Anthracene skeleton compound and photoinitiator application thereof

Abstract

The application discloses a kind of polyhydroxy anthracene skeleton compounds and its photoinitiator application, a kind of polyhydroxy anthracene skeleton compounds of the application is used as photoinitiator precursor, the structure of this series of compounds has anisotropy, hydroxyl is uniformly distributed and steric hindrance is small, and after being combined with diazonium naphthoquinone photosensitizer (DNQ), background absorption cannot be generated to influence.Therefore, the compound of this type can be used as new photoinitiator, and is expected to shine in the field of semiconductors.

Description

TECHNICAL FIELD

[0001] The application discloses a kind of multi-hydroxy anthracene skeleton compound and its photoinitiator application, belong to photochemistry technical field. BACKGROUND

[0002] Photoetching technology is widely used in electronic industry, and is a main process in the production of planar transistors and integrated circuits. As an important part of photoetching process, photoresist is classified from low-end to high-end in panel and semiconductor industries. The main factors that determine the minimum line width of photoetching process are the type of photoresist and the precision of photoetching machine. The composition of G / I line photoresist includes resin, photoinitiator, solvent, and a small amount of additives. The current G / I line photoetching precision is limited by the photosensitivity of photoinitiator. The photoinitiator is mainly composed of diazonaphthoquinone photosensitizer and multi-hydroxy benzene ring derivative condensed under alkaline conditions. The photosensitivity of the photoinitiator is related to the distribution position of DNQ in the molecule. The larger the interval between adjacent DNQ, the better the photosensitivity. For example, the three hydroxyl groups of ɑ, ɑ, ɑ'-tri(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (TPA) are on different benzene rings. The photosensitivity of the grafted DNQ is particularly excellent. Benzophenone and fluorenone, which have multiple grafting sites, are also widely used. Heterocyclic anthracene compounds are commonly used in photochemical research. The unique six-membered ring structure has good symmetry and rigidity in space. The hydroxyl substitution active sites on the benzene ring are uniformly distributed, and the carbon-based sites exist. The photoinitiator can be modified and used for the preparation of G / I line photoinitiator. The G / I line photoinitiator required by the semiconductor industry usually has high stability, multi-stage applicability, high photosensitivity, low cost, and other characteristics. At present, domestic semiconductor enterprises need this kind of domestic substitute high-quality new product. SUMMARY

[0003] The present application aims to solve the problems of lack of new photoinitiator and single type of new photoinitiator precursor skeleton. A synthesis method of a kind of multi-hydroxy anthracene skeleton compound and its photoinitiator is proposed, and the photoinitiator is applied by using photoetching process.

[0004] A kind of multi-hydroxy anthracene skeleton compound, the structural formula of the compound includes the following:

[0005] 、 ; R2', R3' are phenol, R4', R5' are hydrogen or -OH, and are not H at the same time, the position of R4', R5' is not fixed; R1 is selected from one of N, O, S, P elements, then R7 selectively contains H according to R1. The reaction equation is:

[0006]

[0007] wherein R1 is a heteroatom, representing one of N, O, S, P; R2', R3' are phenol groups; R4', R5' are phenolic hydroxyl groups on the benzene ring or hydrogen atoms, and R7 is a hydrogen atom or an optional substituent according to the heteroatom.

[0008] Another technical solution of the present application is to provide a kind of anthracene skeleton compound, using the esterification reaction of the multi-hydroxy anthracene skeleton compound under alkaline conditions with diazonium naphthoquinone compound DNQ in solvent, diazonium naphthoquinone photoinitiator is generated, that is, anthracene skeleton compound, the structural formula of the anthracene skeleton compound is as follows:

[0009] R2, R3 are wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %.

[0010] R4, R5 are hydrogen or -OR6, and the positions of R4 and R5 are not fixed, wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %.

[0011] The structural formula of the anthracene skeleton compound is as follows: R1 is one of N, O, S, P, and the structural formula is as follows: R2, R3 are wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %.

[0012] R4, R5 are hydrogen or -OR6, and the positions of R4 and R5 are not fixed, wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %.

[0013] The anthracene skeleton compound includes any one of the following:

[0014] wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %.

