CN113527112A - Pyrene derivative modified by deuterated group and application thereof - Google Patents

Pyrene derivative modified by deuterated group and application thereof Download PDF

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CN113527112A
CN113527112A CN202010315228.5A CN202010315228A CN113527112A CN 113527112 A CN113527112 A CN 113527112A CN 202010315228 A CN202010315228 A CN 202010315228A CN 113527112 A CN113527112 A CN 113527112A
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CN113527112B (en
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曹旭东
张兆超
李崇
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention relates to a pyrene derivative modified by a deuterated group and application thereof, belonging to the technical field of semiconductors, and the invention provides a pyrene derivative with a structure shown in a general formula (1):
Figure DDA0002459313270000011
the invention also discloses application of the pyrene derivative. The pyrene derivative provided by the invention has narrow half-peak width and high fluorescence quantum yield, when the pyrene derivative is used as a doping material in a luminescent layer material of an OLED luminescent device, the current efficiency and the external quantum efficiency of the device are obviously improved, and meanwhile, the service life of the device is greatly improved.

Description

Pyrene derivative modified by deuterated group and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to a pyrene derivative modified by a deuterated group and application thereof.
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.
Fluorescent doped materials are limited by early technologies, only 25% singlet excitons formed by electrical excitation can emit light, the internal quantum efficiency of the device is low (up to 25%), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is far from that of a phosphorescent 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.
The Thermally Activated Delayed Fluorescence (TADF) material has a controllable structure, stable properties, low price and no need of noble metals, and has a small singlet-triplet energy level difference (delta EST), triplet excitons can be converted into singlet excitons through intersystem crossing to emit light, and the internal quantum efficiency of the final device can also reach 100%. However, most TADF materials are difficult to achieve both high exciton utilization and high fluorescence radiation efficiency, and also suffer from problems of poor color purity, severe roll-off of device efficiency, 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.
The arylamine modified pyrene compounds are often used as luminescent layer materials in the field of organic electroluminescent materials, for example, CN1487778A, CN103165818B, CN105037173A, JP2004083507A and JP2013063929A all disclose the application of the arylamine modified pyrene compounds in the aspect of organic electroluminescent materials, but the existing arylamine modified pyrene compounds have low fluorescence quantum efficiency and poor color purity, and are not suitable for mass production.
Disclosure of Invention
Aiming at the problems in the prior art, the applicant of the invention provides a pyrene derivative modified by a deuterated group and application thereof, the pyrene derivative can effectively improve the molecular stability by limiting the self-vibration of molecules through deuteration under the condition of not changing the molecular space structure, and meanwhile, the pyrene derivative has narrow half-peak width and high fluorescence quantum yield, can be used as a luminescent layer doping material of an organic electroluminescent device, and further improves the luminescent color purity and the service life of the device.
The invention provides a specific technical scheme as follows: a pyrene derivative modified by a deuterated group, wherein the structure of the pyrene derivative is shown as a general formula (1):
Figure BDA0002459313250000011
in the general formula (1), Ar1-Ar8Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30A heteroarylene group;
R1-R8each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30Heteroaryl or a structure of formula (2);
Ra-Rf are each independently represented by a hydrogen atom, protium, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
in the general formula (2), R9、R10Is represented by substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
r of the general formula (1)1-R 10In which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Further, the structure of the pyrene derivative is represented by the general formula (1-1):
Figure BDA0002459313250000021
in the general formula (1-1), R1-R8Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
R1-R 8in which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Further, R1-R 8In which at least two are represented by deuterium atom-substituted C6-30Aryl or C2-30A heteroaryl group.
Further, R1-R 8Wherein two bonded to different nitrogen atoms are represented by deuterium atom-substituted C6-30Aryl or deuterium atom substituted C2-30Heteroaryl, the remainder being represented by C6-30Aryl or C2-30A heteroaryl group.
Further, the compound represented by the general formula (1) has a symmetrical structure.
Further, the compound represented by the general formula (1-1) has a symmetrical structure.
Further, the structure of the pyrene derivative is shown as a general formula (1-2) -a general formula (1-5):
Figure BDA0002459313250000022
general formula (1-2) -general formula (1-5) wherein A, B, C each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
A. b, C at least one of which is C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Further, the structure of the pyrene derivative is represented by general formula (1-6):
Figure BDA0002459313250000031
in the general formula (1-6), Ar1And Ar6Each independently represents substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30A heteroarylene group;
R2、R3、R4、R5、R7、R8、R9、R10each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
R2、R3、R4、R5、R7、R8、R9、R10in which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Further, R9、R10In which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group.
Further, R3R7 represents C substituted by deuterium atom6-30Aryl or deuterium atom substituted C2-30A heteroaryl group.
Further, said C1-10The alkyl is one of methyl, ethyl, isopropyl and tert-butyl;
said C is6-30The aryl group is one of phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl and fluorenyl;
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.
Further, R is1-R8Each independently represents a substituted or unsubstituted group: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl.
Further, the specific structural formula of the pyrene derivative is any one of the following structures:
Figure BDA0002459313250000032
Figure BDA0002459313250000041
Figure BDA0002459313250000051
Figure BDA0002459313250000061
Figure BDA0002459313250000071
Figure BDA0002459313250000081
Figure BDA0002459313250000091
Figure BDA0002459313250000101
Figure BDA0002459313250000111
Figure BDA0002459313250000121
Figure BDA0002459313250000131
Figure BDA0002459313250000141
an organic light-emitting device comprising a cathode, an anode and an organic functional layer comprising the pyrene derivative.
Further, the organic functional layer comprises a light emitting layer, characterized in that: the doped material of the luminescent layer is the pyrene derivative.
Further, the light emitting layer includes a first host material, a second host material, and a dopant material, and is characterized in that: at least one of the first host material and the second host material is a TADF material, and the doping material is the pyrene derivative.
Further, the light-emitting layer comprises a first host material, a second host material and a doping material, wherein the first host material and the second host material are selected from structures shown in a general formula (2) or a general formula (3), and the doping material is the organic electroluminescent material containing the double boron;
Figure BDA0002459313250000151
in the general formula (2), R is6-R9Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms; r6And R7Can be bonded to form a ring between R8And R9Can be bound into a ring;
in the general formula (3), L is1-L2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted 5 to 30 membered heteroarylene containing one or more heteroatoms;
the R ism-RnEach independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms.
Further, the light emitting layer includes a first host material, a second host material, and a dopant material, and is characterized in that: the first main body material and the second main body material are respectively CBP and DMAC-BP, and the doped material is the pyrene derivative;
Figure BDA0002459313250000152
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 doping material of a luminescent layer 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 compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(3) the compound is used as a doping material, and a TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved;
(4) the compound has a narrow spectrum FWHM, and can effectively improve the color gamut of a device and improve the luminous efficiency of the device;
(5) the compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, and effectively prolongs the service life of devices.
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 substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting 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 raw materials involved in the synthesis examples of the present invention were purchased from Zhongjieyanwang Limited.
Preparation of intermediate B-1
Figure BDA0002459313250000153
Adding 0.01mol of raw material M-1, 0.012mol of raw material N-1 and 90ml of toluene into a three-mouth bottle under the protection of nitrogen, stirring and mixing, and then adding 3 multiplied by 10-5mol Pd2(dba)3，3×10-5mol P(t-Bu)3Heating 0.038mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 12 hours, sampling a sample point plate, and completely reacting; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate K-1.
Adding 0.012mol of intermediate K-1, 0.01mol of raw material S-1 and 100ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 3 multiplied by 10-5mol Pd2(dba)3，3×10-5mol P(t-Bu)3Heating 0.021mol of sodium tert-butoxide to 110 ℃, carrying out reflux reaction for 16 hours, sampling a sample, and completely reacting; naturally cooling to room temperature, filtering, carrying out rotary evaporation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate B-1, LC-MS: 339.16.
preparation of intermediate B-5
Figure BDA0002459313250000161
The preparation method of the intermediate B-5 is the same as that of the intermediate K-1 except that the raw material M-1 is replaced by the raw material M-2, the raw material N-1 is replaced by the raw material N-2, and LC-MS: 266.19.
preparation of intermediate B-23
Figure BDA0002459313250000162
The preparation method of the intermediate B-23 is the same as that of the intermediate K-1 except that the raw material M-1 is replaced by the raw material M-3, the raw material N-1 is replaced by the raw material N-2, and LC-MS: 341.25.
preparation example 1:
Figure BDA0002459313250000163
adding 0.01mol of raw material A-1, 0.022mol of intermediate B-1 and 90ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.057mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 12 hours, sampling a sample point plate, and completely reacting; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate C-1.
Adding 0.01mol of intermediate C-1, 0.024mol of raw material D-1 and 100ml of toluene in a three-neck bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.058mol of sodium tert-butoxide to 110 ℃, carrying out reflux reaction for 16 hours, sampling a sample point plate, and completely reacting; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the compound 101.
Preparation example 2:
Figure BDA0002459313250000171
compound 78 was prepared as in preparation example 1, except that intermediate B-1 was replaced with intermediate B-2 and starting material D-1 was replaced with starting material D-2.
Preparation example 3:
Figure BDA0002459313250000172
compound 77 is prepared by the same method as in preparation example 1, except that starting material A-1 is replaced with starting material A-2, intermediate B-1 is replaced with intermediate B-3, and starting material D-1 is replaced with starting material D-3.
Preparation example 4:
Figure BDA0002459313250000173
compound 6 was prepared in the same manner as in preparation example 1 except that intermediate B-4 was used in place of intermediate B-1 and starting material D-4 was used in place of starting material D-1.
Preparation example 5:
Figure BDA0002459313250000174
Figure BDA0002459313250000181
compound 4 was prepared as in preparation example 1, except that intermediate B-1 was replaced with intermediate B-5 and starting material D-1 was replaced with starting material D-5.
Preparation example 6:
Figure BDA0002459313250000182
compound 141 is prepared by the same method as in preparation example 1, except that intermediate B-1 is replaced with intermediate B-6 and starting material D-1 is replaced with starting material D-6.
Preparation example 7:
Figure BDA0002459313250000183
compound 16 was prepared as in preparation example 1, except that intermediate B-7 was used in place of intermediate B-1 and starting material D-7 was used in place of starting material D-1.
Preparation example 8:
Figure BDA0002459313250000184
compound 17 was prepared as in preparation example 1, except that intermediate B-7 was used in place of intermediate B-1 and starting material D-8 was used in place of starting material D-1.
Preparation example 9:
Figure BDA0002459313250000185
Figure BDA0002459313250000191
compound 3 was prepared in the same manner as in preparation example 1 except that intermediate B-1 was replaced with intermediate B-9 and starting material D-1 was replaced with starting material D-9.
Preparation example 10:
Figure BDA0002459313250000192
adding 0.01mol of raw material A-3, 0.047mol of intermediate B-1 and 200ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 9 multiplied by 10-5mol Pd2(dba)3，9×10-5mol P(t-Bu)3Heating 0.12mol of sodium tert-butoxide to 110 ℃, carrying out reflux reaction for 18 hours, sampling a sample, and carrying out complete reaction; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the compound 13.
Preparation example 11:
Figure BDA0002459313250000193
compound 73 was prepared as in preparation example 1, except that intermediate B-7 was used in place of intermediate B-1 and starting material D-9 was used in place of starting material D-1.
Preparation example 12:
Figure BDA0002459313250000194
compound 81 is prepared by the same method as in preparation example 1, except that intermediate B-1 is replaced with intermediate B-12 and starting material D-1 is replaced with starting material D-12.
Preparation example 13:
Figure BDA0002459313250000195
compound 248 was prepared as in preparative example 10 except intermediate B-10 was replaced with intermediate B-7.
Preparation example 14:
Figure BDA0002459313250000201
compound 87 was prepared as in preparation example 1, except that intermediate B-7 was used in place of intermediate B-1 and starting material D-14 was used in place of starting material D-1.
Preparation example 15:
Figure BDA0002459313250000202
compound 91 was prepared as in preparation example 1, except that intermediate B-1 was replaced with intermediate B-10 and starting material D-1 was replaced with starting material D-15.
Preparation example 16:
Figure BDA0002459313250000203
compound 93 was prepared as in preparation example 1, except that intermediate B-1 was replaced with intermediate B-10 and starting material D-1 was replaced with starting material D-2.
Preparation example 17:
Figure BDA0002459313250000204
compound 96 is prepared by the same method as in preparation example 1, except that intermediate B-1 is replaced with intermediate B-17 and starting material D-1 is replaced with starting material D-17.
Preparation example 18:
Figure BDA0002459313250000211
compound 242 is prepared as in preparative example 10 except that intermediate B-23 is substituted for intermediate B-10.
Preparation example 19:
Figure BDA0002459313250000212
compound 227 was prepared as in preparation example 1, except that intermediate B-1 was replaced with intermediate B-9 and starting material D-1 was replaced with starting material D-19.
Preparation example 20:
Figure BDA0002459313250000213
compound 206 was prepared as in preparation example 1, except that intermediate B-7 was used instead of intermediate B-1 and starting material D-8 was used instead of starting material D-1.
Preparation example 21:
Figure BDA0002459313250000221
compound 207 is prepared by the same method as in preparation example 1, except that intermediate B-1 is replaced with intermediate B-21 and starting material D-1 is replaced with starting material D-6.
Preparation example 22:
Figure BDA0002459313250000222
compound 241 was prepared as in preparative example 1, except that intermediate B-10 was replaced with intermediate B-2.
Preparation example 23:
Figure BDA0002459313250000223
compound 266 was prepared as in preparative example 1 except intermediate B-10 was replaced with intermediate B-22.
TABLE 1
Figure BDA0002459313250000224
Figure BDA0002459313250000231
Figure BDA0002459313250000241
The pyrene derivative provided by 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 2:
TABLE 2
Figure BDA0002459313250000242
Figure BDA0002459313250000251
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 is tested by an ionization energy testing system (IPS-3), and the test is 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 by Horiba's Fluorolog-3 series fluorescence spectrometer.
As can be seen from the data in the above table, the compound of the present invention has a higher decomposition temperature than the conventional green-doped GD-19 and the conventional material ref-3. The material is used as a doping material of a light emitting layer, so that the decomposition of the material under high brightness can be inhibited, and the service life of a device is prolonged. In addition, the compound has a shallow HOMO energy level, is doped in a host material as a doping material, is favorable for inhibiting generation of carrier traps, and improves the energy transfer efficiency of a host and an object, so that the luminous efficiency of a device is improved.
The compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; meanwhile, the spectrum FWHM of the material is narrow, so that the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; and finally, the evaporation decomposition temperature of the material is higher, so that the evaporation decomposition of the material can be inhibited, and the service life of the device is effectively prolonged.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-23 and device comparative examples 1-4. Compared with the device example 1, the device examples 2 to 23 and the device comparative examples 1 to 4 of the invention have the same manufacturing process, adopt the same substrate material and electrode material, keep the film thickness of the electrode material consistent, and the difference is that the luminescent layer material in the device is replaced. The layer structures and test results of the device examples are shown in tables 3 and 5, respectively
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 40nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light-emitting layer 6 of the OLED light-emitting device is manufactured, and the structure of the light-emitting layer 6 comprises CBP used as a main material of the OLED light-emitting layer 6, a compound 101 used as a doping material, the mass ratio of the CBP to the compound 101 is 97:3, and the thickness of the light-emitting layer is 40 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 light-emitting layer 6, 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 35nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a Yb layer having a film thickness of 1nm was formed by a vacuum deposition 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 molecular structural formula of the related material is shown as follows:
Figure BDA0002459313250000261
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. The structures of device examples and comparative examples prepared in the same manner are shown in table 3; the results of the current efficiency, external quantum efficiency and lifetime tests of the resulting devices are shown in table 5.
TABLE 3
Figure BDA0002459313250000262
Figure BDA0002459313250000271
The effect of the synthesized OLED material of the present invention in the application of the device is detailed below by device examples 24-29 and device comparative examples 5 and 6. Compared with device example 24, the device examples 25 to 29 and the device comparative examples 5 and 6 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, the film thickness of the electrode material is also kept consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device examples are shown in tables 4 and 5, respectively
Device example 24
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (with a film thickness of 150nm) is washed, namely washed by a cleaning agent (Semiclean M-L20), washed by pure water, dried, and then washed by ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. 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 40nm 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, the structure of the OLED light emitting device comprises CBP and DMAC-BP used by the OLED light emitting layer 6 as double main body materials, a compound 3 as a doping material, the mass ratio of the CBP to the DMAC-BP to the compound 3 is 67:30:3, and the thickness of the light emitting layer is 40 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 light-emitting 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 35nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a Yb layer having a film thickness of 1nm was formed by a vacuum deposition 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.
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 of the device and the lifetime of the device were measured. The structures of device examples and comparative examples prepared in the same manner are shown in table 4; the current efficiency and lifetime test results of the resulting devices are shown in table 5.
TABLE 4
Figure BDA0002459313250000281
TABLE 5
Figure BDA0002459313250000282
Figure BDA0002459313250000291
Note: voltage, current efficiency, 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%.
As can be seen from the device data results in table 5, compared with comparative device examples 1 to 6, 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 the single-host system device and the dual-host system device; 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.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A pyrene derivative modified with a deuterated group, comprising: the structure of the pyrene derivative is shown as a general formula (1):
Figure FDA0002459313240000011
in the general formula (1), Ar1-Ar8Are each independently represented asSingle bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30A heteroarylene group;
R1-R8each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30Heteroaryl or a structure of formula (2);
Ra-Rf are each independently represented by a hydrogen atom, protium, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-20Cycloalkyl, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
in the general formula (2), R9、R10Is represented by substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
r of the general formula (1)1-R10In which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
2. The pyrene derivative according to claim 1, wherein: the structure of the pyrene derivative is shown as a general formula (1-1):
Figure FDA0002459313240000012
in the general formula (1-1), R1-R8Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
R1-R8in which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
3. The pyrene derivative according to claim 2, wherein:
R1-R8in which at least two are represented by deuterium atom-substituted C6-30Aryl or C2-30A heteroaryl group.
4. The pyrene derivative according to claim 1, wherein: the structure of the pyrene derivative is shown as a general formula (1-2) -a general formula (1-5):
Figure FDA0002459313240000021
general formula (1-2) -general formula (1-5) wherein A, B, C each independently represents a substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
A. b, C at least one of which is C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
5. The pyrene derivative according to claim 1, wherein: the structure of the pyrene derivative is shown as a general formula (1-6):
Figure FDA0002459313240000022
in the general formula (1-6), Ar1And Ar6Each independently represents substituted or unsubstituted C6-30Arylene, substituted or unsubstituted C2-30A heteroarylene group;
R2、R3、R4、R5、R7、R8、R9、R10each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C2-30A heteroaryl group;
the substituent for substituting the above-mentioned substitutable group is optionally selected from deuterium, tritium, C1～C10Any one of an alkyl group, an aryl group having 6 to 30 ring atoms, and a heteroaryl group having 5 to 30 ring atoms;
R2、R3、R4、R5、R7、R8、R9、R10in which at least one is represented by C substituted by deuterium atoms6-30Aryl or deuterium atom substituted C2-30A heteroaryl group;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
6. The pyrene derivative according to claim 1, wherein: said C is1-10The alkyl is one of methyl, ethyl, isopropyl and tert-butyl;
said C is6-30The aryl group is one of phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl and fluorenyl;
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.
7. The pyrene derivative according to claim 1, wherein: the specific structural formula of the pyrene derivative is any one of the following structures:
Figure FDA0002459313240000031
Figure FDA0002459313240000041
Figure FDA0002459313240000051
Figure FDA0002459313240000061
Figure FDA0002459313240000071
Figure FDA0002459313240000081
Figure FDA0002459313240000091
Figure FDA0002459313240000101
Figure FDA0002459313240000111
Figure FDA0002459313240000121
Figure FDA0002459313240000131
Figure FDA0002459313240000141
Figure FDA0002459313240000151
Figure FDA0002459313240000161
8. an organic light-emitting device comprising a cathode, an anode and an organic functional layer, characterized in that: the pyrene derivative according to any one of claims 1 to 7 is contained in the organic functional layer.
9. The organic light-emitting device according to claim 8, 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 pyrene derivative according to any one of claims 1 to 7.
10. The organic light-emitting device according to claim 9, the light-emitting layer comprising a first host material, a second host material, and a dopant material, wherein: the first host material and the second host material are selected from structures shown in a general formula (2) or a general formula (3), and the doping material is the organic electroluminescent material containing the diboron according to any one of claims 1 to 7;
Figure FDA0002459313240000162
in the general formula (2), R is6-R9Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms; r6And R7Can be bonded to form a ring between R8And R9Can be bound into a ring;
in the general formula (3), L is1-L2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, substituted or unsubstituted 5 to 30 membered heteroarylene containing one or more heteroatoms;
the R ism-RnEach independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 5 to 30 membered heteroaryl containing one or more heteroatoms.
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CN113921740A (en) * 2021-11-18 2022-01-11 昆山国显光电有限公司 Organic electroluminescent device and display device
WO2024104472A1 (en) * 2022-11-17 2024-05-23 浙江光昊光电科技有限公司 Composition and use thereof in photoelectric field

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KR20110002155A (en) * 2009-07-01 2011-01-07 주식회사 엘지화학 New compounds and organic electronic device using the same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113921740A (en) * 2021-11-18 2022-01-11 昆山国显光电有限公司 Organic electroluminescent device and display device
CN113921740B (en) * 2021-11-18 2023-09-01 昆山国显光电有限公司 Organic electroluminescent device and display device
WO2024104472A1 (en) * 2022-11-17 2024-05-23 浙江光昊光电科技有限公司 Composition and use thereof in photoelectric field

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