Heterocyclic bridged biphenyls

Patent metadata

Field	Value
Publication number	US-9353065-B2
Application number	US-53188508-A
Country	US
Kind code	B2
Filing date	Mar 19, 2008
Priority date	Mar 29, 2007
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

The present invention relates to compounds of the formula (I), a process for their preparation and their use in organic light emitting diodes (OLEDs), especially as host for phosphorescent compounds. The hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or special characteristics of electroluminescent devices.

First claim

The invention claimed is:

1. A compound of the formula

wherein A is

R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently of each other hydrogen, F, or an organic substituent, or
R 1 and R 2 , R 4 and R 6 , R 2 and R 3 , R 5 and R 3 and/or R 5 and R 6 , which are adjacent to each other, together form an aromatic, or heteroaromatic ring, or ring system, which can optionally be substituted,
x is 0, or an integer of 1 to 5;
R 7 has the meaning of R 8 ,
R 8″ has the meaning of R 8 ,
p is 0, 1, 2, or 3,
the dotted line - - - indicates the bonding to the biphenyl unit,
R 8 and R 9 are independently of each other H, CN, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, 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, CN, or —CO—R 28 , or
R 8 and R 9 together form a group

wherein R 206′ , R 208′ , R 205 , R 206 , R 207 , R 208 , R 209 and R 210 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 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, 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 7 -C 25 aralkyl, CN, or —CO—R 28 ,
R 10 is 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 perfluoroalkyl, 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 —CO—R 28 ,
R 8′ and R 9′ are independently of each other H, CN, —COOR 27 ; —CONR 25 R 26 , C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, 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, CN, or —CO—R 28 ;
R 11 and R 14 are independently of each other hydrogen, F, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, 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, CN, or —CO—R 28 ,
R 12 , R 13 , R 15 and R 16 are independently of each other H, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 1 -C 18 perfluoroalkyl, 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, CN or —CO—R 28 ,
X is O, S, or NR 17 , wherein R 17 is C 6 -C 18 aryl; C 2 -C 20 heteroaryl; C 6 -C 18 aryl, or C 2 -C 20 heteroaryl, which are substituted by C 1 -C 18 alkyl, C 1 -C 18 perfluoroalkyl, —N(C 6 -C 18 aryl) 2 , or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
or two substituents R 1 and R 2 , R 4 and R 6 , R 11 and R 12 , and/or R 14 and R 16 , R 2 and R 3 , R 5 and R 6 , R 12 and R 13 , and/or R 15 and R 16 , which are adjacent to each other, together form a group

or two substituents R 15 and R 13 , and/or R 5 and R 3 , which are adjacent to each other, together form a group

wherein X 3 is O, S, C(R 119 )(R 120 ) or NR 17 , wherein R 17 is as defined above, R 105 , R 106 , R 107 , R 108 , R 106′ and R 108′ 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 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D,
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, 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 127 ,
D is —CO—; —COO—; —S—; —SO—; —SO 2 —; —O—; —NR 25 —; —SiR 30 R 31 —; —POR 32 —; —CR 23 ═CR 24 —; or —C≡C—; and
E is —OR 29 ; —SR 29 ; —NR 25 R 26 ; —COR 28 ; —COOR 27 ; —CONR 25 R 26 ; —CN; or halogen; G is E, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is interrupted by D, C 1 -C 18 perfluoroalkyl, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, wherein
R 23 , R 24 , R 25 and R 26 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—; or
R 25 and R 26 together form a five or six membered ring,
R 27 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 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—,
R 29 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 30 and R 31 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,
R 32 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,
Z 1 and Z 2 are independently of each other a group

wherein R 5″ is hydrogen, or has the meaning of R 6 ,
R 6″ , R 7″ , and R 9″ are independently of each other C 6 -C 18 aryl; which may optionally be substituted by G; or C 2 -C 20 heteroaryl, which may optionally be substituted by G,

Assignees

• SCHäFER THOMAS
• Murer Peter
• Wendeborn Frédérique
• Schmidhalter Beat
• Bardon Kristina
• Ricci Andrea
• Pommerehne Joern
• Basf Se

Inventors

• SCHäFER THOMAS
• Murer Peter
• Wendeborn Frédérique
• Schmidhalter Beat
• Bardon Kristina
• Ricci Andrea
• Pommerehne Joern

Classifications

• H01L51/5012

  Electricity · mapped topic

• H01L51/0071

  Electricity · mapped topic

• C07D235/02 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• C07D263/52

  condensed with carbocyclic rings or ring systems · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title