Thermo-oxidatively stable, side chain polyether functionalized polynorbornenes for microelectronic and optoelectronic devices and assemblies thereof

Patent metadata

Field	Value
Publication number	US-9562124-B2
Application number	US-201615209289-A
Country	US
Kind code	B2
Filing date	Jul 13, 2016
Priority date	Jan 16, 2012
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

The present invention relates to polynorbornene (PNB) composition embodiments that are useful for forming microelectronic and/or optoelectronic devices and assemblies thereof, and more specifically to compositions encompassing PNBs having norbornene-type repeating units that are polyether functionalized and an additive package containing a phenolic antioxidant and a diaryl amine synergist, and the microelectronic and/or optoelectronic devices made therefrom are resistant to thermo-oxidative chain degradation of said polyether functionalization.

First claim

What is claimed is:

1. A thermo-oxidatively stabilized composition comprising:
a polymer having repeating units derived from a norbornene-type monomer in accordance with Formula A:

where s is selected from 0 to 3, t is 2, u is an integer from 1 to 3 and R 5 is selected from methyl, ethyl, n-propyl or i-propyl; and
an additive package comprising:
one or more phenolic antioxidant selected from the group consisting of:
2,2′-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(4-methylphenol),
6,6′-methylenebis(2-(2-hydroxy-5-methylbenzyl)-4-methylphenol),
6,6′-(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)bis(2-(2-hydroxy-5-methylbenzyl)-4-methylphenol),
6,6′-methylenebis(2-(2-hydroxy-3,5-dimethylbenzyl)-4-methylphenol), and
6,6′-(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)bis(2,4-dimethylphenol); and
one or more diaryl amine synergist selected from the group consisting of:
N,N′-di-2-naphthyl-p-phenylenediamine,
bis(4-(tert-butyl)phenyl)amine,
bis(4-(2-phenylpropan-2-yl)phenyl)amine,
bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)amine and bis(4-(2,4,4-trimethylpentyl)phenyl)amine; and wherein each of said antioxidant and amine synergist is present in an amount from 3 to 10 parts per hundred parts of said polymer.

2. The thermo-oxidatively stabilized composition of claim 1 , where one or more of the diaryl amine synergist is selected from the group consisting of:
bis(4-(tert-butyl)phenyl)amine,
bis(4-(2-phenylpropan-2-yl)phenyl)amine, and
bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)amine;
and one or more of the phenolic antioxidant is selected from the group consisting of:
2,2′-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(4-methylphenol), and
6,6′-methylenebis(2-(2-hydroxy-5-methylbenzyl)-4-methylphenol).

3. The thermo-oxidatively stabilized composition of claim 1 , where the diaryl amine synergist is bis(4-(2-phenylpropan-2-yl)phenyl)amine and the phenolic antioxidant is 2,2′-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(4-methylphenol).

4. The thermo-oxidatively stabilized composition of claim 1 , where the norbornene-type monomer in accordance with Formula A is trioxanonanenorbornene (NBTON) or tetraoxadodecanenorbornene (NBTODD).

5. The thermo-oxidatively stabilized composition of claim 1 , where the polymer further comprises repeating units derived from one or more norbornene-type monomers selected from the group consisting of:
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB),
norbornene methyl glycidyl ether (MGENB),
5-decylbicyclo[2.2.1]hept-2-ene (DecNB),
5-phenethylbicyclo[2.2.1]hept-2-ene (PENB),
5-phenbutylbicyclo[2.2.1]hept-2-ene (PBNB),
ethyl 3-(bicyclo[2.2.1]hept-2-en-2-yl)propanoate (EPEsNB),
2-(6-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane (EONB),
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (Acid NB) and
norbornenylpropanoic acid (NBEtCOOH).

6. The thermo-oxidatively stabilized composition of claim 1 , further comprising one or more additives selected from the group consisting of:
a photoactive compound;
a cross-linking agent;
a photosensitizer; and
a photoacid generator.

7. The thermo-oxidatively stabilized composition of claim 6 , where the photoactive compound comprises a 1,2-naphthoquinonediazide-5-sulfonyl moiety and/or a 1,2-naphthoquinonediazide-4-sulfonyl moiety as represented by structural formulae 2a and 2b, respectively, or a sulfonyl benzoquinone diazide group represented by structural formula 2c:

8. The thermo-oxidatively stabilized composition of claim 6 , where the photoactive compound is selected from the group consisting of:

and the remaining Q is hydrogen.

9. The thermo-oxidatively stabilized composition of claim 6 , where the photoactive compound is:

where two of Q is a group of formula 2a or 2b:

and the remaining Q is hydrogen.

10. The thermo-oxidatively stabilized composition of claim 6 , where the cross-linking agent is selected from the group consisting of:

11. The thermo-oxidatively stabilized composition of claim 1 , further comprising one or more additives selected from the group consisting of:

12. The thermo-oxidatively stabilized composition of claim 1 , further comprising a solvent selected from the group consisting of: methyl amyl ketone (MAK), γ-butyrolactone (GBL) and propyleneglycol monomethylether acetate (PGMEA).

13. The thermo-oxidatively stabilized composition of claim 6 , where the photoacid generator is:

14. The thermo-oxidatively stabilized composition of claim 13 , further comprising one or more additives selected from the group consisting of:

Assignees

• Promerus Llc
• Sumitomo Bakelite Co

Inventors

• Apanius Christopher
• Bell Andrew
• Burns Cheryl
• Cyrus Crystal
• Elce Edmund
• Groff Royce
• Kaiti Sridevi
• Knapp Brian
• Ng Hendra
• Ohashi Seishi
• Zhang Wei

Classifications

• H10P72/7402

  Wafer tapes, e.g. grinding or dicing support tapes · CPC title

• H10W20/48

  Insulating materials thereof · CPC title

• G03F7/039

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

• H01L21/6836

  Electricity · mapped topic

• C08F2500/25

  Cycloolefine · CPC title