Phenanthro[9, 10-B]furans for electronic applications

Patent metadata

Field	Value
Publication number	US-9079872-B2
Application number	US-201113252482-A
Country	US
Kind code	B2
Filing date	Oct 4, 2011
Priority date	Oct 7, 2010
Publication date	Jul 14, 2015
Grant date	Jul 14, 2015

Abstract

The present invention relates to an electronic device, especially an electroluminescent devices, comprising a compound of the formula

especially as host for phosphorescent compounds. The hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein R 1 and R 2 are a group of formula

R 7 , R 8 and R 9 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkyl which is interrupted by O;
wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula -NA 1 A 1′ , or a group

A 1 and A 1′ are independently of each other

A 1 and A 1′ together with a nitrogen atom to which they are bonded form a heteroaromatic ring, or form a structure

 m′ is 0, 1, or 2; m1 can be same or different at each occurrence and is 0, 1, 2, 3, or 4;
R 116 , R 117 and R 117′ are independently of each other H, halogen, —CN, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, —C(═O)—R 77 , —C(═O)OR 78 , or —C(═O)NR 75 R 76 ,
R 75 , R 76 and R 78 are independently of each other 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; or C 1 -C 18 alkyl which is interrupted by —O—,
R 77 is 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; or C 1 -C 18 alkyl which is interrupted by —O—,
BU is

R 119 and R 120 are independently of each other C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 119 and R 120 together form a group of formula ═CR 121 R 122 , wherein
R 121 and R 122 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 119 and R 120 together form a five or six membered ring selected from the group consisting of cyclohexyl and cyclopentyl, which optionally can be substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 7 -C 25 aralkyl, or —C(═O)—R 28 ,
R 28 is 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; or C 1 -C 18 alkyl which is interrupted by —O—,
D is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—, and
E is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, or halogen,
G is E, or C 1 -C 18 alkyl,
R 63 and R 64 are independently of each other 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; or C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are independently of each other 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; or C 1 -C 18 alkyl which is interrupted by —O—;
R 67 is 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; or C 1 -C 18 alkyl which is interrupted by —O—,
R 68 is 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; or C 1 -C 18 alkyl which is interrupted by —O—,
R 69 is 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; or C 1 -C 18 alkyl which is interrupted by —O—,
R 70 and R 71 are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and
R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl;
R 41 can be the same or different at each occurrence and is C1, F, CN, NR 45 R 45′ , a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, a C 1 -C 25 alkoxy group, wherein one or more hydrogen atoms can be replaced by F, a C 6 -C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 ;
R 45 and R 45′ are independently of each other a C 1 -C 25 alkyl group, a C 4 -C 18 cycloalkyl group, wherein one or more hydrogen atoms can be replaced by F, a C 6 - C 24 aryl group, or a C 6 -C 24 aryloxy group, wherein one or more carbon atoms can be replaced by O, S, or N, and/or which can be substituted by one or more non-aromatic groups R 41 ;
-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

wherein R 116′ is same as R 116 ;
or
-L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula

R 124 , R 125 and R 126 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 fluoroalkyl, C 6 -C 24 aryl, which can optionally be substituted by G, C 2 -C 20 heteroaryl, which can optionally be substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl.

2. The compound according to claim 1 , which is a compound of formula

wherein R 1 and R 2 are a group of formula

R 7 , R 8 and R 9 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkyl which is interrupted by O;
wherein -L 3 -X 1 and -L 4 -X 2 are independently of each other a group of formula -NA 1 A 1′ , or a group

A 1 and A 1′ are independently of each other

Assignees

• Schaefer Thomas
• Schildknecht Christian
• Murer Peter
• Lennartz Christian
• Langer Nicolle
• Wagenblast Gerhard
• Metz Stefan
• Basf Se

Inventors

• Schaefer Thomas
• Schildknecht Christian
• Murer Peter
• Lennartz Christian
• Langer Nicolle
• Wagenblast Gerhard
• Metz Stefan

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D307/77 Primary

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title