Carboxyl group-ontaining polyimide, heat-curable resin composition, and flexible metal-clad laminate

A technology of resin composition and polyimide, applied in the field of thermosetting resin composition and flexible metal-clad laminate, can solve the problems of low heat resistance, insufficient thermosetting, short circuit, etc., and achieve the effect of satisfying thermosetting

Active Publication Date: 2013-12-11
TOYOBO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) Since the acid anhydride group exists only at the end of the resin, sufficient thermosetting properties cannot be obtained
[0011] (2) Since the resin skeleton contains a urethane bond, the heat resistance is low
[0012] (3) Intramolecular crosslinking occurs due to the unique oxidation of the polybutadiene skeleton, the resin gels during the reaction, and the storage stability as a composition is significantly reduced
However, when the dimensional change of the resin at high temperature is large, there is a problem of peeling off from the metal wiring such as copper forming the circuit, resulting in a short circuit or disconnection.
In addition, the thermal dimensional change of the flexible multilayer substrate that has recently attracted attention as a thin and thick substrate, the adhesive layer that bonds single-layer flexible substrates to each other, the polyimide film that forms the flexible substrate, and the metal wiring such as copper that forms the circuit The same problem occurs when the difference of
[0024] Patent Document 6 discloses a technology for improving high-temperature physical properties by combining an epoxy resin with excellent heat resistance and an inorganic compound, but the effect of improving solvent resistance cannot be expected

Method used

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  • Carboxyl group-ontaining polyimide, heat-curable resin composition, and flexible metal-clad laminate
  • Carboxyl group-ontaining polyimide, heat-curable resin composition, and flexible metal-clad laminate
  • Carboxyl group-ontaining polyimide, heat-curable resin composition, and flexible metal-clad laminate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0213] Hereinafter, although an Example demonstrates this invention, this invention is not limited to these Examples. In addition, the evaluation of the characteristic value in each Example was performed by the following method.

[0214]

[0215] Dissolve 15 mg of a sample containing terminal anhydride group imide prepolymer and carboxyl group-containing polyimide in 0.6 ml of deuterated dimethyl sulfoxide, and use a Fourier transform nuclear magnetic resonance spectrometer (BioSpin AVANCE500 manufactured by BRUKER Corporation) )conduct 1 In H-NMR analysis, the molar ratio was obtained from the integral ratio.

[0216]

[0217] Dissolve and / or dilute samples such as imide prepolymers containing terminal anhydride groups and polyimides containing carboxyl groups with tetrahydrofuran so that the resin concentration is about 0.5% by weight. The substance obtained by filtration with a membrane filter was used as a measurement sample, and the molecular weight was measured by ...

Synthetic example 1-2、1-7

[0260] Change the composition of the raw material as shown in Table 1, dissolve the tetracarboxylic dianhydride in the solvent at 180°, and set the reaction conditions with the diisocyanate compound to 180° C. for 3 hours. In addition, the synthesis example 1- 1. Operate in the same way to obtain various carboxyl-containing polyimides. Table 1 shows the composition and physical properties of these resins. In addition, the carboxyl group-containing thermosetting polyimide (1-2) obtained in Synthesis Example 1-2 1 The H-NMR spectrum is shown in figure 2 .

Synthetic example 1-3、1-4、1-5、1-6

[0262] Various carboxyl group-containing polyimides were obtained in the same manner as in Synthesis Example 1-1, except that the composition of the raw materials was changed as shown in Table 1. Table 1 shows the composition and physical properties of these resins.

[0263] [Table 1]

[0264]

[0265] The meanings of the abbreviations in Table 1 are described below.

[0266] TMEG: Ethylene glycol bis(trimellitic anhydride) ester

[0267] PMDA: pyromellitic dianhydride

[0268] BPDA: 3,3’,4,4’-Biphenyltetracarboxylic dianhydride

[0269] BTDA: 3,3',4,4'-Benzophenone tetracarboxylic dianhydride

[0270] ODPA: 4,4'-oxydiphthalic anhydride (ODPA)

[0271] MDI: 4,4'-Diphenylmethane diisocyanate

[0272] TDI: 2,4-Toluene diisocyanate

[0273] C-2090: polycarbonate diol (3-methyl-1,5-pentanediol / 1,6-hexanediol) manufactured by Kuraray Co., Ltd., number average molecular weight about 2000

[0274] T5650E: Asahi Kasei Chemicals Co., Ltd. polycarbonate diol (1,5-pentanediol / ...

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Abstract

Provided are a carboxyl group-containing polyimide and a prepolymer thereof, and the carboxyl group-containing polyimide can provide a cured product that simultaneously exhibits heat curing properties, PCT resistance, solvent resistance and peel strength. The present invention relates to an imide prepolymer containing a terminal acid anhydride group and characterized by being obtained by reacting an acid anhydride group in a tetracarboxylic dianhydride with an isocyanate group in a diisocyanate compound. The present invention also relates to the carboxyl group-containing polyimide characterized by having a structure in which the aforementioned imide prepolymer containing a terminal acid anhydride group undergoes chain extension via a polyol compound. Furthermore, the present invention relates to a heat-curable resin composition and a flexible metal-clad laminate that use the carboxyl group-containing polyimide.

Description

technical field [0001] The present invention relates to: a kind of carboxyl-containing polyimide and its prepolymer as the raw material of thermosetting polyimide resin, described carboxyl-containing polyimide is used as adhesive agent, coating agent in electronic material field, can A cured product excellent in thermosetting properties, PCT resistance, solvent resistance, and peel strength was obtained. [0002] Also, the present invention relates to a thermosetting resin composition that satisfies flame retardancy, solder heat resistance, heat deterioration resistance, and flexibility and is suitable for use as a resist layer of a printed circuit board. [0003] Furthermore, the present invention relates to a flexible metal-clad laminate having a resin layer obtained by thermosetting the above-mentioned carboxyl group-containing polyimide and a metal foil layer, and particularly relates to a product capable of simultaneously satisfying thermosetting properties, peel strength...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/34C08G73/10C08G73/16C08G81/00
CPCC08G18/346C08G73/1035C08G18/7621C08G18/7671C08G18/34C08G73/10C08G73/16C08L75/04C08L79/08
Inventor 川楠哲生
Owner TOYOBO CO LTD
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