CN106467486B - Organic compound containing dimethylanthracene and application thereof - Google Patents

Organic compound containing dimethylanthracene and application thereof Download PDF

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CN106467486B
CN106467486B CN201610738441.0A CN201610738441A CN106467486B CN 106467486 B CN106467486 B CN 106467486B CN 201610738441 A CN201610738441 A CN 201610738441A CN 106467486 B CN106467486 B CN 106467486B
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CN106467486A (en
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张兆超
李崇
叶中华
张小庆
王立春
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Jiangsu Sunera Technology Co Ltd
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Valiant Co Ltd
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Abstract

The compound has higher glass transition temperature and molecular thermal stability, proper HOMO and L UMO energy levels and higher Eg, and can effectively improve the photoelectric property of an O L ED device and the service life of the O L ED device through device structure optimization.

Description

Organic compound containing dimethylanthracene and application thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a compound material containing a dimethylanthracene structure as a central skeleton and application thereof in the field of O L ED.
Background
The Organic electroluminescent (O L ED: Organic L light Emission Diodes) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect.
The O L ED light-emitting device is just like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, wherein the different functional materials are mutually overlapped to form the O L ED light-emitting device according to the application.
Currently, the O L ED display technology has been applied to smart phones, tablet computers, and other fields, and will further expand to large-size application fields such as televisions, however, compared with actual product application requirements, the performance of O L ED devices, such as light-emitting efficiency and service life, needs to be further improved.
In order to realize the continuous improvement of the performance of the O L ED device, the innovation of the O L ED device structure and the manufacturing process is needed, the continuous research and innovation of an O L ED photoelectric functional material are needed, and a functional material with higher performance O L ED is created.
The O L ED photoelectric functional materials applied to O L ED devices can be divided into two broad categories from the aspect of use, namely, charge injection transport materials and light-emitting materials, further, the charge injection transport materials can be divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light-emitting materials can be divided into host light-emitting materials and doping materials.
In order to fabricate a high-performance O L ED light emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, and as a host material of a light emitting layer, a material having good bipolar property, appropriate HOMO/L UMO energy level, etc. is required.
The O L ED photoelectric functional material film layer forming the O L ED device at least comprises more than two layers, and the O L ED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer and other film layers, namely the photoelectric functional material applied to the O L ED device at least comprises a hole injection material, a hole transport material, a luminescent material, an electron transport material and the like, and the material types and the matching forms have the characteristics of richness and diversity.
Therefore, aiming at the industrial application requirements of the current O L ED device and the requirements of different functional film layers and photoelectric characteristics of the O L ED device, a more suitable O L ED functional material or material combination with high performance must be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device, in terms of the actual requirements of the current O L ED display illumination industry, the development of the current O L ED material is far from enough and lags behind the requirements of panel manufacturing enterprises, and the O L ED material is particularly important to be used as a material enterprise for developing higher-performance organic functional materials.
Disclosure of Invention
The compound contains a dimethylanthracene structure, has higher glass transition temperature and molecular thermal stability, proper HOMO and L UMO energy levels and higher Eg, and can effectively improve the photoelectric property of an O L ED device and the service life of an O L ED device through optimization of the device structure.
The technical scheme of the invention is as follows:
the applicant provides an organic compound containing dimethylanthracene, the structural formula of the compound is shown as a general formula (1):
Figure BDA0001093433920000021
wherein Ar is1、Ar2Represented by phenyl, biphenyl or naphthyl;
R1、R2each independently represents a structure represented by the general formula (2); r1And R2May be the same or different; r1May also be represented as a hydrogen atom;
Figure BDA0001093433920000031
in the general formula (2), R3、R4Each independently represents a hydrogen atom, a structure represented by general formula (3) or general formula (4);
Figure BDA0001093433920000032
in the general formula (3), a is selected from
Figure BDA0001093433920000033
X1、X2、X3Each independently represents an oxygen atom, a sulfur atom, a selenium atom, C1-10One of linear or branched alkyl substituted alkylene, aryl substituted alkylene, alkyl or aryl substituted tertiary amine;
through C in the general formula (3) or the general formula (4)L1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Bond or CL‘3-CL’4The bond is linked to formula (2).
