Photoimageable polyolefin compositions containing photobase generators

Patent metadata

Field	Value
Publication number	US-10409160-B2
Application number	US-201815918604-A
Country	US
Kind code	B2
Filing date	Mar 12, 2018
Priority date	Feb 18, 2015
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

Embodiments in accordance with the present invention encompass self-imagable polymer compositions containing a variety of photobase generators which are useful for forming films that can be patterned to create structures for microelectronic devices, microelectronic packaging, microelectromechanical systems, optoelectronic devices and displays. The compositions of this invention can be tailored to form positive tone or negative tone images depending upon the intended application in aqueous developable medium. The images formed therefrom exhibit improved properties including low wafer stress and better thermo-mechanical properties, among other property enhancements.

First claim

What is claimed is:

1. A photoimagable composition comprising:
a) a polymer consisting of one or more first repeating units represented by formula (IA), said first repeating unit is derived from a monomer of formula (I):

wherein:
m is an integer 0, 1 or 2;
R 1 , R 2 , R 3 and R 4 are the same or different and each independently selected from the group consisting of hydrogen, halogen, linear or branched (C 1 -C 12 )alkyl, linear or branched hydroxy(C 1 -C 12 )alkyl, linear or branched 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 6 )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 3 )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, —(CH 2 ) a —C(CF 3 ) 2 OR, —(CH 2 ) a —CO 2 R,
a group of formula (A):
—(CH 2 ) b —(OCH 2 —CH 2 ) c —OR  (A); and

a group of formula (B):

wherein:
a is an integer from 0 to 4
b is an integer from 0 to 10;
c is an integer 0, 1, 2, 3 or 4; and
R is selected from the group consisting of hydrogen, linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl and (C 7 -C 12 )aralkyl;
a second repeating unit represented by formula (IIA), said second 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 the group consisting of hydrogen, linear or branched (C 1 -C 6 )alkyl, (C 5 -C 8 )cycloalkyl, (C 6 -C 10 )aryl and (C 7 -C 12 )aralkyl;
and
a third repeating unit selected from the group consisting of a repeating unit of formula (IIIA) and a repeating unit of formula (IIIB), said third repeating unit is derived from a monomer of formula (III):

wherein:
Z is O or N—R 12 wherein R 12 is selected from the group consisting of hydrogen, linear or branched (C 1 -C 9 )alkyl, (C 3 -C 7 )cycloalkyl and (C 6 -C 12 )aryl;
R 5 , R 6 and R 7 are each independently of one another selected from the group consisting of hydrogen, linear or branched (C 1 -C 9 )alkyl, fluorinated or perfluorinated(C 1 -C 9 )alkyl, (C 6 -C 12 )aryl and (C 6 -C 12 )aryl(C 1 -C 12 )alkyl; and
wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from the group consisting of 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, acetoxy, phenyl, hydroxyphenyl and acetoxyphenyl;
b) a photobase generator selected from the group consisting of:
a compound of formula (IV):

a compound of formula (V):

a compound of formula (VI):

a compound of formula (VIIA):

a compound of formula (VIIB):

 and
a compound of formula (VIIC):

wherein

R 13 and R 14 each independently of each other selected from the group consisting of hydrogen, linear or branched (C 1 -C 8 )alkyl and (C 6 -C 10 )aryl; or
R 13 and R 14 taken together with the nitrogen atom to which they are attached form a 5 to 7 membered monocyclic ring or 6 to 12 membered bicyclic ring, said rings optionally containing one or more heteroatoms selected from O and N, and said rings optionally substituted with a group selected from the group consisting of linear or branched (C 1 -C 8 )alkyl, (C 6 -C 10 )aryl, halogen, hydroxy, linear or branched (C 1 -C 8 )alkoxy and (C 6 -C 10 )aryloxy; and
R 15 , R 16 and R 17 are the same or different and each independently of one another selected from the group consisting of hydrogen, linear or branched (C 1 -C 16 )alkyl, (C 6 -C 10 )aryl, (C 6 -C 10 )aryl(C 1 -C 3 )alkyl, hydroxy, halogen, linear or branched (C 1 -C 12 )alkoxy and (C 6 -C 10 )aryloxy; and
c) a carrier solvent.

2. The composition of claim 1 , wherein the polymer consists of:
one or more first repeat units derived from the corresponding monomers selected from the group consisting of:
bicyclo[2.2.1]hept-2-ene;
5-decylbicyclo[2.2.1]hept-2-ene;
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol;
5-phenethylbicyclo[2.2.1]hept-2-ene; and
norbornenylpropanoic acid;
one or more second repeat units derived from the corresponding monomers selected from the group consisting of:
styrene; and
□-methylstyrene; and
one or more third repeat units derived from the corresponding monomers selected from the group consisting of:
maleic anhydride; and
2-methyl-maleic anhydride.

3. A photoimagable composition comprising:
a) a copolymer containing repeating units derived from styrene and ring opened maleic anhydride repeat units which is ring opened with n-butylamine;
b) a photobase generator selected from the group consisting of:
a compound of formula (IV):

a compound of formula (V):

a compound of formula (VI):

a compound of formula (VIIA):

a compound of formula (VIIB):

 and
a compound of formula (VIIC):

wherein
R 13 and R 14 each independently of each other selected from the group consisting of hydrogen, linear or branched (C 1 -C 8 )alkyl and (C 6 -C 10 )aryl; or
R 13 and R 14 taken together with the nitrogen atom to which they are attached form a 5 to 7 membered monocyclic ring or 6 to 12 membered bicyclic ring, said rings optionally containing one or more heteroatoms selected from O and N, and sa

Assignees

• Promerus Llc

Inventors

• Kandanarachchi Pramod
• Rhodes Larry F
• Ng Hendra
• Zhang Wei
• Knapp Brian

Classifications

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/038 Primary

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

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title