US4828958A — Photosensitive composition and method of forming …

Claim 1

Independent Claim 120 words

A photosensitive composition comprising an admixture of: (a) a resin which comprises a polymer that comprises (i) a structural unit as shown by the following formula: ##STR20## wherein R 1 , R 2 , R 3 , R 4 , and R 5 may be identical or may be different, each representing hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents hydrogen atom, alkyl radical, allyl radical, aryl radical, alkylcarbonyl radical, allylcarbonyl or radical, and (ii) a structural unit as shown by the following formula: ##STR21## and (b) a photosensitive compound of positive or negative type.

Claim 2

Dependent Claim 120 words

A photosensitive composition comprising an admixture of: (a) a resin which comprises a polymer that comprises (i) a structural unit as shown by the following formula: ##STR20## wherein R 1 , R 2 , R 3 , R 4 , and R 5 may be identical or may be different, each representing hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents hydrogen atom, alkyl radical, allyl radical, aryl radical, alkylcarbonyl radical, allylcarbonyl or radical, and (ii) a structural unit as shown by the following formula: ##STR21## and (b) a photosensitive compound of positive or negative type.

Claim 3

Dependent Claim 32 words

The photosensitive composition of claim 1 wherein said resin comprises a copolymer which consist of the structural unit shown by the formula (I) and the structural unit shown by the formula (II).

Claim 4

Dependent Claim 55 words

The photosensitive composition of claim 1 wherein said resin comprises a copolymer consists of (a) a plurality of structural units shown by the formula (I) in which at least one set of the substitutional groups R 1 to R 5 is different from the rest, and (b) a structural unit shown by the formula (II).

Claim 5

Dependent Claim 47 words

The photosensitive composition of claim 1 wherein said resin comprises a mixture of plural kinds of mutually different copolymers as described in claim 2, in which at least one set of the substitutional groups R 1 to R 5 included in the copolymers differs from the rest.

Claim 6

Dependent Claim 59 words

The photosensitive composition of claim 1 wherein said resin comprises a mixture of a copolymer as described in claim 2, and a copolymer which consists of a structural unit shown by the formular (I), a structural unit shown by the formular (II) and a structural unit selected from the group consisting of vinyl chain, vinylidene chanin and ester chain.

Claim 7

Dependent Claim 56 words

The photosensitive composition of claim 1 wherein said resin comprises a mixture of plural kinds of mutually different copolymers each of which consist of a structural unit shown by the formular (I), structural unit shown by the formula (II), and a structural unit selected from the group consisting of vinyl chain, vinylidene chain and ester chain.

Claim 8

Dependent Claim 22 words

The photosensitive composition of claim 1 wherein the number average molecular weight of said resin is 10 3 to 10 5 .

Claim 9

Dependent Claim 19 words

The photosensitive composition of claim 7 wherein the number average molecular weight of said resin is 2,000 to 60,000.

Claim 10

Dependent Claim 34 words

The photosensitive composition of claim 7 wherein the content in said resin of a polymer which comprises structural units shown by the formula (I) and the formula (II), is 10 to 100% by weight.

Claim 11

Dependent Claim 23 words

The photosensitive composition of claim 9 wherein the content of said photosensitive compound in the photosensitive composite is 0.1 to 50% by weight.

Claim 12

Dependent Claim 40 words

The photosensitive composition of claim 9 wherein the number of structural unit shown by the formula (I) is k, and the number of structural unit shown by the formula (II) is l, and k and l satisfy the condition 0.1≦k/(k+l)≦0.5.

Claim 13

Dependent Claim 55 words

The photosensitive composition of claim 9 wherein said photosensitive compound is (a) a condensation product, which is soluble in organic solvent, between a p-quinonediazide, p-iminoquinonediazide, or diazonium salt and formaldehyde, (b) a copolymerization product between an aromatic diazonium salt or an aromatic product and formaldehyde, (c) an aromatic azide, or (d) an organic halogen compound.