Preferably, said R is1、R2Independently expressed as:
Figure BDA0001093433920000034
Figure BDA0001093433920000041
Figure BDA0001093433920000051
Figure BDA0001093433920000061
Figure BDA0001093433920000071
Figure BDA0001093433920000081
Figure BDA0001093433920000091
Figure BDA0001093433920000101
Figure BDA0001093433920000111
Figure BDA0001093433920000121
Figure BDA0001093433920000131
Figure BDA0001093433920000132
any one of them.
Preferably, the specific structural formula of the organic compound containing dimethylanthracene is as follows:
Figure BDA0001093433920000133
Figure BDA0001093433920000141
Figure BDA0001093433920000151
Figure BDA0001093433920000161
Figure BDA0001093433920000171
Figure BDA0001093433920000181
Figure BDA0001093433920000191
Figure BDA0001093433920000201
Figure BDA0001093433920000202
any one of them.
The applicant also provides a process for the preparation of said organic compounds, when R is1Expressed as hydrogen atoms, the reaction equation in this preparation method is:
Figure BDA0001093433920000211
the preparation method uses Br-Ar2MgBr is used as a raw material, a Grignard reagent is prepared through a Grignard reaction, and then the Grignard reagent reacts with dimethyl anthrone to generate tertiary alcohol; followed by tertiary alcohol and H-Ar1Preparing monobromo compound by Friedel-crafts reaction, and then neutralizing
Figure BDA0001093433920000212
The organic compound is prepared by C-N coupling.
The Applicant also provides another process for the preparation of said organic compounds, characterized in that when R is1When the structure is represented by the general formula (2), the reaction equation in the preparation method is:
Figure BDA0001093433920000213
the preparation method uses Br-Ar2Preparing Grignard reagent from MgBr serving as raw material through Grignard reaction, and then reacting with dimethyl anthrone to generate tertiary alcohol, tertiary alcohol and H-Ar1Preparing dibromo compound from-Br by Friedel-crafts reaction, and then neutralizing
Figure BDA0001093433920000214
By C-N couplingThe organic compound is prepared.
The present applicant also provides an organic electroluminescent device comprising at least one functional layer containing the organic compound containing dimethylanthracene.
The beneficial technical effects of the invention are as follows:
the compound takes dimethylanthracene as a mother nucleus, is connected with symmetrical or asymmetrical rigid groups, destroys the crystallinity of molecules, avoids intermolecular aggregation, has high glass transition temperature, and can keep high film stability and prolong the service life of an O L ED device when the material is applied to the O L ED device.
The compound structure of the invention ensures that electrons and holes are distributed more evenly in the luminescent layer, improves the hole injection/transmission performance under the proper HOMO energy level, plays the role of electron blocking under the proper L UMO energy level, improves the recombination efficiency of excitons in the luminescent layer, and when the compound structure is used as a luminescent functional layer material of an O L ED luminescent device, aryl substituted dimethylanthracene can effectively improve the exciton utilization rate and high fluorescence radiation efficiency by matching with branched chains in the range of the invention, reduce the efficiency roll-off under high current density, reduce the voltage of the device, improve the current efficiency of the device and prolong the service life of the device.
The special structural design of the compound enables the material to have high decomposition temperature and low sublimation temperature or vacuum evaporation temperature, and a higher temperature difference window is formed between the sublimation temperature or the evaporation temperature and the decomposition temperature, so that the material has higher operation controllability in industrial application, and is beneficial to mass production application of the material.
