JP2015233023A - Organic electroluminescent device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent device which is driven with a low voltage, and emits light with a high efficiency and a long life.SOLUTION: An organic electroluminescent device comprises: a positive electrode; a negative electrode opposed to the positive electrode; and an organic layer provided between the positive and negative electrodes, and including at least a light-emitting layer. The light-emitting layer includes: an anthracene derivative having a particular structure; and a fluoranthene derivative having a particular structure.

Description

  The present invention relates to an organic electroluminescence element.

  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 is composed of a light emitting layer and a pair of counter electrodes 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. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.

  Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic light-emitting diodes. Further, the characteristic deterioration has been remarkably not put into practical use. Although recent organic EL devices have been gradually improved, further higher light emission efficiency, longer life, improved color reproducibility, and the like are required.

The performance of organic EL elements has been gradually improved by improving the light emitting material for organic EL. In particular, improving the color purity of blue organic EL elements (shortening the emission wavelength) is an important technique that leads to improved color reproducibility of displays.
Patent Document 1 describes an organic EL device including a light-emitting layer containing a fluoranthene derivative as a dopant material and an aryl-substituted anthracene derivative as a host material. Patent Document 1 describes that according to the organic EL element including the light emitting layer, blue light emission can be obtained with a long lifetime and high light emission efficiency.

International Publication No. 2007/100010

  However, the organic EL element described in Patent Document 1 does not have sufficient efficiency and longevity, and when the organic EL element is used as a light source of an electronic device such as a lighting device or a display device, the efficiency is further improved and the life is extended. is necessary.

  Accordingly, an object of the present invention is to provide an organic electroluminescence element that is driven at a low voltage and emits light with high efficiency and a long lifetime.

[1]
The organic electroluminescence device of the present invention includes an anode, a cathode provided opposite to the anode, and an organic layer provided between the anode and the cathode and including at least a light emitting layer, and the light emission The layer includes an anthracene derivative represented by the following general formula (1) and a fluoranthene derivative represented by the following general formula (21).

[In the general formula (1),
Any one of R ^{101 to} R ¹¹⁰ is a single bond and is used for bonding to L ¹ ;
R ^{101 to} R ¹¹⁰ not used for bonding with L ¹ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
Selected from 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 is selected from either a single bond or a linking group;
The linking group is
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 30 carbon atoms,
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 30 ring atoms, or the aromatic hydrocarbon ring structure and the heterocyclic structure A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a structure formed by bonding at least 2 to 4 of any one of them,
a, b, and c each represent an integer of 1 to 4.
Z ¹ represents a structure represented by the following general formula (2). ]

[R ^{119 to} R ¹²⁰ in the general formula (2) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Selected from 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;
Any one of R ^{111 to} R ¹¹⁸ is a single bond used for bonding to L ¹ ;
R ^{111 to} R ^{118 that} are not used for bonding to L ¹ are each independently synonymous with R ^{101 to} R ¹¹⁰ that are not used to bond to L ¹ .
Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). ]

[In the general formula ^(3), y 1, ^{y 2} shows a set of binding position adjacent in ^R 111 ^{to R 118} in the general formula (2).
R ^{121 to} R ¹²⁴ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
It is selected from either 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.
In the general formula (2), any one of R ^{111 to} R ¹¹⁸ that does not form a ring and any one of R ^{121 to} R ^{124 in} the general formula (3) is a single bond, and the general formula (1) used in the coupling with L ^1. ]

[In the said General formula (21), R ^< 21>, R < ²² >, R < ²⁵ >, R < ²⁶ > and R < ²⁸ > -R < ³¹ > are respectively independently,
Hydrogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
Silyl group,
Carboxyl group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 7 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 alkoxycarbonyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
It is selected from the first 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.
R ²³ is selected from the second group constituted by removing hydrogen atoms from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ³¹ .
R ²⁴ is selected from the third group constituted by removing the aromatic hydrocarbon group and the heterocyclic group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. .
R ²⁷ and R ³² are each independently a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a silyl group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. Selected from the fourth group consisting of a group and a carboxyl group.
R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring and may not form a saturated or unsaturated ring, and the ring is substituted or unsubstituted.
Except when R ^{21 to} R ²³ and R ^{25 to} R ³² are monovalent groups derived from benzo [k] fluoranthene.
R ²³ and R ²⁴ are different from each other.
Except when one of R ²³ and R ²⁴ is an α-naphthyl group. ]

[2]
In the organic electroluminescence device according to the above [1],
Z ¹ in the general formula (1) is preferably represented by any one of the following general formulas (2-4), (2-5), and (2-6).

[Ar ^{161 to} Ar ¹⁶² in General Formula (2-4), Ar ^{171 to} Ar ¹⁷² in General Formula (2-5), and Ar ^{181 to} Ar ¹⁸² in General Formula (2-6) are each independently , Which has the same meaning as R ^{119 to} R ¹²⁰ in the general formula (2).
1 one of ^R 161 ^{to R 170} in the general formula (2-4) is used for binding to ^{L 1} represents a single bond, ^R 161 ^{to R 170} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 171 ^{to R 180} in the general formula (2-5) is used for binding to ^{L 1} represents a single bond, ^R 171 ^{to R 180} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 181 ^{to R 190} in the general formula (2-6) is used for binding to ^{L 1} represents a single bond, ^R 181 ^{to R 190} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ . ]

[3]
In the organic electroluminescent element according to the above [1] or [2], b in the general formula (1) is preferably 1.

