CN111675686A - Organic electroluminescent compound and preparation method and application thereof - Google Patents

Organic electroluminescent compound and preparation method and application thereof Download PDF

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CN111675686A
CN111675686A CN202010657588.3A CN202010657588A CN111675686A CN 111675686 A CN111675686 A CN 111675686A CN 202010657588 A CN202010657588 A CN 202010657588A CN 111675686 A CN111675686 A CN 111675686A
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organic electroluminescent
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王士凯
汪康
李贺
杨冰
曹淼
白金凤
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic electroluminescent compound, which has a structural general formula shown in chemical formula 1:
Figure DDA0002577308010000011
wherein, A is at any two adjacent positions on the benzene ring or is not existed; x is S or O; r1～R9Each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C6-C30 arylamine, and adjacent substituents are linked to form a single ring or multiple rings; ar (Ar)1、Ar2Each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroaryl, linked to an adjacent substituent to form a single ring or multiple rings; l is a bond, substituted or unsubstituted C6-C30 aryl; the organic luminescent compound has the advantages of short synthetic route, simple process, easily obtained raw materials and low cost, and is suitable for industrial production.

Description

Organic electroluminescent compound and preparation method and application thereof
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent compound, a preparation method thereof and an organic electroluminescent device.
Background
An electroluminescent device (EL device) is an automatic light emitting device, which is advantageous in that it provides a wide viewing angle, a large contrast ratio, and a fast response time.
In such an organic EL device, when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected into an organic material layer. The generated excitons generate light having a specific wavelength while migrating to a ground state. In order to improve the efficiency and stability of the organic EL device, it is required to have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The hole transport layer can change hole transport efficiency, light emission efficiency, lifetime, and the like of holes to the light emitting layer. Commonly used hole transport materials are copper phthalocyanine (CuPc), 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N ' -diphenyl-N, N ' -bis (3-methylphenyl) - (1, 1 ' -biphenyl) -4, 4' -diamine (TPD), and the like. Organic EL devices using these materials have problems in quantum efficiency and service life, and further improvements in quantum efficiency and life are required.
Therefore, it is an urgent technical problem to be solved by those skilled in the art to provide an organic electroluminescent compound with high quantum efficiency and long lifetime, and a preparation method and application thereof.
Disclosure of Invention
In view of the above, the invention provides an organic electroluminescent compound with a short synthetic route and a simple process;
in order to achieve the purpose, the invention adopts the following technical scheme:
an organic electroluminescent compound, the structural general formula of which is shown in chemical formula 1:
Figure BDA0002577306000000021
wherein, A is at any two adjacent positions on the benzene ring or is not existed;
x is S or O;
R1～R9each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C6-C30 arylamine, and adjacent substituents are linked to form a single ring or multiple rings;
Ar1、Ar2each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroaryl, linked to an adjacent substituent to form a single ring or multiple rings;
l is a bond, or L is a substituted or unsubstituted C6-C30 aryl;
further, the L is preferably benzene or deuterated benzene;
further, the A is substituted or unsubstituted C6-C30 aryl, preferably benzene or deuterated benzene;
the R is1～R9、Ar1、Ar2When taken alone and linked to an adjacent substituent to form a monocyclic or polycyclic ring, the monocyclic or polycyclic ring is a 3-to 30-membered aliphatic or aromatic ring, and the aliphatic or aromatic ring contains at leastOne carbon atom which may be replaced by a nitrogen, oxygen or sulfur heteroatom.
Adopt above-mentioned further beneficial effect to lie in: the structure of the compound limited by the invention improves the thermal stability and the chemical stability of the material, the whole molecule is a larger rigid structure, has high triplet state energy level (T1), and has large steric hindrance and stable three-dimensional space.
