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CN106220649A - Diaryl ketone-based compound and application thereof in organic electroluminescent device - Google Patents

Diaryl ketone-based compound and application thereof in organic electroluminescent device Download PDF

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CN106220649A
CN106220649A CN201610262088.3A CN201610262088A CN106220649A CN 106220649 A CN106220649 A CN 106220649A CN 201610262088 A CN201610262088 A CN 201610262088A CN 106220649 A CN106220649 A CN 106220649A
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ketone
compound
based compound
aryl
substituted alkylene
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CN106220649B (en
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李崇
徐凯
张兆超
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Jiangsu Sunera Technology Co Ltd
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Valiant Co Ltd
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Abstract

The invention discloses a diaryl ketone-based compound and application thereof in an organic electroluminescent device, the compound has the characteristics of difficult intermolecular crystallization and aggregation and good film forming property, and rigid groups in molecules can improve the thermal stability of materials. The compound is used as a luminescent layer material to be applied to an organic electroluminescent device, and the luminescent device using the compound has good photoelectric performance and can better adapt to and meet the application requirements of panel manufacturing enterprises.

Description

Diaryl ketone-based compound and application thereof in organic electroluminescent device
Technical Field
The invention relates to the technical field of semiconductors, in particular to a diaryl ketone-containing compound and application thereof as a light-emitting layer material in an organic light-emitting diode.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect.
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%). The external quantum efficiency is generally lower than 5%,although phosphorescent materials enhance intersystem crossing due to strong spin-orbit coupling of heavy atom centers, singlet excitons and triplet excitons formed by electric excitation can be effectively utilized to emit light, and the internal quantum efficiency of the devices reaches 100%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
In view of the above problems in the prior art, the present applicant provides a diaryl ketone-based compound and its use in an organic electroluminescent device. The compound is applied to the OLED as a light-emitting layer material based on a TADF mechanism, and the manufactured OLED device has good photoelectric property and can meet the requirements of panel manufacturing enterprises.
The technical scheme of the invention is as follows:
a diaryl ketone-based compound having a structure represented by general formula (1):
in the general formula (1), Ar represents C6-30Aryl, furyl, thienyl, pyrrolyl, quinolyl or carbazolyl;
in the general formula (1), R is represented by a general formula (2):
wherein, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group;
R1、R2independently select hydrogen or a structure shown in a general formula (3):
wherein a isX2、X3Respectively represent oxygen atom, sulfur atom, selenium atom, C1-10Straight or branched chain alkyl-substituted alkylene, aryl-substituted alkylene, alkyl orOne of aryl substituted amine groups; a and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Bond or CL‘4-CL’5And (4) key connection.
In the compounds when a representsAnd with CL4-CL5Bond or CL‘4-CL’5When connected to a bond, X1And X2Overlap in position of (2), taking only X1Or X2；X3Represented by oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
In the compound R1、R2Are each hydrogen, X1Is selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
In the compound R1、R2At least one being other than hydrogen, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
The compound is represented by general formula (4) or general formula (5):
the specific structural formula of the compound is as follows:
any one of the above.
A light emitting device comprising the diaryl ketone-based compound as a host material of a light emitting layer, which is applied to an organic light emitting diode.
A light emitting device comprising the diaryl ketone-based compound as a light emitting layer doping material applied to an organic light emitting diode.
A method of preparing the diaryl ketone-based compound, the reaction equation being:
weighing dibromo aryl ketone and RH, and dissolving with toluene; then adding Pd2(dba)3Tri-tert-butylphosphine, sodium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 95-110 ℃ for 10-24 hours under the inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target product; the molar ratio of the dibromo aryl ketone to RH is 1: 2.0-3.0, and Pd2(dba)3The molar ratio of the sodium tert-butoxide to the dibromoaryl ketone is 0.006-0.02: 1, the molar ratio of the tri-tert-butylphosphine to the dibromoaryl ketone is 0.006-0.02: 1, and the molar ratio of the sodium tert-butoxide to the dibromoaryl ketone is 1.0-3.0: 1.
The beneficial technical effects of the invention are as follows:
the compound takes diaryl ketone as a parent nucleus, two sides of the diaryl ketone are connected with two aromatic heterocyclic groups, the aggregation effect among molecules is avoided, most of the molecules are rigid groups, the compound has good film-forming property and fluorescence quantum efficiency, and can be used as a luminescent layer doping material; the compound structure molecule contains a combination of an electron donor (donor, D) and an electron acceptor (acceptor, A), which can increase orbital overlap and improve luminous efficiency, and two sides are connected with two aromatic heterocyclic groups to obtain a charge transfer state material with HOMO and LUMO space separation, so that small energy level difference of S1 state and T1 state is realized, and reverse intersystem crossing is realized under the condition of thermal stimulation, and the compound is suitable for being used as a main material of a luminous layer.
