Lithium metal quinolates and process for preparation thereof as good emitting, interface materials as well as N-type dopent for organic electronic devices

Patent metadata

Field	Value
Publication number	US-9368734-B2
Application number	US-201213529815-A
Country	US
Kind code	B2
Filing date	Jun 21, 2012
Priority date	Jun 21, 2011
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

Invention relates to a single step preparation of alkali metal quinolate of general formula 1

wherein
M=Lithium, sodium or potassium;
R=H, alkyl (C1-C6), alkoxy, aryl, aryloxy, amino, amido or halogen (Cl, F, Br, I)
which is substituted or unsubstituted with direct reaction of metal with 8-hydroxyquinoline. Substituted 8-hydroxyquinoline optionally have at least one substituent selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, amino, amido at 2, 5 or 7 position. Halogen substituted 8-hydroxyquinolates are also prepared from this method in the yield of 90-95% from polar solvents like acetonitrile. These complexes are useful as light emitting and electron injecting materials in organic electronic devices. Also the doping of these materials in electron transport materials improves their electron mobility.

First claim

We claim:

1. A process for the preparation of compound of general formula 1

wherein
M is Lithium, sodium or potassium;
each R is independently H, alkyl, alkoxy, aryl, aryloxy, amino, amido or halogen,
the process comprising the steps of:
i. dissolving substituted 8-hydroxyquinoline of formula X and fresh scratched metal in 1:1 molar ratio in polar solvent with continuous stirring for period in the range of 20 to 25 min to obtain a solution

wherein
each R is independently H, alkyl, alkoxy, aryl, aryloxy, amino, amido or halogen; and
ii. filtering the solution as obtained in step (i), drying in vacuum at temperature in the range of 100 to 120° C. for period in the range of 10 to 12 hrs followed by purification by vacuum sublimation to obtain pure compound of general formula 1.

2. The process according to claim 1 , wherein the metal used in step (i) is lithium, sodium or potassium.

3. The process according to claim 1 , wherein the polar solvent used in step (i) is acetonitrile, methanol, ethanol, propanol, or dichloromethane.

4. The process according to claim 1 , wherein the yield of compound of general formula 1 is in the range of 90 to 95%.

5. The process according to claim 1 , wherein the compound of general formula 1 is one of the following compounds:

6. The process according to claim 4 , wherein the compound of general formula 1 is one of the following compounds:

7. A method for preparing an organic light emitting device, the method comprising forming, among other layers, and electron injecting layer by employing a compound of general formula 1 which is prepared by the process of claim 4 .

8. A method for an organic light emitting device, the method comprising forming an electron injecting layer by employing a compound of general formula 1 which is prepared by the process of claim 1 .

9. The method according to claim 8 , wherein the compound of general formula 1 is additionally a n-dopant in an electron transport layer.

10. The method according to claim 9 , wherein n-dopants are in the range of 10 to 30% by weight.

11. The method according to claim 8 , wherein the electron injecting layer is 1 to 2 nm thick.

12. The method according to claim 8 , wherein the organic emissive layer is 30 to 35 nm thick.

13. The method according to claim 8 , wherein said organic light emitting device comprises:
i. a substrate layer;
ii. an anode layer superimposed on substrate layer;
iii. a hole transport layer deposited on the anode layer;
iv. an organic emissive layer covering the hole transport layer;
v. an electron transport layer covering the organic emissive layer;
vi. an electron injection layer covering the electron transport layer;
vii. a cathode superimposed over the electron injection layer.

14. The method according to claim 13 , wherein substrate layer is composed of transparent glass.

15. The method according to claim 13 , wherein the anode layer is composed of indium tin oxide.

Assignees

• Kamalasanan Modeeparampil Narayanan
• Srivastava Ritu
• Kumar Amit
• Singh Ishwar
• Dhawan Sandeep Kumar
• Bawa Sukhwant Singh
• Council Scient Ind Res

Inventors

• Kamalasanan Modeeparampil Narayanan
• Srivastava Ritu
• Kumar Amit
• Singh Ishwar
• Dhawan Sandeep Kumar
• Bawa Sukhwant Singh

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/181

  of the alkali metals and alkaline earth metals · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H01L51/5092

  Electricity · mapped topic

• H01L51/5076

  Electricity · mapped topic