IP Library Granted Patent US 10,879,477
Granted Patent B2
US 10,879,477 · App. 15/119,959 · Granted Dec 29, 2020

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

Inventors: Malte Jesper (Heidelberg, DE); Manuel Hamburger (Mannheim, DE); Janusz Schinke (Braunschweig, DE); Milan Alt (Heidelberg, DE); Klaus Muellen (Cologne, DE)
Assignees: MERCK PATENT GMBH; INNOVATIONLAB GMBH; TECHNISCHE UNIVERSITAET BRAUNSCHWEIG; MAX-PLANCK-GESELLSCHAFT ZUR FOERDERUNG DER WISSENSCHAFTEN E.V.
H01L51/105C07D221/14C07D455/04C07D471/06H01L51/0053H01L51/0072H01L51/0036H01L51/0541H01L51/0545H01L51/0558H01L51/441H01L51/5203
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Quick Facts
Patent No.
US 10,879,477
App. No.
15/119,959
Granted
Dec 29, 2020
Kind
B2
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.

Claims (44)

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—.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2023
From: FLEXENABLE LIMITED
To: FLEXENABLE TECHNOLOGY LIMITED
Reel/Frame 064283/0914 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2023
From: MERCK PATENT GMBH
To: FLEXENABLE LIMITED
Reel/Frame 064286/0751 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2016
From: JESPER, MALTE; HAMBURGER, MANUEL; SCHINKE, JANUSZ; ALT, MILAN; MUELLEN, KLAUS
To: MERCK PATENT GMBH; INNOVATIONLAB GMBH; TECHNISCHE UNIVERSITAET BRAUNSCHWEIG; MAX-PLANCK-GESELLSCHAFT ZUR FOERDERUNG DER WISSENSCHAFTEN E.V.
Reel/Frame 040631/0173 →
Priority Claims (2)
EP 14000575 · Feb 19, 2014 · regional
EP 14002743 · Aug 6, 2014 · regional
Continuity (1)
Related Publication 20170062744A1 · Mar 2, 2017