CN112062765A - Organic photoelectric luminescent compound and preparation method thereof - Google Patents

Organic photoelectric luminescent compound and preparation method thereof Download PDF

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CN112062765A
CN112062765A CN202010989362.3A CN202010989362A CN112062765A CN 112062765 A CN112062765 A CN 112062765A CN 202010989362 A CN202010989362 A CN 202010989362A CN 112062765 A CN112062765 A CN 112062765A
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CN112062765B (en
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马晓宇
王士凯
赵贺
孙峰
于丹阳
张颖
张思铭
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention provides an organic light-emitting electroluminescent compound and a preparation method thereof, which are used for preparing an organic electroluminescent device as an electron transmission layer, the driving voltage of the prepared organic electroluminescent device is obviously reduced, the luminous efficiency and the service life are obviously improved, and the luminous efficiency and the brightness of the device are improved; the preparation method of the organic luminescent compound provided by the invention has the advantages of simple synthesis steps, easy product purification, high purity and high yield.

Description

Organic photoelectric luminescent compound and preparation method thereof
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to an organic photoelectric luminescent compound and a preparation method thereof.
Background
Electroluminescent devices are auto-luminescent devices which have the advantage that they provide a wider viewing angle, a larger contrast ratio and a faster response time.
The organic electroluminescent element is a self-luminous element utilizing the following principle: by applying an electric field, the fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. It has the following structure: an anode, a cathode, and an organic layer therebetween. In order to improve efficiency and stability of the organic electroluminescent element, the organic material layer includes a plurality of layers having different materials, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In such an organic electroluminescent device, when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected into the organic material layer. The generated excitons generate light having a specific wavelength while migrating to a ground state.
The most important factor determining the luminous efficiency in the organic electroluminescent device is the light emitting material. Up to now, fluorescent materials have been widely used as light emitting materials. However, in view of the mechanism of electroluminescence, since phosphorescent materials theoretically enhance the luminous efficiency four times as compared to fluorescent materials, the development of phosphorescent light emitting materials has been widely studied. Iridium (III) complexes have been widely referred to as phosphorescent dopant materials. Currently, 4,4'-N, N' -dicarbazole-biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), and the like are widely used as known phosphorescent host materials. Although these materials provide good luminescent characteristics, they have the following disadvantages: 1) due to its lower glass transition temperature and poor thermal stability, the lifetime of the device is reduced. 2) Organic electroluminescent devices comprising phosphorescent host materials require higher driving voltages. Meanwhile, in order to improve efficiency and stability of the organic electroluminescent device, it is required to have a multi-layer 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. Therefore, 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 are used as the hole transporting material. However, organic EL devices using these materials have problems in quantum efficiency and service life, and further improvements in quantum efficiency and life are required.
Disclosure of Invention
In view of the above, the present invention provides an organic electroluminescent compound, a method for preparing the same, and an organic electroluminescent device having excellent current efficiency and power efficiency and long lifetime.
An organic electroluminescent compound having the structural formula:
Figure BDA0002690326670000021
in the formula: r1、R2、R3、R4、R5、R6、R7、R8Independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphoric acid, phosphoryl, silyl, boryl, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl; substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy; or are linked to an adjacent substituent(s) to form a mono-or polycyclic C3-C30 aliphatic ring or 3 to 30-membered aromatic ring, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
R9、R10independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine; or are linked to an adjacent substituent(s) to form a mono-or polycyclic C3-C30 aliphatic ring or a substituted or unsubstituted 3-to 30-membered aromatic ring, wherein the carbon atoms may be replaced with one or more heteroatoms selected from nitrogen, oxygen, sulfur, silicon, and the like;
x independently represents-O-, -S-, -SO2-、-C(R11)(R12)-、-N(R13)-、-Si(R14)(R15)-、-Sn(R16)(R17) -and-Ge (R)18)(R19) Or a linking bond, preferably a linking bond;
wherein R is11～R19Each independently represents a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; or are linked to an adjacent substituent to form a mono-or polycyclic, in particular C3-C30, alicyclic or aromatic ring;
Ar1、Ar2each independently represents C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, 3-to 30-membered heteroaryl, 3-to 30-membered heteroarylamino, C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, C3-C30 aliphatic ring linked to an adjacent substituent to form a mono-or polycyclic ring, or 3-to 30-membered aromatic ring;
preferably said Ar is1And Ar2Each independently selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C15-C26 heteroaryl, or triarylamino;
further preferably Ar is1And Ar2Each independently selected from substituted or unsubstituted C10-C14 aryl, substituted or unsubstituted C18-C22 heteroaryl, or triphenylamine;
l is a linking bond or a substituted or unsubstituted C6-C30 aryl; benzene or deuterated benzene is preferred.
