CN111471043A - Organic light-emitting material containing benzo [ c ] [1,2,5] thiadiazole derivative receptor structural unit and application thereof - Google Patents

Abstract

The organic luminescent material is an acceptor-donor separation system, wherein the acceptor is benzo [ c ] [1,2,5] thiadiazole-4-aldehyde group acceptor or 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor, and the donor is carbazole and derivatives or benzoxazine and the like, wherein the lowest unoccupied orbital (L UMO) in the material is located in the acceptor, and the highest occupied orbital (HOMO) is located in the donor, so that the molecular orbital energy level of the luminescent material can be effectively regulated through the electrical regulation of the acceptor structure and the donor, and the luminescent color of the material molecule can be conveniently regulated through regulating the structure of the luminescent material or the electron donating capability of the donor.

Description

Organic light-emitting material containing benzo [ c ] [1,2,5] thiadiazole derivative receptor structural unit and application thereof

Technical Field

The invention relates to the field of organic luminescent materials, in particular to a luminescent material containing benzo [ c ] [1,2,5] thiadiazole-4-aldehyde group and 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor structural unit and application thereof.

Background

O L ED (Organic L light-Emitting Diode) or Organic light-Emitting Device (Organic L light-Emitting Device) is an autonomous light-Emitting material without backlight source, has the advantages of all solid state, wide viewing angle, low temperature resistance, color fidelity, low driving voltage, high response speed, high contrast and definition, ultra-thin property, easy flexible display and the like, can also use glass, flexible metal and plastic with low cost as a substrate, has the advantages of high energy efficiency, low energy consumption, wide material source, simple production process, planar light emission, large-area production and the like, and O36ED 35 is used as a new generation lighting and display technology, is applied to products such as mobile phones, flat panels, space cameras, televisions, computers, detection instruments and the like, and has potential application prospects in the fields of air-vehicle solid state lighting and the like.

The fluorescent material is the first generation O L ED material applied earliest, and is limited to that only singlet excitons can be used for emitting light by electron spin statistics, the internal quantum efficiency of the device is up to 25%. 1988, the Forrest professor of the university of Princeton in the United states reports the phosphorescence electroluminescence phenomenon of the metal organic platinum complex at room temperature, the internal quantum efficiency of the device can reach 100%. although the metal organic phosphorescent material has been developed greatly to date, the red and green iridium complex phosphorescent material has been used in commercial electronic products, but the phosphorescent material is very expensive due to the use of rare and expensive noble metals, and has limited resources.

Disclosure of Invention

The invention aims to provide a luminescent material containing benzo [ c ] [1,2,5] thiadiazole-4-aldehyde group and 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor structural units, and the material can be used for O L ED devices.

The invention adopts the following technical scheme:

an organic luminescent material containing a benzo [ c ] [1,2,5] thiadiazole derivative acceptor structural unit has a structural formula shown as a formula (I) or a formula (II):

in formula (I), the acceptor is benzo [ c ]][1,2,5]Thiadiazole-4-carboxaldehyde radical, R^a1Or R^b1Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof;

m1 and n1 represent the number of substituents; wherein m1 is an integer of 0-2, and n1 is an integer of 0-4;

in formula (II), the acceptor is 2- (benzo [ c ]][1,2,5]Thiadiazole-4-methylene) malononitrile, R^a2Or R^b2Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof;

m2 and n2 represent the number of substituents; wherein m2 is an integer of 0-2, and n2 is an integer of 0-4;

donor D¹Or D²Each independently is one of the following structures:

wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And R¹²Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, silicon, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof, wherein two adjacent substituents can be fused to form a ring;

o1, p1, q1, R1, s1, t1, u1, v1, w1, x1, y1 and z1 are each R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And R¹²The number of (2); o1, p1, q1, r1, s1, t1, u1, v1, w1, x1, y1 and z1 are integers from 0 to 4.

Further, the organic luminescent material is a compound shown in formulas (III) and (IV):

wherein, in the formula (III), R^a3Or R^b3Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof;

m3 and n3 represent the number of substituents; wherein m3 is an integer of 0-2, and n3 is an integer of 0-4;

in the formula (IV), R^a4Or R^b4Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof;

m4 and n4 represent the number of substituents; wherein m4 is an integer of 0-2, and n4 is an integer of 0-4;

said donor D³Or D⁴Each independently is one of the following structures:

wherein R is¹'、R²'、R³'、R⁴'、R⁵'、R⁶'、R⁷'、R⁸'、R⁹'、R¹⁰'、R¹¹' and R¹²' independently of one another are hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, silicon, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof, wherein two adjacent substituents can be fused to form a ring;

o2, p2, q2, R2, s2, t2, u2, v2, w2, x2, y2 and z2 are each R¹'、R²'、R³'、R⁴'、R⁵'、R⁶'、R⁷'、R⁸'、R⁹'、R¹⁰'、R¹¹' and R¹²' number; o2, p2, q2, r2, s2, t2, u2, v2, w2, x2, y2 and z2 are integers from 0 to 4.

Further, the organic light-emitting material is one of the following materials:

further, the organic luminescent material based on the donor-acceptor structure of the benzo [ c ] [1,2,5] thiadiazole-4-aldehyde group acceptor and the 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor is as follows:

the invention also provides an application of the luminescent material based on the benzo [ c ] [1,2,5] thiadiazole-4-aldehyde group and the 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor structural unit as a luminescent layer of an organic electroluminescent device.

Compared with the prior art, the invention has the beneficial effects that:

(1) the molecular orbital energy level of the luminescent material can be effectively regulated and controlled through the electrical regulation of the acceptor structure and the donor.

(2) The luminous color of the material molecules can be conveniently adjusted by regulating the structure of the luminous material or the electron supply capacity of the donor.

(3) Luminescent materials based on novel acceptor structures can be successfully applied to the preparation of O L ED devices.

