An ink composition, an organic layer containing the same, and an organic light-emitting element containing the same.

JP7878805B2Active Publication Date: 2026-06-23LG CHEM LTD

Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
LG CHEM LTD
Filing Date
2023-11-02
Publication Date
2026-06-23

AI Technical Summary

Benefits of technology

【0010】 本発明の一実施態様によるインク組成物は、熱処理または光処理により硬化した薄膜を形成することで、次の溶液工程により損傷しない安定した薄膜を形成するという利点がある。

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Abstract

The present specification relates to an ink composition, an organic layer including the ink composition, and an organic light-emitting device including the ink composition.
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Claims

1. Compound represented by the following chemical formula 1; The first solvent represented by the following chemical formula A; and A second solvent represented by the following chemical formula A, which is different from the first solvent. Ink composition including: 【Chemistry 1】 In the aforementioned chemical formulas 1 and A, La is a substituted or unsubstituted divalent hydrocarbon ring group; or a substituted or unsubstituted divalent heterocyclic group. L1 and L2 are identical or different from each other, and are independently directly bonded; or are substituted or unsubstituted arylene groups. R1 to R4 are either identical or different from each other, and each is independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group. Ar1 and Ar2 are either identical or different from each other, and are independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups. X1 and X2 are either identical or different from each other, and are independently curable groups. L10 is a directly bonded; or an unsubstituted or alkylene group. Z1 and Z2 are either identical or different from each other, and are independently alkyl groups. If r1 and r2 are integers from 1 to 7, r3 and r4 are integers from 1 to 5, and r1 to r4 are each 2 or greater, then two or more substituents in parentheses are either identical or different from each other. f1 is the number of bond positions to which substituents may be attached from 1 to Ar1. f2 is the number of bond positions to which substituents may be attached from 1 to Ar2.

2. The ink composition according to claim 1, wherein the curable group has one of the following structures: 【Chemistry 2】 In the above structure, R32 and R34 are either identical or different from each other, and independently are hydrogen; deuterium; or a substituted or unsubstituted alkyl group. L31 to L38 are either identical or different from each other, and each is independently directly bonded; -O-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group. l34 to l38 are integers from 1 to 10, and if each of l34 to l38 is 2 or greater, then the two or more substituents in parentheses are either identical or different from each other. 【Transformation 3】 This is the site that binds to the remaining part of the molecule in the aforementioned chemical formula 1.

3. The ink composition according to claim 1, wherein the La has one of the following structures: 【Chemistry 4】 In the above structure, R10 to R31 are either identical or different from each other, and each is independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group. n10 to n21 are integers from 1 to 4, n22, n23, n28, and n29 are integers from 1 to 3, n24 and n25 are integers from 1 to 7, n26 is an integer from 1 to 8, n27 is an integer from 1 to 6, and if n10 to n29 are each 2 or greater, then two or more substituents in parentheses are either identical or different from each other. 【Transformation 5】 This is the site that binds to the rest of the molecule in chemical formula 1.

4. The aforementioned -Ar1-(F) f1 and -Ar2-(F) f2 The ink composition according to claim 1, wherein each is identical or different from the others and independently represented by the following chemical formula 1-A: 【Transformation 6】 In the aforementioned chemical formula 1-A, R5 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group. L3 is a directly bonded; or a substituted or unsubstituted arylene group. f3 is an integer between 1 and 5, f4 is an integer between 0 and 4, and f3 + f4 is less than or equal to 5. 【Transformation 7】 This is the part that bonds to the rest of the molecule in chemical formula 1.

5. The ink composition according to claim 1, wherein L1 and L2 are identical or different from each other, and are independently directly bonded; or are substituted or unsubstituted phenylene groups.

6. The ink composition according to claim 1, wherein the chemical formula 1 is one of the following structures: 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 。

7. The ink composition according to claim 1, wherein L10 is directly bonded; or an alkylene group having 1 to 10 carbon atoms, substituted with an alkyl group or unsubstituted.

8. The ink composition according to claim 1, wherein the chemical formula A is one of the following structures: 【Transformation 33】 【Transformation 34】 【Chemistry 35】 。

9. The boiling point of the first solvent is 250°C to 350°C. The boiling point of the second solvent is 180°C to 280°C. The ink composition according to claim 1, wherein the boiling point of the first solvent is higher than the boiling point of the second solvent.

10. The ink composition according to claim 1, further comprising a third solvent different from the first and second solvents.

11. The ink composition according to claim 10, wherein the third solvent, unlike the first and second solvents, comprises one or more of the following: a solvent represented by chemical formula A; a solvent represented by the following chemical formula B; tetralin; 4-methoxytoluene; tripropylene glycol monobutyl ether; and cyclohexylbenzene: 【Transformation 36】 In the aforementioned chemical formula B, L100 is an alkylene group, L101 is -COO-, R100 is hydrogen; or a substituted or unsubstituted alkyl group. R101 is a substituted or unsubstituted alkyl group. l100 is 0 or 1, r100 is an integer from 1 to 5, and if r100 is 2 or greater, the substituents in parentheses are either identical or different.

12. The ink composition according to claim 1, further comprising an ionic compound containing an anionic group represented by the following chemical formula 2: 【Chemistry 37】 In the aforementioned chemical formula 2, At least one of R201 to R220 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group. Of the remaining R201 to R220, at least one is a curable group. The remaining R201 to R220 are either identical or different from each other, and independently represent hydrogen; deuterium; halogen group; nitro group; cyano group; amino group; -OR221; -SR222; -SO 3 R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, R221 to R228 are either identical or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

13. The ink composition according to claim 12, wherein the chemical formula 2 is one of the following structures: 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 In the above structure, n1 is an integer between 1 and 3, m1 is an integer between 1 and 3, and n1 + m1 = 4. n² is an integer between 0 and 3, m² is an integer between 1 and 4, and n² + m² = 4. M1 is deuterium; halogen group; nitro group; cyano group; amino group; -OR221; -SR222; -SO 3 R223; -COOR224; -OC(O)R225; -C(O)NR226R227; -C(O)R228; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, R221 to R228 are either identical or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group. i is an integer from 1 to 4, and if i is 2 or greater, then M1 values ​​of 2 or greater are either identical or different from each other.

14. The ink composition according to claim 12, wherein the ionic compound further comprises a cationic group, the cationic group being a monovalent cationic group, an onium compound, or one of the following structures: 【Chemistry 41】 In the above structure, Q30 to Q105 are either identical or different from each other, and each is independently hydrogen; deuterium; cyano group; nitro group; halogen group; hydroxyl group; -COOR250; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or curable group. R250 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group. x is an integer between 0 and 10. p1 is either 1 or 2, q1 is either 0 or 1, and p1 + q1 = 2.

15. The ink composition according to claim 12, wherein the ionic compound is one of the following chemical formulas D-1 to D-37: 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 。

16. The ink composition according to claim 1, wherein the ink composition is for forming one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron barrier layer.

17. A pixel comprising the ink composition or cured product thereof according to any one of claims 1 to 16.

18. The pixel according to claim 17, wherein the pixel has a flatness of 0.4 or more when its short-axis width is 50 μm or less.

19. An organic layer containing pixels according to claim 17.

20. first electrode; Second electrode; and One or more organic layers provided between the first electrode and the second electrode Includes, An organic light-emitting device wherein one or more of the aforementioned organic layers are organic layers according to claim 19.

21. The organic layer comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron barrier layer. The organic light-emitting element according to claim 20, wherein one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron shielding layer include the ink composition or a cured product thereof.