Optical data carrier comprising a merocyanine dye as light-absorbent compound in the information layer

Abstract

Optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and if desired a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue, red or infrared light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one merocyanine dye is used as light-absorbent compound.

Description

[0001] The invention relates to a write-once optical data carrier comprising a merocyanine dye as light-absorbent compound in the information layer, to a process for its production and also to the application of the above-mentioned dyes to a polymer substrate, in particular polycarbonate, by spin coating or vapour deposition.

[0002] Write-once optical data carriers using specific light-absorbent substances or mixtures thereof are particularly suitable for use in high-density writeable optical data stores which operate with blue laser diodes, in particular GaN or SHG laser diodes (360-460 nm) and/or for use in DVD-R or CD-R disks which operate with red (635-660 nm) or infrared (780-830 nm) laser diodes.

[0003] The write-once compact disk (CD-R, 780 nm) has recently experienced enormous volume growth and represents the technically established system.

[0004] The next generation of optical data stores—DVDs—is currently being introduced onto the market. Through the use of shorter-wave laser radiation (635-660 nm) and higher numerical aperture NA, the storage density can be increased. The writeable format in this case is DVD-R.

[0005] Today, optical data storage formats which use blude laser diodes (based on GaN, JP 08 191 171 or Second Harmonic Generation SHG JP 09 050 629) (360 nm-460 nm) with high laser power are being developed. Writeable optical data stores will therefore also be used in this generation. The achievable storage density depends on the focussing of the laser spot on the information plane. Spot size scales with the laser wavelength λ/NA. NA is the numerical aperture of the objective lens used. In order to obtain the highest possible storage density, the use of the smallest possible wavelength λ is the aim. At present 390 nm is possible on the basis of semiconductor laser diodes.

[0006] The patent literature describes dye-based writeable optical data stores which are equally suitable for CD-R and DVD-R systems (JP-A 11 043 481 and JP-A 10 181 206). To achieve a high reflectivity and a high modulation height of the read-out signal and also to achieve sufficient sensitivity in writing, use is made of the fact that the IR wavelength of 780 nm of CD-Rs is located at the foot of the long wavelength flank of the absorption peak of the dye and the red wavelength of 635 nm or 650 nm of DVD-Rs is located at the foot of the short wavelength flank of the absorption peak of the dye. In JP-A 02 557 335, JP-A 10 058 828, JP-A 06 336 086, JP-A 02 865 955, WO-A 09 917 284 and U.S. Pat. No. 5,266,699, this concept is extended to the 450 nm working wavelength region on the short wavelength flank and the red and IR region on the long wavelength flank of the absorption peak.

[0007] Apart from the abovementioned optical properties, the writeable information layer comprising light-absorbent organic substances has to have a substantially amorphous morphology to keep the noise signal during writing or reading as small as possible. For this reason, it is particularly preferred that crystallization of the light-absorbent substances be prevented in the application of the substances by spin coating from a solution, by vapour deposition and/or sublimation during subsequent covering with metallic or dielectric layers under reduced pressure.

[0008] The amorphous layer comprising light-absorbent substances preferably has a high heat distortion resistance, since otherwise further layers of organic or inorganic material which are applied to the light-absorbent information layer by sputtering or vapour deposition would form blurred boundaries due to diffusion and thus adversely affect the reflectivity. Furthermore, a light-absorbent substance which has insufficient heat distortion resistance can, at the boundary to a polymeric support, diffuse into the latter and once again adversely affect the reflectivity.

[0009] A light-absorbent substance whose vapour pressure is too high can sublime during the above-mentioned deposition of further layers by sputtering or vapour deposition in a high vacuum and thus reduce the layer thicknes to below the desired value. This in turn has an adverse effect on the reflectivity.

[0010] It is therefore an object of the invention to provide suitable compounds which satisfy the high requirements (e.g. light stability, favourable signal/noise ratio, damage-free application to the substrate material, and the like) for use in the information layer in a write-once optical data carrier, in particular for high-density writeable optical data store formats in a laser wavelength range from 340 to 830 nm.

[0011] Surprisingly, it has been found that light-absorbent compounds selected from the group of merocyanine dyes can satisfy the abovementioned requirement profile particularly well.

[0012] The invention accordingly provides an optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and if desired a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue, red or infrared light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one merocyanine dye is used as light-absorbent compound.

[0013] The light-absorbent compound should preferably be able to be changed thermally. The thermal change preferably occurs at a temperature of <600° C., particularly preferably at a temperature of <400° C., very particularly preferably at a temperature of <300° C., in particular <200° C. Such a change can be, for example, a decomposition or chemical change of the chromophoric centre of the light-absorbent compound.

[0014] Preference is given to a merocyanine dye of the formula 1

[0015] where

[0016] A represents a radical of the formula 2

[0017] X1 represents CN, CO—R1, COO—R1, CONHR3, CONR3R4 or SO2R1,

[0018] X2 represents hydrogen, C1-C6-alkyl, C6-C10-aryl, a five- or six-membered heterocyclic radical, CN, CO—R1, COO—R2, CONHR3, CONR3R4, SO2R1 or a radical of the formula 3

[0019] or

[0020] CX1X2 represents a ring of the formula 4

[0021] which may be benzo- or naphtho-fused and/or substituted by nonionic or ionic radicals, where the asterisk (*) indicates the ring atom from which the double bond extends,

[0022] X3 represents N or CH,

[0023] X4 represents O, S, N, N—R6 or CH, where X3 and X4 do not simultaneously represent CH,

[0024] X5 represents O, S or N—R6,

[0025] X6 represents O, S, N, N—R6, CH or CH2,

[0026] the ring B of the formula (II) 5

[0027] together with X4, X3 and the C atom between them

[0028] and the ring C of the formula (V) 6

[0029] together with X5, X6 and the C atom between them

[0030] each represent, independently of one another, a five- or six-membered aromatic, pseudoaromatic or partially hydrogenated heterocyclic ring which can contain from 1 to 4 heteroatoms and/or may be benzo- or naphtho-fused and/or substituted by nonionic or ionic radicals,

[0031] the ring D together with the N atom represents a hydrogenated five- or six-membered heterocyclic ring which can contain from 1 to 4 heteroatoms and/or may be substituted by nonionic or ionic radicals,

[0032] the ring E together with the N atom represents an aromatic, pseudoaromatic or partially hydrogenated five- or six-membered heterocyclic ring which can contain from 1 to 4 heteroatoms and/or may be benzo- or naphtho-fused and/or substituted by nonionic or ionic radicals,

[0033] An− represents an anion,

[0034] Y1 represents N or C—R7,

[0035] Y2 represents N or C—R8,

[0036] R0 represents C1-C6-alkyl or C7-C15-aralkyl,

[0037] R1 to R6 and R5′ represent, independently of one another, hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C5-C7-cycloalkyl, C6-C10-aryl or C7-C15-aralkyl,

[0038] R7 and R8 represent, independently of one another, hydrogen, cyano or C1-C6-alkyl or

[0039] R6 and R8 together represent a CH2)2— or —(CH2)3— bridge,

[0040] R9 and R10 represent, independently of one another, C1-C6-alkyl, C6-C10-aryl, a five- or six-membered heterocyclic radical or C7-C15-aralkyl or

[0041] NR9R10 may form a five- or six-membered ring and

[0042] n represents 1 or 2.

[0043] Possible nonionic radicals are, for example, C1-C4-alkyl, C1-C4-alkoxy, halogen, cyano, nitro, C1-C4-alkoxycarbonyl, C1-C4-alkylthio, phenyl, pyridyl, C1-C4-alkanoylamino, benzoylamino, mono- or di-C1-C4-alkylamino, pyrrolidino, piperidino, piperazino or morpholino.

