KR102339410B1 - Devices containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran - Google Patents

Abstract

The present invention provides a device containing an anode material of 4,6-diphenyl sulphone dibenzofuran, which includes a cathode, an anode and an organic layer, the organic layer comprising a hole transport layer and a hole at least one of a blocking layer, an electron transport layer, and a light emitting layer, wherein the organic layer contains a bipolar host material, wherein the bipolar host material has the structure of Formula (I), wherein R ₁ -R ₆ is an alkyl substituted or Unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamines Derivative, hydrogen, halogen, C1-C4 alkyl, wherein _{at least one of R 1} -R ₆ is alkyl-substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole , diphenylamine or other aromatic diphenylamine derivatives. As a result of the experiment, the organic electroluminescent device made of the bipolar host material has high stability and excellent current efficiency and external quantum efficiency.

Description

Devices containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran

The present invention relates to an organic light emitting diode, and more particularly to a device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, and belongs to the technical field of organic light emitting materials.

Compared with liquid crystal displays that require backlight, organic light emitting diodes (OLEDs) have characteristics such as active light emission, fast response speed, low energy consumption, high luminance, wide viewing angles and flexibility, so they are expected to be used in the flat panel display field. It is considered one of the most promising products of the 21st century, as it is quite large and attracts great attention from academia and industry. Currently, OLED devices have already been mass-produced and are widely used in electronic products such as mobile phones, tablet PCs, automobile meters, and wearable devices. Electrofluorescence and electrophosphorescence are referred to as first-generation and second-generation OLEDs, respectively. Fluorescent material-based OLEDs have high stability, but are limited by quantum statistical laws, and since the ratio of singlet excitons to triplet excitons is 1:3 under electrical activation, the maximum quantum efficiency in the electroluminescence of the fluorescent material is 25% only to On the other hand, phosphorescent materials exhibit the spin orbital bonding action of heavy atoms, so that singlet excitons and triplet excitons can be used comprehensively, and the theoretical internal quantum efficiency can reach 100%. However, phosphorescent OLED has a significant roll-off effect in efficiency, which limits its application to high-brightness fields.

공명 에너지 전달(FRET)에 의해 게스트 물질로 전달되어, 삼중항 엑시톤 농도가 낮아지고 소자의 성능도 개선된다. 따라서 고효율 유기 발광 다이오드를 위해서는 고성능 호스트 물질을 개발하는 것이 상당히 중요하다.The phosphorescent material can use singlet excitons and triplet excitons comprehensively, so 100% internal quantum efficiency can be realized. According to the study, triplet-triplet annihilation (TTA) and triplet-polaron annihilation (TPA) were performed because the excited state exciton lifetime of the transition metal complex is relatively long and triplet excitons can be accumulated under high current densities. It was found that a phenomenon such as an efficiency roll-off appears. To overcome this problem, researchers often dope phosphorescent materials into organic host materials, for example doping into bipolar host materials to better balance carrier injection. Recently, a material having thermally activated delayed fluorescence properties is also applied to a host of a phosphorescent device. The thermally activated delayed fluorescence material has a relatively small singlet-triplet energy level difference, so triplet excitons are reversely crossed into singlets and then again.

It is transferred to the guest material by resonance energy transfer (FRET), which lowers the triplet exciton concentration and improves the device's performance. Therefore, it is very important to develop a high-performance host material for a high-efficiency organic light-emitting diode.

Currently, a widely used host material for phosphorescent devices is CBP (4,4'-bis (9-carbazolyl) biphenyl) (4,4'-bis (9-carbazolyl) biphenyl), but the required driving voltage is high and The glass transition temperature (T _g ) (T _g =62° C.) is low and easy to crystallize. In addition, CBP is a P-type material, and since the hole mobility is much higher than the electron mobility, it is not beneficial to the carrier injection and transport balance, and the luminous efficiency is low.

The present invention provides a device containing a bipolar material of 4,6-diphenyl sulphone dibenzofuran, wherein the bipolar material comprises 4,6-diphenyl sulfone dibenzofuran as an electronic core As an acceptor, a DALAD-type bipolar material is formed by using a derivative such as diphenylamine, carbazole, and acridine as a linker, which has an electron-donating ability, so the glass transition temperature is higher and the host material Since the thermal stability of the organic electroluminescent device prepared with the bipolar host material of the present invention is high, the stability is high.

