CN108863896A - Biindolyl class material, organic electroluminescence device and display device - Google Patents

Abstract

The invention relates to the field of display technology, in particular to a biindole material, an organic electroluminescent device and a display device. Compound according to the present invention is shown in formula (1): Using the compound provided by the invention as the hole transport material, hole injection material and/or host material of the organic electroluminescent device improves the luminous efficiency of the organic electroluminescent device and reduces the driving voltage of the organic electroluminescent device .

Description

Biindole material, organic electroluminescent device and display device

technical field

The invention relates to the field of display technology, in particular to a biindole material, an organic electroluminescent device and a display device.

Background technique

Organic Light Emitting Display (OLED) is a new type of flat-panel display. Compared with Liquid Crystal Display (LCD), it has the advantages of thinness, lightness, wide viewing angle, active luminescence, and continuously adjustable luminous color. , low cost, fast response speed, low energy consumption, low driving voltage, wide operating temperature range, simple production process, high luminous efficiency and flexible display, etc., have attracted great attention from the industrial and scientific circles.

The development of organic electroluminescent devices has promoted the research on organic electroluminescent materials. Compared with inorganic light-emitting materials, organic electroluminescent materials have the following advantages: organic materials have good processability, and can be formed into films on any substrate by evaporation or spin coating; the diversity of organic molecular structures makes it possible to design and Modification methods are used to adjust the thermal stability, mechanical properties, luminescence and electrical conductivity of organic materials, so that there is a lot of room for improvement of materials.

The generation of organic electroluminescence depends on the recombination of carriers (electrons and holes) transported in organic semiconductor materials. As we all know, the conductivity of organic materials is very poor, there is no continuous energy band in organic semiconductors, and the transport of carriers is often described by hopping theory. In order to achieve a breakthrough in the application of organic electroluminescent devices, it is necessary to overcome the difficulties of poor charge injection and transport capabilities of organic materials. Scientists have adjusted the device structure, such as increasing the number of organic material layers of the device, and making different organic layers play different device layers. For example, some functional materials can promote electron injection from the cathode, and some functional materials can promote hole injection from the cathode. For anode injection, some materials can promote the transport of charges, while others can block the transport of electrons or holes. Of course, in organic electroluminescent devices, the most important luminescent materials of various colors must also achieve the purpose of matching with adjacent functional materials. Therefore, organic electroluminescent devices with high efficiency and long life are usually the result of the optimal combination of device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.

In the preparation process of organic electroluminescent devices, one is called evaporation method, that is, each functional material is deposited on the substrate by vacuum thermal evaporation to form a film, which is also the mainstream technology in the industry at present. However, the shortcomings of this process are also obvious. On the one hand, the characteristics of the organic material itself determine that thermal evaporation at high temperature for a long time requires high thermal stability of the material; in addition, the long-term stable control of the evaporation rate, Maintaining the uniformity of material distribution on the substrate is also a very important requirement; and high vacuum, high temperature evaporation, high energy consumption; more importantly, because the production process of the OLED material itself is relatively complicated and the technical content is high, so the price is relatively high. Expensive, and the existing process uses evaporation, and the utilization rate of OLED materials is low, generally below 10%.

In the preparation process of organic electroluminescent devices, the other is called solution method, which uses soluble OLED materials, dissolves them in solvents, and coats them on the substrate by printing, inkjet, spin coating, etc. In order to form certain functional layers, this method distributes materials evenly, saves materials, simplifies the production process of OLED devices, and reduces the production cost of OLED devices.

Contents of the invention

The invention provides a biindole material, an organic electroluminescent device comprising the compound and a display device having the organic electroluminescent device. The organic electroluminescent device comprising the compound has lower driving voltage and higher High luminous efficiency.

