WO2018194035A1

WO2018194035A1 - Novel compound, organic electroluminescent element material using same, organic electroluminescent element, and electronic device

Info

Publication number: WO2018194035A1
Application number: PCT/JP2018/015752
Authority: WO
Inventors: 敬太瀬田; 良多高橋; 裕基中野; 聡美田崎; 祐一郎河村; 舟橋　正和; 池田　秀嗣
Original assignee: 出光興産株式会社
Priority date: 2017-04-17
Filing date: 2018-04-16
Publication date: 2018-10-25

Abstract

A compound represented by formula (1). (In formula (1), at least one pair selected from among a pair of R1 and R2, a pair of R2 and R3, a pair of R3 and R4, a pair of R5 and R6, a pair of R6 and R7, and a pair of R7 and R8 may combine with each other to form a ring represented by formula (1A); and at least one of R1-R12 and R15-R18 represents a cyano group, a substituted or unsubstituted aryl group having 6-50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5-50 ring-forming atoms, or a group represented by formula (2).)

Description

Novel compound, material for organic electroluminescence device using the same, organic electroluminescence device and electronic equipment

The present invention relates to a novel compound, an organic electroluminescence element material using the same, an organic electroluminescence element and an electronic device.

When a voltage is applied to an organic electroluminescence element (hereinafter referred to as an organic EL element), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.

The organic EL element includes a light emitting layer between the anode and the cathode. Moreover, it may have a laminated structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

Patent Documents 1 to 3 disclose compounds used in organic EL elements.

JP 2013-232521 A US Patent Application Publication No. 2010/0032658 International Publication No. 2006/122630

An object of the present invention is to provide a compound having a high fluorescence quantum yield, a material for an organic electroluminescence element using the compound, an organic electroluminescence element, and an electronic apparatus.

According to one aspect of the present invention, the following compounds are provided.
A compound represented by the following formula (1).

(In the formula (1), R ₁ to R ₁₂ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, or a substituted group. Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ), —C (═O) R ₂₄ , —COOR ₂₅ , halogen atom, cyano group, nitro group, substituted or Represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (2): R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are bonded to each other and represented by the following formula (1A). May be formed.

(In the formula (1A), R ₁₅ to R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ), —C (═O) R ₂₄ , —COOR ₂₅ , halogen atom, cyano group, nitro group, substitution Or an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (2).
At least one of R ₁ to R ₁₂ and R ₁₅ to R ₁₈ is a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. It is a group represented by a cyclic group or the following formula (2).
R ₂₁ to R ₂₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms.
X ₁ and X ₂ each independently represent an oxygen atom, a sulfur atom or C (R ₁₃ ) (R ₁₄ ).
R ₁₃ and R ₁₄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms. R ₁₃ and R ₁₄ may combine with each other to form a saturated or unsaturated ring.

(In Formula (2), Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. It is a group.
L ₁ , L ₂ and L ₃ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms. It is. )
If Ar _1, _Ar _2, L 1, _{L 2} and _{L 3} are present 2 or more, two or more _Ar _1, Ar _2, L 1, each of _{L 2} and _{L 3} may be the same or may be different . )

According to another aspect of the present invention, a material for an organic electroluminescence device comprising the above compound is provided.

According to another aspect of the present invention, the following organic EL device is provided.
A cathode,
The anode,
An organic layer disposed between the cathode and the anode;
Have
The organic electroluminescent element in which the said organic layer contains the above-mentioned compound.

According to another aspect of the present invention, the following organic EL device is provided.
A cathode,
The anode,
A light emitting layer disposed between the cathode and the anode;
Have
The organic electroluminescent element in which the said light emitting layer contains the above-mentioned compound.

According to another aspect of the present invention, an electronic device including the organic EL element is provided.

According to the present invention, it is possible to provide a compound having a high fluorescence quantum yield, a material for an organic electroluminescence element, an organic electroluminescence element and an electronic apparatus using the compound.

It is a figure which shows schematic structure of one Embodiment of the organic EL element of this invention.

In this specification, the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (triuterium), and tritium.

In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (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 specification, 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-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming 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.

In the present specification, 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. The carbon number of the substituent in the case where it is present is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

In this specification, “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. In this case, the number of substituent atoms is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

In the case of “substituted or unsubstituted”, “unsubstituted” means that a hydrogen atom is bonded without being substituted with the above substituent.

In the present specification, the heterocyclic group includes the following groups. In addition, the heteroarylene group includes a group in which the following group is a divalent group.

(Wherein X _1A to X _6A , Y _1A to Y _6A are each an oxygen atom, a sulfur atom, a —NZ— group, or a —NH— group. Z represents a substituted or unsubstituted ring-forming carbon number of 6 to 6. An aryl group of 50, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and when Z is 2 or more, 2 or more Z may be the same or different.)

Examples of the aryl group having 6 to 50 ring carbon atoms of Z include those similar to the aryl groups having 6 to 50 ring carbon atoms such as R ₁ to R ₁₂ described later.
Examples of the heterocyclic group having 5 to 50 ring atoms of Z include those similar to the heterocyclic groups having 5 to 50 ring atoms such as R ₁ to R ₁₂ described later.
Examples of the alkyl group having 1 to 50 carbon atoms for Z include those similar to the alkyl groups having 1 to 50 carbon atoms such as R ₁ to R ₁₂ described later.

One embodiment of the compound of the present invention is represented by the following formula (1).

(In the formula (1A), R ₁₅ to R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ), —C (═O) R ₂₄ , —COOR ₂₅ , halogen atom, cyano group, nitro group, substitution Or an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (2).
At least one of R ₁ to R ₁₂ and R ₁₅ to R ₁₈ (preferably 2 or more, more preferably 2) is a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or It is an unsubstituted heterocyclic group having 5 to 50 ring atoms or a group represented by the following formula (2).
R ₂₁ to R ₂₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms.
X ₁ and X ₂ each independently represent an oxygen atom, a sulfur atom or C (R ₁₃ ) (R ₁₄ ).
R ₁₃ and R ₁₄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms. R ₁₃ and R ₁₄ combine with each other to form a saturated or unsaturated ring (preferably a saturated or unsaturated, substituted or unsubstituted 5-membered ring, 6-membered ring, or 7-membered ring or more). May be.

Thereby, the fluorescence quantum yield can be improved.

Two or more (preferably 2 or more and 3 or less) of R ₁ to R ₁₂ and R ₁₅ to R ₁₈ are preferably groups represented by the formula (2).

Two of R ₁ to R ₁₂ and R ₁₅ to R ₁₈ are preferably groups represented by the formula (2).

The compound represented by the formula (1) is preferably represented by the following formula (3).

