JP6100476B2 - ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ORGANIC ELECTROLUMINESCENT ELEMENT - Google Patents

Description

  The present invention relates to an organic electroluminescent element and an organic electroluminescent element material used therefor. 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 color purity and high luminous efficiency is important for application to full-color displays, and various development research results have been reported so far.

  As a material for such an organic electroluminescent device, Patent Document 1 discloses that a naphthalene ring and an aryl group substituted at the 1,5-position of the naphthalene ring are saturated and condensed through an oxygen atom, a nitrogen atom, or a sulfur atom. The compound of the structure is described, and it is described that luminous efficiency is high and durability is high. Patent Document 2 describes a compound in which three aromatic rings are condensed at two positions via a nitrogen atom, and describes that blue light emission luminance and color purity can be improved. Although Patent Document 2 describes a compound in which an amino group is substituted on an aromatic ring, it has not been specifically implemented.

On the other hand, compounds having a structure similar to the compounds described in Patent Documents 1 and 2 are also known in the technical field of organic transistor materials. For example, in Patent Documents 3 and 4, a compound having a structure in which a naphthalene ring and an aryl group substituted at the 2- and 6-positions of the naphthalene ring are saturated and condensed via an oxygen atom, a nitrogen atom, or a sulfur atom, It is described that it shows high carrier mobility as an organic transistor material. Patent Documents 3 and 4 do not describe compounds in which an amino group is substituted on an aryl group substituted at the 2,6-position of the naphthalene ring, and whether the compounds described in these documents can be applied to organic electroluminescence devices. It was not mentioned.
Patent Document 5 discloses a compound having a structure in which a naphthalene ring and an aryl group substituted at the 2- and 6-positions of the naphthalene ring are saturated and condensed via an oxygen atom, a nitrogen atom, or a sulfur atom. It describes that it is excellent in storage stability. Patent Document 5 did not describe a compound in which an amino group was substituted on an aryl group substituted at the 2,6-position of the naphthalene ring.

EP2145936 KR2011-041726 International Publication No. WO2011 / 074231 International Publication No. WO2011 / 074232 JP 2010-087408 A

Under such circumstances, the present inventors examined an organic electroluminescent device using the compound described in Patent Document 1 as a luminescent material. From the viewpoint of blue purity, although high efficiency was obtained. It has been found that dissatisfaction sometimes remains and that the chromaticity after drive deterioration changes. When the present inventors examined the organic electroluminescent element using the compound which substituted the amino group on the aromatic ring which was described in patent document 2, but was not implemented concretely as a luminescent material, it was blue. It was found that dissatisfaction remained from the viewpoint of emission luminance and blue purity. Moreover, when the present inventors examined using the compound described in patent documents 3 and 4 as a luminescent material of an organic electroluminescent element, it turned out that sufficient luminescent property is not obtained.
The present invention aims to solve the above problems. That is, the problem to be solved by the present invention is to provide an organic electroluminescence device having high luminous efficiency, excellent blue purity, and little chromaticity change after driving deterioration.

  As a result of diligent investigations by the present inventors to solve the above-mentioned problems, the naphthalene ring and the aryl group substituted at the 2- and 6-positions of the naphthalene ring are saturated and condensed through an oxygen atom, a nitrogen atom or a sulfur atom. In addition, it was found that the above problem can be solved by using a compound having an amino group on the aryl group substituted at the 2,6-position of the naphthalene ring.

