Amine treated maleic anhydride polymers, compositions and applications thereof

Patent metadata

Field	Value
Publication number	US-9422376-B2
Application number	US-201414477928-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 16, 2013
Publication date	Aug 23, 2016
Grant date	Aug 23, 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 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;
X is CH 2 , CH 2 —CH 2 , O or NR a where R a is linear or branched (C 1 -C 6 )alkyl;
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, 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, 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, oxiranyl(C 0 -C 8 )alkyl, oxiranyl(CH 2 ) a O(CH 2 ) b —, halogen or a group of formula (A):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (A)

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;

and/or
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 (B):
—SiR 5 R 6 R 7   (B)

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
a third type of repeating unit represented by formula (IIIA) or (IIIB), said third type of repeating unit (IIIA) or (IIIB) is derived from a monomer of formula (III):

further comprising a third type of repeating unit represented by formula (IIIE) derived from the 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 14 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
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, wherein said polymer comprises one or more of said first type of repeating units.

2. The polymer of claim 1 wherein said polymer further comprises a third type of repeat unit represented by formula (IIIC) derived from the monomer of formula (III):

wherein R 12 and R 13 are as defined in claim 1 .

3. The polymer of claim 1 wherein said polymer further comprises a third type of repeat unit represented by formula (IIID) derived from the monomer of formula (III):

wherein R 12 and R 13 are as defined in claim 1 .

4. The polymer of claim 1
wherein R 12 and R 13 independently of each other selected from the group consisting of hydrogen, methyl, ethyl and trifluoromethyl; and
R 14 is linear or branched (C 8 -C 20 )alkyl.

5. The polymer of claim 1 wherein:
X=CH 2 ;
m=0;
R 1 , R 2 , R 3 and R 4 independently represents hydrogen, hexyl, decyl, oxiranyl-CH 2 OCH 2 —, di(C 1 -C 2 )alkylmaleimide(C 3 -C 6 )alkyl or a group of formula (A):
—(CH 2 ) a —(OCH 2 —CH 2 ) b —OR  (A)

wherein:
a is 1 or 2;
b is 2 or 3; and
R is methyl, ethyl, n-propyl or n-butyl;

R 8 , R 9 , R 10 and R 11 are the same or different and each independently of one another is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, phenyl, trimethylsilyl and triethylsilyl; or
R 8 and R 10 are the same or different and each independently of one another is selected from hydrogen, methyl or ethyl; and R 9 taken together with R 11 and the carbon atoms to which they are attached form cyclohexyl, cycloheptyl or cyclooctyl ring;
R 12 and R 13 are the same or different and each independently of one another is selected from hydrogen, methyl or ethyl; and
R 14 is (C 4 -C 18 )alkyl.

6. The polymer of claim 1 wherein said polymer comprises one or more second type of repeating units.

7. The polymer of claim 1 wherein said polymer comprises 0 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.

8. 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-2-ene;
5-methylbicyclo[2.2.1]hept-2-ene;
5-ethylbicyclo[2.2.1]hept-2-ene;
5-hexylbicyclo[2.2.1]hept-2-ene;
5-octylbicyclo[2.2.1]hept-2-ene;
5-decylbicyclo[2.2.1]hept-2-ene;
5-((2-(2-methoxyethoxy)ethoxy)methyl)bicyclo[2.2.1]hept-2-ene;
1-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)-3,4-dimethyl-1H-pyrrole-2,5-dione;
2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane; and
5-phenethylbicyclo[2.2.1]hept-2-ene.

9. 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.

10. A photoimageable composition comprising:
a polymer containing:
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;
X is CH 2 , CH 2 —CH 2 , O or NR a where R a is linear or branched (C 1 -C 6 )alkyl;
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, di(C 1 -C 2 )alkylmaleimide(C 3 -C 6 )alkyl, di(C 1 -C 2 )alkylmaleimide(C 2 -C 6 )alkoxy(

Assignees

• Promerus Llc
• Sumitomo Bakelite Co
• Sumitomo Bakelite Co

Inventors

• Kandanarachchi Pramod
• Rhodes Larry F
• Onishi Osamu

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

• C09D145/00

  Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides or imides C09D135/00) · CPC title

• C08F212/08

  Styrene · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• C08F230/08

  containing silicon · CPC title