Compounds that can be used in an organic electronic device as active compounds

Patent metadata

Field	Value
Publication number	US-12178124-B2
Application number	US-201917281166-A
Country	US
Kind code	B2
Filing date	Sep 24, 2019
Priority date	Sep 27, 2018
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

The invention relates to compounds that can be used in an organic electronic device as an active compound, in particular for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention, and to electronic devices comprising same.

First claim

The invention claimed is:

1. A compound usable with preference as active compound in an organic electronic device, wherein the compound has at least one aromatic or heteroaromatic ring system which has 5 to 60 carbon atoms and is fused to an aliphatic polycyclic ring system having at least 3 rings,
wherein the aliphatic polycyclic ring system which has at least 3 rings and is fused to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms forms a substructure of the formulae (N-1) to (N-6)

wherein
R 1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar 1 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , B(OR 2 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent 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 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems;
Ar 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more, nonaromatic R 2 radicals; at the same time, it is possible for two Ar 1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another by a single bond or a bridge selected from B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR 3 ) 2 , NO 2 , C(═O)R 3 , CR 3 ═C(R 3 ) 2 , C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , P(R 3 ) 2 , B(R 3 ) 2 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent 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═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a combination of these systems; at the same time, two or more, adjacent substituents R 2 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
R 3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more adjacent substituents R 3 together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
the index s is 0, 1, 2, 3, 4, 5 or 6;
the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
and the dotted lines represent the bonds of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the aliphatic polycyclic ring system having at least 3 rings is fused, and
wherein the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the aliphatic polycyclic ring system having at least 3 rings is fused forms a substructure of the formulae (Ar-2) to (Ar-11) and (Ar-13) to (Ar-66)

wherein X′ is N or CR 1 ;
Y′ is selected from O, S, C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 and NAr 1 ;
U is selected from O, S, C(R 1 ) 2 , N(R 1 ), B(R 1 ), Si(R 1 ) 2 , C═O, S═O, SO 2 , P(R 1 ) and P(═O)R 1 ;
R 1 is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar 1 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , B(OR 2 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent 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 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems;
Ar 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more, nonaromatic R 2 radicals; at the same time, it is possible for two Ar 1 radicals bonded to the same silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined to one another by a single bond or a bridge selected from B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, B(OR 3 )

Assignees

• Merck Patent Gmbh
• Merck Kgaa

Inventors

• Stoessel Philipp

Classifications

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• C07C2603/86

  containing four rings · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title