are the same as the explanation and preferred range of R ^{1 to} R ⁹ and R ¹² in the general formula (1).

The explanation and the preferred range of R ^{101 to} R ¹⁰⁴ in the general formula (3) are the same as the explanation and the preferred range of R ^{101 to} R ¹⁰⁴ in the general formula (1).

  When the compound represented by the general formula (1) is used as a blue light emitting material, the maximum light emission wavelength of the organic electroluminescent element is usually less than 460 nm. Preferably it is 400 nm or more and less than 460 nm, More preferably, it is 420 nm or more and less than 455 nm, More preferably, it is 425 nm or more and less than 455 nm, Most preferably, it is 430 nm or more and less than 455 nm from a viewpoint of obtaining blue light emission with high color purity. The maximum light emission wavelength in the thin film state of the compound represented by the general formula (1) is preferably 430 nm or more and less than 455 nm because blue light emission having particularly high color purity is obtained.

  The compound represented by the general formula (1) preferably has a molecular weight of 1200 or less, more preferably 1100 or less, still more preferably 1000 or less, and particularly preferably 950 or less. Since the sublimation temperature can be lowered by lowering the molecular weight, thermal decomposition of the compound during vapor deposition can be prevented. Also, the energy required for vapor deposition can be suppressed by shortening the vapor deposition time. Here, since a material having a high sublimation temperature may undergo thermal decomposition during vapor deposition for a long time, the sublimation temperature should not be too high from the viewpoint of vapor deposition suitability. The sublimation temperature of the compound represented by the general formula (1) (in the present specification, meaning a 10% by mass reduction temperature) is preferably 425 ° C. or less, more preferably 400 ° C. or less, and still more preferably It is 375 degrees C or less, Most preferably, it is 350 degrees C or less.

  Specific examples of the compound represented by the general formula (1) are shown below, but the compound represented by the general formula (1) that can be used in the present invention is limitedly interpreted by these specific examples. It shouldn't be.

Furthermore, among the compounds represented by the general formula (1), in the case of the general formula (3), when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula a, R ⁴ And R ⁵ together represent a divalent substituent represented by the general formula c, and R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula d. A more specific example is shown below. These can be similarly considered for combinations other than the exemplified compounds.

The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, J. et al. Org. Chem. , 2011, 76 (4), 1054-1061 and Japanese Patent Application Laid-Open No. 2008-50308.
Although two general synthetic schemes are shown below, the following synthetic route is an example and can be synthesized by another known method. Synthetic methods other than these will be described in Examples described later.

In Synthetic route 1, Z represents a divalent substituent of general formulas a to e. R ¹ , R ² , R ³ and R ⁴ represent an alkyl group, an aryl group or a heteroaryl group. X represents chlorine, bromine or iodine. “Cu” represents a copper catalyst (eg, Cu, CuI, etc.), and “Pd” represents a palladium catalyst (eg, palladium acetate, trisdibenzylideneacetone bispalladium, PdCl ₂ (PPh ₃ ) _2, etc.). Known ligands (for example, phosphorus ligands such as triphenylphosphine, tricyclohexylphosphine, tricyclohexylphosphine / tetrafluoroborate salt, and tritertiary butylphosphine) can also be added. base represents a base, and other known bases (for example, Na ₂ CO ₃ , K ₂ CO ₃ , Cs ₂ CO ₃ , NaHCO ₃ , K ₃ PO ₄ , NaO ^t Bu, KO ^t Bu, Triethylamine, DBU (an organic base such as 1,8-diazabicyclo [5.4.0] undec-7-ene) can be used. Tf represents a trifluoromethanesulfonyl group. These reaction solvents are known (for example, tetrahydrofuran, 1,2-dimethoxyethane, toluene, xylene, N, N-dimethylformamide, N, N-dimethylacetamide, pyridine, dichloromethane, chloroform, 1,2-dichloroethane, Ethanol, methanol, acetone, etc.), and the reaction temperature is also appropriately different. When the final product is a mixture of isomers, either one can be selectively obtained by repeating recrystallization, although the yield decreases. In addition, a mixture of isomers can be used as a material for an organic electroluminescence device.

In Synthetic route 2, Z represents a divalent substituent of general formulas a to e. R ⁵ , R ⁶ , R ⁷ and R ⁸ represent an alkyl group, an aryl group or a heteroaryl group. “Cu” represents a copper catalyst (eg, Cu, CuI, etc.), and “Pd” represents a palladium catalyst (eg, palladium acetate, trisdibenzylideneacetone bispalladium, PdCl ₂ (PPh ₃ ) _2, etc.). Known ligands (for example, phosphorus ligands such as triphenylphosphine, tricyclohexylphosphine, tricyclohexylphosphine / tetrafluoroborate salt, and tritertiary butylphosphine) can also be added. base represents a base, and other known bases (for example, Na ₂ CO ₃ , K ₂ CO ₃ , Cs ₂ CO ₃ , NaHCO ₃ , K ₃ PO ₄ , NaO ^t Bu, KO ^t Bu, Triethylamine, DBU (an organic base such as 1,8-diazabicyclo [5.4.0] undec-7-ene) can be used. Tf represents a trifluoromethanesulfonyl group. These reaction solvents are known (for example, tetrahydrofuran, 1,2-dimethoxyethane, toluene, xylene, N, N-dimethylformamide, N, N-dimethylacetamide, pyridine, dichloromethane, chloroform, 1,2-dichloroethane, Ethanol, methanol, acetone, etc.), and the reaction temperature is also appropriately different. When the product becomes a mixture of isomers, either one can be selectively obtained by repeating recrystallization, although the yield decreases. In addition, a mixture of isomers can be used as a material for an organic electroluminescence device.

