Negative-type photosensitive resin composition, cured film, element and display apparatus that include cured film, production method for the same

Abstract

To provide an alkaline developable negative-type photosensitive resin composition from which a cured film that has a high-resolution and low-taper pattern shape and that are excellent in heat resistance and light blocking property can be obtained. A negative-type photosensitive resin composition is characterized by containing an (A1) first resin, a (A2) second resin, a (C) photopolymerization initiator, and a (D) coloring agent, wherein the (A1) first resin is an (A1-1) polyimide and/or an (A1-2) polybenzo-oxazole, and wherein the (A2) second resin is one or more species selected from a (A2-1) polyimide precursor, a (A2-2) polybenzo-oxazole precursor, a (A2-3) polysiloxane, a (A2-4) cardo based resin, and an (A2-5) acrylic resin, and wherein a content ratio of the (A1) first resin in a total of 100 mass % of the (A1) first resin and the (A2) second resin is within the range of 25 to 90 mass %.

1 . A cured film obtained by curing the negative-type photosensitive resin composition comprising an (A1) first resin, a (A2) second resin, a (C) photopolymerization initiator, and a (D) coloring agent,
 wherein the (A1) first resin is an (A1-1) polyimide and/or an (A1-2) polybenzo-oxazole, and   wherein the (A2) second resin is one or more species selected from a (A2-2) polybenzo-oxazole precursor, a (A2-3) polysiloxane, a (A2-4) cardo based resin, and an (A2-5) acrylic resin, and   wherein a content ratio of the (A1) first resin in a total of 100 mass % of the (A1) first resin and the (A2) second resin is within a range of 25 to 90 mass %.   
     
     
         2 . The cured film according to  claim 1 , wherein the (D) coloring agent contains a (D1) pigment and the (D1) pigment content ratio in the entire solid content of the negative photosensitive resin composition is within a range of 5 to 70 mass %. 
     
     
         3 . The cured film according to  claim 1 , wherein the (D) coloring agent contains a (Da) black coloring agent and the (Da) black coloring agent contains a (D1a) black pigment. 
     
     
         4 . The cured film according to  claim 3 , wherein the (D1a) black pigment is a (D1a-1) black organic pigment and the (D1a-1) black organic pigment is a (D1a-1a) benzofuranone based black pigment, and the (D1a-1a) benzofuranone based black pigment is benzofuranone compound represented by any one of general formulas (63) to (68). 
       
         
           
           
               
               
           
         
         (In general formulas (63) to (65), R 206 , R 207 , R 212 , R 213 , R 218 , and R 219  each independently represent hydrogens, halogen atoms, alkyl groups having a carbon number of 1 to 10, or an alkyl group having a carbon number of 1 to 10 which has 1 to 20 fluorine atoms. R 208 , R 209 , R 214 , R 215 , R 220 , and R 221  each independently represent hydrogen, a halogen atom, R 251 , COOH, COOR 251 , COO − , CONH 2 , CONHR 251 , CONR 251 R 252 , CN, OH, OR 251 , OCOR 251 , OCONH 2 , OCONHR 251 , OCONR 251 R 252 , NO 2 , NH 2 , NHR 251 , NR 251 R 252 , NHCOR 251 , NR 251 COR 252 , N═CH 2 , N═CHR 251 , N═CR 251 R 252 , SH, SR 251 , SOR 251 , SO 2 R 251 , SO 3 R 251 , SO 3 H, SO 3   − , SO 2 NH 2 , SO 2 NHR 251  or SO 2 NR 251 R 252 , and R 251  and R 252  each independently represent an alkyl group having a carbon number of 1 to 10, a cycloalkyl group having a carbon number of 4 to 10, an alkenyl group having a carbon number of 2 to 10, a cycloalkenyl group having a carbon number of 4 to 10, or an alkynyl group having a carbon number of 2 to 10. A plurality of R 208 , R 209 , R 214 , R 215 , R 220  or R 221  may form a ring by a direct bond, an oxygen atom bridge, a sulfur atom bridge, an NH bridge, or an NR 251  bridge. R 210 , R 211 , R 216 , R 217 , R 222 , and R 223  each independently represent hydrogen, an alkyl group having a carbon number of 1 to 10, or an aryl group having a carbon number of 6 to 15. a, b, c, d, e, and f each independently represent an integer of 0 to 4.) 
       
