Photosensitive polyimide compositions

Abstract

A photosensitive resin composition comprising a pre-imidized aromatic polyimide, which when coated on a silicon wafer, has a light transmittance at a wavelength of 365 nm of at least 1% and imparts low residual stress after cure. The composition can be patterned through I-line exposure followed by development with organic or alkaline solutions, and can be cured at relatively mild temperature to yield low-stress polyimide patterns. Electronic components having the polyimide patterns have high reliability.

1 . A composition comprising a polyimide component and an organic solvent, 
 wherein the polyimide component is represented by a polyimide having a repeat unit represented the formula;                          where X can be equal to SO 2  or C(CF 3 ) 2 , C(CF 3 )phenyl, C(CF 3 )CF 2 CF 3 , or C(CF 2 CF 3 )phenyl, and combinations thereof, and    wherein the Y component Y is derived from one or more diamines, wherein at least a portion of the Y component is derived from a hydroxyl- or carboxyl-containing diamine compound,    wherein a percentage of the total hydroxyl or carboxyl groups of the diamine component from between and including any two of the following numbers, 0, 2, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 98 and 100 mole percent have been derivatized to contain an ethylenically unsaturated moiety capable of crosslinking.    
   
   
       2 . The composition of  claim 1  wherein Y is derived from a hydroxyl- or carboxyl-containing diamine compound selected from the group consisting of, 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6F-AP), 3,3′-dihydroxy-4,4′-diaminobiphenyl (HAB), 2,4-diaminophenol, 2,3-diaminophenol, 3,3′-diamino-4,4′-dihydroxy-biphenyl and 2,2′-bis(3-amino-3-hydroxyphenyl)hexafluoropropane, methylene-bis-anthranilic acid and mixtures thereof.  
   
   
       3 . The composition of  claim 1  wherein at least a portion of the Y is derived from a hydroxyl- or carboxyl-containing diamine compound selected from the group consisting of, 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6F-AP), 3,3′-dihydroxy-4,4′-diaminobiphenyl (HAB), 2,4-diaminophenol, 2,3-diaminophenol, 3,3′-diamino-4,4′-dihydroxy-biphenyl and 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, methylene-bis-anthranilic acid and mixtures thereof.  
   
   
       4 . The composition of  claim 1  wherein the Y components provide at least one half mole of hydroxyl or carboxyl moieties per mole of diamine compounds.  
   
   
       5 . The composition of  claim 1  wherein the Y components provide at least one mole of hydroxyl or carboxyl moieties per mole of diamine compounds.  
   
   
       6 . The composition of  claim 1  wherein the polyimide compound is solvent soluble and spin-coatable onto a substrate.  
   
   
       7 . The composition of  claim 1  wherein the polyimide compound is solvent soluble and spin-coatable onto a substrate to form a polyimide film, wherein the maximum temperature the substrate is exposed to during this process is less than 100° C.  
   
   
       8 . The composition of  claim 1  further comprising a polyimide component in which X can be equal to SO 2  or C(CF 3 ) 2 , C(CF 3 )phenyl, C(CF 3 )CF 2 CF 3 , or C(CF 2 CF 3 )phenyl, and combinations thereof, and Y is selected from the group consisting of 3,4′-diaminodiphenyl ether (3,4′-ODA), 4,4′-diamino-2,2′-bis(trifluoromethyl)biphenyl (TFMB), 3,3′,5,5′-tetramethylbenzidine, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 3,3′-diaminodiphenyl sulfone, 3,3′dimethylbenzidine, 3,3′-bis(trifluoromethyl)benzidine, 2,2′-bis-(p-aminophenyl)hexafluoropropane, bis(trifluoromethoxy)benzidine (TFMOB), 2,2′-bis(pentafluoroethoxy)benzidine (TFEOB), 2,2′-trifluoromethyl-4,4′-oxydianiline (OBABTF), 2-phenyl-2-trifluoromethyl-bis(p-aminophenyl)methane, 2-phenyl-2-trifluoromethyl-bis(m-aminophenyl)methane, 2,2′-bis(2-heptafluoroisopropoxy-tetrafluoroethoxy)benzidine (DFPOB), 2,2-bis(m-aminophenyl)hexafluoropropane (6-FmDA), 2,2-bis(3-amino-4-methylphenyl)hexafluoropropane, 3,6-bis(trifluoromethyl)-1,4-diaminobenzene (2TFMPDA), 1-(3,5-diaminophenyl)-2,2-bis(trifluoromethyl)-3,3,4,4,5,5,5-heptafluoropentane, 3,5-diaminobenzotrifluoride (3,5-DABTF), 3,5-diamino-5-(pentafluoroethyl)benzene, 3,5-diamino-5-(heptafluoropropyl)benzene, 2,2′-dimethylbenzidine (DMBZ), 2,2′,6,6′-tetramethylbenzidine (TMBZ), 3,6-diamino-9,9-bis(trifluoromethyl)xanthene (6FCDAM), 3,6-diamino-9-trifluoromethyl-9-phenylxanthene (3FCDAM), 3,6-diamino-9,9-diphenyl xanthene and mixtures thereof.  
   
   
       9 . The composition of  claim 1  wherein at least a portion of the hydroxyl or carboxyl groups of the diamine component have been derivatized to contain an o-quinonediazidosulfonyl moiety.  
   
   
       10 . The composition of  claim 1  wherein at least a portion of the hydroxyl or carboxyl groups of the diamine component have been derivatized to contain an ethylenically unsaturated moiety capable of crosslinking.  
   
   
       11 . The composition of  claim 1  wherein the polyimide material has an end and wherein the end of the polyimide chain has been derivatized to contain an ethylenically unsaturated moiety capable of crosslinking.  
   
   
       12 . A composition comprising a polyimide component and an organic solvent, 
 wherein the polyimide component is represented by a polyimide having a repeat unit represented the formula;                           where X can be equal to SO 2  or C(CF 3 ) 2 , C(CF 3 )phenyl, C(CF 3 )CF 2 CF 3 , or C(CF 2 CF 3 )phenyl, and combinations thereof, and    wherein Y is derived from a hydroxyl- or carboxyl-containing diamine component of a diamine selected from the group consisting of, 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6F-AP), 3,3′-dihydroxy-4,4′-diaminobiphenyl (HAB), 2,4-diaminophenol, 2,3-diaminophenol, 3,3′-diamino-4,4′-dihydroxy-biphenyl and 2,2′-bis(3-amino-3-hydroxyphenyl)hexafluoropropane, methylene-bis-anthranilic acid and mixtures thereof    wherein a percentage of the total hydroxyl or carboxyl groups of the diamine component from between and including any two of the following numbers, 0, 2, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 98 and 100 mole percent have been derivatized to contain an o-quinonediazidosulfonyl moiety.    
   
   
       13 . A composition comprising a polyimide component and an organic solvent. 
 wherein the polyimide component is represented by a polyimide having a repeat unit represented the formula;                           where X can be equal to SO 2  or C(CF 3 ) 2 , C(CF 3 )phenyl, C(CF 3 )CF 2 CF 3 , or C(CF 2 CF 3 )phenyl, and combinations thereof, and    wherein Y is derived from a hydroxyl- or carboxyl-containing diamine component of a diamine selected from the group consisting of, 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6F-AP), 3,3′-dihydroxy-4,4′-diaminobiphenyl (HAB), 2,4-diaminophenol, 2,3-diaminophenol, 3,3′-diamino-4,4′-dihydroxy-biphenyl and 2,2′-bis(3-amino-3-hydroxyphenyl)hexafluoropropane, methylene-bis-anthranilic acid and mixtures thereof    wherein the end of the polyimide chain has been derivatized to contain an ethylenically unsaturated moiety capable of crosslinking.    
   
   
       14 . A process comprising 
 (a) applying the composition of  claim 1  to a substrate;    (b) evaporating at least a portion of the organic solvent to form a polyimide film;    (c) exposing the polyimide film to radiation through a mask;    (d) and developing the exposed image to form a patterned polyimide structure.