CN116023276A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN116023276A
CN116023276A CN202211644055.7A CN202211644055A CN116023276A CN 116023276 A CN116023276 A CN 116023276A CN 202211644055 A CN202211644055 A CN 202211644055A CN 116023276 A CN116023276 A CN 116023276A
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carbon atoms
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organic
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余献康
董青山
郭金涛
徐俏俏
王小利
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Fuyang Sineva Material Technology Co Ltd
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Abstract

The invention provides an organic compound and application thereof, wherein the organic compound has a structure shown in a general formula 1, and is a spirofluorene-based hole transport material, so that an organic electroluminescent device has low driving voltage, high luminous efficiency and long luminous life.

Description

Organic compound and application thereof
The present application claims priority from the application No. 202111585502. X (application date of the previous application is 2021, 12, 20, entitled organic compound and its application). -apply to priority.
Technical Field
The invention belongs to the field of organic electroluminescent materials, relates to an organic compound and application thereof, and in particular relates to a spirofluorene-based organic compound and application thereof in an organic electroluminescent device.
Background
Along with the progress of science and technology, the life quality of people is improved, the product with excellent performance is eager to be more and more strong, the organic electroluminescent display screen is more in line with the human visual requirement, and is favored by consumers, and the production of the OLED display screen with high quality is a common pursuit of industries.
At present, the liquid crystal display is still dominant in the display field, but there is a continuous and active effort to develop a novel flat panel display which is more economical and superior in performance and also different from the liquid crystal display throughout the world. Compared with a liquid crystal display, the organic electroluminescent device has the advantages of low driving voltage, high response speed, wide view angle and the like, and is recognized as the most potential next-generation display.
According to the structure of the organic electroluminescent device, the organic electroluminescent device is composed of a substrate, an anode, a hole injection layer for receiving holes from the anode, a hole transport layer for transporting holes, an electron blocking layer for blocking electrons from entering the hole transport layer from the light emitting layer, a light emitting layer for emitting light by combining holes and electrons, a hole blocking layer for blocking holes from entering the electron transport layer from the light emitting layer, an electron transport layer for receiving electrons from the cathode and transporting electrons to the light emitting layer, an electron injection layer for receiving electrons from the cathode, and a cathode. Depending on the case, a separate light-emitting layer is not required, but an electron-transporting layer or a hole-transporting layer is doped with a small amount of fluorescent or phosphorescent dye to form the light-emitting layer, and in the case of using a polymer, generally, one polymer can perform the roles of the hole-transporting layer, the light-emitting layer, and the electron-transporting layer at the same time. The organic thin film layer between the two electrodes may be formed using a vacuum deposition method or a spin coating method, an inkjet printing method, a laser thermoprinting method, or the like. In this way, the organic electroluminescent device is fabricated in a multi-layer thin film structure in order to stabilize the interface between the electrode and the organic material, and in the case of using the organic material, since the difference in the movement speed of holes and electrons is large, the holes and electrons are efficiently transferred to the light emitting layer using an appropriate hole transporting layer and electron transporting layer, and the density balance of the holes and electrons is achieved, thereby improving the light emitting efficiency.
The driving principle of the organic electroluminescent device is as follows: when a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer through the hole injection layer and the hole transport layer. At the same time, electrons are injected from the cathode to the light emitting layer via the electron injection layer and the electron transport layer, and recombined with carriers in the light emitting layer to form excitons. The excitons change to the ground state in this state, and thus fluorescent molecules of the light-emitting layer emit light, thereby forming an image. At this time, the excited state returns to the ground state through the singlet excited state, and the emitted light is called "fluorescence"; by returning the triplet excited state to the ground state, the emitted light is called "phosphorescence". The probability of returning to the ground state through the singlet excited state is 25%, and the probability of returning to the ground state through the triplet excited state is 75%, and therefore, the light emission efficiency is limited; in the case of phosphorescence, both of the triplet 75% and the singlet 25% are available for light emission, and thus, theoretically, the internal quantum efficiency can reach 100%.