[0044] Possible ionic radicals are, for example, ammonium radicals or COO− or SO3− radicals which may be bound via a direct bond or via —(CH2)n—, where n represents an integer from 1 to 6.

[0045] Alkyl, alkoxy, aryl and heterocyclic radicals may, if desired, bear further radicals such as alkyl, halogen, nitro, cyano, CO—NH2, alkoxy, trialkylsilyl, trialkylsiloxy or phenyl, the alkyl and alkoxy radicals may be straight-chain or branched, the alkyl radicals may be partially halogenated or perhalogenated, the alkyl and alkoxy radicals may be ethoxylated or propoxylated or silylated, adjacent alkyl and/oder alkoxy radicals on aryl or heterocyclic radicals may together form a three- or four-membered bridge and the heterocyclic radicals may be benzo-fused and/or quaternized.

[0046] Preference is given to

[0047] the ring B of the formula (II) representing furan-2-yl, thiophen-2-yl, pyrrol-2-yl, benzofuran-2-yl, benzothiophen-2-yl, thiazol-5-yl, imidazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, where the individual rings may be substituted by C1-C6-alkyl, C1-C6-alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-acylamino, C6-C10-aryl, C6-C10-aryloxy, C6-C10-arylcarbonylamino, mono- or di-C1-C6-alkylamino, N—C1-C6-alkyl-N—C6-C10-arylamino, pyrrolidino, morpholino or piperidino, and

[0048] the ring C of the formula (V) representing benzothiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, pyrrolin-2-ylidene, thiazol-2-ylidene, thiazolin-2-ylidene, isothiazol-3-ylidene, isoxazol-3-ylidene, oxazolin-2-ylidene, imidazol-2-ylidene, pyrazol-5-ylidene, 1,3,4-thiadiazol-2-ylidene, 1,3,4-oxadiazol-2-ylidene, 1,2,4-thiadiazol-5-ylidene, 1,3,4-triazol-2-ylidene, 3H-indol-2-ylidene, dihydropyridin-2- or -4-ylidene, dihydroquinolin-2- or -4-ylidene, where the individual rings may be substituted by C1-C6-alkyl, C1-C6-alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-acylamino, C6-C10-aryl, C6-C10-aryloxy, C6-C10-arylcarbonylamino, mono- or di-C1-C6-alkylamino, N—C1-C6-alkyl-N—C6-C10-arylamino, pyrrolidino, morpholino or piperidino.

[0049] In a particularly preferred embodiment, the merocyanines used are ones of the formula (VI) 7

[0050] where

[0051] X1 represents CN, CO—R1, COO—R2 or SO2R1,

[0052] X2 represents hydrogen, methyl, ethyl, phenyl, 2- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, benzoxazol-2-yl, CN, CO—R1, COO—R2 or a radical of the formula 8

[0053] or

[0054] CX1X2 represents a ring of the formula 9

[0055] which may be substituted by up to 3 radicals selected from the group consisting of methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, phenyl, 10

[0056] SO3−M+, —CH2—SO3−M+,

[0057] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0058] An− represents an anion,

[0059] M+ represents a cation,

[0060] X3 represents CH,

[0061] X4 represents O, S or N—R6,

[0062] the ring B of the formula (II) represents furan-2-yl, thiophen-2-yl, pyrrol-2-yl or thiazol-5-yl, where the rings mentioned may each be substituted by methyl, ethyl, propyl, butyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, phenoxy, tolyloxy, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-phenylamino, pyrrolidino or morpholino,

[0063] Y1 represents N or C—R7,

[0064] R1, R2, R5 and R6 represent, independently of one another, hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl and

[0065] R5 may also represent —(CH2)3—N(CH3)2 or —(CH2)3—N+(CH3)3An−,

[0066] R5′ represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl and

[0067] R7 represents hydrogen or cyano.

[0068] In a likewise particularly preferred embodiment, the merocyanines used are ones of the formula (VII) 11

[0069] where

[0070] X1 represents CN, CO—R1, COO—R2 or SO2R1,

[0071] X2 represents hydrogen, methyl, ethyl, phenyl, 2- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, benzoxazol-2-yl, CN, CO—R1, COO—R2 or a radical of the formula 12

[0072] or

[0073] CX1X2 represents a ring of the formula 13

[0074] which may be substituted by up to 3 radicals selected from the group consisting of methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, phenyl, 14

[0075] SO3−M+, —CH2—SO3−M+,

[0076] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0077] An− represents an anion,

[0078] M+ represents a cation,

[0079] X5 represents N—R6,

[0080] X6 represents S, N—R6 or CH2,

[0081] the ring C of the formula (V) represents benzothiazol-2-ylidene, benzimidazol-2-ylidene, thiazol-2-ylidene, thiazolin-2-ylidene, 1,3,4-thiadiazol-2-ylidene, 1,3,4-triazol-2-ylidene, dihydropyridin-4-ylidene, dihydroquinolin-4-ylidene, pyrrolin-2-ylidene or 3H-indol-2-ylidene, where the rings mentioned may each be substituted by methyl, ethyl, propyl, butyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-phenylamino, pyrrolidino or morpholino,

[0082] Y2Y1 represents N—N or (C—R8)—(C—R7),

[0083] R1, R2, R5 and R6 represent, independently of one another, hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl and

[0084] R5 may also represent —(CH2)3—N(CH3)2 or —(CH2)3—N+(CH3)3An−,

[0085] R5′ represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl,

[0086] R7 and R8 represent hydrogen or

[0087] R6 and R8 together represent a —CH2—CH2— bridge.

[0088] In a likewise particularly preferred embodiment, the merocyanines used are ones of the formula (VIII) 15

[0089] where

[0090] X1 represents CN, CO—R1, COO—R2 or SO2R1,

[0091] X2 represents hydrogen, methyl, ethyl, phenyl, 2- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, benzoxazol-2-yl, CN, CO—R1, COO—R2 or a radical of the formula 16

[0092] or

[0093] CX1X2 represents a ring of the formula 17

[0094] which may be substituted by up to 3 radicals selected from the group consisting of methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, phenyl, 18

[0095] SO3−M+, —CH2—SO3−M+,

[0096] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0097] An− represents an anion,

[0098] M+ represents a cation,

[0099] NR9R10 represents dimethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, N-methyl-N-tolylamino, N-methyl-N-anisylamino, carbazolo, pyrrolidino, piperidino or morpholino,

[0100] Y1 represents N or C—R7,

[0101] R1, R2, R5 and R6 represent, independently of one another, hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl and

[0102] R5 may also represent —(CH2)3—N(CH3)2 or —(CH2)3—N+(CH3)3An−,

[0103] R5′ represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl or benzyl,

[0104] R7 represents hydrogen and

[0105] n represents 0 or 1.

[0106] Possible anions An− are all monovalent anions or one equivalent of a polyvalent anion. Preference is given to colourless anions. Examples of suitable anions are chloride, bromide, iodide, tetrafluoroborate, perchlorate, hexafluorosilicate, hexafluorophosphate, methosulphate, ethosulphate, C1-C10-alkanesulphonate, C1-C10-perfluoroalkanesulphonate, unsubstituted or chlorine-, hydroxy- or C1-C4-alkoxy-substituted C1-C10-alkanoate, unsubstituted or nitro-, cyano-, hydroxy-, C1-C25-alkyl-, perfluoro-C1-C4-alkyl-, C1-C4-alkoxycarbonyl- or chloro-substituted benzene-sulphonate, naphthalenesulphonate or biphenylsulphonate, unsubstituted or nitro-, cyano-, hydroxy-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-alkoxycarbonyl- or chloro-substituted benzenedisulphonate, naphthalenedisulphonate or biphenyldisulphonate, unsubstituted or nitro-, cyano-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-alkoxycarbonyl-, benzoyl-, chlorobenzoyl- or toluoyl-substituted benzoate, the anion of naphthalenedicarboxylic acid, (diphenyl ether)disulphonate, tetraphenylborate, cyanotriphenylborate, tetra-C1-C20-alkoxyborate, tetraphenoxyborate, 7,8- or 7,9-dicarba-nido-undecaborate(1-) or (2-), which may, if desired, be substituted on the B and/or C atoms by one or two C1-C12-alkyl or phenyl groups, dodecahydro-dicarbadodecaborate(2-) and B-C1-C12-alkyl-C-phenyl-dodecahydro-dicarba-dodecaborate(1-).

