Resin Composition, Varnish, Resin Film and Semiconductor Device

A resin composition comprising the following benzoxazole resin precursor and the following cross-linking agent:

• (1) a benzoxazole resin precursor,
• wherein the benzoxazole resin precursor has a first repeating unit obtained by reacting a bisaminophenol compound and a dicarboxylic acid compound and having a diamondoid structure selected from structural units having an adamantane structure as a minimum unit,
• wherein the first repeating unit is one or more kinds selected from:
• (a) a repeating unit obtained by reacting a bisaminophenol compound having a diamondoid structure and a dicarboxylic acid compound not having a diamondoid structure;
• (b) a repeating unit obtained by reacting a bisaminophenol compound not having a diamondoid structure and a dicarboxylic acid compound having a diamondoid structure;
• and
• (c) a repeating unit obtained by reacting a bisaminophenol compound having a diamondoid structure and a dicarboxylic acid compound having a diamondoid structure,
• wherein in the case of using the bisaminophenol compound having a diamondoid structure for obtaining the first repeating unit, a bisaminophenol compound selected from a bisaminophenol compound having a diamondoid structure in a bisaminophenol skeleton and a bisaminophenol compound having a diamondoid structure bonded to a bisaminophenol skeleton directly or via other atom is used, and
• in the case of using the dicarboxylic acid compound having a diamondoid structure for obtaining the first repeating unit, a dicarboxylic acid compound selected from a dicarboxylic acid compound having a diamondoid structure in a dicarboxylic acid skeleton and a dicarboxylic acid compound having a diamondoid structure bonded to a dicarboxylic acid skeleton directly or via other atom;
• and
• (2) a cross-linking agent,
• wherein the cross-linking agent has at least two or more groups capable of causing a cross linking reaction in a molecule by reacting crosslinking agents and has a diamondoid structure selected from structural units having an adamantane structure as a minimum unit.

A resin composition comprising a benzoxazole resin precursor having a third repeating unit represented by the following Formula (1) and a cross-linking agent having at least two or more groups capable of causing a cross linking reaction in a molecule by reacting crosslinking agents and having a diamondoid structure selected from structural units having an adamantane structure as a minimum unit:

• wherein, in the Formula (1), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “k” is an integer of 2 to 1000;
• X1 is at least a group selected from the group consisting of groups represented by the following Formula (2-1) and the following Formula (2-2) and groups represented by the following Formula (3);
• Y1 is at least a group selected from the group consisting of groups represented by the following Formula (4), Formula (6-1), Formula (6-2), Formula (7-1), Formula (7-2), Formula (8) and Formula (9);
• and the hydrogen atom of carbocycle contained in X1 and Y1 may be substituted by an alkyl group and/or a fluoroalkyl group:
• wherein, in the Formula (2-1) and Formula (2-2), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “a” is from 2 to 12;
• “p” is from 1 to 12;
• “i” is from 1 to 12;
• and “r” is from 0 or 1,
• wherein, in the Formula (3), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “p” is from 1 to 12;
• X2 is an ethynyl group or a propargylether group;
• “Z” is —O—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2— or an aromatic group;
• Ar is an aromatic group of trivalent or more;
• “r” is 0 or 1;
• and “q” is an integer of 1 to 4;
• wherein, in the Formula (4), “W” is at least a group selected from the group consisting of groups represented by the following Formula (5):
• wherein, in the Formula (7-1) and Formula (7-2), “R” is an organic group,

A resin composition comprising a benzoxazole resin precursor having a forth repeating unit represented by the following Formula (10) and a cross-linking agent having at least two or more groups capable of causing a cross linking reaction in a molecule by reacting crosslinking agents and having a diamondoid structure selected from structural units having an adamantane structure as a minimum unit:

• wherein, in the Formula (10), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “m” is an integer of 2 to 1000;
• X1 is at least a group selected from the group consisting of groups represented by the Formula (2-1), Formula (2-2) and Formula (3);
• Y2 is at least a group selected from the group consisting of groups represented by the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2);
• and the hydrogen atom of carbocycle contained in X1 and Y1 may be substituted by an alkyl group and/or a fluoroalkyl group:
• wherein, in the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “p” is, from 1 to 12;
• “i” is from 1 to 12.