  After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

<< Configuration of Organic Electroluminescent Element >>
The organic electroluminescent element of the present invention comprises a substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and at least one organic layer disposed between the electrodes and including a light emitting layer, At least one layer of the light emitting layer contains the compound represented by the general formula (1).
The structure of the organic electroluminescent element of the present invention is not particularly limited. FIG. 1 shows an example of the configuration of the organic electroluminescent element of the present invention. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, light emission wavelength, and a use.

<Board>
The organic electroluminescent element of the present invention has a substrate.
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

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

(anode)
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.

(cathode)
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.

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

(Organic layer structure)
In the organic electroluminescent element of the present invention, the organic layer includes a light emitting layer. The organic layer preferably includes a charge transport layer. The charge transport layer is a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescence device. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, a low-cost and highly efficient organic electroluminescent device can be produced.

The compound represented by the general formula (1) is contained in at least one of the light emitting layers in the organic layer disposed between the electrodes of the organic electroluminescent element.
However, the compound represented by the general formula (1) may be contained in the other organic layer of the organic electroluminescent element of the present invention unless it is contrary to the gist of the present invention. Examples of the organic layer other than the light emitting layer that may contain the compound represented by the general formula (1) include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge. Block layer (hole block layer, electron block layer, etc.) can be mentioned, preferably a hole injection layer, a hole transport layer, an exciton block layer, or a charge block layer, more preferably They are a hole transport layer, an exciton block layer, and a charge block layer.

  When the compound represented by the general formula (1) is contained in the light emitting layer, the compound represented by the general formula (1) may be contained in an amount of 0.1 to 100% by mass with respect to the total mass of the light emitting layer. Preferably, 1 to 50% by mass is included, and 2 to 20% by mass is more preferable.

  When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, the compound represented by the general formula (1) is contained in an amount of 70 to 100% by mass with respect to the total mass of the organic layer. It is preferable that 80-100 mass% is contained, It is more preferable that 90-100 mass% is contained.

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

(Light emitting layer)
The light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light. However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism.

  The light emitting layer in the organic electroluminescent element of the present invention may be composed of only the light emitting material, or may be a mixed layer of a host material and the light emitting material. The kind of the light emitting material may be one kind or two kinds or more. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

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

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

  In the organic electroluminescent element of the present invention, the light emitting layer contains the compound represented by the general formula (1), and the compound represented by the general formula (1) is used as a light emitting material of the light emitting layer. This is a more preferred embodiment. Here, in this specification, the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less. The compound represented by the general formula (1) may be used as a host material of the light emitting layer.

(Luminescent material)
In the organic electroluminescent element of the present invention, the compound represented by the general formula (1) is preferably used as a luminescent material, but even in that case, it is different from the compound represented by the general formula (1). These light emitting materials can be used in combination. Moreover, in the organic electroluminescent element of the present invention, when the compound represented by the general formula (1) is used as a host material of the light emitting layer, or when used in an organic layer other than the light emitting layer, the general formula ( A light emitting material different from the compound represented by 1) is used for the light emitting layer.
The light emitting material that can be used in the present invention may be any of a phosphorescent light emitting material, a fluorescent light emitting material, and the like. In addition, the light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve color purity or broaden the light emission wavelength region.

Examples of the fluorescent light-emitting material and phosphorescent light-emitting material that can be used in the organic electroluminescent device of the present invention include, for example, paragraphs [0100] to [0164] of JP-A-2008-270736 and JP-A-2007-266458. Paragraph numbers [0088] to [0090] are described in detail, and the matters described in these publications can be applied to the present invention.
Examples of phosphorescent materials that can be used in the present invention include US Pat. No. 6,303,238, US Pat. No. 6,097,147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01/39234. No., WO01 / 41512, WO02 / 02714, WO02 / 15645, WO02 / 44189, WO05 / 19373, JP2001-247859, JP2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, European Patent Publication No. 121112257, JP 2002 -22649 JP, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-173684, JP 2002-203678, JP 2002-203679. And phosphors described in patent documents such as JP-A No. 2004-357991, JP-A 2006-256999, Ir, JP-A No. 2007-19462, JP-A No. 2007-84635, and JP-A No. 2007-96259. Examples of such a light emitting material include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd. Examples include phosphorescent metal complex compounds such as complexes, Dy complexes, and Ce complexes. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.

  The type of fluorescent light-emitting material that can be used in the present invention is not particularly limited, but in addition to the compound represented by the general formula (1), for example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl , Diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran, perinone, oxadiazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed poly Ring aromatic compounds (anthracene, phenanthroline, pyrene, perylene, rubrene, or pentacene), 8-quinolinol metal complexes, various metal complexes represented by pyromethene complexes and rare earth complexes, polythiol Emissions, polyphenylene, polymeric compounds such as polyphenylene vinylene, organic silane, and may be derivatives of these.

In addition, a compound described in [0082] of JP 2010-111620 A can also be used as a light emitting material.
The light emitting layer in the organic electroluminescent element of the present invention may be composed only of a light emitting material, or may be a mixed layer of a host material and a light emitting material. The kind of the light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light-emitting layer, and is a compound that itself does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.

Examples of the host material that can be used in the organic electroluminescence device of the present invention include the following compounds in addition to the compound represented by the general formula (1).
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin-based compound, condensed aromatic hydrocarbon compound (fluorene, naphthalene, phenanthrene, anthracene, triphenylene Etc.), polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, Conductive polymer oligomers such as lithiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, Fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine, 8-quinolinol metal complexes, metal phthalocyanines, metal complexes with benzoxazole and benzothiazole as ligands And various metal complexes and derivatives thereof (which may have a substituent or a condensed ring). In addition, compounds described in [0081] and [0083] of JP-A 2010-111620 can also be used.
Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, condensed ring aromatic hydrocarbon compounds, and metal complexes are preferable, and the condensed ring aromatic hydrocarbon compound is particularly preferable because it is stable. As the condensed aromatic hydrocarbon compound, naphthalene compounds, anthracene compounds, phenanthrene compounds, triphenylene compounds, and pyrene compounds are preferable, anthracene compounds and pyrene compounds are more preferable, and anthracene compounds are particularly preferable.

