WO2019061796A1 - Organic compound with triazine and quinoxaline as core and application thereof in oled - Google Patents

Abstract

The present invention relates to an organic compound with triazine and quinoxaline as a core and application thereof in an OLED device. The compound of the present invention is high in glass transition temperature and molecular thermal stability, has low absorption and a high refractive index in the field of visible light, and can effectively improve the light extraction efficiency of the OLED device after being applied to a CPL layer of the OLED device. The compound of the present invention also has a deep HOMO energy level and a high electronic mobility, can be taken as a hole blocking/electron transport layer material of the OLED device, and can effectively block holes or energy from being transmitted to one side of an electron layer from a light emitting layer, so that the recombination efficiency of the holes and electrons on the light emitting layer is improved, the light emitting efficiency of the OLED device is improved, and the service life is prolonged.

Description

Organic compound with triazine and quinoxaline as its core and its application in OLED Technical field

The invention relates to the field of semiconductor technology, in particular to an organic compound with triazine and benzopyrazine as its core and its application to OLED.

Background technique

Organic Light Emission Diodes (OLED) device technology can be used to manufacture new display products, as well as to create new lighting products, and is expected to replace existing liquid crystal display and fluorescent lighting, and has broad application prospects. The OLED light-emitting device is a sandwich-like structure, including an electrode material film layer and an organic functional material sandwiched between different electrode film layers, and various functional materials are superposed on each other according to the purpose to form an OLED light-emitting device. The OLED light-emitting device functions as a current device. When a voltage is applied to the electrodes at both ends thereof and the positive and negative charges in the organic layer functional material film layer are applied by the electric field, the positive and negative charges are further recombined in the light-emitting layer, that is, the OLED electroluminescence is generated.

At present, OLED display technology has been applied in the fields of smart phones, tablet computers, etc., and will further expand to large-size applications such as television. However, due to the huge gap between the external quantum efficiency and the internal quantum efficiency of OLED, the development of OLED is greatly restricted. Therefore, how to improve the light extraction efficiency of OLED has become a research hotspot. Total reflection occurs at the interface between the ITO film and the glass substrate and at the interface between the glass substrate and the air, and the light emitted to the external space of the OLED device accounts for about 20% of the total amount of the organic material film EL, and the rest is about 80% of the light. Mainly guided in the form of guided waves in organic material films, ITO films and glass substrates. It can be seen that the light-emitting efficiency of conventional OLED devices is low (about 20%), which seriously restricts the development and application of OLEDs. How to reduce the total reflection effect in OLED devices and increase the ratio of light coupling to the forward space of the device (light extraction efficiency) has attracted widespread attention.

At present, an important method to achieve an increase in the external quantum efficiency of OLEDs is to form structures such as wrinkles, photonic crystals, microlens arrays (MLAs), and surface covering layers on the light-emitting surface of the substrate. The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated in manufacturing process, and the process of using the surface coating layer is simple, and the luminous efficiency is improved by more than 30%, which is particularly concerned. According to the optical principle, when light is transmitted through a substance having a refractive index of n _{1 to} a substance having a refractive index of n ₂ (n ₁ > n ₂ ), the refractive index can be incident only within an angle of arcsin (n ₂ /n ₁ ). In the case of n ₂ , the absorption rate B can be calculated by the following formula:

Let n ₁ =n _{generally OLED organic material} = 1.70, n ₂ = n _glass = 1.46, then 2B = 0.49. Assuming that all of the outwardly propagating light is reflected by the metal electrode, only 51% of the light energy is waveguided by the high refractive index organic film and the ITO layer, and the transmittance of light from the glass substrate to the air can also be calculated. Therefore, when light emitted from the organic layer is emitted from the outside of the device, only about 17% of the light is visible. Therefore, in view of the current low efficiency of light extraction of OLED devices, it is necessary to add a layer of CPL, that is, a light extraction material, to the device structure. According to the principle of optical absorption and refraction, the refractive index of the surface coating material should be as high as possible. At present, research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, it is not only necessary to innovate from the structure and fabrication process of OLED devices, but also to continuously research and innovate OLED photoelectric functional materials, and to create higher performance OLED functional materials.

Summary of the invention

In view of the above problems in the prior art, the Applicant provides an organic compound centered on triazine and quinoxaline and its use in an organic electroluminescent device. The compound of the invention contains a triazine and a quinoxaline structure, has a high glass transition temperature and molecular thermal stability, has low absorption in the visible light field, and has a high refractive index, and can effectively improve the OLED after being applied to the CPL layer of the OLED device. The light extraction efficiency of the device; and because the triazine and quinoxaline have deep HOMO levels, a wide band gap (Eg) level, can be used as a hole blocking/electron transport layer material for OLED devices, blocking holes from luminescence The layer is transferred to the side of the electron layer to improve the recombination of holes and electrons in the light-emitting layer, thereby improving the luminous efficiency and the service life of the OLED device.

The technical solution of the present invention is as follows:

An organic compound having a triazine and a quinoxaline as a core, and the structure of the organic compound is as shown in the formula (1):

In the formula (1), Ar ₁ , Ar ₂ and Ar ₃ are each independently represented by a single bond, a substituted or unsubstituted C _6-60 arylene group, a substituted or unsubstituted 5 having one or more hetero atoms. a 60-membered heteroarylene; the hetero atom is nitrogen, oxygen or sulfur;

Ar ₁ , Ar ₂ , and Ar ₃ may be the same or different;

In the formula (1), R _{1 is} represented by a hydrogen atom; a C _1-10 linear or branched alkyl group; a halogen atom, a ruthenium atom, a ruthenium atom or a ruthenium atom substituted or unsubstituted pyridyl group; a compound of the formula (3); or the formula (4);

In the general formula (2), each X is independently represented as N or C, and at least one X is N;

In the formula (3), each Y is independently represented by N or C, and at least one Y is N; in the formula (4), R ₄ and R ₅ are each independently represented as a substituted or unsubstituted C _{6 a -60} aryl group, a substituted or unsubstituted 5- to 60-membered heteroaryl group containing one or more hetero atoms; the hetero atom is nitrogen, oxygen or sulfur; and R ₄ and R ₅ may be the same or different; In 1), R ₂ and R ₃ are each independently represented by the formula (5) or the formula (6);

Wherein R ₆ , R ₇ and R ₈ are each independently represented by a substituted or unsubstituted C _6-60 aryl group, a substituted or unsubstituted 5- to 60-membered heteroaryl group containing one or more hetero atoms; The hetero atom is nitrogen, oxygen or sulfur.

