Positive-working photoresist compositions comprising an alkali-soluble novolak resin made with four phenolic monomers

Claim 2

An alkali-soluble novolak binder resin made by addition condensation reaction of a phenolic mixture with at least one aldehyde source, the feedstock of said phenolic mixture for said reaction comprising: (1) about 33 to about 83 mole percent of said phenolic mixture being meta-cresol; (2) about 1 to about 4 mole percent of said phenolic mixture being para-cresol; (3) about 10 to about 60 mole percent of said phenolic mixture being a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol and mixtures thereof; and (4) about 5 to about 55 mole percent of said phenolic mixture being a methoxy phenol monomer selected from the group consisting of para-methoxyphenol, meta-methoxyphenol, ortho-methoxyphenol and mixtures thereof; the amount of said aldehyde source being from about 40 to about 200 percent of the stoichiometric amount needed to react with all of the phenolic moieties in said phenolic mixture; and said alkali-soluble novolak binder resin having a weight-average molecular weight (M w ) of about 3,000 to about 20,000 with a molecular weight dispersity (M w /M n ) of 1.5-4.0 and a dissolution rate in a 2.38 percent by weight aqueous solution of tetramethylammonium hydroxide (TMAH) of 3-100 angstroms per second at 23° C.

Claim 3

The alkali-soluble novolak binder resin of claim 1, wherein the feedstock of said phenolic mixture for said reaction comprises about 40 to about 70 mole percent of meta-cresol; about 2 to about 4 mole percent of para-cresol; about 15 to about 45 mole percent of a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol and mixtures thereof; and about 10 to about 40 mole percent of a methoxyphenol monomer selected from the group consisting of para-methoxyphenol, meta-methoxyphenol, ortho-methoxyphenol and mixtures thereof.

Claim 4

The alkali-soluble novolak binder resin of claim 1, wherein the feedstock of said phenolic mixture for said reaction comprises about 45 to about 60 mole percent of meta-cresol; about 1 to about 2 mole percent of para-cresol; about 15 to about 30 mole percent of a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol and mixtures thereof; and about 15 to about 30 mole percent of a methoxy phenol monomer selected from the group consisting of para-methoxyphenol, meta-methoxyphenol, ortho-methoxyphenol and mixtures thereof.

Claim 5

The alkali-soluble novolak binder resin of claim 1, wherein said aldehyde source is selected from the group consisting of formaldehyde, paraformaldehyde, trioxane, acetaldehyde, chloroacetaldehyde and combinations thereof.

Claim 6

The alkali-soluble novolak binder resin of claim 1, wherein said alkali-soluble novolak binder resin has a weight-average molecular weight (M w ) of about 4,000 to about 18,000.

Claim 7

The alkali-soluble novolak binder resin of claim 1, wherein said alkali-soluble novolak binder resin has a weight-average molecular weight (M w ) of about 5,000 to about 16,000.

Claim 8

The alkali-soluble novolak binder resin of claim 1, wherein said alkali-soluble novolak binder resin has a molecular weight dispersity (M w /M n ) of 1.8-3.5.

Claim 9

The alkali-soluble novolak binder resin of claim 1, wherein said alkali-soluble novolak binder resin has a molecular weight dispersity (M w /M n ) of 2.0-3.3.

Claim 10

The alkali-soluble novolak binder resin of claim 1, wherein said addition condensation reaction utilizes and acid catalyst selected from the group consisting of hydrochloric acid, sulfuric acid, formic acid, acetic acid, oxalic acid, and combinations thereof.

Claim 11

A positive-working photoresist composition comprising the admixture of: (a) an alkali-soluble novalak binder resin made by addition condensation reaction of a phenolic mixture with at least one aldehyde source, the feedstock said phenolic mixture for said reaction comprising: (1) about 33 to about 83 mole percent of said phenolic mixture being meta-cresol; (2) about 1 to about 4 mole percent of said phenolic mixture being para-cresol; (3) about 10 to about 60 mole percent of said phenolic mixture being a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol; and mixtures thereof; and (4) about 5 to about 55 mole percent of said phenolic mixture being a methoxy phenol monomer selected from the group consisting of para-methoxyphenol, meta-methoxyphenol, ortho-methoxy phenol the amount of said aldehyde source being from about 40 percent to about 200 percent of the stoichiometric amount needed to react with all of the phenolic moieties in said phenolic mixture and mixtures thereof; and said alkali-soluble novolak binder resin having a weight average molecular weight (M w ) of about 3,000 to about 20,000 with a molecular weight dispersity (M w /M n ) of 1.5-4.0 and a dissolution rate in a 2.38 percent by weight aqueous solution of tetramethylammonium hydroxide (TMAH) of 3-100 Angstroms per second at 23° C.; (b) at least one photoactive compound, the amount of said photoactive compound or compounds being 35 to 100 percent by weight of said novolak binder resin; and (c) at least one polyhydroxy compound having 2 to 7 phenolic groups and a weight average molecular weight (M w ) below about 1000; the amount of said polyhydroxy compound or compounds being about 10 to about 60 percent by weight of said novalak binder resin.

Claim 12

A positive-working photoresist composition comprising the admixture of: (a) an alkali-soluble novalak binder resin made by addition condensation reaction of a phenolic mixture with at least one aldehyde source, the feedstock said phenolic mixture for said reaction comprising: (1) about 33 to about 83 mole percent of said phenolic mixture being meta-cresol; (2) about 1 to about 4 mole percent of said phenolic mixture being para-cresol; (3) about 10 to about 60 mole percent of said phenolic mixture being a phenolic monomer selected from the group consisting of 2,3-xylenol, 3,4-xylenol, 3,5-xylenol; and mixtures thereof; and (4) about 5 to about 55 mole percent of said phenolic mixture being a methoxy phenol monomer selected from the group consisting of para-methoxyphenol, meta-methoxyphenol, ortho-methoxy phenol the amount of said aldehyde source being from about 40 percent to about 200 percent of the stoichiometric amount needed to react with all of the phenolic moieties in said phenolic mixture and mixtures thereof; and said alkali-soluble novolak binder resin having a weight average molecular weight (M w ) of about 3,000 to about 20,000 with a molecular weight dispersity (M w /M n ) of 1.5-4.0 and a dissolution rate in a 2.38 percent by weight aqueous solution of tetramethylammonium hydroxide (TMAH) of 3-100 Angstroms per second at 23° C.; (b) at least one photoactive compound, the amount of said photoactive compound or compounds being 35 to 100 percent by weight of said novolak binder resin; and (c) at least one polyhydroxy compound having 2 to 7 phenolic groups and a weight average molecular weight (M w ) below about 1000; the amount of said polyhydroxy compound or compounds being about 10 to about 60 percent by weight of said novalak binder resin.

Claim 13

The positive-working photoresist composition of claim 10, wherein said photoactive compound is selected from the group consisting of 1,2-napthoquinonediazide-5-sulfonyl chloride, 1,2-naphthoquinonediazide-4-sulfonyl chloride, and combinations thereof.

Claim 14

The positive-working photoresist composition of claim 10, wherein said polyhydroxy compound is selected from the group consisting of formulae (A)-(D) and mixtures thereof: ##STR9## .

Claim 15

The positive-working photoresist composition of claim 10, further comprising a speed enhancer.

Claim 16

The positive-working photoresist composition of claim 13, wherein said speed enhancer is selected from the group consisting of formulae (P-1)-(P-3) and mixtures thereof: ##STR10## .