[4]
In the organic electroluminescence device according to any one of [1] to [3], a in the general formula (1) is preferably 1 or 2.

[5]
In the organic electroluminescent element according to any one of [1] to [4], at least one of R ¹⁰⁹ and R ^{110 in} the general formula (1) is used for bonding to L ^1. It is preferably a single bond.

[6]
In the organic electroluminescence device according to any one of [1] to [4], at least one of R ¹⁰¹ to R ^{104 in} the general formula (1) is used for bonding to L ^1. It is preferable that it is a single bond.

[7]
In the organic electroluminescent element according to the above [6], R ^{102 in the} general formula (1) is preferably a single bond used for bonding to L ¹ .

[8]
In the organic electroluminescent element according to any one of [1] to [7], R ^{109 in the} general formula (1) is:
It is preferably a group selected from 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.

[9]
In the organic electroluminescence device according to [8], R ¹⁰⁹ of the general formula (1) is preferably represented by the following general formula (11).

[In the general formula (11), Ar ¹ represents
A group selected from 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.
Each Ra has the same meaning as R ^{101 to} R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
d shows the integer of 1-4.
When d is 2 to 4, a plurality of Ra are the same or different. ]

[10]
In the organic electroluminescence device according to the above [8], R ^{109 in the} general formula (1) is preferably a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms.

[11]
In the organic electroluminescent element according to any one of [1] to [10], R ^{24 in the} general formula (21) is preferably a hydrogen atom.

[12]
In the organic electroluminescence device according to any one of [1] to [11], R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted 6 to 30 ring carbon atoms. The aromatic hydrocarbon group is preferable.

[13]
In the organic electroluminescence device according to the above [12], it is preferable that R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted phenyl groups.

[14]
In the organic electroluminescence device according to any one of [1] to [10],
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
In the general formula (21), R ²³ , R ²⁷ and R ³² are preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

[15]
In the organic electroluminescence device according to any one of [1] to [10],
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms,
R ^{23 in the} general formula (21) is —Ar ²¹ —Ar ²² ,
Ar ²¹ and Ar ²² are preferably each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

[16]
In the organic electroluminescence device according to any one of [1] to [10],
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms,
R ^{23 in the} general formula (21) is —Ar ²¹ —Ar ²² —Ar ²³ ,
Ar ²¹ , Ar ²² and Ar ²³ are each independently preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

[17]
In the organic electroluminescence device according to the above [15], it is preferable that the Ar ²¹ or the Ar ²² is an aromatic hydrocarbon group having a cyano group as a substituent.

[18]
In the organic electroluminescence device according to the above [16], it is preferable that the Ar ²¹ , the Ar ²² or the Ar ²³ is an aromatic hydrocarbon group having a cyano group as a substituent.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which drives with a low voltage and light-emits with high efficiency and long lifetime can be provided.

It is a figure which shows schematic structure of an example of the organic electroluminescent element which concerns on embodiment of this invention.

(Element structure of organic EL element)
Hereinafter, the element configuration of the organic EL element according to the present invention will be described.
The organic EL device of the present invention includes an organic layer between a pair of electrodes. This organic layer has at least one layer composed of an organic compound. The organic layer may contain an inorganic compound.
In the organic EL device of the present invention, at least one of the organic layers has a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer, or an organic layer such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, or an electron barrier layer. You may have the layer employ | adopted with an EL element.

As a typical element configuration of the organic EL element,
(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 Examples of the structure include 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 (d) is preferably used, but it is of course not limited thereto.
The “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed. At this time, the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function. In the case of a phosphorescent element, the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
The above “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “an electron injection layer and an electron transport layer”. "At least one of them". Here, when it has a positive hole injection layer and a positive hole transport layer, it is preferable that the positive hole injection layer is provided in the anode side. Moreover, when it has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided in the cathode side.

  In the present invention, the electron transport layer refers to an organic layer having the highest electron mobility among the organic layers in the electron transport region existing between the light emitting layer and the cathode. When the electron transport region is composed of one layer, the layer is an electron transport layer. In addition, in the phosphorescent organic EL device, as shown in the configuration (e), a barrier layer that does not necessarily have high electron mobility is used to prevent diffusion of excitation energy generated in the light emitting layer. The organic layer adjacent to the light emitting layer does not necessarily correspond to the electron transport layer.

In FIG. 1, schematic structure of an example of the organic EL element in embodiment of this invention 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 has a light emitting layer 5 containing a host material and a dopant material. The organic layer 10 has a hole transport layer 6 between the light emitting layer 5 and the anode 3. Further, the organic layer 10 has an electron transport layer 7 between the light emitting layer 5 and the cathode 4.

(Light emitting layer)
-Host material As a host material used for the organic EL element of this invention, the anthracene derivative represented by following General formula (1) can be used.

In the general formula (1), any c of R ^{101 to} R ¹¹⁰ is a single bond and is used for bonding to L ¹ .
In the general formula (1), R ^{101 to} R ¹¹⁰ not used for bonding with L ¹ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
It is selected from either 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.

