# US 9,049,778 B2 · Polyamic acid, photosensitive resin composition, dry film and circuit board

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- Number: US 9,049,778 B2
- Document ID: US9049778B2
- Status: Granted
- Kind: B2
- Application number: 14/006,062
- Filed: 2012-03-19
- Published: 2014-01-09
- Granted: 2015-06-02
- Earliest claimed: 2011-03-18
- Assignees: LG Chem, Ltd.
- Applicants: You-Jin Kyung; Hee-Jung Kim; Kwang-Joo Lee; Jung-Hak Kim
- Inventors: You-Jin Kyung; Hee-Jung Kim; Kwang-Joo Lee; Jung-Hak Kim
- Web page: https://patentgrep.com/patent/US9049778B2

## CPC

- H05K 3/0076: {characterised by the composition of the mask}
- C08G 73/1046: {Polyimides containing oxygen in the form of ether bonds in the main chain}
- C08G 73/105: {with oxygen only in the diamino moiety}
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G03F 7/031: Organic compounds not covered by group G03F7/029
- G03F 7/037: the binders being polyamides or polyimides
- H05K 3/287: {Photosensitive compositions}
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

The present invention relates to novel polyamic acid; a photosensitive resin composition satisfying excellent flexibility and low stiffness and exhibiting excellent heat resistance and plating resistance; a dry film obtained from the photosensitive resin composition; and a circuit board including the dry film.

## Claims

### Claim 1

Polyamic acid comprising a repeat unit of the following Chemical Formula 1:
in the Chemical Formula 1,
X1 and X2 are identical or different, and independently a tetravalent organic group,
R1, R2, R3 and R4 are identical or different, and independently a C1-10 linear or branched alkylene group,
R5 is a C1-10 linear or branched alkyl group,
x, y and z are independently an integer greater than or equal to 1, and
n is an integer greater than or equal to 0.

### Claim 2 (depends on 1)

The polyamic acid according to claim 1, wherein in the Chemical Formula 1, R1, R2, R3 and R4 are independently a methylene group, an ethylene group, an n-propylene group, an iso-propylene group, an n-butylene group, an iso-butylene group, an n-pentylene group, an iso-pentylene group or a neo-pentylene group,
x, y and z are independently an integer of from 1 to 30, and
n is an integer of from 0 to 30.

### Claim 3 (depends on 1)

The polyamic acid according to claim 1, comprising a repeat unit of the Chemical Formula 2:
in the Chemical Formula 2,
X1 and X2 are identical or different, and independently a tetravalent organic group, and
x, y and z are independently an integer of from 1 to 30.

### Claim 4 (depends on 1)

The polyamic acid according to claim 1,
wherein X1 and X2 are identical or different, and independently a tetravalent organic group selected from the group consisting of the following Chemical Formulae 11 to 24:
in the Chemical Formula 12, Y1 is a single bond, —O—, —CO—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —CONH—, —COO—, —(CH2)n1—, —O(CH2)n2O—, or —COO(CH2)n3OCO—, and n1, n2 and n3 are independently an integer of from 1 to 10,
in the Chemical Formula 13, Y2 and Y3 are identical or different, and independently a single bond, —O—, —CO—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —CONH—, —COO—, —(CH2)n1—, —O(CH2)n2O—, or —COO(CH2)n3OCO—, and n1, n2 and n3 are independently an integer of from 1 to 10,
in the Chemical Formula 14, Y4, Y5 and Y6 are identical or different, and independently a single bond, —O—, —CO—, —S—, —SO2—, —C(CH3)2—, —C(CF3)2—, —CONH—, —COO—, —(CH2)n1—, —O(CH2)n2O—, or —COO(CH2)n3OCO—, and n1, n2 and n3 are independently an integer of from 1 to 10,
in the Chemical Formula 16 and 17, * is a bonding point,

### Claim 5 (depends on 1)

The polyamic acid according to claim 1, further comprising a repeat unit of the following Chemical Formula 8:
in the Chemical Formula 8,
X5 is a tetravalent organic group, R6 and R7 are identical or different and independently a C1-10 linear or branched alkylene group, and q is an integer greater than equal to 1.

### Claim 6 (depends on 5)

The polyamic acid according to claim 5, further comprising a repeat unit of the following Chemical Formula 3:
in the Chemical Formula 3,
X3 is a tetravalent organic group, and X4 is a divalent organic group.

### Claim 7 (depends on 6)

The polyamic acid according to claim 6, comprising
0.1 to 30 mol % of the repeat unit of the Chemical Formula 1;
2 to 50 mol % of the repeat unit of the Chemical Formula 8; and
20 to 97.9 mol % of the repeat unit of the Chemical Formula 3.

### Claim 8 (depends on 1)

The polyamic acid according to claim 1,
wherein the polyamic acid has a weight average molecular weight of 5,000 to 200,000.

### Claim 9 (depends on 1)

A photosensitive resin composition comprising a polymer resin comprising the polyamic acid of claim 1; a photocrosslinking agent; an organic solvent; and a photopolymerization initiator.

### Claim 10 (depends on 9)

The photosensitive composition according to claim 9, wherein the photocrosslinking agent includes a (meth)acrylate-based compound including a double bond between carbons.

### Claim 11 (depends on 9)

The photosensitive composition according to claim 9, wherein the photopolymerization initiator includes a compound selected from the group consisting of an acetophenone based compound, a biimidazole based compound, a triazine base compound, and an oxime based compound.

### Claim 12 (depends on 9)

The photosensitive composition according to claim 9, wherein the polymer resin has a solid concentration of 20 to 90 wt %, based on the total weight of the photosensitive resin composition.

### Claim 13 (depends on 9)

The photosensitive composition according to claim 9, comprising,
based on 100 parts by weight of the polymer resin composition,
5 to 300 parts by weight of the photocrosslinking agent;
100 to 700 parts by weight of the organic solvent; and
0.3 to 10 parts by weight of the photopolymerization initiator.

### Claim 14 (depends on 9)

The photosensitive composition according to claim 9, further comprising at least one additives selected from the group consisting of a thermal crosslinking agent, a curing accelerator, a photocrosslinking sensitizer, a phosphorus flame retardant, an antifoaming agent, a leveling agent, and an antigelling agent.

### Claim 15 (depends on 9)

A dry film comprising a cured product of the photosensitive resin composition of claim 9.

### Claim 16 (depends on 15)

The dry film according to claim 15, wherein the dry film is used for a protection film for a circuit board, a base film for a circuit board, an insulating layer of a circuit board, a semiconductor interlayer dielectric, or a solder resist.

### Claim 17 (depends on 15)

A circuit board comprising the dry film of claim 15.

### Claim 18 (depends on 17)

The circuit board according to claim 17, wherein the circuit board is a multi-layer printed-circuit board, a flexible circuit board, or a ductile circuit board.