TRANSMITTER FOR TRANSMITTING DATA AND FOR EMITTING ELECTROMAGNETIC RADIATION IN THE VISIBLE SPECTRAL RANGE AND DATA TRANSMISSION SYSTEM

Abstract

The present invention relates to a transmitter for transmitting data and for emitting electromagnetic radiation in the visible spectral range, wherein the transmitter comprises a) a radiation source for generating and emitting first electromagnetic radiation, b) a modulator being adapted to modulate the first electromagnetic radiation depending on the data to be transmitted generating modulated first electromagnetic radiation, and c) a frequency converter for converting at least a part of the modulated first electromagnetic radiation into modulated second electromagnetic radiation, said modulated second electromagnetic radiation being different from the modulated first electromagnetic radiation, wherein the frequency converter comprises a polymeric matrix material comprising at least one organic fluorescent colorant. Furthermore, the invention relates to an illumination device comprising such transmitter. Moreover, the invention relates to a data transmission system comprising such a transmitter as well as a receiver and a data analyzer.

Claims

1: A transmitter for transmitting data and for emitting electromagnetic radiation in a visible spectral range, said transmitter comprising: a radiation source for generating and emitting a first electromagnetic radiation and a modulator adapted to modulate the first electromagnetic radiation depending on the data to be transmitted and generate a modulated first electromagnetic radiation, wherein the transmitter further comprises a frequency converter for converting at least a part of the modulated first electromagnetic radiation into a modulated second electromagnetic radiation, said modulated second electromagnetic radiation being different from the modulated first electromagnetic radiation, wherein the frequency converter comprises a polymeric matrix material and at least one organic fluorescent colorant B selected from: (B1) a naphthoylbenzimidazole compound of formula (I) ##STR00114## wherein at least one of the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently or each other is aryl which comprises one, two or three cyano groups and 0, 1, 2, 3 or 4 substituents R.sup.Ar and the remaining radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently of each other are selected from hydrogen or aryl which is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R.sup.Ar, where R.sup.Ar independently of each other and independently of each occurrence is selected from halogen, C.sub.1-C.sub.30-alkyl, C.sub.2-C.sub.30-alkenyl, C.sub.2-C.sub.30-alkynyl, where the three latter radicals are unsubstituted or comprise one or more R.sup.a groups, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, where the two latter radicals are unsubstituted or comprise one or more R.sup.b groups, aryl or heteroaryl, where the two latter radicals are unsubstituted or comprise one or more R.sup.c groups, where R.sup.a independently of each other and independently of each occurrence is selected from cyano, halogen, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl are unsubstituted or bear one or more R.sup.b1 groups, and where aryl and heteroaryl are unsubstituted or bear one or more R.sup.b1 groups; R.sup.b independently of each other and independently of each occurrence is selected from cyano, halogen, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl are unsubstituted or bear one or more R.sup.b1 groups, and where aryl and heteroaryl are unsubstituted or bear one or more R.sub.c1 groups; R.sup.c independently of each other and independently of each occurrence is selected from cyano, halogen, C.sub.1-C.sub.18-alkyl, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl are unsubstituted or bear one or more R.sup.b1 groups, and where aryl and heteroaryl are unsubstituted or bear one or more R.sup.c1 groups; R.sup.b1 independently of each other and independently of each occurrence is selected from halogen, C.sub.1-C.sub.18-alkyl or C.sub.1-C.sub.18-haloalkyl, R.sup.c1 independently of each other and independently of each occurrence is selected from halogen, C.sub.1-C.sub.18-alkyl or C.sub.1-C.sub.18-haloalkyl; and mixtures thereof; (B2) a cyanated naphthoylbenzimidazole compound of formula (II) ##STR00115## wherein R.sup.21, R.sup.22, R.sup.23, R.sup.24, R.sup.25, R.sup.26, R.sup.27, R.sup.28, R.sup.29 and R.sup.210 are each independently hydrogen, cyano or aryl which is unsubstituted or has one or more identical or different substituents R.sup.2Ar, where each R.sup.2Ar is independently selected from cyano, hydroxyl, mercapto, halogen, C.sub.1-C.sub.20-alkoxy, C.sub.1-C.sub.20-alkylthio, nitro, NR.sup.2Ar2R.sup.2Ar3, NR.sup.2Ar2COR.sup.2Ar3, CONR.sup.2Ar2R.sup.2Ar3, SO.sub.2NR.sup.2Ar2R.sup.2Ar3, COOR.sup.2Ar2, SO.sub.3R.sup.2Ar2, C.sub.1-C.sub.30-alkyl, C.sub.2-C.sub.30-alkenyl, C.sub.2-C.sub.30-alkynyl, where the three latter radicals are unsubstituted or bear one or more R.sup.2a groups, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, where the two latter radicals are unsubstituted or bear one or more R.sup.2b groups, aryl, U-aryl, heteroaryl or U-heteroaryl, where the four latter radicals are unsubstituted or bear one or more R.sup.2b groups, where each R.sup.2a is independently selected from cyano, hydroxyl, mercapto, halogen, C.sub.1-C.sub.20-alkoxy, C.sub.1-C.sub.20-alkylthio, nitro, NR.sup.2Ar2R.sup.Ar3, NR.sup.2Ar2COR.sup.2Ar3, CONR.sup.2Ar2R.sup.Ar3, SO.sub.2NR.sup.2Ar2R.sup.Ar3, COOR.sup.2Ar2, SO.sub.3R.sup.2Ar2, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where the cycloalkyl, heterocyclyl, aryl and heteroaryl radicals are unsubstituted or bear one or more R.sup.2b groups, and where 2 radicals R.sup.2a bound at the same carbon atom may form together a group O; each R.sup.2b is independently selected from cyano, hydroxyl, mercapto, halogen, C.sub.1-C.sub.20-alkoxy, C.sub.1-C.sub.20-alkylthio, nitro, NR.sup.2Ar2R.sup.2Ar3, NR.sup.2Ar2COR.sup.2Ar3, CONR.sup.2Ar2R.sup.2Ar3, SO.sub.2NR.sup.2Ar2R.sup.2Ar3, COOR.sup.2Ar2, SO.sub.3R.sup.2Ar2, C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where the four latter radicals are unsubstituted or bear one or more R.sup.2b1 groups, and where 2 radicals R.sup.2b bound at the same carbon atom may form together a group O; each R.sup.2b1 is independently selected from cyano, hydroxyl, mercapto, nitro, halogen, NR.sup.2Ar2R.sup.2Ar3, NR.sup.2Ar2COR.sup.2Ar3, CONR.sup.2Ar2R.sup.2Ar3, SO.sub.2NR.sup.2Ar2R.sup.2Ar3, COOR.sup.2Ar2, SO.sub.3R.sup.2Ar2, SO.sub.3R.sup.2Ar2, C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl, C.sub.1-C.sub.12-alkoxy, or C.sub.1-C.sub.12-alkylthio, and where 2 radicals R.sup.2b1 bound at the same carbon atom may form together a group O; U is an O, S, NR.sup.2Ar1, CO, SO or SO.sub.2 moiety; R.sup.2Ar1, R.sup.2Ar2, R.sup.2Ar3 are each independently hydrogen, C.sub.1-C.sub.18-alkyl, 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where alkyl is unsubstituted or bears one or more R.sup.2a groups, where 3- to 8-membered cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl are unsubstituted or bear one or more R.sup.2b groups; with the proviso that the compound of formula (II) comprises at least one cyano group, and mixtures thereof, (B3) a cyanated perylene compound of formula (III) ##STR00116## in which one of the Z.sup.3 substituents is cyano and the other Z.sup.3 substituent is CO.sub.2R.sup.39, CONR.sup.310R.sup.311, C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl, where C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl are unsubstituted or bear one or more identical or different Z.sup.3a substituents, C.sub.3-C.sub.12-cycloalkyl is unsubstituted or bears one or more identical or different Z.sup.3b substituents, and C.sub.6-C.sub.14-aryl is unsubstituted or bears one or more identical or different Z.sup.3Ar substituents; one of the Z.sup.3* substituents is cyano and the other Z.sup.3* substituent is CO.sub.2R.sup.39, CONR.sup.310R.sup.311, C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl, where C.sub.1-C.sub.18-alkyl, C.sub.2-C.sub.18-alkenyl, C.sub.2-C.sub.18-alkynyl are unsubstituted or bear one or more identical or different Z.sup.3a substituents, C.sub.3-C.sub.12-cycloalkyl is unsubstituted or bears one or more identical or different Z.sup.3b substituents, and C.sub.6-C.sub.14-aryl is unsubstituted or bears one or more identical or different Z.sup.3Ar substituents; R.sup.31, R.sup.32, R.sup.33, R.sup.34, R.sup.35, R.sup.36, R.sup.37 and R.sup.38 are each independently selected from