CN111718342B - Novel organic material and application thereof - Google Patents

Novel organic material and application thereof Download PDF

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CN111718342B
CN111718342B CN202010662449.XA CN202010662449A CN111718342B CN 111718342 B CN111718342 B CN 111718342B CN 202010662449 A CN202010662449 A CN 202010662449A CN 111718342 B CN111718342 B CN 111718342B
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organic electroluminescent
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electroluminescent device
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CN111718342A (en
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黄春雪
曹占广
范洪涛
段陆萌
杭德余
李仲庆
班全志
陈婷
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

The invention belongs to the technical field of organic electroluminescent display, and particularly relates to a novel organic material and application thereof in an organic electroluminescent device. The structure of the novel organic material compound provided by the invention is shown as a general formula (I). The material has high thermal stability and higher glass transition temperature, and can maintain the phase stability of a formed film. The novel organic material provided by the invention can be well applied to organic electroluminescent devices, and the devices have the advantages of low driving voltage and high current efficiency.

Description

Novel organic material and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent display, and particularly relates to a novel organic material and application thereof in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self-luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like. Compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, and has a response speed 1000 times that of the liquid crystal display device, so that the OLED has a wider application prospect.
In order to meet the requirement of OLED display and lighting clients on the continuous improvement of the performance of a screen, the development of a new material capable of reducing the working voltage of an OLED device, improving the photoelectric performance of the device and prolonging the working life of the device is of great significance. By the molecular design of the material, the improvement and improvement of the device performance in the application of the device by the structural modification of the material molecule are researched, the experience is accumulated in the design and development of the new material, and the updating and upgrading of the new material can be accelerated.
The hole type material can be used in an OLED device in a proportion of 50% to 60%. Therefore, the stable and efficient organic hole transport material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the organic hole transport material has important practical application value.
Disclosure of Invention
The invention aims to provide an OLED hole transport material with good film forming property, high thermal stability and high hole mobility and an OLED element using the material.
In order to develop a compound material having the above properties and an OLED device using such a compound, it has been found that the above object can be achieved by using a compound represented by the general formula (1).
In a first aspect, the present invention provides a compound represented by the general formula (1):
Figure BDA0002579119260000021
wherein the content of the first and second substances,
r is selected from H, linear alkyl with 1-40 carbon atoms, C3-40Atom-containing branched or cycloalkyl-containing radical, C5～C40Aryl of (C)5～C40Substituted aryl of (2), C5～C40Heteroaryl of (A), C5～C40Wherein Ar is C6～C60Substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl aryl, or arylamine having 12 to 30 aromatic ring atoms;
R1～R6each independently selected from H, C5～C40Substituted or unsubstituted aryl of (1), C5～C40Substituted or unsubstituted heteroaryl of (a); or, R1、R2With R or both3、R4、R5、R6Either or both are connected by a bridge;
the substituted or unsubstituted heteroaryl group contains 1-3 heteroatoms selected from one or more of N, O, S and P.
Through long-term experimental groping, it is surprisingly found that the introduction of N atom on benzene ring of carbazole is favorable for adjusting energy level, and meanwhile, in order to avoid the influence of N atom on hole cation on pyridine group after N atom introduction, phenyl group is introduced at ortho position of N atom, so that the change of intermolecular interaction mode is favorable, the thermal stability and film forming stability of the compound are improved, and the effect of improving hole mobility is also achieved.
In a preferred embodiment, in formula (I), R is a substituted or unsubstituted aromatic group containing a phenyl ring and/or a heteroaromatic ring, wherein the substituents are optionally selected from: c1-5Linear or branched alkyl, C3-6Cycloalkyl, phenyl, biphenyl, monocyclic aryl, benzo, pyrido, phenanthro, naphtho, indolo, benzothieno, benzofuro; the number of the substituent groups is an integer of 1 to 5.
In a preferred embodiment, in formula (I), R1～R6Each independently selected from H, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstitutedSubstituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl;
preferably, the substituents may be arbitrarily selected from: phenyl, naphthyl, biphenyl, phenanthryl, anthracyl.