Drawings

FIG. 1 is a comparison of HOMO and L UMO orbital distributions of BTC-1, BTC-2, BTC-3, and BTC-4 calculated by Density Functional Theory (DFT).

FIG. 2 is a comparison of HOMO and L UMO orbital distributions of BTN-1, BTN-2, BTN-3, and BTN-4 calculated by Density Functional Theory (DFT).

FIG. 3(a) is an absorption spectrum of luminescent materials BTC-1, BTC-2, BTC-3 and BTC-4 in a toluene solution at room temperature; (b) the absorption spectra of the luminescent materials BTN-1, BTN-2, BTN-3 and BTN-4 in toluene solution at room temperature.

FIG. 4(c) is an emission spectrum of the luminescent materials BTC-1, BTC-2, BTC-3 and BTC-4 in a toluene solution at room temperature; (d) the emission spectra of the luminescent materials BTN-1, BTN-2 and BTN-3 in toluene solution at room temperature.

FIG. 5 is a comparison of the emission spectra of the light-emitting material BTC-1 at room temperature in various environments, wherein HEX is n-hexane, TO L is toluene, EA is ethyl acetate, THF is tetrahydrofuran, and DCM is dichloromethane.

FIG. 6 is a comparison of the emission spectra of the light-emitting material BTC-2 at room temperature in various environments, wherein HEX is n-hexane, TO L is toluene, EA is ethyl acetate, THF is tetrahydrofuran, and DCM is dichloromethane.

FIG. 7 is a graph showing emission spectra of thin films of the light-emitting materials BTC-1, BTC-2 and BTC-3.

FIG. 8 is a graph of the electroluminescence spectra of the luminescent materials CBP or mCBP as luminescent host respectively doped with BTC-3 with different concentrations.

Fig. 9 is a current density-voltage-luminescence intensity curve of a device with different concentrations of BTC-3 doping of a luminescent material CBP or mCBP as a luminescent host.

FIG. 10 is the device electroluminescence spectrum of the luminescent material mCBP as the luminescent host under the doping of the guest BTC-1, BTC-2 and BTC-3 respectively.

Fig. 11 is a device current density-voltage-luminescence intensity curve of the luminescent material mCBP as a luminescent host under doping of the guest BTC-1, BTC-2 and BTC-3, respectively.

Fig. 12 is a schematic diagram of the structure of the fabricated device and the molecular structure of a part of the material.

Detailed Description

The invention is further illustrated by the following examples, without restricting its scope.

Unless otherwise indicated, all commercial reagents involved in the following experiments were purchased and used directly without further purification. The hydrogen spectrum and the carbon spectrum of the nuclear magnetic resonance are both in deuterated chloroform (CDCl)₃) The hydrogen spectrum and the carbon spectrum are measured in the solution by a nuclear magnetic resonance spectrometer with 400 or 500 MHz and 100 or 126 MHz respectively, and the chemical shifts are based on Tetramethylsilane (TMS) or residual solvent. With deuterated chloroform (CDCl)₃) As solvent, the hydrogen spectrum and the carbon spectrum were respectively expressed in TMS (═ 0.00ppm) and CDCl₃(77.00 ppm) as an internal standard, the following abbreviations (or combinations) are used to interpret the hydrogen peak s singlet, d doublet, t triplet, q quartet, p quintet, m multiplet, br broad, high resolution mass spectra were measured on L TQ FT Ultra mass spectrometer from seimer feishell technologies ltd, and the sample ionization mode was electrospray ionization.

Example 1: the synthesis route of the luminescent material BTN-1 is as follows:

synthesis of intermediate 1 3-methyl-1, 2-phenylenediamine (30.53g,249.87mmol,1.0 equiv.), triethylamine (138.92m L, 999.47mmol,4.0 equiv.) and dichloromethane (300m L) were added in this order to a dry three-necked flask equipped with magnetic stirring and placed in an ice bath, the mixture was stirred for 1 hour or more, after which thionyl chloride (36.25m L, 499.74mmol,2.0 equiv.) and dichloromethane (100m L) were slowly dropped, the mixture was stirred at that temperature for 1 hour, then the mixture was placed in an oil bath, stirred at 40 ℃ for 20 hours, the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, quenched with water, the mixture was extracted three times with ethyl acetate, the combined organic phase was washed with water, dried with anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate 10: 1-4: 1) to give 33.40g of colorless liquid with 89% yield.

Synthesis of intermediate 2, intermediate 1(32.06g,213.43mmol,1.0 equiv.), hydrogen bromide solution (200m L, 48% aqueous solution) and bromine water (11.48m L, 224.10mmol,1.05 equiv.) were added sequentially to a dry three-necked flask equipped with magnetic stirring, the mixture was put in an oil bath and stirred at 120 ℃ for reaction for 24 hours, then the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature and neutralized with a saturated sodium bicarbonate solution, the mixture was extracted three times with ethyl acetate, the combined organic phases were washed with water and dried with anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and a sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate ═ 20: 1-5: 1) to obtain 42.05g of white solid with a yield of 86%.

Synthesis of intermediate 3, intermediate 2(25.34g,110.62mmol,1.0 equiv.), N-bromosuccinimide (59.07g,331.88mmol,3.0 equiv.) and chlorobenzene (250m L) were sequentially added to a dry three-necked flask equipped with magnetic stirring and placed in an oil bath, and stirred at 60 ℃ for 20 minutes, then benzoyl peroxide (5.36g,22.13mmol,0.2 equiv.) was added, the mixture was placed in an oil bath and heated to 100 ℃ for reaction, after 24 hours, the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, quenched with water, the mixture was extracted three times with dichloromethane, the combined organic phase was washed with water, dried with anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the sample was purified by chromatography (eluent: petroleum ether/ethyl acetate 100: 1-10: 1) to obtain 32.10g of pale yellow solid with a yield of 75%.