[0107] Preference is given to bromide, iodide, tetrafluoroborate, perchlorate, methanesulphonate, benzenesulphonate, toluenesulphonate, dodecylbenzenesulphonate, tetradecanesulphonate.

[0108] Possible cations M+ are all monovalent cations or one equivalent of a polyvalent cation. Preference is given to colourless cations. Examples of suitable cations are lithium, sodium, potassium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, trimethyl-benzylammonium, trimethyl-caprylammonium and Fe(C5H5)2+ (where C5H5=cyclopentadienyl).

[0109] Preference is given to tetramethylammonium, tetraethylammonium, tetrabutylammonium.

[0110] In the case of a write-once optical data carrier according to the invention which is written on and read by means of the light of a blue laser, preference is given to merocyanine dyes whose absorption maximum λmax1 is in the range from 340 to 410 nm, where the wavelength λ1/2 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax1 is half of the absorbance value at λmax1 and the wavelength λ1/10 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax1 is one tenth of the absorbance value at λmax1 are preferably not more than 50 nm apart. Such a merocyanine dye preferably has no longer-wavelength maximum λmax2 up to a wavelength of 500 nm, particularly preferably up to 550 nm, very particularly preferably up to 600 nm.

[0111] Preference is given to merocyanine dyes having an absorption maximum λmax1 of from 345 to 400 nm.

[0112] Particular preference is given to merocyanine dyes having an absorption maximum λmax1 of from 350 to 380 nm.

[0113] Very particular preference is given to merocyanine dyes having an absorption maximum λmax1 of from 360 to 370 nm.

[0114] In the case of these merocyanine dyes, λ1/2 and λ1/10, as defined above, are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.

[0115] In the case of a write-once optical data carrier according to the invention which is written on and read by means of the light of a blue laser, preference is given to merocyanine dyes whose absorption maximum λmax2 is in the range from 420 to 550 nm, where the wavelength λ1/2 at which the absorbance in the short wavelength flank of the absorption maximum at the wavelength λmax2 is half of the absorbance value at λmax2 and the wavelength λ1/10 at which the absorbance in the short wavelength flank of the absorption maximum at the wavelength λmax2 is one tenth of the absorbance value at λmax2 are preferably not more than 50 nm apart. Such a merocyanine dye preferably has no shorter-wavelength maximum λmax1 down to a wavelength of 350 nm, particularly preferably down to 320 nm, very particularly preferably down to 290 nm.

[0116] Preference is given to merocyanine dyes having an absorption maximum λmax2 of from 410 to 530 nm.

[0117] Particular preference is given to merocyanine dyes having an absorption maximum λmax2 of from 420 to 510 nm.

[0118] Very particular preference is given to merocyanine dyes having an absorption maximum λmax2 of from 430 to 500 nm.

[0119] In these merocyanine dyes, λ1/2 and λ1/10, as defined above, are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.

[0120] In the case of a write-once optical data carrier according to the invention which is written on and read by means of the light of a red laser, preference is given to merocyanine dyes whose absorption maximum λmax2 is in the range from 500 to 650 nm, where the wavelength λ1/2 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax2 is half of the absorbance value at λmax2 and the wavelength λ1/10 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax2 is one tenth of the absorbance value at λmax2 are preferably not more than 50 nm apart. Such a merocyanine dye preferably has no longer-wavelength maximum λmax3 up to a wavelength of 750 nm, particularly preferably up to 800 nm, very particularly preferably up to 850 nm.

[0121] Preference is given to merocyanine dyes having an absorption maximum λmax2 of from 530 to 630 nm.

[0122] Particular preference is given to merocyanine dyes having an absorption maximum λmax2 of from 550 to 620 nm.

[0123] Very particular preference is given to merocyanine dyes having an absorption maximum λmax2 of from 580 to 610 nm.

[0124] In these merocyanine dyes, λ1/2 and λ1/10, as defined above, are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.

[0125] In the case of a write-once optical data carrier according to the invention which is written on and read by means of the light of a infrared laser, preference is given to merocyanine dyes whose absorption maximum λmax3 is in the range from 650 to 810 nm, where the wavelength λ1/2 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax3 is half of the absorbance value at λmax3 and the wavelength λ1/10 at which the absorbance in the long wavelength flank of the absorption maximum at the wavelength λmax3 is one tenth of the absorbance value at λmax3 are preferably not more than 50 nm apart.

[0126] Preference is given to merocyanine dyes having an absorption maximum λmax3 of from 660 to 790 nm.

[0127] Particular preference is given to merocyanine dyes having an absorption maximum λmax3 of from 670 to 760 nm.

[0128] Very particular preference is given to merocyanine dyes having an absorption maximum λmax3 of from 680 to 740 nm.

[0129] In these merocyanine dyes, λ1/2 and λ1/10, as defined above, are preferably not more than 40 nm apart, particularly preferably not more than 30 nm apart, very particularly preferably not more than 20 nm apart.

[0130] The merocyanine dyes have a molar extinction coefficient ε of >40 000 l/mol cm, preferably >60 000 l/mol cm, particularly preferably >80 000 l/mol cm, very particularly preferably >100 000 l/mol cm, at the absorption maximum λmax1gλmax2 and/or λmax3.

[0131] The absorption spectra are measured, for example, in solution.

[0132] Suitable merocyanines having the required spectral properties are, in particular, those in which the dipole moment change Δμ=|μg−μag|, i.e. the positive difference between the dipole moments in the ground state and in the first excited state, is very small, preferably <5 D, particularly preferably <2 D. A method of determining such a dipole moment change Δμ is described, for example, in F. Würthner et al., Angew. Chem. 1997, 109, 2933, and in the literature cited therein. A low solvent-induced wavelength shift (dioxane/DMF) is likewise a suitable selection criterion. Preference is given to merocyanines whose solvent-induced wavelength shift Δλ=|λDMF−λdioxane|, i.e. the positive difference between the absorption wavelengths in the solvents dimethylformamide and dioxane, is <20 nm, particularly preferably <10 nm, very particularly preferably <5 nm

[0133] Merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 19

[0134] where

[0135] X101 represents O or S,

[0136] X102 represents Nor CR104,

[0137] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0138] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0139] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0140] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 20

[0141] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0142] R104 preferably represents hydrogen or cyano.

[0143] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 21

[0144] where

[0145] X101 represents O or S,

[0146] X102 represents N or CR104,

[0147] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0148] NR101R102 represents pyrrolidino, piperidino or morpholino, R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0149] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or radical of the formula 22

[0150] Y101 represents N or CH,

[0151] CX103X104 represents a ring of the formula 23

[0152] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0153] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0154] a radical of the formula 24

[0155] where in the case of the formula (CX), the two radicals R105 may be different,

[0156] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0157] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl, —CH2SO3−M+ or a radical of the formula 25

[0158] M+ represents a cation and

[0159] An− represents an anion,

[0160] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0161] R104 preferably represents hydrogen or cyano. Y1 preferably represents CH.

