An imidazopyrazine organic compound and its application

Abstract

The present invention relates to the technical field of organic electroluminescent materials, and in particular to an imidazopyrazine organic compound and its application. The structure of the imidazopyrazine organic compound is shown in the following structure:; R is selected from any one of substituted or unsubstituted C6-C24 aromatic hydrocarbons and substituted or unsubstituted C6-C24 heterocyclic aromatic hydrocarbons; the heteroatom in the heterocyclic aromatic hydrocarbon is selected from N, O, and S; wherein the substituted substituent is selected from deuterium and cyano. The imidazopyrazine organic compound is used as a light-emitting layer material of an organic electroluminescent device. The imidazopyrazine organic compound has high carrier transfer efficiency, suitable HOMO and LUMO energy level difference, strong structural rigidity and molecular thermal stability, which is conducive to achieving efficient blue light emission, and can effectively improve the photoelectric performance of OLED devices and the life of OLED devices, and can meet the requirements of panel manufacturing companies.

Description

Technical Field

[0001] The invention relates to an imidazopyrazine organic compound and application thereof, belonging to the technical field of organic electroluminescent materials. Background Art

[0002] OLED, also known as "organic light-emitting diode", is a technology that emits light through carrier injection and recombination, and has the characteristic of automatic light emission. OLED materials (organic light-emitting materials) are the core of its automatic light emission and the key core material of OLED panels. They directly determine the light-emitting characteristics of the panel and are one of the fields with the highest technical barriers. In recent years, display technology has changed rapidly. OLED has quickly occupied the market with its high efficiency, high response speed, excellent contrast and flexibility. Therefore, the research and development of organic light-emitting materials is crucial.

[0003] At present, red and green light emitting materials have been applied in mass production on organic electroluminescent devices, but the performance of blue light emitting materials is not satisfactory. Most of the blue light materials reported so far show CIE coordinates of (x≈0.15, y≈0.10), which do not meet the NTSC standard CIE (x=0.14, y=0.08). On the one hand, it is because blue light materials have a wide band gap, low molecular conjugation, and large energy level difference, and often face problems such as low luminous efficiency and concentration quenching; on the other hand, blue light emission requires higher excitation energy, and the stability of luminescent materials is poor at high energy, resulting in lower luminous efficiency.

[0004] Although blue light materials have many problems that hinder their development, they have advantages over red and green light materials, such as high photoelectric conversion efficiency, low energy consumption, and automatic energy transfer, which will greatly promote the future development of OLED. Therefore, seeking stable and efficient blue light materials has become a top priority in the research and development of new OLED devices. Summary of the invention

[0005] In view of the problems of low luminous efficiency, poor stability, low color purity and the like of existing blue light materials, the present invention provides an imidazopyrazine organic compound and its application. The imidazopyrazine organic compound has high carrier transfer efficiency, suitable HOMO and LUMO energy level difference, strong structural rigidity and molecular thermal stability, making it a good light-emitting layer material, which is conducive to achieving efficient blue light emission, and can effectively improve the photoelectric performance of OLED devices and the life of OLED devices through device structure optimization, and can meet the requirements of panel manufacturing companies.

[0006] The technical solution of the present invention to solve the above technical problem is as follows: an imidazopyrazine organic compound, the structure of the imidazopyrazine organic compound is shown in the following structure:

[0007] ;

[0008] The R is selected from any one of substituted or unsubstituted C6-C24 aromatic hydrocarbons and substituted or unsubstituted C6-C24 heterocyclic aromatic hydrocarbons; the heteroatom in the heterocyclic aromatic hydrocarbon is selected from N, O, and S; and the substituted substituent is selected from deuterium and cyano.

[0009] Further, the R is selected from any one of the following structures:

[0010] .

[0011] Specifically, the R is selected from any one of the following structures:

[0012] .

[0013] Furthermore, the imidazopyrazine organic compound is selected from the following structural formula:

[0014]

[0015]

[0016]

[0017] .

[0018] The invention also discloses an application of an imidazopyrazine organic compound, wherein the imidazopyrazine organic compound is applied to an organic electroluminescent device.

[0019] Furthermore, the organic layer of the organic electroluminescent device includes at least one of the imidazopyrazine organic compounds.

[0020] Furthermore, the imidazopyrazine organic compound is used as a light-emitting layer material of an organic electroluminescent device.

[0021] The imidazopyrazine organic compound is used as a blue light-emitting material in OLED lighting and OLED display panels. The blue light-emitting material is used alone or after being doped in one or more of red light-emitting materials, green light-emitting materials and blue light-emitting materials.

