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CN-121991012-A - Organic compound, organic semiconductor device, and light-emitting device

CN121991012ACN 121991012 ACN121991012 ACN 121991012ACN-121991012-A

Abstract

Provided are an organic compound, an organic semiconductor device, and a light-emitting device, each of which has high heat resistance. Provided is an organic compound represented by the general formula (G1). In the general formula (G1), α 1 represents a substituted or unsubstituted phenylene group, n represents 1 or 2, α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group, m represents 0,1 or 2, ar 2 represents a group represented by the general formula (Ar 2 -a) or the general formula (Ar 2 -b), any one of R 8 to R 17 represents a bond, and X represents oxygen or sulfur.

Inventors

  • Kajiyama Kazutoshi
  • Hashimoto Naoa
  • KAWAKAMI SACHIKO
  • Namiki tsunenori
  • KUBOTA TOMOHIRO

Assignees

  • 株式会社半导体能源研究所

Dates

Publication Date
20260508
Application Date
20251028
Priority Date
20241101

Claims (17)

  1. 1. An organic compound represented by the general formula (G1), Wherein: α 1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0,1 or 2; R 1 to R 7 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted phenyl group; Ar 2 represents a group represented by the general formula (Ar 2 -a) or the general formula (Ar 2 -b); Any one of R 8 to R 17 represents a bond; R 8 to R 17 and R 18 to R 28 and R 31 to R 34 each independently represent any one of hydrogen, halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, silyl having 3 to 18 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and X represents oxygen or sulfur.
  2. 2. The organic compound according to claim 1, Wherein the organic compound is represented by the general formula (G2), And R 1 to R 7 and R 35 to R 38 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.
  3. 3. The organic compound according to claim 2, Wherein m in the general formula (G2) is 0.
  4. 4. The organic compound according to claim 1, Wherein the organic compound is represented by the general formula (G4), Wherein: R 35 to R 38 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and R 9 to R 17 、R 18 to R 28 and R 31 to R 34 each independently represent any one of hydrogen, halogen, cyano, straight-chain or branched alkyl group having 1 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 6 carbon atoms, silyl group having 3 to 18 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  5. 5. The organic compound according to claim 1, Wherein the organic compound is represented by the general formula (G5), Wherein: R 35 to R 38 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and R 9 to R 17 、R 18 to R 28 and R 31 to R 34 each independently represent hydrogen, halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, silyl having 3 to 18 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.
  6. 6. The organic compound according to claim 1, Wherein the organic compound is represented by structural formula (100) or structural formula (101), 。
  7. 7. An organic semiconductor device comprising: The organic compound according to claim 1.
  8. 8. A light emitting device, comprising: The organic compound according to claim 1.
  9. 9. An organic compound represented by the general formula (G7), Wherein: α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0,1 or 2; R 1 to R 7 and R 35 to R 38 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, Ar 2 represents a group represented by the general formula (Ar 2 -b); Any one of R 8 to R 17 represents a bond; R 8 to R 17 and R 18 to R 34 each independently represent any one of hydrogen, halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, silyl having 3 to 18 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and X represents oxygen or sulfur.
  10. 10. The organic compound according to claim 9, Wherein m is 0.
  11. 11. An organic semiconductor device comprising: The organic compound according to claim 9.
  12. 12. A light emitting device, comprising: The organic compound according to claim 9.
  13. 13. A light emitting device, comprising: A first electrode; a second electrode; a light-emitting layer, and The first layer of the material is formed from a first layer, Wherein the light emitting layer is positioned between the first electrode and the second electrode, The first layer is located between the first electrode and the light emitting layer, The first layer contains an organic compound represented by the general formula (G8), Wherein: α 1 and α 2 each independently represent a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n is 1 or 2; m is 0,1 or 2; R 1 to R 7 each independently represent any one of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and a substituted or unsubstituted phenyl group; Ar 2 represents any of a substituted or unsubstituted benzo [ b ] naphtho [2,1-d ] furyl, a substituted or unsubstituted benzo [ b ] naphtho [2,3-d ] furyl, a substituted or unsubstituted benzo [ b ] naphtho [2,1-d ] thienyl and a substituted or unsubstituted benzo [ b ] naphtho [2,3-d ] thienyl, and Ar 3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirobifluorenyl group.
  14. 14. A light emitting device according to claim 13, Wherein the organic compound in the first layer is represented by the general formula (G9), Wherein: Ar 2 represents a group represented by the general formula (Ar 2 -a) or the general formula (Ar 2 -b); Any one of R 8 to R 17 represents a bond; R 8 to R 17 , R 18 to R 28 , and R 31 to R 34 each independently represent any one of hydrogen, halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, silyl having 3 to 18 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; When R 29 and R 30 both represent a bond, R 29 and R 30 are bonded to each other to form a ring; When neither R 29 nor R 30 represents a bond, R 29 and R 30 each independently represent any one of hydrogen, halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, silyl having 3 to 18 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, and X represents oxygen or sulfur.
  15. 15. A light emitting device according to claim 13, Wherein the first layer is in contact with the light emitting layer.
  16. 16. A light emitting device according to claim 13, Wherein the first layer is in contact with the light emitting layer, The light-emitting layer comprises a first host material, a second host material and a light-emitting substance, The combination of the first host material and the second host material is a combination that forms an exciplex, And a difference between a peak wavelength of an emission spectrum of the exciplex and a peak wavelength of an emission spectrum of the light-emitting substance is 30nm or less.
  17. 17. A light emitting device according to claim 13, Wherein the first layer is in contact with the light emitting layer, And the light-emitting layer contains a host material and a fluorescent light-emitting substance.

Description

Organic compound, organic semiconductor device, and light-emitting device Technical Field One embodiment of the present invention relates to an organic compound, an organic semiconductor device, a light-emitting device, a photoelectric conversion device, a light-emitting device, a light-receiving device, a display device, an electronic apparatus, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above-described technical field. The technical field of one embodiment of the invention disclosed in the present specification and the like relates to an object, a method, or a manufacturing method. In addition, one embodiment of the present invention relates to a process, machine, product, or composition (composition of matter). Thus, more specifically, as an example of the technical field of one embodiment of the present invention disclosed in the present specification, a semiconductor device, a display device, a liquid crystal display device, a light emitting device, a lighting device, a power storage device, a storage device, an image pickup device, a driving method of these devices, or a manufacturing method of these devices can be given. Background In recent years, organic semiconductor devices are expected to be applied to various applications. Specific examples of the organic semiconductor device include a light emitting device such as an Organic Light Emitting Diode (OLED), a photoelectric conversion device such as an organic photosensor or an organic thin film solar cell, and an organic field effect transistor. Among them, a light emitting device utilizing an Electroluminescence (hereinafter referred to as EL) phenomenon has been applied to a display device because it is easy to realize a thin and lightweight light emitting device, and it can be driven at a high speed in response to an input signal, and it can be driven using a direct current constant voltage power supply or the like. In order to solve many problems depending on the organic compound, metal compound, and other substances constituting the organic semiconductor device, improvement of the device structure, development of the substances, and the like are performed to improve the characteristics of the organic semiconductor device. For example, patent document 1 discloses a hole transporting material which is an organic compound that can improve the light emitting efficiency of a light emitting device by being used for the light emitting device which is one of organic semiconductor devices. Patent document 1 japanese patent application laid-open No. 2009-298767. Disclosure of Invention It is an object of one embodiment of the present invention to provide a novel organic compound. Furthermore, it is an object of one embodiment of the present invention to provide a novel carrier transporting material. In addition, an object of one embodiment of the present invention is to provide a novel hole transporting material. Another object of one embodiment of the present invention is to provide a carrier transporting material or a hole transporting material having high heat resistance. Another object of another embodiment of the present invention is to provide an organic semiconductor device with small variation in driving voltage with respect to driving time. Another object of another embodiment of the present invention is to provide an organic semiconductor device having a long driving life. Another object of another embodiment of the present invention is to provide an organic semiconductor device, a light-emitting device, an electronic apparatus, a display device, and an electronic device each having low power consumption. Note that the description of these objects does not prevent the existence of other objects. Note that one embodiment of the present invention is not required to achieve all of the above objects. Note that other objects than the above can be obtained and extracted from the description of the specification, drawings, claims, and the like. One embodiment of the present invention is an organic compound represented by the general formula (G1). [ Chemical formula 1] In the general formula (G1), α 1 represents a substituted or unsubstituted phenylene group, n represents 1 or 2, α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group, m represents 0, 1 or 2, and R 1 to R 7 each independently represent hydrogen (including deuterium), Straight or branched alkyl group having 1 to 6 carbon atoms, Substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms or substituted or unsubstituted phenyl, ar 2 is a group represented by the general formula (Ar 2 -a) or the general formula (Ar 2 -b), any one of R 8 to R 17 represents a bond, and R 8 to R 17 and R 18 to R 28 and R 31 to R 34 each independently represent hydrogen (including deuterium), Halogen, cyano, straight-chain or branched alkyl having 1 to 6 carbo