CN113929708A - Boron-containing compound and application thereof in organic electroluminescent device - Google Patents

Boron-containing compound and application thereof in organic electroluminescent device Download PDF

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CN113929708A
CN113929708A CN202010602196.7A CN202010602196A CN113929708A CN 113929708 A CN113929708 A CN 113929708A CN 202010602196 A CN202010602196 A CN 202010602196A CN 113929708 A CN113929708 A CN 113929708A
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substituted
deuterated
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biphenylyl
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侯美慧
曹旭东
张兆超
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention relates to a boron-containing compound and application thereof in an organic electroluminescent device, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (I):
Figure DDA0002559368110000011
the invention also discloses application of the compound. The compound provided by the invention has higher glass transition temperature and molecular thermal stability, appropriate HOMO and LUMO energy levels, narrow half-peak width and high fluorescence quantum yield; forWhen the doping material is arranged in the luminescent layer of the OLED luminescent device, the current efficiency and the external quantum efficiency of the device are obviously improved, the luminescent color purity and the service life of the device are also greatly improved, and the boron-containing compound is used as the doping material of the luminescent layer to ensure that the device has good photoelectric property.

Description

Boron-containing compound and application thereof in organic electroluminescent device
Technical Field
The invention relates to the technical field of semiconductors, in particular to a boron-containing compound and application thereof in an organic electroluminescent device.
Background
Organic electroluminescent devices (OLEDs) are characterized by self-luminescence, flexibility, thinness, and wide viewing angle, and have the advantages of low voltage, fast response speed, good temperature adaptability, etc. during operation, and have attracted wide attention in the industry and academia for application in large-area flat panel displays and lighting.
The traditional fluorescent doping material is limited by the early technology, only 25% singlet excitons formed by electric excitation can emit light, the internal quantum efficiency of the device is low (the highest is 25%), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is far from that of a phosphorescence device. The phosphorescence material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, most phosphorescent materials are limited in application in OLEDs due to problems of high price, poor material stability, poor color purity, severe device efficiency roll-off and the like.
With the advent of the 5G era, higher requirements are put on color development standards, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doped material can realize high fluorescence quantum and narrow half-peak width through molecular engineering, the blue fluorescent doped material has obtained a stepwise breakthrough, and the half-peak width of the boron material can be reduced to below 30 nm; the human eye is a more sensitive green light region, and research is mainly focused on phosphorescent doped materials, but the luminescence peak shape of the phosphorescent doped materials is difficult to narrow by a simple method, so that the research on the high-efficiency green fluorescent doped materials with narrow half-peak width has important significance for meeting higher color development standards.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides a boron-containing compound and its application in an organic electroluminescent device. The compound has higher glass transition temperature, higher molecular thermal stability, proper HOMO and LUMO energy levels, narrow half-peak width and high fluorescence quantum yield; when the boron-containing compound is used as a doping material in a light-emitting layer of an OLED light-emitting device, the light-emitting color purity and the service life of the device are greatly improved, and the boron-containing compound is used as the doping material of the light-emitting layer, so that the device has good photoelectric property.
In order to solve the above technical problems, the present invention provides the following technical solutions: a boron-containing compound as a doping material of an OLED, the structure of the boron-containing compound being represented by the general formula (1):
Figure BDA0002559368090000011
Figure BDA0002559368090000021
in the general formula (1), X is1-X4Represented by-O-, -S-, -C (R)1)(R2) -or-N (R)3) -, and X1-X4At least one of which is represented by-N (R)3)-，R1-R3Each independently represents a hydrogen atom, a substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
z is nitrogen atom or C-R4Each occurrence of Z is the same or different;
i represents 0, 1;
the R is4Represented by a hydrogen atom, a deuterium atom, a tritium atom, a cyano group, a halogen group, a substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
and R is3And R4May be bonded to each other to form a ring;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium atom, tritium atom, cyano group, halogen atom, C1-C10Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, R is3And R4May be bonded to each other to form a five-membered ring or a six-membered ring.
As a further improvement of the invention, the structure of the boron-containing compound is shown as a general formula (1-1) or a general formula (1-2):
Figure BDA0002559368090000022
wherein the symbols have the meanings defined in claim 1.
As a further improvement of the invention, the structure of the boron-containing compound is shown as a general formula (1-3) or a general formula (1-4):
Figure BDA0002559368090000023
wherein the symbols have the meanings defined in claim 1.
