Compound containing diazo group and preparation method thereof

Abstract

The invention discloses a compound containing a diazo group and a preparation method and application thereof, and the compound containing the diazo group has and preferably has the following structure (I): imgabs0 #. The compound containing the diazo group is prepared by adopting a one-pot method, the process is simple, the reaction is mild, and industrial production is facilitated; the raw materials and reagents used in the invention are common reagents in the market, and have the advantage that the raw materials are easy to obtain. In short, the method has the advantages of easiness in operation, low synthesis cost and the like. Most importantly, the method is simple in post-treatment and small in environmental pollution, can be used for large-scale industrial production, is beneficial to accelerating localization of the photosensitizer, and has great social value. Moreover, the compound containing the diazo group, as a photosensitizer, has the advantages of high resolution, good pattern line definition, no influence of oxygen, high contrast, high sensitivity ratio negativity and strong dry etching resistance.

Description

Technical Field

[0001] The present invention relates to a compound and a preparation method thereof, and particularly to a compound containing a diazo group and a preparation method thereof, such as a diazo photosensitizer and a preparation method thereof. Background Art

[0002] Photoresist, also known as photoresist, refers to a corrosion-resistant thin film material whose solubility changes upon irradiation or radiation by ultraviolet light, electron beam, ion beam, X-ray, etc. According to... Photoresist is mainly used in fine pattern processing operations such as display panels, integrated circuits, and semiconductor discrete devices, and is an irreplaceable key material in the semiconductor field. Domestic photoresist mainly relies on imports. With the increasingly fierce international competition, the localization of photoresist is imminent.

[0003] The photosensitizer is an important component of the photoresist composition and can undergo a chemical reaction under the action of light. The type and characteristics of the photosensitizer have a crucial impact on its lithography characteristics and application effects. Diazonaphthoquinone (DNQ) consists of a naphthalene ring and a diazo group and has excellent photosensitivity. It is widely used as a photosensitizer in positive photoresists. After ultraviolet exposure, diazonaphthoquinone chemically decomposes in the photoresist and becomes a solubility enhancer, significantly increasing the solubility factor in the developer to 100 or higher. Currently, the commonly used g / i-line photoresists on the market are mainly linear phenolic resin / diazonaphthoquinone series: that is, using linear phenolic resin as the film-forming material and diazonaphthoquinone compounds as the photosensitizer (also known as diazonaphthoquinone-based positive photoresist, diazonaphthoquinone photosensitizer, diazonaphthoquinone photosensitizer, etc.).

[0004] In recent years, attracted by the market prospect, the research enthusiasm for diazonaphthoquinone in China has continued to rise. For example, Chinese Patent Application (Publication No.: CN104974107A) uses polyphenolic compounds to react with diazonaphthoquinone to obtain a photosensitizer. The synthesis route is relatively long, the post-treatment operation is more cumbersome, the raw materials need to be synthesized separately, and the post-treatment requires adjusting the pH value, etc. The process operations are all relatively cumbersome, increasing the cost.

[0005] In this case, there is an urgent need for a compound that can replace diazonaphthoquinone-based photosensitizers to reduce the synthesis difficulty of the photosensitizer. Summary of the Invention

[0006] The present application provides a compound containing a diazo group, which can be used as a photosensitizer, and provides a method for synthesizing the compound, as well as the application of the compound.

[0007] The first aspect of the present application is to provide a compound containing a diazo group, having and preferably having the following structure (I):

[0008]

[0009] Among them, m and n are each independently integers ≥ 0, and can be each independently selected from: 0, 1, 2, 3, 4, etc., but m and n are not both 0 at the same time.

[0010] Among them, Q is a group -R containing a diazo group 5 -A=N₂, where A can be selected from:

[0011] one or more of the following, and R 5 The CO of the group is connected to the O atom in OQ, and the diazo group and C=O are located on adjacent carbon atoms; R 5 is selected from one or more of -R-CO- and -R-SO₂-.

