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Anthrone

Anthrone is a planar tricyclic aromatic compound with the formula C14H10O.
It is a key intermediate in the synthesis of various organic compounds and has applications in photochemistry, dye chemistry, and biochemical research.
Anthrone and its derivatives exhibit diverse biological activities, including antimicrobial, antioxidant, and anticancer properties.
Researchers utilize anthrone in a variety of experimental protocols, such as spectrophotometric analyses, cell-based assays, and structural studies.
Optimizing anthrone-related experimental methods can enhance the reproducibility and accuracy of scientific findings in this area of chemistry and biology.

Most cited protocols related to «Anthrone»

1
Efficient Cell Wall Composition Analysis
Cited 11 times
Recently, there have been methods published that report comprehensive analysis of cell wall components; for example Pettolino et al. [14 (link)] and Foster et al. [15 (link)]. Most of these methods usually involve relatively larger amounts of cell wall material which is ground into a fine powder. For example, Foster et al. [15 (link)] typically start with 60–70 mg dried AIR. Our analysis on the other hand typically stats with 10 mg stem material for wild type samples and 2 mg for irx mutants. The smaller amount of starting sample amounts and the deliberate avoiding of grinding steps to increase throughput means that not all of the side-analyses can be incorporated into our method. However, we do anticipate that an extraction of intact stems with 2 M trifluoroacetic acid (TFA) prior to acetic/nitric treatment can be performed to yield material for analysis of non-cellulosic polysaccharides with GC–MS [15 (link)].
The time of some steps could be further reduced with the use of additional equipment. For example, although our method means it is convenient to carryout the drying steps overnight; a vacuum desiccator or speed vac could be used for the drying steps to reduce time. Another potential time saving improvement could be performing the anthrone assay in a 96-well plate format. This will need an appropriate plate reader to be available which could be used with strong acids (67 % sulphuric acid). Additionally, it will also need 96-well plates that are resistant to 67 % acid at high temperature. However, both these variations have been previously used [15 (link)].
Kumar M, & Turner S. (2015). Protocol: a medium-throughput method for determination of cellulose content from single stem pieces of Arabidopsis thaliana. Plant Methods, 11, 46.
Publication 2015
Acetic Acid Acids anthrone Biological Assay Cellular Structures Cell Wall Fever Gas Chromatography-Mass Spectrometry IRX 2 Polysaccharides Powder Stem, Plant Sulfuric Acids Vacuum
2
Quantification of Rhamnolipid Biosurfactants
Cited 7 times
Still pictures were taken with a gel doc imager (AlphaInnotech ChemiImager). Time lapse videos were acquired using a Marshall electronics v-1070 surveillance camera, set up in a room acclimatized to 37C. Swarming plates with fluorescently labeled strains were imaged using the Amersham Typhoon 9400 (GE Healthcare). Colony forming units (CFU) were estimated by plating serial dilutions with different strains distinguished by fluorescent color. Data points for number of cells in colony and rhamnose secreted measurements shown in plots represent the median value among all experimental replicates, with error bars representing the 95- and 5-percentile. Cell number ratios were determined by dividing the CFU number of one color by the CFU number of the other color. Error bars for such ratio measurements were estimated from binomial distribution fitting (Johnson et al., 1993 ). rhlA expression in swarming assays was assessed by quantifying the total GFP expression in swarming colonies of a strain containing the PrhlABGFP construct. The total colony fluorescence was measured in Photoshop and normalized by the fluorescence of a colony expressing GFP constitutively (promoter PA1/04/03GFP). Secreted lipids were extracted from growth supernatants using a chloroform/methanol extraction protocol adapted from (Caiazza et al., 2007 (link)). The rhamnolipids in the extract were measured using the anthrone colorimetric assay (Zhu & Rock, 2008 ). The amount of rhamnose in culture supernatant (47.4 mg/L for the WT grown for 24 h in the standard minimal medium) was calibrated using a rhamnose calibration curve. This was converted into rhamnolipid concentration applying a conversion factor of 3.0 to 3.2 (Camilios Neto et al., 2008 (link)), leading to the concentration of biosurfactants of 0.14–0.16 g/L. The concentration of dry mass of cells (0.717 g/L) was measured by gravimetry. Nalgene sterile analytical filter units (Thermo Fisher Scientific, Rochester, NY) with 0.2 μm pore size where pre-dried for 24 h at 65 C and used to filter 120 mL of culture. The filters where then dry for 48 h until mass became stable over time.
Xavier J.B., Kim W, & Foster K.R. (2010). A molecular mechanism that stabilizes cooperative secretions in Pseudomonas aeruginosa. Molecular microbiology, 79(1), 166-179.
Publication 2010
A-factor (Streptomyces) anthrone Biological Assay Chloroform Colorimetry factor A Fluorescence Lipids Methanol rhamnolipid Rhamnose Sterility, Reproductive Technique, Dilution Typhoons
3
Comprehensive Starch and Sugar Analysis
Cited 6 times