[0022] The beneficial effects of the present invention are:

[0023] The imidazopyrazine organic compound of the present invention has a parent structure of a high-rigidity condensed ring structure of nitrogen five-membered ring, six-membered ring and dibenzofuran ring, which has a strong electron-donating and electron-withdrawing effect and a steric hindrance effect, which is conducive to the blue light emission of the material. At the same time, its conjugation effect is conducive to reducing the energy of the system and improving the thermal stability of the material; the conjugation effect and the steric hindrance effect can improve the rigidity of the molecular structure and inhibit the non-radiative transition caused by the interaction between molecules, thereby improving the luminous efficiency of the material.

[0024] The OLED organic light-emitting device prepared from the imidazopyrazine organic compound of the present invention has significantly improved luminous efficiency and lifespan, and has good stability.

[0025] The imidazopyrazine organic compound of the present invention has great application value and commercial value in the application of organic light-emitting devices and has good application prospects. DETAILED DESCRIPTION

[0026] The specific implementation of the present invention is described in detail below. The present invention can be implemented in many other ways than those described herein, and those skilled in the art can make similar improvements without violating the connotation of the present invention, so the present invention is not limited by the specific embodiments disclosed.

[0027] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. The terms used are only for describing specific embodiments and are not intended to limit the present invention.

[0028] 1. Compound Preparation Examples

[0029] Synthesis of the parent compound (compound H):

[0030] ;

[0031] (1) Synthesis of Compound A:

[0032] 100mmol 3-fluoro-2-bromo-4-methylphenol, 250mmol K2CO3, 300g toluene and 80g purified water were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 60.0-70℃, and o-bromophenylboric acid / THF solution (100mmol o-fluorophenylboric acid dissolved in 60g THF) was added dropwise at a temperature control. THF), dropwise addition was completed, and the reaction was kept warm. After TLC tracking detection showed that there was no 3-fluoro-2-bromo-4-methylphenol remaining, the reaction system was allowed to stand for stratification, and the aqueous phase in the reaction system was separated. The temperature was then controlled at 30.0-40.0°C, and the organic phase was washed with purified water until neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 100g of toluene was used to elute the column each time, and the eluent was rinsed twice in total. After the elution was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, 16.5g of compound A was obtained by recrystallization with toluene, with a yield of 75.0%. Mass spectrum: 220.1.

[0033] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.38(s,1H),7.42–7.30(m,3H),7.23–7.13(m,2H), 6.72(d,J=7.5Hz,1H),2.27(d,J=1.0Hz,3H).

[0034] (2) Synthesis of compound B:

[0035] 100mmol compound A, 300mmol K2CO3, 200mmolCs2CO3, 250gDMF were added to the reaction bottle, stirring was started, nitrogen protection was applied, and then the temperature was raised to 130.0-140℃ for heat preservation and reaction. After TLC tracking and detection, no compound A remained, the temperature was lowered to 20.0-30.0℃, filtered, and the filter cake was eluted with 100g DMF. After elution, the filtrate was combined and the solvent was removed under negative pressure. After the solvent was removed, 200g toluene was used to heat the product, and then the temperature was controlled at 30.0-40.0℃. The organic phase was washed with purified water until neutral. After washing, the solvent was removed under negative pressure. After the solvent was removed, 15.6g compound B was recrystallized from toluene, with a yield of 78.0%. Mass spectrum: 200.1.

[0036] Hydrogen spectrum: 1HNMR(500MHz,Chloroform-d)δ7.96(dd,J=7.4,1.6 Hz,1H),7.55(dd,J=7.5,1.5 Hz, 1H),7.45(td,J=7.5,1.6Hz,1H),7.37(td,J=7.5,1.6Hz,1H),7.25(ddq,J=7.0,4.9,1.0Hz,1H),7.19(d,J=7.5Hz,1H),2.28(d,J=1.0Hz,3H).

[0037] (3) Synthesis of compound C:

[0038] 100mmol compound B, 20mmol BPO (dibenzoyl peroxide), 110mmol NBS (N-bromosuccinimide) and 250gCCl4 were added to the reaction bottle, stirred, protected by nitrogen, and then heated to 60.0-70.0℃, kept warm for reaction, and after TLC tracking detection, no compound B remained, then the temperature was controlled at 30.0-40.0℃, and the organic phase was washed with purified water until neutral, and after washing, the solvent was removed under negative pressure, and after the solvent was removed, 16.9g of compound C was recrystallized with dichloroethane, with a yield of 60.8%. Mass spectrum: 278.0.

[0039] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.00(dd,J=7.5,1.7Hz,1H), 7.56(dd,J=7.5,1.6Hz,1H),7.44(td,J=7.4,1.5Hz,1H),7.36(td,J=7.5,1 .5Hz,1H),7.30(dd,J=7.5,4.9Hz,1H),7.20(d,J=7.5Hz,1H),4.50(s,2H).

