Phenanthrene compounds for organic electronic devices

Patent metadata

Field	Value
Publication number	US-10446759-B2
Application number	US-201715783333-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Jun 6, 2012
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

The invention relates to specific phenanthrenes, the use of the compound in an electronic device, and an electronic device containing at least one of said compounds. The invention further relates to a method for producing the compound and a formulation and composition containing one or more of the compounds.

First claim

The invention claimed is:

1. A compound of the general formula (1)

where the following applies to the symbols and indices occurring:
X is on each occurrence, identically or differently, N and CR 1 , where a maximum of 2 of the X is optionally equal to N;
L is a single bond or a divalent aryl or heteroaryl group having 12 to 40 ring atoms, which is optionally substituted by one or more radicals R 2 , where, if L is a single bond, the nitrogen is bonded directly to position 3 of the phenanthrene;
Ar 1 is selected from formulae (9)-(22), (24)-(28), (20′)-(20′″), (29)-(36) (32′)-(34′) and (58)-(100):

Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, where the ring or ring system is optionally substituted by one or more radicals R 4 , where, if both Ar 1 and also Ar 2 are phenyl radicals, at least one R 4 on the phenyl radicals is not equal to H and this at least one radical R 4 optionally contains one or more aromatic or heteroaromatic rings;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 2 , CN, Si(R 2 ) 3 , NO 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, C≡NR 2 , —C(═O)O—, —C(═O)NR 2 —, P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , where two or more radicals R 1 is optionally linked to one another and may form a ring;
R 4 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 2 , CN, Si(R 2 )3, NR 2 , NO 2 , P(═O)(R 2 ) 2 , S(═O) 2 R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 2 C═CR 2 —, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , where two or more radicals R 4 is optionally linked to one another and may form a ring;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 3 , CN, Si(R 3 )3, NO 2 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 3 C═CR 3 —, Si(R 3 ) 2 , CO, ═C═S, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , where two or more radicals R 2 is optionally linked to one another and optionally form a ring;
R 3 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R 3 here is optionally linked to one another and optionally form a ring;
where the compound of the formula (1), besides the phenanthrene, contains no further condensed aromatic or heteroaromatic ring having more than 10 ring atoms and
where the radicals R 1 on the phenanthrene in formula (1) contain no further amine groups.

2. The compound according to claim 1 , wherein the compound is of the general formula

where the definitions from claim 1 apply to the symbols used.

3. The compound according to claim 1 , wherein the compound has the general formula (5)

where Q is on each occurrence, identically or differently, CR 4 or N;
L is a single bond or a biphenylene, terphenylene or a compound of the formula (101a) or (101b),

where Y is equal to C(R 2 ) 2 , NR 2 , O, Si(R 2 ) 2 or S;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R 2 , CN, Si(R 2 ) 3 , NO 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 2 C═CR 2 —, —C═C—, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic ring system having 6 to 30 aromatic rin

Assignees

• Merck Patent Gmbh

Inventors

• Mujica-Fernaud Teresa
• Buesing Arne
• Voges Frank
• Kroeber Jonas

Classifications

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C2603/52

  containing five condensed rings · CPC title

• C07D407/12

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

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09B69/008

  Dyes containing a substituent, which contains a silicium atom · CPC title