Composition of matter and molecular resist made therefrom
Disclosed and claimed herein is a composition of matter having a general structure chosen from (I), (II), (III) or (IV); wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R 1 is a saturated or unsaturated group having from 1-4 carbon atoms, R 2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R 3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R 4 is a saturated or unsaturated group having from 1-4 carbon atoms.
1. A composition of matter comprising: a solvent; and an ester having a chemical structure chosen from (I), (II), (III) or (IV);
wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R 1 is a saturated or unsaturated group having from 1-4 carbon atoms, R 2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R 3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R 4 is a saturated or unsaturated group having from 1-4 carbon atoms.
2. The composition of matter of claim 1 , wherein at least one of X or Y comprises a tert-butyl carbonate group.
3. The composition of matter of claim 1 , wherein at least one of X or Y comprises
-(alkyl) j -(aryl) k -(O) p —(COO) q -LG
wherein i, 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.
4. The composition of matter of claim 3 , wherein LG is a tertiary alkyl or tertiary cycloalkyl group, an allicyclic group, a ketal or cyclic aliphatic ketal, or an acetal.
5. The composition of matter of claim 3 , 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.
6. The composition of matter of claim 1 , further comprising, in admixture, one or more photoacid generators 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.
7. A composition of matter comprising: a solvent; and an ester having a chemical structure chosen from (V), (VI), (VII) or (VIII);
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.
8. The composition of matter of claim 7 , wherein at least one of X or Y comprises a tert-butylcarbonate group.
9. The composition of matter of claim 7 , wherein at least one of X or Y has the structure
E-O p —(COO) q -LG
wherein E is an optional extender group, LG is a leaving group and p and q take values chosen from the following table:
(-E-)
(—O—)
(—COO—)
Present
p
q
Present
1
1
Present
0
1
Present
1
0
Not Present
0
1.
10. The composition of matter of claim 9 , wherein LG is a tert-butyl group.
11. The composition of matter of claim 9 , wherein LG is chosen from a tertiary alkyl or cycloalkyl group, a ketal or cyclic aliphatic ketal, or an acetal.
12. The composition of matter of claim 7 , 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 composition of matter of claim 12 , wherein m=2 and n=3, and wherein the leaving group is a tert-butyl group.
14. The composition of matter of claim 13 , wherein LG is chosen from a tertiary alkyl or cycloalkyl group, a ketal or cyclic aliphatic ketal, or an acetal.
15. The composition of matter 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 composition of matter of claim 13 , further comprising, in admixture, one or more photoacid generators 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 composition of matter of claim 7 , further comprising, in admixture, one or more photoacid generators 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.
18. A photosensitive composition comprising the composition of matter of claim 17 , wherein the photosensitive composition is positive working.
19. The composition of matter of claim 1 , wherein the solvent comprises an ether, an ester, an ether ester, a cyclic ketone, a non-cyclic ketone, a ketone ester, a lactate ester, a phenyl ester, an ethylene glycol monoalkyl ether, a diethylene glycol dialkyl ether, a propylene glycol monoalkyl ether, a propylene glycol dialkyl ether, a methyl phenyl ether, an acetate ester, a hydroxyacetate ester, an ethylene glycol monoalkylether acetate, a propylene glycol monoalkylether acetate, an alkoxyacetate ester, an acetoacetate ester, a pyruvate ester or a propionate ester.
20. The composition of matter of claim 7 , wherein the solvent comprises an ether, an ester, an ether ester, a cyclic ketone, a non-cyclic ketone, a ketone ester, a lactate ester, a phenyl ester, an ethylene glycol monoalkyl ether, a diethylene glycol dialkyl ether, a propylene glycol monoalkyl ether, a propylene glycol dialkyl ether, a methyl phenyl ether, an acetate ester, a hydroxyacetate ester, an ethylene glycol monoalkylether acetate, a propylene glycol monoalkylether acetate, an alkoxyacetate ester, an acetoacetate ester, a pyruvate ester or a propionate ester.