Photoresist compositions

Abstract

The present invention relates to a composition and a process for preparing a composition that comprises: a) a novolak resin partially esterified with from about 1 to about 7 weight percent (further from about 3 to about 7 weight percent) of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; c) at least one photosensitive component in an amount sufficient to photosensitize said composition; and d) at least one solvent.

1 . A composition comprising: a) a novolak resin partially esterified with from about 1 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; c) at least one photosensitive component in an amount sufficient to photosensitize said composition; and d) at least one solvent.  
     
     
         2 . The composition of  claim 1  wherein a) the novolak resin is partially esterified from about 3 to about weight percent of a naphthoquinonediazidosulfonyl group.  
     
     
         3 . The composition of  claim 1  wherein for a) the naphthoquinonediazidosulfonyl group is selected from 1,2-naphthoquinonediazide-4-sulfonyl group, a 1,2-naphthoquinonediazide-5-sulfonyl group, a 7-methyl-1,2-naphthoquinonediazide-4-sulfonyl group, a 2,1-naphthoquinonediazide-4-sulfonyl group, a 2,1-naphthoquinonediazide-6-sulfonyl group, a 2,1-naphthoquinonediazide-7-sulfonyl group, and a 2,1-naphthoquinonediazide-8-sulfonyl group.  
     
     
         4 . The composition of  claim 3  wherein for a) the naphthoquinonediazidosulfonyl group is a 1,2-naphthoquinonediazide-4-sulfonyl group or a 1,2-naphthoquinonediazide-5-sulfonyl group.  
     
     
         5 . The composition of  claim 1  wherein b) one or more dilution resins is selected from the group consisting of a non-esterified novolak resin, polyhydroxy phenols, and mixtures thereof.  
     
     
         6 . The composition of  claim 5  wherein b) one or more dilution resins is a mixture of a non-esterified novolak resin and polyhydroxy phenols.  
     
     
         7 . The composition of  claim 6  wherein b) the partially esterified novolak resin is selected from a resin formed by a condensation reaction between trimethylphenol and formaldehyde, a resin formed by a condensation reaction between acetone and pyrogallol, a resin formed by a condensation reaction between m-cresol, p-cresol, trimethylphenol, and formaldehyde or mixtures thereof.  
     