[0012] Among them, ring Y can be one or more of a benzene ring, a fused ring, and a biphenyl, such as ring Y can be

[0013]

[0014] one or more of the following.

[0015] Among them, R 11 、R 12 、R 21 、R 22 、R 3 、R 4 can be the same or different, and are each independently selected from one or more of HO-R-, alkyl, heterocycle, H, and halogen.

[0016] Among them, in the above content, R 11 、R 12 、R 21 、R 22 、R 3 、R 4 、R 5 in can be the same or different, and R is one or more of a single bond and a sub-alkyl group. For example, R can be one or more of a sub-alkyl group with or without a branch, an aromatic ring with or without a branch, and a cycloaliphatic ring with or without a branch.

[0017] Among them, the sub-alkyl group can be a C1-C10 sub-alkyl group, more preferably a C1-C6 sub-alkyl group, more preferably a C1-C4 sub-alkyl group, and more preferably a C1-C3 sub-alkyl group.

[0018] Among them, the sub-alkyl group can be preferably a sub-alkyl group, such as methylene, ethylene, etc.

[0019] Among them, the aromatic ring can be a carbocyclic ring or an alicyclic ring containing heteroatoms, preferably an aromatic ring with 5 to 15 carbon atoms, more preferably an aromatic ring with 6 to 12 carbon atoms. Preferably, it can be a single ring, a fused ring, a biphenyl ring, etc., such as a benzene ring, a biphenyl, a naphthalene, etc.

[0020] Among them, the alicyclic ring can be a carbocyclic ring or an alicyclic ring containing heteroatoms, preferably an alicyclic ring with 3 to 10 carbon atoms, more preferably an alicyclic ring with 3 to 6 carbon atoms. Preferably, it can be a single ring, a bridged ring, a spiro ring, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclodecane, etc.

[0021] It should be noted that when m is not 0, at most one of R 11 , R 12 , R 3 is -OH. When m is 0, at most one of R 21 , R 22 , R 3 is -OH.

[0022] Preferably, Q is selected from one or more of the following structures:

[0023]

[0024] The second aspect of the present application provides a method for preparing the above-mentioned compound containing a diazo group, and the steps include:

[0025]

[0026] X-R 5 -A=N2 (III), X is a halogen atom, and the acyl group or sulfonyl group in R5 is connected to X;

[0027] The compound of formula (II) and the compound of formula (III) are mixed and reacted, and the reaction product is collected to obtain the compound containing a diazo group shown in formula (I).

[0028] Among them, the X is preferably one or more of chlorine, bromine, and iodine atoms, and particularly preferably one or more of Cl and Br.

[0029] In a preferred embodiment, the molar ratio of the compound of formula (II) to the compound of formula (III) is preferably 1:0.5 - 5, more preferably 1:1 - 3.

[0030] In a preferred embodiment, the mixing reaction is carried out under the catalysis of a basic substance. More preferably, the basic substance can be one or more of ammonia (NH3), organic amines, nitrogen heterocycles, carbonates, and hydroxides.

[0031] More preferably, the organic amine may be one or more of primary amines and secondary amines, and may be a monoamine or a polyamine, such as one or more of diamines, triamines, or polyamines, and more preferably may be one or more of methylamine, ethylamine, ethylenediamine, and triethylamine.

[0032] More preferably, the nitrogen heterocycle may be a cyclic structure in which one or more carbon atoms in an aliphatic and / or aromatic carbocyclic ring are replaced by N, such as one or more of pyridine, pyrrole, piperidine, pyrazole, imidazole, pyrimidine, and quinoline with or without a side chain.

[0033] More preferably, the carbonate may preferably be a carbonate of Group IA and IIA metals, such as one or more of sodium carbonate, potassium carbonate, and calcium carbonate.

[0034] More preferably, the hydroxide is selected from metal hydroxides, such as one or more of potassium hydroxide and sodium hydroxide.