The above-mentioned "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted, that is, a position at which the substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
Preferably, the structural formula of the organic electroluminescent compound is any one of the following structural formulas:
Figure BDA0002577306000000031
Figure BDA0002577306000000041
Figure BDA0002577306000000051
Figure BDA0002577306000000061
Figure BDA0002577306000000071
the invention also provides a preparation method of the organic electroluminescent compound, and the synthetic route when L is a substituent is as follows:
Figure BDA0002577306000000072
or the like, or, alternatively,
the synthetic route is as follows when L is a connecting bond:
Figure BDA0002577306000000081
the method comprises the following steps:
(1) dissolving a compound 1 and a compound 2 in toluene, placing the toluene in a reaction container, replacing gas in the reaction container with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide into a toluene solution under the protection of nitrogen, stirring uniformly, heating to reflux for reaction for 5-8 hours, after the reaction is finished, cooling a reaction solution to room temperature, adding a saturated ammonium chloride aqueous solution into the reaction solution for reaction, and extracting the reaction solution with ethyl acetate after the reaction is finished; the extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator, and the remaining material was purified by column chromatography to give intermediate 1;
(2) dissolving the intermediate 1 and the compound 3 in toluene, adding the mixture into a reaction container, replacing gas in the reaction container with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, continuously stirring, heating to reflux, reacting for 5-8 hours, after the reaction is finished, cooling reaction liquid to room temperature, extracting the reaction solution with dichloromethane and water, drying an extracted organic layer with sodium sulfate, removing the solvent with a rotary evaporator, and purifying the rest substance with column chromatography to obtain an intermediate 2;
dissolving the intermediate 2 and the compound 4 in a mixed solution of toluene, ethanol and water, replacing gas in a reaction container with nitrogen for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, continuously stirring, heating to reflux, reacting for 8-10 hours, cooling a reaction solution to room temperature after the reaction is finished, and extracting the mixture with dichloromethane and water; then drying the extracted organic layer with sodium sulfate, removing the solvent using a rotary evaporator, and purifying the remaining material using column chromatography to obtain a compound represented by chemical formula 1;
or the like, or, alternatively,
dissolving the intermediate 1 and the compound 3 in toluene, adding the mixture into a reaction vessel, replacing gas in the reaction vessel with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, heating to reflux for reaction for 5 hours, after the reaction is finished, cooling the reaction solution to room temperature, extracting the reaction solution with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent with a rotary evaporator, and purifying the rest substance with column chromatography to obtain an intermediate 2.
Further, the stirring speed in the step (1) and the stirring speed in the step (2) are both 80r/min, the water bath temperature of the rotary evaporator is 70 ℃, and the ethyl acetate and the petroleum ether are adopted in the chromatographic column method according to the ratio of 1:25 volume ratio for purification;
furthermore, the molar ratio of the compound 1 to the ammonium chloride in the step (1) is 1: 10;
further, the palladium catalyst is tris (dibenzylideneacetone) dipalladium or tetratriphenylphosphine palladium; the phosphine ligand is tri-tert-butylphosphine;
when L is a substituent or a connecting bond; the molar ratio of the compound 1 to the compound 2 in the step (1) is 1: 1; the molar ratio of the palladium catalyst, the phosphine ligand and the sodium tert-butoxide is 1:5: 200.
Adopt above-mentioned further beneficial effect to lie in: the raw material proportion defined by the invention can ensure that the raw material utilization rate is high, the reaction rate is high, the purity of the obtained crude product is high, the purification is easy, and the product yield is high
Further, when L is a substituent or a connecting bond; the molar ratio of the intermediate 1 to the compound 3 in the step (2) is 1: 1;
the molar ratio of the palladium catalyst, the phosphine ligand and the sodium tert-butoxide is 1:5: 200.
Adopt above-mentioned further beneficial effect to lie in: the raw material proportion defined by the invention can ensure that the raw material utilization rate is high, the reaction rate is high, the purity of the obtained crude product is high, the purification is easy, and the product yield is high
Further, when L is a substituent, the molar ratio of the compound 4 to the intermediate 2 in the step (2) is 1: 1; the volume ratio of the toluene to the ethanol to the water is 3:1: 1;
the molar ratio of the palladium catalyst to the potassium carbonate is 1: 300.
Adopt above-mentioned further beneficial effect to lie in: the raw material proportion limited by the invention can lead the reaction to be rapid, the reaction to be mild, the purification to be easy and the product yield to be high
The invention has the beneficial effects that: the organic luminescent compound has the advantages of short synthetic route, simple process, easily obtained raw materials and low cost, and is suitable for industrial production.
The invention also provides application of the organic electroluminescent compound in preparing organic electroluminescent devices.
An organic electroluminescent device comprising, in order, a first electrode, one or more organic layers, and a second electrode; at least one of the organic layers comprises an organic electroluminescent compound according to claim 1 or 2.
Further, the organic layer is one or more layers of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a hole injection-hole transport functional layer, a light emitting layer, an electron transport layer, an electron injection layer, and at least one of them includes the organic electroluminescent compound according to claim 1 or 2; preferably, at least one of the organic layers comprises a hole injecting substance, a hole transporting substance, a light-emitting auxiliary substance, or a hole injecting-hole transporting functional layer.