The biggest problems of the organic electroluminescent device are short service life and low luminous efficiency, and the short service life and low luminous efficiency become the problems to be solved along with the large-area of the display screen. In particular, for blue, substances such as ADN and DPVBi can be used as a host substance, and substances such as aromatic amine compounds, copper phthalocyanine compounds, carbazole derivatives, perylene derivatives, coumarin derivatives, pyrene derivatives and the like can be used as dopants, but it is difficult to obtain deep blue, and there is a problem that the shorter the wavelength lifetime is, the shorter the lifetime is.
Therefore, in full-color display that exhibits natural colors, development of a material that has a long service life and is capable of emitting deep blue light and other organic materials that are compatible with the energy level of such blue light materials are actually demanded.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an organic compound and application thereof, in particular to an organic compound based on spirofluorene and application thereof in an organic electroluminescent device. The organic compound is a hole transport material based on spirofluorene, and can improve the luminous efficiency and the luminous service life of an organic electroluminescent device.
To achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic compound having a structure represented by the following formula 1:
Figure BDA0004009076990000031
general formula 1
Wherein Ar is 1 Selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted carbon atomsHeteroaryl having a sub-number of 2 to 50, a substituted or unsubstituted heterocycloalkyl having a sub-number of 2 to 30, a substituted or unsubstituted alkoxy having a sub-number of 1 to 30, a substituted or unsubstituted aryloxy having a sub-number of 6 to 30, a substituted or unsubstituted alkylthio having a sub-number of 1 to 30, a substituted or unsubstituted arylthio having a sub-number of 5 to 30, a substituted or unsubstituted alkylamino having a sub-number of 1 to 30, a substituted or unsubstituted arylamino having a sub-number of 5 to 30, a substituted or unsubstituted alkylsilane having a sub-number of 1 to 30, a substituted or unsubstituted arylsilane having a sub-number of 5 to 30, a substituted or unsubstituted alkylgermanium having a sub-number of 1 to 30, or a substituted or unsubstituted arylgermanium having a sub-number of 1 to 30;
L 1 -L 5 each identical to or different from the other and independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
R 1 -R 4 each of which is the same or different from the other and is independently selected from hydrogen, deuterium (D), cyano, halo, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms and having at least one heteroatom selected from O, N, S or Si;
a, b, c, d and e are each the same or different and are each independently 0 or 1.
In the invention, the organic compound shown in the general formula 1 is a hole transport material with excellent performance, the luminous life of the device is prolonged, the luminous efficiency is not reduced, the driving voltage is optimized, the energy consumption is reduced, and the organic electroluminescent device is greatly improved in the aspects of driving voltage, luminous efficiency, luminous life and the like.
In the present invention, the definition of the group defines a range of carbon atoms, the number of carbon atoms is any integer within the defined range, for example, an aryl group having 6 to 50 carbon atoms, the number of carbon atoms representing the aryl group may be any integer within the range of 6 to 50 inclusive, for example, 6, 8, 10, 15, 20, 30, 35, 38, 40, 43, 45, 48, 50, etc., and the carbon atom definition ranges of the other groups and so forth have the same meaning.
In the invention, when one or more of a, b, c, d and e are 0, the connection position where the connection is located is not provided with a connection bond.
In the present invention, when the group described above is a substituted group, the substituent thereof is F, cyano, deuterium, aryl having 6 to 60 carbon atoms, heteroaryl having 2 to 60 carbon atoms, or alkyl having 1 to 40 carbon atoms.
Preferably Ar 1 Selected from phenyl, biphenyl, naphthyl, fluorenyl, thienyl, phenyl-substituted thienyl, furyl, or phenyl-substituted furyl.
Preferably L 1 -L 5 Independently of one another, selected from the group consisting of single bond, phenyl, naphthyl, biphenyl or fluorenyl.
Preferably, R 1 -R 4 Independently selected from methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or phenyl.
Preferably, the organic compound is any one of the following compounds:
Figure BDA0004009076990000061
/>
Figure BDA0004009076990000071
/>
Figure BDA0004009076990000081
/>
Figure BDA0004009076990000091
/>
Figure BDA0004009076990000101
/>
Figure BDA0004009076990000111
/>
Figure BDA0004009076990000121
/>
Figure BDA0004009076990000131
wherein D represents deuterium.
In another aspect, the present invention provides a hole transport material comprising any one or a combination of at least two of the organic compounds described above.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising any one or a combination of at least two of the organic compounds as described above.
