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US-20260130110-A1 - ORGANIC COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT

US20260130110A1US 20260130110 A1US20260130110 A1US 20260130110A1US-20260130110-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), R 1 to R 3 are each a deuterium atom or a substituent. R 4 is an alkyl group or an alkoxy group. 1 and m are each an integer of 0 to 5, and n is an integer of 0 to 3. D 1 is represented by general formula (2). In general formula (2), R 5 to R 7 are each a deuterium atom or a substituent. o and q are each an integer of 0 to 4, and p is an integer of 0 to 2. Z 1 is an oxygen atom, a sulfur atom, a selenium atom, NR 8 , or CR 9 R 10 . R 8 to R 10 are each a hydrogen atom, a deuterium atom, or a substituent. * represents a position of bonding to general formula (1-1) or (1-2).

Inventors

  • Takayoshi Yamada
  • Yuto Ito
  • Kaori FUJISAWA

Assignees

  • CANON KABUSHIKI KAISHA

Dates

Publication Date
20260507
Application Date
20251230
Priority Date
20230707

Claims (20)

  1. 1 . An organic compound represented by general formula (1-1) or (1-2): wherein in general formulas (1-1) and (1-2), R 1 to R 3 are each independently selected from the group consisting of 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; R 4 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkoxy group; I and m are each an integer of 0 to 5, and n is an integer of 0 to 3; a plurality of R 1 's may be the same as or different from each other, a plurality of R 2 's may be the same as or different from each other, and a plurality of R 3 's may be the same as or different from each other; and D 1 is represented by general formula (2): in general formula (2), R 5 to R 7 are each independently selected from the group consisting of 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; o and q are each an integer of 0 to 4, and p is an integer of 0 to 2; a plurality of R 5 's may be the same as or different from each other, a plurality of R 6 's may be the same as or different from each other, and a plurality of R 7 's may be the same as or different from each other; Z 1 is an oxygen atom, a sulfur atom, a selenium atom, NR 8 , or CR 9 R 10 , where R 8 to R 10 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; * represents a position of bonding to general formula (1-1) or (1-2); and when Z 1 is a nitrogen atom having the substituted or unsubstituted heterocyclic group, the heterocyclic group has 3 to 12 carbon atoms.
  2. 2 . The organic compound according to claim 1 , wherein in general formula (2), Z 1 is an oxygen atom, a sulfur atom, or NR 8 .
  3. 3 . The organic compound according to claim 1 , wherein in general formula (2), Z 1 is an oxygen atom.
  4. 4 . The organic compound according to claim 1 , wherein in general formula (1-1) or (1-2), R 4 is an alkyl group having 1 to 7 carbon atoms.
  5. 5 . The organic compound according to claim 1 , wherein in general formula (1-1) or (1-2), R 4 is a methyl group.
  6. 6 . The organic compound according to claim 1 , wherein general formula (2) is general formula (2-1):
  7. 7 . The organic compound according to claim 1 , wherein general formula (1-1) or (1-2) is general formula (3) or (4):
  8. 8 . The organic compound according to claim 1 , wherein general formula (1-1) or (1-2) is general formula (5) or (6):
  9. 9 . 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 at least one layer of the organic compound layer contains the organic compound according to claim 1 .
  10. 10 . The organic light-emitting element according to claim 9 , wherein the organic compound layer includes a light-emitting layer, and the light-emitting layer contains the organic compound.
  11. 11 . The organic light-emitting element according to claim 10 , wherein the light-emitting layer further contains a first compound, and a lowest excited singlet energy of the organic compound is lower than a lowest excited singlet energy of the first compound.
  12. 12 . The organic light-emitting element according to claim 10 , wherein the light-emitting layer further contains a third compound, and a lowest excited singlet energy of the third compound is lower than a lowest excited singlet energy of the organic compound.
  13. 13 . The organic light-emitting element according to claim 12 , wherein the third compound is a fluorescent material.
  14. 14 . The organic light-emitting element according to claim 10 , wherein in the light-emitting layer, a concentration of the organic compound is 0.01 mass % or more and 99 mass % or less relative to the whole light-emitting layer.
  15. 15 . The organic light-emitting element according to claim 10 , wherein in the light-emitting layer, a concentration of the organic compound is 10 mass % or more and 50 mass % or less relative to the whole light-emitting layer.
  16. 16 . 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 claim 9 and a transistor connected to the organic light-emitting element.
  17. 17 . 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 claim 9 .
  18. 18 . An image display apparatus comprising: a display unit including the organic light-emitting element according to claim 9 ; and a housing provided with the display unit.
  19. 19 . An electronic apparatus comprising: a display unit including the organic light-emitting element according to claim 9 ; a housing provided with the display unit; and a communication unit provided in the housing and configured to communicate with an external unit.
  20. 20 . A wearable device comprising: a display unit including the organic light-emitting element according to claim 9 ; an optical system configured to collect light of the display unit; and a controller configured to control display of the display unit.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a Continuation of International Patent Application No. PCT/JP2024/022486, filed Jun. 21, 2024, which claims the benefit of Japanese Patent Application No. 2023-112257, filed Jul. 7, 2023, and Japanese Patent Application No. 2024-088438, filed May 30, 2024, all of which are hereby incorporated by reference herein in their entirety. BACKGROUND Field of the Technology The present disclosure relates to an organic compound and an organic light-emitting element including the organic compound. Description of the Related 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. Japanese Patent Laid-Open No. 2022-019638, International Publication No. 2014/092083, and International Publication No. 2016/159479 respectively disclose compound Ref-1 to compound Ref-3 as donor-acceptor type organic compounds having a donor moiety and an acceptor moiety. However, the above compounds each have a large ΔEST, which is the difference between a lowest excited singlet energy (S1) and a lowest excited triplet energy (T1), and thus have room for improvement. SUMMARY The present disclosure has been made in view of the above problem and is directed to an organic compound having a smaller ΔEST. An organic compound according to the present disclosure is represented by general formula (1-1) or (1-2). In general formulas (1-1) and (1-2), R1 to R3 are each independently selected from the group consisting of 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. R4 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkoxy group. 1 and m are each an integer of 0 to 5, and n is an integer of 0 to 3. A plurality of R1's may be the same as or different from each other, a plurality of R2's may be the same as or different from each other, and a plurality of R3's may be the same as or different from each other. D1 is represented by general formula (2). In general formula (2), R5 to R7 are each independently selected from the group consisting of 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. o and q are each an integer of 0 to 4, and p is an integer of 0 to 2. A plurality of R5's may be the same as or different from each other, a plurality of R6's may be the same as or different from each other, and a plurality of R7's may be the same as or different from each other. Z1 is an oxygen atom, a sulfur atom, a selenium atom, NR8, or CR9R10. R8 to R10 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. * represents a position of bonding to general formula (1-1) or (1-2). When Z1 is a nitrogen atom having the substituted or unsubstituted heterocyclic group, the heterocyclic group has 3 to 12 carbon atoms. Features of the present disclosure will become apparent from the following description of embodiments with reference to the attached drawings. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1A is a schematic sectional view showing an example of a pixel of a display apparatus according to an embodiment of the present disclosure. FIG. 1B is a schematic sectional view of an example of a display apparatus including an organic light-emitting element according to an embodiment of the present disclosure. FIG. 2 is a schematic view showing an example