CN112979535A - Compound and application thereof - Google Patents
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Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I, and a carbazole structure of aromatic heptanes is introduced, so that the planarity of molecules is improved, and the transport barrier of a current carrier is reduced, and an organic electroluminescent device containing the compound has the advantages of low voltage and high efficiency.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and cool optoelectronic products as required, with the advantages of being stronger than inorganic materials. Including Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, and organic sensors, among others. Among them, OLEDs have been developed particularly rapidly, and have been commercially successful in the field of information display.
The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like. The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: a light-emitting host material, a light-emitting guest, a hole-transporting material, a hole-injecting material, an electron-injecting material, a hole-blocking material, an electron-transporting material, an electron-blocking material, and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
At the present stage, researchers have developed various organic materials, and combined with different device structures, the organic materials can improve the carrier mobility, regulate and control the carrier balance, break through the electroluminescent efficiency, and delay the attenuation of the device. For quantum mechanical reasons, common fluorescent emitters mainly utilize singlet excitons generated when electrons and holes are combined to emit light, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-like materials.
However, the current red host material has a high carrier transport barrier, requires a high voltage, and has poor luminous efficiency and molecular structure stability. Therefore, there is a need to develop new material systems to meet the increasing demand for the photoelectric performance of OLED devices.
Disclosure of Invention
An object of the present invention is to provide a compound having high molecular planarity and reduced carrier transport barrier, which has excellent photoelectric properties when applied to an organic electroluminescent device.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
in the formula I, m and n are each independently an integer of 0-3 (such as 0, 1, 2 or 3), and p is an integer of 0-6 (such as 0, 1, 2,4, 5 or 6);
in the formula I, R is1、R2And R3Each independently selected from substituted or unsubstituted C1 to C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) chain alkyl groups, substituted or unsubstituted C3 to C12 (e.g., C4, C5, C6, C7, C8, C9, C10, etc.) cycloalkyl groups, substituted or unsubstituted C1 to C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) alkoxy groups, halogens, cyano groups, nitro groups, hydroxyl groups, silyl groups, amino groups, substituted or unsubstituted C6 to C6 (e.g., C6, etc.) substituted or C6, e.g., substituted or C6, C, C12, C15, C18, C20, C23, C25, C28, etc.) heteroaryl, R is selected from the group consisting of1、R2And R3Each independently fused or unfused to the attached benzene ring;
when m is an integer of 2 or more, i.e. the mother nucleus is substituted with two or more R1Two or more of R1May be the same group or different groups, n, p and R2、R3The same process is carried out;
in formula I, L is selected from one of single bonds, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, C10 and the like) alkylene, substituted or unsubstituted C6-C30 (such as C10, C12, C14, C16, C18, C20, C26, C28 and the like) arylene, substituted or unsubstituted C3-C30 (such as C4, C6, C8, C12, C15, C18, C20, C23, C25, C28 and the like) heteroarylene;
in the formula I, Ar is1Selected from substituted or unsubstituted C6-C30 (e.g., C10, C12, C14, C16, C18, C20, C26, C28, etc.) aryl or substituted or unsubstituted C3-C30 (e.g., C4, C6, C8, C12, C15, C18, C20, C23, C25, C28, etc.) heteroaryl;
when the above-mentioned group has a substituent, the substituent is selected from halogen, chain alkyl groups such as C1 to C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.), cycloalkyl groups such as C3 to C12 (e.g., C4, C5, etc.), alkoxy groups such as C5 to C5 (e.g., C5, etc.), thioalkoxy groups such as C5 to C5 (e.g., C5, etc.) arylamine.g., etc. monocyclic 5, C5, etc., C36, C25, C28, etc.), monocyclic heteroaryl, and fused ring heteroaryl having C6 to C30 (e.g., C7, C8, C10, C12, C14, C16, C18, C20, C26, C28, etc.), or a combination of at least two thereof. The "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected.
In the present invention, the heteroatom of heteroaryl is generally referred to as N, O, S.
In the present invention, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
The invention provides a novel compound, and by introducing a carbazole structure of the aromatic heptanes, the planarity of compound molecules is improved, and the transport barrier of a current carrier is reduced, so that an organic electroluminescent device containing the compound has the advantages of low voltage and high efficiency.