Preferably, the structure of the organic compound is as shown in any one of the formulae (I) to (VI):

Wherein R ₁ to R ₃ have the meanings as defined above.

Preferably, the structure of the compound is as shown in any one of the formulae (I) to (IV):

Wherein R ₁ , R ₆ -R ₈ have the meanings as defined above.

Preferably, the Ar ₁ , Ar ₂ , and Ar ₃ are each independently represented by a single bond, a C _1-10 linear or branched alkyl group, a halogen atom, a halogen atom, a germanium atom, or a germanium atom, substituted or unsubstituted. a phenylene group; a naphthylene group; a bisphenylene group; a subtriphenyl group; a furylene group; a pyridylene group; or a carbazolyl group; R ₄ , R ₅ , R ₆ , R ₇ , R _{8 is} independently represented by a C _1-10 linear or branched alkyl group; a halogen atom, a halogen atom, a halogen atom, or a halogen substituted or unsubstituted phenyl group; a diphenyl group; a terphenyl group; a furyl group; One of a pyridyl group; or a carbazolyl group.

Preferably, R ₁ in the formula (1) can be independently represented as:

One of them. Preferably, the specific structural formula of the organic compound is:

Any of them.

The Applicant also provides a method for preparing the organic compound, and the reaction equation occurring during the preparation is:

First step: when Ar ₁ or R ₁ and the triazine group are bonded by a CN bond,

The specific reaction process is as follows: the raw material 2,4,6-trichloro-1,3,5-triazine and R ₁ -H or R1-Ar ₁ -H are weighed and dissolved in toluene; then Pd ₂ (dba) _{3 is added.} , tri-tert-butylphosphine, sodium tert-butoxide; under a inert atmosphere, the mixed solution of the above reactants is reacted at a reaction temperature of 95 to 110 ° C for 10 to 24 hours, cooled and filtered, and the filtrate is steamed and passed through silica gel. Column, obtaining intermediate I;

The molar ratio of the 2,4,6-trichloro-1,3,5-triazine to R ₁ -H or R1-Ar ₁ -H is 1:1.0 to 1.5, and Pd ₂ (dba) ₃ and 2, The molar ratio of 4,6-trichloro-1,3,5-triazine is 0.006 to 0.02:1, and the molar ratio of tri-tert-butylphosphine to 2,4,6-trichloro-1,3,5-triazine The ratio of 0.006 to 0.02:1, the molar ratio of sodium t-butoxide to 2,4,6-trichloro-1,3,5-triazine is 2.0 to 3.0:1;

When Ar ₁ or R ₁ and a triazine group are bonded by a CC bond,

Under nitrogen atmosphere, weigh 2,4,6-trichloro-1,3,5-triazine in N,N-dimethylformamide, DMF, and then

And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 5 to 15 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, the residue obtained is purified by silica gel column to obtain compound intermediate I;

The 2,4,6-trichloro-1,3,5-triazine and

The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to 2,4,6-trichloro-1,3,5-triazine is 0.001-0.02:1, K ₃ PO ₄ and 2, The molar ratio of 4,6-trichloro-1,3,5-triazine is 1.0 to 2.0:1, and the ratio of 2,4,6-trichloro-1,3,5-triazine to DMF is 1 g: 10 to 20 ml;

The second step:

The specific reaction process is: under the nitrogen atmosphere, the intermediate I is weighed and dissolved in N, N-dimethylformamide, that is, DMF, and then

And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 10 to 24 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, the residue obtained is purified by silica gel column to obtain compound intermediate II;

The intermediate I and

The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to intermediate I is 0.001-0.02:1, and the molar ratio of K ₃ PO ₄ to intermediate I is 1.0-2.0:1, intermediate I The ratio of use to DMF is 1g: 10-20ml;

third step:

The specific reaction process is: under the nitrogen atmosphere, the intermediate II is weighed and dissolved in N, N-dimethylformamide, that is, DMF, and then

And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 10 to 24 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, and purifying the residue by silica gel column to obtain the target compound;

The intermediate II and

The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to intermediate II is 0.001-0.02:1, the molar ratio of K ₃ PO ₄ to intermediate II is 1.0-2.0:1, intermediate II and The dosage ratio of DMF is 1 g: 15 to 30 ml.

The Applicant also provides an application of an organic compound based on triazine and quinoxaline for the preparation of an organic electroluminescent device. The Applicant also provides an illumination or display element comprising the organic electroluminescent device.

The Applicant also provides an organic electroluminescent device comprising at least one functional layer comprising an organic compound centered on triazine and quinoxaline. The Applicant also provides an organic electroluminescent device comprising a hole blocking layer/electron transport layer comprising an organic compound centered on triazine and quinoxaline. The Applicant also provides an organic electroluminescent device comprising a CPL layer comprising an organic compound centered on triazine and quinoxaline. The beneficial technical effects of the present invention are:

The structure of the organic compound of the invention contains two rigid groups of triazine and quinoxaline, which improves the structural stability of the material; the molecular weight of the material of the invention is between 700 and 850, and the space structure, triazine 3 and 5 For the strong electronic quinoxaline group, the one position is separated from the other groups to prevent the group from rotating freely, so that the material has a higher density and a higher refractive index is obtained; at the same time, the materials of the present invention are very High Tg temperature; the evaporation temperature of 700-850 molecular weight materials under vacuum is generally less than 350 ° C, which not only ensures that the material does not decompose for a long time in mass production, but also reduces the thermal radiation due to evaporation temperature. The effect of deformation on the vapor deposited MASK.

The material of the present invention is applied to the CPL layer in an OLED device, does not participate in electron and hole transport of the device, but has very high requirements for thermal stability of the material, film crystallinity, and light transmission (high refractive index). As analyzed above, triazine and benzopyrazine are rigid groups, which improve the stability of the material; high Tg temperature ensures that the material does not crystallize in the film state; low evaporation temperature is the material that can be used for mass production. The premise; high refractive index is the most important factor that can be applied to the CPL layer.

