CN106349251A - Organic electroluminescence material comprising 4,5-diazaspiro thioxanthone structure, application of organic electroluminescence material, and device - Google Patents

Abstract

The invention belongs to the field of organic electroluminescent materials, and in particular relates to an organic electroluminescent material containing a 4,5-diazaspiro-thioxanthene structure and its application and device, which can be used in organic light-emitting diodes and has excellent properties Due to its bipolar transmission properties, it can be used as a host material. The structural formula is as follows: Among them, Ar ₁ and Ar ₂ are independently selected from hydrogen atoms, C ₃ -C ₃₀ substituted or unsubstituted carbazole groups, C ₃ -C ₃₀ substituted or unsubstituted arylamine groups, C ₃ -C ₃₀ Substituted or unsubstituted phenothiazine group, C ₃ ~C ₃₀ substituted or unsubstituted phenoxazine group, C ₃ ~C ₃₀ substituted or unsubstituted phenazine group, C ₃ ~C ₃₀ substituted or unsubstituted In the substituted acridine group, Ar ₁ and Ar ₂ are not hydrogen at the same time. The invention also relates to a device comprising at least one layer of said bipolar compound as a host material and a method of manufacturing said device.

Description

An organic electroluminescent material containing 4,5-diazaspirothioxanthene structure and its Applications and Devices

technical field

The invention belongs to the field of organic electroluminescent materials, and in particular relates to an organic electroluminescent material containing a 4,5-diazaspirothioxanthene structure and its application and device.

Background technique

Phosphorescent materials can make full use of the triplet excitons produced by electron-hole recombination in electroluminescent devices, which account for 75% of the ratio. Sub utilization can even reach 100%. Phosphorescent materials are usually doped as guest materials in the host material. An effective host material should have an ideal band gap for efficient energy transfer to the guest, and good carrier transport properties for balanced recombination of carriers in the emissive layer. , energy level matching with adjacent layers for efficient charge injection, and sufficient thermal and morphological stability for extended device lifetime, so the development of host materials is extremely important for high-efficiency electrophosphorescence.

Traditional host materials usually only have a single carrier transport property, and this unbalanced carrier transport property has been shown to be detrimental to the turn-on voltage and lifetime of OLEDs. The development of new host materials must have good bipolar carrier (hole and electron) injection and transport properties to avoid the accumulation of carriers between the light-emitting layer and the charge-transport layer, causing the exciplexes at the interface to emit light , resulting in low external quantum efficiency, power efficiency, current efficiency and other main parameters of the device, high turn-on voltage, and spectral instability. Therefore, bipolar host materials that can balance carrier transport have attracted considerable attention in recent years.

Contents of the invention

The technical problem to be solved by the present invention is to provide an organic electroluminescent material and its application. The present invention relates to an organic electroluminescent material containing a 4,5-diazaspirothioxanthene structure. The organic electroluminescent material has good thermodynamic stability, good film-forming properties and carrier transport ability, and its structure is shown in the general formula (1):

Among them, Ar ₁ and Ar ₂ are independently selected from hydrogen atoms, C ₃ -C ₃₀ substituted or unsubstituted carbazole groups, C ₃ -C ₃₀ substituted or unsubstituted arylamine groups, C ₃ -C 30 ₃₀ Substituted or unsubstituted phenothiazine groups, C ₃ ~C ₃₀ substituted or unsubstituted phenoxazine groups, C ₃ ~C ₃₀ substituted or unsubstituted acridine groups, Ar ₁ and Ar ₂ are different at the same time for hydrogen.

The inventor unexpectedly found in the research that the bipolar host organic electroluminescent material of the present invention has the following advantages:

1. The ambipolar host organic electroluminescent material of the present invention has relatively high carrier injection and transport capabilities.

2. The bipolar host organic electroluminescent material of the present invention has the advantages of relatively high glass transition temperature and thermal decomposition temperature, and high stability of the compound.

