Diazirine containing organic electronic compositions and device thereof

1. An organic electronic (OE) device comprising a dielectric layer, said dielectric layer comprising a polycycloolefinic polymer selected from the group consisting of:

a) a polymer of formula (III):

and

b) a polymer of formula (IV):

wherein

each occurrence of R 1 , R 2 , R 3 or R 4 may be same or different and each independently is hydrogen or a hydrocarbyl selected from the group consisting of linear or branched (C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 3 -C 12 )cycloalkyl(C 1 -C 12 )alkyl, (C 6 -C 12 )bicycloalkyl, (C 6 -C 12 )bicycloalkyl(C 1 -C 12 )alkyl, (C 7 -C 14 )tricycloalkyl, (C 7 -C 14 )tricycloalkyl(C 1 -C 12 )alkyl, (C 6 -C 10 )aryl and (C 6 -C 10 )aryl(C 1 -C 6 )alkyl;

and a compound of formula (V):

wherein,

L is a divalent linking or a spacer group selected from:

—C(O)O—R 7 —OC(O)—, —C(O)O—R 7 —, —R 7 —OC(O)—R 7 —, —C(O)—R 7 —OC(O)—, —C(O)—R 7 —, —R 7 —C(O)—R 7 —, —O—R 7 —OC(O)—, —O—R 7 —O—, —O—R 7 —, —R 7 —O—R 7 —,

—C(O)NH—(CH 2 ) b —NH(CO)—, where b is 1 to 15, —C(O)NH—(CH 2 CH 2 O) c (CH 2 ) d —NR 5 (CO)—, where c is 2 to 6 and d is 1 to 6, and each occurrence of R 7 may be the same or different which is a divalent group independently selected from (C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )aryl(C 1 -C 12 )alkyl, (C 6 -C 10 )heteroaryl, (C 6 -C 10 )heteroaryl(C 1 -C 12 )alkyl, —(CH 2 —CH 2 —O) a —, where a is an integer from 1 to 10;

R 5 and R 6 are the same or different and each is independently selected from (C 1 -C 12 )alkyl, where portions of hydrogen on alkyl are replaced with fluorine, (C 1 -C 12 )perfluoroalkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )aryl(C 1 -C 12 )alkyl, where portions of hydrogen on alkyl are replaced with fluorine, and (C 6 -C 12 )arylperfluoro(C 1 -C 12 )alkyl; and

Ar 1 and Ar 2 are the same or different and each is independently selected from (C 6 -C 12 )arylene or (C 6 -C 12 )heteroarylene group optionally substituted with a group selected from halogen, —OH, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 6 -C 10 )aryl, (C 6 -C 12 )aryloxy, (C 6 -C 12 )aryl(C 1 -C 4 )alkyl and (C 6 -C 12 )aryl(C 1 -C 4 )alkyloxy.

2. The OE device according to claim 1 , wherein the polycycloolefinic polymer is of Formula (III).

3. The OE device according to claim 1 , wherein the polycycloolefinic polymer is of Formula (IV).

4. The OE device according to claim 1 , which comprises one or more compounds of formula (V) as a crosslinker agent.

5. The OE device according to claim 1 , wherein the compound of formula (V) is selected from the group consisting of:

propane-1,3-diyl bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

where n is 7 or 12;

where n is 3 or 5;

methylene bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

ethane-1,2-diyl bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

butane-1,4-diyl bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

3,3′-((oxybis(methylene))bis(4,1-phenylene))bis(3-(trifluoromethyl)-3H-diazirine);

3,3′-((oxybis(ethane-2,1-diyl))bis(4,1-phenylene))bis(3-(trifluoromethyl)-3H-diazirine);

3-(trifluoromethyl)-3-(4-(3-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)propyl)phenyl)-3H-diazirine;

3-(trifluoromethyl)-3-(4-(2-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)ethyl)phenyl)-3H-diazirine;

4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl 4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate;

4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenethyl 2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetate;

2-oxo-2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethyl 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate;

1,3-bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)propan-1-one;

1,3-bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)propan-2-one;

(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)methyl 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate;

1,2-bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)ethane;

1,3-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)propane;

1,5-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)pentane;

3,3′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(methylene))bis(4,1-phenylene))bis(3-(trifluoromethyl)-3H-diazirine);

3-(trifluoromethyl)-3-(4-(3-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)propyl)phenyl)-3H-diazirine;

(N-methyl-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)methyl 4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate; and

N,N′-methylenebis(N-methyl-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamide).