(In Formula (3), X ₁ and X ₂ are as defined in Formula (1) above. Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ are defined in Formula (2) above. Street.
R ₁ , R ₂ , R ₄ to R ₆ , and R ₈ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms _{_{_{of, -Si (R 21) (R}}} 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R ₁ and R ₂ may combine with each other to form a ring represented by the formula (1A). R ₅ and R ₆ may combine with each other to form a ring represented by the formula (1A).
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

The compound represented by the formula (1) is preferably represented by the following formula (4).

(In Formula (4), X ₁ and X ₂ are as defined in Formula (1) above. Ar ₁ , Ar ₂ , L ₁ and L ₂ are as defined in Formula (2) above. .
R ₁ , R ₂ , R ₄ to R ₆ , and R ₈ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms _{_{_{of, -Si (R 21) (R}}} 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R ₁ and R ₂ may combine with each other to form a ring represented by the formula (1A). R ₅ and R ₆ may combine with each other to form a ring represented by the formula (1A).
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

The compound represented by the formula (1) is preferably represented by the following formula (5).

(In Formula (5), X ₁ and X ₂ are as defined in Formula (1). Ar ₁ and Ar ₂ are as defined in Formula (2) above.
R ₁ , R ₂ , R ₄ to R ₆ , and R ₈ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms _{_{_{of, -Si (R 21) (R}}} 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R ₁ and R ₂ may combine with each other to form a ring represented by the formula (1A). R ₅ and R ₆ may combine with each other to form a ring represented by the formula (1A).
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

In the formula (1), R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are all bonded to each other. Without forming a ring represented by the formula (1A), or R ₂ and R ₃ are bonded to each other to form a ring represented by the formula (1A), and R ₆ and R ₇ are bonded to each other. Forming a ring represented by the formula (1A), and none of R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ , and R ₇ and R ₈ are bonded to each other; It is preferable not to form a ring represented by the formula (1A).

In the formulas (3) to (5), it is preferable that R ₁ and R ₂ and R ₅ and R ₆ are not bonded to each other and do not form a ring represented by the formula (1A).

R ₁ , R ₂ , R ₄ to R ₆ and R ₈ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring carbon number of 6 It is preferably selected from the group consisting of ˜50 aryl groups and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.

R ₁ , R ₂ , R ₄ to R ₆ and R ₈ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring formation. It is preferably selected from the group consisting of a heterocyclic group having 5 to 50 atoms.

R ₁ , R ₂ , R ₄ to R ₆ and R ₈ to R ₁₂ each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted ring formation. It is preferably selected from the group consisting of heterocyclic groups having 5 to 18 atoms.

The compound represented by the formula (1) is preferably represented by the following formula (6).

(In Formula (6), X ₁ and X ₂ are as defined in Formula (1) above. Ar ₁ and Ar ₂ are as defined in Formula (2) above.)

In the compound represented by the formula (1), R ₂ and R ₃ are bonded to each other to form a ring represented by the formula (1A), and R ₆ and R ₇ are bonded to each other. It is preferable to form a ring represented by 1A). Specifically, the following compounds are preferable.

The compound represented by the formula (1) is preferably represented by the following formula (7).

(In Formula (7), X ₁ and X ₂ are as defined in Formula (1) above. Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ are defined in Formula (2) above. Street.
R ₁ , R ₄ , R ₅ , R ₈ to R ₁₂ , R ₁₅ , R ₁₆ and R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of _{_{_{7 ~ 50, -Si (R 21}}} ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R ₁₅ , R ₁₆ and R ₁₈ may be the same or different.
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

The compound represented by the formula (1) is preferably represented by the following formula (8).

(In the formula (8), X ₁ and X ₂ are as defined in the formula (1). Ar ₁ , Ar ₂ , L ₁ and L ₂ are as defined in the formula (2). .
R ₁ , R ₄ , R ₅ , R ₈ to R ₁₂ , R ₁₅ , R ₁₆ and R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of _{_{_{7 ~ 50, -Si (R 21}}} ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R ₁₅ , R ₁₆ and R ₁₈ may be the same or different.
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

The compound represented by the formula (1) is preferably represented by the following formula (9).

(In Formula (9), X ₁ and X ₂ are as defined in Formula (1) above. Ar ₁ and Ar ₂ are as defined in Formula (2) above.
R ₁ , R ₄ , R ₅ , R ₈ to R ₁₂ , R ₁₅ , R ₁₆ and R ₁₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of _{_{_{7 ~ 50, -Si (R 21}}} ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R ₁₅ , R ₁₆ and R ₁₈ may be the same or different.
R ₂₁ to R ₂₅ are as defined in the above formula (1). )

X ₁ and X ₂ are preferably oxygen atoms.

Ar ₁ and Ar ₂ are preferably selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group.

The substituent in the case of “substituted or unsubstituted” will be described later.

One embodiment of the compound of the present invention is preferably a material for an organic electroluminescence element.

R ₁ to R ₁₂ , R ₁₃ and R ₁₄ , R ₁₅ to R ₁₈ , R ₂₁ to R ₂₅ , R ₃₁ to R ₄₃ described later, R ₁₀₁ to R ₁₁₀ described later, and R ₁₂₁ to R ₁₂₅ described later Examples of the alkyl group having 1 to 50 (preferably 1 to 18, more preferably 1 to 5) include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group T-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl 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-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloro Propyl 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 group, 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-aminoiso Butyl 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-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3- A trinitropropyl group etc. are mentioned.

Examples of the alkenyl group having 2 to 50 carbon atoms (preferably 2 to 18) of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include a vinyl group, an allyl group, a 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2-dimethylallyl group, etc. Can be mentioned.

Examples of the alkynyl group having 2 to 50 carbon atoms (preferably 2 to 18) of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include an ethynyl group.

Examples of cycloalkyl groups having 3 to 50 (preferably 3 to 18, more preferably 3 to 6) ring-forming carbon atoms of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include cyclo Examples thereof include a propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

Examples of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and an alkoxy group (preferably 1 to 18) of R ₁₀₁ to R ₁₁₀ described later include an oxygen atom bonded to the alkyl group having 1 to 50 carbon atoms. Group.

Examples of the alkylthio group having 1 to 50 carbon atoms (preferably 1 to 18) of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include, for example, the above-mentioned 1 to 50 carbon atoms. Examples include a group in which a sulfur atom is bonded to an alkyl group.

