JP2016216411A - Compound, organic electroluminescent element, and electronic apparatus - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound which maintains the luminous efficiency and life of an organic EL element and also can reduce its drive voltage, and an organic EL element prepared with the compound.SOLUTION: The present invention provides a compound represented by formula (1), and an organic EL element prepared with the compound [Ais an aromatic hydrocarbon group with 6-30 ring forming carbons, or a heterocyclic group with 5-30 ring forming atoms; Z is formula (2) or formula (3); Xis O or S; Xis CRRor SiRR].SELECTED DRAWING: None

Description

  The present invention relates to a compound, an organic electroluminescence element, and an electronic device.

  Organic electroluminescence devices using organic substances (hereinafter sometimes abbreviated as “organic EL devices”) are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made. ing. In general, an organic EL element includes a light emitting layer and a pair of counter electrodes (anode and cathode) sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. When electrons and holes recombine in the light emitting layer, an excited state is generated. Energy when returning from the excited state to the ground state is emitted as light.

  Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic light-emitting diodes. In recent organic EL devices, compounds used for forming an organic layer have been improved (for example, see Patent Documents 1 to 3).

International Publication No. 2012/036482 US Patent Application Publication No. 2014/0191208 Korean Published Patent No. 10-2015-0012835

  In order to further improve the performance of the organic EL element, it is desired to reduce the driving voltage while maintaining the light emission efficiency and the lifetime.

  An object of the present invention is to provide a compound capable of lowering the driving voltage while maintaining the light emission efficiency and lifetime of the organic EL element, an organic electroluminescence element using the compound, and an electronic device including the organic electroluminescence element. Is to provide.

  According to one embodiment of the present invention, a compound represented by the following general formula (1) is provided.

In the general formula (1),
A ₁ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
L ₁ and L ₂ are each independently a single bond or a linking group,
L ₁ and L ₂ as a linking group are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms. Group,
R ₁ and R ₂ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming carbon. An aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 3 carbon atoms 20 alkylthio groups, substituted or unsubstituted alkylsilyl groups having 1 to 60 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 60 ring carbon atoms, halogen atoms, cyano groups, substituted phosphoryl groups, substituted A group consisting of a carbonyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. Is a group et selected,
a is an integer of 0 or more and 7 or less, and the plurality of R ₁ may be the same or different from each other;
b is an integer greater than or equal to 0, and several R < ₂ > may mutually be same or different,
when a is an integer of 2 or more, R ₁ may be bonded to each other to form a saturated or unsaturated ring;
When b is an integer of 2 or more, R ₂ may be bonded to each other to form a saturated or unsaturated ring,
Z is a substituent represented by the following general formula (2) or (3).

In the general formula (2), X ₂ is O or S;
In the general formula (3), X ₃ is CR ₅ R ₆ or SiR ₇ R ₈ .
In the general formula (2) or the general formula (3),
R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 1 to 20 alkoxy groups, substituted or unsubstituted aralkyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted 6 to 30 ring carbon atoms An arylthio group, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, Halogen atom, cyano group, substituted phosphoryl group, substituted carbonyl group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substituted or unsubstituted ring former Is a group selected from the group consisting of heterocyclic group having from 5 to 30,
c and d are each independently an integer of 0 to 9,
Several R < ₃ > may mutually be same or different,
Several R < ₄ > may mutually be same or different,
* Indicates a binding position with the _{L 2.}

  According to one embodiment of the present invention, the organic layer includes a cathode, an anode, and an organic layer provided between the cathode and the anode. The organic layer includes at least a light-emitting layer, and the organic layer The organic electroluminescent element in which at least 1 layer contains the compound which concerns on 1 aspect of this invention mentioned above is provided.

  According to one aspect of the present invention, there is provided an electronic apparatus including the organic electroluminescence element according to one aspect of the present invention.

  According to one aspect of the present invention, the organic EL device includes a compound capable of reducing the driving voltage while maintaining the light emission efficiency and lifetime of the organic EL device, the organic electroluminescence device using the compound, and the organic electroluminescence device. An electronic device can be provided.

It is a figure which shows schematic structure of an example of the organic EL element which concerns on one Embodiment.

〔Compound〕
The compound according to this embodiment is represented by the following general formula (1).

In the general formula (1),
A ₁ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
L ₁ and L ₂ are each independently a single bond or a linking group,
L ₁ and L ₂ as a linking group are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms. Group,
R ₁ and R ₂ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming carbon. An aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 3 carbon atoms 20 alkylthio groups, substituted or unsubstituted alkylsilyl groups having 1 to 60 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 60 ring carbon atoms, halogen atoms, cyano groups, substituted phosphoryl groups, substituted A group consisting of a carbonyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. Is a group et selected,
a is an integer of 0 or more and 7 or less, and the plurality of R ₁ may be the same or different from each other;
b is an integer of 0 or more, preferably an integer of 0 or more and 5 or less, and the plurality of R ₂ may be the same or different from each other;
when a is an integer of 2 or more, R ₁ may be bonded to each other to form a saturated or unsaturated ring;
When b is an integer of 2 or more, R ₂ may be bonded to each other to form a saturated or unsaturated ring,
Z is a substituent represented by the following general formula (2) or (3). R ₁ is bonded to the carbon atom of the carbazole ring represented by the general formula (1). The bonding site of R ₁ is the same in the following general formula.

In the general formula (2), X ₂ is O or S.
In the general formula (3), X ₃ is CR ₅ R ₆ or SiR ₇ R ₈ .
In the general formula (2) or the general formula (3), R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ are each independently substituted or unsubstituted 1 to 20 carbon atoms. Aliphatic hydrocarbon group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms An oxy group, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 60 carbon atoms, substituted or Unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, halogen atom, cyano group, substituted phosphoryl group, substituted carbonyl group, substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms Hydrocarbon group, and a group selected from the group consisting of substituted or unsubstituted heterocyclic group ring atoms 5 to 30,
c and d are each independently an integer of 0 to 9,
Several R < ₃ > may mutually be same or different,
Several R < ₄ > may mutually be same or different,
* Indicates a binding position with the _{L 2.} R ₃ is bonded to the carbon atom of the condensed ring represented by the general formula (2), and R ₄ is bonded to the carbon atom of the condensed ring represented by the general formula (3). The bonding positions of R ₃ and R ₄ are the same in the following general formula.

  The compound according to this embodiment is also preferably represented by the following general formula (4).

(In the general formula (4), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c are respectively in the general formula (1) or (2). It is synonymous with definition.)