[0162] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 26

[0163] where

[0164] X101 represents O or S,

[0165] X102 represents N or CR104,

[0166] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0167] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0168] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0169] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 27

[0170] Y101 represents N or CH,

[0171] X103 represents cyano, acetyl, methoxycarbonyl or ethoxycarbonyl,

[0172] X104 represents 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, oxazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, N-methylbenzimidazol-2-yl or N-ethylbenzimidazol-2-yl or radical of the formula 28

[0173] R115 and R116 represent, independently of one another, hydrogen, methyl, cyano or 2- or 4-pyridyl and

[0174] An− represents an anion,

[0175] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0176] R104 preferably represents hydrogen or cyano. Y1 preferably represents CH.

[0177] CX103X104 preferably represents a radical of the formula 29

[0178] where the asterisk (*) indicates the ring atom from which the double bond extends, and

[0179] R115, R116 and An are as defined above.

[0180] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 30

[0181] where

[0182] X105 represents S or CR110R111,

[0183] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0184] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0185] R110 and R111 represent, independently of one another, methyl or ethyl or

[0186] CR110R111 represents a bivalent radical of the formula 31

[0187] where two bonds go out from the asterisked (*) atom,

[0188] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0189] X105 preferably represents C(CH3)2.

[0190] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 32

[0191] where

[0192] X105 represents S or CR110R111,

[0193] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0194] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0195] R110 and R111 represent, independently of one another, methyl or ethyl or

[0196] CR110R111 represents a bivalent radical of the formula 33

[0197] where two bonds go out from the asterisked (*) atom,

[0198] Y101 represents N or CH,

[0199] CX103X104 represents a ring of the formula 34

[0200] where the asterisk (*) indiates the ring atom from which the double bond extends,

[0201] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0202] a radical of the formula 35

[0203] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0204] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl, —CH2SO3−M+ or a radical of the formula 36

[0205] M+ represents a cation and

[0206] An− represents an anion,

[0207] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0208] X105 preferably represents C(CH3)2. Y1 preferably represents CH. CX103X104 preferably represents a radical of the formula (CIX), in which R107 represents a radical of the formula (CXII) or (CXIII).

[0209] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 37

[0210] where

[0211] X105 represents S or CR110R111,

[0212] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0213] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0214] R110 and R111 represent, independently of one another, methyl or ethyl or

[0215] CR110R111 represents a bivalent radical of the formula 38

[0216] where two bonds go out from the asterisked (*) atom,

[0217] Y101 represents N or CH,

[0218] X103 represents cyano, acetyl, methoxycarbonyl or ethoxycarbonyl,

[0219] X104 represents 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, oxazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, N-methylbenzimidazol-2-yl- or N-ethyl-benzimidazol-2-yl or a radical of the formula 39

[0220] R115 and R116 represent, independently of one another, hydrogen, methyl, cyano or 2- or 4-pyridyl and

[0221] An− represents an anion,

[0222] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0223] X105 preferably represents C(CH3)2. Y1 preferably represents CH. CX103X104 preferably represents a radical of the formula 40

[0224] where the asterisk (*) indicates the ring atom from which the double bond extends, and

[0225] R115, R116 and An− are as defined above.

[0226] CX103X104 particularly preferably represents a radical of one of the formulae (CXXVIII) to (CXXX).

[0227] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 41

[0228] where

[0229] R112 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0230] R113 and R114 represent hydrogen or together represent a —CH═CH—CH═CH— bridge,

[0231] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0232] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 42

[0233] where

[0234] R112 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0235] R113 and R114 represent hydrogen or together represent a —CH═CH—CH═CH— bridge,

[0236] Y101 represents Nor CH,

[0237] CX103X104 represents a ring of the formula 43

[0238] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0239] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0240] a radical of the formula 44

[0241] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0242] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl, —CH2SO3−M+ or a radical of the formula 45

[0243] M+ represents a cation and

[0244] An− represents an anion,

[0245] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0246] Y1 preferably represents CH.

[0247] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formulae 46

[0248] where

[0249] R112 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0250] R113 and R114 represent hydrogen or together represent a —CH═CH—CH═CH— bridge,

[0251] Y101 represents N or CH,

[0252] X103 represents cyano, acetyl, methoxycarbonyl or ethoxycarbonyl,

[0253] X104 represents 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, oxazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, N-methylbenzimidazol-2-yl or N-ethyl-benzimidazol-2-yl or a radical of the formula 47

[0254] R115 and R116 represent, independently of one another, hydrogen, methyl, cyano or 2- or 4-pyridyl and

[0255] An− represents an anion,

[0256] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0257] Y1 preferably represents CH. CX103X104 preferably represents a radical of the formula 48

[0258] where the asterisk (*) indicates the ring atom from which the double bond extends, and

[0259] R115, R116 and An− are as defined above.

[0260] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 49

[0261] where

[0262] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, benzyl or phenethyl or

[0263] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0264] CX103X104 represents a ring of the formula 50

[0265] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0266] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0267] a radical of the formula 51

[0268] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0269] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl, —CH2SO3−M+ or a radical of the formula 52

[0270] M+ represents a cation,

[0271] An− represents an anion and

[0272] n represents 1 or 2,

[0273] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0274] n preferably represents 2. CX103X104 preferably represents a radical of the formula (CIX), where R107 represents a radical of the formula (CXII) or (CXIII).

[0275] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 53

[0276] where

[0277] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, benzyl or phenethyl or

[0278] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0279] X103 represents cyano, acetyl, methoxycarbonyl or ethoxycarbonyl,

[0280] X104 represents 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, oxazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, N-methylbenzimidazol-2-yl or N-ethyl-benzimidazol-2-yl or a radial of the formula 54

[0281] R115 and R116 represent, independently of one another, hydrogen, methyl, cyano or 2- or 4-pyridyl and

[0282] An− represents an anion,

[0283] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0284] n preferably represents 2. CX103X104 preferably represents a radical of the formula 55

[0285] where the asterisk (*) indicates the ring atom from which the double bond extends, and

[0286] R115, R116 and An are as defined above.

[0287] CX103X104 particularly preferably represents a radical of one of the formulae (CXXVIII) to (CXXX).

[0288] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 56

[0289] where

[0290] X105 represents O, S or CH2,

[0291] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0292] Y101 represents N or CH,

[0293] CX103X104 represents a ring of the formula 57

[0294] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0295] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0296] a radical of the formula 58

[0297] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0298] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl, —CH2SO3−M+ or a radical of the formula 59

[0299] M+ represents a cation and

[0300] An− represents an anion,

[0301] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0302] X105 preferably represents S or CH2. Y1 preferably represents CH. CX103X104 preferably represents a radical of the formula (CIX) in which R107 represents a radical of the formula (CXII) or (CXIII).

[0303] Further merocyanines which are very particularly preferred for the purposes of the invention are those of the formula 60

[0304] where

[0305] X105 represents O, S or CH2,

[0306] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0307] Y101 represents N or CH,

[0308] X103 represents cyano, acetyl, methoxycarbonyl or ethoxycarbonyl,

[0309] X104 represents 2-, 3- or 4-pyridyl, thiazol-2-yl, benzothiazol-2-yl, oxazol-2-yl, benzoxazol-2-yl, benzimidazol-2-yl, N-methylbenzimidazol-2-yl or N-ethylbenzimidazol-2-yl or a radical of the formula 61

[0310] R115 and R116 represent, independently of one another, hydrogen, methyl, cyano or 2- or 4-pyridyl and

[0311] An− represents an anion,

[0312] where the alkyl radicals such as propyl, butyl etc., may be branched.

[0313] X105 preferably represents S or CH2. Y1 preferably represents CH. CX103X104 preferably represents a radical of the formula 62

[0314] where the asterisk (*) indicates the ring atom from which the double bond extends, and

[0315] R115, R116 and An− are as defined above.

[0316] CX103X104 particularly preferably represents a radical of one the formulae (CXXVIII) to (CXXX).

