JPH03215863A - Positive type photoresist composition - Google Patents

Abstract

PURPOSE:To obtain the positive type photoresist compsn. having a high resolving power by incorporating a specific compd. and alkaline-soluble resin into the positive type photoresist compsn. CONSTITUTION:The positive type photoresist compsn. contg. the compd. expressed by general formula (I) and the alkaline-soluble resin has the excellent resolving power, faithful reproducibility, excellent sectional shape of a resist image, developing latitude, sensitivity, and heat resistance. This compd. is obtd. by subjecting a part or the whole of the hydroxyl group of a polyhydroxy compd. to ordinary esterification in the presence of 1, 2-naphthoquinone diazide-5-(and/or -4-) sulfonyl chloride and a basic catalyst. The alkaline-soluble resin is exemplified by a novolak resin, acetone-pyrogallol resin, polyhydroxystyrene and the deriv. thereof.

Description

[Detailed description of the invention] Industrial application field> The present invention relates to a radiation-sensitive positive type photoresist composition, in particular a fine photoresist composition with high resolution and sensitivity, and a good pattern cross-sectional shape. The present invention relates to photoresist compositions for processing.

The positive photoresist according to the present invention is coated onto a substrate such as a semiconductor wafer, glass, ceramic, or metal to a thickness of 0.5 to 3 μm by spin coating or roller coating. After that, it is heated and dried, and the circuit pattern etc. is printed using ultraviolet rays through an exposure mask.
A positive image is formed by development. Furthermore, by etching this positive image as a mask, it is possible to process a pattern on the substrate. Typical application fields include the manufacturing process of semiconductors such as ICs, the manufacturing of circuit boards such as liquid crystals and thermal heads, and other application processes.

<Conventional Technology> As a positive type photoresist composition, a composition containing an alkali-soluble resin and a sodium quinone diazide compound as a photosensitive material is generally used. For example, US Pat.
USP-4,115,128-3- and USP-4,173,470, etc., and the most typical composition is ``Cresol-Formaldehyde/Volac resin/Trihydroxybenzo7 Engineering/
An example of 1,1-na7toquinonediazide sulfonic acid ester is given by L.F.
n [Intro-duetion to M
icrolitho-graphyJ) (ACS Publishing, No. 219, P112-121).

7 Volac resin as a binder is particularly suitable for this application because it can be dissolved in aqueous alkaline solutions without swelling and also provides high resistance to plasma etching, especially when the resulting image is used as an etching mask. Useful. In addition, the sodium quinone diazide compound used in photosensitive materials itself acts as a dissolution inhibitor that reduces the alkali solubility of the novolak resin, but when it decomposes upon exposure to light, it produces alkali-soluble substances and rather the alkali of the novolak resin. It is unique in that it acts to increase solubility, and because of its large change in properties in response to light, it is particularly useful as a photosensitive material for positive type photoresists.

From this point of view, many positive type photoresists containing 7-bod resins and naphthoquinone diazide photosensitive materials have been developed and put into practical use. We have achieved sufficient results.

<Problems to be solved by the present invention> However, the degree of integration of integrated circuits is increasing, and ultra-L
In the manufacture of semiconductor substrates such as SI, it has become necessary to process ultra-fine patterns having line widths of 1 μW or less. In such applications, a photoresist is required that has particularly high resolution, high pattern shape reproduction accuracy to accurately copy the shape of the exposure mask, and high sensitivity from the viewpoint of high productivity. The reality is that we cannot respond.

Therefore, it is an object of the present invention to provide a positive photoresist composition having high resolution, particularly in the production of semiconductor devices. A positive photoresist composition that accurately reproduces mask dimensions over a wide range of mask line widths, and a positive photoresist that can produce a cross-sectional resist pattern with a high aspect ratio in a pattern with a line width of 1 μm or less. composition, a positive photoresist composition capable of producing a pattern in which the sidewalls of the cross section of the pattern are nearly vertical; a positive photoresist composition having a wide development latitude; a positive photoresist composition whose resulting resist image has excellent heat resistance. Cyst composition, Vosi type 7, which is soluble in commonly used l-cyst solvents and has excellent storage stability without the generation of foreign matter even during long-term storage.
An object of the present invention is to provide an otoresist composition.

<Means for Solving the Problems> The present inventors have completed the present invention by paying attention to the above-mentioned characteristics and conducting extensive studies.

That is, the object of the present invention has been achieved by a positive photoresist composition characterized by containing a compound represented by the following general formula (I) and an alkali-soluble resin.

