KR-20260065574-A - ORGANIC COMPOUND, ORGANIC SEMICONDUCTOR DEVICE, AND LIGHT-EMITTING DEVICE

KR20260065574AKR 20260065574 AKR20260065574 AKR 20260065574AKR-20260065574-A

Abstract

The present invention provides an organic compound with high heat resistance. Provides an organic compound represented by the general formula (G1). In general formula (G1), α1 represents a substituted or unsubstituted phenylene group, n represents 1 or 2, α2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group, m represents 0, 1, or 2, R1 to R7 each independently represent 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, or a substituted or unsubstituted phenyl group, Ar2 is a group represented by general formula ( Ar2 -a) or general formula ( Ar2 -b), any one of R8 to R17 represents a bonding hand, and R8 to R17 , R18 to R28 , and R31 to R34 other than bonding hands each independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched group It represents an 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, and X represents oxygen or sulfur. When n is 2, multiple α1 may be the same or different from each other. When m is 2, multiple α2 may be the same or different from each other.

Inventors

가지야마 가즈키
하시모토 나오아키
가와카미 사치코
스즈키 츠네노리
구보타 도모히로

Assignees

가부시키가이샤 한도오따이 에네루기 켄큐쇼

Dates

Publication Date: 20260508
Application Date: 20251031
Priority Date: 20241101

Claims (17)

As an organic compound, Organic compound represented by general formula (G1): In the above general formula (G1), α1 represents a substituted or unsubstituted phenylene group, and n is 1 or 2, and α2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group, and m is 0, 1, or 2, and R1 to R7 each 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, and Ar₂ represents a group expressed by the general formula ( Ar₂ -a) or the general formula ( Ar₂ -b), and Any one of R 8 to R 17 represents a bonding hand, and R 8 to R 17 , R 18 to R 28 , and R 31 to R 34 other than the bonding hands above each independently represent 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. X represents oxygen or sulfur.
In Article 1, The above organic compound is an organic compound represented by the general formula (G2): In the above general formula (G2), R1 to R7 and R35 to R38 each independently represent 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.
In Article 2, An organic compound in which m is 0 in the general formula (G2).
In Article 1, The above organic compound is an organic compound represented by the general formula (G4): In the above general formula (G4), R 35 to R 38 each 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 R 9 to R 17 , R 18 to R 28 , and R 31 to R 34 each independently represent 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 alkyneyl 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.
In Article 1, The above organic compound is an organic compound represented by the general formula (G5): In the above general formula (G5), R 35 to R 38 each 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 R 9 to R 17 , R 18 to R 28 , and R 31 to R 34 each independently represent 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 alkyneyl 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.
In Article 1, The above organic compound is an organic compound represented by structural formula (100) or structural formula (101).
As an organic semiconductor device, An organic semiconductor device comprising the organic compound described in claim 1.
As a light-emitting device, A light-emitting device comprising an organic compound described in claim 1.
As an organic compound, Organic compound represented by the general formula (G7): In the above general formula (G7), α2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalenediyl group, and m is 0, 1, or 2, and R1 to R7 and R35 to R38 each independently represent 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 Ar₂ represents a group expressed by the general formula ( Ar₂ -b), and Any one of R 8 to R 17 represents a bonding hand, and R 8 to R 17 and R 18 to R 34 other than the bonding hands above each independently represent 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 alkyneyl 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. X represents oxygen or sulfur.
In Article 9, An organic compound where m is 0.
As an organic semiconductor device, An organic semiconductor device comprising the organic compound described in claim 9.
As a light-emitting device, A light-emitting device comprising the organic compound described in claim 9.
As a light-emitting device, First electrode; Second electrode; light-emitting layer; and Includes the first floor, The light-emitting layer is located between the first electrode and the second electrode, and The first layer is located between the first electrode and the light-emitting layer, and A light-emitting device wherein the first layer comprises an organic compound represented by the general formula (G8): In the above general formula (G8), α1 and α2 each independently represent a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group, and n is 1 or 2, and m is 0, 1, or 2, and R1 to R7 each 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, and 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 fluorene group or a substituted or unsubstituted spirobifluorene group.
In Article 13, A light-emitting device in which the organic compound in the first layer is represented by the general formula (G9): In the above general formula (G9), Ar₂ represents a group expressed by the general formula ( Ar₂ -a) or the general formula ( Ar₂ -b), and Any one of R 8 to R 17 represents a bonding hand, and R 8 to R 17 , R 18 to R 28 , and R 31 to R 34 other than the bonding hands above each independently represent 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 R 29 and R 30 are each bonding hands, R 29 and R 30 bond together to form a ring, and Where R 29 and R 30 are not bonding hands, R 29 and R 30 each independently represent 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.
In Article 13, The above first layer is a light-emitting device in contact with the above light-emitting layer.
In Article 13, The first layer above is in contact with the light-emitting layer, and The light-emitting layer comprises a first host material, a second host material, and a light-emitting material, and The first host material and the second host material are a combination that forms an excited composite, and A light-emitting device in which the difference between the peak wavelength of the emission spectrum of the excited complex and the peak wavelength of the emission spectrum of the light-emitting material is within 30 nm.
In Article 13, The first layer above is in contact with the light-emitting layer, and The light-emitting layer comprises a host material and a fluorescent light-emitting material, forming a light-emitting device.

