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EP-4741398-A1 - ORGANIC COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT

EP4741398A1EP 4741398 A1EP4741398 A1EP 4741398A1EP-4741398-A1

Abstract

The present disclosure provides an organic compound represented by general formula (1-1) or (1-2). In general formulas (1-1) and (1-2), at least four of bonding sites R a to R h and at least four of bonding sites R i to R p are bonded to a skeleton selected from Structure A group. Among the bonding sites R a to R p , bonding sites not bonded to Structure A group are each independently selected from a hydrogen atom or a substituent. In general formulas (2-1) to (2-10), R 1 to R 90 are each independently selected from a hydrogen atom, a deuterium atom, and various substituents. X is an oxygen atom, a sulfur atom, NR 91 , CR 92 R 93 , or SiR 94 R 95 . R 91 to R 95 are each independently selected from a hydrogen atom or a substituent. Bonding positions * represent positions of bonding to the bonding sites R a to R p .

Inventors

  • SEKIGUCHI, TAKESHI
  • TANAKA, AKANE

Assignees

  • Canon Kabushiki Kaisha

Dates

Publication Date
20260513
Application Date
20240621

Claims (20)

  1. An organic compound represented by general formula (1-1) or (1-2): wherein in general formula (1-1), at least four of bonding sites R a to R h are bonded to a skeleton selected from Structure A group; and among the bonding sites R a to R h , bonding sites not bonded to Structure A group are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, in general formula (1-2), at least four of bonding sites R i to R p are bonded to a skeleton selected from Structure A group; among the bonding sites R i to R p , bonding sites not bonded to Structure A group are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group; and X is an oxygen atom, a sulfur atom, NR 91 , CR 92 R 93 , or SiR 94 R 95 , where R 91 to R 95 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, in general formulas (2-1) to (2-10), R 1 to R 90 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group; X is an oxygen atom, a sulfur atom, NR 91 , CR 92 R 93 , or SiR 94 R 95 , where R 91 to R 95 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; and bonding positions * represent positions of bonding to the bonding sites R a to R p .
  2. The organic compound according to claim 1, wherein in general formula (1-1), four of the bonding sites R a to R h are bonded to the skeleton selected from Structure A group, and in general formula (1-2), four of the bonding sites R i to R p are bonded to the skeleton selected from Structure A group.
  3. The organic compound according to claim 1, wherein in the organic compound represented by general formula (1-1), the bonding sites R d , R c , R f , and R g are bonded to the skeleton selected from Structure A group.
  4. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-2), (2-4), (2-5), (2-6), (2-7), (2-8), (2-9), or (2-10).
  5. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is bonded to general formula (2-1), (2-5), (2-6), (2-7), or (2-8).
  6. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-1) is represented by general formula (3-6) or (3-7): in general formulas (3-6) and (3-7), bonding sites R a , R d , R e , and R h are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, and a cyano group; R 46 to R 63 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group; and X is an oxygen atom, a sulfur atom, NR 91 , CR 92 R 93 , or SiR 94 R 95 , where R 91 to R 95 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
  7. The organic compound according to claim 6, wherein in general formulas (3-6) and (3-7), R 46 to R 63 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 24 carbon atoms.
  8. The organic compound according to claim 7, wherein in general formulas (3-6) and (3-7), R 46 to R 63 are hydrogen atoms.
  9. The organic compound according to claim 1, wherein in the organic compound represented by general formula (1-2), the bonding sites R j , R k , R n , and R o are bonded to the skeleton selected from Structure A group.
  10. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-2) is bonded to general formula (2-6).
  11. The organic compound according to claim 1, wherein the organic compound represented by general formula (1-2) is represented by general formula (4-2): in general formula (4-2), bonding sites R i , R l , R m , and R p are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, and a cyano group; R 46 to R 54 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, and a cyano group; and X is an oxygen atom, a sulfur atom, NR 91 , CR 92 R 93 , or SiR 94 R 95 , where R 91 to R 95 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
  12. The organic compound according to claim 11, wherein in general formula (4-2), R 46 to R 54 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 24 carbon atoms.
  13. The organic compound according to claim 11, wherein in general formula (4-2), R 46 to R 54 are hydrogen atoms.
  14. An organic light-emitting element comprising: a first electrode and a second electrode; and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer contains the organic compound according to claim 1.
  15. The organic light-emitting element according to claim 14, wherein the organic compound layer includes a light-emitting layer, and the light-emitting layer contains the organic compound.
  16. The organic light-emitting element according to claim 15, wherein the light-emitting layer further contains a first compound, and a lowest excited singlet energy of the first compound is higher than a lowest excited singlet energy of the organic compound.
  17. The organic light-emitting element according to claim 16, wherein the first compound includes a fused polycyclic hydrocarbon compound.
  18. The organic light-emitting element according to claim 16, wherein the light-emitting layer further contains a second compound, and a lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.
  19. A display apparatus comprising a plurality of pixels, wherein at least one of the plurality of pixels includes the organic light-emitting element according to any one of claims 14 to 18 and a transistor connected to the organic light-emitting element.
  20. A photoelectric conversion apparatus comprising: an image pickup element configured to receive light; and a display unit configured to display an image captured by the image pickup element, wherein the display unit includes the organic light-emitting element according to any one of claims 14 to 18.