The invention which is a specific means for solving the problems of the present invention is as follows.
[1] A substrate, a pair of electrodes disposed 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. An organic electroluminescent device comprising a compound represented by formula (1).
(In the formula, R ^{1 to} R ⁴ each independently represents a substituent, and at least one of R ³ and R ⁴ is a substituent represented by the following general formula (2). A and b are each independent. 1 to 4 and when a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different, and W, X, Y and Z are each independently O, S or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group and a heteroaryl group) u, m, p and q each independently represent 0 or 1, and m + u = 1 P + q = 1, j and k each independently represent an integer of 0 to 2.)
(In the formula, A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ¹ represents an arylene group or a heteroarylene group. A ¹ and A ² , L ¹ and A ¹ And L ¹ and A ² may combine with each other to form a ring, n represents 0 or 1, and when n is 0,-(L ¹ ) _n- represents a single bond.)
[2] In the organic electroluminescent element according to [1], the compound represented by the general formula (1) is preferably a compound represented by the following general formula (3).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group and Represents any of a heteroaryl group.) U, m, p and q each independently represent 0 or 1, m + u = 1, p + q = 1, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group A ³ and A ⁴ , L ² and a ^3, L ² and a ^4, a ⁵ and a ^6, L ³ and a ⁵ Contact Fine L ³ and A ⁶ are bonded to each represents good .s and t to form a ring independently 0 or 1 to each other, when s or t is 0 - (L ²⁾ _s - or - ( L ³ ) _t − represents a single bond.
[3] In the organic electroluminescence device according to [1] or [2], the compound represented by the general formula (3) is preferably a compound represented by the following general formula (4).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group and Represents any of a heteroaryl group.) U, m, p and q each independently represent 0 or 1, m + u = 1, p + q = 1, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group A ³ and A ⁴ , L ² and a ^3, L ² and a ^4, a ⁵ and a ^6, L ³ and a ⁵ Contact Fine L ³ and A ⁶ are bonded to each represents good .s and t to form a ring independently 0 or 1 to each other, when s or t is 0 - (L ²⁾ _s - or - ( L ³ ) _t − represents a single bond.
[4] In the organic electroluminescent element according to [3], the compound represented by the general formula (4) is preferably a compound represented by the following general formula (5).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and X and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group). J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)
[5] In the organic electroluminescent element according to [3], the compound represented by the general formula (4) is preferably a compound represented by the following general formula (6).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and W and Y each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)
[6] In the organic electroluminescent element according to [3], the compound represented by the general formula (4) is preferably a compound represented by the following general formula (7).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)
[7] In the organic electroluminescent element according to [4], the compound represented by the general formula (5) is preferably a compound represented by the following general formula (8).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and X and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group). J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)
[8] In the organic electroluminescent element according to [7], the compound represented by the general formula (8) is preferably a compound represented by the following general formula (11).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[9] In the organic electroluminescent element according to [7], the compound represented by the general formula (8) is preferably a compound represented by the following general formula (12).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[10] In the organic electroluminescent element according to [7], the compound represented by the general formula (8) is preferably a compound represented by the following general formula (13).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring. .)
[11] In the organic electroluminescent element according to [7], the compound represented by the general formula (8) is preferably a compound represented by the following general formula (20).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group, j and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring.
[12] In the organic electroluminescent element according to [7], the compound represented by the general formula (8) is preferably a compound represented by the following general formula (21).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group, j and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring.
[13] In the organic electroluminescent element according to [5], the compound represented by the general formula (6) is preferably a compound represented by the following general formula (9).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and W and Y each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)
[14] In the organic electroluminescent device according to [13], the compound represented by the general formula (9) is preferably a compound represented by the following general formula (14).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[15] In the organic electroluminescent element according to [13], the compound represented by the general formula (9) is preferably a compound represented by the following general formula (15).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[16] In the organic electroluminescent device according to [13], the compound represented by the general formula (9) is preferably a compound represented by the following general formula (16).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, R ⁷ and R ⁸ each independently represents an alkyl group, an aryl group or a heteroaryl group, j and k are each independently 0 Represents an integer of ˜2, A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ are bonded to each other to form a ring; May be.)
[17] In the organic electroluminescent element according to [6], the compound represented by the general formula (7) is preferably a compound represented by the following general formula (10).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)
[18] In the organic electroluminescent element as described in [17], the compound represented by the general formula (10) is preferably a compound represented by the following general formula (17).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[19] In the organic electroluminescent element according to [17], the compound represented by the general formula (10) is preferably a compound represented by the following general formula (18).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
[20] In the organic electroluminescent device according to [17], the compound represented by the general formula (10) is preferably a compound represented by the following general formula (19).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring. .)
[21] In the organic electroluminescent element according to any one of [1] to [20], at least one organic layer containing the compound represented by the general formula (1) is preferably a light emitting layer. .
[22] In the organic electroluminescent element according to [21], the light emitting layer preferably contains an anthracene host material.
[23] In the organic electroluminescent element according to [22], the anthracene-based host material is preferably represented by the following general formula (An-1).
(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.
[24] In the organic electroluminescent element according to [23], 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.)
[25] The organic electroluminescent element according to any one of [1] to [24] preferably includes a compound represented by the following general formula (P) in at least one layer of the organic layer.
(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). These may have a substituent, nP represents an integer of 1 to 10, and when R ^P is plural, they may be the same or different, and at least one of R ^P is (It is a substituent represented by the following general formulas (P-1) to (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, n ^{P1 to} n ^P2 , n ^P4 , n ^P5 represents an integer of 0 to 4, n ^P3 and n ^P5 represent an integer of 0 to 2, and R ^{P1 to} R ^P5 , R ′ ^{P1 to} R ′ ^P3 , R ′ ^P5 , and R ″ ^P3 are plural L ^{P1 to} L ^{P5 each} represents a single bond, a divalent linking group consisting of an aryl ring or a heteroaryl ring, * represents an anthracene ring of the general formula (P) Represents the bond position with
[26] In the organic electroluminescent element according to [25], the compound represented by the general formula (P) is a substituent represented by the general formula (P-1) as at least one of R ^P. It is preferable that it is a compound which has this.
[27] In the organic electroluminescent element according to [25], the compound represented by the general formula (P) is a substituent represented by the general formula (P-2) as at least one of R ^P. It is preferable that it is a compound which has this.
[28] In the organic electroluminescent element according to [25], the compound represented by the general formula (P) is a substituent represented by the general formula (P-3) as at least one of R ^P. It is preferable that it is a compound which has this.
[29] In the organic electroluminescent element as described in [25], the compound represented by the general formula (P) is a substituent represented by the general formula (P-4) as at least one of R ^P. It is preferable that it is a compound which has this.
[30] In the organic electroluminescent device according to [25], the compound represented by the general formula (P) is a substituent represented by the general formula (P-5) as at least one of R ^P. It is preferable that it is a compound which has this.
[31] In the organic electroluminescent element according to any one of [1] to [30], at least one organic layer containing the compound represented by the general formula (1) is formed by a vacuum deposition process. It is preferable that
[32] In the organic electroluminescent element according to any one of [1] to [30], at least one organic layer containing the compound represented by the general formula (1) is formed by a wet process. It is preferable to become.
[33] A light-emitting device, display device, or illumination device using the organic electroluminescence element according to any one of [1] to [32].
[34] A material for an organic electroluminescent element represented by the following general formula (1).
(In the formula, R ^{1 to} R ⁴ each independently represents a substituent, and at least one of R ³ and R ⁴ is a substituent represented by the following general formula (2). A and b are each independent. 1 to 4 and when a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different, and W, X, Y and Z are each independently O, S or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group and a heteroaryl group) u, m, p and q each independently represent 0 or 1, and m + u = 1 P + q = 1, j and k each independently represent an integer of 0 to 2.)
(In the formula, A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ¹ represents an arylene group or a heteroarylene group. A ¹ and A ² , L ¹ and A ¹ And L ¹ and A ² may combine with each other to form a ring, n represents 0 or 1, and when n is 0,-(L ¹ ) _n- represents a single bond.)
[35] The organic electroluminescent element material according to [34] is preferably represented by the following general formula (3).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group and Represents any of a heteroaryl group.) U, m, p and q each independently represent 0 or 1, m + u = 1, p + q = 1, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group A ³ and A ⁴ , L ² and a ^3, L ² and a ^4, a ⁵ and a ^6, L ³ and a ⁵ Contact Fine L ³ and A ⁶ are bonded to each represents good .s and t to form a ring independently 0 or 1 to each other, when s or t is 0 - (L ²⁾ _s - or - ( L ³ ) _t − represents a single bond.

  The organic electroluminescence device of the present invention has high luminous efficiency, excellent blue purity, and little chromaticity change after driving deterioration. 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 chromaticity.

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.
In the present invention, when used in the description of each general formula without distinction, a hydrogen atom includes an isotope (deuterium atom, etc.), and an atom constituting a substituent further includes the isotope. This means that

[Organic electroluminescent elements, materials for organic electroluminescent elements]
The light emitting material for an organic electroluminescent element of the present invention is represented by the following general formula (1).
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, The organic layer contains a compound represented by the following general formula (1).
(In the formula, R ^{1 to} R ⁴ each independently represents a substituent, and at least one of R ³ and R ⁴ is a substituent represented by the following general formula (2). A and b are each independent. 1 to 4 and when a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different, and W, X, Y and Z are each independently O, S or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group and a heteroaryl group) u, m, p and q each independently represent 0 or 1, and m + u = 1 P + q = 1, j and k each independently represent an integer of 0 to 2.)
(In the formula, A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ¹ represents an arylene group or a heteroarylene group. A ¹ and A ² , L ¹ and A ¹ And L ¹ and A ² may combine with each other to form a ring, n represents 0 or 1, and when n is 0,-(L ¹ ) _n- represents a single bond.)

<Structure of organic electroluminescent element material>
Below, the structure of the compound represented by General formula (1) which is a luminescent material for organic electroluminescent elements of this invention, and the other structure of the organic electroluminescent element of this invention are demonstrated in detail.