The material of the invention has a deep HOMO energy level and high electron mobility, and can effectively block holes or energy from being transmitted from the light-emitting layer to the electron layer side, thereby improving the recombination efficiency of holes and electrons in the light-emitting layer, thereby improving the OLED. The luminous efficiency and lifetime of the device. The invention can effectively improve the light extraction efficiency of the OLED device after being applied to the CPL layer of the OLED device. In summary, the compounds of the present invention have good application effects and industrialization prospects in OLED light-emitting devices.

DRAWINGS

1 is a schematic structural view of an OLED device according to the present invention; wherein, 1, an OLED device substrate, 2, an anode layer, 3, a hole injection layer, 4, a hole transport layer, 5, a light-emitting layer, 6 , hole blocking layer / electron transport layer, 7, electron injection layer, 8, cathode layer, 9, CPL layer.

2 is a refractive index test chart of compound 46.

Figure 3 is a comparison of the film acceleration experiments of Compound 24 and the known material CBP.

Figure 4 is a graph showing the efficiency of the device measured at different temperatures.

Detailed ways

Example 1: Synthesis of Intermediate I: When Ar ₁ or R ₁ and a triazine group are bonded by a CC bond,

Under nitrogen atmosphere, weigh 2,4,6-trichloro-1,3,5-triazine in DMF and then

And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120-150 ° C for 5-15 hours; after the reaction is finished, cooling is added water, the mixture is filtered and dried under vacuum. Drying in a box, the residue obtained is purified by silica gel column to obtain compound intermediate I;

The 2,4,6-trichloro-1,3,5-triazine and

The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to 2,4,6-trichloro-1,3,5-triazine is 0.001-0.02:1, K ₃ PO ₄ and 2, The molar ratio of 4,6-trichloro-1,3,5-triazine is 1.0 to 2.0:1, and the ratio of 2,4,6-trichloro-1,3,5-triazine to DMF is 1 g: 10 to 20 ml;

Take the synthesis of intermediate A1 as an example:

(1) In a 250 mL three-necked flask, nitrogen gas was introduced, and 0.02 mol of 2-bromonaphthalene was added and dissolved in 100 ml of tetrahydrofuran (THF), and then 0.024 mol of bis(pinacolyl)diboron, 0.0002 mol (1,1') was added. - bis(diphenylphosphino)ferrocene)dichloropalladium (II) and 0.05 mol of potassium acetate are added, the mixture is stirred, and the mixed solution of the above reactants is heated under reflux at a reaction temperature of 80 ° C for 5 hours; Cool and add 100 ml of water and filter the mixture and dry in a vacuum oven. The obtained residue was separated and purified on a silica gel column to obtain 2-naphthaleneboronic acid pinacol ester; HPLC purity: 99.8%, yield: 87.8%.

Elemental analysis structure (molecular formula C ₁₆ H ₁₉ BO ₂ ): Theory C, 75.62; H, 7.54; B, 4.25; O, 12.59; Tests: C, 75.61; H, 7.55; B, 4.26; O, 12.58. ESI-MS (m/z) (M ⁺ ): Found: 254.

(2) In a 250 mL three-necked flask, nitrogen gas was introduced, and 0.02 mol of 2,4,6-trichloro-1,3,5-triazine, 150 ml of DMF, 0.03 mol of 2-naphthylboronic acid pinacol ester, 0.0002 was added. Palladium acetate was stirred, then added with 0.02 mol of K ₃ PO ₄ aqueous solution, heated to 130 ° C, refluxed for 10 hours, and the plate was sampled and the reaction was completed. The mixture was cooled with EtOAc (EtOAc) (EtOAc).

Elemental analysis structure (Molecular formula C ₁₃ H ₇ Cl ₂ N ₃ ): Theory C, 56.55; H, 2.56; Cl, 25.68; N, 15.22; Tests: C, 56.56; H, 2.58; Cl, 25.65; 15.21. ESI-MS (m/z) (M ⁺ ): calcd.

The intermediate I was prepared by the synthesis method of the intermediate A1, and the specific structure is shown in Table 1.

Table 1

When Ar ₁ or R ₁ and a triazine group are bonded by a CN bond,

The specific reaction process is as follows: the raw material 2,4,6-trichloro-1,3,5-triazine and R ₁ -H or R ₁ -Ar ₁ -H are weighed and dissolved in toluene; then Pd ₂ (dba) is added. _3. Tri-tert-butylphosphine and sodium tert-butoxide; reacting the mixed solution of the above reactants at a reaction temperature of 95 to 110 ° C for 10 to 24 hours under an inert atmosphere, cooling and filtering the reaction solution, and the filtrate is steamed. Silica gel column to obtain intermediate I;

The molar ratio of the 2,4,6-trichloro-1,3,5-triazine to R ₁ -H or R ₁ -Ar ₁ -H is 1:1.0 to 1.5, and Pd ₂ (dba) ₃ and 2 , the molar ratio of 4,6-trichloro-1,3,5-triazine is 0.006-0.02:1, tri-tert-butylphosphine and 2,4,6-trichloro-1,3,5-triazine a molar ratio of 0.006 to 0.02:1, a molar ratio of sodium t-butoxide to 2,4,6-trichloro-1,3,5-triazine of 2.0 to 3.0:1;

Take the synthesis of intermediate A14 as an example:

A 250 ml three-necked flask was charged with 0.01 mol of 2,4,6-trichloro-1,3,5-triazine, 0.015 mol of diphenylamine, 0.03 mol of sodium t-butoxide, 1 × 10 ^- under a nitrogen atmosphere. ⁴ mol Pd ₂ (dba) ₃ , 1 × 10 ^-4 mol tri-tert-butylphosphine, 150 ml of toluene, heated under reflux for 15 hours, sampling the plate, the reaction is complete; naturally cooled, filtered, the filtrate is steamed, passed through a silica gel column, Intermediate A14, HPLC purity 99.1%, yield 75.2%.

