CN112480155B - Thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and organic electroluminescent device using thermal activation delayed fluorescence material as light emitting layer - Google Patents

Thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and organic electroluminescent device using thermal activation delayed fluorescence material as light emitting layer Download PDF

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CN112480155B
CN112480155B CN202011410143.1A CN202011410143A CN112480155B CN 112480155 B CN112480155 B CN 112480155B CN 202011410143 A CN202011410143 A CN 202011410143A CN 112480155 B CN112480155 B CN 112480155B
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张智博
李成龙
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Abstract

A thermal activation delayed fluorescence material containing double boron polycyclic aromatic hydrocarbon and an organic electroluminescent device using the thermal activation delayed fluorescence material as a luminescent layer belong to the technical field of organic electroluminescent materials. The structural general formula is shown as (I), and-L-is substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene; r-is substituted or unsubstituted carbazolyl, substituted or unsubstituted benzodiindolyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted acridinyl; the substituent is 1 or more than 2 of deuterium, halogen, nitrile group, alkyl, cycloalkyl, alkoxy, aryl or heterocyclic group. The organic electroluminescent device (OLED) prepared by the compound has the characteristics of low turn-on and high efficiency, and can be further used for preparing an organic electroluminescent display, an organic electroluminescent lighting source or a decorative light source.
Figure DDA0002817998270000011

Description

Thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and organic electroluminescent device using thermal activation delayed fluorescence material as light emitting layer
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and an organic electroluminescent device using the thermal activation delayed fluorescence material as a light emitting layer.
Background
Due to the wide application prospect in the fields of smart phones, televisions, wearable displays and solid-state lighting, organic light-emitting diodes (OLEDs) have been widely researched and paid attention to in the scientific and industrial fields for decades. According to the statistical rule of quantum spin, the traditional fluorescent OLED device can utilize 25% of singlet excitons generated by electric excitation at most, and when the light output efficiency of the device is 20%, the maximum external quantum efficiency is generally not more than 5%. In order to improve the efficiency of OLED devices, how to effectively utilize the remaining 75% of triplet excitons of non-radiative transitions has become a major concern for researchers. Among them, the discovery of phosphorescent electroluminescent devices is a milestone event in the history of OLED development, enabling 100% intra-device quantum efficiency (see m.a. baldo, d.f. o' brienetal, Nature,1998,395,151). Currently, devices employing phosphorescent materials of heavy metal complexes of iridium (Ir), platinum (Pt), etc. have achieved external quantum efficiencies in excess of 20%. However, since the phosphorescent materials of noble metals such as Ir and Pt have limited resources and high cost, the development of an OLED device based on a triplet exciton utilization mechanism of a cheap pure organic material has become a hot spot of current research. In recent years, OLED materials and devices based on a Thermally Activated Delayed Fluorescence (TADF) mechanism have attracted considerable attention from researchers (see h.uoyama, k.goushi, k.shizu, h.nomura, c.adachi, nature, 2012,492,234; q.zhang, j.li, k.shizu, s.huang, s.hirata, h.miyazaki, c.adachi, j.am.chem.soc.2012,134, 14706). The organic micromolecule material with smaller energy level difference between the singlet excited state and the triplet excited state is utilized, and the triplet excitons can be converted into the singlet excitons through the reverse intersystem crossing process under the action of environmental heat energy, so that delayed fluorescence is emitted. The mechanism adopts pure organic micromolecular material without noble metal, so that the fluorescent device can effectively utilize the energy of triplet excitons, the external quantum efficiency of the device is close to or even reaches the level of a phosphorescent device, and the method has important significance for effectively saving resources, protecting the environment, reducing the production cost and realizing industrialization.
Currently, the external quantum efficiency of organic electroluminescent devices based on thermally activated delayed fluorescent materials has exceeded 25%, but due to their long delay lifetime, the devices exhibit a severe efficiency roll-off at high current densities. Therefore, in order to further improve the efficiency and stability of the device, the development of a new and efficient thermally activated delayed fluorescence material is currently an important challenge.
Disclosure of Invention
The invention aims to provide a thermal activation delayed fluorescence material containing double-boron polycyclic aromatic hydrocarbon and an organic electroluminescent device using the thermal activation delayed fluorescence material as a luminescent layer.
The invention relates to a thermal activation delayed fluorescence material (TADF) containing diboron polycyclic aromatic hydrocarbon, which has a structural general formula shown in (I):
Figure BDA0002817998250000021
wherein: -L-is substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene;
preferably, -L-is a structure represented by one of the following structural formulae:
Figure BDA0002817998250000022
wherein the dotted lines represent single bonds to B and R, respectively.
R-is substituted or unsubstituted carbazolyl, substituted or unsubstituted benzodiindolyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted acridinyl;
preferably, R-has a structure selected from one of the following:
Figure BDA0002817998250000031
wherein the dotted line represents a single bond to L.
Preferably, the heat-activated delayed fluorescence material containing the diboron polycyclic aromatic hydrocarbon has a structural formula shown in one of the following formulas:
Figure BDA0002817998250000032
Figure BDA0002817998250000041
Figure BDA0002817998250000051
Figure BDA0002817998250000061
Figure BDA0002817998250000071
Figure BDA0002817998250000081
Figure BDA0002817998250000091
the compound shown in the structural general formula (I) can be prepared according to the conventional chemical synthesis method in the field, and the steps and conditions can refer to the steps and conditions of similar reactions in the field.
The invention provides a preparation method of a compound with a structural general formula shown as (I), which has the following reaction formula:
Figure BDA0002817998250000092
in the above reaction formula, L and R are as defined in the general formula (I).
The present invention also provides an organic electroluminescent device (OLED) composed of a cathode, a transparent anode, and one or more organic compound layers interposed between the two electrodes; the organic compound layer at least comprises a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, the heat activation delayed fluorescence material containing the double-boron polycyclic aromatic hydrocarbon is doped into a main material (can be CBP) as a guest material and is used as the light emitting layer, and the weight doping proportion of the guest material in the light emitting layer is 1-50%.
In the OLED device, the transparent anode may be formed by using an electrode material known per se, that is, by vapor-depositing an electrode material having a large work function, such as ITO (indium tin oxide) or gold, on a substrate (a transparent substrate such as a glass substrate).
As the material for the device of the present invention, any material known in the art for organic electroluminescent devices can be used
The organic electroluminescent device is used for preparing organic electroluminescent displays, organic electroluminescent lighting sources and decorative light sources.
Description of the terms
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, and a heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 2-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 2-pentyl group, and the like, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a fluorenyl group, or the like, but is not limited thereto.
In the present specification, the heteroaryl group contains 1 or more heteroatoms other than carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, Si, S, and the like. The number of carbon atoms of the heteroaryl group is not particularly limited, but the number of carbon atoms is preferably 2 to 30. Examples of the heteroaryl group include, but are not limited to, a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, a dibenzothiapyrrolyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenazinyl group, and a fused structure thereof.
In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.
In this specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups applies, except that they are each a 2-valent group.
Drawings
Fig. 1 is a schematic diagram of a device structure used in an effect embodiment.
In fig. 1,1 is ITO, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a metal cathode.
Detailed Description
The present invention will be described in further detail below with reference to specific general formulae, examples and tables, but the embodiments of the present invention are not limited thereto. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
Examples 1 to 112
In order to explain the production method of the present invention in more detail, the production of compound 1 will be described as an example.
Figure BDA0002817998250000111
Under a nitrogen atmosphere, adding a mixture of 7, 7-dimethyl-7H-dinaphtho [2, 1-b: boron tribromide (6mL) was added to a mixture of 1', 2' -d ] silyl (3.86mmol) and aluminum chloride (0.19mmol), and the mixture was reacted in a 50 ℃ oil bath for 18 hours. Removing excessive boron tribromide under reduced pressure to obtain a dibromo intermediate product.
Another 100mL three-necked flask was taken, under nitrogen protection, 4-bromotriphenylamine (3mmol) and diethyl ether (30mL) were added, butyllithium (3.5mmol) was slowly added dropwise at-78 deg.C, the temperature was maintained for 10min, and then the mixture was heated to 0 deg.C and stirred for 30 min. The reaction solution is cooled to-78 ℃ again, and then the dibromo intermediate product and toluene (20mL) are dropped into the reaction system, and slowly heated to room temperature for reaction for 12 hours. After the reaction was complete, the system was concentrated in vacuo and the crude product was purified using dichloromethane: petroleum ether is 1: silica gel column chromatography of 8 (vol) as the mobile phase gave the product as an orange solid in 39% yield.
The preparation processes of the compounds are basically the same, and are not repeated herein, and only specific results are listed in table 1. In addition, in the process of preparing the compound of the present invention, the amount of each substance added can be determined according to the ratio of each substance in the above examples.
TABLE 1 Synthesis example product data
Figure BDA0002817998250000121
Figure BDA0002817998250000131
Figure BDA0002817998250000141
Figure BDA0002817998250000151
Effects of the embodiment
The following embodiments of the electroluminescent device prepared by using the material of the present invention have the following specific device preparation process and device performance test experimental operations: the transparent ITO glass is used as a substrate material for preparing a device, has the thickness of 180nm and the sheet resistance of 10 omega, and is pretreated before use. The pretreatment process comprises the steps of carrying out ultrasonic treatment on 5% ITO washing liquor for 30min, then respectively carrying out ultrasonic washing on the ITO washing liquor for 10min by distilled water (3 times), acetone (3 times) and isopropanol (3 times), and finally storing the ITO glass in the isopropanol. Before each use, the surface of the ITO glass is carefully wiped by using an acetone cotton ball and an isopropanol cotton ball, the ITO glass is dried after being washed by isopropanol, and then O is used2Plasma (Plasma) treatment for 5min under the conditions of a reaction chamber pressure of 100mTorr, a radio frequency power of 7W, and a gas flow rate of 100cm3. The preparation of the device is completed by vacuum evaporation process by using vacuum coating equipment, and when the vacuum degree of a vacuum evaporation system reaches 5 multiplied by 10-4And (3) starting evaporation when the pressure is lower than Pa, monitoring the deposition rate by a Saynes film thickness meter, and sequentially depositing various organic layers, a LiF electron injection layer and a metal Al electrode on the ITO glass by utilizing a vacuum evaporation process (the specific device structure is shown in the following effect examples). The characteristics of the device such as current, voltage, brightness, light-emitting spectrum and the like are synchronously tested by a PR655 spectral scanning luminance meter and a Keithley K2400 digital source meter system. The performance test of the device was performed in air.
Effect examples 1 to 15
The names of the components are: transparent glass or other transparent substrate, ITO anode attached to the transparent substrate, TAPC (4, 4' -cyclohexylbis [ N, N-di (4-methylphenyl) aniline)]) The material comprises a hole transport layer and an mCP (1, 3-di-9-carbazolyl benzene) electron blocking layer, wherein the weight ratio of a light-emitting layer (TADF guest material to a host CBP (4, 4-di (9-carbazole) biphenyl) of the material is 10: 90) b3PyMPM (4, 6-bis)The (3, 5-di (3-pyridyl) phenyl) -2-methylpyrimidine) electron transport layer, the LiF electron injection layer and the metal Al as the cathode. Example 1 the organic electroluminescent device has a structure of [ ITO/TAPC (40nm)/mCP (5nm)/EML (30nm)/B3PyMPM(50nm)/LiF(1nm)/Al(100nm)]And EML represents a light emitting layer. Results of the examples are shown in table 2.
Figure BDA0002817998250000161
In an effect example, basic performance indicators of the OLED device, including the turn-on voltage, the maximum luminance of light emission, and the device efficiency (%) of the device, were characterized by conventional methods.
Table 2: effect embodiment data
Figure BDA0002817998250000162
Figure BDA0002817998250000171
As can be seen from the results of table 2 above, the organic electroluminescent device (OLED) prepared using the compound of the present invention exhibits low turn-on, high efficiency characteristics.
The above description is only exemplary of the present invention, and various modifications may be made by those skilled in the art without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention, but to illustrate the technical idea of the present invention and are not limited to such embodiments. The scope of the invention should be construed in accordance with the appended claims, and all technical ideas within the scope and range of equivalents thereof are included in the scope of the claims.

Claims (7)

1. A heat-activated delayed fluorescence material containing double boron polycyclic aromatic hydrocarbon is shown as the structural general formula (I):
Figure FDA0003508176800000011
wherein L is
Figure FDA0003508176800000012
The dotted lines represent single bonds to B and R, respectively; r-is substituted or unsubstituted carbazolyl, substituted or unsubstituted benzodiindolyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted acridinyl; the substituent is 1 or more than 2 of deuterium, halogen, nitrile group, alkyl, cycloalkyl, alkoxy, aryl or heterocyclic group.
2. The thermally activated delayed fluorescence material comprising a polyboronated aromatic hydrocarbon according to claim 1, wherein: the alkyl is a linear or branched alkyl group with the carbon number of 1 to 30, the cycloalkyl is a cycloalkyl group with the carbon number of 3 to 30, the alkoxy is a linear, branched or cyclic alkoxy with the carbon number of 1 to 30, and the aryl is a monocyclic aryl with the carbon number of 6 to 30 or a polycyclic aryl with the carbon number of 10 to 24; the hetero atom of the heteroaryl is selected from 1 or more than 1 of O, N, Se, Si or S, and the number of carbon atoms is 2 to 30.
3. The thermally activated delayed fluorescence material comprising a polyboronated aromatic hydrocarbon according to claim 1, wherein: the structural formula of R-is shown as the following formula,
Figure FDA0003508176800000021
the dotted line represents a single bond to L.
4. The thermally activated delayed fluorescence material comprising a polyboronated aromatic hydrocarbon according to any of claims 1 to 3, wherein: the structural formula of the compound is shown as one of the following formulas,
Figure FDA0003508176800000022
Figure FDA0003508176800000031
Figure FDA0003508176800000041
Figure FDA0003508176800000051
Figure FDA0003508176800000061
Figure FDA0003508176800000071
Figure FDA0003508176800000081
5. an organic electroluminescent device comprising a cathode, a transparent anode and one or more organic compound layers interposed between the two electrodes; the organic compound layer at least comprises a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, and is characterized in that: the thermally activated delayed fluorescence material containing the diboron polycyclic aromatic hydrocarbon according to any one of claims 1 to 4, which is used as a guest material, is doped into a host material and is used as a light emitting layer.
6. An organic electroluminescent device as claimed in claim 5, wherein: the weight doping proportion of the guest material in the luminescent layer is 1-50%.
7. The use of the thermally activated delayed fluorescence material of a polyboronated aromatic hydrocarbon according to claim 5 or 6 in organic electroluminescent devices, characterized in that: the organic electroluminescent device is used for preparing an organic electroluminescent display, an organic electroluminescent lighting source or a decorative light source.
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