Positive photosensitive resin compositions

Patent metadata

Field	Value
Publication number	US-9519216-B2
Application number	US-36349209-A
Country	US
Kind code	B2
Filing date	Jan 30, 2009
Priority date	Feb 4, 2008
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The present disclosure relates to compositions that include at least one polybenzoxazole precursor polymer, at least one photoacid generator, and at least one basic compound. Articles, films, and methods related to these compositions are also disclosed.

First claim

What is claimed is:

1. A composition, comprising:
(a) at least one polybenzoxazole precursor polymer, the polybenzoxazole precursor polymer has Structure I, II, or II*:

in which Ar 1 is a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof; Ar 2 is a divalent aromatic or a divalent heterocyclic; Ar 3 is a divalent aromatic group, a divalent heterocyclic group, or mixtures thereof; Ar 4 is Ar 1 (OB) k 3 (OH) k 4 or Ar 2 ; x is an integer from about 4 to about 1000, y is an integer from 0 to about 500, provided that (x+y)≦1000; B is an acid sensitive group R 1 or a moiety E-O—R 2 containing an acid sensitive group R 2 , E is a divalent group which is not acid labile and makes an -E-OH moiety an aqueous base solubilizing group, E being selected from the group consisting of an aromatic group, and a heterocyclic group, provided that R 1 , in combination with the O atom attached to the Ar 1 group, is not a carbonate group; k 3 is a fractional number between 0.1 and 2, k 4 is a fractional number between 0 and 1.9 provided that (k 3 +k 4 )=2; G is a substituted or unsubstituted monovalent organic group having a carbonyl, carbonyloxy or sulfonyl group attached directly to the terminal NH of the polymer, and G* is a substituted or unsubstituted divalent organic group having at least one carbonyl or sulfonyl group attached directly to the terminal N of the polymer;
(b) at least one photoacid generator; and
(c) at least a first basic compound selected from the group consisting of
tertiary amines of Structure XIV:

in which R 30 , R 31 , and R 32 are independently selected from the group consisting of a C 1 -C 30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C 3 -C 30 tertiary aminoalkyl, a C 2 -C 30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C 6 -C 30 substituted or unsubstituted aryl, and a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R 30 , R 31 , and R 32 is selected from the group consisting of a C 1 -C 30 substituted or unsubstituted cyclic alkyl, a C 3 -C 30 tertiary aminoalkyl, a C 2 -C 30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C 6 -C 30 substituted or unsubstituted aryl, and a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R 30 , R 31 , and R 32 are a C 6 -C 30 substituted or unsubstituted aryl;
wherein the acid sensitive group R 1 or R 2 is a group capable of reacting with an acid to form an aqueous base solubilizing group and the first basic compound is from about 0.001 wt % to about 3 wt % of the composition.

2. The composition of claim 1 , wherein the first basic compound is selected from the group consisting of
tertiary amines of Structure XIV, in which R 30 , R 31 , and R 32 are independently selected from the group consisting of a C 1 -C 30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C 3 -C 30 tertiary aminoalkyl, a C 2 -C 30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, and a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R 30 , R 31 , and R 32 is selected from the group consisting of a C 1 -C 30 substituted or unsubstituted cyclic alkyl, a C 3 -C 30 tertiary aminoalkyl, a C 2 -C 30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C 6 -C 30 substituted or unsubstituted aryl, and a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R 30 , R 31 , and R 32 are a C 6 -C 30 substituted or unsubstituted aryl.

3. The composition of claim 2 , wherein the first basic compound comprises a tertiary amine of Structure XIV, in which R 30 , R 31 , and R 32 are independently selected from the group consisting of a C 3 -C 30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C 3 -C 15 tertiary aminoalkyl, a C 3 -C 30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, and a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least two of R 30 , R 31 , and R 32 have at least two substituents on the carbon atom bonded to the tertiary nitrogen atom or at least one of R 30 , R 31 , and R 32 has a C 1 -C 30 substituted or unsubstituted alkyl group containing at least one ether linkage.

4. The composition of claim 3 , wherein the first basic compound comprises a tertiary amine of Structure XIV, in which R 30 , R 31 , and R 32 are independently selected from the group consisting of a C 3 -C 15 substituted or unsubstituted linear, branched, or cyclic alkyl, a C 3 -C 10 tertiary aminoalkyl, a C 3 -C 15 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, and a C 3 -C 15 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least two of R 30 , R 31 , and R 32 have at least two substituents on the carbon atom bonded to the tertiary nitrogen atom or at least one of R 30 , R 31 , and R 32 has a C 3 -C 15 substituted or unsubstituted alkyl group containing at least one ether linkage.

5. The composition of claim 2 , further comprising an adhesion promoter.

6. The composition of claim 5 , wherein the adhesion promoter comprises a compound selected from the group consisting of vinylalkoxysilanes, methacryloxalkoxysilanes, mercaptoalkoxysilanes, epoxyalkoxysilanes and glycidoxyalkoxysilanes.

7. The composition of claim 6 , wherein the adhesion promoter comprises a compound selected from the group consisting of epoxyalkoxysilanes and glycidoxyalkoxysilanes.

8. The composition of claim 2 , further comprising a solvent.

9. The composition of claim 2 , wherein the first basic compound is from about 0.01 wt % to about 1.5 wt % of the composition.

10. The composition of claim 1 , further comprising an adhesion promoter.

11. The composition of claim 10 , wherein the adhesion promoter comprises a compound selected from the group consisting of vinylalkoxysilanes, methacryloxalkoxysilanes, mercaptoalkoxysilanes, epoxyalkoxysilanes and glycidoxyalkoxysilanes.

12. The composition of claim 11 , wherein the adhesion promoter comprises a compound selected from the group consisting of epoxyalkoxysilanes and glycidoxyalkoxysilanes.

13. The composition of claim 1 , further comprising a solvent.

14. The composition of claim 1 , wherein the first basic compound is from about 0.01 wt % to about 1.5 wt % of the composition.

15. The composition of claim 1 , further comprising a second basic compound different from the first basic compound, the second basic compound being a tertiary amine of Structure XIV, in which R 30 , R 31 , and R 32 are C 6 -C 30 substituted or unsubstituted aryl.

16. The composition of claim 15 , wherein R 30 , R 31 , and R 32 in the second basic compound are substituted or unsubstituted phenyl.

17. A film comprising a composition of claim 1 .

18. The film of claim 17 , wherein the film has a thickness of at least about 5 μm.

19. The film of claim 17 , wherein the film has a thickness of at least about 8 μm.

20. The film of claim 17 , wherein the film has a thickness of at least about 10 μm.

21.

Assignees

• Naiini Ahmad A
• Rushkin Il'Ya
• Weber William D
• Racicot Donald W
• Fujifilm Electronic Mat Usa Inc

Inventors

• Naiini Ahmad A
• Rushkin Il'Ya
• Weber William D
• Racicot Donald W

Classifications

• Y10T428/265

  1 mil or less · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/0392 Primary

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title