[0040] (4) Synthesis of Compound D:

[0041] Add 100mmol of compound C and 300g of THF into a reaction bottle, start stirring, protect with nitrogen, cool to 0-5.0℃, drop 150mmol of methylmagnesium chloride (in THF, 2.5mol / L), and after the addition is complete, control the temperature at 0-5.0℃ for 1h. Then control the temperature of the mixture at 0-5.0℃ and add it dropwise to a reaction bottle containing 95mmol of 2-bromomethoxypyrazine, 200g of THF, and 1mmol of Ni(dppf)Cl2. After TLC tracking shows that there is no 2-bromomethoxypyrazine remaining, slowly pour the reaction mixture into 100g of water and stir for hydrolysis for 10min. The product was extracted with 800g toluene. After the extraction, the organic phase was washed with purified water until it was neutral. After the washing, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a column at normal pressure. After the column was passed, 150g toluene was used to elute the column each time, for a total of 3 times. After the elution was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, it was recrystallized with toluene to obtain 17.6g of compound D, with a yield of 60%. Mass spectrum: 308.10.

[0042] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.22(d,J=7.5Hz,1H),8.02(d,J=7.5Hz,1H),7.97(dd, J=7.5,1.8Hz,1H),7.56(dd,J=7.5,1.6 Hz,1H),7.44(td,J=7.5,1.5Hz,1H),7.32(td,J=7.4,1.5Hz,1H),7.19(dd,J=7.5,4.8Hz,1H),7.16(d,J=7.5Hz,1H),4.23(s,2H),4.04(s,3H).

[0043] (5) Synthesis of Compound E:

[0044] 100mmol compound D, 120mmol (4-bromophenyl)methylamine, 150mmol concentrated hydrochloric acid, 50mmol FeCl3, 500g anisole were added to the reaction bottle, stirred, nitrogen protection, and then the temperature was controlled at 20.0-25.0℃, 200mmol TFA (trifluoroacetic acid) was added dropwise, and after the addition of the materials was completed, the temperature was raised to 125.0-130.0℃ and kept warm. After TLC tracking showed that there was no compound D left, the reaction temperature was lowered to 20.0-25.0℃, 100g water was slowly added, stirred and hydrolyzed for 10min, and after the hydrolysis was completed, 800g EA was used to extract the product. After the extraction, the aqueous phase was separated and the organic phase was washed with purified water until neutral. After the washing, the organic phase was dried by adding anhydrous sodium sulfate and passed through a silica gel column at normal pressure. After the column was passed, 200g EA was used to elute the column each time for a total of 3 times. After the eluent and the column liquid were combined, the solvent was removed under negative pressure and purified by silica gel column chromatography (PET: EA = 2:1) to obtain 36.5g of compound E with a yield of 75%. Mass spectrum: 487.03.

[0045] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.11(d,J=7.5 Hz,1H),8.02(dd,J=7.5,1.8Hz,1H), 7.90–7.84(m,2H),7.79–7.70(m,4H),7.57(dd,J=7.6,1.5 Hz,1H),7.44(td,J= 7.5,1.5Hz,1H),7.36(d,J=7.5Hz,1H),7.29(td,J=7.4,1.5Hz,1H),4.00(s,3H).

[0046] (6) Synthesis of Compound F:

[0047] 100 mmol of compound E and 1000 g of dichloroethane were added to the reaction bottle, stirred, protected by nitrogen, cooled to -5.0-0°C, and 210 mmol of BBr3 was added dropwise. After the addition was complete, the temperature was kept at -5.0-0°C. After TLC tracking detected that there was no compound E remaining, the reaction solution was slowly added to 200 g of water and stirred for hydrolysis for 10 min. After the hydrolysis was completed, the upper aqueous phase was separated, and the lower organic phase was washed with purified water until neutral. After the washing was completed, the organic phase was added with anhydrous sodium sulfate and dried, and passed through a silica gel column at normal pressure. After the column was passed, the column was eluted with 200 g of dichloroethane each time, and eluted 3 times in total. After the elution was completed, the eluent and the column liquid were combined to remove the solvent under negative pressure, and 39.0 g of compound F was obtained by recrystallization from dichloroethane, with a yield of 82%. Mass spectrum: 475.02.

[0048] Hydrogen spectrum: 1HNMR (500 MHz, Chloroform-d) δ10.89(s,1H),8.12(d,J=7.3Hz,1H),8.02(dd,J=7.5, 1.4Hz,1H),7.90–7.84(m,2H),7.81–7.75(m,2H),7.74(dd,J=7.6,4.9Hz,1H),7.57(dd,J=7.6, 1.5Hz,1H),7.44(td,J=7.6,1.6Hz,1H),7.36(d,J=7.5Hz,1H),7.33–7.26(m,1H),7.25(s,1H).

