Photosensitive compositions and applications thereof

Patent metadata

Field	Value
Publication number	US-9341949-B2
Application number	US-201414261922-A
Country	US
Kind code	B2
Filing date	Apr 25, 2014
Priority date	Apr 26, 2013
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The present invention relates to photosensitive compositions containing polynorbornene (PNB) polymers and certain additives that are useful for forming microelectronic and/or optoelectronic devices and assemblies thereof, and more specifically to compositions encompassing PNBs and certain hindered phenols as additives which are resistant to thermo-oxidative chain degradation.

First claim

What is claimed is:

1. A photosensitive composition comprising:
a) a polymer having a first repeating unit of formula (IA) derived from a monomer of formula (I):

wherein:
represents a position at which the bonding takes place with another repeat unit;
a is an integer from 0 to 3;
b is an integer from 1 to 4;
c is an integer from 1 to 4;
R 1 is selected from hydrogen, methyl, ethyl, n-propyl, i-propyl or n-butyl;

b) a photo active compound containing a diazo-quinone moiety of formula (A):

c) an epoxy compound containing one or more oxirane groups; and
d) an additive selected from:
a compound of formula (IV):

wherein d and e are integers from 1 to 4;
f and g are integers from 0 to 4;
R 2 and R 3 are the same or different and independently of each other selected from hydrogen, methyl, ethyl, linear or branched C 3 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl; or
R 2 and R 3 taken together with the carbon atom to which they are attached form a 5 to 8 membered substituted or unsubstituted carbocyclic ring where said substituents are selected from C 1 -C 8 alkyl;
R 4 and R 5 are the same or different and independently of each other selected from hydrogen, methyl, ethyl, linear or branched C 3 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl;

a compound of formula (V):

wherein h is an integer from 1 to 4;
i is 1 or 2;
R 6 independently is hydrogen, methyl, ethyl, linear or branched C 3 -C 16 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl;

a compound of formula (VI):

wherein j and k are integers from 1 to 4;
l and m are integers from 0 to 4;
R 7 and R 8 are the same or different and independently of each other selected from hydrogen, methyl, ethyl, linear or branched C 3 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl;

a compound of formula (VII):

wherein n and o are integers from 1 to 4;
p and q are integers from 0 to 4;
R 9 , R 10 , R 11 and R 12 are the same or different and independently of each other selected from hydrogen, methyl, ethyl, linear or branched C 3 -C 6 alkyl; or
when R 13 is —(CH 2 ) r —, one of R 9 or R 10 and one of R 11 or R 12 taken together with the carbon atoms to which they are attached form a 5 to 8 membered substituted or unsubstituted carbocyclic ring where said substituents are selected from C 1 -C 6 alkyl;
R 13 is —(CH 2 ) r — or phenylene, where r is 1 to 2;
R 14 and R 15 are the same or different and independently of each other selected from hydrogen, methyl, ethyl, linear or branched C 3 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 6 -C 10 aryl or C 7 -C 12 aralkyl;

a compound of formula (VIII):

wherein R 16 and R 17 are the same or different and independently of each other selected from hydrogen, methyl, ethyl or linear or branched C 3 -C 6 alkyl;

a compound of formula (IX):

or
 a compound of formula (X):

2. The photosensitive composition of claim 1 wherein the polymer further comprises a second repeating unit of formula (IIA) derived from a monomer of formula (II):

wherein represents a position at which the bonding takes place with another repeat unit;
R 18 is selected from —(CH 2 ) s —, —(CH 2 ) t —OCH 2 —
or —(CH 2 ) t —(OCH 2 CH 2 ) 6 —OCH 2 —, where
s is an integer from 0 to 6,
t is an integer from 0 to 4; and
u is an integer from 0 to 3.

3. The photosensitive composition of claim 2 wherein the polymer further comprises a third repeating unit of formula (IIIA) derived from a monomer of formula (III):

wherein represents a position at which the bonding takes place with another repeat unit;
R 19 is —(CH 2 ) v —CO 2 R 20 where v is an integer from 0 to 4, and
R 20 is hydrogen or C 1 -C 4 alkyl.

4. The photosensitive composition of claim 3 wherein the polymer is derived from the monomers selected from the group consisting of:
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB),
trioxanonanenorbornene (NBTON),
tetraoxadodecanenorbornene (NBTODD),
5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM),
5-(3-methoxypropanoxy)methyl-2-norbornene (NB-3-MPM),
ethyl 3-(bicyclo[2.2.1]hept-2-en-2-yl)propanoate (EPEsNB),
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (Acid NB) and
norbornenylpropanoic acid (NBEtCOOH).

5. The photosensitive composition of claim 3 wherein the polymer is derived from the following monomers:
norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB),
3-(bicyclo[2.2.1]hept-2-en-2-yl)propanoic acid (NBEtCOOH), and
trioxanonanenorbornene (NBTON).

6. The photosensitive composition according to claim 3 , which is soluble in an alkali developer.

7. A semiconductor device comprising a laminated semiconductor element where said lamination consists of a photosensitive composition according to claim 3 .

8. A semiconductor device comprising a redistribution layer (RDL) structure where said RDL structure further comprises a photosensitive composition according to claim 3 .

9. A semiconductor device comprising a chip stack structure where said chip stack structure further comprises a photosensitive composition according to claim 3 .

10. A semiconductor device comprising a complementary metal oxide semiconductor (CMOS) image sensor dam structure where said structure further comprises a photosensitive composition according to claim 3 .

11. A film comprising the composition of claim 3 .

12. 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 structures further comprise a composition according to claim 3 .

13. A method of forming a film for the fabrication of a microelectronic or optoelectronic device comprising:
coating a suitable substrate with a composition according to claim 3 to form a film;
patterning the film wit

Assignees

• Promerus Llc
• Sumitomo Bakelite Co
• Sumitomo Bakelite Co

Inventors

• Knapp Brian
• Burns Cheryl
• Elce Edmund
• Seto Keitaro
• Sugiyama Hiromichi
• Horii Makoto
• Fujita Kazuyoshi

Classifications

• H10W90/754

  between a chip and a stacked insulating package substrate, interposer or RDL · CPC title

• H10W90/734

  between a chip and a stacked insulating package substrate, interposer or RDL · CPC title

• H10W90/732

  between stacked chips · CPC title

• H10W90/24

  at least one of the stacked chips being laterally offset from a neighbouring stacked chip, e.g. chip stacks having a staircase shape · CPC title

• H10W72/884

  Die-attach connectors and bond wires · CPC title