JP2008081490A - Anthracene derivative, and light-emitting element, light-emitting device and electronic device using anthracene derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new anthracene derivative, a light-emitting element having high luminous efficiency, a light-emitting element having long lifetime, and a light-emitting device and an electronic device having long lifetime by using the light-emitting elements. <P>SOLUTION: The anthracene derivative is expressed by general formula (1). The anthracene derivative expressed by general formula (1) exhibits high luminous efficiency and, accordingly, a light-emitting element having high luminous efficiency can be produced by using the anthracene derivative as the light-emitting element. A light-emitting element having long lifetime can be produced by using the anthracene derivative expressed by general formula (1) as the light-emitting element. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an anthracene derivative, and a light-emitting element, a light-emitting device, and an electronic device using the anthracene derivative.

  Organic compounds can have various structures compared to inorganic compounds, and materials having various functions may be synthesized by appropriate molecular design. Because of these advantages, in recent years, attention has been focused on photoelectronics and electronics using functional organic materials.

  For example, a solar cell, a light emitting element, an organic transistor, etc. are mentioned as an example of the electronic device which used the organic compound as a functional organic material. These are devices utilizing the electrical properties and optical properties of organic compounds, and particularly light emitting elements are making remarkable progress.

  The light emitting mechanism of a light emitting element is a molecule in which electrons injected from the cathode and holes injected from the anode are recombined at the emission center of the light emitting layer by applying a voltage with the light emitting layer sandwiched between a pair of electrodes. It is said that when excitons are formed and the molecular excitons relax to the ground state, they emit energy and emit light. Singlet excitation and triplet excitation are known as excited states, and light emission is considered to be possible through either excited state.

  In improving the characteristics of such a light emitting element, there are many problems depending on the material, and in order to overcome these problems, the element structure is improved and the material is developed.

  For example, Patent Document 1 describes an anthracene derivative that emits green light. However, Patent Document 1 only shows a PL spectrum of an anthracene derivative, and does not disclose what element characteristics are exhibited when applied to a light-emitting element.

  Patent Document 2 describes a light-emitting element using an anthracene derivative as a charge transport layer. However, Patent Document 2 does not describe the lifetime of the light emitting element.

In view of commercialization, extending the lifetime is an important issue, and the development of light-emitting elements with even better characteristics is desired.
US Patent Application Publication No. 2005/0260442 JP 2004-91334 A

  In view of the above problems, an object of the present invention is to provide a novel anthracene derivative.

  It is another object of the present invention to provide a light emitting element with high luminous efficiency. It is another object of the present invention to provide a light-emitting element with a long lifetime. It is another object of the present invention to provide a light-emitting device and an electronic device having a long lifetime by using these light-emitting elements.

  One aspect of the present invention is an anthracene derivative represented by the general formula (1).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (1-1) to the general formula (1-3). In the general formula (1-1) to the general formula (1-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α is a carbon number having 6 to 25. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

  Another aspect of the present invention is an anthracene derivative represented by the general formula (2).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (2-1) to the general formula (2-3). In the general formulas (2-1) to (2-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.)

  Another aspect of the present invention is an anthracene derivative represented by General Formula (3).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (3-1) to the general formula (3-3). In the general formulas (3-1) to (3-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.)

  Another aspect of the present invention is an anthracene derivative represented by General Formula (4).

(In formula, Ar < ¹ > -Ar < ² > represents a C6-C25 aryl group, respectively, and A is either substitution represented by General formula (4-1)-General formula (4-3). In the general formulas (4-1) to (4-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

In the above configuration, each of Ar ^{1 to} Ar ² is preferably a substituent represented by General Formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.)

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by Structural Formula (11-2) or Structural Formula (11-3).

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by General Formula (11-4).

(In the formula, R ^{6 to} R ⁷ each represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms.)

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by Structural Formula (11-5) or Structural Formula (11-6).

In the above structure, Ar ¹ and Ar ² are preferably substituents having the same structure.

  Another aspect of the present invention is an anthracene derivative represented by the general formula (5).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (5-1) to the general formula (5-3). In the general formula (5-1) to the general formula (5-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α represents an alkyl group having 6 to 25 carbon atoms. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

  Another aspect of the present invention is an anthracene derivative represented by General Formula (6).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (6-1) to the general formula (6-3)). In the general formula (6-1) to the general formula (6-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.)

  Another aspect of the present invention is an anthracene derivative represented by General Formula (7).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (7-1) to the general formula (7-3). In the general formulas (7-1) to (7-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.)

  Another aspect of the present invention is an anthracene derivative represented by General Formula (8).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (8-1) to the general formula (8-3). In the general formulas (8-1) to (8-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

In the above configuration, each of Ar ^{1 to} Ar ² is preferably a substituent represented by General Formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.)

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by Structural Formula (11-2) or Structural Formula (11-3).

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by General Formula (11-4).

(Wherein R ^{6 to} R ⁷ each represent an alkyl group having 1 to 4 carbon atoms or a reel group having 6 to 15 carbon atoms.)

In the above structure, Ar ^{1 to} Ar ² are each preferably a substituent represented by Structural Formula (11-5) or Structural Formula (11-6).

In the above structure, Ar ¹ and Ar ² are preferably substituents having the same structure.

  Another embodiment of the present invention is a light-emitting element using the above anthracene derivative. Specifically, a light-emitting element including the above-described anthracene derivative between a pair of electrodes.

  Another embodiment of the present invention is a light-emitting element including a light-emitting layer between a pair of electrodes, and the light-emitting layer includes the above-described anthracene derivative. In particular, the above-described anthracene derivative is preferably used as the light-emitting substance. That is, it is preferable that the above-described anthracene derivative emit light.

  In addition, a light-emitting device of the present invention includes the above-described light-emitting element. The light-emitting element includes a layer containing a light-emitting substance between a pair of electrodes, and the layer containing the light-emitting substance contains the anthracene derivative. In addition, the light-emitting device of the present invention includes a control unit that controls light emission of the light-emitting element. Note that a light-emitting device in this specification includes an image display device, a light-emitting device, or a light source (including a lighting device). In addition, a module in which a connector such as an FPC (Flexible Printed Circuit) or TAB (Tape Automated Bonding) tape or TCP (Tape Carrier Package) is attached to the panel, a TAB tape or a module having a printed wiring board at the end of TCP, Alternatively, a module in which an IC (integrated circuit) is directly mounted on the light emitting device by a COG (Chip On Glass) method is included in the light emitting device.

  An electronic device using the light-emitting element of the present invention for the display portion is also included in the category of the present invention. Therefore, an electronic device according to the present invention includes a display portion, and the display portion includes the above-described light emitting element and a control unit that controls light emission of the light emitting element.

  The anthracene derivative of the present invention has high luminous efficiency. Therefore, a light-emitting element with high emission efficiency can be obtained by using the anthracene derivative of the present invention for a light-emitting element. In addition, by using the anthracene derivative of the present invention for a light-emitting element, a long-life light-emitting element can be obtained.

  In addition, by using the anthracene derivative of the present invention, a long-life light-emitting device and electronic device can be obtained.

  Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is easily understood by those skilled in the art that modes and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments below.

(Embodiment 1)
In this embodiment mode, an anthracene derivative of the present invention will be described.

  The anthracene derivative of the present invention is an anthracene derivative represented by the general formula (1).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (1-1) to the general formula (1-3). In the general formula (1-1) to the general formula (1-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α is a carbon number having 6 to 25. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

In General formula (1), as a substituent represented by Ar < ¹ > -Ar < ² >, the substituent represented by Structural formula (20-1)-Structural formula (20-9) is mentioned, for example.

In General Formula (1-1), examples of the substituent represented by Ar ^{11 to} Ar ¹³ include substituents represented by Structural Formula (21-1) to Structural Formula (21-9).

  Moreover, in General formula (1-1), as a substituent represented by (alpha), the substituent represented by Structural formula (22-1)-Structural formula (22-9) is mentioned, for example.

  Therefore, as a substituent represented by general formula (1-1), the substituent represented by Structural formula (31-1)-Structural formula (31-23) is mentioned, for example.

In the general formula (1-2), examples of the substituent represented by Ar ²¹ include substituents represented by structural formulas (23-1) to (23-9).

In the general formula ^(1-2), specific examples of ^{R 31} include, for example, structural formula (24-1) to the structural formula (24-18).

In the general formula (1-2), specific examples of R ³² include structural formulas (25-1) to (25-17).

  Therefore, specific examples of the general formula (1-2) include structural formula (32-1) to structural formula (32-42).

In the general formula (1-3), specific examples of Ar ³¹ include structural formula (26-1) to structural formula (26-9).

  In the general formula (1-3), specific examples of β include structural formulas (27-1) to (27-9).

In the general formula (1-3), specific examples of R ^{41 to} R ⁴² include structural formula (28-1) to structural formula (28-18).

  Therefore, specific examples of the general formula (1-3) include the structural formula (33-1) to the structural formula (33-34).

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (2) among the anthracene derivatives represented by General formula (1).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (2-1) to the general formula (2-3). In the general formulas (2-1) to (2-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.)

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (3) among the anthracene derivatives represented by General formula (1).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (3-1) to the general formula (3-3). In the general formulas (3-1) to (3-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.)

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (4) among the anthracene derivatives represented by General formula (1).

(In formula, Ar < ¹ > -Ar < ² > represents a C6-C25 aryl group, respectively, and A is either substitution represented by General formula (4-1)-General formula (4-3). In the general formulas (4-1) to (4-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

In the general formulas (1) to (4), Ar ^{1 to} Ar ² are each preferably a substituent represented by the general formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.)

In General Formulas (1) to (4), Ar ^{1 to} Ar ² are each a substituent represented by Structural Formula (11-2) or Structural Formula (11-3). preferable.

In the general formulas (1) to (4), Ar ^{1 to} Ar ² are each preferably a substituent represented by the general formula (11-4).

(Wherein R ^{6 to} R ⁷ each represent an alkyl group having 1 to 4 carbon atoms or a reel group having 6 to 15 carbon atoms.)

In General Formulas (1) to (4), Ar ^{1 to} Ar ² are each a substituent represented by Structural Formula (11-5) or Structural Formula (11-6). preferable.

In the general formulas (1) to (4), Ar ¹ and Ar ² are preferably substituents having the same structure.

In the general formulas (1) to (4), A is preferably bonded to the 2-position of the anthracene skeleton. By bonding at the 2-position, steric hindrance with Ar ¹ and steric hindrance with Ar ² are reduced.

  That is, an anthracene derivative represented by the general formula (5) is preferable.

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (5-1) to the general formula (5-3). In the general formula (5-1) to the general formula (5-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α represents an alkyl group having 6 to 25 carbon atoms. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (6).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (6-1) to the general formula (6-3)). In the general formula (6-1) to the general formula (6-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.)

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (7).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (7-1) to the general formula (7-3). In the general formulas (7-1) to (7-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.)

  Moreover, it is preferable that it is an anthracene derivative represented by General formula (8).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (8-1) to the general formula (8-3). In the general formulas (8-1) to (8-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

In the general formulas (5) to (8), Ar ^{1 to} Ar ² are each preferably a substituent represented by the general formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.)

In General Formula (5) to General Formula (8), Ar ^{1 to} Ar ² are each a substituent represented by Structural Formula (11-2) or Structural Formula (11-3). preferable.

In the general formulas (5) to (8), Ar ^{1 to} Ar ² are each preferably a substituent represented by the general formula (11-4).

(Wherein R ^{6 to} R ⁷ each represent an alkyl group having 1 to 4 carbon atoms or a reel group having 6 to 15 carbon atoms.)

In General Formula (5) to General Formula (8), Ar ^{1 to} Ar ² are each a substituent represented by Structural Formula (11-5) or Structural Formula (11-6). preferable.

In the general formulas (5) to (8), Ar ¹ and Ar ² are preferably substituents having the same structure.

  Specific examples of the anthracene derivative represented by General Formula (1) include Structural Formula (101) to Structural Formula (118), Structural Formula (201) to Structural Formula (218), and Structural Formula (301) to Structural Formula ( And anthracene derivatives represented by 318). However, the present invention is not limited to these.

  The anthracene derivatives represented by the structural formulas (101) to (118) are specific examples in the case where A is the general formula (1-1) in the general formula (1), and the structural formulas (201) to (201) The anthracene derivative represented by the structural formula (218) is a specific example in the case where A is the general formula (1-2) in the general formula (1), and is represented by the structural formula (301) to the structural formula (318). The anthracene derivative represented is a specific example when A is the general formula (1-3) in the general formula (1).

  As the synthesis method of the anthracene derivative of the present invention, various reactions can be applied. For example, it can synthesize | combine by performing the synthetic reaction shown to the following reaction scheme (A-1)-(A-5) and (B-1)-(B-3).

Compounds containing carbazole in the skeleton (compound A), N-bromosuccinimide (NBS), N-iodosuccinimide (NIS), bromine (Br ₂ ), potassium iodide (KI), iodine (I ₂ ), etc. After reacting with halogen or a halide to synthesize a compound containing 3-halogenated carbazole (Compound B), a coupling reaction with an arylamine using a metal catalyst such as a palladium catalyst (Pd catalyst) is performed. Carry out compound C. In Synthesis Scheme (A-1), the halogen element (X) is preferably iodine or bromine. R ³¹ represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms. Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms.

A compound containing carbazole in the skeleton (compound D) and a dihalide of an aromatic compound were reacted to synthesize a compound containing N- (halogenated aryl) carbazole in the skeleton (compound E). A compound F is obtained by performing a coupling reaction with an arylamine using a metal catalyst such as. In the synthesis scheme (A-2), the halogen element (X ¹ , X ² ) of the dihalide of the aromatic compound is preferably iodine or bromine. X ¹ and X ² may be the same or different. R ⁴¹ and R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Β represents an arylene group having 6 to 25 carbon atoms. Ar ³¹ represents an aryl group having 6 to 25 carbon atoms.

  An anthraquinone halide (Compound H) is synthesized by Sandmyer reaction of 1-aminoanthraquinone or 2-aminoanthraquinone (Compound G). By reacting an anthraquinone halide (compound H) with aryllithium, a diol form (compound I) of a 9,10-dihydroanthracene derivative is synthesized. The 9,10-dihydroanthracene derivative diol compound (Compound I) is subjected to de-OH reaction using sodium phosphinate monohydrate, potassium iodide and acetic acid to obtain 9,10-diaryl halogenated anthracene ( Compound J) is synthesized.

Note that in the synthesis schemes (A-3) to (A-5), X represents a halogen element. Ar ^{1 to} Ar ² each represents an aryl group having 6 to 25 carbon atoms.

The anthracene derivative of the present invention can be synthesized by the reaction shown in the synthesis scheme (B-1) using the compound J synthesized in the synthesis scheme (A-5). An anthracene derivative of the present invention represented by the general formula (1-1a) can be synthesized by subjecting compound J and an arylamine compound to a coupling reaction using a metal catalyst such as a palladium catalyst. In Synthesis Scheme (B-1), Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, Ar ^{11 to} Ar ¹³ each represent an aryl group having 6 to 25 carbon atoms, and α Represents an arylene group having 6 to 25 carbon atoms. In addition, the compound represented by general formula (1-1a) respond | corresponds when A in General formula (1) mentioned above is general formula (1-1).

Using the compound C synthesized in the synthesis scheme (A-1) and the compound J synthesized in the synthesis scheme (A-5), the anthracene derivative of the present invention is synthesized by the reaction shown in the synthesis scheme (B-2). Can do. An anthracene derivative of the present invention represented by the general formula (1-2a) can be synthesized by subjecting compound C and compound J to a coupling reaction using a metal catalyst such as a palladium catalyst. In Synthesis Scheme (B-2), Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, R ³¹ represents hydrogen, Or an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, and R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms. Represents one of the following. In addition, the compound represented by General formula (1-2a) respond | corresponds when A in General formula (1) mentioned above is General formula (1-2).

Synthesis of the anthracene derivative of the present invention by the reaction shown in the synthesis scheme (B-3) using the compound F synthesized in the synthesis scheme (A-2) and the compound J synthesized in the synthesis scheme (A-5). Can do. An anthracene derivative of the present invention represented by the general formula (1-3a) can be synthesized by subjecting Compound F and Compound J to a coupling reaction using a metal catalyst such as a palladium catalyst. In Synthesis Scheme (B-3), Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β represents a carbon number 6 Represents an arylene group having ˜25, and each of R ^{41 to} R ⁴² represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. In addition, the compound represented by general formula (1-3a) respond | corresponds when A in general formula (1) mentioned above is general formula (1-3).

  The anthracene derivative of the present invention has a high emission quantum yield and emits blue-green to yellow-green. Therefore, it can be suitably used for a light-emitting element.

  Further, since the anthracene derivative of the present invention can emit green light with high efficiency, it can be suitably used for a full color display. Further, since long-life green light emission is possible, it can be suitably used for a full-color display.

  Further, since the anthracene derivative of the present invention can emit green light with high efficiency, white light emission can be obtained by combining with other light-emitting materials. For example, when trying to obtain white light emission using red (R), green (G), and blue (B) light emission of NTSC chromaticity coordinates, approximately red (R): green (G): blue (B) = 1: 6: 3 If the light emission of each color is not mixed, it will not become white. In other words, the anthracene derivative of the present invention, which requires high-brightness green light emission and can obtain high-efficiency green light emission, is suitable for a light-emitting device.

  In the anthracene derivative of the present invention, only one substituent A is bonded to the anthracene skeleton as represented by the general formula (1). Therefore, light emission at a short wavelength is possible as compared with a disubstituted product in which two substituents A are bonded to an anthracene skeleton. In addition, since the molecular weight of the 2-substituted product is very large, it is difficult to form a film by a vapor deposition method, but the anthracene derivative of the present invention can be formed by a vapor deposition method. In addition, the synthesis of a disubstituted product requires a higher cost than the anthracene derivative of the present invention which is a monosubstituted product.

  In addition, when applied to a light-emitting element, the present inventors have found that using a mono-substituted product has a longer lifetime than using a di-substituted product. Therefore, a long-life light-emitting element can be obtained by applying the anthracene derivative of the present invention to a light-emitting element.

  In addition, the anthracene derivative of the present invention is stable even when the redox reaction is repeated. Therefore, a long-life light-emitting element can be obtained by using the anthracene derivative of the present invention for a light-emitting element.

(Embodiment 2)
One mode of a light-emitting element using the anthracene derivative of the present invention is described below with reference to FIG.

  The light-emitting element of the present invention has a plurality of layers between a pair of electrodes. The plurality of layers have a high carrier injecting property and a high carrier transporting property so that a light emitting region is formed at a distance from the electrode, that is, a carrier is recombined at a position away from the electrode. It is a combination of layers of materials.

  In this embodiment, the light-emitting element includes a first electrode 102, a first layer 103, a second layer 104, a third layer 105, and a fourth layer 106 that are sequentially stacked over the first electrode 102. And a second electrode 107 provided thereon. Note that in this embodiment mode, the first electrode 102 functions as an anode and the second electrode 107 functions as a cathode.

  The substrate 101 is used as a support for the light emitting element. As the substrate 101, for example, glass or plastic can be used. Note that other materials may be used as long as they function as a support in the manufacturing process of the light-emitting element.

