Nadic anhydride polymers and photosensitive compositions derived therefrom

Patent metadata

Field	Value
Publication number	US-10591818-B2
Application number	US-201715662372-A
Country	US
Kind code	B2
Filing date	Jul 28, 2017
Priority date	Jul 28, 2016
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

Various vinyl addition polymers of nadic anhydride are disclosed. Examples of such polymers include copolymers and terpolymers of nadic anhydride with a wide variety of norbornene-type monomers. The nadic anhydride polymers are found to be useful in forming a wide variety of photosensitive compositions, both positive and negative, which are capable of forming high resolution imagable films exhibiting excellent dielectric properties (low-k) and thermal properties, and thus are useful in the fabrication of a variety of microelectronic and optoelectronic devices, among others.

First claim

What is claimed is:

1. A copolymer consisting of a first repeat unit which is derived from a monomer selected from the group consisting of:

3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione (nadic anhydride); and

5-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione; and a second repeat unit which is derived from a monomer selected from the group consisting of:

2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethyl acetate (NBCH 2 GlyOAc);

2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethanol (NBCH 2 GlyOH);

trioxanonanenorbornene (NBTON);

tetraoxadodecanenorbomnene (NBTODD);

5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM);

5-(3-methoxypropoxy)methyl-2-norbornene (NB-3-MPM);

5-(2-(2-ethoxyethoxy)ethyl)bicyclo[2.2.1]hept-2-ene;

5-(2-(2-(2-propoxyethoxy)ethoxy)ethoxy)bicyclo[2.2.1]hept-2-ene;

2-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (HFANB);

4-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)butan-2-ol (HFACH 2 NB);

5-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)pentan-2-ol (HFACH 2 CH 2 NB);

2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol; and

2-((2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (GlyHFIPNB).

2. A terpolymer consisting of a first repeat unit which is derived from a monomer selected from the group consisting of:

3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione (nadic anhydride); and

5-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione;
and a second re eat unit which is derived from a monomer selected from the group consisting of:

2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethyl acetate (NBCH 2 GlyOAc);

2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethanol (NBCH 2 GlyOH);

trioxanonanenorbornene (NBTON);

tetraoxadodecanenorbornene (NBTODD);

5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM);

5-(3-methoxypropoxy)methyl-2-norbornene (NB3-MPM);

5-(2-(2-(2-propoxyethoxy)ethoxy)ethoxy)bicyclo[2.2.1]hept-2-ene;

2-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (HFANB);

4-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)butan-2-ol (HFACH 2 NB);

5-bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)pentan-2-ol (HFACH 2 CH 2 NB);

2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol; and

2-((2-bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (GlyHFIPNB); and
a third repeat unit which is derived from a monomer selected from the group consisting of:

bicyclo[2.2.1]hept-2-ene (NB);

5-methylbicyclo[2.2.1]hept-2-ene (MeNB);

5-ethylbicyclo[2.2.1]hept-2-ene (EtNB);

5-hexylbicyclo[2.2.1]hept-2-ene (HexNB);

5-octylbicyclo[2.2.1]hept-2-ene (OctNB);

5-decylbicyclo[2.2.1]hept-2-ene (DecNB);

5-(hex-5-en-1-yl)bicyclo[2.2.1]hept-2-ene (HexenylNB);

bicyclo[2.2.1]hept-5-en-2-ylmethanamine;

tert-butyl (bicyclo[2.2.1]hept-5-en-2-ylmethyl)carbamate;

tert-butyl 4-((bicyclo[2.2.1]hept-5-en-2-ylmethyl)amino)-4-oxobutanoate;

(E)-4-((bicyclo[2.2.1]hept-5-en-2-ylmethyl)amino)-2,3-di methyl-4-oxobut-2-enoic acid;

N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-2,3,4,5,7-pentahydroxyheptan

Assignees

• Promerus Llc

Inventors

• Knapp Brian
• Burns Cheryl

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/0233

  characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides · CPC title

• 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

• G03F7/0755

  Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title