The light-emitting element of the present invention preferably contains a compound represented by the following general formula (An-1) as a host material.
(In the general formula (An-1), Ar ¹ and Ar ² each independently represent an aryl group or a heteroaryl group, and R ^{301 to} R ³⁰⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ^307, and R ³⁰⁷ and R ³⁰⁸ may be bonded to each other to form a ring.

In general formula (An-1), the aryl group represented by Ar ¹ and Ar ² is preferably an aryl group having 6 to 36 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, An aryl group having 6 to 14 carbon atoms is particularly preferable, and a phenyl group or a naphthyl group is particularly preferable.
The heteroaryl group represented by Ar ¹ and Ar ² is preferably a heteroaryl group having 5 to 20 ring members, and more preferably a heteroaryl group having 5 to 13 ring members. As a hetero atom contained in the heteroaryl group represented by Ar ¹ and Ar ² , a nitrogen atom, an oxygen atom and a sulfur atom are preferable, and a nitrogen atom is more preferable. The number of heteroatoms contained in the heteroaryl group represented by Ar ¹ and Ar ² is preferably 1 to 3, more preferably 1 or 2, and particularly preferably 1. The heteroaryl group represented by Ar ¹ and Ar ² is particularly preferably a pyridyl group, a carbazolyl group, a dibenzofuryl group, or a dibenzothiophenyl group.
Ar ¹ and Ar ² are preferably a phenyl group, a naphthyl group, a pyridyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothiophenyl group, and a group formed by combining these. Ar ¹ and Ar ² are more preferably a phenyl group or a naphthyl group, and at least one of Ar ¹ and Ar ² is particularly preferably a substituted or unsubstituted phenyl group.
Ar ¹ and Ar ² may further have a substituent, such as an aryl group, heteroaryl group, fluorine atom, alkyl group (preferably having 1 to 4 carbon atoms), alkenyl group, A silyl group and a cyano group can be mentioned.

In the general formula (An-1), examples of the substituent represented by R ^{301 to} R ³⁰⁸ include an aryl group, a heteroaryl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a group formed by combining these. Preferably a phenyl group, a naphthyl group, a pyridyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothiophenyl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a combination thereof, and a phenyl group , A naphthyl group, and an alkyl group having 1 to 5 carbon atoms (particularly preferably a tert-butyl group).
In general formula (An-1), R ^{301 to} R ³⁰⁸ may further have a substituent, and examples of the substituent include an aryl group, a heteroaryl group, and an alkyl group. An aryl group is preferable, and an aryl group having 6 to 18 carbon atoms is more preferable.
In general formula (An-1), the number of substituents contained in R ^{301 to} R ³⁰⁸ is preferably 0 to 4, more preferably 0 or 2, and 0 or 1. Is particularly preferable, and 0 is particularly preferable.
In the general formula (An-1), the position of the substituent contained in R ^{301 to} R ³⁰⁸ is preferably R ³⁰² , R ³⁰³ , R ³⁰⁶ or R ³⁰⁷ , and either R ³⁰² and R ³⁰³ or R More preferably, either one of ³⁰⁶ and R ³⁰⁷ is used.
In general formula (An-1), R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ^307, and R ³⁰⁷ and R ³⁰⁸ are bonded to each other to form a ring. However, it is preferred that they are not bonded to each other to form a ring.

The compound represented by the general formula (An-1) is preferably a compound represented by the following (An-2).
(In General Formula (An-2), R ^{301 to} R ³¹⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ R ³⁰⁶ and R ³⁰⁷ , R ³⁰⁷ and R ³⁰⁸ , R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , R ³¹¹ and R ³¹² , R ³¹² and R ³¹³ , R ³¹⁴ and R ³¹⁵ , R ³¹⁵ and R ³¹⁶ , R ³¹⁶ and R ³¹⁷ and R ³¹⁷ and R ³¹⁸ may be bonded to each other to form a ring.)

A preferred range of R ³⁰¹ to R ³⁰⁸ in formula (An-2) are the same as the preferred ranges of R ³⁰¹ to R ³⁰⁸ in formula (An-1).

Examples of the substituent represented by R ^{309 to} R ³¹⁸ in General Formula (An-2) include an aryl group, a heteroaryl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a group formed by combining these. , Preferably an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 20 ring members, a fluorine atom, an alkyl group, an alkenyl group, a silyl group, a cyano group, and a group formed by combining these, more preferably Phenyl group, naphthyl group, pyridyl group, carbazolyl group, dibenzofuryl group, dibenzothiophenyl group, fluorine atom, alkyl group, alkenyl group, silyl group, cyano group, and a combination of these, particularly preferably phenyl Group, naphthyl group and carbazolyl group.
In general formula (An-1), R ^{309 to} R ³¹⁸ may further have a substituent, and examples of the substituent include an aryl group, an alkyl group, a fluorine atom, and the like. May combine with each other to form a ring.
In general formula (An-1), the number of substituents contained in R ^{309 to} R ³¹⁸ is preferably 0 to 4, more preferably 0 or 2, and 0 or 1. Is particularly preferable, and 0 is particularly preferable.
In general formula (An-1), the position of the substituent contained in R ^{309 to} R ³¹⁸ is not particularly limited, but when it has a substituent, it is preferably contained in at least one of R ³¹¹ and R ³¹⁶ .
In general formula (An-1), R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , R ³¹¹ and R ³¹² , R ³¹² and R ³¹³ , R ³¹⁴ and R ³¹⁵ , R ³¹⁵ and R ³¹⁶ , R ³¹⁶ and R ³¹⁷ R ³¹⁷ and R ³¹⁸ may combine with each other to form a ring, and the formed ring is preferably a 5- or 6-membered ring, and more preferably a 5-membered ring.