In the general formula (1), L ¹ is selected from either a single bond or a linking group.
In the general formula (1), the linking group is
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 30 carbon atoms,
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 30 ring atoms, or the aromatic hydrocarbon ring structure and the heterocyclic structure This is a (a + 1) -valent residue obtained by removing (a + 1) hydrogen atoms from a structure formed by bonding at least 2 to 4 of at least one of them.

In the general formula (1), a, b and c each represent an integer of 1 to 4.
It is preferable that a in the general formula (1) is 1 or 2.
B in the general formula (1) is preferably 1.

In the general formula (1), Z ¹ represents a structure represented by the following general formula (2).

[R ^{119 to} R ¹²⁰ in the general formula (2) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Selected from 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;
Any one of R ^{111 to} R ¹¹⁸ is a single bond used for bonding to L ¹ ;
R ^{111 to} R ^{118 that} are not used for bonding to L ¹ are each independently synonymous with R ^{101 to} R ¹¹⁰ that are not used to bond to L ¹ .
Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). ]

In Formula ^(3), y 1, ^{y 2} shows a set of binding position adjacent in ^R 111 ^{to R 118} in the general formula (2).
R ^{121 to} R ¹²⁴ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
It is selected from either 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.
In the general formula (2), any one of R ^{111 to} R ¹¹⁸ that does not form a ring and any one of R ^{121 to} R ^{124 in} the general formula (3) is a single bond, and the general formula (1) used in the coupling with L ^1.

Further, the ^{Z 1} in the general formula (1) is represented by the following general formula (2-4), (2-5) is preferably represented by any one of (2-6).

Ar ^{161 to} Ar ¹⁶² in the general formula (2-4), Ar ^{171 to} Ar ^{172 in} the general formula (2-5), and Ar ^{181 to} Ar ¹⁸² in the general formula (2-6) are each independently it is synonymous with ^R 119 ^{to R 120} in the general formula (2).
1 one of ^R 161 ^{to R 170} in the general formula (2-4) is used for binding to ^{L 1} represents a single bond, ^R 161 ^{to R 170} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 171 ^{to R 180} in the general formula (2-5) is used for binding to ^{L 1} represents a single bond, ^R 171 ^{to R 180} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 181 ^{to R 190} in the general formula (2-6) is used for binding to ^{L 1} represents a single bond, ^R 181 ^{to R 190} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .

It is preferable that at least one of R ¹⁰⁹ and R ^{110 in} the general formula (1) is a single bond used for bonding to L ¹ .
Alternatively, at least one of R ¹⁰¹ to R ^{104 in} the general formula (1) is preferably a single bond used for bonding to L ¹ .
Alternatively, the ^{R 102} in formula (1) is preferably a single bond for use in binding to ^{L 1.}

R ^{109 of the} general formula (1) is
A group selected from 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 is preferable.
Then, it is preferable that the ^{R 109} in formula (1) is represented by the following general formula (11).

In the general formula (11), Ar ¹ is
A group selected from 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.
In the general formula (11), Ra has the same meaning as R ^{101 to} R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
In the general formula (11), d represents an integer of 1 to 4.
In said General Formula (11), when d is 2-4, several Ra is the same or different.

In addition, it is preferable that R ¹⁰⁹ of the general formula (1) is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms.

In addition, R ¹⁰⁹ in the above (1) is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms, and R ^{110 in the} above general formula (1) is used for bonding to L ^1. It is preferable that it is a single bond.
In the general formula (1), a is 1, and the linking group is formed by removing two hydrogen atoms from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 30 ring carbon atoms. A divalent residue is preferable, a divalent residue having a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 10 ring carbon atoms is more preferable, and a phenylene group is more preferable.

Next, each substituent described in the general formulas (1) to (3), (2-4) to (2-6), and (11) will be described.
Specific examples of the substituents described in the general formulas (1) to (3), (2-4) to (2-6), and (11) include
Halogen atoms,
Hydroxyl group,
A cyano group,
Nitro group,
Carboxyl group,
A substituted or unsubstituted silyl group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group,
A substituted or unsubstituted C1-C20 linear, branched or cyclic haloalkyl group,
A substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 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 aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
Examples thereof include a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

  Examples of the halogen atom in the general formulas (1) to (3), (2-4) to (2-6) and (11) include fluorine, chlorine, bromine and iodine, and fluorine is preferable. .

  Examples of the substituted or unsubstituted amino group in the general formulas (1) to (3), (2-4) to (2-6), (11) include amino groups substituted with each substituent, An amino group substituted with an aromatic hydrocarbon group is preferred, and an amino group substituted with a phenyl group is more preferred. Examples of the aromatic hydrocarbon group substituted for the amino group include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.

The alkyl group having 1 to 20 carbon atoms in the general formulas (1) to (3), (2-4) to (2-6), and (11) may be linear, branched, or cyclic. Examples of the linear or branched alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an 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, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl 3-methylpentyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy -T-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloro Isopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl , Iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2 , 3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3- Diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyano Isopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl Group, 1,2-dinitroethyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1, Examples include 1,1,3,3,3-hexafluoro-2-propyl group.
Examples of the cyclic alkyl group (cycloalkyl group) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group,
Examples include cyclooctyl group, 4-methylcyclohexyl group, 3,5-tetramethylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
Among the alkyl groups, an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable. Of these, a methyl group, an isopropyl group, a t-butyl group, and a cyclohexyl group are preferable.

  Examples of the linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms include those 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, and a trifluoromethylmethyl group.

The linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the general formulas (1) to (3), (2-4) to (2-6) and (11) is -OY ¹ It is expressed. Examples of ^{Y 1,} include an alkyl group having 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. Among the alkoxy groups, an alkoxy group having 1 to 10 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms is more preferable. Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.
Examples of the linear, branched or cyclic haloalkoxy groups having 1 to 20 carbon atoms in the general formulas (1) to (3), (2-4) to (2-6) and (11) include, for example, And those in which the alkoxy group having 1 to 20 carbon atoms is substituted with one or more halogen groups.

The aralkyl group having 7 to 30 carbon atoms in the general formula (1-1) is represented as —R ^X —R ^Y. Examples of R ^X include alkylene groups corresponding to the alkyl groups having 1 to 30 carbon atoms. Examples of this ^RY include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. In this aralkyl group, the aromatic hydrocarbon group portion has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Moreover, in this aralkyl group, the alkyl group moiety has 1 to 30, preferably 1 to 20, more preferably 1 to 10, and further preferably 1 to 6 carbon atoms. 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- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group P-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o -Cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group.

Formula (1) to (3), (2-4) to (2-6), an aryloxy group ring forming C6-30 in (11) is represented as -OZ ^2. Examples of Z ² include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.
Formula (1) to (3), (2-4) to (2-6), ring formation arylthio group having 6 to 30 carbon atoms in the (11) is expressed as -SZ ^3. Examples of Z ³ include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.

  In the general formulas (1) to (3), (2-4) to (2-6) and (11), the aromatic hydrocarbon group having 6 to 30 ring carbon atoms is a non-condensed aromatic hydrocarbon group. More specifically, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a fluoranthenyl group, a pyrenyl group, and a triphenylenyl group. , Phenanthrenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] Examples include a triphenylenyl group, a dibenzo [a, c] triphenylenyl group, and a benzo [b] fluoranthenyl group. Among the aromatic hydrocarbon groups, an aromatic hydrocarbon group having 6 to 20 ring carbon atoms is more preferable, and an aromatic hydrocarbon group having 6 to 12 ring carbon atoms is particularly preferable.

  Examples of the heterocyclic group having 5 to 30 ring atoms in the general formulas (1) to (3), (2-4) to (2-6) and (11) include a non-condensed heterocyclic ring and a condensed heterocyclic ring. More specifically, pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group Group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, thienyl group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring , Pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan Thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, benzo [c] dibenzofuran ring Group to be used. Among the heterocyclic groups, a heterocyclic group having 5 to 20 ring atoms is more preferable, and a heterocyclic group having 5 to 12 ring atoms is particularly preferable.

Examples of the silyl group in the general formulas (1) to (3), (2-4) to (2-6) and (11) include an unsubstituted silyl group, an alkylsilyl group having 1 to 30 carbon atoms, and An arylsilyl group having 6 to 60 carbon atoms is exemplified.
Examples of the alkylsilyl group having 1 to 30 carbon atoms include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, specifically, a trimethylsilyl group, 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-butylsilyl group, diethyl Examples include isopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triisopropylsilyl group and the like. The three alkyl groups may be the same or different from each other.
Examples of the arylsilyl group having 6 to 60 ring carbon atoms include an arylsilyl group, an alkylarylsilyl group, a dialkylarylsilyl group, a diarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. A plurality of aryl groups or alkyl groups may be the same or different.
Examples of the dialkylarylsilyl group include a dialkylarylsilyl group having two alkyl groups exemplified for the alkyl group having 1 to 20 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. . The carbon number of the dialkylarylsilyl group is preferably 8-30. The two alkyl groups may be the same or different.
Examples of the alkyldiarylsilyl group include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 20 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. . The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms. The two aryl groups may be the same or different.
Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30. The three aryl groups may be the same or different from each other.
Examples of such an arylsilyl group include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl-t-butylsilyl group, and a triphenylsilyl group.

In the general formula (1), R ^{101 to} R ¹¹⁰ that are not used for bonding with L ¹ are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
When R ¹⁰⁹ is a condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms, more preferably, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group and 4-methyl-1-anthryl group.

In the general formula (1), when L ¹ is a linking group, a substituted or unsubstituted (a + 1) -valent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted (a + 1) -valent Or a divalent group formed by combining 2 to 4 of these aromatic hydrocarbon groups or heterocyclic groups.
Specific examples of the (a + 1) -valent aromatic hydrocarbon group having 6 to 30 ring carbon atoms include those listed above as the aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Based on this.
Specific examples of the (a + 1) -valent heterocyclic group having 5 to 30 ring atoms include those mentioned as the heterocyclic group having 5 to 30 ring atoms as the (a + 1) -valent group. The thing which was done is mentioned.
When L ¹ is an (a + 1) -valent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, more preferred aromatic hydrocarbon groups include a phenyl group, a biphenyl group, a naphthyl group, and 9,9-dimethylful. The thing which made the oleenyl group into bivalent group is mentioned.
When L ¹ is a (a + 1) -valent heterocyclic group having 6 to 30 ring atoms, a more preferable heterocyclic group is a pyridyl group, pyrimidyl group, dibenzofuranyl group, or carbazolyl group as a divalent group. Things.