[0049] (7) Synthesis of Compound G:

[0050] 100mmol compound F, 300mmol K2CO3, 200mmolCs2CO3, 600g DMF were added to the reaction bottle, stirred, protected by nitrogen, and heated to 130.0-140.0℃ for insulation. After TLC tracking detection showed that there was no compound F left, the reaction temperature was lowered to 20.0-25.0℃ for filtration, and the filter cake was eluted with 200g DMF. After elution, the filtrate was combined and the solvent was removed under negative pressure. After the solvent removal was completed, 1000g toluene was added and the temperature was raised until the product was completely dissolved. Then, the organic phase was washed with hot water until it was neutral. After washing, the organic phase was dried by adding anhydrous sodium sulfate and passed through a silica gel column at normal pressure. After passing through the column, the column was eluted with 200g toluene each time. The column was eluted 3 times in total. After elution was completed, the eluent and the column liquid were combined and the solvent was removed under negative pressure. 36.2g compound F was obtained by recrystallization from toluene with a yield of 80%. Mass spectrum: 453.01.

[0051] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.07(d,J=7.5Hz,1H),7.99(dd,J=7.6,1.5Hz,1H), 7.90–7.84(m,2H),7.76–7.70(m,2H),7.67(d,J=7.5Hz,1H),7.55(dd,J=7.5,1.6Hz,1H), 7.43(td,J=7.5,1.5Hz,1H),7.34(td,J=7.5,1.5Hz,1H),7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0052] (8) Synthesis of the parent compound (Compound H):

[0053] 100mmol compound G, 105mmol biboric acid pinacol ester, 300mmol potassium acetate, 1mmol Pd (dppf) Cl2, 1mmol LiBr, 800g toluene were added to the reaction bottle, stirring was started, nitrogen protection was applied, the temperature was raised to 100.0-110.0℃, after TLC tracking detection showed that there was no compound G remaining, the temperature was controlled at 60.0-70.0℃, the organic phase was washed with purified water until neutral, after washing, anhydrous sodium sulfate was added to dry the organic phase, the dried organic phase was passed through a silica gel column at normal pressure, after passing through the column, 200g toluene was used to elute the column each time, for a total of 3 times, after the eluent and the column liquid were combined, and the solvent was removed under negative pressure, after the solvent was removed, 37.6g compound H was obtained by recrystallization with toluene, with a yield of 75%. Mass spectrum: 501.2.

[0054] Hydrogen spectrum: 1HNMR (500MHz, Chloroform-d) δ8.15 (d, J=7.6Hz, 1H), 8.04–7.99 (m, 1H), 7.73–7.67 (m, 3H), 7.59–7.54 (m, 1H),7.49–7.40(m,3H),7.33(td,J=7.6,1.7Hz,1H),7.26(d,J=7.6Hz,1H),7.11(d,J=7.6Hz,1H),1.24(s,12H).

[0055] Example 1

[0056] Preparation of compound 1:

[0057] ;

[0058] 105mmol bromobenzene, 250mmol potassium carbonate, 80g purified water and 400g toluene were added to a reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 75.0-80°C, and the compound H / toluene solution (100mmol compound H was dissolved in 400g toluene) was added dropwise under temperature control. After the addition was completed, the reaction was kept warm. After TLC tracking and detection showed that no compound H remained, the mixture was allowed to stand and stratify, the aqueous phase in the reaction system was separated, and the temperature was controlled at 60.0-70.0°C. The organic phase was washed with purified water until it was neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g toluene was used to elute the column each time, for a total of 3 times. After the elution was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, 31.6g of compound 1 was recrystallized from toluene, with a yield of 70.0%. Mass spectrum: 451.1.

[0059] Hydrogen spectrum: 1HNMR(500MHz,Chloroform-d)8.09(d,J=7.5Hz,1H),8.00(dd,J=7.4,1.5Hz,1H), 7.87-7.81(m,2H),7.68(d,J=7.5Hz,1H),7.65-7.59(m,4H),7.57(dd,J=7.4,1.5Hz,1H),7.50-7.41 (m,3H),7.41-7.35(m,1H),7.32(td,J=7.4,1.6Hz,1H),7.26(d,J=7.5Hz,1H),7.10(d,J=7.5Hz,1H).

[0060] Example 2

[0061] Preparation of compound 3:

[0062] ;

[0063] 105mmol of p-bromobenzonitrile, 250mmol of potassium carbonate, 80g of purified water and 400g of toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol of tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 75-80°C, and the compound H / toluene solution (100mmol of compound H was dissolved in 400g of toluene) was added dropwise under temperature control. After the addition was completed, the reaction was kept warm. After TLC tracking and detection of no residual compound H, the mixture was allowed to stand for stratification, the aqueous phase in the reaction system was separated, and the temperature was controlled at 60.0-70.0°C. The organic phase was washed with purified water until neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g of toluene was used to elute the column each time, for a total of 3 times. After the eluent was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, 34.3g of compound 3 was obtained by recrystallization from toluene with a yield of 72.0%. Mass spectrum: 476.1.