  The compound according to this embodiment is also preferably represented by the following general formula (5).

(In the general formula (5), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are: Each has the same definition as in general formula (1) or (3).)

    The compound according to this embodiment is also preferably represented by the following general formula (6).

(In the general formula (6), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c are respectively in the general formula (1) or (2). It is synonymous with definition.)

  The compound according to this embodiment is also preferably represented by the following general formula (7).

(In the general formula (7), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are: Each has the same definition as in general formula (1) or (3).)

In the present embodiment, L ₂ is preferably a single bond.

  The compound according to this embodiment is also preferably represented by the following general formula (8).

(In the general formula (8), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c have the same definitions as in the general formula (1) or (2), respectively. .)

  The compound according to this embodiment is also preferably represented by the following general formula (9).

(In the general formula (9), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c have the same definitions as in the general formula (1) or (2), respectively. .)

  The compound according to this embodiment is also preferably represented by the following general formula (10).

(In the general formula (10), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are (It is synonymous with the definition in Formula (1) or (3).)

  The compound according to this embodiment is also preferably represented by the following general formula (11).

(In the general formula (11), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are (It is synonymous with the definition in Formula (1) or (3).)

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (12).

(In the general formula (12), Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are each independently a carbon atom bonded to a nitrogen atom, CR ₂ or L ₁ , and Y ₁ either to Y ₆ is a carbon atom bonded to the L _1, a plurality of R ₂ may be the same or different from each other, combined with R ₂ together, to form a saturated or unsaturated ring The saturated or unsaturated ring may have a substituent, and * represents the bonding position with L _1. )

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (13).

(In the general formula (13), Y ₃ , Y ₄ , Y ₅ , Y ₆ , Y ₇ , Y ₈ , Y ₉ and Y ₁₀ are each independently a carbon atom bonded to a nitrogen atom, CR ₂ or L _1. Any one of Y _{3 to} Y ₁₀ is a carbon atom bonded to L ₁ , and a plurality of R _{2 s} may be the same or different from each other, and R ₂ is bonded to each other to be saturated or unsaturated; And a saturated or unsaturated ring may have a substituent, and * represents a bonding position with L _1. )

In the compound according to this embodiment, at least one of Y _{3 to} Y ₁₀ is preferably a nitrogen atom.

In the compounds according to the present _embodiment, any of Y 3 _{to Y 10,} a carbon atom bonded to the _{L 1,} at least two of Y 3 _{to Y 10} is a nitrogen _atom, Y 3 _{to Y 10} others of is also preferably a CR _2.

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (14).

(In the general formula (14), any one of Y _{3 to} Y ₆ is a carbon atom bonded to L ₁ ,
At least two of Y _{3 to} Y ₆ are nitrogen atoms, Y _{7 to} Y ₁₀ are each independently a nitrogen atom or CR ₂ , and * represents a bonding position with L ₁ . )

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (15).

(In the general formula (15), Y _{6 to} Y ₁₀ are each independently a nitrogen atom or CR ₂ , and * represents a bonding position with L _1. )

In the present embodiment, A ₁ is also preferably a group selected from the group consisting of groups represented by the following general formulas (101) to (133), for example.

(In the general formulas (101) to (133), R _{101 to} R ₁₁₅ are each independently a hydrogen atom or R ₂ , and R ₂ is synonymous with the definition in the general formula (1). R _{2 in the above} may be the same as or different from each other, and * represents the bonding position with L _1. )

In A ₁ of the compound according to the present embodiment, at least one of Y _{1 to} Y ₆ is a nitrogen atom, and any of Y _{1 to} Y ₆ is a carbon atom bonded to L ₁ , and Y ₁ to The remainder of Y ₆ is CR _{2 and} it is also preferred that no ring is formed by the bond between R ₂ .

In the compound according to this embodiment, at least two of Y ₁ , Y ₃ , and Y ₅ are nitrogen atoms, and any of Y ₂ , Y ₄ , and Y ₆ is a carbon atom that binds to L _1. And the remainder of Y ₂ , Y ₄ , and Y ₆ is CR ₂ , and it is also preferable that no ring is formed by the bond between R ₂ .

In the present embodiment, A ₁ is also preferably a group selected from the group consisting of groups represented by the following general formulas (134) to (143), for example.

(In the general formulas (134) to (143), R _{201 to} R ₂₀₄ are each independently a hydrogen atom or R ₂ , and R ₂ is synonymous with the definition in the general formula (1). R _{2 in the above} may be the same as or different from each other, and * represents the bonding position with L _1. )

In the compound according to this embodiment, Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are carbon atoms bonded to CR ₂ or L _1, and any of Y _{1 to} Y ₆ is It is a carbon atom bonded to L ₁ , and a plurality of R ₂ may be the same or different from each other, and it is preferable that R ₂ is bonded to each other to form a saturated or unsaturated ring. The unsaturated ring may have a substituent.

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (16).

(In the general formula (16), Y ₃ , Y ₄ , Y ₅ , Y ₆ , Y ₇ , Y ₈ , Y ₉ and Y ₁₀ are each independently a carbon atom bonded to CR ₂ or L ₁ . , Y _{3 to} Y ₁₀ are carbon atoms bonded to L ₁ , and a plurality of R ₂ may be the same or different from each other, and R ₂ is bonded to each other to form a saturated or unsaturated ring. And a saturated or unsaturated ring may have a substituent, and * represents a bonding position with L _1. )

In the compound according to this embodiment, A ₁ is also preferably represented by the following general formula (17a) or the following general formula (17b).

(In the general formula (17a), Y _{4 to} Y ₉ are each independently a carbon atom bonded to CR ₂ or L ₁ , and Y ₁₁ , Y ₁₂ , Y ₁₃ , and Y ₁₄ are CR ₂ . And any one of Y _{4 to} Y ₉ is a carbon atom bonded to L ₁ ;
In the general formula (17b), Y _{4 to} Y ₉ are CR ₂ , and Y ₁₁ , Y ₁₂ , Y ₁₃ , and Y ₁₄ are each independently a carbon atom bonded to CR ₂ or L ₁ . , Y _{11 to} Y ₁₄ are carbon atoms bonded to L ₁ ,
Formula (17a) or the following general formula (17b), a plurality of R ₂ may be the same or different from each other, combined with R ₂ together may form a saturated or unsaturated ring, The saturated or unsaturated ring may have a substituent, and * represents the bonding position with L ₁ . )

In the compound according to this embodiment,
When A ₁ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
In one aspect, A ₁ is preferably a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted group. Triphenylenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted Benzocrisenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b] fluoranthenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted dibenzophenanthrenyl group, substituted or unsubstituted It consists of a naphthotriphenylenyl group and a substituted or unsubstituted naphthyl group. More preferably, the group is selected from the group consisting of:
On the other hand, as another embodiment, A ₁ is preferably a substituted or unsubstituted non-condensed aromatic hydrocarbon group having 6 to 18 ring carbon atoms, and more preferably a substituted or unsubstituted phenyl group. preferable.

