Cyclic amine surface modifier and organic electronic devices comprising such cyclic amine surface modifier

Patent metadata

Field	Value
Publication number	US-10879477-B2
Application number	US-201515119959-A
Country	US
Kind code	B2
Filing date	Feb 16, 2015
Priority date	Feb 19, 2014
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

The present invention relates to a cyclic amine surface modifier. In addition the present invention also relates to organic electronic devices comprising such cyclic amine surface modifier.

First claim

The invention claimed is:

1. An organic electronic device comprising a self-assembled monolayer on a metal or metal oxide substrate, said self-assembled monolayer comprising a moiety of general formula (IB)

wherein
R 1 is H, F, methyl, ethyl, methyl wherein one or more hydrogen is replaced by fluorine, ethyl wherein one or more hydrogen is replaced by fluorine, or —(C≡C) a —(Ar 1 ) b —(C≡C) c —(R 8 ) d —X 5 —* with
Ar 1 being para-phenylene or a para-phenylene wherein one or more carbon ring atom is replaced by N;
R 8 being —CH 2 — or —CF 2 —;
X 5 being —X a —, —X a —X b —, —C(=X a )—X b —, —X a O 3 —, —X a —X b O 3 —, —PO 2 H— or —PO 3 H—, with X a and X b being independently of each S or Se;
a being 0, 1 or 2;
b being 0, 1 or 2;
c being 0, 1 or 2; and
d being 0, 1 or 2,

and
R 2 and R 4 , are H.

2. An organic electronic device comprising a self-assembled monolayer according to- claim 1 , wherein X 5 is —S—, —S—S—, —C(═S)—S—, —SO 3 —, —S—SO 3 —, —PO 2 H— or —PO 3 H—.

3. An organic electronic device comprising a self-assembled monolayer according to claim 1 , wherein X 5 is —S—.

4. An organic electronic device comprising a self-assembled monolayer according to claim 1 , wherein R 8 is —CH 2 —.

5. An organic electronic device comprising a self-assembled monolayer according to claim 1 , wherein Ar 1 is of formulae (II-1) to (11-7)

6. An organic electronic device comprising a self-assembled monolayer according to claim 1 , wherein a is 0 or 1, b is 0 or 1, c is 0 or 1, and d is 0 or 1.

7. An organic electronic device comprising a self-assembled monolayer according to claim 1 , wherein a+b+c+d≥1.

8. An organic electronic device according to claim 1 , wherein the organic electronic device is an organic field effect transistors (OFET), thin film transistors (TFT), integrated circuits (IC), logic circuits, capacitors, radio frequency identification (RFID) tags, devices or components, organic light emitting diodes (OLED), organic light emitting transistors (OLET), flat panel displays, backlights of displays, organic photovoltaic devices (OPV), organic solar cells (OSC), photodiodes, laser diodes, photoconductors, organic photodetectors (OPD), electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, biosensors, biochips, security markings, security devices, or components or devices for detecting and discriminating DNA sequences.

9. A process for the preparation of the organic electronic device comprising a self-assembled monolayer of claim 1 , said process comprising the steps of
(a) providing a metal surface or a metal oxide surface, and
(c) applying one or more precursor compound to said metal surface or metal oxide surface,
thus obtaining a self-assembled monolayer on said metal surface or metal oxide surface, wherein the precursor compound comprises a moiety of formula (IB)

wherein
R 1 is H, F, methyl, ethyl, methyl wherein one or more hydrogen is replaced by fluorine, ethyl wherein one or more hydrogen is replaced by fluorine, or —(C≡C) a —(Ar l ) b —(C≡C) c —(R 8 ) d —X 5 —* with
Ar 1 being para-phenylene or a para-phenylene wherein one or more carbon ring atom is substituted by N;
R 8 being —CH 2 — or —CF 2 —;
X b being —X a —, —X a —X b —, —C(=X a )—X b —, —X a O 3 —, —X a —X b O 3 —, —PO 2 H— or —PO 3 H—, with X a and X b being independently of each S or Se;
a being 0, 1 or 2;
b being 0, 1 or 2;
c being 0, 1 or 2; and
d being 0, 1 or 2,
R 2 and R 4 are H.

10. A process according to claim 9 , wherein R 1 is H, F, methyl, ethyl, methyl wherein one or more hydrogen is replaced by fluorine, ethyl wherein one or more hydrogen is replaced by fluorine, or —(C≡C) a —(Ar l ) b —(C≡C) c —(R 8 ) d —X 5 —H with
Ar 1 being para-phenylene or a para-phenylene wherein one or more carbon ring atom is substituted by N;
R 8 being —CH 2 — or —CF 2 —;
X 5 being —X a —, X a —X b —, c(═X a )—X b —, —X a —X b O 3 —,—PO 2 H— and —PO 3 H—, with X a or X b being independently of each S or Se;
a being 0, 1 or 2;
b being 0, 1 or 2;
c being 0, 1 or 2; and
d being 0, 1 or 2.

11. A process according to claim 9 , wherein two moieties of formula (IB) are linked by —(C≡C) a —(Ar l ) b —(C≡C) c —(R 8 ) d —S—S—(R 8 ) d —(C≡C) c —(Ar l ) b —(C≡C) a —.

12. A process according to claim 9 , wherein the precursor compound comprises a moiety of formula (IB) wherein
X 5 is —S—, —S—S—, —C(═S)—S—, —SO 3 —, —S—SO 3 —, —PO 2 H— or —PO 3 H—.

Assignees

• Merck Patent Gmbh
• Innovationlab Gmbh
• Univ Braunschweig Tech
• Max Planck Gesellschaft

Inventors

• Jesper Malte
• Hamburger Manuel
• Schinke Janusz
• Alt Milan
• Muellen Klaus

Classifications

• H10K10/84 Primary

  Ohmic electrodes, e.g. source or drain electrodes · CPC title

• C07D455/04 Primary

  containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine · CPC title

• H10K30/81

  Electrodes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D471/06

  Peri-condensed systems · CPC title