In a preferred embodiment, in formula (I), R is phenyl;
and/or, R1～R6Each independently selected from H,
Figure BDA0002579119260000031
In each substituent group, "- - -" represents a substitution position.
In a preferred embodiment, in formula (I), R1～R6Each independently selected from H,
Figure BDA0002579119260000041
In each substituent group, "- - -" represents a substitution position;
preferably, R1、R2Not simultaneously being H or R3、R4、R5、R6Not H at the same time;
more preferably, R1～R6In R2、R3、R5、R6Are all H, R1、R4Is not H.
Optionally introducing R into the benzene ring of carbazole1～R6The substituent is beneficial to improving the glass transition temperature of the material and the film forming stability of the material, and meanwhile, the film forming stability of the material is better when the substituent on the two sides is different, and the effect of adjusting the energy level is better.
As a preferred embodiment of the present invention, the present invention provides a compound represented by the following structural formula:
Figure BDA0002579119260000042
Figure BDA0002579119260000051
Figure BDA0002579119260000061
Figure BDA0002579119260000071
Figure BDA0002579119260000081
Figure BDA0002579119260000091
Figure BDA0002579119260000101
Figure BDA0002579119260000111
in a second aspect, the present invention provides the use of the novel organic material for the preparation of an organic electroluminescent device. Preferably, the present invention provides the use of the novel organic material as a hole transport material for a hole transport layer in the preparation of an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising a hole transport layer comprising the novel organic material. Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer containing the novel organic material, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence.
In a fourth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The present invention provides a novel organic material having a wider bandgap, a high T1 energy level, and a suitable Highest Occupied Molecular Orbital (HOMO) energy level. The material has high thermal stability, is not easy to decompose in the sublimation process, has higher glass transition temperature, and can maintain the phase stability of a formed film. By introducing a group with larger steric hindrance, the hole transport material has good film forming property, high thermal stability and high hole mobility.
The novel organic material provided by the invention can be well applied to organic electroluminescent devices, and the devices have the advantages of low driving voltage and high current efficiency. The device can be applied to the field of display or illumination.
Detailed Description
The technical solution of the present invention will be explained in detail below.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting suitable catalyst and solvent, determining suitable reaction temperature, time, etc., which is not particularly limited by the present invention. The starting materials for the preparation of solvents, catalysts, bases, etc. can be synthesized by published commercial routes or by methods known in the art.
Example 1 Synthesis of intermediate P1
Figure BDA0002579119260000121
The method comprises the following specific steps:
(1) a1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 20.35g (0.189mol) of sodium carbonate, 12g (0.1mol) of phenylboronic acid and 100ml of toluene were sequentially added. After the nitrogen exchange again, 5g (7mmol) of Pd132 were successively added. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution composed of 27.72g of 5, 6-dibromopyridin-2-amine (0.11mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. After the reaction was completed, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to obtain 18.675g of P1-1 as a yellow solid in a yield of 75%.
(2) A1 liter three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 20.35g (0.189mol) of sodium carbonate, 24.5g (0.1mol) of 5-chloro-2-nitrophenyl) boronic acid and 100ml of toluene were sequentially added. After the nitrogen exchange again, 5g (7mmol) of Pd132 were successively added. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 27.39g of compound P1-1(0.11mol) and 100ml of toluene, the temperature being controlled at 75-90 ℃. After the reaction was completed, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to obtain 25.02g of P1-2 as a yellow solid in a yield of 77%.
(3) Adding 280ml of water serving as a solvent into a 1L three-necked bottle with mechanical stirring, slowly dropwise adding concentrated hydrochloric acid (0.25mol), after dropwise adding, adding P1-2(35.02g, 0.1mol), cooling to 8 ℃, controlling the temperature to be below 10 ℃, dropwise adding a sodium nitrite aqueous solution, after dropwise adding and stirring for 1h, dropwise adding a cuprous chloride solution, and increasing the temperature to a certain extent to thicken. The temperature is 22 ℃ after dripping, stirring is carried out for 2h, and the reaction is determined to be complete by a point plate. The organic phase is separated, extracted, dried, and chromatographed, and the solvent is dried, 27.52g white solid P1-3 is obtained, the yield is 80%.