In the present embodiment, R _{1 to} R ₄ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, a cyano group, or a substituted or unsubstituted ring carbon number of 6 to 6 It is preferably a group selected from the group consisting of 30 aromatic hydrocarbon groups and substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms, and substituted or unsubstituted 6 to 6 ring carbon atoms. It is more preferably a group selected from the group consisting of 30 aromatic hydrocarbon groups and substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms.

In this embodiment, R _{5 to} R ₈ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, a cyano group, or a substituted or unsubstituted ring carbon number of 6 to 6 It is preferably a group selected from the group consisting of 30 aromatic hydrocarbon groups and substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms, and substituted or unsubstituted 1 to 20 carbon atoms. It is a group selected from the group consisting of an alkyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. Is more preferable.

In the present embodiment, L ₁ is also preferably a single bond.
Further, in the present embodiment, when L ₁ is a linking group, L ₁ as a linking group, substituted or unsubstituted aromatic ring formed having 6 to 18 carbon atoms hydrocarbon group or a substituted or unsubstituted ring formed It is preferably a heterocyclic group having 5 to 20 atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted dibenzofurandiyl group, More preferably, it is selected from the group consisting of a substituted or unsubstituted dibenzothiophenediyl group and a substituted or unsubstituted carbazolediyl group.

  According to the compound of the present embodiment, it is possible to reduce the driving voltage while maintaining the light emission efficiency and lifetime of the organic EL element. This is considered because the compound of this embodiment has the above-mentioned specific structure. Z in the general formula (1) is, for example, a substituent represented by the general formula (2) or (3). According to the structure such as the substituent represented by the general formula (2) or (3), for example, π electron conjugation as compared with the structures of the compound A, the compound B, and the compound C described in Examples described later. It is considered that the system expands, the HOMO spread of the molecule increases, and the electron donor property increases. As a result, it is considered that the hole injection property is improved and the driving voltage is lowered by using the compound of the present embodiment in the organic layer of the organic EL element. In order to obtain the effect of lowering the driving voltage, the structure represented by the general formula (2) having higher planarity than the structure represented by the general formula (3) is used for the organic EL element. Is preferred.

(Method for producing compound according to the present embodiment)
The compound which concerns on this embodiment can be manufactured by the method as described in the Example mentioned later, for example. The compound according to this embodiment can be synthesized by following the methods described in the examples and using known alternative reactions and raw materials tailored to the target product.

  Examples of the compound according to this embodiment are shown below. In addition, the compound which concerns on this invention is not limited to these examples.

[Materials for organic EL elements]
The compound of this embodiment can be used as an organic EL device material. In this case, the compound of this embodiment may be used alone as a material for an organic EL device, or a mixture of the compound of this embodiment and another material may be used as a material for an organic EL device.

[Organic EL device]
(Element structure of organic EL element)
The configuration of the organic EL element according to this embodiment will be described.
The organic EL element has an anode, a cathode, and an organic layer. The organic layer includes one or more layers composed of an organic compound. The organic layer may further contain an inorganic compound. In the organic EL element of the present embodiment, at least one of the organic layers includes the compound according to the present embodiment.

As typical element configurations of the organic EL element, for example, the following configurations (a) to (e) can be given.
(A) Anode / light emitting layer / cathode (b) Anode / hole injection / transport layer / light emitting layer / cathode (c) Anode / light emitting layer / electron injection / transport layer / cathode (d) Anode / hole injection / transport Layer / light emitting layer / electron injection / transport layer / cathode (e) anode / hole injection / transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode Among the above, the configuration of (d) is preferably used. . However, the present invention is not limited to these configurations. The “light emitting layer” is an organic layer having a light emitting function. The “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”. The “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”. When the organic EL element has a hole injection layer and a hole transport layer, it is preferable that a hole injection layer is provided between the hole transport layer and the anode. Moreover, when an organic EL element has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided between the electron carrying layer and the cathode. Further, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer or a plurality of layers.

In FIG. 1, schematic structure of an example of the organic EL element in this embodiment is shown.
The organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 includes a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and an electron injection layer 9 that are stacked in this order from the anode 3 side.

(Light emitting layer)
The light emitting layer 7 of the organic EL element 1 includes the compound according to the present embodiment described above. In the present embodiment, the light emitting layer 7 preferably further contains a phosphorescent material. In the present embodiment, it is preferable to use the compound according to the present embodiment as the host material and the phosphorescent material as the dopant material for the light emitting layer 7.

  The phosphorescent material is selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt) in that the phosphorescent quantum yield is high and the luminous efficiency of the organic EL element can be improved. It is preferably an orthometalated complex containing a metal atom, more preferably an orthometalated complex containing a metal atom selected from the group consisting of iridium (Ir) and platinum (Pt). More preferred are complexes.

As the blue phosphorescent material that can be used for the light emitting layer 7, for example, a metal complex such as an iridium complex, an osmium complex, and a platinum complex is used. As a more specific blue phosphorescent material, for example, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6) ), Bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIr (pic)), bis [2- (3 ′, 5′bistrifluoromethyl) Phenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: Ir (CF ₃ ppy) ₂ (pic)), and bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′ And iridium (III) acetylacetonate (abbreviation: FIr (acac)).

As the green phosphorescent material that can be used for the light emitting layer 7, for example, an iridium complex or the like is used. As more specific green phosphorescent materials, for example, tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) ₃ ), bis (2-phenylpyridinato) -N, C2 ') iridium (III) acetylacetonate (abbreviation: Ir (ppy) ₂ (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) ₂ (acac)), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) ₂ (acac)), and the like.

