Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof

Patent metadata

Field	Value
Publication number	US-9291901-B2
Application number	US-201414477946-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 16, 2013
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

Disclosed herein are various amine treated maleic anhydride containing polymers and compositions thereof, which are useful for forming self-imageable films. In some embodiments, such polymers encompass norbornene-type repeating units containing pendent silyl groups and maleic anhydride-type repeating units where at least some of such maleic anhydride-type repeating units are either ring-opened or have been transformed into maleimide repeat units. The films formed from such copolymer compositions provide self imageable, low-k, thermally stable layers for use in microelectronic and optoelectronic devices.

First claim

What is claimed is:

1. A polymer comprising:
a first type of repeating unit represented by formula (IA), said first type of repeating unit is derived from a monomer of formula (I):

wherein:

m is an integer 0, 1 or 2;
at least one of R 1 , R 2 , R 3 and R 4 independently represents a group of formula (A):
—SiR 5 R 6 R 7   (A)

wherein:
R 5 , R 6 , and R 7 are the same or different and each independently of one another is selected from linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl;

remaining one or more of R 1 , R 2 , R 3 and R 4 independently represents hydrogen, linear or branched (C 1 -C 16 )alkyl, hydroxy(C 1 -C 16 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryl, (C 5 -C 10 )heteroaryl(C 1 -C 8 )alkyl, hydroxy, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryloxy(C 1 -C 3 )alkyl, (C 6 -C 10 )aryloxy, (C 5 -C 10 )heteroaryloxy, (C 1 -C 6 )acyloxy, halogen, di(C 1 -C 2 )alkylmaleimide(C 3 -C 6 )alkyl, di(C 1 -C 2 )alkylmaleimide(C 2 -C 6 )alkoxy(C 1 -C 2 )alkyl, oxiranyl(C 0 -C 8 )alkyl, oxiranyl(CH 2 ) a O(CH 2 ) b —, or a group of formula (B):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (B)

wherein:
a is an integer 0, 1, 2, 3 or 4;
b is an integer 0, 1, 2, 3 or 4; and
R is linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl;

optionally a second type of repeating unit represented by formula (IIA), said second type of repeating unit is derived from a monomer of formula (II):

wherein
R 8 , R 9 , R 10 and R 11 are the same or different and each independently of one another is selected from hydrogen, linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl or a group of formula (C):
—SiR 5 R 6 R 7   (C)

wherein:
R 5 , R 6 , and R 7 are the same or different and each independently of one other is selected from linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl; or

one of R 8 or R 9 taken together with one of R 10 or R 11 and the carbon atoms to which they are attached form a (C 5 -C 8 )cycloalkyl ring; and
one or more of a third type of repeating unit chosen from formulae (IIIC), (IIIA), (IIIB), (IIID) and (IIIE), said third type of repeating unit is derived from a monomer of formula (III):

wherein:
R 12 and R 13 are each independently of one another represents hydrogen or linear or branched (C 1 -C 9 )alkyl or fluorinated or perfluorinated (C 1 -C 9 )alkyl;
R 18 is hydrogen, linear or branched (C 1 -C 20 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl; and

a fourth type of repeating unit represented by formula (IVA), said fourth type of repeating unit is derived from a monomer of formula (IV):

wherein:
n is an integer 0, 1 or 2;
R 14 , R 15 , R 16 and R 17 independently represents hydrogen, linear or branched (C 1 -C 16 )alkyl, hydroxy(C 1 -C 16 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )bicycloalkyl, (C 7 -C 14 )tricycloalkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, perfluoro(C 6 -C 10 )aryl, perfluoro(C 6 -C 10 )aryl(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryl, (C 5 -C 10 )heteroaryl(C 1 -C 8 )alkyl, hydroxy, (C 1 -C 12 )alkoxy, (C 3 -C 12 )cycloalkoxy, (C 6 -C 12 )bicycloalkoxy, (C 7 -C 14 )tricycloalkoxy, (C 6 -C 10 )aryloxy(C 1 -C 3 )alkyl, (C 5 -C 10 )heteroaryloxy(C 1 -C 3 )alkyl, (C 6 -C 10 )aryloxy, (C 5 -C 10 )heteroaryloxy, (C 1 -C 6 )acyloxy, halogen, oxiranyloxy(C 1 -C 3 )alkyl, oxiranyl(C 0 -C 8 )alkyl, oxiranyl(CH 2 ) a O(CH 2 ) b —, or a group of formula (B):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (B)