A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran includes a cathode, an anode and an organic layer, wherein the organic layer is at least one of a hole transport layer, a hole blocking layer, an electron transport layer, and a light emitting layer, wherein the organic layer comprises 4 ,6-diphenyl sulfone dibenzofuran-based bipolar host material, wherein the bipolar host material has a structure of formula (I).

Here, R ₁ -R ₆ is an alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole ( indenocarbazole), diphenylamine or other aromatic diphenylamine derivatives, hydrogen, halogen, C1-C4 alkyl, and _{at least one of R 1} -R ₆ is alkyl-substituted or unsubstituted acridinyl; phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives.

Preferably _{, two of R 1} , R 2 and R ₃ are hydrogen, halogen or C1-C4 alkyl and the other is C1-C8 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives, wherein two of R ₄ , R ₅ and R ₆ are hydrogen, halogen or C1-C4 alkyl and the other is C1-C8 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives.

Preferably, R ₁ and R ₄ are identical, R ₂ and R ₅ are identical, and R ₃ and R ₆ are identical.

Preferably, R ₂ , R ₃ , R ₅ and R ₆ are hydrogen, halogen or C1-C4 alkyl, R ₁ and R ₄ are C1-C4 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenothiazinyl noxazinyl, carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives.

Preferably R ₂ , R ₃ , R ₅ and R ₆ are hydrogen, and R ₁ and R ₄ are C1-C4 alkyl substituted or unsubstituted acridinyl, carbazole, indenocarbazole.

The compound of formula (I) is one of the compounds of the structures listed below.

The organic light emitting diode device includes a cathode, an anode and an organic layer, wherein the organic layer is at least one of a hole transport layer, a hole blocking layer, an electron transport layer, and a light emitting layer. The organic layer is in accordance with demand, and each layer is not necessarily present in the organic layer.

The compound of formula (I) is a material of the light emitting layer.

The total thickness of the organic layer of the electronic device of the present invention is 1 to 1000 nm, preferably 1 to 500 nm, more preferably 5 to 300 nm.

The organic layer may be formed into a thin film by deposition or spin coating.

As mentioned above, the compounds of formula (I) of the present invention are as follows, but are not limited to the structures listed below.

The method for preparing the bipolar host material includes the following preparation steps.

First, dibenzofuran (a) is formed as a lithium salt under n-butyllithium conditions, and then iodized to 4,6-diiododibenzo furan (4,6-diiododibenzo furan) (b ), and a thioether intermediate (c) was obtained through a Ullmann reaction with a halogenated thiophenol (fluorination, bromination); oxidation of the halogenated thioether intermediate to give the halogenated sulfone compound (d); Finally, the halogenated sulfone compound (d) and substituted or unsubstituted acridine, carbazole, diphenylamine (e), etc. are reacted with the bipolar host through a palladium-catalyzed Buchwald reaction or a nucleophilic substitution reaction. material is obtained.

Experiments showed that the compound of the present invention has a higher glass transition temperature than CBP, which is a commonly used host material, and that the present invention significantly improves the thermal stability of the host material. Since the organic electroluminescent device made of the bipolar host material of the present invention has high stability and high current efficiency and external quantum efficiency, the material better meets the requirements of organic light emitting diodes for the host material.

1 is a DSC curve of compound 2.
2 is a structural diagram of a device according to the present invention.

Hereinafter, the present invention has been described in more detail with reference to Examples, but the Examples of the present invention are not limited thereto.

Example 1

(1) Synthesis of 4,6-diiododibenzofuran (4,6-diiododibenzofuran) (b)

The synthetic route is as follows.

Specific synthesis steps are as follows.

Dibenzofuran (8.41 g, 50 mmol) was weighed and added to a three-necked flask, protected with nitrogen, dry ether (150 mL) was added, and the flask was placed in a -78 ° C low temperature reactor to contain n-butyllithium. (2.2M, 68mL, 150mmol) was slowly added dropwise, and when the dropping was completed, the reaction system was slowly heated to room temperature and stirring was continued for 10 hours. The temperature is lowered to -78°C, a _{tetrahydrofuran solution (38 g, 150 mmol) of I 2} is slowly added dropwise, and when the dropping is completed, the mixture is stirred at room temperature for 4 hours. When the reaction is complete, 10% NaHSO ₃ solution (100 mL) is added and extracted to separate the layers, the inorganic phase is extracted using dichloromethane (3*50 mL), the organic phase is collected, and dried over anhydrous MgSO ₄ and spin-drying the solution to obtain a crude product, followed by ethanol pulping, extraction, filtration and drying to obtain 14 g of a white solid. The yield is 67%.

