Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-2025386664-A1
Application number	US-202318878154-A
Country	US
Kind code	A1
Filing date	Jun 6, 2023
Priority date	Jun 28, 2022
Publication date	Dec 18, 2025
Grant date	—

Abstract

The invention relates to compounds of the formula (I), to methods for producing compounds of the formula (I), to the use of compounds of the formula (I) in electronic devices, and to electronic devices containing a compound of the formula (I).

First claim

1 .- 16 . (canceled)

17 . An electronic device comprising anode, cathode, an emitting layer, and a layer comprising a compound of the formula (I) disposed between the anode and the emitting layer,

where the variables that occur are as follows:
G is a group of formula (G) which is bonded to the remainder of the formula (I) via one of the unoccupied positions on the benzene rings, where the other unoccupied positions on the benzene rings are each substituted by an R 1 radical;

X 1 is O or S;
X 2 is C(R 2 ) 2 or Si(R 2 ) 2 ;
X 3 is C(R 2 ) 2 or Si(R 2 ) 2 ;
Ar L is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R 3 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R 3 radicals;
Ar 1 , Ar 2 is the same or different and is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R 4 radicals, or a heteroaromatic ring system which has 5 to 25 aromatic ring atoms and is substituted by R 4 radicals, where Ar 1 and Ar 2 may optionally be joined together via a bond or an E group;
E is C(R 4 ) 2 , —C(R 4 ) 2 —C(R 4 ) 2 —, —C(R 4 )═C(R 4 )—, C═O, Si(R 4 ) 2 , NR 4 , O, S, S═O, or SO 2 ;
R 1 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 1 , S(═O) 2 R 3 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R 1 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C═C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO or SO 2 ;
R 2 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R 2 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C═C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO or SO 2 ;
R 3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R 3 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 5 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C═C—, Si(R 5 ) 2 , C═O, C═NR, —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO or SO 2 :
R 4 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 5 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO or SO 2 ;
R 5 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R 6 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 6 C═CR 6 —, —C═C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ;
R 6 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN;
n is 0 or 1, where, when n=0, the G group and the nitrogen atom in formula (I) are bonded directly to one another.

18 . The electronic device as claimed in claim 17 , wherein formula (I) conforms to one of formulae (I-1-1), (I-1-2), (I-1-3), (I-1-4), (I-3-1), (I-3-2)

where the variables that occur are as defined in claim 17 , and where the other unoccupied positions on the benzene rings are each substituted by an R 1 radical that, in this case, is preferably H.

19 . The electronic device as claimed in claim 17 , wherein formula (I) conforms to one of formulae (I-4-1), (I-4-2) and (I-4-4), especially formula (I-4-1)

where the variables that occur are as defined in claim 17 , and where the other unoccupied positions on the benzene rings are each substituted by an R 1 radical that, in this case, is prefe

Assignees

• Merck Patent Gmbh

Inventors

• Linge Rouven
• Montenegro Elvira
• Engelhart Jens
• Mujica-Fernaud Teresa

Classifications

• C09K2211/10

  Non-macromolecular compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K85/6572 Primary

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

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title