[0317] In the formulae (CIII), (CXVI), (CXVIII), (CXVIIIa) and (CXXXI),

[0318] Y101 preferably represents CH and/oder

[0319] in the formulae (CIII), (CIIIa), (CXVI), (CXVIII), (CXVIIIa), (CXIX) and (CXXXI) CX103X104 preferably represents a ring of the formula (CV), (CVII), (CIX) or (CXXII) or a radical of one of the formulae (CXXVIII) to (CXXX).

[0320] Some merocyanines of the formula (I) are known, e.g. from F. Würthner, Synthesis 1999, 2103; F. Würthner, R. Sens, K. -H. Etzbach, G. Seybold, Angew. Chem. 1999, 111, 1753; DE-A 43 44 116; DE-A 44 40 066; WO 98/23688; JP 52 99 379; JP 53 14 734.

[0321] The invention further provides merocyanines of the formula 63

[0322] where

[0323] X101 represents O or S,

[0324] X102 represents CH,

[0325] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0326] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0327] R103 represents hydrogen,

[0328] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0329] The invention likewise provides merocyanines of the formula 64

[0330] where

[0331] X101 represents S,

[0332] X102 represents N,

[0333] R101 and R102 represent, independently of one another, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0334] NR101R102 represents pyrrolidino or piperidino,

[0335] R103 represents hydrogen or phenyl,

[0336] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0337] The invention likewise provides merocyanines of the formula 65

[0338] where

[0339] X105 represents C(CH3)2,

[0340] R108 represents propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0341] R109 represents methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy or ethoxycarbonyl,

[0342] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0343] The invention likewise provides merocyanines of the formula 66

[0344] where

[0345] X101 represents O or S,

[0346] X102 represents N or CR104,

[0347] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0348] NR101R112 represents pyrrolidino, piperidino or morpholino,

[0349] R103 represents hydrogen or phenyl,

[0350] R104 represents hydrogen or cyano,

[0351] Y101 represents CH,

[0352] CX103X104 represents a ring of the formula 67

[0353] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0354] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0355] The invention likewise provides merocyanines of the formula 68

[0356] where

[0357] X101 represents O or S,

[0358] X102 represents N or CR104,

[0359] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0360] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0361] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0362] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 69

[0363] Y101 represents N or CH,

[0364] CX103X104 represents a ring of the formula 70

[0365] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0366] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or a radical of the formula 71

[0367] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0368] R107 represents —CH2SO3−M+ or a radical of the formula 72

[0369] M+ represents a cation and

[0370] An− represents an anion,

[0371] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0372] The invention likewise provides merocyanines of the formula 73

[0373] where

[0374] X101 represents O or S,

[0375] X102 represents CR104,

[0376] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0377] NR101R102 represents pyrrolidino or morpholino,

[0378] R103 represents hydrogen, methyl or ethyl,

[0379] R104 represents hydrogen, methyl or ethyl,

[0380] Y101 represents CH,

[0381] CX103X104 represents a ring of the formula 74

[0382] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0383] R105 represents hydrogen, methyl, ethyl, propyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, —(CH2)3—N(CH3)2, —(CH2)3—N+(CH3)3 An− or

[0384] a radical of the formula 75

[0385] R106 represents methyl, ethyl, propyl or butyl,

[0386] R107 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0387] M+ represents a cation and

[0388] An− represents an anion,

[0389] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0390] The invention likewise provides merocyanines of the formula 76

[0391] where

[0392] X101 represents O or S,

[0393] X102 represents N or CR104,

[0394] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0395] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0396] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0397] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 77

[0398] Y101 represents N or CH,

[0399] CX103X104 represents a ring of the formula 78

[0400] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0401] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0402] a radical of the formula 79

[0403] R106 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0404] R107 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0405] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0406] The invention likewise provides merocyanines of the formula 80

[0407] where

[0408] X101 represents O or S,

[0409] X102 represents N or CR104,

[0410] R101 and R102 represent, independently of one another, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0411] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0412] R103 represents hydrogen or phenyl,

[0413] R104 represents hydrogen or cyano,

[0414] Y101 represents CH,

[0415] CX103X104 represents a ring of the formula 81

[0416] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0417] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0418] The invention likewise provides merocyanines of the formula 82

[0419] where

[0420] X101 represents O or S,

[0421] X102 represents N or CR104,

[0422] R101 and R102 represent, independently of one another, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0423] NR101 R102 represents pyrrolidino, piperidino or morpholino,

[0424] R103 represents hydrogen or phenyl,

[0425] R104 represents hydrogen or cyano,

[0426] Y101 represents CH,

[0427] CX103X104 represents a ring of the formula 83

[0428] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0429] R105 represents propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, —(CH2)3—N(CH3)2, —(CH2)3—N+(CH3)3An− or

[0430] a radical of the formula 84

[0431] the two radicals R105 may be different and

[0432] M+ represents a cation,

[0433] An−0 represents an anion, where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0434] The invention likewise provides merocyanines of the formula 85

[0435] where

[0436] X101 represents O or S,

[0437] X102 represents N or CR104,

[0438] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0439] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0440] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0441] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 86

[0442] Y101 represents N or CH,

[0443] CX103X104 represents a ring of the formula 87

[0444] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0445] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl or methoxyphenyl,

[0446] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0447] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl or a radical of the formula 88

[0448] and

[0449] An− represents an anion,

[0450] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0451] The invention likewise provides merocyanines of the formula 89

[0452] where

[0453] X101 represents O or S,

[0454] X102 represents N or CR104,

[0455] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0456] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0457] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0458] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 90

[0459] Y101 represents N or CH,

[0460] X103 represents cyano, methoxycarbonyl or ethoxycarbonyl and

[0461] X104 represents benzothiazol-2-yl, benzoxazol-2-yl or 2- or 4-pyridyl,

[0462] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0463] The invention likewise provides merocyanines of the formula 91

[0464] where

[0465] X101 represents O or S,

[0466] X102 represents N or CR104,

[0467] R101 and R102 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, benzyl or phenyl and R101 may also be hydrogen or

[0468] NR101R102 represents pyrrolidino, piperidino or morpholino,

[0469] R103 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, thienyl, chlorine or NR101R102,

[0470] R104 represents hydrogen, methyl, ethyl, phenyl, chlorine, cyano, formyl or a radical of the formula 92

[0471] Y101 represents N or CH,

[0472] CX103X104 represents a radical of the formula 93

[0473] one of the radicals R115 and R116 represents hydrogen, methyl, cyano or 2- or 4-pyridyl and the other represents hydrogen, and

[0474] An− represents an anion,

[0475] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0476] The invention likewise provides merocyanines of the formula 94

[0477] where

[0478] X105 represents C(CH3)2,

[0479] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0480] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0481] Y101 represents CH,

[0482] CX103X104 represents a ring of the formula 95

[0483] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0484] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0485] The invention likewise provides merocyanines of the formula 96

[0486] where

[0487] X105 represents C(CH3)2,

[0488] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0489] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0490] Y101 represents CH,

[0491] CX103X104 represents a ring of the formula 97

[0492] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0493] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0494] a radical of the formula 98

[0495] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0496] R107 represents —CH2SO3−M+ or a radical of the formula 99

[0497] M+ represents a cation and

[0498] An− represents an anion,

[0499] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0500] The invention likewise provides merocyanines of the formula 100

[0501] where

[0502] X105 represents C(CH3)2,

[0503] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0504] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0505] Y101 represents CH,

[0506] CX103X104 represents a ring of the formula 101

[0507] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0508] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0509] a radical of the formula 102

[0510] R106 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0511] R107 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0512] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0513] The invention likewise provides merocyanines of the formula 103

[0514] where

[0515] X105 represents C(CH3)2,

[0516] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0517] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0518] Y101 represents CH,

