US 12,461,445 B2
Low reflectivity photosensitive resin composition and light-shielding layer using same
Changmin Lee, Cheonan-si (KR); Yun Jong Ko, Cheonan-si (KR); Jun Bae, Cheonan-si (KR); Jun Ki Kim, Cheonan-si (KR); Hyunsang Cho, Cheonan-si (KR); and Soung Yun Mun, Cheonan-si (KR)
Assigned to DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Appl. No. 18/040,184
Filed by DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
PCT Filed Jun. 3, 2021, PCT No. PCT/KR2021/006929
§ 371(c)(1), (2) Date Feb. 1, 2023,
PCT Pub. No. WO2022/039356, PCT Pub. Date Feb. 24, 2022.
Claims priority of application No. 10-2020-0105309 (KR), filed on Aug. 21, 2020.
Prior Publication US 2023/0273517 A1, Aug. 31, 2023
Int. Cl. G03F 7/105 (2006.01); G03F 7/004 (2006.01); G03F 7/031 (2006.01); G03F 7/033 (2006.01); H10K 59/80 (2023.01)
CPC G03F 7/105 (2013.01) [G03F 7/0042 (2013.01); G03F 7/0045 (2013.01); G03F 7/031 (2013.01); G03F 7/033 (2013.01); H10K 59/8792 (2023.02); H10K 59/80 (2023.02)] 18 Claims
 
1. A photosensitive resin composition comprising:
a binder resin containing a repeating unit represented by the following Chemical Formula (1);
a dye represented by the following Chemical Formula (2);
a pigment;
a reactive unsaturated compound;
a photoinitiator; and
a solvent:

OG Complex Work Unit Chemistry
In Chemical Formula (1),
1) * indicates a part where bonds are connected as a repeating unit,
2) R1 and R2 are each independently hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
3) R1 and R2 are each capable of forming a ring with an adjacent group,
4) A and b are each independently an integer of 0 to 4,
5) X1 is a single bond, O, CO, SO2, CR′R″, SIR′R″, Chemical Formula (A), or Chemical Formula (B),
6) X2 is a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; or combinations thereof,
7) R′ and R″ are each independently hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
8) R′ and R″ are each capable of forming a ring with an adjacent group,
9) A1 and A2 are each independently Chemical Formula (C) or Chemical Formula (D),
10) The ratio of Chemical Formula (C) to Chemical Formula (D) within the polymer chain of the resin containing the repeating unit represented by Chemical Formula (1) satisfies 1:9 to 9:1,

OG Complex Work Unit Chemistry
In Chemical Formulas (A) and (B),
11-1) * indicates a binding position,
11-2) X3 is O, S, SO2, or NR′,
11-3) R′ is hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
11-4) R3 to R6 are each independently hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic ring and aromatic ring; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
11-5) R3 to R6 are each capable of forming a ring with an adjacent group, and
11-6) c to f are each independently an integer of 0 to 4,

OG Complex Work Unit Chemistry
In Chemical Formulas (C) and (D),
12-1) * indicates a binding position,
12-2) R7 to R10 are each independently hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group, and
12-3) Y1 and Y2 are Chemical Formula (E),

OG Complex Work Unit Chemistry
In Chemical Formula (E),
13-1) * indicates a binding position,
13-2) R11 is hydrogen; deuterium; a halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
13-3) L1 is a single bond, C1-C30 alkylene, C6-C30 arylene, or C2-C30 heterocycle,
14) R1 to R11, R′, R″, X1 to X2 and L1, and a ring formed by bonding adjacent groups to each other are each further substituted with one or more substituents selected from the group consisting of: deuterium; a halogen; a silane group substituted or unsubstituted with a C1-C30 alkyl group or a C6-C30 aryl group; a siloxane group; a boron group; a germanium group; a cyano group; an amino group; a nitro group; a C1-C30 alkylthio group; a C1-C30 alkoxy group; a C6-C30 arylalkoxy group; a C1-C30 alkyl group; a C2-C30 alkenyl group; a C2-C30 alkynyl group; a C6-C30 aryl group; a C6-C30 aryl group substituted with deuterium; a fluorenyl group; a C2-C30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a C3-C30 aliphatic cyclic group; a C7-C30 arylalkyl group; a C8-C30 arylalkenyl group; and combinations thereof, and adjacent substituents form a ring,

OG Complex Work Unit Chemistry
In Chemical Formula (2),
15-1) M is Zn, Cu, Ti, Fe, V═O, Ni, Mn, or Co;
15-2) R20 to R27 are each independently hydrogen; deuterium; halogen; a C6-C30 aryl group; a C2-C30 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; a fused ring group of C6-C30 aliphatic and aromatic rings; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; a C6-C30 aryloxy group; a fluorenyl group; a carbonyl group; an ether group; or a C1-C20 alkoxycarbonyl group,
15-3) R20 to R27 are each capable of forming a ring with an adjacent group, and
16) the rings formed by bonding R20 to R27 and neighboring groups to each other are each further substituted with one or more substituents selected from the group consisting of: deuterium; halogen; a silane group substituted or unsubstituted with a C1-C30 alkyl group or a C6-C30 aryl group; a siloxane group; a boron group; a germanium group; a cyano group; an amino group; a nitro group; a C1-C30 alkylthio group; a C1-C30 alkoxy group; a C6-C30 arylalkoxy group; a C1-C30 alkyl group; a C2-C30 alkenyl group; a C2-C30 alkynyl group; a C6-C30 aryl group; a C6-C30 aryl group substituted with deuterium; a fluorenyl group; a C2-C30 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a C3-C30 aliphatic ring; a C7-C30 arylalkyl group; a C8-C30 arylalkenyl group; and combinations thereof, and adjacent substituents form a ring.