hydrogen, cyano, bromine or chlorine, with the proviso that 1, 2, 3, 4, 5, 6, 7 or 8 of the R.sup.31, R.sup.32, R.sup.33, R.sup.34, R.sup.35, R.sup.36, R.sup.37 or R.sup.38 substituents are cyano; where R.sup.39 is hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl, where C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl are unsubstituted or bear one or more identical or different R.sup.3a substituents, C.sub.3-C.sub.12-cycloalkyl is unsubstituted or bears one or more identical or different R.sup.3b substituents and C.sub.6-C.sub.14-aryl is unsubstituted or bears one or more identical or different R.sup.3Ar substituents; R.sup.310 and R.sup.311 are each independently hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl, where C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl are unsubstituted or bear one or more identical or different R.sup.3a substituents, C.sub.3-C.sub.12-cycloalkyl is unsubstituted or bears one or more identical or different R.sup.3b substituents and C.sub.6-C.sub.14-aryl is unsubstituted or bears one or more identical or different R.sup.3Ar substituents; each Z.sup.3a is independently halogen, hydroxyl, NR.sup.310aR.sup.311a, C.sub.1-C.sub.10-alkoxy, C.sub.1-C.sub.10-haloalkoxy, C.sub.1-C.sub.10-alkylthio, C.sub.3-C.sub.12-cycloalkyl, C.sub.6-C.sub.14-aryl, C(O)R.sup.39a; C(O)OR.sup.39a or C(O)NR.sup.310aR.sup.311a, where C.sub.3-C.sub.12-cycloalkyl is unsubstituted or bears one or more identical or different R.sup.3b substituents and C.sub.6-C.sub.14-aryl is unsubstituted or bears one or more identical or different R.sup.3Ar substituents; each Z.sup.3b and each Z.sup.3Ar is independently halogen, hydroxyl, NR.sup.310aR.sup.311a, C.sub.1-C.sub.10-alkyl, C.sub.1-C.sub.10-alkoxy, C.sub.1-C.sub.10-haloalkoxy, C.sub.1-C.sub.10-alkylthio, C(O)R.sup.39a; C(O)OR.sup.39a or C(O)NR.sup.310aR.sup.311a; each R.sup.3a is independently halogen, hydroxyl, C.sub.1-C.sub.10-alkoxy, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl; each R.sup.3b is independently halogen, hydroxyl, C.sub.1-C.sub.10-alkyl, C.sub.1-C.sub.10-alkoxy, C.sub.1-C.sub.10-haloalkoxy, C.sub.1-C.sub.10-alkylthio, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl; each R.sup.3Ar is independently halogen, hydroxyl, C.sub.1-C.sub.10-alkyl, C.sub.1-C.sub.10-alkoxy, C.sub.1-C.sub.10-haloalkoxy, C.sub.1-C.sub.10-alkylthio, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl; R.sup.39a is hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl; and R.sup.310a, R.sup.311a are each independently hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, C.sub.3-C.sub.12-cycloalkyl or C.sub.6-C.sub.14-aryl, and mixtures thereof; (B4) a cyanated compound of formula (IV) ##STR00117## wherein m4 is 0, 1, 2, 3 or 4; each R.sup.41 independently from each other is selected from bromine, chlorine, cyano, NR.sup.4aR.sup.4b C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, C.sub.3-C.sub.24-cycloalkyl, heterocycloalkyl, heteroaryl, C.sub.6-C.sub.24-aryl, C.sub.6-C.sub.24-aryloxy or C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl, aryloxy in the six last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R.sup.41a and where C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, and the alkylene moiety of C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene may be interrupted by one or more groups selected from O, S or NR.sup.4c; at least one of the radicals R.sup.42, R.sup.43, R.sup.44 and R.sup.45 is CN, and the remaining radicals, independently from each other, are selected from hydrogen, chlorine or bromine; X.sup.40 is O, S, SO or SO.sub.2; A is a diradical selected from diradicals of the general formulae (A.1), (A.2), (A.3), or (A.4) ##STR00118## wherein * in each case denotes the point of attachments to the remainder of the molecule; n4 is 0, 1, 2, 3 or 4; o4 is 0, 1, 2 or 3; p4 is 0, 1, 2 or 3; R.sup.46 is hydrogen, C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.3-C.sub.24-cycloalkyl, C.sub.6-C.sub.24-aryl or C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene, where the rings of cycloalkyl, aryl, and aryl-alkylene in the three last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R.sup.46a, and where C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl and the alkylene moiety of C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene may be interrupted by one or more heteroatoms or heteroatomic groups selected from O, S and NR.sup.4c; each R.sup.47 independently from each other is selected from bromine, chlorine, cyano, NR.sup.4aR.sup.4b, C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, C.sub.3-C.sub.24-cycloalkyl, heterocycloalkyl, heteroaryl, C.sub.6-C.sub.24-aryl, C.sub.6-C.sub.24-aryloxy, C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in the six last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R.sup.47a and where C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, and the alkylene moiety of C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene may be interrupted by one or more groups selected from O, S and NR.sup.4c; each R.sup.48 independently from each other is selected from bromine, chlorine, cyano, NR.sup.4aR.sup.4b, C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, C.sub.3-C.sub.24-cycloalkyl, heterocycloalkyl, heteroaryl, C.sub.6-C.sub.24-aryl, C.sub.6-C.sub.24-aryloxy, C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in the six last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R.sup.48a and where C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, and the alkylene moiety of C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene may be interrupted by one or more groups selected from O, S or NR.sup.4c; each R.sup.49 independently from each other is selected from bromine, chlorine, cyano, NR.sup.4aR.sup.4b, C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, C.sub.3-C.sub.24-cycloalkyl, heterocycloalkyl, heteroaryl, C.sub.6-C.sub.24-aryl, C.sub.6-C.sub.24-aryloxy, C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene, where the rings of cycloalkyl, heterocycloalkyl, heteroaryl, aryl and aryl-alkylene in the six last-mentioned radicals are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R.sup.49a and where C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-haloalkyl, C.sub.1-C.sub.24-alkoxy, C.sub.1-C.sub.24-haloalkoxy, and the alkylene moiety of C.sub.6-C.sub.24-aryl-C.sub.1-C.sub.10-alkylene may be interrupted by one or more groups selected from O, S or NR.sup.4c; R.sup.41a, R.sup.46a, R.sup.47a, R.sup.48a, R.sup.49a are independently of one another selected from C.sub.1-C.sub.24-alkyl, C.sub.1-C.sub.24-fluoroalkyl, C.sub.1-C.sub.24-alkoxy, fluorine, chlorine or bromine; R.sup.4a, R.sup.4b, R.sup.4c are independently of one another are selected from hydrogen, C.sub.1-C.sub.20-alkyl, C.sub.3-C.sub.24-cycloalkyl, heterocycloalkyl, heteroaryl or C.sub.6-C.sub.24-aryl; and mixtures thereof; (B5) a benz(othi)oxanthene compound of formula (V) ##STR00119## wherein X.sup.5 is oxygen or sulfur; R.sup.51 is C.sub.1-C.sub.24-alkyl which is unsubstituted or substituted by one or more R.sup.a a groups or R.sup.51 is phenyl which is unsubstituted or comprises 1, 2, 3, 4 or 5 substituents selected from halogen, R.sup.511, OR.sup.552, NHR.sup.552 and NR.sup.552R.sup.557; R.sup.51a is independently of each other and independently of each occurrence selected from cyano, halogen, C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl or heteroaryl, where C.sub.3-C.sub.8-cycloalkyl, 3- to 8-membered heterocyclyl, aryl and heteroaryl are unsubstituted or bear one or more substituents selected from halogen, C.sub.1-C.sub.18-alkyl and C.sub.1-C.sub.18-haloalkyl; R.sup.52, R.sup.53, R.sup.54, R.sup.55, R.sup.56, R.sup.57, R.sup.58 and R.sup.59 are independently of each other selected from hydrogen, halogen, R.sup.553, OR.sup.553, NHR.sup.553 or NR.sup.553R.sup.554, wherein R.sup.511 is selected from C.sub.1-C.sub.20-alkyl, C.sub.6-C.sub.24-aryl or heteroaryl; R.sup.552 and R.sup.557 are independently of each other selected from C.sub.1-C.sub.18-alkyl, C.sub.6-C.sub.24-aryl or heteroaryl; and R.sup.553 and R.sup.554 are independently of each other selected from C.sub.1-C.sub.18-alkyl, C.sub.6-C.sub.24-aryl or heteroaryl; and mixtures thereof; (B6) a benzimidazoxanthenisoquinoline compound of formulae (VIA) or (VIB) ##STR00120## wherein X.sup.6 is oxygen or sulfur; R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, R.sup.67, R.sup.68, R.sup.69, R.sup.610, R.sup.611 and R.sup.612 are independently of each other selected from hydrogen, halogen, R.sup.661, OR.sup.661, NHR.sup.661 or NR.sup.661R.sup.662; wherein each