Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-11963442-B2
Application number	US-202117196712-A
Country	US
Kind code	B2
Filing date	Mar 9, 2021
Priority date	Apr 30, 2014
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

The application relates to compounds having functional substituents in a specific spatial arrangement, to devices comprising same, and to the preparation and use thereof.

First claim

The invention claimed is:

1. A compound of the general formula (4)

where the following applies to the symbols and indices used:
W is arylamines, bridged amines, where preferred bridged amines are carbazoles, biscarbazoles, benzocarbazoles, indenocarbazoles and indolocarbazoles; and W is optionally substituted by one or more radicals R 1 , which is optionally identical or different on each occurrence;
V is S;
r is an integer from 0, 1, 2 or 3;
s is an integer from 0, 1, 2 or 3;
X is N or CR 1 , where at least one of the five groups X represents an N atom;
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ,
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, S 02 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of two or more of these groups;
R 3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F;
R 4 , R 5 are, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms.

2. The compound according to claim 1 , wherein
r is 0; and
s is 0.

3. The compound according to claim 1 , wherein W is defined by the formula (W-1)

wherein:
U is N or CR 1 , where the dotted line denotes the bond from the group W to the ring C.

4. The compound according to claim 1 , wherein the compound has the general formula (6):

X is N or CR 1 , where at least one of the three groups X represents an N atom.

5. The compound according to claim 1 , wherein the compound has the general formula (7):

6. The compound according to claim 1 , wherein the group W is a carbazole, indenocarbazole or indolocarbazole.

7. The compound according to claim 1 , wherein the group W is a group of the formula (W-2)

8. A composition comprising at least one compound according to claim 1 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials and hole-blocking materials.

9. The composition according to claim 8 , wherein the further compound is a host material or matrix material.

10. The composition according to claim 8 , wherein the further compound has a band gap of 2.5 eV or more.

11. A formulation comprising at least one compound according to claim 1 and at least one solvent.

12. An electronic device comprising at least one compound according to claim 1 .

13. An electronic device comprising at least one compound according to claim 1 , wherein the compound is in an emission layer (EML), electron-transport layer (ETL) or in a hole-blocking layer (HBL).

14. The electronic device according to claim 13 , wherein the device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device, an organic solar cell (OSC), an organic optical detector, or an organic photoreceptor.

15. The electronic device according to claim 13 , wherein the device is an organic electroluminescent device which is also selected from the group consisting of an organic light-emitting transistor (OLET), an organic field-quench device (OFQD), an organic light-emitting electrochemical cell (OLEC, LEC, LEEC), an organic laser diode (O-laser) and an organic light-emitting diode (OLED).

16. A process for phototherapy of the skin which comprises treating the skin with the electronic device according to claim 15 .

17. A process for the production of the electronic device according to claim 13 , which comprises applying at least one organic layer by gas-phase deposition or from solution.

18. A compound of the general formula (1)

where the following applies to the symbols and indices used:
ETG is selected from the group of the triazines, pyrimidines, pyrazines, pyridines, quinazolines, quinolines, isoquinolines and naphthyridines and the ETG is optionally substituted by one or more radicals R 1 , which is op

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Grossmann Tobias
• Jatsch Anja
• Eberle Thomas
• Kroeber Jonas
• Pflumm Christof
• Dobelmann-Mara Lars

Classifications

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• A61B18/203

  applying laser energy to the outside of the body · CPC title

• A61N5/0616

  Skin treatment other than tanning · CPC title

• C07D405/14 Primary

  containing three or more hetero rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title