  As the first electrode 102, a metal, an alloy, a conductive compound, a mixture thereof, or the like with a high work function (specifically, 4.0 eV or more) is preferably used. Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium zinc oxide (IZO), tungsten oxide, and oxide. Examples thereof include indium oxide containing zinc (IWZO). These conductive metal oxide films are usually formed by sputtering, but may be formed by applying a sol-gel method or the like. For example, an indium oxide-zinc oxide (IZO) film can be formed by a sputtering method using a target in which 1 to 20 wt% of zinc oxide is added to indium oxide. An indium oxide (IWZO) film containing tungsten oxide and zinc oxide is formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide. Can be formed. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), or a metal nitride (for example, titanium nitride: TiN).

The first layer 103 is a layer containing a substance having a high hole injection property. Molybdenum oxide (MoOx), vanadium oxide (VOx), ruthenium oxide (RuOx), tungsten oxide (WOx), manganese oxide (MnOx), or the like can be used. In addition, phthalocyanine compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (CuPC), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N- (3-methylphenyl) -N-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD) Alternatively, the first layer 103 can also be formed by a polymer such as poly (ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS).

  For the first layer 103, a composite material formed by combining an organic compound and an inorganic compound can be used. In particular, in a composite material including an organic compound and an inorganic compound that exhibits an electron-accepting property with respect to the organic compound, electron transfer occurs between the organic compound and the inorganic compound, so that the carrier density increases. And excellent hole transportability.

In addition, when a composite material formed by mixing an organic compound and an inorganic compound is used for the first layer 103, the first electrode 102 can be in ohmic contact with each other, regardless of the work function. A material for forming the first electrode can be selected.

  The inorganic compound used for the composite material is preferably a transition metal oxide. For example, an oxide of a metal belonging to Groups 4 to 8 in the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties. Among these, molybdenum oxide is particularly preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.

As the organic compound used for the composite material, various compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a high molecular compound (such as an oligomer, a dendrimer, and a polymer) can be used. Note that the organic compound used for the composite material is preferably an organic compound having a high hole-transport property. Specifically, a substance having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher is preferable. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Below, the organic compound which can be used for a composite material is listed concretely.

  For example, as an aromatic amine compound, N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4′-bis [N- (4- Diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N- (3-methylphenyl) -N-phenylamino] phenyl} -N-phenyl Amino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), and the like can be given.

  Specific examples of the carbazole derivative that can be used for the composite material include 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3 , 6-Bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9- Phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) and the like.

  As carbazole derivatives that can be used for the composite material, 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (Abbreviation: TCPB), 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5 , 6-tetraphenylbenzene or the like can be used.

Examples of aromatic hydrocarbons that can be used for the composite material include 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9. , 10-di (1-naphthyl) anthracene, 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis (4-phenylphenyl) anthracene ( Abbreviations: t-BuDBA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis (4-methyl-1-naphthyl) anthracene (abbreviation: DMNA), 2-tert-butyl-9, 0-bis [2- (1-naphthyl) phenyl] anthracene, 9,10-bis [2- (1-naphthyl) phenyl] anthracene, 2,3,6,7-tetramethyl-9,10-di (1 -Naphthyl) anthracene, 2,3,6,7-tetramethyl-9,10-di (2-naphthyl) anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10 , 10′-bis (2-phenylphenyl) -9,9′-bianthryl, 10,10′-bis [(2,3,4,5,6-pentaphenyl) phenyl] -9,9′-bianthryl, Anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra (tert-butyl) perylene and the like can be mentioned. In addition, pentacene, coronene, and the like can also be used. Thus, it is more preferable to use an aromatic hydrocarbon having a hole mobility of 1 × 10 ⁻⁶ cm ² / Vs or more and having 14 to 42 carbon atoms.

  Note that the aromatic hydrocarbon that can be used for the composite material may have a vinyl skeleton. As the aromatic hydrocarbon having a vinyl group, for example, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.

  Alternatively, a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can be used.

The substance forming the second layer 104 is preferably a substance having a high hole-transport property, specifically, an aromatic amine (that is, a compound having a benzene ring-nitrogen bond). As a widely used material, 4,4′-bis [N- (3-methylphenyl) -N-phenylamino] biphenyl and its derivative 4,4′-bis [N- (1-naphthyl)- N-phenylamino] biphenyl (hereinafter referred to as NPB), 4,4 ′, 4 ″ -tris (N, N-diphenyl-amino) triphenylamine, 4,4 ′, 4 ″ -tris [N— And starburst aromatic amine compounds such as (3-methylphenyl) -N-phenylamino] triphenylamine. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the second layer 104 is not limited to a single layer, and a mixed layer of the above substances or a layer in which two or more layers are stacked may be used.

  The third layer 105 is a layer containing a light emitting substance. In this embodiment mode, the third layer 105 includes the anthracene derivative of the present invention described in Embodiment Mode 1. Since the anthracene derivative of the present invention emits blue-green to yellow-green light, it can be suitably used for a light-emitting element as a light-emitting substance.

For the fourth layer 106, a substance having a high electron-transport property can be used. For example, tris (8-quinolinolato) aluminum (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (abbreviation: BAlq), and the like, a layer made of a metal complex having a quinoline skeleton or a benzoquinoline skeleton. In addition, bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (abbreviation: Zn (BOX) ₂ ), bis [2- (2-hydroxyphenyl) benzothiazolate] zinc (abbreviation: Zn (BTZ)) A metal complex having an oxazole-based or thiazole-based ligand such as ₂ ) can also be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4-phenyl-5- (4- tert-Butylphenyl) -1,2,4-triazole (abbreviation: TAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and the like can also be used. The substances mentioned here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that other than the above substances, any substance that has a property of transporting more electrons than holes may be used for the electron-transport layer. Further, the electron-transport layer is not limited to a single layer, and two or more layers including the above substances may be stacked.

  As a material for forming the second electrode 107, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) can be used. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), Examples thereof include alkaline earth metals such as strontium (Sr) and alloys (MgAg, AlLi) containing these. Rare earth metals such as europium (Eu) and ytterbium (Yb) and alloys containing these are also suitable. However, by providing a layer having a function of promoting electron injection between the second electrode 107 and the fourth layer 106, Al, Ag, ITO, silicon, or silicon oxide can be used regardless of the work function. Various conductive materials such as contained ITO can be used as the second electrode 107.

As a layer having a function of promoting electron injection, an alkali metal or an alkaline earth metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), or a compound thereof is used. Can be used. Alternatively, a layer formed of a substance having an electron transporting property in which an alkali metal, an alkaline earth metal, or a compound thereof is contained (for example, a material containing magnesium (Mg) in Alq) can be used. . In particular, by using an electron injection layer containing an alkali metal or an alkaline earth metal in a layer made of an electron transporting substance, electron injection from the second electrode 107 occurs more efficiently. preferable.

  In addition, as a method for forming the first layer 103, the second layer 104, the third layer 105, and the fourth layer 106, various methods such as an evaporation method, an inkjet method, and a spin coating method can be used. . Moreover, you may form using the different film-forming method for each electrode or each layer.

  In the light-emitting element of the present invention having the above structure, the third layer 105 which is a layer containing a highly light-emitting substance is applied by applying a voltage between the first electrode 102 and the second electrode 107. In which holes and electrons recombine and emit light. That is, a light emitting region is formed in the third layer 105.

  Light emission is extracted outside through one or both of the first electrode 102 and the second electrode 107. Therefore, either one or both of the first electrode 102 and the second electrode 107 is a light-transmitting electrode. In the case where only the first electrode 102 is a light-transmitting electrode, light emission is extracted from the substrate side through the first electrode 102 as illustrated in FIG. In the case where only the second electrode 107 is a light-transmitting electrode, light emission is extracted from the side opposite to the substrate through the second electrode 107 as illustrated in FIG. In the case where each of the first electrode 102 and the second electrode 107 is a light-transmitting electrode, light emission passes through the first electrode 102 and the second electrode 107 as illustrated in FIG. , Taken out from both the substrate side and the opposite side of the substrate.

  Note that the structure of the layers provided between the first electrode 102 and the second electrode 107 is not limited to the above. In order to prevent the quenching phenomenon caused by the proximity of the light emitting region and the metal, a light emitting region in which holes and electrons are recombined is provided at a site away from the first electrode 102 and the second electrode 107. Any other than the above may be used.

In other words, the layered structure of the layers is not limited to the above structure, and is a substance having a high electron transporting property or a substance having a high hole transporting property, a substance having a high electron injecting property, a substance having a high hole injecting property, A layer made of a substance having a high hole transporting property), a hole blocking material, or the like may be freely combined with the anthracene derivative of the present invention.

  2 includes a first electrode 302 functioning as a cathode, a first layer 303 made of a substance having a high electron-transport property, a second layer 304 containing a luminescent substance, holes, and a substrate. A structure in which a third layer 305 made of a substance having a high transport property, a fourth layer 306 made of a substance having a high hole injection property, and a second electrode 307 functioning as an anode are sequentially stacked.

  In this embodiment mode, a light-emitting element is manufactured over a substrate made of glass, plastic, or the like. A passive light-emitting device can be manufactured by manufacturing a plurality of such light-emitting elements over one substrate. Alternatively, for example, a thin film transistor (TFT) may be formed over a substrate made of glass, plastic, or the like, and a light-emitting element may be formed over an electrode electrically connected to the TFT. Thus, an active matrix light-emitting device in which driving of the light-emitting element is controlled by the TFT can be manufactured. Note that the structure of the TFT is not particularly limited. A staggered TFT or an inverted staggered TFT may be used. Further, there is no particular limitation on the crystallinity of the semiconductor used for the TFT, and an amorphous semiconductor or a crystalline semiconductor may be used. Also, the driving circuit formed on the TFT substrate may be composed of N-type and P-type TFTs, or may be composed of only one of N-type TFTs and P-type TFTs. Good.

  Since the anthracene derivative of the present invention emits blue-green to yellow-green light, it can be used as a light-emitting layer without adding another light-emitting substance as shown in this embodiment mode.

  Since the anthracene derivative of the present invention has high emission efficiency, a light-emitting element with high emission efficiency can be obtained by using it for a light-emitting element. In addition, by using the anthracene derivative of the present invention for a light-emitting element, a long-life light-emitting element can be obtained.

  In addition, since a light-emitting element using the anthracene derivative of the present invention can emit green light with high efficiency, it can be suitably used for a full-color display. Further, since long-life green light emission is possible, it can be suitably used for a full-color display.

  In addition, since the light-emitting element using the anthracene derivative of the present invention can emit green light with high efficiency, white light emission can be obtained by combining with other light-emitting materials. For example, when trying to obtain white light emission using red (R), green (G), and blue (B) light emission of NTSC chromaticity coordinates, approximately red (R): green (G): blue (B) = 1: 6: 3 If the light emission of each color is not mixed, it will not become white. In other words, the anthracene derivative of the present invention, which requires high-brightness green light emission and can obtain high-efficiency green light emission, is suitable for a light-emitting device.

(Embodiment 3)
In this embodiment, a light-emitting element having a structure different from that described in Embodiment 2 will be described.

  In this embodiment mode, light emission from the anthracene derivative of the present invention can be obtained by using the third layer 105 illustrated in FIG. 1 in which the anthracene derivative of the present invention is dispersed in another substance. Since the anthracene derivative of the present invention emits blue-green to yellow-green light, a light-emitting element that emits blue-green to yellow-green can be obtained.

  Here, as the substance for dispersing the anthracene derivative of the present invention, various materials can be used. In addition to the substance with a high hole transport and the substance with a high electron transport property described in Embodiment 2, 4, 4 '-Bis (N-carbazolyl) -biphenyl (abbreviation: CBP) and 2,2', 2 "-(1,3,5-benzenetri-yl) -tris [1-phenyl-1H-benzimidazole] ( Abbreviations: TPBI), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9- [ 4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and the like.

  Since the anthracene derivative of the present invention has high emission efficiency, a light-emitting element with high emission efficiency can be obtained by using it for a light-emitting element. In addition, by using the anthracene derivative of the present invention for a light-emitting element, a long-life light-emitting element can be obtained.

  In addition, since a light-emitting element using the anthracene derivative of the present invention can emit green light with high efficiency, it can be suitably used for a full-color display. Further, since long-life green light emission is possible, it can be suitably used for a full-color display.

  In addition, since the light-emitting element using the anthracene derivative of the present invention can emit green light with high efficiency, white light emission can be obtained by combining with other light-emitting materials. For example, when trying to obtain white light emission using red (R), green (G), and blue (B) light emission of NTSC chromaticity coordinates, approximately red (R): green (G): blue (B) = 1: 6: 3 If the light emission of each color is not mixed, it will not become white. In other words, the anthracene derivative of the present invention, which requires high-brightness green light emission and can obtain high-efficiency green light emission, is suitable for a light-emitting device.

  Note that the structure described in Embodiment 2 can be used as appropriate, except for the third layer 105.

(Embodiment 4)
In this embodiment, a light-emitting element having a structure different from those described in Embodiment 2 and Embodiment 3 will be described.

  In this embodiment, the third layer 105 illustrated in FIGS. 1A and 1B has a structure in which a light-emitting substance is dispersed in the anthracene derivative of the present invention, so that light emission from the light-emitting substance can be obtained.

  When the anthracene derivative of the present invention is used as a material for dispersing other luminescent substances, a luminescent color resulting from the luminescent substance can be obtained. In addition, it is possible to obtain a mixed emission color of the emission color caused by the anthracene derivative of the present invention and the emission color caused by the luminescent substance dispersed in the anthracene derivative.

Here, various materials can be used as the light-emitting substance dispersed in the anthracene derivative of the present invention. Specifically, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran (abbreviation: DCM1), 4- (dicyanomethylene) -2-methyl-6- (julolidine) A fluorescent substance that emits fluorescence, such as -4-yl-vinyl) -4H-pyran (abbreviation: DCM2), N, N-dimethylquinacridone (abbreviation: DMQd), and rubrene, can be used. Further, acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) ₂ (acac)), 2,3,7,8,12,13, A phosphorescent substance that emits phosphorescence, such as 17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation: PtOEP), can be used.

  Note that the structure described in Embodiment 2 can be used as appropriate, except for the third layer 105.

(Embodiment 5)
In this embodiment, a light-emitting element having a structure different from the structures shown in Embodiments 2 to 3 will be described.

  The anthracene derivative of the present invention has a hole transport property. Therefore, a layer containing the anthracene derivative of the present invention can be used between the anode and the light-emitting layer. Specifically, the first layer 103 and the second layer 104 described in Embodiment 1 can be used.

  In the case where the anthracene derivative of the present invention is used for the first layer, it is preferable to combine the anthracene derivative of the present invention with an inorganic compound that exhibits an electron accepting property with respect to the anthracene derivative of the present invention. By using such a composite layer, the carrier density is increased, so that the hole injecting property and the hole transporting property are improved. Further, when the composite layer is used as the first layer 103, the first layer 103 can make ohmic contact with the first electrode 102, and a material for forming the first electrode is selected regardless of the work function. be able to.

  The inorganic compound used for the composite material is preferably a transition metal oxide. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties. Among these, molybdenum oxide is particularly preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.

  Note that this embodiment can be combined with any of the other embodiments as appropriate.

(Embodiment 6)
In this embodiment, a light-emitting element having a structure in which a plurality of light-emitting units according to the present invention is stacked (hereinafter referred to as a stacked element) will be described with reference to FIG. This light-emitting element is a stacked light-emitting element having a plurality of light-emitting units between a first electrode and a second electrode. As the configuration of each light emitting unit, a configuration similar to the configuration shown in Embodiments 2 to 5 can be used. That is, the light-emitting element described in Embodiment 2 is a light-emitting element having one light-emitting unit. In this embodiment, a light-emitting element having a plurality of light-emitting units will be described.

In FIG. 3, a first light emitting unit 511 and a second light emitting unit 512 are stacked between a first electrode 501 and a second electrode 502. The first electrode 501 and the second electrode 502 can be the same as those in Embodiment 2. In addition, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same configuration or different configurations, and the configurations are the same as those in Embodiments 2 to 5. Can do.

The charge generation layer 513 includes a composite material of an organic compound and a metal oxide. This composite material of an organic compound and a metal oxide is the composite material described in Embodiment 2 or 5, and includes an organic compound and a metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. . As the organic compound, various compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a high molecular compound (oligomer, dendrimer, polymer, etc.) can be used. Note that an organic compound having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher is preferably used. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Since the composite material of an organic compound and a metal oxide is excellent in carrier injecting property and carrier transporting property, low voltage driving and low current driving can be realized.

Note that the charge generation layer 513 may be formed by combining a composite material of an organic compound and a metal oxide with another material. For example, a layer including a composite material of an organic compound and a metal oxide may be combined with a layer including one compound selected from electron donating substances and a compound having a high electron transporting property. Alternatively, a layer including a composite material of an organic compound and a metal oxide may be combined with a transparent conductive film.

In any case, when the voltage is applied to the first electrode 501 and the second electrode 502, the charge generation layer 513 sandwiched between the first light emitting unit 511 and the second light emitting unit 512 has one light emitting unit. Any device may be used as long as it injects electrons into the other light emitting unit and injects holes into the other light emitting unit. For example, in the case where a voltage is applied so that the potential of the first electrode is higher than the potential of the second electrode, the charge generation layer 513 injects electrons into the first light-emitting unit 511, Any structure may be used as long as holes are injected into the light emitting unit 512.

  Although the light-emitting element having two light-emitting units has been described in this embodiment mode, the present invention can also be applied to a light-emitting element in which three or more light-emitting units are stacked. By arranging a plurality of light emitting units separated by a charge generation layer between a pair of electrodes, it is possible to emit light with high luminance while keeping the current density low, and as a result, a long-life element can be realized. Further, when illumination is used as an application example, the influence of the voltage drop due to the resistance of the electrode material can be reduced, so that uniform light emission over a large area is possible.

  Note that this embodiment can be combined with any of the other embodiments as appropriate.

(Embodiment 7)
In this embodiment mode, a light-emitting device manufactured using the anthracene derivative of the present invention will be described.

  In this embodiment mode, a light-emitting device manufactured using the anthracene derivative of the present invention will be described with reference to FIGS. 4A is a top view of the light-emitting device, and FIG. 4B is a cross-sectional view of FIG. 4A cut along A-A ′ and B-B ′. Reference numeral 601 indicated by a dotted line denotes a driving circuit portion (source side driving circuit), 602 denotes a pixel portion, and 603 denotes a driving circuit portion (gate side driving circuit). Reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

  A lead wiring 608 is a wiring for transmitting a signal input to the source side driving circuit 601 and the gate side driving circuit 603, and a video signal, a clock signal, and a start signal from an FPC (flexible printed circuit) 609 serving as an external input terminal. Receive a reset signal, etc. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to the FPC. The light-emitting device in this specification includes not only a light-emitting device body but also a state in which an FPC or a PWB is attached thereto.

  Next, a cross-sectional structure is described with reference to FIG. A driver circuit portion and a pixel portion are formed over the element substrate 610. Here, a source-side driver circuit 601 that is a driver circuit portion and one pixel in the pixel portion 602 are illustrated.

  Note that the source side driver circuit 601 is a CMOS circuit in which an n-channel TFT 623 and a p-channel TFT 624 are combined. The drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment mode, a driver integrated type in which a driver circuit is formed over a substrate is shown; however, this is not necessarily required, and the driver circuit can be formed outside the substrate.

  The pixel portion 602 is formed by a plurality of pixels including a switching TFT 611, a current control TFT 612, and a first electrode 613 electrically connected to the drain thereof. Note that an insulator 614 is formed so as to cover an end portion of the first electrode 613. Here, a positive photosensitive acrylic resin film is used.