(2) 4,6-bis[(4-fluorophenyl)thio]dibenzo[ b, d ]furan(c1)(4,6-bis[(4-fluorophenyl)thio]dibenzo)[ b,d ]Synthesis of furan(c1))

The synthetic route is as follows.

Specific synthesis steps are as follows.

4,6-diiododibenzofuran (b) (5.25 g, 12.5 mmol), 4-fluoro thiophenol (3.27 g, 25.5 mmol), CuI (0.48 g, 2.5 mmol), phenan Put phenanthroline (0.9 g, 5 mmol) and potassium carbonate (4.8 g, 35 mmol) in a 100 mL three-necked flask, and replace nitrogen 3 times. Add dry DMSO, raise the temperature to 130° C. and react for 16 hours. When the reaction is complete, 150 mL of water is added, extracted with dichloromethane (3*50 mL), the organic layers are combined, and dried over anhydrous magnesium sulfate. Filtration with a sand core funnel, spin drying the solvent, and ethanol pulping, extraction, filtration and drying were performed to obtain 4.43 g of a white powdery solid. The yield is 84.6%.

(3) 4,6-bis[(4-fluorophenyl)sulfonyl]dibenzo[ b, d ]furan (d1)(4,6-bis[(4-fluorophenyl)sulfonyl]dibenzo)[ b, Synthesis of d ]furan(d1))

The synthetic route is as follows.

Specific synthesis steps are as follows.

Weigh 4,6-bis[(4-fluorophenyl)thio]dibenzo[ b,d ]furan (c1) (1 g, 2.38 mmol) into a flask, dissolve dichloromethane, and place the reaction system in an ice bath (ice bath), 2.2 equivalents of m-chloroperoxybenzoic acid (m-chloroperoxybenzoic acid) was slowly added, and reacted at room temperature for 24 hours. When the reaction is complete, _{50 mL of a 5% NaHSO 3} solution is added, extracted with dichloromethane (3*50 mL), the organic layers are combined, washed with Na ₂ CO ₃ solution, and dried over anhydrous magnesium sulfate. Filtration with a sand core funnel, spin drying the solvent, and ethanol pulping, extraction, filtration and drying were performed to obtain 1.02 g of a white powdery solid. The yield is 88.7%.

(4) 4,6-bis[(4-(9,9'-dimethylacridin-10(9H)-yl)phenylsulfonyl]dibenzo[ b,d ]furan (1)(4,6- Synthesis of bis[(4-(9,9'-dimethylacridin-10(9H)-yl)phenylsulfonyl]dibenzo[ b,d ]furan(1))

The synthetic route is as follows.

Specific synthesis steps are as follows.

Weigh 9,9' dimethylacridine (0.89g, 4.2mmol) into a 50mL flask, add 10mL of dry DMF, and slowly add NaH (60%, 0.21g, 5.2mmol) under 0℃ conditions, After stirring at room temperature for 30 min, 4,6-bis[(4-fluorophenyl)sulfonyl]dibenzo[ b,d ]furan (d1) (1 g, 2.06 mmol) was added in one portion and the reaction was stirred Stir at 60° C. for 6 hours. When the reaction is complete, 20 mL of water is added, a solid is precipitated, extracted, filtered, washed with water, and separated by silica gel column chromatography using dichloromethane: n-hexane=2:1 as an eluent to 1.4 g of a yellow solid were obtained. The yield is 78.6%.

Product sentiment data are as follows.

¹ H NMR (400MHz,CDCl ₃ ) δ =8.73(d, J =8.0Hz,4H), 8.27(d, J =8.0Hz,4H), 7.65-7.59(m,6H), 7.44-7.42(m, 4H), 6.95-6.93(m,8H), 6.34-6.31(m,4H), 1.63(s,6H), 1.57(s,6H)ppm. ¹³ C NMR (100 MHz, CDCl ₃ )=147.1, 140.1, 131.7, 131.0, 130.5, 128.0, 126.2, 125.0, 124.0, 121.5, 115.2, 30.7 ppm.Ms(ESI:Mz 863)(M+1)

Example 2

(1) 4,6-bis[(4-(9H-carbazol-9-yl)phenylsulfonyl]dibenzo[ b,d ]furan(2)(4,6-bis[(4-(9H-) Synthesis of carbazole-9-yl)phenylsulfonyl]dibenzo[ b, d ]furan(2))

The synthetic route is as follows.

Specific synthesis steps are as follows.