-71 The photosensitive compound represented by the general formula (I) used in the present invention is, for example, 2-(3.4-dihydroxy7enyl)-3ts+7-trihydroxybenzobilane, 2
- (3,4.5-}lihydroxy-8-7enyl)-3.5.7-trihydroxybenzobilane, 2-(3.4-:/hydroxy7enyl)-3-
(3,4.5-trihydroxybenzoyloxy)-5
．． 7-dihydroxybenzobilane, 2(3,4.5-}
Polyhydroxy compounds such as 1,2-na7enyl)-3-(3,4.5-trihydroxybenzoyloxy)5,7-dihydroxybenzobilane, and/or -4-) Obtained by reacting sulfonyl chloride. These polyhydroxy compounds may be used alone or in combination of two or more, but are not limited thereto.

In the compound of the present invention, for example, some or all of the hydroxyl groups of the polyhydroxy compound are replaced with 1,2-na7toquinonediazide-5-(and/or -4-)sulfonyl chloride,
It can be obtained by carrying out a conventional esterification reaction in the presence of a basic catalyst.

That is, a predetermined amount of a polyhydroxy compound and a solvent such as 1,2-7toquinone diazido-5-(and/or -4-)sulfonyl chloride, thioxane, acetone, methyl ethyl ketone, N-methyl pyrrolidone, etc. are charged into a flask, and a base is added. A natural catalyst such as sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, triethylamine, etc. is added dropwise to effect condensation. The obtained product is washed with water and dried.6 In the above esterification reactions, mixtures having various esterification numbers and esterification positions are obtained. Therefore, the esterification rate referred to in the present invention is defined as the average value of this mixture.

The esterification rate defined in this way is based on the raw material polyhydroxy compound and the 1,2-na-7-toquinone dianod
It can be controlled by the mixing ratio with 5-(and/or -4-)sulfonyl chloride. That is, since substantially all of the added 1,2-na7-cyazide-5-(and/or -4-)sulfonyl chloride undergoes an esterification reaction,
In order to obtain a mixture with a desired esterification rate, the molar ratio of the raw materials may be adjusted.

If necessary, 1,2-na7toquinone noanodo-5-sulfonic acid ester and 1!2-na7toquinone diazide-4
- A sulfonic acid ester can also be used in combination.

In addition, the reaction temperature in the above method is usually -20 to 60
℃, preferably θ to 40℃.

When the photosensitive compound of the present invention synthesized by the method described above is used as a resin composition, it is used alone or as a mixture of two or more of them in an alkali-soluble resin. is from 5 to 100 parts by weight, preferably from 10 to 50 parts by weight, per 100 parts by weight of the novolak resin. If the usage ratio is less than 5 parts by weight, the residual film rate will be severely reduced, and if it exceeds 100 parts by weight, the sensitivity and solubility in solvents will decrease. Examples of the alkali-soluble resin used in the present invention include novolak resin, acetone-pyrorole resin, polyhydroxystyrene, and derivatives thereof.

Among these, novolac resins are particularly preferred, and can be obtained by addition-condensing a predetermined monomer as a main component with an aldehyde in the presence of an acidic catalyst.

Predetermined monomers include cresols such as 7-enol, 1-cresol, p-cresol, and 0-cresol;
2,5-xylenol, 3,5-xylenol, 3,4
-Xylene/- such as xylenol, 2,3-xylene 7-yl, etc.
Alkyl 7-enols such as I6-ethyl 7-enol, p-ethyl 7-enol, 0-ethylphenol, pt-butyl 7-enol, p-methoxy 7-enol, the best methoxy 7-enol 3,5-dimethoxyphenol, 2-methoxy-4-methyl 7-enol, 1-ethoxy 7-enol, p-ethoxy 7-enol, the best broboxy-7-enol, p-propoxy 7-enol, - Alkoxyphenols such as butoxy 7-enol, p-ptoxyphenol, bisalkyl 7-enols such as 2-methyl-4-isopropylphenol, eyelid-chloro 7-enol, p-chloro 7-enol Hydroxy aromatic compounds such as , 0-chloro 7-enyl, cyhydroxybi-7-enyl, bis-7-enyl A, 7-enyl 7-enol, resorcinol, na-7-tol, etc. are used alone or in combination of two or more. However, it is not limited to these.