As a further development of the invention, X is1-X4At least two of which are represented by-N (R)3)-。
As a further improvement of the invention: the R is1-R4Each independently represents a methyl group, a deuterated methyl group, a tritiated methyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuryl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted phenyl group, a tritiated phenyl group, a, Ethyl substituted biphenylyl, isopropyl substitutedOne of a substituted biphenylyl group, a tert-butyl substituted biphenylyl group, a deuterated methyl substituted phenyl group, a deuterated ethyl substituted phenyl group, a deuterated isopropyl substituted phenyl group, a deuterated tert-butyl substituted phenyl group, a deuterated methyl substituted biphenylyl group, a deuterated ethyl substituted biphenylyl group, a deuterated isopropyl substituted biphenylyl group, a deuterated tert-butyl substituted biphenylyl group, a tritiomethyl substituted phenyl group, a tritioethyl substituted phenyl group, a tritioisopropyl substituted phenyl group, a tritio tert-butyl substituted phenyl group, a tritiomethyl substituted biphenylyl group, a tritioethyl substituted biphenylyl group, a tritio isopropyl substituted biphenylyl group, or a tritio tert-butyl substituted biphenylyl group.
As a further improvement of the invention, said C6-C30The aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
said C is2-30Heteroaryl represents one of pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, dibenzofuryl, 9-dimethylfluorenyl, N-phenylcarbazolyl, quinolyl, isoquinolyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl and benzimidazolyl;
the substituent is one or more of protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, quinoxalyl group, quinazolinyl group, cinnolinyl group, naphthyridinyl group, fluorenyl group, dibenzofuranyl group, N-phenylcarbazolyl group or dibenzothiophenyl group.
As a further improvement of the present invention, the specific structure of the organic compound is any one of the following structures:
Figure BDA0002559368090000031
Figure BDA0002559368090000041
Figure BDA0002559368090000051
Figure BDA0002559368090000061
Figure BDA0002559368090000071
Figure BDA0002559368090000081
Figure BDA0002559368090000091
Figure BDA0002559368090000101
Figure BDA0002559368090000111
Figure BDA0002559368090000121
an organic electroluminescent device comprising a cathode, an anode and an organic functional layer, said organic functional layer being located between the cathode and the anode, said organic electroluminescent device comprising said boron-containing compound in the functional layer.
As a further improvement of the invention, the organic functional layer of the organic electroluminescent device comprises a light-emitting layer, and the doping material of the light-emitting layer is the boron-containing compound.
As a further improvement of the present invention, the light-emitting layer includes a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing compound.
TADF sensitized fluorescent Technology (TSF) combines TADF material and fluorescent doping material, TADF material is used as exciton sensitization medium, triplet excitons formed by electric excitation are converted into singlet excitons, energy is transferred to the fluorescent doping material through the singlet exciton long-range energy transfer, the quantum efficiency in the device can reach 100%, the technology can make up the defect of insufficient utilization rate of the fluorescent doping material excitons, the characteristics of high fluorescent quantum yield, high device stability, high color purity and low price of the fluorescent doping material are effectively exerted, and the technology has wide prospect in the application of OLEDs.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound is applied to OLED devices, can be used as a luminescent layer doping material, can emit fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display;
(2) the spectrum FWHM of the compound material is narrow, and when the compound material is used as a luminescent layer doping material of an organic electroluminescent device, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved;
(3) the compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(4) the compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, can keep the stability of a film layer formed by the materials when being applied to an OLED device, and prolongs the service life of the OLED device.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent glass substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a luminescent layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
All raw materials in the preparation examples were purchased from energy-saving Wangrun Co.
Preparation example 1: synthesis of Compound 1
Figure BDA0002559368090000131
Under nitrogen atmosphere, 1mmol of raw material A1 and 5mmol of raw material B1 were added to a three-necked flask, dissolved in 50ml of tetrahydrofuran, and 15mmol of potassium carbonate and 0.25mmol of Pd (PPh) were added3)4Heating the reaction mixture to 70 ℃, refluxing for 24 hours, taking a sample, indicating that no raw material A1 remains, completely reacting, and naturally cooling to room temperature; then washing with dichloromethane, and purifying the obtained substance with a silica gel column to obtain a target product intermediate C1 with HPLC purity of 99.16% and yield of 73.32%;
adding 0.01mol of intermediate C1, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a three-neck flask under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 1 with the HPLC purity of 98.39 percent and the yield of 33.20 percent;
preparation example 3: synthesis of Compound 11
Figure BDA0002559368090000141
In a three-necked bottle, introducingUnder a nitrogen atmosphere, 1.5mmol of A3 as a starting material, 5mmol of N1 as a starting material were added and dissolved in 100ml of Dioxane, and 15mmol of potassium phosphate and 0.25mmol of Pd (PPh) were added3)4Heating the reaction mixture to 105 ℃, refluxing for 72 hours, taking a sample, indicating that no raw material A3 remains, completely reacting, and naturally cooling the reactant; adding 200mL of dichloromethane, washing the organic phase with 100mL of multiplied by 5 water for five times, and purifying the obtained substance through a silica gel column to obtain a target product intermediate M1, wherein the HPLC purity is 98.86% and the yield is 67.21%;
under nitrogen atmosphere, 1.5mmol of intermediate M1, 5mmol of raw material B2 dissolved in 100ml of DMF was added to a three-necked flask, and 15mmol of potassium carbonate and 0.25mmol of Pd (PPh) were added3)4Heating the reaction mixture to 90 ℃, refluxing for 24 hours, taking a sample, indicating no intermediate M1 remains, completely reacting, and naturally cooling to room temperature; then washing with dichloromethane, and purifying the obtained substance by a silica gel column to obtain a target product intermediate C3, wherein the HPLC purity is 99.08%, and the yield is 58.62%;
adding 0.01mol of intermediate C3, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a three-neck flask under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 11, wherein the HPLC purity is 98.79 percent, and the yield is 35.13 percent;
the preparation of the compounds of the present invention was similar to that of the compounds of preparation example 1 or 3, except that the starting materials used were different, and the specific starting materials and the corresponding compounds are shown in table 1.
