CN111943942A - Compound, thermal activation sensitized fluorescent material, organic electroluminescent device and application - Google Patents
Compound, thermal activation sensitized fluorescent material, organic electroluminescent device and application Download PDFInfo
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Abstract
A compound, a thermal activation sensitized fluorescent material, an organic electroluminescent device and application. The compound has the following structure:
wherein X, n, R1、Y1～Y3、Ar1、Ar2The definition of (A) is the same as that of the specification. The compound can be used as a light-emitting host material or an electron transport material of an organic light-emitting device, and can improve the triplet state energy level of the host material and an exciton blocking materialThe triplet state energy level effectively reduces the luminescence quenching caused by aggregation, improves the luminous efficiency, and enables the turn-on voltage of the organic light-emitting device to be reduced, and the maximum brightness and the maximum external quantum efficiency to be improved.
Description
Technical Field
The invention relates to the technical field of photoelectric luminescent materials, in particular to a compound, a thermal activation sensitized fluorescent material, an organic electroluminescent device containing the compound and application of the compound and the thermal activation sensitized fluorescent material.
Background
Photovoltaic devices employing organic materials are becoming increasingly popular for a number of reasons, such as the relative inexpensiveness of the many materials used to make such devices, and the potential cost advantages of optoelectronic devices over inorganic devices. In the organic electroluminescent device structure in the display and illumination field, blue fluorescence is generally used in combination with red and green phosphorescent materials. The light emitting layer of a common electroluminescent device mainly adopts a host-guest doping mode to adjust the light color, the brightness and the efficiency, thereby improving the performance of the device. The low efficiency of blue OLED devices is a bottleneck problem for OLED technology. The Thermal Activation Sensitized Fluorescence (TASF) technology is expected to solve the problem, and a main material with a high triplet state energy level and an exciton blocking material are important materials for improving the exciton utilization rate of a pure organic small molecule material in a device. When the energy gap of the host emitter is too large, electrons and holes are not easily injected into the host emitter, but are easily injected into the guest emitter directly for recombination to make the guest emitter emit light, if only one of HOMO or LUMO energy levels is contained in the HOMO/LUMO energy level of the host emitter, it is necessary to know whether the Frenkel exciton of the guest emitter is in a lower energy state, if so, the guest emitter exciton tends to be formed to emit light, and if not, an electron-hole pair between the host and guest emitters is formed, which is not favorable for light emission. Due to the wide band gap and the hole-biased unipolar transport property of common host materials, the exciton injection energy barrier is high and can cause deviation of an exciton recombination region under high voltage, so that the electroluminescence spectrum is unstable, the efficiency roll-off is serious, and the like. Therefore, the development of a main body with certain electron transmission capability and an electron transmission material has important significance in the aspects of improving injection, reducing starting voltage, improving luminous efficiency, reducing efficiency roll-off and the like.
Disclosure of Invention
In view of the above, the main objective of the present invention is to provide a compound, a thermal activation sensitized fluorescent material, an organic electroluminescent device containing the same, and applications thereof, so as to at least partially solve the above technical problems.
In order to achieve the above object, as a first aspect of the present invention, there is provided a compound having a structure represented by general formula (I):
wherein:
x is SiR2R3Or CR4R5Wherein R is2～R5The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
n is an integer of 0 to 4, R1The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group; when R is1When two adjacent substituents are present, the two substituents can be fused to form a ring;
Y1～Y3each independently selected from CR6Or N; wherein R is6Selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
Ar1ar2 is independently selected from substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30A heteroaryl group;
when R is1、R2、R3、R4、R5、R6、Ar1、Ar2Or Ar3When the selected group has a substituent, the substituent is respectively and independently selected from halogen and C1～C10Alkyl or cycloalkyl, C2～C10Alkenyl radical, C1～C6Alkoxy or thioalkoxy group, C6～C30Monocyclic aromatic or fused ring aromatic hydrocarbon radical, C3～C30One of monocyclic heteroaromatic group or condensed ring heteroaromatic group.