[0035] In a preferred embodiment, the temperature of the mixed reaction may be -20 to 60 °C, more preferably -10 to 50 °C, more preferably 0 - 40 °C, more preferably 5 - 35 °C, more preferably 10 - 30 °C, and more preferably 15 - 25 °C.

[0036] In a preferred embodiment, the time of the mixed reaction may be at least 15 minutes, more preferably at least 30 minutes, such as 1 - 24 hours, more preferably 2 - 20 hours, more preferably 3 - 18 hours, more preferably 6 - 15 hours, and more preferably 10 - 12 hours.

[0037] In a preferred embodiment, the mixed reaction is carried out in a solvent or a dispersion medium, and the solvent or the dispersion medium may be one or more of water, alcohols, esters, ketones, nitriles, ethers, aromatic hydrocarbons, aliphatic hydrocarbons (chain or cyclic aliphatic hydrocarbons), heterocycles, and halogenated hydrocarbons, and more preferably one or more of water, methanol, ethanol, propanol, isopropanol, dipropanol, acetonitrile, acetone, ethyl acetate, dichloromethane, chloroform, benzene, chlorobenzene, benzyl chloride, benzyl bromide, dioxane, petroleum ether, diethyl ether, and tetrahydrofuran.

[0038] In a preferred embodiment, when an alkaline substance is used as a catalyst, the reaction can be terminated with an acid to end the reaction. Preferably, the acid may be an inorganic acid or an organic acid, such as one or more of acetic acid, sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, formic acid, propionic acid, and succinic acid.

[0039] In a preferred embodiment, the mixed reaction is carried out in a solvent, and after the reaction is completed, the reactants are added to a dispersion medium, and the precipitated solid is collected to obtain the compound containing a diazo group.

[0040] The third aspect of the present application is to provide an application of the compound containing a diazo group. Preferably, it is used as a photosensitive agent, especially as a positive-type photosensitive agent.

[0041] In the above content of the present invention, the branched chain can be one or more of an alkyl group, a heterocyclic ring, and a halogen.

[0042] Among them, in the above content, the alkyl group can be an alkyl group with 1 to 10 carbon atoms, preferably an alkyl group with 1 to 6 carbon atoms, more preferably an alkyl group with 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, etc.

[0043] Among them, in the above content, the heterocyclic ring is a cyclic structure in which one or more carbon atoms on a carbon ring (aliphatic ring or aromatic ring) are replaced by one or more heteroatoms.

[0044] Among them, in the above content, the heteroatom can be one or more of O, N, S, and Si. The heterocyclic ring can be at least a 3-membered ring, preferably at least a 4-membered ring, preferably at least a 5-membered ring, preferably at least a 6-membered ring.

[0045] Among them, in the above content, preferably, the heterocyclic ring can be a monocyclic ring, a spiro ring, a bridged ring, or a fused ring. For example, the heterocyclic ring can be one or more of furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine, pyridazine, aziridine, β-propiolactone, γ-butyrolactone, dioxane, quinoline.

[0046] Among them, in the above content, the halogen can be one or more of F, Cl, Br, and I, and more preferably one or more of F, Cl, and Br.

[0047] Compared with the prior art, the technical solution of the present application has the following beneficial effects: The present application uses a one-pot method to prepare the compound containing a diazo group, with a simple process and mild reaction, which is conducive to industrial production; and the raw materials and reagents used in the present application are all commonly used reagents in the market, having the advantage of easy availability of raw materials. In short, the present application has the advantages of easy operation and low synthesis cost. Most importantly, the post-treatment of the present application is simple, with little environmental pollution, can be used for large-scale industrial production, is conducive to accelerating the localization of photosensitive agents, and has great social value. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] Figure 1 Comparison of the bar exposure effect of the existing photosensitive agent (A) and the bar exposure effect of the compound containing a diazo group of the present invention (B).

