Benzimidazo[1,2-A]benzimidazole derivatives for electronic applications

Patent metadata

Field	Value
Publication number	US-9620724-B2
Application number	US-201314413736-A
Country	US
Kind code	B2
Filing date	Jul 8, 2013
Priority date	Jul 10, 2012
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

A compound of the general formula

a process for the production of the compound and its use in electronic devices, especially electroluminescent devices. Improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices are provided when the compound of formula I is used as host material for phosphorescent emitters in electroluminescent devices.

First claim

The invention claimed is:

1. A process for the preparation of a compound of formula

comprising halogenating a compound of formula

wherein
X 3 is Cl, Br, or I;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of H; a C 1 -C 25 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C 6 -C 24 aryl group, which can optionally be substituted by G; and a C 2 -C 30 heteroaryl group, which can optionally be substituted by G;
X 1 is a group of formula -(A 1 ) o -(A 2 ) p -(A 3 ) q -(A 4 ) r -R 16′ ;
o is 0 or 1, p is 0 or 1, q is 0 or 1, r is 0 or 1,
A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of a C 6 -C 24 arylen group, which can optionally be substituted by G, and a C 2 -C 30 heteroarylen group, which can optionally be substituted by G; wherein
the groups A 1 , A 2 , A 3 and A 4 may be interrupted by a group —(SiR 17 R 18 )—;
R 16′ is a C 6 -C 24 aryl group, which can optionally be substituted by G; or a C 2 -C 30 heteroaryl group, which can optionally be substituted by G;
R 17 and R 18 are independently selected from the group consisting of a C 1 -C 25 alkyl group, and a C 6 -C 24 aryl group, which can optionally be substituted by a C 1 -C 25 alkyl group;
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—,
E is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, or halogen,
G is E; a C 1 -C 18 alkyl group; a C 6 -C 24 aryl group; a C 6 -C 24 aryl group, which is substituted by F, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by O; a C 2 -C 30 heteroaryl group; or a C 2 -C 30 heteroaryl group, which is substituted by F, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by O;
R 63 and R 64 are independently selected from the group consisting of H, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; and C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are independently selected from the group consisting of a C 6 -C 18 aryl group; a C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; and a C 1 -C 18 alkyl group, which is interrupted by —O—; or
R 65 and R 66 together form a five or six membered ring,
R 67 is a C 6 -C 18 aryl group; a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; or a C 1 -C 18 alkyl group, which is interrupted by —O—,
R 68 is H; a C 6 -C 18 aryl group; a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; or a C 1 -C 18 alkyl group, which is interrupted by —O—,
R 69 is a C 6 -C 18 aryl; a C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; or a C 1 -C 18 alkyl group, which is interrupted by —O—,
R 70 and R 71 are independently selected from the group consisting of a C 1 -C 18 alkyl group, a C 6 -C 18 aryl group, and a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl, and
R 72 is a C 1 -C 18 alkyl group, a C 6 -C 18 aryl group, or a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl.

2. A compound of formula

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of H; a C 1 -C 25 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C 6 -C 24 aryl group, which can optionally be substituted by G; and a C 2 -C 30 heteroaryl group, which can optionally be substituted by G;
X 1 is a group of formula -(A 1 ) o -(A 2 ) p -(A 3 ) q -(A 4 ) r -R 16″ ,
o is 0 or 1, p is 0 or 1, q is 0 or 1, r is 0 or 1,
or is a group of the formula A 1 -(A 2 ) p -(A 3 ) q -(A 4 ) r -R 16″ ,
X 3 is a group of formula -(A 5 ) v -(A 6 ) s -(A 7 ) t -(A 8 ) u -R 15′ , wherein v is 0 or 1, s is 0 or 1, t is 0 or 1, u is 0 or 1, wherein R 15′ and R 16″ are independently selected from the group consisting of Cl; Br; I; ZnX 12 , wherein X 12 is a halogen atom; —SnR 207 R 208 R 209 ; wherein R 207 , R 208 and R 209 are identical or different and are H or C 1 -C 8 alkyl, wherein two radicals optionally form a common ring and these radicals are optionally branched or unbranched; —B(OH) 2 ; —B(OY 1 ) 2 ;

—BF 4 Na; and —BF 4 K, wherein each Y 1 is independently a C 1 -C 18 alkyl group and each Y 2 is independently in each occurrence a C 2 -C 10 alkylene group, and Y 13 and Y 14 are independently selected from the group consisting of hydrogen and a C 1 -C 18 alkyl group,
A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of a C 6 -C 24 arylen group, which can optionally be substituted by G, and a C 2 -C 30 heteroarylen group, which can optionally be substituted by G; wherein
the groups A 1 , A 2 , A 3 and A 4 may be interrupted by a group —(SiR 17 R 18 )—;
A 5 , A 6 , A 7 and A 8 are independently selected from the group consisting of a C 6 -C 24 arylen group, which can optionally be substituted by G, and a C 2 -C 30 heteroarylen group, which can optionally be substituted by G; wherein
the groups A 5 , A 6 , A 7 and A 8 may be interrupted by a group —(SiR 17 R 18 )—;
R 16′ is a C 6 -C 24 aryl group, which can optionally be substituted by G; or a C 2 -C 30 heteroaryl group, which can optionally be substituted by G;
R 17 and R 18 are independently selected from the group consisting of a C 1 -C 25 alkyl group, and a C 6 -C 24 aryl group, which can optionally be substituted by a C 1 -C 25 alkyl group;
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—,
E is —OR 69 , —SR 69 , —NR 65 R 66 ; —COR 68 , —COOR 67 , —CONR 65 R 66 ; —CN, or halogen,
G is E; a C 1 -C 18 alkyl group; a C 6 -C 24 aryl group; a C 6 -C 24 aryl group, which is substituted by F, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by 0; a C 2 -C 30 heteroaryl group; or a C 2 -C 30 heteroaryl group, which is substituted by F, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by O;
R 63 and R 64 are independently selected from the group consisting of H, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; and C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are independently selected from the group consisting of a C 6 -C 18 aryl group; a C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; and a C 1 -C 18 alkyl group, which is interrupted by —O—; or
R 65 and R 66 together form a five or six membered ring, R 67 is a C 6 -C 18 aryl group; a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; or a C 1 -C 18 alkyl group, which is interrupted by —O—,
R 68 is H; a C 6 -C 18 aryl group; a C 6 -C 18 aryl group, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl group; or a C 1 -C 18 alkyl group, which is interrupted by —O—,
R 69 is a C 6 -C 18 aryl; a C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; a C 1 -C 18 alkyl gro

Assignees

• Udc Ireland Ltd

Inventors

• Schaefer Thomas
• Benedito Flavio Luiz
• Heinemeyer Ute
• Langer Nicolle
• Wolleb Heinz
• Figueira Duarte Teresa Marina
• Watanabe Soichi
• Lennartz Christian
• Wagenblast Gerhard
• Wolleb Annemarie
• Bardon Kristina

Classifications

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• H05B33/00

  Electroluminescent light sources · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• G03G5/0661

  in different ring systems, each system containing at least one hetero ring · CPC title

• Y02E10/549

  Organic PV cells · CPC title