R.sup.661 is selected from C.sub.1-C.sub.18-alkyl, C.sub.6-C.sub.24-aryl or heteroaryl; and each R.sup.662 is selected from C.sub.1-C.sub.18-alkyl, C.sub.6-C.sub.24-aryl or heteroaryl; and mixtures thereof; (B7) fluorescent compound comprising at least one structural unit of formula (VII) ##STR00121## where one or more CH groups of the six-membered ring of the benzimidazole structure shown may be replaced by nitrogen and where the symbols are each defined as follows: n7 is a number from 0 to (10-p7) for each structural unit of the formula (VII); where p7 is the number of CH units which have been replaced by nitrogen in the six-membered ring of the benzimidazole structure shown; X7 is a chemical bond, O, S, SO, SO.sub.2, NR.sup.71; and R is an aliphatic radical, cycloaliphatic radical, aryl, heteroaryl, each of which may bear substituents, an aromatic or heteroaromatic ring or ring system, each of which is fused to other aromatic rings of the structural unit of the formula (VII), is F, C.sub.1, Br, CN, H when X7 is not a chemical bond; where two R radicals may be joined to give one cyclic radical and where X7 and R, when n7> one, may be the same or different; R.sup.71 is each independently hydrogen, C.sub.1-C.sub.18-alkyl or cycloalkyl, the carbon chain of which may comprise one or more O, S, CO, SO and/or SO.sub.2-moieties and which may be mono- or polysubstituted; aryl or heteroaryl which may be mono- or polysubstituted; and mixtures thereof; (B8) a perylene compound of formulae (VIII) or (IX) ##STR00122## where R.sup.81, R.sup.82 are each independently C.sub.1-C.sub.30-alkyl, C.sub.2-C.sub.30-alkyl which is interrupted by one or more oxygen, C.sub.3-C.sub.8-cycloalkyl, C.sub.6-C.sub.10-aryl, heteroaryl, C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.10-alkylene, where the aromatic ring in the three latter radicals is unsubstituted or mono- or polysubstituted by C.sub.1-C.sub.10-alkyl; R.sup.92 is C.sub.1-C.sub.30-alkyl, C.sub.3-C.sub.8-cycloalkyl, aryl, heteroaryl, aryl-C.sub.1-C.sub.10-alkylene, where the aromatic ring in the three latter radicals is unsubstituted or mono- or polysubstituted by C.sub.1-C.sub.10-alkyl; (B9) a naphthalene monoimide compound of formula (X) ##STR00123## wherein each R.sup.101 independently of each other is hydrogen, C.sub.1-C.sub.30-alkyl, C.sub.2-C.sub.30-alkyl which is interrupted by one or more oxygen, C.sub.3-C.sub.8-cycloalkyl, C.sub.6-C.sub.10-aryl, heteroaryl, C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.10-alkylene, where the aromatic ring in the three latter radicals is unsubstituted or mono- or polysubstituted by C.sub.1-C.sub.10-alkyl; R.sup.102 is hydrogen, C.sub.1-C.sub.30-alkyl, C.sub.2-C.sub.30-alkyl which is interrupted by one or more oxygen, C.sub.3-C.sub.8-cycloalkyl, C.sub.6-C.sub.10-aryl, heteroaryl, C.sub.6-C.sub.10-aryl-C.sub.1-C.sub.10-alkylene, where the aromatic ring in the three latter radicals is unsubstituted or mono- or polysubstituted by C.sub.1-C.sub.10-alkyl; (B10) 7-(diethylamino)-3-(5-methylbenzo[d]oxazol-2-yl)-2H-chromen-2-one; (B11) a perylene compound of formulae (XIA) or (XIB) ##STR00124## wherein each R.sup.111 independently of each other is C.sub.1-C.sub.18 alkyl, C.sub.4-C.sub.8 cycloalkyl, which may be mono- or polysubstituted by halogen or by linear or branched C.sub.1-C.sub.18 alkyl, or phenyl or naphthyl which may be mono- or polysubstituted by halogen or by linear or branched C.sub.1-C.sub.18 alkyl; and mixtures thereof; (B12) a cyanated perylene compound of formulae (XIIA) or (XIIB) ##STR00125## wherein each R.sup.121 independently of each other is C.sub.1-C.sub.18 alkyl, C.sub.4-C.sub.8 cycloalkyl, which may be mono- or polysubstituted by halogen or by linear or branched C.sub.1-C.sub.18 alkyl, or phenyl or naphthyl which may be mono- or polysubstituted by halogen or by linear or branched C.sub.1-C.sub.18 alkyl; and mixtures thereof; (B13) a perylene bisimide compound of formula (XIII) ##STR00126## wherein p13 is 1, 2, 3 or 4; R.sup.131 and R.sup.132 independently of each other are C.sub.1-C.sub.10-alkyl, which is unsubstituted or substituted by C.sub.6-C.sub.10-aryl which in turn is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.20-alkyl, which is interrupted by one or more oxygen, C.sub.3-C.sub.8-cycloalkyl, which is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl, or C.sub.6-C.sub.10-aryl which is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl; each R.sup.133 independently of each other is fluorine, chlorine, C.sub.1-C.sub.16-alkyl, C.sub.2-C.sub.16-alkyl interrupted by one or more oxygen, C.sub.1-C.sub.16-alkoxy, C.sub.6-C.sub.10-aryloxy which is unsubstituted or mono- or polysubstituted by fluorine, chlorine, C.sub.1-C.sub.16-alkyl, C.sub.2-C.sub.16-alkyl interrupted by one or more oxygen, C.sub.1-C.sub.16-alkoxy or C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by 1, 2 or 3 radicals selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-alkoxy, where the R.sup.133 radicals are at the positions indicated by *; and mixtures thereof; (B14) a perylene compound of formula (XIV) ##STR00127## wherein R.sup.141 and R.sup.142, independently of each other, are selected from hydrogen, in each case unsubstituted or substituted C.sub.1-C.sub.30-alkyl, polyalkyleneoxy, C.sub.1-C.sub.30-alkoxy, C.sub.1-C.sub.30-alkylthio, C.sub.3-C.sub.20-cycloalkyl, C.sub.3-C.sub.20-cycloalkyloxy, C.sub.6-C.sub.24-aryl or C.sub.6-C.sub.24-aryloxy; R.sup.143, R.sup.144, R.sup.145, R.sup.146, R.sup.147, R.sup.148, R.sup.149, R.sup.1410, R.sup.1411, R.sup.1412, R.sup.1413, R.sup.1414, R.sup.1415, R.sup.1416, R.sup.1417 and R.sup.1418 independently of each other, are selected from hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, NE.sup.141E.sup.142, NR.sup.Ar141COR.sup.A142, CONR.sup.Ar141R.sup.Ar142, SO.sub.2NR.sup.A141R.sup.A142, COOR.sup.Ar141, SO.sub.3R.sup.Ar142, in each case unsubstituted or substituted C.sub.1-C.sub.30-alkyl, polyalkyleneoxy, C.sub.1-C.sub.30-alkoxy, C.sub.1-C.sub.30-alkylthio, C.sub.3-C.sub.20-cycloalkyl, C.sub.3-C.sub.20-cycloalkoxy, C.sub.6-C.sub.24-aryl, C.sub.6-C.sub.24-aryloxy or C.sub.6-C.sub.24-arylthio, where R.sup.143 and R.sup.144, R.sup.144 and R.sup.145, R.sup.145 and R.sup.146, R.sup.146 and R.sup.147, R.sup.147 and R.sup.148, R.sup.148 and R.sup.149, R.sup.149 and R.sup.1410, R.sup.1411 and R.sup.1412, R.sup.1412 and R.sup.1413, R.sup.1413 and R.sup.1414, R.sup.1414 and R.sup.1415, R.sup.1415 and R.sup.1416, R.sup.1416 and R.sup.1417 and/or R.sup.1417 and R.sup.1418 together with the carbon atoms of the biphenylyl moiety to which they are bonded, may also form a further fused aromatic or non-aromatic ring system wherein the fused ring system is unsubstituted or substituted; where E.sup.141 and E.sup.142, independently of each other, are hydrogen, unsubstituted or substituted C.sub.1-C.sub.18-alkyl, unsubstituted or substituted C.sub.2-C.sub.18-alkenyl, unsubstituted or substituted C.sub.2-C.sub.18-alkynyl, unsubstituted or substituted C.sub.3-C.sub.20-cycloalkyl or unsubstituted or substituted C.sub.6-C.sub.10-aryl; R.sup.Ar141 and R.sup.Ar142, each independently of each other, are hydrogen, unsubstituted or substituted C.sub.1-C.sub.18-alkyl, unsubstituted or substituted C.sub.3-C.sub.20-cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C.sub.6-C.sub.20-aryl or unsubstituted or substituted heteroaryl; and mixtures thereof (B15) a compound of the formula (XV) ##STR00128## (B16) a terrylene bisimide compound of formula (XVI) ##STR00129## wherein p16 is 0, 1, 2, 3 or 4; R.sup.161 and R.sup.162 independently of each other are C.sub.1-C.sub.10-alkyl, which is unsubstituted or substituted by C.sub.6-C.sub.100-aryl which in turn is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl, C.sub.2-C.sub.20-alkyl, which is interrupted by one or more oxygen, C.sub.3-C.sub.8-cycloalkyl, which is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl, or C.sub.6-C.sub.10-aryl which is unsubstituted or substituted by 1, 2 or 3 C.sub.1-C.sub.10-alkyl; R.sup.163 if present, independently of each other is fluorine, chlorine, C.sub.1-C.sub.16-alkyl, C.sub.2-C.sub.16-alkyl interrupted by one or more oxygen, C.sub.1-C.sub.16-alkoxy, C.sub.6-C.sub.10-aryloxy which is unsubstituted or mono- or polysubstituted by fluorine, chlorine, C.sub.1-C.sub.16-alkyl, C.sub.2-C.sub.16-alkyl interrupted by one or more oxygen, C.sub.1-C.sub.16-alkoxy or C.sub.6-C.sub.10-aryl, which is unsubstituted or substituted by 1, 2 or 3 radicals selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-alkoxy, where the R.sup.163 radicals are at the positions indicated by *; and mixtures thereof.