[0015] In some embodiments, taking a compound as an example, the synthesis method of the heterocyclic anthracene photoinitiator is as follows, taking the synthesis of compound (1) as an example:

[0016] wherein, grafting ratio of 80.0-95.0 %, since the obtained product is a mixture, the grafting ratio refers to the amount of The synthesis process of other compounds is the same as this.

[0017] Based on the above synthesis process, all the compounds of the present application including anthracene skeleton compounds and their heterocyclic anthracene photoinitiators have the following structures:

[0018] wherein R6 is selected from H and wherein, grafting ratio of 80.0-95.0 %, since the obtained product is a mixture, the grafting ratio refers to the amount of

[0019] Another technical solution of the present application is to provide a synthesis method of anthracene skeleton compounds, comprising the following steps:

[0020] (1) in an organic solvent, using a strong acid catalyst to activate the carbonyl group of anthrone, and carrying out electrophilic substitution reaction with phenol to generate an anthracene compound with multiple phenolic hydroxyl groups;

[0021] (2) under alkaline conditions, the anthracene compound with multiple phenolic hydroxyl groups and diazonium naphthoquinone compound DNQ undergo esterification reaction in a solvent to generate diazonium naphthoquinone type photoinitiator.

[0022] The anthrone raw material also includes phenol, 3-hydroxy-9H-xanthone-9-ketone, 2-hydroxyanthrone, 2,6-dihydroxyanthrone, pitavastatin impurity 75, compound (7) and compound (8), wherein the structures of compound (7) and compound (8) are as follows:

[0023]

[0024] In the synthesis method of the multi-hydroxyl heterocyclic anthracene skeleton compound, the catalyst used includes one or more of β-mercapto propionic acid, sulfuric acid, trifluoromethyl sulfonic acid, trifluoromethyl sulfonic anhydride, Amberlyst-15 hydrogen type strong acid resin.

[0025] In the synthesis method of the multi-hydroxyl heterocyclic anthracene skeleton compound, the organic solvent used includes one or more of DMF, methanol, acetone, phenol.

[0026] In the synthesis method of the multi-hydroxyl heterocyclic anthracene skeleton compound, the molar feeding ratio of anthrone raw material to phenol is 1:6-30, the reaction temperature is 30-120 ℃, and the reaction time is 12-24 h. Those skilled in the art can understand that in order to avoid oxidation reaction, the whole reaction process of the present application is protected by nitrogen.

[0027] ​The molar feeding ratio of the raw material DNQ to the multi-hydroxyl heterocyclic anthracene skeleton compound is 2-5:1, the synthesis temperature is controlled at 30-35 DEG C, the solvent is 1, 4-dioxane, the catalyst is triethylamine (the dropwise adding time is controlled at 60-65 min), and the reaction time is 5-30 min.

[0028] A G / I line photoinitiator comprises the multi-hydroxyl anthracene skeleton compound and the anthracene photoinitiator.

[0029] A photosensitive material comprises the anthracene skeleton compound.

[0030] The photosensitive material further comprises a composition formed by a phenolic resin and an organic solvent selected from PGMEA.

[0031] The photosensitive material is applied in the field of photolithography.

[0032] The novel heterocyclic anthracene photoinitiator is tested and evaluated in performance, and specifically:

[0033] The photoinitiator is dissolved in propylene glycol methyl ether acetate (PGMEA), and then mixed with a phenolic resin (molecular weight 4500-5400) to form a solution, wherein the photoinitiator accounts for 5.5 wt%, PGMEA accounts for 23.0%, and the phenolic resin accounts for 72.0%; 10 mL of the mixed solution is dropped on an 8-inch circular substrate material, and is uniformly distributed on the substrate material in a film with a thickness of 20 μm by using a spin coating method; a pre-baking treatment is performed; an exposure is performed by using a photolithography machine under a 365 nm light source, and the exposure energy is 120 mJ / cm 2 ; a post-baking treatment is performed; then the material is placed in a developing cylinder containing 2.38 wt% tetramethylammonium hydroxide (TMAH) for 20 s; the surface of the material is washed with ultrapure water to remove the excess developing solution; the height difference of the pattern is observed by using a profilometer; and the height difference is used to judge the pros and cons of the photosensitive performance of the photoinitiator, and the judgment standard is that the greater the height difference of the pattern, the better the photosensitive performance of the photoinitiator.