  Specific examples of the compound represented by the general formula (An-1) are shown below, but the compound represented by the general formula (An-1) that can be used in the present invention is limited by these specific examples. Should not be construed.

  The host material that can be used in the light emitting layer in the organic electroluminescent device of the present invention may be a hole transporting host material or an electron transporting host material.

In the light emitting layer, the singlet minimum excitation energy (S ₁ energy) in the film state of the host material is preferably higher than the S ₁ energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S ₁ is greater than 0.1eV than S ₁ of the light-emitting material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
The host material for S ₁ in the film state of the host material will be quench S ₁ is smaller than the light emission of the light emitting material larger S ₁ is obtained from the luminescent material. Even if the S _{1 of} the host material is larger than the light emitting material, if the S ₁ difference between the two is small, the reverse energy transfer from the light emitting material to the host material occurs in part, resulting in a decrease in efficiency, color purity, and durability. Cause a decline in sex. Therefore, a host material having a sufficiently large S ₁ , high chemical stability and high carrier injection / transport properties is required.

  Further, the content of the host compound in the light emitting layer in the organic electroluminescence device of the present invention is not particularly limited, but is 15 with respect to the total mass of the compound forming the light emitting layer from the viewpoint of light emission efficiency and driving voltage. It is preferable that it is -99 mass%. When the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (An-1), the compound represented by the general formula (An-1) is 50 to 99% by mass or less in the total host compounds. It is preferable that

(Other layers)
The organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The organic electroluminescent element of the present invention preferably comprises (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
The organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
Specifically, an example of a preferred embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. 1, and as the organic layer, a hole injection layer 4, a hole transport layer 5, from the anode 3 side, In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
Hereinafter, other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.

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

(A-1) Hole injection layer, hole transport layer The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.

  The light-emitting element of the present invention preferably includes at least one organic layer between the light-emitting layer and the anode, and the organic layer includes the following general formula (Sa-1), general formula (Sb-1), and general formula ( Among the compounds represented by Sc-1), it is preferable to contain at least one compound.

(Wherein X is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted) Or an unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a group formed by combining these groups, R ^S1 , R ^S2 , R ^S3; Are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, a hydroxy group, and a cyano group Or replace Other represents the unsubstituted amino group. Adjacent R ^S1, R ^S2, R ^S3 each other are bonded to each other, may form a saturated or unsaturated carbon ring .Ar ^S1, Ar ^S2 each independently Represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.)
Wherein R ^S4 , R ^S5 , R ^S6 and R ^S7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. Substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, substituted or unsubstituted carbon Represents a condensed polycyclic group of 5 to 30, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and adjacent R ^S4 , R ^S5 , R ^S6, and R ^S7 are bonded to each other, and are saturated Ar ^S3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
Wherein R ^S8 and R ^S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon, Represents a heterocyclic group having 2 to 30 or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R ^S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted; And an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R ^S11 and R ^S12. Are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, Substituted or unsubstituted aryl having 6 to 30 carbon atoms An oxy group, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group; Adjacent R ^S11 and R ^S12 may be bonded to each other to form a saturated or unsaturated carbocycle, Ar ^S4 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted group, or Represents an unsubstituted heteroaryl group having 2 to 30 carbon atoms, Y ^S1 and Y ^S2 each independently represent a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted carbon number 6 Represents an arylene group of ˜30. N and m each independently represents an integer of 0 to 5.)

The general formula (Sa-1) will be described.
In the general formula (Sa-1), X represents a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 6 to 6 carbon atoms. It represents a 30 arylene group, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a group formed by combining these groups. X is preferably a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, and a substituted or unsubstituted naphthylene, More preferred is substituted or unsubstituted biphenylene.
R ^S1 , R ^S2 and R ^S3 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon atom. An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, a substituted or unsubstituted condensed group having 5 to 30 carbon atoms A cyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group is represented. Adjacent R ^S1 , R ^S2 and R ^S3 may be bonded to each other to form a saturated or unsaturated carbocyclic ring. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R ^S1 , R ^S2 and R ^S3 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number. It is a 5-30 condensed polycyclic group and a cyano group, and more preferably a hydrogen atom.
Ar ^S1 and Ar ^S2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar ^S1 and Ar ^S2 are preferably a substituted or unsubstituted phenyl group.

Next, the general formula (Sb-1) will be described.
In the general formula (Sb-1), R ^S4 , R ^S5 , R ^S6 and R ^S7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number. An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, Alternatively, it represents a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. Adjacent R ^S4 , R ^S5 , R ^S6 and R ^S7 may be bonded to each other to form a saturated or unsaturated carbocycle. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R ^S4 , R ^S5 , R ^S6 and R ^S7 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A condensed polycyclic group having 5 to 30 carbon atoms and a cyano group, more preferably a hydrogen atom.
Ar ^S3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar ^S3 is preferably a substituted or unsubstituted phenyl group.

Next, the general formula (Sc-1) will be described.
In the general formula (Sc-1), R ^S8 and R ^S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, It represents a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms. R ^S8 and R ^S9 are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a methyl group and a phenyl group. It is. R ^S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, It represents an unsubstituted condensed polycyclic group having 5 to 30 carbon atoms. R ^S10 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably a phenyl group. R ^S11 and R ^S12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 6 carbon atoms. 30 aryl groups, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic rings having 2 to 30 carbon atoms, substituted or unsubstituted condensed polycyclic groups having 5 to 30 carbon atoms, It represents a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. Adjacent R ^S11 and R ^S12 may be bonded to each other to form a saturated or unsaturated carbocycle. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R ^S11 and R ^S12 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 5 to 30 carbon atoms. A condensed polycyclic group and a cyano group, and more preferably a hydrogen atom. Ar ^S4 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Y ^S1 and Y ^S2 represent substituted or unsubstituted alkylene having 1 to 30 carbon atoms, or substituted or unsubstituted arylene having 6 to 30 carbon atoms. Y ^S1 and Y ^S2 are preferably substituted or unsubstituted arylene having 6 to 30 carbon atoms, and more preferably substituted or unsubstituted phenylene. n is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 0. m is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 1.

