IP Library Granted Patent US 10,847,727
Granted Patent B2
US 10,847,727 · App. 15/319,459 · Granted Nov 24, 2020

Compositions for electronic devices

Inventors: Anna Hayer (Darmstadt, DE); Florian Maier-Flaig (Weinheim, DE); Tobias Grossmann (Darmstadt, DE); Dominik Joosten (Frankfurt am Main, DE); Holger Heil (Frankfurt am Main, DE); Thomas Eberle (Landau, DE); Rémi Manouk Anémian (Seoul, KR)
Assignee: Merck Patent GmbH
H01L51/0072C07D209/96C07D403/04C07D403/10C07D403/14C07D405/10C07F15/0086C09K11/025C09K11/06H01L51/006H01L51/0052H01L51/0054H01L51/0056H01L51/0059H01L51/0061H01L51/0067H01L51/0073H01L51/0074H01L51/0085H01L51/0087H01L51/5004H01L51/5016C07C2603/18C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1074C09K2211/1088C09K2211/1092C09K2211/185H01L51/0058H01L51/5056H01L51/5072H01L2251/5384H01L2251/552Y02E10/549
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Quick Facts
Patent No.
US 10,847,727
App. No.
15/319,459
Granted
Nov 24, 2020
Kind
B2
Abstract

The present invention relates to compositions and formulations for electronic devices comprising mixtures of organic functional materials.

Claims (59)

1. A composition comprising a bipolar host, a neutral co-host and a light-emitting dopant wherein (a) the following conditions are satisfied:

|HOMO( C )|−min{|HOMO( D )|;|HOMO( B )|}>0.3 eV

|HOMO( B )|−|HOMO( D )|<0.15 eV

|LUMO( B )|−|LUMO( C )|>0.3 eV

|LUMO( B )|−|LUMO( D )|>0,

where HOMO(C) stands for the HOMO energy of the neutral co-host, HOMO(B) and HOMO(D) correspondingly stand for the HOMO energy of the bipolar host and of the dopant respectively, LUMO(C), LUMO(B) and LUMO(D) correspondingly stand for the LUMO energy of the neutral co-host, of the bipolar host and of the dopant respectively, and the function min{|HOMO(D)|;|HOMO(B)|} supplies the smaller of the two values |HOMO(D)| and |HOMO(B)|,

or (b) wherein the following conditions are satisfied:

max{|LUMO( D )|;|LUMO( B )|}−|LUMO( C )|>0.3 eV

|LUMO( D )|−|LUMO( B )|<0.15 eV

|HOMO( C )|−|HOMO( B )|>0.3 eV

|HOMO( D )|−|HOMO( B )|>0,

where the function max{|LUMO(D)|; |LUMO(B)|} supplies the larger of the two values |LUMO(D)| and |LUMO(B)|,

wherein the light emitting dopant is selected from phosphorescent emitters:

and where |HOMO| and |LUMO| are the modulus of the respective value, where the energy values indicated relate to isolated compounds and are determined by quantum-chemical calculations, wherein the bipolar host is selected from the group of the pyridines, pyrimidines, triazines, benzimidazoles, carbazoles, indenocarbazoles, indolocarbazoles, 1,10-phenanthrolines, 1,3,4-oxadiazoles, phosphine oxides, phenylsulfonyls, ketones, lactams and triarylamines, and

wherein the neutral co-host is selected from the group of compounds

2. The composition according to claim 1 , wherein the following conditions are satisfied:

|HOMO( B )|−|HOMO( D )|<0.15 eV and

|HOMO( B )|−|HOMO( D )|>−0.2 eV.

3. The composition according to claim 1 , wherein the following condition is satisfied:

|HOMO( C )|−min{|HOMO( D )|;|HOMO( B )|}>0.4 eV,

or

|HOMO( C )|−min{|HOMO( D )|;|HOMO( B )|}>0.6 eV.

4. The composition according to claim 1 , wherein the following condition is satisfied:

|LUMO( B )|−|LUMO( C )|>0.4 eV,

or

|LUMO( B )|−|LUMO( C )|>0.6 eV.