In the general formula (1), R ^{1 to} R ⁴ each independently represent a substituent, and at least one of R ³ and R ⁴ is a substituent represented by the following general formula (2).
Examples of the substituent other than that represented by the general formula (2) represented by R ^{1 to} R ⁴ include an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group, and a cyano group.
R ^{1 to} R ⁴ may be bonded to each other to form a ring, but R ^{1 to} R ⁴ are preferably not bonded to each other to form a ring.

In the general formula (1), R ¹ and R ² are more preferably an alkyl group, an aryl group or a silyl group from the viewpoint of suppressing the association and increasing the blue purity, and particularly preferably an alkyl group and an aryl group. An isopropyl group, a tert-butyl group, and a phenyl group are more preferable. On the other hand, from the viewpoint of adjusting the emission wavelength of the organic electroluminescence device using the compound represented by the general formula (1), it is preferable that at least one of R ¹ and R ² is an aryl group or a heteroaryl group. An aryl group is more preferable, an aryl group having 6 to 10 carbon atoms is particularly preferable, and a phenyl group is particularly preferable. R ¹ and R ² may further have a substituent, and the substituent on the aryl group is preferably an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a cyano group.

  In the general formula (1), j and k each independently represent an integer of 0 to 2, and each independently preferably represents 0 or 1.

In the general formula (1), R ³ and R ⁴ are both represented by the general formula (2) from the viewpoint of high blue purity by spectral sharpening and high emission efficiency and high durability of an organic EL device by optimization of ionization potential. It is preferable that it is a substituent represented by these.

In the general formula (1), a and b each independently represent 1 to 4, preferably each independently 1 or 2, and particularly preferably 1 each independently.
When a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different.

In the substituent represented by the general formula (2), A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ¹ and A ² , L ¹ and A ¹ and L ¹ and A ² may be bonded to each other to form a ring. A ¹ and A ² are preferably each independently an aryl group or a heteroaryl group, more preferably an aryl group, more preferably an aryl group having 6 to 10 carbon atoms, a phenyl group or 2 -More preferably, it is a naphthyl group.
A ¹ and A ² may have a further substituent, and the further substituent is preferably an alkyl group, an aryl group or a fluorine atom, more preferably an alkyl group having 1 to 5 carbon atoms, a phenyl group or a fluorine atom. A methyl group is preferable, and a methyl group is particularly preferable. When A ¹ and A ² have further substituents, the number of further substituents is preferably 1 to 3 per A ¹ and A ² , more preferably 1 or 2, more preferably 1 It is particularly preferred that

In the substituent represented by the general formula (2), L ¹ represents an arylene group or a heteroarylene group, and is preferably an arylene group having 6 to 10 carbon atoms or a heteroarylene group having 6 to 10 ring members, A phenylene group, a pyridinyl group or a pyrimidinyl group is more preferable, and a phenylene group is particularly preferable.

  In the substituent represented by the general formula (2), n represents 0 or 1, and is preferably 0.

In General Formula (1), W, X, Y, and Z each independently represent O, S, or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group, and a heteroaryl group).
R ⁹ is preferably an aryl group, and more preferably a phenyl group. R ⁹ may have a further substituent, and the further substituent is preferably an alkyl group, a silyl group, an aryl group or a fluorine atom, more preferably an alkyl group having 1 to 5 carbon atoms, a phenyl group or a fluorine atom. A methyl group is preferable, and a methyl group is particularly preferable. The number of further substituents that R ⁹ has is preferably 0 to 3, and more preferably 0 to 2.

  In general formula (1), u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.

In the organic electroluminescent element material of the present invention, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (3).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group and Represents any of a heteroaryl group.) U, m, p and q each independently represent 0 or 1, m + u = 1, p + q = 1, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group A ³ and A ⁴ , L ² and a ^3, L ² and a ^4, a ⁵ and a ^6, L ³ and a ⁵ Contact Fine L ³ and A ⁶ are bonded to each represents good .s and t to form a ring independently 0 or 1 to each other, when s or t is 0 - (L ²⁾ _s - or - ( L ³ ) _t − represents a single bond.

A preferred range of R ¹ and R ² in the general formula (3) is the same as the preferred ranges of R ¹ and R ² in the general formula (1).
The preferable range of j and k in General formula (3) is the same as the preferable range of j and k in General formula (1).

Preferred ranges of R ⁵ and R ⁶ in the general formula (3) are the same as the preferred ranges of substituents other than those represented by the general formula (2) represented by R ³ and R ⁴ in the general formula (1). .
In general formula (3), c and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different. . c and d are preferably each independently 0 or 1, and more preferably 0.

  Preferred ranges of W, X, Y and Z in the general formula (3) are the same as the preferred ranges of W, X, Y and Z in the general formula (1).

In General Formula (3), A ^{3 to} A ⁶ each independently represent an alkyl group, an aryl group, or a heteroaryl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. The preferred ranges of A ³ and A ⁴ in the general formula (3) are the same as the preferred ranges of A ¹ and A ² in the general formula (2), and the preferred ranges of A ⁵ and A ⁶ in the general formula (3) are also general. This is the same as the preferred range of A ¹ and A ² in Formula (2).
In General Formula (3), L ² and L ³ each independently represent an arylene group or a heteroarylene group. The preferred range of L ² and L ³ in the general formula (3) is the same as the preferred range of L ¹ in the general formula (2). A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
In general formula (3), m and t each independently represents 0 or 1. The preferred ranges of s and t in general formula (3) are the same as the preferred ranges of n in general formula (2).

In the organic electroluminescent element of the present invention, the compound represented by the general formula (3) is preferably a compound represented by the following general formula (4).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group and Represents any of a heteroaryl group.) U, m, p and q each independently represent 0 or 1, m + u = 1, p + q = 1, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group A ³ and A ⁴ , L ² and a ^3, L ² and a ^4, a ⁵ and a ^6, L ³ and a ⁵ Contact Fine L ³ and A ⁶ are bonded to each represents good .s and t to form a ring independently 0 or 1 to each other, when s or t is 0 - (L ²⁾ _s - or - ( L ³ ) _t − represents a single bond.
For the explanation and preferred range of each atom and substituent of the general formula (4), the corresponding explanation and preferred range of the general formula (3) can be referred to.

  In the organic electroluminescent element material of the present invention, the compound represented by the general formula (4) is preferably a compound represented by any one of the following general formulas (5) to (7). A compound represented by (5) or (6) is more preferred, and a compound represented by the following general formula (5) is particularly preferred.

(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and X and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group). J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)

(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and W and Y each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)

(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ represent Each independently represents an arylene group or a heteroarylene group, A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ , They may combine with each other to form a ring, and s and t each independently represents 0 or 1; , S or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond.)