When the organic layer is of a single-layer structure, the organic layer is a light-emitting layer, and when the organic layer is of a multilayer structure, the organic layer comprises the light-emitting layer;
adopt above-mentioned further beneficial effect to lie in: the organic matter can effectively improve the luminous efficiency and the hole mobility of the material, simultaneously plays a role in blocking electrons, can reduce the integral driving voltage of the device, improves the luminous efficiency and improves the service life of the device.
Furthermore, the light-emitting layer is one or more of a phosphorescent host, a fluorescent host, a phosphorescent doped material and a fluorescent doped material. When the organic layer includes a hole transport layer or a light emission auxiliary layer, the hole transport layer includes an organic light emitting compound represented by chemical formula 1.
Adopt above-mentioned further beneficial effect to lie in: the sublimation temperature of the material is reduced, the heat-resistant characteristic of the material is greatly improved, the thermal stability of the material is improved, and the luminous efficiency is excellent;
compared with the prior art, the invention has the beneficial effects that: the organic electroluminescent device provided by the invention has the advantages of high quantum efficiency, low driving voltage and longer service life.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1: preparation of Compound 1
Figure BDA0002577306000000111
(1) Adding compound 1-1(210mmol) and compound 2-1(210mmol) in a reaction vessel, adding 300ml of toluene solution and placing in the reaction vessel, displacing gas in the reaction vessel with nitrogen gas 3 times, adding tris (dibenzylideneacetone) dipalladium (2.1mmol), tri-t-butylphosphine (10.5mmol) and sodium t-butoxide (420mmol) under nitrogen atmosphere, heating to reflux, stirring at 80r/min for 5 hours, after completion of the reaction, cooling the reaction solution to room temperature after the reaction is completed, adding an aqueous ammonium chloride solution to the reaction solution to complete the reaction, the molar ratio of compound 1 to ammonium chloride being 1:10, and extracting the reaction solution with ethyl acetate, then drying the extracted organic layer with magnesium sulfate, and heating in a water bath at 70 ℃ using a rotary evaporator to remove the solvent, purifying the remaining substance with column chromatography and with a volume ratio of ethyl acetate to petroleum ether of 1:25 to obtain intermediate 1-1(34.2 g), yield 66.4%, MW: 245.33).
(2) After the intermediate 1-1(130mmol), the compound 3-1(130mmol) and 500mL of toluene were added to a reaction vessel, the gas in the reaction vessel was replaced with nitrogen gas 3 times, tris (dibenzylideneacetone) dipalladium (1.30mmol), tri-tert-butylphosphine (6.50mmol) and sodium tert-butoxide (260mmol) were added under nitrogen atmosphere, the mixture was heated to reflux and stirred at 80r/min for 5 hours, and the reaction was completed. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield intermediate 2-1(24.8g, 52.4% yield, MW: 365.24).
(3) Intermediate 2-1(65mmol), Compound 4-1(65mmol) and solvent (180ml toluene, 60ml ethanol, and 60ml H2O) is added into the reaction vessel, the gas in the reaction vessel is replaced by nitrogen for 3 times, tetratriphenylphosphine palladium (0.65mmol) and potassium carbonate (195mmol) are added under the nitrogen atmosphere, the mixture is heated to reflux, and the mixture is stirred for 10 hours at the speed of 80r/min, thus finishing the reaction. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield compound 1(27.8g, 73.7% yield, MW: 579.74).
Example 2: preparation of Compound 27
Figure BDA0002577306000000131
(1) Adding the compound 1-27(210mmol) and the compound 2-27(210mmol) into a reaction vessel, adding 300ml of toluene solution, placing the mixture into the reaction vessel, replacing the gas in the reaction vessel with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (2.1mmol), tri-tert-butylphosphine (10.5mmol) and sodium tert-butoxide (420mmol) under nitrogen atmosphere, heating to reflux, stirring at 80r/min for 5h, and finishing the reaction. After the reaction was completed, after the reaction liquid was cooled to room temperature, an aqueous ammonium chloride solution was added to the reaction solution to complete the reaction, the molar ratio of compound 1 to ammonium chloride was 1:10, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by heating in a 70 ℃ water bath using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield intermediates 1-27(53.2g, 63.1% yield, MW: 401.55).