[0064] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.05–7.97(m,2H),7.89–7.82(m,4H),7.82–7.76(m, 2H),7.69(d,J=7.5Hz,1H),7.65–7.59(m,2H),7.57(dd,J=7.4,1.5Hz,1H),7.44(td,J=7.5, 1.5Hz,1H),7.32(td,J=7.4,1.6Hz,1H),7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0065] Example 3

[0066] Preparation of compound 7:

[0067] ;

[0068] 105mmol of m-bromobiphenyl, 250mmol of potassium carbonate, 80g of purified water and 400g of toluene were added to a reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol of tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 75-80°C, and a compound H / toluene solution (100mmol of compound H was dissolved in 400g of toluene) was added dropwise under temperature control. After the addition was completed, the reaction was kept warm. After TLC tracking and detection showed that no compound H remained, the mixture was allowed to stand and stratify, the aqueous phase in the reaction system was separated, and the temperature was controlled at 60.0-70.0°C. The organic phase was washed with purified water until it was neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200g of toluene was used to elute the column each time, for a total of 3 times. After the elution was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, 35.8g of compound 7 was recrystallized from toluene to obtain a yield of 68.0%. Mass spectrum: 527.2.

[0069] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.02–7.94(m,2H),7.89–7.83(m,2H),7.79(t,J=1.4 Hz,1H),7.69(d,J=7.6Hz,1H),7.65–7.47(m,8H),7.43(tq,J=8.5,1.7Hz,3H),7.39–7.31(m, 2H),7.26(d,J=7.6Hz,1H),7.11(d,J=7.6Hz,1H).

[0070] Example 4

[0071] Preparation of compound 9:

[0072] ;

[0073] 105mmol 4′-bromo-1,1′-biphenyl-2,2′,3,3′,4,5,5′,6,6′-d9 (CAS: 142475-00-1), 250mmol potassium carbonate, 80g purified water and 400g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol tetrakistriphenylphosphine palladium was added to the reaction flask, the temperature was raised to 75-80°C, and the compound H / toluene solution (100mmol compound H was dissolved in 400g toluene) was added dropwise at the temperature control, and the addition was completed, and the reaction was kept warm. After TLC tracking detected that no compound H remained, the mixture was allowed to stand for stratification, and the aqueous phase in the reaction system was separated. The temperature was then controlled at 60.0-70.0°C, and the organic phase was washed with purified water until neutral. After the washing was completed, anhydrous sodium sulfate was added to dry the organic phase. The dried organic phase was passed through a silica gel column at normal pressure. After the column was passed, 200 g of toluene was used to elute the column each time, for a total of 3 times. After the eluent was completed, the eluent and the column liquid were combined, and the solvent was removed under negative pressure. After the solvent was removed, 40.2 g of compound 9 was obtained by recrystallization with toluene, with a yield of 75.0%. Mass spectrum: 536.2.

[0074] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.00(dd,J=7.5,1.4Hz,1H),7.96(d,J=7.5Hz,1H), 7.86–7.80(m,2H),7.69(d,J=7.5Hz,1H),7.65–7.60(m,2H),7.63–7.54(m,1H),7.44 (td,J= 7.4,1.5Hz, 1H),7.34(td,J=7.5,1.5Hz,1H),7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0075] Example 5

[0076] Synthesis of compound 14:

[0077] ;

[0078] 105 mmol 1-bromodeuteronaphthalene, 250 mmol potassium carbonate, 80 g purified water, and 400 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, eluted 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 36.6g compound 14, yield 72%. Mass spectrum: 508.2.

[0079] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.05–7.99(m,2H),7.87–7.81(m,2H),7.69(d,J= 7.5Hz,1H), 7.59–7.51(m,3H),7.44(td,J=7.5,1.5Hz,1H),7.35(td,J=7.4,1.5Hz,1H),7.26(d,J= 7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0080] Example 6

[0081] Preparation of compound 17:

[0082] ;

[0083] 105mmol 9-bromodeuteranthracene, 250mmol potassium carbonate, 80g purified water, 400g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 42.6g compound 17, yield 76%. Mass spectrum: 560.2.

[0084] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.00(dd,J=7.5,1.4Hz,1H),7.96(d,J=7.5Hz,1H), 7.87.77(m,4H),7.69(d,J=7.5Hz,1H),7.57(dd,J=7.6,1.5Hz,1H),7.44(td,J=7.5, 1.5Hz,1H),7.34(td,J=7.4,1.6Hz,1H),7.26(d,J=7.5Hz,1H),7.10(d,J=7.5Hz,1H).

[0085] Example 7

[0086] Preparation of compound 19:

[0087] ;

[0088] 105mmol 3-bromoterphenyl, 250mmol potassium carbonate, 80g purified water, 400g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, eluted 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 42.8g compound 19, yield 71%. Mass spectrum: 603.2.