Description

Organic compound, organic semiconductor device, light-emitting device One embodiment of the present invention relates to organic compounds, organic semiconductor devices, light-emitting devices, photoelectric conversion devices, light-emitting devices, light-receiving devices, display devices, electronic devices, lighting devices, and electronic devices. Furthermore, one embodiment of the present invention is not limited to the above technical fields. The technical field to which one embodiment of the invention disclosed in this specification, etc. belongs relates to articles, methods, or manufacturing methods. Alternatively, one embodiment of the present invention relates to processes, machines, products, or compositions of matter. Therefore, more specific examples of the technical field to which one embodiment of the present invention disclosed in this specification belongs include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, capacitor devices, memory devices, imaging devices, methods for driving the same, or methods for manufacturing the same. In recent years, organic semiconductor devices are expected to be applied to a wide variety of uses. Specific examples of organic semiconductor devices include light-emitting devices such as organic light-emitting diodes (OLEDs), photoelectric conversion devices such as organic photosensors and organic thin-film solar cells, and organic field-effect transistors. Among these, light-emitting devices utilizing the electroluminescence (hereinafter referred to as EL) phenomenon are being applied to display devices because they have features such as being easy to make thin and lightweight, capable of high-speed response to input signals, and capable of driving using a DC constant voltage power supply. Organic semiconductor devices have many problems that depend on materials such as organic compounds, metals, and metal compounds that constitute the organic semiconductor device in improving the device characteristics, so improvements in device structure and material development are being carried out to overcome these. For example, Patent Document 1 discloses a hole-transporting material, which is a type of organic compound, that can increase the luminescence efficiency of a light-emitting device by using it in a light-emitting device, which is a type of organic semiconductor device. Figures 1 (A) to (C) are drawings illustrating the configuration of an organic semiconductor device according to an embodiment. Figures 2 (A) and (B) are drawings illustrating the configuration of a device according to an embodiment. Figures 3 (A) to (F) are drawings illustrating the configuration of a light-emitting device according to an embodiment. Figures 4 (A) and (B) are a top view and a cross-sectional view of the display device. Figures 5 (A) and (B) are perspective views showing examples of the configuration of a display module. Figures 6 (A) and (B) are cross-sectional views showing examples of the configuration of a display device. FIG. 7 is a perspective view showing an example of the configuration of a display device. Figure 8 (A) is a cross-sectional view showing an example of the configuration of a display device. Figures 8 (B) and (C) are cross-sectional views showing examples of the configuration of a transistor. FIG. 9 is a cross-sectional view showing an example of the configuration of a display device. Figures 10 (A) to (C) are cross-sectional and top views showing examples of configurations of a display device. Figures 11 (A) to (D) are cross-sectional views showing examples of the configuration of a display device. Figures 12 (A) to (C) are cross-sectional and top views showing examples of the configuration of a display device. Figures 13 (A) to (D) are drawings showing examples of electronic devices. Figures 14 (A) to (F) are drawings showing examples of electronic devices. Figures 15 (A) to (G) are drawings showing examples of electronic devices. FIG. 16 is a diagram illustrating the structure of a light-emitting device according to an embodiment. Figure 17 shows the 1H NMR spectrum of SFNBaBnf (10). Figure 18 is a diagram showing the absorption spectrum and emission spectrum of SFNBaBnf (10) in a toluene solution. Figure 19 is a diagram showing the absorption spectrum and emission spectrum of a thin film of SFNBaBnf (10). Figures 20 (A) and (B) show the phosphorescence spectrum of SFNBaBnf (10). Figure 21 shows the 1H NMR spectrum of SFNBBnf(II)(4). Figure 22 is a diagram showing the absorption spectrum and emission spectrum of SFNBBnf(II)(4) in a toluene solution. Figure 23 is a diagram showing the absorption spectrum and emission spectrum of the thin film of SFNBBnf(II)(4). Figures 24 (A) and (B) show the phosphorescence spectrum of SFNBBnf(II)(4). Figure 25 shows the emission spectra of a single film of 8 mpTP-4 mDBtPBfpm, a single film of βNCCP, and a mixed film. Figure 26 shows the absorption and