Granted Patent B2

US 9,122,156 · App. 14/519,924 · Granted Sep 1, 2015

Inventors: Alex Philip Graham Robinson (Birmingham, GB); Dongxu Yang (Selly Oak Birmingham, GB); Andreas Frommhold (Anger, DE); Thomas Lada (Somerville, MA); John L. Roth (Cohasset, MA); Xiang Xue (Winchester, MA); Edward A. Jackson (Franklin, MA)

G03F7/027C07D223/04C07D487/04

Abstract

Claims (124)

1. A photosensitive composition comprising:

a. At least one ester, having a structure chosen from (I), (II), (III) or (IV);

b. at least one photo acid generator;

c. at least one crosslinker; and

d. at least one solvent;

wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R1 is a saturated or unsaturated group having from 1-4 carbon atoms, R2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R4 is a saturated or unsaturated group having from 1-4 carbon atoms.

2. The photosensitive composition of claim 1 , wherein at least one of X or Y comprises

-(alkyl) j -(aryl) k -(O) p —(COO) q -LG

wherein j, k, p, and q take the values in the following table:

-alkyl-

-aryl-

—O—

—COO—

j

k

p

q

1

1

1

1

1

1

0

1

1

1

1

0

1

0

0

1

1

0

1

0

0

1

1

1

0

1

0

1

0

1

1

0

0

0

0

1

wherein alkyl is a branched or unbranched, substituted or unsubstituted divalent alkyl chain of 1-16 carbon atoms having 0-16 heteroatoms substituted into the chain, aryl is a substituted or unsubstituted divalent phenyl group, divalent heteroaromatic group, or divalent fused aromatic or fused heteroaromatic group, and wherein LG is a leaving group.

3. The photosensitive composition of claim 2 , wherein LG is a tertiary alkyl or tertiary cycloalkyl group, an allicyclic group, a ketal or cyclic aliphatic ketal, or an acetal.

4. The photosensitive composition of claim 2 , wherein the leaving group is a tert-butyl group, a tert-pentyl group, a 2,3-dimethylbutan-2-yl group, a 2,3,3-trimethylbutan-2-yl group, a 2,3-dimethylpentan-3-yl group, a 2-methylbicyclo[2.2.1]heptan-2-yl group, a bicyclo[2.2.1]heptan-2-yl group, a 1-methylcyclopentyl group, a 1-ethylcyclopentyl group, a 1-methylcyclohexyl group, a 1-ethylcyclohexyl group, a 2-methyladamantyl group or a 2-ethyladamantyl group.

5. The photosensitive composition of claim 4 , wherein the at least one photoacid generator is chosen from a sulfonium salt, an iodonium salt, a sulfone imide, a halogen-containing compound, a sulfone compound, an ester sulfonate compound, a diazomethane compound, a dicarboximidyl sulfonic acid ester, an ylideneaminooxy sulfonic acid ester, a sulfanyldiazomethane, or a mixture thereof.

6. The photosensitive composition of claim 5 , wherein the at least one photoacid generator comprises a triphenylsulfonium salt or a bis(4-tert-butylphenyl)iodonium salt.

7. The photosensitive composition of claim 4 , wherein the at least one crosslinker comprises an acid sensitive monomer or polymer.

8. The photosensitive composition of claim 4 , wherein the crosslinker comprises at least one of a glycidyl ether, glycidyl ester, glycidyl amine, a methoxymethyl group, an ethoxy methyl group, a butoxymethyl group, a benzyloxymethyl group, dimethylamino methyl group, diethylamino methyl group, a dibutoxymethyl group, a dimethylol amino methyl group, diethylol amino methyl group, a dibutylol amino methyl group, a morpholino methyl group, acetoxymethyl group, benzyloxy methyl group, formyl group, acetyl group, vinyl group or an isopropenyl group.

9. The photoresist composition of claim 8 , wherein the crosslinker comprises one or more glycidyl ether groups attached to a novolac resin.