Synthesis of Br-CHO intermediate 3(30.74g,79.45mmol,1.0 equiv.) and formic acid (100m L) were added sequentially to a dry three-necked flask equipped with magnetic stirring and placed in an oil bath and after heating to 120 ℃ for 24 hours, the reaction was monitored by thin layer chromatography until completion of the reaction the resulting mixture was cooled to room temperature, quenched with water and stirred for 1 hour the resulting mixture was concentrated in vacuo, the residue was washed three times with water and finally dried in a vacuum oven to give 15.45g of a brown solid compound in 80% yield.¹H NMR(500MHz,CDCl₃),8.06(d,J＝9.5Hz,1H),8.10(d,J＝9.5Hz,1H),10.76(s,1H)。¹³C NMR(125MHz，CDCl₃),121.7,126.7,131.5,131.9,152.1,153.8,188.0。HRMS(m/z,FAB+)：C₇H₃ ⁷⁹BrN₂OS calculated 241.9149, found 241.9149, C₇H₃ ⁸¹BrN₂OS calculated 243.9129, found 243.9137.

Synthesis of intermediate 1-Br carbazole (8.39g,50.17mmol,1.0 equiv.), 1-bromo-4-iodobenzene (15.61g,55.19mmol,1.1 equiv.), cuprous iodide (955.6mg,5.02mmol,0.1 equiv.), L-proline (1.16g,10.03mmol,0.2 equiv.), and potassium carbonate (13.87g,100.35mmol,2.0 equiv.) were added in sequence to a dry three-necked flask equipped with magnetic stirring, nitrogen was purged three times, then dimethyl sulfoxide (100m L) was added under nitrogen protection, the mixture was placed in an oil bath and heated to 100 ℃ for reaction, after 36 hours, monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature and diluted with dichloromethane, the mixture was washed three times with brine, dichloromethane was extracted three times, the combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, the filtrate was purified by silica gel column chromatography to give a white solid (eluent: petroleum ether) in a yield of 9.70g, 60%.

Synthesis of intermediate 1-B1-Br (4.99g,15.49mmol,1.0 eq.) was added to a dry three-necked flask equipped with magnetic stirring nitrogen was exchanged three times, then tetrahydrofuran (100m L) was added under nitrogen protection, after the mixture was cooled to-78 ℃ n-butyllithium (9.68m L, 15.49mmol,1.0 eq., 1.6 mol/L in hexane) was slowly added dropwise, the mixture was stirred at that temperature for 1 hour, then the mixture was warmed to room temperature and 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane (3.16m L, 15.49mmol,1.0 eq.) was added to the flask under nitrogen protection, after stirring for 12 hours, the reaction was monitored by thin layer chromatography, the resulting mixture was cooled to room temperature and quenched with saturated ammonium chloride solution, the mixture was extracted three times with dichloromethane, the combined organic sodium sulfate layers were washed with water, dried, the filtrate was filtered, the eluent was concentrated under reduced pressure, the mixture was purified by column chromatography (3.0 eq.: white silica gel column, 79 g, eluent: 52.3 g/79 g).

BTC-1 synthesis: mixing 1-B (1.33g,3.61 mm)ol,1.2 eq), Br-CHO (730.3mg,3.00mmol,1.0 eq), tetrakis (triphenylphosphine) palladium (104.1mg,0.09mmol,0.03 eq) and potassium carbonate (1.04g,7.51mmol,2.5 eq) were added sequentially to a dry three-necked flask equipped with magnetic stirring, nitrogen was pumped three times, then toluene (36m L), ethanol (12m L) and water (12m L) were added under nitrogen, and the mixture was heated to 90 ℃ in an oil bath, monitored by thin layer chromatography until the reaction was complete, the reaction was stopped after 18 hours, the resulting mixture was cooled to room temperature and quenched with water, the mixture was extracted three times with dichloromethane, the combined organic layers were washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1:1.5) to give 779.6mg of a yellow solid in 64% yield.¹H NMR(500MHz,CDCl₃),7.32-7.35(m,2H),7.44–7.47(m,2H),7.57(d,J＝8.2Hz,2H),7.81(dt,J＝8.5,2.2Hz,2H),8.02(d,J＝7.3Hz,1H),8.18(dt,J＝7.8,0.9Hz,2H),8.28(dt,J＝8.5,2.3Hz,2H),8.38(d,J＝7.3Hz,1H),10.84(s,1H)。¹³C NMR(125MHz,CDCl₃),109.99,120.48,120.57,123.79,126.24,126.73,127.23,127.33,131.23,132.65,135.26,139.16,139.41,140.65,153.94,154.01,189.08。

Synthesis of BTN-1 BTC-1(614.3mg,1.51mmol,1.0 equiv.), malononitrile (300.2mg,4.54mmol,3.0 equiv.), sodium acetate (618.5mg,4.54mmol,3.0 equiv.), anhydrous sodium sulfate (1.29g,9.09mmol,6.0 equiv.), and toluene (30m L) were sequentially added to a three-necked flask equipped with magnetic stirring, the mixture was placed in an oil bath, and the reaction was stirred at 90 ℃ for 18 hours, then the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, water was added to quench it, the mixture was extracted three times with dichloromethane, the combined organic layer was washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and a sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1:1) to obtain 680.2mg of an orange yellow solid with a yield of 99%.¹H NMR(500MHz,CDCl₃),7.32–7.35(m,2H),7.44–7.47(m,2H),7.57(d,J＝8.2Hz,2H),7.83(dt,J＝8.6,2.2Hz,2H),8.03(d,J＝7.7Hz,1H),8.17(dt,J＝7.7,1.0Hz,2H),8.30(dt,J＝8.6,2.2Hz,2H),8.86(dd,J＝7.7,0.6Hz,1H),8.90(s,1H)。