Elemental analysis structure (Molecular formula C ₁₅ H ₁₀ Cl ₂ N ₄ ): Theory C, 56.80; H, 3.18; Cl, 22.35; N, 17.66; Test: C, 56.81; H, 3.15; Cl, 22.37; 17.61. ESI-MS (m/z) (M ⁺ ): Theory: 317.17.

Intermediate I was prepared by the synthesis of Intermediate A17, and the specific structure is shown in Table 2.

Table 2

Example 2: Intermediate

Synthesis

When R ₂ or R _{3 is} represented by the structure of the formula (5),

(1) Under a nitrogen atmosphere, weigh 2,3-dibromoquinoxaline in tetrahydrofuran, add R ₆ -B(OH) ₂ and tetrakis(triphenylphosphine)palladium, stir the mixture, and add saturation. The aqueous solution of potassium carbonate is heated and refluxed at a reaction temperature of 70-90 ° C for 10-20 hours. After the reaction is completed, the mixture is cooled, and the mixture is extracted with dichloromethane. And concentrated under reduced pressure, the concentrated solid was purified by silica gel column to obtain compound intermediate M;

(2) Under the nitrogen atmosphere, the intermediate M is weighed and dissolved in N,N-dimethylformamide (DMF), and then bis (pinacol) diboron, (1,1'-bis(diphenyl) a phosphine) ferrocene) dichloropalladium (II) and potassium acetate are added, the mixture is stirred, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 120-150 ° C for 5-10 hours; after the reaction is completed, it is cooled, and The mixture was filtered and dried in a vacuum oven. The obtained residue is separated and purified on a silica gel column to obtain a compound intermediate II-1;

When R ₂ or R _{3 is} represented by the structure of the formula (6),

(1) Under a nitrogen atmosphere, weigh 2,3,6-tribromoquinoxaline in tetrahydrofuran, add R ₇ -B(OH) ₂ and tetrakis(triphenylphosphine)palladium, stir the mixture, and then A saturated aqueous solution of potassium carbonate is added, and the mixed solution of the above-mentioned reactants is heated and refluxed at a reaction temperature of 70 to 90 ° C for 10 to 20 hours. After the reaction is completed, the mixture is cooled, and the mixture is extracted with dichloromethane. Treated, and concentrated under reduced pressure, the concentrated solid was purified by silica gel column to obtain compound intermediate O;

(2) Under a nitrogen atmosphere, the intermediate O is weighed and dissolved in tetrahydrofuran, and then R ₈ -B(OH) ₂ and tetrakis(triphenylphosphine)palladium are added, the mixture is stirred, and then a saturated aqueous solution of potassium carbonate is added thereto. The mixed solution of the reactants is heated and refluxed at a reaction temperature of 70-90 ° C for 10-20 hours. After the reaction is completed, the mixture is cooled, the mixture is extracted with dichloromethane, and the extract is dried over anhydrous sodium sulfate and evaporated. , the concentrated solid is purified through a silica gel column to obtain a compound intermediate P;

(3) Under the nitrogen atmosphere, the intermediate P is weighed and dissolved in N,N-dimethylformamide (DMF), and then bis (pinacol) diboron, (1,1'-bis(diphenyl) a phosphine) ferrocene) dichloropalladium (II) and potassium acetate are added, the mixture is stirred, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 120-150 ° C for 5-10 hours; after the reaction is completed, it is cooled, and The mixture was filtered and dried in a vacuum oven. The obtained residue is separated and purified on a silica gel column to obtain a compound intermediate II-2;

Intermediate

Synthesis

(1) Under the nitrogen atmosphere, the intermediate M or the intermediate P is weighed and dissolved in tetrahydrofuran, then Br-Ar ₂ -B(OH) ₂ and tetrakis(triphenylphosphine)palladium are added, the mixture is stirred, and then saturated. The aqueous solution of potassium carbonate is heated and refluxed at a reaction temperature of 70-90 ° C for 10-20 hours. After the reaction is completed, the mixture is cooled, and the mixture is extracted with dichloromethane. And concentrated under reduced pressure, the concentrated solid was purified by silica gel column to obtain compound intermediate N or intermediate Q;

(2) Under the nitrogen atmosphere, the intermediate N or the intermediate Q is weighed and dissolved in N,N-dimethylformamide (DMF), and then the bis (pinacol) diboron, (1,1'- Bis(diphenylphosphino)ferrocene)dichloropalladium(II) and potassium acetate are added, the mixture is stirred, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 120-150 ° C for 5-10 hours; Cool, and filter the mixture and dry in a vacuum oven. The obtained residue is separated and purified on a silica gel column to obtain compound intermediate II-3 or intermediate II-4;

Taking the synthesis of intermediate B5 as an example

(1) In a 250 mL three-necked flask, nitrogen gas was introduced, 0.04 mol of 2,3,6-tribromoquinoxaline, 100 ml of THF, 0.05 mol of phenylboronic acid, 0.0004 mol of tetrakis(triphenylphosphine)palladium, and stirred. Then, 0.06 mol of an aqueous K ₂ CO ₃ solution (2 M) was added, and the mixture was heated to 80 ° C, refluxed for 10 hours, and the plate was sampled, and the reaction was completed. The mixture was cooled with EtOAc (EtOAc) (EtOAc). Elemental analysis structure (Molecular formula C ₁₄ H ₈ Br ₂ N ₂ ): Theory C, 46.19; H, 2.22; Br, 43.90; N, 7.70; Tests: C, 46.16; H, 2.23; Br, 43.90; 7.71. ESI-MS (m/z) (M ⁺ ): calc.

(2) In a 250 mL three-necked flask, nitrogen gas was introduced, 0.04 mol of the intermediate O1, 100 ml of THF, 0.05 mol of phenylboronic acid, 0.0004 mol of tetrakis(triphenylphosphine)palladium, and stirred, and then 0.06 mol of an aqueous K ₂ CO ₃ solution was added ( 2M), heated to 80 ° C, reflux reaction for 10 hours, sampling the plate, the reaction is complete. The mixture was dried with EtOAc (EtOAc m.). Elemental Analysis Structure (Molecular Formula C ₂₀ H ₁₃ BrN ₂ ): Theory C, 66.50; H, 3.63; Br, 22.12; N, 7.75; Tests: C, 66.49; H, 3.64; Br, 22.13; N, 7.74. ESI-MS (m/z) (M ⁺ ): The theoretical value is 360.03, and the measured value is 360.48.