Claim 14

Dependent Claim 27 words

The photosensitive composition of claim 9 wherein said photosensitive compound is (a) an aromatic ester of o-naphthoquinonediazidosulfonic acid or o-naphthoquinonediazidocarbonic acid, or (b) o-quinonediazide such as amide.

Claim 15

Dependent Claim 26 words

The photosensitive composition of claim 9 wherein said photosensitive compound comprises a compound shown by ##STR22## where A in the above formula is represented by ##STR23##

Claim 16

Dependent Claim 45 words

The photosensitive of claim 14 wherein said resin comprises a copolymer shown by the following formula ##STR24## and the mixing ratio of the resin and the photosensitive compound is 30 parts by weight of the photosensitive compound for 100 parts by weight of the resin.

Claim 17

Dependent Claim 90 words

A method of producing the photosensitive of claim 9 comprising the steps of: (a) obtaining a copolymer shown by the formula ##STR25## by reacting styrene and polyvinylphenol in the molar ratio of 2:10; (b) preparing a resin by introducing benzyl radical to the copolymer in the molar ratio of 1:10 to introduce the benzoyl radical in place of the hydrogen atom in the hydroxyl radical of phenol; and (c) mixing 20 parts by weight of a photosensitive compound shown by ##STR26## and 80 parts by weight of the resin obtained.

Claim 18

Dependent Claim 87 words

A method of producing the photosensitive composition of claim 9 comprising the steps of: (a) obtaining a copolymer shown by the formula ##STR27## by reacting styrene and polyvinylphenol in the molar ratio of 2:10; (b) preparing a resin by supplying benzoyl radical to the copolymer in the molar ratio of 1:10 to introduce the benzoyl radical in place of hydrogen atom in the hydroxyl radical of phenol; and (c) mixing the resin with 1,2-naphthoxydiazido-5-sulfonic acid ester (average esterification factor of 2.0) of 2,3,4-trihydroxybenzophenone as a photosensitive compound.

Claim 19

Dependent Claim 72 words

A method of producing the photosensitive composition of claim 9 comprising the steps of: (a) obtaining a copolymer shown by the formula ##STR28## by reacting styrene and polyvinylphenol in the molar ratio of 2:10; and (b) introducing ##STR29## in place of the hydrogen atom in the hydroxyl radical of phenol, by carrying out esterification in which 1,2-naphthoquinonediazido-5-sulfonic acid chloride and the copolymer are brought into reaction in the molar ratio of 3:10.

Claim 20

Dependent Claim 86 words

A method of producing the photosensitive composition of claim 9 comprising the steps of: (a) obtaining a copolymer shown by the formula ##STR30## by reacting styrene and polyvinylphenol in the molar ratio of 3:10; (b) introducing the methyl radical in place of the hydrogen atom in the hydroxyl radical of phenol by supplying methyl radical to the copolymer in the molar ratio of 3:10; and (c) mixing 20 parts by weight of a photosensitive compound shown by ##STR31## to 80 parts by weight of the resin.

Claim 21

Independent Claim 215 words

A method of forming a resist pattern on the surface of a substrate by the use of a photosensitive composition that consists of a photosensitive compound and a resin which comprises polymers that comprises (i) a structural unit as shown by the following formula, ##STR32## wherein, R 1 , R 2 , R 3 , and R 5 may be identical or may be different, each representing a hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents a hydrogen atom, alkyl radical, allyl radical, aryl radical, alkylcarbonyl radical, allylcarbonyl radical, or quinonediazidosulfonyl radical, and (ii) a structural unit as shown by the following formula: ##STR33## comprising the steps of: (a) dissolving the photosensitive composition in an organic solvent; (b) spreading the photosensitive composition on the surface of the substrate; (c) creating a difference in the solubility to an alkaline aqueous solution between the exposed portion and the unexposed portion by irradiating the surface of the substrate with either one of light or electron beam to form a predetermined pattern; and (d) dissolving either one of the exposed portion or unexposed portion by developing the surface of the substrate with an alkali.

