Polyarylene resins

Patent metadata

Field	Value
Publication number	US-10894848-B2
Application number	US-201715790606-A
Country	US
Kind code	B2
Filing date	Oct 23, 2017
Priority date	Dec 14, 2016
Publication date	Jan 19, 2021
Grant date	Jan 19, 2021

Abstract

Certain cyclopentadienone monomers having polar moieties are useful in forming polyarylene resins having improved solubility in certain organic solvents and are useful in forming polyarylene resin layers in electronics applications.

First claim

What is claimed is:

1. A cyclopentadienone compound of formula (1)

wherein each R 1 is independently chosen from H, C 1-20 -alkyl, optionally substituted C 5-30 -aryl; each R 2 is independently chosen from H, C 1-20 -alkyl, optionally substituted C 5-30 -aryl, and (PG-L) t -Ar 1 —; each PG is —C(═O)OR 5 ; R 5 is H; each Ar 1 is independently optionally substituted C 5-30 -aryl; L is a single chemical bond; and L 1 is chosen from —O—, —C 1-30 -ketoalkyl-, —C 1-30 -ketoalkyl-C 6-30 -aryl, —C 6 H 4 —, —C 10 H 6 —, —C 6 H 4 —C 6 H 4 —, —C 6 H 4 —O—C 6 H 4 —, —C 6 H 4 —O—C 6 H 4 —O—C 6 H 4 —, and groups of formula (1a); a is an integer from 0 to 3; t is an integer from 1 to 4; and w=1; provided that when a=0, L 1 has the formula (1a)

wherein Ar 2 is a C 5-30 -aryl; each R 3 is independently chosen from H, C 1-20 -alkyl, optionally substituted C 5-30 -aryl, and (PG-L) t -Ar 1 —; each of L 2 , L 3 and L 4 is chosen from a single chemical bond, —O—, —C 1-30 -alkyl-, —C 1-30 -ketoalkyl-, —C 1-30 -ketoalkyl-C 6-30 -aryl-, —C 6-30 -aryl-, —C 6-30 -aryl-O—C 6-30 -aryl-, —C 6-30 -aryl-O—C 6-30 -aryl-O—C 6-30 -aryl-, and combinations of the foregoing; t1 is an integer from 1 to 4; b is 0 or 1; and L 2 , L 3 and L 4 may be the same or different.

2. The cyclopentadienone compound of claim 1 wherein each Ar 1 and Ar 2 is independently chosen from pyridyl, phenyl, naphthyl, acenaphthyl, fluorenyl, carbazolyl, anthracenyl, phenanthryl, pyrenyl, coronenyl, tetracenyl, pentacenyl, tetraphenyl, benzotetracenyl, triphenylenyl, perylenyl, tolyl, xylyl, dibenzothiophenyl, thioxanthonyl, indolyl, and acridinyl.

3. A polyarylene resin comprising as polymerized units one or more first cyclopentadienone monomers of claim 1 , and one or more polyalkynyl-substituted second monomers.

4. The polyarylene resin of claim 3 wherein at least one polyalkynyl-substituted second monomer has the formula (2)

wherein each Ar 3 and Ar 4 is independently a C 5-30 aryl moiety; each R 11 is independently chosen from H, optionally substituted C 5-30 -aryl, and (PG-L 5 ) t2 -Ar 5 —; each R 12 is independently chosen from H, optionally substituted C 5-30 aryl, and -L 5 -PG; PG is a polar moiety; each Ar 5 is independently an optionally substituted C 5-30 -aryl; each L 5 is a single chemical bond or a divalent linking group; each Y is independently a single chemical bond or a divalent linking group chosen from —O—, —S—, —S(═O)—, —S(═O) 2 —, —C(═O)—, —(C(R 13 ) 2 ) z —, C 6-30 -aryl, and —(C(R 13 ) 2 ) z1 —(C 6-30 -aryl)-(C(R 13 ) 2 ) z2 —; each R 13 is independently chosen from H, hydroxy, halo, C 1-10 -alkyl, C 1-10 -haloalkyl, and optionally substituted C 6-30 -aryl; t2=1 to 4; b1=1 to 4; each b2=0 to 2; b1+ each b2=2 to 6; c=0 to 4; each c1=3 to 5; d=0 to 2; z=1 to 10; b1+c+d=6; z1=0 to 10; z2=0 to 10; and z1+z2=1 to 10.

5. The polyarylene resin of claim 4 wherein b1=2 or 3 and d=0.

6. The polyarylene resin of claim 4 wherein R 12 is H, or C 6-10-aryl .

7. A polyarylene resin composition comprising the polyarylene resin of claim 3 and one or more organic solvents.

8. A method of manufacturing an electronic device comprising providing a substrate; coating a layer of the polyarylene resin composition of claim 7 on a surface of the substrate; removing any organic solvent; and curing the polyarylene resin to form a dielectric material layer.

9. A method of forming a patterned layer comprising: (a) coating on a substrate a layer of a polyarylene resin composition of claim 7 ; (b) removing organic solvent to form a polyarylene resin layer; (c) coating a layer of a photoresist on the polyarylene resin layer; (d) exposing the photoresist layer to actinic radiation through a mask; (e) developing the exposed photoresist layer to form a resist pattern; and (f) transferring the pattern to the polyarylene resin layer to expose portions of the substrate.

10. The method of claim 9 wherein at least one polyalkynyl-substituted second monomer has the formula (2)

wherein each Ar 3 and Ar 4 is independently a C 5-30 aryl moiety; each R 11 is independently chosen from H, optionally substituted C 5-30 -aryl, and (PG-L 5 ) t2 -Ar 5 —; each R 2 is independently chosen from H, optionally substituted C 5-30 aryl, and -L 5 -PG; PG is a polar moiety; each Ar 5 is independently an optionally substituted C 5-30 -aryl; each L 5 is a single chemical bond or a divalent linking group; each Y is independently a single chemical bond or a divalent linking group chosen from —O—, —S—, —S(═O)—, —S(═O) 2 —, —C(═O)—, —(C(R 13 ) 2 ) z —, C 6-30 -aryl, and —(C(R 13 ) 2 ) z1 —(C 6-30 -aryl)-(C(R 13 ) 2 ) z2 —; each R 13 is independently chosen from H, hydroxy, halo, C 1-10 -alkyl, C 1-10 -haloalkyl, and optionally substituted C 6-30 -aryl; t2=1 to 4; b1=1 to 4; each b2=0 to 2; b1+ each b2=2 to 6; c=0 to 4; each c1=3 to 5; d=0 to 2; z=1 to 10; b1+c+d=6; z1=0 to 10; z2=0 to 10; and z1+z2=1 to 10.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Kinzie Charles R
• Greene Daniel
• Gilmore Christopher
• Cameron James F
• Ding Ping
• Wang Qing Min
• Kim Young-Seok

Classifications

• H10W20/48

  Insulating materials thereof · CPC title

• C08G2261/1424

  containing ether groups, including alkoxy · CPC title

• C08G61/12 Primary

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• C08G61/10 Primary

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C08G61/04

  only aliphatic carbon atoms · CPC title