According to one aspect of the present invention, a kind of biindole material is provided, as shown in formula (1):

Wherein B is selected from carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indenocarbazolyl, indolocarbazolyl, indolospirofluorenyl, dihydroacridinyl, dihydrophen Azinyl, 10H-phenothiazinyl, 10H-phenoxazinyl; B can be replaced by C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl composed of carbon and hydrogen, B- 1 is substituted; the substitution can be single substitution, double substitution, multiple substitution:

In B-1, Ar ₁ and Ar ₂ are independently selected from C6-C40 aryl groups composed of carbon and hydrogen. In B-1, * indicates the position where B is connected to B in formula (1); Ar ₁ , Ar ₂ can be substituted by C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl composed of carbon and hydrogen; the substitution can be single substitution, double substitution or multiple substitution.

Further, the C6-C40 aryl group is selected from: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, fluoranthene, indenofluorenyl, spirofluorene Base, benzofluorenyl, dibenzofluorenyl, phenyl substituted naphthyl, benzanthracenyl; C1-C20 alkyl group selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, ring Hexyl, heptyl, octyl; C1～C20 alkoxy is selected from methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, Octyloxy.

Furthermore, the biindole materials provided by the present invention are selected from the following structures:

According to another aspect of the present invention, an organic electroluminescent device is provided, the organic electroluminescent device comprising the biindole material according to the present invention.

Optionally, the hole-transporting material of the organic electroluminescent device is the biindole-based material according to the present invention.

Optionally, the hole injection material of the organic electroluminescence device is the biindoles material according to the present invention.

Optionally, the host material of the light-emitting layer of the organic electroluminescent device is the biindole-based material according to the present invention.

Further, the light-emitting layer of the organic electroluminescent device is a phosphorescent light-emitting layer.

According to another aspect of the present invention, there is provided a display device comprising the organic electroluminescent device according to the present invention.

The beneficial effects of the present invention are as follows:

Using the compound provided by the invention as a hole injection material or/and a hole transport material or/and a light-emitting layer host material of an organic electroluminescence device improves the luminous efficiency of the organic electroluminescence device and reduces the organic electroluminescence device drive voltage.

Detailed ways

The specific embodiments are only an illustration of the present invention, and do not constitute a limitation to the content of the present invention. The following will further illustrate and describe the present invention in conjunction with specific embodiments.

The invention provides a biindole material, an organic electroluminescent device comprising the compound and a display device having the organic electroluminescent device. The organic electroluminescent device comprising the compound has lower driving voltage and higher High luminous efficiency.

In order to illustrate the compounds of the present invention in more detail, the following will further describe the present invention by enumerating the synthesis methods of the above-mentioned specific compounds.

The synthesis of embodiment 1 compound P-1:

Synthesis of Intermediate 1

In a 2000ml three-necked flask, add 28.6g (0.1mol) 3-(4-bromophenyl)-1-methyl-1H-indole, 800ml anhydrous acetonitrile, and slowly add 65% 10 grams of nitric acid, after the dropwise addition, control the temperature at 0-3°C for 3 hours, then slowly add 10 grams of 65% nitric acid dropwise at 0-3°C, control the temperature at 0-3°C for 3 hours, and then control the temperature at 0-3°C. Slowly add 10 grams of 65% nitric acid dropwise at ~3°C, control the temperature at 0~3°C for 8 hours, add water and dichloromethane to separate liquid, wash with water until neutral, and separate the organic layer by silica gel column chromatography, ethyl acetate: petroleum ether =1:9 (volume ratio) for elution, the eluate was concentrated to dryness, and recrystallized from a methanol/toluene mixed solvent to obtain 10.1 g of the compound shown in Intermediate 1 with a yield of 35.43%.

Mass spectrometry was carried out on the product represented by the obtained intermediate 1, and the m/e of the product was obtained: 570.

The product shown in the obtained intermediate 1 has been subjected to nuclear magnetic detection, and the nuclear magnetic analysis data obtained are as follows:

¹ HNMR (500MHz, CDCl ₃ ): δ7.75(m, 2H), δ7.58～7.48(m, 10H), δ7.26(t, 2H), δ7.02(m, 2H), δ3.81 (s, 6H).