Carbazole (1.7g, 10mmol) was weighed and put into a 50mL flask, dried DMF was added 20mL, NaH (60%, 0.6g, 15mmol) was slowly added under 0℃ condition, and stirred at room temperature for 30 minutes , 4,6-bis[(4-fluorophenyl)sulfonyl]dibenzo[ b, d ]furan (d1) (3 g, 5 mmol) is added in one portion and the reaction is stirred at 60° C. for 6 hours. When the reaction is complete, 60 mL of water is added, and the solid is extracted and filtered, washed with water, and separated by silica gel column chromatography using dichloromethane: n-hexane = 2:1 as an eluent to obtain 3.3 g of a yellow solid. obtained. The yield is 85.7%.

Product sentiment data are as follows.

¹ H NMR(400MHz,CDCl ₃ ) δ =8.62(d, J =8.0Hz,4H), 8.66(d, J =8.0Hz,2H), 8.23(d, J =8.0Hz,2H), 8.15(d) , J =8.0Hz,4H), 7.93(d, J =8.0Hz,4H), 7.72(t, J =8.0Hz,2H), 7.44(d, J =8.0Hz,4H), 7.30(t, J) =8.0Hz,4H), 7.22(t, J =8.0Hz,4H)ppm. ¹³ C NMR (100 MHz, CDCl ₃ )=141.9, 138.9, 129.8, 128.1, 127.6, 126.7, 126.2, 124.7, 124.5, 123.0, 120.6, 120.3, 110.3, 109.6 ppm.Ms(ESI:Mz 779)(M+1) )

Example 3

(1) (4,6-bis[(3-bromophenyl)thio]dibenzo[ b, d ]furan)(c2)(4,6-bis[(3-bromophenyl)thio]dibenzo[ b, d ] Synthesis of furan(c2))

The synthetic route is as follows.

Specific synthesis steps are as follows.

4,6-diiododibenzofuran (b) (1.05 g, 2.5 mmol), 3-bromo thiophenol (0.98 g, 5.2 mmol), CuI (0.095 g, 0.5 mmol), phenan Traline (0.18 g, 1 mmol) and potassium carbonate (0.96 g, 7 mmol) were placed in a 50 mL three-necked flask, and the nitrogen was replaced 3 times. Add 10 mL of dry DMSO, raise the temperature to 130° C. and react for 16 hours. When the reaction is complete, 150 mL of water is added, extracted with dichloromethane (3*20 mL), the organic layers are combined, and dried over anhydrous magnesium sulfate. It was filtered through a sand core funnel, the solvent was spin-dried, and separated by silica gel column chromatography using n-hexane/ethyl acetate = 20/1 as an eluent to obtain 0.9 g of a white solid. The yield is 66%.

(2) 4,6-bis[(3-bromophenyl)sulfonyl]dibenzo[ b,d ]furan(d2)(4,6-bis[(3-bromophenyl)sulfonyl]dibenzo[ b,d Synthesis of ]furan(d2))

The synthetic route is as follows.

Specific synthesis steps are as follows.

Weigh 4,6-bis[(3-bromophenyl)thio]dibenzo[ b,d ]furan (c2) (0.9 g, 1.66 mmol) into a flask, dissolve dichloromethane, and place the reaction system on ice Into the bath, 2.2 equivalents of m-chloroperoxybenzoic acid is slowly added, and the reaction is carried out at room temperature for 24 hours. When the reaction is complete, _{50 mL of a 5% NaHSO 3} solution is added, extracted with dichloromethane (3*50 mL), the organic layers are combined, washed with Na ₂ CO ₃ solution, and dried over anhydrous magnesium sulfate. Filtration with a sand core funnel, spin drying the solvent, and ethanol pulping, extraction, filtration and drying were performed to obtain 0.8 g of a white powdery solid. The yield is 80%.

(3) Synthesis of 4,6-bis[3-(9H-carbazol-9-yl)phenylsulfonyl]dibenzo[ b,d ]furan (3)

The synthetic route is as follows.

Specific synthesis steps are as follows.

4,6-bis[(3-bromophenyl)sulfonyl]dibenzo[ b,d ]furan (d2) (0.136g, 0.3mmol), carbazole (0.1g, 0.6mmol), Pd ₂ (dba) ₃ (28mg, 0.03mmol), P(tBu) ₃ Toluene solution (24mg, 0.06mmol), sodium tert-butoxide (0.115g, 1.2mmol), 5mL toluene Weigh out 10mL Put in a Schlenk flask, protect with nitrogen, and react at 110 ℃ for 10 hours. When the reaction is complete, _{20 mL of a 5% NaHSO 3} solution is added, extracted with dichloromethane (3*20 mL), and separated by silica gel column chromatography using n-hexane/ethyl acetate=2:1 as an eluent, and 0.18 g of yellow A solid was obtained. The yield is 69%.

Product sentiment data are as follows.

Ms(ESI:Mz 779)(M+1)

Example 4

(1) Synthesis of 4,6-bis[(2-bromophenyl)thio]dibenzo[ b,d ]furan (c3)

The synthetic route is as follows.

Specific synthesis steps are as follows.

4,6-diiododibenzofuran (b) (2.1 g, 5 mmol), 2-bromothiophenol (1.96 g, 10.4 mmol), CuI (0.19 g, 1 mmol), phenanthroline (0.36 g, 2 mmol) and potassium carbonate (2g, 14mmol) were placed in a 50mL three-necked flask, and nitrogen was replaced 3 times. Add 20 mL of dry DMSO, raise the temperature to 130° C., and react for 15 hours. When the reaction is complete, 150 mL of water is added, extracted with dichloromethane (3*30 mL), the organic layers are combined, washed with water, and dried over anhydrous magnesium sulfate. Filtration with a sand core funnel, spin-drying the solvent, and separation by silica gel column chromatography using n-hexane/ethyl acetate=20/1 as an eluent gave 1.5 g of a white solid. The yield is 55%.

(2) Synthesis of 4,6-bis[(2-bromophenyl)sulfonyl]dibenzo[ b,d ]furan (d3)

The synthetic route is as follows.

Specific synthesis steps are as follows.

Weigh 4,6-bis[(2-bromophenyl)thio]dibenzo[ b,d ]furan (c3) (1.4 g, 2.58 mmol) into a flask, dissolve dichloromethane, and place the reaction system on ice Into the bath, 2.2 equivalents of m-chloroperoxybenzoic acid is slowly added, and the reaction is carried out at room temperature for 24 hours. When the reaction is complete, _{50 mL of a 5% NaHSO 3} solution is added, extracted with dichloromethane (3*50 mL), the organic layers are combined, washed with Na ₂ CO ₃ solution, and dried over anhydrous magnesium sulfate. Filtration with a sand core funnel, spin drying the solvent, and ethanol pulping, extraction, filtration and drying were performed to obtain 1.4 g of a white powdery solid. The yield is 89%.

(3) Synthesis of 4,6-bis[(2-(9H-carbazol-9-yl)phenylsulfonyl]dibenzo[ b,d ]furan (4)

The synthetic route is as follows.

Specific synthesis steps are as follows.

4,6-bis[(2-bromophenyl)sulfonyl]dibenzo[ b,d ]furan (d3) (1.36 g, 3 mmol), carbazole (1 g, 6 mmol), Pd ₂ (dba) ₃ (0.28) g, 0.3 mmol), P(tBu) ₃ toluene solution (0.24 g, 0.6 mmol), sodium tert-butoxide (1.15 g, 12 mmol), and 10 mL of toluene were weighed and placed in a 25 mL Schlenk flask, protected with nitrogen, and heated at 110 ° C. React for 10 hours. When the reaction is complete, _{30 mL of a 5% NaHSO 3} solution is added, extracted with dichloromethane (3*30 mL), and separated by silica gel column chromatography using n-hexane/ethyl acetate = 2:1 as an eluent, and 1.1 g of yellow A solid was obtained. The yield is 47%.

Product sentiment data are as follows.

Ms(ESI:Mz 779)(M+1)

Example 5

Glass transition temperature test:

The glass transition temperature of compound 2 is tested using differential scanning calorimetry (DSC) at a heating and cooling rate of 20° C./min under nitrogen protection. The measured glass transition temperature T _g of Compound 2 is 180° C. ( FIG. 1 ). The glass transition temperature of CBP reported in the literature is only 62°C.

Therefore, it can be seen that the compound of the present invention has a higher glass transition temperature than the conventionally used host material CBP, and the present invention significantly improves the thermal stability of the host material.

Example 6

Fabrication of organic electroluminescent devices

The device structure is ITO/HATCN (5 nm)/TAPC (50 nm)/Compound 2:Ir(ppy):(4wt%, 20nm)/TmPyPb(50nm)/LiF(1nm)/AL(100nm).

A method of manufacturing the device is as follows, with reference to FIG. 2 .