Preferably, the organic thin film layer comprises a hole transport layer comprising any one or a combination of at least two of the organic compounds as described above.
Preferably, the organic thin film layer comprises a hole transport layer comprising any one or a combination of at least two of the organic compounds as described above, and a light emitting layer comprising any one or a combination of at least two of the organic compounds having the structure shown in formula 2,
Figure BDA0004009076990000132
general formula 2
Wherein Ar is 11 、Ar 12 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 ring-forming carbon atoms.
Preferably, when the group as described above is a substituted group, the substituent thereof is F, cyano, deuterium, aryl having 6 to 60 carbon atoms, heteroaryl having 2 to 60 carbon atoms, or alkyl having 1 to 40 carbon atoms.
Preferably Ar 11 、Ar 12 Each independently selected from any one or a combination of the above groups of phenyl, biphenyl, naphthyl-phenyl, anthryl, phenanthryl, naphthyl-naphthyl, fluorenyl, carbazolyl or pyrenyl.
Preferably, the compound with the structure shown in the general formula 2 is any one of the following compounds:
Figure BDA0004009076990000151
wherein D represents deuterium.
Preferably, the organic thin film layer further includes at least one of a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
Compared with the prior art, the invention has the following beneficial effects:
the organic compound is used for preparing an OLED device, can reduce driving voltage, improves luminous efficiency and prolongs the service life of the device.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Preparation example
Synthesis of intermediate-1
Reactive type
Figure BDA0004009076990000161
Under the protection of nitrogen, 3.38g (20 mmol) of 3-aminobiphenyl and 6.42g (20 mmol) of 3-bromo-N-phenylcarbazole are added, dissolved in 40mL of toluene, and 0.2g of dibenzylideneacetone dipalladium (Pd) are added respectively 2 dba 3 ) 0.6mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.76g (60 mmol) of sodium tert-butoxide (t-Buona), at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 100mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of a small amount of water in the organic layer with anhydrous magnesium sulfate, suction filtration, and concentration of the organic solution gave a compound which was passed through the column with n-heptane, ethyl acetate=5:1 as eluent to give 5.33g (65%) of intermediate-1.
Intermediate-1 MS (FAB): 410 (M+).
Synthesis of Compound 6
Reactive type
Figure BDA0004009076990000171
Under the protection of nitrogen, 10.12g (20 mmol) of 2 '-bromo-2, 7-di-tert-butyl-9, 9' -spirobifluorene and 8.20g (20 mmol) of intermediate-1 are added, dissolved in 60mL of toluene, and 0.2g of Pd are added respectively 2 dba 3 0.6ml of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.76g (60 mmol) of t-Buona at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 100mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of organic layer with anhydrous magnesium sulfateThe organic solution was concentrated by suction filtration to give a compound of 7.15g (43%) of compound 6 by passing the compound through a column with an eluent of n-heptane: ethyl acetate=4:1.
Compound 6MS (FAB): 836 (M+).
Synthesis of intermediate-2
Reactive type
Figure BDA0004009076990000172
Under the protection of nitrogen, 4.79g (17 mmol) of 1-bromo-6-phenylnaphthalene and 3.16g (18.7 mmol) of 4-aminobiphenyl are added, dissolved in 40mL of toluene, and 0.16g of Pd is added respectively 2 dba 3 0.5mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.18g (54 mmol) of t-Buona at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 100mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of a small amount of water in the organic layer with anhydrous magnesium sulfate, suction filtration, and concentration of the organic solution gave a compound which was passed through the column with n-heptane, ethyl acetate=4:1 as eluent to give intermediate-2 as 4.79g (76%).
Intermediate-2 MS (FAB): 371 (M+).
Synthesis of Compound 28
Reactive type
Figure BDA0004009076990000181
Under the protection of nitrogen, 7.96g (20 mmol) of raw material 1 and 6.97g,22mmol of intermediate-2 are added, dissolved in 40mL of toluene, and 0.16g of Pd are added respectively 2 dba 3 0.5mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.18g (54 mmol) of t-Buona at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 100mL of toluene was used as the catalyst, H 2 O100 mL extraction, removing small amount of water in the organic layer by anhydrous magnesium sulfate, suction filtering, concentrating organic solution to obtainThe compound was passed through a column using n-heptane, dichloromethane=3:1 eluent to give compound 28 as 7.01g (51%).