[0089] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.02–7.94(m,2H),7.88–7.82(m,2H),7.77(q,J= 1.2Hz,1H),7.69(d,J=7.5Hz,1H),7.66–7.55(m,9H),7.52(t,J=1.2Hz,3H),7.48–7.38 (m,3H),7.35(ddt,J=7.6,6.2,1.5Hz,2H),7.26(d,J=7.5Hz,1H),7.10(d,J=7.5Hz,1H).

[0090] Example 8

[0091] Preparation of compound 22:

[0092] ;

[0093] 105mmol 9-bromophenanthrene, 250mmol potassium carbonate, 80g purified water, 400g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, eluted 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 41.3g compound 22, yield 75%. Mass spectrum: 551.2.

[0094] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.19–8.12(m,2H) 8.06(dt,J=7.3,1.5 Hz,1H),8.02 –7.94(m,3H),7.89–7.83(m,2H),7.82–7.75(m,1H),7.69(d,J=7.6Hz,1H),7.62–7.48(m,7H),7.44 (td,J=7.3,1.5Hz,1H),7.35(td,J=7.3,1.5Hz,1H),7.26(d,J=7.6Hz,1H),7.11(d,J=7.6Hz,1H).

[0095] Example 9

[0096] Preparation of compound 23:

[0097] ;

[0098] 105mmol 1-bromopyrene, 250mmol potassium carbonate, 80g purified water, and 800g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, eluted 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 39.7g compound 23, yield 69%. Mass spectrum: 575.2.

[0099] Hydrogen spectrum: 1 HNMR (500MHz, Chloroform-d) δ8.18 –8.10(m,2H),8.06 –7.98(m,3H),7.98–7.94 (m,3H),7.87–7.81(m, 2H),7.75–7.71(m,1H),7.68(dd, J=10.0,7.6Hz,2H),7.60–7.51(m,4H), 7.44 (td,J=7.3,1.5Hz,1H),7.35(td,J=7.3,1.5Hz,1H),7.26(d,J=7.6Hz,1H),7.10(d,J=7.6Hz,1H).

[0100] Example 10

[0101] Preparation of compound 25:

[0102] ;

[0103] 105mmol 1,2,3,4,5,6,7,8-d8, 9-bromo-10-(phenyl-2,3,4,5,6-d5)-anthracene (CAS: 2377545-68-9), 250mmol potassium carbonate, 80g purified water, and 800g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate and 2mmol X-phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to dropwise add compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dropwise addition, keep warm for reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 45.6g compound 25, yield 71%. Mass spectrum: 642.3.

[0104] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.02–7.94(m,2H),7.87–7.81(m,2H),7.81–7.75(m, 2H),7.69(d,J=7.6 Hz,1H),7.57(dd,J= 7.5,1.6 Hz,1H),7.44 (td,J=7.6,1.6Hz,1H),7.33(td,J=7.4,1.5Hz,1H),7.26(d,J=7.6Hz,1H),7.10(d,J=7.3Hz,1H).

[0105] Embodiment 11

[0106] Preparation of compound 26:

[0107] ;

[0108] 105 mmol 1-bromobenzofuran, 250 mmol potassium carbonate, 80 g purified water, and 400 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 35.9g compound 26, yield 73%. Mass spectrum: 491.1.

[0109] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.05–7.99(m,2H),7.88(dd,J=7.5,1.5Hz,1H),7.88–7.82( m,2H),7.75(d,J=7.4Hz,1H),7.69(d,J=7.5Hz,1H),7.63–7.54(m,4H),7.48-7.40(m,2H), 7.33(td,J=7.4,1.6Hz,1H),7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H),6.93(dd,J=7.5,1.5Hz,1H).

[0110] Example 12

[0111] Preparation of compound 30:

[0112] ;

[0113] 105 mmol 4-bromobenzothiophene, 250 mmol potassium carbonate, 80 g purified water, and 400 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, eluted 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 38.5g compound 30, yield 76%. Mass spectrum: 507.1.

[0114] Hydrogen spectrum: 1 HNMR(500 MHz,Chloroform-d)δ8.05–7.99(m,2H),7.87–7.82(m,2H),7.81(d,J= 7.5Hz,1H), 7.73–7.67(m,2H),7.59–7.52(m,3H),7.51–7.36(m,4H),7.33(td,J=7.5,1.5Hz,1H), 7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0115] Example 13

[0116] Preparation of compound 34:

[0117] ;

[0118] 105 mmol 4-bromodibenzothiophene, 250 mmol potassium carbonate, 80 g purified water, and 600 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature-controlled dropwise addition of compound H / toluene solution (100mmol compound H dissolved in 400g toluene), heat-retained reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 41.8g compound 34, yield 75%. Mass spectrum: 557.1.