The compound can be used as a luminescent layer material for manufacturing OLED luminescent devices, and can be respectively used as a luminescent layer main body material or a doped material, so that good device performance can be obtained, and the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged.
The compound has good application effect in OLED luminescent devices and good industrialization prospect.
Drawings
FIG. 1 is a schematic diagram of the application of the compounds of the present invention to an OLED device;
wherein, 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a luminescent layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode reflection electrode layer.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
EXAMPLE 1 Compound 1
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 4,4' -dibromobenzophenone and 0.025mol of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] in an atmosphere of nitrogen gas]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotary evaporating the filtrate, and passing through silica gelAnd (5) performing column chromatography to obtain a target product with the purity of 99.2% and the yield of 67.00%.
Elemental analysis Structure (molecular formula C)55H40N2O3): theoretical value C, 85.03; h, 5.19; n, 3.61; o, 6.18; test values are: c, 84.99; h, 5.21; n, 3.70; and O, 6.10.
HPLC-MS: the molecular weight of the material is 776.30, and the measured molecular weight is 776.83.
EXAMPLE 2 Compound 6
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, under a nitrogen-purged atmosphere, 0.01mol of 4,4' -dibromobenzophenone and 0.025mol of 11, 11-dimethyl-4 a,6,11,13 a-tetrahydro-13-thia-6-aza-indole [1,2-b ] were added]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.0 percent and the yield of 69.00 percent.
Elemental analysis Structure (molecular formula C)55H42N2OS2): theoretical value C, 81.45; h, 5.22; n, 3.45; o, 1.97; test values are: c, 81.50; h, 5.21; n, 3.40; and O, 2.01.
HPLC-MS: the molecular weight of the material is 810.27, and the measured molecular weight is 810.65.
EXAMPLE 3 Compound 11
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 2,2' -dibromobenzophenone, and 0.025mol of 6, 6-dimethyl-13-phenyl-11, 13-dihydro-6H-11, 13-diaza-indole [1,2-b ] under a nitrogen-purged atmosphere]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 24 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.5 percent and the yield of 72.00 percent.
Elemental analysis Structure (molecular formula C)66H49N4O): theoretical value C, 86.80; h, 5.44; n, 6.04; o, 1.73; test values are: c, 86.63; h, 5.29; n, 6.30; o, 1.78.
HPLC-MS: the molecular weight of the material is 926.40, and the measured molecular weight is 926.52.
EXAMPLE 4 Compound 16
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of 2,2' -dibromobenzophenone and 0.025mol of 11,11,13, 13-tetramethyl-11, 13-dihydro-6H-6-aza-indole [1,2-b ] in an atmosphere of nitrogen gas]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.2 percent and the yield of 66.00 percent.
Elemental analysis Structure (score)Sub-formula C61H54NO): theoretical value C, 88.16; h, 6.55; n, 3.37; o, 1.93; test values are: c, 88.20; h, 6.62; n, 3.32; o, 1.86.
HPLC-MS: the molecular weight of the material is 830.42, and the measured molecular weight is 830.62.
EXAMPLE 5 Synthesis of Compound 17
Specific synthetic routes for this compound are now provided:
a250 ml four-necked flask was charged with 0.01mol of bis (4-bromo-naphthalen-1-yl) -methanone, 0.025mol of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] under a nitrogen atmosphere]Anthracene, 0.03mol of sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.2 percent and the yield of 66.80 percent.
Elemental analysis Structure (molecular formula C)63H44N2O3): theoretical value C, 86.28; h, 5.06; n, 3.19; o, 5.47; test values are: c, 86.20; h, 5.12; n, 3.12; and O, 5.56.
HPLC-MS: the molecular weight of the material is 876.34, and the measured molecular weight is 876.62.
EXAMPLE 6 Synthesis of Compound 140
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis (4-bromoanthracen-1-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10 mol under a nitrogen atmosphere-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.8 percent and the yield of 82.00 percent.
Elemental analysis Structure (molecular formula C)65H42N4O): theoretical value C, 87.22; h, 4.73; n, 6.26; o, 1.79; test values are: c, 87.20; h, 4.72; n, 6.32; o, 1.76.
HPLC-MS: the molecular weight of the material is 894.34, and the measured molecular weight is 894.38.
EXAMPLE 7 Synthesis of Compound 143
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis- (5-bromo-thiophen-2-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10, 10 mol under an atmosphere of nitrogen gas-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.9 percent and the yield of 86.00 percent.
Elemental analysis Structure (molecular formula C)45H30N4OS2): theoretical value C, 76.46; h, 4.28; n, 7.93; o, 2.26; s, 9.07; test values are: c, 76.40; h, 4.32; n, 7.92; o, 2.32; and S, 9.04.
HPLC-MS: the molecular weight of the material is 706.19, and the measured molecular weight is 706.38.
EXAMPLE 8 Synthesis of Compound 144
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis (5-bromo-1-phenyl-1H-pyrrol-2-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03mol of sodium tert-butoxide, 1 × 10 mol-4molPd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain the target product with the purity of 99.9 percent and the yield of 86.00 percent.
Elemental analysis Structure (molecular formula C)57H40N6O): theoretical value C, 82.99; h, 4.89; n, 10.19; o, 1.94; test values are: c, 82.90; h, 4.92; n, 10.32; o, 1.86.
HPLC-MS: the molecular weight of the material is 824.33, and the measured molecular weight is 824.57.
EXAMPLE 9 Synthesis of Compound 145
Specific synthetic routes for this compound are now provided:
in a 250ml four-necked flask, 0.01mol of bis (8-bromo-quinolin-5-yl) -methanone, 0.025mol of 5-phenyl-5, 10-dihydro-phenazine, 0.03m were added under a nitrogen atmosphereol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampling the spot plate, and the reaction was complete. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.9 percent and the yield of 84.00 percent.
Elemental analysis Structure (molecular formula C)55H36N6O): theoretical value C, 82.89; h, 4.55; n, 10.55; o, 2.01; test values are: c, 82.93; h, 4.50; n, 10.59; o, 1.98.
HPLC-MS: the molecular weight of the material is 796.30, and the measured molecular weight is 796.68.
EXAMPLE 10 Synthesis of Compound 147
Specific synthetic routes for this compound are now provided:
compound 147 was prepared as in example 1 except that the starting material 14, 14-dimethyl-5, 14-dihydro-7, 12-dioxa-5-aza-pentacene was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 11 Synthesis of Compound 151
Specific synthetic routes for this compound are now provided:
compound 151 was prepared as in example 1, except that the starting material, 14H-5-oxa-14-aza-pentacene, was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 12 Synthesis of Compound 159
Specific synthetic routes for this compound are now provided:
compound 159 was prepared as in example 1, except that the starting material 14, 14-dimethyl-5-phenyl-7, 14-dihydro-5H-12-oxa-5, 7-diaza-pentacene was used in place of 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 13 Synthesis of Compound 160
Compound 160 was prepared as in example 1, except that starting material a was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 14 Synthesis of Compound 161
Compound 161 was prepared as in example 1, except that starting material B was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-B ] anthracene.
EXAMPLE 15 Synthesis of Compound 163
Compound 163 was prepared as in example 3, except that starting material C was substituted for 6, 6-dimethyl-13-phenyl-11, 13-dihydro-6H-11, 13-diaza-indole [1,2-b ] anthracene.
EXAMPLE 16 Synthesis of Compound 164
Compound 164 was prepared as in example 1, except that starting material D was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
EXAMPLE 17 Synthesis of Compound 166
Compound 166 was prepared as in example 1, except that starting material E was substituted for 6, 6-dimethyl-6, 11-dihydro-13-oxa-11-aza-indole [1,2-b ] anthracene.
The compound of the invention can be used as a luminescent layer material, and the thermal performance, the luminescence spectrum and the HOMO and LUMO energy levels of the compound 1, the compound 164 and the existing material CBP are measured, and the test results are shown in Table 1.
TABLE 1
Note: the thermal weight loss temperature Td is in a nitrogen atmosphereThe temperature of the medium weight loss of 1 percent is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation in Japan, and the nitrogen flow is 20 mL/min; lambda [ alpha ]PLThe fluorescence emission wavelength of the sample solution is measured by using a Japanese topotecan SR-3 spectroradiometer; phi f is the fluorescence quantum efficiency of the solid powder (measured by using a solid fluorescence quantum efficiency testing system consisting of a Maya2000Pro fiber optic spectrometer of American marine optics, a C-701 integrating sphere of American blue-phenanthrene company and a LLS-LED light source of marine optics, in a method of Adv. Mater.1997, 9, 230-; the highest occupied molecular orbital HOMO energy level and the lowest occupied molecular orbital LUMO energy level were measured by a photoelectron emission spectrometer (AC-2 type PESA) and an ultraviolet-visible spectrophotometer, and the test was conducted in an atmospheric environment.
As can be seen from the data in the table above, the compound of the present invention has suitable HOMO and LUMO energy levels and high thermal stability, and is suitable as a host material of a light emitting layer; meanwhile, the compound has a proper light-emitting spectrum and a high phi f, so that the efficiency and the service life of an OLED device using the compound as a doping material are improved.
The effect of the synthesized OLED material of the present invention as a host material for a light emitting layer in a device is described in detail below by examples 18-34 and comparative example 1. The manufacturing processes of the devices of 19 to 34 of the present invention and comparative example 1 are completely the same as those of example 18, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, except that the host material of the light-emitting layer 5 in the device is changed. The structural composition of the resulting devices of each example is shown in table 2. The test results of the resulting devices are shown in table 3.
Example 18
ITO anode layer 2/hole injection layer 3 (molybdenum trioxide, MoO)3Thickness 10 nm)/hole transport layer 4(TAPC, thickness 80 nm)/light-emitting layer 5 (compound 1 and GD19 as per 100: 5 in a weight ratio of 30 nm/electron transport layer 6(TPBI, thickness 40 nm)/electron injection layer 7(LiF, thickness 1nm)/Al
The preparation process comprises the following steps:
the ITO anode layer 2 (having a film thickness of 150nm) was washed by alkali washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO.
On the ITO ITO anode layer 2 after the above washing, molybdenum trioxide MoO having a film thickness of 10nm was deposited by a vacuum deposition apparatus3The hole injection layer 3 is used. Subsequently, TAPC was evaporated to a thickness of 80nm as the hole transport layer 4.
After the evaporation of the hole transport material is finished, the light-emitting layer 5 of the OLED light-emitting device is manufactured, and the structure of the light-emitting layer 5 comprises the material compound 1 used by the OLED light-emitting layer 5 as a main material, GD19 as a doping material, the doping proportion of the doping material is 5% by weight, and the thickness of the light-emitting layer is 30 nm.
After the light-emitting layer 5, the electron transport layer material is continuously vacuum evaporated to be TPBI. The vacuum evaporation film thickness of the material was 40nm, and this layer was an electron transport layer 6.
On the electron transport layer 6, a lithium fluoride (LiF) layer having a film thickness of 1nm was formed by a vacuum deposition apparatus, and this layer was an electron injection layer 7.
On the electron injection layer 7, an aluminum (Al) layer having a film thickness of 80nm was formed by a vacuum deposition apparatus, and this layer was used as the cathode reflection electrode layer 8.
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, the light emission spectrum, and the lifetime of the device were measured. The test results of the resulting devices are shown in table 3.
TABLE 2
TABLE 3
Device code Current efficiency Color(s) LT95 Life
Example 18 1.6 Green light 3.6
Example 19 1.9 Green light 4.3
Example 20 1.7 Green light 3.7
Example 21 2.2 Green light 4.2
Example 22 1.7 Green light 4.1
Example 23 2.2 Green light 3.7
Example 24 2.1 Green light 3.9
Example 25 1.6 Green light 4.2
Example 26 1.9 Green light 4.0
Example 27 1.6 Green light 4.1
Example 28 2.0 Green light 4.8
Example 29 1.8 Green light 3.2
Example 30 1.4 Green light 1.9
Example 31 1.8 Green light 3.5
Example 32 1.9 Green light 2.7
Example 33 2.0 Green light 2.4
Example 34 1.7 Green light 3.3
Comparative example 1 1.0 Green light 1.0
The device test performance is referred to comparative example 1, and each performance index of the device of comparative example 1 is set to 1.0. The current efficiency of comparative example 1 was 6.5cd/A (@10 mA/cm)2) (ii) a CIE color coordinates (0.32, 0.61); LT95 lifetime decay was 3.8Hr at 5000 brightness.
The life test system is an OLED device life tester which is researched by the owner of the invention together with Shanghai university.
The effect of the synthesized compound of the present invention as a doping material for a light emitting layer in a device is illustrated by examples 35 to 41 and comparative example 2. The manufacturing processes of the devices 35 to 41 and comparative example 2 of the present invention are completely the same as those of the device in example 18, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, except that the doping material in the light-emitting layer 5 in the device is different, and the doping concentration is changed to 7%. The structural composition of each device is shown in table 4. The test results of the resulting devices are shown in table 5.