As a second aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device, preferably as a light-emitting layer in an organic electroluminescent device, more preferably as a light-emitting dye and/or sensitizer in a light-emitting layer of said organic electroluminescent device.
As a third aspect of the present invention, there is also provided a thermally activated sensitized fluorescent material including the compound as described above.
As a fourth aspect of the present invention, there is also provided a use of the thermally activated sensitized fluorescent material as described above in an organic electroluminescent device, preferably as a light emitting layer in an organic electroluminescent device, and more preferably as a light emitting dye and/or sensitizer in a light emitting layer of the organic electroluminescent device.
As a fifth aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, the organic layers containing at least one compound as described above.
Based on the technical scheme, compared with the prior art, the compound, the thermal activation sensitized fluorescent material and the organic electroluminescent device containing the same have at least one of the following advantages:
1. the compound of the present invention can be used as a light emitting host material or an electron transporting material of an organic light emitting device; because dibenzothiophene and triazine groups contained in the compound have higher triplet states, and silicon and carbon of non-conjugated groups are introduced as connecting bonds, the conjugation degree is not greatly improved, and the triplet state energy level of a main material and the triplet state energy level of an exciton blocking material can be improved;
2. after dibenzothiophene and triazine in the compound are connected through a silicon bond, the whole molecule presents a larger rigid twisted structure, so that luminescence quenching caused by aggregation can be effectively reduced, and the luminescence efficiency is improved;
3. when the compound is used as a main body of fluorescent and phosphorescent dyes and an electron transport material, the turn-on voltage is reduced, the maximum brightness and the maximum external quantum efficiency are improved, and excellent device performance is shown.
Detailed Description
The present invention will be described in further detail below with reference to specific embodiments in order to make the present invention better understood by those skilled in the art.
Based on the knowledge of the prior art, when the bridging bond between the dibenzothiophene and triazine groups is selected as an electron-withdrawing group, the scheme has the problem of low exciton utilization rate due to a wider band gap. The present inventors have found, through various researches, that introduction of a non-conjugated group as a connecting bond does not result in a great increase in the degree of conjugation, so that the triplet state energy levels of the host material and the exciton-blocking material can be increased, thereby obtaining the present invention.
Specifically, the invention discloses a silicon biphenyl thiophene-based compound, which has a structure shown in a general formula (I):
wherein:
x is SiR2R3Or CR4R5Wherein R is2～R5The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
n is an integer of 0 to 4, and is, for example, 0, 1, 2, 3 or 4. R1The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group; when R is1When two adjacent substituents are present, the two substituents can be fused to form a ring;
Y1～Y3each independently selected from CR6Or N; wherein R is6Selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
Ar1ar2 is independently selected from substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30Heteroaryl radical；
When R is1、R2、R3、R4、R5、R6、Ar1、Ar2Or Ar3When the selected group has a substituent, the substituent is respectively and independently selected from halogen and C1～C10Alkyl or cycloalkyl, C2～C10Alkenyl radical, C1～C6Alkoxy or thioalkoxy group, C6～C30Monocyclic aromatic or fused ring aromatic hydrocarbon radical, C3～C30One of monocyclic heteroaromatic group or condensed ring heteroaromatic group.
Preferably, R is1～R6Each independently selected from hydrogen, fluorine, chlorine, bromine, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, cyclopentyl, cyclohexyl, and substituted or unsubstituted of the following substituents: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, 9 '-dimethylfluorene, 9' -spirobifluorene, benzofluorene, fluoranthenyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
A phenyl, tetracenyl, furyl, thienyl, pyridyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl, quinolinyl, quinazolinyl group;
more preferably cyclohexyl, phenyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl, quinolyl.
Preferably, Ar is1、Ar2Each independently selected from the following substituted or unsubstituted substituents: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, 9 '-dimethylfluorene, 9' -spirobifluorene, benzofluorene, fluoranthenyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
Phenyl, tetracenyl, furyl, thienyl, pyridyl, pyranylPyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, quinolinyl, quinazolinyl;
more preferably phenyl, tolyl, xylyl, naphthyl, methylnaphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl.
