Conveniently prepared naphthalene and perylene derivatives as building blocks for organic electronic materials and dyestuff

Patent metadata

Field	Value
Publication number	US-9382264-B2
Application number	US-201314424748-A
Country	US
Kind code	B2
Filing date	Aug 27, 2013
Priority date	Aug 30, 2012
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

The present invention provides the compounds of formulae (3) and (1), wherein n is 0 or 1, R 11 and R 12 are the same and are selected from the group consisting of CN, OR 300 , Si(R 301 ) 3 , NHR 302 , NR 303 R 304 , SR 305 and R 306 , or R 11 and R 12 together are selected from the group consisting of (a), (b), and (c) and X is Cl, Br or I, and a process for the preparation of compounds of formula (3) comprising the compounds of formula (1) as key intermediates.

First claim

The invention claimed is:

1. A process for the preparation of compounds of formula

wherein
n is 0 or 1,
R 11 and R 12 are the same and are selected from the group consisting of CN, OR 300 , Si(R 301 ) 3 , NHR 302 , NR 303 R 304 , SR 305 and R 306 ,
wherein
R 300 , R 301 , R 302 , R 303 , R 304 , R 305 and R 306 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3000 R 3001 , O—R 3002 and S—R 3003 and
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3004 R 3005 , O—R 3006 and S—R 3007 ,
wherein R 3000 , R 3001 , R 3002 , R 3003 , R 3004 , R 3005 , R 3006 and R 3007 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 11 and R 12 together are selected from the group consisting of

wherein
L 1 and L 2 are C 1-6 -alkylene, C 6-14 -arylene, or C 1-6 -alkylene-C 6-14 -arylene-C 1-6 -alkylene, R 25 is H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3010 R 3011 , O—R 3012 and S—R 3013 , and
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3014 R 3015 , O—R 3016 and S—R 3017 ,
wherein R 3010 , R 3011 , R 3012, R 3013 , R 3014 , R 3015 , R 3016 and R 3017 are the same or different and are C 1-10 -alkyl or phenyl,

L 3 is a direct bond, C 1-6 -alkylene, C 6-14 -arylene, or C 1-6 -alkylene-C 6-14 -arylene-C 1-6 -alkylene,
and
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R 310 , OR 311 , SR 312 , OC(O)R 313 and C(O)OR 314 ,
wherein R 310 , R 311 , R 312 , R 313 and R 314 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3020 R 3021 , O—R 3022 , S—R 3023 , NO 2 , CN and halogen,
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3024 R 3025 , O—R 3026 , S—R 3027 , NO 2 , CN and halogen,
wherein R 3020 , R 3021 , R 3022 , R 3023 , R 3024 , R 3025 , R 3026 and R 3027 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 17 and R 19 , respectively, R 18 and R 20 together are

which process comprises the step of treating a compound of formula

wherein
n has the meaning as depicted for formula (3),
R 9 and R 10 are the same or different and are COOH or COOR 200 , wherein R 200 is C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 2000 R 2001 , O—R 2002 and S—R 2003 ,
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 2004 R 2005 , O—R 2006 and S—R 2007 ,
wherein R 2000 , R 2001 , R 2002 and R 2003 , R 2004 , R 2005 , R 2006 and R 2007 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 9 and R 10 together are

and
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R 200 , OR 201 , SR 202 , OC(O)R 203 and C(O)OR 204 ,
wherein R 200 , R 201 , R 202 , R 203 and R 204 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 2010 R 2011 , O—R 2012 , S—R 2013 , NO 2 , CN and halogen,
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 2014 R 2015 , O—R 2016 , S—R 2017 , NO 2 , CN and halogen,
wherein R 2010 , R 2011 , R 2012 , R 2013 , R 2014 , R 2015 , R 2016 and R 2017 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 3 and R 5 , respectively, R 4 and R 6 together are

a) with MOH, wherein M is at least one alkali metal selected from the group consisting of Na, K and Li, N(R 400 R 401 R 402 R 403 ), P(R 400 R 401 R 402 R 403 ) or hexa(C 1-10 -alkyl)guanidinium,
wherein R 400 , R 401 , R 402 and R 403 are the same or different and are selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl and C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with phenyl,
C 6-14 -aryl may be substituted with C 1-10 -alkyl,

and
b) at least one X-donor selected from the group consisting of X—X, X-succinimide and N,N′-di-X-isocyanuric acid, wherein X is Cl, Br or I,
in order to obtain a compound of formula

wherein
X has the meaning as depicted for the X-donor,
n has the meaning as depicted for formula (3),
and
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meaning as depicted for formula (2).

2. The process of claim 1 , wherein R 9 and R 10 together are

3. The process of claim 1 , wherein n is 1.

4. The process of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and are selected from the group consisting of H, Cl, Br, I, CN and OR 201 ,
wherein R 201 is C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 2010 R 2011 , O—R 2012 , S—R 2013 , NO 2 , CN and halogen,
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 2014 R 2015 , O—R 2016 , S—R 2017 , NO 2 , CN and halogen, wherein R 2010 , R 2011 , R 2012 , R 2013 , R 2014 , R 2015 , R 2016 and R 2017 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 3 and R 5 , respectively, R 4 and R 6 together are

5. The process of claim 1 , wherein

Assignees

• Basf Se
• Max Planck Gesellschaft

Inventors

• Gessner Thomas
• Reichelt Helmut
• Zagranyarski Yulian
• Chen Long
• Li Chen
• Muellen Klaus

Classifications

• C07C211/42

  with six-membered aromatic rings being part of the condensed ring systems · CPC title

• C09B3/14

  Perylene derivatives · CPC title

• C09B5/026

  only S-containing hetero rings · CPC title

• C09B3/18

  Preparation from starting materials already containing the perylene nucleus · CPC title

• C07C41/16

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title