IP Library › Granted Patent US 10,734,587
Granted Patent B2
US 10,734,587 · App. 15/125,215 · Granted Aug 4, 2020

Formulations of luminescent compounds

Inventors: Amir Hossain Parham (Frankfurt am Main, DE); Philipp Stoessel (Frankfurt am Main, DE); Christof Pflumm (Darmstadt, DE); Anja Jatsch (Frankfurt am Main, DE); Joachim Kaiser (Darmstadt, DE); Anna Hayer (Mainz, DE)
Assignee: Merck Patent GmbH
H01L51/0067C07D209/82C07D221/20C07D251/24C07D403/04C07D403/10C07D403/14C07D413/10C07D413/14C09D5/22C09D5/24C09K11/025C09K11/06H01J9/223H01L51/0039H01L51/0043H01L51/0052H01L51/0072H01L51/5004H01L51/5012C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1092C09K2211/185H01L51/001H01L51/0007H01L51/0085H01L51/5016H01L51/5056H01L51/5072H01L51/56H01L2251/5384H01L2251/55H01L2251/552H01L2251/556
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Quick Facts
Patent No.
US 10,734,587
App. No.
15/125,215
Granted
Aug 4, 2020
Kind
B2
Abstract

The present invention relates to a formulation comprising organic materials for the production of organic electronic devices having a low failure rate.

Claims (17)

1. A formulation comprising at least one type of organic luminescent compound (TADF compound) and an organic solvent or a mixture of multiple organic solvents, wherein the TADF compound has a separation between the lowest triplet state T 1 and the first excited singlet state Si of less than or equal to 0.15 eV;

wherein the formulation comprises a first organic matrix material and a second organic matrix material,

wherein the first organic matrix material is an electron-transporting material or a hole-transporting matrix material, and the second organic matrix material is a compound which has a band gap between HOMO and LUMO of greater than or equal to 3.5 eV.

2. The formulation of claim 1 , wherein the separation between S 1 and T 1 of the TADF compound is less than or equal to 0.10 eV.

3. The formulation of claim 1 , wherein the TADF compound is an aromatic compound which contains both donor and acceptor substituents.

4. The formulation of claim 1 , wherein the surface tension of the solvent or solvents is at least 28 mN/m.

5. The formulation of claim 1 , wherein the boiling or sublimation point of the solvent or solvents is less than 300° C.

6. The formulation of claim 1 , wherein the viscosity of the solvent or of the individual solvents of a solvent mixture is greater than 3 mPa*s.

7. The formulation of claim 1 , wherein the molecular weight of the solvent or of the solvents used in the solvent mixture is less than or equal to 1000 g/mol.

8. The formulation of claim 1 , wherein the concentration of the TADF compound in the formulation, based on the entire formulation, is in the range from 1 to 20% by weight.

9. The formulation of claim 1 , wherein the solvent is selected from the group consisting of toluene, anisole, o-, m- or p-xylene, methylbenzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, (−)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)-ethane and mixtures thereof.

10. The formulation of claim 1 , characterised in that the formulation comprises a matrix material, where the following applies for the lowest unoccupied molecular orbital (LUMO) of the TADF compound LUMO(TADF) and the highest occupied molecular orbital (HOMO) of the matrix HOMO(matrix):

[LUMO(TADF)−HOMO(matrix)] is greater than or equal to [ S 1 (TADF)−0.4 eV],

where S 1 (TADF) is the first excited singlet state S 1 of the TADF compound.

11. A method for producing one or more layers of an organic electronic device from solution comprising utilizing the formulation of claim 1 .

12. A process for the production of an organic electronic device, comprising producing at least one layer of the electronic device from solution with the aid of the formulation of claim 1 .

13. The process of claim 12 , characterised in that the electronic device is an organic electroluminescent device.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2016
From: PARHAM, AMIR HOSSAIN; STOESSEL, PHILIPP; PFLUMM, CHRISTOF; JATSCH, ANJA; KAISER, JOACHIM; HAYER, ANNA
To: MERCK PATENT GMBH
Reel/Frame 039803/0266 →
Priority Claims (1)
EP 14000920 · Mar 13, 2014 · regional
Continuity (1)
Related Publication 20170084844A1 · Mar 23, 2017
Cited By (1)
US 12,649,863