Preferably, the compound is selected from the group consisting of fused substituted compounds represented by the following II-1 to II-4:
wherein, X, Y1、Y2、Y3、Ar1、Ar2The definition of (A) is as shown above; r1' is as defined for R1(ii) a m is an integer of 0 to 10, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
Preferably, the compound is selected from the following compounds represented by I-1 to I-12:
wherein, X, Y1、Y2、Y3、Ar1、Ar2、n、R1The definition of (A) is as shown above.
Preferably, the compound is selected from the following compounds represented by M1 to M87:
the invention also discloses an application of the compound in an organic electroluminescent device, preferably an application of the compound as a luminescent layer in the organic electroluminescent device, and more preferably an application of the compound as a luminescent dye and/or a sensitizer in the luminescent layer of the organic electroluminescent device.
The invention also discloses a Thermal Activation Sensitized Fluorescent (TASF) material, which comprises the compound.
The invention also discloses an application of the thermal activation sensitized fluorescent material in an organic electroluminescent device, preferably an application of the thermal activation sensitized fluorescent material as a light-emitting layer in the organic electroluminescent device, and more preferably an application of the thermal activation sensitized fluorescent material as a light-emitting dye and/or a sensitizer in the light-emitting layer of the organic electroluminescent device.
The invention also discloses an organic electroluminescent device which comprises a first electrode, a second electrode and one or more organic layers which are inserted between the first electrode and the second electrode, wherein the organic layers comprise at least one compound as described above.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device. Preferably, the display screen or panel is an OLED display.
The invention also discloses an electronic device, wherein the electronic device is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device;
specific production methods of the above-mentioned compounds of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production methods of the present invention are not limited to these synthesis examples. Compounds not mentioned in the present invention are all commercially available starting products. Solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole and the like, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bidi medicine, carbofuran, and the like. Further, the resin may be prepared by a known method.
Analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000 QTRAP).
The synthesis of the compounds of the present invention is briefly described below.
Representative synthetic route:
synthetic examples
Synthesis example 1: synthesis of M1
Synthesis of intermediate M1-1
Taking a dry 2L three-neck flask, dissolving 4-bromothiophene dibenzobenzene (52g, 197mmol, 1eq) in anhydrous THF (500mL), replacing nitrogen for 3 times, cooling to-78 ℃ under the protection of nitrogen, slowly dropwise adding n-butyl lithium (2.5M n-hexane solution, 100mL, 237mmol, 1.2eq) under stirring, reacting at-78 ℃ for 0.5 hour, adding dimethoxy diphenylsilicon (48.29g, 217mmol, 1.1eq) into the reaction system, naturally heating to room temperature after 0.5 hour of heat preservation, reacting for 1 hour to obtain an intermediate M1-1 solution, and keeping for later use.
Synthesis of intermediate M1-2
Taking a dry 2L three-neck flask, dissolving p-dibromobenzene (51.2g, 217mmol, 1.1eq) in anhydrous THF (500mL), replacing nitrogen for 3 times, cooling to-78 ℃ under the protection of nitrogen, dropwise adding n-butyllithium (2.5M n-hexane solution, 100mL, 237mmol, 1.2eq) into the system under stirring, keeping the temperature at-78 ℃ for reaction for 0.5 hour after dropwise adding, dropwise adding a THF solution of an intermediate M1-1 into the reaction system, naturally heating to room temperature after dropwise adding, and stirring for reaction overnight. After the reaction, H2O (100M1) is added to quench the reaction, then ethyl acetate 500mL is added to extract for 3 times, the organic phase is dried by anhydrous sodium sulfate and concentrated, and a product purified by silica gel column chromatography (the solvent PE: DCM is 100: 1-30: 1) is eluted and concentrated to obtain 85g of light yellow oily matter. The yield thereof was found to be 82.52%.
