CN104513661A - Organic luminescence material and applications thereof - Google Patents

Abstract

The present invention relates to a kind of organic luminescent material as shown in formula (I), wherein: Ar ₁ -Ar ₉ are independently selected from H, C6-C30 substituted or unsubstituted aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted fused ring aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted condensed heterocyclic groups, or five-membered, six-membered heterocyclic or substituted heterocyclic rings, C6-C30 substituted or unsubstituted triarylamine groups, or aromatic Ether group, one of C1-C12 substituted or unsubstituted aliphatic alkyl groups, Ar ₁ -Ar ₈ are not H at the same time. The present invention also protects the application of such compounds in organic electroluminescent devices, especially as hole injection materials, hole transport layer materials, fluorescent host materials or light emitting materials in OLED devices.

Description

A kind of organic luminescent material and its application

technical field

The invention relates to a novel organic luminescent material, in particular to a compound used in an organic electroluminescent device and its application in the organic electroluminescent device. the

Background technique

Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-illumination, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal display, organic electroluminescent display is not It needs a backlight source, has a large viewing angle, low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, organic electroluminescent devices have broad application prospects. the

The generation of organic electroluminescence depends on the recombination of carriers (electrons and holes) transported in organic electroluminescent materials. As we all know, organic materials have poor electrical conductivity. Unlike inorganic semiconductors, organic semiconductors do not have The continuation of the energy band, the transport of carriers is often described by jumping theory, that is, driven by an electric field, electrons are excited or injected into the LUMO energy level of a molecule, and then jump to the LUMO energy level of another molecule to achieve purpose of charge transport. 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 structure of the device, such as increasing the number of organic material layers in the device, and making different organic layers play different roles. For example, some functional materials help inject electrons from the cathode and holes from the anode, and some materials help the flow of charges. transport, and some materials play a role in blocking the transport of electrons and holes. Of course, the most important luminescent materials of various colors in organic electroluminescence must also achieve the purpose of matching with adjacent functional materials. A high efficiency and long life Long organic electroluminescent devices are usually the result of the optimal combination of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. the

The hole injection and transport materials that have been used in organic electroluminescent devices are generally triarylamine derivatives (for example, Idemitsu Patent: Publication No. CN1152607C, publication date 2004, June, 2), and its general structural characteristics are that, as injection materials , there are at least three triarylamine structural units in one molecule, and two Ns are separated by a benzene ring, see formula 1; as a transmission material, the triarylamine structural unit in one molecule is generally two , and the two Ns are separated by biphenyl. In this type of material, a typical example is NPB, whose structure is shown in formula 2. the

In recent years, the research on this kind of materials has made some new progress, introducing one or more thienyl groups into the molecule, or introducing one or more benzothienyl groups, see formula 3 and formula 4 (Idemitsu Patent: Publication No. CN101506191A , Publication Date 2009, 8, 12), the result is that the hole injection ability of the material is greatly increased; as a transport material, when a triarylamine structural unit in the material is substituted with carbazole or dibenzofuran, the transport of the material Ability has been greatly improved. See Formula 5 and Formula 6 (Idemitsu Patent: Publication No. CN102334210A, application date 2012.1.25; Publication No.: WO 2010/114017A1, publication date 2010.10.7).

Contents of the invention

The purpose of the present invention is to provide a new type of organic luminescent material, which can be used in the field of organic electroluminescence display. the

For this reason, the technical scheme that the present invention takes is:

An organic luminescent material having a structure as shown in formula (I):

in:

Ar ₁ -A ₉ are independently selected from H, C6-C30 substituted or unsubstituted aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted fused ring aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted fused heterocyclic groups, Or five-membered, six-membered heterocycle or substituted heterocycle, C6-C30 substituted or unsubstituted triarylamine group, or aryl ether group, one of C1-C12 substituted or unsubstituted aliphatic alkyl groups species, Ar1-Ar8 are not H at the same time.

Further, said Ar5, Ar6, Ar7, Ar8 and Ar9 are H at the same time. the

Further, the Ar4 is selected from phenyl, substituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, perylenyl, pyrenyl. the

Further, the Ar1, Ar2, and Ar3 are independently selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, chrysene, triphenylene, substituted phenyl, substituted naphthyl, substituted pyrenyl, Substituted chrysyl, substituted anthracenyl, carbazolyl, triphenylene, substituted carbazolyl, dibenzothienyl, substituted dibenzothienyl, dibenzofuryl, substituted dibenzofuranyl, triarylamino , Substituted triarylamine. the

In order to illustrate the content of the present invention more clearly, the preferred structure of the compound that the present invention relates to is described in detail below:

The invention provides an organic luminescent material, which is applied to an organic electroluminescent device. the

Further, the organic luminescent material can be used as a hole injection material, a hole transport material or a host material in an organic electroluminescent device. the

The present invention also provides an organic electroluminescent device, including a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;

The organic light-emitting functional layer includes a hole transport layer, an organic light-emitting layer and an electron transport layer;

The host material of the hole transport layer contains the organic luminescent material. the

The present invention also provides an organic electroluminescent device, including a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;

The organic light-emitting functional layer includes a hole transport layer, an organic light-emitting layer and an electron transport layer;

The host material of the organic light-emitting layer contains the organic light-emitting material. the

For the convenience of description, the hole transport material referred to in the follow-up content of this application is the host material of the hole transport layer, and the host material is the host material of the organic light-emitting layer. the

Compared with prior art, the present invention has following advantage:

In this invention, we propose a new material, so that in the mother core A series of compounds with a general formula of a carbazole bonded on it, this new material is suitable as both a host material and a hole transport material, when the mother nucleus is connected with a condensed ring aromatic hydrocarbon, such a material is suitable as a light-emitting host material, application On the device, the luminous efficiency can be greatly improved, and the device life is longer. When triarylamines or condensed heterocyclic aromatic hydrocarbons are connected to the core, such as carbazole groups, dibenzothiophene groups, dibenzofuran groups, etc., such materials are suitable as hole transport materials. This new material is better used as a hole transport material in red light devices. The use of the material in the invention reduces the turn-on voltage of the device, improves the luminous efficiency of the device, and increases the service life of the device.

(2) The preparation process of the compound of the present invention is simple and easy, and these compounds have good thermal stability and high hole mobility, and the electroluminescent device made of this material has a greatly reduced turn-on voltage and a low luminous efficiency. At the same time, the service life of the device is significantly increased, and it can be used as a hole transport material or a host material of an organic light-emitting layer in an organic electroluminescent device. the

Description of drawings

In order to make the content of the present invention easier to understand, the Gaussian03B3LYP/6-31G (d) method is used in the present invention to obtain the highest occupied molecular orbital (HOMO), the lowest unoccupied orbital (LUMO) and the triplet energy level (T1 ). the

Figure 1 is the highest occupied molecular orbital of compound 9 in Example 10 of the present invention, the HOMO energy level is -5.040ev, and the triplet energy level T1=1.7362ev;

Fig. 2 is the lowest empty orbital of compound 9 in Example 10 of the present invention, and the LUMO energy level is -1.542ev. the

Detailed ways

The basic raw material used in the present invention, 6-bromine 2,4-Dibromonitrobenzene, 2,5-dibromonitrobenzene, and bromocarbazole derivatives, bromodibenzofuran, bromodibenzothiophene, bromo Derivatives, bromotriphenylene, bromopyrene, bromoanthracene derivatives, etc., can be bought in major domestic chemical raw material markets, and the above-mentioned brominated condensed ring aromatics can be synthesized by common laboratory methods to produce their boronic acid derivatives.

Example 1

For the preparation embodiment of the intermediate of the present invention:

main intermediate Synthesis of -6-boronic acid

6.12g of 6-bromo (Molecular weight 306, 0.02mol) was dissolved in 100ml of dry THF, 10ml of n-butyl (2.5M, 0.025mol) was added dropwise at -80°C, stirred for 15min, and 16ml of triisopropyl borate was added dropwise. Hydrolyze, adjust the pH to neutral, and precipitate 5.5 g of white boric acid derivatives, with a yield of nearly 100%.

Example 2

Synthesis of Compound 1,

(1) The first step

1000ml bottle with magnetic stirrer, add -6-boronic acid 5.5g (molecular weight 272, 0.02mol), 2,4-dibromonitrobenzene 5.84g (molecular weight 278, 0.021mol), Pd(PPh3)4 dosage 1.5g (molecular weight 1154, 0.0013mol), Sodium carbonate 150ml (2M), toluene 150ml, ethanol 150ml. After argon replacement, reflux, monitor the reaction with TLC, after 3 hours, the reaction is complete, lower the temperature, separate out the base layer, evaporate to dryness, and use 1/10 ethyl acetate/petroleum ether for column separation to obtain, 7.82g product, molecular weight 427, yield 91.5%.

(2) The second step

In a 50 ml bottle equipped with magnetic stirring, add 7.82 g of the final product of the first step (molecular weight 427, 0.0183 mol), 5.76 g of triphenylphosphine (molecular weight 262, 0.022 mol), and 150 ml of o-dichlorobenzene. The mixture was heated to 175°C, stirred, and the progress of the reaction was monitored with a TCL plate, and the reaction was completed in 15 hours. Cool, evaporate the solvent in vacuo, wash with water, dry, separate by column chromatography, and rinse with a mixture of ethyl acetate and petroleum ether to obtain 6.5 g of the target molecule with a molecular weight of 395 and a yield of 89.6%. the

(3) The third step

500ml one-necked bottle, equipped with magnetic stirring, add 6.5g of the final product of the second step (molecular weight 395, 0.0164mol), p-methyliodobenzene 5.45g (molecular weight 218, 0.025mol), cuprous iodide 1.0g (molecular weight 190, 0.00526 mol), potassium carbonate 8.3g (138, 0.06mol), DMPU solvent 100ml. The mixture was heated to 175°C, stirred, and the progress of the reaction was monitored with a TCL plate, and the reaction was completed in 13 hours. Cooled, poured into water, filtered, dried, separated by column chromatography, eluting with a mixture of ethyl acetate and petroleum ether to obtain 6.88 g of the target molecule with a molecular weight of 487 and a yield of 86.1%. the

(4) The fourth step

1000ml one-necked bottle, equipped with magnetic stirring, add 6.88g of the final product of the third step above (molecular weight: 487, 0.0141mol), 4.74g of triphenylamine-4-boric acid (molecular weight: 289, 0.0164mol), and the amount of Pd(PPh3)4 used is 1.50 g (molecular weight 1154, 0.0013mol), sodium carbonate aqueous solution 130ml (2M), toluene 130ml, ethanol 130ml. After argon replacement, reflux, and monitor the reaction with TLC. After 4 hours, the reaction was complete, and the temperature was lowered. Most of the solid product was precipitated, filtered, and purified by recrystallization (column separation method if necessary) to obtain 6.73g of product. Molecular weight 636, yield 75%. the

Example 3

Synthesis of Compound 2

The synthetic steps are the same as the four-step reaction in Example 2, except that in the third step, p-methyliodobenzene is changed into iodobenzene, and in the fourth step, triphenylamine-4-boronic acid is changed into 4-(N-phenyl- (1-naphthyl)amino)phenylboronic acid to give compound 2. the

Example 4

Synthesis of Compound 3

The synthesis steps are the same as the four-step reaction in Example 2, and in the third step, p-methyliodobenzene is replaced by 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed into N-phenylcarbazole-3 - boronic acid to give compound 3. the

Example 5

Synthesis of Compound 4

The synthesis steps are the same as the four-step reaction in Example 2. In the third step, p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 6,9-diphenylcarba Azole-3-boronic acid to give compound 4. the

Example 6

Synthesis of Compound 5

The synthetic steps are divided into four steps, and the first three steps are the same as the first three steps in the embodiment 2. In the third step, p-methyl iodobenzene is changed to 2-iodonaphthalene; and the fourth step is the same as that in the embodiment 2. In the third step, the p-methyliodobenzene is changed to 4-(carbazol-9-yl)iodobenzene to obtain compound 5. the

Example 7

Synthesis of Compound 6

The synthetic steps are divided into four steps, and the first three steps are the same as the first three steps in the embodiment 2. In the third step, p-methyl iodobenzene is changed to 2-iodonaphthalene; and the fourth step is the same as that in the embodiment 2. The third step of the reaction is to change p-methyliodobenzene into 3-phenylcarbazole to obtain compound 6. the

Example 8

Synthesis of compound 7

The synthesis steps are the same as the four-step reaction in Example 2, and in the third step, p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 8-phenyldibenzothiophene -2-boronic acid to obtain compound 7. the

Example 9

Synthesis of Compound 8

The synthetic steps are the same as the four-step reaction in Example 2, except that in the third step, p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 8-phenyl dibenzo furan-2-boronic acid to obtain compound 8. the

Example 10

Synthesis of Compound 9

The synthetic steps are the same as the four-step reaction in Example 2, except that in the third step, p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 10-(2-naphthyl ) anthracene-9-boronic acid to obtain compound 9. the

Example 11

Synthesis of Compound 10

The synthesis steps are the same as the four-step reaction in Example 2, except that in the third step p-methyliodobenzene is replaced by 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed into pyrene-1-boronic acid to obtain Compound 10. the

Example 12

Synthesis of Compound 11

The synthetic steps are the same as the four-step reaction in Example 2, except that in the third step p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to triphenylene-2-boronic acid, Compound 11 was obtained. the

Example 13

Synthesis of Compound 12

The synthesis steps are the same as the four-step reaction in Example 2, except that in the third step, p-methyliodobenzene is changed to 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to triphenylamine-6-boronic acid to obtain Compound 12. the

Example 14

Synthesis of Compound 13

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; 2-iodonaphthalene; in the fourth step, change triphenylamine-4-boronic acid to 4-(N-phenyl-N(1-naphthyl)amino)phenylboronic acid to obtain compound 13. the

Example 15

Synthesis of Compound 14

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; It is 2-iodonnaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to dibenzothiophene-4-boronic acid to obtain compound 14. the

Example 16

Synthesis of Compound 15

Synthetic steps are the same as the four-step reaction in embodiment 2, just change 2,4-dibromonitrobenzene into 2,5-dibromonitrobenzene in the first step; It is 2-iodonnaphthalene; in the fourth step, change triphenylamine-4-boronic acid to 8-phenyldibenzothiophene-2-boronic acid to obtain compound 15. the

Example 17

Synthesis of Compound 16

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; is 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 8-phenyldibenzofuran-2-boronic acid to obtain compound 16. the

Example 18

Synthesis of Compound 17

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; is 2-iodonnaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 10-(2-naphthyl)anthracene-9-boronic acid to obtain compound 17. the

Example 19

Synthesis of Compound 18

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; is 2-iodonnaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to 4-(10-(2-naphthyl)anthracen-9-yl)phenylboronic acid to obtain compound 18. the

Example 20

Synthesis of Compound 19

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; is 2-iodonaphthalene; in the fourth step, triphenylamine-4-boronic acid is changed to pyrene-1-boronic acid to obtain compound 19. the

Example 21

Synthesis of Compound 20

Synthesis step is the same as the four-step reaction in embodiment 2, just will change 2,4-dibromonitrobenzene into 2,5-dibromonitrobenzene in the first step; Change to 2-iodonaphthalene; change triphenylamine-4-boronic acid to 12-phenyldr-6-boronic acid in the fourth step to obtain compound 20. the

Example 22

Synthesis of Compound 21

The synthetic procedure is the same as the four-step reaction in Example 2, except that 2,4-dibromonitrobenzene is changed to 2,5-dibromonitrobenzene in the first step; is 2-iodonaphthalene; changing triphenylamine-4-boronic acid to triphenylene-2-boronic acid in the fourth step affords compound 21. the

The mass spectrum detection data and elemental analysis data of the obtained compound 1-21 are shown in Table 1. the

The following are the mass spectrometry and elemental analysis data of Compound 1 to Compound 21 of the present invention:

Example 23

Application examples of each compound of the present invention

In order to facilitate the comparison of the properties of these hole transport materials and fluorescent host materials, the present invention designs a simple electroluminescent device, and we use HAT as the material for the hole injection layer and NPB as the material for comparison. The organic light-emitting layer is composed of a light-emitting host and a dopant material. We use the traditional light-emitting host material EM1 as a comparison material, and EM2 as a light-emitting dopant material. The structures of HAT, NPB, EM1, and EM2 are:

The structure of the organic electroluminescence device in the embodiment of the present invention is:

Substrate/anode/hole injection layer (HIL)/hole transport layer (HTL)/organic light-emitting layer (EL)/electron transport layer (ETL)/cathode. the

The substrate can be a substrate in a conventional organic light emitting device, such as glass or plastic. In the manufacture of the organic electroluminescent device of the present invention, a glass substrate is selected, and ITO is used as an anode material. the

Electron injection materials can use various polyarylamines that are very easy to donate electrons, and can also use extremely electron-deficient polycyano-based materials. Such molecules often use their lowest unoccupied orbitals (LUMO) to transfer electrons. The hole injecting material used in the present invention is HAT. the

Various triarylamine materials can be used for the hole transport layer. The materials described in the present invention can be used as hole-transport materials in electroluminescent devices, compared with the conventional hole-transport material NPB. the

There are many kinds of light-emitting layer materials. The materials described in the present invention can be used as luminescent host materials in electroluminescent devices, and the luminescent dopant material is EM2. the

There are many kinds of electron transport layer materials. In order to characterize the materials described in the present invention, here we use ordinary AlQ3 as the electron transport material, the purpose is to compare the performance of the materials in the present invention, not to pursue the excellence of device performance. the

The cathode can adopt metal and its mixture structure, such as Mg:Ag, Ca:Ag, etc., or it can be an electron injection layer/metal layer structure, such as LiF/Al, Li2O/Al and other common cathode structures. The cathode material selected in the fabrication of the organic electroluminescent device of the present invention is LiF/Al. the

Example 24

The compounds in this example are used as hole transport materials in organic electroluminescent devices, and a number of organic electroluminescent devices have been prepared. The structure is: ITO/HAT (5nm)/hole transport material (40nm)/EM1 : EM2(30nm)/Alq ₃ (20nm)/LiF(0.5nm)/Al(150nm);

For a comparative organic electroluminescent device, NPB is selected as the hole transport material, and the material of the present invention is selected for the remaining organic electroluminescent devices. the

The preparation process of the organic electroluminescent device in this embodiment 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, baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light. Light and ozone cleaning, and bombardment of the surface 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 ^-3 Pa, and vacuum-deposit HAT on the above-mentioned anode layer film as a hole injection layer, and the evaporation rate is 0.1nm/s, the vapor deposition film thickness is 5nm;

On the hole injection layer, one layer of specific compound 1, 3, 4, 6, 7, 8, 11, 13, 14, 15 or NPB in the present invention is evaporated as the hole transport layer, and the evaporation rate is 0.1 nm/s, the evaporated film thickness is 40nm;

On top of the hole transport layer, the luminescent layers EM1 and EM2 (ratio 95%:5%) are vacuum evaporated, the evaporation rate is 0.1nm/s, and the total film thickness is 30nm;

A layer of AlQ3 is vacuum-evaporated on the light-emitting layer as the electron transport material, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 20nm;

LiF with a thickness of 0.5nm was vacuum-deposited on the electron transport layer (ETL) as the electron injection layer, and an Al layer with a thickness of 150nm was used as the cathode of the device. the

The properties of organic electroluminescent devices are shown in the table below:

Compound number Required brightness cd/m ² Voltage V Current efficiencycd/A NPB 5000.00 6.8 25.1

[0143] 1 5000.00 6.3 27.0 3 5000.00 6.5 27.2 4 5000.00 6.0 26.8 6 5000.00 6.1 28.1 7 5000.00 6.4 28.3 8 5000.00 6.2 28.1 11 5000.00 6.3 28.0 13 5000.00 6.6 27.9 14 5000.00 6.3 27.3 15 5000.00 6.2 27.6

Example 25

The compounds in this example are used as hole transport materials in organic electroluminescent devices, and a number of organic electroluminescent devices have been prepared. The structure is: ITO/HAT (40nm)/NPB (40nm)/luminescent host material: EM2 (85%: 15%, 30nm)/Alq3 (20nm)/LiF (0.5nm)/Al (150nm);

For a comparative organic electroluminescent device, EM1 was selected as the main light-emitting material, and the materials of the present invention were selected for the remaining organic electroluminescent devices. the

The preparation process of the organic electroluminescent device in this embodiment 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, baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light. Light and ozone cleaning, and bombardment of the surface 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 ^-3 Pa, and vacuum-deposit HAT on the above-mentioned anode layer film as a hole injection layer, and the evaporation rate is is 0.1nm/s, and the evaporated film thickness is 40nm;

On the hole injection layer, a layer of NPB is evaporated as a hole transport layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40nm;

On the hole transport layer, vacuum evaporate the light-emitting layer Compound 1, 9, 11, 12, 17, 18, 19, 20 or EM1 in the present invention, dope and evaporate EM2 (ratio 85%: 15%), evaporate The plating rate is 0.1nm/s, and the total film thickness is 30nm;

A layer of AlQ3 is vacuum-evaporated on the light-emitting layer as the electron transport material, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 20nm;

LiF with a thickness of 0.5nm was vacuum-deposited on the electron transport layer (ETL) as the electron injection layer, and an Al layer with a thickness of 150nm was used as the cathode of the device. the

The performance of the light emitting device is shown in the table below:

Compound number Required brightness cd/m2 Voltage V Current efficiencycd/A EM1 5000.00 6.8 25.1 1 5000.00 6.3 26.9 9 5000.00 6.4 27.3 11 5000.00 6.3 27.7 12 5000.00 6.6 26.7 17 5000.00 6.2 28.1 18 5000.00 6.1 28.3 19 5000.00 6.5 28.5 20 5000.00 6.0 28.0

The above results show that the novel organic luminescent material of the present invention is used in organic electroluminescent devices, can effectively reduce the take-off voltage and improve current efficiency, and is a hole transport material and a luminescent host material with good performance. the

Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the present invention, those skilled in the art can make various modifications and improvements, and the appended claims summarize scope of the invention. the

Claims (9)

1. An organic luminescent material, characterized in that it has a structure as shown in formula (I): in: Independently selected from H, C6-C30 substituted or unsubstituted aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted fused ring aromatic hydrocarbon groups, C6-C30 substituted or unsubstituted fused heterocyclic groups, or five-membered, six-membered membered heterocycle or substituted heterocycle, C6-C30 substituted or unsubstituted triarylamine group, or aryl ether group, one of C1-C12 substituted or unsubstituted aliphatic alkyl groups, Ar ₁ - Ar ₈ is not H at the same time. 2 . The organic luminescent material according to claim 1 , wherein Ar ₅ , Ar ₆ , Ar ₇ , Ar ₈ , and Ar ₉ are H at the same time. 3. The organic luminescent material according to claim 1, wherein the Ar is selected from phenyl, substituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, perylenyl _, pyrenyl. 4. The organic luminescent material according to claim 1, wherein the Ar ₁ , Ar ₂ , and Ar ₃ are independently selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, chrysyl, Triphenylene, substituted phenyl, substituted naphthyl, substituted pyrenyl, substituted chrysyl, substituted anthracenyl, carbazolyl, triphenylene, substituted carbazolyl, dibenzothienyl, substituted dibenzothienyl , Dibenzofuryl, substituted dibenzofuryl, triarylamino, substituted triarylamino. 5. The organic luminescent material according to any one of claims 1-4, wherein the compound is selected from the following structural formulas: 6. An organic luminescent material according to any one of claims 1-5, which is used in an organic electroluminescent device. 7. The organic luminescent material according to claim 6, wherein the organic luminescent material can be used as a hole injection material, a hole transport material or a host material. 8. An organic electroluminescent device, comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; The organic light-emitting functional layer includes a hole transport layer, an organic light-emitting layer and an electron transport layer, characterized in that: The host material of the hole transport layer contains the organic light-emitting material according to any one of claims 1-5. 9. An organic electroluminescent device, comprising a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; The organic light-emitting functional layer includes a hole transport layer, an organic light-emitting layer and an electron transport layer, characterized in that: The host material of the organic light-emitting layer contains the organic light-emitting material according to any one of claims 1-5.