[0119] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.34(dd,J=7.5,1.6Hz,1H),8.11(dd,J=7.4, 1.7Hz,1H), 8.00(dd,J=7.4,1.5Hz,1H),7.96(d,J=7.5Hz,1H),7.86–7.80(m,2H),7.76(dd,J=7.5,1.6Hz,1H),7.69(d,J= 7.5Hz,1H),7.63–7.54(m, 3H),7.52–7.41(m,4H),7.35(tdd,J=7.6,6.2,1.6Hz,2H),7.26(d,J=7.5Hz,1H),7.10(d,J=7.5Hz,1H).

[0120] Embodiment 14

[0121] Preparation of compound 38:

[0122] ;

[0123] 105 mmol 1-bromodibenzothiophene, 250 mmol potassium carbonate, 80 g purified water, and 600 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature-controlled dropwise addition of compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dropwise addition, heat preservation and reaction, after TLC tracking detection without compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, for a total of 3 times, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 42.2g compound 38, yield 78%. Mass spectrum: 541.1.

[0124] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.01(ddd,J=16.4,7.5,1.5Hz,2H),7.96(d,J=7.5Hz, 1H),7.87–7.81(m,2H),7.69(d,J=7.5Hz,1H),7.58(dtd,J=7.2,5.7,1.6Hz,4H),7.49-7.41 (m,4H),7.41–7.36(m,1H),7.36(ddd,J=7.5,6.1,1.4Hz,2H),7.26(d,J=7.5Hz,1H),7.11(d,J=7.5Hz,1H).

[0125] Embodiment 15

[0126] Preparation of compound 45:

[0127] ;

[0128] 105mmol 4-bromo-9,9-dimethylfluorene, 250mmol potassium carbonate, 80g purified water, 500g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to dropwise add compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dropwise addition, keep warm for reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 45.9g compound 45, yield 81%. Mass spectrum: 567.2.

[0129] Hydrogen spectrum: 1 HNMR (500MHz, Chloroform-d) δ8.03–7.94 (m, 2H),7.91–7.85(m, 2H),7.69(d, J=7.6Hz, 1H), 7.64(dd, J=7.4,1.8 Hz,1H),7.60–7.31(m,10H),7.26(d, J=7.6Hz,1H), 7.10(d,J=7.6Hz,1H), 7.06 (dd, J=7.4,1.7Hz,1H),1.55(s,6H).

[0130] Example 16

[0131] Preparation of compound 47:

[0132] ;

[0133] 105 mmol 3-bromo-9-phenyl-9H-carbazole, 250 mmol potassium carbonate, 80 g purified water, and 800 g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1 mmol palladium acetate, 2 mmol X-phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), heated to 75.0-80.0℃, temperature controlled to dropwise add compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dropwise addition, keep warm for reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 51.1g compound 47, yield 83%. Mass spectrum: 616.2.

[0134] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.02–7.94(m,2H),7.94–7.89(m,1H),7.87–7.81(m,2H),7.69(d,J=7.5 Hz,1H),7.63–7.54(m,6H),7.54–7.41(m,5H),7.41–7.24(m,6H),7.10 (d,J=7.5 Hz,1H).

[0135] Embodiment 17

[0136] Preparation of compound 53:

[0137] ;

[0138] 1105mmol 4-bromo-9,9-diphenyl-9H-fluorene, 250mmol potassium carbonate, 80g purified water, and 1200g toluene were added to the reaction flask, stirring was started, nitrogen protection was applied, and then 1mmol palladium acetate, 2mmol X-phos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), heated to 75.0-80℃, temperature controlled to drip compound H / toluene solution (100mmol compound H dissolved in 400g toluene), after dripping, heat preservation reaction, after TLC tracking detection no compound H remaining, stand for stratification, separate the aqueous phase in the reaction system, then control the temperature to 60.0-70.0℃, wash the organic phase with purified water to neutrality, after washing, add anhydrous sodium sulfate to dry the organic phase, the dried organic phase is passed through a silica gel column at normal pressure, after passing through the column, rinse the column with 200g toluene each time, 3 times in total, after elution, combine the eluent and the column liquid, and remove the solvent under negative pressure, after removing the solvent, recrystallize with toluene to obtain 56.7g compound 53, yield 82%. Mass spectrum: 691.2.

[0139] Hydrogen spectrum: 1 HNMR(500MHz,Chloroform-d)δ8.02–7.94(m,2H),7.91–7.85(m,2H),7.69(d,J= 7.5Hz,1H),7.63(dd,J=7.5,1.5Hz,1H),7.57(dd,J=6.9,1.2Hz,1H),7.56(s,1H),7.58–7.52(m,2H),7.55–7.50(m,1H),7.49(t,J=7. 4Hz,1H),7.44(td,J=7.5,1.5Hz,1H),7.37–7.18(m,9H),7.16–7.08(m,5H),6.90(dd,J=7.4,1.5Hz,1H),6.80(dd,J=7.3,1.6Hz,1H).

