Dinaphto[2,3-a:2′3′-H]phenazines and their use as organic semiconductors

Patent metadata

Field	Value
Publication number	US-9236574-B2
Application number	US-201214004566-A
Country	US
Kind code	B2
Filing date	Feb 11, 2012
Priority date	Mar 11, 2011
Publication date	Jan 12, 2016
Grant date	Jan 12, 2016

Abstract

The invention relates to novel dinaphtho[2,3-a:2′,3′-h]phenazine compounds, to methods for their preparation and intermediates used therein, formulations comprising them, the use of these compounds and formulations as semiconductor material in organic electronic (OE) devices, and OE devices comprising these compounds and formulations.

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 to R 4 independently of each other denote —C≡C—R 5
R 5 is an optionally substituted alkyl, silyl or germyl group, or an aryl or heteroaryl group with 1 to 20 ring atoms which is unsubstituted or substituted by one or more groups L, X 1 to X 6 independently of each other, and on each occurrence identically or differently, denote H or have one of the meanings given for L,
L is P-Sp-, F, Cl, Br, I, —OH, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X 0 , —C(═O)R 0 , —NR 0 R 00 , C(═O)OH, optionally substituted silyl or germyl, optionally substituted aryl or heteroaryl having 4 to 20 ring atoms, straight chain, branched or cyclic alkyl, alkoxy, oxaalkyl or thioalkyl with 1 to 20 C atoms which is unsubstituted or substituted with one or more F or Cl atoms or OH groups, or straight chain, branched or cyclic alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 2 to 30 C atoms which is unsubstituted or substituted with one or more F or Cl atoms or OH groups,
P is a polymerisable group,
Sp is a spacer group or a single bond,
X 0 is halogen, and
R 0 , R 00 independently of each other denote H or alkyl with 1 to 20 C-atoms.

2. The compound according to claim 1 , wherein R 5 is a substituted alkyl, silyl or germyl group, or an aryl or heteroaryl group with 1 to 20 ring atoms which is unsubstituted or substituted by one or more groups L.

3. The compound according to claim 1 , wherein R 5 is of formula II
-AR′R″R′″  II

wherein
A is C, Si or Ge,
R′, R″, R′″ are, identical or different, H, a straight-chain, branched or cyclic alkyl or alkoxy group having 1 to 20 C atoms, a straight-chain, branched or cyclic alkenyl group having 2 to 20 C atoms, a straight-chain, branched or cyclic alkynyl group having 2 to 20 C atoms, a straight-chain, branched or cyclic alkylcarbonyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 4 to 20 ring atoms, an arylalkyl or heteroarylalkyl group having 4 to 20 ring atoms, an aryloxy or heteroaryloxy group having 4 to 20 ring atoms, or an arylalkyloxy or heteroarylalkyloxy group having 4 to 20 ring atoms, wherein all the aforementioned groups are optionally substituted with one or more groups L′, and
L′ has one of the meanings given for L in formula I, which is different from a silyl and germyl group.

4. The compound according to claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are H.

5. The compound according to claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are, each independently, H, F, Cl, Br, I, —CN, or straight chain, branched or cyclic alkyl, alkoxy, thioalkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonylamido, alkylamidocarbonyl or alkoxycarbonyloxy with 1 to 20 C atoms which is unsubstituted or substituted with one or more F or Cl atoms or OH groups or is perfluorinated, or an aromatic or heteroaromatic group with 4 to 25 ring atoms, which is mono- or polycyclic, which contains two or more individual rings that are connected to each other via single bonds, or contains two or more fused rings, and wherein each ring is unsubstituted or substituted with one or more groups L.

6. A compound of formula II

wherein
R′, R″, R′″ are, identical or different, H, a straight-chain, branched or cyclic alkyl or alkoxy group having 1 to 20 C atoms, a straight-chain, branched or cyclic alkenyl group having 2 to 20 C atoms, a straight-chain, branched or cyclic alkynyl group having 2 to 20 C atoms, a straight-chain, branched or cyclic alkylcarbonyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 4 to 20 ring atoms, an arylalkyl or heteroarylalkyl group having 4 to 20 ring atoms, an aryloxy or heteroaryloxy group having 4 to 20 ring atoms, or an arylalkyloxy or heteroarylalkyloxy group having 4 to 20 ring atoms, wherein all the aforementioned groups are optionally substituted with one or more groups L′,
L′ is P-Sp-, F, Cl, Br, I, —OH, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X 0 , —C(═O)R 0 R 00 , C(═O)OH, optionally substituted aryl or heteroaryl having 4 to 20 ring atoms, straight chain, branched or cyclic alkyl, alkoxy, oxaalkyl or thioalkyl with 1 to 20-C atoms which is unsubstituted or substituted with one or more F or Cl atoms or OH groups, or straight chain, branched or cyclic alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 2 to 30 C atoms which is unsubstituted or substituted with one or more F or Cl atoms or OH groups,
P is a polymerisable group,
Sp is a spacer group or a single bond,
X 0 is halogen, and
R 0 , R 00 independently of each other denote H or alkyl with 1 to 20 C-atoms.

7. A formulation comprising one or more compounds according to claim 1 and one or more organic solvents.

8. A formulation comprising one or more compounds according to claim 1 , one or more organic binders or precursors thereof, optionally having a permittivity ∈ at 1,000 Hz of 3.3 or less, and optionally one or more solvents.

9. A charge transport, semiconducting, electrically conducting, photoconducting or light emitting material or component comprising one or more compounds according to claim 1 .

10. An optical, electrooptical, electronic, electroluminescent or photoluminescent component or device comprising one or more compounds according to claim 1 .

11. The component or device according to claim 10 , which 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, radio frequency identification (RFID) devices, radio frequency identification (RFID) components, organic light emitting diodes (OLED), organic light emitting transistors (OLET), flat panel displays, backlights of displays, organic photovoltaic devices (OPV), solar cells, laser diodes, photoconductors, photodetectors, electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, charge injection layers, charge transport layers in polymer light emitting diodes (PLEDs), charge transport interlayers in polymer light emitting diodes (PLEDs), organic plasmon-emitting diodes (OPEDs), 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, components for detecting and discriminating DNA sequences, and devices for detecting and discriminating DNA sequences.

12. The compound according to claim 3 , wherein A is Si.

13. A formulation comprising one or more compounds according to claim 6 and one or more organic solvents.

14. A formulation comprising one or more compounds according to claim 6 , one or more organic binders or precursors thereof, optionally having a permittivity ∈ at 1,000 Hz of 3.3 or less, and optionally one or more solvents.

15. A charge transport, semiconducting, electrically conducting, photoconducting or light emitting material or component comprising one or more compounds according to claim 6 .

16. An optical, electrooptical, electronic, electroluminescent or photoluminescent component or device comprising one or more compounds according to

Assignees

• Wang Changsheng
• Mitchell William
• D Lavari Mansoor
• Tierney Steven
• Merck Patent Gmbh

Inventors

• Wang Changsheng
• Mitchell William
• D Lavari Mansoor
• Tierney Steven

Classifications

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• H01L51/0094 Primary

  Electricity · mapped topic

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title