(2) After the intermediate 1 to 27(130mmol), the compound 3 to 27(130mmol) and 500mL of toluene were charged into a reaction vessel, the gas in the reaction vessel was replaced with nitrogen gas 3 times, tris (dibenzylideneacetone) dipalladium (1.30mmol), tri-tert-butylphosphine (6.50mmol) and sodium tert-butoxide (260mmol) were added under nitrogen atmosphere, the mixture was heated to reflux and stirred at 80r/min for 5 hours, and the reaction was completed. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield compound 27(49.6g, 57.9% yield, MW: 659.87).
Example 3: preparation of Compound 41
Figure BDA0002577306000000141
(1) Adding a compound 1-41(210mmol) and a compound 2-41(210mmol) into a reaction vessel, adding 300ml of toluene solution, placing the mixture into the reaction vessel, replacing the gas in the reaction vessel with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (2.1mmol), tri-tert-butylphosphine (10.5mmol) and sodium tert-butoxide (420mmol) under the nitrogen atmosphere, heating to reflux, stirring for 5 hours at 80r/min, and finishing the reaction. After the reaction was completed, after the reaction liquid was cooled to room temperature, an aqueous ammonium chloride solution was added to the reaction solution to complete the reaction, the molar ratio of compound 1 to ammonium chloride was 1:10, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by heating in a 70 ℃ water bath using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield intermediates 1-41(38.5g, 64.3% yield, MW: 285.15).
(2) After the intermediate 1 to 41(130mmol), the compound 3 to 41(130mmol) and 500mL of toluene were added to a reaction vessel, the gas in the reaction vessel was replaced with nitrogen gas 3 times, tris (dibenzylideneacetone) dipalladium (1.30mmol), tri-tert-butylphosphine (6.50mmol) and sodium tert-butoxide (260mmol) were added under nitrogen atmosphere, the mixture was heated to reflux and stirred at 80r/min for 5 hours, and the reaction was completed. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield compound 41(40.0g, 55.1% yield, MW: 559.23).
Example 4: preparation of Compound 46
Figure BDA0002577306000000151
(1) Adding a compound 1-46(210mmol) and a compound 2-46(210mmol) into a reaction vessel, adding 300ml of toluene solution, placing the mixture into the reaction vessel, replacing the gas in the reaction vessel with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (2.1mmol), tri-tert-butylphosphine (10.5mmol) and sodium tert-butoxide (420mmol) under the nitrogen atmosphere, heating to reflux, stirring for 5 hours at 80r/min, and finishing the reaction. After the reaction was completed, after the reaction liquid was cooled to room temperature, an aqueous ammonium chloride solution was added to the reaction solution to complete the reaction, the molar ratio of compound 1 to ammonium chloride was 1:10, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by heating in a 70 ℃ water bath using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield intermediates 1-46(38.2g, 63.8% yield, MW: 285.39).
(2) After the intermediate 1 to 46(130mmol), the compound 3 to 46(130mmol) and 500mL of toluene were added to a reaction vessel, the gas in the reaction vessel was replaced with nitrogen gas 3 times, tris (dibenzylideneacetone) dipalladium (1.30mmol), tri-tert-butylphosphine (6.50mmol) and sodium tert-butoxide (260mmol) were added under nitrogen atmosphere, the mixture was heated to reflux and stirred at 80r/min for 5 hours, and the reaction was completed. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield compound 46(40.0g, 56.6% yield, MW: 543.71).
Example 5: preparation of Compound 54
Figure BDA0002577306000000161
Adding a compound 1-54(210mmol) and a compound 2-54(210mmol) into a reaction vessel, adding 300ml of toluene solution, placing the mixture into the reaction vessel, replacing the gas in the reaction vessel with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (2.1mmol), tri-tert-butylphosphine (10.5mmol) and sodium tert-butoxide (420mmol) under the nitrogen atmosphere, heating to reflux, stirring for 5 hours at 80r/min, and finishing the reaction. After the reaction was completed, after the reaction liquid was cooled to room temperature, an aqueous ammonium chloride solution was added to the reaction solution to complete the reaction, the molar ratio of compound 1 to ammonium chloride was 1:10, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by heating in a 70 ℃ water bath using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to yield intermediates 1-54(33.5g, 65.0% yield, MW: 245.33).