(4) Adding P1-3(34.4g, 0.1mol) into a 1L three-mouth bottle, adding 25.92mL o-dichlorobenzene, starting heating and stirring, heating to 150 ℃, adding triphenylphosphine in 3 batches, wherein the total amount is 60.329g (0.23mol), continuously heating to 165 ℃, controlling the temperature to 170-180 ℃ after stabilization, and preserving the temperature for 5 hours to finish the reaction. The organic phase was separated, extracted, dried, column chromatographed, and the solvent dried to give 21.84g of P1-4 as a yellow solid in 70% yield.
(5) A1 liter three-necked flask was magnetically stirred, and then, after nitrogen substitution, 36.2g (0.376mol) of potassium t-butoxide, 0.1mol of P1-431.2g and 100ml of toluene were added in this order. After nitrogen replacement again, 0.32ml (4.1mmol) of tri-tert-butylphosphine and 1.8314g (0.002mol) of Pd2(dba)3 were added in this order. After the addition, the temperature was raised to 85 ℃. A solution of 15.7g of bromobenzene (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled at 80-120 ℃. The reaction was complete. The organic phase was separated, extracted, dried, column chromatographed, and the solvent dried to give 31.04g of a pale yellow solid in 80% yield.
Product MS (m/e): 388; elemental analysis (C)23H14Cl2N2): theoretical value C: 70.96 percent; h: 3.62 percent; n: 7.20 percent; measured value: c: 70.71 percent; h: 3.82 percent; n: 7.03 percent.
Example 2 Synthesis of intermediate P2
Figure BDA0002579119260000131
In the third step, concentrated hydrobromic acid and cuprous bromide are used to replace concentrated hydrochloric acid and cuprous chloride, a suitable material ratio is selected, and other raw materials and steps are the same as those in example 1, so as to obtain intermediate P2.
Product MS (m/e): 432; elemental analysis (C)23H14BrClN2): theoretical value C: 63.69%, H: 3.25%, N: 6.46 percent; measured value: c: 63.45%, H: 3.49%, N: 6.74 percent.
Example 3 Synthesis of intermediate P3
Figure BDA0002579119260000141
The intermediate P3 was obtained by substituting 5, 6-dibromopyridin-3-amine for 5, 6-dibromopyridin-2-amine in the first step and selecting an appropriate material ratio and the other starting materials and procedures were the same as in example 1.
Product MS (m/e): 388; elemental analysis (C)23H14Cl2N2): theoretical value C: 70.96 percent; h: 3.62 percent; n: 7.20 percent; measured value: c: 70.75 percent; h: 3.79 percent; n: 7.06 percent.
Example 4 Synthesis of intermediate P4
Figure BDA0002579119260000142
In the second step (4-chloro-2-nitrophenyl) boronic acid was used instead of (5-chloro-2-nitrophenyl) boronic acid and in the third step concentrated hydrobromic acid and cuprous bromide were used instead of concentrated hydrochloric acid and cuprous chloride, with the appropriate ratios of materials chosen and the other starting materials and procedures identical to those of example 1, giving intermediate P4.
Product MS (m/e): 432; elemental analysis (C)23H14BrClN2): theoretical value C: 63.69%, H: 3.25%, N: 6.46 percent; measured value: c: 63.45%, H: 3.50%, N: 6.33 percent.
Example 5 Synthesis of intermediate P5
Figure BDA0002579119260000151
In the second step (4-chloro-2-nitrophenyl) boronic acid was used instead of (5-chloro-2-nitrophenyl) boronic acid, the other starting materials and the procedure were the same as in example 1, choosing the appropriate ratios of the materials, obtaining intermediate P5.
Product MS (m/e): 388; elemental analysis (C)23H14Cl2N2): theoretical value C: 70.96 percent; h: 3.62 percent; n: 7.20 percent; measured value: c: 70.71 percent; h: 3.79 percent; n: 6.99 percent.