[0140] The synthesis methods of compounds 1-54 are similar, except for the differences in raw materials. The FD-MS data of compounds 1-54 are shown in Table 1 below.

[0141] Table 1 FD-MS data of compounds 1 to 54

[0142]

[0143] 2. Preparation and application examples of OLED organic light-emitting devices

[0144] (1) Preparation of ITO (indium tin oxide) glass substrate: Place the ITO glass substrate with a coating thickness of 1400Å in distilled water for ultrasonic cleaning for 20 minutes, then use isopropanol, acetone, and methanol for ultrasonic cleaning for 15 minutes each, dry it, transfer it to a plasma cleaning machine, wash the above glass substrate for 5 minutes, and send it to the vapor deposition machine.

[0145] (2) Hole injection layer: On the prepared ITO glass substrate, a hole injection layer 2-TNATA was evaporated to 300Å;

[0146] (3) Hole transport layer: 200Å of compound a-NPD was evaporated;

[0147] (4) Light-emitting layer: PVPP is used as a 95% blue main material and a 5% doping material TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine) is mixed and evaporated to a thickness of 200Å;

[0148] (5) 300Å thick TPBi vapor deposition for the electron transport layer and electron injection layer, and 2000Å thick LiF vapor deposition for the cathode;

[0149] In the above process, the evaporation rate of organic matter is maintained at 1Å / sec, LiF is 0.2Å / sec, and A1 is 3~7Å / sec.

[0150] The application effects of the compounds of the present invention on OLED devices are described in detail below through application examples and application comparison examples.

[0151] The structures of the compounds involved in the application examples and comparative examples are shown below:

[0152] .

[0153] The obtained organic light-emitting device was tested by characterization equipment to evaluate the driving voltage, light-emitting life, light-emitting efficiency and light-emitting color of the light-emitting device; the test results of the light-emitting characteristics of the obtained OLED organic light-emitting device are shown in Table 2, which is the test results of the light-emitting characteristics of the OLED organic light-emitting device prepared by the imidazopyrazine organic compound prepared in the embodiment of the present invention and the comparative substance applied to the light-emitting layer. Among them, the following comparative examples and application example devices were tested under the same external environment (external ambient temperature (25.0℃), humidity (40.0%)) and the same brightness (1000nit). The test results are shown in Table 2.

[0154] Table 2 Light-emitting characteristics test data of organic light-emitting devices (1000nit)

[0155]

[0156] It can be seen from the data in Table 2 that the imidazopyrazine organic compounds of the present invention are selected as the main luminescent materials of OLED devices. Compared with existing luminescent materials, the present invention can reduce the driving voltage of OLED devices, improve the luminous efficiency, color purity and service life of the devices. Because the parent structure of the imidazopyrazine compounds is a high-rigidity condensed ring structure of nitrogen five-membered ring, six-membered ring and dibenzofuran ring arrangement, it has a strong electron supply and withdrawal effect and a steric hindrance effect, which is conducive to the material to achieve blue light emission. At the same time, its conjugation effect is conducive to reducing the energy of the system and improving the thermal stability of the material; the conjugation effect and the steric hindrance effect can improve the rigidity of the molecular structure and inhibit the non-radiative transition caused by intermolecular interactions, thereby improving the luminous efficiency of the material. In addition, it can be seen from Table 2 that the imidazopyrazine organic compounds of the present invention are basically in the blue CIE, and even reach the NTSC standard, achieving deep blue luminescence. In summary, the imidazopyrazine organic compounds of the present invention have great application value and commercial value in the application of OLED devices, and have good industrialization prospects.

[0157] The imidazopyrazine organic compound matrix of the present invention has a special hybrid structure of a dual hybrid system of Sp2 (N) and Sp3 (N), and has push-pull electron properties, which improves the charge migration efficiency and significantly improves the luminescence efficiency of the material; in addition, the conjugation effect and steric hindrance effect of the matrix structure can improve the rigidity of the molecular structure, inhibit the non-radiative transition caused by intermolecular interactions, reduce energy consumption, and enable it to have a suitable HOMO and LUMO energy level difference, which is beneficial for the material to achieve blue light emission.

[0158] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0159] For those skilled in the art, several modifications and improvements may be made without departing from the concept of the present invention, all of which belong to the protection scope of the present invention. The protection scope of the present invention shall be based on the attached claims.

Claims

1. An imidazopyrazine organic compound, characterized in that: The imidazopyrazine organic compound is selected from the following structural formula: 。 2. A use of an imidazopyrazine organic compound according to claim 1, characterized in that: The imidazopyrazine organic compound is used as a light-emitting layer material of an organic electroluminescent device.

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