(3) In a 250 mL three-necked flask, nitrogen gas was introduced, 0.02 mol of intermediate P1, 100 ml of THF, 0.03 mol of phenylboronic acid, 0.0002 mol of tetrakis(triphenylphosphine)palladium, and then stirred, followed by addition of 0.03 mol of an aqueous K ₂ CO ₃ solution ( 2M), heated to 80 ° C, reflux reaction for 10 hours, sampling the plate, the reaction is complete. The organic layer was extracted with EtOAc (EtOAc) (EtOAc). Elemental analysis structure (Molecular formula C ₂₆ H ₁₇ BrN ₂ ): calcd. C, 71.41; H, 3.92; Br, 18.27; N, 6.41; C, 71.40; H, 3.92; Br, 18.28; N, 6.40. ESI-MS (m/z) (M ⁺ ): Found: 436.

(4) In a 500 mL three-necked flask, nitrogen gas was introduced, 0.05 intermediate Q1 was added and dissolved in 300 ml of N,N-dimethylformamide (DMF), and then 0.06 mol of bis(pinacolyl)diboron, 0.0005 mol. (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and 0.125 mol of potassium acetate are added, the mixture is stirred, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 120-150 ° C. After 10 hours; after the reaction was completed, 200 ml of water was added and added, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified on silica gel column to afford compound intermediate B5; HPLC purity 99.2%, yield 81.2%. Elemental analysis structure (Molecular formula C ₃₂ H ₂₉ BN ₂ O ₂ ): Theory C, 79.36; H, 6.04; B, 2.23; N, 5.77; O, 6.60; Tests: C, 79.34; H, 6.03; 2.23; N, 5.78; O, 6.61. ESI-MS (m/z) (M ⁺ ): 484.21.

The intermediate II was prepared by the synthesis method of the intermediate B6, and the specific structure is shown in Table 3.

table 3

Example 3: Synthesis of Compound 1:

In a 250 mL three-necked flask, nitrogen gas was introduced, 0.01 mol of intermediate A4, 150 ml of DMF, 0.03 mol of intermediate B1, 0.0002 mol of palladium acetate, and stirred, and then 0.02 mol of K ₃ PO ₄ aqueous solution was added thereto, and heated to 150 ° C, refluxed. After reacting for 24 hours, the plate was sampled and the reaction was completed. The mixture was cooled with EtOAc (EtOAc) (EtOAc). Elemental analysis structure (Molecular formula C ₄₉ H ₃₁ N ₇ ): Theory C, 81.99; H, 4.35; N, 13.66; Tests: C, 81.97; H, 4.38; N, 13.65. ESI-MS (m/z) (M ⁺ ): ???

Example 4: Synthesis of Compound 3:

Compound 3 was prepared in the same manner as in Example 3 except that Intermediate A4 was replaced with Intermediate A2.

Elemental analysis structure (Molecular Formula C ₅₅ H ₃₅ N ₇ ): Theory C, 83.21.; H, 4.44; N, 12.35; Tests: C, 83.25; H, 4.48; N, 12.38. ESI-MS (m/z) (M ⁺ ): calc. 793.30.

Example 5: Synthesis of Compound 4:

Compound 4 was prepared in the same manner as in Example 3 except that Intermediate A1 was replaced with Intermediate A1.

Elemental analysis structure (Molecular formula C ₅₃ H ₃₃ N ₇ ): Theory C, 82.90; H, 4.33; N, 12.77; Tests: C, 82.97; H, 4.38; N, 12.75. ESI-MS (m/z) (M ⁺ ): calc. 671.28.

Example 6: Synthesis of Compound 23:

Compound 23 was prepared in the same manner as in Example 3 except that Intermediate B3 was replaced with Intermediate B3.

Elemental analysis structure (Molecular formula C ₆₁ H ₃₉ N ₇ ): Theory C, 84.21.; H, 4.52; N, 11.27; Found: C, 84.27; H, 4.48; N, 11.25. ESI-MS (m/z) (M ⁺ ): Theory: 869.33, found 869.62.

Example 7: Synthesis of Compound 24:

Compound 24 was prepared in the same manner as in Example 3 except that the intermediate B1 was replaced with the intermediate B4.

Elemental analysis structure (Molecular formula C ₅₇ H ₃₅ N ₇ ): Theory C, 83.70; H, 4.31; N, 11.99; Tests: C, 83.77; H, 4.38; N, 11.95. ESI-MS (m/z) (M ⁺ ): calcd.

Example 8: Synthesis of Compound 2:

In a 250 mL three-necked flask, nitrogen gas was introduced, 0.01 mol of intermediate A6, 150 ml of DMF, 0.03 mol of intermediate B1, 0.0002 mol of palladium acetate, and stirred, and then 0.02 mol of K ₃ PO ₄ aqueous solution was added thereto, and heated to 150 ° C to reflux 24 Hours, sampling the plate, the reaction is complete. The mixture was cooled with EtOAc (EtOAc) (EtOAc).

Elemental Analysis Structure (Molecular Formula C ₄₈ H ₃₀ N ₈ ): Theory C, 80.20; H, 4.21.; N, 15.59; Tests: C, 80.23; H, 4.23; N, 15.62. ESI-MS (m/z) (M ⁺ ): s.

Example 9: Synthesis of Compound 46:

Compound 46 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A7.

Elemental analysis structure (Molecular formula C ₅₂ H ₃₂ N ₈ ): Theory C, 81.23; H, 4.20; N, 14.57; Tests: C, 81.26; H, 4.22; N, 14.51. ESI-MS (m/z) (M ⁺ ): calc. 768.88.

Example 10: Synthesis of Compound 47:

Compound 47 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A8.

Elemental analysis structure (Molecular formula C ₅₂ H ₃₂ N ₈ ): Theory C, 81.23; H, 4.20; N, 14.57; Tests: C, 81.24; H, 4.31; N, 14.55. ESI-MS (m/z) (M ⁺ ): calc. 768.88.

