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US 9,382,264 B2Granted
Conveniently prepared naphthalene and perylene derivatives as building blocks for organic electronic materials and dyestuff
AssigneesBASF SE, Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
InventorsThomas Gessner, Helmut Reichelt, Yulian Zagranyarski, Long Chen, Chen Li, Klaus Muellen
Life of this patent
Estimating the term…
Abstract
The present invention provides the compounds of formulae (3) and (1), wherein n is 0 or 1, R11 and R12 are the same and are selected from the group consisting of CN, OR300, Si(R301)3, NHR302, NR303R304, SR305 and R306, or R11 and R12 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.
Claims12
A process for the preparation of compounds of formula
- wherein
- n is 0 or 1,
- R11 and R12 are the same and are selected from the group consisting of CN, OR300, Si(R301)3, NHR302, NR303R304, SR305 and R306,
- wherein
- R300, R301, R302, R303, R304, R305 and R306 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl and C2-20-alkynyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3000R3001, O—R3002 and S—R3003 and
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3004R3005, O—R3006 and S—R3007,
- wherein R3000, R3001, R3002, R3003, R3004, R3005, R3006 and R3007 are the same or different and are C1-10-alkyl or phenyl,
- or
- R11 and R12 together are selected from the group consisting of
- wherein
- L1 and L2 are C1-6-alkylene, C6-14-arylene, or C1-6-alkylene-C6-14-arylene-C1-6-alkylene, R25 is H, C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3010R3011, O—R3012 and S—R3013, and
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3014R3015, O—R3016 and S—R3017,
- wherein R3010, R3011, R3012, R3013, R3014, R3015, R3016 and R3017 are the same or different and are C1-10-alkyl or phenyl,
- L3 is a direct bond, C1-6-alkylene, C6-14-arylene, or C1-6-alkylene-C6-14-arylene-C1-6-alkylene,
- and
- R15, R16, R17, R18, R19, R20, R21 and R22 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R310, OR311, SR312, OC(O)R313 and C(O)OR314,
- wherein R310, R311, R312, R313 and R314 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3020R3021, O—R3022, S—R3023, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3024R3025, O—R3026, S—R3027, NO2, CN and halogen,
- wherein R3020, R3021, R3022, R3023, R3024, R3025, R3026 and R3027 are the same or different and are C1-10-alkyl or phenyl,
- or
- R17 and R19, respectively, R18 and R20 together are
- which process comprises the step of treating a compound of formula
- wherein
- n has the meaning as depicted for formula (3),
- R9 and R10 are the same or different and are COOH or COOR200, wherein R200 is C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR2000R2001, O—R2002 and S—R2003,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR2004R2005, O—R2006 and S—R2007,
- wherein R2000, R2001, R2002 and R2003, R2004, R2005, R2006 and R2007 are the same or different and are C1-10-alkyl or phenyl,
- or
- R9 and R10 together are
- and
- R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R200, OR201, SR202, OC(O)R203 and C(O)OR204,
- wherein R200, R201, R202, R203 and R204 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR2010R2011, O—R2012, S—R2013, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR2014R2015, O—R2016, S—R2017, NO2, CN and halogen,
- wherein R2010, R2011, R2012, R2013, R2014, R2015, R2016 and R2017 are the same or different and are C1-10-alkyl or phenyl,
- or
- R3 and R5, respectively, R4 and R6 together are
- a) with MOH, wherein M is at least one alkali metal selected from the group consisting of Na, K and Li, N(R400R401R402R403), P(R400R401R402R403) or hexa(C1-10-alkyl)guanidinium,
- wherein R400, R401, R402 and R403 are the same or different and are selected from the group consisting of H, C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl and C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with phenyl,
- C6-14-aryl may be substituted with C1-10-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
- R1, R2, R3, R4, R5, R6, R7 and R8 have the meaning as depicted for formula (2).