(Compound represented by the general formula (5))
First, the compound represented by the general formula (5) will be described.
For the explanation and preferred range of each atom and substituent of the general formula (5), the corresponding explanation and preferred range of the general formula (3) can be referred to. Furthermore, in the general formula (5), when j is 1, and R ¹ represents an alkyl group or a silyl group, R ¹ is substituted with a carbon atom adjacent to the carbon atom having X in the benzene ring substituted by R ^1. There preferably in terms of that heat resistance which is substituted, if R ¹ represents an aryl group and R ¹ is a substituted carbon atom that is not next to a carbon atom having an X in the benzene ring to which R ¹ is substituted It is preferable from the viewpoint of color purity. When k is 1 and R ² represents an alkyl group or a silyl group, R ² is substituted on the carbon atom adjacent to the carbon atom having Z in the benzene ring substituted by R ² . preferably in the aspect, preferable from the viewpoint that R ² is substituted at the carbon atom that is not next to a carbon atom of the color purity with Z in the benzene ring to which R ² is replaced when R ² represents an aryl group . The preferred wavelength can be adjusted as appropriate depending on the types of R ¹ and R ² and the combination of the substitution positions and A ^{3 to} A ⁶ .

The compound represented by the general formula (5) is preferably a compound represented by the following general formula (8).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and X and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group). J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)

  For the explanation and preferred range of each atom and substituent of the general formula (8), the corresponding explanation and preferred range of the general formula (5) can be referred to.

The compound represented by the general formula (8) is preferably a compound represented by any one of the following general formulas (11) to (13), (20) and (21).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring. .)
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group, j and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group, j and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring.

For the explanation and preferred ranges of the atoms and substituents of the general formulas (11) to (13), (20) and (21), the corresponding explanation and preferred range of the general formula (5) can be referred to.
Among the compounds represented by the general formulas (11) to (13), (20) and (21), the compounds represented by the general formulas (11) to (13) are preferable, and the general formulas (11) or (12) ) Is more preferable, and a compound represented by the general formula (11) is particularly preferable.

(Compound represented by the general formula (6))
Secondly, the compound represented by the general formula (6) will be described.
For the explanation and preferred range of each atom and substituent of the general formula (6), the corresponding explanation and preferred range of the general formula (3) can be referred to.

The compound represented by the general formula (6) is preferably a compound represented by the following general formula (9).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ⁵ or R ⁶ may be the same or different, and W and Y each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)

  For the explanation and preferred range of each atom and substituent of the general formula (9), the corresponding explanation and preferred range of the general formula (6) can be referred to.

The compound represented by the general formula (9) is preferably a compound represented by any one of the following general formulas (14) to (16).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, R ⁷ and R ⁸ each independently represents an alkyl group, an aryl group or a heteroaryl group, j and k are each independently 0 Represents an integer of ˜2, A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ are bonded to each other to form a ring; May be.)

For the explanation and preferred ranges of the atoms and substituents of the general formulas (14) to (16), the corresponding explanation and preferred range of the general formula (3) can be referred to.
Among the compounds represented by the general formulas (14) to (16), the compound represented by the general formula (14) or (15) is preferable, and the compound represented by the general formula (14) is more preferable.

(Compound represented by the general formula (7))
Third, the compound represented by the general formula (7) will be described.
For the explanation and preferred range of each atom and substituent of the general formula (7), the corresponding explanation and preferred range of the general formula (3) can be referred to.

The compound represented by the general formula (7) is preferably a compound represented by the following general formula (10).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents an alkyl group, an aryl group or a heteroaryl group) J and k each independently represents an integer of 0 to 2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.)

  For the explanation and preferred range of each atom and substituent of the general formula (10), the corresponding explanation and preferred range of the general formula (3) can be referred to.

The compound represented by the general formula (10) is preferably a compound represented by any one of the following general formulas (17) to (19).
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and j and k each independently represent an integer of 0 to 2. A ^{3 to} A ⁶ are each independently an aryl group, heteroaryl group or Represents an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring.
(In the formula, R ¹ , R ² , R ⁵ and R ⁶ each independently represents a substituent. C and d each independently represent an integer of 0 to 3, and when c or d is 2 or more, R ^{5 and} R ⁶ may be the same or different, and R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group, j and k each independently represent 0-2. A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may combine with each other to form a ring. .)

For the explanation and preferred ranges of the atoms and substituents of the general formulas (17) to (19), the corresponding explanation and preferred range of the general formula (3) can be referred to.
Among the compounds represented by the general formulas (17) to (19), the compound represented by the general formula (17) or (18) is preferable, and the compound represented by the general formula (17) is more preferable.

<Characteristics of the compound represented by the general formula (1)>
The maximum emission wavelength of the organic electroluminescence device using the compound represented by the general formula (1) is usually less than 455 nm. Preferably it is 400 nm or more and less than 455 nm, More preferably, it is 420 nm or more and less than 455 nm, More preferably, it is 430 nm or more and less than 455 nm, Most preferably, it is 440 nm or more and less than 455 nm from a viewpoint of obtaining blue light emission with high color purity.

  The compound represented by the general formula (1) preferably has a molecular weight of 1000 or less, more preferably 900 or less, particularly preferably 850 or less, and further preferably 800 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) (meaning a 10 mass% reduction temperature in the present specification) is preferably 300 ° C., more preferably 285 ° C. or less, and further preferably 270. It is below ℃.

  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.

The compound represented by the general formula (1) can be synthesized by combining the methods described in WO2011 / 074231, WO2011 / 074232, EP2145936, KR20111041726, and other known reactions. Below, the typical example of the specific synthetic | combination procedure of the compound represented by General formula (1) is described. In the following synthesis scheme examples, the TfO- group represents a trifluoromethanesulfonyloxy group, the Lv group represents a leaving group such as Br, Cl, and -OTf, the Ac group represents an acetyl group, and Ar is an arbitrary group. Represents an aryl group, R represents an arbitrary substituent, and X represents O, S, or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group, and a heteroaryl group).

(Synthesis scheme example 1)

(Synthesis scheme example 2)

(Synthesis scheme example 3)

Synthetic intermediates having various substituents can be synthesized by combining known reactions. The reaction at each stage is as follows. Each substituent may be introduced at any intermediate stage.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

  The light emitting material for an organic electroluminescent element represented by the general formula (1) has a maximum emission wavelength of preferably less than 455 nm, more preferably 400 nm or more and less than 455 nm, and 420 nm or more and less than 455 nm. Is particularly preferably 430 nm or more and less than 455 nm, and most preferably 440 nm or more and less than 455 nm.

[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, The organic layer contains a compound represented by the following general formula (1).
The structure of the organic electroluminescent element of the present invention is not particularly limited. In FIG. 1, an example of a structure of the organic electroluminescent element of this invention is shown. 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 an application.