[0049] Figure 2Comparison between the square exposure effect (A) of the existing photosensitizer and the square exposure effect (B) of the compound containing a diazo group of the present invention (both are photos enlarged 500 times).

[0050] Figure 3 Comparison between the circular exposure effect (A) of the existing photosensitizer and the circular exposure effect (B) of the compound containing a diazo group of the present invention (both are photos enlarged 500 times).

[0051] Figure 4 Comparison between the bar exposure effects (A) in different directions of the existing photosensitizer and the bar exposure effects (B) in different directions of the compound containing a diazo group of the present invention.

[0052] Figure 5 Comparison between the rounded square exposure effect (A) of the existing photosensitizer and the rounded square exposure effect (B) of the compound containing a diazo group of the present invention.

[0053] Figure 6 Comparison between the circular exposure effect (A) of the existing photosensitizer and the circular light effect (B) of the compound containing a diazo group of the present invention. Detailed implementation manners

[0054] The present invention provides a compound containing a diazo group, its preparation method and application. To make the purpose, technical solution and effect of the present invention clearer and more definite, the following further elaborates the present invention with reference to the attached drawings and by way of examples. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0055] It should be noted that the terms "first", "second", etc. in the description and claims of the present invention and the above-mentioned drawings are used to distinguish similar objects and do not necessarily need to describe a specific order or sequence. It should be understood that the data used in this way can be interchanged under appropriate circumstances. In addition, the terms "comprising" and "having" and any variations thereof are intended to cover non-exclusive inclusion. For example, a process, method, system, product or device that includes a series of steps or units does not necessarily have to be limited to those steps or units clearly listed, but may include other steps or units not clearly listed or inherent to these processes, methods, products or devices.

[0056] Example 1:

[0057] 4-[1-(4-hydroxyphenyl)-1-methylethyl]benzene-1,2-diol (CAS No. 79371-66-7):

[0058]

[0059] 2-diazo-1-naphthoquinone-5-sulfonyl chloride:

[0060]

[0061] In a four-necked flask, 2.9 g of 4-[1-(4-hydroxyphenyl)-1-methylethyl]benzene-1,2-diol, 9.5 g of 2-diazo-1-naphthoquinone-5-sulfonyl chloride (refer to the prior art, such as: Shi Lei et al., Synthesis research of 2-diazo-1-naphthoquinone-5-sulfonyl chloride, Fine Chemicals, 1998), and 75 ml of solvent ethyl acetate were added. Stir at room temperature for 5 - 10 min until evenly mixed and clear.

[0062] 5 g of basic catalyst triethylamine was added to the four-necked flask at room temperature, and the reaction was stirred at room temperature for 1 - 3 h.

[0063] Then, 10% hydrochloric acid aqueous solution was added to quench the reaction, and stirring was continued for 0.5 h. The aqueous phase was removed by liquid separation.

[0064] The obtained organic phase was slowly added to the dispersion reagent methanol (125.00 ml) and stirred for dispersion. A large amount of yellow solid precipitated out. The yellow wet product was collected by filtration. Recrystallized with ethyl acetate / methanol to obtain a yellow solid, which was dried in an oven at 50 °C to constant weight, and a yellow solid was obtained with a yield ≥ 96.00%. By liquid phase analysis, the product purity reached over 98.00%. NMR data 1 HNMR(CDCl3 400 MH) 7.96~8.03(m, 6H) 7.75~7.77(m, 6H) 7.11(m, 2H) 6.80(m, 2H) 6.63(m, 2H) 6.55(m, 1H) 6.34(m, 3H) 1.69(s, 6H). Mass spectrum: [M + 1]: 941.93. The NMR and mass spectrum data are consistent with the structure of the actual target compound.

[0065] Example 2:

[0066] In a four-necked reaction flask, 3 g of 4-[1-(4-hydroxyphenyl)-1-methylethyl]benzene-1,2-diol, 8 g of 2-diazo-1-naphthoquinone-5-sulfonyl chloride, and 75 ml of solvent ethyl acetate were added. Stir at room temperature for 5 - 10 min until evenly mixed and clear.

[0067] 3.5 g of basic catalyst triethylamine was added to the four-necked reaction flask at room temperature, and the reaction was stirred at room temperature for 1 - 3 h.

[0068] Then, 10% hydrochloric acid aqueous solution was added to quench the reaction, and stirring was continued for 0.5 h. The aqueous phase was removed by liquid separation.

[0069] The obtained organic phase was slowly added to the dispersing reagent methanol (125.00 ml) and stirred for dispersion. A large amount of yellow solid precipitated out, and the yellow wet product was collected by filtration. It was recrystallized with ethyl acetate / methanol to obtain a yellow solid, which was dried in an oven at 50 °C to constant weight, and thus a yellow solid was obtained with a yield of ≥96.00%. Through liquid phase analysis, the product purity was ≥95%. The main component of this product was a mixed product of trisubstituted compounds and disubstituted compounds. Its mass spectrometry signals [M+1] were 941.93 and 709.72 respectively, and the mass spectrometry data was consistent with the structure of the actual target compound.

[0070] Example 3:

[0071] 4,4',4”-Methylidynetriphenol (CAS No. 603-44-1):

[0072]

[0073] In a four-necked reaction flask, 2 g of 4,4',4”-methylidynetriphenol, 5.5 g of 2-diazo-1-naphthoquinone-5-sulfonyl chloride, and 40 ml of 1,4-dioxane were added, and stirred at room temperature for 5 - 10 min until evenly mixed and clarified.

[0074] At room temperature, 2.5 g of the basic catalyst triethylamine was added to the four-necked reaction flask, and the reaction was stirred at room temperature for 1 - 3 h.

[0075] Then, 10% aqueous hydrochloric acid solution was added to quench the reaction, and stirring was continued for 0.5 h. A yellow solid slowly precipitated out, and the yellow wet product was collected by filtration. The yellow wet product was dried in an oven at 50 °C to constant weight, and thus a yellow powder was obtained with a yield of 92.31%. NMR data 1 HNMR(CDCl3 400MH) 7.96~8.03(m, 6H) 7.75~7.77(m, 6H) 6.94(m, 6H) 6.80(m, 6H) 6.34(m, 3H) 5.41(m, 1H). Mass spectrometry: [M+1]: 989.09. The NMR and mass spectrometry data were consistent with the structure of the actual target compound.

[0076] Example 4

[0077] In a four-necked reaction flask, 2 g of 4,4',4”-methylidynetriphenol, 3 g of 2-diazo-1-naphthoquinone-5-sulfonyl chloride, and 40.00 ml of 1,4-dioxane were added in sequence. Stirred at room temperature for 5.0 min - 10 min until evenly mixed and clarified.

[0078] At room temperature, 2.5 g of the catalyst triethylamine was added to the four-necked reaction flask. The reaction was stirred at room temperature for 1 - 3 h.

[0079] Then it was slowly added to 1% hydrochloric acid aqueous solution and stirred for dispersion, and stirring was continued for 0.5 h. Yellow solid slowly precipitated out, and the yellow wet product was collected by filtration. It was dried in an oven at 50 °C to constant weight to obtain a yellow powder with a yield of 92.00%. The main component of this product is a mixed product of trisubstituted, disubstituted, and monosubstituted compounds. Its mass spectra [M+1] are respectively: [M+1]: 898.09, 757.76, 525.55. The mass spectrometry data is consistent with the structure of the actual target compound.

[0080] The diazo group-containing compound synthesized in this application realizes a "one-pot" synthesis through the improvement and optimization of the synthesis process of this photosensitizer. This route is short, with high yield, high purity, and low cost. Most importantly, the post-treatment of this process is simple, with little environmental pollution, and it can be used for large-scale industrial production, which is conducive to accelerating the localization of photosensitizers and has great social value.

[0081] Table 1, Photoresist sensitivity of the compound of the present invention as a photosensitizer

[0082] Shape / Size Minimum Exposure Value ETH(40um / LS) 340mj / cm2 ETH(40um / S) 320mj / cm2 ETH(40um / v) 320mj / cm2 ETH(5um / LS) 340mj / cm2 ETH(5um / S) 380mj / cm2 ETH(5um / v) 400mj / cm2

[0083] Refer to Figure 1 - 6 And Table 1, by comparison, within the size range of 5 - 40 μm of the photoresist exposure film, the photoresist prepared from this product has high sensitivity, high resolution, and good clarity of graphic lines.

[0084] The specific embodiments of this application have been described in detail above, but they are only examples, and this application is not limited to the specific embodiments described above. For those skilled in the art, any equivalent modifications and substitutions made to this application are also within the scope of this invention. Therefore, equivalent transformations and modifications made without departing from the spirit and scope of this application should all be covered within the scope of this invention.

Claims

1. A compound containing a diazo group, characterized in that, It has the following structure (I): Wherein, m and n are each independently an integer ≥ 0, provided that m and n are not both 0; Q is a diazo group-containing group -R 5 -A=N2, where A is selected from: one or more of them, R 5 is selected from one or more of -R-CO- and -R-SO2-; and R 5 the CO of the group is connected to the O atom in OQ, and the diazo group and C=O are located on adjacent carbon atoms; ring Y is selected from one or more of benzene ring, fused ring, and biphenyl; R 11 、R 12 、R 21 、R 22 、R 3 、R 4 are the same or different and are each independently selected from one or more of HO-R-, alkyl, heterocycle, H, and halogen; R 11 、R 12 、R 21 、R 22 、R 3 、R 4 、R 5 The Rs in 11 to 5 are the same or different, and R is one or more of a single bond and an alkylene group; When m is not 0, at most one of R 11 , R 12 , R 3 is -OH. When m is 0, at most one of R 21 , R 22 , R 3 is -OH.

2. The compound containing a diazo group according to claim 1, characterized in that, Q is selected from one or more of the following structures:

3. The compound containing a diazo group according to claim 1, characterized in that, R is one or more of an alkylene group with or without a side chain, an aromatic ring with or without a side chain, and an alicyclic ring with or without a side chain.

4. The compound containing a diazo group according to claim 3, characterized in that, The alkylene group is a C1-C10 alkylene group, more preferably a C1-C6 alkylene group, more preferably a C1-C4 alkylene group, more preferably a C1-C3 alkylene group; the alkylene group is more preferably an alkylene group, and preferably, it can be a structure such as a monocyclic ring, a fused ring, or a biphenyl ring, such as a benzene ring, a biphenyl, or a naphthalene. The aromatic ring is a carbocyclic ring or an alicyclic ring containing heteroatoms, preferably a C5-C15 aromatic ring, more preferably a C6-C12 aromatic ring; the alicyclic ring can be a carbocyclic ring or an alicyclic ring containing heteroatoms, preferably a C3-C10 alicyclic ring, more preferably a C3-C6 alicyclic ring, and preferably, it can be a monocyclic ring, a bridged ring, or a spiro ring, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, or cyclodecane.

5. The compound containing a diazo group according to claim 3, characterized in that, The side chain is one or more of a rotating alkyl group, a heterocyclic ring, or a halogen.