Example 11: Synthesis of Compound 51:

Compound 51 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A9.

Elemental analysis structure (Molecular formula C ₅₂ H ₃₂ N ₈ ): Theory C, 81.23; H, 4.20; N, 14.57; Tests: C, 81.27; H, 4.25; N, 14.53. ESI-MS (m/z) (M ⁺ ): calc. 768.

Example 12: Synthesis of Compound 48:

Compound 48 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A10.

Elemental analysis structure (Molecular formula C ₅₁ H ₃₁ N ₉ ): Theory C, 79.57; H, 4.06; N, 16.37; Found: C, 79.59; H, 4.08; N, 16.32. ESI-MS (m/z) (M ⁺ ): s.

Example 13: Synthesis of Compound 49:

Compound 49 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A11.

Elemental analysis structure (Molecular formula C ₅₁ H ₃₁ N ₉ ): Theory C, 79.57; H, 4.06; N, 16.37; Found: C, 79.59; H, 4.08; N, 16.32. ESI-MS (m/z) (M ⁺ ): s.

Example 14: Synthesis of Compound 50:

Compound 50 was prepared in the same manner as in Example 8, except that Intermediate A6 was replaced with Intermediate A12.

Elemental analysis structure (Molecular formula C ₅₁ H ₃₁ N ₉ ): Theory C, 79.57; H, 4.06; N, 16.37; Found: C, 79.59; H, 4.08; N, 16.32. ESI-MS (m/z) (M ⁺ ): s.

Example 15: Synthesis of Compound 87:

Compound 87 was prepared in the same manner as in Example 3 except that Intermediate B1 was replaced with Intermediate B5.

Elemental analysis structure (Molecular formula C ₆₁ H ₃₉ N ₇ ): Theory C, 84.21.; H, 4.52; N, 11.27; Tests: C, 84.27; H, 4.58; N, 11.25. ESI-MS (m/z) (M ⁺ ): calc. 870.03.

Example 16: Synthesis of Compound 115:

In a 250 mL three-necked flask, nitrogen gas was introduced, 0.01 mol of intermediate A13, 150 ml of DMF, 0.03 mol of intermediate B1, 0.0002 mol of palladium acetate, and stirred, and then 0.02 mol of K ₃ PO ₄ aqueous solution was added thereto, and the mixture was heated to 150 ° C to reflux 24 Hours, sampling the plate, the reaction is complete. The mixture was cooled with EtOAc (EtOAc) (EtOAc).

Elemental Analysis Structure (Molecular Formula C ₆₁ H ₄₀ N ₈ ): Theory C, 82.78; H, 4.56; N, 12.66; Tests: C, 82.73; H, 4.57; N, 12.63. ESI-MS (m/z) (M ⁺ ): Theory: 885.05, found 885.14.

Example 17: Synthesis of Compound 104:

Compound 104 was prepared in the same manner as in Example 16 except that Intermediate A13 was replaced with Intermediate A14.

Elemental analysis structure (Molecular Formula C ₅₅ H ₃₆ N ₈ ): Theory C, 81.66; H, 4.49; N, 13.85; </ RTI> C, 81.61; H, 4.43; N, 13.86. ESI-MS (m/z) (M ⁺ ): calc.

Example 18: Synthesis of Compound 103:

Compound 103 was prepared in the same manner as in Example 16 except that Intermediate A13 was replaced with Intermediate A17.

Elemental analysis structure (Molecular formula C ₅₄ H ₃₅ N ₉ ): Theory C, 80.08; H, 4.36; N, 15.56; </ RTI> C, 80.09; H, 4.45; N, 15.61. ESI-MS (m/z) (M ⁺ ): calc. s.

Example 19: Synthesis of Compound 119:

Compound 119 was prepared in the same manner as in Example 16 except that Intermediate A13 was replaced with Intermediate A16.

Elemental analysis structure (Molecular formula C ₆₇ H ₄₄ N ₈ ): Theory C, 83.73; H, 4.671; N, 11.66; ESI-MS (m/z) (M ⁺ ): s.

Example 20: Synthesis of Compound 136:

Compound 136 was prepared in the same manner as in Example 3 except that Intermediate A3 was replaced with Intermediate A3.

Elemental analysis structure (Molecular formula C ₅₅ H ₃₄ N ₈ ): Theory C, 81.87; H, 4.25; N, 13.89; </ RTI></RTI> C, 81.81; H, 4.22; N, 13.98. ESI-MS (m/z) (M ⁺ ): calc.

The organic compound of the present invention is used in a light-emitting device, and has a high Tg (glass transition temperature) temperature and a high refractive index as a CPL layer material. The thermal performance and refractive index of the compound of the present invention were tested, and the test results are shown in Table 4. 2 is a refractive index diagram of Compound 46.

Table 4

Note: The glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, Germany), the heating rate is 10 °C / min; the refractive index is determined by the ellipsometer (USA JAWoollam Co. model: ALPHA-SE) is measured and tested to the atmosphere.

It can be seen from the above table data that the organic compound of the present invention has a high glass transition temperature and a high refractive index as compared with the materials currently used for CBP, Alq3 and TPBi, and at the same time, the material is ensured by the inclusion of a triazine and a quinoline rigid group. Thermal stability. Therefore, the organic material with triazine and quinoxaline as the core of the invention can effectively improve the light extraction efficiency of the device after being applied to the CPL layer of the OLED device, and ensure the long life of the OLED device.

The application effects of the OLED material synthesized by the present invention in the device will be described in detail below by the device examples 1 to 21 and the device comparative example 1. The device embodiments 2-21 of the present invention, the device comparative example 1 and the device embodiment 1 have the same fabrication process, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also maintained. Consistently, the difference between the device examples 2 and 18 is that the CPL layer material in the device is changed; the device embodiments 19 to 21 change the hole blocking/electron transport layer material of the device, and the devices obtained in the respective embodiments are The performance test results are shown in Table 5.

