CN116515107A - Copper-clad laminate, polyimide resin, and method for producing same - Google Patents

Copper-clad laminate, polyimide resin, and method for producing same Download PDF

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Publication number
CN116515107A
CN116515107A CN202210195652.XA CN202210195652A CN116515107A CN 116515107 A CN116515107 A CN 116515107A CN 202210195652 A CN202210195652 A CN 202210195652A CN 116515107 A CN116515107 A CN 116515107A
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CN
China
Prior art keywords
chemical formula
polyimide resin
derived
dianhydride
polyphenylene ether
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CN202210195652.XA
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Chinese (zh)
Inventor
廖德超
黄威儒
张宏毅
刘家霖
魏千凯
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Nan Ya Plastics Corp
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Nan Ya Plastics Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Laminated Bodies (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

The present invention provides a polyimide resin comprising dianhydride monomers and diamine monomers, wherein the diamine monomers comprise residues derived from a terminal amine-modified polyphenylene ether oligomer. Since the diamine monomer contains residues derived from the terminal amine-modified polyphenylene ether oligomer, the polyimide resin has the characteristics of low dielectric constant and high peel strength.

Description

Copper-clad laminate, polyimide resin, and method for producing same
Technical Field
The present invention relates to a polyimide resin and a method for producing the same, wherein the polyimide resin can be applied to a copper-clad laminate.
Background
Flexible printed circuit boards (Flexible Printed Circuits, FPCs) have the advantage of being lightweight and flexible, making them an important component of many electronic devices. Currently, an FPC is obtained by patterning a Copper layer in a Copper-Clad Laminate (CCL) to perform wiring processing. With the development of 5G communications, many manufacturers have been working to reduce the dielectric properties of the substrate materials (e.g., polyimide resins) in copper-clad laminates. However, it is difficult for the conventional polyimide resin to have both the adhesive strength with the copper layer and the low dielectric characteristics.
Disclosure of Invention
The invention provides a polyimide resin with low dielectric constant and high adhesive strength.
The invention provides a copper-clad laminate, which has high adhesion strength between a copper layer and polyimide resin.
The present invention provides a method for producing polyimide resin, and the synthesized polyimide resin has the characteristics of low dielectric constant and high adhesive strength.
At least one embodiment of the present invention provides a polyimide resin. Polyimide resins include dianhydride monomers as well as diamine monomers, wherein the diamine monomers comprise residues derived from terminal amine-modified polyphenylene ether oligomers.
At least one embodiment of the present invention provides a copper-clad laminate including a copper layer and a polyimide resin formed on the copper layer.
At least one embodiment of the present invention provides a method for manufacturing a polyimide resin, including: dissolving a diamine monomer in a solvent, wherein the diamine monomer comprises a terminal amine group modified polyphenylene ether oligomer; and adding dianhydride monomer into the solvent, and performing polymerization reaction.
Based on the above, since the diamine monomer in the polyimide resin contains the residue derived from the terminal amine group-modified polyphenylene ether oligomer, the polyimide resin has the characteristics of low dielectric constant and high adhesive strength.
Drawings
FIG. 1 is a schematic cross-sectional view of a copper-clad laminate according to an embodiment of the present invention.
Description of the reference numerals
10, a copper-clad laminate;
100, a copper layer;
200, polyimide resin;
t1 is thickness.
Detailed Description
FIG. 1 is a schematic cross-sectional view of a copper-clad laminate according to an embodiment of the present invention.
Referring to fig. 1, a copper-clad laminate 10 includes a copper layer 100 and a polyimide resin 200 formed on the copper layer 100. In some embodiments, the thickness T1 of the polyimide resin 200 is in the range of 12 micrometers to 50 micrometers.
The method for manufacturing the polyimide resin 200 includes dissolving a diamine monomer in a solvent, then adding a dianhydride monomer to the solvent, and performing a polymerization reaction. In the present embodiment, the polyimide resin 200 synthesized after the polymerization reaction is coated on the copper layer 100, and the foregoing polyimide resin 200 is cured to obtain the copper-clad laminate 10. In some embodiments, the polyimide resin 200 is a thermoplastic polyimide.