Examples of aldehydes include formaldehyde, paraformaldehyde, acetaldehyde, provilaldehyde, benzaldehyde, 7-enyl acetaldehyde,
α-7enylpropylaldehyde, β-7enylpropylaldehyde, 0-hydrotetraxybenzaldehyde,
mono-hydroxybenzaldehyde, p-hydroxybenzaldehyde, o-chlorobenzaldehyde, m-chlorobenzaldehyde, p-chlorobenzaldehyde}%O
-Nitrobenzaldehyde, 11-2trobenzaldehyde, p-nitrobenzaldehyde, 0-methylbenzaldehyde, 1-methylbenzaldehyde, p-methylbenzaldehyde, p-ethylbenzaldehyde, p-n
-"ff Rubenzaldehyde, 7ral, 7ral, chloroacetaldehyde, and acetals thereof, such as chloroa-7taldehyde diethyl acetal, etc. can be used, but among these, formaldehyde is preferably used.

These aldehydes may be used alone or in combination of two or more.

As the acidic catalyst, hydrochloric acid, sulfuric acid, formic acid, acetic acid, oxalic acid, etc. can be used.

The weight average molecular weight of the novolak resin thus obtained is preferably in the range of 2,000 to 30,000.

If it is less than 2000, the film loss after development in the unexposed area will be large;
If it exceeds 30,000, the developing speed will become low.

Particularly preferred is a range of 6,000 to 20,000.

Here, the weight average molecular weight is defined by the value calculated by delvermeation chromatography 7E in terms of boristyrene.

In the present invention, the photosensitive material described above should be mainly used, but if necessary, one of the following polyhydroxy compounds may be used.
, 2-na7toquinonediazide-5-(and/or -4-
) Esterified products with sulfonyl chloride can be used in combination.

Examples of polyhydroxy compounds include 2, 3.
4-}rihydroxybenzo-7-enone, 2,4,4-trihydroxybenzo-7-enone, 2,4.6-trihydroxybenzophenone, 2,3.4-trihydroxy-2'
-Methylbenzo 7/N, 2,3,4.4'-Tetrahydroxybenzo 7/N, 2.2'. 4.4'-Tetrahydroxybenzo7/n, 2,4,6.3',4'-
Pentahydroxybenzo 7/n, 2,3,4.2',
4°-Pentahydroxybenzophenone, 2,3,4.
2',5'-bentahydroxybenzo7enone, 2,4
, 6.3',4',5'hexahydroxybenzo7enone, 2,3,4.3'4',5'polyhydroxybenzo7enone M, such as 2,3'4',5'-hexahydroxybenzo7enone
,3,4-}rihydroxy7ceto7enone,2,3.4
-}rihydroxy7enylbentylketone, 2,3.4
-}Polyhydroxy 7enyl alkyl ketones such as hydroxy7enylhexylketone, bis(2,4-nohydroxy7enyl)methane, bis(2,3.4-}lihydroxy7enyl)methane, bis(2 .4-dihydroxy7enyl)propane-1, bis(2,3.4-}lihydroxy7enyl)propane-1, 7-dihydroguaiaretic acid and other bis((poly)hydroxy7enyl)alkanes; 3,4.5-}probyl-trihydroxybenzoate, phenyl 2,3,4-trihydroxybenzoate, 3
, polyhydroxybenzoic acid esters such as 7enyl 4,5-trihydroxybenzoate, bis(2,3.4-trihydroxybenzoyl)methane, bis(3-acetyl-4,5.6-}rihydroxy7) Bis(polyhydroxybenzoyl)alkanes or bis(polyhydroxybenzoyl)aryls such as enyl)-methane, bis(2,3.4-trihydroxybenzoyl)benzene, bis(2,4.6-}lihydroxybenzoyl)benzene, etc. , alkylene di(polyhydroxybenzoates) such as ethylene glycol di(3,5-dihydroxybenzoate), ethylene glycol di(3,4.5-}dihydroxybenzoate), 2,3.4-bi7! dilutriol, 3,4.5-bi7enyltriol, 3,5,
3'. 5'-bi7enyltetrol, 2,4,2',4
'-bi7enyltetrol, 2,4,6.3'5'-bi7enylpentol, 2,4,6,2',4'6'-bi7enylhexol, 2,3,4.2 ',3'4゛-bi7enylhexol and other polyhydroxybi7enyls,
Bis(polyhydroxy)sulfonamides such as 4,4'-thiobis(I,3-hydroxy)benzene, 2.2'
, 4.4'-tetrahydroxy di7enyl ether and other bis(polyhydroxy 7enyl) ethers, 2.2'
, 4,4'-tetrahydroxycy7enylsul7oxide, etc.; bis(polyhydroxy7enyl) such as 2,2',4.4'-cy7enylsul7one, etc. Sur7ones, 4,4"
3 II,41+-tetrahydroxy-3. 5. 3
',5'tetramethyltri7enylmethane 4,
4T, 2 1 13", 4"-bentahydroxy-3.5.3',5'tetramethyltri7enylmethane, 2t3,4t2'3',4'-hexahydroxy-5,5'-diacetyltri 7-enylmethane, 2.
3,4.2',3',4'3 II,4+1-octahydroxy-5,5'-diacetyltri7enylmethane,
2,4,6.2',4',6'-monohexahydroxy-5
, 5'-diprobionylt 17 722methane and other polyhydroxy MJ7 enylmethanes, 3 , 3 . 3
',3'-tetramethyl-1,1'-spirobeeingine-5.6.5',6'-tetrol, 3,3.
3',3'-tetramethyl-1,1'-spirobeeingin-5. 6,7. 5', 6', 7'
Hexol, 3,3.3',3゜-tetofmethyl-1
,1'-Spirobingen-4.5,6.4',5'
6'-hexol, 3,3. 3′,3′-tetramethyl-1,1′-subilobien-4.5,
6.5'6',? 'Polyhydroxysubibens such as monohexol, 3,3-bis(3,4-cyhydroxy7enyl)7talide, 3,3-bis(2,3.4
-trihydroxy7enyl)7thalide, 3',4",5
゜,6'-tetrahydroxysbiro[7thalide-3.9
Polyhydroxy 7-thallides such as '-xanthene], 7 lab 7 pigments such as morin, quercetin, rutin, etc. can be used.

It is also possible to use a low-nuclear substance of 7-enol resin such as /borac resin.

These photosensitive materials of sodium quinone diazide esters of polyhydroxy compounds may be used alone or in combination of two or more.

In this case, it can be used in an amount of 100 parts by weight or less, preferably 30 parts by weight or less, based on 100 parts by weight of the photosensitive material of the present invention.

The compound of the present invention may further contain a polyhydroxy compound to promote dissolution in a developer. Preferred polyhydroxy compounds include phenols,
Resorcin, 7loroglucin, 2,3,4-trihydroxybenzo7enone, 2,3,4,4'-tetrahydroxybenzo7enone, 2,3,4,3',4',5゜-
Examples include hexahydroxybenzo 7/N, acetone-pyrrole synthetic resin, 7-rologlucide, and the like.

The blending amount of the polyhydroxy compound is usually 100 parts by weight or less, preferably 5 to 50 parts by weight, based on 100 parts by weight of the quinonediazide compound.

Examples of the solvent for dissolving the photosensitive material and alkali-soluble novolac resin of the present invention include ketones such as methyl ethyl ketone and cyclohexanone, 4-ethoxy-2-butanone,
Keto ethers such as 4-methoxy-4-methyl-2-pentanone, ethyl 1/7 glycol monomethyl ether,
Alcohol ethers such as ethylene glycol/ethyl ether; ethers such as dioxane and ethylene glycol dimethyl ether; cellosolve esters such as methyl cellosolve acetate and ethyl cellosolve acetate; fatty acid esters such as butyl acetate, methyl lactate, and ethyl lactate; Examples include halogenated hydrocarbons such as 1,1.2-}lichloroethylene, and highly polar solvents such as dimethylacetamide, N-methylpyrrolidone, dimethylformamide, and dimethylsulfoxide. These solvents can be used alone or in combination.

A surfactant can be added to the composition for positive photoresist of the present invention in order to further improve the coating properties against striae and the like.

Examples of surfactants include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether,
Polyoxyethylene alkyl ethers such as polyoxyethylene cetyl ether and polyoxyethylene oleyl ether; polyoxyethylene alkyl allyl ethers such as polyoxyethylene octyl 7-enol ether and polyoxyethylene nonyl 7-enol ether; Ethylene/polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monobalmitate, sorbitan monostearate, sorbitan monooleate. , sorbitan fatty acid esters such as sorbitan trioleate and sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene 7 diionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as sorbitan tristearate, 7 top EF301, EF303, EF352
(Manufactured by Shin Akita Kasei Co., Ltd.), Me, ly7 Atsuku F171,
F173 (manufactured by Dainippon Ink Co., Ltd.), 7 Lollard F
C430, FC431 (manufactured by Sumitomo 3M Ltd.)
, Asahi Guard AG710, Sir 7 Ron S-382, S
CIOI, SC102, S'CI 0 3, SCI 0
4, SCI O 5, SC1 0 6 (Asahi Glass Co., Ltd.)
(manufactured by Shin-Etsu Chemical Co., Ltd.), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), acrylic acid-based or methacrylic acid-based (co)polymerized polymer 7-Row N
o. 75, No. 95 (manufactured by Kyoeisha Yushi Kagaku Kogyo Co., Ltd.)
etc. can be mentioned. The amount of these surfactants blended is usually 2 parts by weight or less, preferably 1 part by weight or less, per 100 parts by weight of the alkali-soluble resin and quinone diazide compound in the composition of the present invention.

These surfactants may be added alone, or
They can also be added in some combinations.

The developer for the composition for a positive photoresist of the present invention includes inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-probylamine, etc. Primary amines such as diethylamine, di-n-
Secondary amines such as butylamine, tertiary amines such as triethylamine and methyl diethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, and quaternary ammoniums such as tetramethylammonium hydroxide and tetraethylammonium hydroxide. Aqueous solutions of alkalis such as salts, virol, cyclic amines such as bivericin, etc. can be used. Furthermore, appropriate amounts of alcohols and surfactants may be added to the aqueous alkali solution.

The positive photoresist composition of the present invention may contain a dye, a plasticizer, and an adhesion aid, if necessary.

Examples include dyes such as methyl violet, crystal violet, and malachite green, plasticizers such as stearic acid, acetal resin, 7-enoxy resin, and alkyd resin, and adhesion aids such as hexamethyldisilazane and chloromethylsilane. .

The composition for a positive photoresist is coated onto a substrate (e.g. silicone/silicon dioxide coated) used in the manufacture of precision integrated circuit elements using an appropriate coating method such as a spinner or coater, and then coated in a prescribed manner. A good resist can be obtained by exposing the resist to light through a mask and developing it.

<Effects of the Invention> The positive photoresist of the present invention is excellent in high resolution, faithful reproducibility, cross-sectional shape of resist image, development latitude, sensitivity, and heat resistance.

Examples> Examples of the present invention are shown below, but the present invention is not limited thereto. Note that % indicates weight % unless otherwise specified.

Examples (I) to (2), Comparative Examples (I) to (2) (I)
Synthesis of photosensitive material a 2-(3,4.5-}lihydroxy7enyl)-3.
5.7-}rihydroxybenzobilane 5,o. i, 1.
2-Na7toquinonediazide-5-sulfonyl chloride 1
9.9 g and 200+ al of acetone were charged into a three-necked flask and uniformly dissolved. Then triethylamine/acetone=7. 7 g/50 ml was gradually added dropwise and reacted at 25°C for 3 hours. The reaction mixture was poured into 1500 ml of a 1% aqueous hydrochloric acid solution, and the resulting precipitate was filtered off, washed with water, and dried (40°C) to give 2-(3,4.5-trihydroxy7enyl)-3. 5.7-}1,2-Na7-toquinonezoacide 5- of hydroxybenzopyran
17.4 g of sulfonic acid ester was obtained.

(2) Synthesis of photosensitive material b 2-(3,4.5-}lihydroxy7enyl)-3-
(3,4.5-trihydroxybenzoyloxy)
-5.7-dihydroxybenzopyran 5.0g, 1.2
Ichina 7 Toki/Nnoazido 5-Sulfonyl chloride 18
．． 2 and 200 ml of acetone were placed in a three-necked flask and uniformly dissolved.

Then, triethylamine/acetone=7, o. ,/5
0 ml of the mixed solution was gradually added dropwise, and the mixture was reacted at 25° C. for 3 hours. The reaction mixture was poured into 1500 ml of a 1% aqueous hydrochloric acid solution, and the resulting precipitate was filtered, washed with water, and dried (40°C) to give 2-(3,4.5-trihydroxy7enyl).
-3- (3,4.5-}ri゜hydroxybenzoyloxy)-5.7-dihydroxybenzobilane 1,2
-na7toquinonediazide-5-sulfonic acid ester 16
．． 2g was obtained.

(3) Synthesis of photosensitive material C 11.5 g of 2,3.4-}lyhydroxybenzo7enone
30.2 g of 11,2-na7toquinonecyanodo-5-sulfonyl chloride and 30.1 g of acetone were charged into a three-necked flask and uniformly dissolved. Then triethylamine/
A mixed solution of 11.4 g of acetone/50% was gradually added dropwise, and the mixture was reacted at 25° C. for 3 hours. The reaction mixture was poured into 1500 liters of 1% aqueous hydrochloric acid solution, and the resulting precipitate was filtered, washed with water, and dried (40°C). 29.8 g of 2-Na7toquinonediazide-5-sulfonic acid ester was obtained.