The resin composition comprising a benzoxazole resin precursor having a fifth repeating unit represented by the following Formula (13) and a cross-linking agent having at least two or more groups capable of causing a cross linking reaction in a molecule by reacting crosslinking agents and having a diamondoid structure selected from structural units having an adamantane structure as a minimum unit:

• wherein, in the Formula (13), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “n” is an integer of 2 to 1,000;
• X3 is at least a group selected from the group consisting of groups represented by the following Formula (14) and Formula (15);
• Y2 is at least a group selected from the group consisting of groups represented by the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2);
• and the hydrogen atom of carbocycle contained in X3 or Y2 may be substituted with an alkyl group and/or fluoroalkyl group:
• wherein, in the Formula (14), X2 is an ethynyl group or a propargylether group;
• “Z” is —O—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2— or an aromatic group;
• “Ar” is an aromatic group of trivalent or more;
• “R” is a hydrogen or an organic group;
• “r” is 0 or 1;
• and “q” is an integer of 1 to 4,
• wherein, in Formula (15), X4 is at least a group selected from the group consisting of groups represented by the following Formula (16):

A resin composition comprising a benzoxazole resin precursor composition containing, as an essential component, a benzoxazole resin precursor having a third repeating unit represented by the following Formula (1), a benzoxazole resin precursor having a forth repeating unit represented by the following Formula (10) or a benzoxazole resin precursor having a fifth repeating unit represented by the following Formula (13), and two or more kinds selected from the group consisting of the benzoxazole resin precursor having the third repeating unit, the benzoxazole resin precursor having the forth repeating unit, the benzoxazole resin precursor having the fifth repeating unit and a benzoxazole resin precursor having a sixth repeating unit represented by the following Formula (17):

• wherein, in the Formula (1), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “k” is an integer of 2 to 1000;
• X1 is at least a group selected from the group consisting of groups represented by the following Formula (2-1) and the following Formula (2-2) and groups represented by the following Formula (3);
• Y1 is at least a group selected from the group consisting of groups represented by the following Formula (4), Formula (6-1), Formula (6-2), Formula (7-1), Formula (7-2), Formula (8) and Formula (9);
• and the hydrogen atom of carbocycle contained in X1 and Y1 may be substituted by an alkyl group and/or a fluoroalkyl group:
• wherein, in the Formula (2-1) and Formula (2-2), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “a” is from 2 to 12;
• “p” is from 1 to 12;
• “i” is from 1 to 12;
• and “r” is from 0 or 1,
• wherein, in the Formula (3), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “p” is from 1 to 12;
• X2 is an ethynyl group or a propargylether group;
• “Z” is —O—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2— or an aromatic group;
• Ar is an aromatic group of trivalent or more;
• “r” is 0 or 1;
• and “q” is an integer of 1 to 4;
• wherein, in the Formula (4), “W” is at least a group selected from the group consisting of groups represented by the following Formula (5):
• wherein, in the Formula (7-1) and Formula (7-2), “R” is an organic group,
• wherein, in the Formula (10), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “m” is an integer of 2 to 1000;
• X1 is at least a group selected from the group consisting of groups represented by the Formula (2-1), Formula (2-2) and Formula (3);
• Y2 is at least a group selected from the group consisting of groups represented by the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2);
• and the hydrogen atom of carbocycle contained in X1 and Y1 may be substituted by an alkyl group and/or a fluoroalkyl group:
• wherein, in the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2), “Adm” represents a diamondoid structural unit based on an adamantane structure;
• “p” is from 1 to 12;
• “i” is from 1 to 12,
• wherein, in the Formula (13), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “n” is an integer of 2 to 1,000;
• X3 is at least a group selected from the group consisting of groups represented by the following Formula (14) and Formula (15);
• Y2 is at least a group selected from the group consisting of groups represented by the Formula (11-1), Formula (11-2), Formula (12-1) and Formula (12-2);
• and the hydrogen atom of carbocycle contained in X3 or Y2 may be substituted with an alkyl group and/or fluoroalkyl group:
• wherein, in the Formula (14), X2 is an ethynyl group or a propargylether group;
• “Z” is —O—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2— or an aromatic group;
• “Ar” is an aromatic group of trivalent or more;
• “R” is a hydrogen or an organic group;
• “r” is 0 or 1;
• and “q” is an integer of 1 to 4,
• wherein, in Formula (15), X4 is at least a group selected from the group consisting of groups represented by the following Formula (16):
• wherein, in the Formula (17), each of R1 and R2 is independently a hydrogen atom or an organic group;
• “n” is an integer of 2 to 1,000;
• X3 is at least a group selected from the group consisting of groups represented by the Formula (14) and Formula (15);
• Y1 is at least a group selected from the group consisting of groups represented by the Formula (4), Formula (6-1), Formula (6-2), Formula (7-1), Formula (7-2), Formula (8) and Formula (9);
• and a hydrogen atom of carbocycle contained in X3 or Y1 may be substituted with an alkyl group and/or a fluoroalkyl group.