After the intermediate 1 to 54(130mmol), the compound 3 to 54(130mmol) and 500mL of toluene were added to a reaction vessel, the gas in the reaction vessel was replaced with nitrogen gas 3 times, tris (dibenzylideneacetone) dipalladium (1.30mmol), tri-tert-butylphosphine (6.50mmol) and sodium tert-butoxide (260mmol) were added under nitrogen atmosphere, the mixture was heated to reflux and stirred at 80r/min for 5 hours, and the reaction was completed. After the reaction was completed, the reaction solution was cooled to room temperature, the mixture was extracted with dichloromethane, the extracted organic layer was dried with sodium sulfate, and the solvent was removed by heating in a water bath at 70 ℃ using a rotary evaporator. The remaining material was purified by column chromatography using ethyl acetate and petroleum ether at a volume ratio of 1:25 to give compound 54(25.2g, 53.0% yield, MW: 365.24).
The synthesis of the other compounds was the same as in the above-mentioned examples, and thus, they are not illustrated, and some of the mass spectra and molecular formulae are shown in Table 1 below.
Table 1:
Figure BDA0002577306000000171
Figure BDA0002577306000000181
example 17 preparation of organic electroluminescent device Using light-emitting Compound
The compound synthesized by the embodiment of the invention is used as a hole transport material, and an organic electroluminescent device is prepared by adopting a common method. Firstly, evaporating N1- (naphthalene-2-yl) -N4, N4-di (4- (naphthalene-2-yl (phenyl) amino) phenyl) -N1-phenyl-1, 4-diamine ("2-TNATA") on an ITO (anode) in a thickness of 60nm, and then evaporating a compound 1 synthesized by the invention in a thickness of 60nm, a host substance 4,4'-N, N' -dicarbazole-biphenyl ("CBP") and a doping substance (btp)2Ir (acac) is mixed according to a weight ratio of 90:10 to be evaporated with a thickness of 30nm, an evaporated hole blocking layer (' BALq ') with a thickness of 10nm, an evaporated Alq3 ' with a thickness of 40nm, an evaporated electron injection layer with a thickness of 0.3nm LiF and an evaporated cathode with a thickness of 150nm Al to form the organic electroluminescent device.
Device example 2 device example 16 organic electroluminescent device
Organic electroluminescent devices were produced in the same manner as in example 1, except that the substances described in examples 2 to 5 and table 1 were used as hole transport materials instead of compound 1 in device example 1.
Device comparative example 1 [ device comparative example 3]
Organic electroluminescent devices were produced in the same manner as in device example 1 except that in example 1, except for compound 1, comparative compounds 1 to 3 were used to produce device comparative example 1 to device comparative example 3, respectively.
Figure BDA0002577306000000182
Device example 1 device example of the inventionEXAMPLE 16, DEVICE COMPARATIVE EXAMPLE 1-DEVICE COMPARATIVE EXAMPLE 3 the organic electroluminescent device prepared was biased and tested for electroluminescent characteristics (EL) at 6000cd/m using PR-650 from Photoreearch corporation2Life equipment test T95 prepared with Mcscience at baseline brightness. The measurement results are shown in Table 2.
TABLE 2
Figure BDA0002577306000000191
From the results of table 2, it can be confirmed that the organic electroluminescent device prepared using the compound provided by the present invention as a hole material exhibits high luminous efficiency and long life and reduced driving voltage. Compared with the comparative example, the driving voltage is reduced by about 1.5V, the luminous efficiency is improved by about 10 percent, and the service life of the device is also obviously improved.
The above description is a simple illustration of the invention, the application of the invention is not limited to the above examples, and it will be obvious to a person skilled in the art that modifications and variations can be made within the scope of the above description, and all such modifications and variations are intended to fall within the scope of the claims. In the following description, the scope of the present disclosure is not limited to the embodiments described in the embodiments. The scope of the present invention must be interpreted within the scope of the following claims, and all techniques that are equivalent to the scope of the present invention are included in the scope of the claims.

Claims (10)

1. An organic electroluminescent compound, wherein the structural general formula of the organic electroluminescent compound is shown in chemical formula 1:
Figure FDA0002577305990000011
wherein, A is at any two adjacent positions on the benzene ring or is not existed;
x is S or O;
R1～R9each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroAryl, substituted or unsubstituted arylamine of C6-C30 or linked with adjacent substituents to form a single ring or multiple rings;
Ar1、Ar2each independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted heteroaryl, or are linked to an adjacent substituent to form a single ring or multiple rings;
l is a chemical bond; or L is a substituted or unsubstituted C6-C30 aryl group.