       
         
           
           
               
               
           
         
         (In general formulas (66) to (68), R 253 , R 254 , R 259 , R 260 , R 265 , and R 266  each independently represent hydrogen, a halogen atom, an alkyl group having a carbon number of 1 to 10, or an alkyl group having a carbon number of 1 to 10 which has 1 to 20 fluorine atoms. R 255 , R 256 , R 261 , R 262 , R 267 , and R 268  each independently represent hydrogen, halogen atom, R 271 , COOH, COOR 271 , COO − , CONH 2 , CONHR 271 , CONR 271 R 272 , CN, OH, OR 271 , OCOR 271 , OCONH 2 , OCONHR 271 , OCONR 271 R 272 , NO 2 , NH 2 , NHR 271 , NR 271 R 272 , NHCOR 271 , NR 271 COR 272 , N═CH 2 , N═CHR 271 , N═CR 271 R 272 , SH, SR 271 , SOR 271 , SO 2 R 271 , SO 3 R 271 , SO 3 H, SO 3   − , SO 2 NH 2 , SO 2 NHR 271  or SO 2 NR 271 R 272 . R 271  and R 272  each independently represent an alkyl group having a carbon number of 1 to 10, a cycloalkyl group having a carbon number of 4 to 10, an alkenyl group having a carbon number of 2 to 10, a cycloalkenyl group having a carbon number of 4 to 10, or an alkynyl group having a carbon number of 2 to 10. A plurality of R 255 , R 256 , R 261 , R 262 , R 267  or R 268  may form a ring by a direct bond, an oxygen atom bridge, a sulfur atom bridge, an NH bridge, or an NR 271  bridge. R 257 , R 258 , R 263 , R 264 , R 269 , and R 270  each independently represent hydrogen, an alkyl group having a carbon number of 1 to 10, or an aryl group having a carbon number of 6 to 15. a, b, c, d, e, and f each independently represent an integer of 0 to 4.) 
       
     
     
         5 . The cured film according to  claim 1 , wherein one or more species selected from the (A1-1) polyimide, the (A1-2) polybenzo-oxazole, and the (A2-2) polybenzo-oxazole precursor contain a structural unit that has a fluorine atom. 
     
     
         6 . The cured film according to  claim 1 , wherein one or more species selected from the (A1-1) polyimide, the (A1-2) polybenzo-oxazole, and the (A2-2) polybenzo-oxazole precursor contain a structural unit originating from an amine having an oxyalkylene structure and/or amine derivative having an oxyalkylene structure. 
     
     
         7 . An element comprising the cured film according to  claim 1 . 
     
     
         8 . A display apparatus comprising the cured film according to  claim 1 . 
     
     
         9 . The display apparatus according to  claim 8 , wherein the display apparatus is an organic EL display, and the cured film is put to uses as at least one of a planarization layer on a drive circuit, an electrically insulating layer on a first electrode, pixel-separating layer, a planarization film for TFTs, and TFT protective layer. 
     
     
         10 . The display apparatus according to  claim 9 ,
 wherein an optical density per 1 μm of film thickness of the cured film is within a range of 0.3 to 5.0,   wherein the organic EL display does not have either a polarizing plate or a quarter-wavelength plate at the light extraction side of the light-emitting elements,   wherein the display apparatus is a flexible organic EL display, and the flexible organic EL display has a structure stacked on a flexible substrate,   wherein the flexible substrate contains polyimide.   
     
     
         11 . The display apparatus according to  claim 8 , wherein the cured film is put to uses as a black matrix and/or a black column spacer.