  In order to obtain good coverage, a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614. For example, in the case where a positive photosensitive acrylic resin is used as the material of the insulator 614, it is preferable that only the upper end portion of the insulator 614 has a curved surface having a curvature radius (0.2 μm to 3 μm). As the insulator 614, either a negative resin that becomes insoluble in an etchant by light irradiation or a positive resin that becomes soluble in an etchant by light irradiation can be used.

  Over the first electrode 613, a layer 616 containing a light-emitting substance and a second electrode 617 are formed. Here, as a material used for the first electrode 613 functioning as an anode, a material having a high work function is preferably used. For example, an ITO film or an indium tin oxide film containing silicon, an indium oxide film containing 2 to 20 wt% zinc oxide, a single layer film such as a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film In addition, a stack of titanium nitride and a film containing aluminum as a main component, a three-layer structure including a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film can be used. Note that with a stacked structure, resistance as a wiring is low, good ohmic contact can be obtained, and a function as an anode can be obtained.

  The layer 616 containing a light-emitting substance is formed by various methods such as an evaporation method using an evaporation mask, an inkjet method, and a spin coating method. The layer 616 containing a light-emitting substance contains the anthracene derivative of the present invention described in Embodiment Mode 1. Further, as another material constituting the layer 616 containing a light-emitting substance, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) may be used.

Further, as a material used for the second electrode 617 formed over the light-emitting substance-containing layer 616 and functioning as a cathode, a material having a low work function (Al, Mg, Li, Ca, or an alloy or compound thereof, MgAg, or the like) , MgIn, AlLi, LiF, be used or CaF ₂₎ preferred. Note that in the case where light generated in the layer 616 containing a light-emitting substance passes through the second electrode 617, the second electrode 617 includes a thin metal film and a transparent conductive film (ITO, 2 to 20 wt. It is preferable to use a stack of indium oxide containing 1% zinc oxide, silicon, indium oxide-tin oxide containing silicon oxide, zinc oxide (ZnO), or the like.

  Further, the sealing substrate 604 is bonded to the element substrate 610 with the sealant 605, whereby the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. Yes. Note that the space 607 is filled with a filler, and may be filled with a sealant 605 in addition to an inert gas (such as nitrogen or argon).

  Note that an epoxy-based resin is preferably used for the sealant 605. Moreover, it is desirable that these materials are materials that do not transmit moisture and oxygen as much as possible. In addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiberglass-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as a material used for the sealing substrate 604.

  Through the above process, a light-emitting device manufactured using the anthracene derivative of the present invention can be obtained.

  Since the anthracene derivative described in Embodiment Mode 1 is used for the light-emitting device of the present invention, a light-emitting device having excellent characteristics can be obtained. Specifically, a light-emitting device with a long lifetime can be obtained.

  In addition, since the anthracene derivative of the present invention has high emission efficiency, a light-emitting device with low power consumption can be obtained.

  Further, since the anthracene derivative of the present invention can emit green light with high efficiency, it can be suitably used for a full color display. In addition, since the power consumption is low and long-life green light emission is possible, it can be suitably used for a full-color display.

  Further, since the anthracene derivative of the present invention can emit green light with high efficiency, white light emission can be obtained by combining with other light-emitting materials. For example, when trying to obtain white light emission using red (R), green (G), and blue (B) light emission of NTSC chromaticity coordinates, approximately red (R): green (G): blue (B) = 1: 6: 3 If the light emission of each color is not mixed, it will not become white. In other words, the anthracene derivative of the present invention, which requires high-brightness green light emission and can obtain high-efficiency green light emission, is suitable for a light-emitting device.

  As described above, in this embodiment mode, an active light-emitting device that controls driving of a light-emitting element using a transistor has been described, but in addition, a passive device that drives a light-emitting element without providing a driving element such as a transistor is used. It may be a type of light emitting device. FIG. 5 is a perspective view of a passive light emitting device manufactured by applying the present invention. In FIG. 5, a layer 955 containing a light-emitting substance is provided over the substrate 951 between the electrode 952 and the electrode 956. An end portion of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided over the insulating layer 953. The side wall of the partition wall layer 954 has an inclination such that the distance between one side wall and the other side wall becomes narrower as it approaches the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 has a trapezoidal shape, and the bottom side (the side facing the insulating layer 953 in the same direction as the surface direction of the insulating layer 953) is the top side (the surface of the insulating layer 953). The direction is the same as the direction and is shorter than the side not in contact with the insulating layer 953. Thus, by providing the partition layer 954, the cathode can be patterned. Even in a passive light-emitting device, a light-emitting device with a long lifetime can be obtained by using the light-emitting element of the present invention. In addition, a light-emitting device with low power consumption can be obtained.

(Embodiment 8)
In this embodiment, electronic devices of the present invention including the light-emitting device described in Embodiment 7 will be described. An electronic device of the present invention includes the anthracene derivative described in Embodiment 1 and has a display portion with a long lifetime. In addition, a display portion with reduced power consumption is included.

  As an electronic device having a light-emitting element manufactured using the anthracene derivative of the present invention, a video camera, a digital camera, a goggle type display, a navigation system, a sound reproduction device (car audio, audio component, etc.), a computer, a game device, a mobile phone An information terminal (mobile computer, mobile phone, portable game machine, electronic book, etc.), an image playback device (specifically, Digital Versatile Disc (DVD)) provided with a recording medium, and the image is displayed. And a device provided with a display device capable of performing the above. Specific examples of these electronic devices are shown in FIGS.

  FIG. 6A illustrates a television device according to the present invention, which includes a housing 9101, a supporting base 9102, a display portion 9103, a speaker portion 9104, a video input terminal 9105, and the like. In this television device, the display portion 9103 is formed by arranging light-emitting elements similar to those described in Embodiment Modes 2 to 5 in a matrix. The light-emitting element has characteristics of high light emission efficiency and long life. Since the display portion 9103 including the light-emitting elements has similar features, this television set has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation function circuit and the power supply circuit can be significantly reduced or reduced in the television device; therefore, the housing 9101 and the support base 9102 can be reduced in size and weight. In the television device according to the present invention, low power consumption, high image quality, and reduction in size and weight are achieved, so that a product suitable for a living environment can be provided. Further, since the anthracene derivative described in Embodiment 1 can emit green light, a full-color display is possible and a television device having a display portion with a long lifetime can be obtained.

  FIG. 6B illustrates a computer according to the present invention, which includes a main body 9201, a housing 9202, a display portion 9203, a keyboard 9204, an external connection port 9205, a pointing device 9206, and the like. In this computer, the display portion 9203 is formed by arranging light-emitting elements similar to those described in Embodiment Modes 2 to 5 in a matrix. The light-emitting element has characteristics of high light emission efficiency and long life. The display portion 9203 which includes the light-emitting elements has similar features. Therefore, in this computer, image quality is hardly deteriorated and low power consumption is achieved. With such a feature, deterioration compensation functional circuits and power supply circuits can be significantly reduced or reduced in the computer, so that the main body 9201 and the housing 9202 can be reduced in size and weight. In the computer according to the present invention, low power consumption, high image quality, and reduction in size and weight are achieved; therefore, a product suitable for the environment can be provided. Further, since the anthracene derivative described in Embodiment 1 can emit green light, a full-color display is possible and a computer having a display portion with a long lifetime can be obtained.

  6C illustrates a cellular phone according to the present invention, which includes a main body 9401, a housing 9402, a display portion 9403, an audio input portion 9404, an audio output portion 9405, operation keys 9406, an external connection port 9407, an antenna 9408, and the like. . In this cellular phone, the display portion 9403 is formed by arranging light-emitting elements similar to those described in Embodiments 2 to 5 in a matrix. The light-emitting element has characteristics of high light emission efficiency and long life. Since the display portion 9403 including the light-emitting elements has similar features, the cellular phone has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation functional circuit and the power supply circuit can be significantly reduced or reduced in the mobile phone, so that the main body 9401 and the housing 9402 can be reduced in size and weight. Since the cellular phone according to the present invention has low power consumption, high image quality, and reduced size and weight, a product suitable for carrying can be provided. In addition, since the anthracene derivative described in Embodiment 1 can emit green light, full-color display is possible and a mobile phone having a display portion with a long lifetime can be obtained.

  6D illustrates a camera according to the present invention, which includes a main body 9501, a display portion 9502, a housing 9503, an external connection port 9504, a remote control receiving portion 9505, an image receiving portion 9506, a battery 9507, an audio input portion 9508, and operation keys 9509. , An eyepiece 9510 and the like. In this camera, the display portion 9502 is configured by arranging light-emitting elements similar to those described in Embodiment Modes 2 to 5 in a matrix. The light-emitting element has characteristics of high light emission efficiency and long life. Since the display portion 9502 including the light-emitting elements has similar features, this camera has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation function circuit and the power supply circuit can be significantly reduced or reduced in the camera, so that the main body 9501 can be reduced in size and weight. Since the camera according to the present invention has low power consumption, high image quality, and small size and light weight, a product suitable for carrying can be provided. In addition, since the anthracene derivative described in Embodiment Mode 1 can emit green light, full color display is possible and a camera having a display portion with a long lifetime can be obtained.

  As described above, the applicable range of the light-emitting device of the present invention is so wide that the light-emitting device can be applied to electronic devices in various fields. By using the anthracene derivative of the present invention, an electronic device having a display portion with a long lifetime can be provided.

  The light-emitting device of the present invention can also be used as a lighting device. One mode in which the light-emitting element of the present invention is used as a lighting device will be described with reference to FIGS.

  FIG. 7 illustrates an example of a liquid crystal display device using the light-emitting device of the present invention as a backlight. The liquid crystal display device illustrated in FIG. 7 includes a housing 901, a liquid crystal layer 902, a backlight 903, and a housing 904, and the liquid crystal layer 902 is connected to a driver IC 905. The backlight 903 uses the light-emitting device of the present invention, and a current is supplied from a terminal 906.

  By using the light emitting device of the present invention as a backlight of a liquid crystal display device, a backlight with high luminous efficiency and reduced power consumption can be obtained. Further, the light-emitting device of the present invention is a surface-emitting illumination device and can have a large area, so that the backlight can have a large area and a liquid crystal display device can have a large area. Further, since the light-emitting device of the present invention is thin and has low power consumption, the display device can be thinned and the power consumption can be reduced. In addition, since the light emitting device of the present invention has a long life, a liquid crystal display device using the light emitting device of the present invention also has a long life.

  FIG. 8 shows an example of a light emitting device to which the present invention is applied. FIG. 8 shows an example in which a desk lamp is applied as a lighting device. A table lamp illustrated in FIG. 8 includes a housing 2001 and a light source 2002, and the light-emitting device of the present invention is used as the light source 2002. Since the light-emitting device of the present invention has high light emission efficiency and a long life, the desk lamp also has high light emission efficiency and a long life.

  FIG. 9 shows an example in which the present invention is applied to a light emitting device. FIG. 9 shows an example applied to an indoor lighting device 3001. Since the light-emitting device of the present invention can have a large area, it can be used as a large-area lighting device. In addition, since the light-emitting device of the present invention is thin and has low power consumption, it can be used as a lighting device with low thickness and low power consumption. Therefore, a television set 3002 according to the present invention as described with reference to FIG. 6A is installed in a room where the light-emitting device manufactured according to the present invention is used as an indoor lighting device 3001, so that a public broadcast or a movie can be played. You can appreciate it. In such a case, since both devices have low power consumption, powerful images can be viewed in a bright room without worrying about electricity charges.

  In this example, 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA) which is an anthracene derivative of the present invention represented by the structural formula (101) ) Will be described in detail.

[Step 1] Synthesis of 2-bromo-9,10-diphenylanthracene

(I) Synthesis of 2-bromo-9,10-anthraquinone A synthesis scheme of 2-bromo-9,10-anthraquinone is shown in (C-1).

  Put 46 g (206 mmol) of copper (II) bromide and 500 mL of acetonitrile in a 1 L three-necked flask, add 17.3 g (168 mmol) of tert-butyl nitrite, heat to 65 ° C., and heat 25 g of 2-amino-9,10-anthraquinone ( 111.0 mmol) was added, and the mixture was stirred at the same temperature for 6 hours. After the reaction, the reaction mixture was poured into 3M hydrochloric acid and stirred for 3 hours, and the precipitate was filtered and washed with water and ethanol. The filtrate was dissolved in toluene and filtered through Florisil, Celite, and alumina, and the filtrate was concentrated and recrystallized with chloroform and hexane to obtain 18.6 g of 2-bromo-9,10-anthraquinone cream solid, yield. Obtained at 58%.

(Ii) Synthesis of 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol of 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol The synthesis scheme is shown in (C-2).

  2.90 g (16.95 mmol) of 2-bromo-9,10-anthraquinone was placed in a 300 mL three-necked flask, purged with nitrogen, 100 mL of tetrahydrofuran (THF) was added, and 17.76 mL (37.29 mmol) of a phenylbutyl dibutyl ether solution. Was added dropwise and stirred at room temperature for about 12 hours. After the reaction, the solution was washed with water, the aqueous layer was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. The organic layer was filtered and concentrated to obtain the desired 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol.

(Iii) Synthesis of 2-bromo-9,10-diphenylanthracene A synthesis scheme of 2-bromo-9,10-diphenylanthracene is shown in (C-3).

  The obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol 7.55 g (16.95 mmol), potassium iodide 5.06 g (30.51 mmol), sodium phosphinate 9.70 g (91.52 mmol) of hydrate and 50 mL of glacial acetic acid were placed in a 500 mL three-necked flask and stirred at 120 ° C. for 2 hours. Thereafter, 30 mL of 50% phosphinic acid was added and stirred at 120 ° C. for 1 hour. After the reaction, the reaction mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting residue was dissolved in toluene and filtered through celite, florisil and alumina. The filtrate was concentrated and recrystallized with chloroform and hexane to obtain 5.1 g (yield: 74%) of 2-bromo-9,10-diphenylanthracene as a target product.

[Step 2] Synthesis method of 2DPAPA A synthesis scheme of 2DPAPA is shown in (C-4).

  1.8 g (4.40 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Example 1, 1.78 g of N, N, N′-triphenyl-1,4-phenylenediamine (DPA) (5.28 mmol), 0.126 g (0.220 mmol) of bis (dibenzylideneacetone) palladium (0), and 2.11 g (21.99 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask and purged with nitrogen. 30 mL, 0.44 g (0.220 mmol) of tri (tert-butyl) phosphine (10% hexane solution) was added, and the mixture was heated at 80 ° C. for 6 hours. After the reaction, the solution was washed with water, the aqueous layer was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. After drying, the organic layer was filtered and concentrated, and the resulting residue was dissolved in toluene and then filtered through Celite, Florisil, and alumina. The filtrate was concentrated and the residue was recrystallized with chloroform, methanol and hexane to obtain 2.24 g of the objective yellow solid in a yield of 77%. This compound was confirmed to be 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA) by nuclear magnetic resonance measurement (NMR).

The ¹ H NMR data of 2DPAPA is shown below. ¹ H-NMR (DMSO-d _6, 300 MHz): δ = 6.90-7.14 (m, 15H), 7.25-7.37 (m, 10H), 7.44-7.52 (m , 8H), 7.57-7.66 (m, 3H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 11B is a chart in which the range of 6.5 ppm to 8.0 ppm in FIG.

  When the decomposition temperature (Td) of 2DPAPA was measured with a differential thermothermal gravimetric simultaneous measurement device (Seiko Denshi Co., Ltd., TG / DTA320 type), it was found that Td = 395.9 ° C., indicating high thermal stability. It was.

  Further, FIG. 12 shows an absorption spectrum of a 2DPAPA toluene solution. Further, FIG. 13 shows an absorption spectrum of a thin film of 2DPAPA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by vapor-depositing 2DPAPA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIGS. 12 and 13, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 442 nm, and in the case of the thin film, absorption was observed at around 452 nm. Further, FIG. 14 shows an emission spectrum of a toluene solution of 2DPAPA (excitation wavelength: 430 nm). An emission spectrum of a 2DPAPA thin film (excitation wavelength: 452 nm) is shown in FIG. 14 and 15, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 539 nm (excitation wavelength: 430 nm) in the case of the toluene solution, and 543 nm (excitation wavelength: 452 nm) in the case of the thin film.

  As a result of measuring the HOMO level of 2DPAPA in a thin film state by photoelectron spectroscopy in the atmosphere (AC-2, manufactured by Riken Keiki Co., Ltd.), it was -5.28 eV. The optical energy gap was estimated from the absorption edge obtained from the Tauc plot of the absorption spectrum of the 2DPAPA thin film in FIG. 13 and found to be 2.46 eV. Therefore, the LUMO level is -2.82 eV.

  In this example, 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino which is an anthracene derivative of the present invention represented by the structural formula (201) is used. A method for synthesizing anthracene (abbreviation: 2PCAPA) will be specifically described.

[Step 1] Synthesis of N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA)

(I) Synthesis of 3-bromo-9-phenylcarbazole A synthesis scheme of 3-bromo-9-phenylcarbazole is shown in (C-5).

  To a 2 L Meyer flask, 24.3 g (100 mmol) of 9-phenylcarbazole was added, dissolved in 600 mL of glacial acetic acid, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added, and the mixture was stirred at room temperature for about 12 hours. This glacial acetic acid solution was added dropwise to 1 L of ice water with stirring. The precipitated white solid was collected by suction filtration and washed with water three times. This solid was dissolved in 150 mL of diethyl ether and washed with a saturated aqueous sodium hydrogen carbonate solution and water. The organic layer was dried over magnesium sulfate, filtered, the obtained filtrate was concentrated, and the residue was dissolved in about 50 mL of methanol. The precipitated white solid was collected by suction filtration and dried to obtain 28.4 g (yield 88%) of 3-bromo-9-phenylcarbazole as a white powder.

(Ii) Synthesis of N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA) N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA) ) Shows a synthesis scheme of (C-6).

  In a 500 mL three-necked flask, 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 340 mg (0.6 mmol) of bis (dibenzylideneacetone) palladium (0), 1 of 1,1-bis (diphenylphosphino) ferrocene 1.6 g (3.0 mmol) and 13 g (180 mmol) of sodium tert-butoxide were added, and after nitrogen substitution, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added. This mixture was heated and stirred at 90 ° C. for 7.5 hours under a nitrogen atmosphere. After completion of the reaction, about 500 mL of heated toluene was added to the reaction solution, and this was filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, and hexane and ethyl acetate were added to the residue and irradiated with ultrasonic waves. The precipitated solid was collected by suction filtration to obtain 15 g (yield: 75%) of cream-colored powder of N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA). This compound was confirmed to be N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA) by nuclear magnetic resonance measurement (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): 6.84 (t, J = 6.9 Hz, 1H), 6.97 (d, J = 7.8 Hz, 2H), 7.20-7.61 (m, 13H), 7.90 (s, 1H), 8.04 (d, J = 7.8 Hz, 1H). ¹ H NMR charts are shown in FIGS. 16 (A) and 16 (B). Note that FIG. 16B is a chart in which the range of 5.0 ppm to 9.0 ppm in FIG.

[Step 2] Synthesis method of 2PCAPA The synthesis scheme of 2PCAPA is shown in (C-7).