Synthesis of intermediate M1-3
Intermediate M1-2(40g, 76mmol, 1eq) was dissolved in dioxane (500mL) in a 1L single neck flask and pinacol ester of bis (boronic acid) (29g, 115mmol, 1.5eq) and catalyst Pd (dppf) Cl were added2(1.4g, 1mmol, 3% eq), potassium acetate (15g, 150mmol, 2eq), nitrogen was replaced 3 times, and the mixture was heated to reflux under nitrogen protection and stirring overnight. And (5) detecting the reaction is complete, and stopping the reaction. Filtering to remove solid inorganic salt, performing decompression spin-drying on the solvent, dissolving a sample by using ethyl acetate, adding a silica gel column chromatography purified product (the solvent PE: DCM is 100: 1-30: 1) for elution, concentrating the solvent to obtain oily liquid, recrystallizing by using normal hexane to separate out a solid, and performing suction filtration and drying to obtain 35 g of a white powder solid. The mass of the molecular ions determined by mass spectrometry was: 569.2 (calculated value: 568.21); the above analysis results show that the obtained product is the expected product.
Synthesis of Compound M1
A clean dry 1L single neck bottle was charged with M1-3(40g, 70.35mmol, 1eq), 2-chloro-4, 6-diphenyltriazine (18.8g, 70.35mmol, 1eq) dissolved in a THF/water (400/100mL) mixture and Pd as a catalyst (PPh)3)4(1.63g, 1.41mmol, 1% eq), potassium carbonate (18g, 140.69mmol, 2eq), nitrogen was replaced by 3 times, and the mixture was heated to reflux under stirring under nitrogen atmosphere overnight. The reaction was followed by TLC (PE/EA ═ 30: 1), the reaction was complete, the reaction was cooled to room temperature and the solution was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases are combined, dried over anhydrous sodium sulfate, filtered, spin-dried under reduced pressure and rinsed with toluene. Drying under reduced pressure to obtain 26g white solid, recrystallizing with 800mL toluene, decocting with ethanol, filtering to obtain 22g white powder, and separating by mass spectrometryThe mass of the molecular ions determined by the analysis is as follows: 674.30 (calculated value: 673.20); the above analysis results show that the obtained product is the expected product.
Synthesis example 2: synthesis of M8
A clean dry 1L single neck bottle was charged with M1-3(40g, 70.35mmol, 1eq), 4-chloro-2, 6-diphenylpyrimidine (18.7g, 70.35mmol, 1eq) dissolved in a THF/water (400/100mL) mixture and Pd as a catalyst (PPh)3)4(1.63g, 1.41mmol, 1% eq), potassium carbonate (18g, 140.69mmol, 2eq), nitrogen was replaced by 3 times, and the mixture was heated to reflux under stirring under nitrogen atmosphere overnight. The reaction was followed by TLC (PE/EA ═ 30: 1), the reaction was complete, the reaction was cooled to room temperature and the solution was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases are combined, dried over anhydrous sodium sulfate, filtered, spin-dried under reduced pressure and rinsed with toluene. Decompression spin-drying to obtain 25g of white solid, recrystallizing with 800mL of toluene, boiling and filtering with ethanol to obtain 21g of white powder, wherein the mass of molecular ions determined by mass spectrometry is as follows: 672.20 (calculated value: 672.21); the above analysis results show that the obtained product is the expected product.
Synthesis example 3: synthesis of M20
The synthesis was similar to that of M1, except that 4-bromothiophene dibenzo was replaced with an equivalent amount of 2-bromothiophene dibenzo, and p-dibromobenzene was replaced with an equivalent amount of M-dibromobenzene. 19g of white powder are finally obtained, the mass of the molecular ions determined by mass spectrometry being: 673.18 (calculated value: 673.20); the above analysis results show that the obtained product is the expected product.
Synthesis example 4: synthesis of M79
The synthesis method is similar to that of M1, except that dimethoxy diphenylsilicon is replaced by equal amount of 2, 2-dimethoxy propane. 20g of white powder are finally obtained, and the mass of the molecular ions determined by mass spectrometry is as follows: 533.17 (calculated value: 533.19); the above analysis results show that the obtained product is the expected product.
Device embodiments
The light-emitting layer of the organic electroluminescent device and the organic electroluminescent device of the present invention will be explained below.
The light-emitting layer of the organic electroluminescent device comprises a host material and a dye. The compound of the present invention can be used as a host material or an electron transport layer material.