Example 2: the synthesis route of the luminescent material BTN-2 is as follows:

synthesis of 2-Br 3, 6-di-tert-butylcarbazole (3.19g,11.41mmol,1.0 equiv.), 1-bromo-4-iodobenzene (3.55g,12.55mmol,1.1 equiv.), cuprous iodide (217.2mg,1.14mmol,0.1 equiv.), L-proline (262.6mg,2.28mmol,0.2 equiv.) and potassium carbonate (2.63g,22.81mmol,2.0 equiv.) were added in this order to a dry three-necked flask equipped with magnetic stirring, nitrogen was evacuated three times, then dimethyl sulfoxide (60m L) was added under nitrogen protection, the mixture was placed in an oil bath and heated to 100 ℃ for reaction, after 36 hours, the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, and diluted with dichloromethane, the mixture was washed three times with brine, dichloromethane was extracted three times, the combined organic layers were dried over anhydrous sodium sulfate and the filtrate was concentrated, and the eluent was purified by silica gel column chromatography to give a white solid (3.32 g, 67.32% yield).

2-B Synthesis 2-Br (2.01g,4.63mmol,1.0 equiv.) is added to a dry three-necked flask equipped with magnetic stirring nitrogen is exchanged three times, then tetrahydrofuran (50m L) is added under nitrogen protection, after cooling the mixture to-78 ℃ n-butyllithium (2.89m L, 4.63mmol,1.0 equiv, 1.6 mol/L in hexane) is slowly added dropwise, stirring is carried out at that temperature for 1 hour, then the mixture is warmed to room temperature and 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane (0.94m L, 4.63mmol,1.0 equiv.) is added to the flask under nitrogen protection, after stirring for 12 hours, the reaction is monitored by thin layer chromatography until the reaction is complete, the resulting mixture is cooled to room temperature and quenched with saturated ammonium chloride solution, the mixture is extracted three times with dichloromethane, the combined organic sodium sulfate layers are washed with water, dried, the filtrate is filtered, the eluent is concentrated under reduced pressure, the filtrate is purified by thin layer chromatography, and the silica gel column is obtained (96 g: 96.88 g).

Synthesis of BTC-2: 2-B (1.72g,3.57mmol,1.2 eq), Br-CHO (722.2mg,2.97mmol,1.0 eq), tetrakis (triphenylphosphine) palladium (103.0mg,0.09mmol,0.03 eq) and potassium carbonate (1.03g,7.43mmol,2.5 eq) were added sequentially to a dry three-necked flask equipped with magnetic stirring, nitrogen was pumped three times, then toluene (36m L), ethanol (12m L) and water (12m L) were added under nitrogen, and the mixture was placed in an oil bath and heated to 90 ℃, monitored by thin layer chromatography until the reaction was complete, the reaction was stopped after 18 hours, the resulting mixture was cooled to room temperature and quenched with water, the mixture was extracted three times with dichloromethane, the combined organic layers were washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1:1.5) to give 676.8mg of a yellow solid in 44% yield.¹H NMR(500MHz,CDCl₃),1.48(s,18H),7.48–7.52(m,4H),7.80(dd,J＝6.5,1.9Hz,2H),8.01(d,J＝7.3Hz,1H),8.16(s,2H),8.26(dt,J＝8.5,2.2Hz,2H),8.37(d,J＝7.3Hz,1H),10.84(s,1H)。

Synthesis of BTN-2 BTC-2(518.2mg,1.00mmol,1.0 equiv.), malononitrile (198.4mg,3.00mmol,3.0 equiv.), sodium acetate (408.7mg,3.00mmol,3.0 equiv.), anhydrous sodium sulfate (853.1mg,6.01mmol,6.0 equiv.), and toluene (20m L) were sequentially added to a three-necked flask equipped with magnetic stirring, the mixture was put in an oil bath and stirred at 90 ℃ for reaction for 18 hours, then the reaction was monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, water was added to quench it, the combined organic layer was extracted three times with dichloromethane, the combined organic layer was washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and a sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1.5:1) to obtain 368.1mg of a brown solid in 65% yield.¹H NMR(500MHz,CDCl₃),1.48(s,18H),7.48–7.52(m,4H),7.82(dd,J＝6.6,1.9Hz,2H),8.03(d,J＝7.7Hz,1H),8.16(s,2H),8.28(dt,J＝8.6,2.2Hz,2H),8.86(d,J＝7.7Hz,1H),8.89(s,1H)。¹³C NMR(125MHz,CDCl₃),32.14,34.93,83.84,109.47,113.00,113.78,116.54,122.89,123.90,123.93,126.73,127.54,130.79,131.18,134.07,138.86,139.53,140.13,143.61,152.92,153.06,154.49。

Example 3: the synthesis route of the luminescent material BTN-3 is as follows:

synthesis of 3-Br 3, 6-diphenylcarbazole (3.33g,10.42mmol,1.0 equiv.), 1-bromo-4-iodobenzene (3.24g,11.46mmol,1.1 equiv.), cuprous iodide (39.7mg,0.21mmol,0.02 equiv.), and sodium tert-butoxide (2.00g,20.81mmol,2.0 equiv.) were sequentially added to a dry three-necked flask equipped with magnetic stirring, nitrogen was purged three times, then 1, 2-trans-cyclohexanediamine (0.13m L, 1.04mmol,0.1 equiv.) and 1, 4-dioxane (100m L) were added under nitrogen protection, the mixture was placed in an oil bath, and the reaction was stirred at 100 ℃ until the reaction was completed, the reaction was stopped after 48 hours, the resulting mixture was cooled to room temperature and quenched by adding water, the combined organic layer was extracted three times with dichloromethane, the anhydrous sodium sulfate was dried, the filtrate was filtered on a silica gel column, and the eluate was purified by vacuum chromatography (yield: 20.85 g).

