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CN-121986095-A - Compound, luminescent material and delayed fluorescence material

CN121986095ACN 121986095 ACN121986095 ACN 121986095ACN-121986095-A

Abstract

The compound represented by the following general formula is useful as a compound for an organic optical semiconductor element. One of X 1 and X 2 is N and the other is 1 of C-Y 3 ;Y 1 ～Y 3 is cyano, the remaining 2 and Y 4 and Y 5 are aryl or heteroaryl, R 1 is H or D, 1-3 of R 2 ～R 4 are donor groups, and the remainder is H, D, alkyl or aryl.

Inventors

  • Harasaki taro
  • MATSUOKA KENICHI
  • Kailing Youbarajie
  • Kaibiki Yuta
  • Niki iroku
  • MORIO Momoko
  • HIGA Takuya
  • Suzuki Shantake
  • Kotobuki Akira
  • Lower level Yukiko
  • Kinbara Yukihiro

Assignees

  • 九州有机光材股份有限公司

Dates

Publication Date
20260505
Application Date
20240927
Priority Date
20230927

Claims (13)

  1. 1. A compound represented by the following general formula (1), General formula (1) [ Chemical formula 1] In the general formula (1), one of X 1 and X 2 represents N, the other represents 1 of C-Y 3 ,Y 1 ～Y 3 represents cyano, the remaining 2 and Y 4 and Y 5 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 1 represents a hydrogen atom or a deuterium atom, and 1 to 3 of R 2 ～R 4 each independently represent a donor group, the remaining portion represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  2. 2. The compound according to claim 1, wherein, X 1 is N, X 2 is C-Y 3 ,Y 3 is cyano.
  3. 3. The compound according to claim 1, wherein, R 2 ～R 4 are each independently a donor group.
  4. 4. The compound according to claim 3, wherein, R 2 and R 4 are identical.
  5. 5. The compound according to claim 1, wherein, R 2 and R 4 are each independently a donor group, R 3 is a substituted or unsubstituted aryl group.
  6. 6. The compound according to claim 5, wherein, R 3 is aryl which may be substituted by deuterium atom, alkyl or aryl.
  7. 7. The compound according to claim 5, wherein, R 2 and R 4 are identical.
  8. 8. The compound according to claim 1, wherein, 1 Of Y 1 ～Y 3 is cyano, and the remaining 2 are each independently substituted or unsubstituted phenyl or substituted or unsubstituted carbazol-9-yl which may be fused.
  9. 9. The compound according to claim 1, wherein, At least 1 of 1 to 3 of the donor groups in R 2 ～R 4 is a substituted or unsubstituted diarylamino group, and 2 aryl groups in the diarylamino group may be bonded to each other.
  10. 10. The compound according to claim 9, wherein, At least 1 to 3 donor groups in R 2 ～R 4 are substituted or unsubstituted carbazol-9-yl groups which can be condensed rings.
  11. 11. The compound according to claim 1, wherein, At least 1 of the donor groups and Y 1 ～Y 5 contain deuterium atoms.
  12. 12. A luminescent material consisting of the compound according to any one of claims 1 to 11.
  13. 13. A delayed fluorescence material consisting of the compound of any one of claims 1 to 11.

Description

Compound, luminescent material and delayed fluorescence material Technical Field The present invention relates to a compound, a luminescent material and a delayed fluorescence material using the compound. Background Research related to organic light emitting elements is actively underway. For example, studies for improving the light-emitting efficiency of a light-emitting element such as an organic electroluminescent element (organic EL element) are actively being conducted. In particular, there has been much effort in improving the luminous efficiency by newly developing and combining an electron transporting material, a hole transporting material, a light emitting material, and the like constituting an organic electroluminescent element. Among them, studies on organic electroluminescent devices using delayed fluorescent materials have also been made. The delayed fluorescent material is a material that emits fluorescence when returning from an excited triplet state to a ground state after an intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence generated by this approach is observed later than fluorescence from an excited singlet state (normal fluorescence) generated directly from the ground state, and is therefore referred to as delayed fluorescence. Here, for example, in the case where a luminescent compound is excited by injection of carriers, the probability of occurrence of excited singlet and excited triplet is 25% to 75% in total, and therefore, there is a limit to improvement in light emission efficiency by fluorescence from only the excited singlet that is directly generated. On the other hand, in the delayed fluorescent material, in addition to the excited singlet state, the excited triplet state can be used for fluorescence emission by passing through the above-described pathway of intersystem crossing, and therefore, a high emission efficiency can be obtained compared with a usual fluorescent material. After this principle is clarified, various delayed fluorescent materials have been found through various studies, and application to organic light emitting elements such as organic electroluminescent elements has been proposed. Among them, compounds comprising a number of benzene rings substituted with a donor group and an acceptor group. For example, a compound having a skeleton in which a benzene ring is substituted with a carbazol-9-yl group as a donor group, a cyano group as an acceptor group, and a substituted triazinyl group has been proposed (refer to patent document 1). Technical literature of the prior art Patent literature Patent document 1 WO2019/191665A1 Disclosure of Invention Technical problem to be solved by the invention Heretofore, there has not been provided a compound which is extremely good in performance and free from practical problems when applied to an organic light-emitting element. Therefore, it is more useful to develop a compound capable of providing an organic light-emitting element having more excellent performance. However, the improvement of the compound is in a trial-and-error stage, and it is not easy to generalize the chemical structure of the useful compound. Under such circumstances, the present inventors have conducted studies with a view to providing a compound more useful as a compound for an organic light-emitting element. Further, intensive studies have been made for the purpose of deriving general formulae of compounds useful for organic light-emitting elements and generalizing them. Means for solving the technical problems As a result of intensive studies to achieve the above object, the present inventors have found that a compound having a structure satisfying specific conditions is useful as a compound for an organic light-emitting element. The present invention has been made in view of such an observation, and specifically 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), one of X 1 and X 2 represents N, the other represents 1 of C-Y 3.Y1～Y3 represents cyano, and the remaining 2 and Y 4 and Y 5 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 represents a hydrogen atom or a deuterium atom, and 1 to 3 of R 2～R4 each independently represent a donor group, and the remainder represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. ] [2] The compound according to [1], wherein X 1 is N, X 2 is C-Y 3,Y3 is cyano. [3] The compound according to [1] or [2], wherein R 2～R4 is each independently a donor group. [4] The compound according to any one of [1] to [3], wherein R 2 and R 4 are the same. [5] The compound according to [1] or [2], wherein R 2 and R 4 are each independently a donor group, and R 3 is a substituted or unsub