2: The transmitter of claim 1, wherein the first electromagnetic radiation comprises at least one wavelength in a spectral range between 350 nm and 500 nm.

3: The transmitter of claim 1, wherein the radiation source is a light emitting diode (LED) or a laser diode.

4: The transmitter of claim 3, wherein the radiation source is a blue LED with a center wavelength of emission between 400 nm and 480 nm.

5: The transmitter of claim 3, wherein the radiation source is selected from the group consisting of a UV-LED, an RGB LED system, an organic LED and a cool white LED, said cool white LED having a correlated color temperature between 4 000 K and 20 000 K.

6: The transmitter of claim 1, wherein the frequency converter comprises at least one colorant B selected from the groups B1, B2, B3, B4, B5, B7, B8, B11, B12, B13, B14, B15, B16 or mixtures thereof.

7: The transmitter of claim 1, wherein the frequency converter comprises a combination of organic fluorescent colorants selected from a compound of group B7 and a compound of group B13.

8: The transmitter of claim 1, wherein the polymeric matrix material of the frequency converter is selected from a polystyrene, polycarbonate, polymethylmethacrylate, polymethacrylate, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl chloride, polybutene, silicone, polyacrylate, epoxy resin, polyvinyl alcohol, poly(ethylene vinylalcohol)-copolymer, polyacrylonitrile, polyvinylidene chloride, polystyrene acrylonitrile (SAN), polybutylene terephthalate, polyethylene terephthalate, polyvinyl butyrate, polyvinyl chloride, polyamide, polyoxymethylene, polyimide, polyetherimide, 2,5-furandicarboxylate polyester or mixtures thereof.

9: The transmitter of claim 1, wherein the frequency converter additionally comprises at least one scattering body.

10: The transmitter of claim 1, wherein the frequency converter has a fluorescence decay time (excited-state lifetime) in a range from 0.1 to 9 ns.

11: The transmitter of claim 1, wherein the frequency converter is arranged in a remote arrangement from the radiation source, wherein a distance to the radiation source is in a range from 0.01 to 10 cm.

12: The transmitter of claim 1, wherein the frequency converter is formed by extrusion, printing, coating or moulding.

13: The transmitter of claim 1, wherein the modulator is coupled to the radiation source and wherein the modulator is adapted to control the radiation source so that an intensity of at least a part of the first electromagnetic radiation emitted by the radiation source varies depending on the data to be transmitted.

14: An illumination device, comprising the transmitter of claim 1 transmitting modulated second electromagnetic radiation in the visible spectral range wherein the illumination device is adapted to generate a value of a luminous flux of the modulated second electromagnetic radiation being at least in a range from 100 lm to 30 000 lm.

15: A data transmission system, comprising: the transmitter of claim 1; a receiver, adapted to detect at least a part of the modulated second electromagnetic radiation emitted by the transmitter; and a data analyzer for extracting data from the modulated second electromagnetic radiation detected by the receiver.

Description

DESCRIPTION OF THE DRAWINGS

[0447] Embodiments of the present invention are now described with reference to the drawings.

[0448] FIG. 1 shows a schematic representation of an embodiment of the data transmission system according to the invention including an embodiment of a transmitter according to the present invention.