Device Embodiment 1: As shown in FIG. 1, an electroluminescent device, the preparation steps of which include:

a) cleaning the ITO anode layer 2 on the transparent OLED device substrate 1, respectively, ultrasonically cleaning with deionized water, acetone, ethanol for 15 minutes, and then treating in a plasma cleaner for 2 minutes; b) on the ITO anode layer 2 The hole injection layer material HAT-CN is deposited by vacuum evaporation to a thickness of 10 nm, which is used as the hole injection layer 3; c) on the hole injection layer 3, vapor deposition is carried out by vacuum evaporation. The material NPB has a thickness of 80 nm, the layer is a hole transport layer 4; d) the light-emitting layer 5 is evaporated on the hole transport layer 4, CBP is used as a host material, and Ir(ppy) _{3 is} used as a dopant material, Ir ( Ppy) ₃ and CBP have a mass ratio of 1:9 and a thickness of 30 nm; e) over the light-emitting layer 5, the electron transport material TPBI is evaporated by vacuum evaporation to a thickness of 40 nm, and this layer of organic material acts as a hole block /electron transport layer 6 is used; f) over the hole blocking / electron transport layer 6, vacuum evaporation of the electron injection layer LiF, the thickness is 1 nm, the layer is the electron injection layer 7; g) above the electron injection layer 7 Vacuum-deposited cathode Mg:Ag/Ag layer, Mg:Ag doping ratio is 9:1, thickness 15nm, Ag thickness 3nm, the layer is cathode layer 8; On the cathode layer 8, a CPL material compound 1 was deposited by vacuum evaporation to a thickness of 50 nm, and this organic material was used as the CPL layer 9. After the fabrication of the electroluminescent device was completed as described above, the current efficiency and lifetime of the device were measured, and the results are shown in Table 5. The molecular organization of the relevant material is as follows:

Device Example 2: The CPL layer was Compound 2 of the present invention. Device Example 3: The CPL layer was Compound 3 of the present invention. Device Example 4: The CPL layer was Compound 4 of the present invention. Device Example 5: The CPL layer was Compound 23 of the present invention. Device Example 6: The CPL layer is Compound 24 of the present invention. Device Example 7: The CPL layer is Compound 46 of the present invention. Device Example 8: The CPL layer was Compound 47 of the present invention. Device Example 9: The CPL layer is Compound 48 of the present invention. Device Example 10: The CPL layer is Compound 49 of the present invention. Device Example 11: The CPL layer is Compound 50 of the present invention. Device Example 12: The CPL layer is Compound 51 of the present invention. Device Example 13: The CPL layer is Compound 87 of the present invention. Device Example 14: The CPL layer is the compound 103 of the present invention. Device Example 15: The CPL layer is Compound 104 of the present invention. Device Example 16: The CPL layer is Compound 115 of the present invention. Device Example 17: The CPL layer is Compound 119 of the invention. Device Example 18: The CPL layer is Compound 136 of the invention. Device Example 19: The hole blocking/electron transport layer was Compound 49 of the present invention. Device Example 20: The hole blocking/electron transport layer was the compound 51 of the present invention. Device Example 21: The hole blocking/electron transport layer was Compound 119 of the present invention. Device Comparative Example 1: The CPL layer was a well-known material Alq3. The detection data of the obtained electroluminescent device is shown in Table 5.

table 5

It can be seen from the results of Table 5 that the organic compound with triazine and quinoxaline as the core of the present invention is applied to the OLED light-emitting device, and the light extraction is significantly improved compared with the device comparative example 1, under the same current density. The brightness of the device and the efficiency of the device are improved. As the brightness and efficiency are improved, the power consumption of the OLED device under the fixed brightness is relatively reduced, and the service life is also improved. In order to illustrate the phase stability crystallization stability of the material of the present invention, the material of the present invention 24 and the known material CBP were subjected to a film accelerated crystallization experiment: vacuum evaporation was used to vapor-deposit compound 24 and CBP on an alkali-free glass. And packaged in a glove box (water oxygen content <0.1ppm), the packaged sample is placed in a double 85 (temperature 85 ° C, humidity 85%), periodically with a microscope (LEICA, DM8000M, 5 * 10 times Observe the crystal state of the material film. The experimental results are shown in Table 6. The surface morphology of the material is shown in Figure 3:

Table 6

Material name	Compound 24	CBP
After film formation	Smooth and even surface	Smooth and even surface
72 hours after the experiment	Smooth and even surface, no crystal	The surface forms a number of discrete circular crystal faces
600 hours after the experiment	Smooth and even surface, no crystal	Surface crack

The above experiments show that the film crystallization stability of the material of the present invention is much higher than that of the known materials, and has a beneficial effect on the service life after application to the OLED device.

Further, the OLED device prepared by the material of the invention is more stable when operating at a low temperature, and the device examples 19, 20, 21 and the device comparative example 1 are tested in the range of -10 to 80 ° C, and the results are shown in Table 7 and Figure 4 shows.

Table 7

As can be seen from the data in Table 7 and FIG. 4, device embodiments 19, 20, and 21 are device structures in which the materials of the present invention and known materials are matched, and compared with the device of Comparative Example 1, not only the low temperature efficiency but also the temperature rise process. In the middle, efficiency has increased steadily.

In the above, the above description is only the preferred embodiment of the present invention, and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., which are included in the spirit and principles of the present invention, should be included in the present invention. Within the scope of protection of the invention.

Claims (12)

1. An organic compound having triazine and quinoxaline as its core, wherein the structure of the organic compound is as shown in the formula (1):

   

   In the formula (1), Ar ₁ , Ar ₂ and Ar ₃ are each independently represented by a single bond, a substituted or unsubstituted C _6-60 arylene group, a substituted or unsubstituted 5 having one or more hetero atoms. a 60-membered heteroarylene; the hetero atom is nitrogen, oxygen or sulfur;

   Ar ₁ , Ar ₂ , and Ar ₃ may be the same or different;

   In the formula (1), R _{1 is} represented by a hydrogen atom; a C _1-10 linear or branched alkyl group; a halogen atom, a ruthenium atom, a ruthenium atom or a ruthenium atom substituted or unsubstituted pyridyl group; a compound of the formula (3); or the formula (4);

   

   In the general formula (2), each X is independently represented as N or C, and at least one X is N;

   In the general formula (3), each Y is independently represented as N or C, and at least one Y is N;