In this example, the diamine monomer used for synthesizing the polyimide resin 200 comprises a terminal amine group-modified polyphenylene ether oligomer having a structure shown in chemical formula 1:
[ chemical formula 1]
In chemical formula 1, m is an integer of 4 to 10.
In some embodiments, the molecular weight of the terminal amine-modified polyphenylene ether oligomer is from 1500 to 3000. In some embodiments, the amine-terminated polyphenylene ether oligomer has a solubility of greater than 50% in solvents such as butanone (Methyl Ethyl Ketone, MEK), cyclohexanone, toluene, dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP).
In some embodiments, the terminal amine-modified polyphenylene ether oligomer is 20 mole percent or more, such as 20 mole percent to 100 mole percent, 30 mole percent to 90 mole percent, 40 mole percent to 80 mole percent, or 50 mole percent to 70 mole percent, based on 100 mole percent total diamine monomer.
In some embodiments, the diamine monomer further comprises at least one of the diamine monomers represented by the following chemical formulas 3 to 9 in addition to the amine-terminated polyphenylene ether oligomer:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
[ chemical formula 9]
Wherein in chemical formulas 3 to 9, R 4 Independently represents hydrogen or a monovalent hydrocarbon group of 1 to 6 carbon atoms or an alkoxy group, the linking groups A independently represent a member selected from the group consisting of-O-, -S-, -CO-, -SO-, -SO2-, divalent radicals in-COO-, -CH2-, -C (CH 3) 2-, -NH-or-CONH-, n is n 1 Independently represents an integer of 0 to 4.
It should be noted that, although the present disclosure proposes that the diamine monomer used for synthesizing the polyimide resin 200 includes a terminal amine-modified polyphenylene ether oligomer and at least one selected from chemical formulas 3 to 9, the present invention is not limited thereto. In other embodiments, the diamine monomer used to synthesize the polyimide resin 200 includes a terminal amine group-modified polyphenylene ether oligomer and other types of diamine monomers other than chemical formulas 3 to 9. The terminal amine-modified polyphenylene ether oligomer is dissolved in a solvent, which may comprise butanone, cyclohexanone, toluene, dimethylacetamide, N-methylpyrrolidone, other organic solvents, or a combination of the above, with optional other diamine monomers.
In some embodiments, the dianhydride monomer used to synthesize the polyimide resin 200 is selected from at least one of the following materials: 3,3', 4' -biphenyltetracarboxylic dianhydride (3, 3', 4' -biphenyl tetracarboxylic dianhydride, BPDA), 1, 4-phenylenedi (trimellitic monoester) dianhydride (1, 4-phenylenebis (trimellitic acid monoester) dianhydride, TAHQ), pyromellitic dianhydride (pyromellitic dianhydride, PMDA), 4'-oxydiphthalic anhydride (4, 4' -Oxydiphthalic anhydride), 4'- (hexafluoroisopropenyl) diphthalic anhydride (4, 4' - (hexafluorofluoropropylene) diphthalic anhydride), 2,3,6,7-naphthalene tetracarboxylic dianhydride (2, 3,6,7-naphthalene tetracarboxylic dianhydride, NTCDA), 3'4,4' -Benzophenone tetracarboxylic dianhydride (Benzophenone-3, 3', 4' -tetracarboxylic dianhydride), 1,2,3, 4-Cyclobutane tetracarboxylic dianhydride (Cyclobutane-1, 2,3,4-tetracarboxylic dianhydride), 1,2,4,5-cyclohexane tetracarboxylic dianhydride (1, 2,4,5-cyclohexanetetracarboxylic dianhydride), 4'-bisphenol a dianhydride (4, 4' -Bisphenol A dianhydride), and other suitable dianhydride monomers.
In some embodiments, the terminal amine-modified polyphenylene ether oligomer is derived from more than 20 moles, such as 20 to 100 moles, 30 to 90 moles, 40 to 80 moles, or 50 to 70 moles of residues in the polyimide resin 200, with a total diamine monomer fraction of 100 moles.
In some embodiments, the polyimide resin 200 has a structure as shown in chemical formula 2:
[ chemical formula 2]
In chemical formula 2, m is an integer of 4 to 10, x is 0.2 to 1, and y is 0.8 to 0. For example, x is 0.2 and y is 0.8, x is 0.3 and y is 0.7, x is 0.4 and y is 0.6, x is 0.5 and y is 0.5, x is 0.6 and y is 0.4, x is 0.7 and y is 0.3, x is 0.8 and y is 0.2, x is 0.9 and y is 0.1, x is 1 and y is 0.
In some embodiments, R in chemical formula 2 1 And R is R 2 Each being a residue derived from a dianhydride monomer (or a tetracarboxylic dianhydride monomer). For example, R in chemical formula 2 1 And R is R 2 Each selected from at least one of the following options: 3,3', residues derived from 4,4' -biphenyltetracarboxylic dianhydride, residues derived from 1,4-phenylene bis (trimellitic monoester) dianhydride, residues derived from pyromellitic dianhydride, residues derived from 4,4' -oxydiphthalic anhydride, residues derived from 4,4' - (hexafluoro-isopropenyl) diphthalic anhydride, residues derived from 2,3,6,7-naphthalene tetracarboxylic dianhydride, residues derived from 3,3', 4' -benzophenone tetracarboxylic dianhydride, residues derived from 1,2,3, 4-cyclobutane tetracarboxylic dianhydride, residues derived from 1,2,4,5-cyclohexane tetracarboxylic dianhydride, residues derived from 4,4' -bisphenol A dianhydride, and residues derived from other suitable dianhydride monomers.