Compound 28MS (FAB): 689 (M+).
Synthesis of Compound 45
Reactive type
Figure BDA0004009076990000182
Under the protection of nitrogen, 10.00g (20 mmol) of raw material 2 and 13.60g (50 mmol) of 2-bromo-9, 9-dimethylfluorene are added, dissolved in 60mL of toluene, and 0.16g of Pd is added respectively 2 dba 3 0.5mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.76g (60 mmol) of t-Buona at 110℃for 24 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 200mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of a small amount of water in the organic layer with anhydrous magnesium sulfate, suction filtration, concentration of the organic solution produced a compound which was passed through the column with n-heptane, ethyl acetate=3:1 eluent to give compound 45 as 11.81g (67%).
Compound 45MS (FAB): 883 (M+).
Synthesis of intermediate-3
Reactive type
Figure BDA0004009076990000191
Under the protection of nitrogen, 4.18g (20 mmol) of 2-amino-9, 9-dimethylfluorene and 5.64g (20 mmol) of 4- (1-naphthyl) -bromobenzene are added, dissolved in 40mL of toluene, and 0.16g of Pd are added respectively 2 dba 3 0.5mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.76g (60 mmol) of t-Buona at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 100mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of small amount of water in the organic layer with anhydrous magnesium sulfate, suction filtration, concentration of the organic solution to give a compound with n-heptane: ethylThe eluate of ethyl acetate=5:1 was passed through a chromatographic column to give intermediate-3 as 5.59g (68%).
Intermediate-3 MS (FAB): 411 (M+).
Synthesis of Compound 62
Reactive type
Figure BDA0004009076990000201
Under the protection of nitrogen, 10.48g (20 mmol) of raw material 3 and 8.22g (20 mmol) of intermediate-3 are added, dissolved in 100mL of toluene, and 0.16g of Pd are added respectively 2 dba 3 0.5mL of 10% tri-tert-butylphosphine (t-Bu) 3 P) and 5.76g (60 mmol) of t-Buona at 110℃for 8 hours.
After the reaction, the temperature of the reaction mixture was lowered to room temperature, 200mL of toluene was used as the catalyst, H 2 O100 mL extraction, removal of a small amount of water in the organic layer with anhydrous magnesium sulfate, suction filtration, concentration of the organic solution produced a compound which was passed through a column with n-heptane: ethyl acetate=3:1 eluent to give compound 62 as 9.51g (57%).
Compound 62MS (FAB): 839 (M+).
Synthesis of Compound 112
Reactive type
Figure BDA0004009076990000202
Synthetic method referring to the synthesis of compound 6, only 2 '-bromo-2, 7-di-tert-butyl-9, 9' -spirobifluorene was exchanged for starting material 4 to give compound 112.
Compound 112MS (FAB): 838 (M+).
Synthesis of Compound 113
Reactive type
Figure BDA0004009076990000211
Synthetic method referring to the synthesis of compound 6, only 2 '-bromo-2, 7-di-tert-butyl-9, 9' -spirobifluorene was exchanged for starting material 5 to give compound 113.
Compound 113MS (FAB): 840 (M+).
Synthesis of Compound 114
Reactive type
Figure BDA0004009076990000212
Synthetic method referring to the synthesis of compound 6, only 2 '-bromo-2, 7-di-tert-butyl-9, 9' -spirobifluorene was exchanged for starting material 6 to give compound 114.
Compound 114MS (FAB): 848 (M+).
The compounds of the other general formula 1 in the present invention can be prepared by a preparation method similar to the above, and the structural correctness of the compounds is verified by mass spectrometry.
Device example 1
Transparent electrode Indium Tin Oxide (ITO) thin film (15 Ω/sq) (samsung Corning company (Sa msung Corning) in korea) on glass substrate for Organic Light Emitting Diode (OLED) device was sequentially ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water, and then stored in isopropyl alcohol. Next, the ITO substrate was mounted on a substrate holder (holder) of a vacuum vapor deposition apparatus.
Introducing HAT-CN into the chamber of the vacuum vapor deposition apparatus, and then controlling the chamber pressure of the apparatus to 10 -6 And (5) a bracket. A20 nm HAT-CN was deposited as a Hole Injection Layer (HIL) on the ITO substrate.
Then transferred to another chamber where compound 6 of formula 1 according to the present invention was deposited as a Hole Transport Layer (HTL) by evaporation over the HIL layer to a thickness of 40 nm.
Transferring to another chamber, introducing the compound ADN into one chamber of the vacuum vapor deposition apparatus as a matrix material, and introducing the compound 2,5,8, 11-tetra-tert-butylperylene into the other chamber as a dopant. The two materials were evaporated at different rates and deposited at a doping amount of 5 wt% (based on the total weight of the host material and the dopant), thereby forming a light emitting layer having a thickness of 30nm on the hole transport layer.
Alq3 of 30nm was vacuum-evaporated on top of the organic light-emitting layer as an electron transport layer of the organic electroluminescent device.
LiF of 0.5nm and Al of 150nm are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.
According to the above-described method for manufacturing an organic electroluminescent device, the anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode may be manufactured in this order, and the cathode/electron injection layer/electron transport layer/light emitting layer/hole transport layer/hole injection layer/anode may be manufactured in this order.
Device examples 2 to 14
Examples 2 to 14 differ from example 1, respectively, in that the compound 6 in HTL in example 1 was replaced with the compound 14, 28, 39, 45, 62, 67, 78, 87, 97, 109, 112, 113 or 114, respectively, and the organic electroluminescent device was produced in the same manner as in device example 1.
Device example 15
The ITO substrate was mounted on a substrate holder (holder) of a vacuum vapor deposition apparatus.
Introducing HAT-CN into the chamber of the vacuum vapor deposition apparatus, and then controlling the chamber pressure of the apparatus to 10 -6 And (5) a bracket. A20 nm HAT-CN was deposited as a Hole Injection Layer (HIL) on the ITO substrate.
Then transferred to another chamber where compound 6 of formula 1 according to the present invention was deposited as a Hole Transport Layer (HTL) by evaporation over the HIL layer to a thickness of 40 nm.
Transferring to another chamber, introducing the compound H1 in the general formula 2 into one chamber of a vacuum vapor deposition apparatus as a matrix material, and introducing the compound 2,5,8, 11-tetra-tert-butylperylene into the other chamber as a dopant. The two materials were evaporated at different rates and deposited at a doping amount of 5 wt% (based on the total weight of the host material and the dopant), thereby forming a light emitting layer having a thickness of 30nm on the hole transport layer.
Alq3 of 30nm was vacuum-evaporated on top of the organic light-emitting layer as an electron transport layer of the organic electroluminescent device.
LiF of 0.5nm and Al of 150nm are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.
According to the above-described method for manufacturing an organic electroluminescent device, the anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode may be manufactured in this order, and the cathode/electron injection layer/electron transport layer/light emitting layer/hole transport layer/hole injection layer/anode may be manufactured in this order.
Device examples 16 to 28
Device examples 16 to 28 differ from example 15, respectively, in that compound 14, 28, 39, 45, 62, 67, 78, 87, 97, 109, 112, 113 or 114, respectively, was used as compound 6 in HTL in device example 15 instead of compound 14, 28, 39, 97, 109, 112, 113 or 114, respectively, and the method of manufacturing an organic electroluminescent device was the same as that of device example 15.
Device examples 29 to 30
Device examples 29 to 30 differ from example 15, respectively, in that the compound H1 in the EML layer as in device example 15 was replaced with the compounds H9, H14, respectively, and the organic electroluminescent device was produced in the same manner as in device example 15.
Comparative example 1
The difference from device example 1 is that compound HTL-1 was used instead of compound 6 in this comparative example, and the organic electroluminescent device was produced in the same manner as in device example 1.
Comparative example 2
The difference from device example 15 is that HTL-1 was used instead of compound 6 in this comparative example, and the organic electroluminescent device was produced in the same manner as in device example 15.
The structures of the compounds used in the above device examples 1 to 30 and comparative examples 1 and 2 are as follows.
Figure BDA0004009076990000241
Evaluation of the Performance of the organic electroluminescent device obtained by the preparation of device example
Evaluation of the organic electroluminescent devices of examples 1 to 14 and comparative example 1 at a current density of 10mA/cm 2 The results are shown in Table 1. T95 is kept at the initial 10mA/cm 2 The current density of (2) is unchanged, and the time required for the brightness of the device to drop to 95% of the initial brightness is expressed in hours.
TABLE 1
Figure BDA0004009076990000251
As can be seen from the experimental results shown in table 1, in example 1 in which the organic compound of formula 1 of the present invention was used as a hole transport layer, the organic electroluminescent device obtained was improved in efficiency and reduced in driving voltage as compared with the conventional organic electroluminescent device described in comparative example 1.
Further, as can be seen from the results of T95, the organic electroluminescent device of comparative example 1 has a lifetime of 100 hours or less, whereas the organic electroluminescent devices prepared in examples 1 to 14 have lifetimes of 100 hours or more, particularly the organic electroluminescent devices of examples 4, 5, 6, 9, 12 and 14 have lifetimes of 280 hours or more, wherein the organic electroluminescent devices of examples 5, 9 and 12 have lifetimes of more than 300 hours. It is shown that the spirofluorene HTL material has obvious improvement on the service life of the device when the spirofluorene HTL material contains tertiary butyl or has deuterium atom substitution. It can be seen from examples 1, 12, 13, 14 that the properties of spirofluorene > the properties of spirobifluorene > the properties of bifluorene subunit > the properties of tetraphenyl methane.
The organic compound of the general formula 1 is adopted as a hole transport layer, and the efficiency, the driving voltage and the service life of the obtained organic electroluminescent device are obviously improved compared with the prior art.
Evaluation of organic electroluminescent device Performance of device examples 15 to 30 and comparative example 2
The performance of the organic electroluminescent devices obtained in the above device examples 15 to 24 and comparative example 2 was measured at a current density of 10mA/cm 2 The results are shown in Table 2. T95 is kept at the initial 10mA/cm 2 The current density of (2) is unchanged, and the time required for the brightness of the device to drop to 95% of the initial brightness is expressed in hours.
TABLE 2
Figure BDA0004009076990000261
As can be seen from the experimental results shown in table 2, the organic electroluminescent devices prepared in examples 15 to 28 using the organic compounds of general formulae 1 and 2 as the hole transport layer and the light emitting layer according to the present invention have improved efficiency and voltage characteristics compared to the conventional organic electroluminescent device described in comparative example 1. In particular, the organic electroluminescent devices of examples 17 and 26 were significantly improved in voltage characteristics and luminous efficiency performance.
Further, as can be seen from the results of T95, the organic electroluminescent device of comparative example 2 had a lifetime of 100 hours or less, whereas the organic electroluminescent devices of examples 15 to 28 had a lifetime of 240 hours or more. In particular, the organic electroluminescent devices of examples 17, 18, 19, 23, 26 and 28 have a lifetime of more than 300 hours, wherein the organic electroluminescent device of example 23 has a lifetime of more than 331 hours. The spirofluorene HTL material has obviously improved service life of devices when containing tert-butyl or substituting deuterium atoms, and has more excellent performance when being matched with the compound shown in the general formula 2.
Therefore, the organic compound of the general formula 1 is used as a hole transport layer, and the efficiency, the driving voltage and the service life performance of the organic electroluminescent device of the luminescent layer prepared by the compound of the general formula 2 are all remarkably improved compared with the prior art.
Evaluation of organic electroluminescent device Performance of device examples 1, 15, 29 and 30 and comparative examples 1 and 2
The performance of the organic electroluminescent devices manufactured in examples 1, 15, 29 and 30 and comparative examples 1-2 above was that at a current density of 10mA/cm 2 The results of the environmental measurements are shown in Table 3. T95 is kept at the initial 10mA/cm 2 Is (1) the current of the (a)The density is unchanged and the time required for the brightness of the device to drop to 95% of the initial brightness is in hours.
TABLE 3 Table 3
Figure BDA0004009076990000271
Figure BDA0004009076990000281
As can be seen from the experimental results shown in table 3, the organic electroluminescent devices prepared in examples 15, 29, 30 using the organic compounds of the general formulae 1 and 2 according to the present invention as the hole transport layer and the light emitting layer have significantly improved voltage characteristics, light emitting efficiency, and lifetime characteristics compared to comparative examples 1 and 2 and compared to example 1 using the organic compound of the general formula 2 according to the present invention as the light emitting layer.