3-B Synthesis [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (153.2mg,0.21mmol,0.03 equiv.) and potassium acetate (2.05g,20.93mmol,3.0 equiv.) are added sequentially to a dry three-necked flask equipped with magnetic stirring, nitrogen is purged three times, then dimethyl sulfoxide (60m L) is added under nitrogen protection, the mixture is placed in an oil bath, the reaction is stirred at 90 ℃ for 24 hours, the reaction is monitored by thin layer chromatography until the reaction is complete, the resulting mixture is cooled to room temperature and diluted with dichloromethane, the mixture is washed three times with brine, dichloromethane is extracted three times, the combined organic layers are dried with anhydrous sodium sulfate and filtered, the filtrate is concentrated under reduced pressure, and the silica gel is purified (column chromatography: petroleum ether/dichloromethane ═ 2:1) to obtain a white solid with a yield of 2.33g, 64%.

Synthesis of BTC-3: 3-B (1.87g,3.59mmol,1.2 equiv.), Br-CHO (727.5mg,2.99mmol,1.0 equiv.), tetrakis (triphenylphosphine) palladium (103.8mg,0.09mmol,0.03 equiv.), carbonic acidPotassium (1.03g,7.48mmol,2.5 eq) was added sequentially to a dry three-necked flask equipped with magnetic stirring nitrogen was purged three times, then toluene (36m L), ethanol (12m L) and water (12m L) were added under nitrogen protection and the mixture was placed in an oil bath and heated to 90 ℃ until the reaction was complete, the reaction was stopped after 24 hours, the resulting mixture was cooled to room temperature and quenched with water, the mixture was extracted three times with dichloromethane, the combined organic layers were washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure and the sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1:4) to give 918.0mg of an orange solid in 55% yield.¹H NMR(500MHz,CDCl₃),7.35–7.39(m,2H),7.49–7.52(m,4H),7.64(d,J＝8.5Hz,2H),7.72(dd,J＝8.5,1.8Hz,2H),7.74(d,J＝0.9Hz,2H),7.76(d,J＝1.2Hz,2H),7.86(dt,J＝8.5,2.3,2H),8.03(d,J＝7.2Hz,1H),8.31(dt,J＝9.1,2.3Hz,2H),8.39(d,J＝7.3Hz,1H),8.43(d,J＝1.4Hz,2H),10.85(s,1H)。¹³C NMR(125MHz,CDCl₃),110.42,119.13,124.49,125.98,126.78,126.89,127.09,127.38,127.47,128.99,131.34,132.64,134.23,135.40,139.07,139.35,140.57,141.88,154.03,189.07。

Synthesis of BTN-3 BTC-3(555.0mg,1.00mmol,1.0 equiv.), malononitrile (197.2mg,2.99mmol,3.0 equiv.), sodium acetate (406.3mg,2.99mmol,3.0 equiv.), anhydrous sodium sulfate (848.2g,5.97mmol,6.0 equiv.), and toluene (25m L) were sequentially added to a three-necked flask equipped with magnetic stirring, the mixture was put in an oil bath and stirred at 90 ℃ for reaction, the reaction was stopped after 24 hours by monitoring with thin layer chromatography, the resulting mixture was cooled to room temperature, quenched by addition of water, the mixture was extracted three times with dichloromethane, the combined organic layer was washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and a sample was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane ═ 1:4) to obtain 403.9mg of a red solid with a yield of 67%.¹H NMR(500MHz,CDCl₃),7.36–7.39(m,2H),7.49–7.52(m,4H),7.65(d,J＝8.6Hz,2H),7.72(dd,J＝8.6,1.8Hz,2H),7.74(d,J＝1.2Hz,2H),7.76(d,J＝1.4Hz,2H),7.88(dt,J＝8.5,2.2Hz,2H),8.05(d,J＝7.7Hz,1H),8.33(dt,J＝8.6,2.3Hz,2H),8.43(d,J＝1.6Hz,2H),8.87(dd,J＝7.6,0.8Hz,1H),8.90(s,1H)。

Example 4: the synthesis route of the luminescent material BTN-4 is as follows:

synthesis of 4-Br Phenoxazine (3.66g,19.98mmol,1.0 equiv.), 1-bromo-4-iodobenzene (6.22g,21.97mmol,1.1 equiv.), cuprous iodide (76.1mg,0.40mmol,0.02 equiv.), and sodium tert-butoxide (3.84g,39.95mmol,2.0 equiv.) were added sequentially to a dry three-necked flask equipped with magnetic stirring, nitrogen was evacuated three times, then 1, 2-trans-cyclohexanediamine (0.25m L, 2.00mmol,0.1 equiv.) and 1, 4-dioxane (80m L) were added under nitrogen protection, the mixture was placed in an oil bath and stirred at 90 ℃ for reaction, the reaction was monitored until completion with thin layer chromatography, stopped after 48 hours, the resulting mixture was cooled to room temperature, water was added and the mixture was quenched, extracted three times with dichloromethane, the anhydrous bound organic layer was washed with water, dried over sodium sulfate, filtered under reduced pressure, the silica gel column chromatography sample was concentrated, and the eluate was purified (2.41 g, 2.41 g of white solid).

Synthesis of 4-B4-Br (2.36g,6.98mmol,1.0 equiv.), Bipinol Borate (3.19g,12.56mmol,1.8 equiv), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (153.1mg,0.21mmol,0.03 equiv.) and potassium acetate (2.05g,20.94mmol,3.0 equiv.) were added in this order to a dry three-necked flask equipped with magnetic stirring, nitrogen was purged three times, then dimethyl sulfoxide (60m L) was added under nitrogen protection, the mixture was placed in an oil bath and stirred at 90 ℃ until the reaction was completed, the reaction was stopped after 24 hours, the resulting mixture was cooled to room temperature and diluted with dichloromethane, the mixture was washed three times with brine, extracted with dichloromethane three times, the combined organic layers were dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the silica gel was purified (column chromatography: 5: 1.45% as a white solid, yield 1.45 g.

