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)].
Anthrone
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»
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)].
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 ).
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.
Most recents protocols related to «Anthrone»
Total sugar (mg/100 g) = (Amount of carbohydrate /1 g x volume of test sample)/100
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).
Example 1
(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.
(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.
(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.
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:
(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.
(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.
(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.
(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.
As shown in
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.
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.
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
As can be seen from the results in Table 5 and
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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.
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.
The formula for calculating liver glycogen content is as follows:
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More about "Anthrone"
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.