[0449] With reference to FIG. 1, an embodiment of the transmitter 1 according to the present invention is described:

[0450] The transmitter comprises a radiation source 2 for generating and emitting first electromagnetic radiation 3. The radiation source 2 is a LED emitting blue light, wherein the center wavelength of emission is between 400 nm and 480 nm, in particular between 440 nm and 470 nm.

[0451] Furthermore, the transmitter 1 comprises a frequency converter 4 that is positioned in the direction of the first electromagnetic radiation 3 emitted by the radiation source 2, so that the first electromagnetic radiation 3 irradiates the frequency converter 4. The frequency converter 4 is arranged in a remote arrangement from the radiation source 2. In the present embodiment, the distance between the radiation source 2 and the frequency converter is 0.1-10 cm.

[0452] According to one embodiment, the radiation source 2 and the frequency converter 4 may be arranged within a housing 5. The housing 5 is partly transparent for electromagnetic radiation to be emitted by the transmitter. According to a preferred embodiment, the radiation source 2 and the frequency converter 4 are not arranged within a housing 5. The frequency converter 4 is applied to the inside surface of the transparent part of the housing 5. In particular, the frequency converter 4 is formed by extrusion, printing, coating or molding.

[0453] The frequency converter 4 converts at least a part of the first electromagnetic radiation 3 emitted by the radiation source 2 into second electromagnetic radiation 6. The second electromagnetic radiation 6 is different from the first electromagnetic radiation 3. The frequency converter 4 is adapted to convert a first wavelength of the first electromagnetic radiation 3 into a second wavelength of the second electromagnetic radiation 6, wherein the second wavelength is longer than the first wavelength.

[0454] The second electromagnetic radiation 6 has a band spectrum comprising wavelengths in the range from 450 nm to 700 nm, so that the frequency converter 4 converts the blue light emitted by the radiation source 2 into a band spectrum within the visible spectral range forming white light. The bandwidth of the first electromagnetic radiation, i. e. the blue light emitted by the blue LED, is narrower than the bandwidth of the second electromagnetic radiation. Therefore, the emitted blue light is broadened to white light.

[0455] The white light generated by the frequency converter 4 is finally emitted by the transmitter 1. Transmitter 1 therefore emits electromagnetic radiation in the visible spectral range.

[0456] Furthermore, the transmitter 1 comprises a control unit 7 for controlling the radiation source 2. In particular, the radiation source 2 may be turned on and turned off by the control unit 7. Furthermore, the control unit 7 may control the intensity of the blue light emission of the blue LED forming the radiation source 2. For example, the intensity may be controlled by pulse width modulation (PWM).

[0457] Moreover, the transmitter 1 comprises a modulator 8 being adapted to modulate the first electromagnetic radiation emitted by the radiation source 2 depending on data to be transmitted. In the present embodiment, the modulator 8 is coupled to the control unit 7. The modulator 8 transfers a modulation signal to control unit 7. Control unit 7 then applies this modulation signal to the control of the radiation source 2. It is noted that the modulation signal is independent from the pulse width modulation for controlling the light intensity. The data to be transmitted are coded by the modulation signal. In particular, intensity modulation may be used to transmit the data, i. e. the intensity of the first electromagnetic radiation 3 emitted by the radiation source 2 varies depending on the data to be transmitted. However, the variations are so small, so that they are imperceptible for the viewer.

[0458] Furthermore, the modulator 8 is coupled to a data source 9. Data source 9 transfers the data to be transmitted to the modulator 8 that converts such data into a modulation signal that can be used by the control unit.

[0459] Therefore, the blue LED forming the radiation source 2 emits blue light as first electromagnetic radiation 3 that is modulated in accordance with the data to be transmitted. Such modulated blue light is converted by the frequency converter 4 into modulated white light that forms modulated second electromagnetic radiation 6. Therefore, the frequency converter 4 of the present embodiment may also be designated as light converter or frequency converter.

[0460] The frequency converter 4 has particular properties that will be described in further detail below. One property of the frequency converter 4 is that the converted electromagnetic radiation that is white light in the present embodiment is modulated in correspondence to the modulation of the first electromagnetic radiation 3. The modulation used for data transmission is maintained by the frequency converter 4. As it will be described in further detail below, fluorescence is used for frequency conversion by the frequency converter 4. However, the fluorescence decay time is rather short, so that the modulation is not blurred.

[0461] The value of the luminous flux of the second electromagnetic radiation 6, i.e. of the white light, may be at least in the range from 100 lm to 30 000 lm. Therefore, an illumination device is formed comprising the transmitter 1 for transmitting data on the one hand and for emitting illumination light on the other hand. Such illumination device may be used wherever a luminaire, a lamp or any other lighting device may conventionally be used.

[0462] In addition, the illumination device may also be dimmed, so that a lower luminous flux that is not perceptible may also be generated, so that data transmission may also be carried out when the illumination device is not used for lighting.

[0463] In the following, an embodiment of a data transmission system in accordance with the present invention is described:

[0464] The data transmission system comprises the transmitter 1 as described above. Furthermore, the data transmission system comprises a receiving unit 10. The receiving unit 10 comprises a receiver 11 to detect at least a part of the modulated second electromagnetic radiation 6 emitted by the transmitter 1. Therefore, the receiver 11 is located to be irradiated by the second electromagnetic radiation 6. Furthermore, an optical filter 12 may be arranged before the receiver 11 for filtering the modulated second electromagnetic radiation 6 emitted by the transmitter 1. The receiver 11 may be a photodetector, a solar cell or a camera, such as a camera of a computer or smartphone.

[0465] The receiving unit 10 further comprises a data analyzer 13 that is coupled to the receiver 11. The data analyzer 13 is adapted to extract data from the detected modulated second electromagnetic radiation 6 as it is known in the art.

[0466] It is noted that the modulation applied by the modulator 8 may be applied differently. In the above described embodiment, the modulator 8 is coupled to the control unit 7, so that the modulation is directly applied to the radiation source 2 by means of intensity variations. According to other embodiments, the modulator 8 may also be located between the radiation source 2 and the frequency converter 4. In this case, unmodulated first electromagnetic radiation is generated and emitted by the radiation source 2. The first unmodulated electromagnetic radiation 3 is then modulated by the modulator, so that modulated first electromagnetic radiation 3 is generated that irradiates the frequency converter 4. As described above, the frequency converter 4 then converts the modulated first electromagnetic radiation 3 into modulated second electromagnetic radiation 6 that is in particular white light of an illumination device. In other embodiments, the modulator may even be integrated in the frequency converter 4. However, in this case, the frequency converter 4 must be an active element that may be controlled by the modulator.

[0467] In the following, an example of a frequency converter 4 is described in detail that is used in the embodiment of the transmitter 1 and the data transmission system using transmitter 1:

LIST OF REFERENCE SIGNS

[0468] 1 transmitter [0469] 2 radiation source [0470] 3 first electromagnetic radiation [0471] 4 frequency converter [0472] 5 housing [0473] 6 second electromagnetic radiation [0474] 7 control unit [0475] 8 modulator [0476] 9 data source [0477] 10 receiving unit [0478] 11 receiver [0479] 12 infrared filter [0480] 13 analysing unit

EXAMPLES

[0481] The following figures and examples serve to illustrate the invention and should not be interpreted as limiting.

[0482] The following dyes 1 to 24 were employed in the examples.

Dye 1: (Colorant from Group B13)

N, N-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboximide

[0483] Dye 1 can be purchased from, e.g. from BASF SE.

Dye 2: (Colorant from Group B12)

diisobutyl 4,10-dicyanoperylene-3,9-dicarboxylate mixture with diisobutyl 4,9-dicyanoperylene-3,10-dicarboxylate

[0484] ##STR00088##

[0485] Dye 2 can be purchased, e.g. from BASF SE.

Dye 3: (Colorant from Group B8)

##STR00089##

[0486] Dye 3 can be purchased, e.g. from BASF SE.