Synthesis of BTC-4: mixing 4-B (1.04g,2.71mmol,1.2 equivalent),Br-CHO (548.4mg,2.26mmol,1.0 equivalent), tetrakis (triphenylphosphine) palladium (78.2mg,0.07mmol,0.03 equivalent), potassium carbonate (779.5mg,5.64mmol,2.5 equivalent) were added in sequence to a dry three-necked flask equipped with magnetic stirring, nitrogen was pumped three times, then toluene (30m L), ethanol (10m L) and water (10m L) were added under nitrogen protection, and after the mixture was heated to 90 ℃ in an oil bath for 24 hours, the reaction was monitored by thin layer chromatography until completion, the resulting mixture was cooled to room temperature and quenched with water, the mixture was extracted three times with dichloromethane, the combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (petroleum ether/dichloromethane ═ 1:3) to give 561.0mg of a deep red solid in 59% yield.¹H NMR(500MHz,CDCl₃),6.08(dd,J＝7.9,1.5Hz,2H),6.63(td,J＝7.3,1.8Hz,2H),6.68(td,J＝7.8,1.6Hz,2H),6.73(dd,J＝7.8,1.7Hz,2H),7.57(dt,J＝8.5,2.2Hz,2H),7.99(d,J＝7.3Hz,1H),8.25(dt,J＝8.5,2.3Hz,2H),10.84(s,1H)。¹³C NMR(125MHz,CDCl₃),113.50,115.68,121.76,123.39,126.83,127.56,131.43,132.32,134.10,136.55,139.15,140.35,144.07,153.89,189.01。

Synthesis of BTN-4 BTC-4(614.3mg,1.51mmol,1.0 equiv.), malononitrile (199.2mg,3.02mmol,3.0 equiv.), sodium acetate (410.4mg,3.02mmol,3.0 equiv.), anhydrous sodium sulfate (856.6mg,6.03mmol,6.0 equiv.), and toluene (20m L) were sequentially added to a three-necked flask equipped with magnetic stirring, the mixture was put in an oil bath and stirred at 90 ℃ for reaction for 24 hours, then monitored by thin layer chromatography until the reaction was completed, the resulting mixture was cooled to room temperature, quenched by addition of water, the mixture was extracted three times with dichloromethane, the combined organic layer was washed with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and a sample was purified by chromatography on a silica gel column (eluent: petroleum ether/dichloromethane ═ 1:3) to obtain 387.0mg of a dark green solid in a yield of 82%.¹HNMR(500MHz,CDCl₃),6.07(dd,J＝7.9,1.5Hz,2H),6.63(td,J＝7.4,1.7Hz,2H),6.69(td,J＝7.8,1.5Hz,2H),6.73(dd,J＝7.8,1.7Hz,2H),7.58(dt,J＝8.5,2.2Hz,2H),8.00(d,J＝7.7Hz,1H),8.27(dt,J＝8.5,2.3Hz,2H),8.84(dd,J＝7.7,0.8Hz,2H),8.89(s,1H)。¹³C NMR(125MHz,CDCl₃),84.30,112.89,113.54,113.66,115.79,121.86,123.25,123.44,127.89,130.66,131.53,132.34,134.08,136.04,139.16,140.88,144.13,152.85,152.98,154.41。

Electrochemical, photophysical testing, theoretical calculations, and device data elucidation

Cyclic Voltammetry (CV) and Differential Pulse Voltammetry (DPV) characterizations using a CH1760E electrochemical analyzer measurements of oxidation and reduction potentials were performed with 0.1 mol/L tetra-N-butyl ammonium hexafluorophosphate as the electrolyte and anhydrous N, N-dimethylformamide as the solvent, the solution was bubbled with nitrogen for 15min before testing, silver, platinum and glassy carbon as pseudo-reference electrodes, counter and working electrodes, respectively, at a scan rate of 300mV/s, and ferrocene ion pair (CP)₂Fe/Cp₂Fe⁺) And (5) making an internal standard. And measuring the oxidation-reduction potential by differential pulse voltammetry. Redox reversibility was measured by cyclic voltammetry. The process is considered reversible if the magnitudes of the peak anodic current and the peak cathodic current are equal at a scan speed of 100mV/s or less; if the magnitudes of the peak anode current and the peak cathode current are not equal, but the return sweep is not zero, then the process is considered to be quasi-reversible; otherwise the process is not reversible. Containing benzo [ c ]][1,2,5]The electrochemical properties and energy comparison of each energy level of the light-emitting material with the thiadiazole derivative structural unit are shown in the following table.

Table one: luminescent material containing benzo [ c ] [1,2,5] thiadiazole derivative structural unit has electrochemical property and energy comparison of individual energy level

Luminescent material	EOxidation by oxygen[V]	EReduction of[V]	HOMOa[eV]	LUMOb[eV]
					BTN-1	1.06	-0.58	-5.86	-4.22
BTN-2	1.08	-0.60	-5.88	-4.20
					BTN-3	1.27	-0.60	-6.07	-4.20
BTN-4	1.38	-0.68	-6.18	-4.12

Note:^aHOMO＝-(E_{oxidation by oxygen}+4.8)eV。^bLUMO＝-(E_{Reduction of}+4.8)eV。

FIGS. 1-2 are theoretical calculations of the luminescent material using the Titan software package in the gas phase using L ACVP and B3L YP functional the ground state (S) was optimized using Density Functional Theory (DFT)₀) As can be seen from FIG. 1, the lowest unoccupied orbitals (L UMO) of the luminescent materials BTC-1, BTC-2, BTC-3 and BTC-4 are all at the receptor benzo [ c ]][1,2,5]Thiadiazole-4-aldehyde moiety, as can be seen from FIG. 2, L UMO for BTN-1, BTN-2, BTN-3 and BTN-4 are all at receptor 2- (benzo [ c)][1,2,5]Thiadiazole-4-methylene) malononitrile moiety; the eight Highest Occupied Molecular Orbitals (HOMO) are all positioned at the carbazole and derivative or benzoxazine part of the donor, and all form a receptor-donor separation system, so that the charge transfer in excited-state molecules can be realized, and further radiation transition luminescence can be realized.

