US 12,448,534 B2
Method of forming hole injection layer, hole injection layer ink composition, and light-emitting device manufactured by using hole injection layer ink composition
Juyon Lee, Yongin-si (KR); Sehun Kim, Yongin-si (KR); Hyojin Ko, Yongin-si (KR); Heunggyu Kim, Yongin-si (KR); Wonjun Park, Yongin-si (KR); Junbo Sim, Yongin-si (KR); Seungmook Lee, Yongin-si (KR); and Jaekook Ha, Yongin-si (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Aug. 4, 2021, as Appl. No. 17/393,435.
Claims priority of application No. 10-2020-0159090 (KR), filed on Nov. 24, 2020.
Prior Publication US 2022/0162467 A1, May 26, 2022
Int. Cl. C09D 11/50 (2014.01); C09D 11/38 (2014.01); G03F 7/42 (2006.01); H10K 50/17 (2023.01); H10K 71/00 (2023.01); H10K 71/13 (2023.01); H10K 85/60 (2023.01)
CPC C09D 11/50 (2013.01) [C09D 11/38 (2013.01); G03F 7/427 (2013.01); H10K 50/17 (2023.02); H10K 71/135 (2023.02); H10K 85/626 (2023.02); H10K 85/633 (2023.02); H10K 71/00 (2023.02)] 15 Claims
OG exemplary drawing
 
1. A method of forming a hole injection layer of a light-emitting device, the method comprising:
forming a pixel electrode on a substrate;
coating the pixel electrode with a composition to provide a pixel-defining film on the pixel electrode;
forming by photolithography a patterned pixel-defining film having an opening that exposes a portion of the pixel electrode;
descumming; and
forming the hole injection layer on the exposed and descummed pixel electrode with a hole injection composition,
wherein the hole injection composition comprises a hole injection layer compound, a solvent, and a polymer compound comprising a group represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
X is a single bond or a divalent organic linking group,
R1 is a C1-C10 alkylene group that is unsubstituted or substituted with at least one of R10a,
R2 is hydrogen, deuterium, a hydroxyl group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one of R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one of R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one of R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one of R10a, and a C1-C60 alkylether group that is unsubstituted or substituted with at least one of R10a,
1l is an integer from 2 to 100,
indicates a connection site to an adjacent atom of the polymer compound, and
each R10a is independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each of which is independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each of which is independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each of which is independently unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
wherein the polymer compound comprises a polyurethane unit, a polyamide unit, a polyurea unit, or a combination thereof, and
wherein a content of the polymer compound in the hole injection composition is in a range of about 0.05 percent by weight to about 1 percent by weight based on a total composition of the hole injection composition.