EXAMPLE 6 Synthesis of Compound I-1
Figure BDA0002579119260000152
Synthesis of (Compound I-1)
The synthetic route is as follows:
Figure BDA0002579119260000153
synthesis of Compound I-1:
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, 38.8g of compound P1(0.1mol), (9-phenyl-9H-carbazol-3-yl) boronic acid 60.27g (0.21mol), cesium carbonate (78g, 0.24mol) and dioxane 500ml were added in this order, and stirring was started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added, and after the addition, the reaction was heated to 80-90 ℃ for 5 hours, and the completion of the reaction was monitored by TLC. Then, the temperature is reduced to room temperature, the pH value is adjusted to be neutral, an organic phase is separated, extraction, drying and column chromatography are carried out, and a solvent is dried in a spinning mode, so that 64.16g of light yellow solid is obtained, and the yield is 80%.
Product MS (m/e): 802, a first step of; elemental analysis (C)59H38N4): theoretical value C: 88.25%, H: 4.77%, N: 6.98 percent; measured value: c: 88.02%, H: 4.93%, N: 6.87 percent.
EXAMPLE 7 Synthesis of Compound I-9
Figure BDA0002579119260000161
Synthesis of (Compound I-9)
The synthetic route is as follows:
Figure BDA0002579119260000162
(1) synthesis of Compound I-9-1:
A1L three-necked flask is stirred by magnetic stirring and then is added with 3.69g (0.035mol) of sodium carbonate, 36.3g (0.1mol) of (9- ([1,1' -biphenyl ] -4-yl) -9H-carbazole-3-yl) boric acid and 100ml of xylene in turn after nitrogen replacement. After the nitrogen exchange again, 4g (3.5mmol) of Pd132 were successively added. After the addition, the temperature was raised to 80 ℃. Dropwise addition was started in a solution consisting of 47.52g of compound P2(0.11mol) and 100ml of xylene, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, filtering, performing column chromatography on the filter cake, crystallizing, filtering, and drying to obtain 32.88g of light yellow solid with a yield of 49%.
(2) Synthesis of Compound I-9:
A1L three-necked flask is stirred by magnetic force, after nitrogen replacement, I-9-1(57.6g, 0.1mol), (9-phenyl-9H-carbazol-3-yl) boric acid (28.7g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml are sequentially added, and stirring is started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 66.728g of light yellow solid I-9 with the yield of about 76%.
Product MS (m/e): 878; elemental analysis (C)65H42N4): theoretical value C: 88.81%, H: 4.82%, N: 6.37 percent; measured value: c: 88.60%, H: 5.03%, N: 6.26 percent.
EXAMPLE 8 Synthesis of Compound I-14
Figure BDA0002579119260000171
Synthesis of (Compound I-14)
The synthetic route is as follows:
Figure BDA0002579119260000172
compound I-14 was prepared in the same manner as in example 7 except that (9-phenyl-9H-carbazol-9-yl) phenyl) boronic acid was replaced with (9-phenyl-9H-carbazol-3-yl) boronic acid in an equivalent amount and the other steps were completely the same.
Product MS (m/e): 878; elemental analysis (C)65H42N4): theoretical value C: 88.81%, H: 4.82%, N: 6.37 percent; measured value: c: 88.61%, H: 5.02%, N: 6.29 percent.
EXAMPLE 9 Synthesis of Compound I-21
Figure BDA0002579119260000173
Synthesis of (Compound I-21)
The synthetic route is as follows:
Figure BDA0002579119260000181
compound I-21 was prepared in the same manner as in example 7 except that (9- ([1,1' -biphenyl ] -4-yl) -9H-carbazol-3-yl) boronic acid was replaced with an equivalent amount of (4- (9H-carbazol-9-yl) phenyl) boronic acid and the other steps were completely identical.
Product MS (m/e): 876; elemental analysis (C)69H44N4): theoretical value C: 89.20%, H: 4.77%, N: 6.03 percent; measured value: c: 88.98%, H: 4.99%, N: 5.89 percent.