First, the transparent conductive ITO glass substrates (including 10 and 20) are sequentially cleaned with a detergent solution, deionized water, ethanol, acetone, and deionized water, and then treated again with oxygen plasma for 30 seconds.

Thereafter, 5 nm thick HATCN is deposited on the ITO as the hole injection layer 30 .

Thereafter, TAPC having a thickness of 50 nm is deposited on the hole injection layer to be used as the hole transport layer 40 .

Thereafter, a compound 2:Ir(ppy):(4wt%) having a thickness of 20 nm is deposited on the hole transport layer to be used as the light emitting layer 50 .

Thereafter, TmPyPb having a thickness of 50 nm is deposited on the emission layer and used as the hole transport layer 60 .

Thereafter, LiF having a thickness of 1 nm is deposited on the electron transport layer and used as the electron injection layer 70 .

Finally, 100 nm thick aluminum is deposited on the electron injection layer and used as the cathode 80 .

comparative example

Manufacturing of electroluminescent devices

The device structure is ITO/HATCN(5nm)/TAPC(50nm)/CBP:Ir(ppy):(4wt%, 20nm)/TmPyPb(50nm)/LiF(1nm)/AL(100nm).

The method is the same as in Example 6, but a commercially available compound CBP is used as a host material to prepare an electroluminescent organic semiconductor diode device for comparison.

According to the experiment, the electroluminescent device made of the bipolar host material of the present invention has a voltage of 6.99V, a luminance of 7082 cd/m ² , a current efficiency of 35.41 cd/A, and a power efficiency of 15.91lm ^{at a current density of 20 mA/cm 2 .} Although /W, external quantum efficiency EQE is 9.98%, a commercially available electroluminescent device manufactured with host CBP has a voltage of 7.71V, a luminance of 5845cd/m ² , a current efficiency of 29.23cd/A, and a power efficiency at the same current density. 11.91lm/W, external quantum efficiency EQE was found to be 8.5%. Therefore, when the bipolar host material of the present invention is used, the current efficiency is 21% higher and the external quantum efficiency is 17.4% higher than that of the device made of CBP, so the stability of the device can be further improved, the application prospect is bright, and the organic material for the host material Better meet the requirements of light emitting diodes.

10: glass substrate
20: positive electrode
30: hole injection layer
40: hole transport layer
50: light emitting layer
60: electron transport layer
70: electron injection layer
80: cathode

Claims (10)

A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, the device comprising:
a cathode, an anode, and an organic layer, wherein the organic layer is at least one of a hole transport layer, a hole blocking layer, an electron transport layer, and a light emitting layer, and the organic layer contains a 4,6-diphenyl sulfone dibenzofuran-based bipolar host material, The bipolar host material has the structure of formula (I),

wherein two of R ₁ , R ₂ and R ₃ are hydrogen, halogen or C1-C4 alkyl, and the other is C1-C8 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole , indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives; 2 of R ₄ , R ₅ and R ₆ are hydrogen, halogen or C1-C4 alkyl and the other is C1-C8 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl, carbazole, indeno A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that it is a carbazole, diphenylamine or other aromatic diphenylamine derivative. delete According to claim 1,
wherein R ₁ and R ₄ are identical, R ₂ and R ₅ are identical, and R ₃ and R ₆ are identical. 4. The method of claim 3,
wherein R ₂ , R ₃ , R ₅ and R ₆ are hydrogen, halogen or C1-C4 alkyl, R ₁ and R ₄ are C1-C4 alkyl substituted or unsubstituted acridinyl, phenothiazinyl, phenoxazinyl , carbazole, indenocarbazole, diphenylamine or other aromatic diphenylamine derivatives containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran. 5. The method of claim 4,
wherein R ₂ , R ₃ , R ₅ and R ₆ are hydrogen, R ₁ and R ₄ are C1-C4 alkyl substituted or unsubstituted acridinyl, carbazole, indenocarbazole 4, Devices containing a bipolar material of 6-diphenyl sulfone dibenzofuran. According to claim 1,
A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that formula (I) is one of the following structures.

7. The method of claim 6,
A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that formula (I) is one of the following structures.

According to claim 1,
A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that the 4,6-diphenyl sulfone dibenzofuran-based bipolar host material is a material of the light emitting layer. According to claim 1,
A device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that the total thickness of the organic layer is 1 to 1000 nm. According to claim 1,
The organic layer is a device containing a bipolar material of 4,6-diphenyl sulfone dibenzofuran, characterized in that to form a thin film by evaporation or spin coating.

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