6. A dielectric layer in an OE device, said dielectric layer comprising a polycycloolefinic polymer as defined in claim 1 .

7. A dielectric layer in an OE device, said dielectric layer comprising a compound of formula (V) as defined in claim 1 .

8. A dielectric layer in an OE device, said dielectric layer comprising a compound of formula (V) as defined in claim 1 , said compound of formula (V) is selected from the group consisting of:

propane-1,3-diyl bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

3,3′-((oxybis(ethane-2,1-diyl))bis(4,1-phenylene))bis(3-(trifluoromethyl)-3H-diazirine); and

4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl 4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate.

9. A process for preparing an Organic Field Effect Transistor (OFET), which comprises:

A) forming a gate electrode ( 5 ) on a substrate ( 1 ),

B) forming a dielectric layer ( 4 ) by deposition of a polycycloolefinic polymer as defined in claim 1 on the substrate ( 1 ) and the gate electrode ( 5 ),

C) forming source and drain electrodes ( 2 a , 2 b ) on the dielectric layer ( 4 ),

D) forming an OSC layer ( 3 ) by deposition of an OSC material on the source and drain electrodes ( 2 a , 2 b ) and the dielectric layer ( 4 ),

E) optionally forming a passivation layer ( 6 ) on the OSC layer ( 3 ).

10. The process according to claim 9 , wherein the OSC material of the OSC layer ( 3 ) and the polycycloolefinic polymer of the dielectric layer ( 4 ) are deposited from an organic solution.

11. A composition comprising:

a) a polymer of formula (III):

and

b) a polymer of formula (IV):

wherein

each occurrence of R 1 , R 2 , R 3 or R 4 may be same or different and each independently is hydrogen or a hydrocarbyl selected from the group consisting of linear or branched (C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 3 -C 2 )cycloalkyl(C 1 -C 12 )alkyl, (C 6 -C 12 )bicycloalkyl, (C 6 -C 12 )bicycloalkyl(C 1 -C 12 )alkyl, (C 7 -C 14 )tricycloalkyl, (C 7 -C 14 )tricycloalkyl(C 1 -C 12 )alkyl, (C 6 -C 10 )aryl and (C 6 -C 10 )aryl(C 1 -C 6 )alkyl; and

a compound of formula (V):

wherein,

L is a divalent linking or a spacer group selected from:

—C(O)O—R 7 —OC(O)—, —C(O)O—R 7 —, —R 7 —OC(O)—R 7 —, —C(O)—R 7 —OC(O)—, —C(O)—R 7 —, —R 7 —C(O)—R 7 —, —O—R 7 —OC(O)—, —O—R 7 —O—, —O—R 7 —, —R 7 —O—R 7 —, —C(O)NH—(CH 2 ) b —NH(CO)—, where b is 1 to 15,

—C(O)NH—(CH 2 CH 2 O) c (CH 2 ) d —NR 5 (CO)—, where c is 2 to 6 and d is 1 to 6, and each occurrence of R 7 may be the same or different which is a divalent group independently selected from (C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )aryl(C 1 -C 12 )alkyl, (C 6 -C 10 )heteroaryl, (C 6 -C 10 )heteroaryl(C 1 -C 12 )alkyl, —(CH 2 —CH 2 —O) a —, where a is an integer from 1 to 10;

R 5 and R 6 are the same or different and each is independently selected from (C 1 -C 12 )alkyl, where portions of hydrogen on alkyl are replaced with fluorine, (C 1 -C 12 )perfluoroalkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )aryl(C 1 -C 12 )alkyl, where portions of hydrogen on alkyl are replaced with fluorine, and (C 6 -C 12 )arylperfluoro(C 1 -C 12 )alkyl; and

Ar 1 and Ar 2 are the same or different and each is independently selected from (C 6 -C 12 )arylene or (C 6 -C 12 )heteroarylene group optionally substituted with a group selected from halogen, —OH, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 6 -C 10 )aryl, (C 6 -C 12 )aryloxy, (C 6 -C 12 )aryl(C 1 -C 4 )alkyl and (C 6 -C 12 )aryl(C 1 -C 4 )alkyloxy.

12. The composition according to claim 11 wherein said compound of formula (V) is selected from the group consisting of:

propane-1,3-diyl bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate);

3,3′-((oxybis(ethane-2,1-diyl))bis(4,1-phenylene))bis(3-(trifluoromethyl)-3H-diazirine); and

4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl 4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate.