Polyarylene materials

Patent metadata

Field	Value
Publication number	US-9868820-B2
Application number	US-201414472429-A
Country	US
Kind code	B2
Filing date	Aug 29, 2014
Priority date	Aug 29, 2014
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

Certain polyarylene oligomers having improved solubility are useful in forming dielectric material layers in electronics applications.

First claim

What is claimed is:

1. An oligomer comprising as polymerized units a first monomer comprising two cyclopentadienone moieties, a second monomer having the formula (1), and a third monomer having the formula (2)

wherein a is the number of R groups and is an integer from 0 to 4; b is 1 or 2; each R is independently chosen from C 1-4 alkyl, halo C 1-4 alkyl, C 1-4 alkoxy, C 1-4 aralkyl, and optionally substituted C 6-10 aryl; each R 1 is independently H or optionally substituted C 6-10 aryl; R 2 is H, optionally substituted C 1-10 alkyl, optionally substituted C 7-12 aralkyl, optionally substituted C 6-10 aryl, or R 3 ; and R 3 is a polar moiety selected from the group consisting of carboxyl, C 2-12 aliphatic carboxylate, hydroxy C 1-10 alkyl, C 7-20 aryl carboxylic acid, C 8-20 aryl carboxylic acid anhydride, C 7-20 aryl carboxylates, C 7-20 aryl amide, and C 8-20 aryl imide.

2. The oligomer of claim 1 wherein the third monomer is selected from the group consisting of propiolic acid, acetylene dicarboxylic acid, phenyl propiolic acid, ethynyl benzoic acid, ethynyl phthalic acid, propargyl alcohol, 2-methyl-3-butyn-2-ol, xylityl propiolate, ethynyl phthalic anhydride, ethynyl phthalimide, ethynyl benzamide, 2-butyn-1,4-diol diacetate; 3-butyn-2-one; 1-ethynyl-1-cyclohexanol; 1-ethynylcyclohexylamine; 1-ethnylcyclopentanol; ethynylaniline; N-(ethynylphenyl)acetamide; 2-carbamoyl-5-ethynylbenzoic acid; ethynyl-nitrobenzene; propioamaide; N-hydroxyl -propiolamide; 2-aminobut-3-ynoic acid, and mixtures thereof.

3. The oligomer of claim 1 wherein the first monomer and the second monomer are present in a mole ratio of from 1:1.001 to 1:1.95.

4. The oligomer of claim 1 wherein the first monomer has the formula

wherein each R 4 is independently chosen from H, or optionally substituted phenyl; and Ar 1 is an aromatic moiety.

5. The oligomer of claim 1 wherein b=1.

6. The oligomer of claim 5 further comprising another second monomer wherein b=2.

7. A composition comprising the oligomer of claim 1 and an organic solvent.

8. The composition of claim 7 wherein the organic solvent is chosen from propylene glycol methyl ether, propylene glycol methyl ether acetate, methyl 3-methoxypropionate, ethyl lactate, anisole, N-methyl pyrrolidone, gamma-butyrolactone, ethoxybenzene, benzyl propionate, and mixtures thereof.

9. A method of forming a dielectric material layer comprising: disposing a layer of the composition of claim 7 on a substrate surface; removing the organic solvent; and curing the oligomer to form a dielectric material layer.

10. An oligomer comprising as polymerized units a first monomer comprising two cyclopentadienone moieties, a second monomer having the formula (1), and a third monomer having the formula (2)

wherein a is the number of R groups and is an integer from 0 to 4; b is 1 or 2; each R is independently chosen from C 1-4 alkyl, halo C 1-4 alkyl, C 1-4 alkoxy, C 1-4 aralkyl, and optionally substituted C 6-10 aryl; each R 1 is independently H or optionally substituted C 6-10 aryl; R 2 is H, optionally substituted C 1-10 alkyl, optionally substituted C 7-12 aralkyl, optionally substituted C 6-10 aryl, or R 3 ; and R 3 is a a hydrocarbyl moiety having from 1 to 20 carbon atoms and one or more functional groups chosen from —C(O)—, —NO 2 , and —NR 9 R 10 , where R 9 and R 10 are independently chosen from H, C 1-10 alkyl, C 7-16 aralkyl, and C 6-10 aryl.

Assignees

• Rohm & Haas Elect Mat
• Rohm & Haas Elect Materials Korea Ltd
• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Gilmore Christopher D
• Bu Lujia
• Chuang Peng-Wei
• Wang Deyan
• Kang Yerang
• Ding Ping
• Kim Young Seok
• O'Connell Kathleen M

Classifications

• H10W70/69

  Insulating materials thereof · CPC title

• H10W20/48

  Insulating materials thereof · CPC title

• C09D165/02

  Polyphenylenes · CPC title

• H01L23/49894

  Electricity · mapped topic

• C08G2261/135

  Cross-linked structures · CPC title