  1.8 g (4.40 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Example 1, N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA) ) 1.76 g (5.28 mmol), bis (dibenzylideneacetone) palladium (0) 0.126 g (0.220 mmol), sodium tert-butoxide 2.11 g (21.99 mmol) were placed in a 100 mL three-necked flask and purged with nitrogen. Further, 30 mL of toluene and 0.44 g (0.220 mmol) of tri (tert-butyl) phosphine (10% hexane solution) were added and stirred at 80 ° C. for 6 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate and dried over magnesium sulfate. After drying, the reaction mixture obtained by filtration and concentration was dissolved in toluene, and then filtered through Celite, Florisil, and alumina. The filtrate was concentrated, and the residue was recrystallized from chloroform, methanol and hexane to obtain 2.33 g of the objective yellow solid in a yield of 80%. By nuclear magnetic resonance measurement (NMR), this compound is 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). It was confirmed.

¹ H NMR data of this compound is shown below. ¹ H-NMR (CDCl _3, 300 MHz): δ = 6.92-6.97 (m, 1H), 7.11-7.32 (m, 16H), 7.39-7.66 (m, 15H) ), 7.88-7.97 (m, 2H). ¹ H NMR charts are shown in FIGS. 17 (A) and 17 (B). Note that FIG. 17B is a chart in which the range of 6.5 ppm to 8.0 ppm in FIG.

  When the decomposition temperature (Td) of 2PCAPA was measured with a differential thermothermal gravimetric simultaneous measurement apparatus (Seiko Denshi Co., Ltd., TG / DTA320 type), it was found that Td = 410.1 ° C., indicating high thermal stability. It was.

  Further, FIG. 18 shows an absorption spectrum of a toluene solution of 2PCAPA. Further, FIG. 19 shows an absorption spectrum of a thin film of 2PCAPA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2PCAPA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIGS. 18 and 19, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 442 nm, and in the case of the thin film, absorption was observed near 448 nm. Further, FIG. 20 shows an emission spectrum of a toluene solution of 2PCAPA (excitation wavelength: 430 nm). In addition, FIG. 21 shows an emission spectrum of a thin film of 2PCAPA (excitation wavelength: 448 nm). 20 and 21, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 508 nm (excitation wavelength 430 nm) in the case of the toluene solution, and 537 nm (excitation wavelength 448 nm) in the case of the thin film.

  As a result of measuring the HOMO level of 2PCAPA in a thin film state by photoelectron spectroscopy in the atmosphere (AC-2, manufactured by Riken Keiki Co., Ltd.), it was -5.26 eV. The optical energy gap was estimated from the absorption edge obtained from the Tauc plot of the absorption spectrum of the 2PCAPA thin film in FIG. 19, and found to be 2.47 eV. Therefore, the LUMO level is −2.79 eV.

  The oxidation-reduction characteristics of 2PCAPA were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

The solution in the CV measurement was dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number; 22705-6) as a solvent. The supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved in DMF to a concentration of 100 mmol / L, and electrolysis was performed. The solution was adjusted. Furthermore, the measurement object was dissolved in the electrolytic solution so as to have a concentration of 1 mmol / L. In addition, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) is used as the working electrode, and a platinum electrode (manufactured by BAS Corp., Pt counter electrode for VC-3 (as a counter electrode) 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of 2PCAPA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.23 V to 0.60 V, scanning for changing from 0.60 V to −0.23 V was set as one cycle, and 100 cycles were performed. The reduction reaction characteristics of 2PCAPA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.41 V to −2.50 V, scanning for changing from −2.50 V to −0.41 V was taken as one cycle, and 100 cycles were performed. The scan speed for CV measurement was set to 0.1 V / s.

FIG. 22 shows the CV measurement result on the oxidation side of 2PCAPA, and FIG. 23 shows the CV measurement result on the reduction side of 2PCAPA. 22 and 23, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the counter electrode. From FIG. 22, a current indicating oxidation was observed around −0.47 V (vs. Ag / Ag ⁺ ). Further, from FIG. 23, a current indicating reduction was observed in the vicinity of -2.22 V (vs. Ag / Ag ⁺ ).

  Despite repeated measurements for 100 cycles, there is almost no change in the peak position or peak intensity of the CV curve in the oxidation and reduction reactions. From this, it was found that the anthracene derivative of the present invention is extremely stable against repeated redox reactions.

  In this example, 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino], which is an anthracene derivative of the present invention represented by the structural formula (115), is used. A method for synthesizing anthracene (abbreviation: 2DPABPhA) will be specifically described.

[Step 1] Synthesis of 9,10-di (2-biphenylyl) -2-bromoanthracene The synthesis scheme of 9,10-di (2-biphenylyl) -2-bromoanthracene was changed from (C-8) to (C-10). ).

  2-Bromobiphenyl (22.84 g, 98.00 mmol) was placed in a 500 mL three-necked flask and purged with nitrogen. Tetrahydrofuran (THF) (100 mL) was added and n-butyllithium (1.57 mol / L hexane solution) (68.66 mL) at -78 ° C. (107.80 mmol) was added dropwise and stirred for 5 hours. To this solution was added dropwise a solution of 8.5 g (29.40 mmol) of 2-bromo-9,10-anthraquinone in 160 mL of THF under nitrogen, and the mixture was stirred for about 12 hours while returning to room temperature. After the reaction, water was added to the solution, and the precipitate was filtered to obtain 9,10-di (2-biphenylyl) -2-bromo-9,10-dihydroanthracene-9,10-diol cream colored solid.

  The resulting 9,10-di (2-biphenylyl) -2-bromo-9,10-dihydroanthracene-9,10-diol 18.32 g (30.66 mmol), potassium iodide 9.16 g (55.19 mmol) , Sodium phosphinate monohydrate (17.55 g, 165.56 mmol) and glacial acetic acid (150 mL) were put into a 500 mL three-necked flask and stirred at 120 ° C. for 5 hours. Thereafter, 100 mL of 50% phosphinic acid was added and stirred at 120 ° C. for 1 hour. After the reaction, the solution was washed with water, and the precipitate was filtered and recrystallized from chloroform and hexane. As a result, 11.4 g of a light yellow solid of 9,10-di (2-biphenylyl) -2-bromoanthracene was obtained. Obtained at 66%.

[Step 2] Synthesis method of 2DPABPhA A synthesis scheme of 2DPABPhA is shown in (C-11).

  9,10-di (2-biphenylyl) -2-bromoanthracene 2.0 g (3.56 mmol) synthesized in Step 1 of Example 3, N, N, N′-triphenyl-1,4-phenylenediamine ( DPA) 1.44 g (4.27 mmol), bis (dibenzylideneacetone) palladium (0) 0.102 g (0.178 mmol), sodium tert-butoxide 1.71 g (17.81 mmol) was placed in a 100 mL three-necked flask and replaced with nitrogen. Further, 30 mL of toluene and 0.36 g (0.178 mmol) of tri (tert-butyl) phosphine (10% hexane solution) were added and stirred at 80 ° C. for 7 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated, and the resulting residue was dissolved in toluene. This solution was filtered through Celite, Florisil, and alumina. The filtrate was concentrated and recrystallized with chloroform and methanol to obtain 2.5 g of the objective yellow solid in a yield of 87%. This compound is 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA) by nuclear magnetic resonance measurement (NMR). It was confirmed.

¹ H NMR data of this compound is shown below. ¹ H-NMR (CDCl _3, 300 MHz): δ = 6.78-7.08 (m, 24H), 7.12-7.30 (m, 10H), 7.32-7.59 (m, 10H) ). ¹ H NMR charts are shown in FIGS. 24 (A) and 24 (B). Note that FIG. 24B is a chart in which the range of 6.5 ppm to 8.0 ppm in FIG.

  When the decomposition temperature (Td) of 2DPABPhA was measured with a differential thermothermal gravimetric simultaneous measurement apparatus (Seiko Denshi Co., Ltd., TG / DTA320 type), it was found that Td = 419.8 ° C., indicating high thermal stability. It was.

  In addition, FIG. 25 shows an absorption spectrum of a toluene solution of 2DPABPhA. Further, FIG. 26 shows an absorption spectrum of a thin film of 2DPABPhA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2DPABPhA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIG. 25 and FIG. 25 and 26, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 446 nm, and in the case of the thin film, absorption was observed at around 449 nm. In addition, FIG. 27 shows an emission spectrum of a toluene solution of 2DPABPhA (excitation wavelength: 430 nm). In addition, FIG. 28 shows an emission spectrum of a 2DPABPhA thin film (excitation wavelength: 449 nm). 27 and 28, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 542 nm (excitation wavelength 430 nm) in the case of the toluene solution, and 548 nm (excitation wavelength 449 nm) in the case of the thin film.

  As a result of measuring the HOMO level of 2DPABPhA in a thin film state by photoelectron spectroscopy in the atmosphere (manufactured by Riken Keiki Co., Ltd., AC-2), it was −5.28 eV. The optical energy gap estimated from the absorption edge obtained by Tauc plot of the absorption spectrum of the 2DPABPhA thin film in FIG. 26 was 2.47 eV. Therefore, the LUMO level is -2.81 eV.

  In this example, 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazole-) which is an anthracene derivative of the present invention represented by the structural formula (215) is used. A method for synthesizing 3-yl) amino] anthracene (abbreviation: 2PCABPhA) will be specifically described.

[Step 1] Synthesis method of 2PCABPhA A synthesis scheme of 2PCABPhA is shown in (C-12).

  2.8 g (5.0 mmol) of 9,10-di (2-biphenylyl) -2-bromoanthracene synthesized in Step 1 of Example 3, N-phenyl- (9-phenyl) synthesized in Step 1 of Example 2 -9H-carbazol-3-yl) amine (abbreviation: PCA) 1.67 g (5.0 mmol), bis (dibenzylideneacetone) palladium 0.14 g (0.25 mmol), sodium tert-butoxide 2.4 g (25 mmol) Was placed in a 100 mL three-necked flask, the atmosphere was replaced with nitrogen, 20 mL of toluene and 1.5 g (0.75 mmol) of tri (tert-butyl) phosphine (10% hexane solution) were added, and the mixture was stirred at 80 ° C. for 4 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated, and the resulting residue was dissolved in toluene. This solution was filtered through Celite, Florisil, and alumina. The filtrate was concentrated and recrystallized with toluene and hexane to obtain 3.4 g of the objective yellow solid in a yield of 83%. This compound was analyzed by nuclear magnetic resonance (NMR) to give 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation) : 2PCABPhA).

¹ H NMR data of this compound is shown below. ¹ H-NMR (CDCl _3, 300 MHz): δ = 6.74-7.09 (m, 16H), 7.14-7.29 (m, 8H), 7.32-7.62 (m, 16H) ), 7.75-7.97 (m, 2H). ¹ H NMR charts are shown in FIGS. 29 (A) and 29 (B). Note that FIG. 29B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  When the decomposition temperature (Td) of 2PCABPhA was measured with a differential thermothermal gravimetric simultaneous measurement apparatus (Seiko Denshi Co., Ltd., TG / DTA320 type), Td = decomposition temperature: 423.7 ° C., indicating high thermal stability. I understood that.

  Further, FIG. 30 shows an absorption spectrum of a toluene solution of 2PCABPhA. Further, FIG. 31 shows an absorption spectrum of a thin film of 2PCABPhA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2PCABPhA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIG. 30 and FIG. 30 and 31, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 440 nm, and in the case of the thin film, absorption was observed near 449 nm. FIG. 32 shows the emission spectrum of a toluene solution of 2PCABPhA (excitation wavelength: 430 nm). In addition, FIG. 33 shows an emission spectrum of a thin film of 2PCABPhA (excitation wavelength: 449 nm). 32 and 33, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 509 nm (excitation wavelength: 430 nm) in the case of the toluene solution, and 534 nm (excitation wavelength: 449 nm) in the case of the thin film.

  It was -5.29 eV as a result of measuring the HOMO level in the thin film state of 2PCABPhA by the photoelectron spectroscopy in the air (the Riken Keiki Co., Ltd. make, AC-2). When the optical energy gap was estimated from the absorption edge obtained by Tauc plot of the absorption spectrum of the 2PCABPhA thin film in FIG. 31, it was 2.46 eV. Therefore, the LUMO level is −2.83 eV.

  Moreover, the oxidation-reduction characteristics of 2PCABPhA were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

The solution in the CV measurement was dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number; 22705-6) as a solvent. The supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved in DMF to a concentration of 100 mmol / L, and electrolysis was performed. The solution was adjusted. Furthermore, the measurement object was dissolved in the electrolytic solution so as to have a concentration of 1 mmol / L. In addition, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) is used as the working electrode, and a platinum electrode (manufactured by BAS Corp., Pt counter electrode for VC-3 (as a counter electrode) 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of 2PCABPhA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.23 V to 0.70 V, scanning for changing from 0.70 V to −0.23 V was taken as one cycle, and 100 cycles were performed. Further, the reduction characteristics of 2PCABPhA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.36 V to −2.50 V, scanning for changing from −2.50 V to −0.36 V was taken as one cycle, and 100 cycles were performed. The scan speed for CV measurement was set to 0.1 V / s.

FIG. 34 shows the CV measurement result on the oxidation side of 2PCABPhA, and FIG. 35 shows the CV measurement result on the reduction side of 2PCABPhA. 34 and 35, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the counter electrode. From FIG. 34, a current indicating oxidation was observed in the vicinity of 0.49 V (vs. Ag / Ag ⁺ ). From FIG. 35, a current indicating reduction was observed in the vicinity of -2.20 V (vs. Ag / Ag ⁺ ).

  Despite repeated measurements for 100 cycles, there is almost no change in the peak position or peak intensity of the CV curve in the oxidation and reduction reactions. From this, it was found that the anthracene derivative of the present invention is extremely stable against repeated redox reactions.

  In this example, 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl which is an anthracene derivative of the present invention represented by the structural formula (315) is used. ] -N-phenylamino} anthracene (abbreviation: 2YGABPhA) will be specifically described.

[Step 1] Synthesis of 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA)

(I) Synthesis of N- (4-bromophenyl) carbazole A synthesis scheme of N- (4-bromophenyl) carbazole is shown in (C-13).

  In a 300 mL three-necked flask, 56.3 g (0.24 mol) of 1,4-dibromobenzene, 31.3 g (0.18 mol) of carbazole, 4.6 g (0.024 mol) of copper (I) iodide, carbonic acid 66.3 g (0.48 mol) of potassium and 2.1 g (0.008 mol) of 18-crown-6-ether were added, and the atmosphere was purged with nitrogen to obtain 1,3-dimethyl-3,4,5,6-tetrahydro-2. 8 mL of (1H) -pyrimidinone (abbreviation: DMPU) was added and stirred at 180 ° C. for 6 hours. The reaction mixture was cooled to room temperature, the precipitate was removed by suction filtration, and the filtrate was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order, and dried over magnesium sulfate. After drying, the reaction mixture was naturally filtered, the filtrate was concentrated, and the obtained oily substance was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1). The obtained solid was recrystallized from chloroform and hexane to obtain 20.7 g of a light brown plate crystal of N- (4-bromophenyl) carbazole in a yield of 35%. The compound was confirmed to be N- (4-bromophenyl) carbazole by nuclear magnetic resonance measurement (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 8.14 (d, J = 7.8 Hz, 2H), 7.73 (d, J = 8.7 Hz, 2H), 7.46 (d, J = 8.4 Hz, 2H), 7.42-7.26 (m, 6H).

(Ii) Synthesis of 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA) A synthesis scheme of 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA) is shown in (C-14).

  In a 200 mL three-necked flask, 5.4 g (17.0 mmol) of N- (4-bromophenyl) carbazole obtained in (i) above, 1.8 mL (20.0 mmol) of aniline, bis (dibenzylideneacetone) palladium 100 mg (0.17 mmol) of (0) and 3.9 g (40 mmol) of sodium tert-butoxide were added, and the atmosphere was replaced with nitrogen. 0.1 mL of tri-tert-butylphosphine (10 wt% hexane solution) and 50 mL of toluene were added. , And stirred at 80 ° C. for 6 hours. The reaction mixture was filtered through Florisil, Celite, and alumina, and the filtrate was washed with water and saturated brine, and then dried over magnesium sulfate. The reaction mixture was naturally filtered, and the oil obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to give 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA) was obtained in an amount of 4.1 g in a yield of 73%. It was confirmed by nuclear magnetic resonance measurement (NMR) that this compound was 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 8.47 (s, 1H), 8.22 (d, J = 7.8 Hz, 2H), 7.44-7.16 (m, 14H) , 6.92-6.87 (m, 1H). ¹ H NMR charts are shown in FIGS. 36 (A) and 36 (B). Note that FIG. 36B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

[Step 2] Synthesis method of 2YGABPhA A synthesis scheme of 2YGABPhA is shown in (C-15).

  2.0 g (3.5 mmol) of 9,10-di (2-biphenylyl) -2-bromoanthracene synthesized in Step 1 of Example 3 and 4- (carbazol-9-yl synthesized in Step 1 of Example 5 ) Diphenylamine (abbreviation: YGA) 597 mg (3.5 mmol), sodium tert-butoxide 2.0 g (21 mmol) was placed in a 100 mL three-necked flask and purged with nitrogen, followed by 30 mL of toluene, tri (tert-butyl) phosphine (10% hexane) Solution) 0.1 mL was added and degassed under reduced pressure. After deaeration, 20 mg (0.035 mmol) of bis (dibenzylideneacetone) palladium (0) was added, followed by stirring at 80 ° C. for 3 hours. After the reaction, the reaction solution was washed with water and saturated brine in this order, and the organic layer was dried over magnesium sulfate. After spontaneous filtration, the solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 6: 4). When the obtained solid was recrystallized from dichloromethane-hexane, 2.0 g of a target yellow solid was obtained in a yield of 69%. By nuclear magnetic resonance measurement (NMR), this compound was converted to 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene ( (Abbreviation: 2YGABPhA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ -d): δ = 6.86-7.08 (m, 14H), 7.13 (d, J = 9.0 Hz, 2H), 7.21-7.24 ( m, 3H), 7.26-7.64 (m, 19H), 8.15 (d, J = 7.8 Hz, 2H). ¹ H NMR charts are shown in FIGS. 37A and 37B. Note that FIG. 37B is a chart in which the range of 6.5 ppm to 8.0 ppm in FIG.

  Further, FIG. 38 shows an absorption spectrum of a toluene solution of 2YGABPhA. Further, FIG. 39 shows an absorption spectrum of a thin film of 2YGABPhA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2YGABPhA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIG. 38 and FIG. 38 and 39, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 430 nm, and in the case of the thin film, absorption was observed at around 435 nm. In addition, FIG. 40 shows an emission spectrum of a toluene solution of 2YGABPhA (excitation wavelength: 370 nm). Further, FIG. 41 shows an emission spectrum of a thin film of 2YGABPhA (excitation wavelength: 435 nm). 40 and 41, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 491 nm (excitation wavelength 370 nm) in the case of the toluene solution, and 495 nm (excitation wavelength 435 nm) in the case of the thin film.

  The HOMO level in the thin film state of 2YGABPhA was measured by photoelectron spectroscopy in the atmosphere (manufactured by Riken Keiki Co., Ltd., AC-2), and was found to be −5.36 eV. The optical energy gap was estimated from the absorption edge obtained from the Tauc plot of the absorption spectrum of the 2YGABPhA thin film in FIG. 39, and it was 2.56 eV. Therefore, the LUMO level is −2.80 eV.

  In this example, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material used in this example is shown below.

  Table 1 shows an element structure of the light-emitting element manufactured in this example. In Table 1, all the mixing ratios are expressed by weight ratio.

  A method for manufacturing the light-emitting element of this example is described below.