Embryos and pericarps were removed from the dehulled grains, and the endosperms were ground to a powder. The starch content was measured using a starch assay kit (K-TSTA; Megazyme) according to the manufacturer’s instructions. Apparent amylose content (AAC) was measured according to the method described by Tan et al. (1999) (link). For analysis of soluble sugars with anthrone reagent, 50mg of powder was washed twice in 80% (v/v) ethanol at 80 °C for 40min. The supernatant was collected and diluted to a volume of 15ml with water. An aliquot (0.1–0.3ml) of this solution was analysed for sugar content using the anthrone method.
To determine the chain length distributions of amylopectin, 5mg of rice powder was digested with Pseudomonas amyloderamosa isoamylase (Sigma-Aldrich) and then analysed by high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) using an ICS3000 model (Dionex) equipped with a pulsed amperometric detector and a CarboPac PA-20 column (Nagamine and Komae, 1996 ).
Wang J.C., Xu H., Zhu Y., Liu Q.Q, & Cai X.L. (2013). OsbZIP58, a basic leucine zipper transcription factor, regulates starch biosynthesis in rice endosperm. Journal of Experimental Botany, 64(11), 3453-3466.
Publication 2013
Amylopectin Amylose Anions anthrone Biological Assay Carbohydrates Cereals Chromatography Embryo Endosperm Ethanol Isoamylase Oryza sativa Powder Pseudomonas Starch Sugars tumor-associated transplantation antigen
4
Soluble Sugar and Sucrose Analysis
Cited 6 times
Dried samples were ground to a fine powder for soluble sugar and sucrose analysis. The sample powder (~0.2g) with three replications was extracted using 6 mL of 80% (v/v) ethanol for 30 min in a water bath at 80°C, then the supernatant was collected after centrifugation at 5,000g for 10 min. This extraction procedure was repeated three times. The three supernatants were pooled and then diluted with 80% ethanol to 25 mL for the measurement of soluble sugar and sucrose content. Soluble sugar content was determined by using the anthrone reagent method and calculated based on the absorbance at a wavelength of 625 nm and a standard curve [39 (link)]. Sucrose content was measured by using the resorcinol method and estimated on the basis of the absorbance at a wavelength of 480 nm and a standard curve [40 (link)]. The mobilized soluble sugar content was calculated by the difference between the largest sugar content and the sugar content at 30 days after anthesis.
Shi H., Wang B., Yang P., Li Y, & Miao F. (2016). Differences in Sugar Accumulation and Mobilization between Sequential and Non-Sequential Senescence Wheat Cultivars under Natural and Drought Conditions. PLoS ONE, 11(11), e0166155.
Publication 2016
anthrone Bath Carbohydrates Centrifugation DNA Replication Ethanol Powder resorcinol Sucrose
5
Biomass Enzyme Hydrolysis Optimization
Cited 6 times
Enzyme hydrolysis was performed in a 96-deep well format using the GLBRC Enzyme Platform (GENPLAT) as described earlier [4 (link),5 (link)]. Feedstocks were suspended and dispensed at 0.5% glucan, and final glucan loadings were 0.2%. Unless otherwise specified, enzyme loadings for all commercial benchmarks and for all mixture experiments were kept constant at 15 mg/g glucan, and reaction mixtures were incubated for 48 h at 50°C.
Design-Expert software (Stat-Ease Inc., Minneapolis, MN, USA) was used for experimental design and analysis. An augmented quadratic design was used throughout; thus, mixtures containing 6 and 16 components required 28 and 153 individual reactions, respectively. The lowest proportion of any enzyme in the core set (defined as CBH1, CBH2, EG1, BG, EX3, and BX) was set to 4%, because earlier studies indicated that for most of the core set, allowing them to go to 0% led to such poor Glc yields that reliable models could not be predicted [4 (link)]. The lowest proportion of all other enzymes ("accessory" proteins) was set to 0%. All assays were replicated once, sampled twice and assayed for Glc and Xyl twice, for a total of eight replicates of each mixture. Glc and Xyl were assayed colorimetrically [4 (link)]. Model predictions were tested experimentally as indicated in each table.
The monosaccharide composition of feedstocks was determined by the GLBRC Analytical Laboratory at Michigan State University. Briefly, samples were ground and washed sequentially with water, 70% ethanol, 1:1 chloroform:methanol, and acetone. The samples were then treated with amyloglucosidase + α-amylase, and the released Glc was quantitated as starch. The remaining material was then hydrolyzed with 2 N trifluoroacetic acid, and the released sugars were quantitated by GC of the alditol acetates. The insoluble residue from this step was treated with Updegraff's reagent, and the insoluble material was hydrolyzed with strong sulfuric acid and quantitated as cellulose using anthrone [16 (link),17 (link)].
The proteins in the commercial preparation Novozyme 188 and in β-mannanase (Megazyme catalog E-BMANN) were analyzed using standard mass spectrometry-based proteomics [3 (link)]. Scaffold version 01_07_00 (Proteome Software, Portland, OR, USA) was used to probabilistically validate protein identifications (DOE Joint Genome Institute) using the X!Tandem and ProteinProphet computer algorithms.
Banerjee G., Car S., Scott-Craig J.S., Borrusch M.S, & Walton J.D. (2010). Rapid optimization of enzyme mixtures for deconstruction of diverse pretreatment/biomass feedstock combinations. Biotechnology for Biofuels, 3, 22.
Publication 2010
Acetates Acetone Amylase anthrone beta Mannosidase Cellulose Chloroform Enzymes Ethanol Genome Glucan 1,4-alpha-Glucosidase Glucans Hydrolysis Joints Mass Spectrometry Methanol Monosaccharides Novozym 188 Proteins Proteome Starch Sugar Alcohols Sugars Sulfuric Acids Trifluoroacetic Acid