In the organic electroluminescent device in the prior art, electrons are diffused to the hole transport layer through the interface while thermalizing is performed in the interface between the hole transport layer and the light emitting layer, and the life of the organic electroluminescent device is reduced due to acceleration of thermalization. In the present invention, since the compound of formula 1 is used as a hole transport layer, charge balance of the device is achieved while ensuring that excitons do not move within the light emitting layer, and efficiency of the organic electroluminescent device is improved. In addition, the compound of formula 1 blocks diffusion of excitons to the hole transport layer, so that thermalization of the entire device can be prevented, thereby extending the lifetime of the organic electroluminescent device.
The applicant states that the organic compounds of the present invention and their use are illustrated by the above examples, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (10)

1. An organic compound, characterized in that the organic compound has a structure represented by the following formula 1:
Figure FDA0004009076980000011
wherein Ar is 1 Selected from the group consisting of hydrogen, heavy hydrogen, cyano, nitro, halogen, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted alkenyl having 6 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted alkylthio having 6 to 30 carbon atoms, substituted or unsubstituted arylthio having 5 to 30 carbon atoms, substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, substituted or unsubstituted silyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 1 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 30 carbon atoms, substituted or unsubstituted germanium having 1 to 30 carbon atoms;
L 1 -L 5 are each identical to or different from one another and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms,A substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
R 1 -R 4 each of which is the same or different from the other and is independently selected from hydrogen, deuterium (D), cyano, halo, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms and having at least one heteroatom selected from O, N, S or Si;
a, b, c, d and e are each the same or different and are each independently 0 or 1.
2. The organic compound according to claim 1, wherein when the group is the substituted group, the substituent is F, cyano, deuterium, aryl having 6 to 60 carbon atoms, heteroaryl having 2 to 60 carbon atoms, or alkyl having 1 to 40 carbon atoms;
preferably Ar 1 Selected from phenyl, biphenyl, naphthyl, fluorenyl, thienyl, phenyl-substituted thienyl, furyl, or phenyl-substituted furyl;
preferably L 1 -L 5 Independently of each other selected from single bond, phenyl, naphthyl, biphenyl or fluorenyl;
preferably, R 1 -R 4 Independently selected from methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or phenyl.
3. The organic compound according to claim 1 or 2, characterized in that the organic compound is any one of the following compounds:
Figure FDA0004009076980000041
/>
Figure FDA0004009076980000051
/>
Figure FDA0004009076980000061
/>
Figure FDA0004009076980000071
/>
Figure FDA0004009076980000081
/>
Figure FDA0004009076980000091
/>
Figure FDA0004009076980000101
/>
Figure FDA0004009076980000111
wherein D represents deuterium.
4. A hole transport material comprising any one or a combination of at least two of the organic compounds according to any one of claims 1 to 3.
5. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising any one or a combination of at least two of the organic compounds according to any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 5, wherein the organic thin film layer comprises a hole transport layer comprising any one or a combination of at least two of the organic compounds according to any one of claims 1 to 3.
7. The organic electroluminescent device according to claim 5 or 6, wherein the organic thin film layer comprises a hole transport layer comprising any one or a combination of at least two of the organic compounds as described above and a light emitting layer comprising any one or a combination of at least two of the organic compounds having the structure represented by formula 2,
Figure FDA0004009076980000112
wherein Ar is 11 、Ar 12 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 ring-forming carbon atoms.
8. The organic electroluminescent device according to claim 7, wherein when the group is the substituted group, the substituent is F, cyano, deuterium, aryl having 6 to 60 carbon atoms, heteroaryl having 2 to 60 carbon atoms, or alkyl having 1 to 40 carbon atoms;
preferably Ar 11 、Ar 12 Each independently selected from any one or a combination of the above groups of phenyl, biphenyl, naphthyl-phenyl, anthryl, phenanthryl, naphthyl-naphthyl, fluorenyl, carbazolyl or pyrenyl.
9. The organic electroluminescent device according to claim 7 or 8, wherein the compound of the structure represented by formula 2 is any one of the following compounds:
Figure FDA0004009076980000131
wherein D represents deuterium.
10. The organic electroluminescent device according to any one of claims 5 to 9, wherein the organic thin film layer further comprises at least one of a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
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