Dye 4: (Colorant from Group B8)

N,N-Bis(2,6-diisopropylphenyl)-3,4,9,10-perylenetetracarboxylic diimide

[0487] ##STR00090##

[0488] Dye 4 can be purchased, e.g. from BASF SE.

Dye 5: (Colorant from Group B13)

##STR00091##

[0489] Dye 5 can be prepared in analogy to the methods described in EP 3072887.

Dye 6: (Colorant from Group B13)

##STR00092##

[0490] A mixture of 2.2 g (2.6 mmol) of 1,6,7,12-tetrachloro-N,N-2,6-diisopropylphenyl-perylene-3,4,9,10-tetracarboxylic acid diimide, 4.25 g (31.2 mmol) of 2-isopropylphenol, 2.52 g (18.2 mmol) of K.sub.2CO.sub.3 and 170 mL of N-methylpyrrolidone were heated to 90 C. for 17 hours. Afterwards, the mixture was heated to 110 C. for 10 hours. Further 2.12 g (15.6 mmol) of 2-isopropylphenol and 1.26 g of K.sub.2CO.sub.3 were added and heating continued for 23 hours. Further 2.12 g (15.6 mmol) of 2-isopropylphenol and 1.26 g of K.sub.2CO.sub.3 were added and heating continued for 6 hours. The product was precipitated with 1 L of diluted HCl. After extraction with dichloromethane 7.5 g of a liquid crude material was obtained which was further purified by column chromatography using toluene dicholoromethane. 0.28 g of pure title compound were isolated.

Rf (petroleum ether/ethylacetate 8:1)=0.3.
Lambda max emission: 616 nm (in polycarbonate).
Dye 7: (Colorant from Group B11)

diisobutyl perylene-3,9-dicarboxylate mixture with diisobutyl perylene-3,10-dicarboxylate

[0491] ##STR00093##

[0492] Dye 7 can be purchased, e.g. from BASF SE.

Dye 8: (Colorant from Group B5)

##STR00094##

[0493] Dye 8 can be prepared as described in WO 2014/131628.

Dye 9: (Colorant from Group B7)

##STR00095##

[0494] Dye 9 can be prepared as described in example 10 of WO 2012/168395.

Dye 10: (Colorant from Group B3)

Mixture of Compounds (10.a) and (10.b)

[0495] ##STR00096##

in which
three of the R.sup.2, R.sup.3, R.sup.6 and R.sup.7 substituents are hydrogen; and
one of the R.sup.2, R.sup.3, R.sup.6 and R.sup.7 substituents is cyano.

[0496] Dye 10 can be prepared as described in example 3 of WO 2015/169935.

Dye 11: (Colorant from Group B1)

##STR00097##

11.1 Preparation of

[0497] ##STR00098##

[0498] Following the procedure described in example 6 of WO 2012/168395, a mixture of the title compound and of the corresponding mono- and di- and tetrabrominated compounds were obtained. The tribrominated compound constitutes about 40% by weight.

11.2 Preparation of the Title Compound

[0499] A mixture of 2.5 g (0.005 mol) g of the tribrominated compound of example 11.1, 4.41 g (0.03 mol) of 4-cyanophenylboronic acid, 2.07 g (0.015 mol) of potassium carbonate dissolved in 5 mL of water and 0.174 g (0.00015 mol) of tetrakistriphenylphosphinepalladium(0) was heated at 90 C. for 4 hours. After cooling to room temperature, the residue was filtered off, washed with methanol and water and dried in vacuum to give 2.29 g of a crude product. The compound was purified by column chromatography (silica gel; toluene/ethyl acetate 20:1) to afford 0.92 g (32%) of a yellow solid.

R.sub.f(toluene/ethyl acetate 10:1)=0.3.
Lambda max emission=508 nm (polycarbonate).
Dye 12: (Colorant from Group B2)

Mixture of

[0500] ##STR00099## ##STR00100##

[0501] Dye 12 can be prepared as described in example 3 of WO 2015/019270.

Dye 13: (Colorant from Group B5)

##STR00101##

[0502] Dye 13 can be prepared as described in WO 2014/131628 (compound 2401).

Dye 14: (Colorant from Group B13)

##STR00102##

[0503] A mixture of 5 g (5.9 mmol) of N,N-(2,6-diisopropylphenyl)-1,6,7,12,-tetrachloro-perylenetetracarboxylic diimide, 4.23 g of (24.9 mmol) biphenyl-2-ol, 138.21 g (16.9 mmol) of potassium carbonate and 30 mL of N-methyl-2-pyrrolidone (NMP) were stirred at room temperature for 24 h and then for 48 h at 115 C. After cooling to 80 C., the reaction mixture was added tropwise to a mixture of 10 mL of acetic acid and 20 mL of water within 15 min, cooled to room temperature over a period of 2 h and then filtered. The residue was washed with 300 mL of a mixture of ethanol/water (1:1) and then with 600 mL of a mixture of ethanol/water/NMP (4:4:1). The residue was dissolved in a mixture of 35 mL of ethanol and 5 mL of NMP under reflux, then cooled to room temperature and separated to obtain 5.6 g (62%) of a red dye which was purified by chromatography using cyclohexane/ethyl acetate. The yield was 2.06 g (23%). Rf (cylohexane/ethyl acetate 10:1)=0.29.

Dye 15: (Colorant from Group B14)

##STR00103##

[0504] Dye 15 can be prepared as described in example 1 of WO 2017/121833 A1.

Dye 16: (Colorant from Group B5)

##STR00104##

[0505] Dye 16 can be prepared in analogy to the compounds described in WO 2014/131628.

Dye 17: (Colorant from Group B4)

##STR00105##

[0506] Dye 17 can be prepared as described in example 6 of WO 2016/151068.

Dye 18: (Colorant from Group B4)

##STR00106##

[0507] Dye 18 can be prepared as described in example 5 of WO 2016/151068.

Dye 19: (Colorant from Group B1)

Mixture of Compounds

[0508] ##STR00107##

19.1 2,4-Dibromo-6-nitroaniline

[0509] A mixture of 10 g (0.072 mol) of 2-nitroaniline, 100 mL of glacial acid, 14.5 mL (0.29 mol; 46.4 g) of bromine were heated at about 45 C. After 2 hours, further 3.0 mL (0.06 mol) of bromine were added, and the reaction mixture was stirred for two further hours. Excess bromine was outgassed. To the reaction mixture water was added. The precipitate was sucked off, washed with water and dried to give 21.0 g (98%) of a yellow solid.

[0510] R.sub.f(toluene/ethyl acetate 10:1)=0.8.

19.2 4-[4-Amino-3-(4-cyanophenyl)-5-nitro-phenyl]benzonitrile

[0511] A mixture of 367 mL of toluene, 19.45 g (0.066 mol) of the compound of 19.1, 21.72 g (0.242 mol) of 4-cyanophenylboronic acid, 31.6 g (0.114 mol) of potassium carbonate dissolved in 50 mL of water, 6.02 g (0.0066 mol) of tris(dibenzylidene-acetone)dipalladium and 26 mL (0.0264 mol) of a tri-tert-butylphosphine solution in toluene were heated under nitrogen at 80 to 90 C. for 3 hours. The reaction mixture was cooled to room temperature. The precipitate was filtered, washed with water and dried to 21.6 g (96%) of a yellow solid.

R.sub.f(toluene/ethyl acetate 10:1)=0.29.

19.3 4-[3,4-Diamino-5-(4-cyanophenyl)phenyl]benzonitrile

[0512] A mixture of 19.9 g (0.0584 mol) of the compound of 19.2, 400 mL of ethanol, 100 mL of N-methylpyrrolidone and 44.0 g (0.2328 mol) of zinc(II) chloride were heated under reflux at 85 C. for 2 hours. After cooling to room temperature and filtration, ethanol was removed from the filtrate by distillation. The title compound was precipitated by addition of water and ethanol. The precipitate was filtered off, washed with hot water and dried in vacuum to give 25.9 g (143%) of a yellow compound containing inorganic salts.