56 more elements
Compounds of formula
- wherein
- X is Cl, Br or I,
- n is 1,
- and
- R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R200, OR201, SR202, OC(O)R203 and C(O)OR204, wherein R200, R201, R202, R203 and R204 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR2010R2011, O—R2012, S—R2013, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR2014R2015, O—R2016, S—R2017, NO2, CN and halogen,
- wherein R2010, R2011, R2012, R2013, R2014R2015, R2016 and R2017 are the same or different and are C1-10-alkyl or phenyl,
- or
- R3 and R5, respectively, R4 and R6 together are
- with the proviso
- that if n is 1 and X is Cl or Br, R1, R2, R3, R4, R5, R6, R7 and R8 are not H;
- and
- wherein R1, R2, R7 and R8 are H, and R3, R4, R5 and R6 are the same or different and are selected from the group consisting of F, Cl, Br, I, CN, R200, OR201, SR202, OC(O)R203 and C(O)OR204,
- wherein R200, R201, R202, R203 and R204 are C1-20-alkyl, C2-20-alkenyl, C7-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR2010R2011, O—R2012, S—R2013, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR2014R2015, O—R2016, S—R2017, NO2, CN and halogen,
- wherein R2010, R2011, R2012, R2013, R2014, R2015, R2016 and R2017 are the same or different and are C1-10-alkyl or phenyl,
- or
- R3 and R5, respectively, R4 and R6 together are
19 more elements
Compounds of formula
- wherein
- n is 1,
- R11 and R12 are the same and are selected from the group consisting of CN, OR300, Si(R301)3, NHR302, NR303R304, SR305 and R306
- wherein
- R300, R301, R302, R303, R304, R305 and R306 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3000R3001, O—R3002 and S—R3003 and
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3004R3005, O—R3006 and S—R3007,
- wherein R3000, R3001, R3002, R3003, R3004, R3005, R3006 and R3007 are the same or different and are C1-10-alkyl or phenyl,
- or
- R11 and R12 together are selected from the group consisting of
- wherein
- L1 and L2 are C1-6-alkylene, C6-14-arylene, or C1-6-alkylene-C6-14-arylene-C1-6-alkylene,
- R25 is H, C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3010R3011, O—R3012 and S—R3013, and
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3014R3015, O—R3016 and S—R3017,
- wherein R3010, R3011, R3012, R3013, R3014, R3015, R3016 and R3017 are the same or different and are C1-10-alkyl or phenyl,
- L3 is a direct bond, C1-6-alkylene, C6-14-arylene, or C1-6-alkylene-C6-14-arylene-C1-6-alkylene,
- and
- R15, R16, R17, R18, R19, R20, R21 and R22 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R310, OR311, SR312, OC(O)R313 and C(O)OR314,
- wherein R310, R311, R312, R313 and R314 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3020R3021, O—R3022, S—R3023, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3024R3025, O—R3026, S—R3027, NO2, CN and halogen,
- wherein R3020, R3021, R3022, R3023, R3024, R3025, R3026 and R3027 are the same or different and are C1-10-alkyl or phenyl,
- or
- R17 and R19, respectively, R18 and R20 together are
- with the proviso that if
- R11 and R12 are both CN or phenyl, and R15, R16, R18, R19, R20, R21 and R22 are H, then R17 and R20 are not Br;
- and
- wherein
- R15, R16, R21 and R22 are H, and R17, R18, R19 and R20, are the same or different and are selected from the group consisting of F, Cl, Br, I, CN, R310, OR311, R312, OC(O)R313 and C(O)OR314,
- wherein R310, R311, R312, R313 and R314 are C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-8-cycloalkyl or C6-14-aryl,
- wherein
- C1-20-alkyl, C7-20-alkenyl, C2-20-alkynyl and C5-8-cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR3020R3021, O—R3022, S—R3023, NO2, CN and halogen,
- C6-14-aryl may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, NR3024R3025, O—R3026, S—R3027, NO2, CN and halogen,
- wherein R3020, R3021, R3022, R3023, R3024, R3025, R3026 and R3027 are the same or different and are C1-10-alkyl or phenyl,
- or
- R17 and R19, respectively, R18 and R20 together are
37 more elements
Dependencies are inferred from the claim text.