3. The bipolar host organic electroluminescent material of the present invention has higher singlet and triplet energy levels, and can be used as a blue or green host material. Using the organic compound of the invention as a host material, the prepared device can effectively improve external quantum efficiency, power efficiency and current efficiency.

Further, the Ar ₁ and Ar ₂ are independently selected from the following structures:

The beneficial effect of adopting the above-mentioned further technical solution is: the inventor unexpectedly found in the research that Ar ₁ and Ar ₂ are independently selected from the above-mentioned groups, which is conducive to improving the thermal stability and carrier transport efficiency of the material.

Further, the structural formula of the compound is preferably selected from any one of the structural formulas in C1-C52:

Compounds C01-C52 are representative structures or preferred structures conforming to the spirit and principle of the present invention. It should be understood that the above compound structures are listed only for better explanation of the present invention, not to limit the present invention.

The beneficial effect of adopting the above-mentioned further technical solution is: the above-mentioned compounds C01-C52 have the advantages of good thermodynamic stability, good carrier transport properties, and good film-forming properties through experimental verification.

The present invention also provides the application of the above bipolar host organic electroluminescence material in the field of organic electroluminescence. The bipolar host organic electroluminescent material can be used as a host material, especially as a blue light host material or a green light host material.

For example: the above materials are used as green light host materials in the field of organic electroluminescence, especially in the light-emitting layer of organic electroluminescence devices. In the specific application process, the implementation process and results are only for better explaining the present invention, not limiting the present invention.

The invention provides an organic electroluminescent device, comprising:

An anode, a cathode, and an organic light-emitting functional layer located between the anode and the cathode, wherein the organic light-emitting functional layer includes the above-mentioned bipolar host organic electroluminescent material.

If there are multiple organic light-emitting functional layers, at least one organic light-emitting functional layer contains the above-mentioned bipolar host organic electroluminescent material.

The beneficial effect of adopting the above-mentioned technical solution is: since the bipolar host organic electroluminescent material of the present invention has good bipolar characteristics of transporting holes and electrons, the organic electroluminescent device prepared by using this material has a brightening effect. Low voltage, high luminous efficiency and other advantages; the bipolar host organic electroluminescent material of the present invention has a higher glass transition temperature and thermal decomposition temperature, and the stability of the compound is high, which is conducive to significantly improving the life of the device; the present invention The bipolar host organic electroluminescent material has relatively high singlet and triplet energy levels, and preferably can be used as a green host material. Using the bipolar host organic electroluminescent material of the present invention as the host material, the prepared device can effectively improve the external quantum efficiency, power efficiency and current efficiency.

Further, the organic light-emitting functional layer includes any one or any combination of hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, hole blocking layer, and electron blocking layer.

Further, the light-emitting layer includes a host material and a guest light-emitting material, wherein the host material includes the bipolar host organic electroluminescent material.

Taking the green light OLED device as an example, it generally includes an ITO conductive glass substrate (anode), a hole injection layer (HATCN), a hole transport layer (TAPC), and a light-emitting layer (the organic electroluminescent material involved in the present invention) stacked in sequence. ), electron transport layer (TmPyPB), electron injection layer (LiF) and cathode layer (Al). All functional layers are made by vacuum evaporation process. The molecular structure formulas of some organic compounds used in such devices are shown below.

In the present invention, the functional layer of the device is not limited to the use of the above materials, these materials can be replaced by other materials, in order to further improve the performance of the device, such as the hole transport layer can be replaced by NPB, etc., and the electron transport layer can be replaced by TpPyPB, TPBi, etc. Instead, the molecular structures of these materials are as follows:

Description of drawings

Fig. 1 is the structural representation of the organic electroluminescence device prepared by the present invention, from lower layer to upper layer, is successively 101, ITO conductive glass substrate, 102, hole injection layer, 103, hole transport layer, 104, light-emitting layer, 105. Electron transport layer, 106. Electron injection layer, 107. Cathode layer, wherein the light-emitting layer relates to the organic electroluminescence material described in the present invention.

detailed description

The principles and features of the present invention are described below, and the examples given are only used to explain the present invention, and are not intended to limit the scope of the present invention.