R.sub.f(toluene/ethyl acetate 10:1)=0.1.

19.4 Mixture of

[0513] ##STR00108##

[0514] A mixture of 250 mL of quinoline, 8.8 g (0.032 mol) of 4-bromo-1,8-naphthalic anhydride, 11.0 g (0.032 mol; 90% purity) of the mixture from 19.3, 6.0 g (0.032 mol) of zinc acetate was heated at 130 C. for 2 hours under nitrogen. After cooling to room temperature, 200 mL of methanol were added. The mixture was stirred over night followed by filtration. The residue was washed with methanol and water. 11.45 g (65%) of a yellow precipitate were obtained.

R.sub.f(toluene/ethyl acetate 10:1)=0.5.

19.5 Mixture of the Title Compounds

[0515] A mixture of 11.0 g (0.02 mol) of the mixture of compounds from 19.4, 2.68 g (0.02 mol) of phenylboronic acid, 5.52 g (0.04 mol) of potassium carbonate, 30 mL of water, 250 mL of toluene and 0.23 g (0.0002 mol) of tetrakistriphenylphosphinepalladium was heated at 90 C. for 2 hours. After cooling to room temperature, the residue was filtered off, washed with methanol and water and dried in vacuum to give 10.5 (95%) of a yellow-black residue. This residue was dissolved in 400 mL of toluene by heating under reflux, 2.0 g of activated charcoal were added, the mixture was stirred for 30 minutes followed by hot filtration. The filtrate was allowed to cool up over night and the precipitate was filtered off. Yield: 2.3 g of the title compound which is free of palladium.

R.sub.f(toluene/ethyl acetate 10:1)=0.5.
Lambda max emission: 519 nm (in polycarbonate).
Dye 20: (Colorant from Group B5)

##STR00109##

[0516] Dye 20 can be prepared as described in WO 2014/131628.

Dye 21: (Colorant from Group B15)

##STR00110##

[0517] Dye 21 can be prepared in analogy to the methods described in WO 2012/168395.

Dye 22: (Colorant from Group B7)

Mixture of

[0518] ##STR00111##

[0519] Dye 22 can be prepared as described in WO 2012/168395.

Dye 23: (Colorant from Group B16)

##STR00112##

[0520] Dye 23 can be prepared as described in example 2 of WO 2007/006717.

Dye 24: (Colorant from Group B16)

##STR00113##

[0521] Dye 24 can be prepared as described in Chem. Eur. J. 1997, 3, pages 219-225.

Production of the Frequency Converters for Testing of the Dyes:

[0522] The afore-mentioned fluorescent dyes were used to produce frequency converters by incorporation into a polymer matrix by the method described in the following. The polymers used were polymethylmethacrylate (PMMA, Plexiglas 6N from Evonik), polystyrene (PS, 168 N from BASF) and polycarbonate (PC, Macrolon 2808 from Bayer). About 2.5 g of polymer and 0.008% to 0.06% by weight of the dye was dissolved in about 5 mL of methylene chloride, and 0.5% by weight of TiO.sub.2 (Kronos 2220) were dispersed therein, based in each case on the amount of polymer used. The exact composition of each converter is described in table 1. The solutions/dispersion obtained were coated onto a glass surface using an applicator frame (from Ericsen, wet film thickness 400 m). After the solvent had dried off, the film was detached from the glass and dried in a vacuum drying cabinet at 50 C. overnight. Two circular film pieces of 80 to 85 m thickness having a diameter of 15 mm were punched out of each film, and used as analysis samples.

Measurement of Quantum Yields:

[0523] Fluorescence quantum yields (QY) of the analysis samples were measured with the C9920-02 quantum yield measuring system from Hamamatsu. This was done by illuminating each of the samples with light of 445 to 455 nm in an integrating sphere (Ulbricht sphere). By comparison with the reference measurement in the Ulbricht sphere without sample, the unabsorbed fraction of the excitation light and the fluorescent light emitted by the sample are determined by means of a CCD spectrometer. Integration of the intensities of the spectrum of the unabsorbed excitation light and of that of the emitted fluorescent light gives the degree of absorption and fluorescence intensity, respectively, and thus the fluorescence quantum yield of each sample can be calculated. All measurements were performed at room temperature.

Determination of the Excited-State Lifetime .sub.v and the Emissive Lifetime .sub.0:

[0524] The excited-state lifetime (.sub.v) of the prepared thin films is measured by exciting the thin films with a pulsed diode laser with an excitation wavelength of 450 nm (Picoquant) operated at 10 kHz (85 W, 105 W/cm.sup.2) and detecting the emission with time correlated single photon counting (TCSPC). This wavelength was chosen in order to be close to the lighting application, where a blue LED with 450 nm emission maximum is used. A mono-exponential fit to the decay curve was used to determine the excited-state lifetime (.sub.v). All measurements were performed at room temperature.

[0525] The emissive lifetime .sub.0 is calculated by .sub.0=.sub.v/QY. This value is important to compare between different materials as only radiative decay processes are considered here. The following table 1 summarizes the results. Excitation was at 450 nm, the decay rate was determined at the emission maximum which is given in the second column. Some of the materials were measured in different matrices, and some samples were also measured without adding TiO.sub.2 to the film to see the influence of the scattering bodies.

TABLE-US-00001 TABLE 1 Emission Frequency converter maximum [nm] .sub.v [ns] .sub.0 [ns] QY [%] 0.03% dye 1 in PC 606 6.0 6.8 88.7 0.03% dye 1 in PS 600 5.9 6.5 90.5 0.03% dye 2 in PS 520 4.0 4.3 92.7 0.03% dye 3 in PS 520 4.7 5.3 88.5 0.03% dye 4 in PS 540 5.1 5.5 91.9 0.03% dye 4 in PS 576 4.9 5.3 91.9 0.03% dye 4 in PMMA 540 5.1 5.4 94.8 0.03% dye 4 in PMMA 576 4.9 5.2 94.8 0.03% dye 4 in PMMA 618 5.0 5.3 94.8 0.04% dye 5 in PC 576 5.3 0.03% dye 5 in PS 566 4.9 5.2 94.3 0.015% dye 6 in PS 600 5.3 5.5 95.2 0.05% dye 7 in PMMA 520 6.0 6.4 93.2 0.03% dye 7 in PC 540 5.6 6.0 92.8 0.02% dye 7 in PS 540 5.4 5.8 92.7 0.02% dye 8 in PMMA 525 6.7 7.6 88.6 0.02% dye 9 in PS 520 4.9 5.7 85.8 0.02% dye 9 in PC 520 5.2 5.9 88.1 0.01% dye 10 in PMMA 506 5.5 6.1 90.0 0.01% dye 10 in PMMA 530 5.8 6.4 90.0 0.01% dye 10 in PC 508 5.2 5.8 89.3 0.01% dye 10 in PC 533 5.3 6.0 89.3 0.01% dye 10 in PS 534 5.3 5.9 89.9 0.01% dye 10 in PS 506 5.2 5.8 89.9 0.04% dye 11 in PC 560 4.7 5.3 87.9 0.04% dye 11 in PS 560 4.6 5.3 86.6 0.01% dye 12 in PS 550 5.3 6.0 87.4 0.01% dye 12 in PC 540 5.3 6.1 86.7 0.01% dye 13 in PS 540 7.1 7.8 90.4 0.01% dye 13 in PC 540 7.1 7.7 91.8 0.03% dye 14 in PC 560 6.5 6.9 94.7 0.03% dye 14 in PS 560 6.4 6.8 95.2 0.035% dye 15 in PC 573 5.8 6.0 97.4 0.035% dye 15 in PC 610 6.0 6.1 97.4 0.035% dye 15 in PS 610 6.0 6.0 99.4 0.035% dye 15 in PS 573 6.0 6.0 99.4 0.0176% dye 16 in PC 530 5.4 5.7 94.7 0.012% dye 16 in PS 525 5.2 5.6 93.6 0.0192% dye 17 in PC 535 7.5 9.0 82.9 0.017% dye 17 in PS 535 7.3 8.8 83.4 0.123% dye 18 in PC 502 7.1 7.6 93.7 0.123% dye 18 in PC 532 7.6 8.1 93.7 0.02% dye 19 in PC 520 4.4 4.7 92.1 0.012% dye 20 in PS 525 5.4 5.7 93.8 0.016% dye 20 in PC 525 5.5 5.8 94.3 0.008% dye 21 in PC 540 4.7 6.0 78.5 0.034% dye 22 in PC 520 5.5 6.4 86.3

[0526] In addition, for the dyes 23 and 24 excitation was done at 635 nm, as they absorb very little at 450 nm. The following table 2 summarizes the results.