As shown in the table I, the reduction potentials of the luminescent materials BTN-1, BTN-2, BTN-3 and BTN-4 are close (-0.58 to-0.68V), the oxidation potentials are greatly different (1.06 to 1.38V), the BTN-1, BTN-2 and BTN-3 have similar L UMO orbital levels (-4.20eV to-4.22 eV), but the HOMO orbital levels are greatly different (-5.86eV to-6.07 eV), the result also obtains the support of Density Functional Theory (DFT) calculation (figure 2), the power supply capability of the donor is changed under the condition that the acceptor structure is kept unchanged, the three materials L UMO have quite similar orbital distributions but different HOMO orbital distributions, and the molecular orbital levels of the luminescent materials can be effectively adjusted by adjusting the molecular structures of the luminescent materials.

In addition, the absorption spectra were measured on an Agilent 8453 uv-vis spectrometer, all samples being toluene (chromatographic grade) dilute solutions (10)^-5-10^-6M) as shown in FIG. 3, FIGS. 4-7 are graphs of steady state emission spectrum test results using a Horiba Jobin Yvon Fluoro L og-3 spectrometer, where FIG. 7 is a graph of film sample tests, where the film samples are DEPEO films doped with 10 wt% of a luminescent material, the DEPEO structure is shown in the following formula:

the photophysical property data of the luminescent material containing the structural unit of the benzo [ c ] [1,2,5] thiadiazole derivative are shown in the following table II.

Table two: photophysical property of luminescent material containing benzo [ c ] [1,2,5] thiadiazole derivative structural unit

Luminescent material

BTC-1

BTC-2

BTC-3

BTC-4

BTN-1

BTN-2

BTN-3

Peak/nm

476

547

542

553

579

607

603

Color of light emission

Blue light

Green light

Green light

Green light

Yellow light

Orange light

Orange light

Quantum efficiency of solution (toluene)

69.5％

43.9％

26.1％

0.87％

42.3％

24.0％

24.4％

Film quantum efficiency (DPEPO)

28.7％

15.6％

15.9％

4.4％

26.3％

6.2％

2.3％

Note: peak refers to the strongest emission Peak of the emission spectrum of the luminescent material in toluene solution at room temperature.

As can be seen from FIGS. 3-6 and Table II, one of which: the luminescent color of the material is easy to adjust: the luminous color of the material molecule can be effectively adjusted by adjusting the acceptor unit or adjusting the structure of the donor under the condition of keeping the acceptor structure unchanged. The second step is as follows: the emission spectrum characteristics of the luminescent material in different solvents are consistent with the characteristics of intramolecular charge transfer, which indicates that the luminescent material is a thermally induced delayed fluorescent material. And thirdly: the material molecules can emit strong light, and the light emission can respectively reach 69.5 percent and 28.7 percent in a toluene solution and a DPEPO film at room temperature.

FIG. 8 is the electroluminescence spectrum of the luminescent material CBP or mCBP as the luminescent host doped with BTC-3 with different concentrations, and it can be seen from the graph that the luminescent material containing the structural unit of the benzo [ c ] [1,2,5] thiadiazole derivative of the present invention can emit light strongly.

Further, the organic luminescent material provided by the invention is applied to a luminescent layer of an organic electroluminescent device. In an organic light-emitting element, carriers are injected into a light-emitting material from both positive and negative electrodes, and the light-emitting material in an excited state is generated and emits light. The complex of the present invention represented by the general formula (1) can be used as a light-emitting material for an excellent organic light-emitting device such as an organic photoluminescent device or an organic electroluminescent device. The organic photoluminescent element has a structure in which at least a light-emitting layer is formed over a substrate. The organic electroluminescent element has a structure in which at least an anode, a cathode, and an organic layer between the anode and the cathode are formed. The organic layer may be composed of only the light-emitting layer, or may have 1 or more organic layers other than the light-emitting layer. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. Fig. 12 shows a schematic structure of a specific organic light-emitting element. In fig. 12, the left device includes 7 layers from bottom to top, which sequentially represent a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, where the light emitting layer is a mixed layer of a guest material doped with a host material.

The compound shown in the embodiment is used as an organic luminescent material applied to an O L ED device, and the device structure of the luminescent material CBP or mCBP used as a luminescent host under different concentrations of BTC-3 doping is shown as follows, wherein the device 1 comprises ITO/HATCN (10nm)/TAPC (65nm)/CBP, BTC-3 (x%, 20nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al, x 10%. device 2: ITO/HATCN (10nm)/TAPC (65 nm)/CBP: BTC-3 (x%, 20nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al, x ═ 20%. device 3: ITO/HATCN (10nm)/TAPC (65 nm)/mCBP: BTC-3 (x%, 20nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al, x 10%. device 4: ITO/HATCN (10nm)/TAPC (65 nm)/mCBP: BTC-3 (x%, 20nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al，x＝20％。

The device structure of the luminescent material mCBP as a luminescent host under the doping of the guest BTC-1, BTC-2 and BTC-3 is as follows: device 5: ITO/HATCN (10nm)/TAPC (40nm)/TCTA (10nm)/mCBP：BTC-1(x％,30nm)/PPT(40nm)/Li₂CO₃(1nm)/Al, x 10%. device 6: ITO/HATCN (10nm)/TAPC (40nm)/TCTA (10 nm)/mCBP: BTC-2 (x%, 30nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al, x 10%. device 7: ITO/HATCN (10nm)/TAPC (40nm)/TCTA (10 nm)/mCBP: BTC-3 (x%, 30nm)/PPT (40 nm)/L i₂CO₃(1nm)/Al, and x is 10%. The molecular structure of the materials used in the above devices is as follows:

taking the diagram in FIG. 12a as an example, in which ITO is a transparent anode, HAT-CN is a hole injection layer, TAPC is a hole transport layer, TCTA is an electron blocking layer, CBP is a host material, the compounds shown in examples 1-4 are guest materials, 10-20 wt.% are doping concentration, 30nm or 20nm is the thickness of a light emitting layer, PPT is an electron transport layer, L i₂CO₃Is an electron injection layer and Al is a cathode. The number in parentheses in nanometers (nm) is the thickness of the film.

