CN108586352B - Organic material and application thereof in organic electroluminescent device - Google Patents
Organic material and application thereof in organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to the field of organic electroluminescence (OLED) display, in particular to an organic material and application thereof in an organic electroluminescent device, the novel OLED material provided by the invention has a structure shown in a general formula I, a fused aromatic compound is taken as a center, benzimidazole containing fluorine atoms is taken as an end group, and a substituent group (2- (3-fluorophenyl) phenylimidazole) with electron transmission performance is introduced into an active position of the fused aromatic compound to obtain the novel OLED material with the electron transmission performance. The material has high electron mobility, good film stability and proper molecular energy level, and can be applied to the field of organic electroluminescence and used as an electron transport material.
Description
Technical Field
The invention relates to a novel organic material and application thereof in an organic electroluminescent device, belonging to the technical field of organic electroluminescent display.
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 electron 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 electron 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 method has important practical application value.
Disclosure of Invention
The purpose of the present invention is to provide an OLED element that can be driven at low voltage, has a long lifetime, and has high efficiency, and a compound that can provide such an OLED element.
In order to develop a compound having the above-mentioned properties and an OLED device using the compound, it has been found that the above-mentioned object can be achieved by using the compound represented by the general formula (1).
That is, the present invention provides a novel organic material having a general structural formula as follows:
in the above formula, Ar is selected from:
m is an integer selected from 1 to 4.
Preferably, in formula I:
ar is selected from:
and/or m is 1,2 or 3.
Preferably, when m is 1, the structure of formula I is selected from one of the following:
when m is 2, the structure shown in the general formula I is selected from one of the following:
when m is 3, the structure shown in the general formula I is selected from one of the following structures:
as a further preferred technical solution, the organic material is selected from one of the following compounds:
the organic material contains fluorine atoms on the terminal benzimidazole, so that the distance between molecules can be increased, association between compounds is prevented, and the probability of stacking molecules is reduced. Crystallization is not easy to occur during evaporation, and the OLED device can effectively improve the OLED yield, reduce the driving voltage, improve the luminous efficiency and prolong the service life when being applied to the OLED device.
The invention also provides a preparation method of the organic material, and relates to two parallel schemes.
As one of the schemes, when Ar is:
the method specifically comprises the following steps:
(a) reacting a compound I-1 serving as a starting material with n-butyllithium to obtain a lithiation reagent, then performing lithiation reaction with unsaturated cyclic diketone, acidifying, and performing conventional treatment to obtain a compound I-2 under the action of sodium hypophosphite and potassium iodide;
(b) compound I-2 and
carrying out coupling reaction to obtain a compound I;
wherein m is an integer of 1 to 4 (in accordance with the definition in the organic material described above).
The above 2 steps can be realized by the ordinary means known to those skilled in the art, such as selecting suitable catalyst, solvent, determining suitable reaction temperature, time and the like.
Preferably, the preparation method comprises the following steps:
(a) taking a compound I-1 as a starting material, taking tetrahydrofuran as a solvent, reacting with n-butyl lithium at a temperature of between 90 ℃ below zero and 80 ℃ below zero, then controlling the temperature of between 90 ℃ below zero and 80 ℃ below zero, adding unsaturated cyclic diketone, and stirring for 20 +/-2 hours. Acidifying with acid, performing reflux reaction with sodium hypophosphite and potassium iodide for 20 +/-2 hours by using acetic acid as a solvent after conventional treatment to obtain a compound I-2;
(b) starting from the compound I-2, with
The compound I is obtained through the coupling reaction of piperidine formic acid and cuprous iodide.
Wherein m is an integer of 1 to 4 (in accordance with the definition in the organic material described above).
As a second alternative, when Ar is:
the method comprises the following steps:
(e) taking the compound I-1 as a starting material, and firstly reacting with
Coupling reaction to obtain a compound I-3;
(f) the compound I-3 is subjected to lithiation reaction with n-butyl lithium, then is subjected to reaction with trimethyl borate, and is acidified to obtain a compound I-4;
(g) carrying out SUZUKI coupling reaction on the compound I-4 and dibromo polycyclic aromatic hydrocarbon to obtain a compound I;
wherein m is an integer of 1 to 4.
More preferably, the method comprises the steps of:
(e) starting from the compound I-1, with
Carrying out coupling reaction on piperidine formic acid and cuprous iodide to obtain a compound I-3;
(f) taking a compound I-3 as a starting material, taking tetrahydrofuran as a solvent, carrying out lithiation reaction with n-butyl lithium at a temperature of between 90 ℃ below zero and 80 ℃ below zero, then carrying out reaction with trimethyl borate, and acidifying with hydrochloric acid to obtain a compound I-4;
(g) taking methylbenzene, ethanol and water as solvents, palladium tetratriphenylphosphine as a catalyst, sodium carbonate as alkali, and under the protection of nitrogen, carrying out SUZUKI coupling reaction on the compound I-4 and dibromo polycyclic aromatic hydrocarbon under reflux to obtain a compound I;
wherein m is an integer of 1 to 4.
