Phenanthrene compounds for organic electronic devices

Patent metadata

Field	Value
Publication number	US-2018102479-A1
Application number	US-201715783333-A
Country	US
Kind code	A1
Filing date	Oct 13, 2017
Priority date	Jun 6, 2012
Publication date	Apr 12, 2018
Grant date	—

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

1 .- 17 . (canceled)

18 . 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)-(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(=0) 2 R 2 , a straight-chain alkyl, alkoxy or thio-alkyl 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 CH2 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)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 CH2 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 thio-alkyl 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.

19 . The compound according to claim 18 , wherein the compound is of the general formula

where the definitions from claim 18 apply to the symbols used.

20 . The compound according to claim 18 , wherein the compound has the general formula (5)

where Q is on each occurrence, identically or differently, CR 4 or N.

21 . The compound according to claim 18 , wherein the compound has the general (6)

where Q is on each occurrence, identically or differently, CR 4 or N.

22 . The compound according to claim 18 , wherein the compound has the general (7)

where Q is on each occurrence, identically or differently, CR 4 or N.

23 . The compound according to claim 18 , wherein L is an aromatic ring system selected from the group consisting of biphenylenes, terphenylenes and the compounds of the formula (101a) and (101b),

where Y is equal to C(R 2 ) 2 , NR 2 , O, Si(R 2 ) 2 or S.

24 . The compound according to claim 23 , wherein Y is C(R 2 ) 2 or NR 2 .

25 . The compound according to cl

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07C217/80

  having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C07D471/06

  Peri-condensed systems · CPC title

• C07D311/80

  Dibenzopyrans; Hydrogenated dibenzopyrans · CPC title