  First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the first electrode is formed is downward, and the vacuum deposition apparatus is set to 10 ^−4. After reducing the pressure to about Pa, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and molybdenum oxide (VI) were combined on the first electrode 2102. By vapor deposition, a layer 2103 containing a composite material containing an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

  Next, a 4 nm film of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) is formed over the layer 2103 containing the composite material by an evaporation method using resistance heating. The hole transport layer 2104 was formed by forming the film so as to have a thickness.

  Further, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and the anthracene derivative of the present invention are co-evaporated to form a film with a thickness of 40 nm on the hole-transport layer 2104. A light emitting layer 2105 was formed. The weight ratio of CzPA to the anthracene derivative in each light-emitting element was adjusted to have the values shown in Table 1.

  Thereafter, tris (8-quinolinolato) aluminum (abbreviation: Alq) is used for the light-emitting element 1, the light-emitting element 3, the light-emitting element 5, the light-emitting element 7, and the light-emitting element 9 on the light-emitting layer 2105 by vapor deposition using resistance heating. An electron transport layer 2106 was formed by forming a film so as to have a thickness of 30 nm. In the light-emitting element 2, the light-emitting element 4, the light-emitting element 6, the light-emitting element 8, and the light-emitting element 10, bathophenanthroline (abbreviation: BPhen) was formed to a thickness of 30 nm to form an electron-transport layer 2106.

  Further, lithium fluoride (LiF) was formed to a thickness of 1 nm over the electron-transport layer 2106, whereby an electron-injection layer 2107 was formed.

  Finally, a second electrode 2108 is formed by depositing aluminum on the electron injection layer 2107 so as to have a thickness of 200 nm by using a resistance heating vapor deposition method. 10 was produced.

42 shows current density-luminance characteristics of the light-emitting element 1, FIG. 43 shows voltage-luminance characteristics, and FIG. 44 shows luminance-current efficiency characteristics. In addition, FIG. 45 shows an emission spectrum when a current of 1 mA is passed. FIG. 46 shows the normalized luminance time change of the light-emitting element 1 when the initial luminance is 3000 cd / m ^2, and FIG. 47 shows the drive voltage time change. The light-emitting element 1 had a CIE chromaticity coordinate (x = 0.36, y = 0.60) at a luminance of 3000 cd / m ² and emitted yellow-green light. The current efficiency at a luminance of 3000 cd / m ² was 17.4 cd / A, indicating a high current efficiency. As shown in FIG. 45, the maximum emission wavelength when a current of 1 mA was passed was 540 nm. FIG. 46 indicates that the light-emitting element 1 maintains 84% of the initial luminance even after 600 hours and has a long lifetime.

48 shows current density-luminance characteristics of the light-emitting element 2, FIG. 49 shows voltage-luminance characteristics, and FIG. 50 shows luminance-current efficiency characteristics. In addition, FIG. 51 shows an emission spectrum when a current of 1 mA is passed. The light emitting element 2 had a CIE chromaticity coordinate (x = 0.33, y = 0.63) at a luminance of 3000 cd / m ² and emitted green light. The current efficiency at a luminance of 3000 cd / m ² was 19.3 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 17.8 lm / W, and it can be said that the light-emitting element 2 can be driven with low power consumption. Further, as shown in FIG. 51, the maximum emission wavelength when a current of 1 mA was passed was 535 nm.

FIG. 52 shows current density-luminance characteristics of the light-emitting element 3, FIG. 53 shows voltage-luminance characteristics, and FIG. 54 shows luminance-current efficiency characteristics. In addition, FIG. 55 shows an emission spectrum when a current of 1 mA is passed. FIG. 56 shows a change in normalized luminance time of the light-emitting element 3 when the initial luminance is 3000 cd / m ^2, and FIG. 57 shows a change in drive voltage time. The light emitting element 3 had a CIE chromaticity coordinate (x = 0.31, y = 0.63) at a luminance of 3000 cd / m ² and emitted green light. The current efficiency at a luminance of 3000 cd / m ² was 14.5 cd / A, indicating a high current efficiency. As shown in FIG. 55, the maximum emission wavelength when a current of 1 mA was passed was 521 nm. In addition, FIG. 56 shows that the light-emitting element 3 maintains 87% of the initial luminance even after 300 hours and has a long lifetime.

58 shows current density-luminance characteristics of the light-emitting element 4, FIG. 59 shows voltage-luminance characteristics, and FIG. 60 shows luminance-current efficiency characteristics. In addition, FIG. 61 shows an emission spectrum when a current of 1 mA is passed. The light-emitting element 4 had a CIE chromaticity coordinate (x = 0.30, y = 0.62) at a luminance of 3000 cd / m ² and emitted green light. The current efficiency at a luminance of 3000 cd / m ² was 16.3 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 16.4 lm / W, and it can be said that the light-emitting element 4 can be driven with low power consumption. As shown in FIG. 61, the maximum emission wavelength when a current of 1 mA was passed was 520 nm.

62 shows current density-luminance characteristics of the light-emitting element 5, FIG. 63 shows voltage-luminance characteristics, and FIG. 64 shows luminance-current efficiency characteristics. In addition, FIG. 65 shows an emission spectrum when a current of 1 mA is passed. FIG. 66 shows the normalized luminance time change of the light-emitting element 5 when the initial luminance is 3000 cd / m ^2, and FIG. 67 shows the drive voltage time change. The light-emitting element 5 had a CIE chromaticity coordinate (x = 0.39, y = 0.59) at a luminance of 3000 cd / m ² and emitted yellow-green light. The current efficiency at a luminance of 3000 cd / m ² was 16.3 cd / A, indicating a high current efficiency. As shown in FIG. 65, the maximum emission wavelength when a current of 1 mA was passed was 546 nm. In addition, it can be seen from FIG. 66 that the light-emitting element 5 maintains 74% of the initial luminance even after 1600 hours and has a long lifetime.

68 shows current density-luminance characteristics of the light-emitting element 6, FIG. 69 shows voltage-luminance characteristics, and FIG. 70 shows luminance-current efficiency characteristics. In addition, FIG. 71 shows an emission spectrum when a current of 1 mA is passed. The light-emitting element 6 had a CIE chromaticity coordinate (x = 0.37, y = 0.60) at a luminance of 3000 cd / m ² and emitted yellow-green light. The current efficiency at a luminance of 3000 cd / m ² was 17.6 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 18.6 lm / W, and it can be said that the light-emitting element 6 can be driven with low power consumption. As shown in FIG. 71, the maximum emission wavelength when a current of 1 mA was passed was 545 nm.

72 shows current density-luminance characteristics of the light-emitting element 7, FIG. 73 shows voltage-luminance characteristics, and FIG. 74 shows luminance-current efficiency characteristics. FIG. 75 shows an emission spectrum when a current of 1 mA is passed. FIG. 76 shows a change in normalized luminance time of the light-emitting element 7 when the initial luminance is 3000 cd / m ^2, and FIG. 77 shows a change in drive voltage time. The light-emitting element 7 emitted green light with a CIE chromaticity coordinate (x = 0.31, y = 0.63) when the luminance was 3000 cd / m ² . The current efficiency at a luminance of 3000 cd / m ² was 13.0 cd / A, indicating a high current efficiency. As shown in FIG. 75, the maximum emission wavelength when a current of 1 mA was passed was 520 nm. FIG. 76 shows that the light-emitting element 7 maintains 69% of the initial luminance even after 1300 hours and has a long lifetime.

78 shows current density-luminance characteristics of the light-emitting element 8, FIG. 79 shows voltage-luminance characteristics, and FIG. 80 shows luminance-current efficiency characteristics. In addition, FIG. 81 shows an emission spectrum when a current of 1 mA is passed. The light-emitting element 8 had a CIE chromaticity coordinate (x = 0.31, y = 0.63) at a luminance of 3000 cd / m ² and emitted green light. The current efficiency at a luminance of 3000 cd / m ² was 15.7 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 14.9 lm / W, and it can be said that the light-emitting element 8 can be driven with low power consumption. Further, as shown in FIG. 81, the maximum emission wavelength when a current of 1 mA was passed was 522 nm.

82 shows current density-luminance characteristics of the light-emitting element 9, FIG. 83 shows voltage-luminance characteristics, and FIG. 84 shows luminance-current efficiency characteristics. In addition, FIG. 85 shows an emission spectrum when a current of 1 mA is passed. The light-emitting element 9 had CIE chromaticity coordinates (x = 0.21, y = 0.49) at a luminance of 3000 cd / m ² and emitted blue-green light. The current efficiency at a luminance of 3000 cd / m ² was 8.9 cd / A, indicating a high current efficiency. As shown in FIG. 85, the maximum emission wavelength when a current of 1 mA was passed was 491 nm.

86 shows current density-luminance characteristics of the light-emitting element 10, FIG. 87 shows voltage-luminance characteristics, and FIG. 88 shows luminance-current efficiency characteristics. FIG. 89 shows an emission spectrum when a current of 1 mA is passed. The light-emitting element 10 had a CIE chromaticity coordinate (x = 0.21, y = 0.49) at a luminance of 3000 cd / m ² and emitted blue-green light. The current efficiency at a luminance of 3000 cd / m ² was 12.1 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 11.6 lm / W, and it can be said that the light-emitting element 10 can be driven with low power consumption. As shown in FIG. 89, the maximum emission wavelength when a current of 1 mA was passed was 492 nm.

  In this example, 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9, which is an anthracene derivative of the present invention represented by the structural formula (219), A method for synthesizing 10-diphenylanthracene (abbreviation: 2PCNPA) will be specifically described.

[Step 1] Synthesis of N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amine (abbreviation: PCN) N- (1-naphthyl) -N- (9-phenylcarbazole-3- Il) A synthetic scheme of amine (abbreviation: PCN) is shown in (C-16).

  3-iodo-9-phenylcarbazole 3.7 g (10 mmol), 1-aminonaphthalene 1.6 g (5 mmol), bis (dibenzylideneacetone) palladium (0) 60 mg (0.1 mmol), tri (tert-butyl) phosphine (10 wt% hexane solution) 0.2 mL (0.5 mmol) and sodium tert-butoxide 3.0 g (30 mmol) were placed in a 100 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen, and then 12 mL of dehydrated xylene was added. The reaction mixture was heated and stirred at 90 ° C. for 7 hours under a nitrogen stream. After completion of the reaction, about 200 mL of heated toluene was added to the reaction mixture, and the mixture was filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, and the concentrate was purified by silica gel column chromatography (developing solvent: toluene: hexane = 1: 1). When the obtained solid was recrystallized with a mixed solvent of ethyl acetate and hexane, 1.5 g of a light brown powder of N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amine was collected. Obtained at a rate of 79%. This compound was confirmed to be N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amine (abbreviation: PCN) by nuclear magnetic resonance measurement (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 7.13-7.71 (m, 15H), 7.85-7.88 (m, 1H), 8.03 (s, 1H), 8 .15 (d, J = 7.8, 1H), 8.24 (s, 1H), 8.36-8.39 (m, 1H).

[Step 2] Synthesis of 2PCNPA A synthesis scheme of 2PCNPA is shown in (C-17).

  3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Example 1, N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amine ( Abbreviation: PCN) 3.2 g (9.4 mmol), bis (dibenzylideneacetone) palladium (0) 0.25 g (0.43 mmol), sodium tert-butoxide 2.1 g (21 mmol) was put into a 200 mL three-necked flask and replaced with nitrogen. Toluene 50 mL, tri (tert-butyl) phosphine (10% hexane solution) 0.86 g (0.43 mmol) were added, and the reaction mixture was stirred at 80 ° C. for 5 hours. After completion of the reaction, the reaction solution was washed with water, the aqueous layer was extracted with ethyl acetate, and the extracted solution was combined with the organic layer and dried over magnesium sulfate. After drying, the mixture was suction filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene), and the resulting solution was concentrated. The obtained solid was recrystallized with a mixed solvent of chloroform and hexane to give 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene. 2.6 g of a yellow powder (abbreviation: 2PCNPA) was obtained in a yield of 42%. By nuclear magnetic resonance measurement (NMR), this compound was converted into 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). It was confirmed that.

¹ H NMR data of this compound is shown below. ¹ H NMR (CDCl _3, 300 MHz): δ = 6.67-6.68 (m, 1H), 7.02-7.38 (m, 15H), 7.44-7.70 (m, 16H) , 7.88-8.01 (m, 4H). Further, the ¹ H NMR chart is shown in FIGS. 90 (A) and 90 (B). Note that FIG. 90B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  Thermogravimetry-differential thermal analysis (TG-DTA) of 2PCNPA was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the 5% weight loss temperature was 289 ° C., and 2PCNPA was found to exhibit high thermal stability.

  In addition, FIG. 91 shows an absorption spectrum of a toluene solution of 2PCNPA. In addition, FIG. 92 shows an absorption spectrum of a 2PCNPA thin film. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2PCNPA on a quartz substrate. 91 and 92 show the absorption spectra obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement. 91 and 92, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 438 nm, and in the case of the thin film, absorption was observed at around 442 nm. In addition, FIG. 93 shows an emission spectrum of a toluene solution of 2PCNPA (excitation wavelength: 430 nm). In addition, FIG. 94 shows an emission spectrum of a 2PCNPA thin film (excitation wavelength: 442 nm). 93 and 94, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 503 nm (excitation wavelength 445 nm) in the case of the toluene solution, and 522 nm (excitation wavelength 430 nm) in the case of the thin film.

  It was -5.21 eV as a result of measuring the HOMO level in the thin film state of 2PCNPA by the photoelectron spectroscopy in the air (the Riken Keiki Co., Ltd. make, AC-2). When the optical energy gap was estimated from the absorption edge obtained by Tauc plot of the absorption spectrum of the 2PCNPA thin film in FIG. 92, it was 2.48 eV. Therefore, the LUMO level is -2.73 eV.

  In addition, the oxidation-reduction characteristics of 2PCNPA were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

The solution in the CV measurement was dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number; 22705-6) as a solvent. The supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved in DMF to a concentration of 100 mmol / L, and electrolysis was performed. The solution was adjusted. Furthermore, the measurement object was dissolved in the electrolytic solution so as to have a concentration of 1 mmol / L. In addition, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) is used as the working electrode, and a platinum electrode (manufactured by BAS Corp., Pt counter electrode for VC-3 (as a counter electrode) 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of 2PCNPA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.40 V to 0.60 V, scanning for changing from 0.60 V to −0.40 V was taken as one cycle, and 100 cycles were performed. Further, the reduction reaction characteristics of 2PCNPA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.15 V to −2.55 V, scanning for changing from −2.55 V to −0.15 V was taken as one cycle, and 100 cycles were performed. The scan speed for CV measurement was set to 0.1 V / s.

FIG. 95 shows the CV measurement result on the oxidation side of 2PCNPA, and FIG. 96 shows the CV measurement result on the reduction side of 2PCNPA. 95 and 96, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the counter electrode. From FIG. 95, an electric current indicating oxidation was observed in the vicinity of 0.41 V (vs. Ag ^/ Ag ⁺ ). In addition, from FIG. 96, a current indicating reduction was observed around −2.33 V (vs. Ag / Ag ⁺ ).

  Despite repeated measurements for 100 cycles, there is almost no change in the peak position or peak intensity of the CV curve in the oxidation and reduction reactions. From this, it was found that the anthracene derivative of the present invention is extremely stable against repeated redox reactions.

  In this example, 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} which is an anthracene derivative of the present invention represented by the structural formula (220) A method for synthesizing -9,10-diphenylanthracene (abbreviation: 2NCNPA) will be specifically described.

[Step 1] Synthesis of N, 9-di (1-naphthyl) -9H-carbazol-3-amine (abbreviation: NCN)

(I) Synthesis of 9- (1-naphthyl) carbazole A synthesis scheme of 9- (1-naphthyl) carbazole is shown in (C-18).

  21 g (0.1 mol) of 1-bromonaphthalene, 17 g (0.1 mol) of carbazole, 950 mg (5 mmol) of copper (I) iodide, 33 g (240 mmol) of potassium carbonate, 660 mg of 18-crown-6-ether (2.5 mmol) was placed in a 500 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. 80 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (abbreviation: DMPU) was added to this mixture, and the mixture was stirred at 170 ° C. for 6 hours under a nitrogen stream. To this reaction mixture, 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper (I) iodide and 2.6 g (10 mmol) of 18-crown-6-ether were further added at 170 ° C. Stir for 7.5 hours. 10 g (50 mmol) of 1-bromonaphthalene was further added to the reaction mixture, and the mixture was further stirred at 180 ° C. for 6 hours. After completion of the reaction, about 200 mL of toluene and about 100 mL of 1 mol / L hydrochloric acid were added to the reaction mixture, followed by filtration through celite. The obtained filtrate was filtered through Florisil and Celite. The obtained filtrate was divided into an organic layer and an aqueous layer. The organic layer was washed with 1 mol / L hydrochloric acid and water in this order, and dried by adding magnesium sulfate. This suspension was filtered through Florisil and Celite. To the oily substance obtained by concentrating the obtained filtrate, hexane was added and irradiated with ultrasonic waves to precipitate a solid. The precipitated solid was collected by suction filtration to obtain 22 g of 9- (1-naphthyl) carbazole as a white powder (yield 75%). The Rf value (developing solvent was hexane: ethyl acetate = 10: 1) was 0.61 for 9- (1-naphthyl) carbazole, 0.74 for 1-bromonaphthalene, and 0.24 for carbazole.

(Ii) Synthesis of 3-bromo-9- (1-naphthyl) carbazole A synthesis scheme of 3-bromo-9- (1-naphthyl) carbazole is shown in (C-19).

  5.9 g (20 mmol) of 9- (1-naphthyl) carbazole was placed in a 500 mL Meyer flask, and 50 mL of ethyl acetate and 50 mL of toluene were added thereto and stirred. To this reaction solution, 3.6 g (20 mmol) of N-bromosuccinimide was slowly added and stirred at room temperature for about 170 hours (one week). After this reaction solution was washed with water, the organic layer was dried over magnesium sulfate. This suspension was filtered, and the obtained filtrate was concentrated to obtain 7.4 g of white powder of 3-bromo-9- (1-naphthyl) carbazole (yield 99%). Rf values (developing solvent: hexane: chloroform = 2: 1) were 0.43 for 3-bromo-9- (1-naphthyl) carbazole and 0.35 for 9- (1-naphthyl) carbazole.

(Iii) Synthesis of N, 9-di (1-naphthyl) -9H-carbazol-3-amine (abbreviation: NCN) N, 9-di (1-naphthyl) -9H-carbazol-3-amine (abbreviation: NCN) ) Shows a synthesis scheme of (C-20).

  3.7 g (10 mmol) of 3-bromo-9- (1-naphthyl) carbazole, 1.7 g (12 mmol) of 1-naphthylamine, 58 mg (0.1 mmol) of bis (dibenzylideneacetone) palladium (0), tri 600 μL (0.3 mmol) of (tert-butyl) phosphine (10% hexane solution) and 1.5 g (15 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. 20 mL of dehydrated xylene was added. The reaction mixture was heated and stirred at 110 ° C. for 7 hours under a nitrogen stream. After completion of the reaction, about 400 mL of toluene was added to the reaction mixture, which was filtered through Florisil, alumina, and celite. The obtained filtrate was washed with water, and then the organic layer was dried over magnesium sulfate. The suspension was filtered through Florisil, alumina, and celite, and the obtained filtrate was concentrated. The obtained solid was purified by silica gel column chromatography (toluene: hexane = 1: 1) to obtain 2.2 g of a light brown powder (yield 51%). It was confirmed by nuclear magnetic resonance measurement (NMR) that this light brown powder was the target N, 9-di (1-naphthyl) -9H-carbazol-3-amine (abbreviation: NCN). The Rf value (developing solvent is hexane: ethyl acetate = 5: 1) is 0.46 for (1-naphthyl) -9H-carbazol-3-amine, and 0 for 3-bromo-9- (1-naphthyl) carbazole. 68, 1-naphthylamine was 0.22.