As described above
Trimethyl borate, piperidinecarboxylic acid, n-butyllithium and the like can be synthesized by publicly available commercial methods or methods known per se in the literature.
The invention further provides application of the organic material in an organic electroluminescent device.
Preferably, the organic material of the present invention is used as an electron transport layer in an organic electroluminescent device.
The invention also provides an organic electroluminescent device, wherein the organic functional layer of the organic electroluminescent device comprises the compound with the general formula, and the compound is used as an electron transport material in the organic functional layer.
Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an organic light emitting layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence.
The material for forming the transparent substrate is a glass substrate or a flexible substrate;
the substrate may be a substrate used in a conventional organic light emitting device, for example: glass or plastic. In the device manufacturing process, a glass substrate and ITO are selected as anode materials.
The anode layer is made of inorganic materials; wherein the inorganic material is at least one of Indium Tin Oxide (ITO), zinc oxide, zinc tin oxide, gold, silver or copper, preferably Indium Tin Oxide (ITO);
the material constituting the hole transport layer is selected from various triarylamine-based materials. The hole transport material selected for use in the fabrication of the devices of the present invention is at least one of the compounds represented by NPB and TPD:
the material constituting the organic light emitting layer is composed of a host material;
wherein the host material is any one of the following compounds:
the material for forming the electron transport layer is a compound shown in a formula I;
the material of the electron injection layer is selected from LiF and Li2O, MgO or Al2O3Preferably LiF.
The cathode is made of a material selected from the group consisting of lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver, preferably aluminum.
In particular, the amount of the solvent to be used,
the thickness of the hole transport layer is 5-10nm, specifically 6 nm;
the thickness of the organic light-emitting layer is 10-80nm, specifically 40 nm;
the thickness of the electron transmission layer is 10-30nm, specifically 20 nm;
the thickness of the electron injection layer is 2-30nm, specifically 5 nm;
the thickness of the Al layer is 30-110nm, and is specifically 50 nm.
The novel OLED material provided by the invention takes a condensed-ring aromatic compound as a center, takes benzimidazole containing fluorine atoms as an end group, and introduces a substituent (2- (3-fluorophenyl) phenylimidazole) with electron transport performance at an active position of the condensed-ring aromatic compound to obtain the novel OLED material with the electron transport performance. The material has high electron mobility, good film stability and proper molecular energy level, and can be applied to the field of organic electroluminescence and used as an electron transport material.
Detailed Description
The basic chemical raw materials of various phenylbenzimidazole boric acids, various bromo-anthracene, bromo-perylene, bromo-pyrene, anthraquinone, benzoanthraquinone and the like used in the invention can be conveniently purchased in domestic chemical product markets, and various phenylbenzimidazole boric acids can be synthesized by using a common organic method.
The synthesis of the compounds in the present invention can be carried out by referring to the methods of example 1, example 2 and example 3. The following describes the synthesis of some of the main compounds of the present invention.
Example 1
The synthetic route is as follows:
1) synthesis of Compound 1-1
A1000 ml three-mouth bottle is stirred by magnetic force, 26.49g (purity 99 percent, 0.094mol) of 1-bromo-4-iodobenzene and THF500ml are added according to the amount after argon replacement. At-90 deg.c, n-BuLi38ml (2.5M concentration, 0.095mol) is dropped, 8.4g anthraquinone (99% purity, 0.04mol) is added, after the addition, the solution is naturally heated to room temperature, the solution is bright yellow, and the reaction is stirred for 20 h. Adding 500m of water for hydrolysis, separating liquid, extracting an aqueous phase by using dichloromethane, combining organic layers, evaporating the solvent to dryness, adding 600ml of acetic acid, 36g of KI and 36g of sodium hypophosphite, refluxing, reacting for 20 hours, cooling, filtering, and leaching by using water to obtain 17.49g of a yellow product with the purity of 99.5 percent and the yield of 90 percent.
