Curable composition for permanent resist films, and permanent resist film

Patent metadata

Field	Value
Publication number	US-10179828-B2
Application number	US-201515535839-A
Country	US
Kind code	B2
Filing date	Nov 19, 2015
Priority date	Jan 16, 2015
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

A curable composition and a permanent resist film made using this curable composition are provided. The composition dissolves well in solvents, gives coatings superior in alkali developability, thermal decomposition resistance, light sensitivity, and resolution, and is particularly suitable for the formation of permanent resist films. Specifically, the composition is a curable composition for permanent resist films and contains a phenolic hydroxyl-containing compound (A) that has a molecular structure represented by structural formula (1):

(where R 1 is hydrogen, alkyl, or aryl, and n is an integer of 2 to 10; R 2 is alkyl, alkoxy, aryl, aralkyl, or halogen, and m is an integer of 0 to 4; if m is 2 or more, the plurality of R 2 s may be the same or different from one another, and may be bonded to either of the two aromatic rings in the naphthylene structure) and a photosensitizer (B1) or curing agent (B2).

First claim

The invention claimed is:

1. A calix[2-10]arene compound which is obtained by reacting only an 1,6-dihydroxynaphthalene compound with an aromatic aldehyde as reactants in the presence of a catalyst;
wherein the 1,6-dihydroxynaphthalene is unsubstituted or substituted by any of alkyl, alkoxy, aryl, aralkyl or halogen; and
wherein the aromatic aldehyde is represented by structure

where R 6 and R 7 are each independently hydroxyl, halogen, alkyl, alkoxy, aryl, or aralkyl, p is an integer of 0 to 5, and q is an integer of 0 to 7; and if p or q is 2 or more, the plurality of R 6 s or R 7 s may be the same or different from one another.

2. The calix[2-10]arene compound according to claim 1 , wherein the aromatic aldehyde is selected from a group consisting of salicylaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 2-hydroxy-4-methylbenzaldehyde, 2,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 3-hydroxy-4-methoxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 4-hydroxy-3,5-dimethoxybenzaldehyde, methoxybenzaldehyde, ethoxybenzaldehyde, 1-hydroxy-2-naphthaldehyde, 2-hydroxy-1-naphthaldehyde, 6-hydroxy-2-naphthaldehyde, or combination thereof.

3. A composition comprising the calix[2-10]arene compound according to claim 2 and a photosensitizer (B1) or curing agent (B2), wherein the composition is a curable composition.

4. A permanent resist film comprising the curable composition according to claim 3 .

5. The calix[2-10]arene compound according to claim 1 is a product of reacting the 1,6-dihydroxynaphthalene compound with the aromatic aldehyde in the presence of an acidic catalyst.

6. The calix[2-10]arene compound according to claim 5 , wherein the aromatic aldehyde is 4-hydroxybenzaldehyde or salicylaldehyde.

7. A composition comprising the calix[2-10]arene compound according to claim 6 and a photosensitizer (B1) or curing agent (B2), wherein the composition is a curable composition.

8. A permanent resist film comprising the curable composition according to claim 7 .

9. A composition comprising the calix[2-10]arene compound according to claim 5 and a photosensitizer (B1) or curing agent (B2) wherein the composition is a curable composition.

10. A permanent resist film comprising the curable composition according to claim 9 .

11. A composition comprising the calix[2-10]arene compound according to claim 1 and a photosensitizer (B1) or curing agent (B2).

12. The composition according to claim 11 , wherein the photosensitizer (B1) constitutes 5 to 50 parts by mass per 100 parts by mass of the phenolic hydroxyl-containing compound (A).

13. The composition according to claim 12 , wherein the composition is a curable composition.

14. A permanent resist film comprising the curable composition according to claim 13 .

15. The composition according to claim 11 , wherein the curing agent (B2) constitutes 0.5 to 20 parts by mass per 100 parts by mass of the phenolic hydroxyl-containing compound (A).

16. The composition according to claim 15 , wherein the composition is a curable composition.

17. A permanent resist film comprising the curable composition according to claim 16 .

18. The composition according to claim 11 , wherein the composition is a curable composition for permanent resist films.

19. A permanent resist film comprising the curable composition according to claim 18 for permanent resist films.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Imada Tomoyuki

Classifications

• G03F7/0226

  characterised by the non-macromolecular additives · CPC title

• C08G8/04 Primary

  of aldehydes · CPC title

• G03F7/168

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title

• C09D161/12

  with polyhydric phenols · CPC title

• C07C39/14

  with at least one hydroxy group on a condensed ring system containing two rings · CPC title