Organic electronic compositions and device thereof

Patent metadata

Field	Value
Publication number	US-9978944-B2
Application number	US-201515123891-A
Country	US
Kind code	B2
Filing date	Feb 13, 2015
Priority date	Mar 12, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

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 with an olefinic side chain.

First claim

The invention claimed is:

1. An organic electronic (OE) device comprising a dielectric layer, said dielectric layer comprising, or being obtained through the use of, a polycycloolefinic polymer comprising one or more repeating units selected from the following formulae:

where n is an integer from 0 to 8, a and b are independently of each other an integer from 0 to 7, and wherein a+b≤7.

2. The OE device according to claim 1 , wherein the polycycloolefinic polymer comprises one or more repeating units selected from the following formulae

3. The OE device according to claim 1 , wherein the polycycloolefinic polymer is a copolymer comprising two or more repeating units, each repeating unit comprising a different isomeric form of the same pendant alkenyl group.

4. The OE device according to claim 3 , wherein the polycycloolefinic polymer is selected of Formula II

where n is an integer from 0 to 8, a and b are independently of each other an integer from 0 to 7, and wherein a+b≤7, d is an integer >1, P is the molar ratio of units P with a terminal pendant alkenyl group, and Pi is the molar ratio of units Pi with an isomerized pendant alkenyl group, and P is >0 and <1 and Pi is >0 and <1.

5. The OE device according to claim 1 , wherein the polycycloolefinic polymer comprises units P with a terminal pendant alkenyl group and units Pi with an isomerized pendant alkenyl group, wherein the ratio of units P to units Pi is from 1:6 to 20:1.

6. The OE device according to claim 4 , wherein the polycycloolefinic polymer is selected of formula IIa

wherein the ratio of units P with a terminal pendant alkenyl group to units Pi with an isomerized pendant alkenyl group is from 1:6 to 20:1.

7. A dielectric layer in an OE device, said dielectric layer comprising, or being obtained through the use of, a polycycloolefinic polymer as defined in claim 1 .

8. The OE device according to claim 1 , which is an Organic Field Effect Transistor (OFET), Organic Thin Film Transistor (OTFT), Organic Light Emitting Diode (OLED) or Organic Photovoltaic (OPV) device or Organic Photodetector (OPD).

9. The OE device according to claim 8 , which is a top gate OFET or bottom gate OFET.

10. The top gate OFET according to claim 9 , which comprises a substrate ( 1 ), source and drain electrodes ( 2 a , 2 b ), an organic semiconductor (OSC) layer ( 3 ), a dielectric layer ( 4 ) comprising a polycycloolefinic polymer as defined in one or more of claims 1 to 6 and serving as gate insulator, and gate electrode ( 5 ).

11. A process for preparing an OFET according to claim 10 , which comprises:
A) forming source and drain electrodes ( 2 a , 2 b ) on a substrate ( 1 ),
B) forming an OSC layer ( 3 ) by deposition of an OSC material on the source and drain electrodes ( 2 a , 2 b ),
C) forming a dielectric layer ( 4 ) by deposition of a polycycloolefinic polymer as defined in one or more of claims 1 to 6 on the OSC layer ( 3 ),
D) forming a gate electrode ( 5 ) on the dielectric layer ( 4 ).

12. The bottom gate OFET according to claim 9 , which comprises a substrate ( 1 ), a gate electrode ( 5 ), a dielectric layer ( 4 ) comprising a polycycloolefinic polymer as defined in one or more of claims 1 to 6 and serving as gate insulator, source and drain electrodes ( 2 a , 2 b ), an OSC layer ( 3 ), and optionally a passivation layer ( 6 ).

13. A process for preparing an OFET according to claim 12 , 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 one or more of claims 1 to 6 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 ).

14. A process according to claim 11 , wherein the OSC material of the OSC layer ( 3 ) and the polycycloolefinic polymer of the dielectric layer ( 4 ) are deposited from an organic solution.

15. A product or assembly comprising an OE device according to claim 1 , which is an Integrated Circuit (IC), a Radio Frequency Identification (RFID) tag, a security marking or security device containing an RFID tag, a Flat Panel Display (FPD), a backplane of an FPD, a backlight of an FPD, an electrophotographic device, an electrophotographic recording device, an organic memory device, a pressure sensor, an optical sensor, a chemical sensor, a biosensor or a biochip.

16. A method of controlling the isomerization of terminal double bond in a polycycloolefinic polymer comprising:
subjecting a polycycloolefinic polymer comprising an initial repeat unit of formula P:

to sufficient length of time in a suitable reaction solvent at a temperature range of 60° C. to 80° C. so as to form the isomerized reheat unit of formula Pi:

and
isolating the resulting polycycloolefinic polymer of formula (IIa):

where n is an integer from 0 to 8, a and b are independently of each other an integer from 0 to 7, and wherein a+b≤7; d is an integer >1, and the ratio of units P with a terminal pendant alkenyl group to units Pi with an isomerized pendant alkenyl group is from 1:6 to 20:1.

17. A composition comprising:
a polycycloolefinic polymer of formula (IIa):

where n is an integer from 0 to 8, a and b are independently of each other an integer from 0 to 7, and wherein a+b≤7; d is an integer >1, and the ratio of units P with a terminal pendant alkenyl group to units Pi with an isomerized pendant alkenyl group is from 1:6 to 20:1;
a photoactive cross-linker; and
a carrier solvent.

18. A process according to claim 13 , wherein the OSC material of the OSC layer ( 3 ) and the polycycloolefinic polymer of the dielectric layer ( 4 ) are deposited from an organic solution.

19. A product or assembly comprising an OE device according to claim 8 , which is an Integrated Circuit (IC), a Radio Frequency Identification (RFID) tag, a security marking or security device containing an RFID tag, a Flat Panel Display (FPD), a backplane of an FPD, a backlight of an FPD, an electrophotographic device, an electrophotographic recording device, an organic memory device, a pressure sensor, an optical sensor, a chemical sensor, a biosensor or a biochip.

20. A product or assembly comprising an OE device according to claim 12 , which is an Integrated Circuit (IC), a Radio Frequency Identification (RFID) tag, a security marking or security device containing

Assignees

• Promerus Llc
• Merck Patent Gmbh

Inventors

• Rhodes Larry F
• Cyrus Crystal D
• Burgoon Hugh A
• Afonina Irina
• Cull Toby

Classifications

• C08F232/00

  Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system · CPC title

• C08F232/08

  having condensed rings (coumarone-indene polymers C08F244/00) · CPC title

• H01L51/052

  Electricity · mapped topic

• H01L51/0541

  Electricity · mapped topic

• H01L51/0545

  Electricity · mapped topic