(4) Synthesis of photosensitive material d 2,3,4,4'-teto2hydroxybenzo7enone 12,3gs 1s2-na7toquinonediazide-'5
-40.3 g of sulfonyl chloride and 300 I of acetone
Ill was charged into a three-necked flask and uniformly dissolved. Then triethylamine/acetone = 15.2g/50ml
The mixed solution was gradually added dropwise, and the mixture was reacted at 25° C. for 3 hours.

Pour the reaction mixture into 1500a+l of 1% aqueous hydrochloric acid solution,
The resulting precipitate was filtered, washed with water, and dried (40°C). Esters 39.7. I got it.

(5) Synthetic eyelids made of novolak resin - 40 gs of cresol9-60 g of cresol 137%
49 g of formalin aqueous solution and 0.13 g of oxalic acid were placed in a three-necked flask, heated to 100° C. with stirring, and reacted for 15 hours.

After that, the temperature was raised to 200℃ and gradually 5+eIIIH
Water, unreacted monomers, formaldehyde, oxalic acid, and the like were removed by reducing the pressure to 1.5 g. Then, the molten alkali-soluble novolak resin was returned to room temperature and recovered. The obtained volac resin had a weight average molecular weight of 7,100 (calculated as boristyrene).

(6) Preparation and evaluation of positive type photorenost composition 1.3 g each of photosensitive materials a to d obtained in the above (I) to (4)
and the cresol novolak resin obtained in (5) above (
Molecular weight 7100) 5g ethyl cellosolve acetate}1
The solution was dissolved in 5 g and filtered using a 0.2 µm micro 7 filter to prepare 7 otongist composition. This photoresist composition was applied to a silicon wafer using a spinner, and heated at 90°C for 3 hours in a convection open environment under a nitrogen atmosphere.
After drying for 0 minutes, a glossy resist film with a film thickness of 1.5 μm was obtained.

A reduction projection exposure device (NSR150 manufactured by Nikon Corporation) was applied to this film.
5G), developed for 1 minute with a 2.38% tetramethylammonium hydroxide aqueous solution, and
Washed with water for a second and dried.

The resist pattern of the silicon wafer thus obtained was observed with a scanning electron microscope and the resist was evaluated. The results are shown in Table-1.

The sensitivity was defined as the reciprocal of the exposure amount for reproducing a mask pattern of 2.0 μm theory, and was expressed as a relative value of the sensitivity of Comparative Example 1.

The residual film rate was expressed as a percentage of the ratio of the unexposed area before and after development.

The resolution represents the limit resolution at an exposure amount that reproduces a mask pattern of 2.0 .mu.m.

Heat resistance was determined by baking a silicon wafer on which a resist pattern was formed for 30 minutes in a convection open environment, and showing the temperature at which the pattern did not deform.

The shape of the resist was expressed as the angle (e) between the resist wall surface and the plane of the silicon wafer in the cross section of the resist pattern of 1.0 μm.

As can be seen, the resists using the photoreceptors a and b of the present invention were particularly excellent in resolution and resist shape.

The photosensitive materials of the present invention also have excellent solubility in ethylene glycol molybdenum/ethyl ether acetate, and resist composition solutions using these photosensitive materials show no precipitation even when left at 40°C for 50 days. However, when the resist composition solutions using photosensitive materials c and d of comparative examples were left to stand under the same conditions, precipitation was observed in the resist compositions.

Claims (1)

[Scope of Claims] A positive photoresist composition characterized by containing a compound represented by the following general formula (I) and an alkali-soluble resin. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) R_2: Hydroxyl group, -OR_4 group, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼Group, R_3, R_5: May be the same or different, hydrogen atom,
Represents a halogen atom, alkyl group, aryl group, aralkyl group, alkoxy group, acyl group, alkoxycarbonyl group, alkyloxy group, aryloyloxy group, cyano group or nitro group, and these groups have a substituent. R_4, R_6: may be the same or different, 1,2-naphthoquinonediazide-4-sulfonyl group, or 1,2-naphthoquinonediazide-5-sulfonyl group, a, b: may be the same or different , an integer of 1 to 3, m, n: may be the same or different, and is 0 or an integer of 1 to 3, and (am) and (bn) are integers of 1 or more.