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

(Wherein R ^S1 , R ^S2 and R ^S3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or An unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 5 to 5 carbon atoms 30 represents a condensed polycyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and adjacent R ^S1 , R ^S2 , and R ^S3 are bonded to each other to form a saturated or unsaturated carbocyclic ring. Q ^Sa each independently represents a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or 6 to 30 carbon atoms. Aryloxy group, substituted or unsubstituted It represents an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group.)

The general formula (Sa-2) will be described. R ^S1 , R ^S2 and R ^S3 have the same meanings as those in formula (Sa-1), and preferred ranges are also the same. Q ^Sa each independently represents a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a substituted group. Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group; Q ^Sa is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably A hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom.

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

Wherein R ^S4 , R ^S5 , R ^S6 and R ^S7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. Substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, substituted or unsubstituted carbon Represents a condensed polycyclic group of 5 to 30, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group, and adjacent R ^S4 , R ^S5 , R ^S6 and R ^S7 are bonded to each other to form a saturated carbocyclic ring; Alternatively, an unsaturated carbocycle may be formed, and Q ^Sb is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, carbon number 6-30 aryloxy groups, substituted or Represents an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group.)

The general formula (Sb-2) will be described. R ^S4 , R ^S5 , R ^S6 and R ^S7 have the same meanings as those in formula (Sb-1), and preferred ranges are also the same. Q ^Sa is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted. Represents an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group. Q ^Sa is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably A hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom.

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

Wherein R ^S8 and R ^S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon, Represents a heterocyclic group having 2 to 30 or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R ^S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted; And an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, R ^S11 and R ^S12. Are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, Substituted or unsubstituted aryl having 6 to 30 carbon atoms An oxy group, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group; R ^S11 and R ^S12 adjacent to each other may be bonded to each other to form a saturated or unsaturated carbocycle, and Q ^Sc is a hydrogen atom, a cyano group, a fluorine atom, or an alkoxy having 1 to 30 carbon atoms. Group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Or a substituted or unsubstituted amino group.)

The general formula (Sc-2) will be described. R ^S8 , R ^S9 , R ^S10 , R ^S11 and R ^S12 have the same meanings as those in formula (Sc-1), and preferred ranges are also the same. Q ^Sc is a hydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted. Represents an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted amino group. Q ^Sc is preferably a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a hydrogen atom. A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably a phenyl group.

  Specific examples of the compounds represented by the general formulas (Sa-1), (Sb-1), and (Sc-1) include the following. However, the present invention is not limited to the following specific examples.

  The compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) can be synthesized by the method described in JP-A-2007-318101. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the light emitting device of the present invention, the compound represented by the general formula (Sa-1), (Sb-1), or (Sc-1) is contained in an organic layer between the light emitting layer and the anode. Among them, it is more preferable that it be contained in a layer on the anode side adjacent to the light emitting layer, and a hole transport material contained in the hole transport layer is particularly preferable.
The compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) is preferably contained in an amount of 70 to 100% by mass with respect to the total mass of the organic layer to be added. It is more preferable that 100 mass% is contained.

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

The compound represented by the general formula (M-3) is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited, and the organic layer It may be further contained in any of the layers. As the introduction layer of the compound represented by the general formula (M-3), a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge blocking layer, or a plurality of layers are included. Can be contained.
The organic layer adjacent to the light emitting layer between the light emitting layer and the anode, which contains the compound represented by the general formula (M-3), is more preferably an electron block layer or a hole transport layer.

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

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

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

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

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

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

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

When the compound represented by the general formula (M-3) is used in a hole transport layer, the compound represented by the general formula (M-3) is preferably contained in an amount of 50 to 100% by mass. It is preferable that 80-100 mass% is contained, and it is especially preferable that 95-100 mass% is contained.
Moreover, when using the compound represented by the said general formula (M-3) for a some organic layer, it is preferable to contain in said layer in each layer.

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

  Specific examples of the compound represented by the general formula (M-3) are shown below, but the present invention is not limited thereto.

  In addition, for the hole injection layer and the hole transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention. In addition, the matters described in [0250] to [0339] of JP 2011-71452 A can also be applied to the hole injection layer and the hole transport layer of the present invention. It is also preferable to apply the compound represented by the general formula (1) to the hole injection layer and the hole transport layer.

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

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

(A-2) Electron Blocking Layer The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and still more preferably 5 nm to 50 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
The material used for the electron blocking layer is preferably higher than the S ₁ energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S ₁ is greater than 0.1eV than S ₁ of the light-emitting material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.

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

(B-1) Electron injection layer and electron transport layer The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, for example, a compound represented by the general formula (1) can be used. Other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives. , Fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, Metal complexes of phthalocyanine derivatives and 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands Various metal complexes typified by metal complexes, organosilane derivatives typified by siloles, condensed hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., are preferred, pyridine derivatives, benzimidazole derivatives , An imidazopyridine derivative, a metal complex, or a condensed ring hydrocarbon compound is more preferable.

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

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

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

(B-2) Hole blocking layer The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
The S ₁ energy in the film state of the organic compound constituting the hole blocking layer is higher than the S ₁ energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
As an example of the organic compound constituting the hole blocking layer, for example, a compound represented by the general formula (1) can be used.
Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (iii) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum (iii) bis (2-methyl-8-q
uiolinato) 4-phenylphenolate (abbreviated as BAlq))
Aluminum complexes such as, triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-
And phenanthroline derivatives such as 1,10-phenanthroline (abbreviated as BCP).
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and still more preferably 5 nm to 50 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
The material used for the hole blocking layer is preferably higher than the S ₁ energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S ₁ is greater than 0.1eV than S ₁ of the light-emitting material in the film state of the material used in the hole blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.