TABLE 1
Figure BDA0002559368090000142
Figure BDA0002559368090000151
Figure BDA0002559368090000161
Figure BDA0002559368090000171
For structural analysis of the compounds prepared in examples, the molecular weight was measured using LC-MS, and the molecular weight was measured by dissolving the prepared compound in deuterated chloroform solvent and measuring using NMR apparatus of 500MHz1The results of H-NMR are shown in Table 2.
TABLE 2
Figure BDA0002559368090000172
Figure BDA0002559368090000181
Figure BDA0002559368090000191
The compound of the invention is used in a light-emitting device and can be used as a doping material of a light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were measured, and the results are shown in Table 3.
TABLE 3
Figure BDA0002559368090000201
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in a nitrogen environment; eg was measured by a two-beam uv-vis spectrophotometer (model: TU-1901), LUMO being HOMO + Eg; PLQY and FWHM were tested in the thin film state by the Fluorolog-3 series fluorescence spectrometer from Horiba.
The data in the table show that the compound has a shallow HOMO energy level, and is used as a doping material of a light emitting layer, so that the generation of carrier traps is inhibited, the energy transfer efficiency of a host and an object is improved, and the light emitting efficiency of a device is improved. Compared with the conventional green light doped ref-1, the compound has higher glass transition temperature and decomposition temperature. As a doping material is doped in the host material, the crystallization of the material and the film phase separation can be inhibited; meanwhile, the decomposition of the material under high brightness can be inhibited, and the service life of the device is prolonged.
The compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, and effectively prolongs the service life of devices; the compound has high fluorescence quantum efficiency as a doping material, the fluorescence quantum efficiency of the material is close to 100%, the spectrum FWHM of the material is narrow, and when the compound is used as a luminescent layer doping material of an organic electroluminescent device, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved.
The effect of the compound synthesized by the present invention as a doping material for a light emitting layer in a device will be described in detail below by device examples 1 to 44 and device comparative examples 1 and 2. Compared with the device example 1, the device examples 2 to 44 and the device comparative examples 1 and 2 of the present invention have the same manufacturing process, and the same substrate material and electrode material are adopted, and the film thickness of the electrode material is also kept consistent, except that the material of the light emitting layer in the device is changed, the composition of each layer of each device is shown in table 4, and the performance test result of each device is shown in table 5.
Device example 1
As shown in FIG. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (having a film thickness of 150nm) is washed, i.e., washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO layer. On the ITO anode layer 2 after the above washing, HT-1 and P-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. Then, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, CBP is used as a main material, a compound 1 is used as a doping material, the mass ratio of the CBP to the compound 1 is 97:3, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9.
The compound synthesized by the invention can be used as a doping material in a double-main-body light-emitting layer in a device, the manufacturing process of the device is completely the same as that of the device in embodiment 1, the same substrate material and electrode material are adopted, the film thickness of the electrode material is kept consistent, the difference is that the light-emitting layer in the device is CBP and DMAC-BP which are used as double-main-body materials, the compound synthesized by the invention is used as the doping material, the mass ratio of the CBP to the DMAC-BP to the compound synthesized by the invention is 67:30:3, and the film thickness of the light-emitting layer is 30 nm.
The molecular structural formula of the related material is shown as follows:
Figure BDA0002559368090000211
Figure BDA0002559368090000221
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 4; the results of the current efficiency, external quantum efficiency and lifetime tests of the resulting devices are shown in table 5.
TABLE 4
Figure BDA0002559368090000222
Figure BDA0002559368090000231
Figure BDA0002559368090000241
Figure BDA0002559368090000251
TABLE 5
Figure BDA0002559368090000261
Note: voltage, current efficiency and luminescence peak using IVL (current-voltage-brightness) test system (frastd scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device brightness to decay to 95%; all data were at 10mA/cm2And (4) testing.
From the results in table 5, it can be seen that compared with comparative device examples 1 and 2, the current efficiency and the device lifetime of the organic light emitting device of the present invention are greatly improved compared with the OLED device of the known material in both single-host system and dual-host system. When the TADF material is used as the second body, the efficiency of the device is obviously improved compared with that of a single body.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (11)

1. A boron-containing compound as a doping material for OLEDs, wherein the structure of the boron-containing compound is represented by the general formula (1):
Figure FDA0002559368080000011
in the general formula (1), X is1-X4Represented by-O-, -S-, -C (R)1)(R2) -or-N (R)3) -, and X1-X4At least one of which is represented by-N (R)3)-，R1-R3Each independently represents a hydrogen atom, a substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
z is nitrogen atom or C-R4Each occurrence of Z is the same or different;
i represents 0, 1;
the R is4Represented by a hydrogen atom, a deuterium atom, a tritium atom, a cyano group, a halogen group, a substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
and R is3And R4May be bonded to each other to form a ring;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium atom, tritium atom, cyano group, halogen atom, C1-C10Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The organic compound of claim 1, wherein R is3And R4May be bonded to each other to form a five-membered ring or a six-membered ring.
3. The organic compound according to claim 2, wherein the structure of the boron-containing compound is represented by general formula (1-1) or general formula (1-2):
Figure FDA0002559368080000012
wherein the symbols have the meanings defined in claim 1.
4. The organic compound according to claim 1, wherein the structure of the boron-containing compound is represented by general formula (1-3) or general formula (1-4):
Figure FDA0002559368080000021
wherein the symbols have the meanings defined in claim 1.
5. The organic compound of claim 1, wherein X is1-X4At least two of which are represented by-N (R)3)-。
6. An organic compound according to claim 1, characterized in that: the R is1-R4Each independently represents methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, phenyl, deuterated phenyl, tritiated phenyl, di-tritiated phenylBiphenyl, deuterated biphenylyl, tritiated biphenylyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenylyl, deuterated ethyl-substituted biphenylyl, deuterated biphenyl, naphthyl-substituted biphenylyl, anthracenyl, phenanthrenyl-substituted phenyl, phenanthrenyl, substituted biphenyl, and phenanthrenyl, One of a deuterated isopropyl-substituted biphenylyl, a deuterated tert-butyl-substituted biphenylyl, a tritiomethyl-substituted phenyl, a tritioethyl-substituted phenyl, a tritiomethyl-substituted biphenylyl, a tritioethyl-substituted biphenylyl, a tritiomethyl-substituted biphenylyl, or a tritiomethyl-substituted biphenylyl.
7. The organic compound according to claim 1, wherein C is6-C30The aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
said C is2-30Heteroaryl represents one of pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, dibenzofuryl, 9-dimethylfluorenyl, N-phenylcarbazolyl, quinolyl, isoquinolyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl and benzimidazolyl;
the substituent is one or more of protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, quinoxalyl group, quinazolinyl group, cinnolinyl group, naphthyridinyl group, fluorenyl group, dibenzofuranyl group, N-phenylcarbazolyl group or dibenzothiophenyl group.
8. The organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
Figure FDA0002559368080000031
Figure FDA0002559368080000041
Figure FDA0002559368080000051
Figure FDA0002559368080000061
Figure FDA0002559368080000071
Figure FDA0002559368080000081
Figure FDA0002559368080000091
Figure FDA0002559368080000101
Figure FDA0002559368080000111
Figure FDA0002559368080000121
9. an organic electroluminescent device comprising a cathode, an anode and an organic functional layer disposed between the cathode and the anode, characterized in that the functional layer of the organic electroluminescent device comprises a boron-containing compound according to any one of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, wherein the organic functional layer comprises a light-emitting layer, and the dopant material of the light-emitting layer is the boron-containing compound according to any one of claims 1 to 8.
11. The organic light-emitting device according to claim 10, the light-emitting layer comprising a first host material, a second host material, and a dopant material, wherein: at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing compound according to any one of claims 1 to 8.
CN202010602196.7A 2020-06-29 2020-06-29 Boron-containing compound and application thereof in organic electroluminescent device Pending CN113929708A (en)

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CN115197254A (en) * 2022-07-25 2022-10-18 上海交通大学 Nitrogen boron nitrogen hetero-bispiro alkene containing (HN) -B- (NH) structure, eutectic assembly and preparation method thereof
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