Formulations and electronic devices

Patent metadata

Field	Value
Publication number	US-9159930-B2
Application number	US-201013695703-A
Country	US
Kind code	B2
Filing date	Nov 26, 2010
Priority date	Nov 26, 2010
Publication date	Oct 13, 2015
Grant date	Oct 13, 2015

Abstract

The present invention relates to a formulation comprising at least one solvent and at least two functional compounds of the general formula (I) where A is a functional structural element, B is a solubility-promoting structural element and k is an integer in the range from 1 to 20, the molecular weight of the functional compound is at least 550 g/mol and the solubility-promoting structural element B conforms to the general formula (L-I) where Ar1, Ar2 is each, independently of one another, an aryl or heteroaryl group, which may be substituted by one or more radicals R of any desired type, X is in each case, independently of one another, N or CR2, preferably CH, R1, R2 is each, independently of one another, hydrogen, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or is a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a cyano group (CN), a carbamoyl group (C(═O)NH2), a haloformyl group (C(═O)—X, in which X represents a halogen atom), a formyl group (C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or a thio-isocyanate group, a hydroxyl group, a nitro group, a CF3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where one or more of the groups R1 and/or R2 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another and/or with the ring to which the group R1 is bonded; and l is 0, 1, 2, 3 or 4; where the dashed bond indicates the bond to the functional structural element A. The present invention furthermore relates to electronic devices which comprise mixtures of these compounds.

First claim

The invention claimed is:

1. A formulation comprising at least one solvent and at least two different functional compounds of formula (I)
A B] k   (I)

wherein
A is a functional structural element, the structural element serving as a host material, as a unit that has hole-injection and/or hole-transport properties, as a unit that has electron-injection and/or electron-transport properties, as a unit which has light-emitting properties, or as a unit which improves the transfer from the singlet state to the triplet state of light-emitting compounds;
B is a solubility-promoting structural element; and
k is an integer in the range from 1 to 20;
the molecular weight of the functional compound is at least 800 g/mol and the solubility-promoting structural element B conforms to the general formula (L-II)

wherein
R 1 , R 2 , R 3 , and R 4
are each, independently of one another, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or is a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a formyl group (—C(═O)—H), a CF 3 group, Cl, Br, F, a crosslinkable group or an optionally substituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, where one or more of the groups R 1 , R 2 , R 3 and/or R 4 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another and/or with another ring;

m is 0, 1, 2 or 3,
n and o are each, independently of one another, 0, 1, 2, 3, 4, or 5, and
the dashed bond indicates the bond to the functional structural element A.

2. The formulation of claim 1 , wherein the functional structural element A in formula (I) serves as host material.

3. The formulation of claim 1 , wherein the functional structural element A in formula (I) is a unit which has hole-injection and/or hole-transport properties.

4. The formulation of claim 1 , wherein the functional structural element A in formula (I) is a unit which has electron-injection and/or electron-transport properties.

5. The formulation of claim 1 , wherein the functional structural element A in formula (I) is a unit which has light-emitting properties.

6. The formulation of claim 1 , wherein the formulation comprises at least one functional compound in which the functional structural element A in formula (I) is a unit having phosphorescent properties.

7. The formulation of claim 5 , wherein the formulation comprises at least one functional compound in which the functional structural element A in formula (I) is a unit which includes at least one heavy atom having an atomic number of greater than 36.

8. The formulation of claim 1 , wherein the functional structural element A in formula (I) is a unit which improves the transfer from the singlet state to the triplet state of light-emitting compounds.

9. The formulation of claim 1 , wherein the formulation comprises at least one functional compound in which the functional structural element A in formula (I) is a unit which has light-emitting properties, and at least one functional compound in which the functional structural element A in formula (I) is a unit which can serve as host material.

10. The formulation of claim 1 , wherein the formulation comprises at least two functional compounds in which the functional structural element A in formula (I) is a unit which can serve as host material.

11. The formulation of claim 1 , wherein the formulation comprises at least one functional compound in which the functional structural element A in formula (I) is a unit which can serve as host material, where the functional structural element A has at least one nitrogen atom.

12. The formulation of claim 1 , wherein the formulation comprises at least one functional compound which comprises no solubility-promoting structural element B of the general formula (L-I).

13. The formulation of claim 1 , wherein the proportion of functional compounds in the formulation which comprise no solubility-promoting structural element B of the general formula (L-I) is at most 50% by weight, based on the total weight of the functional compounds.

14. The formulation of claim 1 , wherein the formulation comprises at least 80% by weight of aromatic or heteroaromatic solvent.

15. The formulation of claim 1 , wherein the index k in formula (I) is an integer greater than or equal to 2.

16. The formulation of claim 1 , wherein the functional compound of the general formula (I) has a glass-transition temperature of at least 70° C.

17. The formulation of claim 1 , wherein the weight ratio of structural element A to structural element B in formula (I) is in the range from 2:1 to 1:20.

18. An electronic device produced from the formulation of claim 1 .

19. The electronic device of claim 18 , wherein the at least two functional compounds of the general formula (I) is present in the device as hole-transport, hole-injection, emitter, electron-transport, electron-injection, charge-blocking and/or charge-generation layer.

20. The electronic device of claim 18 , wherein the electronic device is an organic electroluminescent device, a polymeric electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, or an organic laser diode.

21. A process for producing an electronic device comprising (1) applying the formulation of claim 1 to a substrate and (2) drying the applied formulation.

Assignees

• Anémian Rémi Manouk
• Heun Susanne
• Eberle Thomas
• Stoessel Philipp
• Ludemann Aurélie
• Kunkel Dietmar
• Merck Patent Gmbh

Inventors

• Anémian Rémi Manouk
• Heun Susanne
• Eberle Thomas
• Stoessel Philipp
• Ludemann Aurélie
• Kunkel Dietmar

Classifications

• H10K50/171

  Electron injection layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/1135

  Polyethylene dioxythiophene [PEDOT]; Derivatives thereof · CPC title

• C07C15/30 Primary

  Phenanthrenes · CPC title

• H01L51/0072

  Electricity · mapped topic