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 or intermediate layers, the problems of driving voltage and current efficiency caused by oxygen and water exposure in lithography processing are solved, and high-quality light-emitting devices and display devices are achieved.

CN120659788APending Publication Date: 2025-09-16SEMICON ENERGY LAB CO LTD
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Patent Information

Application Number
CN202480011459.3
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 the existing technology uses lithography technology to process organic compound layers, the electron injection layer is exposed to oxygen, water, etc., resulting in a significant increase in driving voltage and a significant decrease in current efficiency, which is particularly obvious during the processing of the intermediate layer in a series-type light-emitting device.

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, improve hydrophobicity to reduce water solubility, and are processed through lithography technology to avoid property degradation.

Benefits of technology

The invention effectively prevents the driving voltage of the light-emitting device from rising and the current efficiency from decreasing, improves the display quality and reliability of the light-emitting device, and realizes a display device with high definition, high resolution and high aperture ratio.

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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). Note that 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 4, 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, ring B represents a naphthalene ring, an anthracene ring, or a phenanthrene ring, alpha represents oxygen, sulfur, carbon having a substituent, silicon having a substituent, or germanium having a substituent, and any m carbon atoms included in general formula (Ar-1) have m bonds in general formula (G1). # 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 is 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 4, 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, 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 as or different from each other. In the general formula (Ar-1), ring A represents a benzene ring or a naphthalene ring, ring B represents a naphthalene ring, anthracene ring or a phenanthrene ring, α represents oxygen, sulfur, substituted carbon, substituted silicon or substituted germanium, and any m of the carbon atoms included in the general formula (Ar-1) have m bonds in the general formula (G1).

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 4, 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, 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-2), ring B represents a naphthalene ring, anthracene ring or phenanthrene ring, α represents oxygen, sulfur, carbon with a substituent, silicon with a substituent or germanium with a substituent, and R 21 to R 24 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, and any m of the carbon atoms included in the general formula (Ar-2) have m bonds in the general formula (G1).

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 4, 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, 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-3), α represents oxygen, sulfur, carbon with a substituent, silicon with a substituent or germanium with a substituent, and R 21 to R 32 Any m of them represent m bonding positions in the general formula (G1), R 21 to R 32 The rest of the residues 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] (In general formula (G2), 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 more, L may be the same or different. α represents oxygen, sulfur, carbon with a substituent, silicon with a substituent, or germanium with a substituent, and R 21 、R 23 to R 32 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 . The organic compound according to claim 1 , wherein the α is represented by the general formula (α-1). [Chemical Formula 5] (In the general formula (α-1), X represents carbon, silicon or germanium, R 33 and R 34 Each independently represents hydrogen (including deuterium), a substituted or unsubstituted 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, and * represents a bonding position.) 6. An organic compound represented by structural formula (100). [Chemical Formula 6] 7. A light-emitting device using the organic compound according to any one of claims 1 to 4 and 6.

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

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

Citation Information

Patent Citations

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

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