US 12,289,983 B2
Hole-transporting ink composition, light-emitting device, and method of preparing the light-emitting device
Hyojin Ko, Yongin-si (KR); Changhee Lee, Yongin-si (KR); Dukki Kim, Yongin-si (KR); Sehun Kim, Yongin-si (KR); Youngil Kim, Yongin-si (KR); Seungmook Lee, Yongin-si (KR); and Jaekook Ha, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on May 28, 2021, as Appl. No. 17/333,354.
Claims priority of application No. 10-2020-0065183 (KR), filed on May 29, 2020.
Prior Publication US 2021/0376244 A1, Dec. 2, 2021
Int. Cl. H10K 85/10 (2023.01); C09D 11/38 (2014.01); C09D 11/52 (2014.01); H10K 50/115 (2023.01); H10K 50/17 (2023.01); H10K 71/00 (2023.01); H10K 71/12 (2023.01)
CPC H10K 85/111 (2023.02) [C09D 11/38 (2013.01); C09D 11/52 (2013.01); H10K 50/115 (2023.02); H10K 50/17 (2023.02); H10K 71/00 (2023.02); H10K 71/12 (2023.02)] 8 Claims
OG exemplary drawing
 
1. A hole-transporting ink composition for a light emitting device, the hole-transporting ink composition comprising:
an adhesion-promoting compound represented by Formula 1; and
a hole-transporting compound comprising a polymeric compound including a repeating unit made from a compound represented by Formula 201 or 202:
A1—B1—C1   Formula 1

OG Complex Work Unit Chemistry
wherein, in Formula 1,
A1 is —Si(Q1)(Q2)(Q3), —S(Q1), —P(═O)(Q1)(Q2), or —C(═O)(Q1),
B1 is a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 alkenylene group, or a substituted or unsubstituted C2-C60 alkynylene group,
C1 is —O(Q4), —S(Q4), —C(═O)(Q4), —N(Q4)(Q5), a substituted or unsubstituted acryl group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, or a substituted or unsubstituted C1-C60 fluoroalkyl group, and
Q1 to Q5 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a is hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6—C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
in Formulae 201 and 202
L201 to L204 are each independently a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
L205 is a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
xa1 to xa4 are each independently 0, 1, 2, or 3, and
xa5 is an integer from 2 to 10,
in Formula 201,
R201 and R202 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
R203 is a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
in Formula 202,
R201 to R204 and Q201 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
provided that in Formula 202, each of R201 to R203 does not comprise a substituted or unsubstituted fluorenyl group.