[0519] CX103X104 represents a ring of the formula 104

[0520] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0521] R105 represents propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl, —(CH2)3—N(CH3)2, —(CH2)3—N+(CH3)3An− or

[0522] a radical of the formula 105

[0523] the two radicals R105 may be different and

[0524] M+ represents a cation,

[0525] An− represents an anion,

[0526] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0527] The invention likewise provides merocyanines of the formula 106

[0528] where

[0529] X105 represents C(CH3)2,

[0530] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0531] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0532] Y101 represents CH,

[0533] CX103X104 represents a ring of the formula 107

[0534] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0535] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl or methoxyphenyl,

[0536] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0537] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl or a radical of the formula 108

[0538] and

[0539] An− represents an anion,

[0540] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0541] The invention likewise provides merocyanines of the formula 109

[0542] where

[0543] X105 represents C(CH3)2,

[0544] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0545] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0546] Y101 represents CH,

[0547] X103 represents cyano, methoxycarbonyl or ethoxycarbonyl and

[0548] X104 represents benzothiazol-2-yl, benzoxazol-2-yl or 2- or 4-pyridyl, preferably 2-pyridyl,

[0549] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0550] The invention likewise provides merocyanines of the formula 110

[0551] where

[0552] X105 represents C(CH3)2,

[0553] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0554] R109 represents hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, chlorine, trifluoromethyl, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

[0555] Y101 represents CH,

[0556] CX103X104 represents a radical of the formula 111

[0557] one of the radicals R115 and R116 represents hydrogen, methyl, cyano or 2- or 4-pyridyl and the other represents hydrogen, and

[0558] An−represents an anion,

[0559] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0560] The invention likewise provides merocyanines of the formula 112

[0561] where

[0562] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, tolyl, anisyl, benzyl or phenethyl or

[0563] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0564] n represents 1 or 2,

[0565] CX103X104 represents a ring of the formula 113

[0566] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0567] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0568] a radical of the formula 114

[0569] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl, R107 represents —CH2SO3−M+or a radical of the formula 115

[0570] M+ represents a cation and

[0571] An− represents an anion,

[0572] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0573] The invention likewise provides merocyanines of the formula 116

[0574] where

[0575] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, tolyl, anisyl, benzyl or phenethyl or

[0576] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0577] n represents 1 or 2,

[0578] CX103X104 represents a ring of the formula 117

[0579] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0580] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0581] a radical of the formula 118

[0582] R106 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0583] R107 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0584] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0585] The invention likewise provides merocyanines of the formula 119

[0586] where

[0587] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, tolyl, anisyl, benzyl or phenethyl or

[0588] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0589] n represents 1 or 2,

[0590] CX103X104 represents a ring of the formula 120

[0591] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0592] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl or methoxyphenyl,

[0593] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0594] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl or a radical of the formula 121

[0595] and

[0596] An− represents an anion,

[0597] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0598] The invention likewise provides merocyanines of the formula 122

[0599] where

[0600] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, tolyl, anisyl, benzyl or phenethyl or

[0601] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0602] n represents 1 or 2,

[0603] X103 represents cyano, methoxycarbonyl or ethoxycarbonyl and

[0604] X104 represents benzothiazol-2-yl, benzoxazol-2-yl or 2- or 4-pyridyl, preferably 2-pyridyl,

[0605] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0606] The invention likewise provides merocyanines of the formula 123

[0607] where

[0608] R115 and R116 represent, independently of one another, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, tolyl, anisyl, benzyl or phenethyl or

[0609] NR115R116 represents pyrrolidino, piperidino or morpholino,

[0610] n represents 1 or 2,

[0611] CX103X104 represents a radical of the formula 124

[0612] one of the radicals R115 and R116 represents hydrogen, methyl, cyano or 2- or 4-pyridyl and the other represents hydrogen, and

[0613] An− represents an anion,

[0614] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0615] The invention likewise provides merocyanines of the formula 125

[0616] where

[0617] X105 represents O, S or CH2,

[0618] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0619] Y101 represents CH,

[0620] CX103X104 represents a ring of the formula 126

[0621] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0622] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0623] a radical of the formula 127

[0624] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0625] R107 represents —CH2SO3− M+ or a radical of the formula 128

[0626] M+ represents a cation and

[0627] An− represents an anion,

[0628] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0629] The invention likewise provides merocyanines of the formula 129

[0630] where

[0631] X105 represents O, S or CH2,

[0632] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0633] Y101 represents CH,

[0634] CX103X104 represents a ring of the formula 130

[0635] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0636] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl, methoxyphenyl or

[0637] a radical of the formula 131

[0638] R106 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0639] R107 represents cyano, methoxycarbonyl or ethoxycarbonyl,

[0640] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0641] The invention likewise provides merocyanines of the formula 132

[0642] where

[0643] X105 represents O, S or CH2,

[0644] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0645] Y101 represents CH,

[0646] CX103X104 represents a ring of the formula 133

[0647] where the asterisk (*) indicates the ring atom from which the double bond extends,

[0648] R105 represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, phenyl, tolyl or methoxyphenyl,

[0649] R106 represents hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, cyano, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenyl,

[0650] R107 represents cyano, methoxycarbonyl, ethoxycarbonyl or a radical of the formula 134

[0651] and

[0652] An− represents an anion,

[0653] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0654] The invention likewise provides merocyanines of the formula 135

[0655] where

[0656] X105 represents O, S or CH2,

[0657] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0658] Y101 represents CH,

[0659] X103 represents cyano, methoxycarbonyl or ethoxycarbonyl and

[0660] X104 represents benzothiazol-2-yl, benzoxazol-2-yl or 2- or 4-pyridyl, preferably 2-pyridyl,

[0661] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0662] The invention likewise provides merocyanines of the formula 136

[0663] where

[0664] X105 represents O, S or CH2,

[0665] R108 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxyethyl, methoxypropyl, cyanoethyl, hydroxyethyl, acetoxyethyl, chloroethyl, cyclohexyl, benzyl or phenethyl,

[0666] Y101 represents CH,

[0667] CX103X104 represents a radical of the formula 137

[0668] one of the radicals R115 and R116 represents hydrogen, methyl, cyano or 2- or 4-pyridyl and the other represents hydrogen, and

[0669] An− represents an anion,

[0670] where the alkyl radicals such as propyl, butyl, etc., may be branched.

[0671] The light-absorbent compounds described guarantee a sufficiently high reflectivity (>10%) of the optical data carrier in the unwritten state and a sufficiently high absorption for thermal degradation of the information layer on point-wise illumination with focused light if the wavelength of the light is in the range from 360 to 460 nm, from 600 to 680 nm and from 750 to 820 nm. The contrast between written and unwritten points on the data carrier is achieved by the reflectivity change of the amplitude and also the phase of the incident light due to the changed optical properties of the information layer after the thermal degradation.

[0672] The merocyanine dyes are preferably applied to the optical data carrier by spin coating or vacuum vapour deposition. The merocyanines can be mixed with one another or with other dyes having similar spectral properties. The information layer can comprise not only the merocyanine dyes but also additives such as binders, wetting agents, stabilizers, diluents and sensitizers and also further constituents.

[0673] Apart from the information layer, further layers such as metal layers, dielectric layers and protective layers may be present in the optical data carrier. Metals and dielectric layers serve, inter alia, to adjust the reflectivity and the heat absorption/retention. Metals can be, depending on the laser wavelength, gold, silver, aluminium, etc. Examples of dielectric layers are silicon dioxide and silicon nitride. Protective layers are, for example, photocurable surface coatings, (pressure-sensitive) adhesive layers and protective films.

[0674] Pressure-sensitive adhesive layers consist mainly of acrylic adhesives. Nitto Denko DA-8320 or DA-8310, disclosed in the patent JP-A 11-2731471, can, for example, be used for this purpose.

[0675] The optical data carrier has, for example, the following layer structure (cf. FIG. 1): a transparent substrate (1), if desired a protective layer (2), an information layer (3), if desired a protective layer (4), if desired an adhesive layer (5), a covering layer(6).

[0676] The structure of the optical data carrier preferably:

[0677] comprises a preferably transparent substrate (1) to whose surface at least one light-writeable information layer (3) which can be written on by means of light, preferably laser light, if desired a protective layer (4), if desired an adhesive layer (5) and a transparent covering layer (6) have been applied.

[0678] comprises a preferably transparent substrate (1) to whose surface a protective layer (2), at least one information layer (3) which can be written on by means of light, preferably laser light, if desired an adhesive layer (5) and a transparent covering layer (6) have been applied.

[0679] comprises a preferably transparent substrate (1) to whose surface a protective layer (2) if desired, at least one information layer (3) which can be written on by means of light, preferably laser light, if desired a protective layer (4), if desired an adhesive layer (5) and a transparent covering layer (6) have been applied.

[0680] comprises a preferably transparent substrate (1) to whose surface at least one information layer (3) which can be written on by means of light, preferably laser light, if desired an adhesive layer (5) and a transparent covering layer (6) have been applied.

[0681] Alternatively, the optical data carrier has, for example, the following layer structure (cf. FIG. 2): a preferably transparent substrate (11), an information layer (12), if desired a reflection layer (13), if desired an adhesive layer (14), a further preferably transparent substrate (15).

[0682] Alternatively, the optical data carrier has, for example, the following layer structure (cf. FIG. 3): a preferably transparent substrate (21), an information layer (22), if desired a reflection layer (23), a protective layer (24).

[0683] The invention further provides optical data carriers according to the invention which have been written on by means of blue, red or infrared light, in particular laser light.

[0684] The following examples illustrate the subject-matter of the invention.

EXAMPLES

Example 1

[0685] 2.2 g of 1-methyl-3-cyano-4-ethoxycarbonyl-6-hydroxy-2-pyridone and 2.0 g of 1,3,3-trimethylindole-2-methylene-ω-aldehyde were stirred in 5 ml of acetic anhydride at 90° C. for 2 hours. After cooling, the mixture was poured into 100 ml of ice water, filtered with suction and the solid was washed with water. The solid was stirred in 20 ml of water/methanol 3:1, filtered off with suction and dried. This gave 3.0 g (74% of theory) of a blue powder of the formula 138

[0686] m.p.=183-185° C.

[0687] UV (dioxane): λmax=587 nm

[0688] UV (DMF): λmax=609 nm

[0689] ε=56010 l/mol cm

[0690] Δλ=22 nm

[0691] λ1/2-λ1/10(long wavelength flank)=27 nm

[0692] Solubility: >2% in TFP (2,2,3,3-tetrafluoropropanol).

Example 2

[0693] An analogous procedure using 1.0 g of dimethylacrolein instead of 1,3,3-trimethylindole-2-methylene-ω-aldehyde gave 1.9 g (63% of theory) of a reddish violet powder of the formula 139

[0694] m.p.=160-165° C.

[0695] UV (dioxane): λmax=542 nm

[0696] UV (DMF): λmax=567 nm

[0697] ε=31630 l/mol cm

[0698] Δλ=25 nm

[0699] λ1/2-λ1/10(short wavelength flank)=42 nm

[0700] Solubility: >2% in TFP.

Example 3

[0701] 2.03 g of 3-pyridino-4-methyl-6-hydroxy-pyridone chloride and 2.0 g of 1,3,3-trimethylindole-2-methylene-ω-aldehyde were stirred in 10 ml of acetic anhydride at 90° C. for 2 hours. After cooling, the mixture was poured into 200 ml of water. 2.8 g of sodium tetrafluoroborate were added to the orange solution. After stirring overnight, the mixture was filtered with suction, the solid was washed with 20 ml of water and dried. This gave 3.3 g (74% of theory) of a reddish orange powder of the formula 140

[0702] m.p. >300° C.

[0703] UV (methanol): λmax=513 m

[0704] ε=86510 l/mol cm

[0705] λ1/2-λ1/10(short wavelength flank)=38 nm

[0706] Solubility: >2% in TFP.

Example 4

[0707] 0.7 g of 5-dimethylaminofuran-2-carbaldehyde and 1.5 g of N-methyl-N′-dodecyl-barbituric acid were stirred in 15 ml of acetic anhydride at 90° C. for 30 minutes. After cooling, the mixture was poured into 100 ml of ice water, filtered with suction and the solid was washed with water. This gave 1.7 g (79% of theory) of an orange powder of the formula 141

[0708] m.p. 118-120° C.

[0709] UV (dioxane): λmax=483 nm

[0710] ε=53360 l/mol cm

[0711] λ1/2-λ1/10(short wavelength flank)=32 nm

[0712] Solubility: >1% in benzyl alcohol.

[0713] Further examples according to the invention are shown in the following tables:

TABLE 1
(formula (VI))
Ex- ample	142	Y1	═CX1X2	λmax1)/ nm	ε/ l/mol cm	λ1/2-λ1/10/ nm	Δλ2)/ nm
5	143	C—CN	═C(CN)2	470	40990	323)	16
6	″	CH	144	502	62860	333)
7	145	CH	″	539	146480	184)	1.5
8	″	CH	146	472	70880	323)	5
9	″	CH	147	4906)	117700
10	″	CH	148	539	106640
11	149	CH	150
12	151	CH	152
13	153	CH	154	508	78400
14	155	CH	156	535	112260	134)
15	157	CH	158	483	53360
16	″	CH	159	535	128960		1.3
17	160	CH	161	5366)	115603		2
18	162	CH	163	535	112260	134)
19	164	CH	165
20	″	CH	166
21	167	N	168
22	″	C—CN	═C(CN)2
23	169	CH	170
24	171	CH	172
25	173	CH	174
26	175	CH	176
27	177	CH	178
28	179	CH	180	490	35000	403)	23
29	181	CH	182	508	153420	114)
30	183	CH	184	537	85995	165)
31	″	CH	185	469	46735
32	186	CH	187	472	62026	423)
33	″	CH	188	4325)	28360
34	189	CH	190
35	191	CH	192
36	193	CH	194
1)in dioxane unless indicated otherwise
2)= |λDMF-λ-dioxane|
3)on the short wavelength flank
4)on the long wavelength flank
5)in methanol
6)in DMF

[0714]

TABLE 2
(formula (VII))
Ex- ample	195	Y2-Y1	═CX1X2	λmax1)/ nm	ε/ l/mol cm	λ1/2-λ1/10/ nm	Δλ2)/ nm
37	196	CH—C(CN)	═C(CN)2	499	46470	363)	5
38	″	CH—CH	197	429	60390	303)	7
39	″	CH—CH	198	487	102220	353)	6
40	″	CH—CH	199	448	76260	273)	2
41	″	CH—CH	200	469	76130	283)	3
42	″	CH—CH	201	520	113100	124)	2
43	202	CH—C(CN)	═C(CN)2	511	31345	363)	6
44	203	CH—C(CN)	″	503	41530	363)	6
45	204	CH—CH	205	519	55910	114)
46	206	CH—CH	207
47	″	CH—CH	208
48	209	CH—CH	210
49	211	CH—CH	212
50	″	CH—CH	213	473	47640
51	214	CH—CH	215
52	″	CH—CH	216	496	62720
53	″	CH—CH	217	500	110332
54	218	CH—CH	219
55	220	CH—CH	221	4906)	109380		5
56	222	CH—CH	223	450
57	224	CH—CH	225	462	57230	343)
58	226	CH—CH	227	4595)	36010
59	228	CH—CH	″	4625)	24400
60	″	CH—CH	229	466	75006	104)
61	230	CH—CH	″	5126)	36610	254)	367)
62	231	═C(CN)2
63	232	CH—CH	233	5148)	63510	403)
64	234	CH—CH	235	5775)
65	236	CH—CH	″	5875)	142900
66	237	CH—CH	238	5465)
67	239	CH—CH	″	5545)	50900
1) in dioxane unless indicated otherwise
2) = |λDMF - λdioxane|
3) on the short wavelength flank
4) on the long wavelength flank
5) in methanol
6) in methylene chloride
7) = |λmethylene chloride-λmethanol|
8) in DMF