Most recents protocols related to «Anthrone»

1
Determination of Total Sugar in Enriched Rice Biscuits
Not available on PMC !
Reagent was used for the determination of the total sugar content of the enriched rice biscuit. One gram of the sample was hydrolysed with 5 mL of 2.5 N hydrochloric acid in a water bath for a period of three hours. It was allowed to cool and neutralized with Na2CO3 until effervescence ceased. The resulting mixture was made up to 100 mL and centrifugation was carried out for 5 min at 6000 rev per min. Anthrone reagent (4 mL) was added to the aliquot supernatant (1 mL), boiled in a water bath for 8 min, cooled and the resultant green to dark green colour was measured using a spectrometer (HITACHI spectrophotometer. Model: EA6000VX) at 630 nm. The absorbance value was compared with the standard curve of total carbohydrate and total sugar (glucose) was estimated as follows:
Total sugar (mg/100 g) = (Amount of carbohydrate /1 g x volume of test sample)/100
Akande O.A. (2024). Comparison of Inclusion of Skimmed Milk and Edible Insects on the Nutritional, Sensory and Microbial Qualities of Enriched High Energy Rice Biscuits. European Journal of Nutrition & Food Safety, 16(4), 85-94.
Publication 2024
2
Quantitative Estimation of Carbohydrates
Not available on PMC !
The Anthrone test is a simple method for the quantitative estimation of carbohydrates in different classes of samples like plant extracts, milk, blood serum, etc. The test was performed according to the mentioned protocol (Richards et al. 2020 (link)) with slight modifications. In brief, glucose stock solution (1 mg/ml) was prepared, and further diluted tenfold, glucose concentrations (200-1000 µg/mL) including an unknown sample (AZOME) extract.
Freshly, prepared (0.2%) anthrone reagent in Sulphuric acid of which 3 mL was added to each test tube. Tubes were kept at a temperature of 90°C for 10 min in a water bath. Meanwhile, the carbohydrate gets reacted with concentrated Sulphuric acid to form furfural. Then furfural reacts with the anthrone reagent to give different shades of bluish-green complex solutions. The absorbance was taken at 630 nm of all samples spectrophotometrically on a multi-mode microplate reader (synergy H1, BioTek, USA).
Antioxidant, Antimicrobial, Antidiabetic, Antiglycation, and Biocompatibility Potential of Aqueous Zingiber officinale Rhizome (AZOME) Extract. (2024). Journal of Angiotherapy, 8(5).
Publication 2024
3
Quantifying Total Reducing Sugars
To quantify the total reducing sugars (TRS), a microplate adapted version of the anthrone-sulfuric acid method [30 (link)] was used. Briefly, 133 µl of anthrone solution (2 g/L anthrone in sulfuric acid) were added to 67 µl of each sample or the standard and mixed up and down with the micropipette in 96-well plates. The plates were heated to 95 °C for 10 min and allowed to cool for 10 min. Absorbance was measured in a microplate reader with a 630 nm filter. A glucose standard curve (15 to 350 µg/ml) was used for quantification. An internal standard of known concentration of CβG was included in each measurement to verify that the polysaccharide hydrolysis was complete. Results for CβG concentration were expressed as mg of glucose equivalents per L.
Guidolin L.S., Caillava A.J., Landoni M., Couto A.S., Comerci D.J, & Ciocchini A.E. (2024). Development of a scalable recombinant system for cyclic beta-1,2-glucans production. Microbial Cell Factories, 23, 130.
Publication 2024
4
Novel OLED Material Synthesis and Device Fabrication
Not available on PMC !

Example 1

[Figure (not displayed)]

(1) in a nitrogen atmosphere, raw material B was weighed and dissolved in tetrahydrofuran (THF), then, raw material C and tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, an aqueous solution of potassium carbonate was then added, and the mixed solution containing the above reactants was heated and refluxed for 5-20 hours at a reaction temperature of 70° C. to 90° C. After completion of the reaction, the mixed solution was cooled and added with water, the mixture was extracted with dichloromethane, extract liquid was dried over anhydrous sodium sulfate, then filtered and concentrated under reduced pressure, and the resulting residue was purified using a silica gel column to obtain intermediate I;

wherein the molar ratio of raw material B to raw material C is 1:1.0-1.5, the molar ratio of tetrakis (triphenylphosphine) palladium to raw material B is 0.001-0.02:1, the molar ratio of potassium carbonate to raw material B is 1.0-2.0:1, and the dosage ratio of THF to raw material B is 1 g:10-30 ml.

[Figure (not displayed)]

(2) In a nitrogen atmosphere, intermediate I was weighed and dissolved in tetrahydrofuran (THF), then, raw material D and tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, an aqueous solution of potassium carbonate was then added, and the mixed solution containing the above reactants was heated and refluxed for 5-20 hours at a reaction temperature of 70° C. to 90° C. After completion of the reaction, the mixed solution was cooled and added with water, the mixture was extracted with dichloromethane, extract liquid was dried over anhydrous sodium sulfate, then filtered and concentrated under reduced pressure, and the resulting residue was purified using a silica gel column to obtain intermediate II;

wherein the molar ratio of intermediate I to raw material D is 1:1.0-1.5, the molar ratio of tetrakis (triphenylphosphine) palladium to intermediate I is 0.001-0.02:1, the molar ratio of potassium carbonate to intermediate I is 1.0-2.0:1, and the dosage ratio of THF to intermediate I is 1 g:10-30 ml.

[Figure (not displayed)]

(3) In a nitrogen atmosphere, intermediate II was weighed and dissolved in tetrahydrofuran (THF), then, raw material E and tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, an aqueous solution of potassium carbonate was then added, and the mixed solution containing the above reactants was heated and refluxed for 5-20 hours at a reaction temperature of 70° C. to 90° C. After completion of the reaction, the mixed solution was cooled and added with water, the mixture was extracted with dichloromethane, extract liquid was dried over anhydrous sodium sulfate, then filtered and concentrated under reduced pressure, and the resulting residue was purified using a silica gel column to obtain intermediate III;

wherein the molar ratio of intermediate II to raw material E is 1:1.0-1.5, the molar ratio of tetrakis (triphenylphosphine) palladium to intermediate II is 0.001-0.02:1, the molar ratio of potassium carbonate to intermediate II is 1.0-2.0:1, and the dosage ratio of THF to intermediate II is 1 g:10-30 ml.

[Figure (not displayed)]

In a nitrogen atmosphere, intermediate III was weighed and dissolved in tetrahydrofuran (THF), then, bis (pinacolyl) diboron, (1,1′-bis (diphenylphosphino) ferrocene) dichloropalladium (II) and potassium acetate were added, the mixture was stirred, and the mixed solution containing the above reactants was heated and refluxed for 5-10 hours at a reaction temperature of 70° C. to 90° C.; after completion of the reaction, the reaction solution was added with water and cooled and then the mixture was filtered and dried in a vacuum oven. The resulting residue was separated and purified using a silica gel column to obtain an intermediate M.

Taking the synthesis of intermediate M-5 as an example:

[Figure (not displayed)]

(1) In a 250 ml three-necked flask, nitrogen gas was introduced, 0.04 mol of raw material 2,4,6-Trichloropyridine, 150 ml of THF, 0.05 mol of 4-biphenylboronic acid, and 0.0004 mol of tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, 0.06 mol of the aqueous solution of K2CO3 (2M) was added, and the mixed solution was heated to 80° C. and refluxed for 10 hours, sampled and spotted until completion of the reaction. The mixed solution was cooled naturally, extracted with 200 ml of dichloromethane, and layered, the extract liquid was dried over anhydrous sodium sulfate, and filtered, the filtrate was rotarily evaporated, and purified using a silica gel column to obtain intermediate X; the purity of the product by HPLC was 99.5%, and the yield was 75.4%. Elemental analysis structure (molecular formula C9H5Cl2N3): theoretical values: C, 47.82; H, 2.23; Cl, 31.36; N, 18.59; test values: C, 47.81; H, 2.23; Cl, 31.36; N, 18.60. ESI-MS(m/z)(M+): the theoretical value is 224.99, and the test value is 225.20.

[Figure (not displayed)]

(2) In a 250 ml three-necked flask, nitrogen gas was introduced, 0.02 mol of intermediate X, 120 ml of THF, 0.025 mol of 9,9-dimethyl-2-boronic acid, and 0.0002 mol of tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, 0.03 mol of the aqueous solution of K2CO3 (2M) was added, and the mixed solution was heated to 80° C. and refluxed for 10 hours, sampled and spotted until completion of the reaction. The mixed solution was cooled naturally, extracted with 200 ml of dichloromethane, and layered, the extract liquid was dried over anhydrous sodium sulfate, and filtered, the filtrate was rotarily evaporated, and purified using a silica gel column to obtain an intermediate Y; the purity of the product by HPLC was 99.1%, and the yield was 67.3%. Elemental analysis structure (molecular formula C14H9ClN4): theoretical values: C, 62.58; H, 3.38; Cl, 13.19; N, 20.85; test values: C, 62.58; H, 3.38; Cl, 13.20; N, 20.84. ESI-MS(m/z)(M+): the theoretical value is 268.05, and the test value is 268.65.

[Figure (not displayed)]

(3) In a 250 ml three-necked flask, nitrogen gas was introduced, 0.02 mol of intermediate Y, 150 ml of THF, 0.025 mol of chlorophenylboronic acid, and 0.0002 mol of tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, 0.03 mol of the aqueous solution of K2CO3 (2M) was added, and the mixed solution was heated to 80° C. and refluxed for 10 hours, sampled and spotted until completion of the reaction. The mixed solution was cooled naturally, extracted with 200 ml of dichloromethane, and layered, the extract liquid was dried over anhydrous sodium sulfate, and filtered, the filtrate was rotarily evaporated, and purified using a silica gel column to obtain an intermediate Z; the purity of the product by HPLC was 99.2%, and the yield was 67.1%. Elemental analysis structure (molecular formula C26H17ClN4): theoretical values: C, 74.19; H, 4.07; Cl, 8.42; N, 13.31; test values: C, 74.20; H, 4.07; Cl, 8.42; N, 13.30. ESI-MS(m/z)(M+): the theoretical value is 420.11, and the test value is 420.70.

[Figure (not displayed)]

(4) In a 250 ml three-necked flask, nitrogen gas was introduced, 0.02 mol of intermediate Z was added and dissolved to 150 ml of THF, 0.024 mol of bis (pinacolyl) diboron, 0.0002 mol of (1,1′-bis (diphenylphosphino) ferrocene) dichloropalladium (II) and 0.05 mol of potassium acetate were added, the mixture was stirred, the mixed solution of the above reactants was heated and refluxed for 5 hours at a reaction temperature of 80° C.; after completion of the reaction, the reaction solution was cooled and added with 100 ml of water, and the mixture was filtered and dried in a vacuum oven. The resulting residue was separated and purified using a silica gel column to obtain intermediate M-5. The purity of the product by HPLC was 99.6%, and the yield was 91.2%. Elemental analysis structure (molecular formula C32H29BN4O2): theoretical values: C, 75.01; H, 5.70; B, 2.11; N, 10.93; test values: C, 75.00; H, 5.70; B, 2.11; N, 10.94. ESI-MS(m/z)(M+): the theoretical value is 512.24, and the test value is 512.53.

Intermediate M was prepared by the synthesis method of intermediate M-5. The specific structure is shown in Table 1.

TABLE 1
Raw material BRaw material CRaw material DRaw material EIntermediate M
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-1
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-2
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-3
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
/[Figure (not displayed)]
Intermediate M-4
[Figure (not displayed)]
[Figure (not displayed)]
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[Figure (not displayed)]
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Intermediate M-5
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[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
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Intermediate M-6
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Intermediate M-7
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Intermediate M-8
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-9
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-10
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
/[Figure (not displayed)]
Intermediate M-11
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
Intermediate M-12
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
/[Figure (not displayed)]
Intermediate M-13
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Intermediate M-14
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Intermediate M-15
[Figure (not displayed)]
[Figure (not displayed)]
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/[Figure (not displayed)]
Intermediate M-16

As shown in FIG. 1, an electroluminescent device was prepared by the steps of: a) cleaning an ITO anode layer 2 on a transparent substrate layer 1, ultrasonic cleaning in deionized water, acetone and alcohol each for 15 minutes, and then treating in a plasma cleaner for 2 minutes; b) vapor-depositing a hole injection layer material HAT-CN with a thickness of 10 nm on the ITO anode layer 2 by vacuum vapor deposition, wherein, this layer functions as a hole injection layer 3; c) vapor-depositing a hole transport material NPB with a thickness of 80 nm on the hole injection layer 3 by vacuum vapor deposition, wherein, this layer functions as a hole transport layer or electron block layer 4; d) vapor-depositing a light-emitting layer 5 with a thickness of 40 nm on the hole transport layer or electron block layer 4, wherein, compound 3 of the present functions and compound GH function as the host material, Ir(ppy)3 functions as a doping material, and a mass ratio of the compound 3 to GH to Ir(ppy)3 is 50:50:10; e) vapor-depositing an electron transport material TPBI with a thickness of 35 nm on the light-emitting layer 5 by vacuum vapor deposition, wherein, this organic material layer is used as a hole block or electron transport layer 6; f) vapor-depositing an electron injection layer LiF with a thickness of 1 nm by vacuum vapor deposition on the hole block or electron transport layer 6, wherein, this layer functions as an electron injection layer 7; g) vapor-depositing a cathode A1 (100 nm) on the electron injection layer 7 by vacuum vapor deposition, and this layer is a cathode reflective electrode layer 8. After completing the fabrication of the electroluminescent device according to the above steps, the driving voltage and current efficiency of the device were measured, and the results are shown in Table 3. Molecular structural formulas of related materials are as shown below:

[Figure (not displayed)]
[Figure (not displayed)]

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection Layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm). The measured data of the electroluminescent device obtained is as shown in Table 3.

TABLE 3
CurrentLT95 life
efficiency(Hr) @
No.(cd/A)Color5000 nits
Device example 146.4Green light27.3
Device example 245.5Green light26.5
Device example 346.7Green light25.1
Device example 445.9Green light25.7
Device example 545.4Green light25.5
Device example 636.9Green light27.6
Device example 737.1Green light27.1
Device example 842.9Green light25.6
Device example 945.5Green light27.3
Device example 1045.7Green light25.1
Device example 1147.1Green light27.2
Device example 1246.3Green light25.9
Device example 1347.9Green light25.3
Device example 1445.1Green light26.1
Device example 1546.5Green light26.2
Device example 1636.3Green light35.3
Device example 1735.9Green light33.4
Device example 1836.5Green light32.1
Device example 1935.3Green light32.8
Device example 2038.1Green light33.9
Device example 2137.3Green light37.8
Device example 2236.4Green light32.0
Device comparative28  Green light10.5
example 1

As can be seen from the results in Table 3, the organic compound of the present invention can be applied to the fabrication of OLED light-emitting devices, and compared with the comparative examples, the organic compound of the present invention is greatly improved in both the efficiency and the life over the known OLED materials, especially the service life of the devices is improved greatly. Further, the OLED device prepared using the material of the present invention can maintain a long life at a high temperature. Device examples 1 to 22 and Device comparative example 1 were subjected to a high-temperature driving life test at 85° C. The results are shown in Table 4.

TABLE 4
High-temperature
Device No.:LT95 life
Device example 122.8
Device example 220.7
Device example 322.1
Device example 423.3
Device example 522.5
Device example 623.3
Device example 723  
Device example 822.7
Device example 921.9
Device example 1023.6
Device example 1123.7
Device example 1224.1
Device example 1322.7
Device example 1421.2
Device example 1522.0
Device example 1627.5
Device example 1729.7
Device example 1828.6
Device example 1929.4
Device example 2030.6
Device example 2129.9
Device example 2229.4
Device comparative 0.7
example 1

As can be seen from the results in Table 4, Device examples 1 to 22 disclose device structures using both the material of the present invention and known materials. Compared with Device comparative example 1, at a high temperature, the OLED device provided by the present invention has a very good driving life.

Further, the efficiency of the OLED device prepared by using the material of the present invention is relatively stable when operating at a low temperature. Device examples 2, 10 and 18 and Device comparative example 1 were tested for efficiency in the range of −10° C. to 80° C. The results are shown in Table 5 and the FIG. 2.

TABLE 5
Temperature (° C.)
Current efficiency (cd/A)−1001020304050607080
Device example 243.344.445.145.546.246.748.147.446.646.9
Device example 1043.644.244.845.746.347.047.947.747.047.5
Device example 1834.435.235.736.537.237.738.038.237.837.4
Device comparative23.525.127.128.028.528.928.927.125.322.4
example 1

As can be seen from the results in Table 5 and FIG. 2, Device examples 2, 10 and 18 disclose device structures using both the material of the present invention and known materials. Compared with Device comparative example 1, these Device examples have higher low-temperature efficiency, and also have the efficiency increased steadily during the temperature rise.

To sum up, the embodiments mentioned above are merely preferred embodiments of the present invention and not intended to limit the present invention. Any of modifications, equivalent substitutions and improvements, etc. made within the spirit and principle of the present invention shall be covered in the protection scope of the present invention.

Example 2

[Figure (not displayed)]

In a 250 ml three-necked flask, nitrogen gas was introduced, 0.01 mol of raw material A1, 150 ml of THF, 0.015 mol of intermediate M-1, and 0.0001 mol of tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, 0.02 mol of the aqueous solution of K2CO3 (2M) was added, and the mixed solution was heated to 80° C. and refluxed for 15 hours, sampled and spotted until completion of the reaction. The mixed solution was cooled naturally, extracted with 200 ml of dichloromethane, and layered, the extract liquid was dried over anhydrous sodium sulfate, and filtered, the filtrate was rotarily evaporated, and purified using a silica gel column to obtain a target compound; the purity of the target compound by HPLC was 99.1%, and the yield was 77.3%. Elemental analysis structure (molecular formula C34H21N3O2): theoretical values: C, 81.10; H, 4.20; N, 8.34; test values: C, 81.10; H, 4.20; N, 8.33. ESI-MS(m/z)(M+): the theoretical value is 503.16, and the test value is 503.65.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 10, GH and Ir(ppy)3 mixed in a weight ratio of 40:60:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 3

[Figure (not displayed)]

In a 250 ml three-necked flask, nitrogen gas was introduced, 0.01 mol of raw material A1, 150 ml of THF, 0.015 mol of intermediate M-2, and 0.0001 mol of tetrakis (triphenylphosphine) palladium were added, the mixture was stirred, 0.02 mol of the aqueous solution of K2CO3 (2M) was added, and the mixed solution was heated to 80° C. and refluxed for 15 hours, sampled and spotted until completion of the reaction. The mixed solution was cooled naturally, extracted with 200 ml of dichloromethane, and layered, the extract liquid was dried over anhydrous sodium sulfate, and filtered, the filtrate was rotarily evaporated, and purified using a silica gel column to obtain a target compound; the purity of the target compound by HPLC was 99.3%, and the yield was 71.9%. Elemental analysis structure (molecular formula C40H25N3O2): theoretical values: C, 82.88; H, 4.35; N, 7.25; test values: C, 82.88; H, 4.35; N, 7.24. ESI-MS(m/z)(M+): the theoretical value is 579.19, and the test value is 579.75.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 11, GH and Ir(ppy)3 mixed in a weight ratio of 60:40:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 4

[Figure (not displayed)]

The preparation method of the compound 11 was the same with that in Example 2, except that the intermediate M-1 was replaced with the intermediate M-3. Elemental analysis structure (molecular formula C40H25N3O2): theoretical values: C, 82.88; H, 4.35; N, 7.25; test values: C, 82.88; H, 4.35; N, 7.24. ESI-MS(m/z)(M+): the theoretical value is 579.19, and the test value is 580.10.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 20, GH and Ir(ppy)3 mixed in a weight ratio of 70:30:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 5

[Figure (not displayed)]