Embodiment 1: the preparation of intermediate M1

Under nitrogen protection, diphenylsulfone (10.9 g, 0.05 mol) and tetrahydrofuran (109 mL) were added into a 500 mL three-necked flask. The bath temperature was set at -85°C, and the temperature was lowered with stirring. When the internal temperature dropped to -80°C, a solution of n-butyllithium in n-hexane (24 mL, 2.5M) was added dropwise, and the dropping rate was controlled to keep the internal temperature below -80°C. After the dropwise addition, keep the reaction for 3h, move to room temperature at 25°C and stir for 2h. A solution of methyl 5-bromo-[2,2'-bipyridine]-3-carboxylate (14.6 g, 0.05 mol) in tetrahydrofuran (100 mL) was added dropwise. After the dropwise addition was completed, the mixture was stirred for 10 h at room temperature at 25°C. 100mL of saturated ammonium chloride aqueous solution was used to quench the reaction, and hydrolyzed to generate corresponding alcohol intermediates. Separate the liquid, keep the upper organic phase, dry the organic phase with anhydrous sodium sulfate, pass through the column directly, and remove the solvent through the column liquid to obtain 21.5 g of off-white powdery solid.

Add the alcohol intermediate obtained above, 200mL toluene, p-toluenesulfonic acid (0.95g, 0.005mol) into a 500mL three-necked flask, stir and reflux at an internal temperature of 110°C for 3h under nitrogen protection, and monitor the reaction progress by TLC. After the reaction was completed, the reaction liquid was poured into 300 mL of the water phase, and the liquid was separated. The water phase was extracted with 200 mL of ethyl acetate, the liquid was separated, and the organic phase was combined. Dry over anhydrous sodium sulfate, filter with suction, and remove the solvent to obtain a light yellow powdery solid. Silica gel column chromatography separated to obtain 12.4 g of off-white powdery intermediate M1, yield: 54%.

Mass spectrum MS (m/e), molecular formula C ₂₃ H ₁₃ BrN ₂ O ₂ S, theoretical value 459.9, test value 459.0.

Elemental analysis (C ₂₃ H ₁₃ BrN ₂ O ₂ S), theoretical value C: 59.88%, H: 2.84%, Br: 17.32, O: 6.94%, N: 6.07%, S: 6.95%; found value C: 59.77 %, H: 2.74%, Br: 17.35, O: 7.01%, N: 6.07%, S: 7.06%.

Embodiment 2: the preparation of intermediate M2

Using a method similar to Example 1, using an equivalent amount of 6-bromo-[2,2'-bipyridine]-3-methyl carboxylate instead of 5-bromo-[2,2'-bipyridine]-3- Methyl formate, with other conditions unchanged, intermediate M2 was obtained, 5.3 g of off-white solid, yield 23%.

Mass spectrum MS (m/e), molecular formula C ₂₃ H ₁₃ BrN ₂ O ₂ S, theoretical value 459.9, test value 459.6.

Elemental analysis (C ₂₃ H ₁₃ BrN ₂ O ₂ S), theoretical value C: 59.88%, H: 2.84%, Br: 17.32, O: 6.94%, N: 6.07%, S: 6.95%; found value C: 59.87 %, H: 2.79%, Br: 17.40, O: 6.99%, N: 6.10%, S: 6.85%.

Embodiment 3: the preparation of intermediate M3

Using a method similar to Example 1, using an equivalent amount of 5,5'-dibromo-[2,2'-bipyridine]-3-methyl carboxylate instead of 5-bromo-[2,2'-bipyridine ]-3-Methyl carboxylate, other conditions remained unchanged, to obtain intermediate M3, off-white solid 11.3g, yield 42%.