5. The composition according to claim 1 , wherein the following conditions are satisfied:

|LUMO( D )|−|LUMO( B )|<0.15 eV and

|LUMO( D )|−|LUMO( B )|>−0.2 eV,

or

|LUMO( D )|−|LUMO( B )|<0.1 eV and

|LUMO( D )|−|LUMO( B )|>−0.1 eV.

6. The composition according to claim 1 , wherein the following condition is satisfied:

max{|LUMO( D )|;|LUMO( B )|}−|LUMO( C )|>0.4 eV,

or

max{|LUMO( D )|;|LUMO( B )|}−|LUMO( C )|>0.6 eV.

7. The composition according to claim 1 , wherein the following condition is satisfied:

|HOMO( C )|−|HOMO( B )|>0.4 eV,

or

|HOMO( C )|−|HOMO( B )|>0.6 eV.

8. The composition according to claim 1 , wherein the composition comprises further organic functional materials which are selected from the group consisting of the hole-injection materials, hole-transport materials, hole-blocking materials, host materials, emitter materials, electron-blocking materials, electron-transport materials and electron-injection materials.

9. The composition according to claim 1 , wherein the composition comprises a further host material selected from the group consisting of a bipolar host material, a neutral host material, a hole-transporting material, and an electron-transporting material.

10. The composition according to claim 1 , wherein the composition comprises a further, second light-emitting dopant which is a phosphorescent emitter.

11. The composition according to claim 10 , wherein the composition comprises a further, third light-emitting dopant which is a phosphorescent emitter.

12. The composition according to claim 1 , wherein the composition comprises no further organic or inorganic constituents besides the said organic constituents.

13. A formulation comprising the composition according to claim 1 and at least one solvent.

14. A method for the production of an electronic device comprising utilizing the formulation according to claim 13 to process an emission layer of the device from solution.

15. A method comprising utilizing the composition according to claim 1 in an organic electronic device.

16. An organic electronic device comprising at least one composition according to claim 1 , where the device is selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

17. The device according to claim 16 , wherein the device is an organic electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

18. The device according to claim 16 , wherein it is an organic electroluminescent device which comprises the composition in the emission layer.

19. The device according to claim 18 , wherein the emission layer comprises the composition and where a hole-transport layer which comprises a hole-transport material (HTM) is directly adjacent to the emission layer, where the following condition applies to the moduli of the HOMO energies of the bipolar host in the emission layer and of the hole-transport material in the hole-transport layer:

|HOMO( B )|−|HOMO(HTM)|<0.3 eV.

20. The device according to claim 18 , wherein the emission layer comprises the composition and where an electron-transport layer which comprises an electron-transport material, ETM, is directly adjacent to the emission layer, where the following condition applies to the moduli of the LUMO energies of the bipolar host in the emission layer and of the electron-transport material in the electron-transport layer:

|LUMO( B )|−|LUMO(ETM)|<0.3 eV.

21. The composition according to claim 1 , wherein the following conditions are satisfied:

|HOMO( B )|−|HOMO( D )|<0.1 eV and

|HOMO( B )|−|HOMO( D )|>−0.1 eV.

22. The composition according to claim 1 , wherein the bipolar host is a carbazole/triazine hybrid system, indenocarbazole/triazine hybrid system, indolocarba zole/triazine hybrid system, carbazole-carbazole/triazine hybrid system, indenocarbazole-carbazole/triazine hybrid system or an amine/triazine hybrid system.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2016
From: HAYER, ANNA; MAIER-FLAIG, FLORIAN; GROSSMANN, TOBIAS; JOOSTEN, DOMINIK; HEIL, HOLGER; EBERLE, THOMAS; ANEMIAN, REMI MANOUK
To: MERCK PATENT GMBH
Reel/Frame 040662/0042 →
Priority Claims (1)
DE 10 2014 008 722 · Jun 18, 2014 · national
Continuity (1)
Related Publication 20170141328A1 · May 18, 2017
Cited By (5)
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