CN111116602B - OLED material and application thereof in organic electroluminescent device - Google Patents
OLED material and application thereof in organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to an OLED material which has any one structure shown in general formulas I to III. The OLED material provided by the invention is a compound which takes tonne-to-tonne as a center and has a high T1 energy level, a narrow band gap and a shallow Highest Occupied Molecular Orbital (HOMO) energy level. The perixanthenoxanthene is easily sublimable, stable in air, and does not undergo oxidative decomposition. Has high thermal stability and high glass transition temperature in air. By introducing a group with larger steric hindrance, the luminescent material is not easy to crystallize and quench and has good film-forming property. In a preferred embodiment of the present invention, the OLED material is used as a hole transport material for a hole transport layer.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to an OLED 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, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.
The organic hole transport material reported at present has the defects that the molecular weight is generally small, the glass transition temperature of the material is low, the material is easy to crystallize after repeated charging and discharging in the use process of the material, and the uniformity of a thin film is damaged, so that the service life of the material is influenced. 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.
The Peri-xanthoxanthene (PXX) is a condensed ring aromatic compound having 22 pi electrons in a divalent cation and a conjugated system of 22 atoms (20 carbon atoms and 2 oxygen atoms) and is very stable. The xanthenoxanthene is often used as an electron donor in charge transfer complexes and therefore has potential as a hole transport material.
Disclosure of Invention
The invention aims to provide an OLED hole transport material which is not easy to quench, crystallize and has good film forming property, and an OLED device using the compound.
Specifically, the invention provides an OLED material, which has any one of the structures shown in general formulas I-III:
in the general formulas I to III, R1By substitution of H atoms at any one or two positions on the phenyl ring in which it is located, R2By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R3By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R4Substituted with H atoms at any one, two or three positions on the phenyl ring on which it is located.
The R is1、R2、R3、R4Each independently represents-H, -F, -Cl, -Br, -I, -n (Ar), -C (═ O) Ar, -P (═ O) Ar, -S (═ O)2Ar、-OAr、-SAr、-CN、-NO2An alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms or a sulfoalkoxy group having 1 to 40 carbon atoms.
The alkyl group having 1 to 40 carbon atoms may be a straight-chain alkyl group having 1 to 40 carbon atoms, a branched-chain alkyl group having 3 to 40 carbon atoms, or a cyclic alkyl group having 3 to 40 carbon atoms.
The alkoxy group having 1 to 40 carbon atoms may be a linear alkoxy group having 1 to 40 carbon atoms, a branched alkoxy group having 3 to 40 carbon atoms, or a cyclic alkoxy group having 3 to 40 carbon atoms.
The thioalkoxy group having 1 to 40 carbon atoms may be a linear thioalkoxy group having 1 to 40 carbon atoms, a branched thioalkoxy group having 3 to 40 carbon atoms, or a cyclic thioalkoxy group having 3 to 40 carbon atoms.
The R is1、R2、R3、R4The groups represented by each may be different, any two of them may be the same and different from the remaining two, any three of them may be the same and different from the remaining one, or four of them may be the same.
As a specific embodiment of the present invention, R is1、R2、R3、R4All represent H atoms.
In the general formulas I to III of the present invention for Ar1、Ar2The respective substitution positions are preferably selected to enhance the overall performance of the compound. Specifically, the method comprises the following steps:
in the general formula II, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae II-1 to II-3.
In the general formula III, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae III-1 to III-6.
As a specific embodiment of the invention, the OLED material has a structure shown as a general formula II-1.
As a specific embodiment of the present invention, the OLED material has a structure shown in the general formula II-1'.
Ar of the invention1、Ar2Each independently represents a group having an N-phenylcarbazole parent nucleus or represents an H atom, and Ar1、Ar2Not being H atoms at the same time。
Preferably, Ar is1、Ar2Each independently selected from the group consisting of:
ar is1、Ar2The substituents represented by each may be the same or different.
As a particular embodiment of the present invention, the OLED material is selected from compounds of the following specific structures:
the invention also provides a preparation method of the OLED material.