As the red phosphorescent material that can be used for the light emitting layer 7, for example, a metal complex such as an iridium complex, a platinum complex, a terbium complex, and a europium complex is used. As a more specific red phosphorescent material, for example, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (Btp) ₂ (acac)), bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) ₂ (acac)), (acetylacetonato) bis [ 2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) ₂ (acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H , 23H-porphyrin platinum (II) (abbreviation: PtOEP).
For example, tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionate) (monophenanthroline) ) Europium (III) (abbreviation: Eu (DBM) ₃ (Phen)), and tris [1- (2-thenoyl) -3,3,3-trifluoroacetonate] (monophenanthroline) europium (III) (abbreviation) : Eu (TTA) ₃ (Phen)) and other rare earth metal complexes emit light from rare earth metal ions (electron transition between different multiplicity), and can therefore be used as phosphorescent materials.

In the present embodiment, at least one of the phosphorescent materials contained in the light emitting layer 7 preferably has a maximum emission wavelength of 450 nm or more and 750 nm or less. As a suitable phosphorescent material, a compound having a maximum emission wavelength of 450 nm to 495 nm, 495 nm to 590 nm, or 590 nm to 750 nm can be given.
By configuring a light emitting layer including the phosphorescent light emitting material having such an emission wavelength and the compound according to this embodiment, the light emission efficiency of the organic EL element can be improved.

  When the light emitting layer 7 contains a phosphorescent material, the content of the phosphorescent material in the light emitting layer 7 is preferably 0.1% by mass or more and 70% by mass or less, and preferably 1% by mass or more and 30% by mass or less. It is more preferable that

-Film thickness of a light emitting layer The film thickness of the light emitting layer 7 in the organic EL element 1 of this embodiment becomes like this. Preferably they are 5 nm or more and 50 nm or less, More preferably, they are 7 nm or more and 50 nm or less, More preferably, they are 10 nm or more and 50 nm or less. If the film thickness of the light emitting layer 7 is 5 nm or more, it will become easy to form the light emitting layer 7, and it will become easy to adjust chromaticity. If the film thickness of the light emitting layer 7 is 50 nm or less, a raise of a drive voltage can be suppressed.

(substrate)
The substrate 2 is used as a support for the organic EL element 1. As the substrate 2, for example, glass, quartz, plastic, or the like can be used. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and is made of, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, or polyethylene naphthalate. Examples include a plastic substrate. Moreover, an inorganic vapor deposition film can also be used.

(anode)
For the anode 3 formed on the substrate 2, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).
These materials are usually formed by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide. For example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method etc.
Of the organic layers formed on the anode 3, the hole injection layer 5 formed in contact with the anode 3 is made of a composite material that facilitates hole injection regardless of the work function of the anode 3. Because it is formed, a material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) is used. You can also.
An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. In addition, when forming the anode 3 using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method and a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(Hole injection layer)
The hole injection layer 5 is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
As a substance having a high hole injection property, 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low molecular organic compound, is used. , 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N -F Enylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- Aromatic amine compounds such as [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino [2,3-f: 20 , 30-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
As the substance having a high hole injecting property, a high molecular compound (an oligomer, a dendrimer, a polymer, or the like) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also

(Hole transport layer)
The hole transport layer 6 is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer 6. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / (V · s) or more.
The hole transport layer 6 includes CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl. A carbazole derivative such as -9H-carbazole (PCzPA) or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
However, any substance other than these may be used as long as it has a property of transporting more holes than electrons. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a layer in which two or more layers containing the above substances are stacked.
When two or more hole transport layers are arranged, it is preferable to arrange a layer containing a material having a larger energy gap on the side closer to the light emitting layer 7.

(Electron transport layer)
The electron transport layer 8 is a layer containing a substance having a high electron transport property. The electron transport layer 8 includes 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymers. Compounds can be used. Specifically, as a low-molecular organic compound, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), A metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Pert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4- Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: B) Heteroaromatic compounds such as zOs) can also be used. In this embodiment, a benzimidazole compound can be suitably used. The substances described here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / (V · s) or more. Note that a substance other than the above may be used as the electron transport layer 8 as long as the substance has a higher electron transport property than the hole transport property. Further, the electron transport layer 8 is not limited to a single layer, and may be a layer in which two or more layers made of the above substances are stacked.
In addition, a polymer compound can be used for the electron transport layer 8. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.

(Electron injection layer)
The electron injection layer 9 is a layer containing a substance having a high electron injection property. The electron injection layer 9 includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx). Alkali metals, alkaline earth metals, or compounds thereof can be used. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode 4 can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer 9. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer 8 described above is used. Can be used. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(cathode)
The cathode 4 is preferably made of a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
In addition, when forming the cathode 4 using an alkali metal, alkaline-earth metal, and an alloy containing these, a vacuum evaporation method and sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.
In addition, by providing the electron injection layer 9, the cathode 4 is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. Can be formed. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Layer formation method)
A method for forming each layer of the organic EL element 1 of the present embodiment is not limited to those described above, and a known method such as a dry film forming method or a wet film forming method can be employed. Examples of the dry film forming method include a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method. Examples of the wet film forming method include a spin coating method, a dipping method, a flow coating method, and an ink jet method.

(Film thickness)
The film thickness of each organic layer of the organic EL element 1 of the present embodiment is not limited except as specifically mentioned above. In general, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a high applied voltage is required and the efficiency is deteriorated.

  In the present embodiment, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” described below is the same unless otherwise specified. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.

In the present embodiment, the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly). Of the ring compound) represents the number of atoms constituting the ring itself. An atom that does not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the pyridine ring has 6 ring atoms, the quinazoline ring has 10 ring atoms, and the furan ring has 5 ring atoms. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
Next, each substituent described in the general formula will be described.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment (in the present specification, the aromatic hydrocarbon group may be referred to as an aryl group) include, for example, a phenyl group, a biphenyl group, Terphenyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluorane Examples include a tenenyl group, a benzo [g] chrycenyl group, a benzo [b] triphenylenyl group, a picenyl group, and a perylenyl group.
The aromatic hydrocarbon group in the present embodiment preferably has 6 to 20 ring carbon atoms, more preferably 6 to 14 carbon atoms, and 6 to 12 carbon atoms unless otherwise specifically mentioned above. Is more preferable. Of the aromatic hydrocarbon groups, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, and 4-fluorenyl group, the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or substitution in the present embodiment described later on the 9-position carbon atom Alternatively, it is preferable that an unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms is substituted.