The compound has good application effect in an O L ED light-emitting device and good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an O L ED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport/electron blocking layer, 5 is a luminescent layer, 6 is an electron transport/hole blocking 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: synthesis of intermediate a 1:
the synthetic route is as follows:
Figure BDA0001093433920000221
Figure BDA0001093433920000231
adding 11.8g of 1, 4-dibromobenzene (0.05mol), 1.33g of Mg powder (0.055mol) and 60ml of tetrahydrofuran into a 250ml four-mouth bottle under the atmosphere of introducing nitrogen, heating and refluxing for 4 hours, and completely reacting to generate a Grignard reagent;
11.1g10, 10-dimethylanthrone (0.05mol) was dissolved in 50ml tetrahydrofuran, the above Grignard reagent was added dropwise, reaction was carried out at 60 ℃ for 24 hours to form a large amount of white precipitate, and saturated NHCl was added finally4Converting the grignard salt to an alcohol; after the reaction is finished, extracting with diethyl ether, drying and rotary steaming, and mixing petroleum ether: purifying the dichloromethane mixed solvent (3:2) by a silica gel column to obtain solid tertiary alcohol with slight yellow color (the yield is 88 percent); the compound was identified using DEI-MS, formula C22H19BrO, detection value [ M +1]+379.03, calculate value 378.06;
15.2g of the tertiary alcohol (0.04mol) and 12.5g of bromobenzene (0.08mol) are dissolved in 100ml of dichloromethane according to 1:2 equivalent, 8ml of boron trifluoride diethyl etherate complex is added dropwise at room temperature for reaction for 30 minutes, 20ml of ethanol and 20ml of water are added for quenching reaction, extraction is carried out with dichloromethane (20ml × 3), drying and rotary evaporation are carried out, and petroleum ether silica gel column purification is carried out by ethanol: recrystallizing the dichloromethane with the yield of 75 percent; the compound was identified using DEI-MS, formula C28H22Br2Detection value [ M +1 ]]+516.87, calculate value 516.01;
example 2: synthesis of intermediate a 2:
the synthetic route is as follows:
Figure BDA0001093433920000232
intermediate a2 was prepared as the synthetic method for intermediate a1 in example 1, except that 1, 1' -biphenyl was used in place of the compound bromobenzene;
the compound was identified using DEI-MS, formula C34H27Br, detected value [ M +1]+514.85, calculate value 514.13.
Example 3: synthesis of intermediate a 3:
the synthetic route is as follows:
Figure BDA0001093433920000241
intermediate A3 was prepared as the synthesis of intermediate a1 in example 1, except that in the third reaction step, benzene was used instead of bromobenzene;
the compound was identified using DEI-MS, formula C28H23Br, detected value [ M +1]+438.10, calculate value 438.87.
Example 4: synthesis of intermediate a 4:
the synthetic route is as follows:
Figure BDA0001093433920000242
intermediate A4 was prepared following the procedure for the synthesis of intermediate A1 in example 1, except that 1, 3-dibromobenzene was used instead of 1, 4-dibromobenzene in the first reaction step;
the compound was identified using DEI-MS, formula C28H23Br, detected value [ M +1]+438.10, calculate value 438.84.
Example 5: synthesis of intermediate a 5:
the synthetic route is as follows:
Figure BDA0001093433920000251
intermediate a5 was prepared following the synthesis of intermediate a1 in example 1, except that 1, 3-dibromonaphthalene was used in place of 1, 4-dibromobenzene in the first reaction step;
the compound was identified using DEI-MS, formula C32H25Br, detected value [ M +1]+488.93, calculate value 488.11.
Example 6: synthesis of Compound 1:
the synthetic route is as follows:
Figure BDA0001093433920000252
adding 0.01mol of intermediate A1, 0.024mol of intermediate B1, 0.04mol of sodium tert-butoxide and 1 × 10 into a 250ml three-neck flask under the protection of nitrogen-4molpd2(dba)3，1×10-4Heating and refluxing 150ml of tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and carrying out column chromatography to obtain a target product, wherein the purity of HP L C is 99.5%, and the yield is 65.2%;
elemental analysis Structure (molecular formula C)60H42N2): theoretical value C, 91.11; h, 5.35; n, 3.54; test values are: c, 91.09; h, 5.33; and N, 3.58.
HP L C-MS material molecular weight 790.99, found molecular weight 791.25.