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

  The organic electroluminescent device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). It is preferable from the viewpoint of device efficiency and driving voltage. Below, general formula (O-1) is demonstrated.

In (formula (O1), R ^O1 represents an alkyl group, an aryl group, or .A ^O1 to A ^O4 representing the heteroaryl group each independently may .R ^A representing a C-R ^A or a nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different, L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring or a heteroaryl ring; N ^O1 represents an integer of 2 to 6.)

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

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

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

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

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n ^O1 is most preferably 3 in terms of device efficiency, and most preferably 2 in terms of device durability.

  The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stability at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably ˜300 ° C., more preferably 120 ° C. to 300 ° C., and further preferably 140 ° C. to 300 ° C.

  Specific examples of the compound represented by the general formula (O-1) are shown below, but the compound represented by the general formula (O-1) that can be used in the present invention is limitedly interpreted by these specific examples. It will never be done.

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

In the organic electroluminescent device of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the cathode side layer adjacent to the light emitting layer. It is more preferable that it is contained.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (O-1), it is more preferable that 85-100 mass% is contained.

  The organic electroluminescent element of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (P) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (P) is demonstrated.

(In General Formula (P), R ^P represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). And these may have a substituent selected from the aforementioned substituent group A. nP represents an integer of 1 to 10, and when there are a plurality of R ^P , they may be the same or different. At least one of R ^P is a substituent represented by the following general formulas (P-1) to (P-5).

The general formula (P-4) is more preferably the following general formula (P-4 ′).

The general formula (P-5) is more preferably the following general formula (P-5 ′).

(In the general formulas (P-1) to (P-5), R ^{P1 to} R ^P5 , R ′ ^{P1 to} R ′ ^P3 , R ′ ^P5 and R ″ ^P3 are each an alkyl group (preferably having 1 to 8 carbon atoms). , An aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), which may have a substituent selected from the aforementioned substituent group A. n ^P1 , n ^P2 , n ^P4 and n ^P5 represent integers of 0 to 4, n ^P3 and n ^P5 represent integers of 0 to 2, R ^{P1 to} R ^P5 , R ′ ^{P1 to} R ′ ^P3 and R ′ ^When there are a plurality of ^P5 and R ″ ^P3 , they may be the same or different. L ^{P1 to} L ^P5 each represents a divalent linking group consisting of a single bond, an aryl ring or a heteroaryl ring. Represents a bonding position with the anthracene ring of the general formula (P).)

As R ^P , a preferable substituent other than the substituents represented by (P-1) to (P-5) is an aryl group, and more preferably one of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. And more preferably a naphthyl group.
R ^{P1 to} R ^P5 , R ′ ^{P1 to} R ′ ^P3 , R ′ ^P5 and R ″ ^P3 are preferably either an aryl group or a heteroaryl group, more preferably an aryl group, and still more preferably a phenyl group , A biphenyl group, a terphenyl group, or a naphthyl group, and most preferably a phenyl group.
L ^{P1 to} L ^P5 are preferably any of a single bond and a divalent linking group consisting of an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene, or naphthylene, and even more preferably It is either a single bond, phenylene, or naphthylene.

  Specific examples of the compound represented by the general formula (P) are shown below, but the compound represented by the general formula (P) that can be used in the present invention is interpreted in a limited manner by these specific examples. Absent.

  The compound represented by the general formula (P) can be synthesized by the methods described in WO2003 / 060956, WO2004 / 080975, and the like. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent element of the present invention, the compound represented by the general formula (P) is preferably contained in an organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (P), it is more preferable that 85-100 mass% is contained.

  In the organic electroluminescent device of the present invention, other preferable materials used for the electron injection layer and the electron transport layer include, for example, silole compounds described in JP-A-9-194487, JP-A-2006-73581, and the like. Phosphine oxide compounds described in JP-A-2005-276801, JP-A-2006-225320, WO2005 / 085387, etc., nitrogen-containing aromatic hetero 6-membered ring compounds, WO2003 / 080760, WO2005 / 085387 Compounds having a nitrogen-containing aromatic hetero 6-membered structure and a carbazole structure described in Japanese Patent Publication No. Gazette, etc., aromatic hydrocarbon compounds described in US2009 / 0009065, WO2010 / 134350, JP2010-535806, etc. Naphthalene compounds, anthracene Compounds, triphenylene compounds, phenanthrene compounds, pyrene compounds, fluoranthene compounds, etc.), and the like.

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

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

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

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 6% or more, and further preferably 7% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency around 300 to 400 cd / m ² when the device is driven at 20 ° C. Can do.

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

<Emission wavelength>
The organic electroluminescence device of the present invention is not limited in its emission wavelength, but is preferably used for blue or white light emission. Among them, in the organic electroluminescent element of the present invention, it is preferable to emit light using the compound represented by the general formula (1) as a light emitting material, and it is particularly preferable to emit blue light.

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

[Light emitting device]
The light emitting device of the present invention includes the organic electroluminescent element of the present invention.
Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 in FIG. 2 includes a transparent substrate (supporting substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.

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

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

[Lighting device]
The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.
Next, the illumination device of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention. As shown in FIG. 3, the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.

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

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

[Example 1]
<Synthesis Example of Compound 1 used in Examples>
Compound 1 was synthesized by the method described below.

<Synthesis Example of Compound 3 used in Examples>
Compound 3 was synthesized by the method described below. Intermediate a was synthesized with reference to the method described in Journal of Materials Chemistry, 2011, 21 (13), 4918-4926.