     
         8 . The composition of  claim 7  wherein the polyhydroxy phenols is selected from the group consisting of 1,1-bis(4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,5-dimethyl-2-hydoxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(4-hydroxy-3-methylphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(2,6-dimethyl-4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,4-dihydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,4,5-trihydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1.1-bis(4-hydroxy-3-methylphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(2,6-dimethyl-4-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,4-dihydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,4,5-trihydroxyphenyl)-1-[4-(1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 4,4′,4″,4′″-(1,4-phenylenedimethylidyne)tetrakisphenol, 4,4′-[(3-hydroxyphenyl)methylene]bis[2-methylethylphenol], 2,2′-[(3-hydroxyphenyl)methylene]bis[3,5,6-trimethylphenol],2,2′-[(2-hydroxy-3-methoxylphenyl)methylene]bis[3,5-dimethylphenol], 2,2′-[(4-hydroxy-3-methoxyphenyl)methylene]bis[3,5-dimethylphenol], 4-[bis(4-hydroxyphenyl)methyl]-2-ethoxyphenol, 4-[bis(4-hydroxyphenyl)methyl]-2-methoxyphenol, 2,4,6-tris(4-hydroxyphenylmethyl)-1,3-benzenediol, 4,4′-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol, 4-(2,3,5-trimethyl-4-hydroxyphenyl)methyl-1,3-benzenediol, 6,6′-methylenebis[4-(4-hydroxy-3,5-dimethylphenylmethyl)-1,2,3-benzenetriol], 2,6-bis[(2,4-dihydroxyphenyl)methyl]-4-ethylphenol, 2,4-bis[(2,4-dihydroxyphenyl)methyl]-6-cyclohexylphenol, 2,6-bis[[2,3-dihydroxy-5-(1,1-dimethylethyl)phenyl]methyl]-4-methylphenol, 4,4′-[(3,4-dihydroxyphenyl)methylen]bis[2-(methylethyl)phenol], 2,2′-[(3,4-dihydroxyphenyl)methylene]bis[3,5,6-trimethylphenol], 2,2′-[(3-hydroxy-4-methoxyphenyl)methylene]bis[3,5-dimethylphenol], 2,4′,4″-methylidynetrisphenol, 4,4′-[(2-hydroxyphenyl)methylene]bis[3-methylphenol], 4,4′,4″-(3-methyl-1-propanyl-3-ylidene)trisphenol, 2,2′-[(3-hydroxyphenyl)methylene]bis[3,5-dimethylphenol], 4,4′,4″,4′″-(1,2-ethanediylidene)tetrakisphenol, 4,6-bis[(4-hydroxyphenyl)methyl]-1,3-benzenediol, 4,4′-[(3,4-dihydroxyphenyl)methylene]bis[2-methylphenol], 2,2′-[(2-hydroxyphenyl)methylene]bis[3,5-dimethylphenol], 2,2′-[(4-hydroxyphenyl)methylene]bis[3,5-dimethylphenol], (2,4-dihydroxyphenyl)(4-hydroxyphenyl)methane, 4-[1-(4-hydroxyphenyl)-1-methylethyl]-1,3-benzenediol, 4-[(3,5-dimethyl-4-hydroxyphenyl)methyl]-1,2,3-benzenetriol, 4,4′-[1,4-phenylenebis(1-methylethylidene)]bis[benzene-1,2-diol], 5,5′-[1,4-phenylenebis(1-methylethylidene)]bis[benzene-1,2,3-triol], 4-[(2,3,5-trimethyl-4-hydroxyphenyl)methyl]-1,2,3-benzenetriol, 4,4′-methylenebis[6-methylcarbonyl-1,3-benzenediol], 6,6′-methylenebis[4-(4-hydroxyphenylmethyl)-1,2,3-benzenetriol], 6,6′-ethylidenebis[4-(4-hydroxyphenylcarboxy)-1,2,3-benzenetriol], 4,4′,4″-methylidynetris[2,6-bis[(hydroxyphenyl)methyl]phenol], 4,4′,4″-ethylidenetris[2,6-bis[(hydroxyphenyl)methyl]phenol], 2,2′-bis[(3,4-dihydroxyphenyl)methylene]bis [3,5-dimethylphenol], 4-[(4-hydroxyphenyl)methyl]-1,2,3-benzenetriol, and 4,4′-[1,4-phenylenebis(1-methylethylidene)]bis[benzene-1,2,3-triol].  
     
     
         9 . The composition of  claim 8  wherein b) is a mixture between a resin formed by a condensation reaction between m-cresol, p-cresol, trimethylphenol, and formaldehyde and 4,4′-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphenol.  
     
     
         10 . The composition of  claim 5  wherein b) is a mixture of non-esterified novolak resins.  
     
     
         11 . The composition of  claim 10  wherein b) is a mixture of any two resins formed by a condensation reaction between trimethylphenol and formaldehyde, a resin formed by a condensation reaction between acetone and pyrogallol, a condensation reaction between xylenol, m- and/or p-cresol, and formaldehyde, or a resin formed by a condensation reaction between m-cresol, p-cresol, trimethylphenol, and formaldehyde.  
     
