Compound with novel six-membered ring structure for use in organic electronic devices

Patent metadata

Field	Value
Publication number	US-10374167-B2
Application number	US-201415036311-A
Country	US
Kind code	B2
Filing date	Oct 20, 2014
Priority date	Nov 15, 2013
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

The present invention relates to novel compounds according to formula (I) having a six-membered ring structure substituted with electron donor, electron acceptor and sterically demanding groups. Said compound is suited for use in organic electronic devices, particularly in organic electroluminescent devices (OLEDs). Formula (I) wherein Q 1 and Q 2 are independently of each other selected from the group consisting of N, CR A , CR D , and CR S ; Z 1 and Z 2 are independently of each other selected from the group consisting of N, CR A and CR D ; R A is a group with −M-effect; R D is a group with +M-effect; and R S is a sterically demanding group, with the provision that the compound of general formula (I) comprises at least one group CR A and at least one group CR D .

First claim

The invention claimed is:

1. A compound
selected from the group consisting of

wherein
R A wherein at each occurrence R A is independently of each other selected from the group consisting of fluoroalkyl, F, BR 1 2 , B(OR 1 ) 2 , CHO, C(═O)R 1 , C(═O)OR 1 , C(═O)N(R 1 ) 2 , CR 1 ═C(CN) 2 , N 3 , NO 2 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , heteroaryl, heteroaryl substituted with one or more electron withdrawing groups and aryl substituted with one or more electron withdrawing groups, wherein the electron withdrawing groups are selected from the group consisting of fluoroalkyl, F, B(OR 1 ) 2 , CHO, C(═O)R 1 , CN, C(═O)OR 1 , C(═O)N(R 1 ) 2 , NO 2 , P(═O)(R 1 ) 2 , S(═O)R 1 , and S(═O) 2 R 1 ;
R D is independently of each other of general formula (N-a)
Ar 1′ ) m —NR 1 2   (N-a)

wherein
Ar 1′ is a substituted or unsubstituted aromatic with 6 to 30 aromatic ring atoms, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms;
m is 0 or 1;
and
two R S together form a five-membered ring,

wherein two groups R S together form a five-membered ring of the following formulae (II-A)

A 1 and A 3 are at each occurrence independently selected from the group consisting of C(R 3 ) 2 , O, S, NR 3 and C(═O);
A 2 is at each occurrence independently selected from the group consisting of C(R 1 ) 2 , O, S, NR 3 and C(═O); and in case two groups A 2 are adjacent to each other, A 2 -A 2 may also be selected from the group consisting of ortho-linked arylene- or heteroarylene-group with 5 to 14 aromatic ring atoms, each of which may independently of the other be substituted with R 2 as defined above;
R 1 is at each occurrence independently selected from the group consisting of 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 , OH, SH, linear alkyl-, alkoxy- or thioalkyl-group with 1 to 20 C-atoms or a branched or cyclic alkyl-, alkoxy- or thioalkyl-group with 3 to 20 C-atoms or a alkenyl- or alkinyl-group with 2 to 20 C-atoms, wherein the group may be substituted with one or more of groups R 2 and wherein one or more CH 2 -groups in the group may be 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 —, NR 2 , P(═O)(R 2 ), O, S, SO or SO 2 , and wherein one or more H-atoms in the group may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , or an aryloxy- or heteroaryloxy-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , or an aralkyl- or heteroaralkyl-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , wherein two or more groups R 2 may be linked with each other and form an aliphatic or aromatic or heteroaromatic ring;
R 2 is at each occurrence independently selected from the group consisting of H, D, F, alkyl having from 1 to 20 C-atoms, aromatic groups having from 1 to 20 aromatic carbon atoms and heteroaromatic groups having from 1 to 20 aromatic ring atoms, wherein the aromatic groups and the heteroaromatic groups may be substituted with an alkyl having from 1 to 20 carbon atoms; and
R 3 is at each occurrence independently selected from the group consisting of F, linear alkyl- or alkoxy-group with 1 to 20 C-atoms, a branched or cyclic alkyl- or alkoxy-group with 3 to 20 C-atoms, each of which may be substituted with one or more of groups R 2 , wherein 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, NR 2 , O, S or CONR 2 , and wherein one or more H-atom may be replaced with D or F, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may each be substituted with one or more of groups R 2 , or an aryloxy- or heteroaryloxy-group with 5 to 24 aromatic ring atoms, which can be substituted with one or more groups R 2 , or an aralkyl- or heteroaralkyl-group with 5 to 24 aromatic ring atoms, which can be substituted with one or more groups R 2 , wherein two R 2 bound to the same carbon atom may form an aliphatic or aromatic ring system and thus a spiro system; or R 3 can form together with a neighboring group R 1 or R 2 an aliphatic ring system,
provided that in A 1 -A 2 -A 3 no two heteroatoms are adjacent.

2. The compound according to claim 1 of the formula (I-e).

3. The compound according to claim 1 , wherein at each occurrence R D is
Ar 1 ) m —NAr 2 2   (N-b)

wherein
Ar 1 is a substituted or unsubstituted aromatic with 6 to 30 aromatic ring atoms, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms;
Ar 2 is a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 30 aromatic carbon atoms, wherein the two groups Ar 2 may be linked by a group Y, so that together with the N-atom of the NAr 2 2 -group, irrespective of any N-atoms that might be present in Ar 2 , a ring is formed;
Y is selected from the group consisting of a single bond, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , P(═S)R 1 , O, S, S═O and S(═O) 2 ; and
R 1 is at each occurrence independently selected from the group consisting of 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 , OH, SH, linear alkyl-, alkoxy- or thioalkyl-group with 1 to 20 C-atoms or a branched or cyclic alkyl-, alkoxy- or thioalkyl-group with 3 to 20 C-atoms or a alkenyl- or alkinyl-group with 2 to 20 C-atoms, wherein the group may be substituted with one or more of groups R 2 and wherein one or more CH 2 -groups in the group may be 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 , NR 2 , P(═O)(R 2 ), O, S, SO or SO 2 , and wherein one or more H-atoms in the group may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , or an aryloxy- or heteroaryloxy-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , or an aralkyl- or heteroaralkyl-group with 5 to 60 aromatic ring atoms, which can be substituted with one or more groups R 2 , wherein two or more groups R 2 may be linked with each other and form an aliphatic or aromatic or heteroaromatic ring;
R 2 is at each occurrence independently selected from the group consisting of H, D, F, alkyl having from 1 to 20 C-atoms, aromatic groups having from 1 to 20 aromatic carbon atoms and heteroaromatic groups having from 1 to 20 aromatic ring atoms, wherein the aromatic groups and the heteroaromatic groups may be substituted with an alkyl having from 1 to 20 carbon atoms; and
m is 0 or 1.

4. The compound according to claim 1 , wherein at each occurrence R D is independently of each other selected from the group consisting of groups of formula (N-b)
Ar 1 ) m —NAr 2 2   (N-b)

wherein
Ar 1 is a substituted or unsubstituted aromatic with 6 to 30 aromatic ring atoms, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms; and
NAr 2 2 is selected from the group consisting of aromatic amines, heteroaromatic amines, carbazoles, azacarbazoles, annealed carbazoles, annealed azacarbazoles, 5,10-dihydro-phenazaboranes, 9,10-dihy

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Parham Amir Hossain
• Pflumm Christof
• Jatsch Anja

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C07D307/87

  Benzo [c] furans; Hydrogenated benzo [c] furans · CPC title

• C07D491/107

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title