The preparation method of the compound 20 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A2, and the intermediate M-1 was replaced with the intermediate M-3. Elemental analysis structure (molecular formula C40H25N3O2): theoretical values: C, 82.88; H, 4.35; N, 7.25; test values: C, 82.88; H, 4.35; N, 7.26. ESI-MS(m/z)(M+): the theoretical value is 579.19, and the test value is 579.45.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 27, GH and Ir(ppy)3 mixed in a weight ratio of 60:40:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 6

[Figure (not displayed)]

The preparation method of the compound 27 was the same with that in Example 2, except that raw material A1 was replaced with raw material A3. Elemental analysis structure (molecular formula C37H27N3O): theoretical values: C, 83.91; H, 5.14; N, 7.93; test values: C, 83.91; H, 5.14; N, 7.94. ESI-MS(m/z)(M+): the theoretical value is 529.22, and the test value is 529.55.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 35 and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 7

[Figure (not displayed)]

The preparation method of the compound 35 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A3, and the intermediate M-1 was replaced with the intermediate M-3. Elemental analysis structure (molecular formula C43H31N3O): theoretical values: C, 85.26; H, 5.16; N, 6.94; test values: C, 85.26; H, 5.16; N, 6.94. ESI-MS(m/z)(M+): the theoretical value is 605.74, and the test value is 605.94.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 44 and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 8

[Figure (not displayed)]

The preparation method of the compound 44 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A4, and the intermediate M-1 was replaced with the intermediate M-3. Elemental analysis structure (molecular formula C43H31N3O): theoretical values: C, 85.26; H, 5.16; N, 6.94; test values: C, 85.27; H, 5.16; N, 6.93. ESI-MS(m/z)(M+): the theoretical value is 605.25, and the test value is 605.88.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 59, GH and Ir(ppy)3 mixed in a weight ratio of 50:50:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 9

[Figure (not displayed)]

The preparation method of the compound 50 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A5, and the intermediate M-1 was replaced with the intermediate M-4. Elemental analysis structure (molecular formula C41H27N3O): theoretical values: C, 85.25; H, 4.71; N, 7.27; test values: C, 85.25; H, 4.71; N, 7.26. ESI-MS(m/z)(M+): the theoretical value is 577.22, and the test value is 577.81.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 69, GH and Ir(ppy)3 mixed in a weight ratio of 50:50:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 10

[Figure (not displayed)]

The preparation method of the compound 59 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A6, and the intermediate M-1 was replaced with the intermediate M-4. Elemental analysis structure (molecular formula C41H27N3O): theoretical values: C, 85.25; H, 4.71; N, 7.27; test values: C, 85.25; H, 4.71; N, 7.26. ESI-MS(m/z)(M+): the theoretical value is 577.22, and the test value is 577.82.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 95, GH and Ir(ppy)3 mixed in a weight ratio of 50:50:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 11

[Figure (not displayed)]

The preparation method of the compound 69 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A6, and the intermediate M-1 was replaced with the intermediate M-11. Elemental analysis structure (molecular formula C42H28N2O): theoretical values: C, 87.47; H, 4.89; N, 4.86; test values: C, 87.47; H, 4.89; N, 4.85. ESI-MS(m/z)(M+): the theoretical value is 576.22, and the test value is 576.55.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 104, GH and Ir(ppy)3 mixed in a weight ratio of 60:40:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 12

[Figure (not displayed)]

The preparation method of the compound 79 was the same with that in Example 2, except that the intermediate M-1 was replaced with the intermediate M-5. Elemental analysis structure (molecular formula C39H24N4O2): theoretical values: C, 80.67; H, 4.17; N, 9.65; test values: C, 80.67; H, 4.17; N, 9.64. ESI-MS(m/z)(M+): the theoretical value is 580.19, and the test value is 580.56.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 113, GH and Ir(ppy)3 mixed in a weight ratio of 70:30:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 13

[Figure (not displayed)]

The preparation method of the compound 80 was the same with that in Example 2, except that the intermediate M-1 was replaced with the intermediate M-6. Elemental analysis structure (molecular formula C38H23N5O2): theoretical values: C, 78.47; H, 3.99; N, 12.04; test values: C, 78.46; H, 3.99; N, 12.04. ESI-MS(m/z)(M+): the theoretical value is 581.19, and the test value is 581.75.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 128, GH and Ir(ppy)3 mixed in a weight ratio of 50:50:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 14

[Figure (not displayed)]

The preparation method of the compound 89 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A2, and the intermediate M-1 was replaced with the intermediate M-7. Elemental analysis structure (molecular formula C43H26N4O2): theoretical values: C, 81.89; H, 4.16; N, 8.88; test values: C, 81.89; H, 4.16; N, 8.89. ESI-MS(m/z)(M+): the theoretical value is 630.21, and the test value is 630.81.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 153, GH and Ir(ppy)3 mixed in a weight ratio of 50:50:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 15

[Figure (not displayed)]

The preparation method of the compound 95 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A3, and the intermediate M-1 was replaced with the intermediate M-8. Elemental analysis structure (molecular formula C39H29NO): theoretical values: C, 88.77; H, 5.54; N, 2.65; test values: C, 88.78; H, 5.54; N, 2.65. ESI-MS(m/z)(M+): the theoretical value is 527.22, and the test value is 527.62.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: compound 167, GH and Ir(ppy)3 mixed in a weight ratio of 40:60:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: TPBI)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 16

[Figure (not displayed)]

The preparation method of the compound 104 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A3, and the intermediate M-1 was replaced with the intermediate M-9. Elemental analysis structure (molecular formula C45H33NO): theoretical values: C, 89.52; H, 5.51; N, 2.32; test values: C, 89.52; H, 5.51; N, 2.33. ESI-MS(m/z)(M+): the theoretical value is 603.26, and the test value is 603.76.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 50)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 17

[Figure (not displayed)]

The preparation method of the compound 113 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A4, and the intermediate M-1 was replaced with the intermediate M-10. Elemental analysis structure (molecular formula C45H33NO): theoretical values: C, 89.52; H, 5.51; N, 2.32; test values: C, 89.52; H, 5.51; N, 2.33. ESI-MS(m/z)(M+): the theoretical value is 603.26, and the test value is 603.36.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 79)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 18

[Figure (not displayed)]