When in formula I Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When all Ar is contained, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I as a raw material, and carrying out a coupling reaction with Ar to obtain a compound I;
the reaction process is as follows:
when in formula I Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I' as a raw material, and sequentially reacting with Ar1、Ar2Carrying out coupling reaction to obtain a compound I;
the reaction process is as follows:
when in formula II Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II as a raw material, and carrying out a coupling reaction with Ar to obtain a compound II;
the reaction process is as follows:
when in formula II Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II 'as a raw material, and reacting the compound P-II' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound II;
the reaction process is as follows:
when in formula III Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III as a raw material, and carrying out a coupling reaction with Ar to obtain a compound III;
the reaction process is as follows:
when in formula III Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III 'as a raw material, and reacting the compound P-III' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound III;
the reaction process is as follows:
the above steps can be carried out by a person skilled in the art by known and conventional means, such as selecting a suitable catalyst, solvent, determining a suitable reaction temperature, time, etc.
In the above process for preparing a compound represented by any one of the general formulae I to III, when Ar is Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, as a preferred embodiment of the present invention, the method comprises: and (2) taking xylene as a reaction solvent, cuprous chloride as a catalyst, potassium hydroxide as an alkali, controlling the temperature to be 75-85 ℃ under the protection of nitrogen, and performing a coupling reaction on the raw materials and Ar to obtain the target compound.
Any one of the above-mentioned preparation general formulas I to IIIIn the process of the compound (1), when Ar is1、Ar2When the groups are different, as a preferred embodiment of the present invention, the method comprises: firstly, dimethylbenzene is used as a reaction solvent, cuprous chloride is used as a catalyst, potassium hydroxide is used as alkali, nitrogen is used for protection, the temperature is controlled to be 75-85 ℃, and the raw material and Ar are mixed1Coupling reaction is carried out to obtain an intermediate product; and then taking toluene as a solvent, palladium acetate and tri-tert-butylphosphine as catalysts, potassium tert-butoxide as an alkali, protecting with nitrogen, controlling the temperature to be 90-120 ℃, and reacting the intermediate product and Ar2Coupling reaction is carried out to obtain the target compound.
The starting materials for the solvents, catalysts, bases, etc., used in the present invention can be synthesized by published commercial routes or methods known in the art.
The invention also protects the application of the OLED material in an organic electroluminescent device. Preferably, the OLED material is used as a hole transport material in a hole transport layer.
The invention also provides an organic electroluminescent device, and a hole transport layer of the organic electroluminescent device contains the OLED material. Specifically, the organic electroluminescent device protected by the invention sequentially comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer, wherein the hole transport layer, the electroluminescent layer, the electron transport layer, the electron injection layer and the cathode layer are formed by the OLED material.
The OLED material provided by the invention is a compound which takes tonne-to-tonne as a center and has a high T1 energy level, a narrow band gap and a shallow Highest Occupied Molecular Orbital (HOMO) energy level. The perixanthenoxanthene is easily sublimable, stable in air, and does not undergo oxidative decomposition. Has high thermal stability and high glass transition temperature in air. By introducing a group with larger steric hindrance, the luminescent material is not easy to crystallize and quench and has good film-forming property.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
According to some embodiments of the present invention, the preferred solvent for preparing the organic electroluminescent device according to the present invention is selected from toluene, DMF or a mixture of these solvents. The reagents are analytically pure reagents, and the intermediate is purchased from an online shopping mall or is custom-synthesized from outsourcing companies.
Example 1
The synthetic route is as follows:
synthesis of Compound II-1-4
A1L three-necked flask was stirred with magnetic stirring and then charged with 40.07g (0.378mol) of sodium carbonate, 60.27g (99% purity, 0.21mol) of 4- (9H-carbazol-9-yl) phenyl) boronic acid and 100ml of toluene in this order after nitrogen substitution. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 60.36g of light yellow solid with purity of 99% and yield of 79%.
Product MS (m/e): 523; elemental analysis (C)38H21NO2): theoretical value C: 87.17%, H: 4.04%, N: 2.68%, O: 6.11 percent; found value C: 87.16%, H: 4.05%, N: 2.68%, O: 6.11 percent.
Example 2
The synthetic route is as follows:
synthesis of Compound II-1-14
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, 70.77g (purity 99%, 0.21mol) of (5-phenyl-5H-benzo [ b ] carbazol-3-yl) boric acid and 100ml of toluene in sequence after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 46.41g of light yellow solid with purity of 99% and yield of 81%.
Product MS (m/e): 573; elemental analysis (C)42H23NO2): theoretical value C: 87.94%, H: 4.04%, N: 2.44%, O: 5.58 percent; found value C: 87.93%, H: 4.05%, N: 2.44%, O: 5.58 percent.
