TW557322B - Novel benzo [4,5] imidazo [2,1-a] isoindol-11-ones, the composition comprising the same, the process for the preparation of said composition, and the applications thereof - Google Patents

Abstract

A composition comprising (a) an effective amount of a guest chromophore embedded in a matrix of a host chromophore, or (b) a host chromophore and an effective amount of a guest chromophore both embedded in a polymer matrix, wherein the absorption spectrum of the guest chromophore overlaps with the fluorescence emission spectrum of the host chromophore, and wherein the host chromophore is selected from the group consisting of benzo [4,5] imidazo [2,1-a] isoindol-11-ones.

Description

Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention (l) The present invention relates to a composition which contains (a)-an effective amount of a guest chromophore embedded in the main chromophore matrix Or, (b) —the host chromophore and an effective amount of guest chromophore are embedded in the polymer matrix, where the absorption spectrum of the guest chromophore overlaps with the fluorescence emission spectrum of the host chromophore, and Wherein the main chromophore is selected from the group consisting of benzo [4,5] imidazo [2, Ι-a] isonazin-11-ones. What's more, the present invention relates to a method for preparing the composition. A polymerizable composition containing the product, and the contained carrier is a highly embossable polymerizable photoresist material containing the composition. Composition • There is a method for preparing a fluorescent high relief image on a carrier, there is a use for the use of the composition as a fluorescent material, especially for an electroluminescent device, and there is a novel non-functional group Benzo [4,5] oxazo [2, Ι-a] isoazaindene-U-one derivatives. Composition containing host chromophore and guest hip chromophore dissolved in it • This dissolution can produce a material with enhanced fluorescence and a large difference between maximum absorption and maximum emission. This composition is highly sought after Materials, which have a wide range of potential and practical technical applications. The large difference between the maximum absorption (excitation) and the maximum emission is due to the resonance energy transfer between the individual host chirp and the guest chromophore. The possibility of energy transfer between chromophores with regions where the absorption spectrum of the guest chromophore and the fluorescence emission spectrum of the host overlap is well known. For example, H. Port and his research colleagues described in Z. Naturforsch., 36a, pp. 697 to 704 (1981), erbium-doped dibenzofuran or benzodihydroindene mixed crystals-3 -This paper size applies to China National Standard (CNS) A4 (210X297 mm)

557322 A7 B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (>) The body has enhanced fluorescence in the U V area at temperatures below 100K. However, low temperature fluorescence has no practical value and is only scientific interest. CW Tang and his research colleagues in J. Appl. Phys., 65, pp. 3610 to 3616 (1989) disclosed a multi-calendar electric luminescent device containing a light-emission calendar composed of 8-hydroxyquinoline aluminum. A region doped with fluorescent molecules, such as coumarin. The device displays improved electroluminescence and Stoke color shift depending on the specific dopant. The manufacture of this device is extremely complex and therefore unsuitable for industrial manufacturing. J · M · L a τιg and his research colleagues in J · P hys · C he in. 97, pages 505 8-5064 (1993) mentioned the combination of coumarin as the main body and rhodamine as the object, Both of these components were dissolved in polyacrylic acid * but the study only showed enhanced fluorescence under high pressure. W0 93/23492 shows fluorescent particles with enhanced Stokes shift. It contains soluble and fluorescent host and guest dyes that absorb or bond to polymeric particles. This material is used for the optical measurement of nucleic acids such as DNA or RN A. Unfortunately, the solid state fluorescence of these particles is not good. US 5, 2 2 7 and 2 5 2 disclose a fluorescent composition in which 8-hydroxyphosphonium aluminum is the main body and quinacridone is the guest. Similarly, JP-A-05 320 633 discloses a fluorescent composition in which 8-hydroxyquinoline aluminum is a main component and diketopyrrolopyrrole is a guest falcon. However, in both documents * the objects are insoluble materials * and they are mainly dissolved as small cross product spheres. The small volume sphere is produced because the preparation method is a co-sublimation method. These materials have larger Stokes offset fluorescence than the general single-component fluorescent materials to be used and are, for example, -4- (Please read the precautions on the back before this page) ϋϋ ϋϋ ϋ · ^ IL · — ϋ_ϋ ^ 1- ^ 1 ϋ ^ ϋ --5

-, I. This paper size is in accordance with Chinese National Standard (CNS) A4 specification (21 〇 × 297 mm) 557322 A7 B7 V. Description of the invention (Clever) Use as a light emitting material for electrical cold light device. The manufacturing cost of such equipment is extremely high, which ensures the precise control of manufacturing conditions such as vacuum and temperature to achieve the required mixed materials. This method is not suitable for large-scale manufacturing. Preparation of 1,2,3,4-tetrachlorobenzo [4, 5] imidazo [2, bua] isoazepine in the presence of a hydrocarbon selective solvent in EP-Α-0 4 56 6 09 And its derivatives. These compounds are pigments that exhibit solid fluorescence and have improved outdoor durability. It was also mentioned that 9 5% yellow 1,2,3,4-tetrabenz [4, 5] imidazo [2, bua] isoazepine-11-pyrene and 5% indanthrene blue Combination produces green fluorescent pigments. Therefore, this system is a pigment compound, in which the generation of a new color is only the sum of the two component colors. This color is not due to the formation of the complex required for close interaction between the components of the mixture, the molecule Hiragaki * energy transfer process *, is cut out. FW · Harris and his research colleagues in ACS Synip. Ser. 132, 39 (1980) mentioned 1,2,3,4-tetraphenylbenzo [4,5] imidazo [2,1- &] Please Read the back notice first

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Without radicals, benzene is formed. The research is designed to be used in the system, and the materials and materials are used to make the spacecraft. The ketone is 1-, Tltt, and indoxazolium nitrogen isomerized. It is printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. The lack of description above shows that there are hundreds of light-emitting luminescent screens that can be used to provide the system.

For the sake of comparison, the light emitted by the responding group is better than the fluorescent group, and the group of the enhanced light has the I-spectrum magnetoelectricity of the fluorescent light. It is obvious that this paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297mm) printed on the paper scale. Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (α)-Use of UV and visible area All wavelengths can be excited *-Shows excellent light stability and outdoor durability ·-Shows the emission spectrum of Guangfanyuan through «wave (color adjustment)] of appropriate guest molecules,-has high thermal stability, Is prepared, ie, by (co) precipitation method, -can be used to prepare an electroluminescent device · if the host chromophore is selected from the group consisting of benzo [4, 5] imidazo [2, Ι-a] isoazepine "-11-ones" means benzo [4,5] imidazo [2, Ι-a] isoazaindene-11-fluorene derivatives as a basic substance. Furthermore, the enhancement factor of the present invention should preferably be positive and at least 1.3, more preferably at least 2 and more preferably at least 5. As used herein, "enhancement factor" is defined as a factor that increases or decreases based on the peak height emission intensity of a solid powder containing the fluorescent part of the host and the guest compared to the same powder that does not contain any fluorescent guest component . As long as the wavelength of the excitatory radiation is the same • The comparison can be considered true. In general, when compared to the same material without the composition of the guest hip, the emission wavelength of the subject / guest material results in a longer wavelength (lower energy). Therefore, a composition was found that contained (a)-an effective amount of the guest chromophore embedded in the host chromophore matrix * or (b)-both the host chromophore and an effective amount of the guest chromophore. Embedded in a polymer matrix, where the absorption spectrum of the guest chromophore overlaps with the pyrene light emission spectrum of the main hip chromophore, and the host chromophore is selected from the group consisting of benzo [4, 5] oxazo [ 2,1- This paper size applies to China National Standard (CNS) A4 (210X297 mm)

557322 A7 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

i. Description of the invention (ί) a] Isoazakyl-11-ones. What's more, a method for preparing the composition and a polymerizable composition containing the composition is also found. The carrier included is a composition of a highly embossable polymerizable photoresist material containing the composition, and a preparation method Method for fluorescent high relief image on a carrier, the composition is used as a fluorescent material, especially for an electroluminescent device, and a novel non-functionalized benzo [4, 5] imidazo [2, Ι -a] isoazepin-11-fluorene derivatives. The first specific embodiment of the present invention consists in a composition * which * comprises (a)-an effective amount of guest hip chromophores embedded in the host chromophore matrix, or (b)-the host hair color The chromophore and an effective amount of the guest chromophore are embedded in the polymer matrix, where the absorption spectrum of the guest chromophore overlaps with the fluorescence emission spectrum of the main chromophore • and the host chromophore is selected from the group consisting of Benzo [4,5] imidazo [2, I-a] isoazepin-11-ones. The main chromophore is selected from the group consisting of benzo [4, 5] imidazo [2, Ι-a] isoazepine-11-_ derivatives and benzo [4,5] pyrazolo [2,1 ^ ] Isoindene-1B_ itself (hereinafter referred to as benzimidazoisoisoindane). These compounds are preferably derivatives which are soluble in organic or aqueous solvents. In the scope of the present invention, the solubility of the host chromophore means that the benzimidazoloisoazaindenone derivative is preferably at least 10 g, more preferably at least 50 mg, and most preferably at least 100 g. * 0 dissolved in 1 liter of solvent such as dimethylformamide. It can be judged by oneself that the solubility is higher at elevated temperature and depends on the choice of solvent. The benzimidazoisoindenones can be corresponding to formula I. Please read first | read back I

I thing I item I

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This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 A7 B7 V. Description of invention (heart) 〇

Among them, the vicinal carbon atoms of benzene 1 and 2 are unconfirmed or condensed with a heterocyclic ring, a heterocyclic ring, or a heteroalicyclic ring, and the condensed ring of benzene ring 1 or 2 or both Some or all are unsubstituted or substituted with an organic group and / or a halogen atom. The group forming the condensed ring is preferably selected from the group consisting of divalent residues of the formula -CH = CH-CH = CH- »-CH = CH-N = CH- * -CH = CH-CH = N- * -CH = n_CH = N- · -CH = CH-NRg-, -CH = N-CH2 -CH = CH-S-, -CH = CH +,-(CHz) 3 ·, _ (CH2) 4-· -CHz- CHz -NRg-CHz —, — ch2-CH2 -CHz -NR9-, -CHz -CH2 ~ 〇 ~ CH2 — $ -CHz -CH2 -C Hz -G-, «CHz -CH2 -S-CH2 —f -ch2 -CHz -CH2 -s- ^ -CH2 -0 -C Hz ~ *-CHz -CHz -0-, -CH 2 ~ S ~ CH 2 and printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs -CH2 -CH2 -S -,; wherein R! Is 1 ^ or an organic substituent 'and the divalent residues are unsubstituted or substituted with a fluorenyl group.

Rt is an organic substituent which may be linear or branched Ci to Cz alkyl, C5 to C7 cycloalkyl, benzyl, or R2-c (o)-, where R2 is unsubstituted or substituted by F, C1 or CiSCi2 alkoxy-substituted Ci to C20 alkyl, or unsubstituted or substituted (: 1.01 to (: 12 -8-This paper size applies to Chinese National Standard (CNS) A4 specifications (210X297 male f) 2 2 73 5 5 A7 B7 Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Five Ministry of Economic Affairs. (1) Alkyl or Ci to Ci 2 alkoxy substituted Cs to C7 cycloalkyl, phenyl or benzyl. Please Read Back Matters

Preferable examples of Ri are fluorene, methyl • ethyl • propyl • butyl • pentyl * hexyl, benzyl, methylbenzyl * dimethylbenzyl, ethylfluorenyl * propanyl, Butanyl, benzyl-C (0)-, phenyl-C (0)-, methylbenzylmethyl-c (o)-, single, dione or tris (1,4-ethyl) ethyl, and single, dione Or trisfluorofluorofluorenyl, mono- and dichlorophenyl-c (o)-. Available from c 1 3 to C i cycloalkyl to C i heteroarane • C 6 C 1 2 c 1 7 cycloalkylthioalkylalkylthio, so- to C i -S 0 2, C 1 8 machine The group substituent may conform to halogen, -CN, No2, (: ^ to alkyl to ci8 alkenyl, C2 to Cl8 alkynyl, Ci 8 carboyl, Cl to Ci 8 _ sulfonyl, Cs to Cl 2, C 6 to (: 1 8 aryl, C 5 to (7 7 heteroaryl, C 3 2 cycloalkylalkyl, c 6 -C 8 aralkyl · C 5 to Ci 7 group, Ci to (1 18 alkane) C3 to Ci 2 cycloalkoxy to Ci 8 aryloxy C5 to Ci 7 heteroaryloxy C3 to cycloalkylalkoxy C6 to (^ 8aralkoxy * CS to heteroaryl Alkoxy · Ci to (: 1 8 alkylthio * C3 to (: 1 2 thio, C6 to Ci 8 arylthio, C5 to Ci 7 aryl, C3 to 0 2 cycloalkylalkyl Thio, C6 to (: i 8 aryl, C 5 to Ci 7 heteroaralkylthio, Cl to Ci 8 alkane or -S〇2, C3 to C 1 2 cyclofluorenyl-SO- or-S〇2 , Ce 8aryl-SO- or -S02, C5 to C1 7 aryl-SO-or, C3 to Ci 2 cycloalkylalkyl-so- or -S02, c6 to aralkyl-SO -Or- S〇2, Ci to (: 1 8 alkyl-CO-, c6) This paper is applicable in National Standard (CNS) Α4 specification (210 × 297 mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (again) to Ci δ-aryl-c0_, C3 to Cl 2 cycloalkyl, C6 to

Ci 8 aryl-C0-, Cs to ^^! 7 heteroaryl-C0- · C3 to Cl 2 cycloalkylalkyl- C0-, c6 to (^ aralkyl-C〇-, C5 to (^ 7

Heteroarylfluorenyl-CO-, -NR3 R4, alkoxyalkyl having 2 to 20 carbon atoms, polyoxyalkylene -ORe, -X- (R5 IU .-X- (Rs) kC (〇)- 〇Re ^ -X- (Rs) k-S02 -0R6, -X-U5) kS〇2 -NRs R4, _NH-C (0) -R6 and -〇_C (0) -R6 where R3 and R4 are respectively Is H, Ci to Cz. O'yl-'cyclopentyl 'cyclohexyl, benzyl, Ci to Ci £ alkylphenyl, or Ci to Ci 2 amidylbenzyl, or Ri i and Ri 2 together are tetramethylene The group 'pentamethyl or -CH2 CH2 CHz-or -CH2 CHz -NRi 5 _CH2 CH2-group, R5 is Ci to ^ 2 alkylene, phenylene or phenylene, R6 means fluorene, Ci to (: 2 alkyl, cyclopentyl, cyclohexyl, benzyl, benzyl, Ci to Ci 2 fluorenyl benzyl or Ci to Ci 2 fluorenyl benzyl, X is a direct bond, -0- or s , K is 0 or 1, and its acid species. The preferred species are Sickle Gold Clam and Sickle Gold Clam, such as those obtained from Li · Na, R * Mg, Ca, Sr · Bao cycloaliphatic And aromatic residues (substituents of organic groups) can also be substituted-10- This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) "

557322 kl B7, for example substituted MF, Cl or Br, -CN, -N02, Ci to 〇8 alkyl, C3 to C12 cycloalkyl, € 6 to (: 18 aryl, C3 to Ci 2 Cycloalkylalkyl, C6 to Ci 8 aralkyl · C5 to (: 1 7 heteroaralkyl, Ci-Ci 8 alkoxy, C3 to 〇 ^ 2 cycloalkoxy * C 6 to Ci 8 aryl In the context of the present invention, the alkyl substituent may be linear or branched, and contains 1 to 12, preferably 1 to 8, most preferably 1 to 6, and particularly preferably 1 to 4 Carbon atoms. Some examples are methyl • ethyl, n- or iso-propyl, n- or iso- or tertiary butyl, and pentyl, hexyl, heptyl * octyl, nonyl, decyl Isomers of amyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl. In the present invention, the halogen of the organic substituent may be F, C1, Br or I. Preferably, the halogen of the organic substituent may be linear or branched, and may contain 2 to Twelve, preferably two to eight, most preferably two to six, and particularly preferably two to four carbon atoms. Some examples are vinyl, allyl, methylvinyl, but-1-en-4-yl, but-2-en-4-yl, but-3-en-4-yl, 3-methyl Prop-1-en-3-yl, and pentenyl, hexenyl, heptyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecane Alkenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, and octadecenyl isomers. In the context of the present invention, alkynyl substituents may be linear Or branch with -11- This paper size applies to China National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the back before filling in the page) ----- Order

Printed by the Employees' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of Invention (ί (7) There are 2 to 12, preferably 2 to 8, most preferably 2 to 6, and particularly preferably 2 to 6 4 carbon atoms. Some examples are ethynyl, crotonyl, methylethynyl, but-1-yn-4-yl, but-2--2--4--4-yl, but-3-yn-4- Isomers of the 3-methylprop-1-yn-3-yl, and nonyl, nonynyl, decynyl * decynyl * tetradecanyl, pentadecyl and octadecynyl groups In the present invention, the hydroxyl group contains 1 to 12, preferably 1 to 4 carbon atoms, particularly preferably pentynyl, hexynyl, heptynyl, octynyl-alkynyl, dodecynyl, Tridecanealkynyl * hexadecynyl * heptadeynylalkyl substituents may be from 1 to 8, preferably 1. Some examples are hydroxymethyl or branched * to 6 * Alkyl · hydroxyethyl, n- or iso-hydroxypropyl, n- * iso-or tertiary monohydroxybutyl, and hydroxypentyl, hydroxy • hydroxydecyl, hydroxyalkyl, hydroxytetradecyl Heptaalkyl and hydroxy are in the content or branch of the present invention, and contain 16 and are particularly preferred Or I, and preferably F or chloromethyl, fluoromethyl, iso-chloropropyl, n-hexyl fluorenyl-k group, octadecane, there are up to 12 1 to 4 C1. Isomers of hydroxyheptyl and hydroxypentadecyl are substituted. • Preferred is one carbon atom. For example, please read the precautions on the back before m. Benzyl * hydroxyoctyldodecyl, hydroxydecyl 1 to 8 halogen alkane groups of 0 groups. The halogen may be chloromethyl * dimethyl • chloroethylchlorobutyl * allyl · hydroxynonon, hydroxytridecane, and hydroxy may be 1 or more. To F * C, Br, chloromethyl * triyl, n- or fluoroethyl and all

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs, difluoromethyl * lanfluoro, iso- or tertiary mono-fluorobutyl. In the content of the present invention, the cycloalkyl substituent preferably contains 4 to 8 and -12- This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 2 2 73 5 5 A7 B7 The Central Bureau of Standards Bureau ’s Consumer Cooperatives printed invention descriptions (0) more preferably 5 to 7 ring carbon atoms. Some examples are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclododecyl. Preferred radicals are cyclopentyl and cyclohexyl. In the content of the present invention, the aryl substituent may be a aryl group or preferably a phenyl group. In the content of the present invention, the heteroaryl substituent preferably contains 5 or 6 ring atoms, and preferably has 1 to 3 , More preferably 1 or 2 heteroatoms selected from the group consisting of 0, S, N. Some examples are pyridyl, pyrimidinyl, furyl, pyrrolyl and fluorenylphenyl. In the context of the present invention, the cycloalkylalkyl substituent is preferably cycloalkylmonomethyl or monoethyl, and cycloalkyl preferably means cyclopentyl or cyclohexyl. In the context of the present invention, the aralkyl substituent is preferably an aryl monomethyl or monoethyl group, and the aryl group preferably means a phenyl group or a tea group. Some examples are benzyl, phenylethyl, and tidylmethyl. In the context of the present invention, the heteroaralkyl substituent is preferably a heteroaryl monomethyl or monoethyl group, and the fluorenyl group preferably contains 5 or 6 ring atoms, and preferably has 1 to 3, more Preferably, 1 or 2 heteroatoms are selected from the group consisting of O, S, and N. Some examples are pyridylmethyl or monoethyl, oxidyl, furylmethyl, pyrrolylmethyl and thiophenylmethyl. In the context of the present invention, the alkoxy group of the organic substituent may be linear or branched, and contains 1 to 12, preferably 1 to 8, most preferably 1 to 6, and particularly preferably 1 to 4 carbon atoms. Some examples are methoxy * ethoxy, n- or iso-propoxy, n-, iso- or tertiary-butoxy, -13- This paper size applies to China National Standard (CNS) A4 specifications ( 210X 297 mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (4) and pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decoxy, Isomers of undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy In the context of the present invention, the cycloalkoxy substituent preferably contains 4 to 8 and more preferably 5 to 7 ring carbon atoms. Some examples are cyclopropoxy * cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy * cyclooctyloxy and cyclododecyloxy. Preferred radicals are cyclopentyloxy and cyclohexyloxy. In the context of the present invention, the aryloxy substituent may be mandoxy or preferably phenoxy. In the context of the present invention, the heteroaryloxy substituent preferably contains 5 or 6 ring atoms, and preferably has 1 to 3 *, more preferably 1 or 2 heteroatoms selected from the group consisting of 0, S, and N. Some examples are pyridyloxy, pyrimidinyloxy, furanoxy * pyrrolidinyl and thiophenoxy. In the context of the present invention, the cycloalkyl-alkoxy substituent is preferably cycloalkyl-methoxy or monoethoxy •, and the cycloalkyl group preferably means cyclopentyl or cyclohexyl. In the context of the present invention, the aralkyloxy substituent is preferably an aryl monomethoxy group or a monoethoxy group, and the aryl group preferably means a phenyl group or a tea group. Some examples are benzyloxy, phenylethoxy, and tylmethoxy.

In the present invention, the heteroarylalkoxy substituent is preferably a heteroaryl monomethyl or monoethyl group, and the heteroaryl group preferably contains 5 or 6 ring atoms, and preferably has 1 to 3 * More preferably, 1 or 2 heteroatoms comply with 0, S -14- This paper size applies to China National Standard (CNS) A4 (210X297 mm)

557322 A7 B7 V. Description of the invention (Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, N. Aromatics are based on and contain particularly good bases, n-, and pentyl, decylthio, hepta-alkyl and more The thio group is preferably benzene, and the cyclic group is selected from the group consisting of clinylfurfuryl and cyclohexyl. Examples are pyridylmethoxy or monoethoxy, pyrrolylmethoxy and fluorenylbenzene. In the content, the alkyl fluorenyl substituent is 1 to 12, preferably 1 to 8, and most 1 to 4 carbon atoms. Some examples are oxy, pyrimidinyloxy, and methoxy. It may be linear or Branching, preferably from 1 to 6 and methylthio, ethylthiomono or isopropylpropylthio, n-mono or iso- or tertiary monobutylthiothiothiotetradecane The thio group and the present invention are preferably a thio group, a thio group, and a cyclic group. The thio group of the present invention is the basic inventor, and contains 0 * sulfanylthio. The methylthio group of the present invention. In the content of octadecylsulfur, among the content of ring to 7 ring carbocyclopentylthiododecylsulfur, the content of aryl is preferably 1 S, N. Partial, pyrrolyl • Cyclic or isoethyl sulfur atoms of monoethyl, heptylthio, pentaalkyl. Cyclohexyl. Thiothio * Dodecylthio Examples of the substituents are thiol, octylthio, nonylthio, hexadecylthio, tridecyl, and decyl preferably contains 4 to 8 members as cyclopropylfluorenyl. ,, cycloheptylfluorenyl, the ring substituent may be a thiothio group or more than 5 or 6 to 3 aryl substituents, more preferably 1 or 2 heteroatoms. An example is pyridylthio. Radical, pyrimidinylthiothio and thiophenylthio. The alkyl-alkylthio substituent is preferably epithio, and the cycloalkyl is preferably cyclopentyl-15.-Applicable to this paper size China National Standard (CNS) A4 specification (210X297 mm)

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557322 A7 B7 5. Description of the Invention (In the context of the present invention, the aralkylthio substituent is preferably aryl-methylthio or monoethylthio, and aryl is preferably phenyl or Tuji. Some examples are benzylthio, phenylethylthio, and thiomethylthio. In the context of the present invention, the heteroaralkylthio substituent is preferably a heteroaryl-methylthio or monoethylthio group, and the aryl group preferably contains 5 or 6 ring atoms, and preferably has One to three, more preferably one or two, heteroatoms are selected from the group consisting of 0, S, and N. Some examples are pyridylmethylthio or monoethylthio, pyrimidinylthio, furylmethylthio, pyrrolylmethylthio and tellurylphenylmethylthio. In the context of the present invention, the alkyl-so- or -so2-substituent may be linear or branched, and contains 1 to 12 * preferably 1 to 8 * most preferably 1 to 6 and particularly preferably For 1 to 4 carbon atoms. Some examples are methyl-S0- or -S〇2-, ethyl-so- or -S〇2-, n- or isopropyl-so- or -S〇2-, n-one or hetero- Or tertiary monobutyl-SO- or -S〇2 and pentyl-SO __- S〇2_, hexyl-SO- or -S〇2- -heptyl-SO- or -S〇2-, octyl -SO- or -S〇2-, nonyl-so- or -S〇2-, decyl-so- or -S〇2-, fluorenyl--fluorenyl-SO- or -S〇2-, ten Dialkyl-s0- or -s〇2-'Printed alkyl-SO- or -S02-, Tetradecyl-SO- or -S〇2-, Tensyl-SO- or -S〇2-printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Pentaalkyl-S 0-or -S 0 2-, hexadecyl-s 0-or -S 0 2--heptadecyl -s 0-or -S02-and octadecyl -SO- or -S02- isomer. In the context of the present invention, the cycloalkyl-SO- or -S02- substituent preferably contains 4 to 8 and more preferably 5 to 7 ring carbon atoms. Some examples are cyclopropyl-SO- or -S〇 2 _, cyclobutyl-SO- or -S〇 2-, cyclopentyl-SO- or -16-. This paper applies Chinese national standard (CNS) A4 specification (210X 297 mm) 557322 A7 B7 V. Description of the invention (J) -S02-, cyclohexyl -so- or -S02-, cycloheptyl -SO- or -S〇 2-, cyclooctyl-SO -Or-S02- and cyclododecyl-SO- or -S02-. Preferred groups are cyclopentyl-so- or -Soz- and cyclohexyl-SO- or -S02-. In the context of the present invention, the aryl-so-or-S02-substituent may be a thio-SO- or -S02- or preferably a phenyl-so- or -S02. In the context of the present invention, The heteroaryl-SO- or -S02- substituent preferably contains 5 or 6 ring atoms, and preferably has 1 to 3 · more preferably 1 or 2 heteroatoms selected from the group consisting of 0, s * N . Some examples are benzyl_so- or -S02-, pyrimidinyl-SO- or -S02-, furyl_s0- or " * s〇2_, pyrrolyl-SO- or -S02- and Thiophenyl-SO- or -SO2 In the context of the present invention, the cycloalkyl-alkyl-SO- or -SO2-substituent is preferably cycloalkyl-methyl-SO- or -S O2- or monoethyl-so- or -S02-, and cycloalkyl preferably means cyclopentyl or cyclohexyl. Printed in the context of the present invention by the Consumers' Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs. The aralkyl-SO- or -s02-substituent is preferably aryl-methyl-SO- or -S02- or -ethyl. The radical -SO- or -S02- .. and aryl preferably means phenyl-so- or -S02- or tardyl-SO- or -S02-. Some examples are stupid methyl-SO- or -S02-, phenylethyl-SO- or -S02- and tsamethyl-SO- or -S02-. In the context of the present invention, the heteroaralkyl-SO- or -S02-substituent is preferably heteroaryl-methyl-80- or -S02- or -ethyl-SO- or -S. 2-, and the heteroaryl group preferably contains 5 or 6 ring atoms, and preferably has 1 to 3 ', more preferably 1 or 2 heteroatoms, and optionally contains 0, s, N. Some examples are pyridylmethyl-SO- or -S〇2-or monoethyl-SO- or -S〇2 sulfanyl-1 7-This paper size applies to China National Standard (CNS) A4 specifications (210X297 (Mm) 557322 A7 B7 V. Description of the invention (mountain) -so- or -S〇2-, furan-SO- or -S〇2-and sulfur are based on the content of the present invention and contain 1 to 12, compared with base A -So- or -s02 ·, atrylmethylphenylmethyl-SO- or -S02-. The alkyl-CO-substituent may be linear or branched, preferably from 1 to 8, most preferably from 1 to 6 •, and particularly preferably from 1 to 4 carbon atoms. Some examples are methyl-C0-, ethyl-C0-, n- or iso-propyl-C0-, n- or iso- or tertiary mono-butyl-C0-, and pentyl-C0-, -C0-, decyl-C0-, hexyl-C0-, tetradecyl, heptadecyl-C0- and ten or more in the context of the present invention are 5 to 7 cyclobutyl-C0- , Cyclopentyloctyl-C0- and cyclododecylhexyl-C0-. Hexyl-C0-'heptyl-C0-, octyl-C0-, nonundecyl-C0-, dodecyl-C0-, tridecyl-C0-, pentadecyl-C0-, hexadecyl Alkyl-C0-octadecyl-C0- isomers. The cycloalkyl-C0-substituent preferably contains 4 to 8 ring carbon atoms. Some examples are cyclopropyl-C0- · -C0-, cyclohexyl-C0-, cycloheptyl-C0- · cycloyl-C0-. Preferred radicals are cyclopentyl-C0- and cyclo

It is printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. In the context of the present invention, the * aryl-C0-substituent may be d-C0- or more preferably benzyl-C0-. In the context of the present invention, the heteroaryl-CO-substituent preferably contains 5 or 6 ring atoms * and preferably has 1 to 3, more preferably 1 or 2 fluorene atoms selected from the group consisting of 0, S, N . Some examples are pyridinyl-C0-, pyrimidinyl-C0-, furyl-CO-, atryl-C0- and thiophenyl-C0-. In the context of the present invention, the cycloalkyl-alkyl-C0-substituent is preferably cycloalkyl-methyl-C0- or monoethyl-C0-, and cycloalkyl is preferably cyclopentyl-18 -This paper size applies to China National Standard (CNS) A4 (210X 297mm)

2 2 73 5 5 A7 Description of the Invention (β) or cyclohexyl. In the context of the present invention, the aralkyl-CO-substituent is preferably aryl-methyl-C0- or monoethyl-C0-, and aryl is preferably a benzyl group or an aryl group. Some examples are benzyl-C0-, phenylethyl-C0- and d-methyl-C0-. The heteroaralkyl-C0-substituent is preferably heteroaryl-methyl-C0- or monoethyl-C0-, and the fluorenyl group preferably contains 5 or 6 ring atoms, and preferably has 1 to 3, more preferably 1 or 2 (heteroatoms) self-contained 0, S, N. Some examples are pyridylmethyl-C0- or monoethylfurylmethyl-C0 ... pyrrolylmethyl-C0- and in the context of the present invention, please read the precautions beforehand. Cooperative printed -C0- * Thiobenzene contains more than 1 group * A, ethoxyethoxy groups up to 12 ethene R 6 contains 1 to and better than S • Oh The methyl group of the present invention is preferably 2 to 4 oxypropylmethylpentyl groups, and the present invention and preferred are -C0- * -C 0-° content to 8 carbon atoms. "Methyl * ethoxyethoxy content Medium is 2 to, 1, 2-or 1, 3-, preferably fluorene or Ci. In the context of the present invention, there are 1 to 12 carbons and 6 carbon atoms, * alkoxy and the best. Part of the oxybutyl ethylhexyl, polyoxy 6 oxo propyl to C 4, when the R atom, and especially alkyl substituents preferably contain 2 to 6 carbon atoms. Examples of alkane are methoxyethyl, methyl * methoxypentyl * methoxy, ethoxypropyl, ethoxypropoxymethyl and butoxymethene-0-R6 substituents are preferred Alkenyl units in which alkylene or 1,1,3- or 1,4-alkylene are used. 3 and R4 are sickle or branched, preferably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. 19-2 to 12 ethoxyoxyethylhexyl butyl. Containing 2 is preferably butyl. Alkyl *, best example

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This paper size applies to Chinese National Standard (CNS) A4 specification (210X29 * 7 mm) 557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention () Methyl, ethyl, positive one or different Monopropyl, n- or iso- or tertiary monobutyl, and pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, ten Isomers of tetraalkyl, pentadecyl, hexadecyl, decyl and octadecyl. In the context of the present invention, when R3 and R4 are alkylphenyl, they are more preferably Cjl to C8 alkylphenyl and Ci to fluorene 4-alkylphenyl. Some examples are methylphenyl, ethylphenyl, n- or iso-propylphenyl, n-, iso- or tertiary monobutylphenyl, hexylphenyl, octylphenyl, dodecane Phenyl, and dimethylphenyl. In the context of the present invention, when R3 and R4 are alkyl benzyl, they are preferably Ci to C8 alkyl benzyl * Ci to C4 alkyl benzyl. Some examples are methyl benzyl, ethyl benzyl, n- or iso-propyl benzyl, n-, iso- or tertiary mono-butyl benzyl, hexyl benzyl, octylbenzene Methyl, dodecyl benzyl, and dimethyl benzyl. In the context of the present invention, R3 and R4 are preferably Η Ci to C4, cyclohexyl, phenyl, benzyl, C, to 0,4 alkylphenyl or Ci to c4 alkylbenzyl, or Rs and R4 have a tetramethylene group, a pentamethyl group, or a -CH2 CH2-O-CH2 CH2- group in total. In the present invention, when Rs is an alkylene group, it is preferably C i

I to c6 alkylene, Cl to 〇4 alkylene. Some examples are dimethyl, propyl, propyl or butyl. R5 is most preferably methyl, ethyl, phenyl or phenylene. In the context of the present invention, when R6 is a linear or branched alkyl group, it contains -20- This paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) (Please read the precautions on the back before filling this page ) Order