10. The photosensitive composition of claim 1 , wherein the solvent comprises an ester, an ether, an ether-ester, a hydroxy ester, a hydroxy ether, a ketone, a keto-ester, a hydrocarbon, an aromatic compound, a halogenated solvent, an alkyl-aryl ether or a combination thereof.

11. A photosensitive composition comprising:

a. At least one ester, having a structure chosen from (V), (VI), (VII) or (VIII);

b. at least one photo acid generator; and

c. at least one crosslinker;

wherein m=1-4, n=1-4, and wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group.

12. The photosensitive composition of claim 11 , wherein at least one of X or Y comprises

-(alkyl) j (aryl) k -(O) p —(COO) q -LG

wherein j, k, p, and q take the values in the following table:

-alkyl-

-aryl-

—O—

—COO—

j

k

p

q

1

1

1

1

1

1

0

1

1

1

1

0

1

0

0

1

1

0

1

0

0

1

1

1

0

1

0

1

0

1

1

0

0

0

0

1

wherein alkyl is a branched or unbranched, substituted or unsubstituted divalent alkyl chain of 1-16 carbon atoms having 0-16 heteroatoms substituted into the chain, aryl is a substituted or unsubstituted divalent phenyl group, divalent heteroaromatic group, or divalent fused aromatic or fused heteroaromatic group, and wherein LG is a leaving group.

13. The photosensitive composition of claim 12 , wherein LG is a tertiary alkyl or tertiary cycloalkyl group, an allicyclic group, a ketal or cyclic aliphatic ketal, or an acetal.

14. The photosensitive composition of claim 12 , wherein m=2, n=3, and LG is a tert-butyl carbonate group.

15. The photosensitive composition of claim 13 , wherein LG is a tert-butyl group, a tert-pentyl group, a 2,3-dimethylbutan-2-yl group, a 2,3,3-trimethylbutan-2-yl group, a 2,3-dimethylpentan-3-yl group, a 2-methylbicyclo[2.2.1]heptan-2-yl group, a bicyclo[2.2.1]heptan-2-yl group, a 1-methylcyclopentyl group, a 1-ethylcyclopentyl group, a 1-methylcyclohexyl group, a 1-ethylcyclohexyl group, a 2-methyladamantyl group or a 2-ethyladamantyl group.

16. The photosensitive composition of claim 15 , wherein the at least one photoacid generator is chosen from a sulfonium salt, an iodonium salt, a sulfone imide, a halogen-containing compound, a sulfone compound, an ester sulfonate compound, a diazomethane compound, a dicarboximidyl sulfonic acid ester, an ylideneaminooxy sulfonic acid ester, a sulfanyldiazomethane, or a mixture thereof.

17. The photosensitive composition of claim 16 , wherein the at least one photoacid generator comprises a triphenylsulfonium salt or a bis(4-tert-butylphenyl)iodonium salt.

18. The photosensitive composition of claim 12 , wherein the at least one crosslinker comprises an acid sensitive monomer or polymer.

19. The photosensitive composition of claim 12 , wherein the crosslinker comprises at least one of a glycidyl ether, glycidyl ester, glycidyl amine, a methoxymethyl group, an ethoxy methyl group, a butoxymethyl group, a benzyloxymethyl group, dimethylamino methyl group, diethylamino methyl group, a dibutoxymethyl group, a dimethylol amino methyl group, diethylol amino methyl group, a dibutylol amino methyl group, a morpholino methyl group, acetoxymethyl group, benzyloxy methyl group, formyl group, acetyl group, vinyl group or an isopropenyl group.

20. The photosensitive composition of claim 12 , wherein the crosslinker comprises one or more glycidyl ether groups attached to a novolac resin.

21. The photosensitive composition of claim 12 , further comprising a solvent, wherein the solvent comprises an ester, an ether, an ether-ester, a hydroxy ester, a hydroxy ether, a ketone, a keto-ester, a hydrocarbon, an aromatic compound, a halogenated solvent, an alkyl-aryl ether or a combination thereof.

Assignments (9)

Continuity (2)