CN108346756B - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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CN108346756B
CN108346756B CN201710062699.8A CN201710062699A CN108346756B CN 108346756 B CN108346756 B CN 108346756B CN 201710062699 A CN201710062699 A CN 201710062699A CN 108346756 B CN108346756 B CN 108346756B
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electroluminescent device
organic electroluminescent
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CN108346756A (en
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缪康健
徐凯
张兆超
李崇
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention relates to an organic electroluminescent device, belonging to the field of photoelectric materials. The structure of the organic light-emitting device prepared by the invention comprises: a hole transport region, an electron transport region, and a light-emitting layer containing a host material represented by general formula (1), the organic light-emitting device having characteristics of high efficiency, long lifetime, and low efficiency roll-off:
Figure DDA0001218737900000011

Description

Organic electroluminescent device
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic electroluminescent device.
Background
The use of Organic Light Emitting Diodes (OLEDs) for large area flat panel displays and lighting has attracted considerable attention in the industry and academia. However, the conventional organic fluorescent material can emit light only by using 25% singlet excitons formed by electric excitation, and the internal quantum efficiency of the device is low (up to 25%). External quantum efficiencies are generally below 5%, and are far from the efficiencies of phosphorescent devices. Although the phosphorescent material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom centers, singlet excitons and triplet excitons formed by electric excitation can be effectively used for emitting light, so that the internal quantum efficiency of the device reaches 100%. However, the application of phosphorescent materials in OLEDs is limited by the problems of high price, poor material stability, serious device efficiency roll-off and the like. A Thermally Activated Delayed Fluorescence (TADF) material is a third generation organic light emitting material that has been developed following organic fluorescent materials and organic phosphorescent materials. Such materials typically have a small singlet-triplet energy level difference (Δ E)ST) The triplet excitons may be converted to singlet excitons by intersystem crossing to emit light. This can make full use of singlet excitons and triplet excitons formed under electrical excitation, and the internal quantum efficiency of the device can reach 100%. Meanwhile, the material has controllable structure, stable property, low price and no need of precious metal, and has wide application prospect in the field of OLEDs.
Although TADF materials can theoretically achieve 100% exciton utilization, there are actually the following problems: (1) the T1 and S1 states of the designed molecule have strong CT characteristics, a very small energy gap of S1-T1 states, although high T can be achieved by the TADF process1→S1State exciton conversion but at the same time results in a low S1 state radiative transition rate, and therefore it is difficult to achieve both (or both) high exciton utilization and high fluorescence radiation efficiency; (2) even though doped devices have been employed to mitigate the T exciton concentration quenching effect, most devices of TADF materials suffer from severe roll-off in efficiency at high current densities.
In terms of the actual demand of the current OLED display illumination industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and the development of organic functional materials with higher performance is very important as a material enterprise.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an organic light-emitting device, which can effectively improve the efficiency and the service life of the organic light-emitting device and reduce the efficiency roll-off.
The technical scheme of the invention is as follows: an organic electroluminescent device comprising a hole transporting region, an electron transporting region and a light-emitting layer comprising a host material represented by the general formula (1):
Figure BDA0001218737880000021
in the general formula (1), n is 1 or 2;
Ar1represents one of C1-C10 alkyl substituted or unsubstituted phenyl, C1-C10 alkyl substituted or unsubstituted biphenyl, C1-C10 alkyl substituted or unsubstituted terphenyl, C1-C10 alkyl substituted or unsubstituted naphthyl and C1-C10 alkyl substituted or unsubstituted anthryl;
Figure BDA0001218737880000022
in the general formulae (2) and (3), X1And X2Each independently represents an oxygen atom, a sulfur atom, C (R)2)(R3)、Si(R2)(R3)、P(R2)、B(R2)、P(＝O)(R2) Or N (R)2)；
R2And R3Each independently represents one of substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, substituted or unsubstituted C3-C60 cycloalkenyl, substituted or unsubstituted C1-C60 heterocycloalkenyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C1-C60 heteroaryl.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, R in the general formula (1)1Expressed as:
Figure BDA0001218737880000023
Figure BDA0001218737880000031
Figure BDA0001218737880000041
Figure BDA0001218737880000042
any one of them.
Further, the light emitting layer further includes a guest dopant, wherein the guest dopant is represented by general formula (4):
Figure BDA0001218737880000043
wherein M is metal platinum (Pt), iridium (Ir), osmium (Os) orOne of copper (Cu); x2、X3、X4And X5Each independently represents one of oxygen, carbon or nitrogen atoms; a. the5、A6Is an aromatic radical, A7Is an organic ligand; n is10, 1,2 or 3; n is21,2 or 3.
Further, the specific structural formula of the compound represented by the general formula (4) is:
Figure BDA0001218737880000051
Figure BDA0001218737880000061
Figure BDA0001218737880000071
Figure BDA0001218737880000072
any one of them.
Further, the hole transport region comprises one or more of a hole injection layer, a hole transport layer, a buffer layer and an electron blocking layer, wherein the hole injection layer is made of one of the following structural general formulas (5), (6) or (7):
Figure BDA0001218737880000081
wherein, in the general formula (5), Er1-Er3Each independently represents one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl; er1-Er3May be the same or different;
wherein in the general formula (6) and the general formula (7), Fr1-Fr6Independently represent hydrogen atom, nitrile group, halogen, amide group, alkoxy group, ester group, nitro group, C1-C60 straight chain or branched chain alkyl substituted carbon atom, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroarylOne of the groups.
Further, specific structural formulae of the compounds represented by the general formulae (5), (6) and (7) are:
Figure BDA0001218737880000082
Figure BDA0001218737880000091
Figure BDA0001218737880000092
any one of them.
Further, the hole transport layer material is a triarylamine group compound, and the structural formula is shown as a general formula (8):
Figure BDA0001218737880000093
wherein, Ar in the general formula (8)3、Ar4And Ar5Independently represent any one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C1-C60 heteroaryl.
Further, the specific structural formula of the compound represented by the general formula (8) is:
Figure BDA0001218737880000101
Figure BDA0001218737880000111
Figure BDA0001218737880000121
Figure BDA0001218737880000122
any one of them.
Further, the electron transport region includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer.
Further, the material of the electron injection layer is one of lithium, lithium salt or cesium salt, wherein the lithium salt is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; the cesium salt is cesium fluoride, cesium carbonate, cesium chloride or cesium azide.
Further, the material of the electron transport layer is any one of compounds represented by the following general formula (9), (10), (11), (12) or (13):
Figure BDA0001218737880000123
Figure BDA0001218737880000131
wherein Dr in the general formulae (9), (10), (11), (12) and (13)1-Dr10Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group.
Further, the specific structural formulae of the compounds represented by the general formulae (9), (10), (11), (12) and (13) are:
Figure BDA0001218737880000132
Figure BDA0001218737880000141
Figure BDA0001218737880000142
any one of them.
Further, the organic light-emitting device sequentially comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer and an electron injection layer from bottom to top, wherein the light-emitting layer comprises a host material and a guest dopant.
The invention has the beneficial effects that:
the invention provides an organic electroluminescent device, wherein the main material of a luminescent layer of the organic electroluminescent device is a compound taking xanthone as a core, and the compound has small energy level difference between an S1 state and a T1 state, so that reverse intersystem crossing is realized under the condition of thermal stimulation, the effective utilization of energy is realized, and the luminescent efficiency of the device is improved. The organic electroluminescent device using the compound as a main material has the characteristics of high efficiency and long service life. The organic electroluminescent device has good application effect and good industrialization prospect.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device prepared according to an embodiment of the present invention. It should be noted that the structure of fig. 1 is only for convenience of understanding of the embodiment, and does not represent the entire structure of 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/electron transport layer, 8 is an electron injection layer, and 9 is a cathode reflection electrode layer.
Detailed Description
Referring to fig. 1, the transparent substrate layer 1 may be a glass substrate or a plastic substrate having good mechanical strength, thermal stability, transparency, surface flatness, handling convenience, and water resistance.
The anode layer 2 may be made of a conductor having a high work function (specifically, 4.0eV or more) to assist hole injection. The anode may be a metal, metal oxide and/or conductive polymer, such as: metallic nickel, platinum, vanadium, chromium, copper, zinc, gold or alloy, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene), polypyrrole, and polyaniline, but are not limited thereto.
The cathode reflective electrode layer 9 may be made of a conductor having a low work function (specifically, 3.8eV or less) to assist electron injection. The cathode can be metal, metal oxide andand/or conductive polymers, such as: magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, and the like; multilayer structures, such as: LiF/Al, LiF/Ca, LiO2/Al、BaF2But not limited thereto,/Ca.
The hole transport region may include one or more of a hole injection layer 3(HIL), a hole transport layer 4(HTL), a buffer layer (not shown in the drawings, but the organic light emitting device provided herein may include this layer), and an electron blocking layer 5 (EBL); the hole transport region may have a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure formed of a plurality of different materials. For example, the hole transport region may be a single layer structure formed of different materials, or may have a structure of a hole injection layer/a hole transport layer, a structure of a hole injection layer/a hole transport layer/a buffer layer, a structure of a hole injection layer/a buffer layer, a structure of a hole transport layer/a buffer layer, a structure of a hole injection layer/a hole transport layer/an electron blocking layer, or a structure of a hole transport layer/an electron blocking layer, but the hole transport region is not limited thereto.
The electron transport region may include one or more of a Hole Blocking Layer (HBL)/electron transport layer 7(ETL) and an electron injection layer 8 (EIL). For example, the electron transport region may have a structure of an electron transport layer/an electron injection layer, a structure of a hole blocking layer/an electron transport layer/an electron injection layer, but is not limited thereto.
As a method for forming each layer of the organic light-emitting device in this embodiment mode, a vacuum deposition method, spin coating, drop casting, ink jet printing, laser printing, or an LB film method can be used.
When the thin film is formed by vacuum evaporation, it may be deposited at a deposition temperature in the range of 100 ℃ to 500 ℃ to
Figure BDA0001218737880000162
To
Figure BDA0001218737880000163
Vacuum deposition is performed at a deposition rate within the range of (1). When the thin film is formed by spin coating, the spin may be performed at a speed in the range of 2000rpm to about 5000rpmThe spin coating is performed at a coating rate and at a temperature in the range of 20 ℃ to 200 ℃.
In the organic light emitting device of the present embodiment, the thickness of each thin film is not limited, but generally, when the thin film is too thin, defects such as pinholes tend to occur, whereas when the thin film is too thick, a high applied voltage is required to deteriorate the efficiency, and therefore, a range of 0.1nm to 1000nm is generally preferable.
The present invention will be described in further detail with reference to examples.
Synthesis of the Compounds:
example 1: synthesis of Compound 3:
the synthetic route is as follows:
Figure BDA0001218737880000161
under the protection of nitrogen, 0.3mol of acridine, 0.3mol of p-dibromobenzene, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, sampling a spot plate, showing that no acridine remains and completely reacting; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N1;
weighing 0.2mol of intermediate N1, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N1 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M1;
0.1mol of starting material A1 and 0.12mol of intermediate M1 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours under inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, passing the crude product through a silica gel column,the target product is obtained, the HPLC purity is 99.1 percent, and the yield is 75.7 percent;
elemental analysis Structure (molecular formula C)34H25NO2): theoretical value C, 85.15; h, 5.25; n, 2.92; test values are: c, 85.21; h, 5.24; and N, 2.92.
HPLC-MS: the molecular weight of the material is 479.57, and the measured molecular weight is 479.99.
Example 2: synthesis of Compound 4:
the synthetic route is as follows:
Figure BDA0001218737880000171
under the protection of nitrogen, 0.3mol of 5-phenyl-5, 10-dihydrophenazine, 0.3mol of p-dibromobenzene, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, and sampling a sample point plate to show that no raw material remains and the reaction is complete; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N2;
weighing 0.2mol of intermediate N2, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N2 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M2;
0.1mol of starting material A1 and 0.12mol of intermediate M2 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.5%, and the yield is 77.4%;
elemental analysis Structure (molecular formula C)37H24N2O2): theoretical value C, 84.07; h, 4.58; n, 5.30; test values are: c, 84.12; h, 4.55; n, 5.31.
HPLC-MS: the molecular weight of the material is 528.60, and the measured molecular weight is 528.66.
Example 3: synthesis of Compound 5:
the synthetic route is as follows:
Figure BDA0001218737880000181
Figure BDA0001218737880000191
under the protection of nitrogen, 0.3mol of 9, 9-diphenyl-5, 10-dihydrophenacridine, 0.3mol of p-dibromobenzene, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, and sampling a sample point plate to show that no raw material remains and the reaction is complete; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N3;
weighing 0.2mol of intermediate N3, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N3 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M3;
0.1mol of starting material A1 and 0.12mol of intermediate M3 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.4%, and the yield is 75.8%;
elemental analysisStructure (molecular formula C)44H29NO2): theoretical value C, 87.54; h, 4.84; n, 2.32; test values are: c, 87.58; h, 4.82; n, 2.33.
HPLC-MS: the molecular weight of the material is 603.71, and the measured molecular weight is 603.99.
Example 4: synthesis of compound 15:
the synthetic route is as follows:
Figure BDA0001218737880000201
0.1mol of starting material A2 and 0.12mol of intermediate M1 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.6%, and the yield is 79.3%;
elemental analysis Structure (molecular formula C)34H25NO2): theoretical value C, 85.15; h, 5.25; n, 2.92; test values are: c, 85.20; h, 5.25; and N, 2.91.
HPLC-MS: the molecular weight of the material is 479.57, and the measured molecular weight is 479.94.
Example 5: synthesis of compound 18:
the synthetic route is as follows:
Figure BDA0001218737880000202
Figure BDA0001218737880000211
under the protection of nitrogen, 0.3mol of raw material B1, 0.3mol of p-dibromobenzene, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, and sampling a sample point plate to show that no raw material remains and the reaction is complete; naturally cooling to room temperatureFiltering, carrying out reduced pressure rotary evaporation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N4;
weighing 0.2mol of intermediate N4, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N4 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M4;
0.1mol of starting material A1 and 0.12mol of intermediate M4 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.5%, and the yield is 70.4%;
elemental analysis Structure (molecular formula C)45H27NO3): theoretical value C, 85.83; h, 4.32; n, 2.22; test values are: c, 85.91; h, 4.33; and N, 2.20.
HPLC-MS: the molecular weight of the material is 629.70, and the measured molecular weight is 629.84.
Example 6: synthesis of compound 25:
the synthetic route is as follows:
Figure BDA0001218737880000221
under the protection of nitrogen, 0.3mol of acridine, 0.3mol of o-dibromobenzene, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, sampling a spot plate, showing that no acridine remains and completely reacting; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N5;
weighing 0.2mol of intermediate under the protection of nitrogenN5, 0.25mol pinacol diboron, 0.25mol potassium acetate, 0.01mol Pd (dppf) Cl2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N5 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M5;
0.1mol of starting material A1 and 0.12mol of intermediate M5 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.4%, and the yield is 75.9%;
elemental analysis Structure (molecular formula C)34H25NO2): theoretical value C, 85.15; h, 5.25; n, 2.92; test values are: c, 85.22; h, 5.24; and N, 2.91.
HPLC-MS: the molecular weight of the material is 479.57, and the measured molecular weight is 479.87.
Example 7: synthesis of Compound 30
The synthetic route is as follows:
Figure BDA0001218737880000231
under the protection of nitrogen, 0.3mol of acridine, 0.3mol of 4, 4' -dibromobiphenyl, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, sampling a spot plate, showing that no acridine remains and completely reacting; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N6;
weighing 0.2mol of intermediate N6, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours,a sample point panel indicated no intermediate N6 remained and the reaction was complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M6;
0.1mol of starting material A1 and 0.12mol of intermediate M6 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.5%, and the yield is 70.6%;
elemental analysis Structure (molecular formula C)40H29NO2): theoretical value C, 86.46; h, 5.26; n, 2.52; test values are: c, 86.52; h, 5.24; n, 2.51.
HPLC-MS: the molecular weight of the material is 555.66, and the measured molecular weight is 555.87.
Example 8: synthesis of compound 38:
Figure BDA0001218737880000241
under the protection of nitrogen, 0.3mol of acridine, 0.3mol of 3, 4' -dibromobiphenyl, 0.3mol of sodium tert-butoxide and 0.015mol of Pd are weighed in sequence2(dba)3And 0.3mol of tri-tert-butylphosphine, stirring and mixing with 500mL of toluene, heating to 110 ℃, refluxing and reacting for 24 hours, sampling a spot plate, showing that no acridine remains and completely reacting; naturally cooling to room temperature, filtering, carrying out reduced pressure rotary distillation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate N7;
weighing 0.2mol of intermediate N7, 0.25mol of pinacol diboron, 0.25mol of potassium acetate and 0.01mol of Pd (dppf) Cl under the protection of nitrogen2250mL of 1, 4-dioxane, mixing and stirring, heating to 100 ℃, reacting for 24 hours, and sampling a sample point plate to show that no intermediate N7 remains and the reaction is complete; naturally cooling to room temperature, adding water, precipitating solid, filtering, drying the filter cake in a vacuum drying oven, and passing through a neutral silica gel column to obtain an intermediate M7;
0.1mol of starting material A1 and 0.12mol of intermediate M7 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.5%, and the yield is 71.3%;
elemental analysis Structure (molecular formula C)40H29NO2): theoretical value C, 86.46; h, 5.26; n, 2.52; test values are: c, 86.52; h, 5.24; n, 2.51.
HPLC-MS: the molecular weight of the material is 555.66, and the measured molecular weight is 555.89.
Example 9: synthesis of compound 44:
the synthetic route is as follows:
Figure BDA0001218737880000251
0.1mol of raw material A2 and 0.12mol of intermediate M7 were dissolved in 150mL of anhydrous toluene, deoxygenated and 0.005mol of Pd was added2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.6 percent, and the yield is 74.2 percent;
elemental analysis Structure (molecular formula C)40H29NO2): theoretical value C, 86.46; h, 5.26; n, 2.52; test values are: c, 86.53; h, 5.24; and N, 2.52.
HPLC-MS: the molecular weight of the material is 555.66, and the measured molecular weight is 555.97.
Example 10: synthesis of compound 66:
Figure BDA0001218737880000252
0.1mol of starting material A3 and 0.12mol of intermediate M1 were dissolved in 150mL ofAdding 0.005mol of Pd into water toluene after deoxygenation2(dba)3Reacting with 0.15mol of tri-tert-butylphosphine at 110 ℃ for 24 hours in an inert atmosphere, continuously monitoring the reaction process by TLC in the reaction process, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a target product, wherein the HPLC purity is 99.2%, and the yield is 74.5%;
elemental analysis Structure (molecular formula C)55H42N2O2): theoretical value C, 86.59; h, 5.55; n, 3.67; test values are: c, 86.62; h, 5.54; and N, 3.66.
HPLC-MS: the molecular weight of the material is 762.93, and the measured molecular weight is 763.15.
Preparing a device:
the effect of the compound synthesized by the present invention as a host material for a light emitting layer in a device is described in detail by examples 11 to 20 and comparative examples 1 and 2. In examples 12 to 20 and comparative examples 1 and 2, compared with example 11, the manufacturing process of the device was completely the same, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept the same, except that the material of the light emitting layer in the device was changed.
Example 11
Examples ITO was used as anode, Al as cathode, compound DP-1 as guest material, compound HI-1 as hole injection layer material, compound HT-14 as hole transport layer and electron barrier layer material, compound ET-14 as electron transport layer material, LiF as electron injection layer material. The specific manufacturing steps are as follows:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating a hole injection layer material HI-1 on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HI-1 is 10nm, and the hole injection layer material HI-1 is used as a hole injection layer 3;
c) evaporating a hole transport material HT-14 on the hole injection layer 3 in a vacuum evaporation mode, wherein the thickness of the hole transport material HT-14 is 60nm, and the hole transport material HT-14 is a hole transport layer 4;
d) evaporating an electron barrier layer material HT-14 on the hole transport layer 4 in a vacuum evaporation mode, wherein the thickness of the electron barrier layer material is 20nm, and the electron barrier layer material is an electron barrier layer 5;
e) a light-emitting layer 6 is evaporated on the electron blocking layer 5, the compound 3 prepared in the embodiment of the invention is used as a host material, DP-1 is used as a doping material, and the mass ratio of the compound 3 to the DP-1 is 9:1, and the thickness is 30 nm;
f) an electron transport material ET-14 is evaporated on the luminescent layer 6 in a vacuum evaporation mode, the thickness is 40nm, and the organic material of the layer is used as a hole blocking/electron transport layer 7;
g) vacuum evaporating an electron injection layer LiF with the thickness of 1nm on the hole blocking/electron transport layer 7, wherein the layer is an electron injection layer 8;
h) on the electron injection layer 8, cathode Al (100nm) was vacuum-evaporated, and this layer was a cathode reflective electrode layer 9.
After the fabrication of the electroluminescent device was completed according to the above steps, IVL data, light decay life and color Coordinates (CIE) of the device were measured, and the results thereof are shown in table 2. The molecular mechanism formula of the related material is as follows:
Figure BDA0001218737880000271
examples 12 to 20 and comparative example 1
The devices of examples 12 to 20 and comparative examples 1 to 2 were fabricated by the same process as that of example 11, using the same substrate material and electrode material, and the film thickness of the electrode material was kept the same, except that the material used for the main body was different. See table 1 for specific data.
TABLE 1
Figure BDA0001218737880000272
Figure BDA0001218737880000281
The efficiency and lifetime data for each of the example and comparative example devices are shown in table 2.
TABLE 2
Figure BDA0001218737880000282
Figure BDA0001218737880000291
As can be seen from the device data results of table 2, the dual host organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over OLED devices of known materials.
In order to compare the efficiency attenuation conditions of different devices under high current density, the efficiency attenuation coefficient is defined
Figure BDA0001218737880000293
It is shown that the drive current is 100mA/cm2The ratio between the difference between the maximum efficiency μ 100 of the device and the maximum efficiency μm of the device and the maximum efficiency,
Figure BDA0001218737880000294
the larger the value, the more serious the efficiency roll-off of the device is, and conversely, the problem that the device rapidly decays under high current density is controlled. The efficiency attenuation coefficients of examples 11 to 20 and comparative examples 1 to 2 were measured respectively
Figure BDA0001218737880000295
The results of the measurements are shown in Table 3:
TABLE 3
Figure BDA0001218737880000292
From the data in table 3, it can be seen from the comparison of the efficiency roll-off coefficients of the examples and the comparative examples that the organic light emitting device of the present invention can effectively reduce the efficiency roll-off.
It is to be understood that the specific examples described above are intended to be illustrative only and are not intended to be limiting. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (15)

1. An organic electroluminescent device, comprising a hole transport region, an electron transport region and a light-emitting layer, wherein the light-emitting layer comprises a host material having the following specific structure:
Figure FDA0002200456540000011
Figure FDA0002200456540000021
Figure FDA0002200456540000031
Figure FDA0002200456540000032
any one of them.
2. The organic electroluminescent device of claim 1, wherein the light-emitting layer further comprises a guest dopant.
3. The organic electroluminescent device according to claim 2, wherein the guest dopant is represented by general formula (4):
Figure FDA0002200456540000033
wherein M is one of metal platinum (Pt), iridium (Ir), osmium (Os) or copper (Cu); x2、X3、X4And X5Each independently represents one of oxygen, carbon or nitrogen atoms; a. the5、A6Is an aromatic radical, A7Is an organic ligand; n is10, 1,2 or 3; n is21,2 or 3.
4. The organic electroluminescent device according to claim 3, wherein the specific structural formula of the compound represented by the general formula (4) is:
Figure FDA0002200456540000041
Figure FDA0002200456540000051
Figure FDA0002200456540000061
Figure FDA0002200456540000071
any one of them.
5. The organic electroluminescent device of claim 1, wherein the hole transport region comprises one or more of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer.
6. The organic electroluminescent device according to claim 5, wherein the hole injection layer material is one of the following structural formulas (6):
Figure FDA0002200456540000072
wherein, in the general formula (6), Fr1-Fr6Independently represent one of hydrogen atom, nitrile group, halogen, amide group, alkoxy group, ester group, nitro group, C1-C60 straight chain or branched chain alkyl substituted carbon atom, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C1-C60 heteroaryl.
7. The organic electroluminescent device according to claim 6, wherein the specific structural formula of the compound represented by the general formula (6) is:
Figure FDA0002200456540000073
Figure FDA0002200456540000081
any one of them.
8. The organic electroluminescent device according to claim 5, wherein the hole transport layer is a triarylamine group compound having a formula shown in formula (8):
Figure FDA0002200456540000082
wherein, Ar in the general formula (8)3、Ar4And Ar5Independently represent any one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C1-C60 heteroaryl.
9. The organic electroluminescent device according to claim 8, wherein the specific structural formula of the compound represented by the general formula (8) is:
Figure FDA0002200456540000083
Figure FDA0002200456540000091
Figure FDA0002200456540000101
Figure FDA0002200456540000111
Figure FDA0002200456540000112
any one of them.
10. The organic electroluminescent device of claim 1, wherein the electron transport region comprises one or more of an electron injection layer, an electron transport layer, and a hole blocking layer.
11. The organic electroluminescent device according to claim 10, wherein the material of the electron injection layer is one of lithium, lithium salt or cesium salt.
12. The organic electroluminescent device according to claim 11, wherein the lithium salt is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate, or lithium azide; the cesium salt is cesium fluoride, cesium carbonate, cesium chloride or cesium azide.
13. The organic electroluminescent device according to claim 10, wherein the material of the electron transport layer is a compound represented by the following general formula (10):
Figure FDA0002200456540000113
wherein, Dr in the general formula (10)1-Dr10Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group.
14. The organic electroluminescent device according to claim 13, wherein the specific structural formula of the compound represented by the general formula (10) is:
Figure FDA0002200456540000121
Figure FDA0002200456540000122
any one of them.
15. The organic electroluminescent device as claimed in claim 1, wherein the organic electroluminescent device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer from bottom to top, and the light emitting layer comprises a host material and a guest dopant.
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Granted publication date: 20200320

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Granted publication date: 20200320

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Registration number: Y2021980013807

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Effective date of registration: 20221024

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Patentee before: VALIANT Co.,Ltd.