The organic electroluminescent device comprises a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer which are sequentially formed on the substrate;
the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; the light-emitting layer is the light-emitting layer of the organic electroluminescent device.
Specifically, the anode material may be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO)2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT, and multilayer structures of these materials.
A hole injection layer including, but not limited to, one or a combination of more of the HI1-HI3 listed below.
And a hole transport layer including, but not limited to, one or more of HT1-HT33 listed below.
The host material may be one or more selected from GPH-44 to GPH-80 listed below.
Fluorescent dyes including, but not limited to, combinations of one or more of TDE1-TDE39 listed below.
Phosphorescent dyes, including but not limited to combinations of one or more of PD1-PD17 listed below.
And an electron transport layer including, but not limited to, one or more of ET1-ET62 in combination as listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the material of the electron injection layer including, but not limited to, one or a combination of more of the following: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3、BaO、Na、Li、Ca。
The cathode can be a magnesium silver mixture, LiF/A1, ITO and other metals, metal mixtures or oxides.
Examples of the compounds of the invention as host materials in fluorescent electroluminescent devices are examples 1 to 6; examples as host materials in phosphorescent electroluminescent devices are examples 7 to 12; examples of the use as electron transport materials are examples 13 to 18.
Device example 1
The device structure is as follows:
ITO(150nm)/HI-2(10nm)/HT-2(40nm)/M1：TDE7(30nm，5％wt)/M1(5nm)/ET59(25nm)/LiF(0.5nm)/Al(150nm)。
the preparation process of the organic electroluminescent device is as follows: glass plates coated with ITO (thickness 150nm) transparent conductive layers were sonicated in commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～1×10-4Pa, vacuum evaporating HI-2 and H on the anode layer filmT-2 is respectively used as a hole injection layer and a hole transmission layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm and 40nm respectively;
vacuum evaporation of "M1: TDE7(30nm, 5% wt)' as the luminescent layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm; wherein "5% wt" refers to the doping ratio of the blue dye, i.e., the weight ratio of the host material to TDE7 is 95: 5.
ET59 is evaporated on the luminescent layer in vacuum to be used as an electron transport layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 20 nm;
and (3) evaporating LiF with the thickness of 0.5nm as an electron injection layer and Al with the thickness of 150nm as a cathode on the electron transport layer in vacuum.
Device examples 2-6 and comparative examples 1-2 were fabricated in the same manner as in device example 1 except that the host materials were changed to M12, M21, M25, M27, M46, and R-1 and R-2.
Device example 7
The device structure is as follows:
ITO(150nm)/HI-2(10nm)/HT-2(40nm)/M1：PD1(30nm，10％wt)/ET58(25nm)/LiF(0.5nm)/Al(150nm)。
the process was essentially the same as for device example 1, except that the electron transporting material was changed from ET59 to ET58 and the dye was changed from TDE7 to PD1, with the host material still being M1.
Device examples 8-12 and comparative examples 3-4 were fabricated as in example 7, except that the host materials were changed to M12, M21, M22, M27, M47, and R-1 and R-2.
Device example 13
ITO(150nm)/HT32(20nm)/GPH77：TDE7(30nm，5wt％)/M29(30nm)/LiF(0.5nm)/Al(150nm)。
The preparation process of the organic electroluminescent device is as follows: glass plates coated with ITO (thickness 150nm) transparent conductive layers were sonicated in commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, vacuum evaporating a hole transport layer HT32 on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
vacuum evaporating a luminescent main body material and a dye on the hole transport layer to be used as a luminescent layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
vacuum evaporating M29 on the luminescent layer to form an electron transport layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 20 nm;
and (3) evaporating LiF with the thickness of 0.5nm and Al with the thickness of 150nm on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
Device examples 14-18 and comparative examples 5 and 6 were prepared as in example 13 except that the electron transport material was replaced with M35, M49, M53, M75, M82, and ET35, ET58 from M29.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the turn-on voltage and the maximum luminance of the organic electroluminescent devices prepared in examples 1 to 18 and comparative examples 1 to 6 were measured using a digital source meter and a luminance meter, and the maximum external quantum efficiency was calculated. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1cd/m2The voltage is the starting voltage, the current density at the moment is measured, and the maximum external quantum efficiency is calculated according to data such as spectrum and the like. The prepared organic electroluminescent device has maximum brightness, turn-on voltage and maximum external quantityThe related properties such as the sub-efficiencies are shown in tables 1 to 3.