The preparation method of the compound 119 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A5, and the intermediate M-1 was replaced with the intermediate M-11. Elemental analysis structure (molecular formula C42H28N2O): theoretical values: C, 87.47; H, 4.89; N, 4.86; test values: C, 87.47; H, 4.89; N, 4.87. ESI-MS(m/z)(M+): the theoretical value is 576.22, and the test value is 576.82.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 80)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 19

[Figure (not displayed)]

The preparation method of the compound 126 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A5, and the intermediate M-1 was replaced with the intermediate M-12. Elemental analysis structure (molecular formula C48H32N2O): theoretical values: C, 88.32; H, 4.94; N, 4.29; test values: C, 88.31; H, 4.94; N, 4.29. ESI-MS(m/z)(M+): the theoretical value is 652.25, and the test value is 652.45.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 89)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 20

[Figure (not displayed)]

The preparation method of the compound 128 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A6, and the intermediate M-1 was replaced with the intermediate M-13. Elemental analysis structure (molecular formula C42H28N2O): theoretical values: C, 87.47; H, 4.89; N, 4.86; test values: C, 87.47; H, 4.89; N, 4.85. ESI-MS(m/z)(M+): the theoretical value is 576.22, and the test value is 576.98.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 119)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 21

[Figure (not displayed)]

The preparation method of the compound 139 was the same with that in Example 2, except that the intermediate M-1 was replaced with the intermediate M-14. Elemental analysis structure (molecular formula C42H25N3O2): theoretical values: C, 83.56; H, 4.17; N, 6.96; test values: C, 83.56; H, 4.17; N, 6.95. ESI-MS(m/z)(M+): the theoretical value is 603.19, and the test value is 603.77.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 126)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 22

[Figure (not displayed)]

The preparation method of the compound 153 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A3, and the intermediate M-1 was replaced with the intermediate M-15. Elemental analysis structure (molecular formula C45H31N3O): theoretical values: C, 85.83; H, 4.96; N, 6.67; test values: C, 85.83; H, 4.96; N, 6.66. ESI-MS(m/z)(M+): the theoretical value is 629.25, and the test value is 629.65.

ITO anode layer 2 (thickness: 150 nm)/hole injection layer 3 (thickness: 10 nm, material: HAT-CN)/hole transport layer 4 (thickness: 80 nm, material: NPB)/light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy)3 mixed in a weight ratio of 90:10)/hole block or electron transport layer 6 (thickness: 35 nm, material: compound 139)/electron injection layer 7 (thickness: 1 nm, material: LiF)/A1 (thickness: 100 nm).

Example 23

[Figure (not displayed)]

The preparation method of the compound 167 was the same with that in Example 2, except that the raw material A1 was replaced with raw material A6, and the intermediate M-1 was replaced with the intermediate M-16. Elemental analysis structure (molecular formula C45H27N3O): theoretical values: C, 86.38; H, 4.35; N, 6.72; test values: C, 86.38; H, 4.35; N, 6.73. ESI-MS(m/z)(M+): the theoretical value is 625.22, and the test value is 625.76.

When applied to a light-emitting device, the organic compound with a high Tg temperature (glass transition temperature) and triplet energy level (T1) and suitable HOMO and LUMO energy level can be used as a hole block/electron transport material and can also be uses as light-emitting layer material. Thermal property tests, T1 energy level tests and HOMO energy level tests were performed on the compounds of the present invention and the existing materials, respectively, and the results are as shown in Table 2.

TABLE 2
HOMO
energy
levelFunctional
CompoundT1 (ev)Tg (° C.)Td (° C.)(ev)layer
Compound 32.85136406−6.23Light-emitting
layer
Compound 102.86148427−6.21Light-emitting
layer
Compound 112.76150434−6.18Light-emitting
layer
Compound 202.78146417−6.23Light-emitting
layer
Compound 272.77143422−6.18Light-emitting
layer
Compound 352.82144423−6.18Light-emitting
layer
Compound 442.79145429−6.21Light-emitting
layer
Compound 502.81136405−6.47Hole block
or electron
transport layer
Compound 592.81142424−6.21Light-emitting
layer
Compound 692.78142416−6.19Light-emitting
layer
Compound 792.82139408−6.39Hole block
or electron
transport layer
Compound 802.80157436−6.46Hole block
or electron
transport layer
Compound 892.81137413−6.44Hole block
or electron
transport layer
Compound 952.82143424−6.19Light-emitting
layer
Compound 1042.71140400−6.18Light-emitting
layer
Compound 1132.74146429−6.16Light-emitting
layer
Compound 1192.80154436−6.45Hole block
or electron
transport layer
Compound 1262.82139410−6.41Hole block
or electron
transport layer
Compound 1282.85148426−6.20Light-emitting
layer
Compound 1392.82135413−6.45Hole block
or electron
transport layer
Compound 1532.77145424−6.23Light-emitting
layer
Compound 1672.81144436−6.21Light-emitting
layer
CBP2.52—373−6.17Light-emitting
layer
TPBi2.58121390−6.44Hole block
or electron
transport layer
Note:
The triplet energy level T1 was tested by F4600 fluorescence spectrometer provided by Hitachi, and the test condition of the materials was 2*10−5 toluene solution;
the glass transition temperature Tg was differential scanning calorimetry (DSC, DSC204F1 Differential Scanning Calorimeter, NETZSCH, Germany) at a heating rate of 10° C/min;
the thermal weight loss temperature Td which refers to the temperature in the case of 1% weight loss in a nitrogen atmosphere was measured on the TGA-50H thermogravimetric analyzer provided by Shimadzu Corporation with a nitrogen flow rate of 20 mL/min;
the HOMO energy level was tested by the ionization energy test system (IPS3) in an atmospheric environment.

As can be seen from the data in the above table, compared with the currently used CBP and TPBi materials, the organic compound of the present invention has a high glass transition temperature, can improve the phase-state stability of the material film and further improve the service life of the device; the organic compound of the present invention has a high triplet energy level and can block the energy loss of the light-emitting layer, thereby improving the light-emitting efficiency of the device. Meanwhile, the material of the present invention and the applied material have similar HOMO energy levels. Therefore, the organic material with anthrone and N-containing heterocycle of the present invention can effectively improve the light-emitting efficiency and service life of an OLED device after being applied to different functional layers of the OLED device.