Synthesis of Compound P-1

In a 500 ml three-necked flask, under nitrogen protection, add 300 ml of dry toluene, 28.5 g (0.05 mol) of the compound shown in Intermediate 1, 20.04 g (0.12 mol) of carbazole, 14.4 g (0.15 mol) of sodium tert-butoxide , 0.58 gram (0.001mol) two (dibenzylideneacetone) palladium, 2.02 gram (0.001mol) the toluene solution of 10% tri-tert-butylphosphine, be down to room temperature after heating to reflux reaction for 8 hours, add dilute hydrochloric acid, Separation, the organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, separated by silica gel column, eluted with ethyl acetate:petroleum ether=1:5 (volume ratio), the eluate was concentrated to dryness, washed with ethanol /toluene mixed solvent recrystallization to obtain 26.6 g of the compound represented by formula P-1, with a yield of 71.6%.

The obtained product represented by the formula P-1 was detected by mass spectrometry, and the m/e of the product was obtained: 742.

The product shown in the obtained formula P-1 has been carried out nuclear magnetic detection, and the obtained nuclear magnetic analysis data is as follows:

¹ HNMR (500MHz, CDCl ₃ ): δ8.51(m, 2H), δ8.12(m, 2H), δ7.90(m, 8H), δ7.76(m, 2H), δ7.51(m , 4H), δ7.40 (m, 2H), δ7.28 (m, 2H), δ7.23～7.03 (m, 10H), δ3.78 (s, 6H).

Synthesis of other part compounds of embodiment 2

Referring to the synthesis method of compound P-1, only the carbazole therein is replaced with the corresponding nitrogen-containing aromatic compound as required. The used nitrogen-containing aromatic compound of concrete reaction and the obtained compound mass spectrum data list of the present invention are as follows:

The synthesis of embodiment 3 compound P-33

1000 milliliter three-neck flask, nitrogen protection, add 200 milliliters of toluene, 200 milliliters of ethanol, 100 milliliters of water, 2.85 grams (0.005mol) of the compound shown in intermediate 1, 3.34 grams (0.012mol) of N-phenylcarbazole-3-boronic acid , 0.112 grams (0.0001mol) tetrakistriphenylphosphine palladium, 2.12 grams (0.02mol) sodium carbonate, slowly heated to reflux reaction for 12 hours, cooling, liquid separation, organic layer magnesium sulfate drying, silica gel column chromatography separation, ethyl acetate Ester: petroleum ether = 1:5 (volume ratio) for elution, and the eluate was concentrated to dryness to obtain 3.06 g of the product shown in formula P-33, with a yield of 68.37%.

The product represented by the obtained formula P-33 was detected by mass spectrometry, and the m/e of the product was obtained: 894.

The product shown in the obtained formula P-33 has been carried out nuclear magnetic detection, and the obtained nuclear magnetic analysis data is as follows:

¹ HNMR (500MHz, CDCl ₃ ): δ8.52(m, 1H), δ8.22(m, 3H), δ7.87(m, 1H), δ7.76(m, 2H), δ7.70(d , 1H), δ7.66～7.56(m, 7H), δ7.51(m, 8H), δ7.38(m, 1H), δ7.34～7.22(m, 10H), δ7.20～7.13( m, 4H), δ7.02 (m, 2H), δ3.79 (s, 6H).

Synthesis of other part compounds of embodiment 4

Referring to the synthesis method of compound P-33, only the N-phenylcarbazole-3-boronic acid is replaced with the corresponding boronic acid compound as required. The boronic acid compounds used in the specific reaction and the obtained compound mass spectrum data list of the present invention are as follows:

According to another aspect of the present invention, an organic electroluminescent device is provided, the hole injection material/hole transport material/light-emitting layer host material of the organic electroluminescent device is the biindole material according to the present invention .

The typical structure of an organic electroluminescent device is: substrate/anode/hole injection layer/hole transport layer (HTL)/organic light-emitting layer (EL)/electron transport layer (ETL)/electron injection layer/cathode. The organic electroluminescent device structure can be a single light emitting layer or multiple light emitting layers.

Wherein, the substrate can be a substrate in a traditional organic electroluminescent device, such as glass or plastic. The anode can be made of transparent high-conductivity materials, such as: indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO ₂ ), zinc oxide (ZnO).

The hole injection material (HIM for short) of the hole injection layer is required to have high thermal stability (high Tg), and has a small potential barrier with the anode or the hole injection material. It is prepared by evaporation method. For electroluminescent devices, it is required that the material can be vacuum evaporated to form a pinhole-free film. Commonly used HIMs are aromatic polyamine compounds, mainly triarylamine derivatives. For the preparation of organic electroluminescent devices by the solution method, the materials are required to have appropriate solubility. After the solution is coated on the substrate and the solution evaporates, a dense and uniform amorphous film can be formed on the substrate. Commonly used HIM materials mainly include PEDOT:PSS.

The hole transport material (HTM for short) of the hole transport layer is required to have high thermal stability (high Tg), high hole transport ability, and can be vacuum evaporated to form a pinhole-free film. Commonly used HTMs are aromatic polyamine compounds, mainly triarylamine derivatives.

The organic light-emitting layer includes a host material (host) and a guest material, wherein the guest material is a light-emitting material, such as a dye, and the host material needs to have the following characteristics: reversible electrochemical redox potential, and the adjacent hole transport layer and electron transport layer Matching HOMO energy level and LUMO energy level, good and matching hole and electron transport ability, good high thermal stability and film formation, and suitable singlet or triplet energy gap to control excitons In the emitting layer there is also a good energy transfer with the corresponding fluorescent or phosphorescent dyes. The light-emitting material of the organic light-emitting layer, taking the dye as an example, needs to have the following characteristics: high fluorescence or phosphorescence quantum efficiency; the absorption spectrum of the dye and the emission spectrum of the host have a good overlap, that is, the energy of the host and the dye is adapted, and the energy from the host The dye can effectively transfer energy; the emission peaks of red, green, and blue are as narrow as possible to obtain good color purity; the stability is good, and it can be evaporated.

The electron transport material (Electron transport Material, referred to as ETM) of the electron transport layer requires that the ETM has a reversible and sufficiently high electrochemical reduction potential, and a suitable HOMO energy level and LUMO (Lowest Unoccupied Molecular Orbital, the lowest unoccupied molecular orbital) energy level value makes Electrons can be injected better, and it is better to have hole blocking ability; higher electron transport ability, good film formation and thermal stability. ETMs are generally aromatic compounds with conjugated planes of electron-deficient structures. When preparing organic electroluminescent devices by evaporation method, Alq3 (8-hydroxyquinoline aluminum) or TAZ (3-phenyl-4-(1'-naphthyl)-5-benzene-1,2 ,4-triazole) or TPBi (1,3,5-tris(N-phenyl-2-benzimidazole)benzene) or a combination of any two of these three materials.

According to another aspect of the present invention, there is provided a display device comprising the organic electroluminescent device according to the present invention.

It can be seen that there are many optional factors for the compound, organic electroluminescent device and display device according to the present invention, and different embodiments can be combined according to the claims of the present invention. The embodiments of the present invention are only used as a specific description of the present invention, not as a limitation of the present invention. The present invention will be further described below with reference to an organic electroluminescent device containing the compound of the present invention as an example.

The concrete structure of material used in the embodiment sees below:

Example 5

The compound of the present invention is used as the hole transport material in the organic electroluminescent device, and as a comparative organic electroluminescent device, the hole transport material is NPB.

The structure of the organic electroluminescence device is: ITO/HIL02 (100nm)/HTL (40nm)/EM1 (30nm)/ETL (20nm)/LiF (0.5nm)/Al (150nm).

In the production of the organic electroluminescent device in this embodiment, a glass substrate is selected, ITO is used as the anode material, HIL02 is used as the hole injection layer, EM1 is used as the main material of the organic light-emitting layer, TAZ is used as the electron transport layer material, and LiF/Al is used as the electron injection layer. layer/cathode material.

The preparation process of the organic electroluminescent device in this embodiment is as follows:

The glass substrate coated with the ITO transparent conductive layer (as the anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, then ultrasonically degreased in acetone and ethanol mixed solvent, and then baked in a clean environment until Completely remove water, clean with ultraviolet light and ozone, and bombard the surface with low-energy cation beams to improve the properties of the surface and improve the binding ability with the hole transport layer.

