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US 9,519,216 B2Granted
Positive photosensitive resin compositions
AssigneeFujifilm Electronic Materials U.S.A., Inc.
InventorsAhmad A. Naiini, Il'ya Rushkin, William D. Weber, Donald W. Racicot
Life of this patent
Estimating the term…
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.
Claims40
A composition, comprising:
- (a) at least one polybenzoxazole precursor polymer, the polybenzoxazole precursor polymer has Structure I, II, or II*:
- in which Ar1 is a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof;
- Ar2 is a divalent aromatic or a divalent heterocyclic;
- Ar3 is a divalent aromatic group, a divalent heterocyclic group, or mixtures thereof;
- Ar4 is Ar1(OB)k3(OH)k4 or Ar2;
- 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 R1 or a moiety E-O—R2 containing an acid sensitive group R2, 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 R1, in combination with the O atom attached to the Ar1 group, is not a carbonate group;
- k3 is a fractional number between 0.1 and 2, k4 is a fractional number between 0 and 1.9 provided that (k3+k4)=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 R30, R31, and R32 are independently selected from the group consisting of a C1-C30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R30, R31, and R32 is selected from the group consisting of a C1-C30 substituted or unsubstituted cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R30, R31, and R32 are a C6-C30 substituted or unsubstituted aryl;
- wherein the acid sensitive group R1 or R2 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.
12 more elements
A composition, comprising:
- (a) at least one polybenzoxazole precursor polymer, the polybenzoxazole precursor polymer has Structure I, II, or II*:
- in which Ar1 is a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof;
- Ar2 is a divalent aromatic or a divalent heterocyclic;
- Ar3 is a divalent aromatic group, a divalent heterocyclic group, or mixtures thereof;
- Ar4 is Ar1(OB)k3(OH)k4 or Ar2;
- 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 R1 or a moiety E-O—R2 containing an acid sensitive group R2, 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
- provided that R1, in combination with the O atom attached to the Ar1 group, is not a carbonate group;
- k3 is a fractional number between 0.1 and 2, k4 is a fractional number between 0 and 1.9 provided that (k3+k4)=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 R30, R31, and R32 are independently selected from the group consisting of a C1-C30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R30, R31, and R32 is selected from the group consisting of a C1-C30 substituted or unsubstituted cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R30, R31, and R32 are a C6-C30 substituted or unsubstituted aryl;
- wherein the acid sensitive group R1 or R2 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.
13 more elements
A composition, comprising:
- (a) at least one polybenzoxazole precursor polymer, the polybenzoxazole precursor polymer has Structure I, II, or II*:
- in which Ar1 is a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof;
- Ar2 is a divalent aromatic, a divalent heterocyclic, a divalent alicyclic, or a divalent aliphatic group that optionally contains silicon;
- Ar3 is a divalent aromatic group, a divalent aliphatic group, a divalent heterocyclic group, or mixtures thereof;
- Ar4 is Ar1(OB)k3(OH)k4 or Ar2;
- x is an integer from about 10 to about 1000, y is an integer from 0 to about 500, provided that (x+y)≦1000;
- B is an acid sensitive group R1 or a moiety E-O—R2 containing an acid sensitive group R2, 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, an aliphatic group, and a heterocyclic group, provided that R1, in combination with the O atom attached to the Ar1 group, is not a carbonate group;
- k3 is a fractional number between 0.1 and 2, k4 is a fractional number between 0 and 1.9 provided that (k3+k4)=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 R30, R31, and R32 are independently selected from the group consisting of a C1-C30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R30, R31, and R32 is selected from the group consisting of a C1-C30 substituted or unsubstituted cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R30, R31, and R32 are a C6-C30 substituted or unsubstituted aryl;
- wherein the acid sensitive group R1 or R2 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.
12 more elements
A composition, comprising:
- (a) at least one polybenzoxazole precursor polymer, the polybenzoxazole precursor polymer has Structure I, II, or II*:
- in which Ar1 is a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof;
- Ar2 is a divalent aromatic, or a divalent heterocyclic, a divalent alicyclic, or a divalent aliphatic group that optionally contains silicon;
- Ar3 is a divalent aromatic group, a divalent aliphatic group, a divalent heterocyclic group, or mixtures thereof;
- Ar4 is Ar1(OB)k3(OH)k4 or Ar2;
- x is an integer from about 10 to about 1000, y is an integer from 0 to about 500, provided that (x+y)≦1000;
- B is an acid sensitive group R1 or a moiety E-O—R2 containing an acid sensitive group R2, 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
- provided that R1, in combination with the O atom attached to the Ar1 group, is not a carbonate group;
- k3 is a fractional number between 0.1 and 2, k4 is a fractional number between 0 and 1.9 provided that (k3+k4)=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 R30, R31, and R32 are independently selected from the group consisting of a C1-C30 substituted or unsubstituted linear, branched, or cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, in which at least one of R30, R31, and R32 is selected from the group consisting of a C1-C30 substituted or unsubstituted cyclic alkyl, a C3-C30 tertiary aminoalkyl, a C2-C30 substituted or unsubstituted linear, branched, or cyclic hydroxyalkyl, a C6-C30 substituted or unsubstituted aryl, and a C1-C30 substituted or unsubstituted alkyl group containing at least one ether linkage, and not all of R30, R31, and R32 are a C6-C30 substituted or unsubstituted aryl;
- wherein the acid sensitive group R1 or R2 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.
13 more elements
Dependencies are inferred from the claim text.