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CN-116710456-B - Compound, light-emitting material, and organic light-emitting element

CN116710456BCN 116710456 BCN116710456 BCN 116710456BCN-116710456-B

Abstract

The compound represented by the following general formula has excellent light-emitting characteristics. Ar 1 represents a benzene ring, naphthalene ring, phenanthrene ring or the like, D represents 5H-indole [3,2,1-de ] phenazin-5-yl or the like, A represents cyano, phenyl, pyrimidinyl, triazolyl or the like, m represents 1 or 2;n represents 0 to 2, and R 1 ～R 4 represents H, aryl, cyano or the like.

Inventors

  • U. Barigapari
  • Suzuki Shantake
  • Shan Genyou
  • SAIDALIMU.YIWUREYIMUJIANG
  • YAMASHITA MASAYOSHI
  • Cui Shenjiong
  • HIGA Takuya

Assignees

  • 九州有机光材股份有限公司

Dates

Publication Date
20260505
Application Date
20220204
Priority Date
20210728

Claims (11)

  1. 1. A compound represented by any one of the following general formulae (4 a) to (4 c), General formula (4 a) general formula (4 b) general formula (4 c) In the general formulae (4 a) - (4 c), R 21 ～R 28 、R 41 ～R 44 、R 51 、R 52 、R 61 ～R 68 independently represents a hydrogen atom, a deuterium atom or D, wherein 1 or 2 of R 21 ～R 28 are D, 1 or 2 of R 41 ～R 44 、R 51 and R 52 are D, 1 or 2 of R 61 ～R 68 are D, D represents a group represented by the following general formula (2), R 29 ～R 36 independently represents a hydrogen atom, a deuterium atom or an alkyl group selected from the group consisting of 1 to 4 carbon atoms, R 45 ～R 50 、R 69 ～R 72 independently represents a hydrogen atom, a deuterium atom or one group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 10 ring skeleton, or a combination of two or more groups, General formula (2) [ Chemical formula 2] In the general formula (2), R 5 ～R 15 each independently represents a hydrogen atom, a deuterium atom or a substituent, the substituent is a cyano group or an aryl group having 6 to 10 atoms which is formed by a ring skeleton that may be substituted by 1 group or 2 or more groups selected from the group consisting of a cyano group and an alkyl group having 1 to 20 carbon atoms, X represents a single bond, Indicating the bonding location.
  2. 2. Use of a compound according to claim 1 as a luminescent material.
  3. 3. A membrane comprising the compound of claim 1.
  4. 4. An organic semiconductor element comprising the compound according to claim 1.
  5. 5. An organic light-emitting element comprising the compound of claim 1.
  6. 6. The organic light-emitting device according to claim 5, wherein, The element has a layer comprising the compound, the layer further comprising a host material.
  7. 7. The organic light-emitting device according to claim 6, wherein, In addition to the host material, the layer comprising the compound also comprises a delayed fluorescent material having a lowest excited singlet energy below the host material and above the compound.
  8. 8. The organic light-emitting element according to claim 5 or 6, wherein, The element has a layer containing the compound, the layer further containing a light-emitting material having a structure different from that of the compound.
  9. 9. The organic light-emitting element according to any one of claims 5 to 7, wherein, The amount of light emitted from the compound is greatest among the materials contained in the element.
  10. 10. The organic light-emitting device according to claim 8, wherein, The amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound.
  11. 11. The organic light-emitting element according to any one of claims 5 to 7, which emits delayed fluorescence.

Description

Compound, light-emitting material, and organic light-emitting element Technical Field The present invention relates to a compound having good light-emitting characteristics. The present invention also relates to a light-emitting material and an organic light-emitting element using the compound. Background The organic light-emitting element is a light-emitting element using an organic material, can be manufactured by coating, and is not using a rare element, and therefore, attention has been paid in recent years. Among them, since the organic electroluminescent element (organic EL element) emits self light and does not require a backlight, there is an advantage that a lightweight and flexible element can be manufactured. Further, the light source has characteristics such as quick response and high visibility, and is expected as a next-generation light source. Accordingly, research related to development of materials useful for organic light-emitting elements typified by organic electroluminescent elements is actively being conducted. In particular, studies on light-emitting materials are actively being conducted (for example, non-patent document 1). Technical literature of the prior art Non-patent literature Non-patent document 1: chem.Soc.Rev.,2017,46,915 Disclosure of Invention Technical problem to be solved by the invention On the other hand, there is room for improvement in the light emission characteristics of organic light emitting elements, and further improvement in the light emission characteristics is required. Accordingly, the present inventors have conducted intensive studies in order to develop a novel compound contributing to improvement of the light-emitting characteristics of an organic light-emitting element. Means for solving the technical problems As a result of intensive studies, the present inventors have found that a compound obtained by bonding a group having a characteristic structure to a specific skeleton is a compound useful for a light-emitting element. The present invention has been made based on such an insight, and has the following structure. [1] A compound represented by the following general formula (1). General formula (1) [ Chemical formula 1] [ In the general formula (1), ar 1 represents a cyclic structure, and represents a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. D represents a group represented by the following general formula (2). A represents one group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl and alkyl, or a combination of two or more groups (excluding substituted alkyl). m is 1 or 2, n is 0, 1 or 2. When m is 2, two D may be the same or different. When n is 2, two A may be the same or different. R 1～R4 independently represents a hydrogen atom, a deuterium atom, or one group selected from the group consisting of an alkyl group, an aryl group, a heteroaryl group, and a cyano group, or a combination of two or more groups. R 1 and R 2、R3 and R 4 may be bonded to each other to form a cyclic structure selected from the group consisting of a benzene ring, a naphthalene ring and a pyridine ring, and the formed cyclic structure may be substituted with one group selected from the group consisting of an alkyl group, an aryl group, a heteroaryl group and a cyano group or two or more groups. ] General formula (2) [ Chemical formula 2] [ In the general formula (2), R 5～R15 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 5 and R 6、R6 and R 7、R8 and R 9、R9 and R 10、R10 and R 11、R11 and R 12、R12 and R 13、R13 and R 14、R14 and R 15 may be bonded to each other to form a cyclic structure. X represents a single bond, an oxygen atom or a sulfur atom. * Indicating the bonding location. ] [2] A compound according to [1], which is represented by the following general formula (3). General formula (3) [ Chemical formula 3] [ In the general formula (3), ar 1 represents a cyclic structure, and represents a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. D represents a group represented by the general formula (2). A represents one group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl and alkyl, or a combination of two or more groups (excluding substituted alkyl). m is 1 or2, n is 0, 1 or 2. When m is 2, two D may be the same or different. When n is 2, two A may be the same or different. Ar 2、Ar3 may independently form a cyclic structure selected from the group consisting of a benzene ring, a naphthalene ring, and a pyridine ring, and the formed cyclic structure may be substituted with one group selected from the group consisting of an alkyl group, an aryl group, a heteroaryl group, and a cyano group, or a combination of two or more groups. ] [3] The compound according to [1], which has any one of the following backbones. [ Chemical formula 4] Each of the above skeletons may have a substituent in the range of the general formula (1), b