Mass spectrum MS (m/e), molecular formula C ₂₃ H ₁₂ Br ₂ N ₂ O ₂ S, theoretical value 537.9, test value 538.1.

Elemental analysis (C ₂₃ H ₁₂ Br ₂ N ₂ O ₂ S), theoretical value C: 51.14%, H: 2.24%, Br: 29.58, O: 5.92%, N: 5.19%, S: 5.94%; found value C : 51.22%, H: 2.25%, Br: 29.47, O: 5.95%, N: 5.20%, S: 5.91%.

Embodiment 4: the preparation of intermediate M4

Using a method similar to Example 1, using an equivalent amount of 6,6'-dibromo-[2,2'-bipyridine]-3-methyl carboxylate instead of 5-bromo-[2,2'-bipyridine ]-3-Methyl carboxylate, other conditions remained unchanged, to obtain intermediate M4, off-white solid 5.1 g, yield 19%.

Mass spectrum MS (m/e), molecular formula C ₂₃ H ₁₂ Br ₂ N ₂ O ₂ S, theoretical value 537.9, test value 537.3.

Elemental analysis (C ₂₃ H ₁₂ Br ₂ N ₂ O ₂ S), theoretical value C: 51.14%, H: 2.24%, Br: 29.58, O: 5.92%, N: 5.19%, S: 5.94%; found value C : 51.16%, H: 2.22%, Br: 29.57, O: 5.95%, N: 5.15%, S: 5.95%.

Embodiment 5: the preparation of compound C1

Under nitrogen atmosphere, add M1 (4.6g, 0.01mol), carbazole (2g, 0.012mol), N,N-dimethylpropenyl urea (DMPU) (100mL), cuprous iodide to a 250ml three-necked flask in sequence (190 mg, 0.001 mol), 18-C-6 (528 mg, 0.002 mol), K ₂ CO ₃ (4.2 g, 0.03 mol). The bath temperature was set at 155° C., and the reaction was stirred for 16.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after monitoring the complete reaction of the raw materials by TLC. Extract with dichloroethane, separate the layers, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, and remove the solvent from the filtrate. Purified by column chromatography, purified and separated to obtain 3.6 g of white powdery solid with a yield of 66%.

Embodiment 6: the preparation of compound C2

Using a method similar to Example 5, using equimolar equivalents of M2 instead of M1, and other conditions unchanged, C2 was obtained, 2.5 g of white solid, with a yield of 45%.

Embodiment 7: the preparation of compound C3

Using a method similar to that of Example 5, using equimolar equivalents of 3,6-di-tert-butylcarbazole instead of carbazole, and other conditions unchanged, C3 was obtained, 2.2 g of white solid, with a yield of 33%.

Embodiment 8: the preparation of compound C5

Under nitrogen atmosphere, add M1 (4.6g, 0.01mol), diphenylamine (2g, 0.012mol), o-xylene (100mL), sodium tert-butoxide (2.9g, 0.03mol) to a 250ml three-necked flask in sequence, and stir at room temperature After 15 min, palladium acetate (22.5 mg, 0.1 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-phos) (84 mg, 0.2 mmol) were added. The bath temperature was set at 150° C., and the reaction was stirred for 12.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after the complete reaction of the raw materials was monitored by TLC. Wash the organic phase with water until neutral, separate the layers, dry the organic phase with anhydrous sodium sulfate, filter with suction, and remove the solvent from the filtrate. Purified by column chromatography, purified and separated to obtain 4.1 g of white powdery solid with a yield of 75%.

Embodiment 9: the preparation of compound C6

Using a method similar to that of Example 8, using equimolar equivalents of 4,4'-di-tert-butyldiphenylamine instead of diphenylamine, and other conditions unchanged, C6 was obtained as a white solid, 5.4 g, with a yield of 82%.

Embodiment 10: the preparation of compound C7

Using a method similar to that of Example 8, using equimolar equivalents of M2 instead of M1, and other conditions unchanged, C7 was obtained, 2.4 g of a white solid, with a yield of 44%.

