COMPOSITION, MULTILAYER BODY AND METHOD FOR PRODUCING MULTILAYER BODY

Abstract

A composition includes: a compound (A), having an Si—O bond and a cationic functional group that includes at least one selected from the group consisting of a primary nitrogen atom and a secondary nitrogen atom; a compound (B), having at least three —C(═O)OX groups, wherein X is a hydrogen atom or an alkyl group with a carbon number of from 1 to 6, and from one to six of the —C(═O)OX groups is a —C(═O)OH group; and a compound (C), having a cyclic structure and at least one primary nitrogen atom that is directly bonded to the cyclic structure, the composition having a percentage of the primary and the secondary nitrogen atoms in the compound (A), with respect to a total amount of the primary and the secondary nitrogen atoms in the compound (A) and the primary nitrogen atom in the compound (C), of from 3 mol % to 95 mol %.

Claims

1. A composition, comprising: a compound (A), having an Si—O bond and a cationic functional group that includes at least one selected from the group consisting of a primary nitrogen atom and a secondary nitrogen atom; a compound (B), having at least three —C(═O)OX groups, wherein X is a hydrogen atom or an alkyl group with a carbon number of from 1 to 6, and from one to six of the —C(═O)OX groups is a —C(═O)OH group; and a compound (C), having a cyclic structure and at least one primary nitrogen atom that is directly bonded to the cyclic structure, the composition having a percentage of the primary nitrogen atom and the secondary nitrogen atom in the compound (A), with respect to a total amount of the primary nitrogen atom and the secondary nitrogen atom in the compound (A) and the primary nitrogen atom in the compound (C), of from 3 mol % to 95 mol %.

2. The composition according to claim 1, wherein the compound (C) has two or more primary nitrogen atoms that are directly bonded to the cyclic structure.

3. The composition according to claim 1, wherein the compound (C) has a weight average molecular weight of from 80 to 600.

4. The composition according to claim 1, wherein the compound (A) has two alkyl groups that are bonded to an oxygen atom in the Si—O bond.

5. The composition according to claim 1, wherein the compound (B) has a weight average molecular weight of from 200 to 600.

6. The composition according to claim 1, further comprising a polar solvent.

7. The composition according to claim 1, which is used for producing a semiconductor device.

8. The composition according to claim 1, which is used for forming a layer on a substrate or between substrates.

9. A multilayer body comprising a substrate and a layer, the layer comprising a reaction product of: a compound (A), having an Si—O bond and a cationic functional group that includes at least one selected from the group consisting of a primary nitrogen atom and a secondary nitrogen atom; a compound (B), having at least three —C(═O)OX groups, wherein X is a hydrogen atom or an alkyl group with a carbon number of from 1 to 6, and from one to six of the —C(═O)OX groups is a —C(═O)OH group; and a compound (C), having a cyclic structure and at least one primary nitrogen atom that is directly bonded to the cyclic structure, the layer having a percentage of the primary nitrogen atom and the secondary nitrogen atom in the compound (A), with respect to a total amount of the primary nitrogen atom and the secondary nitrogen atom in the compound (A) and the primary nitrogen atom in the compound (C), of from 3 mol % to 95 mol %.

10. The multilayer body according to claim 9, wherein the substrate comprises a first substrate and a second substrate, and the first substrate, the layer comprising the reaction product, and the second substrate are disposed in this order.

11. A method for producing a multilayer body, the method comprising forming a layer on a substrate or between substrates and curing the layer, the layer comprising: a compound (A), having an Si—O bond and a cationic functional group that includes at least one selected from the group consisting of a primary nitrogen atom and a secondary nitrogen atom; a compound (B), having at least three —C(═O)OX groups, wherein X is a hydrogen atom or an alkyl group with a carbon number of from 1 to 6, and from one to six of the —C(═O)OX groups is a —C(═O)OH group; and a compound (C), having a cyclic structure and at least one primary nitrogen atom that is directly bonded to the cyclic structure, the layer having a percentage of the primary nitrogen atom and the secondary nitrogen atom in the compound (A), with respect to a total amount of the primary nitrogen atom and the secondary nitrogen atom in the compound (A) and the primary nitrogen atom in the compound (C), of from 3 mol % to 95 mol %.

12. The composition according to claim 2, wherein the compound (A) has two alkyl groups that are bonded to an oxygen atom in the Si—O bond.

Description

EXAMPLES

[0277] In the following, the present invention is explained in a more specific manner by referring the Examples. However, the present invention is not limited to the Examples.

[0278] (Preparation of Composition)

[0279] Compositions for the Examples and the Comparative Examples including the components shown in Table 1 were prepared.

[0280] The amount of the components were adjusted such that the amine equivalent amount of the compound (A) and the compound (C) in total was equal to the carboxy group equivalent amount of the compound (C), and that the percentage of the primary nitrogen atom and the secondary nitrogen atom in the compound (A), with respect to a total amount of the primary nitrogen atom and the secondary nitrogen atom in the compound (A) and the primary nitrogen atom in the compound (C), was a value (mol %) shown in Table 1. The percentage (% by mass) described in the compound (A) refers to a value with respect to the compound (A).