In some embodiments, diamine monomers used when synthesizing the polyimide resin 200When diamine monomers other than the terminal amine-modified polyphenylene ether oligomer are included, R 3 Residues derived from diamine monomers other than the terminal amine-modified polyphenylene ether oligomer. For example, R in chemical formula 2 3 Residues derived from at least one of diamine monomers represented by chemical formulas 3 to 9.
In some embodiments, the copper-clad laminate 10 has a dielectric loss tangent (Dissipation factor, df) of 0.004 or less at a signal of 10 GHz. In some embodiments, the water absorption of the copper-clad laminate 10 is less than 0.5% (e.g., 0.3%), and the adhesive strength between the copper layer 100 and the polyimide resin 200 is greater than 0.5kgf/cm (e.g., 0.8 kgf/cm).
Hereinafter, some examples of the polyimide resin of the present invention are provided, however, these examples are illustrative, and the present invention is not limited to these examples.
Comparative example 1
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers of 4, 4-diaminodicyclohexylmethane (PACM).
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 1
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers containing 75mol% PACM and 25mol% terminal amine-modified polyphenylene ether oligomer (PPE-NH 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 2
Polyimide resin is synthesized by dianhydride monomer and diamine monomer, wherein the dianhydride monomer comprises 20mol percent PMDA and 80mol percent BPDA,and the diamine monomer comprises 50mol% PACM and 50mol% of terminal amine-modified polyphenylene ether oligomer (PPE-NH 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 3
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers containing 25mol% PACM and 75mol% terminal amine-modified polyphenylene ether oligomer (PPE-NH 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 4
Polyimide resin is synthesized by dianhydride monomer and diamine monomer, wherein the dianhydride monomer comprises 20mol percent PMDA and 80mol percent BPDA, and the diamine monomer is polyphenyl ether oligomer (PPE-NH) modified by terminal amino group 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
The formulations of comparative example 1 and examples 1 to 4 and the characteristics of the copper clad laminate formed are collated in table 1.
TABLE 1
As can be seen from comparative example 1 and examples 1 to 4, when the terminal amine group-modified polyphenylene ether oligomer is used as a monomer, the synthesized polyimide resin has a low dielectric constant and the peel strength with the copper layer can be improved. In table 1, the flame resistance was different from the flame resistance of UL94V0, and the polyimide resins synthesized in example 3 and example 4 were excellent in flame resistance. In addition, when the amount of the terminal amine-modified polyphenylene ether oligomer used is larger, the flame resistance of the synthesized polyimide resin is better and the water absorption is lower.
Comparative example 2
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers containing 50mol% 1,3-Bis (4-aminophenoxy) benzene (1, 3-Bis (4-aminophenoxy) benzene, TPE-R) and 50mol% 2,2-Bis [4- (4-aminophenoxy) phenyl ] propane (2, 2-Bis [4- (4-aminophenoxy) phenyl ] propane, BAPP).
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 5
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers containing 50mol% TPE-R, 30mol% BAPP and 20mol% terminal amine-modified polyphenylene ether oligomer (PPE-NH 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
Example 6
Polyimide resins were synthesized with dianhydride monomers containing 20mol% PMDA and 80mol% BPDA and diamine monomers containing 50mol% TPE-R and 50mol% terminal amine-modified polyphenylene ether oligomer (PPE-NH 2 )。
Polyimide resin was coated on the copper layer to form a copper-clad laminate, and water absorption, dielectric constant (Dk), dielectric loss tangent (Df), peel strength, and flame resistance were measured.
The formulations of comparative example 2 and examples 4 to 6 and the characteristics of the copper clad laminate formed are collated in table 2.
TABLE 2
As can be seen from comparative example 2 and examples 4 to 6, when the terminal amine group-modified polyphenylene ether oligomer is used as the diamine monomer, the synthesized polyimide resin has a low dielectric constant and the peel strength with the copper layer can be improved. In addition, the flame resistance in table 2 is the flame resistance properties of different materials distinguished by UL94V 0. In addition, when the amount of the terminal amine-modified polyphenylene ether oligomer used is larger, the water absorption of the synthesized polyimide resin is lower.

