Diazirine containing organic electronic compositions and device thereof

Patent metadata

Field	Value
Publication number	US-10256409-B2
Application number	US-201715465758-A
Country	US
Kind code	B2
Filing date	Mar 22, 2017
Priority date	Mar 22, 2016
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

Abstract

The present invention relates to organic electronic devices, and more specifically to organic field effect transistors, comprising a dielectric layer that comprises a polycycloolefinic polymer and a diazirine compound.

First claim

What is claimed is:

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 formul

Assignees

• Promerus Llc
• Merck Patent Gmbh

Inventors

• Rhodes Larry F
• Burgoon Hugh
• Afonina Irina
• Backlund Tomas
• Morley Aurelie

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/004 Primary

  Electricity · mapped topic

• C08F132/08

  having condensed rings · CPC title

• H01L51/0021

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic