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US-12624046-B2 - Organic compound, light-emitting device, electronic device, electronic apparatus, light-emitting apparatus, and lighting apparatus

US12624046B2US 12624046 B2US12624046 B2US 12624046B2US-12624046-B2

Abstract

An organic compound that easily exhibits thermally activated delayed fluorescence (TADF) is provided. An organic compound represented by General Formula (G1) is provided. In General Formula (G1), R 1 to R 8 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted diarylamino group; at least one of R 1 to R 8 is a substituted or unsubstituted diarylamino group; α is a substituted or unsubstituted phenylene group; n is an integer of 0 to 4; and A represents a substituted or unsubstituted benzofuropyrimidine skeleton or benzothienopyrimidine skeleton.

Inventors

  • Tomoya Hirose
  • Yasuhiro Niikura
  • Hiroshi Kadoma
  • Nobuharu Ohsawa
  • Harue Osaka
  • Satoshi Seo

Assignees

  • SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Dates

Publication Date
20260512
Application Date
20210201
Priority Date
20200214

Claims (20)

  1. 1 . An organic compound represented by General Formula (G1): wherein in General Formula (G1), R 1 to R 8 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted diarylamino group; at least one of R 1 to R 8 is the substituted or unsubstituted diarylamino group; α is a substituted or unsubstituted phenylene group; n is an integer of 0 to 4; and A is a group represented by General Formula (g1): wherein in General Formula (g1), one of R 11 and R 16 is a bond; R 12 to R 15 and the other of R 11 and R 16 are each independently any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; and Q represents an oxygen atom or a sulfur atom.
  2. 2 . An organic compound represented by General Formula (G2): wherein in General Formula (G2), R 1 to R 8 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted diarylamino group; at least one of R 1 to R 8 is the substituted or unsubstituted diarylamino group; α is a substituted or unsubstituted phenylene group; n is an integer of 0 to 4; R 11 to R 15 are each independently any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; and Q represents an oxygen atom or a sulfur atom.
  3. 3 . The organic compound according to claim 1 , wherein the substituted or unsubstituted diarylamino group is a group represented by General Formula (g2): wherein in General Formula (g2), Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring.
  4. 4 . The organic compound according to claim 3 , wherein one or both of R 3 and R 6 are groups represented by General Formula (g2).
  5. 5 . An organic compound represented by General Formula (G3): wherein in General Formula (G3), Ar 3 to Ar 6 are each independently any of a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; R 1 , R 2 , R 4 , R 5 , R 7 , and R 8 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 3 to 7 carbon atoms; α represents a substituted or unsubstituted phenylene group; n is an integer of 0 to 4; R 11 to R 15 are each independently any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; and Q represents an oxygen atom or a sulfur atom.
  6. 6 . The organic compound according to claim 5 , wherein the organic compound is represented by General Formula (G4): wherein in General Formula (G4), Ar 3 to Ar 6 are each independently any of a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; α is a substituted or unsubstituted phenylene group; n is an integer of 0 to 4; R 13 is any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; and Q represents an oxygen atom or a sulfur atom.
  7. 7 . The organic compound according to claim 5 , wherein the organic compound is represented by General Formula (G5): wherein in General Formula (G5), Ar 3 to Ar 6 are each independently any of a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; R 13 is any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring; and Q represents an oxygen atom or a sulfur atom.
  8. 8 . The organic compound according to claim 1 , wherein the organic compound is represented by Structural Formula (100):
  9. 9 . The organic compound according to claim 1 , wherein the organic compound is represented by Structural Formula (101):
  10. 10 . The organic compound according to claim 1 , wherein the organic compound is represented by Structural Formula (102):
  11. 11 . The organic compound according to claim 1 , wherein a difference between a lowest singlet excited level and a lowest triplet excited level of the organic compound is less than or equal to 0.2 eV.
  12. 12 . The organic compound according to claim 1 , wherein a difference between a lowest singlet excited level and a lowest triplet excited level of the organic compound is less than or equal to 0.1 eV.
  13. 13 . The organic compound according to claim 1 , wherein Q is an oxygen atom.
  14. 14 . An electronic device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the organic compound according to claim 1 .
  15. 15 . A light-emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the organic compound according to claim 1 .
  16. 16 . The light-emitting device according to claim 15 , wherein the organic layer comprises a light-emitting layer, and wherein the organic compound is included in the light-emitting layer.
  17. 17 . The light-emitting device according to claim 15 , wherein light emission from the organic layer is delayed fluorescence.
  18. 18 . The light-emitting device according to claim 17 , wherein a transient lifetime of the delayed fluorescence is longer than or equal to 100 nanoseconds and shorter than or equal to 10 milliseconds.
  19. 19 . The light-emitting device according to claim 16 , wherein the light-emitting layer further comprises a fluorescent light-emitting material.
  20. 20 . The light-emitting device according to claim 16 , wherein the light-emitting layer further comprises a phosphorescent light-emitting material.

Description

This application is a 371 of international application PCT/IB2021/050763 filed on Feb. 1, 2021 which is incorporated herein by reference. TECHNICAL FIELD One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting module, a display device, a light-emitting apparatus, an electronic apparatus, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the invention disclosed in this specification and the like relates to an object, a method, or a manufacturing method. One embodiment of the present invention relates to a process, a machine, manufacture, or a composition of matter. Specifically, examples of the technical field of one embodiment of the present invention disclosed in this specification include a semiconductor device, a display device, a liquid crystal display device, a light-emitting apparatus, a lighting device, a power storage device, a memory device, an imaging device, a driving method thereof, and a manufacturing method thereof. BACKGROUND ART Light-emitting devices (organic EL devices) including organic compounds and utilizing electroluminescence (EL) have been put into practical use. In the basic structure of such light-emitting devices, an organic compound layer containing a light-emitting material (an EL layer) is interposed between a pair of electrodes. Carriers are injected by application of voltage to the element, and recombination energy of the carriers is used, whereby light emission can be obtained from the light-emitting material. Such light-emitting devices are of self-light-emitting type and thus have advantages over liquid crystal, such as high visibility and no need for backlight when used for pixels of a display, and are suitable as flat panel display elements. Displays including such light-emitting devices are also highly advantageous in that they can be thin and lightweight. Moreover, an extremely fast response speed is also a feature. Since light-emitting layers of such light-emitting devices can be successively formed two-dimensionally, planar light emission can be achieved. This feature is difficult to realize with point light sources typified by incandescent lamps and LEDs or linear light sources typified by fluorescent lamps; thus, the light-emitting devices also have great potential as planar light sources, which can be applied to lighting and the like. Displays or lighting devices using light-emitting devices can be suitably used for a variety of electronic apparatuses as described above, and research and development of light-emitting devices has progressed for more favorable characteristics (see Patent Document 1, for example). REFERENCE Patent Document [Patent Document 1] Japanese Published Patent Application No. 2016-174161 SUMMARY OF THE INVENTION Problems to be Solved by the Invention An object of one embodiment of the present invention is to provide a novel organic compound. Alternatively, an object of one embodiment of the present invention is to provide an organic compound that easily exhibits delayed fluorescence and thermally activated delayed fluorescence (TADF). Alternatively, an object of one embodiment of the present invention is to provide an organic compound that exhibits TADF light emission. Alternatively, an object of one embodiment of the present invention is to provide an organic compound capable of providing a light-emitting element having favorable emission efficiency. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting device having favorable emission efficiency. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting device that exhibits TADF light emission. Alternatively, an object of one embodiment of the present invention is to provide a light-emitting apparatus, an electronic apparatus, a display device, and an electronic device each having low power consumption. Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not have to have all of these effects. Other effects will be apparent from the descriptions of the specification, the drawings, the claims, and the like, and other effects can be derived from the descriptions of the specification, the drawings, the claims, and the like. It is only necessary that at least one of the above-described objects be achieved in the present invention. Means for Solving the Problems An embodiment of the present invention is an organic compound represented by General Formula (G1). In General Formula (G1), R1 to R8 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted diarylamino group; at least one of R1 to R8 is