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

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

The compound represented by the general formula (1) is preferably contained in the light emitting layer in the organic layer disposed between the electrodes among the organic layers disposed between the electrodes of the organic electroluminescent element. .
The compound represented by the general formula (1) may be contained in another organic layer of the organic electroluminescent element 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. A block layer (a hole block layer, an electron block layer, etc.) can be mentioned, and preferably an exciton block layer, a charge block layer, an electron transport layer, or an electron injection layer, more preferably an exciton. Block layer, charge blocking layer, or electron transport layer.

  The compound represented by the general formula (1) is preferably contained in an amount of 0.1 to 100% by mass, more preferably 0.1 to 50% by mass, based on the total mass of the light emitting layer. More preferably, it is contained in an amount of ˜20% by mass, and more preferably in an amount of 0.5-10% by mass.

  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 included in an amount of 70 to 100% by mass with respect to the total mass of the organic layer. It is preferable that 85-100 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 light emitting layer disposed between the pair of electrodes is preferably formed by forming the light emitting layer by a vacuum deposition process or a wet process, and the light emitting layer includes at least one layer of the light emitting layer. More preferably, it is formed by vapor deposition of a composition containing the 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 300 nm, more preferably 5 nm to 100 nm, and more preferably 10 nm to 50 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. preferable. There is no restriction | limiting in particular in the host material used for the said 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 this invention, when using the compound represented by the said General formula (1) as a host material of a light emitting layer, or when using it for organic layers other than a light emitting layer, the said general formula ( A light emitting material different from the compound represented by 1) may be 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. Phosphorescent light emitting compounds described in patent literatures such as JP-A No. 2004-357991, JP-A 2006-256999, JP-A 2007-19462, JP-A 2007-84635, and JP-A 2007-96259. Among them, more preferable light emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Examples thereof include phosphorescent metal complex compounds such as 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 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.

(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.
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 compound, condensed aromatic hydrocarbon compound (fluorene, naphthalene, phenanthrene, triphenylene, etc.) , Polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, polythiophene Conductive polymer oligomer, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandi Oxides, carbodiimides, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles, Examples thereof include various metal complexes represented by metal complexes having benzothiazol as a ligand 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, a condensed ring aromatic hydrocarbon compound, and a metal complex are preferable, and a 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. As the anthracene-based compound, those described in [0033] to [0064] of WO2010 / 134350 are particularly preferable, and examples thereof include compounds H-1, H-2, and H-4 described below.

The organic electroluminescent 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 the 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. 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 combination thereof, and more 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, an alkenyl group, a silyl group, a cyano group, and a combination thereof, particularly preferably a phenyl group, A naphthyl group and a 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.

The organic electroluminescent element of the present invention is represented by any one of the general formulas (1) to (21) and any one of the general formulas (An-1) and (An-2). A combination of compounds is preferably used for the light emitting layer.
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 lower efficiency, lower 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 -98 mass%, and it is more preferable that it is 80-99 mass%. When the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (1), the compound represented by the general formula (1) may be 50 to 99% by mass or less in the total host compounds. preferable.

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

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

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

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

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

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

When the compound represented by the general formula (M-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.

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 complexes such as Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
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 a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). 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.

<< 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.

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., still more preferably 120 ° C. to 300 ° C., and still more 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 layer on the cathode side 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.

The organic electroluminescent element of the present invention uses a compound represented by any one of the general formulas (1) to (21) as a luminescent material, and as R ^P , (P-1) to (P-5) A combination in which the compound represented by the general formula (P) having a substituent represented by any one is used in at least one organic layer between the light emitting layer and the cathode is preferable.
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 fluorescent 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 illumination device of the present invention includes the organic electroluminescent element of the present 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 of Organic Electroluminescent Device Material Represented by General Formula (1)>
Synthesis Example 1 Synthesis of Compound 1

(Synthesis of Compound 1a)
According to the synthesis method of WO2011 / 074231, the compound 1a was synthesized from the above starting materials.

(Compound 1b)
Compound 1a (27.6 g), 1-bromo-2-fluoro-4-nitrobenzene (manufactured by Tokyo Chemical Industry) (52.8 g), sodium carbonate (70 g) in DME / water (200 ml / 100 ml) with 5 mol% Pd ( PPh ₃ ) ₄ was added, and the mixture was stirred at 80 ° C. for 12 hours under a nitrogen atmosphere. The reaction solution was poured into ethyl acetate / dilute hydrochloric acid (mixing ratio: ethyl acetate / dilute hydrochloric acid = 1/1), and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography to obtain Compound 1b (28 g).

(Synthesis of Compound 1c)
To a dichloromethane solution (200 ml) of compound 1b (28 g), 1 MBBr ₃ in dichloromethane (132 ml) was added dropwise and stirred at room temperature for 3 hours. The reaction solution was poured into ethyl acetate / water, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography to obtain Compound 1c (23.7 g).

(Synthesis of Compound 1d)
An NMP solution (400 ml) of compound 1c (22 g) and potassium carbonate (27.6 g) was stirred at 170 ° C. for 8 hours. The reaction solution was allowed to cool, and the precipitated solid was collected by filtration. The obtained crude crystal was washed with water and purified by repeating recrystallization to obtain Compound 1d (11.3 g).

(Synthesis of Compound 1e)
Reduced iron (9.8 g), ammonium chloride (1.3 g), IPA (130 ml) / water (13 ml) were stirred with heating under reflux for 1 hour, and compound 1d (10 g) was added in portions. After stirring for 2 hours, the reaction solution was filtered through Celite, and water was poured into the obtained filtrate. The precipitated solid was collected by filtration, and the crude crystal was purified by recrystallization to obtain Compound 1e (7.8 g).

(Synthesis of Compound 1)
To a xylene solution (100 ml) of compound 1e (6.7 g), tBuONa (4.6 g) and iodobenzene (manufactured by Wako Pure Chemical Industries, Ltd.) (17.1 g) under a nitrogen atmosphere, Pd ₂ (dba) ₃ (0.37 g ) And tritertiary butylphosphine (0.16 g) were added, and the mixture was stirred at 100 ° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and the concentrated residue was purified by silica gel column chromatography to obtain Compound 1 (9.5 g).
The obtained compound was identified by elemental analysis, NMR and MASS spectrum.

(Synthesis of other compounds)
Compounds 1, 2, 4, 6, 7, 13, 14, 16, 17, 19, 20, 23, 24, 29, 32, 34, 39, 40, 43, 45, 60, 63, used in Examples 67, 70, 73 and 79 were also synthesized in a similar manner to compound 1.