R ^{111 to} R ¹¹⁸ that are not used for bonding to L ¹ in the general formula (2) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
R ^{119 to} R ¹²⁰ in the general formula (2) are preferably alkyl groups, more preferably methyl groups, and R ¹¹⁹ and R ¹²⁰ are both methyl groups. preferable.
R ^{121 to} R ¹²⁴ in the general formula (3) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

In the general formula (11), Ar ¹ is particularly preferably a phenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, or a biphenyl group.
Ra is particularly preferably a hydrogen atom, an aryl group, or a heterocyclic group.

In the present invention, “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 invention, 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. , Alkoxy group, aryloxy group, aralkyl group, haloalkoxy group, alkylsilyl group, dialkylarylsilyl group, alkyldiarylsilyl group, triarylsilyl group, halogen atom, cyano group, hydroxyl group, nitro group, and carboxy group Can be mentioned. In addition, an alkenyl group and an alkynyl group are also included.
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.
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 specification, “carbon number ab” in the expression “XX group having a substituted or unsubstituted carbon number ab” represents the number of carbon atoms when the XX group is unsubstituted. The number of carbon atoms of the substituent when the XX group is substituted is not included.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

  Specific examples of the anthracene derivative represented by the general formula (1) are shown below, but the present invention is not limited to these exemplified compounds.

-Dopant material As a dopant material used for the organic EL element of this invention, the fluoranthene derivative represented by following General formula (21) can be used.

In the general formula (21), R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ³¹ are each independently
Hydrogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
Silyl group,
Carboxyl group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 7 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 alkoxycarbonyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
It is selected from the first 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.

In the general formula ^{(21), R 23 is} selected from the second group constituted by a hydrogen atom is removed from ^{R 21, R 22, R 25} , the first gun given for ^{R 26} and ^R 28 ^{to R 31} It is. That is, the second group is
Hydroxyl group,
A cyano group,
Nitro group,
Silyl group,
Carboxyl group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 7 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 alkoxycarbonyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
It consists 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.

In the general formula (21), R ²⁴ is constituted by removing an aromatic hydrocarbon group and a heterocyclic group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. Selected from the third group. That is, the third group is
Hydrogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
Silyl group,
Carboxyl group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 7 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,
It consists of a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms and a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms.

In the general formula (21), R ²⁷ and R ³² are each independently a hydrogen atom or a hydroxyl group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. , A cyano group, a nitro group, a silyl group and a carboxyl group are selected from the fourth group. That is, the fourth group is
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 7 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 alkoxycarbonyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
It consists 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.

In the general formula (21), R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , and R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring, or may not form a saturated or unsaturated ring. Substituted or unsubstituted.
However, in the general formula (21), the case where R ^{21 to} R ²³ and R ^{25 to} R ³² are monovalent groups derived from benzo [k] fluoranthene is excluded.
In the general formula (21), R ²³ and R ²⁴ are different from each other.
In the general formula (21), the case where any of R ²³ and R ²⁴ is an α-naphthyl group is excluded.

R ^{24 in the} general formula (21) is preferably a hydrogen atom.
In the general formula (21), R ²⁷ and R ³² are preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Further, it is preferable that the ^{R 27} and ^{R 32} in the general formula (21) is a substituted or unsubstituted phenyl group.

Alternatively, R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms, and R ²³ , R ²⁷ and R ^{32 in the} general formula (21) are substituted. Alternatively, it is preferably an unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms, and R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted rings. an aromatic hydrocarbon group having 6 to 30 carbon atoms, ^{R 23} in the general formula (21) ^is a -Ar 21 ^{-Ar 22, Ar 21} and ^{Ar 22} each independently substituted or unsubstituted It is preferably an aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
In this case, it is preferable that Ar ²¹ or Ar ²² is an aromatic hydrocarbon group having a cyano group as a substituent.

Alternatively, R ^{21 to} R ²² , R ^{24 to} R ^26, and R ^{28 to} R ³¹ in the general formula (21) are hydrogen atoms, and R ²⁷ and R ^{32 in} the general formula (21) are substituted or not. A substituted aromatic hydrocarbon group having 6 to 30 carbon atoms in the ring, R ^{23 in the} general formula (21) is —Ar ²¹ —Ar ²² —Ar ²³ , and Ar ²¹ , Ar ^22, and Ar ²³ are And each independently preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
In this case, it is preferable that the Ar ²¹ , the Ar ²² or the Ar ²³ is an aromatic hydrocarbon group having a cyano group as a substituent.

Specific examples of the groups listed in the first group to the fourth group selected for R ^{21 to} R ³² of the general formula (21) include the general formulas (1) to (3) and (2-4). ) To (2-6), those exemplified in the description of (11).

  Specific examples of the fluoranthene derivative represented by the general formula (21) are shown below, but the present invention is not limited to these exemplified compounds.

  There is no restriction | limiting in particular in content in the light emitting layer of dopant material, Although it can select suitably according to the objective, For example, 0.1 to 70 mass% is preferable, and 1 to 30 mass% is preferable. Is more preferable. When the content of the dopant material is 0.1% by mass or more, sufficient light emission can be obtained, and when it is 70% by mass or less, concentration quenching can be avoided.

