Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-10487262-B2
Application number	US-201615560575-A
Country	US
Kind code	B2
Filing date	Feb 26, 2016
Priority date	Mar 25, 2015
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

The present invention relates to a compound of formula (I) or (II), which is suitable for use as functional material in an electronic device, in particular as emitter material in an organic electroluminescent device.

First claim

The invention claimed is:

1. A compound of formula (I) or formula (II):

wherein
X is selected from the group consisting of C(R 1 ) 2 , Si(R 1 ) 2 , Ge(R 1 ) 2 , O, S, NR 1 , and Se;
V is, on each occurrence, identically or differently, selected from the group consisting of N or CR 2 ;
Ar 1 and Ar 2
 are, identically or differently, selected from group consisting of formulae (3) through (8):

wherein
Ar 1 and Ar 2

 are connected to the 5-membered ring of formula (I) or (II) via one group Y of one of formulae (3) through (8);
Y is C if the 5-membered ring of formula (I) or (II) is bonded to Y and is CR 3 or N if the 5-membered ring of formula (I) or (II) is not bonded to the group Y;
E is, on each occurrence, identically or differently, a divalent bridge selected from the group consisting of 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 ;
W is C if a bridge E is bonded to the group W and is CR 3 or N if no bridge E is bonded to the group W;
R 1 , R 2 , and R 3
is, on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein these groups are each optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in these groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , and wherein two or more substituents R 1 , two or more substituents R 2 , or two or more substituents R 3 are optionally linked to one another so as to define a ring;

R 4 is on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where these groups are each optionally substituted by one or more radicals R 5 and wherein one or more CH 2 groups in these groups are optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 5 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 , and wherein two or more radicals R 4 are optionally linked to one another so as to define a ring;
R 5 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F; and
a, b, c, d, e, and f

 are, on each occurrence, identically or differently, 0 or 1, with the proviso that a +b =1 or 2, c +d =1 or 2, and e +f =1 or 2, wherein when a =0, or b =0, or c =0, or d 0, or e =0, or f=0, in each case the corresponding bridge X is not present.

2. The compound of claim 1 , wherein a +b =1, c +d =1, and e +f =1 or 2.

3. The compound of claim 1 , wherein X is selected from C(R 1 ) 2 , Si(R 1 ) 2 , O, or S.

4. The compound of claim 1 , wherein E is, on each occurrence, identically or differently, a divalent bridge selected from the group consisting of C(R 1 ) 2 , Si(R 1 ) 2 , O, S, and N(R 1 ), more preferably C(R 1 ) 2 .

5. The compound of claim 1 , wherein E is C(R 1 ) 2 .

6. The compound of claim 1 , wherein V is CR 2 .

7. The compound of claim 1 , wherein
Ar 1 and Ar 2
 are, identically or differently, selected from one of formulae (3-1) through (8-3):

8. The compound of claim 1 , wherein
Ar 1 and Ar 2
 are, identically or differently, selected from one of the following formulae (3-1-1) to (8-3-2):

 wherein the dashed lines represent the bonds to the 5-membered ring of formula (I) or (II).

9. The compound of claim 1 , wherein it is a compound of formula (I) or formula (II):

wherein
X is C(R 1 ) 2 , Si(R 1 ) 2 , O, or S;
V is CR 2 ;
Ar 1 and A 2
 is, identically or differently, selected from the group consisting of formulae (3-1) through (8-3):

 wherein E is C(R 1 ) 2 and Y is C if the 5-membered ring of formula (I) or (II) is bonded to Y and CR 3 otherwise;
R 1 , R 2 , and R 3
 is on each occurrence, identically or differently, H, D, F, CN, Si(R 4 ) 3 , N(R 4 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, where these groups are each optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in these groups are optionally replaced by —C≡C—, —R 4 C═CR 4 —, Si(R 4 ) 2 , C═O, C═NR 4 ,—NR 4 —, —O—, —S—, —C(═O)O—, or —C(═O)NR 4 —, an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 4 , and wherein two radicals R 1 are optionally linked to one another so as to define a ring, two radicals R 2 are optionally linked to one another so as to define a ring, or two radicals R 3 are optionally linked to one another so as to define a ring; and
R 4 is on each occurrence, identically or differently, H, D, F, CN, Si(R 5 ) 3 , N(R 5 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10

Assignees

• Merck Patent Gmbh

Inventors

• Burkhart Beate
• Heil Holger
• Rodriguez Lara-Isabel
• Meyer Sebastian
• Darsy Amandine
• Linge Rouven

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D333/08

  Hydrogen atoms or radicals containing only hydrogen and carbon atoms · CPC title

• C07D307/36

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D207/323

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms · CPC title