[0281] Each composition includes water, ethanol and N,N-dimethylacetamide as a polar solvent.

TABLE-US-00001 TABLE 1 Examples Comparative Examples 1 2 3 4 5 6 7 8 1 2 3 Compound (A) 3APDES 3APDES 3APDES 3APDES 3APDES 3APDES 3APDES 3APDES 3APDES 3APDES — (90 mass %)/ (80 mass %)/ M3TMSPA APTES (10 mass %) (20 mass %) Compound (B) ODPA BPDA ODPA PMDA ODPA ODPA ODPA ODPA ODPA ODPA ODPA Compound (C) TFDB AAPD AAPD AAPD TFDB TFDB TFDB TFDB — pXDA AAPD Percentage of 20 10 20 95 3 20 40 40 100  20  0 primary/ secondary nitrogen atoms in Compound (A) [mol %] Surface energy over over over over 0.48 over over over over over below [J/m.sup.2] 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 0.1 CTE 77 26 44 97 56 76 83 95 145 125 38 [ppm/° C.]

[0282] The details of the components shown in Table 1 are as follows. [0283] 3APDES: 3-aminopropyldiethoxymethylsilane [0284] 3APTES: 3-aminopropyltriethoxysilane [0285] M3TEMSPA: N-methyl-3-(trimethoxysilyl)propylamine [0286] ODPA: half-esterified compound obtained by ring-opening of 4,4′-oxydiphthalic anhydride with ethanol [0287] BPDA: half-esterified compound obtained by ring-opening of 4,4′-biphenyltetracarboxylic dianhydride with ethanol [0288] PMDA: half-esterified compound obtained by ring-opening of pyromellitic dianhydride with ethanol [0289] TFDB: 4,4′-diamino-2,2′-bis(trifluoromethyl)biphenyl [0290] AAPD: 4,4′-diamino-2,2′-dimethylbiphenyl [0291] pXDA: p-xylylenediamine

[0292] (Evaluation of Bonding Strength)

[0293] The composition was applied onto a silicon substrate (substrate 1) by spin coating, and a different silicon substrate (substrate 2) was disposed thereon. The composition was cured by heating at 250° C. while applying a pressure of 1 MPa, thereby obtaining a multilayer body having a cured product layer between the substrate 1 and the substrate 2.

[0294] The multilayer body was subjected to a blade insert test to measure a surface energy at an interface between the substrate and the cured product layer, by a method according to Journal of Applied Physics, 64 (1988) 4943-4950.

[0295] Specifically, a blade with a thickness of 0.25 mm was inserted between the substrate 1 and the substrate 2, and a distance from a tip of the blade to a position at which the substrates separate from each other was measured using an infrared light source and an infrared camera. The surface energy was calculated by the following formula. The greater the surface energy is, the greater the bonding strength of the cured product layer with respect to the substrate is. When the surface energy is 0.2 J/m.sup.2 or more, the bonding strength is regarded as acceptable. The results are shown in Table 1.

γ=3×10.sup.9×t.sub.b.sup.2×E.sup.2×t.sup.6/(32×L.sup.4×E×t.sup.3)

[0296] In the formula, γ represents a surface energy (J/m.sup.2), t.sub.b represents a thickness of blade (m), E represents a Young's modulus of substrate 1 and substrate 2 (GPa), t represents a total thickness of substrate 1 and substrate 2 (m), and L represents a distance from a tip of blade to a position at which substrate 1 and substrate 2 separate from each other.

[0297] (Evaluation of Thermal Expansion Coefficient)

[0298] The composition was applied onto a polyimide film (UPILEX, UBE Corporation) by spin coating, and the composition was cured at 350° C. to form a cured product layer.

[0299] After separating the polyimide film, an average linear expansion coefficient (CTE) of the cured product layer was measured using a thermomechanical analyzer (TMA 7100C, Hitachi High-Tech Science Corporation) in a nitrogen atmosphere at 250° C. The smaller the CTE is, the smaller the thermal expansion coefficient of the cured product layer is. The results are shown in Table 1.

[0300] As shown in Table 1, the Examples using the composition according to the present embodiment exhibit a smaller CTE of a cured product layer than Comparative Example 1, in which the composition does not include compound (C), or Comparative Example 2, in which the composition includes a diamine compound not having an amino group directly bonded to a cyclic structure instead of compound (C). The results indicate that the Examples achieve a lower thermal expansion coefficient than the Comparative Examples.

[0301] Further, the Examples exhibit a greater surface energy than Comparative Example 3, in which the composition does not include compound (A), indicating that the Examples achieve a better bonding strength than Comparative Example 3.

[0302] The disclosure of Japanese Patent Application No. 2020-152329 is incorporated herein by reference in its entirety.

[0303] All publications, patent applications, and technical standards mentioned in the present specification are incorporated herein by reference to the same extent as if each individual publication, patent application, or technical standard was specifically and individually indicated to be incorporated by reference.