R ₁ to R ₁₂ , R ₁₃ and R ₁₄ , R ₁₅ to R ₁₈ , R ₂₁ to R ₂₅ , R ₃₁ to R ₄₃ described later, Ar ₁ and Ar ₂ , R ₁₀₁ to R ₁₁₀ described later, and R ₁₂₁ described later. the aryl group ~ _{R 125,} and ring carbon atoms 6 to 50 _{Ar 101} described later (preferably 6 to 18), for example, a phenyl group, 1-naphthyl, 2-naphthyl, 1-anthryl group, 2-anthryl group, 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, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl 4-yl group, p-terphenyl 3-yl group, p-terphenyl 2-yl group, m-terphenyl 4-yl group, m-terphenyl 3-yl group, m-terphenyl 2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, pt-butylphenyl group, meta-t-butylphenyl group, ortho -T-butylphenyl group, 3,4,5-trimethylphenyl group, 4-phenoxyphenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4- (Phenylsulfanyl) phenyl group, 4- (methylsulfanyl) phenyl group, N ′, N′-dimethyl-N-phenyl group, N ′, N′-dimethyl-N-phenyl group, 2 6-dimethylphenyl group, (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9′-spirobifluorenyl group, 9, 9-di (4-methylphenyl) fluorenyl group, 9,9-di (4-isopropylphenyl) fluorenyl group, 9,9-di (4-tbutylphenyl) fluorenyl group, chrysenyl group, fluoranthenyl group, etc. Can be mentioned.
Among these, preferably a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a pyrenyl group, a phenanthryl group and a fluorenyl group, more preferably a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a pyrenyl group and Fluorenyl group.

R ₁ to R ₁₂ , R ₁₃ and R ₁₄ , R ₁₅ to R ₁₈ , R ₂₁ to R ₂₅ , R ₃₁ to R ₄₃ described later, Ar ₁ and Ar ₂ , R ₁₀₁ to R ₁₁₀ described later, and R ₁₂₁ described later. the heterocyclic group ~ _{R 125,} and ring atoms 5-50 of _{Ar 101} to be described later (preferably 5 to 18), a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group, isoindolyl group, furyl group, benzofuranyl Group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, and thienyl group and pyridine Ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acrylic Ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, 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 [a] dibenzofuran ring, benzo [b] dibenzofuran ring and benzo [c] dibenzofuran ring, 1,3-benzodioxole ring, 2,3 -A monovalent group formed from a dihydro-1,4-benzodioxin ring, a phenanthro [4,5-bcd] furan ring, a benzophenoxazine ring, and the like.

Examples of the aryloxy group having 6 to 50 ring carbon atoms (preferably 6 to 18) of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include, for example, the above ring carbon atoms Examples include groups in which an oxygen atom is bonded to 6 to 50 aryl groups.

Examples of the arylthio group having 6 to 50 (preferably 6 to 18) ring carbon atoms of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include, for example, the above ring carbon atoms of 6 And groups having a sulfur atom bonded to ˜50 aryl groups.

Examples of the aralkyl group having 7 to 50 carbon atoms (preferably 7 to 18) of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include, for example, a benzyl group, a 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, 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-chloro Robenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl 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 and the like.

Examples of the halogen atoms of R ₁ to R ₁₂ , R ₁₅ to R ₁₈ , and R ₁₀₁ to R ₁₁₀ described later include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the arylene group having 6 to 30 ring carbon atoms (preferably 6 to 18, more preferably 6 to 12) of L ₁ to L ₃ and L ₁₀₁ described later include a phenylene group (for example, m-phenylene group) and naphthylene. Group, biphenylene group, anthranylene group, pyrenylene group and the like.

Examples of the heteroarylene group having 5 to 30 (preferably 5 to 18) ring-forming atoms of L ₁ to L ₃ and L ₁₀₁ described later include non-condensed heteroarylene groups and condensed heteroarylene groups, and more specifically Pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl Group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, and thienyl group as a divalent group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring , Acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, mole Oline ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, Examples thereof include divalent groups formed from a dibenzofuran ring, a benzo [a] dibenzofuran ring, a benzo [b] dibenzofuran ring, and a benzo [c] dibenzofuran ring.

In the present specification, the substituent (hereinafter also referred to as an optional substituent) in the case of “substituted or unsubstituted” is, for example, an alkyl group having 1 to 50 carbon atoms described above with respect to R ₁ to R _{12 and the} like. An alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, a ring Aryloxy group having 6 to 50 carbon atoms, arylthio group having 6 to 50 ring carbon atoms, aralkyl group having 7 to 50 carbon atoms, —Si (R ₃₁ ) (R ₃₂ ) (R ₃₃ ), —C (= O) R ₃₄ , —COOR ₃₅ , —N (R ₃₆ ) (R ₃₇ ), —S (═O) ₂ R ₃₈ , —P (═O) (R ₃₉ ) (R ₄₀ ), —Ge (R ₄₁₎ ) (R ₄₂ ) (R ₄₃ ) (where R ₃₁ to R ₄₃ are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms.) , Halogen atoms, cyano groups, nitro groups, aryl groups having 6 to 50 ring carbon atoms, and heterocyclic groups having 5 to 50 ring atoms. Among these, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms is preferable.

Specific examples of these substituents are the same as those described above as the substituents such as R ₁ to R ₁₂ .

In the present specification, adjacent arbitrary substituents (or ring-forming substituents) are saturated or unsaturated rings (preferably saturated or unsaturated, substituted or unsubstituted 5-membered rings, A 6-membered ring or a 7-membered ring or more, more preferably a benzene ring).
In this specification, an arbitrary substituent may further have a substituent. Examples of the substituent further included in the arbitrary substituent include the same substituents as those described above.

Specific examples of one embodiment of the compound of the present invention include the following compounds. Me represents a methyl group.

One embodiment of the material for an organic electroluminescence element of the present invention contains the above-described compound.

The first aspect of the organic EL device of the present invention has a cathode, an anode, and an organic layer disposed between the cathode and the anode, and the organic layer contains the above-described compound.

The second aspect of the organic EL device of the present invention has a cathode, an anode, and a light emitting layer disposed between the cathode and the anode, and the light emitting layer contains the above-mentioned compound.

The first aspect and the second aspect of the organic EL element of the present invention are collectively referred to as one aspect of the organic EL element of the present invention.
Thereby, the fluorescence quantum yield can be improved.

In the first aspect of the organic EL device of the present invention, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, and the like. It is preferable that one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer contain the above-described compound. The light emitting layer may contain a compound represented by the following formula (11).

In the second aspect of the organic EL device of the present invention, it is preferable that the light emitting layer further contains a compound represented by the following formula (11).

(In the formula (11), R ₁₀₁ to R ₁₁₀ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R ₁₂₁ ) (R ₁₂₂ ) (R ₁₂₃ ), —C (═O) R ₁₂₄ , —COOR ₁₂₅ , halogen atom, cyano group, A tro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by -L ₁₀₁ -Ar _101. .
R ₁₂₁ to R ₁₂₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms.
However, at least one of R ₁₀₁ to R ₁₁₀ is a group represented by —L ₁₀₁ —Ar ₁₀₁ . L ₁₀₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, and Ar ₁₀₁ is substituted or unsubstituted. A substituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. When two or more L ₁₀₁ are present, the two or more L ₁₀₁ may be the same or different. When two or more Ar ₁₀₁ are present, the two or more Ar ₁₀₁ may be the same or different. )

In the second aspect of the organic EL device of the present invention, at least one of R ₁₀₉ and R ₁₁₀ is preferably a group represented by —L ₁₀₁ —Ar ₁₀₁ .