EXAMPLE 10 Synthesis of Compound I-26
Figure BDA0002579119260000182
Synthesis of (Compound I-26)
The synthetic route is as follows:
Figure BDA0002579119260000183
synthesis of Compound I-26:
a1000 ml three-necked flask is taken, magnetic stirring is carried out, 38.8g of a compound P3(0.1mol), 60.27g (0.21mol) of (11-phenyl-11H-benzo [ a ] carbazole-8-yl) boric acid, 78g of cesium carbonate (0.24 mol) and 500ml of dioxane are sequentially added after nitrogen replacement, and stirring is started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added, and after the addition, the reaction was heated to 80-90 ℃ for 5 hours, and the completion of the reaction was monitored by TLC. Then, the temperature is reduced to room temperature, the pH value is adjusted to be neutral, an organic phase is separated, extraction, drying and column chromatography are carried out, and the solvent is dried in a spinning mode, so that 66.57g of light yellow solid is obtained, and the yield is 83%.
Product MS (m/e): 802, a first step of; elemental analysis (C)59H38N4): theoretical value C: 88.25%, H: 4.77%, N: 6.98 percent; measured value: c: 88.02%, H: 5.00%, N: 6.89 percent.
EXAMPLE 11 Synthesis of Compound I-31
Figure BDA0002579119260000191
(Compound I-31) SynthesisBecome into
The synthetic route is as follows:
Figure BDA0002579119260000192
synthesis of Compound I-31:
a1000 ml three-necked flask is taken, magnetic stirring is carried out, 38.8g of a compound P3(0.1mol), 70.77g (0.21mol) of (9-phenyl-9H-carbazole-3-yl) boric acid, cesium carbonate (78g, 0.24mol) and 500ml of dioxane are sequentially added after nitrogen replacement, and stirring is started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added, and after the addition, the reaction was heated to 80-90 ℃ for 5 hours, and the completion of the reaction was monitored by TLC. Then, the temperature is reduced to room temperature, the pH value is adjusted to be neutral, an organic phase is separated, extraction, drying and column chromatography are carried out, and a solvent is dried in a spinning mode, so that 66.74g of light yellow solid is obtained, and the yield is 74%.
Product MS (m/e): 902; elemental analysis (C)67H42N4): theoretical value C: 89.11%, H: 4.69%, N: 6.20 percent; measured value: c: 88.92%, H: 4.88%, N: 6.06 percent.
EXAMPLE 12 Synthesis of Compounds I-36
Figure BDA0002579119260000193
Synthesis of (Compound I-36)
The synthetic route is as follows:
Figure BDA0002579119260000194
compound I-36 was prepared in the same manner as in example 7 except that (9- ([1,1' -biphenyl ] -4-yl) -9H-carbazol-3-yl) boronic acid was replaced with (11-phenyl-11H-benzo [ a ] carbazol-8-yl) boronic acid by equivalent amount of P4 instead of P2, and the other steps were completely identical.
Product MS (m/e): 852; elemental analysis (C)63H40N4): theoretical value C: 88.71%, H: 4.73%, N: 6.57 percent;measured value: c: 88.45%, H: 4.99%, N: 6.48 percent.
EXAMPLE 13 Synthesis of Compound I-77
Figure BDA0002579119260000201
Synthesis of (Compound I-77)
The synthetic route is as follows:
Figure BDA0002579119260000202
synthesis of Compound I-77:
a1000 ml three-necked flask was charged with stirring by magnetic force, and after nitrogen substitution, 38.8g of Compound P5(0.1mol), 53.34g (0.21mol) of (3-phenylbenzo [ b ] thiophen-2-yl) boronic acid, 78g (0.24 mol) of cesium carbonate and 500ml of dioxane were added in this order, followed by stirring. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added, and after the addition, the reaction was heated to 80-90 ℃ for 5 hours, and the completion of the reaction was monitored by TLC. Then, the temperature is reduced to room temperature, the pH value is adjusted to be neutral, an organic phase is separated, extraction, drying and column chromatography are carried out, and the solvent is dried in a spinning mode, so that 51.52g of light yellow solid is obtained, and the yield is 70%.
