Formulations and electronic devices

• US 9,882,135 B2
• Filed: 08/27/2015
• Issued: 01/30/2018
• Est. Priority Date: 05/03/2010
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Anmian, Rmi Manouk, Heun, Susanne, Eberle, Thomas, Stoessel, Philipp, Ludemann, Aurlie, Kunkel, Dietmar
• Primary Examiner(s): MC GINTY, DOUGLAS J
• Application Number:
  US14/837,724
• Publication Number:
  US 20150364689A1
• Time in Patent Office: 887 Days
• Field of Search: 25251921, 2525192, 252500, 438 99
• CPC Class Codes: C07C 15/30 Phenanthrenes
• CPC Class Codes: C07C 15/38 containing four rings
• CPC Class Codes: C07C 2603/24 Anthracenes; Hydrogenated anthracenes
• CPC Class Codes: C07C 2603/42 containing only six-membered rings
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 9/65683 the ring phosphorus atom being part of a phosphine
• CPC Class Codes: C07F 9/65685 the ring phosphorus atom being part of a phosphine oxide or thioxide
• CPC Class Codes: C07F 9/65848 Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
• CPC Class Codes: C09D 139/04 Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 : Carrier injection layers
• CPC Class Codes: H10K 50/171 : Electron injection layers
• CPC Class Codes: H10K 50/18 : Carrier blocking layers
• CPC Class Codes: H10K 71/12 : using liquid deposition, e.g. spin coating
• CPC Class Codes: H10K 85/1135 : Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/151 : Copolymers
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/60 : Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

A formulation comprising at least one solvent and at least two different functional compounds of formula (I)
AB]_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 550 g/mol, and the solubility-promoting structural element B conforms to the general formula (L-I)

Claims

1. A formulation comprising at least one solvent, at least one functional compounds of formula (I)

AB]_k 

 

(I)

and at least one functional compound of formula (I′

)

AB′

]_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;

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, the solubility-promoting structural element B′

conforms to the general formula (L-I′

) and the solubility-promoting structural element B conforms to the general formula (L-I)

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 that 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 that 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 6, 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 molecular weight of the functional compound of the general formula (I) is at least 800 g/mol.

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

C.

18. 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.

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

20. The electronic device of claim 19, 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.

21. The electronic device of claim 19, 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.

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

23. The formulation of claim 1, wherein the functional compounds of formula (I) have a molecular weight of at most 5000 g/mol.