Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12433160-B2
Application number	US-202118021560-A
Country	US
Kind code	B2
Filing date	Aug 16, 2021
Priority date	Aug 18, 2020
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

The invention relates to compounds which are suitable for use in electronic devices, and electronic devices, in particular organic electroluminescent devices, containing said compounds.

First claim

The invention claimed is:

1. A compound of formula (1)

comprising a structure of formula (2)

wherein:
X is the same or different at each instance and is CR or N, with the proviso that not more than two X groups per cycle are N; and two adjacent X groups that are part of the same cycle are C, at which a group of the formula (2), via the bonds identified by *, form an aromatic or heteroaromatic ring system fused onto the cycle;
Q is the same or different at each instance and is CR 1 or N, with the proviso that at most two Q groups per ring are N;
Y is the same or different at each instance and is a BR, C(R) 2 , C═O, Si(R) 2 , NR, NAr 1 , O, Se, SO, SO 2 , PR or P(═O)R, where, in the case that m or n is 0, the carbon atoms that bind to Y are each X;
m and n are 0 or 1, where m+n is 1;
Ar 1 is an aromatic ring system which has 6 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals;
R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar 2 ′) 2 , N(R 1 ) 2 , OAr 2 ′, SAr 2 ′, B(OR 1 ) 2 , CHO, C(═O)R 1 , CR 1 ═C(R 1 ) 2 , CN, C(═O)OR 1 , C(═O)NR 1 , Si(R 1 ) 3 , NO 2 , P(═O)(R 1 ) 2 , OSO 2 R 1 , OR 1 , S(═O)R 1 , S(═O) 2 R 1 , SR 1 , a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may be substituted in each case by one or more R 1 radicals, where one or more nonadjacent CH 2 groups may be replaced by —R 1 C═CR 1 —, —C≡C—, Si(R 1 ) 2 , NR 1 , CONR 1 , C═O, C═S, —C(═O)O—, P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R 1 radicals, where two or more R radicals bonded to the same cycle may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 1 radicals;
Ar 2 ′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals;
R 1 is the same or different at each instance and is H, D, F, I, B(OR 2 ) 2 , N(R 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , Si(R 2 ) 3 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , SR 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R 2 radicals and where one or more CH 2 groups in the abovementioned groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, —C(═O)O—, NR 2 , CONR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 , and where one or more hydrogen atoms in the abovementioned groups may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, where two or more R 1 radicals together may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
R 2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F; at the same time, two or more R 2 substituents may be joined to one another and may form a ring.

2. The compound as claimed in claim 1 , selected from the compounds of the formulae (3) and (4)

wherein:
X is the same or different at each instance and is CR or N, with the proviso that not more than two X groups per cycle are N; and two adjacent X groups that are part of the same cycle are C;
Q is the same or different at each instance and is CR 1 or N, with the proviso that at most two Q groups per ring are N.

3. The compound as claimed in claim 1 , selected from the compounds of the formulae (5) to (8)

wherein:
X is the same or different at each instance and is CR or N, with the proviso that not more than two X groups per cycle are N; and two adjacent X groups that are part of the same cycle are C;
Q is the same or different at each instance and is CR 1 or N, with the proviso that at most two Q groups per ring are N.

4. The compound as claimed in claim 1 , selected from the compounds of the formulae (5-1) to (8-1)

5. The compound as claimed in claim 1 , wherein Y is NAr 1 , O or S.

6. A formulation comprising at least one compound as claimed in claim 1 at least one further compound and/or at least one solvent.

7. A method comprising providing the compound as claimed in claim 1 incorporating the compound in an electronic device.

8. An electronic device comprising at least one compound as claimed in claim 1 .

9. The electronic device as claimed in claim 8 is an organic electroluminescent device, wherein the compound is used in an emitting layer as matrix material for phosphorescent or fluorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), or in an electron transport layer and/or in a hole blocker layer and/or in a hole transport layer and/or in an exciton blocker layer.

10. The compound as claimed in claim 1 , selected from the compounds of the formulae (5-1-1) to (8-1-4):

wherein
R′ is the same or different at each instance or is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, optionally substituted by one or more R 1 groups.

11. The compound as claimed in claim 1 , wherein the compound is selected from

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Stoessel Philipp
• Ehrenreich Christian

Classifications

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title