   In the formula (4), R ₄ and R ₅ are each independently represented by a substituted or unsubstituted C _6-60 aryl group, a substituted or unsubstituted 5- to 60-membered heteroaryl group having one or more hetero atoms; The hetero atom is nitrogen, oxygen or sulfur;

   R ₄ and R ₅ may be the same or different;

   In the formula (1), R ₂ and R ₃ are each independently represented by the formula (5) or the formula (6);

   

   Wherein R ₆ , R ₇ and R ₈ are each independently represented by a substituted or unsubstituted C _6-60 aryl group, a substituted or unsubstituted 5- to 60-membered heteroaryl group containing one or more hetero atoms; The hetero atom is nitrogen, oxygen or sulfur.
2. The organic compound according to claim 1, wherein the organic compound has a structure of the formula (I) - As shown in any of (VI):

   
3. According to claim 1, characterized in that the structure of the compound is as shown in any one of the formulae (I) to (IV):

   
4. The compound according to claim 1, wherein said Ar ₁ , Ar ₂ and Ar ₃ are each independently represented by a single bond, a C _1-10 linear or branched alkyl group, a halogen atom, a halogen atom or a halogen atom. Or a substituted or unsubstituted phenylene group of a halogen atom; a naphthylene group; a subdiphenyl group; a subtriphenyl group; a furylene group; a pyridylene group; or a carbazolyl group; R ₄ , R ₅ , R ₆ , R ₇ , and R ₈ are each independently represented by a C _1-10 linear or branched alkyl group; a halogen atom, a halogen atom, a halogen atom, or a halogen substituted or unsubstituted phenyl group; One of a terphenyl group; a furyl group; a pyridyl group; or a carbazolyl group.
5. The compound according to claim 1, wherein R ₁ in the formula (1) can be independently represented as:

   

   

   

   One of them.
6. The organic compound according to claim 1, wherein the specific structural formula of the organic compound is:

   

   

   

   

   

   

   

   

   

   

   

   Any of (147).
7. A method for preparing an organic compound according to any one of claims 1 to 6, wherein the reaction equation occurring during the preparation is:

   first step:

   When Ar ₁ or R ₁ and a triazine group are bonded by a CN bond,

   

   The specific reaction process is as follows: the raw material 2,4,6-trichloro-1,3,5-triazine and R ₁ -H or R1-Ar ₁ -H are weighed and dissolved in toluene; then Pd ₂ (dba) _{3 is added.} , tri-tert-butylphosphine, sodium tert-butoxide; under a inert atmosphere, the mixed solution of the above reactants is reacted at a reaction temperature of 95 to 110 ° C for 10 to 24 hours, cooled and filtered, and the filtrate is steamed and passed through silica gel. Column, obtaining intermediate I;

   The molar ratio of the 2,4,6-trichloro-1,3,5-triazine to R ₁ -H or R1-Ar ₁ -H is 1:1.0 to 1.5, and Pd ₂ (dba) ₃ and 2, The molar ratio of 4,6-trichloro-1,3,5-triazine is 0.006 to 0.02:1, and the molar ratio of tri-tert-butylphosphine to 2,4,6-trichloro-1,3,5-triazine The ratio of 0.006 to 0.02:1, the molar ratio of sodium t-butoxide to 2,4,6-trichloro-1,3,5-triazine is 2.0 to 3.0:1;

   When Ar ₁ or R ₁ and a triazine group are bonded by a CC bond,

   

   Under nitrogen atmosphere, weigh 2,4,6-trichloro-1,3,5-triazine in N,N-dimethylformamide, DMF, and then

   

   And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 5 to 15 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, the residue obtained is purified by silica gel column to obtain compound intermediate I;

   The 2,4,6-trichloro-1,3,5-triazine and

   

   The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to 2,4,6-trichloro-1,3,5-triazine is 0.001-0.02:1, K ₃ PO ₄ and 2, The molar ratio of 4,6-trichloro-1,3,5-triazine is 1.0 to 2.0:1, and the ratio of 2,4,6-trichloro-1,3,5-triazine to DMF is 1 g: 10 to 20 ml;

   The second step:

   

   The specific reaction process is: under the nitrogen atmosphere, the intermediate I is weighed and dissolved in N, N-dimethylformamide, that is, DMF, and then

   

   And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 10 to 24 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, the residue obtained is purified by silica gel column to obtain compound intermediate II;

   The intermediate I and

   

   The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to intermediate I is 0.001-0.02:1, and the molar ratio of K ₃ PO ₄ to intermediate I is 1.0-2.0:1, intermediate I The ratio of use to DMF is 1g: 10-20ml;

   third step:

   

   The specific reaction process is: under the nitrogen atmosphere, the intermediate II is weighed and dissolved in N, N-dimethylformamide, that is, DMF, and then

   

   And adding palladium acetate, stirring the mixture, adding potassium phosphate aqueous solution, and heating the mixed solution of the above reactants at a reaction temperature of 120 to 150 ° C for 10 to 24 hours; after the reaction is finished, cooling is added, the mixture is filtered and dried under vacuum. Drying in a box, and purifying the residue by silica gel column to obtain the target compound;

   The intermediate II and

   

   The molar ratio is 1:1.0-1.5, the molar ratio of Pd(OAc) ₂ to intermediate II is 0.001-0.02:1, the molar ratio of K ₃ PO ₄ to intermediate II is 1.0-2.0:1, intermediate II and The dosage ratio of DMF is 1 g: 15 to 30 ml.
8. An organic compound having a triazine and a quinoxaline as a core according to claims 1 to 6 for use in the preparation of an organic electroluminescent device.
9. An organic electroluminescent device characterized in that the organic electroluminescent device comprises at least one functional layer comprising the organic compound having triazine and quinoxaline as the core according to claims 1 to 6.
10. An organic electroluminescent device comprising a hole blocking layer/electron transport layer, characterized in that the hole blocking layer/electron transport layer comprises triazine and quinoxaline as claimed in claims 1 to 6 Organic compounds.
11. An organic electroluminescent device comprising a CPL layer, characterized in that the CPL layer comprises the organic compound having triazine and quinoxaline as the core according to claims 1 to 6.
12. An illumination or display element comprising the organic electroluminescent device of claim 8.

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