2) Synthesis of Compound 1
N2Under the protection of gas, 16.53g (purity 94.5%, 0.034mol) of 9, 10-bis- (4-bromophenyl) anthracene, 21.63g (purity 99% 0.102mol) of 2- (3-fluorophenyl) benzimidazolyl, 2.6g (purity AR0.0136mol) of copper iodide, 5.4g (purity AR0.0136mol) of piperidinecarboxylic acid, and 35g (purity AR0.254mol) of potassium carbonate were charged in a 500mL three-necked flask. DMF 500ml, magnetic stirring, refluxing for 20 hours, cool filtration, yellow solid crude product with ethanol repeatedly boiled several times, yellow solid 13.22g, purity 99.4%, yield 80%.
Product MS (m/e): 750.26, respectively;
elemental analysis (C)52H32F2N4): theoretical value C: 83.18%, H: 4.30%, F: 5.06%, N: 7.46 percent; found value C: 83.15%, H: 4.33%, F: 5.02%, N: 7.50 percent.
According to the technical scheme of the example 1, the following compounds can be synthesized only by simply replacing corresponding raw materials without changing any substantial operation.
Example 2
The synthetic route is as follows:
1) synthesis of Compound 2-1
N2Under the protection of gas, 9.58g (0.034mol) of 4-bromoiodobenzene, 7.21g (0.034mol) of 2- (3-fluorophenyl) benzimidazolyl, 2.6g (purity AR0.0136mol) of copper iodide, 5.4g (purity AR0.0136mol) of piperidinecarboxylic acid and 35g (purity AR0.254mol) of potassium carbonate were put into a 500mL three-necked flask. DMF (600 ml) is stirred magnetically, refluxed for 30 hours, cooled and filtered, and the crude yellow solid is boiled with ethanol for several times to obtain 9.96g of yellow solid with the purity of 99.6 percent and the yield of 80 percent.
2) Synthesis of Compound 2-2
73.20g of 4- (2- (3-fluorophenyl) benzimidazolyl) bromobenzene (compound 1-1, 0.2mol) and 1000ml of tetrahydrofuran are added into a 2L dry and clean three-necked bottle, nitrogen is protected, liquid nitrogen is cooled to minus 80 ℃, 80ml of butyllithium is added dropwise, temperature control reaction is carried out for 1h after dropwise addition, 32g of trimethyl borate (0.30mol) is added dropwise, temperature control reaction is carried out for 30 minutes at minus 80 ℃, then natural temperature rise to minus 20 ℃ is carried out, and 600ml of hydrochloric acid aqueous solution is added dropwise. Separating, extracting the water phase twice with 400ml × 2 ethyl acetate, combining the organic phases, and spin-drying to obtain a white solid with liquid phase purity (LC) of 99.1%, theoretical yield of 66.42g, actual yield of 63.10g and yield of 95%;
3) synthesis of Compound 2
N2Under the protection of gas, 7.34g (purity 98%, 0.02mol) of 1, 6-di-bromopyrene, 16.61g (purity 98%, 0.050mol) of 4- (2- (3-fluorophenyl) benzimidazolyl) phenylboronic acid, 0.46g (purity AR, 0.0004mol) of palladium tetrakistriphenylphosphine, 17.3g (purity AR, 0.125mol) of potassium carbonate, 300mL of toluene, 300mL of ethanol, and 100mL of water were added to a 1000mL three-necked flask. Heating and refluxing the materials. After 15 hours the reaction was stopped, allowed to cool and filtered to give a yellow solid which was recrystallized twice from 16 times THF. 13.63g of a pale yellow product are obtained, with a purity of 99.80% and a yield of 88%.
Product MS (m/e): 774.26; elemental analysis (C)54H32F2N4): theoretical value C: 83.70%, H: 4.16%, F: 4.90%, N: 7.23 percent; found value C: 83.68%, H: 4.18%, F: 4.87%, N: 7.27 percent
Example 3: synthesis of Compound 3
N2Under the protection of gas, 11.52g (purity 98%, 0.03mol) of 6, 12-dibromochrysene, 24.91g (purity 99%, 0.075mol) of 4- (2- (3-fluorophenyl) benzimidazolyl) phenylboronic acid, 0.69g (purity AR, 0.0006mol) of palladium tetratriphenylphosphine, 25.88g (purity AR, 0.188mol) of potassium carbonate, 300mL of toluene, 50mL of ethanol and 50mL of water were charged into a 1000mL three-necked flask. Heating and refluxing the materials. After 30 hours the reaction was stopped, allowed to cool, filtered to give a yellow solid, which was recrystallized from THF and repeated twice. 19.21g of a pale yellow product are obtained, with a purity of 99.80% and a yield of 80%.
Product MS (m/e): 800.28, respectively; elemental analysis (C)56H34F2N4): theoretical value C: 83.98%, H: 4.28%, F: 4.74%, N: 7.00 percent; found value C: 83.97%, H: 4.29%, F: 4.72%, N: 7.02 percent
According to the technical schemes of the embodiment 2 and the embodiment 3, the following compounds can be synthesized only by simply replacing corresponding raw materials without changing any substantial operation.