[0034] The present application has the following beneficial effects:

[0035] 1. Compared with common benzophenone, fluorenone and TPA, the multi-hydroxyl anthracene skeleton compound has a larger non-conjugated benzene ring system, a farther hydroxyl site spacing, an easy rotation of carbon-carbon bond between benzene rings, and a better exposure of the hydroxyl group in space, which is beneficial to grafting DNQ and easy to form a photoinitiator with excellent effect.

[0036] 2. The anthracene photoinitiator has good photosensitivity when mixed with resin, can be developed as a G / I line photoinitiator, and has great industrial value.

[0037] 2. The synthesis method of the multi-hydroxyl anthracene skeleton compound is simple, has low process cost and reaction hazard risk, and has actual industrialization value. BRIEF DESCRIPTION OF DRAWINGS

[0038] Figure 1 is a nuclear magnetic resonance hydrogen spectrum of compound (1-1).

[0039] Figure 2 is a nuclear magnetic resonance hydrogen spectrum of compound (2-1).

[0040] Figure 3 is a nuclear magnetic resonance hydrogen spectrum of compound (3-1).

[0041] Figure 4 is a nuclear magnetic resonance hydrogen spectrum of compound (4-1).

[0042] Figure 5 is a nuclear magnetic resonance hydrogen spectrum of compound (5-1).

[0043] Figure 6 is a nuclear magnetic resonance hydrogen spectrum of compound (6-1).

[0044] Figure 7 is a graph of the change of the light irradiation residual rate of the six photoinitiator compounds with time. DETAILED DESCRIPTION

[0045] The application will be further described below in conjunction with examples, but the scope of the application claimed is not limited to the scope expressed by the examples.

[0046] The reaction raw materials described in the application include phenol, anthrone, 3-hydroxy-9H-xanthone-9-ketone, 2-hydroxyanthrone, 2,6-dihydroxyanthrone, pitavastatin impurity 75, compound (7) and compound (8), wherein the structural formulas of the compound (7) and the compound (8) are as follows:

[0047] .

[0048] Synthesis steps (method one) of the multi-hydroxyl heterocyclic anthracene skeleton compound:

[0049] a. The raw materials are mixed with solvents in a 250 mL flask according to the reaction ratio, and nitrogen bubbling is carried out to discharge the air in the bottle;

[0050] b(l). When the catalyst is β-mercaptopropionic acid and sulfuric acid: first, place the mixed solution of step (a) in a 30 °C oil bath, and then add β-mercaptopropionic acid to the reaction system under nitrogen protection, and react at 30 °C for 30 min, and then slowly add sulfuric acid, and after the addition is completed, the reaction temperature is raised to 60-120 °C (according to the type of solvent), and the reaction is continued for 12-24 h;

[0051] b(2). When the catalyst is triflic acid and triflic anhydride: the temperature of the mixed solution of step (a) is raised to the reaction temperature (60-120 °C), and then the catalyst is slowly added dropwise, and the reaction is continued for 12-24 h;

[0052] b(3). When the catalyst is Amberlyst-15 hydrogen type strong acid resin: the Amberlyst-15 hydrogen type strong acid resin is added to the flask together with the raw materials and solvents in step (a) to form a solid-liquid mixed system, and the reaction is carried out at 60-120 °C for 12-24 h;

[0053] c. The reaction of the raw materials is monitored by thin layer chromatography (TLC), and the reaction is carried out in a nitrogen atmosphere. After the reaction is completed, the temperature is lowered to room temperature, 2 times the volume of water at room temperature is added to the reaction system, and the product solid is analyzed and separated. After the product solid is filtered and washed with water at room temperature, the product solid is collected and dried at 40 °C. Finally, the product is recrystallized in acetone solution to obtain a product with a purity of more than 99.00 %;

[0054] d. The product is tested by HPLC (purity) and nuclear magnetic resonance.

[0055] Photoinitiator synthesis step (method two):

[0056] a. Dissolve 1.000 mmol of the multi-hydroxyl anthracene skeleton compound and DNQ in 1,4-dioxane according to a certain molar ratio, and stir and dissolve at 35 °C;

[0057] b. After the reaction system is cooled to 30 °C, slowly add triethylamine catalyst and the same volume of solvent 1,4-dioxane (the dropwise addition time is about 1 h), and the temperature is maintained between 30-31 °C. After the addition is completed, the temperature is raised to 35 °C and the reaction is continued for 30 min;

[0058] c. Add 30 % hydrochloric acid to the reaction system for quenching, and filter and collect the filtrate;

[0059] d. Slowly pour the filtrate into an ultrapure water containing 5 times the volume of organic solution (mixed with 30 % hydrochloric acid) with vigorous mechanical stirring, and perform the beating operation;

[0060] e. The mixed solution was filtered, and the solid product was washed with ultrapure water until the pH of the filtrate was greater than 6. The solid was collected and dried at 40°C.

[0061] Examples 1-11:

[0062] Examples 1-11 prepared compound (1-1) and compound (1-2), the structural formula is respectively:

[0063]

[0064] Compound (1-1) preparation selection synthesis method one, the preparation process required medicines include: raw materials (3-hydroxy-9H-xanthene-9-ketone, phenol), solvents (DMF, acetone, methanol, phenol), catalysts (β-mercapto propionic acid and sulfuric acid, trifluoromethanesulfonic acid, trifluoromethanesulfonic anhydride, Amberlyst-15 hydrogen type strong acid resin)

[0065] The reaction conditions of each example are shown in the following table:

[0066]

[0067] Examples 1-4 on compound (1-1) synthesis reaction solvent experiment, it can be seen that the use of the technical solutions of the present application can achieve a yield of more than 45%, further can reach more than 60%, further reach more than 70%, the highest can reach 86%. Examples 5-11 phenol and DMF as the reaction solvent respectively on trifluoromethanesulfonic acid, trifluoromethanesulfonic anhydride, Amberlyst-15 hydrogen type strong acid resin three kinds of catalysts are compared, wherein the reaction yield using trifluoromethanesulfonic acid can reach the highest to 86%. The results of nuclear magnetic resonance data are shown in Figure 1 .

[0068] Compound (1-2) synthesis selection method two, the preparation process required medicines include: raw materials (compound (1-1), DNQ), solvent (1,4-dioxane), catalyst (triethylamine). The amount of each medicine is shown in the following table:

[0069]

[0070] Compound (1-2) is a mixture, the color of the solid is bright yellow, and the DNQ grafting rate is 92.3%.

[0071] Examples 12-13:

[0072] Examples 12-13 prepared compound (2-1) and compound (2-2), the structural formula is respectively:

[0073]

[0074] The compound (2-1) is prepared by the selected synthesis method one, and the required medicines in the preparation process include: raw materials (pitavastatin impurity 75 and phenol), a solvent (DMF), and a catalyst (β-mercaptopropionic acid and sulfuric acid, trifluoromethanesulfonic acid).

[0075] The reaction conditions of each embodiment are shown in the following table:

[0076]

[0077] The catalyst screening for the synthesis of compound (2-1) is carried out in Examples 12-13, and the results show that the reaction yield is the highest when the catalyst is trifluoromethanesulfonic acid, reaching 92 %. Therefore, the optimal reaction conditions for the synthesis of compound (2-1) are as follows: based on the molar amount of the raw material pitavastatin impurity 75, the molar amount of phenol is 6 eq, the molar amount of the catalyst trifluoromethanesulfonic acid is 1.2 eq, the solvent is DMF, the reaction temperature is 120 ℃, the reaction time is 24 h, the product purity is 99.18 %, and the yield is 92 %. The nuclear magnetic test results of compound (2-1) are shown in Figure 2

[0078] The compound (2-2) is synthesized by the selected synthesis method two, and the required medicines in the preparation process include: raw materials (compound (2-1) and DNQ), a solvent (1,4-dioxane), and a catalyst (triethylamine). The amounts of each medicine are shown in the following table:

[0079]

[0080] The compound (2-2) is a mixture, the solid color is bright yellow, and the DNQ grafting rate is 86.9 %.

[0081] Example 14:

[0082] The compound (3-1) and the compound (3-2) are prepared in Example 14, and the structural formula is:

[0083]

[0084] The compound (3-1) is prepared by the selected synthesis method one, and the required medicines in the preparation process include: raw materials (compound (7) and phenol), a solvent (DMF), and a catalyst (trifluoromethanesulfonic acid), and the reaction conditions are:

[0085]

[0086] The yield of compound (3-1) reaches 85 %, the purity reaches 99.57 % by HPLC test, and the nuclear magnetic data results are shown in Figure 3

[0087] ​​The synthesis of compound (3-2) is performed using method two. The reagents required for the preparation process include: raw materials (compound (3-1), DNQ), solvent (1,4-dioxane), and catalyst (triethylamine). The amounts of each reagent are shown in the table below.

[0088]

[0089] Compound (3-2) is a mixture, the solid is bright yellow in color, and the DNQ grafting rate is 82.4%.

[0090] Example 15:

[0091] Example 15: Compounds (4-1) and (4-2) were prepared with the following structural formulas:

[0092]

[0093] Compound (4-1) was prepared using synthetic method one. The reagents required for the preparation process included: raw materials (compound (8) and phenol), solvent (DMF), and catalyst (trifluoromethanesulfonic acid). The reaction conditions were as follows:

[0094]

[0095] The yield of compound (4-1) reached 91%, and the purity was 99.52% as determined by HPLC. The NMR data are as follows: Figure 4 As shown.

[0096] The synthesis of compound (4-2) is performed using method two. The reagents required for the preparation process include: raw materials (compound (4-1), DNQ), solvent (1,4-dioxane), and catalyst (triethylamine). The amounts of each reagent are shown in the table below.

[0097]

[0098] Compound (4-2) is a mixture, the solid is bright yellow, and the DNQ grafting rate is 83.2%.

[0099] Examples 16-19:

[0100] Examples 16-19 prepared compounds (5-1) and (5-2) with the following structural formulas:

[0101]

[0102] Compound (5-1) was prepared by synthetic method one. The reagents required for the preparation process include: raw materials (2-hydroxyanthraquinone, phenol), solvent (DMF, phenol), and catalyst (β-mercaptopropionic acid, sulfuric acid, and trifluoromethanesulfonic acid).

[0103] The reaction conditions for each embodiment are shown in the table below:

[0104]

[0105] Example 16-19 screened solvents and catalysts for the synthesis reaction of compound (5-1). The test process used phenol and DMF as solvents to screen β-mercaptopropionic acid and sulfuric acid, triflic acid as catalysts, respectively. The results showed that when DMF was used as the solvent and triflic acid was used as the catalyst, the reaction yield could reach more than 60%, further reaching more than 70%, and the highest reaching 88%. At the same time, the optimal conditions for synthesizing compound (5-1) were as follows: based on the molar amount of raw material 2-hydroxyanthraquinone, the molar amount of phenol was 6 eq, the molar amount of catalyst triflic acid was 1.2 eq, the solvent was DMF, the reaction temperature was 120 °C, the reaction time was 24 h, the product purity was 99.48%, the yield was 88%, and the nuclear magnetic resonance test results are shown in Figure 5

[0106] The second selected method for synthesizing compound (5-2) required the following drugs: raw material (compound (5-1), DNQ), solvent (1,4-dioxane), and catalyst (triethylamine). The amounts of the drugs are shown in the following table:

[0107]

[0108] Compound (5-2) is a mixture, and the solid color is bright yellow, with a DNQ grafting rate of 82.8%.

[0109] Examples 20-22:

[0110] Examples 20-22 prepared compound (6-1) and compound (6-2), and the structural formula is:

[0111]

[0112] The first selected method for synthesizing compound (6-1) required the following drugs: raw material (2,6-dihydroxyanthraquinone, phenol), solvent (DMF, phenol), and catalyst (β-mercaptopropionic acid and sulfuric acid, triflic acid).

[0113] The reaction conditions of each example are shown in the following table:

[0114]

[0115] ​Example 20-22 The solvent and catalyst screening was carried out for the synthesis of compound (6-1). The reaction solvents were DMF and phenol, and the reactivity of β-mercaptopropionic acid and sulfuric acid, triflic acid was compared respectively, the results showed that for the reaction DMF as the solvent was conducive to the reaction, the catalyst was triflic acid, the reaction effect was better, the yield was more than 60%, further more than 70%, the highest was 76%. Therefore, the optimal reaction conditions for the synthesis of compound (6-1) were as follows: based on the molar amount of raw material 2,6-dihydroxyanthraquinone, the molar amount of phenol was 6 eq, the molar amount of catalyst triflic acid was 1.2 eq, the solvent was DMF, the reaction temperature was 120 ℃, the reaction time was 24 h, the product purity was 99.28%, the yield was 76%, and the nuclear magnetic resonance test results were as shown in Figure 6 .

[0116] The preparation process of compound (6-2) selected method two required drugs included: raw materials (compound (6-1), DNQ), solvent (1,4-dioxane), catalyst (triethylamine). The amount of each drug was as shown in the following table:

[0117]

[0118] Compound (6-2) was a mixture, the solid color was yellow, and the DNQ grafting rate was 84.9%.

[0119] Example 23:

[0120] a. The photo initiator compounds (1-2), (2-2), (3-2), (4-2), (5-2), (6-2) of the application were dissolved in acetonitrile to prepare samples with a concentration of 0.0378 g / L, and the numbers were (1-2), (2-2), (3-2), (4-2), (5-2), (6-2) respectively;

[0121] b. The wavelength of the ultraviolet light source was set to 365 nm, and the light intensity was set to 10 mW / cm 2 ;

[0122] c. (1-2), (2-2), (3-2), (4-2), (5-2), (6-2) were irradiated under the ultraviolet light source, the ultraviolet spectrum of the sample solution was detected every 10 s, and the highest peak absorbance greater than 300 nm was recorded, and the highest peak absorbance of each sample was normalized, and a linear relationship graph of time and residual rate was drawn, as shown in Figure 7 .

[0123] Observation Figure 7The greater the slope of each curve in the same time, the stronger the photosensitivity. When the light irradiation time is 20s, the residual rate of the compositions (5-2) and (6-2) is obviously lower than that of the compositions (1-2), (2-2), (3-2) and (4-2), indicating that the compositions (5-2) and (6-2) have stronger photosensitivity.

[0124] Example 24:

[0125] a. 5.000 g of each of the compounds (1-2), (2-2), (3-2), (4-2), (5-2) and (6-2) was weighed and mixed with 20.000 g of phenolic resin and 65.000 g of organic solvent PGMEA to prepare a photosensitive composition, which was numbered as composition (1-2), (2-2), (3-2), (4-2), (5-2) and (6-2), respectively;

[0126] b. The six compositions in a were subjected to the same condition of photoetching process, and the process flow included spin coating, pre-baking, exposure, post-baking, development, and the process parameters of the flow were shown in the table:

[0127]

[0128] c. The height difference of the film covered on each group of substrates was detected by a profilometer, and the detection results were shown in the table:

[0129]

[0130] It can be seen that the height difference values of the compositions (1-2), (2-2), (3-2), (4-2), (5-2) and (6-2) are all larger, and all have photosensitivity. Among them, the compositions (3-2), (1-2), (5-2) and (6-2) have more specific photosensitivity than (1-2) and (4-2), and it is proved by the above examples that the photosensitivity of the compounds (6-2) and (5-2) is obviously higher than that of other compounds, and they can be used as photoinitiators.

[0131] It should be noted that the embodiments of the present application have better implementation, and do not limit the present application in any form. Any skilled person in the art can change or modify the above disclosed technical content into equivalent effective embodiments, as long as it does not deviate from the technical solution of the present application. Any modification or equivalent change and modification of the above embodiments according to the technical essence of the present application, still belongs to the scope of the technical solution of the present application.

Claims

1. A class of anthracene skeleton compounds characterized in that, The esterification reaction of the multi-hydroxyl anthracene skeleton compound with the diazonium naphthoquinone compound DNQ in a solvent under alkaline conditions generates a diazonium naphthoquinone photoinitiator, i.e. an anthracene skeleton compound, and the structural formula of the anthracene skeleton compound is as follows: ; R2, R3 are wherein R6 is selected from H and wherein, grafting rate of 80-95 %; R4, R5 are hydrogen or -OR6, the R4, R5 positions are not fixed, wherein R6 is selected from H wherein, grafting rate of 80.0-95.0 %.

2. The anthracene-based backbone compound according to claim 1, characterized by The structural formula of the anthracene skeleton compound is: R7 is H when R1 is N, O, S, or P; R2 and R3 are wherein R6 is selected from H and wherein, The grafting rate of the compound is 80.0-95.0 %. R4, R5are hydrogen or -OR6, the positions of R4, R5not fixed, wherein R6is selected from H and wherein, grafting rate of 80.0-95.0 %.

3. The anthracene-based backbone compound according to claim 2, characterized by The anthracene skeleton compound includes any one of the following: wherein R6is selected from H and wherein, grafting rate of 80.0-95.0 %.

4. A method for synthesizing the anthracene skeleton compound according to any one of claims 1 to 3, characterized by, The method includes the following steps: (1) In an organic solvent, the carbonyl group of anthracene is activated by a strong acid catalyst, and an electrophilic substitution reaction is performed with phenol to generate an anthracene compound with multiple phenolic hydroxyl groups, and the reaction formula is as follows: R2', R3' is phenol, R4', R5' is hydrogen or -OH, and is not H at the same time, R4', R5' position is not fixed; R1 is selected from one of N, O, S, P elements, and R7 selectively contains H according to R1; (2) Under alkaline conditions, the esterification reaction of the anthracene compound with multiple phenolic hydroxyl groups with the diazonium naphthoquinone compound DNQ in a solvent generates a diazonium naphthoquinone photoinitiator.

5. The method of synthesizing an anthracene-based backbone compound according to claim 4, wherein The anthracene ketone is replaced by anthracene ketone derivatives, heterocyclic anthracene ketone or heterocyclic anthracene ketone derivatives; wherein the anthrone derivative has the structure , the heterocyclic anthrone is selected from , the heterocyclic anthrone derivative is selected from .

6. The method of synthesizing an anthracene-based backbone compound according to claim 4, wherein The strong acid catalyst includes one or more of β-mercapto propionic acid, sulfuric acid, trifluoromethyl sulfonic acid, trifluoromethyl sulfonic anhydride, and Amberlyst-15 hydrogen type strong acid resin.

7. The method of synthesizing an anthracene-based backbone compound according to claim 4, wherein In the esterification reaction process, the molar feeding ratio of the raw material DNQ to the multi-hydroxyl heterocyclic anthracene skeleton compound is 2-5:1, the synthesis temperature is controlled at 30-35℃, and the reaction time is 5-30min.

8. The method of synthesizing an anthracene-based backbone compound according to claim 4, wherein The organic solvent in step (1) includes one or more of DMF, methanol, acetone, and phenol; The solvent in step (2) includes 1,4-dioxane.

9. The method of synthesizing an anthracene-based backbone compound according to claim 4, wherein In the esterification reaction process in step (2), the diazonium naphthoquinone compound realizes the esterification reaction of the hydroxyl groups of each compound in the anthracene compound with multiple phenolic hydroxyl groups, and the esterification reaction includes one or more of mono-esterification, di-esterification, tri-esterification, tetra-esterification, penta-esterification, and hexa-esterification products.

10. A G / I line photoinitiator characterized by, The anthracene skeleton compound includes any one of claims 1-3.

11. A photosensitive material, characterized by, The anthracene skeleton compound includes any one of claims 1-3.

12. The photosensitive material of claim 11, wherein, The photosensitive material further includes a composition formed by phenolic resin and an organic solvent selected from propylene glycol methyl ether acetate PGMEA.

13. The photosensitive material of claim 11 or 12 in the field of photolithography process.

13. The photosensitive material of claim 11 or 12 in the field of photolithography process.

Images