TABLE 4
TABLE 5
Device code Current efficiency Color(s) LT95 Life
Example 35 1.5 Green light 4.6
Example 36 1.6 Green light 3.5
Example 37 1.8 Green light 2.6
Example 38 1.9 Green light 5.7
Example 39 1.5 Green light 3.1
Example 40 1.6 Green light 5.6
EXAMPLE 41 2.1 Green light 4.4
Comparative example 2 1.0 Green light 1.0
Note: the device test performance was defined as comparative example 2, and each performance index of the device of comparative example 2 was 1.0. Comparative example 2 has a current efficiency of 9.5cd/A (@10 mA/cm)2) (ii) a CIE color coordinates (0.27, 0.65); LT95 lifetime decay was 8.2Hr at 5000 brightness. The life test system isThe invention relates to an OLED device life tester jointly developed by owners of the OLED device and Shanghai university.
The results in table 3 show that the compound of the present invention can be used as a host material of a light emitting layer for fabrication of an OLED light emitting device, and compared with comparative example 1, the efficiency and lifetime of the OLED light emitting device are greatly improved compared with those of the known OLED material, and especially the driving lifetime of the device is greatly prolonged.
The results in table 5 show that the compound of the present invention can be applied to the fabrication of OLED light emitting devices as a doping material of a light emitting layer, and compared with comparative example 2, the efficiency and lifetime of the compound are greatly improved compared with those of known OLED materials, especially the driving lifetime of the device is greatly improved.
From the data application, the compound has good application effect in an OLED light-emitting device as a light-emitting layer material, and has good industrialization prospect.
Although the present invention has been disclosed by way of examples and preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, it is intended to cover various modifications and similar arrangements as would be apparent to those skilled in the art. The scope of the following claims is, therefore, to be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.

Claims (9)

1. A diaryl ketone-based compound, characterized in that the compound has the structure represented by the general formula (1):
in the general formula (1), Ar represents C6-30Aryl, furyl, thienyl, pyrrolyl, quinolyl or carbazolyl;
in the general formula (1), R is represented by a general formula (2):
wherein,
X1is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group;
R1、R2independently select hydrogen or a structure shown in a general formula (3):
wherein a isX2、X3Respectively represent oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted amine group; a and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Bond or CL‘4-CL’5And (4) key connection.
2. The diaryl ketone-based compound according to claim 1, wherein when a representsAnd with CL4-CL5Bond or CL‘4-CL’5When connected to a bond, X1And X2Overlap in position of (2), taking only X1Or X2；X3Represented by oxygen atom, sulfur atom, selenium atom, C1-10Linear or branched alkyl substituted alkyleneOne of a group, an aryl-substituted alkylene group, an alkyl group or an aryl-substituted amine group.
3. The diaryl ketone-based compound according to claim 1, wherein R is1、R2Are each hydrogen, X1Is selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
4. The diaryl ketone-based compound according to claim 1, wherein R is1、R2At least one being other than hydrogen, X1Is oxygen atom, sulfur atom, selenium atom, C1-10One of a linear or branched alkyl substituted alkylene, an aryl substituted alkylene, an alkyl or an aryl substituted amine.
5. The diaryl ketone-based compound according to claim 1, wherein the compound is represented by general formula (4) or general formula (5):
6. the diaryl ketone-based compound according to claim 1, wherein the compound has the following specific structural formula:
any one of the above.
7. A light-emitting device comprising the diaryl ketone-based compound according to any one of claims 1 to 6, wherein the compound is used as a host material for a light-emitting layer in an organic light-emitting diode.
8. A light-emitting device comprising the diaryl ketone-based compound according to any one of claims 1 to 6, wherein the compound is used as a doping material for a light-emitting layer in an organic light-emitting diode.
9. A process for preparing the diaryl ketone-based compound according to any one of claims 1 to 6, wherein the reaction equation is:
weighing dibromo aryl ketone and RH, and dissolving with toluene; then adding Pd2(dba)3Tri-tert-butylphosphine, sodium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 95-110 ℃ for 10-24 hours under the inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target product; the molar ratio of the dibromo aryl ketone to RH is 1: 2.0-3.0, and Pd2(dba)3The molar ratio of the sodium tert-butoxide to the dibromoaryl ketone is 0.006-0.02: 1, the molar ratio of the tri-tert-butylphosphine to the dibromoaryl ketone is 0.006-0.02: 1, and the molar ratio of the sodium tert-butoxide to the dibromoaryl ketone is 1.0-3.0: 1.
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