In the second aspect of the organic EL device of the present invention, R ₁₀₉ and R ₁₁₀ are preferably each independently a group represented by -L ₁₀₁ -Ar ₁₀₁ .

Specific examples of the compound represented by the formula (11) include the following compounds.

In the 2nd aspect of the organic EL element of this invention, when the above-mentioned light emitting layer contains the compound represented by Formula (1) and the compound represented by Formula (11), it represents with Formula (1). The content of the compound to be formed is preferably 1% by mass or more and 20% by mass or less based on the entire light emitting layer.
In the second aspect of the organic EL device of the present invention, when the light emitting layer includes a compound represented by the formula (1) and a compound represented by the formula (11), the formula (11) The content of the compound represented by is preferably 80% by mass or more and 99% by mass or less with respect to the entire light emitting layer.

In the second aspect of the organic EL device of the present invention, it is preferable to have a hole transport layer between the anode and the light emitting layer.

In the second aspect of the organic EL device of the present invention, it is preferable to have an electron transport layer between the cathode and the light emitting layer.

As a typical element configuration of the organic EL element of the present invention,
(1) Anode / light emitting layer / cathode (2) Anode / hole injection layer / light emitting layer / cathode (3) Anode / light emitting layer / electron injection / transport layer / cathode (4) Anode / hole injection layer / light emitting layer / Electron injection / transport layer / cathode (5) anode / organic semiconductor layer / light emitting layer / cathode (6) anode / organic semiconductor layer / electron barrier layer / light emitting layer / cathode (7) anode / organic semiconductor layer / light emitting layer / Adhesion improving layer / cathode (8) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode (9) anode / insulating layer / light emitting layer / insulating layer / cathode (10) anode / inorganic semiconductor layer / Insulating layer / light emitting layer / insulating layer / cathode (11) anode / organic semiconductor layer / insulating layer / light emitting layer / insulating layer / cathode (12) anode / insulating layer / hole injection / transport layer / light emitting layer / insulating layer / Cathode (13) Anode / insulating layer / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode structure.
Among the above, the configuration (8) is preferably used, but is not limited thereto.

The light emitting layer may be a phosphorescent light emitting layer or a fluorescent light emitting layer, and a plurality of light emitting layers may be provided. When there are a plurality of light emitting layers, a space layer may be provided between the light emitting layers for the purpose of preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting 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 transparent substrate 2, an anode 3, a cathode 4, and an organic thin film layer 10 disposed between the anode 3 and the cathode 4.
The organic thin film layer 10 has the above-described light emitting layer 5, but a hole injection / transport layer 6 or the like between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 between the light emitting layer 5 and the cathode 4. Etc. may be provided.
Further, an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5.
Thereby, electrons and holes can be confined in the light emitting layer 5, and the exciton generation probability in the light emitting layer 5 can be increased.

In the present specification, “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “electron injection layer” And / or “at least one of the electron transport layers”.

The substrate is used as a support for the light emitting element. As the substrate, 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 examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.

For the anode formed on the substrate, 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), a nitride of a metal material (for example, titanium nitride), or the like can be given.

The hole injection layer 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, Ladder compounds such as tungsten oxides, manganese oxides, aromatic amine compounds, and fluorene derivatives, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

The hole transport layer 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. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.

The electron transport layer is a layer containing a substance having a high electron transport property. For the electron transport layer, 1) metal complexes such as lithium complexes, aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, 3) Polymeric compounds can be used.

The electron injection layer is a layer containing a substance having a high electron injection property. The electron injection layer includes an alkali metal such as lithium (Li), a lithium complex, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), and alkali. An earth metal or a compound thereof can be used.

For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small 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 alkaline earth such as magnesium (Mg). Examples thereof include metals and alloys containing these metals (for example, MgAg, AlLi).

In one embodiment of the organic EL device of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. Each layer such as the light-emitting layer is known by a coating method such as a vacuum deposition method, a molecular beam deposition method (MBE method) or a solution dipping method in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, etc. Can be formed by a method.

In one embodiment of the organic EL device of the present invention, the thickness of each layer is not particularly limited, but generally it is several nm to 1 μm in order to suppress defects such as pinholes, suppress applied voltage, and improve luminous efficiency. The range of is preferable.

The organic EL element of the present invention can be used for display parts such as an organic EL panel module, display devices such as a television, a mobile phone, or a personal computer, and electronic equipment such as a light emitting device such as a lighting or a vehicle lamp. .

Next, the present invention will be described in further detail with reference to examples and comparative examples, but the present invention is not limited to the description of these examples.

Example 1
(Synthesis of Compound 1)

(1-1) Synthesis of 3,6-dibromonaphthalene-2,7-diyl diacetate 3,6-Dibromonaphthalene-2,7-diol (6.28 g), triethylamine (Et ₃ N) (under argon atmosphere) A mixture of 9.6 mL) and acetic anhydride (Ac ₂ O) (5.0 mL) was stirred at room temperature (rt) for 8 hours. Dichloromethane was added to the resulting reaction solution for extraction, and the organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 3,6-dibromonaphthalene-2,7-diyl diacetate (4.36 g, yield 55%).

(1-2) Synthesis of 3,6-bis (4-chloro-2-fluorophenyl) naphthalene-2,7-diyl diacetate 3,6-Dibromonaphthalene obtained in (1-1) under argon atmosphere -2,7-diyl diacetate (6.93 g), (4-chloro-2-fluorophenyl) boronic acid (7.81 g), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II ) (Dichloromethane adduct) (Pd (dppf) Cl ₂ DMC) (0.704 g), 2 mol / L aqueous sodium carbonate solution (2 mol / L Na ₂ CO ₃ aq) (51.5 mL), toluene (86 mL), 1 , 2-Dimethoxyethane (DME) (86 mL) was refluxed for 8 hours. The resulting reaction solution was cooled to room temperature and extracted with toluene, and then the organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 3,6-bis (4-chloro-2-fluorophenyl) naphthalene-2,7-diyl diacetate (5.81 g, yield 67%). .

(1-3) Synthesis of 3,10-dichlorodibenzo [d, d ′] naphtho [2,3-b: 7,6-b ′] difuran 3, obtained in (1-2) under an argon atmosphere 6-bis (4-chloro-2-fluorophenyl) naphthalene-2,7-diyl diacetate (5.0 g), potassium carbonate (8.27 g), N-methyl-2-pyrrolidone (NMP) (142 mL) The mixture was stirred at 160 ° C. for 8 hours. The resulting reaction solution was cooled to room temperature, and the precipitated solid was filtered and washed with water to obtain a crude dichloro-form. The obtained crude product was purified by recrystallization to give 3,10-dichlorodibenzo [d, d ′] naphtho [2,3-b: 7,6-b ′] difuran (1.5 g, yield 40 %).