[0715]

TABLE 3
(formula (VIII))
Ex- ample	240	Y1	═CX1X2	λmax1)/ nm	ε/ l/mol cm	λ1/2-λ1/10/ nm	Δλ2)/ nm
68	241	CH	242	462	77180	283)	8
69	″	CH	243
70	″	CH	244	4465)
71	″	CH	245	5646)	89100
72	246	CH	247	480	79685		1.3
73	″	CH	248	447	84070
74	249	CH	250	482	73010		4.3
75	″	CH	251	4695)	62780
76	252	CH	253	458	89800	283)
77	″	CH	254	3906)	80200	114)
78	″	CH	255	366
79	″	CH	256	382	62900
80	257	CH	258	585	119800	284)
81	″	CH	259
82	260	CH	″	452	61685
83	261	CH	262	337
84	263	CH	264	5526)	149800
85	265	CH	266	5095)
1) in dioxane unless indicated otherwise
2) = |λDMF-λdioxane|
3) on the short wavelength flank
4) on the long wavelength flank
5) in methanol
6) in DMF

Example 86

[0716] A 4% strength by weight solution of the dye from Example 7 in 2,2,3,3-tetrafluoropropanol was prepared at room temperature. This solution was applied by means of spin coating to a pregrooved polycarbonate substrate. The pregrooved polycarbonate substrate had been produced as a disk by means of injection moulding. The dimensions of the disk and the groove structure corresponded to those customarily used for DVD-Rs. The disk with the dye layer as information carrier was coated with 100 nm of silver by vapour deposition. A UV-curable acrylic coating composition was subsequently applied by spin coating and cured by means of a UV lamp. The disk was tested by means of a dynamic writing test apparatus constructed on an optical tester bench comprising a diode laser (λ=405 nm) for generating linearly polarized light, a polarization-sensitive beam splitter, a λ/4 plate and a movably suspended collecting lens having a numerical aperture NA=0.65 (actuator lens). The light reflected from the reflection layer of the disk was taken out from the beam path by means of the abovementioned polarization-sensitive beam splitter and focused by means of an astigmatic lens onto a four-quadrant detector. At a linear velocity V=5.2 m/s and a writing power Pw=13.2 mW, a signal-noise ratio C/N=48 dB was measured. The writing power was applied as an oscillating pulse sequence, with the disk being irradiated alternately for 1 μs with the above-mentioned writing power Pw and for 4 μs with the reading power Pr≈0.44 mW. The disk was irradiated with this oscillating pulse sequence until it had rotated once. The marking produced in this way was then read using the reading power Pr≈0.44 mW and the abovementioned signal/noise ratio C/N was measured.

Example 87

[0717] A procedure analogous to that of Example 86 was used to produce and measure a disk with the dye from Example 2. At a writing power Pw=13.2 mW and a linear velocity V=2.6 m/s, C/N=45 dB was obtained.

Example 88

[0718] A disk with the dye from Example 65 which had been produced using a method analogous to Example 86 was measured in a test apparatus which was similar to that in Example 86 but differed in the diode laser (λ=656 nm) and the actuator lens (NA=0.60). At a writing power Pw=24 mW and a linear velocity V=3.5 m/s, C/N=39.5 dB was obtained.

Claims

1. Optical data carrier comprising a preferably transparent substrate which may, if desired, have previously been coated with one or more reflection layers and to whose surface a light-writeable information layer, if desired one or more reflection layers and if desired a protective layer or a further substrate or a covering layer have been applied, which can be written on or read by means of blue, red or infrared light, preferably laser light, where the information layer comprises a light-absorbent compound and, if desired, a binder, characterized in that at least one merocyanine dye is used as light-absorbent compound.

2. Optical data carrier according to claim 1, characterized in that the merocyanine dye has the formula

3. Optical data carrier according to claim 2, characterized in that the ring B of the formula (II) represents furan-2-yl, thiophen-2-yl, pyrrol-2-yl, benzofuran-2-yl, benzothiophen-2-yl, thiazol-5-yl, imidazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2- or 4-pyridyl, 2- or 4-quinolyl, where the individual rings may be substituted by C1-C6-alkyl, C1-C6-alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-acylamino, C6-C10-aryl, C6-C10-aryloxy, C6-C10-arylcarbonylamino, mono- or di-C1-C6-alkylamino, N—C1-C6-alkyl-N—C6-C10-arylamino, pyrrolidino, morpholino or piperidino, and the ring C of the formula (V) represents benzothiazol-2-ylidene, benzoxazol-2-ylidene, benzimidazol-2-ylidene, pyrrolin-2-ylidene, thiazol-2-ylidene, thiazolin-2-ylidene, isothiazol-3-ylidene, isoxazol-3-ylidene, oxazolin-2-ylidene, imidazol-2-ylidene, pyrazol-5-ylidene, 1,3,4-thiadiazol-2-ylidene, 1,3,4-oxadiazol-2-ylidene, 1,2,4-thiadiazol-5-ylidene, 1,3,4-triazol-2-ylidene, 3H-indol-2-ylidene, dihydropyridin-2- or -4-ylidene, dihydroquinolin-2- or -4-ylidene, where the individual rings may be substituted by C1-C6-alkyl, C1-C6-alkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-acylamino, C6-C10-aryl, C6-C10-aryloxy, C6-C10-arylcarbonylamino, mono- or di-C1-C6-alkylamino, N—C1-C6-alkyl-N—C6-C10-arylamino, pyrrolidino, morpholino or piperidino.

4. Optical data carrier according to one or more of claims 1 to 3, characterized in that the merocyanine dye has the formula (VI)

5. Optical data carrier according to one or more of claims 1 to 3, characterized in that the merocyanine dye has the formula (VII)

6. Optical data carrier according to one or more of claims 1 to 3, characterized in that the merocyanine dye has the formula (VIII)

7. Optical data carrier according to one or more of claims 1 to 6, characterized in that the merocyanine dye of the formula (I) has a solvent-induced wavelength shift Δλ of <20 nm, where Δλ=|λDMF−λdioxane|, viz. the positive difference between the absorption wavelengths in the solvents dimethylformamide and dioxane.

8. Optical data carrier according to one or more of claims 1 to 6, characterized in that the merocyanine dye has a dipole moment difference Δμ of <5 D, where Δμ=|μg−μex|, viz. the positive difference between the dipole moments in the ground state and the first excited state.

9. Use of merocyanines in the information layer of write-once optical data carriers, where the merocyanines have an absorption maximum λmax1 in the range from 340 to 410 nm, a λmax2 in the range from 420 to 650 nm or a λmax3 in the range from 650 to 810 nm.

10. Use of merocyanines in the information layer of write-once optical data carriers, where the data carriers are written on and read by means of blue laser light.

11. Process for producing the optical data carriers according to claim 1, which is characterized in that a preferably transparent substrate which may, if desired, have previously been coated with a reflection layer is coated with the merocyanines, if desired in combination with suitable binders and additives and, if desired, suitable solvents, and provided, if desired, with a reflection layer, further intermediate layers and, if desired, a protective layer or a further substrate or a covering layer.

12. Optical data carrier according to claim 1 which can be written on by means of blue, red or infrared light, in particular laser light.

13. Merocyanines of the formula (CI)