Preferably, the L is selected from one of a single bond, a substituted or unsubstituted C6-C18 arylene, a substituted or unsubstituted C3-C18 heteroarylene, preferably a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene or biphenylene.
When the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, Ar is1Selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, Ar is1Has one of the structures shown by the following formulas (3-1) to (3-4):
in the formula (3-1), the Z1、Z2、Z3、Z4And Z5Each independently selected from CR4Or an N atom, and Z1、Z2、Z3、Z4And Z5At least one of which is an N atom,
in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR4Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom,
in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23Each independently selected from CR4Or an N atom, and Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least one of which is an N atom,
in the formula (3-4), Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33Each independently selected from CR4Or an N atom, and Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least one of which is an N atom,
the R is4One selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, Ar is1Has a structure represented by formula (3-1) or formula (3-2).
Preferably, Ar is1Containing at least two N atoms.
Preferably, in the formula (3-1), Z1、Z2、Z3、Z4And Z5At least two of which are N atoms;
or, in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms;
or, in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least two of which are N atoms;
or, in the formula (3-4), the Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least two of which are N atoms.
Preferably, Ar is1One selected from the following substituted or unsubstituted groups: quinazolinyl, triazinyl, pyrimidinyl, or quinoxalinyl.
When the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, Ar is1One selected from substituted or unsubstituted A1-A14 groups:
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
Preferably, Ar is1One selected from the group consisting of B1-B19:
wherein denotes the access bond of the group.
Preferably, any one or at least two of m, n and p is 0, preferably all of m, n and p are 0.
Preferably, the compound has one of the following structures shown as P1-P82:
the second purpose of the invention is to provide the application of the compound in the first purpose, and the compound is applied to an organic electroluminescent device.
Preferably, the compound is used as a material of a light emitting layer of the organic electroluminescent device, preferably as a host material of the light emitting layer.
The invention also provides an organic electroluminescent device which comprises a substrate, a first electrode, a second electrode and at least one organic layer positioned between the first electrode and the second electrode, wherein the organic layer contains at least one compound for one purpose.
Preferably, the organic layer includes a light-emitting layer containing at least one compound described for one of the purposes.
Preferably, the compound serves as a host material of the light-emitting layer.
Specifically, an organic electroluminescent device (OLED) includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In) can be used) Metals or alloys such as magnesium-silver (Mg-Ag), and any combinations thereof.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
The light emitting layer includes a light emitting dye (i.e., Dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
The device may also include a bitAn electron injection layer between the electron transport layer and the cathode, the electron injection layer being made of materials including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3BaO, Na, Li and/or Ca.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel compound, and by introducing a carbazole structure of the aromatic heptanes, the planarity of compound molecules is improved, and the transport barrier of a current carrier is reduced, so that an organic electroluminescent device containing the compound has the advantages of low voltage and high efficiency.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. The solvents and reagents used in the present invention, such as methylene chloride, ethanol, tetrahydrofuran, quinazoline, triazine, quinoxaline and other chemical reagents, are commercially available from the domestic chemical product market, such as from national drug group reagent company, TCI company, shanghai Biddy pharmaceutical company, carbofuran reagent company, zhengzhou Haika, etc. In addition, they can be synthesized by a known method by those skilled in the art.
A representative synthetic route for the compounds of formula I of the present invention is as follows:
m, n, p, R1、R2、R3L and Ar1All have the same meaning as in formula I.
The method for synthesizing the organic compound of the present invention will be briefly described below by way of specific synthesis examples.
Synthesis example 1: synthesis of intermediate E
Adding 1, 8-dibromonaphthalene (1mol), phenylboronic acid (1mol), potassium carbonate (1.2mol), tetrakis (triphenylphosphine) palladium (0.01mmol), dioxane 1000mol and 100mL of water into a reaction bottle, heating until reflux reaction is carried out for 6h, monitoring the reaction completion by Thin Layer Chromatography (TLC), adding ethyl acetate and water for extraction, and concentrating an organic phase to obtain an intermediate A.