(1-4) Synthesis of Compound 1 Dichloro compound (100 mg), diphenylamine (90 mg), tris (dibenzylideneacetone) dipalladium (0) (Pd ₂ (dba) obtained in (1-3) under an argon atmosphere ₃ ) (4.86 mg), 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropyl-1,1′-biphenyl (XPhos (10.1 mg), sodium-t-butoxide (NaOtBu) (76 mg) ) And xylene (5 mL) were refluxed for 4 hours, the resulting reaction solution was cooled to room temperature, the precipitated solid was filtered and washed with methanol, and the resulting residue was subjected to silica gel column chromatography and Purification by recrystallization gave compound 1 (49 mg, 28% yield), which had a molecular weight of 642.758, Analysis of obtained mass spectrum of compound 1, since was m / z (mass to charge ratio) = 643.05, was identified as Compound 1.

(Preparation of toluene solution)
The obtained compound 1 was dissolved in toluene so that the concentration was 5 μmol / L, and a toluene solution of compound 1 was prepared.

(Measurement of fluorescence quantum yield (PLQY))
About the toluene solution of the obtained compound 1, PLQY was measured using absolute PL (photoluminescence) quantum yield measuring device Quantaurus-QY (made by Hamamatsu Photonics Co., Ltd.). The PLQY value of Compound 1 was 91%.

(Measurement of fluorescence emission peak wavelength (FL-peak))
When the obtained toluene solution of Compound 1 was measured using a fluorescence spectrum measuring apparatus spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Co., Ltd.), the fluorescence emission peak wavelength when excited at 356 nm was 420 nm. Observed.

Following the above reaction, a compound within the scope of the present invention can be synthesized by using a known alternative reaction or raw material suitable for the target product.

Example 2
The following compound 2 was synthesized in the same manner as in Example 1 except that bis (3,4,5-trimethylphenyl) amine (134 mg) was used instead of diphenylamine (90 mg).

The molecular weight of Compound 2 was 811.082, and the mass spectrum of Compound 2 obtained was measured in the same manner as in Example 1. As a result, it was identified as Compound 2 because m / z = 811.2.

For Compound 2, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 3
The following compound was used in the same manner as in Example 1 except that bis (4-methoxyphenyl) amine (AK-96671, manufactured by Ark Pharm) (128 mg) was used instead of diphenylamine (90 mg), and xylene was changed to 3 mL. 3 was synthesized (34 mg, 16% yield).

The molecular weight of Compound 3 was 762.86, and the mass spectrum of Compound 3 obtained was measured in the same manner as in Example 1. As a result, m / z = 762.27.

For Compound 3, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 4
The same as Example 1 except that bis (4- (tert-butyl) phenyl) amine (SC-484676, manufactured by Santa Cruz Biotechnology) (157 mg) was used instead of diphenylamine (90 mg) and xylene was changed to 3 mL. Then, the following compound 4 was synthesized (76 mg, yield 31%).

Compound 4 had a molecular weight of 867.19. As in Example 1, when the mass spectrum of the obtained compound 4 was measured, m / z = 867.30.

For Compound 4, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 5
(5-1) Synthesis of bis (3,4-dimethoxyphenyl) amine

Under an argon atmosphere, 3,4-dimethoxyaniline (4.23 g), 4-bromo-1,2-dimethoxybenzene (5.0 g), tris (dibenzylideneacetone) dipalladium (0) (0.444 g), John Phos A mixture of ((2-biphenyl) di-tert-butylphosphine) (0.550 g), sodium-t-butoxide (4.43 g) and toluene (100 mL) was refluxed for 5 hours. Silica gel was added to the resulting reaction solution, and the mixture was filtered through Celite, and the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography to obtain bis (3,4-dimethoxyphenyl) amine (6.45 g, yield 91%).

(5-2) Synthesis of Compound 5 In place of diphenylamine (90 mg), bis (3,4-dimethoxyphenyl) amine (161 mg) obtained in (5-1) was used, and xylene was changed to 3 mL. The following compound 5 was synthesized in the same manner as Example 1 (53 mg, yield 22%).

The molecular weight of Compound 5 was 882.97, and the mass spectrum of Compound 5 obtained was measured in the same manner as in Example 1. As a result, m / z = 882.32 was identified, and thus Compound 5 was identified.

For Compound 5, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 6
(6-1) Synthesis of N- (3,4,5-trimethylphenyl) -2-dibenzofuranamine

Under an argon atmosphere, 2-bromo-dibenzofuran (1.0 g), 3,4,5-trimethylaniline (0.657 g), tris (dibenzylideneacetone) dipalladium (0) (0.074), BINAP (rac- A mixture of 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl) (0.101 g), sodium-t-butoxide (0.778 g) and toluene (20 mL) was refluxed for 5 hours. Silica gel was added to the resulting reaction solution, and the mixture was filtered through Celite, and the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography to obtain N- (3,4,5-trimethylphenyl) -2-dibenzofuranamine (0.92 g, yield 75%).

(6-2) Synthesis of Compound 6 Using N- (3,4,5-trimethylphenyl) -2-dibenzofuranamine (168 mg) obtained in (6-1) instead of diphenylamine (90 mg), xylene The following compound 6 was synthesized in the same manner as in Example 1 except that the amount was changed to 3 mL (27 mg, yield 10%).

The molecular weight of Compound 6 was 907.08, and the mass spectrum of Compound 6 obtained was measured in the same manner as in Example 1. As a result, m / z = 907.30 was identified, and it was identified as Compound 6.

For Compound 6, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 7
(7-1) Synthesis of 3,4,5-trimethyl-N- (4-phenoxyphenyl) aniline

Under an argon atmosphere, 4-bromodiphenyl ether (1.0 g), 3,4,5-trimethylaniline (0.651 g), tris (dibenzylideneacetone) dipalladium (0) (0.074), rac-2,2 A mixture of '-bis (diphenylphosphino) -1,1'-binaphthyl (0.10 g), sodium-t-butoxide (0.772 g) and toluene (20 mL) was refluxed for 5 hours. Silica gel was added to the resulting reaction solution, and the mixture was filtered through Celite, and the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography to obtain 3,4,5-trimethyl-N- (4-phenoxyphenyl) aniline (0.68 g, yield 52%).

(7-2) Synthesis of Compound 7 Using 3,4,5-trimethyl-N- (4-phenoxyphenyl) aniline (169 mg) obtained in (7-1) instead of diphenylamine (90 mg), xylene The following compound 7 was synthesized in the same manner as in Example 1 except that was changed to 3 mL (33 mg, 13% yield).

Compound 7 had a molecular weight of 911.11. The mass spectrum of Compound 7 obtained was measured in the same manner as in Example 1. As a result, m / z = 911.30 was identified. Thus, Compound 7 was identified.

For Compound 7, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 8
Synthesis of N- (3,4,5-trimethylphenyl) -1,3-benzodioxol-5-amine

Under an argon atmosphere, 4-bromo-1,2-methylenedioxybenzene (1.0 g), 3,4,5-trimethylaniline (0.807 g), tris (dibenzylideneacetone) dipalladium (0) (0. 091), rac-2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.124 g), sodium-t-butoxide (0.956 g), toluene (20 mL) was refluxed for 5 hours. did. Silica gel was added to the resulting reaction solution, and the mixture was filtered through Celite, and the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography to obtain N- (3,4,5-trimethylphenyl) -1,3-benzodioxol-5-amine (0.76 g, yield 56%). It was.

(8-2) Synthesis of Compound 8 Instead of diphenylamine (90 mg), N- (3,4,5-trimethylphenyl) -1,3-benzodioxole-5- (5) obtained in (8-1) The following compound 8 was synthesized in the same manner as in Example 1 except that amine (142 mg) was used and xylene was changed to 3 mL (61 mg, yield 28%).

The molecular weight of Compound 8 was 814.94, and the mass spectrum of Compound 8 obtained was measured in the same manner as in Example 1. As a result, it was m / z = 814.60.

For Compound 8, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 9
(9-1) Synthesis of N- (3,4,5-trimethylphenyl) -2,3-dihydro-1,4-benzodioxin-6-amine

Under an argon atmosphere, 6-bromo-1,4-benzodioxane (1.0 g), 3,4,5-trimethylaniline (0.754 g), tris (dibenzylideneacetone) dipalladium (0) (0.085) , Rac-2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (0.116 g), sodium t-butoxide (0.894 g), toluene (20 mL) was refluxed for 5 hours. Silica gel was added to the resulting reaction solution, and the mixture was filtered through Celite, and the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography, and N- (3,4,5-trimethylphenyl) -2,3-dihydro-1,4-benzodioxin-6-amine (1.19 g, yield 94) %).

(9-2) Synthesis of Compound 9 N- (3,4,5-trimethylphenyl) -2,3-dihydro-1,4-benzoate obtained in (9-1) instead of diphenylamine (90 mg) The following compound 9 was synthesized in the same manner as in Example 1 except that dioxin-6-amine (150 mg) was used and xylene was changed to 3 mL (71 mg, 31% yield).

The molecular weight of Compound 9 was 842.99, and the mass spectrum of Compound 9 obtained was measured in the same manner as in Example 1. As a result, m / z = 842.35, which was identified as Compound 9.

For Compound 9, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Example 10
(Synthesis of Compound 10)

(10-1) Synthesis of Intermediate X Under argon atmosphere, 350 ml of tetrahydrofuran (THF) solution of 2,7-dimethoxynaphthalene (10 g) was cooled to 0 ° C., and 1.55 mol / L of n-butyllithium (n— A BuLi) hexane solution (34.3 ml) was added dropwise over 20 minutes, and the mixture was further stirred at 0 ° C. for 1 hour.
Next, the mixture was cooled to −78 ° C., and triisopropyl borate (B (O ⁱ Pr) ₃ ) (17.1 ml) was added dropwise. After stirring for 2 hours while returning to room temperature, 50 ml of 4N hydrochloric acid was added. The solvent was removed from the reaction solution, and the precipitated crystals were washed with water and hexane to obtain Intermediate X (10.9 g, yield 88%).

(10-2) Synthesis of Intermediate 2X Under an argon atmosphere, a mixture of 2,7-dimethoxynaphthalene (8.0 g) and tetrahydrofuran (160 mL) was cooled to 0 ° C. in an ice bath, and 1.6 mol / L of n- A butyllithium hexane solution (63.8 mL) was slowly added dropwise and stirred for 2 hours. Next, TMSCl (chlorotrimethylsilane) (12.9 mL) was slowly added dropwise, and the mixture was warmed to room temperature and stirred for 2 hours.
Thereafter, the mixture was cooled again to 0 ° C., and a 1.6 mol / L n-butyllithium hexane solution (53.1 mL) was slowly added dropwise and stirred for 2 hours. Next, chlorotrimethylsilane (10.7 mL) was slowly added dropwise, and the mixture was warmed to room temperature and stirred for 2 hours. A saturated aqueous ammonium chloride solution (200 mL) was added to the resulting reaction solution, and the mixture was stirred at room temperature for 2 hours. Extraction was performed with dichloromethane by a liquid separation operation, and the organic phase was dehydrated and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate, the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain Intermediate 2X (TMS represents a trimethylsilyl group) (6.6 g, yield 46%).

(10-3) Synthesis of Intermediate 3X Under an argon atmosphere, a mixture of Intermediate 2X (6.6 g) obtained in (10-2) and dichloromethane (60 mL) was cooled to 0 ° C. with an ice bath. 0 mol / L iodine monochloride (ICl) in dichloromethane (42 mL) was slowly added dropwise, and the mixture was warmed to room temperature and stirred for 6 hours. A saturated aqueous sodium sulfite solution was added to the resulting reaction solution, and the mixture was stirred for 1 hour. Extraction was performed with dichloromethane by a liquid separation operation, and the organic phase was dehydrated and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate, the filtrate was concentrated with a rotary evaporator. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain Intermediate 3X (3.6 g, yield 53%).

(10-4) Synthesis of Intermediate 4X Intermediate 3X (2.5 g) obtained in (10-3), Intermediate X (3.9 g) obtained in (10-1) under an argon atmosphere, Bis {di-tert-butyl (4-dimethylaminophenyl) phosphine} dichloropalladium (II) (PdCl ₂ (AmPhos) ₂ ) (0.201 g), potassium phosphate (3.6 g), toluene (180 ml), isopropyl A mixture of alcohol (IPA) (60 ml) and water (30 ml) was refluxed for 18 hours. The resulting reaction solution was cooled to room temperature and extracted with toluene, and then the organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate 4X (2.2 g, yield 70%).

(10-5) Synthesis of Intermediate 5X Under an argon atmosphere, a 50 ml dichloromethane solution of Intermediate 4X (2.2 g) obtained in (10-4) was cooled to −10 ° C., and 1 mol / L boron tribromide. In dichloromethane (27.5 ml) was added dropwise. The reaction was continued for 1 hour at −10 ° C. and stirred for 2 hours while returning to room temperature. The obtained solution was poured into ice water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain Intermediate 5X (1.7 g, yield 95). %).

(10-6) Synthesis of Intermediate 6X Under an argon atmosphere, Intermediate 5X (800 mg) obtained in (10-5), Zeolite (zeolite HSZ-360HUA (manufactured by Tosoh Corporation)) (250 mg), o -Dichlorobenzene (o-DCB) (600 mL) was mixed and stirred at 160 ° C. for 6 hours. After cooling to room temperature, the mixture was allowed to stand overnight, and the precipitated solid was washed with methanol. Extraction from the solid with tetrahydrofuran gave a brown solid (700 mg, yield 95%).
The molecular weight of intermediate 6X was 440.454. The mass spectrum of the obtained brown solid was measured in the same manner as in Example 1. As a result, m / z = 440, and thus the intermediate 6X was identified.

(10-7) Synthesis of Intermediate 7X Intermediate 6X (860 mg) obtained in (10-6), pyridine (40 mL), and dichloromethane (40 mL) were mixed in an argon atmosphere at 0 ° C. Anhydrous triflate (Tf2O) (2.3 mL) was added dropwise. After stirring at room temperature for 1 hour, methanol was added to stop the reaction. Water was added to the reaction solution, and dichloromethane was removed by concentration under reduced pressure. The precipitated solid was collected by filtration and washed with methanol to obtain a tan solid (1.1 g, yield 84%).
Intermediate 7X had a molecular weight of 704.566, and the mass spectrum of the obtained tan solid was measured in the same manner as in Example 1. As a result, m / z = 704. Therefore, Intermediate 7X (TfO— Is identified as CF ₃ S (═O) ₂ O—.

(10-8) Synthesis of Compound 10 Intermediate 7X (900 mg) obtained by (10-7), diphenylamine (540 mg), tris (dibenzylideneacetone) dipalladium (0) (23 mg), dioxygen under argon atmosphere -Tert-butyl (2,2-diphenyl-1-methyl-1-cyclopropyl) phosphine (cBRIDP) (36 mg), 1.0 mol / L lithium bis (trimethylsilyl) amide (LiHMDS) in THF (3.2 mL) ), Xylene (90 mL) was refluxed for 6 hours. The resulting reaction solution was cooled to room temperature and extracted with toluene, and then the organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 10 (420 mg, yield 44%).
The molecular weight of the compound 10 was 742.88, and when the mass spectrum of the obtained compound 10 was measured, it was m / z = 742. Therefore, the compound 10 was identified.

For Compound 10, a toluene solution was prepared and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Comparative Examples 1 and 2
A toluene solution was prepared and evaluated in the same manner as in Example 1 using the following Comparative Example Compounds 1 and 2. The results are shown in Table 1.

Example 1 and Example 2 had higher PLQY values than Comparative Examples 1 and 2.
In addition, Examples 3 to 10 had higher PLQY values than Comparative Examples 1 and 2.

Example 21
(Production of organic EL element)
A glass substrate (manufactured by Geomat Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning 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 after cleaning is attached to the substrate holder of the vacuum deposition apparatus, and the compound HI-1 is deposited on the surface where the transparent electrode is formed so as to cover the transparent electrode, and the film thickness is 5 nm. The HI-1 film was formed. This HI-1 film functions as a hole injection layer.

Compound HT-1 was vapor-deposited on this HI-1 film to form an HT-1 film having a thickness of 80 nm. This HT-1 film functions as a first hole transport layer.
Subsequently, Compound HT-2 was vapor-deposited on this HT-1 film to form an HT-2 film having a thickness of 10 nm. This HT-2 film functions as a second hole transport layer.
Subsequently, Compound BH-1 and Compound 2 (dopant material) described above were co-evaporated on this HT-2 film to form a light emitting layer having a thickness of 25 nm. The concentration of Compound 2 (dopant material) in the light emitting layer was 4 mass%.

Subsequently, ET-1 was vapor-deposited on the light emitting layer to form a first electron transport layer having a thickness of 10 nm.
Subsequently, ET-2 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
Further, lithium fluoride (LiF) was vapor-deposited on the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
And metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal cathode with a film thickness of 80 nm was formed.

The organic EL element was produced as described above. The compounds used are shown below.

(Measurement of drive voltage)
The voltage (unit: V) when a voltage was applied to the obtained organic EL element was measured so that the current density was 10 mA / cm ² . The results are shown in Table 2.

(Measurement of CIE 1931 chromaticity, evaluation of main peak wavelength λ _p , and calculation of external quantum efficiency EQE)
CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the obtained organic EL device so that the current density was 10 mA / cm ² , a spectral radiance meter CS-1000 (manufactured by Konica Minolta, Inc.) Was used to obtain a spectral radiance spectrum, and CIEx and CIEy were measured.
The main peak wavelength λ _p (unit: nm) was determined from the obtained spectral radiance spectrum.
The external quantum efficiency EQE (unit:%) was calculated from the obtained spectral radiance spectrum on the assumption that Lambtian radiation was performed.
The results are shown in Table 2.

As can be seen from Table 2, it was confirmed that the organic EL device using Compound 2 as a dopant showed blue light emission.

Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will appreciate that these exemplary embodiments and / or embodiments are substantially without departing from the novel teachings and advantages of the present invention. It is easy to make many changes to the embodiment. Accordingly, many of these modifications are within the scope of the present invention.
All the contents of the Japanese application specification that is the basis of the priority of Paris in this application are incorporated herein.

Claims

A compound represented by the following formula (1).

(In the formula (1), R 1 to R 12 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, or a substituted group. Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R 21 ) (R 22 ) (R 23 ), —C (═O) R 24 , —COOR 25 , halogen atom, cyano group, nitro group, substituted or Represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (2): R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are bonded to each other and represented by the following formula (1A). May be formed.

(In the formula (1A), R 15 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R 21 ) (R 22 ) (R 23 ), —C (═O) R 24 , —COOR 25 , halogen atom, cyano group, nitro group, substitution Or an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (2).
At least one of R 1 to R 12 and R 15 to R 18 is a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. It is a group represented by a cyclic group or the following formula (2).
R 21 to R 25 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms.
X 1 and X 2 each independently represent an oxygen atom, a sulfur atom or C (R 13 ) (R 14 ).
R 13 and R 14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms. R 13 and R 14 may combine with each other to form a saturated or unsaturated ring.

(In Formula (2), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. It is a group.
L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms. It is. )
If Ar 1, Ar 2, L 1, L 2 and L 3 are present 2 or more, two or more Ar 1, Ar 2, L 1, each of L 2 and L 3 may be the same or may be different . )
2. The compound according to claim 1, wherein two or more of R 1 to R 12 and R 15 to R 18 are a group represented by the formula (2).
The compound according to claim 1 or 2, wherein two of R 1 to R 12 and R 15 to R 18 are groups represented by the formula (2).
The compound according to any one of claims 1 to 3, which is represented by the following formula (3):

(In Formula (3), X 1 and X 2 are as defined in Formula (1) above. Ar 1 , Ar 2 , L 1 , L 2 and L 3 are defined in Formula (2) above. Street.
R 1 , R 2 , R 4 to R 6 , and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms of, -Si (R 21) (R 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R 1 and R 2 may combine with each other to form a ring represented by the formula (1A). R 5 and R 6 may combine with each other to form a ring represented by the formula (1A).
R 21 to R 25 are as defined in the above formula (1). )
The compound according to any one of claims 1 to 4, which is represented by the following formula (4):