[Step 2] Synthesis of 2NCNPA A synthesis scheme of 2NCNPA is shown in (C-21).

  2.1 g (5.0 mmol) of 2-bromo-9,10-diphenylanthracene, 2.2 g (5.1 mmol) of NCN, 29 mg (50 μmol) of bis (dibenzylideneacetone) palladium (0), tri (tert -Butyl) phosphine (10% hexane solution) 300 μL (0.2 mmol), sodium tert-butoxide 1.0 g (10 mmol) In a 100 mL three-necked flask, the flask was purged with nitrogen, and then 20 mL of dehydrated xylene was added to the mixture. Was added. The reaction mixture was heated and stirred at 110 ° C. for 4 hours under a nitrogen stream. After completion of the reaction, about 300 mL of toluene was added to the reaction mixture, and this was filtered through Florisil, alumina, and celite. The obtained filtrate was washed with water, and then the organic layer was dried over magnesium sulfate. The suspension was filtered through Florisil, alumina, and celite, and the obtained filtrate was concentrated. The obtained solid was purified by silica gel column chromatography (toluene: hexane = 1: 1). When hexane was added to the obtained oily substance and irradiated with ultrasonic waves, a solid was precipitated. When this solid was collected by suction filtration, 1.1 g of yellowish green powder was obtained (yield 29%). According to nuclear magnetic resonance measurement (NMR), this yellowish green powder was converted into the desired 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10 -It was confirmed that it was diphenylanthracene (abbreviation: 2NCNPA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.73 (d, J = 2.4 Hz, 1H), 6.84 (d, J = 8.7 Hz, 1H), 6.96 (d , J = 8.1 Hz, 1H), 7.04-7.70 (m, 29H), 7.89 (d, J = 7.8 Hz, 1H), 7.99-8.06 (m, 5H) . ¹ H NMR charts are shown in FIGS. 97A and 97B. Note that FIG. 97B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG. 97A is enlarged.

  In addition, FIG. 98 shows an absorption spectrum of a 2NCNPA toluene solution. In addition, FIG. 99 shows an absorption spectrum of the 2NCNPA thin film. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The spectrum of the solution was measured in a quartz cell. The thin film sample was prepared by evaporating 2NCNPA on a quartz substrate. The absorption spectrum obtained by subtracting the absorption spectrum of quartz from the spectrum immediately after the measurement is shown in FIGS. 98 and 99, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 448 nm, and in the case of the thin film, absorption was observed at around 465 nm. Further, FIG. 100 shows an emission spectrum of a 2NCNPA toluene solution (excitation wavelength: 300 nm). FIG. 101 shows an emission spectrum of a 2NCNPA thin film (excitation wavelength: 446 nm). 100 and 101, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 505 nm (excitation wavelength 300 nm) in the case of the toluene solution, and 529 nm (excitation wavelength 446 nm) in the case of the thin film.

  As a result of measuring the HOMO level of 2NCNPA in a thin film state by photoelectron spectroscopy in the air (manufactured by Riken Keiki Co., Ltd., AC-2), it was -5.26 eV. When the optical energy gap was estimated from the absorption edge obtained by the Tauc plot of the absorption spectrum of the 2NCNPA thin film in FIG. 99, it was 2.47 eV. Therefore, the LUMO level is −2.79 eV.

  Thermogravimetry-differential thermal analysis (TG-DTA) of 2NCNPA was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the 5% weight loss temperature was 400 ° C., and 2NCNPA was found to exhibit high thermal stability.

  Moreover, the glass transition point was measured using the differential scanning calorimeter (DSC, the Perkin Elmer company make, Pyris1). First, the sample was heated to 300 ° C. at 40 ° C./min to melt the sample, and then cooled to room temperature at 10 ° C./min. Thereafter, the temperature was raised to 300 ° C. at 10 ° C./min. As a result, it was found that the glass transition point (Tg) of 2NCNPA was 174 ° C., and it had a high glass transition point.

  In addition, the oxidation-reduction characteristics of 2NCNPA were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

The solution in the CV measurement was dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number; 22705-6) as a solvent. The supporting electrolyte tetra-n-butylammonium perchlorate (n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved in DMF to a concentration of 100 mmol / L, and electrolysis was performed. The solution was adjusted. Furthermore, the measurement object was dissolved in the electrolytic solution so as to have a concentration of 1 mmol / L. Moreover, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as a counter electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of 2NCNPA were examined as follows. After changing the potential of the working electrode with respect to the reference electrode from −0.07 V to 0.55 V, scanning for changing from 0.55 V to −0.07 V was taken as one cycle, and 100 cycles were performed. Further, the reduction reaction characteristics of 2PCNPA were examined as follows. A scan in which the potential of the working electrode with respect to the reference electrode was changed from −0.32 V to −2.45 V and then changed from −2.45 V to −0.32 V was set as one cycle, and 100 cycles were performed. The scan speed for CV measurement was set to 0.1 V / s.

FIG. 110 shows the CV measurement result on the oxidation side of 2NCNPA, and FIG. 111 shows the CV measurement result on the reduction side of 2NCNPA. 110 and 111, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the counter electrode. From FIG. 110, a current indicating oxidation was observed in the vicinity of 0.39 V (vs. Ag / Ag ⁺ ). In addition, from FIG. 111, a current indicating reduction was observed in the vicinity of −2.32 V (vs. Ag / Ag ⁺ ).

  Despite repeated measurements for 100 cycles, there is almost no change in the peak position or peak intensity of the CV curve in the oxidation and reduction reactions. From this, it was found that the anthracene derivative of the present invention is extremely stable against repeated redox reactions.

  In this example, a light-emitting element of the present invention will be described with reference to FIG.

  A method for manufacturing the light-emitting element of this example is described below.

  First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the first electrode is formed is downward, and the vacuum deposition apparatus is set to 10 ^−4. After reducing the pressure to about Pa, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and molybdenum oxide (VI) were combined on the first electrode 2102. By vapor deposition, a layer 2103 containing a composite material containing an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide).

  Next, a 4 nm film of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) is formed over the layer 2103 containing the composite material by an evaporation method using resistance heating. The hole transport layer 2104 was formed by forming the film so as to have a thickness.

  Furthermore, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and 2- [N- (1-naphthyl) which is an anthracene derivative of the present invention represented by the structural formula (219) ) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA) is co-evaporated to emit light with a thickness of 40 nm on the hole-transport layer 2104. Layer 2105 was formed. Here, the deposition rate was adjusted so that the weight ratio of CzPA to 2PCNPA was 1: 0.05 (= CzPA: 2PCNPA).

  Then, using a vapor deposition method using resistance heating, bathophenanthroline (abbreviation: BPhen) was formed to a thickness of 30 nm over the light-emitting layer 2105, whereby an electron-transport layer 2106 was formed.

  Further, lithium fluoride (LiF) was formed to a thickness of 1 nm over the electron-transport layer 2106, whereby an electron-injection layer 2107 was formed.

  Finally, a light-emitting element 11 was manufactured by forming a second electrode 2108 by depositing aluminum to a thickness of 200 nm on the electron injection layer 2107 using a resistance heating evaporation method. .

102 shows current density-luminance characteristics of the light-emitting element 11, FIG. 103 shows voltage-luminance characteristics, and FIG. 104 shows luminance-current efficiency characteristics. In addition, FIG. 105 shows an emission spectrum when a current of 1 mA is passed. The light emitting element 11 had a CIE chromaticity coordinate (x = 0.27, y = 0.62) at a luminance of 3270 cd / m ² and emitted green light. The current efficiency at a luminance of 3270 cd / m ² was 16.1 cd / A, indicating a high current efficiency. In addition, as shown in FIG. 105, the maximum emission wavelength when a current of 1 mA was passed was 518 nm.

  In this example, a light-emitting element of the present invention will be described with reference to FIG.

  A method for manufacturing the light-emitting element of this example is described below.

  First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode is formed is downward, and the pressure is reduced to about 10 ⁻⁴ Pa. Then, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and molybdenum oxide (VI) are co-evaporated on the first electrode 2102. A layer 2103 containing a composite material formed by combining an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide).

  Next, a 4 nm film of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) is formed over the layer 2103 containing the composite material by an evaporation method using resistance heating. The hole transport layer 2104 was formed by forming the film so as to have a thickness.

  Furthermore, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and 2- {N- (1-naphthyl) which is an anthracene derivative of the present invention represented by the structural formula (220) ) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA) is co-evaporated to form a 40 nm film on the hole transport layer 2104. A thick light emitting layer 2105 was formed. Here, the deposition rate was adjusted so that the weight ratio of CzPA to 2NCNPA was 1: 0.01 (= CzPA: 2NCNPA).

  Then, using a vapor deposition method using resistance heating, bathophenanthroline (abbreviation: BPhen) was formed to a thickness of 30 nm over the light-emitting layer 2105, whereby an electron-transport layer 2106 was formed.

  Further, lithium fluoride (LiF) was formed to a thickness of 1 nm over the electron-transport layer 2106, whereby an electron-injection layer 2107 was formed.

  Finally, a light-emitting element 12 was manufactured by forming a second electrode 2108 by depositing aluminum on the electron injection layer 2107 to a thickness of 200 nm by using a resistance heating vapor deposition method. .

106 shows current density-luminance characteristics of the light-emitting element 12, FIG. 107 shows voltage-luminance characteristics, and FIG. 108 shows luminance-current efficiency characteristics. FIG. 109 shows an emission spectrum when a current of 1 mA is passed. The light emitting element 12 had a CIE chromaticity coordinate (x = 0.28, y = 0.62) at a luminance of 3090 cd / m ² , and emitted green light. The current efficiency at a luminance of 3090 cd / m ² was 14.0 cd / A, indicating a high current efficiency. Further, as shown in FIG. 109, the maximum emission wavelength when a current of 1 mA was passed was 511 nm.

  In this example, 2- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} -9,10-diphenyl which is an anthracene derivative of the present invention represented by the structural formula (301) A method for synthesizing anthracene (abbreviation: 2YGAPA) will be specifically described.

[Step 1] Synthesis method of 2YGAPA The synthesis scheme of 2YGAPA is shown in (C-22).

  2-Bromo-9,10-diphenylanthracene 2.0 g (4.1 mmol), sodium tert-butoxide 1.0 g (10 mmol), 4- (carbazol-9-yl) diphenylamine 1 synthesized in Step 1 of Example 1 .4 g (4.1 mmol), 0.1 g (0.2 mmol) of bis (dibenzylideneacetone) palladium (0) was placed in a 100 mL three-necked flask, and the inside of the flask was purged with nitrogen. To this mixture, 30 mL of toluene, tri (tert- 0.1 mL of a 10 wt% hexane solution of butyl) phosphine was added, and the mixture was heated and stirred for 5 hours at 80 ° C. After the reaction, toluene was added to the reaction mixture, and the suspension was saturated with aqueous sodium carbonate and saturated brine. The aqueous layer and the organic layer were separated, and the organic layer was separated from Florisil, Celite, A filtrate was obtained by suction filtration through Mina, and the resulting filtrate was concentrated to obtain a solid, which was recrystallized with a mixed solvent of chloroform and hexane, yielding the desired yellow solid in a yield of 2. 2 g, 81% yield, obtained by nuclear magnetic resonance (NMR) analysis of the compound as 2- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} -9,10- It was confirmed that it was diphenylanthracene (abbreviation: 2YGAPA).

The ¹ H NMR data of 2YGAPA is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 7.05-7.12 (m, 1H), 7.13-7.74 (m, 31H), 8.16 (d, J = 6.8 Hz, 2H). ¹ H NMR charts are shown in FIGS. 112 (A) and 112 (B). Note that FIG. 112B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG. 112A is enlarged.

  An absorption spectrum of a toluene solution of 2YGAPA is shown in FIG. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. An absorption spectrum is obtained by subtracting the absorption spectrum of quartz from the spectrum of the sample solution in the quartz cell, and this is shown in FIG. In FIG. 113, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 428 nm. In addition, FIG. 114 shows an emission spectrum of a toluene solution of 2YGAPA (excitation wavelength: 430 nm). In FIG. 114, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 486 nm (excitation wavelength: 430 nm).

  As a result of measuring the HOMO level of 2YGAPA in a thin film state by photoelectron spectroscopy in the atmosphere (manufactured by Riken Keiki Co., Ltd., AC-2), it was −5.47 eV. The optical energy gap was estimated from the absorption edge obtained by Tauc plot of the absorption spectrum of the 2YGAPA thin film, and it was 2.55 eV. Therefore, the LUMO level is -2.92 eV.

  In this example, 9,10-diphenyl-1- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene which is an anthracene derivative of the present invention represented by the structural formula (202) ( A method for synthesizing (abbreviation: 1PCAPA) will be specifically described.

[Step 1] Synthesis of 1-bromo-9,10-diphenylanthracene

(I) Synthesis of 1-bromo-9,10-anthraquinone A synthesis scheme of 1-bromo-9,10-anthraquinone is shown in (C-23).

  1-Amino-9,10-anthraquinone 20.0 g (88.8 mmol), copper bromide (II) 36.7 g (164 mmol), and acetonitrile 240 mL were placed in a 500 mL three-necked flask and purged with nitrogen, and tert-butyl nitrite 15 .8 mL (133 mmol) was added and stirred at 65 ° C. for 6 hours. After completion of the reaction, the reaction mixture was poured into about 1.3 L of 3 mol / L hydrochloric acid and stirred at room temperature for 3 hours. The precipitate in the mixture was collected by suction filtration, and the solid was washed with water and ethanol. The obtained solid was dissolved in a mixed solvent of toluene and chloroform and suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene). When the obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 9.37 g of yellow powder of 1-bromo-9,10-anthraquinone was obtained in a yield of 36%.

(Ii) Synthesis of 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol The synthesis scheme is shown in (C-24).

  9.37 g (32.4 mmol) of 1-bromoanthraquinone was placed in a 500 mL three-necked flask and purged with nitrogen, 150 mL of tetrahydrofuran (abbreviation: THF) was added, and 34.0 mL of phenyl lithium (2.1 mol / L dibutyl ether solution) ( 71.3 mmol) was added at once and stirred at room temperature for 24 hours. After completion of the reaction, the reaction solution was washed with water, the aqueous layer was extracted with ethyl acetate, and the extract and the organic layer were combined and dried over magnesium sulfate. After drying, the mixture was filtered with suction, and the filtrate was concentrated. As a result, 14.4 g of a brown oily substance of 1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol was obtained, and the yield was about Obtained at 100%.

(Iii) Synthesis of 1-bromo-9,10-diphenylanthracene A synthesis scheme of 1-bromo-9,10-diphenylanthracene is shown in (C-25).

  1-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol 14.4 g (32.4 mmol), potassium iodide 9.68 g (58.3 mmol), sodium phosphinate monohydrate 18.6 g (175 mmol) and 100 mL of glacial acetic acid were placed in a 500 mL three-necked flask and refluxed at 120 ° C. for 5 hours. After completion of the reaction, 40 mL of 50% phosphinic acid solution was added and stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was washed with water, the aqueous layer was extracted with ethyl acetate, and the extract and the organic layer were combined and dried over magnesium sulfate. After drying, the mixture was filtered with suction, and the filtrate was concentrated. The obtained residue was dissolved in toluene and suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; toluene: hexane = 1: 5). The obtained solid was washed with methanol to obtain 0.50 g of light yellow powder of 1-bromo-9,10-diphenylanthracene in a yield of 3.8%.

[Step 2] Synthesis method of 1PCAPA A synthesis scheme of 1PCAPA is shown in (C-26).

  0.50 g (1.2 mmol) of 1-bromo-9,10-diphenylanthracene synthesized in Step 1 of Example 12, N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA) ) 0.45 g (1.3 mmol), bis (dibenzylideneacetone) palladium (0) 0.035 g (0.061 mmol), sodium tert-butoxide 0.29 g (3.1 mmol) was placed in a 100 mL three-necked flask, and the atmosphere was replaced with nitrogen. 10 mL of toluene and 0.12 g (0.061 mmol) of tri (tert-butyl) phosphine (10% hexane solution) were added, and the reaction mixture was stirred at 80 ° C. for 18 hours. After completion of the reaction, toluene was added to the reaction mixture, and suction filtration was performed through Florisil, Celite, and alumina, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane: toluene = 3: 2), and the obtained solid was recrystallized from chloroform and hexane to obtain 0.08 g of the objective orange powder. Obtained at a rate of 10%. It was confirmed by nuclear magnetic resonance (NMR) that this compound was 9,10-diphenyl-1- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene (abbreviation: 1PCAPA). did.

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 6.93-6.97 (m, 1H), 7.12-7.32 (m, 16H), 7.39-7.41 (m, 2H) 7.47-7.66 (m, 13H), 7.88-7.97 (m, 2H). ¹ H NMR charts are shown in FIGS. 115A and 115B. Note that FIG. 115B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  In addition, FIG. 116 shows an absorption spectrum of a toluene solution of 1PCAPA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. An absorption spectrum is obtained by subtracting the absorption spectrum of quartz from the spectrum of the sample solution in the quartz cell, and this is shown in FIG. In FIG. 116, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 443 nm. An emission spectrum of a 1PCAPA toluene solution (excitation wavelength: 430 nm) is shown in FIG. In FIG. 117, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 512 nm (excitation wavelength: 430 nm).

  In this example, 9,10-bis (9,9-dimethylfluoren-2-yl) -2- [N-phenyl-N- (9) which is an anthracene derivative of the present invention represented by the structural formula (207) A method for synthesizing -phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCADFA) is specifically described.

[Step 1] Synthesis of 2-bromo-9,9-dimethylfluorene

(I) Synthesis of 2-bromo-9,9-dimethylfluorene A synthesis scheme of 2-bromo-9,9-dimethylfluorene is shown in (C-27).

  2-Bromofluorene 12.5 g (51 mmol), potassium iodide 8.5 g (51 mmol), potassium hydroxide 14.3 g (0.50 mol) and dimethyl sulfoxide 250 mL were stirred in a 500 mL Erlenmeyer flask for 30 minutes. To this mixture, 10 mL of methyl iodide was added in small portions. The mixture was stirred at room temperature for 48 hours. After the reaction, 400 mL of chloroform was added to the reaction solution and stirred. This solution was washed with 1N hydrochloric acid, saturated aqueous sodium carbonate solution and saturated brine in this order. Magnesium sulfate was added to the organic layer and dried. After drying, the mixture was suction filtered and concentrated, and the residue was purified by column chromatography. In column chromatography, first, hexane was used as a developing solvent, and then a mixed solvent of ethyl acetate: hexane = 1: 5 was used as a developing solvent. Corresponding fractions were concentrated and dried to yield 12 g of a brown oil in 97% yield.

(Ii) Synthesis of 9,10-bis (9,9-dimethylfluoren-2-yl) -2-bromo-9,10-dihydroanthracene-9,10-diol 9,10-bis (9,9-dimethyl) The synthesis schemes of (fluoren-2-yl) -2-bromo-9,10-dihydroanthracene-9,10-diol are shown in (C-28) and (C-29).

