Heterocyclic compounds for use in electronic devices

Patent metadata

Field	Value
Publication number	US-11329233-B2
Application number	US-201716463908-A
Country	US
Kind code	B2
Filing date	Nov 30, 2017
Priority date	Dec 2, 2016
Publication date	May 10, 2022
Grant date	May 10, 2022

Abstract

The invention relates to heterocyclic compounds, particularly 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 comprising at least one structure of the formula (I) and/or (II):

where the symbols used are as follows:
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , X 24 is N or CR 1 ,
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;
Ar 10 is the same or different at each instance and is of the formula (H-1)

Ar 2 is an aromatic or heteroaromatic ring system which has 5 to 14 aromatic or heteroaromatic ring atoms, which may be substituted by one or more R 21 radicals;
p is 0 or 1,
Ar 3 and Ar 4 are the same or different at each instance and are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which may be substituted by one or more R 21 radicals;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , 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 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 , NR 2 , P(═O)(R 2 ), —C(═O)O—, —C(═O)NR 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 and may be substituted in each case 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 diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 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 R 1 radicals together may form a ring system;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , 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 , Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , NR 3 , P(═O)(R 3 ), —C(═O)O—, —C(═O)NR 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 an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 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 R 2 substituents together may also form a ring system;
R 21 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , 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 , 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 ), —C(═O)O—, —C(═O)NR 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 an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals and with the proviso that the aromatic or heteroaromatic ring system does not contain triarylamine;
R 3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R 3 substituents together may also form a ring system.

2. A compound as claimed in claim 1 , comprising at least one structure of the formula (III) and/or (IV)

where the symbols R 1 , Ar 10 and Ar used have the definition given in claim 1 and m at each instance is in each case independently 0, 1, 2, 3 or 4, and n at each instance is in each case independently 0, 1, 2 or 3.

3. A compound as claimed in claim 1 , comprising at least one structure of the formula (V) and/or (VI)

where
R a is F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , 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 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 , NR 2 , P(═O)(R 2 ), —C(═O)O—, —C(═O)NR 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 and may be substituted in each case 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 diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals; or a combination of these systems; at the same time, the R a radical may form a ring system together with an R 1 radical or with the ring to which it is bonded;
the symbols X 1 , X 2 , X

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils
• Harbach Philipp
• Joosten Dominik
• Parham Amir
• Jatsch Anja

Classifications

• C07D487/06

  Peri-condensed systems · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title