Place the above-mentioned glass substrate in a vacuum chamber, evacuate to 1×10 ^-5 -9×10 ^-3 Pa, vacuum-deposit HIL02 on the anode as a hole injection layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100nm.

The hole transport layer was vacuum evaporated on the hole injection layer, the evaporation rate was 0.1 nm/s, and the evaporation film thickness was 40 nm.

On top of the hole transport layer, EM1 was vacuum evaporated as the organic light-emitting layer of the device. The evaporation rate was 0.1 nm/s, and the total film thickness was 30 nm.

TAZ is vacuum-deposited on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 20nm.

Vacuum-evaporated 0.5nm LiF on the electron transport layer (ETL) as the electron injection layer;

150 nm of aluminum (Al) was vacuum-deposited as a cathode on the electron injection layer.

The properties of organic electroluminescent devices are shown in Table 1:

Table 1

It can be seen from the above table that using the compound of the present invention as the hole transport layer can improve the luminous efficiency of the organic electroluminescent device and reduce the driving voltage of the organic electroluminescent device.

Example 6

The compound of the present invention is used as the hole injection material in the organic electroluminescence device, and HIL02 is selected as the hole injection material in the organic electroluminescence device for comparison.

The structure of the organic electroluminescence device is: ITO/HIL (100nm)/HTL (40nm)/EM1 (30nm)/ETL (20nm)/LiF (0.5nm)/Al (150nm).

In the production of the organic electroluminescent device in this embodiment, a glass substrate is selected, ITO is used as the anode material, NPB is used as the hole transport layer, EM1 is used as the main material of the organic light-emitting layer, TAZ is used as the electron transport layer material, and LiF/Al is used as the electron injection layer/cathode material.

The preparation process of the organic electroluminescent device in this embodiment is as follows:

The glass substrate coated with the ITO transparent conductive layer (as the anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, then ultrasonically degreased in acetone and ethanol mixed solvent, and then baked in a clean environment until Completely remove water, clean with ultraviolet light and ozone, and bombard the surface with low-energy cation beams to improve the properties of the surface and improve the binding ability with the hole transport layer.

The above glass substrate was placed in a vacuum chamber, and a hole injection layer was vacuum evaporated on the anode with an evaporation rate of 0.1 nm/s and an evaporation film thickness of 100 nm.

NPB was vacuum evaporated on the hole injection layer as the hole transport layer, the evaporation rate was 0.1 nm/s, and the evaporation film thickness was 40 nm.

On top of the hole transport layer, EM1 was vacuum evaporated as the organic light-emitting layer of the device. The evaporation rate was 0.1 nm/s, and the total film thickness was 30 nm.

TAZ is vacuum-deposited on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 20nm.

Vacuum-evaporated 0.5nm LiF on the electron transport layer (ETL) as the electron injection layer;

150 nm of aluminum (Al) was vacuum-deposited as a cathode on the electron injection layer.

The performance of the organic electroluminescent device is shown in Table 2:

Table 2

It can be seen from the above table that using the compound of the present invention as the hole injection layer can improve the luminous efficiency of the organic electroluminescent device and reduce the driving voltage of the organic electroluminescent device.

Example 7

Compounds of the present invention are used as host materials in red phosphorescent OLED organic electroluminescent devices:

The organic electroluminescent device structure is:

ITO/NPB (20nm)/Red host material (30nm): Ir(piq)3[5%]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm).

One of them is a comparative organic electroluminescent device, the red light host material is selected from CBP, and the other seven organic electroluminescent devices are selected from the material of the present invention.

The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, and baked in a clean environment. Baked until completely dehydrated, cleaned with UV light and ozone, and bombarded with a beam of low-energy cations;

Put the above-mentioned glass substrate with an anode in a vacuum chamber, evacuate to 1×10-5～9×10-3Pa, and vacuum-deposit the hole-transport layer NPB on the above-mentioned anode layer film, and the evaporation rate is 0.1 nm/s, the evaporated film thickness is 20nm;

On the hole transport layer, the luminescent host material and dye are vacuum-deposited as the light-emitting layer of the organic electroluminescence device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;

On the light-emitting layer, the electron transport layer TPBI and Alq3 were vacuum-evaporated sequentially, the evaporation rate was 0.1nm/s, and the evaporation film thickness was 10nm and 15nm respectively;

0.5nm LiF was vacuum-deposited on the electron transport layer, and 150nm Al was used as a cathode.

The properties of organic electroluminescent devices are shown in Table 3:

table 3

As can be seen from the above table, the organic electroluminescent device using the chemical composition of the present invention as the phosphorescent main body has obtained a better effect than the organic electroluminescent device using CBP as the main body, and has obtained higher current efficiency and lower the drive voltage.

Embodiment 8:

Compounds of the present invention are used as host materials in green phosphorescent OLED organic electroluminescent devices:

A total of 9 organic electroluminescent devices were prepared, and the structure of the organic electroluminescent device was as follows:

ITO/NPB (20nm)/green host material (30nm): Ir(ppy)3[7%]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm).

One of them is a comparative organic electroluminescent device, the main material of the green light is CBP, and the other eight organic electroluminescent devices are selected from the material of the present invention.

The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, and baked in a clean environment. Baked until completely dehydrated, cleaned with UV light and ozone, and bombarded with a beam of low-energy cations;

Put the above-mentioned glass substrate with an anode in a vacuum chamber, evacuate to 1×10-5～9×10-3Pa, and vacuum-deposit the hole-transport layer NPB on the above-mentioned anode layer film, and the evaporation rate is 0.1 nm/s, the evaporated film thickness is 20nm;

On the hole transport layer, the luminescent host material and dye are vacuum-deposited as the light-emitting layer of the organic electroluminescence device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;

On the light-emitting layer, the electron transport layer TPBI and Alq3 were vacuum-evaporated sequentially, the evaporation rate was 0.1nm/s, and the evaporation film thickness was 10nm and 15nm respectively;

0.5nm LiF was vacuum evaporated on the electron transport layer, and 150nm Al was used as the electron injection layer and cathode.

The performance of the organic electroluminescent device is shown in Table 4:

Table 4

As can be seen from the above table, the organic electroluminescent device using the chemical composition of the present invention as the phosphorescent main body has obtained a better effect than the organic electroluminescent device using CBP as the main body, and has obtained higher current efficiency and lower the drive voltage.

Obviously, those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if these modifications and variations of the present invention fall within the scope of the claims of the present invention and equivalent technologies thereof, the present invention also intends to include these modifications and variations.

Claims (5)

1. an organic electroluminescence device, is characterized in that, described organic electroluminescence device comprises the biindole material shown in formula (1): Wherein B is selected from carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indenocarbazolyl, indolocarbazolyl, indolospirofluorenyl, dihydroacridinyl, dihydrophen Azinyl, 10H-phenothiazinyl, 10H-phenoxazinyl; B can be substituted by C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl composed of carbon and hydrogen, B-1; the substitution can be single substitution, double substitution, multiple substitution : Ar ₁ and Ar ₂ are independently selected from C6-C40 aryl groups composed of carbon and hydrogen, and * in B-1 represents the position where B-1 is connected to B in formula (1); Ar ₁ and Ar ₂ can be substituted by C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl composed of carbon and hydrogen; the substitution can be single substitution, double substitution, multiple substitution . 2. The organic electroluminescence device according to claim 1, wherein the aryl group of C6～C40 is selected from: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorene Base, fluoranthenyl, indenofluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenyl substituted naphthyl, benzanthracenyl; C1～C20 alkyl group is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl; The C1-C20 alkoxy group is selected from methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy and octyloxy. 3. The organic electroluminescent device according to claim 1, the biindole materials shown in formula (1) are selected from: 4. The organic electroluminescent device according to claim 1, wherein the hole injection material of the organic electroluminescent device is a biindole material shown in formula (1). 5. A display device, characterized by comprising the organic electroluminescence device as claimed in claim 1.