  2-Bromo-9,9-dimethylfluorene (12 g, 46 mmol) and tetrahydrofuran (abbreviation: THF) (150 mL) were placed in a 500 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. To this solution, 35 mL of a 1.6 mol / L n-butyllithium hexane solution was slowly added dropwise at −78 ° C. and stirred for 1.5 hours. After the reaction, 5.4 g (19 mmol) of 2-bromo-9,10-anthraquinone dissolved in 100 mL of THF was added to the reaction mixture. The solution was stirred at room temperature for 18 hours. After stirring, 1N hydrochloric acid was added to this solution and stirred for 30 minutes. The mixture was transferred to a separatory funnel and the aqueous layer was extracted with ethyl acetate. The extract and the organic layer were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. After washing, magnesium sulfate was added to the organic layer and dried. After drying, the mixture is suction filtered. The obtained filtrate was suction filtered through Celite, Florisil, and alumina, and the obtained filtrate was concentrated to obtain the title compound as a brown oil.

(Iii) Synthesis of 9,10-bis (9,9-dimethylfluoren-2-yl) -2-bromoanthracene of 9,10-bis (9,9-dimethylfluoren-2-yl) -2-bromoanthracene The synthesis scheme is shown in (C-30).

  9,10-bis (9,9-dimethylfluoren-2-yl) -2-bromo-9,10-dihydroanthracene-9,10-diol 46 mmol, sodium phosphinate monohydrate 24 g (0.23 mol), A solution of 15 g (91 mmol) of potassium iodide in 100 mL of glacial acetic acid was heated and stirred at 120 ° C. for 4 hours. After the reaction, 60 mL of 50% phosphinic acid solution was added to the reaction mixture, and the mixture was further heated and stirred at 120 ° C. for 2 hours. After adding water to the mixture and stirring for 1 hour, the mixture was filtered with suction. The obtained solid was washed with water, the solid was dissolved in toluene, and this solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. Magnesium sulfate was added to the organic layer and dried. After drying, the mixture was filtered with suction. The obtained filtrate was suction filtered through Celite, Florisil, and alumina. The solid obtained by concentrating the obtained filtrate was dissolved in a mixed solvent of chloroform and methanol and irradiated with ultrasonic waves, whereby 14 g of the title compound was obtained as a pale yellow solid. The overall yield in the two stages of steps (ii) and (iii) was 47%.

[Step 2] Synthesis of 2PCADFA A synthesis scheme of 2PCADFA is shown in (C-31).

  9,10-bis (9,9-dimethylfluoren-2-yl) -2-bromoanthracene 1.5 g (2.3 mmol), sodium tert-butoxide 1.0 g (10 mmol), N-phenyl- (9-phenyl) -9H-carbazol-3-yl) amine (abbreviation: PCA) 0.78 g (2.3 mmol) and bis (dibenzylideneacetone) palladium (0) 0.08 g (0.16 mmol) were placed in a 100 mL three-necked flask, The flask was purged with nitrogen. To this mixture, 30 mL of toluene and 0.05 mL of a 10% hexane solution of tri (tert-butyl) phosphine were added, and the mixture was heated and stirred at 80 ° C. for 5 hours. After stirring, toluene was added to the reaction mixture, and the suspension was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was suction filtered through Florisil, Celite, and alumina, washed with water and saturated brine, and dried by adding magnesium sulfate. The mixture was suction filtered to remove magnesium sulfate, and the resulting filtrate was concentrated. The obtained solid was purified by silica gel column chromatography (developing solution: toluene: hexane = 1: 9, then toluene: hexane = 1: 5, then toluene: hexane = 1: 2), and the obtained solid was combined with dichloromethane. Recrystallization from a mixed solvent of hexane gave 0.70 g of a powdery yellow solid in a yield of 77%. By nuclear magnetic resonance measurement (NMR), the compound was converted to 9,10-bis (9,9-dimethylfluoren-2-yl) -2- [N-phenyl-N- (9-phenyl-9H-carbazole-3- Yl) amino] anthracene (abbreviation: 2PCADFA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 1.04 (d, J = 1.95, 3H), 1.41 (s, 3H), 1.54-1.59 (m, 6H), 6 .83-6.90 (m, 1H), 7.09-7.24 (m, 10H), 7.25-7.64 (m, 20H), 7.63-7.70 (m, 2H) 7.70-7.75 (m, 1H), 7.82 (dd, J1 = 2.0 Hz, J2 = 6.8 Hz, 1H), 7.88 (s, 1H), 7.92 (d, J = 8.3 Hz, 2H). A ¹ H NMR chart is shown in FIGS. 118A and 118B. 118B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG. 118A is enlarged.

  Sublimation purification of 0.70 g of the obtained yellow solid was performed by a train sublimation method. Sublimation purification was performed at 352 ° C. for 15 hours under a reduced pressure of 7.0 Pa with an argon flow rate of 3 mL / min. The yield was 0.62 g and the recovery rate was 89%.

  In addition, FIG. 119 shows an absorption spectrum of a toluene solution of 2PCADFA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. An absorption spectrum was obtained by subtracting the absorption spectrum of quartz from the spectrum of the sample solution in the quartz cell, and this is shown in FIG. In FIG. 119, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 442 nm. In addition, an emission spectrum of a toluene solution of 2PCADFA (excitation wavelength: 439 nm) is shown in FIG. In FIG. 119, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 516 nm (excitation wavelength: 439 nm).

In this example, 9,10-diphenyl-2- [N- (4′-diphenylamino-1,1′-biphenyl-4-yl) which is an anthracene derivative of the present invention represented by the structural formula (119) is used. A method for synthesizing [N-phenylamino] anthracene (abbreviation: 2DPBAPA) will be specifically described. Note that 2DPBAPA represented by the structural formula (119) is a case where, in the general formula (5), Ar ¹ and Ar ² are the structural formula (20-1), and A is the structural formula (31-18). Corresponding to

[Step 1] Synthesis of triphenylamine-4-boronic acid A synthesis scheme of triphenylamine-4-boronic acid is shown in (C-32).

  Under nitrogen, 10 g (31 mmol) of 4-bromotriphenylamine in tetrahydrofuran (THF, 150 mL) solution was added dropwise at −80 ° C. with 20 mL (32 mmol) of n-butyllithium (1.58 mol / L hexane solution) with a syringe. After completion of the dropwise addition, the solution was stirred at the same temperature for 1 hour. 3.8 mL (34 mmol) of trimethyl borate was added to this solution, and then stirred for about 15 hours while returning the reaction temperature to room temperature. About 150 mL of diluted hydrochloric acid (1.0 mol / L) was added to this solution and stirred for 1 hour. After stirring, the aqueous layer of this mixture was extracted with ethyl acetate, and the extracted solution and the organic layer were combined and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give a light brown oil. About 20 mL of chloroform was added to the oil to dissolve it, and then about 50 mL of hexane was further added and allowed to stand for 1 hour to precipitate a white solid. When this solid was collected by suction filtration, 5.2 g of a target white solid was obtained in a yield of 58%.

[Step 2] Synthesis of N, N ′, N′-triphenylbenzidine (abbreviation: DPBA) A synthesis scheme of N, N ′, N′-triphenylbenzidine (abbreviation: DPBA) is shown in (C-33).

  4.3 g (17 mmol) of 4-bromodiphenylamine, 5 g (17 mmol) of triphenylamine-4-boronic acid, and 532 mg (1.8 mmol) of tri (o-tolyl) phosphine were placed in a 500 mL three-necked flask. The inside was replaced with nitrogen. To this mixture, 60 mL of toluene, 40 mL of ethanol, and 14 mL of an aqueous potassium carbonate solution (0.2 mol / L) were added. The mixture was deaerated while being stirred under reduced pressure. After deaeration, 75 mg (0.35 mmol) of palladium (II) acetate was added. The mixture was refluxed at 100 ° C. for 10.5 hours. The aqueous layer of this mixture was extracted with toluene. The extracted solution and the organic layer were combined and washed with saturated brine, dried over magnesium sulfate, filtered and concentrated to give a light brown oil. This oily substance was dissolved in about 50 mL of toluene, and then suction filtered through Celite, alumina, and Florisil. The solid obtained by concentrating the filtrate was purified by silica gel column chromatography (developing solvent: hexane: toluene = 4: 6), and the obtained white solid was recrystallized from chloroform / hexane to obtain the white product of interest. 3.5 g of solid was obtained with a yield of 49%.

[Step 3] Synthesis of 2DPBAPA A synthesis scheme of 2DPBAPA is shown in (C-34).

  1.5 g (3.6 mmol) of 2-bromo-9,10-diphenylanthracene, 1.5 g (3.6 mmol) of N, N ′, N′-triphenylbenzidine (abbreviation: DPBA), 5 g (16 mmol) of sodium tert-butoxide was put into a 100 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture, 20 mL of toluene and 0.10 mL of tri (tert-butyl) phosphine (10 wt% hexane solution) were added. The mixture was degassed with stirring under reduced pressure and 41 mg (0.072 mmol) of bis (dibenzylideneacetone) palladium (0) was added. The mixture was stirred at 100 ° C. for 3 hours. About 50 mL of toluene was added to the reaction mixture, and the mixture was suction filtered through celite, florisil, and alumina. The obtained filtrate was concentrated to give an oily substance. When about 10 mL of toluene was added to this oily substance and allowed to stand for about 2 hours, a yellow solid was precipitated. When this solid was recovered by suction filtration, 2.5 g of a target yellow powder was obtained in a yield of 91%. By nuclear magnetic resonance measurement (NMR), this compound was converted into 9,10-diphenyl-2- [N- (4′-diphenylamino-1,1′-biphenyl-4-yl) -N-phenylamino] anthracene (abbreviation). : 2DPBAPA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 7.01-7.08 (m, 11H), 7.13-7.17 (m, 5H), 7.22-7.89 (m, 12H), 7.42-7.66 (m, 12H). ¹ H NMR charts are shown in FIGS. 120 (A) and 120 (B). Note that FIG. 120B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  In addition, FIG. 121 shows an absorption spectrum of a 2DPBAPA toluene solution. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. An absorption spectrum is obtained by subtracting the absorption spectrum of quartz from the spectrum of the sample solution in the quartz cell, and this is shown in FIG. 121, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 355 nm. In addition, FIG. 122 shows an emission spectrum of a toluene solution of 2DPBAPA (excitation wavelength: 370 nm). 122, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 493 nm (excitation wavelength: 370 nm).

In this example, 2- {N- [4 ′-(9H-carbazol-9-yl) -1,1′-biphenyl-4-yl] which is an anthracene derivative of the present invention represented by the structural formula (319) is used. ] A method for synthesizing -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGBAPA) will be specifically described. Note that 2YGBAPA represented by the structural formula (319) is a case where, in the general formula (5), Ar ¹ and Ar ² are the structural formula (20-1) and A is the structural formula (33-10). Corresponding to

[Step 1] Synthesis of 9-phenylcarbazol-3-ylboronic acid A synthesis scheme of 9-phenylcarbazol-3-ylboronic acid is shown in (C-35).

  To a solution of 19.6 g (60.7 mmol) of 3-bromo-9-phenylcarbazole synthesized in Step 1 of Example 2 in THF (100 mL) was added n-butyllithium hexane solution (1) at −78 ° C. under nitrogen. .58 mol / L) 66.8 mL (42.3 mmol) was added dropwise, and the mixture was stirred at the same temperature for 3 hours. Thereafter, 13.5 mL (140 mmol) of trimethyl borate was added and stirred for 24 hours while returning to room temperature. To this solution, 200 mL of 2.0 mol / L hydrochloric acid was added and stirred at room temperature for 1 hour. This solution was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. When the obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 10.2 g of white powder of 9-phenylcarbazol-3-ylboronic acid was obtained in a yield of 58%.

[Step 2] Synthesis of 4- [4- (9H-carbazol-9-yl) phenyl] diphenylamine (abbreviation: YGBA) 4- [4- (9H-carbazol-9-yl) phenyl] diphenylamine (abbreviation: YGBA) The synthesis scheme of is shown in (C-36).

  200 mL of 2.2 g (8.8 mmol) 4-bromodiphenylamine, 2.5 g (8.8 mmol) triphenylamine-4-boronic acid and 398 mg (1.3 mmol) tri (o-tolyl) phosphine The flask was placed in a three-neck flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture, 30 mL of toluene, 20 mL of ethanol, and 14 mL of an aqueous potassium carbonate solution (0.2 mol / L) were added. The mixture was degassed with stirring under reduced pressure and 59 mg (0.26 mmol) of palladium (II) acetate was added. The mixture was refluxed at 100 ° C. for 6.5 hours. When this mixture was allowed to cool for about 15 hours, a light black-brown solid precipitated. When this solid was collected by suction filtration, 2.5 g of a target light black-brown solid was obtained in a yield of 70%.

[Step 4] Synthesis of 2YGBAPA A synthesis scheme of 2YGBAPA is shown in (C-37).

  1.2 g (3.0 mmol) 2-bromo-9,10-diphenylanthracene, 1.2 g (3.0 mmol) YGBA and 1.5 g (16 mmol) sodium tert-butoxide were placed in a 100 mL three-necked flask. The inside of the flask was purged with nitrogen. To this mixture, 15 mL of toluene and 0.20 mL of tri (tert-butyl) phosphine (10 wt% hexane solution) were added. The mixture was degassed with stirring under reduced pressure and 86 mg (0.15 mmol) of bis (dibenzylideneacetone) palladium (0) was added. The mixture was stirred at 100 ° C. for 3 hours. After stirring, the mixture was suction filtered through celite, alumina, and florisil. The oil obtained by concentrating the obtained filtrate was purified by silica gel column chromatography (developing solvent: hexane: toluene = 7: 3), and the resulting yellow solid was recrystallized from chloroform / methanol. As a result, 462 mg of a yellow solid was obtained in a yield of 21%. By nuclear magnetic resonance measurement (NMR), this compound was converted into 2- {N- [4 ′-(9H-carbazol-9-yl) -1,1′-biphenyl-4-yl] -N-phenylamino} -9. , 10-diphenylanthracene (abbreviation: 2YGBAPA).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 7.08-7.14 (m, 5H), 7.20 (dd, J = 2.4, 9.5 Hz, 1H), 7.28- 7.61 (m, 22H), 7.64 (d, J = 7.2 Hz, 2H), 7.70 (dd, J = 2.4, 7.7 Hz, 4H), 7.91 (d, J = 8.4 Hz, 2H), 8.26 (d, J = 7.8 Hz, 2H). ¹ H NMR charts are shown in FIGS. 123 (A) and 123 (B). Note that FIG. 123B is a chart in which the range of 6.5 ppm to 9.0 ppm in FIG. 123A is enlarged.

  In addition, FIG. 124 shows an absorption spectrum of a toluene solution of 2YGBAPA. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. An absorption spectrum is obtained by subtracting the absorption spectrum of quartz from the spectrum of the sample solution in the quartz cell, and this is shown in FIG. In FIG. 124, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 344 nm. In addition, FIG. 125 shows an emission spectrum of a toluene solution of 2YGBAPA (excitation wavelength: 370 nm). In FIG 125, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 485 nm (excitation wavelength: 370 nm).

  In this example, a light-emitting element of the present invention will be described with reference to FIG.

  A method for manufacturing the light-emitting element of this example is described below.

  First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the first electrode is formed is downward, and the vacuum deposition apparatus is set to 10 ^−4. After reducing the pressure to about Pa, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and molybdenum oxide (VI) were combined on the first electrode 2102. By vapor deposition, a layer 2103 containing a composite material containing an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide).

  Next, a 4 nm film of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) is formed over the layer 2103 containing the composite material by an evaporation method using resistance heating. The hole transport layer 2104 was formed by forming the film so as to have a thickness.

  Furthermore, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and the anthracene derivative of the present invention represented by the structural formula (301) are 2- {N- [4- ( Carbazole-9-yl) phenyl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGAPA) is co-evaporated to form a light-emitting layer 2105 having a thickness of 30 nm on the hole-transport layer 2104. Formed. Here, the deposition rate was adjusted so that the weight ratio of CzPA to 2YGAPA was 1: 0.05 (= CzPA: 2YGAPA).

  Then, tris (8-quinolinolato) aluminum (abbreviation: Alq) was formed to a thickness of 10 nm over the light-emitting layer 2105 by an evaporation method using resistance heating, so that an electron-transport layer 2106 was formed.

  Further, tris (8-quinolinolato) aluminum (abbreviation: Alq) and lithium (Li) were co-evaporated on the electron transport layer 2106, whereby the electron injection layer 2107 was formed to a thickness of 20 nm. Here, the deposition rate was adjusted so that the weight ratio of Alq to Li was 1: 0.01 (= Alq: Li).

  Finally, a light-emitting element 13 was manufactured by forming a second electrode 2108 by depositing aluminum on the electron injection layer 2107 so as to have a thickness of 200 nm using a resistance heating vapor deposition method. .

126 shows current density-luminance characteristics of the light-emitting element 13, FIG. 127 shows voltage-luminance characteristics, and FIG. 128 shows luminance-current efficiency characteristics. In addition, an emission spectrum when a current of 1 mA is passed is shown in FIG. 130 shows a change in normalized luminance time of the light-emitting element 13 when the initial luminance is 1000 cd / m ^2, and FIG. 131 shows a change in drive voltage time. The light-emitting element 13 had CIE chromaticity coordinates (x = 0.21, y = 0.51) at a luminance of 1000 cd / m ² and emitted blue-green light. The current efficiency at a luminance of 1000 cd / m ² was 9.6 cd / A, indicating a high current efficiency. In addition, as shown in FIG. 129, the maximum emission wavelength when a current of 1 mA was passed was 489 nm. In addition, it can be seen from FIG. 130 that the light-emitting element 13 maintains 82% of the initial luminance even after 640 hours and has a long lifetime.

  In this example, a light-emitting element of the present invention will be described with reference to FIG.

  A method for manufacturing the light-emitting element of this example is described below.

  First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum deposition apparatus so that the surface on which the first electrode is formed is downward, and the vacuum deposition apparatus is set to 10 ^−4. After reducing the pressure to about Pa, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and molybdenum oxide (VI) were combined on the first electrode 2102. By vapor deposition, a layer 2103 containing a composite material containing an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide).

  Next, a 4 nm film of 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) is formed over the layer 2103 containing the composite material by an evaporation method using resistance heating. The hole transport layer 2104 was formed by forming the film so as to have a thickness.

  Furthermore, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and 9,10-diphenyl-1- [which is an anthracene derivative of the present invention represented by the structural formula (202) N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene (abbreviation: 1PCAPA) was co-evaporated to form a light-emitting layer 2105 having a thickness of 40 nm on the hole-transport layer 2104. . Here, the deposition rate was adjusted so that the weight ratio of CzPA to 1PCAPA was 1: 0.05 (= CzPA: 1PCAPA).

  Then, using a vapor deposition method using resistance heating, in the light-emitting element 14, tris (8-quinolinolato) aluminum (abbreviation: Alq) is formed to a thickness of 30 nm on the light-emitting element 2105, and the electron-transport layer 2106 is formed. Formed. In the light-emitting element 15, bathophenanthroline (abbreviation: BPhen) was formed to a thickness of 30 nm, so that the electron-transport layer 2106 was formed.

  Further, lithium fluoride (LiF) was formed to a thickness of 1 nm over the electron-transport layer 2106, whereby an electron-injection layer 2107 was formed.

  Finally, a second electrode 2108 is formed by depositing aluminum to a thickness of 200 nm on the electron injection layer 2107 using a vapor deposition method using resistance heating, whereby the light-emitting element 14 to the light-emitting element. 15 was produced.