-Combination of host material and dopant material In the organic EL element of this embodiment, the anthracene derivative substituted by the fluorene ring is used as a host material, and the fluoranthene derivative represented by Formula (21) is used as a dopant material. When an anthracene derivative having such a structure is used as a host material, it is expected that packing between molecules is improved and charge mobility is increased due to the planarity of the fluorene ring. In that case, electric charges may leak from the light emitting layer, and efficiency and lifetime may be reduced. Therefore, it is considered that high efficiency and long life can be achieved by confining carriers in the light emitting layer by using a dopant having an electron or hole trapping property and a condensed ring structure.
Since the fluoranthene derivative is considered to have an electron trapping property and a condensed ring structure, when it is used as a dopant material with respect to the host material, it can be expected to increase the efficiency and life of the organic EL element in particular. .

(Hole injection / transport layer)
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and a compound having a high hole mobility and a low ionization energy is used.
As a material for forming the hole injecting / transporting layer, a material that transports holes to the light emitting layer with lower electric field strength is preferable. For example, an aromatic amine compound is preferably used.

(Electron injection / transport layer)
The electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer and transports it to the light emitting region, and a compound having a high electron mobility is used.
As the compound used in the electron injecting / transporting layer, for example, an aromatic heterocyclic compound containing one or more hetero atoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. As the nitrogen-containing ring derivative, a heterocyclic compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton is preferable.

  In the organic EL device of the present invention, any compound other than the above-exemplified compounds can be selected and used for the organic layers other than the light emitting layer from materials used in conventional organic EL devices.

(substrate)
The organic EL element of the present invention is produced on a light-transmitting substrate. The translucent substrate referred to here is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
Specifically, a glass plate, a polymer plate, etc. are mentioned.
Examples of the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
Examples of the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.

(Anode and cathode)
The anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
The anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
When light emitted from the light emitting layer is extracted from the anode as in the present embodiment, it is preferable that the light transmittance in the visible region of the anode be greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ (ohm / square) or less. The film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 10 nm to 200 nm.

As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer, or the light emitting layer.
The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
Similarly to the anode, the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, the aspect which takes out light emission from a cathode side is also employable. Moreover, the aspect which takes out light emission from a light emitting layer from a cathode side is also employable. When light emitted from the light emitting layer is extracted from the cathode side, it is preferable that the light transmittance in the visible region of the cathode be greater than 10%.
The sheet resistance of the cathode is preferably several hundred Ω / □ or less.
The layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 50 nm to 200 nm.

(Method for forming each layer of organic EL element)
The formation method of each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. The organic layer used in the organic EL device of the present invention may be formed by vacuum deposition, molecular beam deposition (MBE, MBE; Molecular Beam Epitaxy) or a solution dipping method in a solvent, spin coating method, casting method, bar coating. It can be formed by a known method using a coating method such as a method or a roll coating method.

(Thickness of each layer of organic EL element)
The thickness of the light emitting layer is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. By setting the thickness of the light emitting layer to 5 nm or more, it becomes easy to form the light emitting layer and adjust the chromaticity. By setting the film thickness of the light emitting layer to 50 nm or less, an increase in driving voltage can be suppressed.
The film thickness of each of the other organic layers is not particularly limited, but usually a range of several nm to 1 μm is preferable. By making such a film thickness range, defects such as pinholes caused by the film thickness being too thin are prevented, and an increase in driving voltage caused by the film thickness being too thick is suppressed, resulting in deterioration of efficiency. Can be prevented.

[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 included in this invention.

The light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL device has a plurality of light emitting layers, at least one light emitting layer may contain the compound represented by the general formula (1) and the compound represented by the general formula (21). The other light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer.
In addition, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.

In the present invention, it is also preferable that the light emitting layer contains a charge injection auxiliary material.
When a light emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light emitting layer. This may make it difficult to increase the driving voltage for obtaining sufficient luminance.
In such a case, by adding a hole injection / transport charge injection auxiliary agent to the light emitting layer, hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.

As the charge injection auxiliary agent, for example, a general hole injection / transport material or the like can be used.
Specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, fluorenone derivatives, hydrazone derivatives, stilbenes. Derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), and the like can be given.

  Examples of the hole-injecting material include those described above, and porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.

In addition, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD) having two condensed aromatic rings in the molecule, or triphenylamine 4,4 ′, 4 ″ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA) and the like in which three units are connected in a starburst type. it can.
A hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.

  The organic EL element of the present invention can be suitably used as an electronic device such as a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicular lamp.

  EXAMPLES Next, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not restrict | limited at all to the description content of these Examples.

[Example of manufacturing organic EL element]
Example 1
A glass substrate with an ITO transparent electrode of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
The glass substrate with the ITO transparent electrode line after washing is mounted on the substrate holder of the vacuum evaporation apparatus, and the following compound (HI-1) is first covered so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed. ) To form a HI-1 film having a thickness of 5 nm to form a hole injection layer.
Next, on the HI-1 film, the following compound HT-1 was deposited as a first hole transport material to form an HT-1 film having a thickness of 80 nm to form a first hole transport layer.
Next, on this HT-1 film, the following compound HT-2 (compound 1 obtained in Synthesis Example 1) is deposited to form an HT-2 film having a film thickness of 15 nm, and the second hole transport A layer was formed.
Furthermore, on this HT-2 film | membrane, compound BH-1 was vapor-deposited and the light emitting layer with a film thickness of 25 nm was formed into a film. At the same time, the following compound (BD-1) was co-deposited as a fluorescent material. The concentration of Compound BD-1 was 5.0% by mass. This co-deposited film functions as a light emitting layer.
And on this light emitting layer, the following compound ET-1 was vapor-deposited and the ET-1 film | membrane with a film thickness of 25 nm was formed into a film, and the 1st electron carrying layer was formed.
Next, LiF was deposited on the ET-1 film at a deposition rate of 0.1 angstrom / min to form a 1 nm-thick LiF film to form an electron injecting electrode (cathode).
And metal Al was vapor-deposited on this LiF film | membrane, the metal Al film | membrane with a film thickness of 80 nm was formed into a film, and the metal Al cathode was formed.