Embodiment 11: the preparation of compound C10

Using a method similar to Example 5, using equimolar equivalents of 7H-benzofuro[2,3-b]carbazole instead of carbazole, and other conditions unchanged, C10 was obtained, 3.8g of white solid, yield 60% .

Embodiment 12: the preparation of compound C12

Using a method similar to that of Example 5, using an equimolar equivalent of the intermediate M5 instead of carbazole, and other conditions unchanged, C12 was obtained as an off-white solid of 3.7 g with a yield of 56%.

Embodiment 13: Preparation of compound C13

Using a method similar to that of Example 5, using an equimolar equivalent of M6 instead of carbazole, and other conditions unchanged, C13 was obtained, 4.6 g of a white solid, with a yield of 65%.

Embodiment 14: the preparation of compound C15

Using a method similar to Example 5, using equimolar equivalents of M2 to replace M1, equimolar equivalents of M5 to replace carbazole, and other conditions unchanged, C15 was obtained as a white solid of 3.8 g with a yield of 57%.

Embodiment 15: Preparation of compound C19

Using a method similar to that of Example 8, using equimolar equivalents of phenoxazine instead of diphenylamine, and other conditions unchanged, C19 was obtained, 1.7 g of white solid, with a yield of 30%.

Embodiment 16: Preparation of Compound C20

Using a method similar to Example 8, using equimolar equivalents of phenothiazine instead of diphenylamine, and other conditions unchanged, C20 was obtained, 1.8 g of white solid, with a yield of 31%.

Embodiment 17: Preparation of compound C21

Using a method similar to that of Example 8, using equimolar equivalents of 9,9-dimethylacridine instead of diphenylamine, and other conditions unchanged, C21 was obtained, 2.0 g of white solid, with a yield of 34%.

Embodiment 18: Preparation of Compound C22

Using a method similar to Example 8, using equimolar equivalents of 5,10-dihydro-5-phenylphenazine instead of diphenylamine, and other conditions unchanged, C22 was obtained, 2.5 g of yellow-white solid, yield 39% .

Embodiment 19: Preparation of compound C25

Using a method similar to Example 8, using equimolar equivalents of intermediate M7 instead of diphenylamine, and other conditions unchanged, C25 was obtained, 3.6 g of a yellow-white solid, with a yield of 53%.

Embodiment 20: Preparation of compound C27

Using a method similar to that of Example 8, using equimolar equivalents of intermediate M8 instead of diphenylamine, and other conditions unchanged, C27 was obtained, 2.2 g of white solid, with a yield of 31%.

Embodiment 21: Preparation of compound C31

Using a method similar to that of Example 8, using equimolar equivalents of diphenylidine instead of diphenylamine, and other conditions unchanged, C27 was obtained as a white solid of 3.5 g with a yield of 50%.

Embodiment 22: Preparation of Compound C33

Using a method similar to that of Example 8, using equimolar equivalents of the intermediate M9 instead of diphenylamine, and other conditions unchanged, C33 was obtained, 4.9 g of a white solid, with a yield of 66%.

Embodiment 23: Preparation of compound C35

Using a method similar to that of Example 8, using equimolar equivalents of the intermediate M10 instead of diphenylamine, and other conditions unchanged, C35 was obtained as a white solid, 5.0 g, with a yield of 73%.

Embodiment 24: Preparation of compound C38

Under nitrogen atmosphere, M3 (5.4g, 0.01mol), phenoxazine (4g, 0.022mol), o-xylene (100mL), sodium tert-butoxide (2.9g, 0.03mol) were added to a 250ml three-necked flask in sequence, at room temperature After stirring for 15 min, palladium acetate (22.5 mg, 0.1 mmol), 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-phos) (84 mg, 0.2 mmol) were added. The bath temperature was set at 150° C., and the reaction was stirred for 12.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after the complete reaction of the raw materials was monitored by TLC. Wash the organic phase with water until neutral, separate the layers, dry the organic phase with anhydrous sodium sulfate, filter with suction, and remove the solvent from the filtrate. Purified by column chromatography, purified and separated to obtain 4.3 g of white powdery solid with a yield of 58%.

Embodiment 25: Preparation of compound C39

Under nitrogen atmosphere, add M3 (5.4g, 0.01mol), carbazole (3.7g, 0.022mol), N,N-dimethylpropenyl urea (DMPU) (100mL), iodinous Copper (190 mg, 0.001 mol), 18-C-6 (528 mg, 0.002 mol), K ₂ CO ₃ (4.2 g, 0.03 mol). The bath temperature was set at 155° C., and the reaction was stirred for 16.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after monitoring the complete reaction of the raw materials by TLC. Extract with dichloroethane, separate the layers, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, and remove the solvent from the filtrate. Purified by column chromatography, purified and separated to obtain 5.2 g of white powdery solid with a yield of 73%.

Embodiment 26: Preparation of Compound C45

Using a method similar to that in Example 24, using equimolar equivalents of 9,9-dimethylacridine instead of phenoxazine, and other conditions unchanged, C45 was obtained as a white solid, 5.0 g, with a yield of 63%.

Embodiment 27: Preparation of compound C47

Under nitrogen atmosphere, add M3 (5.4g, 0.01mol), bis-boronic acid pinacol ester (12.7g, 0.05mol), toluene (100mL), and potassium carbonate (7g, 0.05mol) to a 250ml three-necked flask in turn, at room temperature After stirring for 15 min, tetrakis(triphenylphosphine)palladium (116 mg, 0.1 mmol) was added. The bath temperature was set at 100° C., and the reaction was stirred for 12.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after monitoring the complete reaction of the raw materials by TLC. Purified by column chromatography, purified and separated to obtain 4g of intermediate M11.

Under nitrogen atmosphere, add above-mentioned intermediate M11 (4.0g, 0.0063mol), 9-(4-bromophenyl)carbazole (4.5g, 0.014mol), toluene (150mL), potassium carbonate ( 2.6g, 0.019mol), after stirring at room temperature for 15min, add palladium acetate (67mg, 0.3mmol), 2-bicyclohexylphosphine-2', 6'-dimethoxybiphenyl (S-phos) (252mg, 0.6mmol ). The bath temperature was set at 110° C., and the reaction was stirred for 10.0 h under the protection of nitrogen, and the temperature was lowered to room temperature after monitoring the complete reaction of the raw materials by TLC. Purified by column chromatography, purified and separated to obtain C47, 6.7 g of white solid, with a total yield of 77%.

Example 28: Preparation of Compound C51

Using a method similar to Example 27, use 10-(4-bromophenyl)-9,9-dimethylacridine instead of 9-(4-bromophenyl)carbazole, molar ratio: 10-(4 -Bromophenyl)-9,9-dimethylacridine/M11=2.2/1, and other conditions remained unchanged, C51 was obtained, 6.5 g of white solid, yield 68%.

Compound Mass Spectrometry and Elemental Analysis:

Below are the application examples of the compounds of the present invention:

Example 29: Preparation of Device 1-Device 8

Preparation:

a) Cleaning ITO (indium tin oxide) glass: ultrasonically clean the ITO glass with deionized water, acetone, and ethanol for 30 minutes each, and then treat it in a plasma cleaner for 5 minutes;

b) Vacuum evaporation of the hole injection layer HAT-CN on the anode ITO glass with a thickness of 10nm;

c) Vacuum-evaporating a hole-transport layer TAPC on the hole-injection layer with a thickness of 40 nm;

d) On the hole transport layer, vacuum evaporate the light-emitting layer bipolar host compound: 15%wt Ir(ppy) ₃ with a thickness of 30nm;

e) On the light-emitting layer, TmPyPB as an electron transport layer is vacuum mixed and evaporated, with a thickness of 30nm;

f) On top of the electron transport layer, an electron injection layer LiF is vacuum evaporated with a thickness of 1 nm;

g) On the electron injection layer, a cathode Al is vacuum-evaporated to a thickness of 100 nm.

The structure of the device is ITO/HAT-CN(10nm)/TAPC(40nm)/bipolar host compound: 15%wt Ir(ppy) ₃ (30nm)/TmPyPB(30nm)/LiF(1nm)/Al(100nm) , during the vacuum evaporation process, the pressure was <4.0×10 ^-4 Pa, and the test results of the obtained devices are shown in Table 1.

Comparative Example 1: An organic electroluminescent device was fabricated according to the same method as in Example 29, except that 4,4'-bis(9H-carbazole)-1,1'-biphenyl (CBP) was used as the main body of the light-emitting layer Substitute the bipolar compound prepared in the examples. The test results of the obtained devices are shown in Table 1.

Table 1 Device optoelectronic data sheet

For comparison, the present invention fabricated a reference device using the conventional host material CBP. Compared with the conventional host material CBP, the organic electroluminescent device prepared based on the host material of the present invention shows excellent characteristics in terms of efficiency, driving voltage and stability. In particular, high light emitting characteristics are exhibited in terms of efficiency, and the host material of the present invention has remarkable bipolar characteristics.

The above descriptions are only preferred embodiments of the present invention, and are not limitations of the present invention. The present invention aims to provide a spirothioxanthene organic electroluminescent material containing 4,5-diaza, and the electroluminescent device made of the material provided by the present invention has room for further improvement in device performance, such as Using other materials instead of TAPC as the hole transport layer, using other materials instead of TmPyPB as the electron transport layer, using other doping methods to make the light emitting layer, etc., similar improvements should be understood as belonging to the protection category of the present invention.

Claims (7)

1. the electroluminescent organic material that one kind comprises 4,5- diaza spiro formula thioxanthene is it is characterised in that have formula (1) institute The structure shown,

Wherein, ar₁、ar₂It is independently selected from hydrogen atom, c₃～c₃₀Replace or non-substituted carbazole group, c₃～c₃₀Take Generation or non-substituted arylamine group, c₃～c₃₀Replace or non-substituted phenothiazine group, c₃～c₃₀Replace or non-substituted Azophenlyene group, c₃～c₃₀Replace or non-substituted azophenlyene group, c₃～c₃₀Replace or non-substituted acridine group, ar₁、ar₂It is asynchronously hydrogen.

2. the electroluminescent organic material comprising 4,5- diaza spiro formula thioxanthene according to claim 1, its feature exists In described ar₁、ar₂It is independently selected from following structure:

3. the electroluminescent organic material comprising 4,5- diaza spiro formula thioxanthene according to claim 1, its feature exists In any one in c1-c52 of structural formula of compound:

4. a kind of according to the arbitrary described organic electroluminescence material comprising 4,5- diaza spiro formula thioxanthene of claims 1 to 3 Material application it is characterised in that: as material of main part or charge transport materials.

5. a kind of organic electroluminescence device it is characterised in that include: anode, negative electrode and be located at described anode and described the moon Organic luminescence function layer between pole, wherein, described organic luminescence function layer is included described in any one in claims 1 to 3 The electroluminescent organic material comprising 4,5- diaza spiro formula thioxanthene.

6. organic electroluminescence device according to claim 5 it is characterised in that: described organic luminescence function layer includes sky Appointing in cave implanted layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, hole blocking layer or electronic barrier layer Anticipate one or more layers combination.

7. organic electroluminescence device according to claim 6 it is characterised in that: described hole transmission layer, luminescent layer Or at least one of electron transfer layer comprises to comprise 4,5- diaza spiro formula sulfur described in claims 1 to 3 any one The electroluminescent organic material of miscellaneous anthracene.