In the present embodiment, the heterocyclic group having 5 to 30 ring atoms (in this specification, the heterocyclic group may be referred to as a heteroaryl group, a heteroaromatic cyclic group, or an aromatic heterocyclic group). The heteroatom preferably contains at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium atom, and germanium atom, and at least selected from the group consisting of nitrogen, sulfur, and oxygen More preferably, any atom is included.
Examples of the heterocyclic group having 5 to 30 ring atoms in the present embodiment include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl Group, benzothiazolyl group, benzisoxazolyl group, benzoisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl group, pyrrolidinyl group, piperazinyl group, morpholyl Group, phenazinyl group, phenothiazinyl group, phenoxazinyl group and the like.
The number of ring-forming atoms of the heterocyclic group in this embodiment is preferably 5-20, and more preferably 5-14. Among the above heterocyclic groups, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are particularly preferable. With respect to the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present embodiment or substitution on the 9th-position nitrogen atom Alternatively, an unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.

  In this embodiment, the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.

  In the general formulas (XY-1) to (XY-18), X and Y are each independently a hetero atom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. . The partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.

  In the present embodiment, the substituted or unsubstituted carbazolyl group may include, for example, a group obtained by further condensing a ring with a carbazole ring represented by the following formula. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.

As a C1-C20 aliphatic hydrocarbon group in this embodiment, any of linear, a branched chain, or cyclic | annular (alicyclic) may be sufficient. In the present embodiment, the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be a group composed of a saturated bond or a group containing an unsaturated bond.
As a C1-C20 aliphatic hydrocarbon group in this embodiment, a C1-C20 alkyl group is mentioned, for example. Examples of the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1- A heptyloctyl group and a 3-methylpentyl group.
The linear or branched alkyl group in the present embodiment preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Among the linear or branched alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group , An amyl group, an isoamyl group, and a neopentyl group are particularly preferable.
Examples of the cycloalkyl group having 3 to 20 carbon atoms in the present embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. The ring-forming carbon number of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8. Among the cycloalkyl groups, a cyclopentyl group and a cyclohexyl group are particularly preferable.
Examples of the halogenated alkyl group in which the alkyl group is substituted with a halogen atom include groups in which the alkyl group having 1 to 20 carbon atoms is substituted with one or more halogen atoms. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.

  Moreover, as a C1-C20 aliphatic hydrocarbon group in this embodiment, a C2-C20 alkenyl group is mentioned. For example, the alkenyl group having 2 to 20 carbon atoms in the present embodiment may be linear, branched, or cyclic, and examples thereof include a vinyl group, a propenyl group, a butenyl group, an oleyl group, and an eicosapenta. Enyl, docosahexaenyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2-propenyl, cyclopentadienyl, cyclopentenyl, cyclo A hexenyl group, a cyclohexadienyl group, etc. are mentioned.

  Moreover, as a C1-C20 aliphatic hydrocarbon group in this embodiment, a C2-C20 alkynyl group is mentioned. In the present embodiment, the alkynyl group having 2 to 20 carbon atoms may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.

Examples of the substituted silyl group in the present embodiment include an alkylsilyl group having 1 to 60 carbon atoms and an arylsilyl group having 6 to 60 ring carbon atoms.
Examples of the alkylsilyl group having 1 to 60 carbon atoms in the present embodiment include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group. , Tri-n-butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t- Examples thereof include a butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. The three alkyl groups in the trialkylsilyl group may be the same or different.

Examples of the arylsilyl group having 6 to 60 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
The dialkylarylsilyl group has, for example, two alkyl groups exemplified as the above alkyl group having 1 to 20 carbon atoms, and one dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Is mentioned. The carbon number of the dialkylarylsilyl group is preferably 8-30.
The alkyldiarylsilyl group has, for example, one alkyl group exemplified for the alkyl group having 1 to 20 carbon atoms, and two alkyl diarylsilyl groups having the two aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Is mentioned. The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30.

Alkoxy group having 1 to 20 carbon atoms in the present embodiment is represented as -OZ _1. Examples of _{Z 1,} include alkyl groups of 1 to 20 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group preferably has 1 to 20 carbon atoms.
As a halogenated alkoxy group by which the alkoxy group was substituted by the halogen atom, the group by which the said C1-C20 alkoxy group was substituted by the 1 or more fluorine atom is mentioned, for example.

Aryloxy group ring forming C6-30 in this embodiment is expressed as -OZ _2. Examples of this Z ₂ include the aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. The ring-forming carbon number of the aryloxy group is preferably 6-20. Examples of the aryloxy group include a phenoxy group.

Alkylthio group having 1 to 20 carbon atoms is represented as -SR _V. Examples of _{R V,} include alkyl groups of 1 to 20 carbon atoms. The alkylthio group preferably has 1 to 10 carbon atoms.
Ring formation arylthio group having 6 to 30 carbon atoms is expressed as -SR _W. Examples of R _W, and an aromatic hydrocarbon group of the ring-forming C6-30. The ring-forming carbon number of the arylthio group is preferably 6-20.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

  The substituted phosphoryl group is represented by the following general formula (P).

In the general formula (P), Ar _P1 and Ar _P2 are each independently a substituent selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms. A substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 ring carbon atoms, more preferably 1 to 6 carbon atoms. And more preferably a substituent selected from the group consisting of an alkyl group having a ring structure and an aryl group having 6 to 14 ring carbon atoms.

  Examples of the substituted carbonyl group include a benzoyl group, a naphthoyl group, and an acetyl group.

In this embodiment, “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. “Ring-forming atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
In the present embodiment, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

In the case of “substituted or unsubstituted”, examples of the substituent include the aromatic hydrocarbon group, the heterocyclic group, and the alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group) as described above. , Alkenyl group, alkynyl group, alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, halogen atom, cyano group, aralkyl group, alkylamino group, arylamino group, hydroxyl group , A nitro group, and a carboxy group.
Among the substituents mentioned here, an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and more preferable in the description of each substituent. The specific substituents are preferred.
These substituents are the above aromatic hydrocarbon group, heterocyclic group, alkyl group, alkenyl group, alkynyl group, alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, halogen atom In addition to the cyano group, it may be further substituted with an aralkyl group, an alkylamino group, an arylamino group, a hydroxyl group, a nitro group, and a carboxy group. A plurality of these substituents may be bonded to each other to form a ring.

As the aralkyl group, an aralkyl group having 6 to 30 ring carbon atoms is preferable and represented by -Z ₃ -Z ₄ . Examples of Z ₃ include alkylene groups corresponding to the alkyl groups having 1 to 30 carbon atoms. Examples of this Z ₄ include the above aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. The aralkyl group is an aralkyl group having 7 to 30 carbon atoms (the aromatic hydrocarbon portion is 6 to 30, preferably 6 to 20, more preferably 6 to 12), and the alkyl portion is 1 to 30 carbon atoms (preferably Is preferably 1 to 20, more preferably 1 to 10, and still more preferably 1 to 6). Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Examples include naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

Alkylamino group having 2 to 30 carbon atoms is represented as -NHR _V or -N _{(R V) 2,.} Examples of _{R V,} include alkyl groups of 1 to 30 carbon atoms.

The arylamino group having 6 to 60 ring carbon atoms is represented as —NHR _W or —N (R _W ) ₂ . Examples of R _W, and an aromatic hydrocarbon group of the ring-forming C6-30.

The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
In the present embodiment, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the present embodiment, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted and substituted. The number of atoms of the substituent in the case is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

  In this embodiment, when substituents are bonded to each other to form a ring structure, the ring structure is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring. In the present embodiment, examples of the aromatic hydrocarbon ring and the heterocyclic ring include a ring structure derived from the above-described monovalent group.

  In the present embodiment, examples of the aromatic hydrocarbon group and the heterocyclic group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-described monovalent group.

(Electronics)
The organic EL element 1 according to an embodiment of the present invention can be used for electronic devices such as a display device and a light emitting device. Examples of the display device include display components such as an organic EL panel module, a television, a mobile phone, a tablet, or a personal computer. Examples of the light emitting device include lighting or a vehicular lamp.

[Modification of Embodiment]
In addition, this invention is not limited to the above-mentioned embodiment, The change in the range which can achieve the objective of this invention, improvement, etc. are contained in this invention.

The configuration of the organic EL element is not limited to the configuration described in the above embodiment.
For example, a barrier layer may be provided adjacent to the anode side or cathode side of the light emitting layer. The barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, and excitons.
For example, when a barrier layer is disposed in contact with the cathode side of the light emitting layer, the barrier layer transports electrons, and the holes reach a layer (for example, an electron transport layer) on the cathode side of the barrier layer. Stop that. When an organic EL element contains an electron carrying layer, it is also preferable to contain the said barrier layer between a light emitting layer and an electron carrying layer.
In addition, when a barrier layer is disposed in contact with the anode side of the light emitting layer, the barrier layer transports holes, and the electrons reach a layer on the anode side of the barrier layer (for example, a hole transport layer). To stop doing. When the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light emitting layer and the hole transport layer.
Further, a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer. The excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
The light emitting layer and the barrier layer are preferably joined.

  The compound according to the embodiment may be contained in an organic layer other than the light emitting layer.

  In addition, the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.

  Examples according to the present invention will be described below. The present invention is not limited by these examples.

(Synthesis of Intermediate 1)
Under an argon atmosphere, 37 g of 3-bromocarbazole, 39 g of intermediate A synthesized by the method described in WO2014 / 141725A1, 2.5 g of [1,1-bis (diphenylphosphino) ferrocene] dichloropalladium (II), 200 mL of 2 mol of sodium carbonate aqueous solution and 680 mL of cyclopentyl methyl ether were charged into a flask, and the mixture was heated and stirred at 80 ° C. for 6 hours. After heating and stirring, the mixture was cooled to room temperature, and the precipitated crystals were filtered and recrystallized to obtain 29 g of Intermediate 1. The yield of intermediate 1 was 50%.
As a result of mass spectrum analysis, it was m / e = 383 with respect to the molecular weight 383 of Intermediate 1.

(Synthesis of Compound 1)
Under an argon atmosphere, 700 mg of intermediate 1, 440 mg of 2-chloro-4-phenylquinazoline, 30 mg of tris (dibenzylideneacetone) dipalladium (0), 38 mg of tri-t-butylphosphonium tetrafluoroborate, sodium-t -226 mg of butoxide and 8 mL of toluene were charged in a flask and heated to reflux for 5 hours. After heating to reflux, the reaction solution was cooled to room temperature, and the reaction solution was extracted with toluene. The obtained organic layer was dried and concentrated. The obtained residue was purified by column chromatography to obtain 412 mg of Compound 1. The yield of compound 1 was 38%.
As a result of mass spectrum analysis, it was m / e = 587 with respect to the molecular weight 587 of Compound 1.

(Synthesis of Compound 2)
Compound 2 was synthesized in the same manner using 3-bromofluoranthene instead of 2-chloro-4-phenylquinazoline in the synthesis of compound 1.
As a result of mass spectrum analysis, it was m / e = 583 with respect to the molecular weight 583 of Compound 2.

(Synthesis of Intermediate 2)
Intermediate 2 was synthesized in the same manner using 2-bromocarbazole instead of 3-bromocarbazole in the synthesis of intermediate 1.
As a result of mass spectrum analysis, it was m / e = 383 with respect to the molecular weight 383 of Intermediate 2.

(Synthesis of Compound 3)
Compound 3 was synthesized in the same manner using Intermediate 2 instead of Intermediate 1 in the synthesis of Compound 1.
As a result of mass spectrum analysis, it was m / e = 587 with respect to the molecular weight 587 of compound 3.

(Synthesis of Compound 4)
Compound 4 was synthesized in the same manner using Intermediate 2 instead of Intermediate 1 in the synthesis of Compound 2.
As a result of mass spectrum analysis, it was m / e = 583 with respect to the molecular weight 583 of compound 4.

(Synthesis of Intermediate 3)
Intermediate 3 was synthesized in the same manner using Intermediate B instead of Intermediate A in the synthesis of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 409 with respect to the molecular weight 409 of Intermediate 3.

(Synthesis of Compound 5)
Compound 5 was synthesized in the same manner using Intermediate 3 instead of Intermediate 1 in the synthesis of Compound 1.
As a result of mass spectrum analysis, it was m / e = 613 with respect to the molecular weight 613 of compound 5.

(Synthesis of Compound 6)
Compound 5 was synthesized in the same manner using Intermediate 3 instead of Intermediate 1 in the synthesis of Compound 2.
As a result of mass spectrum analysis, it was m / e = 609 with respect to the molecular weight 609 of compound 6.

(Synthesis of Intermediate 4)
Intermediate 4 was synthesized in the same manner using 10-bromo-7H-benzo [c] carbazole instead of 3-bromocarbazole in the synthesis of intermediate 1.
As a result of mass spectrum analysis, it was m / e = 433 with respect to the molecular weight 433 of the intermediate 4.

(Synthesis of Compound 7)
Compound 7 was synthesized in the same manner using Intermediate 4 instead of Intermediate 1 in the synthesis of Compound 1.
As a result of mass spectrum analysis, it was m / e = 637 with respect to the molecular weight 637 of compound 7.

