Aromatic compounds for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12595271-B2
Application number	US-202017785421-A
Country	US
Kind code	B2
Filing date	Dec 15, 2020
Priority date	Dec 18, 2019
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

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

First claim

The invention claimed is:

1 . A compound including at least one structure of the formula (Ia) and/or (Ib):

where the symbols and indices used are as follows:
Z 1 , Z 2 is the same or different at each instance and is N, P, B, Al, P(═O), P(═S), or Ga;
Y 1 , Y 2 , Y 3 is the same or different at each instance and is a bond, N(Ar), N(R), P(Ar), P(R), P(═O)Ar, P(═O)R, P(═S)Ar, P(═S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr, C═C(R) 2 , O, S, Se, S═O, or SO 2 ;
p 2 , p 3 are the same or different and are 0 or 1;
X is N, CR, or C if a Y 1 , Y 2 or Y 3 group binds thereto, with the proviso that not more than two of the X groups in one cycle are N;
R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 1 ) 2 , C(═O)N(Ar) 2 , C(═O)N(R 1 ) 2 , C(Ar) 3 , C(R 1 ) 3 , Si(Ar) 3 , Si(R 1 ) 3 , B(Ar) 2 , B(R 1 ) 2 , C(═O)Ar, C(═O)R 1 , P(═O)(Ar) 2 , P(═O)(R 1 ) 2 , P(Ar) 2 , P(R 1 ) 2 , S(═O)Ar, S(═O)R 1 , S(═O) 2 Ar, S(═O) 2 R 1 , OSO 2 Ar, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R 1 radicals, where one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —C(═O)O—, —C(═O)NR 1 —, NR 1 , 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 and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R radicals may also together form a ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, it is possible for two Ar radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ) and P(═O)R 1 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 2 ) 2 , C(═O)Ar′, C(═O)R 2 , P(═O)(Ar′) 2 , P(Ar′) 2 , B(Ar′) 2 , B(R 2 ) 2 , C(Ar′) 3 , C(R 2 ) 3 , Si(Ar′) 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 group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(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 60 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 60 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems; at the same time, two or more, preferably adjacent R 1 radicals together may form a ring system; at the same time, one or more R 1 radicals may form a ring system with a further part of the compound;
Ar′ 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 R 2 radicals; at the same time, it is possible for two Ar′ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge 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 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 which has 5 to 30 aromatic ring atoms and 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; or two or more substituents R 2 together may form a ring system; and
wherein at least two R radicals form a fused ring together with the further groups to which the two R radicals bind, where the two R radicals form at least one structure of the formulae (RA-1) to (RA-12);
where R 1 has the definition set out above, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R radicals bind, and the further symbols have the following definition,

Y 4 is the same or different at each instance and is C(R 1 ) 2 , (R 1 ) 2 C—C(R 1 ) 2 , (R 1 )C═C(R 1 ), NR 1 , NAr, O or S;
R a is the same or different at each instance and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R 2 radicals, where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —O(═O)O—, —C(═O)NR 2 —, NR 2 , 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 and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 2 radicals; or two R a radicals together may form a ring system;
s is 0, 1, 2, 3, 4, 5 or 6;
t is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

2 . A compound as claimed in claim 1 , comprising at least one structure of the formulae (IIa), (IIb), (IIc) and (IId):

where p 2 , p 3 , Y 1 , Y 2 , Y 3 , X, Z 1 , Z 2 and R have the definitions given in claim 1 , the index n is 0, 1, 2 or 3, the index j is 0, 1 or 2, and the index k is 0 or 1, where the sum total of the indices k, j and n is 0, 1, 2, 3, 4, 5 or 6.

3 . A compound as claimed in claim 1 , selected from the compounds of the formulae (IIIa), (IIIb), (IIIc) and (IIId):

where Y 1 , Y2, Y 3 , X, Z 1 , Z 2 and R have the definitions given in claim 1 , the index l is 0, 1, 2, 3, 4 or 5, the index m is 0, 1, 2, 3 or 4, and the index n is 0, 1, 2 or 3, where the sum total of the indices l, m and n is 2, 3, 4, 5, 6, 7 or 8, preference being given to structures of the formulae (IIIa) a

Assignees

• Udc Ireland Ltd

Inventors

• Stoessel Philipp
• Linge Rouven

Classifications

• H10K85/658

  Organoboranes · CPC title

• C09K2211/104

  with other heteroatoms · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D279/14

  condensed with carbocyclic rings or ring systems · CPC title