US 12,189,291 B2
Epoxy formulations and processes for fabrication of relief patterns on low surface energy substrates
Daniel J. Nawrocki, Chicopee, MA (US); Jeremy V. Golden, Burlington, MA (US); and William D. Weber, East Providence, RI (US)
Assigned to KAYAKU ADVANCED MATERIALS, INC., Westborough, MA (US)
Appl. No. 14/241,745
Filed by Daniel J. Nawrocki, Chicopee, MA (US); Jeremy V. Golden, Burlington, MA (US); and William D. Weber, East Providence, RI (US)
PCT Filed Sep. 5, 2012, PCT No. PCT/US2012/053738
§ 371(c)(1), (2), (4) Date Jun. 11, 2014,
PCT Pub. No. WO2013/036502, PCT Pub. Date Mar. 14, 2013.
Claims priority of provisional application 61/573,491, filed on Sep. 7, 2011.
Prior Publication US 2014/0302430 A1, Oct. 9, 2014
Int. Cl. G03F 7/038 (2006.01); C08G 59/32 (2006.01); C08L 63/00 (2006.01); G03F 7/004 (2006.01); G03F 7/11 (2006.01)
CPC G03F 7/038 (2013.01) [C08G 59/3218 (2013.01); C08L 63/00 (2013.01); G03F 7/0046 (2013.01); G03F 7/11 (2013.01)] 12 Claims
OG exemplary drawing
 
1. A layer of permanent epoxy photoresist composition useful for making negative-tone, permanent photoresist relief patterns on low surface energy polymer substrates, comprising:
(A) one or more epoxy resins selected from the group consisting of one or more epoxy resins according to Formula I through Formula VI:

OG Complex Work Unit Chemistry
wherein each group R in Formula I is individually selected from glycidyl or hydrogen and k in Formula I is a real number ranging from 0 to about 30;

OG Complex Work Unit Chemistry
wherein each R1, R2 and R3 in Formula II are independently selected from the group consisting of hydrogen or alkyl groups having 1 to 4 carbon atoms and the value of p in Formula II is a real number ranging from 1 to about 30;

OG Complex Work Unit Chemistry
wherein each R4 and R5 in Formula III are independently selected for the group consisting of hydrogen, alkyl groups having 1 to 4 carbon atoms, or trifluoromethyl groups and the values of n and m in Formula III are independently real numbers ranging from 1 to about 30;

OG Complex Work Unit Chemistry
wherein x in Formula IV is a real number ranging from 1 to about 30;

OG Complex Work Unit Chemistry
wherein R1 in Formula V represents a residue of an organic compound having z active hydrogen atoms, n1 through nz each represents 0 or an integer from 1 to 100, the sum of the integers represented by n1 through nz is from 1 to 100, z represents an integer from 1 to 100 and E represents separately either groups E1 or E2; and

OG Complex Work Unit Chemistry
wherein each group R in Formula VI is individually selected from glycidyl or hydrogen and x in Formula VI is a real number ranging from 0 to about 30;
(B) one or more cationic photoinitiators;
(C) one or more film casting solvents selected from the group consisting of methyl acetate, ethyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl carbonate and combinations thereof; and
(D) one or more fluorinated compounds selected from the group consisting of 2,3-dihydroperfluoropentane, ethoxy-nonafluorobutane, 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)-pentane, and combinations thereof;
wherein said fluorinated compounds (D) are present in said composition in an amount ranging from 0.75 wt % to 1.65 wt % based on the total weight of the composition and wherein said composition is applied onto a low surface energy polymer substrate to make a negative-tone, permanent photoresist layer.