In the above technical scheme, the organic electroluminescent compound is selected from compounds having structures shown in chemical formulas 1 to 50:
Figure BDA0002690326670000041
Figure BDA0002690326670000051
the invention also provides a preparation method of the organic luminescent compound, when R is9And R10When the aryl is aryl, the method comprises the following steps:
the method comprises the following steps: dissolving the raw material 2 in THF, ventilating for 3 times, cooling to-78 deg.C, adding N-BuLi, reacting for 2h, and reacting2Adding the raw material 1 under protection, heating to 25 ℃, stirring for 10h, adding distilled water into the reaction solution to quench the reaction, extracting the reaction solution with DCM, drying the extracted organic layer with magnesium sulfate, removing the solvent by rotary evaporation, and then adding the mixture into a reactor with a mass ratio of 1: 5, DCM and PE precipitate out solid to obtain an intermediate 1;
step two: r is to be10And intermediate 1 dissolved in 1, 4-dioxane followed by 3 ventilations, N2Adding trifluoromethanesulfonic acid under protection, heating to 120 ℃, reacting for 12h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and reacting with a solvent in a mass ratio of 1: 3, DCM and absolute ethyl alcohol are separated out to obtain an intermediate 2;
step three: dissolving the intermediate 2 in DCM, adding NBS, and reacting for 5 h; the mixture was then extracted with dichloromethane and water; then drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and separating out with DCM and ethanol to obtain an intermediate 3;
step four:
(4.1) preparation of chemical formula 1
Adding the intermediate 3 and the raw material 3Adding into mixed solution of toluene, ethanol and water, and ventilating for 3 times, N2Adding palladium catalyst and potassium carbonate under protection, stirring uniformly, heating to 95 ℃, reacting for 10h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the residual substance by column chromatography to obtain the compound shown in chemical formula 1;
(4.2) preparation of chemical formula 2
Intermediate 3 and starting material 4 were added to the toluene solution followed by 3 ventilation, N2Adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under protection, stirring uniformly, heating to 110 ℃, reacting for 8h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 2;
the specific reaction is as follows:
Figure BDA0002690326670000061
when R is9And R10When the alkyl is alkyl, the method comprises the following steps:
the method comprises the following steps: adding raw material 1 into anhydrous ether, and then ventilating for 3 times, N2Under protection, adding AlCl3Stirring for 15min, cooling to 0 deg.C, adding LiAlH4Heating to 50 ℃, stirring for 1h, then dropwise adding EA and 6mol/L hydrochloric acid solution at the water bath temperature, extracting the reaction solution with DCM, drying the extracted organic layer with magnesium sulfate, removing the solvent by rotary evaporation, and precipitating with DCM and ethanol to obtain an intermediate 1;
step two: dissolving intermediate 1 and potassium tert-butoxide in THF at room temperature, ventilating for 3 times, stirring for 30min, N2Adding methyl iodide under protection, heating to 40 deg.C, reacting for 12h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with magnesium sulfate, rotary evaporating to remove solvent, and purifying the remaining material by column chromatography to obtain intermediate 2;
step three: dissolving the intermediate 2 in DCM, adding NBS, and reacting for 5 h; the mixture was then extracted with dichloromethane and water, the extracted organic layer was dried over sodium sulfate, the solvent was removed by rotary evaporation and the intermediate 3 was isolated by DCM and ethanol; (ii) a
Step four:
(4.1) preparation of chemical formula 4
Adding the intermediate 3 and the raw material 2 into a mixed solution of toluol and water, and then ventilating for 3 times, N2Adding a palladium catalyst and potassium carbonate under protection, stirring uniformly, heating to 95 ℃, reacting for 10h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 4;
(4.2) preparation of chemical formula 3
Intermediate 3 and starting material 3 were added to the toluene solution followed by 3 ventilation, N2Adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under protection, stirring uniformly, heating to 110 ℃, reacting for 8h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 3;
the synthetic route is as follows:
Figure BDA0002690326670000071
through the scheme, compared with the prior art, the invention has the following beneficial effects:
the invention provides an organic electroluminescent compound with a novel structure and a preparation method thereof, the luminescent material is used as a novel structure complex, an organic metal compound is obtained by combining metal iridium with a specific heterocyclic ligand, and the luminous efficiency of an organic electroluminescent device can be obviously improved after the luminescent material is applied to the organic electroluminescent device;
the preparation method of the luminescent material provided by the invention has the characteristics of simple synthesis steps, mild condition requirements and high yield of target products, solves the problems of high synthesis price and higher synthesis process requirements of the existing phosphor luminescent material, and has higher practical popularization significance and application value.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the 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 BDA0002690326670000081
the method specifically comprises the following steps: the starting material 1(37mmol) and 215ml of anhydrous ether were added to a reaction vessel and N was passed through2In N at2Slowly adding AlCl under protection3(46mmol) stirring for 15min, cooling to 0 deg.C, slowly adding LiAlH4(56.6mmol) is heated to 50 ℃, stirred for 1h, and the reaction is finished; then dropping 10ml of EA and 20ml of 6mol/L hydrochloric acid solution at the temperature of an ice water bath, and extracting the reaction solution by using DCM; the extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator; precipitation with DCM and ethanol gave intermediate 1(6.2g, 65.7% yield, MW: 255.32);
after adding the intermediate 1(24.3mmol), t-BuOk (170.1mmol) and 200ml of THF into a reaction vessel, stirring for 30min, adding MeI (212.5mmol), heating to 40 ℃, and stirring for 12h, wherein the reaction is finished; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (petroleum ether as eluent) to afford intermediate 2(5.3g, 77% yield, MW: 283.37);
intermediate 2(20mmol) was dissolved in DCM, NBS was added, reaction 5h, followed by extraction of the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; precipitation with DCM and ethanol (1: 5 v/v) afforded intermediate 3(6.3g, 87.5% yield, MW: 361.07);
adding the intermediate 3(16.5mmol) and the raw material 2(16.5mmol) into a toluene solution, then ventilating for 3 times, adding a palladium catalyst (0.165mmol), tri-tert-butylphosphine (0.825mmol) and sodium tert-butoxide (33mmol) under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 8h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (DCM: PE ═ 1: 8) to give compound 1(7.5g, 70.1% yield, MW: 642.85).
Example 2
Preparation of compound 12:
Figure BDA0002690326670000101
bromobenzene (44.4mmol) and 100ml THF are added into a reaction vessel, and the temperature is reduced to-78 ℃ under the condition of N after 3 times of ventilation2Adding n-BuLi (44.4mmol) under the atmosphere, stirring for 2h, adding raw material 1(10g, 37mmol), heating to 25 ℃, stirring for 10h, and finishing the reaction; distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM, followed by drying the extracted organic layer with magnesium sulfate and removing the solvent using a rotary evaporator, and a solid was precipitated with DCM and PE (1: 5) to obtain intermediate 1(8g, yield 62%, MW: 347.42);
intermediate 1(23mmol) and benzene (23mmol) were dissolved in 150mL of 1, 4-dioxane and ventilated 3 times with N2Adding trifluoromethanesulfonic acid (115mmol) under the atmosphere, heating to 120 ℃, stirring for 12h, and finishing the reaction; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; DCM and absolute ethanol (volume ratio 1: 3) gave intermediate 2(5g, 53.3% yield, MW: 407.52);
dissolving the intermediate 2(12.26mmol) in DCM, adding NBS (14.7mmol), and reacting for 5 h; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; precipitation with DCM and ethanol (1: 5 v/v) afforded intermediate 3(5g, 83.8% yield, MW: 486.41);
adding the intermediate 3(10.3mmol) and the raw material 2(10.3mmol) into a toluene solution, then ventilating for 3 times, adding a palladium catalyst (0.103mmol), tri-tert-butylphosphine (0.515mmol) and sodium tert-butoxide (20.6mmol) under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 8h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (DCM: PE ═ 1: 6) to afford compound 12(4g, 60.4% yield, MW: 766.99).