557322 A7 B7 V. Description of the invention (β) 1 to 12 carbon atoms • More preferably 1 to 8 carbon atoms 9 most preferably 1 to 6 carbon atoms 9 and particularly preferably 1 to 4 carbon atoms. Some examples are methyl, ethyl, n- or iso-propyl $ n- or iso- or tris-monobutyl, and pentyl, hexyl, heptyl, octyl t nonyl • decyl, eleven Isomers of alkyl * dodecyl, decadecyl, tetradecyl, pentadecyl, cetyl, heptyl and octadecyl 0 R 6 is preferably Η t C 1 To C 1 Z alkyl, cyclopentyl, cyclohexyl, phenyl, phenylmethyl. Examples of substituents are F 9 C 1, Br, methyl, ethyl, propyl, butyl, hexyl $ methoxy * ethoxy, propoxy, butoxy · hexyl # methylthio $ Ethylthio 9 Methyl mono or ethyl-S0-methyl-r or ethyl-S 0 2, phenyl, benzyl, tolyl * xylyl * • methylbenzylmethyl »dimethyl Phenylbenzyl * diphenylphenyl »Diphenylphenyl, methoxyphenyl f mono- * methoxyphenyl 9 methoxybenzyl t dimethoxybenzyl, CH3 -co- $ 9 C 6 Hs -C0-, ch3 -C0- 0-, c6 Hs -C 0 * 0-, CH3 -S 0 2-0-, C6 Η 5 -S 0 2 -0- •-N Η 2 '-NHCH3 f -NHC 2 Hs 1 丨-NHC8 Η 1 7 > -N (CH3) zf -C00H, -C 0 · OCH3,,-CO-OCz Η 5 t -S03 Η * -SO2-OCHa, -SOz -OCz Hs »« CO-NHz * -CO-NCH3 · -CO-NHCz Hs (Please read the notes on the back before filling this page)

, 1T

Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs -C0-MHC8 7, -C0-HH (CH3) 2, -S〇2 -NH2 · -SOz -NHCH3 »-S02 -NHC2 Hs» ~ S〇z " NHCe Hi 7 -SO2 _N (CH3) 2, H2 N-SO2-, methoxymethyl 'methylamino, ethoxyethyl,-(OCH2 CH2) 2-0H, -CN and -NO2- . The number of substituents is any number and it depends on the synthetic possibility, which is 萤 -21- ------------------ This paper size is applicable to China National Standard (CNS) A4 (210X297 public attack) 557322 A7 B7 V. Description of the invention (π) The optical properties of light and absorptivity depend on the solubility. In a preferred embodiment of the present invention, the compound of formula I corresponds to formula E,

(Please read the notes on the back before filling out this page) # · Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Among which R 7 · R 8, feet 9 and 10 are respectively! ^, 卩, (: 1,81 ', I, 〇1 to (: 18 alkyl, 〇1 to (: 18 alkoxy to C! 8 alkylthio, aryl, aralkyl, Ci to € : 1 2 alkyl-aryl or Ci to (: 12 alkyl-aralkyl, and the second ring is unsubstituted or substituted with a preferred substituent as described above. Preferably, at least one of R7, R8, R9 and one of the defined substituents. Preferably, R8 and R9 are one of the defined substituents. More preferably, R7, Rs, R9S: R10 are substituents 0 in the present invention In the content, R7, R8, 1 ^ 9 and 10 may be linear or branched alkyl groups, and contain 1 to 12, preferably 1 to 8, most preferably 1 to 6, and particularly preferably 1 to 4 carbon atoms. Some examples are methyl, ethyl, n- or iso-propyl, n- or iso- or tertiary butyl, and pentyl, hexyl, heptyl, octyl, Nonyl, decyl, undecyl · -22-, This paper size applies to China National Standard (CNS) A4 (210x297 mm) Order

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7__ 5. Description of the Invention (v 丨) Dodecyl, Tridecyl, Tetradecyl • Pentadecyl • Hexadecyl, Heptadecyl And octadecyl isomers. In the context of the present invention, R7 and Rio may be linear or branched alkoxy groups "and contain 1 to 12, preferably 1 to 8, most preferably 1 to 6 俪, and particularly preferably 1 to 4 Carbon atoms. Some examples are methoxy, ethoxy, n- or iso-propoxy, n-, iso- or tertiary butoxy, and pentoxy, hexyloxy, heptyloxy, octyloxy , Nonyloxy, decyloxy, undecyloxy, dodecyloxy * tridecyloxy, tetradecyloxy, pentadecyloxy • hexadecyloxy • heptadecyloxy And octadecyloxy isomers. In the context of the present invention, R7, R8, R9 and Ri0 may be linear or branched alkylthio groups, and contain 1 to 12, preferably 1 to 8 * and most preferably 1 to 6, and Particularly preferred is 1 to 4 carbon atoms. Some examples are methylthio, ethylthio * n- or iso-propylthio, n- or iso- or tertiary monobutylthio, and amylthio, hexylthio, heptyl Thio, octylthio * nonylthio, decylthio, undecylthio, dodecylthio, tridecylthio, tetradecylthio, pentadecyl Isomers of thio, hexadecylthio, heptadecylthio, and octadecylthio In the context of the present invention, R7, Rs, R9 and Ri0 may be aryl or better Is phenyl. In the content of the present invention, "R7 * R8, R9 and Ri0 may be an aralkyl group, preferably an aryl monomethyl group or an ethyl group, and the aryl group preferably means phenyl-23. This paper is applicable to China National Standard (CNS) A4 specification (210X 297 mm) (Please read the precautions on the back before filling this page)

557322 A7 B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of invention (α) or foundation. Some examples are benzyl, phenylethyl, and tidylmethyl. In the context of the present invention, R7, R8, R9 and Rio may be a fluorenyl-aryl group, preferably a phenyl group, more preferably a C1 to C8 group, and most preferably a Ci to 04 alkylbenzene base. Some examples are methylphenyl, ethylphenyl, n- or isopropylpropyl, n-, iso- or tertiary monobutylphenyl, hexylphenyl, octylphenyl, dodecane Phenyl, and dimethylbenzyl. In the context of the present invention, R7, Rs, R9 and Rio may be alkyl-aralkyl, preferably alkyl benzyl, more preferably Ci to 08 alkyl benzyl, most preferably Ci to ( : 4 alkyl benzyl. Some examples are methyl benzyl, ethyl benzyl, n- or iso-propyl benzyl, n-, iso- or tertiary mono-butyl benzyl, Hexyl benzyl, octyl benzyl, dodecyl benzyl • and dimethyl benzamidine. In a particularly preferred embodiment of the present invention, the second ring is also substituted, especially The 7 position is substituted with an organic substituent at the 8 position or both positions. In a particularly preferred embodiment of the present invention, the compound of the formula I corresponds to the formula I, 1

R

-24- This paper size applies to Chinese National Standard (CNS) A4 (210X 297mm) (Please read the precautions on the back before filling this page)

Order

557322 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the Invention (A) where R 7, R 8, R 9 and Rio are Cl, phenyl or Ci-Ciz alkyl phenyl, Rii is fluorene or fluorenyl Substituents, and Ri 2 is fluorene or a fluorenyl substituent. The second ring is preferably mono-substituted, meaning that one of Ri i and Ri 2 is an organic substituent. Particularly preferred R7, R9 and R10 are chlorine or phenyl. In the context of the present invention, when Ri i or Ri 2 is substituted with a fluorenyl group, it is preferably selected from the group consisting of -CN, N02, (: 1 to 018 alkyl, C 2 to Ci 8 alkenyl, C 2 to Ci 8 alkyne Group, Ci to 01 8 hydroxyalkyl • Ci to 0 ^ 8 haloalkyl, C3 to Ci 2 cycloalkyl, c6 to Ci 8 aryl, c6 to (: 1 8 aralkyl, Ci to (: 1 8 Alkoxy, C3 to. ^ 2 cycloalkoxy, C6 to (: 1 8 aryloxy · C3 to Ci 2 cycloalkyl monoalkoxy * C6 to 〇 8 8 aralkyloxy · Ci to Ci 8 Alkylthio, C3 to Ci2 cycloalkylthio, C6-Ci 8 arylthio, C3 to Ci 2 cycloalkyl monoalkylfluorenyl * C6 to fluorene! 8 Aralkylthio, Ci to ( : ^ 8 alkyl-CO-, C3 SCi 2 cycloalkyl- CO-, Ce to Ci 8 aryl-C0-, C3 to Ci 2 cyclofluorenylfluorenyl- CO- · C6 to 8 aralkyl- CO -, -NR3 R4, alkoxyalkyl group with 2 to 20 carbon atoms, polyoxyalkylene-0Re * -X- (R5) kC (0) -NR3 R4, -X- (RS) kC (〇) -〇Re, -X- (R5) k_S〇2 -〇R6, -X-Us) kS〇2_NR3 R4, -25- (Please read the precautions on the back before filling this page)

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This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 A7 B7 V. Description of the invention (7Ψ) -NH-C (〇)-"and -0 ^ (0) ^ 6 'where r3 and R4 H, Cl SC2 0 fluorenyl 'cyclopentyl' cyclohexyl, benzyl, Ci to 2 alkylphenyl or Ci to (2 alkyl benzyl, or R3 and R4 together are tetramethyl , Pentamethyl or CH2 -O-CHz CH2 · or -CH2 CHz -NR3 -CHz CH2-printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs R 5 is R 6 meaning, benzyl, X is straight k is 0 and its acids up to R 6 R -CN »

Ci to Ci 2 alkylene, phenylene or phenylene, H, Ci to Cz oxenyl'cyclopentyl'cyclohexyl'benzyl, Ci to C12 alkenylbenzyl or Ci to Ci 2 Fluorenylbenzene bond, -0- or s, or 1, salt. The better meaning mentioned is also valid for the meaning of R. _ i i and R 1 2 are NOz iCi-Cia alkyl C7 cycloalkyl, C6 to Ci aryl, C7 to C

R X and R 3 organic substituents are more preferably selected from the group consisting of C i to C i 8 hydroxyalkyl (please read the notes on the back before filling this page)

to

, C 5 aralkyl C 6 to C! Cycloalkylthio, c6 to C alkoxy, 03 to 012 cycloalkoxy, Ci 〇 aryloxy, Cs to C7 cycloalkyl monoalkoxy · C7 aralkoxy, Ci to (: 1 8 alkylthio, Cs to C7 〇 arylthio, Cs to C7 cycloalkyl-2 6-This paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) 557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (/) Monoalkylthio, C7 to Ci 1 arylthio, c! SCi 8 fluorenyl-CO- , Cs to C7 alkynyl — CO- ′ Ce to C i 〇aryl-co-, (: 5 to 〇7 cycloalkyl monoalkyl- (; 〇-, 〇7 to 〇11 arylalkyl-co -, -NRs Re, alkoxyalkyl group with 2 to 12 carbon atoms, polyoxyalkylene-0R6, -X-Us) kC (0) -NR3 R4, -X-Us) kC (0) -0Re »-X- (Rs) kS〇z -ORe * -X- (Rs) kS〇z -NRs R4 · -NH-C (0) -IU and -〇-C (〇) _r6 'where R3 and R4 are respectively Is H, Ci to 〇6 alkyl, cyclopentyl, cyclohexyl, benzyl, Ci to Ce alkylphenyl or Ci to (: 6 alkylbenzylmethyl, or R3 and R4 together are tetramethyl , Pentamethyl or _CH2 CHz _ O-CH2 C H2 * " group, R5 is Cl to C4 alkylene, phenylene or phenylene, R6 means fluorene, Ci to (^ 2 alkyl, cyclopentyl, cyclohexyl, phenyl, phenylmethyl, Ci to C6 alkyl phenyl or Ci to (: 6 alkyl benzyl) $ X is direct hydrazone, -0- or S, k is 0 or 1, and its acid "and the like. A particularly preferred one in the present invention In a specific embodiment, 1 * Rl 2 is selected from the group consisting of -NOz, linear or branched Ci-Ci8 alkyl • linear or branched Ci to 〇8 alkoxy, _C (0) 0H, or- (; (〇) -〇_ Ci to Ci 8 alkyl. -27- This paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) (Please read the precautions on the back before filling out this page)

557322 Printed by A7 B7, Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China 5. Description of the Invention (4) The compounds of formula I and I are part of the conventional or can be easily prepared from, for example, described in EP-A- 0 4 5 6 6 0 9. It is prepared from unsubstituted or substituted o-phenylenediamine, and from unsubstituted or substituted phthalic anhydride. Guest chromophores can be selected from a wide range of pigments, pigment derivatives, dyes and their derivatives and fluorene mixtures * as long as they are cold light in the molecular state * and their absorption spectrum overlaps with the emission spectrum of the main hip chromophore . Suitable guest chromophores are, for example, WO 9 3/2 34 9 2. In a specific embodiment of the present invention, the guest hair color is preferably dissolved, at least to a certain extent, in a solvent, and if necessary, dissolved in the main chromophore to form a homogeneous solid solution formulation . In the context of the present invention * the solubility of the guest chromophore means at least 200 mg, more preferably at least 300 ¾ g and most preferably at least 500 * g of the guest chromophore is dissolved in 1 liter of solvent, such as two Methylformamide. This definition can also be applied to compositions where the host and guest chromophores are embedded in a polymer matrix. The guest chromophore can be selected from the group consisting of quinacridone-1, peri-nones, dione mono and dithioketone pyrrolopyrrole, rhodamine, coumarin, gutan, oxazine, oxazole , Cyanine, phthalocyanine, laver sickle, styryl dye, gold tincture complex and fluorene mixture. Preferred guest chromophores can be selected from the group consisting of 嗤 acridine, 1E, poise, diketopyrrolopyrrole, rhodamine, coumarin, cyanine, peptone, seaweed, styryl dye, and fluorene. mixture. Particularly preferred are quinacridine, 1, rhodamine * coumarin and a mixture of fluorene. This paper size applies to China National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the back before filling this page)

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(VI printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention) The guest compounds and their derivatives are known to those skilled in the art or can be prepared by similar methods. Quinacridine can be found in Chemical Reviews 67 (1) * Pages 1 to 18 (19 6 7).

Quinacridine corresponds to formula W

Where R2 6 to R2 9 and R3 2 to R3 5 are H »Ci to C6 alkylalkoxy, F, C1, Br, CN, No2 or -NR2 1R22, where R21 and R22 are H, Ci, respectively To C2 0 alkyl, phenyl, Ci to (^ 2 alkyl benzyl, benzyl or Ci to (: 12 alkyl benzyl, or Rz 1 and Rz 2 together are tetramethyl, penta) Methyl or -CH2CH2 -0- (; {12 (^ 2-; or two adjacent residues of 1126 to Rz 9 and / Rs 2 to R3 5 together form a 5-or 6-member with the carbon atom to which it is attached) Aliphatic, heteroaliphatic 'aromatic or fluorene aromatic rings, and these heteroatoms are in conformity with 1 and 2 ^; and 30 and R3! Are H, C1-Ci8 alkyl, and c2 to Ci8 alkenyl, respectively • C2 Ci 8 alkynyl, phenyl, benzyl · Cl to C6 alkylphenyl, Ci to (: 6 alkyl benzyl or R3 6 -0_C (0)-'where R3 6 -29- this paper Standards are applicable to China National Standard (CNS) A4 specifications (210X297 mm) (Please read the precautions on the back before filling this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of Invention (J) means Ci to 0: 1 8 alkyl, C 2 8 alkenyl, C 2 to (: 1 8 alkynyl, phenyl, benzoyl , Ci to (: 6 alkylphenyl, or Ci to 06 alkyl benzyl.?) Can be described in US-A-4,446,324 and US-A-5,470,502. Preferred examples are formulas IX and 3E of X,

among them

Rs 7 and R3 8 are F, Cl, Br or CN, R3 9 and R4 〇 means R3 6 -〇-C (0)-»where R3 6 means Ci-Cis alkyl , C2 to Cl8 alkynyl, phenyl, benzyl * Ci to C6 alkylphenyl, or Ci to C6 alkylbenzyl. R4 ^ and R42 are ^ 1, (: 1 to (: 18 alkyl, C2 to Ci 8 alkenyl, C2 to Ci 8 alkynyl, phenyl, benzyl. Ci to C6 alkylphenyl, C i to (: 6 alkyl benzyl or R3 6 -〇-C (0)--30- This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) (Fill in this page again)

557322 A7 B7

(LU bio gen F yellow) 5. Description of the invention U1), wherein R3 6 means Ci to Cl 8 alkyl, C2 to Cl 8 alkenyl, C2 to ^^ 8 alkynyl, phenyl, benzyl, Ci To (: 6 alkylbenzyl, or Ci to C6 alkylbenzylmethyl and R 4 3 alkylphenoxy. Some examples of commercial compounds are shown; (Lumogen F Orange) (Please read the note on the back first Please fill in this page for further information.) Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

Lumogen F Red) Dipyridine and dithioketopyrrolopyrrole can be found in US-A-4 415 685 and JP-A-6 1 1 6 2 5 5 5 0 Examples of dipyrrolopyrrole Corresponding to the formula XI, 31 paper sizes are applicable to Chinese National Standard (CNS) A4 specifications (210X297 mm) 557322 A7 B7 V. Description of invention (π)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs where R 4 4 is Η, respectively, replacing KC i to C 6 to C 4 alkylphenyl, where R 2 ^ and R groups, C i to C i 2 benzyl , Or R 2 1 -CH2 ch2 -o-ch2 R 4 5 means hydrazone, CC 2 to Ci 8 alkynyl, Ci to C 6 alkyl means Ci to Ci 8 alkynyl * phenyl, Methyl benzyl. Specific range of commercials) Book 1 (XI), halogen, or phenyl, which is unsubstituted or substituted with alkyl, CiMCe alkoxy, phenyl F * C1 * Br * CN, N02 or -NRz % Rz z 22 is H, C1 to C2o alkyl, benzylphenyl • benzyl, or Ci-Ci 2 alkyl and R2 2 together are tetramethyl, pentamethyl or CH2-; and i To Ci8 alkyl, C2 to Ci8 alkenyl,, benzyl, benzyl • (: 1 to 06 alkylphenyl benzyl or R3 0-OC (O)-, of which 0 alkyl, C2 to Cl8 alkenyl Radical, (: 2 to 0 1 radical, (: 1 to 06 alkyl phenyl, or (^ to 0) available from rhodamine using fine (1 9 9 6) ACORS ORGAHICSg A better example is Equation XI [

'47 46 This paper size applies Chinese National Standard (CNS) A4 specification (210X297mm> (XII), 32 (Please read the precautions on the back before filling this page)

557322 A7 B7 Printed by the Consumer Cooperatives of the Central Government Bureau of the Ministry of Economic Affairs. 5. Description of the Invention (i) where i and Rz 2 are Η, Ci to C2 0 yl, phenyl, Ci to Ci 2 alkylphenyl, benzene Methyl or Cl MCi 2 alkylbenzyl, or R2 i and Rz 2 together are tetramethyl, pentamethyl or -CH2 CHz -O-CH2 CH2-; and R46 means 1 ^, (: 1 To (: 18 alkyl * C2 to Ci8 alkenyl, C2 to ^^^ alkynyl, phenyl, benzyl, Ci to 〇6 alkylphenyl, or Ci to C6 alkyl benzyl or one equivalent Metal or ammonium anion; and r4 7 means = NR4 8 group, or = + HR4 8 R4 9 X-group, R4 8 and R49 are 1 ^, (: 1 to 〇18 alkyl, phenyl, Ci to Ci 2 alkylphenyl, benzyl or Ci to (: 12 alkyl benzyl; and X is a monovalent cation. Commercially available coumarin, oxazine, cyanine, glutamic acid, and styryl dyes can be used in specific ranges. Available from the Fine Chemicals Book 1 (1996) ACORS ORGANICS catalogue. A specific range of commercial oxazoles is available from the 18th dealer (1 992) D0JIND0 LABORATORIES. Cyanine and peptides are described, for example, in "phthalocyanine" Book (Frank H. Moser and his research colleagues, Published by Franklin, 1 983). In the context of the present invention * an effective amount of guest chromophores means, for example, that the composition may contain from 0.001 to 30, preferably from 0.01 to 20, relative to the total amount of host and guest chromophores. , More preferably from 0.01 to 10 and best from 0.01 to 5 weight percent of the guest chromophore. -33- (Please read the precautions on the back before filling out this page)

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This paper size applies to China National Standard (CNS) A4 (210X297 mm) 557322 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (a) In the present invention, the absorption spectrum of the chromophore of the object The significance of overlapping with the fluorescence emission spectrum of the host chromophore is clear to those skilled in the art. However, to help others understand, the overlap can be defined as "spectral overlap" by the following integration S = / 〇, F (v) / A (v) dv where / F (V) is normalized, so / f (v ) The fluorescence quantum yield of the host is equal, and where V is the wave number, / "is the fluorescence spectrum of the host measured by quantum, and Ά is the spectral distribution of the moire extinction coefficient of the guest. The M spectrum overlaps to understand that the light cold light enhancement is usually greater than 10 , Preferably greater than 100, more preferably greater than 500. The upper limit does not make any sense, because the amount of "overlap" does not have a maximum value (ie, the larger, the better). In the context of the present invention, embedding means the color of the object. The mass (or both host and guest chromophores if a polymer matrix is used) is distributed in the matrix or host chromophore (or, of course, in the polymer matrix). Better • The distribution is homogeneous. Therefore * In another preferred embodiment of the present invention, (a) the guest chromophore is homogeneously distributed in the host chromophore matrix • or (b) both the host chromophore and the guest chromophore are homogeneous Is distributed in the polymer matrix. In the context of the present invention, the term "homogeneous" For the components in the matrix, such as guest chromophores, are evenly or uniformly distributed or dispersed in the matrix (or host or guest / polymer matrix), and ideally, the spring texture distances are preferably equal to each other. Today According to the observation result * Because there are areas with high and weak fluorescence reduction and hair color, the color of the subject is more than the color of the object -34- This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm (please read first) (Notes on the back then fill out this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention (V)) In areas close to each other, a more even or even distribution is better fluorescent properties. In addition, a homogeneous or even distribution is better because the usual chance of aggregation is reduced.

In another preferred embodiment of the present invention, the general particle size of the guest chromophore (or the host and guest chromosphere if the polymer matrix is applied) is not larger than the required diameter * The amount of guest chromophores (or host and guest chromophores if the polymer matrix is applied) is preferably in its molecular state. Best • Guest chromophores (or host and guest chromophores if the polymer matrix is applied) are molecularly dissolved and homogeneously distributed in the host chromophore matrix (or polymer matrix). In the context of the present invention, the term "dissolved" means that the molecule exists in the free state of M in the given matrix and is completely separated, preferably in this way any interaction between the same kind of molecules that are sickened, and its completeness The ground is surrounded by matrix molecules. Usually the matrix can be a liquid solvent or a solid material such as a polymer or other fluorescent material (host), which has a different chemical structure. The concentration limit of molecules in the dissolved state is usually extremely dependent on the merging properties * between the molecules and the matrix medium and / or the intrinsic cohesion between the guest molecules. Accordingly, it is not possible to define a general norm * for a better concentration, and therefore, it is often necessary to handle noise based on noisy trials, for example, by some simple experiments. The polymers that can be used as the polymer matrix can be selected from the group consisting of thermoplastic polymer blends, thermoset and structural crosslinked polymers. These polymers can be homopolymers, copolymers, block copolymers, graft polymers, or random polymers. -35- ^ Zhang scale standard applicable to China National Standard (CNS) A4 specifications (210X297 mm) (Please (Read the notes on the back before filling out this page)

Printed by the Employees' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention (艸) 〇 These polymers may be opaque * translucent or transparent * preferably transparent. The polymer may be selected from, for example, a thermoplastic polymer such as polyester * polyamide * polyimide, polyamine-imide • polyimide, polyacetic acid, polyurea, polyolefin; Polymers that replace olefins such as ethylene fluorene, ethyl acetate, vinyl fermentation, vinyl chloride, dichloroethylene, propylene, propylene. Acrylic methacrylic acid and methacrylic acid esters and ammonium, styrene, chlorostyrene * a Styrene, styrene sulfonic acid and its amines, vinyloxazole, vinylpyridine * vinylpyrrolidone; polymaleic acid and hydrazones derived therefrom; polyethers (such as bisphenol A Diglycidyl ether), polymill, polyketone, polyphenylsulfide, and polyacetal; and natural polymers and their derivatives such as cellulose and its esters and ethers * and starch or starch derivatives. Examples of thermosetting resins and structural crosslinked resins are polyepoxides, unsaturated polyesters, light crosslinked resins such as those obtained from acrylic and / or methacrylic acid esters and / or polyamines and / or polyvalent enzymes. Amines • melamines / formaldehyde resins, and phenol / formaldehyde resins; polymers derived from butadiene, isoprene and / or chlorobutadiene, and copolymers with olefins, which may be crosslinked and Rubber-like properties, including lattices; and silicates such as are obtained from the conventional sol / gel process. The polymerizable composition of the present invention may contain further ingredients such as reinforced parts > properties such as electrical, physical and mechanical properties * and / or processing capabilities, such as a dispersant for achieving a uniform particle distribution • lubricant * plasticizer , Antistatic agent, solvent, forming agent • antioxidant, light stabilizer * filler and -36- This paper size applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) .n — ^ ϋ emmmtmt .ml am- — 、 One and one " Jmi ΙΒΙϋ —Bl ^ in ^ i (Please read the precautions on the back before filling out this page) kf Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 5. Description of the invention Agents such as glass beads and glass entanglement * quartz powder, silicates (such as mica, white clay, wollastonite), gold tincture and semiconductor gold tin oxide, gold tin carbonate, gold tin salt, gold tin and semiconductor gold tincture It is powdered carbon black or carbon fiber, whisker, metal and semiconductor gold hafnium carbide, gold hafnium and semiconducting pith metal nitride, dyes, pigments and others. (Host chromophore plus guest chromophore): The species ratio of the polymer matrix depends on the actual application, so except for the wide range of 90: 10 to 1: 9 9 9 of Guangfanpu. In partial applications where both color intensity and fluorescence are required, the preferred ratio of chromophore to polymer matrix is 20:80 to 99: 1, preferably 50:50 to 99: 1 and more preferably 80: 20 to 99: 1. In an environment where fluorescence is required but color intensity is not required, the preferred ratio of host chromophore to polymer matrix is 20: 80 to 1: 999, preferably 10: 90 to 1: 99 9 and More preferably, it is 5:95 to 1:99. The composition of the present invention is prepared from conventional methods such as the sublimation action described in JP-A- 0 3 2 5 5 190 or a new method using the solubility of a guest chromophore. A further specific embodiment of the present invention is a method for preparing the aforementioned chromophore comprising a host chromophore and a guest chromophore, and a polymer matrix composition if necessary, wherein the absorption spectrum of the guest chromophore and the host chromophore The fluorescence emission spectra overlapped are characterized by (a) the host chromophore is selected from the group consisting of benzo [4,5] oxazolo [2, Ι-a] isoazepin-11-ones, (b ) Mix the host chromophore and an effective amount of at least one guest chromophore in the presence of a solvent, and a selective polymer or polymerizable precursor 'and -37- This paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) (Please read the notes on the back before filling this page)

557322 A7 B7 V. Description of the invention (bucket) (c) Precipitation of the main hip and guest chromophore, when the polymer of step (b) is selectively stored, or (d) the polymer precursor in the polymerization step (b) During the precipitation of the main hip and guest chromophores. In the context of the present invention, * the materials are mixed to obtain dissolved ingredients in common solvents and then evaporate the solvents; precipitation from good solvents to bad solvents (violent stirring can be used); freeze drying; and polymerization polymerization Precipitation during polymerization of monomers or oligomers, preferably under vigorous stirring. Suitable inert solvents are, for example, aprotic and aprotic solvents, which can be used alone or as a mixture of at least two solvents. Examples are: water, leaven (methanol • ethyl leaven, propionate, butyrate), ethanediol monomethyl mono or monoethyl ether, ether (dibutyl ether) tetrahydrofuran * dioxane, ethanediol dimethyl Ether, diethyl ether diethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether), halogenated hydrocarbons (methylene diamine, atmospheric imitation, 1,2-dichloroethane, 1, 1, Trichloroethane, 1,1,2,2-tetrahydroethane), carboxylic acid esters and lactones (ethyl acetate, methyl propionate, ethyl benzoate) 2-methoxyethyl Glycolic acid _, 7-butyrolactone, cis-valerolactone • pivalolactone _) * Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs, the Ministry of Economic Affairs (Please read the precautions on the back before filling out this page ) Amines and lactams; N, N-dimethylformamide, N, budiethylformamide, N, N-dimethylacetamide, tetramethylurea, hexamethylphosphite tris Styramine · 7-butyrolactam, e-hexanolactam, p-methylpyrrolidine, N-ethylpyrrolidone, N-methylhexanolide, linamine (dimethyl Asia "), mill (dimethyl«, diethyl mill, trimethylol mill, tetramethylammonium Mill), tertiary amine (N-methylpyridine * N-methylmorpholine), aliphatic and aromatic hydrocarbons such as petroleum ether, pentane, hexane, cyclohexane, methylcyclohexane, benzene or Substituted benzene-38- This paper size applies Chinese National Standard (CNS) A4 (2 丨 0'〆297mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention (η) 〇-dichlorobenzene, 1,2,4-trichlorobenzene, nitrobenzene, toluene, xylene) and nitriles (acetonitrile • propionitrile, benzonitrile, phenylacetonitrile), ketones (acetone, methyl-iso Butyl-ketone). Precipitation can be performed in a number of ways. When the solubility of the main medulla and guest crocodile chromophore in the final composition provides the required weight range for sufficient K, the precipitation can be completed by adding the solution to a non-solvent * filtration and then precipitation and removal of the solvent. " It is preferred to dry the solids at an elevated temperature and preferably under vacuum. Another possibility is evaporation of the solvent under vacuum and / or elevated temperature. In the freeze-drying method, stable components and solvents are usually formed by freezing a solution, where each component is homogeneously distributed. This state is usually maintained when solvent K is lyophilized and removed. The final product is usually high in fluorescence and displays all the characteristic properties of the host / guest material. In another preferred pulpy embodiment of the present invention, the host and guest chromophores are dissolved in a suitable solvent * and the solution is added to a polymer gel (the polymer swells with the solvent). The main pulp and guest chromophores usually penetrate the gel. The solvent is removed in principle and the K is dried to form the composition of the present invention. In another preferred embodiment of the present invention, the subject and guest chromophores are ground together using a ball mill. The high-shear-guest chromophore particles and / or molecules penetrate into the host chromophore matrix to form the fluorescent composition of the present invention. In another preferred embodiment of the present invention, the host and guest chromophores are mixed * selectively mixed with the polymer and melt-mixed at a temperature below the decomposition temperature of the respective components. -39- This paper size applies to Chinese National Standards (CNS) 8 4 ^ grid (210X297 mm) (Please read the precautions on the back before filling this page)

557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Α7 Β7 V. Description of the Invention (U) The composition of the present invention can be applied to a wide range of applications. For example, the composition of the present invention can be usefully used as a coloring agent in applications such as road markings and traffic signs used at night or white, because they present extremely bright daylight fluorescent light and can also be used by Excited by UV radiation from car halogen lamps. This provides intense * bright colors during white and night. Other applications include their use as pigments, colorants, scintillator materials, solar collector materials, light-emitting electrical chillers, and fluorescent image materials. Moreover, the selection of the host compound can have many kinds of elasticity M to obtain the emission wavelength required by the total system, in which the ability to adjust the color is given by the adjustment of the wavelength and the reduction of the core system correction to a specific color application. It is also possible to generate fluorescent images (highly embossed structures) by conventional photoresist technology. The composition of the present invention can also be used in coatings, lacquers and printing inks. The composition of the present invention can be used in various forms depending on the end use purpose. The composition of the present invention can be ground into a powder to be used in industrial applications. Another embodiment of the present invention is that the composition of the present invention is in the form of a powder containing particles. The particles may have an average diameter ranging from 10 nm to 500 m, preferably from 50 nm to 100 m, and most preferably from 50 nm to 50 m. Powders also include polymers containing the host and guest chromophores dissolved and uniformly distributed, and can be obtained by milling or emulsion polymerization, or both. The particles of the composition of the present invention can be encapsulated with the polymer by conventional means. -40- This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) (Please read the precautions on the back before filling this page) Order > τ 557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of Invention (M) M generates pigments used in dyeing polymers, for example. The composition of the present invention can be used as a coating layer to form a layer on a supporting material, preferably by a co-sublimation method. A further specific embodiment of the present invention is a support material in which at least a portion is coated with a layer of the composition of the present invention. Suitable support (or carrier) materials may be selected from materials containing rhenium or rhenium-free materials such as glass, ceramics, minerals, plastics, paper, wood * semiconductors, gold alloys, metal oxides and semiconductor gold oxides, and gold. Samarium or semiconducting samarium gold samarium nitride or a carbide. The thickness of the calendar depends on the requirements of use and is usually from 0.01 to 100 microns, preferably from 0.05 to 500 microns, and particularly preferably from 0.1 to 100 microns. The coating may be preferably a transparent coating Calendar protection. Such coatings are generally known. Especially photocrosslinked coatings are mainly used for this purpose and are known in the art. The powder of the present invention may be mixed with a polymer. A further specific embodiment of the present invention is a composition comprising (a) a polymer matrix, and (b) particles of the composition of the present invention are homogeneously distributed therein. The amount of particles may be, for example, 0.0001 to 90% by weight of the total composition, preferably 0.1 to 90% by weight and more preferably 1 to 50% by weight. The polymer matrix may be selected from the group consisting of thermoplastics * polymer blends, thermosets, and structural crosslinked polymers. These polymers can be homopolymers * copolymers, block copolymers, graft polymers, or random polymers. These polymers can be opaque • translucent or transparent • preferably transparent-4 1- This paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) (Please read the precautions on the back before filling out this Page) --- ϋ- When 557322 A7 B7 V. Description of Invention () Printed by the Consumers' Cooperative of the Central Bureau of Economic Standards. Polymerized fluorene imide, polyurea, polyester, ethylene methacryl, methacrylamide; fluorene, polyphenylenes such as cellulose thermosetting saturated polyene esters and / or resins, and / or neoprene Nature silicate. Soluble and structural particles of thermoplastic polymers are usually selected from the group consisting of polyamines, alkylenes, alcohols, acetic acids, and methylethylene, pyridine and ethyl polyethers , Or from phenol / methadiene, including from ethylene * propylene styrene styrenyl pyrimide such as dimers and its esters and structural photocrosslinked polyenzyme resins and olefinic lattices; thermoplastic polymeric amines Polyvinylamine replaces dichloroethylene of olefins, acid brewing and sulfonic acid and its esters, rolidone; polyphenol A diglycid polyacetal; and ether * and starch cross-linked resins such as acetamide and /; Copolymers of polymers derived from hydrocarbons and, for example, polymers such as poly (vinyl alcohol), poly (fluorene) * poly (fluorene) * polyaminoacetic acid, polymers such as vinyl ether, ethylene propylene, acrylonitrile, amine acrylate, styrene, Styrene and ammonium, vinyloxazole, maleic acid and glyceryl ether derived therefrom), polymills, polynatural polymers and their derivatives or starch derivatives. Examples are polyepoxides, not from acrylic acid and / or methacrylic acid or polyamines • melamine / formaldehyde from butadiene, isoprene and • which may be cross-linked and like conventional sols / gels The sexual composition of the method is, for example, obtainable by a conventional mixing method such as a mixing solution and removing the solvent * injection molding method and extrusion molding method. The thermosetting crosslinked composition can be obtained by a conventional method such as a compression molding method, in which the precursor composition is dispersed before polymerization. The polymerizable composition may contain further components such as electrical, physical and mechanical properties, and / or processing capabilities, such as -42- This paper size applies the Chinese National Standard (CNS) Α4 specification (210X297 mm) (please first Read the notes on the back and fill in this page) 557322 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (called) Dispersants are used to achieve uniform particle distribution, lubricants, plasticizers, antistatic Agents, solvents, forming agents, antioxidants, light stabilizers, fillers and reinforcing fillers such as glass beads and glass fibers, quartz powder, silicates (such as mica, clay, wollastonite), gold tincture and semiconductor metal oxidation Materials, gold tin carbonate, metal salts * gold tin and semiconductor gold tin * are powdered carbon black • or carbon fiber, whisker, metal and semiconductor gold tin carbide, gold tin and semiconductor gold tin nitride, dye , Pigments and others. The polymer composition of the present invention can be used in the form of shaped articles. The polymer composition or polymerizable precursor composition and the host / guest particles may contain a solvent M to form a coating composition. Suitable solvents are as described above. In another aspect of the present invention, a polymer composition containing host / guest composition particles or particles obtained from a polymer and dissolved host / guest chromophore can be used for coating a carrier material using the above-mentioned composition. Cover. Another embodiment of the present invention is a composition comprising (a) a support material and (b) a coating composition on at least one surface, which comprises (a) a polymer matrix, and (b) a composition Particles or particles obtained from polymers and dissolved host / guest chromophores, or both of the present invention, are homogeneously distributed therein. In another aspect of the present invention, a composition containing a polymer and a soluble host / guest chromophore can be used as a coating material for a carrier material. Another embodiment of the present invention is a composition comprising (a) a carrier material and (b) a coating composition on at least one surface, which contains -4 3-(Please read the precautions on the back before (Fill in this page). · #

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This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (") (a) polymer matrix, and (b) the present invention The polymer and the soluble host / guest chromophore are homogeneously distributed therein. Suitable carrier materials may be selected from the group consisting of organic or inorganic materials such as glass, ceramics, minerals, plastics, paper, wood, semiconductors, gold and gold Samarium oxide and semiconducting samarium oxide, and metal or semiconductor Au samarium nitride or a carbide. The thickness of the calendar depends on the use and is usually from 0.01 to 100 μm, preferably from 0.0 5 to 500 micrometers, and particularly preferably from 0.1 to 100 micrometers. 0 Coatings can be protected by preferably transparent coatings. Such coatings are generally conventional, especially photocrosslinking coatings are mainly used in This purpose * is known in the art. Coated materials can usually be obtained from conventional methods, such as directly or using a dispersion of a polymerizable composition, inlay or spin coating. It is also possible to use a polymerization A product comprising a polymer formed from a monomer or an oligomeric precursor, in particular a crosslinkable olefin unsaturated monomer, the composition is generally useful as a coating. The induction of polymerization can be thermal Or by actinic radiation or both. The polymerization is preferably performed in the presence of a radiation initiator species. These coating compositions are novel and are further specific embodiments of the present invention. Further specifics of the present invention The example is a solvent whose liquid composition contains (a) soluble polymer • and -44- This paper size is applicable to Chinese National Standard (CNS) grid (210X297 mm) (Please read the precautions on the back first Fill out this page again), 1T printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (A) (b) The subject of the composition of the present invention and the particles of the guest chromophore, or dissolved in it The host and guest chromophores of the present invention. These compositions may contain a solvent, such as those mentioned herein and optional surfactants and dispersants. The viscosity range of the composition depends on the desired application, and Simple By the choice of the amount of solvent, polymer binder and fluorescent materials. To further achieve the required viscosity, thickeners can be added in the field. Solvents have been mentioned. The preparation of the composition can be The ingredients are mixed together by using mixing equipment. Dispersion is usually fixed according to viscosity. Aggregated particles can be redispersed by stirring. In a very good specific example, the coating can be prepared. Use a polymerizable composition in which at least one surface of the carrier material is coated * and then polymerized by heat, radiation, or both. The photopolymerizable mixture can also be used to produce fluorescent light by conventional photoresist technology. Light image. A further embodiment of the present invention is a polymerizable composition comprising a polymerizable monomer or prepolymer mixed with a particle-containing powder form composition of the present invention, or with the subject of the present invention and a guest hair color The pellets are mixed, or mixed with both, and are preferably dissolved therein. Compositions which can be used to produce the polymers or polymer particles of the present invention are as described above. Preferred * when the coating or image is produced * the composition contains a solvent. The foregoing specific embodiments are also applicable to the composition, including the preferred specific embodiments. In another preferred embodiment, based on polymerizable monomers and / or pre-45- this paper size applies Chinese National Standard (CNS) A4g (210X297 mm) (Please read the precautions on the back before filling this page )

557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention () The composition of the polymer contains a functional group s from an olefinic unsaturated group "is preferably obtained from -ch = ch2 and -C (CH3) = CH2, which can be thermally polymerized or photopolymerized. Photopolymerizable monomers and prepolymers are known to those skilled in the art and are described, for example, in EP-A- 0 6 5 4 7 1 1. Preferred photopolymerizable monomers and prepolymers are esters or amines based on acrylic or methacrylic acid and enzymes, polyenzymes, amines and polyamines. The preferred ethylenically unsaturated photopolymerizable agent may be selected from acrylic or methacrylic acid esters containing aliphatic, cycloaliphatic, and cycloaliphatic-aliphatic enzymes, and preferably contains 2 to 12, more preferably For two to eight carbon atoms, two to four, and amines and diamines to tetraamines. Some examples of these two enzymes and dialkylenzymes such as diethylenzyme, 1,2- or 1,3-propyldiase, 1,2-, 1,3- and 1,4-butyl Glycol, pentyl secondary, hexyl secondary, octyl secondary, decyl secondary, dodecyl secondary, cyclohexyl secondary, bis (hydroxymethyl) -cyclohexane Cz _C6 alkylene glycols and preferably 2 to 100 alkylene glycol units, more preferably 2 to 50 alkylene glycol units, and most preferably 2 to 20 alkylene glycol units Polyoxyalkylenes * such as polyethylene glycols * Polypropylene glycols Polybutylene glycols and Polyethylene / polypropylene glycols • Further 1,1,1-trihydroxyl Methylethane or -propane, pentaerythritol and dipentaerythritol. Some examples of polyamines are ethylene diamine, 1,2- and 1,3-propyldiamine, 1,2-, 1,3- and 1,4-butanediamine, 1,6- Hexanediamine, diethylenetriamine, triethylenetetraamine, cyclohexanediamine, (aminomethyl) cyclohexaneamine, isophoronediamine and bis (aminomethyl) Cyclohexane. Examples of yeasts are linear or branched Ci-C2oxane. -4 6-This # 's Zhang scale is applicable to China National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7__ 5. Description of the Invention (/) The photopolymerizable composition is particularly suitable for producing coatings and images. Another preferred embodiment of the present invention is in a composition * which comprises a carrier material and a polymerized photoresist material with a high relief image. The subject and object chromophores of the invention * or both contain the above, if necessary, dissolved and / or homogeneously distributed therein. A further specific embodiment of the present invention is a method for preparing a fluorescent high relief image on a carrier. Preferably, this involves the above-mentioned coated photopolymerizable composition (which is preferably dried and the solvent removed) written on a carrier irradiated under a photomask or by laser, and the radiated composition is developed And finally remove the non-radiated areas. Removal of non-radiated sites is most often treated with M solvents. All the above-mentioned fluorescent materials can be widely used in optical and electro-optical devices. A further embodiment of the present invention is a method for manufacturing fluorescent radiation, which requires the use of electricity or UV or visible radiation, or both to excite the fluorescent composition of the present invention. Another embodiment of the present invention is to use the composition of the present invention to act as a fluorescent material. As mentioned above, benzo [4, 5] oxazolo [2, Ι-a] isoazaindene-1 ketone, 1,2,3,4-tetrabenz [4,5] imidazole [2, la] Isoindan-11-one and some substituted derivatives are known in the art. According to my observation, when measuring the exposure test determined from K time, benzo [4, -47- This paper size applies to China National Standard (CNS) 8 4 ^ grid (210X297 mm) (Please read the back (Please fill in this page again)

557322 A7 B7 V. Description of the invention (sand) 5] Pyrazolo [2, Bua] isoazaindene-1 Bu_ and 1,2, 3, 4-tetra-benzobenzo [4,5] pyrazole The ac [2, Ι-a] isoazaindene-U-ones show extremely high photo-horizon characterization. Furthermore, it has been found that the stability of these compounds decreases when the 7- and / or 8-position is substituted. The cases of 1,2,3,4-tetrabenzobenzo [4, 5] sialo [2, Ια] isoazepine-11-fluorene have shown adequate light stability sufficient for a variety of applications. However, it was found that when solid-state cold light was maintained, the light stability was more improved, and when benzo [4, 5] oxazo [2, Ι-a] isoazepine-1indene was replaced by the selected one These compounds have the required solubility based on 1-, 2-, 3- and / or 4-positions and substitutions at the 7- and / or 8-positions. A further specific embodiment of the present invention is a compound of formula V (please read the precautions on the back before filling this page)

, ^ T

Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs where at most one of R 1 3, Rl 4, Ri 5 and R 16 is Η, and at least one of R 1 3, Rl 4, RlS and Rl 6 is a substituent selected from the package. Ci To you! 8 alkyl, Ci to Ci 8 alkoxy, Ci to Ci 8 fluorenylthio, Cl to Ci 2 alkoxy monopoly Cz to Ce alkylene oxide; unsubstituted or via F, C 1, Br, -CN Ci to Cl -4 8-This paper size applies to the Chinese National Standard (CNS) A4 (210x297 mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (β) Burning base, Ci to Cl 2 alkoxy 'Cl to Ci 2 fluorenylthio or -NR2 1 R2 2 substituted Cs to C8 cycloalkyl, cs to C8 cycloalkoxy, C5 to C8 cycloalkylthio, c5 to c8 ring Alkyl-Ci to C4 alkyl, C5 to C8 cycloalkyl-Ci to C4 alkoxy, Cs to C8 cycloalkyl-Ci to (: 4 alkylthio, phenyl, phenoxy, phenylthio Group, phenyl-C1 to C4 alkyl, phenyl-Ci to O4 alkoxy, phenyl-Ci to C4 alkylthio; or

Ri3 in common with R14, Ri5 in common with Rle, or Ri3 in common with Ri4 and Ris in common with Rie, or Ri4 in common with Ris is selected from -CH = CR2 4 -CR2 5 = CH-, surface N = CR2 4 -CR2 5 = CH ·, -CH = CR2 4 " CR2 5 = N-, -CH = N-CRe 5 = CH- »-CH = CR2 4 ** N = CH-» -N = CR2 4 -CRz 5 = N- , -N = CR2 4 -N = CH- * -CH = CH-0- * -CH = CH-S- * -CH = CH-NR2 3-·,

Ri 7 and R 2 〇 are H or have the meaning of Ri 8;

One of Ri 8 and Ri 9 is H, and the other or both of Ri 8 and R 19 are substituents selected from the group consisting of Ci to Ci 8 alkyl * Ci to Ci 8 alkoxy, C: to 0 : 1 8 alkylthio 'Ci MCi 2 alkoxy monopoly C: 2 to C6 alkylene oxide; unsubstituted or via F, C 1,

Br, -CN, Ci-Cl2 alkyl, Ci to alkoxy,

Ci to 〇 ^ 2 alkylthio or _NRz i Rz 2 substituted C 5 to C 8 cycloalkyl, C5 to 0: 8 cycloalkoxy, C5 to C8 cycloalkylthio, C5 to C8 cycloalkane -Cji to C4 alkyl * Cs to C8 cycloalkyl-Cl to C4 alkoxy, C5 to C8 cycloalkyl-Cl to C4 焼-49- This paper size applies to China National Standard (CNS) A4 specifications (210x297 (Envy) (Please read the notes on the back before filling this page)

557322

5. Description of the invention (4) thiol, phenyl, phenoxy, phenylthio, phenyl-C1 to C4 fluorenyl, phenyl-Ci to 〇4 alkoxy, phenyl-Ci gC4 alkyl Thio, phenyl-ci to (: ji 2 alkylene • phenyl-c (〇) _, phenyl-NR2 3 -c (0)-, phenyl-NRz 3 -S (0) 2-, Phenyl-S (0)-, Phenyl-s (0) 2, Phenyl-C〇2-, Phenyl-s (o) -o-, Phenyl-s03-Employees of the Central Standards Bureau of the Ministry of Economic Affairs Printed by consumer cooperative f phenyl-NRz 3-* or phenyl — CH = CH-1 or R 1 7 together with R 1 8, R 1 9 together with R 2 0 f or R 1 7 and R 1 8 and R 1 9 in common with R 2 0 9 or R 1 8 in common with R 1 -CH = CR2 4 -CR 2 5 = CH --i N = CR2 4 -cr2 5 CH-9 -CH = CR2 4 -CR2 ; 5 = N- 9 -CH = N-CRz 5 = CH- -CH = CRz 4 -N = CH- * > -N = CR 2 4-cr2 5 = N —it plane N = CRz 4-N = CH —1 1-CH = CH- 0- -CH = CH -s —i 1 -CH = CH- nr2 3 1 R 2 1 and R 2 z are C 1 to CZ 0 fluorenyl $ phenyl f C 1 To C 1 2 alkylphenyl f benzyl or c 1 to c 1 z Alkyl benzyl or R 2 1 and R 2 z both agree to be tetramethyl, f pentamethyl or -CHz CHz -0 -CHz CHz, > R 2 3 is Η f C 1 to C 4 alkyl Or benzyl l and R 2 4 and 2 5 are fluorene, C 1 to C 6 alkyl% c 1 to C 6 alkoxy 9 C 1 to C 6 alkylthio 9 or F tc 1 or B r 〇 In a preferred embodiment 9 R 1 3 and R 1 4 are substituents f and most preferably R 1 3 > R 1 4 R 1 5 and R 1 6 are substituents 0 in another preferred embodiment In the embodiment, R 1 3 and R 1 4 R 1 5 and R 1 $ R 1 4 and R 1 5 $ or R 1 3 and R 1 4 and R 1 5 and RI 6 -50- This paper size is applicable to China Standard (CNS) A4 specification (2 丨 0'〆297mm) (Please read the precautions on the back before filling this page)

A 557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (correction) A total of -CH = CR2 4 -CR2 同意 = CH- · = 4 -Ch 5 = CH-, -CH = CR2 4 -CRz 5 = N-, -CH: N-CR2 5 = CH-, -CH = CRz 4 -N = CH-〇 In a preferred embodiment, R17 and 1 ^ 2〇 means H, And Ri 7 and Ri 9 or both are substituents. In another preferred embodiment, Ri7 and Rl8, Rl9 and R20 '1 ^ 18 and 1 ^ 19, or Ri7 and Ri8 and Rl9 and R2 0 agree -CH = CR2 4 -CR2 5 = CH- »-N = CR2 4 -CR2 s = CH-» -CH = CR2 4 -CR2 5 = N- »-CH = N-CRz 5 = CH-» -CH = CRz 4 -N = CH-〇 In the present invention, when one or more of Rl3'Rl4, Ri5 and Rl6 are simultaneously Ri7, Rl8, Rl9 and Rz0 are linear or branched alkyl groups, and contain 1 to 12, preferably 1 To 6 carbon atoms. Examples of alkyl groups have been described above. Preferred alkyl groups are the isomers of methyl, ethyl, n- or iso-propyl, n- or iso- or tertiary mono-butyl ', and pentyl, hexyl. In the context of the present invention, when one or more of Rl 3, Rl4 and Rl6 are simultaneously Rl 7 'Rl9 and R20 are linear or branched alkoxy groups * and contain 1 to 12, preferably 1 to 6 Carbon atoms. Examples of alkoxy groups have been described above. Preferred alkoxy groups are the isomers of methoxy, ethoxy, n- or iso-propoxy, n-or-iso-or tertiary-butoxy, and pentyloxy, hexyloxy. In the content of the present invention, when one or more of them, R14 -5 1-This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page)

557322 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of Invention (π) 'Rl5 and Rjl7, Rl8 and Rz〇 are linear or branched alkoxysulfur enzymes, and contain 1 to 12 锢For 1 to 6 carbon atoms. Examples of alkoxythio groups have been described above. Preferred alkoxythio groups are methylthio, ethylthio, n- or iso-propylthio, n- or iso- or tertiary monobutylthio, and pentylthiohexylthio Of its isomers. In the context of the present invention, when one or more of Ri3, R14, Ri5, and R16 are simultaneously Ri7, R18, and R20 are Ci to Ci 2 alkoxy-poly C2 to C6 alkylene oxide, wherein the alkoxy group may be Linear alkoxy or branched alkoxy and contains 1 to 6 and preferably 1 to 4 and may be, for example, methoxy, ethoxy, propoxy and butoxy. The oxyalkylene group preferably contains 2 to 4, more preferably 2 to 4 and most preferably 2 to 3 carbon atoms * and may be vinyloxy or 1,2-propenyloxy. Residues may contain 1 to 12, preferably 1 to 6, and more preferably 1 to 4 repeat alkylene oxide units. In the context of the present invention, when one or more of these are ^ 3 · R 1 4 'Rl5 and Rl6 and Rl7, Rl8, Rl9 and R20 are cycloalkyl, it is preferably cyclopentyl or cyclohexyl . In the context of the present invention, when one or more of Ri3, Ri4'Rl5 and Rl6 are simultaneously Rl7, R18, Rl9 and are cycloalkoxy groups * it is preferably cyclopentyloxy or cyclohexyloxy. In the content of the present invention * When one or more of Ri 3 · R 1 4, Ri5 and Rl6 are simultaneously Ri7, Rl8, Ri9 and R20 -52- This paper size applies to Chinese National Standard (CNS) Α4 specification (210X 297 Mm) (Please read the notes on the back before filling this page), π

Printed by the Employees' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7_ 5. The description of the invention (W) is cycloalkylthio, which is preferably cyclopentylthio or cyclohexylthio. In the context of the present invention, when one or more of Ri3, Ri4, Rl5, and R16 are simultaneously Ri7, Ri8, R19, and R20 are cycloalkyl monoalkyl groups, the alkyl group is preferably an ethyl group and more preferably a methyl group. And cycloalkyl are preferably cyclopentyl or cyclohexyl. Preferred examples are cyclopentylmethyl and cyclohexylmethyl. In the context of the present invention, when one or more of 1 ^ 3, Ri4, Rl5 and Rl7, Rl8, Ri9 and R20 are cycloalkyl-alkoxy, alkoxy is preferably ethoxy and More preferred is methoxy, and cycloalkyl is preferably cyclopentyl or cyclohexyl. Preferred examples are cyclopentylmethoxy and cyclohexylmethoxy. In the context of the present invention * when one or more of them are 3. R14 'RiS and R16 and R17, Ri8, R19 and R20 are cycloalkyl-alkylthio, alkylthio is preferably ethylthio and More preferably, methylthio * and cycloalkyl are cyclopentyl or cyclohexyl. Preferred examples are cyclopentylmethylthio and cyclohexylmethylthio. In the context of the present invention, when one or more of 3 * R14, Ri5 and R16 are simultaneously R17, Ri8, Rjl9 and R20 are phenylalkyl groups, the alkyl group preferably contains 1 or 2 carbon atoms and the most preferable Is methyl. Particularly preferred is benzyl. In the context of the present invention, when one or more of R 3 'R 14' R 1 S and Ri 6 are simultaneously Ri 7, R 18, R 19 and R 2 0 are phenylalkoxy groups, the alkyl group preferably contains 1 or 2 carbon atoms and most preferably A-53- ^ Zhang scale is applicable to China National Standard (CNS) A4 specifications (, 210X297 mm) (Please read the precautions on the back before filling this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the Invention Particularly preferred is benzyloxy. In the context of the present invention, when one or more of Ri3, Ri4, R15, and R16 are simultaneously Ri7, R18, Ri9, and R2o are phenylalkylthio groups, the alkylthio group preferably contains 1 or 2 carbon atoms And most preferably methylthio. Particularly preferred is benzylthio. In the context of the present invention, when one or more of Ri 7, R 1 8, R 19 and Rzo are phenyl-(: 1 to 0:12 alkylene, alkylene may be linear or branched and may be Contains 2 or 6 and preferably 2 to 4 carbon atoms. Some examples are ethylene, 1,2 or 2,2-propylene • and 1,2, or 2,2-butylene. The substituents are F, C1, 01 to O4 alkyl, < 31 to C4 alkoxy and to-NRz 1 Rz 2, where R2 i and R2 2 are ^^ to 〇 ^ 2 alkyl "phenyl or benzene In the context of the present invention, when Rz i and R22 are alkyl groups, they may be linear or branched alkyl groups and contain 1 to 12 and preferably 1 to 6 carbon atoms. In the context of the present invention, When R2 i and R22 are alkylphenyl * alkyl may be a linear or branched alkyl group and contain 1 to 12 and preferably 1 to 6 carbon atoms. R23 is preferably H, methyl or ethyl. In the context of the present invention, R 2 4 and 25 are alkyl, alkoxy, and alkylthio groups, which may be linear or branched alkyl groups and contain 1 to 4 and preferably 1 to 2 carbon atoms. -5 4-This paper size is applicable to China National Standard (CNS) A4 (210X297mm) (please first (Read the notes on the back and fill out this page)

557322 A7 B7 and

R

R 18 R Ί9 V. Description of the Invention (^) In a preferred embodiment, Ri 3 »R 1 4

Ri 6 is preferably Ci to (4 alkyl, Ci to 0 4 alkoxy, phenyl, or 0 to 4: 4 alkylphenyl. Most preferably R 1 4 R 1 and Ri s are both In another preferred embodiment, Ri 7 and R 2 0 mean fluorene, and Ri 8 and Ri 9 or both are Ci MCi 8 alkyl, ^^ to Cl8 alkoxy, or 1117 and 1 ^ 18, Rl9 and Rzo · Rl8 and R19, or Ri7 and Ri8 and Rl9 and R2, respectively, agree as-CH = CR2 4 -CR2 5 = CH-, where R2 4 and R2 5 respectively mean H, F, C1 , (: 1 to 08 alkyl or 0 to 08 alkoxy.

In a particularly preferred embodiment, formula V corresponds to formula VI (VI),

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs where R 1 7 and R 2 〇 are Η 9 and R 1 8 and R 1 9 or both are C 1 to C 1 8 burners, C 1 to C 1 8 burners Oxygen, or R 1 8 together with R 1 9 means -CH:: CR2 4 -CRz 5 = CH-; R 1 7 together with R i 8 9 or R 1 9 together with R 2 〇, or R 1 7 Together with R 1 8 »or R 1 9 together with R z 〇 > or R 1 7 together with R 1 8 and R 1 9 total 55 This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 A7 B7 V. Description of the invention (points) Same as R 2 〇 means -c H = c R 2 4-C β 2 5 = C Η 'where R 2 4 and R25 mean H, F, C1, CiMC8 respectively. Or (:! To Cs alkoxy. The alkyl group is preferably branched at α or α, α-position. It has been found to have 1,2,3,4-tetrapyrene with a cx-branched alkyl substituent. Benzo [4,5] pyrazolo [2,1 ^] isoazindene-11-_ has higher photogenicity than methyl-substituted compounds • H3,4-tetrabenzylbenzene substituted with fluorenyl groups Benzo [4,5] imidazo [2, Ι-a] isonitro? 0-11-ones also have high Light stability and a desired solubility. Further particular embodiments of the present invention is a compound of formula VI a y

(Please read the notes on the back before filling this page)-

, 1T Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Via), where X i is C 1 or B r, and one or both of R 'i 8 and R' 1 9 are -COOH, or α-or oc, a-branched C3 to C2o alkyl or Ra-C (O)-, where Ra means Ci to 02 alkyl; or Cs to C8 cycloalkyl, Cs to C8 cycloalkyl-CHz -, Phenyl, benzyl, etc. are unsubstituted or substituted with halogen · Cl to (: 12 alkyl or Ci to. ^ 2 alkoxy substituted, or one of R 'and R' 19 is a One or a, CX-branched C 3 to C 2 0 alkynyl or Ra_C (0)-, where Ra means Ci to Cz 〇 焼 -56-

This paper size applies the Chinese National Standard (CNS) A4 specification (21 × 297 mm) 557322 A7 B7 group; or group, benzene or C i is a linear group. Alkane 8 carbons R, benzyl to C6 are 1 to formula, for example a is preferably C3 to ^ 2, benzyl, etc. are unalkylated or Ci to 06 alkoxy. In the context of the present invention, Linear alkane 6 涸, and preferably 1 to 4 V, compounds of VI and 6a can be described in EP-A-456 609, V. Description of the invention (6) c5 to C8 cycloalkyl, C5 to C8 cycloalkyl- CH2-, benzyl, etc. are unsubstituted or substituted with halogen, Ci to 〇2 alkyl to Ci 2 alkoxy, and another R '18 and 1 ^ 1 C i to C 2 〇 alkyl . The branched alkyl group is selected from the group consisting of 1-methyl or 1,2-dimethyl-substituted alkane-1 groups, preferably containing 3 to 18, preferably 3 to 12, and most preferably 3 to atoms. X i is preferably C 1. Alkyl; either cyclopentyl, cyclohexyl or substituted with F, Cl, Br, C1 groups. The radical preferably contains 1 to 8 carbon atoms. Phase K is prepared in a conventional manner. The preparation method is based on the following. Please read the notes on the back first and then the page.

AcOH reflux

D R R

R

R

R

R Two kinds of isomers usually shown in the above formula are obtained * and can be used if necessary. B7 Description of the invention (Call) If separated by column chromatography. In principle, the present invention does not require separation of these two structural isomers. Another preferred embodiment of the present invention and Via compounds are known as organic materials, such as luminescence, " El ") and are described in, for example, US 5,59 3, cited documents. For example, a layer (combined thickness < 1.0 micron is particularly selected for injection and transfer) and provides pressure for injection and transfer of electrons and a very thin organic cold light medium. The positioning standard allows higher current density through the organic radiation and The thin layer of transmission efficiency can accommodate low voltages within the range of brightness levels that can be visually detected by ambient light. For example, the embodiment is based on this material for preparing electric cold light. These EL devices are based on 788 »W0 94 / 15441, a commonly used EL device includes) separate anode and cathode holes and another device as the organic cold to reduce the resistance, for the current density. Because of the light-cooled optical medium, the coupling has an increased acceptance The light emission level of the device reaches and the integrated electrical transmission layer is also used as the device's Ming type V, VI electro-the technique learned in this technology and two extremely thin ones in this article. One of the calendars is particularly selected for the light area. The given electrically biased emission is directly charged by the charge (for example, in the cold light region of the driver phase)

Order

Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs In another preferred embodiment of the present invention, the subject / object composition of the present invention can be used as a layer of organic emitting material in an EL device and can be used to prepare the EL device. These devices are known in principle, for example, from US 5,59 3,788 and the previous case cited in this text, so it is not necessary to repeat further details for those skilled in the art. Therefore, the electric cold light device containing the compound or composition of the present invention is also -58- This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 A7 B7 V. Description of the invention (θ) Central Bureau of Standards, Ministry of Economic Affairs The Employee Consumer Cooperative prints part of this invention. The emission intensity of the fluorescent composition of the present invention is 118 5,59 3, 788 or "0" when compared with those containing a host unit or an object military position but lacking willpower. Compared with a), the composition of the present invention produces large enhancement and strong b) shows strong solid-state fluorescence, regions, c) the composition uses UV and d) can achieve excellent light stability e) via appropriate guest molecules Its emission wavelength, f) can achieve high thermal spike characterization g) For materials that are easy to be prepared, the following examples are used to illustrate the present benzo [4,5] imidazo [2, the preparation is detailed in the column As mentioned above, the powder of 9 4/1 54 4 10 but lacking any guest units, the solid-state emission of the powder of the host unit has a strong emission of solid fluorescent light. The conventional composition has significantly enhanced the following advantages: Fluorescence Emission, where the emission wavelength can be excited in the visible and visible region of the electromagnetic spectrum, and outdoor and long-lasting properties * Selection (color adjustment) can reach a wide range, which can be made clear by co-precipitation of dissolved ingredients 1 -a] Isoindan-11-fluorenes have the following formula.

This paper size applies Chinese National Standard (CNS) A4 specification (210 × 297 mm) Please read the back first 557322 A7 B7 Invention Description (θ) A) Cangyou U · W 眯 晔 you "2 · 1-a" ···奚 · &节; section: 11: ._ 之 _ 制 _ ^ ^ Fen 妩 Example A 妩 yl 'Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 1,2,3,4-tetraphenylbenzo [4, 5] oxazolo [2, 1-a] isoazepin-11-one-7- (8, A, l) -carboxylic acid / (in 1). A 300-liter round bottom flask equipped with a stirrer and a reflux condenser was placed with 4.58 g (30.1 mmol) of 3,4-diaminobenzoic acid '13.6 g (30.0 mmol) 1, 2, 3,4-tetraphenylphthalic anhydride, and 100 ml of glacial acetic acid. The mixture was stirred and heated under reflux for 5 hours under a nitrogen atmosphere. The mud was cooled and the yellow solid was separated by filtration. The solids were washed with water followed by M formase. Obtained 10.9 g of a yellow solid (64%) ° 1 H-NMR (CDCI3, TMS): 58.43 (d, J = 1.2 Hz, 1Η'H (A9) or H (A, 6)), 8.33 ( d, J = 0.9 Hz, 1H, H (A9) or H (A, 6)), 8.05 (dd, J = 1.5, 8.4 Hz, 1H, H (A7) or H (A, 8)), 7.96 (dd, J = 1.6, 8.5 Hz '1H' H (A7) or H (A, 8)), 7.72 (d, J = 8.3 Hz, 1H, H (A6) or H (A'9) ), 7.61 (d, J = 8.5 Hz, 1H, H (A6) or H (A, 9)), 7.30—7 · 24 (®, 8Η), 7.18—7.15 (hi, 2H) » 6.92—6.89 (m, 6H) and 6.81 — 6.76 (ffl '4H) ο g AZ— 1,2,3,4-tetraphenyl-7- (tertiary butyl) benzo [4 , 5] oxazolo [2, Bua] isoazepin-11-pyrene (A2) and 1,2,3,4-tetraphenyl-8- (tertiary butyl) benzo [4,5] Imidazolo [2, I-a] isoazin-11-one (A '2). -60- This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 A7 B7 V. Description of the invention (4) The device has a stirrer and a reflux condenser 100 A liter round bottom bottle was filled with 0.99 g (6.0 mmole) 4- (tertiary butyl) -0-phenylene diamine, 2.73 g (6.03 mmole) 1, 2, 3, 4-tetraphenylphthalic anhydride, and 15 ml of glacial acetic acid. The mixture was stirred and heated under reflux for 3 hours under a nitrogen atmosphere. The mud was cooled and the yellow solid was separated by filtration. The solid M was washed with water. 2.5 g of a yellow solid are obtained (total of 71%; A2 is 42% and A ′ 2 is 29%). The two isomers can be purified by column chromatography using CH2Clz as the eluent. A 2 (7-position) 1 H-NMR (CDC13, TMS): 57.60 (d, J = 1.3 Hz, 1H, H6), 7.58 (d, J = 8.4 Hz, 1H, H9), 7.30 (dd , J = 8.5, 1.4Hz, 1H, H8) »7.30-7.16 (m» 10H), 6.8 7-6. 8 3 (m, 6H), 6.81-6.76 (m, 4H), 1.29 (s, 9H) 〇 1 3 C-NMR (CDCI3): δ 160.3 (s »C = 0), 156.1 (s, C4 b), 149 · 6 (dt, C5 a)» 148.3 (m, C7), 147.9 (t »C3), 145.5 (t, Cz), 141.9 (t, C4 or C1), 138.4 (n), 138.1 (m), 137.7 (C4 or Ci), 136.1 (in), 135.5 (m), 130.9, 130.8 , 130.3, 130.1 (s) * 129.8, 127.7 * 127.5, 127.1 * 127.0, 126.4, 126.3, 123, 9 (dm, J 1 = 160 Hz, C8), 118.7 (dd »J 1 = 160 Hz» C6) ^ 1 1 1 · 6 (d »J1 = 170 Hz · C9), 35.0 (CMe3), 31 · 6 (CH3) 0 -61- This paper size applies to China National Standard (CNS) A4 (210X 297 mm)

\\ Printed by the Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ 557322 A7 s_______ V. Description of the invention (π) A ^ ρ. (S-part Jin) 1 H-NMR (CDCI3, TMS): δ 7.73 (d »J = 1.6 Hz, 1H, H9), 7.47 (d, J = 8.6 Hz, 1H, H6), 7.28— 7.22 (ffl, 9H), 7.20— 7.17 (诳, 2H), 6,93— 6.89 (a * 6H ) * 6 · 82— 6 · 78 (in, 4H), 1 · 32 (s, 9H) 〇1 3 c-NMR (CDCI3): δ 1 6 0.1 6 0.6 (s, C = 0), 155.6 (s , C2), 150.6 (s, C2), 150.3 (bi, C8), 147.9 (t, C3), 147.4 (ddd, C5 a), 145.4 (t, C2), 141.9 (t), 138.4 (ffl) 138.0 (m), 137.6 (t), 136.0 (m), 135.6 (m), 130.9, 130.8, 130.4, 130.2 (s), 129.8, 127.7, 127.5, 127.4, 127.1, 127.0, 126.3, 122.4 (dd, J 1 = 160 Hz, C7), 121.1 (d, J 1 = 160 Hz, C6), 109-3 (ddd, J1 = 160 Hz, C9), 35 · 2 (CMe3), 31.5 ( CH3) 0 S mm A Pi 1, 2,3,4-tetraphenylbenzo [4,5] oxazolo [2, Bua] isonitro ί β -11-one (A 3) The device has a stirrer and 500 奄 of reflux condenser A round bottom bottle was filled with 8.34 g (73.3 mol) of 0-phenylene diamine (95%) and 33.0 g (66 · 3 mmol) of 1,2,3,4-tetraphenyl Phthalic anhydride, and 200 liters of glacial acetic acid. Under nitrogen atmosphere, the mixture was stirred and heated under reflux for 11 hours. The mud was cooled and the yellow solids were separated by filtration. The solid was washed with M water and then M methanol. 35.1 g of a yellow solid (92%) were obtained. -62-Please read the note on the back first. The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 557322 A7 B7 V. Description of the invention U 丨) 1 H-NMR (CDC13, TMS): 5 7.66 (d, j = 7.6 Hz, 1H), 7.55 (d, J = 7.7Hz, 1H), 7.30-7.15 (sister, 12H), 6.9 3— 6.88 (ffl, 6H), 6.81— 6.76 (ffl , 4H) °

MS: 524 ([M] +) 〇 Example A 1,2,3,4-tetraphenyl-7 (or 8) -nitrobenzo [4, 5] oxazo [2,1-a ] Isoindan-1 hydrazone (A 4, A / 4). A 100-liter round-bottomed bottle equipped with a stirrer and a flow condenser was placed with 1.53 g (9.99 mol) of 4-nitro-o-phenylene diamine (95%) and 4.53 g (1 〇〇molol) 1,2,3,4-tetraphenylphthalate, and 25 ml of glacial acetic acid. Under a nitrogen atmosphere, the mixture was stirred under reflux and heated for 1.33 hours. The mud was cooled and the yellow solid was separated by quenching. The solid was washed with K water and then M methanol. Obtained 6.1 g of light yellow solid (100%). 0 1 H-NMR (CDCI3, TMS): 58.57 (d, J = 2.2 Hz '1Η' H (A9) or H (A, 6)), 8.48 (d, J = 2.1 Hz, 1H 'H (A9) or H (A, 6)), 8.22 (dd, J = 2.1, 8.8 Hz * 1H, H (A7) or printed by the staff consumer cooperative of the Central Standards Bureau of the Ministry of Economic Affairs H (A, 8)), 8.13 (dd, 1H, H (A7) or H (A, 8)), 7.75 (d, J = 8.8 Hz, 1H, H (A6) or H (A, 9)), 7.65 (d 'J = 8.9 Hz, 1H, H (A6) or H (A, 9)), 7.32- 7.23 (m, 8H) * 7.18- 7.15 (m, 2H), 6.95-6.90 (m, 6H) and 6.81-6.76 (Di, 4H) 〇MS: 5 6 9 ([M] +) 0 -6 3-This paper size applies to China National Standard (CNS) A4 (210X 297) (Foot) 557322 A7 B7 ___ V. Description of the invention (noisy) Serenyl A 5 1,2, 3,4-tetraphenyl-7 (or 8) -methylbenzo [4,5] imidazo [2, 1-a] isoniazine-11-moe (A 5 * A 7 5). A milliliter round bottom bottle equipped with a stirrer and a reflux condenser was placed with 1.30 g (10.64 millimoles) of 4-methyl phenylenediamine (95%) and 4.53 g (10.01 mol) 1,2,3,4-tetraphenylphthalic anhydride, and 25 ml of glacial acetic acid. The mixture was stirred and heated under reflux for 5 hours under a nitrogen atmosphere. The mud was cooled and the yellow solids were filtered by fractal degrees. The solids were washed with water and then with formic acid. Obtained 4 · 16 g of yellow solid ship (77%) 〇 1 H-NMR (CDCls, TMS) 57.52 (d, J = 8.1 Hz, 1'H (A6) or H (A, 9)), 7 · 48 (width s, 1H, H (A9) or H (A'6)), 7.42 (d, J = 8.2 Hz, 1H, H (A6) or H (A, 9)), 7.36 (width s , 1H, H (A9) or 11 (Aug, 6)), 7. 2 7- 7. 2 4 (111,811), 7-18 — 7.15 (ιη, 2Η), 7.06 (width d , LH, H (A7) or H (A'8)) '6.99 (width d, 1H, H (A7) or H (A, 8)), 6.92 — 6 · 88 (ro' 6H) And 6 · 8 0 — 6 · 7 5 (π », 4 Η). MS: 538 ([Μ] +), 537 ([Μ] +) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs. Fenmin A β 1,2,3,4-tetraphenyl-7 (or 8) -methoxybenzo [4,5] imidobenzo2,1, a] isoazepine (A6, A '6). A milliliter round bottom bottle equipped with a stirrer and a reflux condenser was placed with 1.38 grams (9.99 millimoles) of 4-methoxyphenylenediamine (95%) -64- This paper size applies to Chinese national standards ( CNS) Α4 specification (21〇'297 mm) 557322 Α7 Β7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (0), 4.52 grams (9.99 millimoles) 1, 2, 3, 4- Tetraphenylphthalic anhydride, and 20 ml of glacial acetic acid. The mixture was stirred and heated under reflux for 7 hours under a nitrogen atmosphere. The sludge was cooled and the yellow solid was separated by filtration. The solid K water was washed and purified by K-column analysis. 3.5 g of a yellow solid (68%) were obtained. 1 H-NMR (CDCI3, TMS): 57.52 (d, J = 8.6 Hz, 1H, H (A6) or H (A'9)), 7.42 (d, J = 8.9 Hz, 1H, H (A6 ) Or H (A, 9)), 7.27-7.23 (βι, 8Η), 7.20 (d, 1H, J = 2.6 Hz, 1H, H (A9) or H (A'6)), 7 · 19— 7 · 14 ('2H)' 7.08 (d, J = 2.4 Hz, 1H, H (A9) or H (A, 6)), 6.92—6 · 88 (m, 6H), 6.85 ( dd »1H, J = 2.4» 8.7 Hz, H (A7) or H (A, 8)), and 6.80-6_74 (m, 1H, H (A7) or H (A'6) + 4H) O MS: 554 ([M] +) 〇V mm A 7 1,2, 3,4-tetraphenyl-6,7,8,9-dibenzobenzo [4,5] oxazo [2,1- a] Isoindan-1 ketone (A 7). A 100 ml round bottom bottle equipped with a stirrer and a reflux condenser was placed with 0.84 g (4.03 mol) of 9,10-diaminophene, 1.83 g (4.04 mmol) 1, 2,3,4-tetraphenylphthalic anhydride, and 15 liters of glacial acetic acid. The mixture was stirred and heated under reflux for 5 hours under a nitrogen atmosphere. The mud was cooled and the orange solids were separated by filtration. The solid vessel was washed with M water and then washed with methyl formaldehyde, and then purified by M column chromatography. Obtained 2.01 g of orange solid -65-

This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 kl -..._____ B7 V. Description of the invention "V" (80%) 〇1 H-NMR (CDC13, TMS): 5 9.19 (dd , J = 1.5, 8.0 Hz, 1H, H9 or Hi 〇), 8.70 (dd, J = 7.8 Hz, 1H, H9 or

Hi 0), 8.64 (ffl, lH, H6_Hi3), 8.32 (ιπ, 1Η · H 6 or Hi 3) · 7.64-7.59 (m »4H, H 7» β »1 1, iz), 7 · 37 — 7 · 28 (m, 8H), 7 · 2 5— 7 · 2 2 (field, 2 H) f 6.96 — 6. 90 (shift, 6H), 6.86— 6.79 (m, 4H).蓳 L ife Example A 8 1,2,3,4-tetrachloro-7 (or 8) -nitrobenz [4,5] oxazolo [2, 1-a] isoindan-1 ketone ( A 8, A '8). A 200-liter round bottom flask equipped with a stirrer and a reflux condenser was placed with 2.30 g (15.0 mmol) of 4-nitro-o-phenylene diamine, 4.29 g (15.0 mmol) of 1,2 , 3,4-tetrachlorophthalic anhydride, and liters of glacial acetic acid. The mixture was stirred and heated under reflux under a nitrogen atmosphere for 2 hours. The mud was cooled and the yellow solid was separated by filtration. The solids are washed with water and then with formazan. This gave 5.48 g of a pale yellow solid (91%). 1 H-NMR (CDCI3, TMS) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: δ 8.75 (dd * J = 1. 7 Hz, 1H, H (A9) or H (A, 6)), 8.74 (dd, J = 2.3 Hz, 1H, H (A9) or H (A, 6)), 8.40 (dd, J = 2.2, 8.8 Hz, 1H, H (A7) or H (A, 8)), 8 · 32 (dd, J = 2.3, 8.9 Hz, 1H, H (A7) or H (A, 8))., 7.97 (dd, J = 8.7 Ηζ · 1H, H (A6) or H (A, 9)), 7.96 (dd, J = 9.0 Hz, 1H, H (A6) or H (A, 9)) 0 MS: 4 0 3 ([M + 2] +), 401 ([M] ".- 66- This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 4-tetrachlorobenzo [4,5] pyrazolo [2,1-a] isoazepine-1 (or 8) -carboxylic acid (A 9, A / 9). The device has a stirrer A 1-liter round-bottomed flask with a bypass condenser was placed with 15.2 g (100 mmol) of 3,4-diaminobenzoic acid, 28.6 g (100 mmol) of tetrachlorophthalic anhydride, And 450 ml of glacial acetic acid. The mixture was stirred and heated under a stream of nitrogen under a nitrogen atmosphere for 15 minutes. At that time, the mud was cooled and the green-yellow solid was separated by centrifugation. The solid was first washed with water and then with formazan. 37.0 g of green-yellow solid (92%) was obtained. MS: 404 ([M + 4] +) 402 ([Μ + 2] +) · 400 ([Μ] +), 387 ([M + 4-0H] +), 385 ([M + 2-OH] +), 383

([M-OH] +) 〇 窨) fe case A 1 O 1,2,3,4-tetrazol-7 (or 8)-(tri-butyl) benzo [4,5] oxazo [ 2, la] isoazaindene-11-fluorene (A10.A'10). A milliliter round bottom bottle equipped with a stirrer and a reflux condenser was placed with 2.48 g (15.1 mmol) of 4- (2, -methyl-2'-propyl) -〇-phenylene diamine, 4 30 g (15.0 mmol) of tetrachlorophthalic anhydride 'and 40 ml of glacial acetic acid. The mixture was stirred and heated under reflux under a nitrogen atmosphere for 3-5 hours. The mud was cooled and the yellow solid was separated by filtration. First, rinse with water and then methanol. Obtained 5.22 grams of light yellow solid hips (84%). 0 1 H-NMR (CDC13, TMS): δ7 · 82 (dd, J = 0.5 Hz, 1H, -67-) This paper size applies Chinese National Standard (CNS) A4 size (210 X 297 mm)

557322 A7 B7 V. Description of the invention (recognition) H (A9) or Η (Α, 6)), 7.73 (dd · J = 0.5, 8.6 Hz, 1H, H (A6) or H (A, 9 )), 7.42 (dd, J = 1.8, 8.6 Hz, 1H, H (A7) or H (A'8)), 1 · 40 (Bi, 9H). MS: 416 ([M + 4] +), 414 ([M + 2] +), 412 ([M] +), 401 ([M + 4-CH3] +), 399 ([M + 2_CH3] " j 397 ([M-cu3] +) 〇 Example of window A 1 1 1, 2,3,4-tetrachloro-7 (or 8) -benzylidenebenzo [4,5] pyrazolo [2 (A) Isoindan-11-one (All, A '11). A 100-liter round-bottomed flask equipped with a stirrer and a reflux condenser was placed into 2.13 g (10.0 millimoles). 3,4-diaminodibenzoic acid 2.87 g (10.0 mmol) of tetrachlorophthalic anhydride, and 23 liters of glacial acetic acid. The mixture was stirred and heated under reflux in a nitrogen atmosphere. 3 • 5 hours. The mud was cooled and the yellow solid was separated by filtration. The solid was washed with M water and then M methanol, then dissolved in hot CHC13, and the Soxhlet extractor was used to remove insoluble impurities. After that, 3.36 g of yellow solid «(72%) ° Printed by the Consumers Cooperative of the Central Bureau of Standards of the Ministry of Economy 1 H-NMR (CDC13 · TMS): δ 8.28 (dd * 1H, H (A9) or H (A, 6 )), 7.93 (dd, J = 0.7, 8.5 Hz, 1H, H (A6) or H (A, 9)), 7.87-7.82 (m, 3H, H (A7) or H (A, 8) and H2 ,, 6,) , 7.64 (tt, J = 1.2, 7.5 Hz, 1H, H3 ,, 3,), 7.52 (t, J = 7 · 6 Hz, 2H, H4,) 〇MS: 464 ([M + 4] + ), 462 ([M + 2] +), 460 ([M] +), -6 8-This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) 557322 A7 B7 V. Description of the invention (¢ /] 387 ([M + 4-C6 Hs] +) J 385 ([M + 2-C6 Hs] +) »383 ([M-C6 IU] +), 359 ([M + 4-C6 Hs C0] +), 357 ([M + 2-C6 H5 C0] +), 355 ([M-C6 H5 C0] +). Example A 1 P. 1,2, 3,4-tetrachlorobenzo [4 , 5] imidazo [2,1-a] isoindane-11-one (A12) 〇 Compound A 1 2 is prepared according to the procedure described in EP-A- 0 4 5 6 6 0 9 R) Xuan The color of the hair is very bright. Example 1 R 1 Ν, Ν'-Benzylquinacridone (B1). A 500 ml round bottom bottle equipped with a stirrer and a reflux condenser was placed with 3.13 g (10.0 mmol) of quinacridone (hereinafter referred to as QA): 17.11 g (100 mmol) ) Benzyl bromide, 138.21 g (1,000 mmol) K2 C03 and 200 ml dimethylformamide (DMF). The mixture was stirred and heated under reflux under a nitrogen atmosphere for 7.5 hours. The mud was cooled and the orange solids were separated by filtration. The solid was washed with M water, then M acetone and formic acid. This gave 4.34 g of an orange solid (88%). 1 H-NMR (DMSO-d6, dimethylimine (DMS0)) ·· S8.43 (s »2H · Η1), 8.35 (dd, J = 7.9Hz, 2H, H5), 7.79

(dt, J = 8.2 Hz, 2H, H4), 7.67 (d, J = 8.6 Hz »2H, H2), 7.37 (t, 4H, H3), 7.33 (t, 2H, H6), 7.31 (t , 2H, H7), 7.27 (d, 4H, H8), 5.29 (s, 4H, H9) 〇-6 9-This paper size applies to China National Standard (CNS) A4 (210X297 mm) Please read the back Note the item printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 557322 Μ B7 V. Description of the Invention (β) Example B 1 N, N'-Diphenylmethyldiphenyldiketopyrrolopyrrole. Please read the precautions on the back. A 100-liter round bottom bottle with a stirrer and a reflux condenser was placed with 1.47 g (5.1 mmol) of diphenyl dimenopyrrolopyrrole (hereinafter referred to as DPP). ), 3.44 g (20.1 mmol) of benzyl bromide, 1.38 g (1.00 mmol) of K2 C03 and 50 ml of DMF. Under a nitrogen atmosphere, the mixture was stirred and heated to 100 ° for 42.5 hours. The mud was cooled and the orange solid was separated by filtration. The solids were washed with water followed by Kappa yeast and then dissolved in hot CHCls. The CHC13 solution was applied to a silica gel column using C Hz Cl2 as the eluent. After concentration, 1.21 g of an orange solid (51%) 1 H-NMR (CDC13, TMS) was obtained: 5 7.75 (d, J = 7.1 Hz, 4H, Η 1), 7.49-7 · 43 (m, 6Η, Η2 and Η3), 7 · 30 (t, J = 7.4 · ζ, 4Η, Η5), 7.24 (t, J = 7.3Hz, 2H, H6), 7.19 (d, J = 7.4 Hz, 4H, H4 ), 4.99 (s, 4H, H7) Π) light emitting composition Ximubei. Example C 1 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs as 1.01 x 10-4 moles (0.0557 g) of A 1 as the main compound and different Dong Zhi-Rhodamine 19 (Kodak Lab Chemicals) as a passenger compound (B3) or Rhodamine 6G (Kodak Lab Chemicals) was dissolved as a guest compound (B4) in 20 ml of 1,2-dichloroethane and mixed. The solvent was then evaporated using a rotary evaporator (RE47, Yaioato Science Co., Ltd.) to obtain fluorescent powders including A 1 and B 3 or B 4 at various concentrations. -7 0-This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 557322 Α7 Β7 The measurement of the luminescence spectrum of fluorescent powder is based on a spectrophotometer (F-4) 5 00, HITACHI Co., Ltd.), using a solid-state sample holder * in its absorption band K army color light (Aaax = 360 mm) to excite the host compound. The results are shown in Table 1. Table 1: Fluorescent properties of fluorescent powders. Please read the note of τέ. Note the concentration of the subject, the guest, the light, the cold light spectrum (the ear%), the peak wavelength (na), and the peak intensity. Α1 None 0 512 545 Α1 Β3 0. 1 571 987 Α1 Β3 0. 2 573 1040 Α1 Β3 0. 5 580 869 Α1 Β4 0. 2 579 968 Example of printing by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs C: 2 1 · 0 X 10 1-4 ears (0.0557 g) A 1 and different amounts of B1 were dissolved in 20 ml of 1,2-dioxane and mixed. Solvent K lyophilizer (FD81, Tokyo Rikakikai Co., Ltd.) was freeze-dried and sublimated to obtain fluorescent powders including A1 and B1 in various concentrations. The photoluminescence spectrum M of the fluorescent powder was measured in the same manner as in Example C1. The results are shown in Table 2 〇 Table 1: Fluorescent properties of fluorescent powders including A1 and B1 -71- This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 557322 Α7 B7 V. Description of the invention () Main body Guest 艚 Guest Concentration Light Cold Light Spectrum (Molar%) Peak Wavelength (ηπι) Peak Intensity A1 None 0 510 570 Α1 Β1 0. 1 563 687 Α1 Β1 0. 2 565 1014 Α1 Β1 0. 5 564 964 (Please read the back first (Notes for filling in this page)

Li Li C: 3 3.0 × 10-4 moles (0.1706 g) of A2 or A '2 as the host compound and different amounts of B 1 or B 2 as the guest compound and dissolved in 2 0 liter 1- Methyl-2-¾lorrolidine and mixed. The solution was then poured into 400 ml of water and its K homogenizer (RLTRA-TURRAX T25, IKA-Labortechnik) was vigorously stirred. The precipitate was filtered and dried under a vacuum of 60 ° to obtain fluorescent powders including A2 or A3 and B1 or B2 at various concentrations. The light cold light spectrum M of the fluorescent powder was measured in the same manner as in Example C1. The results are shown in Tables 3 and 4. Table 3: Fluorescent properties of fluorescent powder including Α2 and Β1 or Β2. Concentration of host and guest. Concentration of light. Cold light spectrum (mol%). Peak wavelength (η ·). Peak intensity -72. Specifications (210 × 297 mm) 'Order

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 6 A2 B1 5. 0 529 1579 A2 B2 1. 0 534 2 0 54 A2 B2 2. 0 537 2 3 2 4 A2 B2 5. 0 542 2160 Table 4: Fluorescence including A '2 and B 1 fluorescent powder Nature Host Object Concentration Light Cold Light Spectrum (mol%) Peak Wavelength (nm) Peak Intensity A, 2 None 0 522 552 A, 2 B1 1. .0 524 285 4 A, 2 B1 2 .0 525 3 9 4 2 A , 2 B1 5 .0 529 2 2 2 7 Window) Fei Li printed at the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs carefully measured as the host compound of A 1, as the guest compound of B 1 and acrylic polymer (PMMA; Polymethylmethacrylic acid, -73- This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 557322 Μ B7 V. Description of the invention (

Aldrich Chemical Co., Ltd.) and dissolved in CHCI3 / formaldehyde (95/5 vol%) (Wako Chemical Co., Ltd.) K to produce a clear, homogeneous solution (5% by weight). The mixture was then plated with a M metal rod (KCC, No. 8 rod, RK Print-Coat instrument) on a glass substrate and the solvent was removed. At this point the polymer film had the visible color and spectral characteristics of a typical precursor. The light cold light spectrum K of the fluorescent film was measured in the same manner as in Example C1. The results are shown in Table 5.

Printed by the Employees' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 74 This paper size applies to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) 557322

7 B V. Description of the invention (,) Table 5: Fluorescent properties of thin polymer A1 (wt%) B1 (wt%) PMMA (wt%) Wavelength light wavelength Cold light spectrum Um) Peak intensity 5 0 95 501 401 5 0.05 95 545 561 5 0. 1 95 548 564 5 0. 2 95 552 586 5 0. 3 95 555 788 10 0 90 501 440 10 0.05 90 546 593 10 0. 1 90 551 819 10 0. 2 90 553 811 10 0. 3 90 559 896 30 0 70 501 461 30 0.05 70 551 62 1 30 0. 1 70 552 781 30 0. 2 70 556 734 30 0. 3 70 558 799

Example C FS Printed 0.1 grams of the fluorescent powder of Example C3 by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, which includes the main body of A2 and -75- This paper size applies to China National Standard (CNS) A4 specifications (210X 297) (Centi) 557322 Α7 B7 5. Description of the invention (called) As the object of B2, its M homogenizer (RLTRA-TURRAX T25, IKA-Labortechnik) is dispersed to 1.0 g of functionalized acrylate monomer [KAYARAD D310 (Nippon Kayaku Company) )]. 5.0 grams of a 10% by weight aqueous solution of polyvinyl alcohol (PVA-117, Kurare) was added to the vigorously stirred dispersion M over a period of about 10 minutes to obtain a homogeneous suspension, and recrystallized K2 S2 as an initiator 08 was added at room temperature. The reaction mixture was aerated with KNz gas for about 30 minutes. K was used to remove oxygen and then placed in a water bath controlled at 80 ° C for 10 hours. Highly crosslinked fluorescent powder-containing polymer particles were obtained and separated by filtration. Those particles were then washed multiple times with M water and methanol. Drying was performed overnight in a vacuum box of 60 ^. The yield was 34.4%. The photoluminescence spectrum of the luminescent polymer particles was measured in the same manner as in Example C1. The results are shown in Table 6. Table 6: Fluorescent properties of fluorescent polymer powder. (Please read the notes on the back before filling this page)

. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Subject Matter Guest Object Concentration Light Cold Light Spectrum (Moire%) Peak Wavelength (n in) Peak Intensity Α2 None 0 525 370 Α2 Β2 5. 0 538 1520

Fen _ Example Γ: ft 0.1 g A2 as main «, without or 〇.002 g B2 as a guest and 1.0 g of functionalized acrylic acid monomer (KAYARAD D310) was dissolved in -76- This paper size applies to China National Standard (CNS) A4 specification (210 × 297 mm) 557322 Α7 B7 V. Description of the invention (7 $ 10 ml of p-methyl-2-pyrrolidine hydrazone. The solution was then poured dropwise to a K homogenizer and vigorously stirred for 200%. Milliliter of a 2% by weight aqueous solution of polyethylene ferment (PVA-117, Kurare). A yellow precipitate with green fluorescence was immediately formed, in which the recrystallization initiator K2 S2 08 was added. The reaction mixture KNz was aerated for about 30 minutes. The oxygen was removed and then placed in a water bath controlled at 80TC for 10 hours. Highly crosslinked polymer particles were obtained and separated by filtration. These particles were then washed multiple times with water and methanol. The drying was performed in a vacuum box of 60¾ Overnight. Yield 42.5%. The light cold light spectrum M of the fluorescent polymer particles was measured in the same manner as in Example C1. The results are shown in Table 7. Table 7: Fluorescent properties of the fluorescent polymer powder. Cold light spectrum (mol%) peak Wavelength (ηηι) Peak Intensity A2 None 0 524 410 Α2 Β2 2. 0 531 1790 Fendi Example C 7 There is a rubber seal installed in a glass reaction bottle, a magnetic stir bar and maintained in a nitrogen atmosphere, 30 ml degassing Water was added and heated to 60¾. Maintaining the reaction temperature at 60 ^ 0, degassed 2.08 grams (20% by weight) of pills 12, 5.12 grams (49% by weight) of ethanedial dimethacrylate, 3.1 grams (30% by weight) methyl (methacrylate), without or 0.13 g (1 heavy -77- This paper size applies to China National Standard (CNS) A4 specifications (210 乂 297 mm), please Read the notes on the back page printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs and printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs and printed by 557322 A7 B7. 3)), 0.16 g of 2,2'-azobis (isobutyric acid nitrile) and 10 ml of chloroform were added in one portion. The reaction was performed under vigorous stirring for 6 hours, and then the reaction mixture was filtered. Precipitate Contains bright orange particles of uneven shape and size. These particles M water was washed several times and the M water aspirator was dried. The final drying was performed overnight in a vacuum box of 60 °. The yield was 90%. The obtained polymer powder was ground into a fine using a standardized laboratory mortar and pestle. Powder. The light cold light spectrum K of the fluorescent polymer particles was measured in the same manner as in Example C 1. The results are shown in Table 6. Table 8: Fluorescent properties of the fluorescent polymer powder. Ear%) Peak wavelength (nm) Peak intensity A12 None 0 511 242

Al2 Lumogen F orange 1.0 584 680 Fen) fe case Γ «1,2,3,4-tetraphenylbenzo [4,5] imidazo [2, bua] isoazepin-11-ones light-stable Sex. 1,2, 3,4-tetraphenyl-7 (or 8) -methoxybenzo [4, 5] imidazo [2, la] isoazepine-1 and other derivatives were placed The sample holder used in Example C1. Those samples were tested using a xenon lamp aging tester (WEL-15X-HC-B.Ec, Suga Test Instrument Co., Ltd.) under the following conditions for light-78. )

557322

7 B Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Description of the invention (7?) Exposure for up to 100 hours. Light intensity: 0 · 35 W / cm2 at 340 nm, temperature: 631C on black panel, humidity: 50%. The cold light intensity is measured before the light exposure and the percentage of intensity loss is measured as K. The peak height is compared after the light exposure is as described in Example C1. Table 9: Light spike characterization of 1,2,3,4-tetraphenylbenzo [4,5] imidazo [2, Ι-a] isoazepin-11-ones. Compound λ max (nm) Intensity before exposure Intensity loss after exposure U) A3 505 1211 759 37 A2 517 80 1 751 7 AJ2 505 2 0 3 3 1595 22 Α5 533 488 390 20 Α6 556 45 45 < 1 Α7 598 159 152 4 Fenton example π g 1,2, 3,4-tetrachloro-7-methylbenzo [4, 5] oxazo [2, la] isoazepine-11-fluorene and other derivatives Light stability. -79- This paper size applies to China National Standard (CNS) A4 (210X 297mm) (Please read the precautions on the back before filling this page)

557322 B7 V. Description of the invention (β) The procedure of Example C 8 was repeated, but this time, 1,2,3,4-tetrachloro-7-methylbenzo [4, 5] oxazo [2, A] Isoindan-1 ketone (A〃) and 1,2,3,4-tetrachloro-7-tert-butylbenzo [4,5] oxazo [2, Ι-a] iso Indene-ll-_ (A10) and 1,2,3,4-tetrachloro-7-benzylidenebenzo [4,5] oxazolo [2, Bua] isoazepine-U- All (All) comparison. The results are described in Table 10. Table 1 0: (Please read the precautions on the back before filling in the page) Printed compound λ max (na) by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Before exposure intensity Intensity loss rate after exposure U) A " 534 170 142 17 A10 546 156 136 11 All 524 273 247 10 -80- This paper size applies to China National Standard (CNS) A4 (210X297 mm)

Claims (1)

557322 A8 B8 C8 D8 VI. Application scope of patents where X i is C 1, R'i 8 and R, i 9 or one or both of them is a COOH, or unitary or α, α-branched C3 to C8 Alkyl or Ra—C (〇) one, wherein R a represents phenyl, and wherein the guest chromophore is selected from the group consisting of quinopyridine, north, di_pyrrole, pyridyl, and rhodamine And the effective amount of the guest chromophore is selected from the range of 0.001 to 30% by weight relative to the total amount of the subject and the guest chromophore, wherein (a) the guest chromophore is uniformly distributed in the The host chromophore matrix, or (b) both the host chromophore and the guest chromophore are homogeneously distributed in the polymer matrix. 2 ♦ —A method for preparing a composition according to item 1 of the scope of the patent application, the composition comprising a host chromophore and a guest chromophore and, if necessary, a polymer matrix, wherein the absorption spectrum of the guest chromophore and the host chromophore The fluorescence emission spectra of the groups overlap, which is characterized in that (a) the host chromophore is selected from the benzo [4, 5] pyrimidazo [2, 1-a] isoazepin-1 ketone of formula VI a. Read the back of the © -2-This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 557322 A8 B8 C8 D8 VI. Patent application scope where Ri 0 is 1'1, and ruler 1 8 and Rl 9 or both At the same time, C, to (: 6 alkyl or Ci to (: 6 alkoxy, or Ri 7 together with Ri 8 and only! 9 together with R 2) means one CH = CRz 4 — C R2 5 = CH —, Wherein R2 4 and Rz 5 are fluorene, or [4,5] imidazo [2,1 -a] isoazindene-1 1 -ones of the formula Via Where X! Is C 1, one or both of R'i 8 and R'i 9 are a COOH ′ or cx or a, cx —branched C3 to C8 alkyl or Ra — C (0) — Where R a represents phenyl. (b) mixing the host chromophore and an effective amount of at least one guest chromophore, and a selective polymer or polymerizable precursor in the presence of a solvent, and (c) precipitating the host and guest chromophore, optionally When the polymer of step (b) is present, or (d) the host and guest chromophores are precipitated during the polymer precursor of step (b). 3 ♦ —Polymerizable composition containing polymerizable monomers or prepolymers -3- This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) (Please read the precautions on the back before (Fill in this page) 557322 A8B8C8D8 6. The scope of the patent application, which is mixed with the composition according to item 1 of the patent application scope in the form of powder containing particles, or with the subject and object chromophores in the composition according to item 1 of the patent application scope. , Or mixed with both. 4 ♦ Polymerizable composition according to item 3 of the scope of patent application 'wherein the polymerizable monomer or prepolymer is dissolved in powder form containing particles, the composition according to item 1 of the scope of patent application or the scope of patent application The subject and object chromophores in the composition of item 1. 5 ♦ —A composition of a polymerized photoresist material comprising a carrier material and a highly embossed image, which contains a composition in the form of powder containing particles of 圼, or a composition according to item 1 of the scope of patent application, or according to item 1 The subject and object in the composition of the item are colored, or both, and if necessary, are dissolved and / or homogeneously distributed therein. 6 ♦ —A method for preparing a fluorescent high relief image on a carrier, characterized in that the coated photopolymerizable composition according to item 3 of the scope of the patent application is irradiated under a photomask or engraved on the carrier by laser. , Develop the radiated composition, and finally remove the non-radiated parts. 7. The method according to item 6 of the scope of patent application, wherein the coated photopolymerizable composition is dried and the solvent is removed. 8 ♦ The composition according to item 1 of the scope of patent application, which is used as a fluorescent material. 9 ♦ A compound characterized by its correspondence to Formula VI-4-This paper is sized to the Chinese National Standard (CNS) A4 (210 X 297 mm) -------------- ------------- (Please read the notes on the back before filling this page) Order: 557322 Or both are C 1 7 and R i 8 CRz 5 = CH-, which X A8 B8 C8 D8 Patent Application Park R, (VI) R, where 17 and 1-20 are 1 ^, and only 18 and 1 ^ to alkyl or Ci to Cs alkoxy, and R and R i 9 Together with R 2 〇 means -CH = CR2 4 where R 2 4 and R 2 5 are Η, respectively. 1〇 · A compound of the formula R ·, (Via) where X! Is one or both of C 1, r, 18 and R ′ are ~ C00H 'or σ or α, α-branched C3 to C8 alkyl or Ra-C (0)-, where Ra means phenyl. 1 1 · The composition according to item 1 of the scope of patent application, which is used as an organic emitting material and is used to prepare an electric cold light (EL) device. 1 2 ♦ —An electro-luminescence device containing a composition in the scope of patent application 1 or a compound in scope of patent applications 9 and 10. -^-This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) • (Please read the precautions on the back before writing this page) 557322 A8B8C8D8 Patent application scope 1 3 ♦ Compounds according to item 9 or 10 of the patent application scope, which are used as organic emitting materials and used to prepare electroluminescent (EL) devices. -6 This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) (Please read the precautions on the back before writing this page).