TABLE 1
TABLE 2
TABLE 3
As can be seen from the above table, when the compound of the present invention is used as a host of fluorescent and phosphorescent dyes and an electron transport material, the turn-on voltage is reduced, the maximum brightness and the maximum external quantum efficiency are improved, and excellent device performance is shown.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are intended to be within the scope of the invention.
Claims (10)
1. A compound having the structure of formula (I):
wherein:
x is SiR2R3Or CR4R5Wherein R is2～R5The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
n is an integer of 0 to 4, R1The same or different, each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group; when R is1When two adjacent substituents are present, the two substituents can be fused to form a ring;
Y1～Y3each independently selected from CR6Or N; wherein R is6Selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30A heteroaryl group;
Ar1、Ar2each independently selected from substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30A heteroaryl group;
when R is1、R2、R3、R4、R5、R6、Ar1Or Ar2When a substituent is present in the selected group,the substituents are respectively and independently selected from halogen and C1～C10Alkyl or cycloalkyl, C2～C10Alkenyl radical, C1～C6Alkoxy or thioalkoxy group, C6～C30Monocyclic aromatic or fused ring aromatic hydrocarbon radical, C3～C30One of monocyclic heteroaromatic group or condensed ring heteroaromatic group.
2. The compound of claim 1, wherein R is1～R6Each independently selected from hydrogen, fluorine, chlorine, bromine, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, cyclopentyl, cyclohexyl, and substituted or unsubstituted of the following substituents: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, 9 '-dimethylfluorene, 9' -spirobifluorene, benzofluorene, fluoranthenyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
A phenyl, tetracenyl, furyl, thienyl, pyridyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl, quinolinyl, quinazolinyl group;
more preferably cyclohexyl, phenyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl, quinolyl.
3. The compound of claim 1, wherein Ar is1、Ar2Each independently selected from the following substituted or unsubstituted substituents: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, 9 '-dimethylfluorene, 9' -spirobifluorene, benzofluorene, fluoranthenyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
A phenyl group, a tetracenyl group, a furyl group, a thienyl group, a pyridyl group, a pyrrolyl group,Benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, quinolinyl, quinazolinyl;
more preferably phenyl, tolyl, xylyl, naphthyl, methylnaphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl.
4. The compound according to any one of claims 1 to 3, wherein the compound is selected from the group consisting of compounds represented by the following II-1 to II-4:
wherein, X, Y1、Y2、Y3、Ar1、Ar2The definition of (A) is as shown above; r1' is as defined for R1(ii) a m is an integer of 0 to 10.
5. The compound according to any one of claims 1 to 3, wherein the compound is selected from the group consisting of compounds represented by I-1 to I-12:
wherein, X, Y1、Y2、Y3、Ar1、Ar2、n、R1The definition of (A) is as shown above.
6. The compound of any one of claims 1 to 5, wherein the compound is selected from the group consisting of compounds represented by M1 to M87:
7. use of a compound according to any one of claims 1 to 6 in an organic electroluminescent device, preferably as a light-emitting layer in an organic electroluminescent device, more preferably as a light-emitting dye and/or sensitizer in a light-emitting layer of said organic electroluminescent device.
8. A thermally activated sensitized fluorescent material, characterized in that it comprises a compound according to any one of claims 1 to 6.
9. Use of the thermally activated sensitized fluorescent material according to claim 8 in an organic electroluminescent device, preferably as a light emitting layer in an organic electroluminescent device, more preferably as a light emitting dye and/or sensitizer in a light emitting layer of said organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first and second electrodes, characterized in that the organic layers comprise at least one compound according to any one of claims 1 to 6.
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