EXAMPLE 4 preparation of devices OLED-1-OLED-4
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to
1×10-5～9×10-4Pa, evaporating a compound NPB on the anode layer film to form a hole transport layer, wherein the evaporation rate is 0.2nm/s, and the evaporation film thickness is 6 nm;
3) continuously evaporating ADN on the hole transport layer to be used as a main material and an organic light-emitting layer of the device, wherein the evaporation rate is 0.2nm/s, and the thickness of the organic light-emitting layer obtained by evaporation is 40 nm;
4) continuously evaporating a layer of the compound 1 which is prepared in the embodiment 1 and belongs to the formula I on the organic light-emitting layer to be used as an electron transport layer of a device, wherein the evaporation rate is 0.2nm/s, and the evaporation film thickness is 20 nm;
5) continuously evaporating a layer of LiF on the electron transport layer to be used as an electron injection layer of the device, wherein the evaporation rate is 0.2nm/s, and the evaporation film thickness is 5 nm;
6) continuously evaporating a layer of Al on the electron injection layer to be used as a cathode of the device, wherein the evaporation rate is 0.2nm/s, and the evaporation film thickness is 50 nm; obtaining the OLED device provided by the invention, and marking as OLED-1;
replacing the compound 1 in the step 4) with the compound 2 prepared in the example 2 according to the same procedure as above to obtain the OLED-2 provided by the invention;
replacing the compound 1 in the step 4) with the compound 3 prepared in the example 3 according to the same procedure as above to obtain the OLED-3 provided by the present invention;
replacing compound 1 in step 4) with ET1 following the same procedure as above to give a comparative device OLED-4;
The results of the performance tests of the obtained devices OLED-1 to OLED-4 are shown in Table 1.
TABLE 1 measurement results of OLED-1 to OLED-4
From the above, the light-emitting voltage of the devices OLED-1 to OLED-4 prepared by using the organic material shown in formula I provided by the present invention is lower, the current efficiency is obviously much higher than that of the device OLED-4 using ET1 as an electron transport material under the same brightness condition, and the lifetime of the device is obviously prolonged.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
Claims (8)
1. An organic material, characterized by: the organic material is selected from the following compounds:
2. a method for producing an organic material according to claim 1, characterized in that: when the organic material is:
the method specifically comprises the following steps:
(a) to be provided with
The initial raw material is firstly reacted with n-butyl lithium to obtain lithiation reagent, then the lithiation reagent is reacted with unsaturated cyclic diketone to obtain lithiation reagent, and the lithiation reagent is acidified and obtained under the action of sodium hypophosphite and potassium iodide
Wherein the unsaturated cyclic diketone has the chemical formula
(b)
And
by coupling reaction to obtain
When the organic material is:
the method comprises the following steps:
(e) to be provided with
As starting materials, first with
By coupling reaction to obtain
(f)
Lithiation reaction with n-butyl lithium, reaction with trimethyl borate, and acidification to obtain the final product
(g)
Carrying out SUZUKI coupling reaction with dibromo polycyclic aromatic hydrocarbon to obtain
Wherein the dibromo polycyclic aromatic hydrocarbon has a chemical formula of
3. Use of the organic material of claim 1 in an organic electroluminescent device.
4. Use according to claim 3, characterized in that: the organic material is used as an electron transport layer in the organic electroluminescent device.
5. An organic electroluminescent device, characterized in that: comprising an electron transport layer made of the organic material of claim 1.
6. The organic electroluminescent device according to claim 5, wherein: the organic electroluminescent device consists of a transparent substrate, an anode layer, a hole transport layer, an organic luminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence.
7. The organic electroluminescent device according to claim 6, wherein: the material for forming the transparent substrate is a glass substrate or a flexible substrate;
and/or; the anode layer is made of at least one of indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper;
and/or; the material constituting the hole transport layer is at least one of compounds represented by NPB and TPD:
and/or; the material for forming the organic light-emitting layer is any one of the following compounds:
and/or; the material of the electron injection layer is selected from LiF and Li2O, MgO or Al2O3One of (1);
and/or; the cathode is made of one material selected from lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold and silver.
8. The organic electroluminescent device according to claim 7, wherein:
the thickness of the hole transport layer is 5-10 nm; the thickness of the organic light-emitting layer is 10-80 nm; the thickness of the electron transmission layer is 10-30 nm; the thickness of the electron injection layer is 2-30 nm; the thickness of the Al layer is 30-110 nm.
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