Example 3
The synthetic route is as follows:
synthesis of Compounds II-1-19
A1 liter three-necked flask was stirred with magnetic stirring and then charged with 40.07g (0.378mol) of sodium carbonate, (81.27 g (purity 99%, 0.21mol) of 9-phenyl-9H-dibenzo [ a, c ] carbazol-11-yl) boronic acid and 100ml of toluene in this order after nitrogen substitution. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 49.84g of light yellow solid with purity of 99% and yield of 80%.
Product MS (m/e): 623; elemental analysis (C)46H25NO2): theoretical value C: 88.58 percent; h: 4.04 percent; n: 2.25 percent; o: 5.13 percent; found value C: 88.57 percent; h: 4.05 percent; n: 2.25 percent; o: 5.13 percent.
Example 4
The synthetic route is as follows:
synthesis of Compound II-1-21
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, 60.27g (purity 99 percent, 0.21mol) of (9-phenyl-9H-carbazole-2-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 60.36g of light yellow solid with purity of 99% and yield of 79%.
Product MS (m/e): 764; elemental analysis (C)56H32N2O2): theoretical value C: 87.94%, H: 3.66%, N: 3.66%, O: 4.18 percent; found value C: 87.93%, H: 3.67%, N: 3.66%, O: 4.18 percent.
Example 5
The synthetic route is as follows:
synthesis of Compound II-1-25
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, (76.23 g (purity 99%, 0.21mol) of 9- ([1,1' -biphenyl ] -4-yl) -9H-carbazol-3-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 71.45g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m/e): 916; elemental analysis (C)68H40N2O2): theoretical value C: 89.06%, H: 4.40%, N: 3.05%, O: 3.49 percent; found value C: 89.05%, H: 4.41%, N: 3.05%, O: 3.49 percent.
Example 6
The synthetic route is as follows:
synthesis of Compound II-1-27
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, (76.23 g (purity 99%, 0.21mol) of 9- ([1,1' -biphenyl ] -3-yl) -9H-carbazol-3-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, 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, and filtering to obtain 71.45g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m-e) The method comprises the following steps 916; elemental analysis (C)68H40N2O2): theoretical value C: 89.06 percent; h: 4.40 percent; n: 3.05 percent; o: 3.49 percent; found value C: 89.05 percent; h: 4.41 percent; n: 3.05 percent; o: 3.49 percent.
According to the technical schemes of the examples 1 to 6, the compounds shown in II-1-1 to II-1-44 can be synthesized only by simply replacing the corresponding raw materials without changing any substantial operation.
Preparation of device examples
(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 × 10-5~9×10-3PP1, evaporating HATCN as a first hole injection layer on the anode layer film in vacuum, 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;
(3) a layer II-1-4 is evaporated on the hole injection layer film to form a hole transmission layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
(4) EML is evaporated on the hole transport layer in vacuum 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;
(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;
(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, replacing the compound II-1-4 in the step (3) with the compound prepared in the embodiment 2-6 of the invention to obtain the devices OLED-2-OLED-6 provided by the invention.
According to the same procedure as above, compound II-1-4 in step (3) was replaced with a comparative compound (structure shown below), to give a comparative device OLED-7.
The results of the performance tests of the obtained devices OLED-1 to OLED-7 are shown in Table 1.
Table 1: performance test results of OLED-1 to OLED-7
From the above results, the current efficiency of the devices OLED-1 to OLED-6 prepared by using the OLED material provided by the present invention is higher, and the operating voltage is significantly lower than that of the device OLED-7 using the comparative compound 1 as the hole transport material under the same brightness condition.
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 (7)
1. An OLED material, characterized in that it has a structure represented by the general formula II-1':
ar is1、Ar2Each independently of the others represents a group having a N-phenylcarbazole parent nucleus or represents a H atom, Ar1、Ar2May be the same or different, and Ar1、Ar2Not H atoms at the same time.
4. use of the OLED material of any one of claims 1 to 3 in an organic electroluminescent device.
5. Use according to claim 4, wherein the OLED material is used as a hole transport material for a hole transport layer.
6. An organic electroluminescent device, characterized in that the hole transport layer contains the OLED material according to any one of claims 1 to 3.
7. An organic electroluminescent device, comprising a transparent substrate, an anode layer, a hole transport layer made of the OLED material according to any one of claims 1 to 3, an electroluminescent layer, an electron transport layer, an electron injection layer, and a cathode layer in this order from bottom to top.
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