<Synthesis Example of Compound 5 used in Examples>
Compound 5 was synthesized by the method described below.

<Synthesis Example of Compound 6 used in Examples>
Compound 6 was synthesized by the method described below.

Each compound obtained above was identified by ¹ H NMR, MS-spectrum.

  Other compounds 2, 4, 7, 8, and 9 were also synthesized and confirmed by a method according to the synthesis of the above compound.

The structural formulas of the compounds used in Examples and Comparative Examples are summarized below.

  Comparative compounds 1 and 2 are described in J. Am. Org. Chem. , 2011, 76 (4), 1054-1061, Comparative Compound 3 is a compound described in EP23089945, and Comparative Compound 4 is International Publication WO2011 / 139129 and JP2009-292760. Comparative compound 5 is a compound described in KR2011123106, Comparative compound 6 is a compound described in JP2002-319490A, and Comparative compound 7 is JP2010-270103A. It is a compound described in the publication.

[Example 2]
<Material property evaluation>
On a quartz glass substrate having a thickness of 0.7 mm and a 2.5 cm square, H-1 and each light emitting material described in Table 1 below were vapor-deposited at a mass ratio (95: 5) by a vacuum vapor deposition method. A thin film having a thickness of 50 nm was formed. The obtained film was irradiated with 350 nm UV light to emit light, and the emission spectrum was measured using a fluorescence spectrophotometer (FP-6300 manufactured by JASCO Corporation), and the emission maximum wavelength (nm) and the spectrum half width. The energy difference (eV) between the short wavelength and the long wavelength, which is 0.5 when the light emission maximum value is 1, was determined. At this time, the emission maximum wavelength was evaluated in three stages according to the following criteria, and the spectrum half width was evaluated in two steps according to the following criteria. Further, chromaticity (x, y) was determined from the emission spectrum (CIE 1931 color system). The y value at this time was evaluated in three stages according to the following criteria. Furthermore, the luminescence quantum yield was measured using spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Table 1 below shows the results of evaluation in three stages according to the following criteria, assuming that the value of the quantum yield of light emission of Comparative Example 2 is 1.0.

(Emission wavelength)
○: 425 nm or more and less than 455 nm Δ: less than 425 nm x: 455 nm or more

(Spectral half width)
○: Less than 0.35 eV ×: 0.35 eV or more

(Color purity)
○: Less than 0.10 Δ: 0.10 or more and less than 0.15 ×: 0.15 or more

(Luminescence efficiency)
○: 1.5 or more Δ: greater than 1.0 and less than 1.5 ×: 1.0 or less

[Example 3]
<Device fabrication and evaluation>
All materials used for device fabrication were purified by sublimation.

A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on this transparent anode (iTO film) by vacuum deposition.
First layer: HAT-CN: film thickness 10 nm
Second layer: HT-1: film thickness 30 nm
Third layer: H-2 and luminescent materials described in Table 2 below (mass ratio 95: 5): film thickness 30 nm
Fourth layer: ET-1: film thickness 30 nm
On this, 1 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order, and it was set as the cathode.
The obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. The organic electroluminescent elements of Comparative Examples 8 to 14 and Examples B1 to B9, in which the light emitting portion was a square of 2 mm × 2 mm, were obtained. The following tests were performed on each of the obtained organic electroluminescent elements. The results of evaluation in terms of color purity and luminous efficiency are shown in Table 2 below.

(A) Color purity Chromaticity (x, y) was determined from the emission spectrum when each organic electroluminescent device was caused to emit light having a luminance of 1000 cd / m ² (CIE 1931 color system). The y value at this time was evaluated in three stages according to the following criteria.
○: Less than 0.10 Δ: 0.10 or more and less than 0.15 ×: 0.15 or more

(B) Luminous efficiency Using a source measure unit 2400 manufactured by Toyo Technica, a direct current voltage was applied to each element to emit light, and the luminance was measured using a luminance meter (BM-8, manufactured by Topcon Corporation). . The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency (η) with a luminance of around 1000 cd / m ² was calculated by the luminance conversion method. In Table 2 below, the value of the external quantum efficiency of Comparative Example 9 was set to 1.0, and evaluation was performed in three stages according to the following criteria.
○: 1.5 or more Δ: greater than 1.0 and less than 1.5 ×: 1.0 or less

[Example 4]
An organic electroluminescent element was produced in the same manner as in Example 3 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 3 was performed. The results are shown in Table 3 below. Note that the luminous efficiencies in Table 3 below are expressed as relative values when the external quantum efficiency of Comparative Example 16 is 1.0.
First layer: HI-1: film thickness 50 nm
Second layer: HT-2: film thickness 45 nm
Third layer: H-3 and light emitting materials described in Table 3 below (mass ratio 95: 5): film thickness 25 nm
Fourth layer: ET-2: film thickness 5 nm
Fifth layer: ET-3: Film thickness 20 nm

From the above Tables 1 to 3, it was found that all of the organic electroluminescent elements using the compounds of the present invention as the luminescent material had high blue purity, a sharp spectrum, and good luminous efficiency.
On the other hand, it turned out that the organic electroluminescent element which used the comparative compounds 1-7 as a luminescent material is inferior to blue purity or luminous efficiency.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ... -Cathode 10 ... Organic electroluminescent element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 31 ··· Transparent substrate 30A · · Light incident surface 30B · · Light exit surface 32 · · · Fine particles 40 · · · Lighting device

Claims (16)