wherein:
a is an integer 0, 1, 2, 3 or 4;
b is an integer 0, 1, 2, 3 or 4; and

R is linear or branched (C 1 -C 6 )alkyl, (C 5 -C 5 )cycloalkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl; and
wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from linear or branched (C 1 -C 6 )alkyl, (C 3 -C 7 )cycloalkyl, (C 1 -C 6 )perfluoroalkyl, (C 1 -C 6 )alkoxy, (C 3 -C 7 )cycloalkoxy, (C 1 -C 6 )perfluoroalkoxy, halogen, hydroxy, linear or branched hydroxy(C 1 -C 6 )alkyl, (C 6 -C 10 )aryl or (C 7 -C 12 )aralkyl.

2. The polymer of claim 1 wherein said polymer comprises 10 to 75 mole percent of first type of repeating units, 0 to 90 mole percent of second type of repeating units and 10 to 60 mole percent of third type of repeating units.

3. The polymer of claim 1 wherein:
at least one of R 1 , R 2 , R 3 and R 4 independently represents a group of formula (A):
—SiR 5 R 6 R 7   (A)

wherein:
R 5 , R 6 , and R 7 are the same or different and each independently of one other is selected from linear or branched (C 1 -C 6 )alkyl;

remaining one or more of R 1 , R 2 , R 3 and R 4 independently represents hydrogen, linear or branched (C 1 -C 12 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 5 -C 10 )heteroaryl(C 1 -C 8 )alkyl, oxiranyl(C 0 -C 8 )alkyl, oxiranyl(CH 2 ) a O(CH 2 ) b —, or a group of formula (B):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (B)

wherein:
a is an integer 0, 1, 2, 3 or 4;
b is an integer 0, 1, 2, 3 or 4; and
R is linear or branched (C 1 -C 6 )alkyl; and

R 12 and R 13 are each hydrogen.

4. The polymer of claim 1 , wherein:
n is an integer 0 or 1;
R 14 , R 15 , R 16 and R 17 independently represents hydrogen, linear or branched (C 1 -C 16 )alkyl, perfluoro(C 1 -C 12 )alkyl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, perfluoro(C 6 -C 10 )aryl, (C 5 -C 10 )heteroaryl(C 1 -C 8 )alkyl, oxiranyloxy(C 1 -C 3 )alkyl, oxiranyl(C 0 -C 8 )alkyl or a group of formula (B):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (B)

wherein:
a is an integer 0, 1, 2, 3 or 4;
b is an integer 0, 1, 2, 3 or 4; and
R is linear or branched C 1 -C 6 -alkyl.

5. The polymer of claim 1 wherein said third type of repeating unit is of the formula (IIIA) or (IIIB):

wherein:
R 12 and R 13 are each independently of one another represents hydrogen or methyl; and
R 18 is selected from hydrogen, n-octyl, n-dodecyl, n-hexadecyl and n-octadecyl.

6. The polymer of claim 1 wherein first type of repeating unit is derived from a monomer selected from the group consisting of:
bicyclo[2.2.1]hept-5-en-2-yltrimethylsilane;
bicyclo[2.2.1]hept-5-en-2-yltriethylsilane;
bicyclo[2.2.1]hept-5-en-2-yldimethyl-tert-butylsilane; and
bicyclo[2.2.1]hept-5-en-2-yldimethylphenylsilane.

7. The polymer of claim 1 wherein second type of repeating unit is derived from a monomer selected from the group consisting of:
2-methylprop-1-ene;
2-methylpent-1-ene;
2,4,4-trimethylpent-1-ene;
2,4,4-trimethylpent-2-ene;
trimethyl(vinyl)silane; and
styrene.

8. The polymer of claim 1 wherein fourth type of repe

Assignees

• Promerus Llc
• Sumitomo Bakelite Co

Inventors

• Kandanarachchi Pramod
• Rhodes Larry F

Classifications

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C09D135/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers · CPC title

• G03F7/30

  Imagewise removal using liquid means · CPC title

• C08F232/04

  having one carbon-to-carbon double bond · CPC title

• C08F8/48

  Isomerisation; Cyclisation · CPC title