2. An organic electroluminescent compound according to claim 1, wherein a is a substituted or unsubstituted C6-C30 aryl group;
the R is1～R9、Ar1、Ar2When taken alone and linked to an adjacent substituent to form a mono-or polycyclic ring, the mono-or polycyclic ring is a 3-to 30-membered aliphatic or aromatic ring, and at least one carbon atom of the aliphatic or aromatic ring may be replaced with nitrogen, oxygen, or sulfur.
3. A method for preparing an organic electroluminescent compound is characterized in that,
the synthetic route is as follows when L is a substituent group:
Figure FDA0002577305990000021
or the like, or, alternatively,
the synthetic route is as follows when L is a connecting bond:
Figure FDA0002577305990000022
the method comprises the following steps:
(1) dissolving a compound 1 and a compound 2 in toluene, placing the toluene in a reaction container, replacing gas in the reaction container with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide into a toluene solution under the protection of nitrogen, stirring uniformly, stirring and heating until reflux reaction is carried out for 5-7 hours, after the reaction is finished, cooling a reaction solution to 20 ℃, adding a saturated ammonium chloride aqueous solution into the reaction solution for reaction, and extracting the reaction solution with ethyl acetate after the reaction is finished; the extracted organic layer was then dried over magnesium sulfate and concentrated using a rotary evaporator to remove the solvent, followed by purification by column chromatography to give intermediate 1;
(2) dissolving the intermediate 1 and the compound 3 in toluene, adding the mixture into a reaction container, replacing gas in the reaction container with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, continuously stirring and heating to reflux for 5-7 hours, after the reaction is finished, cooling reaction liquid to room temperature, extracting the reaction solution with dichloromethane and water, drying an extracted organic layer with sodium sulfate, removing the solvent with a rotary evaporator, and purifying the rest substance with a column chromatography to obtain an intermediate 2;
dissolving the intermediate 2 and the compound 4 in a mixed solution of toluene, ethanol and water, replacing gas in a reaction container with nitrogen for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, continuously stirring, heating to reflux, reacting for 8-10 hours, cooling a reaction solution to room temperature after the reaction is finished, and extracting the mixture with dichloromethane and water; then drying the extracted organic layer with sodium sulfate, removing the solvent using a rotary evaporator, and purifying the remaining material using column chromatography to obtain a compound represented by chemical formula 1;
or the like, or, alternatively,
dissolving the intermediate 1 and the compound 3 in toluene, adding the mixture into a reaction container, replacing gas in the reaction container with nitrogen for 3 times, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, continuously stirring, heating to reflux, reacting for 5-8 hours, after the reaction is finished, cooling reaction liquid to room temperature, extracting the reaction solution with dichloromethane and water, drying an extracted organic layer with sodium sulfate, removing the solvent by using a rotary evaporator, and purifying the rest substance by using column chromatography to obtain an intermediate 2.
4. The method for producing an organic electroluminescent compound according to claim 3, wherein L is a substituent or a connecting bond; the molar ratio of the compound 1 to the compound 2 in the step (1) is 1: 1;
the molar ratio of the palladium catalyst, the phosphine ligand and the sodium tert-butoxide is 1:5: 200.
5. The method for producing an organic electroluminescent compound according to claim 3, wherein L is a substituent or a connecting bond; the molar ratio of the intermediate 1 to the compound 3 in the step (2) is 1: 1;
the molar ratio of the palladium catalyst, the phosphine ligand and the sodium tert-butoxide is 1:5: 200.
6. The method for producing an organic electroluminescent compound according to claim 3, wherein when L is a substituent, the molar ratio of the compound 4 to the intermediate 2 in the step (2) is 1: 1; the volume ratio of the toluene to the ethanol to the water is 3:1: 1;
the molar ratio of the palladium catalyst to the potassium carbonate is 1: 300.
7. Use of the organic electroluminescent compound according to claim 1 or 2 for the preparation of organic electroluminescent devices.
8. An organic electroluminescent device comprising, in order, a first electrode, one or more organic layers, and a second electrode; at least one of the organic layers comprises the organic electroluminescent compound according to claim 1 or 2.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole injection-hole transport functional layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one layer comprises the organic electroluminescent compound according to claim 1 or 2.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises one or more of a phosphorescent host material, a fluorescent host material, a phosphorescent dopant material and a fluorescent dopant material.
CN202010657588.3A 2020-07-09 2020-07-09 Organic electroluminescent compound and preparation method and application thereof Pending CN111675686A (en)

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Application publication date: 20200918