  The compound used for manufacture of an organic EL element is shown below.

・ Comparative Examples 1-3
The organic EL elements of Comparative Examples 1 to 3 were produced in the same manner as in Example 1 except that at least one of the host material and the dopant material of the light emitting layer in Example 1 was changed to the compounds shown in Table 1.

[Evaluation of organic EL elements]
With respect to the produced organic EL element, voltage was applied so that the current density was 10 mA / cm ^2, and CIE1931 chromaticity, current efficiency L / J, external quantum efficiency EQE, main peak wavelength λ _p , and lifetime LT90 were evaluated. went. The results are shown in Table 2. About each evaluation item of a drive voltage, current efficiency L / J, external quantum efficiency EQE, and lifetime LT90, the value of each evaluation item of Example 1 and Comparative Examples 1-3 with respect to the value of each evaluation item of Comparative Example 1 It is a value obtained by calculating the ratio.

CIE1931 chromaticity CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the element so that the current density was 10 mA / cm ² were measured with the spectral radiance meter.

・ Current efficiency L / J,
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 10 mA / cm ² was measured with the above spectral radiance meter, and the current efficiency (unit: cd / A) was calculated from the obtained spectral radiance spectrum. ) Was calculated.

・ External quantum efficiency EQE
From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit:%) was calculated on the assumption that Lambtian radiation was performed.

・ Main peak wavelength λ _p
The main peak wavelength λ _p was determined from the obtained spectral radiance spectrum.

・ Lifetime LT90
A voltage was applied to the device so that the current density was 50 mA / cm ^2, and the time (unit: h) until the luminance became 90% with respect to the initial luminance was measured.

  As Table 2 shows, it was found that the organic EL element of Example 1 was a long-life organic EL element with higher luminous efficiency than the organic EL elements of Comparative Examples 1 to 3. For example, the organic EL element of Example 1 has an external quantum efficiency EQE of about 2.6 times, a life LT90 of about 11 times, a high light emission efficiency, and a long life as compared with the organic EL element of Comparative Example 1. It turns out that.

  The organic EL element of the present invention can be used as a light emitting element in a display device or a lighting device.

1 ... Organic EL element 2 ... Substrate
3 ... Anode
4 ... Cathode
5 ... Light emitting layer
6 ... Hole transport layer
7 ... Electron transport layer
10 ... Organic layer

Claims (18)

The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode and including at least a light-emitting layer,
The said light emitting layer contains the anthracene derivative represented by following General formula (1), and the fluoranthene derivative represented by following General formula (21). The organic electroluminescent element characterized by the above-mentioned.
[In the general formula (1),
Any one of R ^{101 to} R ¹¹⁰ is a single bond and is used for bonding to L ¹ ;
R ^{101 to} R ¹¹⁰ not used for bonding with L ¹ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
Selected from 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 is selected from either a single bond or a linking group;
The linking group is
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 30 carbon atoms,
A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 30 ring atoms, or the aromatic hydrocarbon ring structure and the heterocyclic structure A (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a structure formed by bonding at least 2 to 4 of any one of them,
a, b, and c each represent an integer of 1 to 4.
Z ¹ represents a structure represented by the following general formula (2). ]
[R ^{119 to} R ¹²⁰ in the general formula (2) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted trialkylsilyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Selected from 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;
Any one of R ^{111 to} R ¹¹⁸ is a single bond used for bonding to L ¹ ;
R ^{111 to} R ^{118 that} are not used for bonding to L ¹ are each independently synonymous with R ^{101 to} R ¹¹⁰ that are not used to bond to L ¹ .
Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). ]
[In the general formula ^(3), y 1, ^{y 2} shows a set of binding position adjacent in ^R 111 ^{to R 118} in the general formula (2).
R ^{121 to} R ¹²⁴ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted amino group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms,
It is selected from either 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.
In the general formula (2), any one of R ^{111 to} R ¹¹⁸ that does not form a ring and any one of R ^{121 to} R ^{124 in} the general formula (3) is a single bond, and the general formula (1) used in the coupling with L ^1. ]