Hereinafter, the application effect of the OLED material synthesized in the present invention in the device will be described in detail through Device examples 1 to 22 and Device comparative example 1. Compared to Device example 1, Device examples 2 to 22 and Device comparative example 1 of the present invention have identical device fabricating processes, adopt the same substrate materials and electrode materials, and maintain consistency in film thickness of the electrode material, except that Device examples 2 to 15 replace the light-emitting layer material in the device; Device examples 16 to 22 replace the hole block layer or the electron transport layer material, and performance test results of the device in each example are as shown in Table 3.

US11873294B2. Compound containing anthrone and nitrogen-containing heterocycle and application in OLED devices (2024-01-16). JIANGSU SUNERA TECHNOLOGY CO., LTD. [CN]. Inventors: Haifeng Chen [CN], Chong Li [CN], Zhaochao Zhang [CN], Xiaoqing Zhang [CN], Dandan Tang [CN].
Patent 2024
5
Quantifying Liver Glycogen Content in Mice
After 4 weeks of electroacupuncture treatment in each group of mice, inhaled isoflurane anesthetic fully exposed the liver of the mice, and the left leaf of the liver was placed in liquid nitrogen for follow-up testing. After liver sample collection, mice were euthanized by cervical dislocation. Each mouse took 50 mg of liver tissue and added liver tissue and lye to the test tube at 1 : 3 as hydrolysate, boiling water bath for 20 min, flowing water cooling. The liver glycogen hydrolysate was configured into 1% liver glycogen assay solution, and the assay reagents were configured according to Table 2, mixed and boiled in a water bath for 5 min, cooled, and colorimetric at 620 nm wavelength; the OD value of each tube was measured; the standard curve was drawn; the concentration of liver tissue homogenate was calculated from the standard curve; and the liver glycogen content was calculated by the formula.
The formula for calculating liver glycogen content is as follows: Liver glycogen contentmggtissue=Measure the OD value of the tubeStandard TUBE OD value×standard tube content0.01mg×dilution ratio of the sample before test×10÷1.11.
Guo Y., Zhang L., Li M., Lin L., Xue F., Gao W., Xu X, & Huang H. (2024). Metabolomics of Mice with Type 2 Diabetes and Nonalcoholic Fatty Liver Treated by Acupuncture. International Journal of Endocrinology, 2024, 5568337.
Publication 2024

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Sulfuric acid is a highly corrosive, colorless, and dense liquid chemical compound. It is widely used in various industrial processes and laboratory settings due to its strong oxidizing properties and ability to act as a dehydrating agent.
5
Anthrone by Sinopharm
Sourced in China
Anthrone is a chemical compound used as a reagent in analytical chemistry. It is a heterocyclic aromatic compound with the formula C14H10O. Anthrone is commonly used in colorimetric assays for the quantitative determination of carbohydrates.
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Libra s22 by Harvard Bioscience
Sourced in United Kingdom, United States
The Libra S22 is a general-purpose microvolume UV/Vis spectrophotometer designed for routine analysis of small sample volumes. It features high-quality optics, a xenon flash lamp, and a CCD array detector to provide accurate and reliable absorbance measurements across a wide wavelength range.
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Gallic acid by Merck Group
Sourced in United States, Germany, Italy, Spain, France, India, China, Poland, Australia, United Kingdom, Sao Tome and Principe, Brazil, Chile, Ireland, Canada, Singapore, Switzerland, Malaysia, Portugal, Mexico, Hungary, New Zealand, Belgium, Czechia, Macao, Hong Kong, Sweden, Argentina, Cameroon, Japan, Slovakia, Serbia
Gallic acid is a naturally occurring organic compound that can be used as a laboratory reagent. It is a white to light tan crystalline solid with the chemical formula C6H2(OH)3COOH. Gallic acid is commonly used in various analytical and research applications.
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Chloroform by Merck Group
Sourced in United States, Germany, United Kingdom, India, Italy, Spain, France, Canada, Switzerland, China, Australia, Brazil, Poland, Ireland, Sao Tome and Principe, Chile, Japan, Belgium, Portugal, Netherlands, Macao, Singapore, Sweden, Czechia, Cameroon, Austria, Pakistan, Indonesia, Israel, Malaysia, Norway, Mexico, Hungary, New Zealand, Argentina
Chloroform is a colorless, volatile liquid with a characteristic sweet odor. It is a commonly used solvent in a variety of laboratory applications, including extraction, purification, and sample preparation processes. Chloroform has a high density and is immiscible with water, making it a useful solvent for a range of organic compounds.
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Lambda 25 by PerkinElmer
Sourced in United States, Singapore, United Kingdom, Italy, Germany, Japan
The Lambda 25 is a UV/Vis spectrophotometer designed for routine analysis. It features a double-beam optical system and a deuterium and tungsten halogen light source to provide accurate measurements across the UV and visible spectrum.

More about "Anthrone"

Anthrone, a planar tricyclic aromatic compound with the formula C14H10O, is a pivotal intermediate in the synthesis of diverse organic compounds.
It has widespread applications in photochemistry, dye chemistry, and biochemical research, where it exhibits valuable biological activities such as antimicrobial, antioxidant, and anticancer properties.
Researchers commonly utilize anthrone in spectrophotometric analyses, cell-based assays, and structural studies to gain insights into various chemical and biological processes.
Anthrone reagent, a solution of anthrone in sulfuric acid, is a widely used analytical tool for the quantitative determination of carbohydrates, particularly in the presence of bovine serum albumin (BSA).
The Libra S22 UV/Vis spectrophotometer is often employed to measure the absorbance of anthrone-based assays, while gallic acid can serve as a standard in these analyses.
Chloroform is frequently used as a solvent in experiments involving anthrone, as it aids in the extraction and purification of anthrone and its derivatives.
The Lambda 25 UV/Vis spectrophotometer is another common instrument utilized to characterize the spectral properties of anthrone-related compounds.
By optimizing experimental methods and leveraging the insights gained from the literature, researchers can enhance the reproducibility and accuracy of their scientific findings in the field of anthrone chemistry and biology.
The PubCompare.ai platform can be a valuable tool in this endeavor, helping researchers identify the best protocols and solutions for their anthrone-based experiments.