Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-12336428-B2
Application number	US-202318513954-A
Country	US
Kind code	B2
Filing date	Nov 20, 2023
Priority date	Oct 8, 2013
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

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. Compound of the general formula (1)

where the following applies to the symbols and indices used:
A and A′ are, identically or differently from one another, an aromatic or heteroaromatic ring having 5 or 6 ring atoms, which may be substituted by one or more radicals R 1 , which may be independent of one another;
ETG is an organic electron-transporting group (ETG) from the group of electron-deficient heteroaromatic groups, where the ETG is selected from the group consisting of triazines, pyrimidines, pyrazines, pyrazoles, pyridazines, quinoles, isoquinolines, thiazoles, benzothiazoles, oxazoles, benzoxazoles, imidazoles, benzimidazoles, and pyridines, and where the group ETG may be substituted by one or more radicals R 1 , which are independent of one another;
Z is a single bond or a divalent group; if Z is a single bond, the group ETG is then bonded directly to the carbon atom of ring A;
V is O;
W is a single bond;
m is 1;
n is 1,
where m=n;
Ar 3 is an aromatic or heteroaromatic ring or ring system having 5 to 30 ring atoms, where the ring or ring system may in each case be substituted by one or more radicals R 2 where two or more radicals R 2 do not form a ring closure with one another;
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 may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be 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 may be 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 may be 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 may be substituted by one or more radicals R 2 , or a combination of two or more of these groups or a crosslinkable group Q; two or more adjacent radicals R 1 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred for two or more adjacent radicals R 1 not to form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
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 may be substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups may be 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, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms may be 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 may be 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 may be substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 here do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another
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 may be replaced by F; two or more substituents R 3 here do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
p is 1;
R 4 is, identically or differently on each occurrence, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more H atoms may be 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 a combination of two or more of these groups.

2. Compound according to claim 1 , characterised in that it has the formula (2)

where the above definitions apply to the indices and symbols used, and where:
X is, identically or differently on each occurrence, N or CR 1 ;
Q is, identically or differently on each occurrence, X═X, S, O or NR 1 .

3. Compound according to claim 1 , characterised in that it has the formula (3)

4. Compound according to claim 1 , characterised in that it has the formula (3a)

where s and t can be integers from 0 to 3 and where s+t is equal to an integer from 0 to 6.

5. Compound according to claim 1 , characterised in that it has the formula (3b)

6. Compound according to claim 1 , characterised in that it has the formula (3c)

7. Compound according to claim 1 , characterised in that Z is a single bond or a divalent aromatic or heteroaromatic ring or ring system having 5 to 60 ring atoms.

8. Process for the preparation of the compound according to claim 1 with the aid of Suzuki coupling.

9. Process for the preparation of the compound according to claim 1 with the aid of Buchwald or Ullmann coupling.

10. 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, hole-blocking materials, n-dopants and p-dopants.

11. Composition according to claim 10 , characterised in that the additional compound is a phosphorescent emitter.

12. Composition according to claim 10 , characterised in that the additional compound is a host material or matrix material.

13. Composition according to claim 11 , characterised in that the additional compound

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Martynova Irina
• Jatsch Anja
• Eberle Thomas
• Kroeber Jonas Valentin
• Pflumm Christof

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D495/14

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• A61N2005/0653

  Organic light emitting diodes · CPC title

• A61N5/0621

  Hyperbilirubinemia, jaundice treatment · CPC title

• A61N5/0616

  Skin treatment other than tanning · CPC title