Granted Patent B2

US 12,189,291 · App. 14/241,745 · Granted Jan 7, 2025

Inventors: Daniel J. Nawrocki (Chicopee, MA); Jeremy V. Golden (Burlington, MA); William D. Weber (East Providence, RI)

Assignee: KAYAKU ADVANCED MATERIALS, INC.

G03F7/038C08G59/3218C08L63/00G03F7/0046G03F7/11

Abstract

Claims (29)

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:

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;

wherein each R 1 , R 2 and R 3 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;

wherein each R 4 and R 5 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;

wherein x in Formula IV is a real number ranging from 1 to about 30;

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

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.

2. The layer of claim 1 , further comprising one or more of the following additive materials:

(E) one or more surfactants,

(F) one or more optional epoxy resins;

(G) one or more reactive monomers;

(H) one or more photosensitizers;

(I) one or more adhesion promoters; and

(J) one or more light absorbing compounds including dyes and pigments.

3. The layer of claim 1 , further comprising one or more additional materials selected from the group consisting of thermal acid generator compounds, flow control agents, thermoplastic and thermosetting organic or organometallic polymers and resins, inorganic filler materials, and radical photoinitiators.

4. The layer of claim 1 , wherein one or more of the epoxy resins (A) is a bisphenol A novolac epoxy resin.

5. A method of forming a permanent photoresist relief pattern on a low surface energy polymer substrate comprising the steps of: (1) providing a low surface energy polymer layer on a substrate by coating a low surface energy polymer solution on the substrate; (2) forming a layer of the photoresist composition of claim 1 on the low surface energy polymer substrate; (3) evaporating most of the solvent from the photoresist layer by heating the coated substrate to form a film of the photoresist composition on the substrate; (4) irradiating the photoresist film with active rays through a mask; (5) crosslinking the irradiated photoresist film segments by heating; (6) developing the mask image in the photoresist film with a solvent to form an negative-tone relief image of the mask in the photoresist film; and (7) heat-treating the photoresist relief structure to further cure the photoresist and low surface energy polymer layers to form a permanent photoresist relief pattern on the low surface energy polymer substrate.

6. The method of claim 5 , wherein said layer is applied to a substrate using the slot coating method.

7. The method of claim 5 , wherein said layer is applied to a substrate using a piezoelectric ink jet printing device.

8. The method of claim 5 , wherein said layer is applied to low surface energy substrates.

9. The method of claim 5 , wherein the active rays comprise ultraviolet rays with wavelength ranging from about 200 to about 450 nanometers.

10. The permanent photoresist relief pattern made by the method of claim 5 for use in a display device.

11. The permanent photoresist relief pattern of claim 10 , where said display device comprises smart phone displays, computer displays, and active signage.

12. The permanent photoresist relief pattern made by the method of claim 5 for use in a microfluidic device.

Assignments (2)

Continuity (2)

References Cited (112)