TABLE-US-00002 TABLE 2 Emission Frequency converter maximum [nm] .sub.v [ns] .sub.0 [ns] QY [%] 0.04% dye 23 in PS 715 4.2 6.8 88.7 0.06% dye 23 in PC 715 3.9 6.5 90.5 0.04% dye 24 in PC 688 4.4 10.5 42.0 0.04% dye 24 in PS 680 4.1 8.0 51.0 0.04% dye 24 in PS 720 4.3 8.5 51.0
Frequency Converter Films with Two Dyes

[0527] Frequency converter films with two dyes (1 and 9) were prepared and measured. The films C1-C5 were prepared by extrusion, C6 and C7 by doctor-blading. The following table 3 summarizes the concentration of the components which were mixed in PC as matrix polymer.

TABLE-US-00003 TABLE 3 dye 9 dye 1 TiO.sub.2 Film thickness Example [weight %] [weight %] [weight %] [m] C1 0.0115 0.0036 0.25 240 C2 0.0136 0.0042 0.25 270 C3 0.0136 0.0042 0.25 300 C4 0.0136 0.0042 0.25 300 C5 0.0156 0.0048 0.25 300 C6 0.129 0.009 0.5 137 C7 0.140 0.009 0.5 137

[0528] LED 1 and LED 2, respectively, were used as light source for pumping the converter film.

[0529] The cool-white LEDs 1 with CCT of 9108 K were inserted into a transparent plastic tube of T8 format. Rectangular pieces of the converter films are shaped to semitubes and inserted into the tube. The converter film therefore covers the cool white LEDs.

[0530] LED 2: A down-light equipped with blue LEDs (450 nm) inside a mixing chamber are totally covered by a planar, circular platelet of the converter film with 61 mm diameter.

[0531] The light irradiated from the surface of these devices was subjected to the photometric measurement, where the total light irradiated from the device was measured by a photometric measurement tool equipped with an integrating sphere, ISP 500-100, and the CCD detector CAS 140CT-156 (from Instrument Systems, Munich). The measured radiance spectrum was used to derive all relevant photometric data, such as CCT (=correlated color temperature) in Kelvin [K], distance of color point from Planck-curve (BBL), average color rendering index CRI and color rendering index for reference color no. 9 (R9), efficacy data, etc. The results are given in the table 4 below, C1-C5 was optimized and measured with cool-white LED 1, C6 and C7 with blue LED 2. All measurements were performed at room temperature.

TABLE-US-00004 TABLE 4 CCT distance from average CIE-x CIE-y CIE-u [K] BBL (duv) CRI (R.sub.a) R9 LED 1 0.2933 0.2785 0.2038 9108 1.34E02 77.66 28.76 C1 0.4326 0.4023 0.2486 3059 1.18E04 90.07 33.40 C2 0.4575 0.4082 0.2620 2714 6.75E04 92.55 38.84 C3 0.4680 0.4105 0.2678 2590 6.40E04 93.31 42.76 C4 0.4695 0.4106 0.2687 2570 6.83E04 93.19 43.42 C5 0.4786 0.4100 0.2749 2454 1.35E03 92.23 47.24 LED 2 0.1539 0.0235 0.2069 C6 0.4277 0.4014 0.2457 3140 3.06E04 93.65 67.54 C7 0.4335 0.4022 0.2491 3044 2.65E04 93.30 66.25

[0532] For these frequency converter films, the decay time was measured as described above (it is not possible to determine the fluorescence quantum yield for an individual colorant in a mixture and thus the emissive lifetime .sub.0 cannot be calculated). Small peak maximum changes in the fluorescence spectra were observed for the different colorant concentrations. The emission was measured both at the maximum of the yellow and the red dye, respectively. As the red dye is also excited by re-absorption from the yellow emission, its decay time is longer. The results are shown in table 5.

TABLE-US-00005 TABLE 5 Emission maximum [nm] .sub.v [ns] C1 530 5.3 600 7.2 C2 520 5.4 600 7.7 C3 520 5.4 600 7.8 C4 520 5.3 600 7.8 C5 520 5.4 600 8.0 C6 518 5.4 600 6.4 C7 518 5.4 600 6.5

Lifetime of the Colorants Under Irradiation Conditions

[0533] The photostability of the colorants in polymer matrix of the frequence converter used according to the invention were investigated by measuring the T80 values. The measurements were performed at room temperature. T80 in days is the time that the product of quantum yield and absorption decreases to 80% of its initial value. To this end, PC-polymer-films doped with fluorescent colorants according to the present invention and 0.5% by weight of TiO.sub.2 were prepared as described above. For comparison purpose, a frequency converter comprising Super Yellow and 0.5% by weight of TiO.sub.2 in PS was prepared by doctor blading, since it was not possible to prepare a frequency converter comprising Super Yellow in PC. The concentration of Super Yellow was 1%, film thickness: ca 20 m. The concentration of the dyes 1 to 22 and of comparison colorant Super Yellow was chosen in a way so that they absorb about 50% of incoming blue light. The concentration of the dyes 23 and 24 was chosen in a way so that they absorb about 50% of incoming light at at 635 nm.

[0534] Dyes 1 to 22 and comparison colorant Super Yellow were illuminated with blue light illumination (450 nm) at 120 mW/cm.sup.2, whereas dyes 23 and 24 were illuminated with white light at 100 mW/cm.sup.2 as their absorption at 450 nm is negligible. The results are summarized in table 6.

TABLE-US-00006 TABLE 6 Frequency converter T80 [days] 0.036% dye 1 in PC 252 0.01% dye 2 in PC in N2 atmosphere 9 0.03% dye 3 in PC in N2 atmosphere >30 0.04% dye 4 in PC 32 0.04% dye 5 in PC in N2 atmosphere >30 0.03% dye 6 in PC 255 0.03% dye 7 in PC in N2 atmosphere >15 0.02% dye 8 in PC 8 0.015% dye 9 in PC 20 0.01% dye 10 in PC in N2 atmosphere 10 0.04% dye 11 in PC 15 0.01% dye 12 in PC 24 0.02% dye 13 in PC 6 0.048% dye 14 in PC 200 0.04% dye 15 in PC 211 0.019% dye 17 in PC 8 0.123% dye 18 in PC 14 0.022% dye 19 in PC 14 0.008% dye 21 in PC 8 0.034% dye 22 in PC 20 0.06% dye 23 in PC >500 0.04% dye 24 in PC >500 1% Super Yellow# in PS <1 #Comparison, Super Yellow; PDY132, available from Aldrich (https://www.sigmaaldrich.com/catalog/product/aldrich/900438?lang=de&region=DE), conjugated copolymer of poly para-phenylene vinylene

[0535] As can be seen from table 6, the colorants used according to the present invention have a long lifetime under real irradiation conditions, since the measurements were done in films and therefore are real application values. The T80 values are much longer for the colorants used according to the present invention than for the prior art colorant Super Yellow.