Negative-type photosensitive resin composition, cured film, display device provided with cured film, and production method therefor

A negative photosensitive resin composition comprising,

• as an alkali-soluble resin (A), at least a weakly acidic group-containing resin (A1), and an unsaturated group-containing resin (A2),
• a radical-polymerizable compound (B),
• a photosensitive agent (C), and
• a coloring agent (D),
• the weakly acidic group-containing resin (A1) containing an acidic group having an acid dissociation constant in the range of 13.0 to 23.0 in dimethyl sulfoxide, and
• the unsaturated group-containing resin (A2) having an ethylenically unsaturated double bond group,
• wherein
• the weakly acidic group-containing resin (A1) includes one or more selected from the group consisting of polyimide (A1a-1), polyimide precursor (A1a-2), carboxylic acid-modified polysiloxane (A1a-3), carboxylic acid-modified novolac resin (A1a-4), carboxylic acid-modified polyhydroxystyrene (A1a-5), polybenzoxazole (A1b-1), polybenzoxazole precursor (A1b-2), polysiloxane (A1b-3), novolac resin (A1b-4), and polyhydroxystyrene (A1b-5),
• the coloring agent (D) contains a black pigment (D1a) as a pigment (D1),
• the black pigment (D1a) contains a benzofuranone based black pigment (D1a-1a) and/or a perylene based black pigment (D1a-1b) as a black organic pigment (D1a-1),
• the benzofuranone based black pigment (D1a-1a) includes a benzofuranone compound as represented by any of general formulae (63) to (68), a geometrical isomer thereof, a salt thereof, or a geometrical isomer salt thereof, and
• the perylene based black pigment (D1a-1b) includes a perylene compound as represented by any of general formulae (69) to (71), a geometrical isomer thereof, a salt thereof, or a geometrical isomer salt thereof;
• wherein in formulae (63) to (65),
• R206, R207, R212, R213, R218, and R219 are each independently a hydrogen atom, a halogen atom, an alkyl group containing 1 to 10 carbon atoms, or an alkyl group containing 1 to 10 carbon atoms and 1 to 20 fluorine atoms;
• R208, R209, R214, R215, R220, and R221 are each independently a hydrogen atom, a halogen atom, R251, COOH, COOR251, COO—, CONH2, CONHR251, CONR251R252, CN, OH, OR251, OCOR251, OCONH2, OCONHR251, OCONR251R252, NO2, NH2, NHR251, NR251R252, NHCOR251, NR251COR252, N═CH2, N═CHR251, N═CR251R252, SH, SR251, SOR251, SO2R251, SO3R251, SO3H, SO3−, SO2NH2, SO2NHR251, or SO2NR251R252, and R251 and R252 are each independently an alkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 4 to 10 carbon atoms, an alkenyl group containing 2 to 10 carbon atoms, a cycloalkenyl group containing 4 to 10 carbon atoms, or alkynyl group containing carbon atoms 2 to 10;
• a plurality selected from R208, R209, R214, R215, R220, and R221 may be connected by a direct bond, oxygen atom bridge, sulfur atom bridge, NH bridge, or NR251 bridge to form a ring;
• R210, R211, R216, R217, R222, and R223 are each independently a hydrogen atom, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 15 carbon atoms;
• and
• a, b, c, d, e, and f are each independently an integer of 0 to 4;
• wherein in formulae (66) to (68),
• R253, R254, R259, R260, R265, and R266 are each independently a hydrogen atom, a halogen atom, an alkyl group containing 1 to 10 carbon atoms, or an alkyl group containing 1 to 10 carbon atoms and 1 to 20 fluorine atoms;
• R255, R256, R261, R262, R267, and R268 are each independently a hydrogen atom, a halogen atom, R271, COOH, COOR271, COO—, CONH2, CONHR271, CONR271R272, CN, OH, OR271, OCOR271, OCONH2, OCONHR271, OCONR271R272, NO2, NH2, NHR271, NR271R272, NHCOR271, NR271COR272, N═CH2, N═CHR271, N═CR271R272, SH, SR271, SOR271, SO2R271, SO3R271, SO3H, SO3−, SO2NH2, SO2NHR271, or SO2NR271R272, and R271 and R272 are each independently an alkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 4 to 10 carbon atoms, an alkenyl group containing 2 to 10 carbon atoms, a cycloalkenyl group containing 4 to 10 carbon atoms, or alkynyl group containing 2 to 10 carbon atoms;
• a plurality selected from R255, R256, R261, R262, R267, and R268 may be connected by a direct bond, oxygen atom bridge, sulfur atom bridge, NH bridge, or NR271 bridge to form a ring;
• R257, R258, R263, R264, R269, and R270 are each independently a hydrogen atom, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 15 carbon atoms;
• and
• a, b, c, d, e, and f are each independently an integer of 0 to 4;
• wherein in formulae (69) to (71),
• X92, X93, X94, and X95 are each independently an alkylene chain containing 1 to 10 carbon atoms;
• R224 and R225 are each independently a hydrogen atom, a hydroxyl group, an alkoxy group containing 1 to 6 carbon atoms, or an acyl group containing 2 to 6 carbon atoms;
• R273 and R274 are each independently a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms;
• and
• a and b are each an integer of 0 to 5.

A negative photosensitive resin composition comprising,

• as an alkali-soluble resin (A), at least a weakly acidic group-containing resin (A1), and an unsaturated group-containing resin (A2),
• a radical-polymerizable compound (B) and
• a photosensitive agent (C),
• the weakly acidic group-containing resin (A1) containing an acidic group having an acid dissociation constant in the range of 13.0 to 23.0 in dimethyl sulfoxide,
• the weakly acidic group-containing resin (A1) including one or more selected from the group consisting of polyimide (A1a-1), polyimide precursor (A1a-2), carboxylic acid-modified polysiloxane (A1a-3), carboxylic acid-modified novolac resin (A1a-4), carboxylic acid-modified polyhydroxystyrene (A1a-5), polybenzoxazole (A1b-1), polybenzoxazole precursor (A1b-2), polysiloxane (A1b-3), novolac resin (A1b-4), and polyhydroxystyrene (A1b-5), and
• the unsaturated group-containing resin (A2) having an ethylenically unsaturated double bond group,
• wherein the unsaturated group-containing resin (A2) includes one or more selected from the group consisting of unsaturated group-containing polyimide (A2a-1), unsaturated group-containing polyimide precursor (A2a-2), carboxylic acid-modified unsaturated group-containing polysiloxane (A2a-3), unsaturated group-containing polybenzoxazole (A2b-1), unsaturated group-containing polybenzoxazole precursor (A2b-2), and unsaturated group-containing polysiloxane (A2b-3).