Semiconducting material comprising aza-substituted phosphine oxide matrix and metal salt

Patent metadata

Field	Value
Publication number	US-10069078-B2
Application number	US-201414782721-A
Country	US
Kind code	B2
Filing date	Apr 9, 2014
Priority date	Apr 10, 2013
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

The present invention relates to a semiconducting material including at least one salt or complex of a metal cation and an aza-substituted phosphine oxide compound with improved electrical properties, and to a compound suitable for this organic semiconducting material and an electronic device utilizing the improved electrical properties of the semiconducting material.

First claim

The invention claimed is:

1. A semiconducting material comprising at least one salt or complex of a metal cation, and 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 spacer unit comprising a trivalent nitrogen atom having a lone electron pair, wherein the spacer unit has a structure which allows formation of a 5-, 6- or 7-membered chelate ring with the metal cation, wherein the chelate ring comprises the oxygen atom of formula (I) and the trivalent nitrogen atom of the spacer unit coordinated to the metal cation, and E is an electron transporting unit comprising a conjugated system of at least 10 delocalized electrons, and
wherein at least one group selected from R 1 , R 2 or R 3 is E-A-, wherein the electron transport unit E in the at least one group selected from R 1 , R 2 , and R 3 is selected from the group consisting of biphenyl, bithienyl, phenylthiophene, phenylpyridine, and an aromatic or heteroaromatic skeleton having at least two condensed aromatic rings.

2. The semiconducting material according to claim 1 , wherein the metal cation is a cation of a metallic element selected from the main groups of the Periodic Table.

3. The semiconducting material according to claim 2 , wherein the metallic element is selected from the first or second main group of the Periodic Table.

4. The semiconducting material according to claim 1 , wherein the spacer A is a divalent six-membered aromatic heterocyclic group.

5. The semiconducting material according to claim 4 , wherein the spacer A is selected from azine-2,4-diyl, azine-2,5-diyl, azine-2,6-diyl, 1,3-diazine-2,4-diyl, or 1,3-diazine-2,5-diyl.

6. The semiconducting material according to claim 1 , wherein the electron transporting unit E is a C 14 -C 50 -aryl or a C 8 -C 50 heteroaryl.

7. The semiconducting material according to claim 1 , wherein in the compound of formula (I), the group E-A- is a group represented by the following formula:

wherein the dashed line represents the single bond to the phosphorus atom,
Y 1 and Y 3 are independently selected from H, C 6 -C 50 aryl, C 3 -C 50 heteroaryl, or P(O)R 4 R 5 ;
Y 2 and Y 4 are independently selected from H, C 6 -C 50 aryl, or C 3 -C 50 heteroaryl;
R 4 and R 5 are independently selected from C 6 -C 30 aryl, C 3 -C 30 cycloalkyl, or C 3 -C 30 heteroaryl,
X 1 and X 2 are independently selected from C and N, with the proviso that
i) both X 1 and X 2 are not N at the same time, and if any of X 1 and X 2 is N, the adjacent Y is an electron lone pair,
ii) none of Y 1 and Y 3 is P(O)R 4 R 5 if any of X 1 and X 2 is N, and
iii) at least one of Y 1 , Y 2 , Y 3 , or Y 4 is a 1,1′-biphenylyl or comprises at least two condensed aromatic rings.

8. The semiconducting material according to claim 7 , wherein at least two groups selected from Y 1 , Y 2 , Y 3 and Y 4 are H.

9. The semiconducting material according to claim 1 , wherein the metal cation is selected from Li + and Mg 2+ .

10. The semiconducting material according to claim 1 , wherein the salt of the metal cation is selected from 8-hydroxyquinolinolate, pyrazolylborate, or phenolate substituted with a phosphine oxide group.

11. 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.

12. The electronic device according to claim 11 , 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.

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

14. A compound having the 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 3 O-heteroaryl, C 1 -C 30 -alkoxy, C 3 -C 30 -cycloalkyloxy, or C 6 -C 30 -aryloxy,
at least one of R 1 , R 2 and R 3 is a group represented by the following formula—

wherein the dashed line represents the single bond to the phosphorus atom of formula (I),
Y 1 and Y 3 are independently selected from H, phenyl, naphtyl, 1,1′-biphenylyl, quinolinyl, anthracenyl, phenanthrenyl, pyrenyl, or P(O)R 4 R 5 ;
Y 2 and Y 4 are independently selected from H, phenyl, naphtyl, 1,1′-biphenylyl, quinolinyl, anthracenyl, phenanthrenyl, or pyrenyl;
R 4 and R 5 are independently selected from C 6 -C 30 aryl, C 3 -C 30 cycloalkyl, or C 3 -C 30 heteroaryl,
X 1 and X 2 are independently selected from C and N, with the proviso that
iv) both X 1 and X 2 are not N at the same time, and if any of X 1 and X 2 is N, the adjacent Y is an electron lone pair,
v) none of Y 1 and Y 3 is P(O)R 4 R 5 if any of X 1 and X 2 is N, and
vi) at least one of Y 1 , Y 2 , Y 3 , or Y 4 is 1,1′-biphenylyl or comprises at least two condensed aromatic rings.

15. The compound according to claim 14 , wherein the compound of formula (I) has the structure (Ia) or (Ib):

wherein R 6 , R 7 and R 8 are independently selected from C 6 -C 30 aryl, C 3 -C 30 cycloalkyl, or C 3 -C 30 heteroaryl,
Y 5 , Y 7 , Y 9 and Y 11 are independently selected from H, C 6 -C 50 aryl, C 3 -C 50 heteroaryl, or P(O)R 4 R 5 ,
Y 6 , Y 8 , Y 10 and Y 12 are independently selected from H, C 6 -C 50 aryl, or C 3 -C 50 heteroaryl,
X 3 , X 4 , X 5 and X 6 are independently selected from C and N, with the proviso that
i) both X 3 and X 4 or both X 5 and X 6 are not N at the same time, and if any of X 3 and X 4 or any of X 5 and X 6 is N, the adjacent Y is an electron lone pair,
ii) neither Y 5 nor Y 7 and neither Y 9 nor Y 11 is P(O)R 4 R 5 if any of X 3 and X 4 or any of X 5 and X 6 is N, and
iii) at least one of Y 5 , Y 6 , Y 7 , or Y 8 and at least one of Y 9 , Y 10 , Y 11 , or Y 12 is 1,1′-biphenylyl or comprises at least two condensed aromatic rings.

Assignees

• Novaled Gmbh

Inventors

• Zoellner Mike

Classifications

• C07F9/65583

  each of the hetero rings containing nitrogen as ring hetero atom · CPC title

• C07F9/6512

  having the nitrogen atoms in positions 1 and 3 · CPC title

• C07F9/5728 Primary

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/58

  Pyridine rings · CPC title

• H01L51/5076

  Electricity · mapped topic