Adding A (0.7mol) into 1L Tetrahydrofuran (THF), cooling to-78 ℃, dropwise adding n-butyllithium (0.8mol), reacting for 30min after dropwise adding, dropwise adding triisopropyl borate (1mol), gradually returning to room temperature for reaction for 3h after finishing adding, adding water and ethyl acetate for extraction, concentrating an organic phase, washing with methanol, and filtering to obtain an intermediate B.
Adding B (0.5mol), 2-bromo-6-nitroaniline (0.7mol), potassium carbonate (1.0mol), tetrakis (triphenylphosphine) palladium (0.005mmol), dioxane 800mol and 80mL of water into a reaction bottle, heating until reflux reaction is carried out for 6h, monitoring by TLC for complete reaction, adding ethyl acetate and water for extraction, and concentrating an organic phase to obtain an intermediate C.
Adding C (0.4mol) into 500mL of acetic acid, adding copper powder (1mol), dropwise adding tert-butyl nitrite (1mol) at 20 ℃, reacting at room temperature for 4h after dropwise adding, monitoring by TLC to complete the reaction, adding water and dichloromethane for extraction, separating an organic phase, filtering by using kieselguhr, concentrating the filtrate, and purifying by column chromatography to obtain an intermediate D.
And (3) adding D (0.2mol) into 300mL of o-dichlorobenzene, adding triphenylphosphine (0.4mol), refluxing for 5h, directly removing o-dichlorobenzene after complete reaction, and purifying by column chromatography to obtain an intermediate E.
Synthesis example 2: synthesis of Compound P7
Adding E (50mmol), 2-chloro-4- (1-naphthyl) quinazoline (55mmol), cesium carbonate (60mmol) and N, N-dimethylformamide (DMF, 150mL) into a reaction bottle, carrying out reflux reaction for 8h, cooling to room temperature after complete reaction, pouring the reaction liquid into water, filtering, washing a filter cake with ethanol once, and recrystallizing with toluene to obtain a compound P7.
Synthesis example 3: synthesis of Compound P15
Adding 2, 4-dichloroquinazoline (0.2mol), 4- (pyridine-3-yl) phenylboronic acid (1mol), potassium carbonate (0.35mol), tetrakis (triphenylphosphine) palladium (0.002mmol), dioxane (300 mol) and 50mL of water into a reaction bottle, heating to 80 ℃ for reaction for 4h, monitoring the reaction by TLC, cooling and filtering to obtain P15-A.
Adding E (50mmol), P15-A (55mmol), cesium carbonate (60mmol) and DMF (150mL) into a reaction bottle, refluxing for 8h, cooling to room temperature after complete reaction, pouring the reaction liquid into water, filtering, washing the filter cake with ethanol once, and recrystallizing with toluene to obtain the compound P15.
Synthesis example 4: synthesis of Compound P18
The difference from Synthesis example 2 was that 2-chloro-4- (1-naphthyl) quinazoline was replaced with an equivalent amount of 2- (4-fluorophenyl) -4-phenylquinazoline to obtain Compound P18.
Synthesis example 5: synthesis of Compound P22
The difference from synthetic example 2 is that 2-chloro-4- (1-naphthyl) quinazoline was replaced with 2- (3-biphenyl) -3-chloroquinoxaline in an equivalent amount to obtain compound P22.
Synthesis example 6: synthesis of Compound P36
The difference from synthetic example 2 is that 2-chloro-4- (1-naphthyl) quinazoline was replaced with an equivalent amount of 2, 4-diphenyl-4- (4-fluorophenyl) -1,3,5 triazine to give compound P36.
Synthesis example 7: synthesis of Compound P59
Adding D (0.2mol) and DMF (200mL) into a reaction bottle, cooling to 0 ℃, dropwise adding a DMF solution of N-bromosuccinimide (NBS, 0.3mol), reacting at room temperature for 2h after the dropwise adding is finished, monitoring the reaction completion by a gas chromatography-mass spectrometer (GC-MS), adding water and ethyl acetate for extraction, concentrating an organic phase, and washing with methanol to obtain an intermediate D1.
The synthesis of intermediate E1 was identical to intermediate E except that D was replaced with D1 in equal amounts.