<Material property evaluation>
(Test Example 1) Evaluation of chromaticity Mass of the following host material H-5 and each light-emitting material described in Table 1 below on a quartz glass substrate of 25 mm × 25 mm × 0.7 mm by vacuum deposition. A thin film having a thickness of 50 nm was formed by vapor deposition so as to have a ratio (99: 1). 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 chromaticity (x, y). Asked. Based on the y value at this time, the chromaticity was evaluated in the following four stages.
◎ 0.03 ≦ y ≦ 0.08
○ 0.025 ≦ y <0.03, 0.08 <y ≦ 0.10
Δ 0.02 ≦ y <0.025, 0.10 <y ≦ 0.12
X y <0.02, 0.12 <y

(Test Example 2) Evaluation of association formation property The chromaticity was measured using the emission spectrum of a thin film formed so that the mass ratio of the host material H-5 to the light emitting material described in Table 1 below was 95: 5. (X, y) was determined. The chromaticity difference between the y value at this time and the y value of the chromaticity (x, y) of the emission spectrum obtained in Test Example 1 was calculated and evaluated in the following four stages.
◎ Chromaticity difference ≤ 0.02
○ 0.02 <Chromaticity difference ≦ 0.05
Δ 0.05 <chromaticity difference ≦ 0.10
× 0.10 <chromaticity difference

(Test Example 3) Evaluation of Quantum Yield The PL quantum yield of the thin film produced in Test Example 2 was measured using an absolute PL quantum yield measuring apparatus (C9920-02, manufactured by Hamamatsu Photonics Co., Ltd.). The quantum yield at this time was evaluated in the following four stages.
◎ 0.9 ≦ φPL
○ 0.7 ≦ φPL <0.9
△ 0.5 ≦ φPL <0.7
× φPL <0.5

(Test Example 4) Evaluation of orientation The host compound H-5 and the light emitting material were deposited on a 25 mm × 25 mm × 0.7 mm quartz glass substrate by a vacuum deposition method so as to have a mass ratio (95: 5). To form a film. The degree of orientation of the luminescent material was calculated as the degree of horizontal alignment order S by polarized ATR-IR analysis, and was evaluated in the following four stages.
◎ 0.8 ≦ S
○ 0.7 ≦ S <0.8
Δ0.5 ≦ S <0.7
× S <0.5

(Test Example 5) Evaluation of heat resistance 10 mg of the light-emitting material was weighed on a φ5 mm glass tube, decompressed to 0.05 Pa with a vacuum pump, and then sealed with a gas burner. The temperature of the muffle furnace was set to a temperature 50 ° C. higher than the sublimation temperature of the luminescent material measured by vacuum TG-DTA, and the sealed glass tube was heated for 24 hours. The HPLC purity before and after aging was measured and evaluated in the following three stages.
○ 90% ≦ remaining rate △ 70% ≦ remaining rate <90%
× Residual rate <70%

Comparative materials 1 to 12 used as comparative light-emitting materials in Table 1 below have the following structure.

<Production and evaluation of organic electroluminescence device>
All the materials used for the production of the organic electroluminescence device were subjected to sublimation purification, and it was confirmed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z) that the purity (254 nm absorption intensity area ratio) was 99.9% or more. .

The structure of a material other than the light emitting material used in the manufacture of the organic electroluminescent element in each example and comparative example is shown below.

[Example 2]
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
In addition, the vapor deposition rate in the following examples and comparative examples is 0.1 nm / second unless otherwise specified. The deposition rate was measured using a quartz resonator. The thickness of each layer below was measured using a quartz resonator.
First layer: HAT-CN: film thickness 10 nm
Second layer: HT-2: film thickness 60 nm
Third layer: H-1 and luminescent materials described in Table 2 below (mass ratio = 97: 3): film thickness 30 nm
Fourth layer: ET-1: Liq = 1: 1: Film thickness 20 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. At this time, a patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed on the lithium fluoride layer, and metallic aluminum was deposited.
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. Then, organic electroluminescent elements 1-1 to 1-39 having a light emitting portion of 2 mm × 2 mm square and comparative organic electroluminescent elements 1-1 to 1-12 were obtained. In each element, light emission derived from the light emitting material was observed. The following tests were performed on each organic electroluminescent element obtained.

(A) External quantum efficiency Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage is applied to each element to emit light, and the luminance is measured using a luminance meter (BM-8, manufactured by Topcon Corporation). did. 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, and expressed as a relative value with the value of the organic electroluminescent element using Comparative Compound 8 being 1.0. A larger number indicates that the efficiency is better.

(B) Chromaticity Chromaticity (x, y) was determined from the emission spectrum when each organic electroluminescent element was made to emit light by applying a DC voltage so that the luminance was 1000 cd / m ² . The chromaticity was evaluated in the following four steps from the y value at this time.
◎ 0.03 ≦ y ≦ 0.08
○ 0.025 ≦ y <0.03, 0.08 <y ≦ 0.10
Δ 0.02 ≦ y <0.025, 0.10 <y ≦ 0.12
X y <0.02, 0.12 <y

(C) Chromaticity after drive deterioration Chromaticity (x) when each organic electroluminescent element is continuously caused to emit light by applying a DC voltage so that the luminance becomes 1000 cd / m ² , and the luminance decreases to 500 cd / m ² ', Y') was determined from the emission spectrum. From the change Δy (= | y′−Δy |) of the y value before and after the drive deterioration, the chromaticity change after the drive deterioration was evaluated in the following three stages.
○ Δy ≦ 0.01
Δ 0.01 <Δy ≦ 0.02
× 0.02 <Δy

[Example 3]
An organic electroluminescent element was produced in the same manner as in Example 2 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 2 was performed. The results are shown in Table 3 below. In addition, the external quantum efficiency of the following Table 3 is displayed as a relative value when the external quantum efficiency of the organic electroluminescent element using the comparative compound 8 is 1.0.
First layer: HT-4: film thickness 50 nm
Second layer: HT-3: Film thickness 45 nm
Third layer: H-2 and light emitting materials described in Table 3 below (mass ratio = 95: 5): film thickness 25 nm
Fourth layer: ET-5: film thickness 5 nm
Fifth layer: ET-3: Film thickness 20 nm

[Example 4]
An organic electroluminescent element was produced in the same manner as in Example 2 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 2 was performed. The results are shown in Table 4 below. In addition, the external quantum efficiency of the following Table 4 is displayed as a relative value when the external quantum efficiency of the organic electroluminescent element using the comparative compound 8 is 1.0.
First layer: HAT-CN: film thickness 10 nm
Second layer: HT-2: film thickness 30 nm
Third layer: H-1 and luminescent materials described in Table 4 below (mass ratio = 97: 3): film thickness 30 nm
Fourth layer: ET-4: Film thickness 30 nm

[Example 5]
An organic electroluminescent element was produced in the same manner as in Example 2 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 2 was performed. The results are shown in Table 5 below. In addition, the external quantum efficiency of the following Table 5 is displayed as a relative value when the external quantum efficiency of the organic electroluminescent element using the comparative compound 8 is 1.0.
First layer: HAT-CN: film thickness 10 nm
Second layer: HT-1: film thickness 30 nm
Third layer: H-3 and luminescent materials described in Table 5 below (mass ratio = 93: 7): film thickness 30 nm
Fourth layer: ET-4: Film thickness 30 nm