[In the said General formula (21), R ^< 21>, R < ²² >, R < ²⁵ >, R < ²⁶ > and R < ²⁸ > -R < ³¹ > are respectively independently,
Hydrogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
Silyl group,
Carboxyl group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl 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 20 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 alkoxycarbonyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms,
It is selected from the first 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.
R ²³ is selected from the second group constituted by removing hydrogen atoms from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ³¹ .
R ²⁴ is selected from the third group constituted by removing the aromatic hydrocarbon group and the heterocyclic group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. .
R ²⁷ and R ³² are each independently a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a silyl group from the first group shown for R ²¹ , R ²² , R ²⁵ , R ²⁶ and R ^{28 to} R ^31. Selected from the fourth group consisting of a group and a carboxyl group.
R ²¹ and R ²² , R ²² and R ²³ , R ²⁵ and R ²⁶ , R ²⁶ and R ²⁷ , R ²⁷ and R ²⁸ , R ²⁸ and R ²⁹ , R ²⁹ and R ³⁰ , R ³⁰ and R ³¹ , R ³¹ and R ³² may be bonded to each other to form a saturated or unsaturated ring and may not form a saturated or unsaturated ring, and the ring is substituted or unsubstituted.
Except when R ^{21 to} R ²³ and R ^{25 to} R ³² are monovalent groups derived from benzo [k] fluoranthene.
R ²³ and R ²⁴ are different from each other.
Except when one of R ²³ and R ²⁴ is an α-naphthyl group. ] The organic electroluminescent device according to claim 1,
Wherein the ^{Z 1} in the general formula (1), the following general formula (2-4), (2-5), an organic electroluminescent device characterized by being represented by any one of (2-6).
[Ar ^{161 to} Ar ¹⁶² in General Formula (2-4), Ar ^{171 to} Ar ¹⁷² in General Formula (2-5), and Ar ^{181 to} Ar ¹⁸² in General Formula (2-6) are each independently , Which has the same meaning as R ^{119 to} R ¹²⁰ in the general formula (2).
1 one of ^R 161 ^{to R 170} in the general formula (2-4) is used for binding to ^{L 1} represents a single bond, ^R 161 ^{to R 170} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 171 ^{to R 180} in the general formula (2-5) is used for binding to ^{L 1} represents a single bond, ^R 171 ^{to R 180} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ .
1 one of ^R 181 ^{to R 190} in the general formula (2-6) is used for binding to ^{L 1} represents a single bond, ^R 181 ^{to R 190} which are not used in binding to ^{L 1} is, Each is independently synonymous with R ^{101 to} R ¹¹⁰ not used for bonding to L ¹ . ] In the organic electroluminescent element according to claim 1 or 2,
B of the said General formula (1) is 1. The organic electroluminescent element characterized by the above-mentioned. In the organic electroluminescent element according to any one of claims 1 to 3,
A of the said General formula (1) is 1 or 2. The organic electroluminescent element characterized by the above-mentioned. In the organic electroluminescent element according to any one of claims 1 to 4,
At least one of R ¹⁰⁹ and R ^{110 in} the general formula (1) is a single bond used for bonding to L ^1. An organic electroluminescence device, wherein: In the organic electroluminescent element according to any one of claims 1 to 4,
At least one of R ¹⁰¹ to R ^{104 in} the general formula (1) is a single bond used for bonding to L ^1. An organic electroluminescence element, wherein: The organic electroluminescence device according to claim 6,
The organic electroluminescence device, wherein R ^{102 in the} general formula (1) is a single bond used for bonding to L ¹ . In the organic electroluminescent element according to any one of claims 1 to 7,
R ^{109 of the} general formula (1) is
Organic electroluminescence characterized by being a group selected from 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 element. The organic electroluminescent device according to claim 8, wherein
R ¹⁰⁹ of the general formula (1) is represented by the following general formula (11), an organic electroluminescence element.
[In the general formula (11), Ar ¹ represents
A group selected from 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.
Each Ra has the same meaning as R ^{101 to} R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
d shows the integer of 1-4.
When d is 2 to 4, a plurality of Ra are the same or different. ] The organic electroluminescent device according to claim 8, wherein
R ¹⁰⁹ of the general formula (1) is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms. In the organic electroluminescent element according to any one of claims 1 to 10,
Wherein R ²⁴ in formula (21) The organic electroluminescent device which is a hydrogen atom. In the organic electroluminescent element according to any one of claims 1 to 11,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. An organic electroluminescence device, wherein: The organic electroluminescence device according to claim 12,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted phenyl groups. An organic electroluminescence device, wherein: In the organic electroluminescent element according to any one of claims 1 to 10,
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
R <^23> , R <^27> and R ^<32 > of the said General formula (21) are substituted or unsubstituted aromatic hydrocarbon groups with 6-30 ring forming carbon atoms. The organic electroluminescent element characterized by the above-mentioned. In the organic electroluminescent element according to any one of claims 1 to 10,
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms,
R ^{23 in the} general formula (21) is —Ar ²¹ —Ar ²² ,
Ar ²¹ and Ar ²² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. An organic electroluminescence device, wherein: In the organic electroluminescent element according to any one of claims 1 to 10,
R ^{21 to} R ²² , R ^{24 to} R ²⁶ and R ^{28 to} R ^{31 in the} general formula (21) are hydrogen atoms,
R ²⁷ and R ^{32 in} the general formula (21) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms,
R ^{23 in the} general formula (21) is —Ar ²¹ —Ar ²² —Ar ²³ ,
Ar < ²¹ >, Ar < ²² > and Ar < ²³ > are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. The organic electroluminescence device according to claim 15,
The Ar ²¹ or Ar ²² is an aromatic hydrocarbon group having a cyano group as a substituent. An organic electroluminescence device, wherein: The organic electroluminescence device according to claim 16,
Ar ²¹ , Ar ^22, or Ar ²³ is an aromatic hydrocarbon group having a cyano group as a substituent. An organic electroluminescence device, wherein: