CN112661778A - Boron-containing aryl imide organic electroluminescent material and application thereof - Google Patents
Boron-containing aryl imide organic electroluminescent material and application thereof Download PDFInfo
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Abstract
The invention relates to a boron-containing aryl imide organic electroluminescent material, which is represented by the following formula (I):
wherein, X1Represents any one of tetra-substituted aryl with the number of benzene rings not more than 3 and derivatives thereof; x2Represents any one of an oxygen atom and a 2-substituted propyl group; x3Represents a benzene ring or any one of its derivatives, X1、X3Identical or different, X1、X3Are all reacted with X2Different. The organic electroluminescent material is used as a green phosphorescent main body material to be applied to the luminescent layer. The organic electroluminescent material has a structureThe organic electroluminescent device has proper molecular energy level and higher glass transition temperature, and is applied to the organic electroluminescent device, so that the organic electroluminescent device has better current efficiency and longer device life.
Description
Technical Field
The invention relates to a boron-containing aryl imide organic electroluminescent material and application thereof, belonging to the technical field of organic electroluminescent materials.
Background
Pope et al first discovered the electroluminescent properties of single-crystal anthracene in 1965, which is the first electroluminescent phenomenon of organic compounds. Through the continuous development for many years, the organic electroluminescent device can be used for manufacturing novel display products and novel illumination products, and is expected to replace the existing liquid crystal display and fluorescent lamp illumination. Compared with the liquid crystal display technology, the OLED display technology has many advantages of self-luminescence, no radiation, light weight, thin thickness, wide viewing angle, wide color gamut, stable color, fast response speed, strong environmental adaptation, flexible display and the like, and therefore, the OLED display technology is gaining more and more attention and corresponding technical investment.
In a phosphorescent device having a host/guest as a light emitting layer, there are generally three ways to achieve light emission of the guest: (i) under the excitation of an electric field, singlet excitons formed in a Host (Host) are transferred to a guest (guest) through Forster and Dexter energy, then the phosphorescent heavy metal guest material changes the singlet excitons into triplet excitons through intersystem crossing, and finally the excited triplet state radiation of the guest is attenuated to emit light; (ii) triplet excitons formed in the host are transferred to the guest by Dexter energy, and the guest returns to a ground state after undergoing radiative decay luminescence in an excited triplet state; (iii) holes and electrons injected from the anode and the cathode, respectively, are directly trapped by the phosphorescent guest to form excitons, and then the guest returns to a ground state to emit light.
Since the realization of electrophosphorescence by Forrest et al in 1997, phosphorescent light-emitting materials based on heavy metal complexes have been developed rapidly, so far, many review articles have summarized the phosphorescent complexes, and metal organic complexes centering on heavy metal atoms of Vlll groups such as Re, Ru, Os, Ir, Pt and the like have strong spin-orbit coupling effect. Of the reported phosphorescent emitters, complexes centered on the trivalent metal iridium are of particular interest, and the iridium complexes most widely studied are FIrpic, green Ir (ppy)3 and (ppy)2Ir (acac) and red (piq)2Ir (acac) emitting blue light.
In order to obtain high performance of the electroluminescent device, it is important to develop a new and effective host material as a guest material, and in the process of developing a new electroluminescent host material, it is concluded that the effective host material should have the following basic requirements: (i) in order to suppress the triplet energy flux from the guest to the host, confining triplet excitons within the light emitting layer requires that the triplet state of the host material should be higher than the guest; (ii) the HOMO energy level of the host material should be matched with that of the adjacent hole transport material, otherwise, the HOMO energy level of the host material is too low, a larger hole injection barrier is generated, the driving voltage of the device is increased, similarly, the LUMO energy level of the host should be matched with that of the electron transport material so as to reduce the electron injection barrier, and in addition, the HOMO and LUMO energy level widths of the host are larger than those of the guest material, so that the energy transfer from the host to the guest and the direct capture of carriers on the guest are facilitated; (iii) the host material should have a high carrier transport rate and balanced carrier transport performance to facilitate the recombination of holes and electrons in the device and obtain a wide carrier recombination region, and therefore, the molecular structure of the host should include a conjugated unit suitable for carrier transport; (iv) consistent with other organic electroluminescent materials, the host material should have good thermal stability and film-forming property, so as to form a stable and uniform thin film during vacuum thermal evaporation, reduce phase separation, and maintain the stability of the device.
CDBP is a green phosphorescent host material for commercial early low-generation OLED production lines, but the high requirements of the production lines on the green phosphorescent host material are difficult to meet due to the low glass transition temperature, the current efficiency and the service life of the CDBP.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a boron-containing aryl imide organic electroluminescent material and application thereof.
The technical scheme for solving the technical problems is as follows: a boron-containing aryl imide organic electroluminescent material is disclosed, which is represented by the following formula (I):
wherein, X1Represents any one of tetra-substituted aryl with the number of benzene rings not more than 3 and derivatives thereof; x2Represents any one of an oxygen atom and a 2-substituted propyl group; x3Represents a benzene ring or any one of its derivatives, X1、X3Identical or different, X1、X3Are all reacted with X2Different.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, said X1Any one selected from the following groups:
the beneficial effect of adopting the further scheme is that: more suitable molecular size, non-planar spatial structure and suitable molecular energy level distribution are obtained.
Further, said X3Any one selected from the following groups:
the beneficial effect of adopting the further scheme is that: more suitable molecular size, non-planar spatial structure and suitable molecular energy level distribution are obtained.
Further, the organic electroluminescent material is selected from any one of the following structural formulas of C01-C15:
the beneficial effect of adopting the further scheme is that: the HOMO and LUMO energy levels and the S1 energy level are calculated through molecular simulation, the existing commercial finished product materials can be matched, and the excellent photoelectric properties are confirmed through later device evaluation tests.
The invention also discloses application of the boron-containing aryl imide organic electroluminescent material, and the organic electroluminescent material is applied to at least one functional layer in an organic electroluminescent device.
Furthermore, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode; and the positive electrode is sequentially superposed with the hole injection layer, the hole transport layer, the luminescent layer, the electron transport layer, the electron injection layer and the negative electrode.
The organic electroluminescent material is used as a green phosphorescent main body material to be applied to the luminescent layer.
The invention has the beneficial effects that:
1) through a conventional organic synthesis method, compound molecules taking boron-containing aryl imide as a core structure are constructed, and are original structures which are not reported, and the molecular structure of the organic electroluminescent material has proper molecular weight (400-1200), higher glass transition temperature Tg (above 120 ℃), good film stability (difficult crystallization), proper molecular energy level (can be matched with materials of various existing functional layers), and is suitable for being used as a main material of a light-emitting layer;
2) in the molecular structure of the organic electroluminescent material, an aryl imine ring is taken as a central coplanar structure and is respectively connected with two groups of carbon-nitrogen bonds and carbon-boron bonds, so that an obvious inclination angle is formed, and the spatial three-dimensional structure of the whole molecule is increased through the two groups of different types of twisted configurations, thereby being more beneficial to the conduction and combination of electrons and holes in a light-emitting layer and having important significance for improving the current efficiency;
3) the organic electroluminescent material is used as a main material, and the existing luminescent material Ir (PPy)3 is doped to be used as a luminescent layer, so that the current efficiency and the service life of the prepared organic electroluminescent device are remarkably improved;
4) compared with the commercial host material CDBP, the organic electroluminescent device manufactured by using the organic electroluminescent material as the host material has better current efficiency and longer device life.
The organic electroluminescent material has good application effect in OLED luminescent devices and good industrialization prospect.
Drawings
FIG. 1 is a schematic view of the structure of an organic electroluminescent device described in the device example;
FIG. 2 is a nuclear magnetic hydrogen spectrum of Compound C01 described in the examples;
FIG. 3 is a mass spectrum of Compound C01 described in the examples;
in the figure, 1 anode, 2 hole injection layer, 3 hole transport layer, 4 light emitting layer, 5 electron transport layer, 6 electron injection layer, 7 cathode.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the aforementioned objects, features and advantages of the invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
Compound preparation example:
EXAMPLE 1 preparation of Compound C01
In a 250mL three-necked flask, pyromellitic anhydride (4.36g, 0.02mol), a boron amine intermediate 1(15.89g, 0.04mol) and propionic acid (120g) are added, and the temperature of the system is slowly raised to 100-120 ℃ under the protection of nitrogen. After the reaction is carried out for 24 hours under the condition of heat preservation, light yellow solid powder is separated out from the reaction system. Cooling the system to room temperature, and performing suction filtration to obtain a light yellow filter cake. Heating and dissolving a filter cake by using 150g of tetrahydrofuran, quickly passing the obtained solution through a silica gel column with the thickness of 20cm, and removing the solvent through the column liquid to obtain a light yellow solid crude product, wherein the crude product uses toluene: purification by recrystallization from 1:1 petroleum ether, cooling, suction filtration and drying gave compound C01 as a pale yellow solid 15.82g with a yield of 81.0%.
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C64H62B2N2O6Theoretical value 976.48, test value 976.41. Elemental analysis (C)64H62B2N2O6) Theoretical value C: 78.69, H: 6.40, O: 9.83, found C: 78.62, H: 6.45, O: 9.78.
EXAMPLE 2 preparation of Compound C03
Compound C03 was obtained as a pale yellow solid in 14.83g and 72.1% yield by the method described in example 1 (preparation of compound C01) in which boramine intermediate 2(16.94g, 0.04mol) was charged instead of boramine intermediate 1(15.89g, 0.04 mol).
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C70H74B2N2O4Theoretical value 1028.58, test value 1028.36. Elemental analysis (C)70H74B2N2O4) Theoretical value C: 81.71, H: 7.25, O: 6.22, found C: 81.76, H: 7.20, O: 6.20.
EXAMPLE 3 preparation of Compound C05
The procedure described in example 1 (preparation of Compound C01) was followed, and 3,3 ', 4, 4' -biphenyltetracarboxylic dianhydride (5.88g, 0.02mol) was charged in place of pyromellitic anhydride (4.36g, 0.02mol) to give Compound C05 as a pale yellow solid (14.47 g, yield 68.7%).
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C70H66B2N2O6Theoretical value 1052.51, test value 1052.11. Elemental analysis (C)70H66B2N2O6) Theoretical value C: 79.85, H: 6.32, O: 9.12, found C: 79.78, H: 6.37, O: 9.16.
EXAMPLE 4 preparation of Compound C08
According to the procedure described in example 1 (preparation of Compound C01), 1,4,5, 8-naphthalenetetracarboxylic anhydride (5.36g, 0.02mol) was charged in place of pyromellitic anhydride (4.36g, 0.02mol) to give Compound C08 as a pale yellow solid (15.69 g) with a yield of 76.4%.
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C68H64B2N2O6Theoretical value 1026.50, test value 1026.39. Elemental analysis (C)68H64B2N2O6) Theoretical value C: 79.54, H: 6.28, O: 9.35, found C: 79.49, H: 6.33, O: 9.32.
EXAMPLE 5 preparation of Compound C10
According to the procedure described in example 2 (preparation of Compound C03), 1,4,5, 8-naphthalenetetracarboxylic anhydride (5.36g, 0.02mol) was charged in place of pyromellitic anhydride (4.36g, 0.02mol) to give Compound C10 as a pale yellow solid (14.18 g, 65.7% yield).
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C74H76B2N2O4Theoretical value 1078.60, test value 1078.44. Elemental analysis (C)74H76B2N2O4) Theoretical value C: 82.37, H: 7.10, O: 5.93, found C: 82.31, H: 7.13, O: 5.89.
EXAMPLE 6 preparation of Compound C12
According to the procedure described in example 1 (preparation of Compound C01), 1,2,5, 6-naphthalenetetracarboxylic anhydride (5.36g, 0.02mol) was charged in place of pyromellitic anhydride (4.36g, 0.02mol) to give Compound C12 as a pale yellow solid (14.95 g, yield 72.8%).
Mass Spectrometry, APCI Source, negative ion mode, molecular formula C68H64B2N2O6Theoretical value 1026.50, test value 1026.43. Elemental analysis (C)68H64B2N2O6) Theoretical value C: 79.54, H: 6.28, O: 9.35, found C: 79.47, H: 6.35, O: 9.33.
organic electroluminescent device example:
the effect of the compound synthesized by the present invention as a host material for a light emitting layer in a device is explained in detail by device examples 1 to 6 and comparative example 1 below. Compared with the embodiment 1, the embodiments 2 to 6 and the comparative example 1 of the present invention have the same device manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the host material of the light emitting layer in the device is changed. The structural composition of the device is shown in table 1; the test results of the resulting devices are shown in table 2.
Device example 1
Transparent substrate layer + ITO Anode layer 1/hole injection layer 2(HAT-CN, thickness 10 nm)/hole transport layer 3(TAPC, thickness 50 nm)/light-emitting layer 4 (Compounds C01 and Ir (PPy)3According to the following steps of 95: 5, thickness of 30 nm)/electron transport layer 5(TPBI, thickness of 30 nm)/electron injection layer 6(LiF, thickness of 1 nm)/cathode electrode layer 7 (Al). The molecular structural formula of each compound is as follows:
the preparation process comprises the following steps:
the transparent substrate layer 1 is made of transparent materials such as glass; the ITO anode layer 1 (film thickness: 140nm) was washed by sequentially performing alkali washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO.
HAT-CN with a thickness of 10nm was deposited on the washed ITO anode layer 1 by a vacuum deposition apparatus to be used as the hole injection layer 2. Subsequently, TAPC was evaporated to a thickness of 50nm as the hole transport layer 3.
After the evaporation of the hole transport material is finished, the light emitting layer 4 of the OLED light emitting device is manufactured, and the structure of the light emitting layer 4 includes that a material compound C01 used by the OLED light emitting layer 4 is used as a main material, ir (ppy)3 is used as a doping material, and the doping proportion of the doping material is 95: 5 wt% and the thickness of the light-emitting layer was 30 nm.
After the light-emitting layer 4, the electron transport layer material is continuously vacuum-evaporated to obtain TPBI, the vacuum-evaporated film thickness of the material is 30nm, and the electron transport layer 5 is formed.
On the electron transport layer 5, a lithium fluoride (LiF) layer having a film thickness of 1nm was formed by a vacuum deposition apparatus, and this layer was an electron injection layer 6.
On the electron injection layer 6, an aluminum (Al) layer having a film thickness of 100nm was formed by a vacuum deposition apparatus, and this layer was used as the cathode reflection electrode layer 7.
After the OLED light emitting device was completed in the above-described manufacturing process, the anode and the cathode were connected by a known driving circuit, and the light emitting efficiency, the light emission spectrum, and the current-voltage characteristics of the device were measured. The test results of the fabricated OLED light emitting device are shown in table 2.
TABLE 1
TABLE 2
The current efficiency in comparative example 1 was 14.4cd/A (@10mA/cm 2); the starting voltage was 5.2V (@1cd/m2), and the LT95 lifetime decay at 5000nit luminance was 4.3 Hr.
From the results in table 2, it can be seen that the organic electroluminescent material of the present invention can be applied to the fabrication of OLED light emitting devices as a host material of a light emitting layer, and compared with comparative example 1, the organic electroluminescent material has a better improvement in efficiency and lifetime than known OLED materials, and particularly the driving lifetime of the device is greatly improved.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. A boron-containing aryl imide organic electroluminescent material is characterized in that the organic electroluminescent material is represented by the following formula (I):
wherein, X1Represents any one of tetra-substituted aryl with the number of benzene rings not more than 3 and derivatives thereof; x2Represents any one of an oxygen atom and a 2-substituted propyl group; x3Represents a benzene ring or any one of its derivatives, X1、X3Identical or different, X1、X3Are all reacted with X2Different.
2. The boron-containing arylimide organic electroluminescent material as claimed in claim 1, wherein X is1Any one selected from the following groups:
3. the boron-containing arylimide organic electroluminescent material as claimed in claim 1, wherein X is3Any one selected from the following groups:
4. the boron-containing arylimide organic electroluminescent material as claimed in claim 1, wherein the organic electroluminescent material is selected from any one of the following structural formulas C01-C15:
5. use of a boron-containing arylimide organic electroluminescent material according to any one of claims 1 to 4 in an organic electroluminescent device comprising at least one functional layer.
6. The use of the boron-containing arylimide organic electroluminescent material as claimed in claim 5, wherein the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode; and the positive electrode is sequentially superposed with the hole injection layer, the hole transport layer, the luminescent layer, the electron transport layer, the electron injection layer and the negative electrode.
7. The use of the boron-containing arylimide organic electroluminescent material as claimed in claim 6, wherein the organic electroluminescent material is used as a green phosphorescent host material in the light-emitting layer.
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