(In Formula (4), X 1 and X 2 are as defined in Formula (1) above. Ar 1 , Ar 2 , L 1 and L 2 are as defined in Formula (2) above. .
R 1 , R 2 , R 4 to R 6 , and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms of, -Si (R 21) (R 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R 1 and R 2 may combine with each other to form a ring represented by the formula (1A). R 5 and R 6 may combine with each other to form a ring represented by the formula (1A).
R 21 to R 25 are as defined in the above formula (1). )
The compound according to any one of claims 1 to 5 represented by the following formula (5):

(In Formula (5), X 1 and X 2 are as defined in Formula (1). Ar 1 and Ar 2 are as defined in Formula (2) above.
R 1 , R 2 , R 4 to R 6 , and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted carbon number having 2 to 50 carbon atoms. Alkenyl group, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted Or an unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms of, -Si (R 21) (R 22) (R 23), - C (= O) R 24, -COOR 25, a halogen atom, a cyano group, a nitro group, Showing substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted ring atoms 5-50 heterocyclic group, or a group represented by the formula (2). R 1 and R 2 may combine with each other to form a ring represented by the formula (1A). R 5 and R 6 may combine with each other to form a ring represented by the formula (1A).
R 21 to R 25 are as defined in the above formula (1). )
R 1 , R 2 , R 4 to R 6 and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring carbon number of 6 The compound according to any one of claims 1 to 6, which is selected from the group consisting of an aryl group having -50 atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
R 1 , R 2 , R 4 to R 6 and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring formation. The compound according to any one of claims 1 to 7, which is selected from the group consisting of heterocyclic groups having 5 to 50 atoms.
R 1 , R 2 , R 4 to R 6 and R 8 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted ring formation. The compound according to any one of claims 1 to 8, which is selected from the group consisting of a heterocyclic group having 5 to 18 atoms.
The compound of Claim 1 represented by following formula (6).

(In Formula (6), X 1 and X 2 are as defined in Formula (1) above. Ar 1 and Ar 2 are as defined in Formula (2) above.)
R 2 and R 3 are bonded to each other to form a ring represented by the formula (1A),
The compound according to any one of claims 1 to 3, wherein R 6 and R 7 are bonded to each other to form a ring represented by the formula (1A).
The compound according to any one of claims 1 to 3, which is represented by the following formula (7):

(In Formula (7), X 1 and X 2 are as defined in Formula (1) above. Ar 1 , Ar 2 , L 1 , L 2 and L 3 are defined in Formula (2) above. Street.
R 1 , R 4 , R 5 , R 8 to R 12 , R 15 , R 16 and R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of 7 ~ 50, -Si (R 21 ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R 15 , R 16 and R 18 may be the same or different.
R 21 to R 25 are as defined in the above formula (1). )
The compound according to any one of claims 1 to 3, which is represented by the following formula (8):

(In the formula (8), X 1 and X 2 are as defined in the formula (1). Ar 1 , Ar 2 , L 1 and L 2 are as defined in the formula (2). .
R 1 , R 4 , R 5 , R 8 to R 12 , R 15 , R 16 and R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of 7 ~ 50, -Si (R 21 ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R 15 , R 16 and R 18 may be the same or different.
R 21 to R 25 are as defined in the above formula (1). )
The compound according to any one of claims 1 to 3, which is represented by the following formula (9):

(In Formula (9), X 1 and X 2 are as defined in Formula (1) above. Ar 1 and Ar 2 are as defined in Formula (2) above.
R 1 , R 4 , R 5 , R 8 to R 12 , R 15 , R 16 and R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms group, a substituted or unsubstituted aralkyl group having a carbon number of 7 ~ 50, -Si (R 21 ) (R 22) (R 23), - C (= O) R 24, -COOR 25, halogen atom A cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (2) Indicates.
Each of the two R 15 , R 16 and R 18 may be the same or different.
R 21 to R 25 are as defined in the above formula (1). )
The compound according to any one of claims 1 to 14, wherein X 1 and X 2 are oxygen atoms.
Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group. Compound described in 1.
In the case of “substituted or unsubstituted”, the substituent is an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, or a cyclocarbon having 3 to 50 ring carbon atoms. Alkyl group, alkoxy group having 1 to 50 carbon atoms, alkylthio group having 1 to 50 carbon atoms, aryloxy group having 6 to 50 ring carbon atoms, arylthio group having 6 to 50 ring carbon atoms, 7 to 50 carbon atoms Aralkyl group, —Si (R 31 ) (R 32 ) (R 33 ), —C (═O) R 34 , —COOR 35 , —N (R 36 ) (R 37 ), —S (═O) 2 R 38 , —P (═O) (R 39 ) (R 40 ), —Ge (R 41 ) (R 42 ) (R 43 ) (where R 31 to R 43 are each independently a hydrogen atom, carbon An alkyl group having 1 to 50 carbon atoms and 6 to 50 ring carbon atoms An aryl group or a heterocyclic group having 5 to 50 ring atoms.), A halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, or a heterocycle having 5 to 50 ring atoms. The compound according to any one of claims 1 to 16, which is a cyclic group.
The substituent in the case of “substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. The compound according to any one of 1 to 17.
The compound according to any one of claims 1 to 18, which is a material for an organic electroluminescence device.
An organic electroluminescent element material comprising the compound according to any one of claims 1 to 19.
A cathode,
The anode,
An organic layer disposed between the cathode and the anode;
Have
An organic electroluminescence device, wherein the organic layer contains the compound according to any one of claims 1 to 19.
A cathode,
The anode,
A light emitting layer disposed between the cathode and the anode;
Have
An organic electroluminescence device, wherein the light emitting layer contains the compound according to any one of claims 1 to 19.
The organic electroluminescence device according to claim 22, wherein the light emitting layer further contains a compound represented by the following formula (11).

(In the formula (11), R 101 to R 110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted Or an unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon; 1 to 50 alkylthio groups, substituted or unsubstituted aryloxy groups having 6 to 50 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 50 aralkyl groups, —Si (R 121 ) (R 122 ) (R 123 ), —C (═O) R 124 , —COOR 125 , halogen atom, cyano group, A tro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by -L 101 -Ar 101. .
R 121 to R 125 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted group. A heterocyclic group having 5 to 50 ring atoms.
However, at least one of R 101 to R 110 is a group represented by —L 101 —Ar 101 . L 101 is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, and Ar 101 is substituted or unsubstituted. A substituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. When two or more L 101 are present, the two or more L 101 may be the same or different. When two or more Ar 101 are present, the two or more Ar 101 may be the same or different. )
The organic electroluminescent device according to claim 23, wherein at least one of R 109 and R 110 is a group represented by the -L 101 -Ar 101 .
The organic electroluminescent device according to claim 23, wherein R 109 and R 110 are each independently a group represented by -L 101 -Ar 101 .
The organic electroluminescence device according to any one of claims 22 to 25, further comprising a hole transport layer between the anode and the light emitting layer.
The organic electroluminescence device according to any one of claims 22 to 26, 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 21 to 27.