Photosensitive resin composition, cured product of same, interlayer insulating film, surface protective film and electronic component

Abstract

Provided is a photosensitive resin composition containing; (A) a polymer having an acidic functional group or a substituent derived therefrom; (B) a photoreactive compound; (C) a solvent; and (D) a nitrogen-containing aromatic compound represented by the following general formula (1). ##STR00001##

Claims

1. A photosensitive resin composition, comprising: (A) polybenzoxazole precursor; (B) a photoreactive compound; (C) a solvent; (D) a nitrogen-containing aromatic compound represented by the following general formula (1): ##STR00018## (wherein, R.sup.1 is a hydrogen atom or a hydrocarbon group, R.sup.2 is a hydrogen atom, an amino group, an alkyl group, an alkenyl group, a cyclic aliphatic group having 3 to 10 carbon atoms or a phenyl group, and A, B, and E are each independently N or CR.sup.3; R.sup.3 is a hydrogen atom or a monovalent organic group; and when a plurality of R.sup.3 exist, the plurality of R.sup.3 may be identical to or different from each other); and (F) one or more selected from the group consisting of a melamine, and a melamine in which a site in an N position is substituted by a methylol group or an alkoxymethyl group.

2. The photosensitive resin composition according to claim 1, wherein the polybenzoxazole precursor has a structural unit represented by the following general formula (2-1) and a structural unit represented by the following general formula (2-2): ##STR00019## (wherein, X and T are each independently a divalent organic group, and X is a group different from T; Y is a tetravalent organic group, and R is each independently a hydrogen atom or a monovalent organic group; and I and m are a mole fraction, and when a sum of I and m is taken as 100 mol %, I is 60 to 100 mol % and m is 0 to 40 mol %).

3. The photosensitive resin composition according to claim 1, wherein the component (D) is a compound having a triazole skeleton or a tetrazole skeleton.

4. A cured product of the photosensitive resin composition according to claim 1.

5. An interlayer insulating film or a surface protective film, using the cured product according to claim 4.

6. An electronic component, comprising the interlayer insulating film according to claim 5.

7. An electronic component, comprising the surface protective film according to claim 5.

Description

EXAMPLES

(1) Hereinafter, Examples and Comparative Examples will be described, but the invention is not limited to Examples and Comparative Examples described below.

(2) Manufacturing Example 1 (Synthesis of A-1)

(3) In a 0.2-L flask provided with a stirrer and a thermometer, 60 g of N-methylpyrrolidone was put, 13.92 g (38 mmol) of 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane was added thereto, and the resulting mixture was stirred and dissolved therein. Subsequently, while keeping a temperature at 0 to 5° C., 8.55 g (32 mmol) of dodecanedioic acid dichloride and 2.36 g (8 mmol) of diphenyl ether dicarboxylic acid dichloride were each added thereto while taking 10 minutes, and then the resulting mixture was required to room temperature, and continuously stirred for 3 hours.

(4) The stirred solution was put in 3 L of water, and precipitates were collected and washed with pure water 3 times, and then dried under reduced pressure to obtain polyhydroxyamide (polybenzoxazole precursor) A-1. GPC measurement under the following measuring conditions was performed on A-1, and from the measured value obtained, weight-average molecular weight determined by a standard polystyrene equivalent according to a GPC method was 39,500, and a degree of dispersion was 1.9. On A-1, a mole fraction of a structural unit derived from dodecanedioic acid was 80 mol %, and a mole fraction of a structural unit derived from diphenyl ether dicarboxylic acid was 20 mol %.

(5) (Measuring Conditions of Weight-Average Molecular Weight According to the GPC Method)

(6) Measuring instrument: Detector L4000 UV, made by Hitachi, Ltd.

(7) Pump: L6000, made by Hitachi, Ltd.

(8) Recorder: C-R4A Chromatopac, made by Shimadzu Corporation

(9) Measuring conditions: column: Gelpack GL-S300MDT-5×2

(10) Eluent: THF (tetrahydrofuran)/DMF (N,N-dimethylformamide)=1/1 (volume ratio)

(11) LiBr (0.03 mol/L), H.sub.3PO.sub.4 (0.06 mol/L)

(12) Flow rate: 1.0 mL/min, detector: UV 270 nm

(13) Measurement was performed by using a solution having 1 mL of a solvent [THF/DMF=1/1 (volume ratio)], based on 0.5 mg of a polymer.

(14) Manufacturing Example 2 (Synthesis of A-2)

(15) In a 1.0-L flask provided with a stirrer and a thermometer, 62.0 g (199.9 mmol) of 4,4′-oxydiphthalic dianhydride, 5.2 g (40.0 mmol) of 2-hydroxyethyl methacrylate and a catalyst amount of 1,4-diazabicyclo[2.2.2.]octane triethylenediamine were dissolved in 250.0 g of N-methyl-2-pyrrolidone, the resulting mixture was stirred at 45° C. for 1 hour, and then cooled down to 25° C., and 5.5 g (50.9 mmol) of m-phenylenediamine, 23.8 g (118.9 mmol) of oxydianiline and 100 mL of dry N-methyl-2-pyrrolidone were added thereto, and then the resulting mixture was stirred at 45° C. for 150 minutes, and cooled down to room temperature.

(16) To the solution, 78.5 g (373.8 mmol) of trifluoroacetic anhydride was added dropwise, and then the resulting mixture was stirred for 20 minutes, and 53.1 g (408.0 mmol) of 2-hydroxyethyl methacrylate was added thereto, and the resulting mixture was stirred at 45° C. for 20 hours. The reaction solution was added dropwise to distilled water, and deposits were collected by filtration, and dried under reduced pressure to obtain polyamide acid ester A-2. Weight-average molecular weight of A-2 was determined in the same manner as in Manufacturing Example 1. The weight-average molecular weight was 35,000.

(17) Examples 1 to 13 and Comparative Examples 1 to 2

(18) A-1 obtained in Manufacturing Example 1, A-2 obtained in Manufacturing Example 2 and the following components (B) to (F) were blended at a blending amount (parts by mass) described in Table 1 to prepare a photosensitive resin composition.

(19) In Table 1, in each column of a component other than a component (A), each numeric value represents an amount of addition (parts by mass) based on 100 parts by mass of the component (A).

(20) The following component was arranged as the component (B).

(21) ##STR00015##

(22) B-3: 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(O-benzoyloxime) (IRGACURE-OXE-01, made by BASF SE)

(23) The following component was arranged as the component (C).

(24) C-1: γ-butyrolactone/propylene glycol 1-monomethyl ether 2-acetate (9/1 in a volume ratio)

(25) C-2: γ-butyrolactone

(26) C-3: N-methyl-2-pyrrolidone

(27) The following component was arranged as the component (D).

(28) D-1: 5-aminotetrazole

(29) D-2: 1,2,4-triazole

(30) The following component was arranged as the component (E). Et denotes an ethyl group.

(31) ##STR00016##

(32) The following component was arranged as the component (F). Me denotes a methyl group.

(33) ##STR00017##

(34) In order to uniformize surface conditions, a Cu substrate was washed with acetic acid. The photosensitive resin composition obtained was spin-coated on the above-described Cu substrate, and heated at 120° C. for 3 minutes to form a resin film having a thickness of 11 to 12 μm.

(35) The resin film was heat-treated by using Vertical Diffusion Furnace p-TF (made by Koyo Thermo Systems Co., Ltd.) at 100° C. for 0.5 hour in a nitrogen atmosphere, and further heated at 200° C. for 1 hour to obtain a cured film having a thickness of 10 μm.

(36) (Evaluation of Discoloration Suppression)

(37) Appearance was visually evaluated on the cured film obtained. A color of the cured film in Comparative Example 1 was deemed as being discolored and a color of the cured film in Example 1 was deemed as being not discolored, and suppression of discoloration was evaluated as described below. The results are shown in Table 1.

(38) A: Discoloration was suppressed.

(39) B: Discoloration was not suppressed.

(40) (Evaluation of Adhesion)

(41) The cured film obtained was cut into a cross cut of 10×10 with a razor by using Cross Cut Guide (made by COTEC Corporation), and the cured film was divided into 100 small pieces.

(42) A pressure sensitive adhesive tape (made by 3M Japan Limited) was stuck thereonto, and the pressure sensitive adhesive tape was peeled. Adhesion was evaluated depending on the number of small pieces of the cured film peeled from the substrate upon peeling the pressure sensitive adhesive tape as described below. The results are shown in Table 1.

(43) A: No peel was caused.

(44) B: Peel of one or more pieces was caused.

(45) (Evaluation of Adhesion after an Accelerated Test)

(46) As an accelerated test, the cured film obtained was treated at 121° C., 100 RH (Relative Humidity) % and 2 atm for 100 hours. Adhesion was evaluated on the cured film after treatment in the same manner as in the above-described evaluation of adhesion. The results are shown in Table 1.

(47) The present evaluation was not performed on the cured film of B in the results in (Evaluation of adhesion).

(48) TABLE-US-00001 TABLE 1 Adhesion after Component Component Component Component Component Component Discoloration accelerated (A) (B) (C) (D) (E) (F) suppression Adhesive test Example 1 A-1 B-1 C-1 D-1 — F-1 A A A (100) (11) (200) (2) (25) Example 2 A-1 B-1 C-1 D-1 — F-1 A A A (100) (11) (200)   (0.5) (25) Example 3 A-1 B-1 C-1 D-1 E-1 F-1 A A A (100) (11) (200) (2) (6) (25) Example 4 A-1 B-1 C-1 D-1 E-1 F-1 A A A (100) (11) (200)   (0.5) (6) (25) Example 5 A-1 B-1 C-1 D-1 — F-2 A A A (100) (11) (200) (2) (25) Example 6 A-1 B-1 C-1 D-1 — F-3 A A A (100) (11) (200) (2) (25) Example 7 A-1 B-1 C-1 D-2 E-1 F-1 A A A (100) (11) (200) (2) (6) (25) Example 8 A-1 B-2 C-1 D-1 E-1 F-2 A A A (100) (11) (200) (2) (6) (25) Example 9 A-1 B-2 C-2 D-1 E-1 F-2 A A A (100) (11) (200)   (0.5) (6) (25) Example 10 A-2 B-3 C-3 D-1 E-1 F-2 A A A (100)  (5) (200)   (0.5) (3) (35) Example 11 A-1 B-1 C-1 D-1 — F-1 A A A (100) (11) (200) (2) (25) Example 12 A-1 B-1 C-1 D-1 — F-2 A A A (100) (11) (200) (2) (25) Comparative A-1 B-1 C-1 — — F-1 B B — Example 1 (100) (11) (200) (25) Comparative A-1 B-1 C-1 — E-1 F-1 B A A Example 2 (100) (11) (200) (6) (25)

INDUSTRIAL APPLICABILITY

(49) A photosensitive resin composition of the invention can be used for a semiconductor device or the like. The semiconductor device of the invention can be used for various electronic devices or the like.

(50) Several embodiments and/or Examples of the invention have been described in detail above, but those skilled in the art will readily make a great number of modifications to the exemplary embodiments and/or Examples without substantially departing from new teachings and advantageous effects of the invention. Accordingly, all such modifications are included within the scope of the invention.

(51) The entire contents of the description of the Japanese application serving as a basis of claiming the priority concerning the present application to the Paris Convention are incorporated by reference herein.