A substrate,
A pair of electrodes arranged on the substrate and comprising an anode and a cathode;
And at least one organic layer including a light emitting layer disposed between the electrodes,
One of the at least one organic layer contains a compound represented by the following general formula (1).
(In the general formula (1), R ^{1 to} R ¹² each independently represents a hydrogen atom or a substituent. R ¹⁰ and R ¹¹ may jointly form a ring, but R ¹¹ and R ¹² are And one of R ⁴ and R ⁵ or R ⁸ and R ⁹ together represents any one of the divalent substituents represented by the following general formulas a to e, However, R ⁴ and R ⁵ , and both sets of R ⁸ and R ⁹ do not jointly form a ring, and R ⁴ and R ⁵ jointly form the following general formula a In the formula, R ³ and R ⁹ represent a substituent other than an unsubstituted phenyl group or a hydrogen atom.
R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group.
X ¹ to X ¹² represents a carbon atom. )
(In the general formulas a to e, * represents a binding site between X ⁴ and X ⁵ or a binding site between X ⁸ and X ^9. R ^{105 to} R ¹⁰⁹ are each independently an alkyl group, an aryl group, or Represents a heteroaryl group.) The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).
(In General Formula (2), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom or a substituent. One set of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the general formulas a to e, and forms a ring, provided that both R ⁴ and R ⁵ , and R ⁸ and R ⁹ are combined. In addition, when R ⁴ and R ⁵ together represent a divalent substituent represented by the following general formula a, R ³ and R ⁹ are other than an unsubstituted phenyl group. Represents a substituent or a hydrogen atom, and when R ⁴ and R ⁵ together represent a divalent substituent represented by the general formula c, R ¹⁵ is other than an aryl group, a heteroaryl group or an arylamino group. Represents a substituent or a hydrogen atom.
R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group.
X ^{1 to} X ⁹ and X ^{12 to} X ¹⁶ each represent a carbon atom . ) The organic electroluminescent element according to claim 1 or 2 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).
(In General Formula (3), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom, an alkyl group or a fluorine atom. One set of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the above general formulas a to e to form a ring, provided that both R ⁴ and R ⁵ and R ⁸ and R ⁹ are combined. Do not jointly form a ring.
R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group. ) The molecular weight of the compound represented by the said General formula (1) is 1200 or less, The organic electroluminescent element as described in any one of Claims 1-3 characterized by the above-mentioned. The organic electroluminescent element according to any one of claims 1 to 4, at least one organic layer containing the compound represented by the general formula (1) is characterized in that said light emitting layer. The organic electroluminescent element according to any one of claims 1 to 5, wherein the compound represented by the general formula (1) is a light-emitting material. The organic electroluminescence device according to any one of claims 1 to 6, at least, characterized in that further comprises a compound represented by the following general formula (An-1) of the organic layer.
(In General Formula (An-1), Ar ¹ and Ar ² each independently represent an aryl group or a heteroaryl group, and R ^{301 to} R ³⁰⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ^307, and R ³⁰⁷ and R ³⁰⁸ may be bonded to each other to form a ring. The organic electroluminescent element according to claim 7 , wherein the compound represented by the general formula (An-1) is a compound represented by the following general formula (An-2).
(In General Formula (An-2), R ^{301 to} R ³¹⁸ each independently represent a hydrogen atom or a substituent. R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰³ and R ³⁰⁴ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ³⁰⁷ , R ³⁰⁷ and R ³⁰⁸ , R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , R ³¹¹ and R ³¹² , R ³¹² and R ³¹³ , R ³¹⁴ and R ³¹⁵ , R ³¹⁵ and R ³¹⁶ , R ³¹⁶ and R ³¹⁷ and R ³¹⁷ and R ³¹⁸ may combine with each other to form a ring.) The organic electroluminescence device according to claim 7 or 8 at least one organic layer containing the compound represented by the general formula (An-1) is characterized in that it is a light emitting layer. A light emitting device using the organic electroluminescent element according to any one of claims 1-9. A display device using an organic electroluminescent element according to any one of claims 1-9. An illumination device using the organic electroluminescent element according to any one of claims 1-9. A compound represented by the following general formula (1):
(In the general formula (1), R ¹ ~ R ¹² Each independently represents a hydrogen atom or a substituent. R ¹⁰ And R ¹¹ May jointly form a ring, but R ¹¹ And R ¹² Do not jointly form a ring. R ⁴ And R ⁵ Or R ⁸ And R ⁹ One of the groups together represents any one of divalent substituents represented by the following general formulas a to e to form a ring. However, R ⁴ And R ⁵ And R ⁸ And R ⁹ Neither pair forms a ring together. R ⁴ And R ⁵ Together represent a divalent substituent represented by the following general formula a: ³ And R ⁹ Represents a substituent other than an unsubstituted phenyl group or a hydrogen atom.
R ¹⁰¹ ~ R ¹⁰⁴ Each independently represents an alkyl group, an aryl group or a heteroaryl group.
X ¹ ~ X ¹² Represents a carbon atom. )
(In general formulas a to e, * indicates X ⁴ And X ⁵ Binding site or X ⁸ And X ⁹ Represents the binding site. R ¹⁰⁵ ~ R ¹⁰⁹ Each independently represents an alkyl group, an aryl group or a heteroaryl group. ) The compound represented by following General formula (3).
(In General Formula (3), R ^{1 to} R ⁹ and R ^{12 to} R ¹⁶ each independently represent a hydrogen atom, an alkyl group or a fluorine atom. One set of R ⁴ and R ⁵ or R ⁸ and R ⁹ is It represents any one of the divalent substituents represented by the following general formulas a to e to form a ring, provided that R ⁴ and R ⁵ , and both R ⁸ and R ⁹ are combined. Do not jointly form a ring.
R ^{101 to} R ¹⁰⁴ each independently represents an alkyl group, an aryl group, or a heteroaryl group. )
(In the general formulas a to e, * represents a binding site between X ⁴ and X ⁵ or a binding site between X ⁸ and X ^9. R ^{105 to} R ¹⁰⁹ are each independently an alkyl group, an aryl group, or Represents a heteroaryl group.) The organic electroluminescent element material which consists of a compound of Claim 13 or 14 . The organic electroluminescent element material according to claim 15 , which is a light emitting material.