Claims (10)

1. A polyimide resin comprising:
dianhydride monomers, and diamine monomers, wherein the diamine monomers comprise residues derived from a terminal amine-modified polyphenylene ether oligomer.
2. The polyimide resin according to claim 1, wherein the terminal amine group-modified polyphenylene ether oligomer is derived from 20 mole parts or more of residues based on 100 mole parts of the total amount of the diamine monomers.
3. The polyimide resin according to claim 1, wherein the structure of the terminal amine-modified polyphenylene ether oligomer is represented by chemical formula 1:
[ chemical formula 1]
In chemical formula 1, m is an integer of 4 to 10.
4. The polyimide resin according to claim 1, wherein the polyimide resin has a structure as shown in chemical formula 2:
[ chemical formula 2]
In chemical formula 2, R 1 And R is R 2 Each being a residue derived from a dianhydride monomer, R 3 Residues derived from diamine monomers other than the terminal amine-modified polyphenylene ether oligomer, m is an integer of 4 to 10, x is 0.2 to 1, and y is 0.8 to 0.
5. The polyimide resin according to claim 4, wherein in chemical formula 2:
R 1 and R is R 2 Each selected from at least one of the following options: 3,3', 4' -biphenyltetracarboxylic dianhydride derived residue, 1,4-phenylene bis (trimellitic monoester) dianhydride derived residue, pyromellitic dianhydride derived residue, 4' -oxydiphthalic anhydride derived residue, 4' - (hexafluoro-isopropenyl) diphthalic anhydride derived residue, 2,3,6,7-naphthalene tetracarboxylic dianhydride derived residue, 3', 4' -benzophenone tetracarboxylic dianhydride derived residue, 1,2,3, 4-cyclobutane tetracarboxylic dianhydride derived residue, 1,2,4,5-cyclohexane tetracarboxylic dianhydride derived residue, 4' -bisphenol A dianhydride derived residue,
R 3 a residue derived from at least one of diamine monomers represented by chemical formulas 3 to 9:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
[ chemical formula 9]
Wherein in chemical formulas 3 to 9, R 4 Independently represents hydrogen or a monovalent hydrocarbon group of 1 to 6 carbon atoms or an alkoxy group, the linking groups A independently represent a member selected from the group consisting of-O-, -S-, -CO-, -SO-, -SO2-, divalent radicals in-COO-, -CH2-, -C (CH 3) 2-, -NH-or-CONH-, n is n 1 Independently represents an integer of 0 to 4.
6. A copper clad laminate comprising:
a copper layer; and
the polyimide resin according to any one of claims 1 to 5, wherein the polyimide resin is formed on the copper layer.
7. A method for producing a polyimide resin, comprising:
dissolving a diamine monomer in a solvent, wherein the diamine monomer comprises a terminal amine group modified polyphenylene ether oligomer; and
dianhydride monomer is added into the solvent and polymerized.
8. The method for producing a polyimide resin according to claim 7, wherein the structure of the terminal amine group-modified polyphenylene ether oligomer is represented by chemical formula 1:
[ chemical formula 1]
In chemical formula 1, m is an integer of 4 to 10.
9. The method for producing a polyimide resin according to claim 7, wherein the amine-terminated modified polyphenylene ether oligomer is 20mol or more based on 100 mol of the total amount of the diamine monomers.
10. The method for producing a polyimide resin according to claim 7, wherein the polyimide resin has a structure represented by chemical formula 2:
[ chemical formula 2]
In chemical formula 2, R 1 And R is R 2 Each being a residue derived from said dianhydride monomer, R 3 Residues derived from diamine monomers other than the terminal amine-modified polyphenylene ether oligomer, m is an integer of 4 to 10, x is 0.2 to 1, and y is 0.8 to 0.
CN202210195652.XA 2022-01-22 2022-03-01 Copper-clad laminate, polyimide resin, and method for producing same Pending CN116515107A (en)

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JP2960281B2 (en) * 1992-05-25 1999-10-06 三井化学株式会社 Polyimide and method for producing the same
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