Example 3
Preparation of compound 21:
Figure BDA0002690326670000111
charging raw material 2(44.4mmol) and 100ml THF into reaction vessel, ventilating 3 times, cooling to-78 deg.C, and reacting under N2Adding n-BuLi (44.4mmol) under the atmosphere, stirring for 2h, adding raw material 1(10g, 37mmol), heating to 25 ℃, stirring for 10h, and finishing the reaction; distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator and the solid precipitated with DCM and PE (1: 5) to give intermediate 1(10g, 77.82% yield, MW: 347.40);
intermediate 1(23mmol) and starting material 3(23mmol) were dissolved in 150mL of 1, 4-dioxane and purged 3 times with N2Adding trifluoromethanesulfonic acid (115mmol) under the atmosphere, heating to 120 ℃, stirring for 12h, and finishing the reaction; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; DCM and absolute ethanol (volume ratio 1: 3) were precipitated to give intermediate 2(7g, yield 7)4.79％，MW:407.18)；
Dissolving the intermediate 2(12.26mmol) in DCM, adding NBS (14.7mmol), and reacting for 5 h; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; precipitation with DCM and ethanol (1: 5 v/v) afforded intermediate 3(4.5g, 76.27% yield, MW: 485.05);
adding the intermediate 3(9mmol) and the raw material 4(9mmol) into a mixed solution of toluol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, heating to 95 ℃, reacting for 10 hours, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain compound 21(5.0g, 84.75% yield, MW: 650.25).
Example 4
Preparation of compound 18:
Figure BDA0002690326670000121
the starting material 1(37mmol) and 215ml of anhydrous ether were added to a reaction vessel and N was passed through2In N at2Slowly adding AlCl under protection3(46mmol) stirring for 15min, cooling to 0 deg.C, slowly adding LiAlH4(56.6mmol) is heated to 50 ℃, stirred for 1h, and the reaction is finished; then dropping 10ml of EA and 20ml of 6mol/L hydrochloric acid solution at the temperature of an ice water bath, and extracting the reaction solution by using DCM; the extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator; intermediate 1(8.0g, 85.11% yield, MW:255.13) was obtained by precipitation with DCM and ethanol;
after adding the intermediate 1(24.3mmol), t-BuOk (170.1mmol) and 200ml of THF into a reaction vessel, stirring for 30min, adding MeI (212.5mmol), heating to 40 ℃, and stirring for 12h, wherein the reaction is finished; the mixture was then extracted with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (petroleum ether as eluent) to afford intermediate 2(5.8g, 84.1% yield, MW: 283.17);
intermediate 2(20mmol) was dissolved in DCM, NBS was added, reaction 5h, followed by extraction of the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; precipitation with DCM and ethanol (1: 5 v/v) gave intermediate 3(6.5g, 90.3% yield, MW: 361.03);
adding the intermediate 3(16.5mmol) and the raw material 2(16.5mmol) into a mixed solution of toluol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, heating to 95 ℃, reacting for 10 hours, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain compound 18(8.5g, 80.7% yield, MW: 642.35).
The synthesis methods of other compounds are the same as the above examples, which are not repeated herein, and the mass spectra and molecular formulas of other synthesis examples are shown in table 1 below, to form examples 5-9:
Figure BDA0002690326670000131
Figure BDA0002690326670000141
test example 1
An organic electroluminescent device 1 is prepared by using the compound 1 prepared in the above example 1, and the specific preparation method is as follows:
firstly, evaporating N1- (naphthalene-2-yl) -N4, N4-di (4- (naphthalene-2-yl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine ("2-TNATA") on an ITO (anode) for 50nm, then evaporating the compound 1 synthesized by the invention for 50nm to be a hole transport layer, a host substance 4,4'-N, N' -dicarbazole-biphenyl ("CBP") and a doping substance tris (2-phenylpyridine) iridium ("Ir (ppy)3") according to a weight ratio of 95:5, mixing and evaporating 25nm to be a luminescent layer, evaporating a hole blocking layer ("BALq") for 10nm, evaporating "Alq3" for 35nm to be an electron transport layer, evaporating an electron injection layer LiF for 0.2nm and evaporating a cathode Al for 135nm, forming an organic electroluminescent device.
With reference to the above-described method for producing the organic electroluminescent element 1, the corresponding organic electroluminescent elements 2 to 9 were produced by substituting the compound 1 with the compound 12, the compound 21, the compound 18, the compound 26, the compound 28, the compound 31, the compound 34, and the compound 45, respectively.
Comparative example
An organic electroluminescent device was prepared in the same manner as in experimental example 1, wherein the organic compound doped in the light-emitting layer had the following structure, to form comparative examples 1 to 3:
Figure BDA0002690326670000142
the prepared organic electroluminescent device is detected in the same way as the experimental example, and the test method comprises the following steps:
after biasing the organic electroluminescent device, the electroluminescent characteristics (EL) were tested at 6000cd/m using PR-650 from Photoresearch2Life equipment test T95 prepared with Mcscience at baseline brightness. The measurement results are shown in Table 2.