Adding E1(0.1mol), dibenzothiophene-4-boric acid (0.12mol), potassium carbonate (0.2mol), tetrakis (triphenylphosphine) palladium (0.001mmol), dioxane 200mol and 30mL of water into a reaction bottle, heating to 100 ℃ for reacting for 4h, monitoring by TLC to complete reaction, cooling and filtering to obtain an intermediate E2.
P59 was synthesized in the same manner as in Synthesis example 2 except that E was replaced with E2 in an equivalent amount.
In order to verify the certainty of the molecular structure, we confirmed the molecular structure by elemental analysis (measuring instrument: Sammerfed FLASH 2000 CHNS/O organic element analyzer) and mass spectrometry information (measuring instrument: ZAB-HS type mass spectrometer measurement, manufactured by Micromass Co., UK), as shown in Table 1.
TABLE 1
Example 1
The embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:
ultrasonically treating the glass plate coated with the ITO transparent conducting layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent, baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer, a 40nm compound P6: RPD-8(100:3, w/w) binary mixture as a light emitting layer, a 25nm compound ET-46: ET-57(50/50, w/w) mixture as an electron transport layer, 1nm LiF as an electron injection layer, and 150nm metal aluminum as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Examples 2 to 8 and comparative examples 1 to 2
The manufacturing processes of examples 2 to 8 and comparative examples 1 to 2 were the same as example 1 except that the luminescent layer material P6 was replaced with P15, P18, P22, P36, P59, P40, P51, C1, and C2, respectively.
Wherein the comparative compounds C1 and C2 used in comparative examples 1-2 have the following structural formulae:
among them, compound C1 is described in detail in patent KR1020180099547A, and C2 is described in detail in patent KR 1020150121337A.
Performance testing
The driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 2 were measured at the same luminance using a PR750 type photoradiometer from Photo Research, a ST-86LA type luminance meter (photoelectric Instrument factory, university of Beijing) and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and the current density as measured when the organic electroluminescent device reached 10mA/cm2The voltage is the driving voltage, and the brightness at the moment is measured; the ratio of the luminance to the current density was defined as the current efficiency, and the current efficiency of comparative example 1 was set to 1, and the current efficiencies of the other compounds were relative values to those of comparative example 1.
The results of the above performance tests are shown in table 2.
TABLE 2
As shown in Table 2, when the compound of formula I provided by the invention is used as a host material of a light-emitting layer of an organic electroluminescent device, the device using the compound has higher current efficiency and lower driving voltage.
The compound C1 in comparative example 1 is different from the compound P6 in example 1 only in the difference of the mother nucleus, the overall performance of the device in comparative example 1 is worse than that in example 1, and the reason for this analysis may be that the triplet level of the compound C1 in comparative example 1 is around 2.3eV, the triplet level of the compound C1 in example 1 of the present invention is around 2.2eV, and when it is used as a red light host material, the more appropriate triplet level can promote the transfer of excitons to the guest and prevent the annihilation of triplet-triplet states, the triplet level of the material of the present invention just satisfies the level requirement of the red light host, and is not too high, and the device example 1 using the compound P6 of the present invention shows more excellent device performance than the device 1 using the comparative compound.
The compound C2 in comparative example 2 is different from the compound P6 in example 1 in the parent nucleus, and the driving voltage and the current efficiency of the device in comparative example 2 are both worse than those of example 1 because the parent nucleus of the compound C2 in comparative example 2 adopts a 7-membered conjugated structure with indolocarbazole as a main body and the triplet level (T) is caused by too much conjugation of the molecule1) The organic electroluminescent device has the advantages that the organic electroluminescent device is small in size and incapable of effectively transferring excitons to a guest for luminescence, so that the voltage and the efficiency of a device using the compound C2 in a comparative example 1 are poor, and further, the compound using the carbazole structure of the ar-heptanes as a parent nucleus provided by the invention is proved to be more beneficial to the improvement of the device performance when being used as a luminescent host material of the organic electroluminescent device.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (12)
1. A compound having a structure according to formula I;
in the formula I, m and n are respectively and independently integers of 0-3, and p is an integer of 0-6;
in the formula I, R is1、R2And R3Each independently selected from one of substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of1、R2And R3Each independently fused or unfused to the attached benzene ring;
in the formula I, L is selected from one of single bond, substituted or unsubstituted C1-C10 alkylene, substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C3-C30 heteroarylene;
in the formula I, Ar is1Selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
2. The compound of claim 1, wherein L is selected from one of a single bond, substituted or unsubstituted C6-C18 arylene, substituted or unsubstituted C3-C18 heteroarylene;
preferably a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene, or biphenylene;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
3. The compound of claim 1 or 2, wherein Ar is1Selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
4. A compound according to any one of claims 1 to 3 wherein Ar is Ar1Has one of the structures shown by the following formulas (3-1) to (3-4):
in the formula (3-1), the Z1、Z2、Z3、Z4And Z5Each independently selected from CR4Or an N atom, and Z1、Z2、Z3、Z4And Z5At least one of which is an N atom,
in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR4Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom,
in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23Each independently selected from CR4Or an N atom, and Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least one of which is an N atom,
in the formula (3-4), Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33Each independently selected from CR4Or an N atom, and Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least one of which is an N atom,
the R is4One selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl;
preferably, Ar is1Has a structure represented by formula (3-1) or formula (3-2).
5. The compound according to claim 4, wherein in formula (3-1), Z is1、Z2、Z3、Z4And Z5At least two of which are N atoms;
or, in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms;
or, in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least two of which are N atoms;
or, in the formula (3-4), the Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least two of which are N atoms.
6. The compound of claim 1 or 2, wherein Ar is1One selected from the following substituted or unsubstituted groups: quinazolinyl, triazinyl, pyrimidinyl, or quinoxalinyl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
7. The compound of claim 1 or 2, wherein Ar is1Selected from substituted or unsubstitutedOne of the groups A1 to A14:
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
8. The compound of claim 1 or 2, wherein Ar is1One selected from the group consisting of B1-B19:
wherein denotes the access bond of the group.
9. A compound according to any one of claims 1 to 8, wherein any one or at least two of m, n and p is 0, preferably all of m, n and p are 0.
10. The compound of claim 1, wherein the compound has one of the following structures P1-P82:
11. use of a compound according to any one of claims 1 to 10 in an organic electroluminescent device;
preferably, the compound is used as a material of a light emitting layer of the organic electroluminescent device, preferably as a host material of the light emitting layer.
12. An organic electroluminescent device comprising a substrate, a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one compound according to any one of claims 1 to 10;
preferably, the organic layer includes a light-emitting layer containing at least one compound according to any one of claims 1 to 10;
preferably, the compound serves as a host material of the light-emitting layer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113149964A (en) * | 2020-01-22 | 2021-07-23 | 北京绿人科技有限责任公司 | Compound containing conjugated condensed ring aromatic structure, application thereof and organic electroluminescent device |
| CN114349741A (en) * | 2021-12-31 | 2022-04-15 | 武汉天马微电子有限公司 | Organic compound and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452182A (en) * | 2019-08-01 | 2019-11-15 | 浙江华显光电科技有限公司 | A kind of host compound and the organic electroluminescence device using the compound |
| CN110746401A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN110862381A (en) * | 2019-12-04 | 2020-03-06 | 宁波卢米蓝新材料有限公司 | Organic electroluminescent compound and preparation method and application thereof |
| CN110872301A (en) * | 2019-10-15 | 2020-03-10 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
-
2019
- 2019-12-17 CN CN201911302601.7A patent/CN112979535A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452182A (en) * | 2019-08-01 | 2019-11-15 | 浙江华显光电科技有限公司 | A kind of host compound and the organic electroluminescence device using the compound |
| CN110746401A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN110872301A (en) * | 2019-10-15 | 2020-03-10 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN110862381A (en) * | 2019-12-04 | 2020-03-06 | 宁波卢米蓝新材料有限公司 | Organic electroluminescent compound and preparation method and application thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113149964A (en) * | 2020-01-22 | 2021-07-23 | 北京绿人科技有限责任公司 | Compound containing conjugated condensed ring aromatic structure, application thereof and organic electroluminescent device |
| CN114349741A (en) * | 2021-12-31 | 2022-04-15 | 武汉天马微电子有限公司 | Organic compound and application thereof |
| CN114349741B (en) * | 2021-12-31 | 2023-03-24 | 武汉天马微电子有限公司 | Organic compound and application thereof |
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