Methoxyaryl surface modifier and organic electronic devices comprising such methoxyaryl surface modifier

Patent metadata

Field	Value
Publication number	US-10164191-B2
Application number	US-201515119752-A
Country	US
Kind code	B2
Filing date	Feb 16, 2015
Priority date	Feb 19, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

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

First claim

The invention claimed is:

1. An assembly comprising a substrate and a self-assembled monolayer, said substrate having a metal or metal oxide surface and said self-assembled monolayer being on said surface, wherein said self-assembled monolayer comprises a moiety of formula (I)

wherein
R 1 is selected from the group consisting of methyl, ethyl, methyl wherein one or more hydrogen is substituted by fluorine and ethyl wherein one or more hydrogen is substituted by fluorine;
R 2 is —CH 2 — or —CF 2 —;
Ar 1 is selected from formulae (II-2) to (II-7)

wherein optionally one or more hydrogen present on Ar1 is replaced by fluorine;

X 1 is selected from the group consisting of —X a —, —X a —X b —, —C(═X a )—X b —, —X a O 3 —, —X a —X b O 3 —, —PO 2 H— and —PO 3 H—, with X a and X b being independently of each S or Se;
a is 2, 3, 4 or 5;
b is 0, 1 or 2;
c is 1 or 2;
d is 0, 1 or 2; and
e is 0, 1 or 2.

2. The assembly according to claim 1 , wherein R 1 is methyl.

3. The assembly according to claim 1 , wherein R 2 is —CH 2 —.

4. The assembly according to claim 1 , wherein X 1 is selected from the group consisting of —S—, —S—S—, —C(═S)—S—, —SO 3 —, —S—SO 3 —, —PO 2 H— and —PO 3 H—.

5. The assembly according to claim 1 , wherein X 1 is —S—.

6. The assembly according to claim 1 , wherein a is 3.

7. The assembly according to claim 1 , wherein b+d is 1.

8. The assembly according to claim 1 , wherein e is 1.

9. The assembly according to claim 1 , wherein b is 1, c is 1, d is 0, and e is 0 or 1; or wherein b is 0, c is 1, d is 0, and e is 0 or 1.

10. An organic electronic device comprising the assembly of claim 1 .

11. The organic electronic device according to claim 10 , wherein the organic electronic device is selected from the group consisting of 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, charge injection layers, charge transport layers or interlayers in polymer light emitting diodes (PLEDs), Schottky diodes, planarising layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates, conducting patterns, electrode materials in batteries, alignment layers, biosensors, biochips, security markings, security devices, and components or devices for detecting and discriminating DNA sequences.

12. A process for the preparation of the assembly of claim 1 , said process comprising:
(a) providing a substrate having a metal surface or a metal oxide surface, and
(c) applying one or more precursor compound to said metal surface or metal oxide surface,
to thereby obtain said self-assembled monolayer on said metal surface or metal oxide surface, wherein the precursor compound comprises a moiety of said formula (I)

13. The process according to claim 12 , wherein the precursor compound is of formula (I′) or (I″)

14. The process according to claim 12 , wherein R 1 is methyl.

15. The process according to claim 12 , wherein R 2 is —CH 2 —.

16. The process according to claim 12 , wherein X 1 is selected from the group consisting of —S—, —S—S—, —C(═S)—S—, —SO 3 —, —S—SO 3 —, —PO 2 H— and —PO 3 H—.

17. The process according to claim 12 , wherein X 1 is —S—.

18. The process according to claim 12 , wherein a is 3.

19. The assembly according to claim 1 , wherein e is 1 and R 2 is —CH 2 —.

20. The assembly according to claim 1 , wherein b is 1.

21. The assembly according to claim 1 , wherein b, c and e are each 1, and d is 0.

22. The assembly according to claim 1 , wherein b, c, d and e are each 1.

23. An assembly comprising a substrate and a self-assembled monolayer, said substrate having a metal or metal oxide surface and said self-assembled monolayer being on said surface, wherein said self-assembled monolayer comprises a moiety selected from the following formulae (I-1) to (I-6) and (I-8) to (I-10):

24. The assembly according to claim 23 , wherein said moiety is selected from formulae (I-1) to (I-4) and (I-8).

25. An assembly comprising a substrate and a self-assembled monolayer, said substrate having a metal or metal oxide surface and said self-assembled monolayer being on said surface, wherein said self-assembled monolayer comprises a moiety of formula (I)

wherein
R 1 is selected from the group consisting of methyl, ethyl, methyl wherein one or more hydrogen is substituted by fluorine and ethyl wherein one or more hydrogen is substituted by fluorine;
R 2 is —CH 2 — or —CF 2 —;
Ar 1 is para-phenylene or a para-phenylene wherein one or more carbon ring atom is replaced by N;
X 1 is selected from the group consisting of —X a —, —X a —X b —, —C(═X a )—X b —, —X a O 3 —, —X a —X b O 3 —, —PO 2 H— and —PO 3 H—, with X a and X b being independently of each S or Se;
a is 2, 3, 4 or 5;
b is 1 or 2;
c is 0, 1 or 2;
d is 0, 1 or 2; and
e is 0, 1 or 2.

Assignees

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

Inventors

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

Classifications

• C08G2261/3424

  non-conjugated, e.g. paracyclophanes or xylenes · CPC title

• C08G2261/1646

  comprising aromatic or heteroaromatic end groups · CPC title

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• H01L51/105

  Electricity · mapped topic

• C08G2261/344

  containing heteroatoms · CPC title