TABLE 2 test results
Compound (I) Drive voltage (V) Luminance (cd/m)2) Efficiency (cd/A) T(95)
Comparative Compound 1 5.6 6000 28.0 110
Comparative Compound 2 5.7 6000 23.2 98
Comparative Compound 3 5.5 6000 30.6 105
Compound 1 4.3 6000 45.1 185
Compound 12 3.5 6000 46.8 163
Compound 21 3.9 6000 39.8 159
Compound 18 4.0 6000 42.5 148
Compound 26 4.3 6000 45.3 135
Compound 28 4.1 6000 46.2 139
Compound 31 4.2 6000 43.1 165
Compound 34 4.5 6000 46.3 142
Compound 45 4.3 6000 45.4 148
As can be seen from the results of table 2 above, the organic electroluminescent device prepared using the compound provided by the present invention as a hole transport material exhibits high luminous efficiency and long lifetime and reduced driving voltage.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (7)

1. An organic electroluminescent compound, characterized by the structural formula:
Figure FDA0002690326660000011
in the formula: r1、R2、R3、R4、R5、R6、R7、R8Independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic group, sulfonyl, phosphate group, phosphoryl, silicon group, boryl, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, 3-30 membered heteroaryl, 3-30 membered heteroarylamino, C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy or withAdjacent substituents are joined to form a mono-or polycyclic 3-30 membered aliphatic ring or a C3-C30 aromatic ring;
R9、R10independently selected from C1-C30 alkyl, C1-C30 alkoxy, C3-C30 cycloalkyl, 3-to 30-membered heterocycloalkyl, C6-C30 aryl, 3-to 30-membered heteroaryl, C6-C30 aryloxy, arylamine group C6-C30, C3-C30 aliphatic ring linked to an adjacent substituent to form a mono-or polycyclic ring, or aromatic ring 3-to 30-membered;
x independently represents-O-, -S-, -SO2-、-C(R11)(R12)-、-N(R13)-、-Si(R14)(R15)-、-Sn(R16)(R17) -and-Ge (R)18)(R19) Or a link key;
Ar1、Ar2each independently represents C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, 3-to 30-membered heteroaryl, 3-to 30-membered heteroarylamino, C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, C3-C30 aliphatic ring linked to an adjacent substituent to form a mono-or polycyclic ring, or 3-to 30-membered aromatic ring;
l is a linking bond or a C6-C30 aryl group.
2. The organic electroluminescent compound according to claim 1, wherein R is1、R2、R3、R4、R5、R6、R7、R8When linked to an adjacent substituent to form a mono-or polycyclic 3-30 membered aliphatic ring or a C3-C30 aromatic ring, the carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur.
3. The organic electroluminescent compound according to claim 1, wherein R is9、R10Independently selected from the group consisting of a monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 30-membered aromatic ring linked to adjacent substituents, the carbon atom(s) may be replaced with one or more heteroatoms such as nitrogen, oxygen, sulfur, silicon, etc.
4. The organic electroluminescent compound according to claim 1, wherein R is11～R19Each independently represents C1-C30 alkyl, C6-C30 aryl, C3-C30 heteroaryl, or is linked to an adjacent substituent to form a single ring or multiple rings.
5. An organic electroluminescent compound according to claim 4, wherein the adjacent substituents are linked to form a single ring or multiple rings, in particular a C3-C30 alicyclic or aromatic ring.
6. A method for preparing an organic light-emitting compound according to any one of claims 1 to 5, wherein when R is9And R10When the aryl is aryl, the method comprises the following steps:
the method comprises the following steps: dissolving the raw material 2 in THF, then replacing air with nitrogen, repeatedly ventilating for 3 times, cooling to-78 deg.C, adding N-BuLi, reacting for 2h, and reacting with N2Adding the raw material 1 under protection, heating to 25 ℃, stirring for 10h, adding distilled water into the reaction solution to quench the reaction, extracting the reaction solution with DCM, drying the extracted organic layer with magnesium sulfate, removing the solvent by rotary evaporation, and then adding the mixture into a reactor with a mass ratio of 1: 5, DCM and PE precipitate out solid to obtain an intermediate 1;
step two: r is to be10And intermediate 1 dissolved in 1, 4-dioxane followed by 3 ventilations, N2Adding trifluoromethanesulfonic acid under protection, heating to 120 ℃, reacting for 12h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and reacting with a solvent in a mass ratio of 1: 3, DCM and absolute ethyl alcohol are separated out to obtain an intermediate 2;
step three: dissolving the intermediate 2 in DCM, adding NBS, and reacting for 5 h; the mixture was then extracted with dichloromethane and water; then drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and separating out with DCM and ethanol to obtain an intermediate 3;
step four:
(4.1) preparation of chemical formula 1
Adding the intermediate 3 and the raw material 3 into the mixture of the toluol and the waterMixing the solution, then ventilating for 3 times, N2Adding palladium catalyst and potassium carbonate under protection, stirring uniformly, heating to 95 ℃, reacting for 10h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the residual substance by column chromatography to obtain the compound shown in chemical formula 1;
(4.2) preparation of chemical formula 2
Intermediate 3 and starting material 4 were added to the toluene solution followed by 3 ventilation, N2Adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under protection, stirring uniformly, heating to 110 ℃, reacting for 8h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 2;
the specific reaction is as follows:
Figure FDA0002690326660000031
7. a method for preparing an organic light-emitting compound according to any one of claims 1 to 5, wherein when R is9And R10When the alkyl is alkyl, the method comprises the following steps:
the method comprises the following steps: raw material 1 was added to anhydrous ether at a concentration of 0.17mol/L, followed by N2Ventilation 3 times, N2Under protection, adding AlCl3Stirring for 15min, cooling to 0 deg.C, adding LiAlH4Heating to 50 deg.C, stirring for 1h, wherein the raw materials 1 and AlCl3And LiAlH4Is 37:46:56.6, then EA and a 6mol/L hydrochloric acid solution are added dropwise at the temperature of a water bath, wherein the volume ratio of anhydrous ether, EA and hydrochloric acid is 43:2:4, after the reaction solution is extracted with DCM, the extracted organic layer is dried with magnesium sulfate, after the solvent is removed by rotary evaporation, DCM and ethanol are used for precipitation to obtain an intermediate 1;
step two: dissolving intermediate 1 and potassium tert-butoxide in THF at room temperature, ventilating for 3 times, stirring for 30min, N2Adding methyl iodide under protection, heating to 40 ℃, reacting for 12h, wherein the molar ratio of the intermediate 1, potassium tert-butoxide and methyl iodide is 1:7:8.75, the concentration of the intermediate 1 in THF is 0.1215mol/L, extracting the mixture with dichloromethane and water, drying the extracted organic layer with magnesium sulfate, removing the solvent by rotary evaporation, and purifying the residual substance by column chromatography to obtain an intermediate 2;
step three: dissolving the intermediate 2 in DCM, adding NBS, and reacting for 5 h; the mixture was then extracted with dichloromethane and water, the extracted organic layer was dried over sodium sulfate, the solvent was removed by rotary evaporation and the intermediate 3 was isolated by DCM and ethanol; (ii) a
Step four:
(4.1) preparation of chemical formula 4
Adding the intermediate 3 and the raw material 2 into a mixed solution of toluol and water, and then ventilating for 3 times, N2Adding a palladium catalyst and potassium carbonate under protection, stirring uniformly, heating to 95 ℃, reacting for 10h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 4;
(4.2) preparation of chemical formula 3
Intermediate 3 and starting material 3 were added to the toluene solution followed by 3 ventilation, N2Adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under protection, stirring uniformly, heating to 110 ℃, reacting for 8h, extracting the mixture with dichloromethane and water, drying the extracted organic layer with sodium sulfate, removing the solvent by rotary evaporation, and purifying the remaining substances by column chromatography to obtain a compound shown in chemical formula 3;
the synthetic route is as follows:
Figure FDA0002690326660000051
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010104047A1 (en) * 2009-03-11 2010-09-16 国立大学法人京都大学 Polycyclic aromatic compound
CN102869662A (en) * 2010-05-04 2013-01-09 默克专利有限公司 Organic electroluminescence devices
CN104871329B (en) * 2012-12-18 2017-10-24 默克专利有限公司 Organic electroluminescence device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010104047A1 (en) * 2009-03-11 2010-09-16 国立大学法人京都大学 Polycyclic aromatic compound
CN102869662A (en) * 2010-05-04 2013-01-09 默克专利有限公司 Organic electroluminescence devices
CN104871329B (en) * 2012-12-18 2017-10-24 默克专利有限公司 Organic electroluminescence device

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