6. The diazo group-containing compound according to claim 5, characterized in that, The alkyl group is selected from C1-C10 alkyl groups, preferably C1-C6 alkyl groups, more preferably C1-C5 alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, or n-hexyl. The heterocyclic ring is a cyclic structure in which one or more carbon atoms on the carbocyclic ring are replaced by heteroatoms, and the heteroatoms are selected from one or more of O, N, S, and Si; and preferably, it is at least a 3-membered ring, preferably at least a 4-membered ring, preferably at least a 5-membered ring, preferably at least a 6-membered ring; more preferably, the heterocyclic ring is selected from one or more of a monocyclic ring, a spiro ring, a bridged ring, or a fused ring, and for example, it can be one or more of furan, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrazine, pyrimidine, pyridazine, aziridine, β-propiolactone, γ-butyrolactone, dioxane, or quinoline. The halogen is selected from one or more of F, Cl, Br, and I.

7. A method for preparing a compound containing a diazo group according to claim 1, characterized in that the step It includes: X-R 5 -A = N2(III), X is a halogen atom, and the acyl or sulfonyl group in R5 is linked to X; The compound of structural formula (II) and the compound of structural formula (III) are mixed and reacted, and the reaction product is collected to obtain the diazo group-containing compound shown in structural formula (I).

8. The method for preparing a compound containing a diazo group according to claim 7, characterized in that, The molar ratio of the compound of structural formula (II) to the compound of structural formula (III) is preferably 1:0.5 - 5, more preferably 1:1 - 3.

9. The method for preparing a compound containing a diazo group according to claim 7, characterized in that, The mixed reaction is carried out using an alkaline substance as a catalyst. More preferably, the alkaline substance can be one or more of ammonia (NH3), organic amines, nitrogen heterocycles, carbonates, and hydroxides; more preferably: the organic amine can be one or more of primary amines and secondary amines, and can be a monoamine or a polyamine, such as one or more of a diamine, a triamine, or a polyamine, more preferably one or more of methylamine, ethylamine, ethylenediamine, and triethylamine; the nitrogen heterocycle can be a cyclic structure in which one or more carbon atoms in an aliphatic and / or aromatic carbocycle are replaced by N, such as one or more of pyridine, pyrrole, piperidine, pyrazole, imidazole, pyrimidine, and quinoline with or without branches; the carbonate can preferably be a carbonate of Group IA and IIA metals, such as one or more of sodium carbonate, potassium carbonate, and calcium carbonate; the hydroxide is selected from metal hydroxides, such as one or more of potassium hydroxide and sodium hydroxide; more preferably, an alkaline substance is used as a catalyst and the reaction is terminated with an acid to achieve the end of the reaction. Preferably, the acid can be an inorganic acid or an organic acid, such as one or more of acetic acid, sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, formic acid, propionic acid, and succinic acid; and / or The temperature of the mixed reaction can be -20 to 60 °C, more preferably -10 to 50 °C, more preferably 0 - 40 °C, more preferably 5 - 35 °C, more preferably 10 - 30 °C, more preferably 15 - 25 °C; and / or The time of the mixed reaction can be at least 15 minutes, more preferably at least 30 minutes, such as 1 - 24 hours, more preferably 2 - 20 hours, more preferably 3 - 18 hours, more preferably 6 - 15 hours, more preferably 10 - 12 hours; and / or The mixed reaction is carried out in a solvent or a dispersion medium. The solvent or dispersion medium can be one or more of water, alcohols, esters, ketones, nitriles, ethers, aromatic hydrocarbons, aliphatic hydrocarbons (linear or cyclic aliphatic hydrocarbons), heterocycles, and halogenated hydrocarbons. More preferably, it is one or more of water, methanol, ethanol, propanol, isopropanol, dipropanol, acetonitrile, acetone, ethyl acetate, dichloromethane, chloroform, benzene, chlorobenzene, benzyl chloride, benzyl bromide, dioxane, petroleum ether, diethyl ether, and tetrahydrofuran; more preferably, the mixed reaction is carried out in a solvent, and after the reaction is completed, the reactants are added to the dispersion medium, and the precipitated solid is collected to obtain the compound containing a diazo group.

10. Use of the compound containing a diazo group according to claim 1, characterized in that, It is used as a photosensitizer, especially as a positive - type photosensitizer.

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