US2011068328A1PendingUtilityA1
Halogen-containing perylenetetracarboxylic acid derivatives and the use thereof
Est. expiryAug 17, 2027(~1.1 yrs left)· nominal 20-yr term from priority
C09B 5/62H10K 71/164H10K 85/6574H10K 71/311H10K 85/621H10K 85/654H10K 10/466H10K 85/653H10K 85/6572C09K 2211/1088C09K 11/06Y02P70/50Y02E10/549C09K 2211/1044C09K 2211/1029C09K 2211/1011
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Claims
Abstract
The invention relates to compounds of the formula (I) in which Y 1 and Y 2 are each O or, respectively, NR a or NR b , where R a and R b are each H or organyl; Z 1 to Z 4 are each O or S; R 11 to R 14 , R 21 to R 24 are each Cl, F; where 1 or 2 of the R 11 to R 14 , R 21 to R 24 radicals may also be CN and/or 1 R 11 to R 14 , R 21 to R 24 radical may be H; and where, when Y 1 is NR a , Z 1 or Z 2 may also be NR c , where R a and R c together are a bridging X group having from 2 to 5 atoms; and where, when Y 2 is NR b , Z 3 or Z 4 may also be NR d , where R b and R d together are a bridging X group having from 2 to 5 atoms; to a process for preparation thereof, and to their use as emitter materials, charge transport materials or exciton transport materials.
Claims
exact text as granted — not AI-modified1 . A compound represented by general formula (I)
in which
Y 1 is O or NR a where R a is hydrogen or an organyl radical,
Y 2 is O or NR b where R b is hydrogen or an organyl radical,
Z 1 , Z 2 , Z 3 and Z 4 are each O or S and
the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals are each chlorine and/or fluorine,
where 1 or 2 of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals may also be CN and/or 1 R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radical may be hydrogen, and
where, in the case that Y 1 is NR a , one of the Z 1 and Z 2 radicals may also be NR C , where the R a and R c radicals together are a bridging X group having from 2 to 5 atoms between the flanking bonds, and
where, in the case that Y 2 is NR b , one of the Z 3 and Z 4 radicals may also be NR d , where the R b and R d radicals together are a bridging X group having from 2 to 5 atoms between the flanking bonds.
2 . The compound according to claim 1 , wherein the compounds of the formula (I) are selected from compounds of the formula (I.A)
in which R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 each have one of the definitions given in claim 1 .
3 . The compound according to claim 1 , wherein the compounds of the formula (I) are selected from compounds of the formula (I.Ba)
in which R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 each have one of the definitions given in claim 1 , and R a and R b are each independently hydrogen or unsubstituted or substituted alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, bicycloalkyl, cycloalkenyl, heterocycloalkyl, aryl or heteroaryl.
4 . The compound according to claim 1 , wherein the compounds of the formula (I) are selected from compounds of the formulae (I.Bb1) and (I.Bb2)
in which R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 each have one of the definitions given in claim 1 , and X is a divalent bridging group having from 2 to 5 atoms between the flanking bonds.
5 . The compound according to claim 1 , wherein none of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals is hydrogen.
6 . The compound according to claim 5 , wherein the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals are all chlorine.
7 . The compound according to claim 5 , wherein the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals are all fluorine.
8 - 14 . (canceled)
15 . A process for preparing a compound represented by formula (I)
where R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 , Y 1 , Y 2 , Z 1 , Z 2 , Z 3 and Z 4 each have one of the definitions given in claim 1 ,
comprising
a) chlorinating a compound of the formula (II)
in which
R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 are each selected from hydrogen, Cl and CN, and Y 1 , Y 2 , Z 1 , Z 2 , Z 3 and Z 4 each have one of the definitions given in claim 1 ,
where at least one of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 radicals is hydrogen, from 0 to 7 of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 radicals are each Cl and from 0 to 2 of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 radicals are each CN,
to obtain a compound of the formula (I)
in which the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals are each chlorine, where 1 or 2 of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals may also be CN, and one of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals may be hydrogen.
16 . The process according to claim 15 , wherein the chlorinating of the compound of the formula (II) is brought about by reaction with chlorine in chlorosulfonic acid and in the presence of catalytic amounts of iodine.
17 . The process according to claim 15 , wherein the exchange of chlorine for fluorine on the compound of the formula (I) is brought about by reaction with an alkali metal fluoride under essentially anhydrous conditions.
18 . A compound of the general formula (I)
in which R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , R 24 , Y 1 , Y 2 , Z 1 , Z 2 , Z 3 and Z 4 each have one of the definitions given in claim 1 , excluding N,N′-dimethyl-heptachloroperylimide and N,N′-dimethyloctachloroperylimide.
19 - 21 . (canceled)
22 . A compound according to claim 18 , in which R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 are each fluorine, where 1 or 2 of the R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radicals may also be CN and/or 1 R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 radical may be hydrogen.
23 . An organic field-effect transistor comprising a substrate having at least one gate structure, a source electrode and a drain electrode, and at least one compound of the formula (I) as defined in claim 1 as an n-semiconductor.
24 . An organic solar cell comprising at least one compound of the formula (I) as defined in claim 1 .
25 . An OLED comprising at least one compound of the formula (I) as defined in claim 1 .
26 . A substrate having a multitude of organic field-effect transistors, wherein at least some of the field-effect transistors comprise at least one compound of the formula (I) as defined in claim 1 as an n-semiconductor.
27 . A semiconductor component comprising at least one substrate as defined in claim 26 .
28 . An emitter material in an organic OLED, comprising the compound defined in claim 1 .
29 . A light absorber comprising the compound defined in claim 1 .
30 . A fluorescent dye comprising the compound defined in claim 1 .
31 . The process according to claim 15 , further comprising subjecting the compound of the formula (I), obtained from said chlorinating, to a partial or full exchange of chlorine for fluorine.
32 . A method of emitting light comprising emitting light through a material comprising the compound according to claim 1 .
33 . A method of transporting a charge comprising conducting electrons through a material comprising the compound according to claim 1 .
34 . A method of transporting excitons, comprising conducting excited states along a material comprising the compound according to claim 1 .Join the waitlist — get patent alerts
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