(Synthesis of Compound 8)
Compound 8 was synthesized in the same manner using Intermediate 4 instead of Intermediate 1 in the synthesis of Compound 2.
As a result of mass spectrum analysis, it was m / e = 633 with respect to the molecular weight 633 of compound 8.

[Manufacture of organic EL elements]
The compound used for manufacture of an organic EL element is shown below.

Example 1
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, the compound HT1 is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. A 60 nm HT1 film was formed to form a hole injection layer.
Next, a compound HT2 was vapor-deposited on the hole injection layer to form a 20 nm-thick HT2 film, thereby forming a hole transport layer.
Next, Compound 1 and Compound PD were formed on the hole transport layer by co-evaporation to form a light emitting layer having a thickness of 30 nm. The concentration of the compound PD contained in the light emitting layer was 5% by mass.
Subsequent to the formation of the light emitting layer, the compound ET and 8-quinolinolatolithium (Liq) were formed by co-evaporation at a mass ratio of 50:50 to form an electron transport layer having a thickness of 30 nm.
Liq was vapor-deposited on this electron transport layer to form an electron injection layer having a thickness of 1 nm.
Metal Al was vapor-deposited on the electron injection layer to form a metal cathode having a thickness of 80 nm.
Thus, the organic EL device according to Example 1 was produced.
A device arrangement of the organic EL device of Example 1 is schematically shown as follows.
ITO (130) / HT1 (60) / HT2 (20) / Compound 1: PD (30, 5%) / ET1: Liq (30, 50%) / Liq (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the number displayed as a percentage indicates the concentration (mass%) of the compound PD in the light emitting layer or the concentration (mass%) of Liq in the electron transport layer.

(Comparative Example 1)
The organic EL device of Comparative Example 1 was prepared in the same manner as in Example 1 except that Compound A was used instead of Compound 1 in Example 1.
A device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HT1 (60) / HT2 (20) / Compound A: PD (30, 5%) / ET1: Liq (30, 50%) / Liq (1) / Al (80)

(Comparative Example 2)
The organic EL device of Comparative Example 2 was prepared in the same manner as in Example 1 except that Compound B was used instead of Compound 1 in Example 1.
A device arrangement of the organic EL device of Comparative Example 2 is schematically shown as follows.
ITO (130) / HT1 (60) / HT2 (20) / Compound B: PD (30, 5%) / ET1: Liq (30, 50%) / Liq (1) / Al (80)

(Comparative Example 3)
The organic EL device of Comparative Example 3 was produced in the same manner as in Example 1 except that Compound C was used instead of Compound 1 in Example 1.
A device arrangement of the organic EL device of Comparative Example 3 is schematically shown as follows.
ITO (130) / HT1 (60) / HT2 (20) / Compound C: PD (30, 5%) / ET1: Liq (30, 50%) / Liq (1) / Al (80)

  About the produced organic EL element, it measured in accordance with the following method and evaluated performance. The results are shown in Table 1.

(1) Driving voltage The voltage (unit: V) when energized between the anode (ITO transparent electrode) and the metal cathode (metal Al) was measured so that the current density was 10 mA / cm ² .

(2) External quantum efficiency (EQE)
A spectral radiance spectrum when a voltage was applied to the device so that the current density was 10 mA / cm ² was measured using a spectral radiance meter “CS-1000” (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency (10 mA / cm ² , unit:%) was calculated on the assumption that Lambtian radiation was performed.

(3) Life (LT90)
A direct current energization test was performed with the initial current density set to 10 mA / cm ² , the time when the luminance decreased to 90% of the luminance at the start of the test was measured, and the measurement time was defined as the life (LT90). did.

  As shown in Table 1, according to the compound of the present invention, the driving voltage can be lowered while maintaining the light emission efficiency and life of the organic EL element.

  DESCRIPTION OF SYMBOLS 1 ... Organic EL element, 2 ... Board | substrate, 3 ... Anode, 4 ... Cathode, 6 ... Hole transport layer, 7 ... Light emitting layer, 8 ... Electron transport layer, 10 ... Organic layer.

Claims (30)

A compound represented by the following general formula (1).

(In the general formula (1),
A ₁ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
L ₁ and L ₂ are each independently a single bond or a linking group,
L ₁ and L ₂ as a linking group are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms. Group,
R ₁ and R ₂ are each independently
A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 1 to 60 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
Halogen atoms,
A cyano group,
A substituted phosphoryl group,
A substituted carbonyl group,
A group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
a is an integer of 0 or more and 7 or less, and the plurality of R ₁ may be the same or different from each other;
b is an integer greater than or equal to 0, and several R < ₂ > may mutually be same or different,
when a is an integer of 2 or more, R ₁ may be bonded to each other to form a saturated or unsaturated ring;
When b is an integer of 2 or more, R ₂ may be bonded to each other to form a saturated or unsaturated ring,
Z is a substituent represented by the following general formula (2) or (3). )

(In the general formula (2), X ₂ is O or S;
In the general formula (3), X ₃ is CR ₅ R ₆ or SiR ₇ R ₈ .
In the general formula (2) or the general formula (3),
R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ are each independently
A substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 1 to 60 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
Halogen atoms,
A cyano group,
A substituted phosphoryl group,
A substituted carbonyl group,
A group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
c and d are each independently an integer of 0 to 9,
Several R < ₃ > may mutually be same or different,
Several R < ₄ > may mutually be same or different,
* Indicates a binding position with the _{L 2.} )
The compound of Claim 1 represented by following General formula (4).

(In the general formula (4), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c are respectively in the general formula (1) or (2). It is synonymous with definition.)
The compound of Claim 1 represented by following General formula (5).

(In the general formula (5), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are: Each has the same definition as in general formula (1) or (3).)
The compound of Claim 1 or Claim 2 represented by following General formula (6).

(In the general formula (6), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c are respectively in the general formula (1) or (2). It is synonymous with definition.)
The compound of Claim 1 or Claim 3 represented by following General formula (7).

(In the general formula (7), A ₁ , L ₁ , L ₂ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are: Each has the same definition as in general formula (1) or (3).)
The compound according to any one of claims 1 to 5, wherein L ₂ is a single bond.
The compound of Claim 1, Claim 2, or Claim 4 represented by following General formula (8).

(In the general formula (8), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c have the same definitions as in the general formula (1) or (2), respectively. .)
The compound of Claim 1, Claim 2, or Claim 4 represented by following General formula (9).

(In the general formula (9), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₂ , R ₃ , and c have the same definitions as in the general formula (1) or (2), respectively. .)
The compound of Claim 1, Claim 3, or Claim 5 represented by following General formula (10).