FIG. 132 shows current density-luminance characteristics of the light-emitting element 14, FIG. 133 shows voltage-luminance characteristics, and FIG. 134 shows luminance-current efficiency characteristics. In addition, FIG. 135 shows an emission spectrum obtained when a current of 1 mA was passed. In addition, FIG. 136 shows a change in normalized luminance time of the light-emitting element 14 when the initial luminance is 3000 cd / m ^2, and FIG. 137 shows a change in drive voltage time. The light-emitting element 14 emitted green light with a CIE chromaticity coordinate (x = 0.31, y = 0.61) when the luminance was 3000 cd / m ² . The current efficiency at a luminance of 3000 cd / m ² was 13.9 cd / A, indicating a high current efficiency. As shown in FIG. 135, the maximum emission wavelength when a current of 1 mA was passed was 515 nm. In addition, it can be seen from FIG. 136 that the light-emitting element 14 maintains 74% of the initial luminance even after 500 hours and has a long lifetime.

FIG. 138 shows current density-luminance characteristics of the light-emitting element 15, FIG. 139 shows voltage-luminance characteristics, and FIG. 140 shows luminance-current efficiency characteristics. In addition, an emission spectrum when a current of 1 mA is passed is shown in FIG. The light emitting element 15 had a CIE chromaticity coordinate (x = 0.32, y = 0.59) at a luminance of 3000 cd / m ² and emitted green light. The current efficiency at a luminance of 3000 cd / m ² was 15.9 cd / A, indicating a high current efficiency. The power efficiency at a luminance of 3000 cd / m ² is 16.7 lm / W, and it can be said that the element 15 can be driven with low power consumption. In addition, as shown in FIG. 141, the maximum emission wavelength when a current of 1 mA was passed was 515 nm.

4A and 4B illustrate a light-emitting element of the present invention. 4A and 4B illustrate a light-emitting element of the present invention. 4A and 4B illustrate a light-emitting element of the present invention. 4A and 4B illustrate a light-emitting device of the present invention. 4A and 4B illustrate a light-emitting device of the present invention. 8A and 8B each illustrate an electronic device of the invention. 8A and 8B each illustrate an electronic device of the invention. The figure explaining the illuminating device of this invention. The figure explaining the illuminating device of this invention. 3A and 3B illustrate a light-emitting element of an example. FIG. 9 shows a ¹ H NMR chart of 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA). FIG. 9 shows an absorption spectrum of a toluene solution of 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA). FIG. 9 shows an absorption spectrum of a thin film of 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA). 9A and 9B show an excitation spectrum and an emission spectrum of a toluene solution of 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA). FIG. 9 shows an emission spectrum of a thin film of 9,10-diphenyl-2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPAPA). FIG. 9 shows a ¹ H NMR chart of N-phenyl- (9-phenyl-9H-carbazol-3-yl) amine (abbreviation: PCA). FIG. 9 shows a ¹ H NMR chart of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows an absorption spectrum of a toluene solution of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows an absorption spectrum of a thin film of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). 9A and 9B show an excitation spectrum and an emission spectrum of a toluene solution of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows an emission spectrum of a thin film of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows CV measurement results of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows CV measurement results of 9,10-diphenyl-2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCAPA). FIG. 9 shows a ¹ H NMR chart of 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA). FIG. 9 shows an absorption spectrum of a toluene solution of 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA). FIG. 9 shows an absorption spectrum of a thin film of 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA). FIG. 9 shows an emission spectrum of a toluene solution of 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA). FIG. 9 shows an emission spectrum of a thin film of 9,10-di (2-biphenylyl) -2- [N- (4-diphenylaminophenyl) -N-phenylamino] anthracene (abbreviation: 2DPABPhA). FIG. 9 shows a ¹ H NMR chart of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). FIG. 9 shows an absorption spectrum of a toluene solution of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). . FIG. 9 shows an absorption spectrum of a thin film of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). . FIG. 11 shows an emission spectrum of a toluene solution of 9,10-bis (2-biphenyl) -2- [N-phenyl-N- (9-phenyl (9H) carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). . FIG. 9 shows an emission spectrum of a thin film of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). FIG. 9 shows CV measurement results of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). FIG. 9 shows CV measurement results of 9,10-di (2-biphenylyl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCABPhA). A diagram showing a ¹ H NMR chart of 4- (carbazol-9-yl) diphenylamine (abbreviation: YGA) FIG. 9 shows a ¹ H NMR chart of 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene (abbreviation: 2YGABPhA). . 9 shows an absorption spectrum of a toluene solution of 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene (abbreviation: 2YGABPhA). Figure. FIG. 9 shows an absorption spectrum of a thin film of 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene (abbreviation: 2YGABPhA). . 9 shows an emission spectrum of a toluene solution of 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene (abbreviation: 2YGABPhA). Figure. FIG. 9 shows an emission spectrum of a thin film of 9,10-di (2-biphenylyl) -2- {N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylamino} anthracene (abbreviation: 2YGABPhA). . FIG. 14 shows current density-luminance characteristics of Light-emitting Element 1. FIG. 6 shows voltage-luminance characteristics of the light-emitting element 1. FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 1. FIG. 9 shows an emission spectrum of the light-emitting element 1. FIG. 9 shows changes in normalized luminance time of the light-emitting element 1; FIG. 6 shows changes in driving voltage of the light emitting element 1 with time. FIG. 11 shows current density-luminance characteristics of Light-Emitting Element 2. FIG. 10 shows voltage-luminance characteristics of the light-emitting element 2; FIG. 14 shows luminance-current efficiency characteristics of the light-emitting element 2; FIG. 9 shows an emission spectrum of the light-emitting element 2; FIG. 11 shows current density-luminance characteristics of Light-Emitting Element 3. FIG. 10 shows voltage-luminance characteristics of the light-emitting element 3; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 3; FIG. 6 shows an emission spectrum of the light-emitting element 3. FIG. 5 shows changes in normalized luminance time of the light-emitting element 3; FIG. 6 shows a change in drive voltage time of the light-emitting element 3; FIG. 6 shows current density-luminance characteristics of the light-emitting element 4; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 4; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 4; FIG. 6 shows an emission spectrum of the light-emitting element 4. FIG. 14 shows current density-luminance characteristics of the light-emitting element 5; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 5; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 5; FIG. 9 shows an emission spectrum of the light-emitting element 5. FIG. 9 shows changes in normalized luminance time of the light-emitting element 5; FIG. 9 shows a change in drive voltage time of the light-emitting element 5; FIG. 14 shows current density-luminance characteristics of the light-emitting element 6; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 6; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 6; FIG. 9 shows an emission spectrum of the light-emitting element 6. FIG. 11 shows current density-luminance characteristics of the light-emitting element 7. FIG. 14 shows voltage-luminance characteristics of the light-emitting element 7; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 7; FIG. 9 shows an emission spectrum of the light-emitting element 7. FIG. 9 shows changes in normalized luminance time of the light-emitting element 7; FIG. 9 shows a change in driving voltage with time of the light-emitting element 7; FIG. 10 shows current density-luminance characteristics of the light-emitting element 8; FIG. 14 shows voltage-luminance characteristics of the light-emitting element 8; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 8; FIG. 9 shows an emission spectrum of the light-emitting element 8. FIG. 10 shows current density-luminance characteristics of the light-emitting element 9; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 9; FIG. 14 shows luminance-current efficiency characteristics of the light-emitting element 9; FIG. 9 shows an emission spectrum of the light-emitting element 9; FIG. 10 shows current density-luminance characteristics of the light-emitting element 10; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 10. FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 10. FIG. 9 shows an emission spectrum of the light-emitting element 10. FIG. 6 shows a ¹ H NMR chart of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). FIG. 9 shows an absorption spectrum of a toluene solution of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). FIG. 9 shows an absorption spectrum of a thin film of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). FIG. 9 shows an emission spectrum of a toluene solution of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). FIG. 9 shows an emission spectrum of a thin film of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). The figure which shows the CV measurement result of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). The figure which shows the CV measurement result of 2- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) -amino] -9,10-diphenylanthracene (abbreviation: 2PCNPA). FIG. 6 shows a ¹ H NMR chart of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). The figure which shows the absorption spectrum of the toluene solution of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). . FIG. 6 shows an absorption spectrum of a thin film of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). The figure which shows the emission spectrum of the toluene solution of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). . FIG. 9 shows an emission spectrum of a thin film of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). FIG. 11 shows current density-luminance characteristics of the light-emitting element 11. FIG. 11 shows voltage-luminance characteristics of the light-emitting element 11. FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 11. FIG. 11 shows an emission spectrum of the light-emitting element 11. FIG. 11 shows current density-luminance characteristics of the light-emitting element 12. FIG. 10 shows voltage-luminance characteristics of the light-emitting element 12; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 12. FIG. 11 shows an emission spectrum of the light-emitting element 12. The figure which shows the CV measurement result of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). The figure which shows the CV measurement result of 2- {N- (1-naphthyl) -N- [9- (1-naphthyl) carbazol-3-yl] amino} -9,10-diphenylanthracene (abbreviation: 2NCNPA). FIG. 3 shows a ¹ H NMR chart of 2- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGAPA). The figure which shows the absorption spectrum of the toluene solution of 2- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGAPA). The figure which shows the emission spectrum of the toluene solution of 2- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGAPA). FIG. 9 shows a ¹ H NMR chart of 9,10-diphenyl-1- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene (abbreviation: 1PCAPA). FIG. 9 shows an absorption spectrum of a toluene solution of 9,10-diphenyl-1- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene (abbreviation: 1PCAPA). FIG. 10 shows an emission spectrum of a toluene solution of 9,10-diphenyl-1- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] anthracene (abbreviation: 1PCAPA). 9,10-bis (9,9-dimethyl-fluoren-2-yl) -2- [N-phenyl--N-(9-phenyl--9H- carbazol-3-yl) amino] anthracene (abbreviation: 2PCADFA) of ¹ The figure which shows a H NMR chart. Toluene of 9,10-bis (9,9-dimethylfluoren-2-yl) -2- [N-phenyl-N- (9-phenyl-9H-carbazol-3-yl) amino] anthracene (abbreviation: 2PCADFA) The figure which shows the absorption spectrum and emission spectrum of a solution. FIG. 9 shows a ¹ H NMR chart of 9,10-diphenyl-2- [N- (4′-diphenylamino-1,1′-biphenyl-4-yl) -N-phenylamino] anthracene (abbreviation: 2DPBAPA). FIG. 10 shows an absorption spectrum of a toluene solution of 9,10-diphenyl-2- [N- (4′-diphenylamino-1,1′-biphenyl-4-yl) -N-phenylamino] anthracene (abbreviation: 2DPBAPA). . FIG. 9 shows an emission spectrum of a toluene solution of 9,10-diphenyl-2- [N- (4′-diphenylamino-1,1′-biphenyl-4-yl) -N-phenylamino] anthracene (abbreviation: 2DPBAPA). . 2- {N- [4 '- ( 9H- carbazol-9-yl) -1,1'-biphenyl-4-yl] -N- phenylamino} -9,10 diphenyl anthracene (abbreviation: 2YGBAPA) of ¹ The figure which shows a H NMR chart. 2- {N- [4 ′-(9H-carbazol-9-yl) -1,1′-biphenyl-4-yl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGBAPA) toluene The figure which shows the absorption spectrum of a solution. 2- {N- [4 ′-(9H-carbazol-9-yl) -1,1′-biphenyl-4-yl] -N-phenylamino} -9,10-diphenylanthracene (abbreviation: 2YGBAPA) toluene The figure which shows the emission spectrum of a solution. FIG. 13 shows current density-luminance characteristics of the light-emitting element 13; FIG. 11 shows voltage-luminance characteristics of the light-emitting element 13. FIG. 14 shows luminance-current efficiency characteristics of the light-emitting element 13; FIG. 9 shows an emission spectrum of the light-emitting element 13. FIG. 10 shows changes in normalized luminance time of the light-emitting element 13; FIG. 9 shows a change in drive voltage time of the light-emitting element 13; FIG. 14 shows current density-luminance characteristics of the light-emitting element 14; FIG. 14 shows voltage-luminance characteristics of the light-emitting element 14. FIG. 14 shows luminance-current efficiency characteristics of the light-emitting element 14; FIG. 9 shows an emission spectrum of the light-emitting element 14. FIG. 10 shows changes in normalized luminance time of the light-emitting element 14; FIG. 14 shows a change in driving voltage with time of the light-emitting element 14; FIG. 11 shows current density-luminance characteristics of the light-emitting element 15. FIG. 16 shows voltage-luminance characteristics of the light-emitting element 15; FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element 15. FIG. 9 shows an emission spectrum of the light-emitting element 15.

Explanation of symbols

101 substrate 102 first electrode 103 first layer 104 second layer 105 third layer 106 fourth layer 107 second electrode 301 substrate 302 first electrode 303 first layer 304 second layer 305 3rd layer 306 4th layer 307 2nd electrode 501 1st electrode 502 2nd electrode 511 1st light emission unit 512 2nd light emission unit 513 Charge generation layer 601 Source side drive circuit 602 Pixel part 603 Gate Side drive circuit 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (flexible printed circuit)
610 Element substrate 611 TFT for switching
612 Current control TFT
613 First electrode 614 Insulator 616 Layer containing light emitting substance 617 Second electrode 618 Light emitting element 623 n-channel TFT
624 p-channel TFT
901 Case 902 Liquid crystal layer 903 Backlight 904 Case 905 Driver IC
906 Terminal 951 Substrate 952 Electrode 953 Insulating layer 954 Partition layer 955 Layer containing light emitting material 956 Electrode 2001 Housing 2002 Light source 2101 Glass substrate 2102 First electrode 2103 Layer containing composite material 2104 Hole transport layer 2105 Light emitting layer 2106 Electron transport Layer 2107 Electron injection layer 2108 Second electrode 3001 Lighting device 3002 Television apparatus 9101 Housing 9102 Support base 9103 Display unit 9104 Speaker unit 9105 Video input terminal 9201 Body 9202 Housing 9203 Display unit 9204 Keyboard 9205 External connection port 9206 Pointing device 9401 Main body 9402 Housing 9403 Display unit 9404 Audio input unit 9405 Audio output unit 9406 Operation key 9407 External connection port 9408 Antenna 9501 Main unit 9502 Display unit 950 3 Housing 9504 External connection port 9505 Remote control receiving unit 9506 Image receiving unit 9507 Battery 9508 Audio input unit 9509 Operation key 9510 Eyepiece unit

Claims (23)

An anthracene derivative represented by the general formula (1).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (1-1) to the general formula (1-3). In the general formula (1-1) to the general formula (1-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α is a carbon number having 6 to 25. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.) An anthracene derivative represented by the general formula (2).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (2-1) to the general formula (2-3). In the general formulas (2-1) to (2-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.) An anthracene derivative represented by the general formula (3).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (3-1) to the general formula (3-3). In the general formulas (3-1) to (3-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.) An anthracene derivative represented by the general formula (4).

(In formula, Ar < ¹ > -Ar < ² > represents a C6-C25 aryl group, respectively, and A is either substitution represented by General formula (4-1)-General formula (4-3). In the general formulas (4-1) to (4-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.) 5. The anthracene derivative according to claim 1, wherein Ar ^{1 to} Ar ² are each a substituent represented by the general formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.) 5. The anthracene derivative according to claim 1, wherein Ar ^{1 to} Ar ² are substituents represented by the structural formula (11-2) or the structural formula (11-3), respectively.

5. The anthracene derivative according to claim 1, wherein Ar ^{1 to} Ar ² are each a substituent represented by the general formula (11-4).

(In the formula, R ^{6 to} R ⁷ each represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms.) 5. The anthracene derivative according to claim 1, wherein Ar ^{1 to} Ar ² are substituents represented by the structural formula (11-5) or the structural formula (11-6), respectively.

The anthracene derivative according to any one of claims 1 to 8, wherein Ar ¹ and Ar ² are substituents having the same structure. An anthracene derivative represented by the general formula (5).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (5-1) to the general formula (5-3). In the general formula (5-1) to the general formula (5-3), Ar ^{11 to} Ar ¹³ each represents an aryl group having 6 to 25 carbon atoms, and α represents an alkyl group having 6 to 25 carbon atoms. Represents an arylene group, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. R ³² represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and β is represents an arylene group having 6 to 25 carbon ^atoms, R 41 ^{to R 42} are each hydrogen, also , Alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.) An anthracene derivative represented by the general formula (6).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (6-1) to the general formula (6-3)). In the general formula (6-1) to the general formula (6-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{11 to} R ²⁴ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 or an aryl group having 6 to 25 carbon atoms, and R ^{33 to} R ³⁷ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms. Any one of 15 aryl groups, Ar ³¹ is aryl having 6 to 25 carbon atoms R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{43 to} R ⁴⁶ are each represented by , Hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms.) An anthracene derivative represented by the general formula (7).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (7-1) to the general formula (7-3). In the general formulas (7-1) to (7-3), Ar ¹¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{25 to} R ²⁶ represent hydrogen or carbon, respectively. It represents either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms, Ar ²¹ represents an aryl group having 6 to 25 carbon atoms, and R ³¹ represents hydrogen or 1 carbon atom. Represents an alkyl group having 4 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents an aryl group having 6 to 25 carbon atoms, and R ^{41 to} R ⁴² each represents hydrogen or Either an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms Represents.) An anthracene derivative represented by the general formula (8).

(In the formula, Ar ^{1 to} Ar ² each represent an aryl group having 6 to 25 carbon atoms, and A represents any one of the substitutions represented by the general formula (8-1) to the general formula (8-3). In the general formulas (8-1) to (8-3), Ar ¹¹ represents a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and R ^{25 to} R. ²⁶ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms, and Ar ²¹ represents a phenyl group, a 1-naphthyl group, or 2 -Represents any of naphthyl groups, R ³¹ represents either hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, Ar ³¹ represents a phenyl group, or , 1-naphthyl group, or 2-naphthyl group R ^{41 to} R ⁴² each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.) 14. The anthracene derivative according to claim 9, wherein Ar ^{1 to} Ar ² are each a substituent represented by the general formula (11-1).

(Wherein R ^{1 to} R ⁵ are each hydrogen, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms. Represents.) 14. The anthracene derivative according to claim 9, wherein Ar ^{1 to} Ar ² are substituents represented by the structural formula (11-2) or the structural formula (11-3), respectively.

14. The anthracene derivative according to claim 9, wherein Ar ^{1 to} Ar ² are each a substituent represented by the general formula (11-4).

(In the formula, R ^{6 to} R ⁷ each represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 15 carbon atoms.) 14. The anthracene derivative according to claim 9, wherein Ar ^{1 to} Ar ² are substituents represented by the structural formula (11-5) or the structural formula (11-6), respectively.

The anthracene derivative according to any one of claims 9 to 17, wherein Ar ¹ and Ar ² are substituents having the same structure. Between a pair of electrodes,
A light-emitting element comprising the anthracene derivative according to any one of claims 1 to 18. Having a light emitting layer between a pair of electrodes,
The light emitting layer has the anthracene derivative according to any one of claims 1 to 18. Having a light emitting layer between a pair of electrodes,
The light emitting layer has the anthracene derivative according to any one of claims 1 to 18,
A light-emitting element in which the anthracene derivative emits light. A light-emitting device comprising: the light-emitting element according to any one of claims 19 to 21; and a control unit that controls light emission of the light-emitting element. Having a display,
An electronic apparatus comprising: the light-emitting element according to any one of claims 19 to 21; and a control unit that controls light emission of the light-emitting element.

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