Description

Technical Field The present invention relates to an organic compound and an organic light-emitting element including the organic compound. Background Art An organic light-emitting element (hereinafter also referred to as an "organic electroluminescent element" or an "organic EL element") is an electronic element including a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes into the organic compound layer through the pair of electrodes, excitons of a luminescent organic compound in the organic compound layer are generated, and the organic light-emitting element emits light when the excitons return to their ground state. Compounds suitable for organic light-emitting elements have been actively created to date. PTL 1 discloses compound Ref-1 and compound Ref-2 as compounds having an indolocarbazole skeleton. Citation List Patent Literature PTL 1: International Publication No. 2019/111971 Summary of Invention Technical Problem However, the above compounds each have room for improvement in terms of thermal stability. The present invention has been made in view of the above problem, and an object thereof is to provide an organic compound having high thermal stability. Solution to Problem An organic compound according to the present invention is represented by general formula (1-1) or (1-2). In general formula (1-1), at least four of bonding sites Ra to Rh are bonded to a skeleton selected from Structure A group. Among the bonding sites Ra to Rh, bonding sites not bonded to Structure A group are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. In general formula (1-2), at least four of bonding sites Ri to Rp are bonded to a skeleton selected from Structure A group. Among the bonding sites Ri to Rp, bonding sites not bonded to Structure A group are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. In general formulas (2-1) to (2-10), R1 to R90 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom, a sulfur atom, NR91, CR92R93, or SiR94R95. R91 to R95 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Bonding positions * represent positions of bonding to the bonding sites Ra to Rp. Advantageous Effects of Invention According to the present invention, an organic compound having high thermal stability can be provided. Brief Description of Drawings [Fig. 1A] Fig. 1A is a schematic sectional view showing an example of a pixel of a display apparatus according to an embodiment of the present invention.[Fig. 1B] Fig. 1B is a schematic sectional view of an example of a display apparatus including an organic EL element according to an embodiment of the present invention.[Fig. 2] Fig. 2 is a schematic view showing an example of a display apparatus according to an embodiment of the present invention.[Fig. 3A] Fig. 3A is a schematic view showing an example of an image pickup apparatus according to an embodiment of the present invention.[Fig. 3B] Fig. 3B is a schematic view showing an example of an electronic apparatus according to an embodiment of the present invention.[Fig. 4A] Fig. 4A is a schematic view showing an example of a display apparatus according to an embodiment of the present invention.[Fig. 4B] Fig. 4B is a schematic view showing an example of a foldable display apparatus.[Fig. 5A] Fig. 5A is a schematic view showing an example of a lighting apparatus according to an embodiment of the present invention.[Fig. 5B] Fig. 5B is a schematic