Photoimageable polyolefin compositions containing photobase generators

Patent metadata

Field	Value
Publication number	US-9952507-B2
Application number	US-201615042240-A
Country	US
Kind code	B2
Filing date	Feb 12, 2016
Priority date	Feb 18, 2015
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

Embodiments in accordance with the present invention encompass self-imageable 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 photoimageable composition comprising:
a) a polymer consisting of one or more repeating units of formula (VIIIA) derived from a monomer of formula (VIII):

wherein represents a position at which the bonding takes place with another repeat unit;
R 18 is selected from the group consisting of (C 6 -C 18 )alkyl; perfluoro(C 1 -C 18 )alkyl; (C 6 -C 10 )aryl(C 1 -C 6 )alkyl; —(CH 2 ) a —C(CF 3 ) 2 OR; —(CH 2 ) a —CO 2 R 2 ;
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;
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; and
R 2 is selected from the group consisting of hydrogen and (C 1 -C 4 )alkyl;
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):

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

a) a carrier solvent.

2. The composition of claim 1 , wherein the polymer consisting of one or more repeat units derived from the corresponding monomer of formula (VIII) selected from the group consisting of:
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol;
trioxanonanenorbornene;
tetraoxadodecanenorbornene;
5-(3-methoxybutoxy)methyl-2-norbornene;
5-(3-methoxypropanoxy)methyl-2-norbornene;
ethyl 3-(bicyclo[2.2.1]hept-2-en-2-yl)propanoate;
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; and
norbornenylpropanoic acid.

3. The composition of claim 1 , wherein the polymer consisting of one or more repeat units derived from the corresponding monomers selected from the group consisting of:
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol; and
norbornenylpropanoic acid.

4. The composition of claim 1 , wherein the photobase generator is selected from the group consisting of:
2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one;
2-(dimethylamino)-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one;
2-nitrobenzyl 4-hydroxypiperidine-1-carboxylate;
4,5-dimethoxy-2-nitrobenzyl 2,6-dimethylpiperidine-1-carboxylate;
1-(9,10-dioxo-9,10-dihydroanthracen-2-yl)ethyl cyclohexylcarbamate;
1-(9,10-dioxo-9,10-dihydroanthracen-2-yl)ethyl 1H-imidazole-1-carboxylate;
diaminomethaniminium 2-(3-benzoylphenyl)propanoate; and
(Z)—N-(((bis(dimethylamino)methylene)amino)(isopropylamino)-methylene)propan-2-aminium 2-(3-benzoylphenyl)propanoate.

5. The composition of claim 1 further comprises one or more additives selected from the group consisting of:
a crosslinking agent;
an antioxidant; and
an adhesion promoter.

6. The composition of claim 5 , wherein the crosslinking agent is selected from:
2,2′-(((2-ethyl-2-((oxiran-2-ylmethoxy)methyl)propane-1,3-diyl)bis(oxy))-bis(methylene))bis(oxirane); and
triglycidyl ether of poly(oxypropylene)epoxide ether of glycerol.

7. A microelectronic or optoelectronic device comprising one or more of a redistribution layer (RDL) structure, a chip-stack structure, or a CMOS image sensor dam structure, where said structure further comprises a composition according to any one of claims 1 to 6 .

Assignees

• Promerus Llc

Inventors

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

Classifications

• G03F7/0392

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

• G03F7/0046

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

• G03F7/0045 Primary

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

• G03F7/0395

  the macromolecular compound having a backbone with alicyclic moieties · CPC title