     
         12 . The composition of  claim 1  wherein the photosensitive compound is selected from a reaction product between a naphthoquinonediazidesulfonyl halide or benzoquinonediazidesulfonyl halide and a compound containing at least one hydroxyl group selected from hydroquinone; resorcinol; phenol, p-methoxyphenol, dimethylphenol, bisphenol A, naphthol, pyrocatechol, pyrogallol monomethyl ether, pyrogallol-1,3-dimethyl ether, gallic acid, partially esterified or partially etherified gallic acid and other phenols; 2,4-dihydroxybenzophenone, 2,3,4-trihydroxybenzophenone, 2,4,6-trihydroxybenzophenone, 2,4,4′-trihydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2,2′,4,4′-tetrahydroxybenzophenone, 2,2′,3,4,6′-pentahydroxybenzophenone, 2,3′,4,4′,6-pentahydroxybenzophenone, 2,2′,3,4,4′-pentahydroxybenzophenone, 2,2′,3,4,5′-pentahydroxybenzophenone, 2,3′,4,5,5′-pentahydroxybenzophenone, 2,3,3′,4,4′,5′-hexahydroxybenzophenone and other polyhydroxybenzophenones; bis(2,4-dihydroxyphenyl)methane, bis(2,3,4-trihydroxyphenyl)methane, bis(2,4-dihydroxyphenyl)propane and other hydroxyphenylalkanes; 4,4′,3″,4″-tetrahydroxy-3,5,3′,5′-tetramethylphenylmethane, 4,4′,2″,3″,4″-pentahydroxy-3,5,3′,5′-tetramethyltriphenylmethane and other hydroxytriphenylmethanes; bis[3-(3,5-dimethyl-4-hydroxybenzyl)-4-hydroxy-5-methylphenyl]methane, bis[3-(3,5-dimethyl-4-hydroxybenzyl)-4-hydroxy-5-ethylphenyl]methane, bis[3-(3,5-diethyl-4-hydroxybenzyl)-4-hydroxy-5-methylphenyl]methane, bis[3-(3,5-diethyl-4-hydroxybenzyl)4-hydroxy-5-ethylphenyl]methane and other terminal xylenol linear tetranuclear compounds; 2,4-bis[2-hydroxy-3-(4-hydroxybenzyl)-5-methylbenzyl]-6-cyclohexylphenol, 2,4-bis[4-hydroxy-3-(4-hydroxybenzyl)-5-methylbenzyl]-6-cyclohexylphenol and other linear pentanuclear compounds and other linear polyphenolic compounds; bis[2-hydroxy-3-(3,5-dimethyl-4-hydroxybenzyl )-5-methylphenyl]methane, bis[2-hydroxy-3-(2-hydroxy-5-methylbenzyl)-5-methylphenyl]methane, bis[4-hydroxy-3-(2-hydroxy-5-methylbenzyl)-5-methylphenyl]methane, bis[2,5-dimethyl-3-(4-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane, bis[2,5-dimethyl-3-(4-hydroxybenzyl)-4-hydroxyphenyl]methane, bis[2,5-dimethyl-3-(2-hydroxybenzyl)-4-hydroxyphenyl]methane and other linear tetranuclear compounds; 1,1-bis(4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,5-dimethyl-2-hydoxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(4-hydroxy-3-methylphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(2,6-dimethyl-4-hydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,4-dihydroxyphenyl)-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(3,4,5-trihydroxyphenyl )-1-[4-(4-hydroxybenzyl)phenyl]ethane, 1,1-bis(4-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,5-dimethyl-4-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1.1-bis(4-hydroxy-3-methylphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(2,6-dimethyl-4-hydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, 1,1-bis(3,4-dihydroxyphenyl)-1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl ]ethane, 1,1-bis(3,4,5-trihydroxyphenyl)-1-[4-(1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethane, and other non-linear tetranuclear compounds; bis(4-hydroxy-2,3,5-trimethylphenyl)-2-hydroxyphenylmethane, 1,4-bis[1-(3,5-dimethyl-4-hydroxyphenyl)isopropyl]benzene, 2,4-bis(3,5-dimethyl-4-hydroxyphenylmethyl)-6-methylphenol, bis(4-hydroxy-3,5-dimethylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy-2,5-dimethylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy-3,5-dimethylphenyl)-3,4-dihydroxyphenylmethane, 1-[1-(4-hydroxyphenyl)isopropyl]-4-[1,1-bis(4-hydroxyphenyl)ethyl]benzene, 1-[1-(3-methyl-4-hydroxyphenyl)isopropyl]-4-[1,1-bis(3-methyl-4-hydroxyphenyl)ethyl]benzene, 2,6-bis[1-(2,4-dihydroxyphenyl)isopropyl]-4-methylphenol, 4,6-bis[1-(4-hydroxyphenyl)isopropyl]resorcin, 4,6-bis(3,5-dimethoxy-4-hydroxyphenylmethyl)pyrogallol, 4,6-bis(3,5-dimethyl-4-hydroxyphenylmethyl)pyrogallol, 2,6-bis(3-methyl-4,6-dihydroxyphenylmethyl)-4-methylphenol, 2,6-bis(2,3,4-trihydroxyphenylmethyl)-4-methylphenol, 1,1-bis(4-hydroxyphenyl)cyclohexane and other hydroxyaryls, and a compound represented by formula (I) or (II)  
       
         
           
           
               
               
           
         
       
       wherein R 3 , R 4  and R 5  are independently selected from the group consisting of a hydrogen atom, a 1,2-naphthoquinonediazide-4-sulfonyl group, a 1,2-naphthoquinonediazide-5-sulfonyl group, a 7-methyl-1,2-naphthoquinonediazide-4-sulfonyl group, a 2,1-naphthoquinonediazide-4-sulfonyl group, a 2,1-naphthoquinonediazide-6-sulfonyl group, a 2,1-naphthoquinonediazide-7-sulfonyl group, a 2,1-naphthoquinonediazide-8-sulfonyl group, and mixtures thereof, and R 3 , R 4  and R 5  cannot be a hydrogen atom at the same time, R 6a , R 6b , R 6c , R 7a , R 7b , R 7c , and R 7d  are independently selected from a hydrogen atom or C 1-4  alkyl group, and n represents 1 or 2.  
     
     
         13 . The composition of  claim 12  wherein b) the photosensitive compound is selected from  
       
         
           
           
               
               
           
         
       
       where DNQ is 2,1-diazonaphthoquinone-5-sulfonyl-.  
     
     
         14 . The composition of  claim 1  wherein d) at least one solvent is selected from 2-heptanone, anisole, ethyl lactate, n-butyl acetate, propylene glycol methyl ether, propylene glycol methyl ether, ethyl 3-ethoxypropionate and mixtures thereof.  
     
     
         15 . The composition of  claim 1  wherein d) at least one solvent is 2-heptanone.  
     
     
         16 . The composition of  claim 1  wherein d) at least one solvent is a mixture of ethyl lactate and with n-butyl acetate.  
     
     
         17 . The composition of  claim 1  wherein d) at least one solvent is and propylene glycol methyl ether acetate.  
     
     
         18 . A process for preparing a composition comprising providing an admixture of: a composition comprising: a) a novolak resin partially esterified with from about 1 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; c) at least one photosensitive component in an amount sufficient to photosensitize said composition; and d) at least one solvent.  
     
     
         19 . The process of  claim 18  wherein for a) the novolak resin is partially esterified with from about 3 to about 7 weight percent of a naphthoquinonediazidosulfonyl group.  
     
     
         20 . A process for forming an image on a substrate comprising coating a substrate with a composition according to  claim 1;  imagewise exposing through a mask with ultraviolet radiation; and developing the exposed photoresist composition with a developer.  
     
     
         21 . A method for producing a microelectronic device by forming an image on a substrate comprising: 
 i) providing an admixture of a photoresist composition comprising: a) a novolak resin partially esterified with from about 1 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; c) at least one photosensitive component in an amount sufficient to photosensitive said composition; and d) at least one solvent    ii) coating a suitable substrate with the photoresist composition of step i); and    iii) heat treating the coated substrate of step ii) until substantially all of the photoresist solvent is removed; image-wise exposing the photoresist composition and removing the image-wise exposed areas of such composition with a suitable developer.