Photosensitive compositions and applications thereof

1. A photosensitive composition comprising:

a) a polymer having a first type of repeating unit of formula (IA) derived from a monomer of formula (I):

a second type of repeating unit of formula (IIA) derived from a monomer of formula (II):

and

a third type of 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;

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 the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl and n-butyl;

R 18 is selected from —(CH 2 ) s —, —(CH 2 ) t —OCH 2 — or —(CH 2 ) t —(OCH 2 CH 2 ) u —OCH 2 —, where

s is an integer from 0 to 6,

t is an integer from 0 to 4;

u is an integer from 0 to 3;

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;

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

c) a multifunctional crosslinking agent selected from the group consisting of:

d) a phenolic compound selected from the group consisting of:

e) a compound of formula (VI):

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 and 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; and

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 5 )cycloalkyl, (C 6 -C 10 )aryl and (C 7 -C 12 )aralkyl.

2. The photosensitive composition of claim 1 wherein the first repeat unit of the polymer is derived from a monomer selected from the group consisting of:

trioxanonanenorbornene (NBTON);

tetraoxadodecanenorbornene (NBTODD);

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

5-(3-methoxypropanoxy)methyl-2-norbornene (NB-3-MPM).

3. The photosensitive composition of claim 2 wherein the second repeat unit of the polymer is derived from a monomer selected from the group consisting of:

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

norbornenyl-2-trifluoromethyl-3,3,3-trifluoropropan-2-ol (HFANB); and

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

4. The photosensitive composition of claim 3 wherein the third repeat unit of the polymer is derived from a monomer selected from the group consisting of:

3-(bicyclo[2.2.1]hept-5-en-2-yl)acetic acid (NBMeCOOH);

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 norbomenylpropanoic acid (NBEtCOOH).

5. The photosensitive composition of claim 1 wherein the diazo-quinone moiety is represented by formula (C), (D) or (E):

6. The photosensitive composition of claim 1 wherein the photo active compound is selected from one or more of the following:

where at least one of Q is a group of the formula (C) or (D):

and

the remaining Q is hydrogen.

7. The photosensitive composition of claim 1 wherein the multifunctional crosslinking agent is selected from the group consisting of:

8. The photosensitive composition of claim 1 wherein the compound of formula (VI) is selected from the group consisting of:

2,2′-methylenediphenol;

4,4′-methylenediphenol;

2,2′-(ethane-1,1-diyl)diphenol;

4,4′-(ethane-1,1-diyl)diphenol;

2,2′-(propane-1,1-diyl)diphenol;

4,4′-(propane-1,1-diyl)diphenol;

2,2′-(propane-2,2-diyl)diphenol;

4,4′-(propane-2,2-diyl)diphenol;

2,2′-(4-methylpentane-2,2-diyl)diphenol;

4,4′-(4-methylpentane-2,2-diyl)diphenol;

2,2′-(5-methylheptane-3,3-diyl)diphenol;

4,4′-(5-methylheptane-3,3-diyl)diphenol;

4,4′-(propane-2,2-diyl)bis(2-cyclohexylphenol);

4,4′-(2-methylpropane-1,1-diyl)bis(2-cyclohexyl-5-methylphenol);

5,5″-(cyclohexane-1,1-diyl)bis(([1,1′-biphenyl]-2-01));

4,4′-(cyclohexane-1,1-diyl)bis(2-cyclohexylphenol);

4,4′-(4-methylcyclohexane-1,1-diyl)diphenol;

2-cyclohexyl-4-(2-(4-hydroxyphenyl)propan-2-yl)-5-methylphenol;

6,6′-methylenebis(2-(tert-butyl)-4-methylphenol);

6,6′-(2-methylpropane-1,1-diyl)bis(2,4-dimethylphenol);

4,4′-(2-methylpropane-1,1-diyl)bis(2-(tert-butyl)-5-methylphenol);

and mixtures in any combination thereof.

9. The photosensitive composition of claim 1 wherein the phenolic compound is selected from the group consisting of:

10. The photosensitive composition of claim 1 wherein the compound of formula (VI) is selected from the group consisting of:

2,2′-(4-methylpentane-2,2-diyl)diphenol;

4,4′-(4-methylpentane-2,2-diyl)diphenol;

2,2′-(5-methylheptane-3,3-diyl)diphenol;

4,4′-(5-methylheptane-3,3-diyl)diphenol;

and mixtures in any combination thereof.

11. The photosensitive composition of claim 1 further comprising one or more compounds selected from the group consisting of:

and mixtures in any combination thereof.

12. The photosensitive composition according to claim 1 , which is soluble in an alkali developer.

13. A semiconductor or an optoelectronic device comprising a laminated semiconductor element or an adhesive element where said element consists of a photosensitive composition according to claim 1 .

14. A semiconductor device comprising a chip stack structure where said chip stack structure further comprises a photosensitive composition according to claim 1 .

15. A film comprising the composition of claim 1 .

16. A microelectronic or optoelectronic device comprising one or more of a redistribution layer (RDL) structure, a chip-stack structure, a CMOS image sensor dam structure, where said structures further comprise a composition according to claim 1 .

17. 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 1 to form a film;

patterning the film with a mask by exposing to a suitable radiation;

developing the film after exposure to form a photo-pattern; and

curing the film by heating to a suitable temperature.

18. The method of claim 17 , where said developing is performed by an aqueous developer.

19. The method of claim 17 , where the substrate is first hardbaked before said curing at a temperature of from 120° C. to 160° C. for 20 minutes to 60 minutes.

20. The method of claim 17 , where said curing is performed at a temperature of from 150° C. to 200° C. at an incremental heating ramp of 5° C. and for 1 to 5 hours.