Semiconducting material comprising a phosphine oxide matrix and metal salt

Patent metadata

Field	Value
Publication number	US-10026902-B2
Application number	US-201415023569-A
Country	US
Kind code	B2
Filing date	Oct 9, 2014
Priority date	Oct 9, 2013
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

The disclosure refers to a semiconducting material comprising a phosphorous-containing compound and at least one lithium complex. Also provided are electronic devices comprising a cathode, an anode, and the semiconducting material comprising a phosphorous-containing compound arranged between the cathode and the anode. Furthermore, a compound and an electronic device are disclosed.

First claim

The invention claimed is:

1. A semiconducting material comprising:
i) a compound according to formula (I)

wherein R 1 , R 2 , and R 3 are independently selected from C 1 -C 30- alkyl, C 3 -C 30 cycloalkyl, C 2 -C 30 -heteroalkyl, C 6 -C 30 -aryl, C 2 -C 30 -heteroaryl, C 1 -C 30 -alkoxy, C 3 -C 30 -cycloalkyloxy, C 6 -C 30 -aryloxy, or a structural unit having general formula E-A-,
wherein
A is a phenylene spacer unit, and
E is an electron transporting unit selected from C 10 -C 60 aryl or C 6 -C 60 heteroaryl, wherein the C 6 -C 60 heteroaryl comprises from 1 to 6 heteroatoms independently selected from O, S, P, Si, or B, and the C 10 -C 60 aryl or C 6 -C 60 heteroaryl comprises a conjugated system of at least 10 delocalized electrons, and
wherein at least one of R 1 , R 2 , and R 3 has the general formula E-A-;
and
ii) at least one lithium complex having formula (II)

wherein A 1 is a C 6 -C 30 arylene or C 2 -C 30 heteroarylene comprising at least one atom selected from O, S, or N in an aromatic ring, and each of A 2 and A 3 is independently selected from C 6 -C 30 aryl or C 2 -C 30 heteroaryl comprising at least one atom selected from O, S, or N in an aromatic ring.

2. The semiconducting material according to claim 1 , wherein in the compound of formula (I), spacer A is selected from m- or p-phenylene.

3. The semiconducting material according to claim 1 , wherein in the compound of formula (I), electron transporting unit E is a C 14 -C 50 aryl or a C 8 -C 50 heteroaryl.

4. The semiconducting material according to claim 3 , wherein in the compound of formula (I), electron transporting unit E is a C 14 -C 44 aryl.

5. The semiconducting material according to claim 4 , wherein in the compound of formula (I), at least one group E is selected from C 16 -C 44 pyrenyl or C 14 -C 38 anthryl.

6. The semiconducting material according to claim 4 , wherein in the compound of formula (I), in at least one electron transporting unit E-A-,
i) A is m- or p- phenylene, and E is C 16 -C 44 pyrenyl; or
ii) A is m-phenylene, and E is C 14 -C 34 anthryl.

7. The semiconducting material according to claim 1 , wherein in the compound of formula (I), at least one of substituents R 1 , R 2 , and R 3 is phenyl.

8. The semiconducting material according to claim 1 , wherein in the compound of formula (II), A 1 is phenylene.

9. The semiconducting material according to claim 1 , wherein in the compound of formula (II), at least one of substituents A 2 and A 3 is phenyl.

10. An electronic device comprising a cathode, an anode and the semiconducting material according to claim 1 , wherein the semiconducting material is arranged between the cathode and the anode.

11. The electronic device according to claim 10 , further comprising an electron transporting layer or an electron injecting layer, wherein the semiconducting material is present in the electron transporting layer or the electron injecting layer.

12. The electronic device according to claim 11 , wherein the electronic device is a light emitting device.

13. A compound having a structure according to formula (I):

wherein R 1 , R 2 , and R 3 are independently selected from C 1 -C 30 -alkyl, C 3 -C 30 -cycloalkyl, C 2 -C 30 -heteroalkyl, C 6 -C 30 -aryl, C 2 -C 30 -heteroaryl, C 1 -C 30 -alkoxy, C 3 -C 30 -cycloalkyloxy, C 6 -C 30 -aryloxy, or a structural unit having general formula E-A-,
wherein at least one group selected from R 1 , R 2 , or R 3 has the general formula E-A-,
wherein
A is m-phenylene, and
each E is an electron transporting unit independently selected from C 14 -C 60 aryl or C 6 -C 60 heteroaryl, wherein the C 6 -C 60 heteroaryl comprises from 1 to 6 heteroatoms independently selected from O, S, P, Si, or B, and the C 14 -C 60 aryl or C 6 -C 60 heteroaryl comprises a conjugated system of at least 10 delocalized electrons.

14. A compound having a structure according to formula (I):

wherein R 1 , R 2 , and R 3 are independently selected from C 1 -C 30 -alkyl, C 3 -C 30 -cycloalkyl, C 2 -C 30 -heteroalkyl, C 6 -C 30 -aryl, C 2 -C 30 -heteroaryl, C 1 -C 30 -alkoxy, C 3 -C 30 -cycloalkyloxy, C 6 -C 30 -aryloxy, or a structural unit having general formula E-A-,
wherein at least one group selected from R 1 , R 2 , or R 3 has the general formula E-A-,
wherein
i) A is m- or p-phenylene, and E is C 16 - C 44 pyrenyl; or
ii) A is m-phenylene, and E is C 14 - C 38 anthryl.

15. A compound having a structure according to formula (I):

wherein R 1 , R 2 , and R 3 are independently selected from C 1 -C 30 -alkyl, C 3 -C 30 -cycloalkyl, C 2 -C 30 -heteroalkyl, C 6 -C 30 -aryl, C 2 -C 30 -heteroaryl, C 1 -C 30 -alkoxy, C 3 -C 30 -cycloalkyloxy, C 6 -C 30 -aryloxy, or a structural unit having general formula E-A-,
wherein at least one group selected from R 1 , R 2 , or R 3 has the general formula E-A-,
wherein
A is o-phenylene, and
each E is an electron transporting unit independently selected from C 14 -C 60 aryl or C 6 -C 60 heteroaryl, wherein the C 6 -C 60 heteroaryl comprises from 1 to 6 heteroatoms independently selected from O, S, P, Si, or B, and the C 14 -C 60 aryl or C 6 -C 60 heteroaryl comprises a conjugated system of at least 10 delocalized electrons.

Assignees

• Novaled Gmbh

Inventors

• Rothe Carsten
• Zöllner Mike

Classifications

• C07F5/025

  Boronic and borinic acid compounds · CPC title

• C07F9/58

  Pyridine rings · CPC title

• C07F9/5325 Primary

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title

• H01L51/5072

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic