US-20260130046-A1 - ORGANIC COMPOUND, ORGANIC SEMICONDUCTOR DEVICE, AND LIGHT-EMITTING DEVICE

US20260130046A1US 20260130046 A1US20260130046 A1US 20260130046A1US-20260130046-A1

Abstract

An organic compound having high heat resistance is provided. The organic compound is represented by General Formula (G1). In General Formula (G1), 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; Ar 2 represents a group represented by General Formula (Ar 2 -a) or General Formula (Ar 2 -b); any one of R 8 to R 17 represents a bond; and X represents oxygen or sulfur.

Inventors

Kazuki Kajiyama
Naoaki HASHIMOTO
Sachiko Kawakami
Tsunenori Suzuki
Tomohiro Kubota

Assignees

SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Dates

Publication Date: 20260507
Application Date: 20251021
Priority Date: 20241101

Claims (17)

1 . An organic compound represented by 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; each of R 1 to R 7 independently represents any one of hydrogen, a straight-chain or branched-chain 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 General Formula (Ar 2 -a) or General Formula (Ar 2 -b); any one of R 8 to R 17 represents a bond; each of R 8 to R 17 other than the bond and each of R 18 to R 28 and R 31 to R 34 independently represents any one of hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and X represents oxygen or sulfur.
2 . The organic compound according to claim 1 , wherein the organic compound is represented by General Formula (G2), and wherein each of R 1 to R 7 and R 35 to R 38 independently represents any one of hydrogen, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.
3 . The organic compound according to claim 2 , wherein m in General Formula (G2) is 0.
4 . The organic compound according to claim 1 , wherein the organic compound is represented by General Formula (G4), and wherein: each of R 35 to R 38 independently represents any one of hydrogen, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; and each of R 9 to R 17 , R 18 to R 28 , and R 31 to R 34 independently represents any one of hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
5 . The organic compound according to claim 1 , wherein the organic compound is represented by General Formula (G5), and wherein: each of R 35 to R 38 independently represents any one of hydrogen, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; and each of R 9 to R 17 , R 18 to R 28 , and R 31 to R 34 independently represents hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
6 . The organic compound according to claim 1 , wherein the organic compound is represented by Structural Formula (100) or Structural Formula (101),
7 . An organic semiconductor device comprising: the organic compound according to claim 1 .
8 . A light-emitting device comprising: the organic compound according to claim 1 .
9 . An organic compound represented by 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; each of R 1 to R 7 and R 35 to R 38 independently represents any one of hydrogen, a straight-chain or branched-chain 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 General Formula (Ar 2 -b); any one of R 8 to R 17 represents a bond; each of R 8 to R 17 other than the bond and each of R 18 to R 34 independently represents any one of hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and X represents oxygen or sulfur.
10 . The organic compound according to claim 9 , wherein m is 0.
11 . An organic semiconductor device comprising: the organic compound according to claim 9 .
12 . A light-emitting device comprising: the organic compound according to claim 9 .
13 . A light-emitting device comprising: a first electrode; a second electrode; a light-emitting layer; and a first layer, wherein the light-emitting layer is between the first electrode and the second electrode, wherein the first layer is between the first electrode and the light-emitting layer, wherein the first layer comprises an organic compound represented by General Formula (G8), and wherein: each of α 1 and α 2 independently represents 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; each of R 1 to R 7 independently represents any one of hydrogen, a straight-chain or branched-chain 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 one of a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]thiophenyl group, and a substituted or unsubstituted benzo[b]naphtho[2,3-d]thiophenyl group; and Ar 3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirobifluorenyl group.
14 . The light-emitting device according to claim 13 , wherein the organic compound in the first layer is represented by General Formula (G9), and wherein: Ar 2 represents a group represented by General Formula (Ar 2 -a) or General Formula (Ar 2 -b); any one of R 8 to R 17 represents a bond; each of R 8 to R 17 other than the bond and each of R 18 to R 28 and R 31 to R 34 independently represents any one of hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; when each of R 29 and R 30 represents 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, each of R 29 and R 30 independently represents any one of hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and X represents oxygen or sulfur.
15 . The light-emitting device according to claim 13 , wherein the first layer is in contact with the light-emitting layer.
16 . The light-emitting device according to claim 13 , wherein the first layer is in contact with the light-emitting layer, wherein the light-emitting layer comprises a first host material, a second host material, and a light-emitting substance, wherein the first host material and the second host material form an exciplex in combination, and wherein 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 less than or equal to 30 nm.
17 . The light-emitting device according to claim 13 , wherein the first layer is in contact with the light-emitting layer, and wherein the light-emitting layer comprises a host material and a fluorescent substance.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention 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 apparatus, a light-receiving apparatus, a display device, an electronic appliance, 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 apparatus, a display device, a liquid crystal display apparatus, 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. 2. Description of the Related Art In recent years, organic semiconductor devices have been expected to be applied to a variety of uses. Specific examples of the organic semiconductor devices include a light-emitting device such as an organic light-emitting diode (OLED), a photoelectric conversion device such as an organic optical sensor or an organic thin film solar cell, and an organic field-effect transistor. Among them, light-emitting devices utilizing electroluminescence (hereinafter referred to as EL) have features such as ease of reduction in thickness and weight, high-speed response to input signals, and driving with a constant DC voltage power source, and thus have been used in display devices. In improving device characteristics of the organic semiconductor device, there are many problems which depend on a substance contained in the organic semiconductor device, such as an organic compound, a metal, and a metal compound. In order to solve the problems, improvement of a device structure, development of a substance, and the like have been carried out. For example, Patent Document 1 discloses a hole-transport material, a kind of organic compound that can increase emission efficiency of a light-emitting device, a kind of organic semiconductor device, when used for the light-emitting device. REFERENCE [Patent Document 1]Japanese Published Patent Application No. 2009-298767 SUMMARY OF THE INVENTION An object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide a novel carrier-transport material. Another object of one embodiment of the present invention is to provide a novel hole-transport material. Another object of one embodiment of the present invention is to provide a highly heat-resistant carrier-transport material or hole-transport material. Another object of one embodiment of the present invention is to provide an organic semiconductor device with small change in driving voltage over driving time. Another object of one embodiment of the present invention is to provide an organic semiconductor device having a long driving lifetime. Another object of one embodiment of the present invention is to provide an organic semiconductor device, a light-emitting apparatus, an electronic appliance, a display device, and an electronic device each having low power consumption. Note that the description of these objects does not preclude the existence of other objects. One embodiment of the present invention does not need to achieve all of these objects. Other objects will be apparent from and can be derived from the description of the specification, the drawings, the claims, and the like. One embodiment of the present invention is an organic compound represented by General Formula (G1). In General Formula (G1), α1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1, or 2; each of R1 to R7 independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar2 represents a group represented by General Formula (Ar2-a) or General Formula (Ar2-b); any one of R8 to R17 represents a bond; each of R8 to R17 other than the bond and each of R18 to R28 and R31 to R34 independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group