Product MS (m/e): 736; elemental analysis (C)51H32N2S2): theoretical value C: 83.12%, H: 4.38%, N: 3.80 percent; measured value: c: 82.92%, H: 4.57%, N: 3.68 percent.
According to the technical schemes of the embodiments 1 to 13, the following compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation:
Figure BDA0002579119260000211
Figure BDA0002579119260000221
Figure BDA0002579119260000231
Figure BDA0002579119260000241
Figure BDA0002579119260000251
Figure BDA0002579119260000261
example 12: preparation of OLED device
The invention provides a group of OLED red light devices, the compound of the invention is used as a hole transport material, and the preparation steps are as follows:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm;
Figure BDA0002579119260000271
(3) evaporating and plating a layer of compound I-1 on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
(4) in the hole transport layerThe EML is vacuum evaporated on the substrate and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material PRH01 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, and the dye material Ir (piq)2The acac concentration is 5%, and the total film thickness of evaporation plating is 30 nm;
Figure BDA0002579119260000272
(5) continuously evaporating a layer of compound Bphen on the organic light-emitting layer to be used as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30 nm;
Figure BDA0002579119260000273
(6) continuously evaporating a layer of LiF on the electron transport layer to be used as an electron injection layer of the device, wherein the thickness of the evaporated film is 0.5 nm;
(7) continuously evaporating a layer of Al on the electron injection layer to be used as a cathode of the device, wherein the thickness of the evaporated film is 150 nm; the OLED device provided by the invention is obtained and is marked as a device OLED-1.
According to the same steps as the above, the compound I-1 in the step (3) is replaced by the compounds I-9, I-14, I-21, I-26, I-31, I-36 and I-77 prepared by the invention, and the devices OLED-2 to OLED-8 provided by the invention are obtained respectively.
According to the same procedure as above, compound I-1 in step (3) was replaced with comparative compound 1(NPB, structure shown below), giving comparative device OLED-9.
Figure BDA0002579119260000281
The results of the performance tests of the obtained devices OLED-1 to OLED-9 are shown in Table 1.
Table 1: performance test results of OLED-1 to OLED-9
Figure BDA0002579119260000282
From the above results, it can be seen that the devices OLED-1 to OLED-8 prepared from the organic material shown in formula I provided by the present invention have higher current efficiency, and under the same brightness, the operating voltage is significantly lower than that of the device OLED-9 using the comparative compound 1 as the organic light emitting host material, and the material is a hole transport material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. A compound of the general formula (I):
Figure FDA0003129693380000011
wherein the content of the first and second substances,
r is phenyl;
R1～R6each independently selected from H,
Figure FDA0003129693380000012
Figure FDA0003129693380000021
R1、R2Not simultaneously being H or R3、R4、R5、R6Not H at the same time;
in each substituent group, "- - -" represents a substitution position.
2. The compound of claim 1Wherein R is1～R6Each independently selected from H,
Figure FDA0003129693380000022
3. The compound of claim 1, wherein R1～R6In R2、R3、R5、R6Are all H, R1、R4Is not H.
4. A compound represented by the following structural formula:
Figure FDA0003129693380000023
Figure FDA0003129693380000031
Figure FDA0003129693380000041
Figure FDA0003129693380000051
Figure FDA0003129693380000061
Figure FDA0003129693380000071
Figure FDA0003129693380000081
Figure FDA0003129693380000091
5. use of a compound according to any one of claims 1 to 4 for the preparation of an organic electroluminescent device.
6. Use of a compound according to any one of claims 1 to 4 as a hole transport material for a hole transport layer in the preparation of an organic electroluminescent device.
7. An organic electroluminescent device comprising the compound according to any one of claims 1 to 4 in a hole transport layer.
8. An organic electroluminescent device comprising, in order from bottom to top, a transparent substrate, an anode layer, a hole transport layer comprising the compound of any one of claims 1 to 4, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer.
9. A display apparatus, wherein the display apparatus comprises the organic electroluminescent device according to claim 7 or 8.
10. A lighting apparatus, wherein the lighting apparatus comprises the organic electroluminescent device according to claim 7 or 8.
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