US 11,940,732 B2
Coating compositions and methods of forming electronic devices
Sheng Liu, Bow, NH (US); James F. Cameron, Brookline, MA (US); Shintaro Yamada, Shrewsbury, MA (US); Iou-Sheng Ke, Andover, MA (US); Keren Zhang, Kirkland, WA (US); Suzanne M. Coley, Mansfield, MA (US); Li Cui, Westborough, MA (US); Paul J. LaBeaume, Auburn, MA (US); and Deyan Wang, Hudson, MA (US)
Assigned to Rohm and Haas Electronic Materials LLC, Marlborough, MA (US)
Filed by Rohm and Haas Electronic Materials LLC, Marlborough, MA (US)
Filed on Apr. 15, 2021, as Appl. No. 17/231,417.
Claims priority of provisional application 63/019,326, filed on May 2, 2020.
Prior Publication US 2021/0341840 A1, Nov. 4, 2021
Int. Cl. G03F 7/11 (2006.01); C09D 4/06 (2006.01); C09D 7/47 (2018.01); C09D 7/63 (2018.01); G03F 7/025 (2006.01); G03F 7/075 (2006.01); G03F 7/09 (2006.01); G03F 7/16 (2006.01); G03F 7/20 (2006.01)
CPC G03F 7/11 (2013.01) [C09D 4/06 (2013.01); C09D 7/47 (2018.01); C09D 7/63 (2018.01); G03F 7/025 (2013.01); G03F 7/0752 (2013.01); G03F 7/091 (2013.01); G03F 7/094 (2013.01); G03F 7/16 (2013.01); G03F 7/2016 (2013.01)] 18 Claims
 
1. A coating composition, comprising:
a first curable compound comprising: a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and three or more substituents of formula (1)

OG Complex Work Unit Chemistry
wherein at least two substituents of formula (1) are attached to the core, wherein the core is optionally further substituted; and wherein: Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NHR2 wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2-R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to the core or to a portion of the curable compound other than the core; provided that no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core;
a polymer chosen from: acrylates, vinyl aromatic polymers, novolacs, polyphenylenes, polybenzoxazoles, polybenzimidazoles, polyetheresulfones, and combinations thereof, or a B-staged reaction product of a second curable compound comprising a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and two or more substituents of formula (B-1) attached to the core, wherein the core is optionally further substituted:

OG Complex Work Unit Chemistry
wherein in formula (B-1): Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NHR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2-R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to the core or to a portion of the curable compound other than the core; provided that no substituents of formula (B-1) are in an ortho position to each other on the same aromatic ring of the core; and
one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.