Organic compound, light-emitting device, display device, and electronic apparatus

By using organic compounds with bicyclic guanidine skeletons and aromatic skeletons as electron injection layers, the problem of degradation of the organic compound layer during lithography processing is solved, efficient electron injection is achieved, and the reliability of light-emitting devices and the performance of display devices are improved.

CN120659786APending Publication Date: 2025-09-16SEMICON ENERGY LAB CO LTD
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Patent Information

Application Number
CN202480011261.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2023-02-24
Filing Date
2024-02-16
Publication Date
2025-09-16

AI Technical Summary

Technical Problem

When using existing lithography technology to process organic semiconductor films, especially organic compound layers containing donor substances, they are easily affected by oxygen or water in the atmosphere, resulting in increased driving voltage and decreased current efficiency, which is particularly significant in series-type light-emitting devices.

Method used

Organic compounds with bicyclic guanidine skeletons and aromatic skeletons are used as electron injection layers or intermediate layers to replace traditional donor substances. By increasing the hydrophobicity and alkalinity of the aromatic skeleton, the solubility in water is reduced, and the planarity is reduced by the distortion within the polysubstituted aromatic skeleton, thereby avoiding the degradation of properties during the lithography process.

Benefits of technology

It effectively prevents the driving voltage of the light-emitting device from rising sharply and the current efficiency from decreasing significantly, increases the glass transition temperature of the organic compound, and enhances the reliability of the light-emitting device and the resolution, aperture ratio and reliability of the display device.

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Abstract

Provided is an organic compound having electron injection properties and low solubility in water. Provided is an organic compound represented by general formula (G1). In general formula (G1), Ar is an aromatic skeleton represented by general formula (Ar-1), L represents an alkylene group, an arylene group, or a heteroarylene group, n represents an integer of 0 to 3, m represents an integer of 1 to 6, and R1 to R12 each independently represent hydrogen or an alkyl group. In general formula (Ar-1), ring A represents a benzene ring or a naphthalene ring, Ar1 to Ar3 each independently represents an aryl group or a heteroaryl group, any m of the carbons contained in ring A and Ar1 to Ar3 have m bonds in general formula (G1), k represents an integer of 1 to 3, and p represents an integer of 2 to 6. # imgabs0 #
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Claims

1. An organic compound represented by the general formula (G1). [Chemical Formula 1] (Note that in the general formula (G1), Ar is an aromatic skeleton represented by the general formula (Ar-1), L represents an alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 11 carbon atoms, n represents an integer from 0 to 3, m represents an integer from 1 to 6, and R 1 to R 12 Each independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms. In addition, when n is 2 or more, L may be the same or different from each other, and when m is 2 or more, L may be the same or different from each other, n may be the same or different from each other, and R 1 to R 12 In the general formula (Ar-1), ring A represents a benzene ring or a naphthalene ring, and Ar 1 to Ar 3 Each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, Ring A and Ar 1 to Ar 3 Any m of the included carbon atoms have m bonds in the general formula (G1), k represents an integer from 1 to 3, and p represents an integer from 2 to 6. Note that a plurality of Ar 2 In addition, when k is 2 or more, p may be the same or different, and ring A may be the same or different, and Ar 2 They may be the same or different from each other.) 2. An organic compound represented by the general formula (G1). [Chemical Formula 2] (Note that in the general formula (G1), Ar is an aromatic skeleton represented by the general formula (Ar-2), L represents an alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 11 carbon atoms, n represents an integer from 0 to 3, m represents an integer from 1 to 6, and R 1 to R 12 Each independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms. In addition, when n is 2 or more, L may be the same or different from each other, and when m is 2 or more, L may be the same or different from each other, n may be the same or different from each other, and R 1 to R 12 They may be the same or different from each other. 1 to Ar 3 Each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, Ar 1 to Ar 3 Any m of the included carbon atoms have m bonds in the general formula (G1), R 26 represents hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, k represents an integer from 1 to 3, and q represents an integer from 2 to 4. Note that multiple Ar 2 Also, when k is 2 or more, p may be the same or different from each other. 26 They may also be the same or different from each other, and Ar 2 They may be the same or different from each other.) 3. An organic compound represented by the general formula (G1). [Chemical Formula 3] (Note that in the general formula (G1), Ar is an aromatic skeleton represented by the general formula (Ar-3), L represents an alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 11 carbon atoms, n represents an integer from 0 to 3, m represents an integer from 1 to 6, and R 1 to R 12 Each independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms. In addition, when n is 2 or more, L may be the same or different from each other, and when m is 2 or more, L may be the same or different from each other, n may be the same or different from each other, and R 1 to R 12 They may be the same or different from each other. 21 to R 46 Any m of them represent m bonding positions in the general formula (G1), R 21 to R 46 The others in the group independently represent hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms.

4. An organic compound represented by the general formula (G2). [Chemical Formula 4] (Note that in the general formula (G2), L represents an alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 11 carbon atoms, n represents an integer from 0 to 3, and R 1 to R 12 Each independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms. When n is 2 or greater, L may be the same or different. 21 to R 27 and R 29 to R 46 Each independently represents hydrogen (including deuterium), an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms.

5. An organic compound represented by structural formula (100). [Chemical Formula 5] 6 . A light-emitting device using the organic compound according to claim 1 .

7. A display device comprising: The light-emitting device according to claim 6; as well as transistor or substrate.

8. An electronic device comprising: The display device according to claim 7; as well as Detection unit, input unit or communication unit.

Citation Information

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  • Light emitting device, display device, electronic device, and lighting device

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