(Example 6)
An organic electroluminescent element was produced in the same manner as in Example 2 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 2 was performed. The results are shown in Table 6 below. In addition, the external quantum efficiency of the following Table 6 is displayed as a relative value when the external quantum efficiency of the organic electroluminescent element using the comparative compound 8 is 1.0.
First layer: HAT-CN: film thickness 10 nm
Second layer: HT-2: film thickness 60 nm
Third layer: H-4 and luminescent materials described in Table 6 below (mass ratio = 97: 3): film thickness 30 nm
Fourth layer: ET-2: film thickness 20 nm

[Example 7]
(Evaluation of organic electroluminescence device (coating))
-Preparation of coating solution for forming light emitting layer-
Compound 14 (0.03% by mass) and the following host material PH-1 (0.97% by mass) were mixed with methyl ethyl ketone (99.0% by mass) to obtain a light emitting layer forming coating solution 1.

Luminescent layer forming coating solutions 2 to 5 were prepared in the same manner as the luminous layer forming coating solution 1, except that the compound 14 in the luminous layer forming coating solution 1 was changed to compounds 16, 17, 20, and 74, respectively.
Further, in the light emitting layer forming coating solutions 1 to 5, the light emitting layer forming coating solution is the same as the light emitting layer forming coating solutions 1 to 5 except that the host material PH-1 is changed to the host material H-2. 6-10 were prepared respectively.
For comparison, a comparative light emitting layer forming coating solution 1 was prepared in the same manner as the light emitting layer forming coating solution 1 except that the compound 14 in the light emitting layer forming coating solution 1 was changed to the comparative compound 8. The comparative light emitting layer forming coating solution 2 was prepared in the same manner as the light emitting layer forming coating solution 1 except that the compound 14 in the light emitting layer forming coating solution 6 was changed to the comparative compound 8.

(Element fabrication procedure)
-Fabrication of organic electroluminescence device-
A transparent support substrate was formed by depositing ITO to a thickness of 150 nm on a 25 mm × 25 mm × 0.7 mm glass substrate. This transparent support substrate was etched and washed.
On this ITO glass substrate, 2 parts by mass of PTPDES-2 (manufactured by Chemipro Kasei, Tg = 205 ° C.) represented by the following structural formula was dissolved in 98 parts by mass of cyclohexanone for electronics industry (manufactured by Kanto Chemical), and the thickness was about After spin coating (2,000 rpm, 20 seconds) to 40 nm, a hole injection layer was formed by drying at 120 ° C. for 30 minutes and annealing at 160 ° C. for 10 minutes.

On the hole injection layer, the light emitting layer forming coating solution 1 was spin-coated (1,300 rpm, 30 seconds) so as to have a thickness of about 40 nm to obtain a light emitting layer.
Next, BAlq (bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminum (III)) represented by the following structural formula is formed on the light emitting layer as an electron transporting layer. It formed by the vacuum evaporation method so that it might become 40 nm.

On the electron transport layer, lithium fluoride (LiF) was formed as an electron injection layer by a vacuum deposition method so as to have a thickness of 1 nm. Furthermore, 70 nm of metal aluminum was vapor-deposited to make a cathode.
The laminate produced as described above is placed in a glove box substituted with argon gas, and sealed using a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, an organic electroluminescent element P1 was produced.

Organic electroluminescent devices P2 to P10 were produced in the same manner as the organic electroluminescent device P1, except that the coating solution 1 for forming the luminescent layer was changed to 2 to 10 in the organic electroluminescent device P1.
For comparison, in the organic electroluminescent element P1, the organic electroluminescence was the same as the organic electroluminescent element P1 except that the light emitting layer forming coating solution 1 was changed to the comparative light emitting layer forming coating solutions 1 and 2, respectively. Elements P11 and P12 were produced.

  Evaluation similar to Example 2 was performed about produced organic electroluminescent element P1-P12. The results are shown in Table 7 below. In addition, the external quantum efficiency of the following Table 7 is displayed by the relative value when the external quantum efficiency of the organic electroluminescent element using the comparative compound 1 for each type of each host material is 1.0.

From the results of Tables 2 to 7, it was found that the organic electroluminescent device of the present invention using the compound of the present invention has high luminous efficiency, excellent blue purity, and little chromaticity change after driving deterioration. .
On the other hand, although the naphthalene ring and the aryl group substituted at the 2,6-position of the naphthalene ring are saturated condensed via an oxygen atom, nitrogen atom or sulfur atom, the aryl substituted at the 2,6-position of the naphthalene ring Each comparison element using Comparative Compound 1 described in International Publication WO2011 / 074231, and Comparative Compound 4 described in International Publication WO2011 / 074232, which has no amino group on the group and has an alkyl group Were found to be inferior in luminous efficiency and inferior in chromaticity.
On the aryl group substituted at the 2,6-position of the naphthalene ring, although the naphthalene ring and the aryl group substituted at the 2,6-position of the naphthalene ring are saturated condensed via an oxygen atom, nitrogen atom or sulfur atom Instead, each comparison using Comparative Compounds 2 and 3 described in International Publication WO2011 / 074231, which has an amino group on the naphthalene ring, or Comparative Compound 5 described in International Publication WO2011 / 074232. It was found that all the elements were inferior in luminous efficiency at least.
On the aryl group substituted at the 2,6-position of the naphthalene ring, although the naphthalene ring and the aryl group substituted at the 2,6-position of the naphthalene ring are saturated condensed via an oxygen atom, nitrogen atom or sulfur atom It was found that Comparative Compound 6 described in KR2011-041726 which does not have an amino group and has a halogen atom is inferior in luminous efficiency.
It was found that the comparative compound 7 described in KR2011-041726 in which the central skeleton is not a naphthalene ring but a pyrene ring is inferior in chromaticity and in chromaticity change after driving deterioration.
Each of the comparison elements using Comparative Compounds 8 to 12 described in EP 2145936 in which an aryl group is substituted at the 1 and 5 positions of the naphthalene ring, not at the 2 and 6 positions of the naphthalene ring, is at least a color after driving deterioration. It turned out that it is inferior to a degree change.

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 (35)

A substrate,
A pair of electrodes disposed on the substrate, including an anode and a cathode;
And at least one organic layer including a light emitting layer disposed between the electrodes,
The organic layer contains a compound represented by the following general formula (1).
(Wherein R ^{1 to} R ⁴ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group , and at least one of R ³ and R ⁴ is represented by the following general formula (2 ).
a and b each independently represent 1 to 4, and when a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different.
W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group and a heteroaryl group).
u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.
j and k each independently represents an integer of 0 to 2. )
(In the formula, A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ¹ represents an arylene group or a heteroarylene group. A ¹ and A ² , L ¹ and A ¹ L ¹ and A ² may be bonded to each other to form a ring.
n represents 0 or 1, and when n is 0,-(L ₁ ) _n- represents a single bond. ) 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 (3).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group and a heteroaryl group).
u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. ) The organic electroluminescent element according to claim 1 or 2, wherein the compound represented by the general formula (3) is a compound represented by the following general formula (4).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group and a heteroaryl group).
u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. ) The organic electroluminescent element according to claim 3, wherein the compound represented by the general formula (4) is a compound represented by the following general formula (5).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
X and Z each independently represent O, S, or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group, and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. ) The organic electroluminescent element according to claim 3, wherein the compound represented by the general formula (4) is a compound represented by the following general formula (6).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
W and Y each independently represent O, S, or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group, and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. ) The organic electroluminescence device according to claim 3, wherein the compound represented by the general formula (4) is a compound represented by the following general formula (7).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. ) The organic electroluminescent element according to claim 4, wherein the compound represented by the general formula (5) is a compound represented by the following general formula (8).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
X and Z each independently represent O, S, or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group, and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ 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 (8) is a compound represented by the following general formula (11).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ 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 (8) is a compound represented by the following general formula (12).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescence device according to claim 7, wherein the compound represented by the general formula (8) is a compound represented by the following general formula (13).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ 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 (8) is a compound represented by the following general formula (20).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ 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 (8) is a compound represented by the following general formula (21).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
R ⁷ represents any of an alkyl group, an aryl group, and a heteroaryl group.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 5, wherein the compound represented by the general formula (6) is a compound represented by the following general formula (9).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
W and Y each independently represent O, S, or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group, and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 13, wherein the compound represented by the general formula (9) is a compound represented by the following general formula (14).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 13, wherein the compound represented by the general formula (9) is a compound represented by the following general formula (15).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 13, wherein the compound represented by the general formula (9) is a compound represented by the following general formula (16).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
R ⁷ and R ⁸ each independently represents an alkyl group, an aryl group, or a heteroaryl group.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 6, wherein the compound represented by the general formula (7) is a compound represented by the following general formula (10).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any of an alkyl group, an aryl group and a heteroaryl group).
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 17, wherein the compound represented by the general formula (10) is a compound represented by the following general formula (17).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 17, wherein the compound represented by the general formula (10) is a compound represented by the following general formula (18).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. ) The organic electroluminescent element according to claim 17, wherein the compound represented by the general formula (10) is a compound represented by the following general formula (19).
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
R ⁷ and R ^{8 each} represents an alkyl group, an aryl group, or a heteroaryl group.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and A ³ and A ⁴ and A ⁵ and A ⁶ may be bonded to each other to form a ring. )   21. The organic electroluminescent element according to claim 1, wherein at least one organic layer containing the compound represented by the general formula (1) is a light emitting layer.   The organic electroluminescent device according to claim 21, wherein the light emitting layer contains an anthracene-based host material. The organic electroluminescent element according to claim 22, wherein the anthracene-based host material is represented by the following general formula (An-1).
(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. The organic electroluminescent device according to claim 23, wherein the compound represented by the general formula (An-1) is a compound represented by the following general formula (An-2).
(In the 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. ) The organic electroluminescent element according to claim 1, wherein a compound represented by the following general formula (P) is contained in at least one layer of the organic layer.
(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). These may have a substituent, nP represents an integer of 1 to 10, and when R ^P is plural, they may be the same or different, and at least one of R ^P is (It is a substituent represented by the following general formulas (P-1) to (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, n ^{P1 to} n ^P2 , n ^P4 , n ^P5 represents an integer of 0 to 4, n ^P3 and n ^P5 represent an integer of 0 to 2, and R ^{P1 to} R ^P5 , R ′ ^{P1 to} R ′ ^P3 , R ′ ^P5 , and R ″ ^P3 are plural L ^{P1 to} L ^{P5 each} represents a single bond, a divalent linking group consisting of an aryl ring or a heteroaryl ring, * represents an anthracene ring of the general formula (P) Represents the bond position with The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-1) as at least one of R ^P. Organic electroluminescent element. 26. The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-2) as at least one of R ^P. Organic electroluminescent element. The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-3) as at least one of R ^P. Organic electroluminescent element. The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-4) as at least one of R ^P. Organic electroluminescent element. The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-5) as at least one of R ^P. Organic electroluminescent element.   The organic electroluminescent element according to any one of claims 1 to 30, wherein at least one organic layer containing the compound represented by the general formula (1) is formed by a vacuum deposition process. .   The organic electroluminescent device according to any one of claims 1 to 30, wherein at least one organic layer containing the compound represented by the general formula (1) is formed by a wet process.   A light-emitting device, a display device, or an illumination device using the organic electroluminescent element according to any one of claims 1 to 32. An organic electroluminescent element material represented by the following general formula (1):
(Wherein R ^{1 to} R ⁴ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group , and at least one of R ³ and R ⁴ is represented by the following general formula (2 ).
a and b each independently represent 1 to 4, and when a or b is 2 or more, a plurality of R ³ or R ⁴ may be the same or different.
W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group and a heteroaryl group).
u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.
j and k each independently represents an integer of 0 to 2. )
(In the formula, A ¹ and A ² each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ¹ represents an arylene group or a heteroarylene group. A ¹ and A ² , L ¹ and A ¹ L ¹ and A ² may be bonded to each other to form a ring.
n represents 0 or 1, and when n is 0,-(L ¹ ) _n- represents a single bond. ) The organic electroluminescent element material according to claim 34, which is represented by the following general formula (3):
(Wherein R ¹ , R ² , R ⁵ and R ⁶ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or a cyano group .
c and d each independently represents an integer of 0 to 3. When c or d is 2 or more, a plurality of R ⁵ or R ⁶ may be the same or different.
W, X, Y and Z each independently represent O, S or N—R ⁹ (R ⁹ represents any one of an alkyl group, an aryl group and a heteroaryl group).
u, m, p and q each independently represent 0 or 1, and m + u = 1 and p + q = 1.
j and k each independently represents an integer of 0 to 2.
A ^{3 to} A ⁶ each independently represents an aryl group, a heteroaryl group or an alkyl group, and L ² and L ³ each independently represent an arylene group or a heteroarylene group. A ³ and A ⁴ , L ² and A ³ , L ² and A ⁴ , A ⁵ and A ⁶ , L ³ and A ^5, and L ³ and A ⁶ may be bonded to each other to form a ring.
s and t each independently represent 0 or 1, and when s or t is 0,-(L ² ) _s-or- (L ³ ) _t- represents a single bond. )