The materials used to make the devices are subjected to a high vacuum (10) prior to use^-5-10^-6Torr) is heated and sublimated in gradient, Indium Tin Oxide (ITO) substrates used by the device are sequentially subjected to ultrasonic treatment in deionized water, acetone and isopropanol, an anode electrode is Indium Tin Oxide (ITO), and a cathode is formed by L i₂CO₃And Al. The device passes through the vacuum degree of less than 10^-7And vacuum thermal evaporation is carried out under the pressure of Torr. After all devices are prepared, the glass cover and the epoxy resin are packaged in a nitrogen glove box, and a moisture absorbent is added into the package.

FIG. 9 is a graph of device current density-voltage-luminous intensity for devices 1-4, FIGS. 10 and 11 are a graph of electroluminescence spectra and a graph of current density-voltage-luminous intensity for devices 5-7, respectively, and it can be seen from the characterization of the performance data for the devices in FIGS. 8, 9, 10 and 11 that the maximum luminous intensity of the luminescent material molecule-doped O L ED device developed in the present application can exceed 10000cd/m²Indicating that the material molecule can successfully work as O L ED luminescent material.

It should be noted that the structure is an example of an application of the light-emitting material of the present invention, and does not constitute a limitation of the specific O L ED device structure of the light-emitting material of the present invention, nor is the light-emitting material limited to the compounds shown in examples 1 to 4.

It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the invention, and that various changes in form and details may be made therein without departing from the spirit and scope of the invention in practice. For example, many of the substituent structures described herein may be substituted with other structures without departing from the spirit of the invention.

Claims (5)

1. An organic luminescent material containing a benzo [ c ] [1,2,5] thiadiazole derivative acceptor structural unit is characterized in that the structural formula is shown as a formula (I) or a formula (II):

in formula (I), the acceptor is benzo [ c ]][1,2,5]Thiadiazole-4-carboxaldehyde radical, R^a1Or R^b1Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, and the like, or combinations thereof.

m1 and n1 represent the number of substituents; wherein m1 is an integer of 0-2, and n1 is an integer of 0-4.

In formula (II), the acceptor is 2- (benzo [ c ]][1,2,5]Thiadiazole-4-methylene) malononitrile, R^a2Or R^b2Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, and the like, or combinations thereof.

m2 and n2 represent the number of substituents; wherein m2 is an integer of 0-2, and n2 is an integer of 0-4.

Donor D¹Or D²Each independently is one of the following structures:

wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And R¹²Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Wherein adjacent two substituents may be fused to form a ring, a halogen, a silicon group, a mono-or dialkylamino group, a mono-or diarylamino group, a cyano group, or a combination thereof.

o1, p1, q1, R1, s1, t1, u1, v1, w1, x1, y1 and z1 are each R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And R¹²The number of (2); o1, p1, q1, r1, s1, t1, u1, v1, w1, x1, y1 and z1 are integers from 0 to 4.

2. The organic light-emitting material according to claim 1, wherein: the organic luminescent material is a compound shown in formulas (III) and (IV):

wherein, in the formula (III), R^a3Or R^b3Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof.

m3 and n3 represent the number of substituents; wherein m3 is an integer of 0-2, and n3 is an integer of 0-4.

In the formula (IV), R^a4Or R^b4Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof.

m4 and n4 represent the number of substituents; wherein m4 is an integer of 0-2, and n4 is an integer of 0-4;

said donor D³Or D⁴Each independently is one of the following structures:

wherein R is^1'、R^2'、R^3'、R^4'、R^5'、R^6'、R^7'、R^8'、R^9'、R^10'、R^11'And R^12'Each independently is hydrogen or deuterium, C₁-C₂₄Alkyl of (C)₁-C₂₄Alkoxy group of (C)₃-C₂₄Cycloalkyl of, C₁-C₂₄Ether of (C)₁-C₂₄Heterocyclic group of (A), C₁-C₂₄Aryl of (C)₄-C₂₄Aryloxy, halogen, silicon, mono-or dialkylamino, mono-or diarylamino, cyano, or a combination thereof, wherein two adjacent substituents can be fused to form a ring;

o2, p2, q2, R2, s2, t2, u2, v2, w2, x2, y2 and z2 are each R^1'、R^2'、R^3'、R^4'、R^5'、R^6'、R^7'、R^8'、R^9'、R^10'、R^11'And R^12'The number of (2); o2, p2, q2, r2, s2, t2, u2, v2, w2, x2, y2 and z2 are integers from 0 to 4.

3. The organic light-emitting material according to claim 1, wherein: the organic luminescent material is one of the following materials:

4. the organic light-emitting material according to claim 1, wherein: the organic luminescent material is:

5. use of a luminescent material based on benzo [ c ] [1,2,5] thiadiazole-4-aldehyde groups and 2- (benzo [ c ] [1,2,5] thiadiazole-4-methylene) malononitrile acceptor building blocks according to any one of claims 1 to 5 in an organic electroluminescent device, characterized in that the organic material is used as a luminescent layer material.

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