(In the general formula (10), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are (It is synonymous with the definition in Formula (1) or (3).)
The compound of Claim 1, Claim 3, or Claim 5 represented by following General formula (11).

(In the general formula (11), A ₁ , L ₁ , R ₁ , R ₂ , a, b, X ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , and d are (It is synonymous with the definition in Formula (1) or (3).)
A ₁ is represented by the following general formula (12), the compound as claimed in any one of claims 10.

(In the general formula (12), Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are each independently a carbon atom bonded to a nitrogen atom, CR ₂ or L ₁ ;
Any of Y _{1 to} Y ₆ is a carbon atom bonded to L ₁ ;
Several R < ₂ > may mutually be same or different,
R ₂ may be bonded to each other to form a saturated or unsaturated ring, and the saturated or unsaturated ring may have a substituent,
* Indicates a binding position with the _{L 1.} )
A ₁ is represented by the following general formula (13), the compound as claimed in any one of claims 11.

(In the general formula (13), Y ₃ , Y ₄ , Y ₅ , Y ₆ , Y ₇ , Y ₈ , Y ₉ and Y ₁₀ are each independently a carbon atom bonded to a nitrogen atom, CR ₂ or L _1. Is an atom,
Any of Y _{3 to} Y ₁₀ is a carbon atom bonded to L ₁ ;
Several R < ₂ > may mutually be same or different,
R ₂ may be bonded to each other to form a saturated or unsaturated ring, and the saturated or unsaturated ring may have a substituent,
* Indicates a binding position with the _{L 1.} )
The compound according to claim 12, wherein at least one of Y _{3 to} Y ₁₀ is a nitrogen atom.
Any of Y _{3 to} Y ₁₀ is a carbon atom bonded to L ₁ ;
At least two of Y _{3 to} Y ₁₀ are nitrogen atoms;
Others of Y ₃ to Y ₁₀ is CR _2, A compound according to claim 12 or claim 13.
A ₁ is represented by the following general formula (14), compound according to claims 12 to any one of claims 14.

(In the general formula (14),
Any of Y _{3 to} Y ₆ is a carbon atom bonded to L ₁ ;
At least two of Y _{3 to} Y ₆ are nitrogen atoms;
Y _{7 to} Y ₁₀ are each independently a nitrogen atom or CR ₂ ,
* Indicates a binding position with the _{L 1.} )
A ₁ is represented by the following general formula (15), the compound as claimed in any one of claims 15.

(In the general formula (15), Y _{6 to} Y ₁₀ are each independently a nitrogen atom or CR ₂ ,
* Indicates a binding position with the _{L 1.} )
At least one of Y _{1 to} Y ₆ is a nitrogen atom;
Any of Y _{1 to} Y ₆ is a carbon atom bonded to L ₁ ;
The rest of Y _{1 to} Y ₆ is CR ₂ ,
R ₂ do not ring by binding to each other is formed, the compound according to claim 11.
Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ and Y ₆ are carbon atoms bonded to CR ₂ or L ₁ ;
Any of Y _{1 to} Y ₆ is a carbon atom bonded to L ₁ ;
Several R < ₂ > may mutually be same or different,
R ₂ is bonded to each other to form a saturated or unsaturated ring,
The compound according to claim 11, wherein the saturated or unsaturated ring may have a substituent.
A ₁ is represented by the following general formula (16), the compound as claimed in any one of claims 11.

(In the general formula (16), Y ₃ , Y ₄ , Y ₅ , Y ₆ , Y ₇ , Y ₈ , Y ₉ and Y ₁₀ are each independently a carbon atom bonded to CR ₂ or L ₁ . ,
Any of Y _{3 to} Y ₁₀ is a carbon atom bonded to L ₁ ;
Several R < ₂ > may mutually be same or different,
R ₂ may be bonded to each other to form a saturated or unsaturated ring, and the saturated or unsaturated ring may have a substituent,
* Indicates a binding position with the _{L 1.} )
The compound according to claim 19, wherein A ₁ is represented by the following general formula (17a) or the following general formula (17b).

(In the general formula (17a), Y _{4 to} Y ₉ are each independently a carbon atom bonded to CR ₂ or L ₁ , and Y ₁₁ , Y ₁₂ , Y ₁₃ , and Y ₁₄ are CR ₂ . And any one of Y _{4 to} Y ₉ is a carbon atom bonded to L ₁ ;
In the general formula (17b), Y _{4 to} Y ₉ are CR ₂ , and Y ₁₁ , Y ₁₂ , Y ₁₃ , and Y ₁₄ are each independently a carbon atom bonded to CR ₂ or L ₁ . , Y _{11 to} Y ₁₄ are carbon atoms bonded to L ₁ ,
In the general formula (17a) or the following general formula (17b),
Several R < ₂ > may mutually be same or different,
R ₂ may be bonded to each other to form a saturated or unsaturated ring, and the saturated or unsaturated ring may have a substituent,
* Indicates a binding position with the _{L 1.} )
R _{1 to} R ₈ are each independently a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, a cyano group, or a substituted or unsubstituted aromatic carbon atom having 6 to 30 ring carbon atoms. 21. The compound according to any one of claims 1 to 20, which is a group selected from the group consisting of a hydrogen group and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
The compound according to any one of claims 1 to 21, wherein L ₁ is a single bond.
L ₁ as a linking group is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted dibenzofurandiyl group, a substituted or unsubstituted dibenzothiophene. The compound according to any one of claims 1 to 21, which is selected from the group consisting of a diyl group and a substituted or unsubstituted carbazole diyl group.
A cathode, an anode, and an organic layer provided between the cathode and the anode,
The organic layer has at least a light emitting layer,
The organic electroluminescent element in which at least 1 layer contains the compound as described in any one of Claims 1-23 among the said organic layers.
The organic light-emitting device according to claim 24, wherein the light-emitting layer contains the compound.
The light emitting layer further contains a phosphorescent material.
The organic electroluminescence device according to claim 24 or 25.
The phosphorescent material is an orthometalated complex containing a metal atom selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt).
The organic electroluminescent device according to claim 26.
The organic electroluminescence device according to any one of claims 24 to 27, further comprising a hole transport layer between the anode and the light emitting layer.
The organic electroluminescence device according to any one of claims 24 to 28, further comprising an electron transport layer between the cathode and the light emitting layer.
  An electronic device comprising the organic electroluminescence element according to any one of claims 24 to 29.