Materials for electronic devices

• US 9,893,297 B2
• Filed: 07/12/2011
• Issued: 02/13/2018
• Est. Priority Date: 08/05/2010
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Martynova, Irina, Franz, Adam W., Pflumm, Christof, Parham, Amir Hossain, Buesing, Arne, Anmian, Rmi Manouk, Gerhard, Anja
• Primary Examiner(s): Frost, Anthony J
• Application Number:
  US13/813,162
• Publication Number:
  US 20130126792A1
• Time in Patent Office: 2,408 Days
• Field of Search: None
• CPC Class Codes: B32B 2457/202 LCD, i.e. liquid crystal displays
• CPC Class Codes: C07D 491/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/14 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/14 Ortho-condensed systems
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• 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: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• 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 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/624 containing six or more rings
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

The present invention relates to compounds of the formula (I), to the use of compounds of the formula (I) in electronic devices and electronic devices comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compounds of the formula (I) and to formulations comprising one or more compounds of the formula (I).

Claims

1. A compound of the formulae (Ia-1)-(Ia-10), (Ib-5)-(Ib-8), (Ib-11)-(Ib-19) or (Ib-20)

2. The compound according to claim 1, wherein 0, 1 or 2 groups Z per aromatic or heteroaromatic six-membered ring are equal to N.

3. The compound according to claim 1, wherein R¹ represents on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R³.

4. The compound according to claim 1, wherein at least one group is present as substituent R¹ or R² which is selected from electron-deficient heteroaryl groups, aromatic or heteroaromatic ring systems having 10 to 30 aromatic ring atoms and from arylamine groups, each of which is optionally substituted by one or more radicals as defined in claim 1.

5. A process for the preparation of the compound of the formulae (Ia-1)-(Ia-10), according to claim 1, which comprises ring-closure reacting one or more condensed heteroaromatic five-membered rings.

6. An oligomer, polymer or dendrimer comprising one or more compounds of the formulae (Ia-1)-(Ia-10), according to claim 1, where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any position in formulae (Ia-1)-(Ia-10), substituted by R¹ or R².

7. A formulation comprising at least one compound of the formulae (Ia-1)-(Ia-10), according to claim 1 and at least one solvent.

8. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 6 and at least one solvent.

9. An electronic device comprising the compound according to claim 1.

10. An electronic device comprising the polymer, oligomer or dendrimer according to claim 6.

11. An organic electroluminescent device (OLED) comprising the compound according to claim 1.

12. The Electronic device according to claim 9, wherein in the device is 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, an organic laser diode or an organic electroluminescent device.

13. An organic electroluminescent device which comprises the compound according to claim 1 is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or is employed as matrix material in an emitting layer and/or as electron-transport material in an electron-transport layer.

14. An organic electroluminescent device which comprises the polymer, oligomer or dendrimer according to claim 6 is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or is employed as matrix material in an emitting layer and/or as electron-transport material in an electron-transport layer.

15. The compound according to claim 1, wherein two or more radicals R² are linked to one another and form an aliphatic ring or a condensed aryl or heteroaryl group.

16. The compound according to claim 15, wherein two or more radicals R² are linked to one another and form a heteroaryl group which has 4 to 8 aromatic ring atoms.