Claim 22

Independent Claim 215 words

A method of forming a resist pattern on the surface of a substrate by the use of a photosensitive composition that consists of a photosensitive compound and a resin which comprises polymers that comprises (i) a structural unit as shown by the following formula, ##STR32## wherein, R 1 , R 2 , R 3 , and R 5 may be identical or may be different, each representing a hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents a hydrogen atom, alkyl radical, allyl radical, aryl radical, alkylcarbonyl radical, allylcarbonyl radical, or quinonediazidosulfonyl radical, and (ii) a structural unit as shown by the following formula: ##STR33## comprising the steps of: (a) dissolving the photosensitive composition in an organic solvent; (b) spreading the photosensitive composition on the surface of the substrate; (c) creating a difference in the solubility to an alkaline aqueous solution between the exposed portion and the unexposed portion by irradiating the surface of the substrate with either one of light or electron beam to form a predetermined pattern; and (d) dissolving either one of the exposed portion or unexposed portion by developing the surface of the substrate with an alkali.

Claim 23

Dependent Claim 29 words

The method of forming a resist pattern of claim 20 wherein said photosensitive compound is of positive type so that the exposed portion is dissolved in said alkaline developer.

Claim 24

Dependent Claim 29 words

The method of forming a resist pattern of claim 20 wherein said photosensitive compound is of negative type so that the unexposed portion is dissolved in said alkaline development.

Claim 25

Dependent Claim 62 words

The method of forming a resist pattern of claim 20 wherein said organic solvent is (i) a ketone-based solvent such as cyclohexanone, acetone, methylethylketone, and methylisobutylketone, (ii) a cellosolve-based solvent such as methylcellosolve, methylcellosolve acetate, and ethylcellosolve acetate, or (iii) an ester-based solvent such as acetic acid ethyl, acetic acid butyl, and acetic acid isoamyl, (iv) or a mixture of these solvents.

Claim 26

Dependent Claim 32 words

The method of forming a resist pattern of claim 20 wherein said alkaline solution for the alkaline development comprises an aqueous solution of tetraalkylammonium or an aqueous solution of an inorganic alkali.

Claim 27

Dependent Claim 54 words

A method of fabricating a substrate by the use of a resist pattern formed on the surface of the substrate according to the method described in claim 20 comprising the steps of: (a) etching the substrate using said resist pattern as the mask; and (b) removing the resist material that remains on the substrate.

Claim 28

Dependent Claim 92 words

A photosensitive composition comprising a polymer that comprises (i) a structural unit as shown by the following formula: ##STR34## wherein R 1 , R 2 , R 3 , R 4 , and R 5 may be identical or may be different, each representing hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents quinonediazide sulfonyl radical, and (ii) a structural unit as shown by the following formula: ##STR35##

Claim 29

Dependent Claim 92 words

A photosensitive composition comprising a polymer that comprises (i) a structural unit as shown by the following formula: ##STR34## wherein R 1 , R 2 , R 3 , R 4 , and R 5 may be identical or may be different, each representing hydrogen atom, halogen atom, alkyl radical, carboxyl radical, alkylcarbonyl radical, alkoxycarbonyl radical, alkoxy radical, acyloxy radical, allyl radical, aryl radical, hydroxy radical, halogenoalkyl radical, cyanoalkyl radical, or alkoxyalkyl radical, and R 6 represents quinonediazide sulfonyl radical, and (ii) a structural unit as shown by the following formula: ##STR35##

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1992-05-08	1992-11-07	1993-05-09	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1996-05-08	1996-11-07	1997-05-09	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2000-05-08	2000-11-07	2001-05-09	$7700.00	Window Closed / Lapsed

Photosensitive composition and method of forming a resist pattern with copolymer of polyvinyl phenol

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