Example 7: synthesis of Compound 3:
the synthetic route is as follows:
Figure BDA0001093433920000261
adding 0.01mol of intermediate A2, 0.012mol of intermediate B2, 0.03mol of sodium tert-butoxide and 5 × 10 into a 250ml three-neck flask under the protection of nitrogen-5mol pd2(dba)3，5×10-5Heating and refluxing 150ml of tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and carrying out column chromatography to obtain a target product, wherein the purity of HP L C is 99.3%, and the yield is 72.5%;
elemental analysis Structure (molecular formula C)54H39N): theoretical value C, 92.40; h, 5.60; n, 2.00; test values are: c, 92.37; h, 5.61; and N, 2.02.
HP L C-MS material molecular weight 701.89, found molecular weight 702.21.
Example 8: synthesis of compound 10:
the synthetic route is as follows:
Figure BDA0001093433920000262
adding 0.01mol of intermediate A3, 0.012mol of intermediate C1, 0.03mol of sodium tert-butoxide and 5 × 10 into a 250ml three-neck flask under the protection of nitrogen-5mol pd2(dba)3，5×10-5Heating and refluxing the tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and carrying out column chromatography to obtain a target product, wherein the purity of HP L C is 99.4%, and the yield is 71.9%;
elemental analysis Structure (molecular formula C)52H38N2): theoretical value C, 90.40; h, 5.54; n, 4.05; test values are: c, 90.46; h, 5.52; and N, 4.02.
HP L C-MS material molecular weight 690.87, found molecular weight 691.18.
Example 9: synthesis of compound 11:
the synthetic route is as follows:
Figure BDA0001093433920000271
prepared according to the synthetic method for compound 10 in example 8, except that intermediate C2 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)46H33NO): theoretical value C, 89.73; h, 5.40; n, 2.27; o, 2.60; test values are: c, 89.73; h, 5.42; n, 2.26; o, 2.59.
HP L C-MS material molecular weight 615.76, found molecular weight 616.02.
Example 10: synthesis of compound 14:
the synthetic route is as follows:
Figure BDA0001093433920000272
prepared according to the synthetic method for compound 10 in example 8, except that intermediate D1 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)50H35NO): theoretical value C, 90.19; h, 5.30; n, 2.10; o, 2.40; test values are: c, 90.16; h, 5.32; n, 2.11; o, 2.41.
HP L C-MS material molecular weight 665.82, found molecular weight 666.03.
Example 11: synthesis of compound 18:
the synthetic route is as follows:
Figure BDA0001093433920000273
prepared according to the synthetic method for compound 10 in example 8, except that intermediate C3 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)52H38N2): theoretical value C, 90.40; h, 5.54; n, 4.05; test values are: c, 90.16; h, 5.32; n, 2.11.
HP L C-MS material molecular weight 665.82, found molecular weight 666.03.
Example 12: synthesis of compound 31:
the synthetic route is as follows:
Figure BDA0001093433920000281
prepared according to the synthetic method for compound 10 in example 8, except that intermediate E1 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)58H47N): theoretical value C, 91.90; h, 6.25; n, 1.85; test values are: c, 91.90; h, 6.24; n, 1.86.
HP L C-MS material molecular weight 758.00, found molecular weight 758.32.
Example 13: synthesis of compound 40:
the synthetic route is as follows:
Figure BDA0001093433920000282
prepared according to the synthetic method for compound 10 in example 8, except that intermediate E2 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)58H47N): theoretical value C, 91.90; h, 6.25; n, 1.85; test values are: c, 91.89; h, 6.26; n, 1.85.
HP L C-MS material molecular weight 758.00, found molecular weight 758.31.
Example 14: synthesis of compound 41:
the synthetic route is as follows:
Figure BDA0001093433920000291
adding 0.01mol of intermediate A5, 0.012mol of intermediate E1, 0.03mol of sodium tert-butoxide and 5 × 10 into a 250ml three-neck flask under the protection of nitrogen-5mol pd2(dba)3，5×10-5Heating and refluxing 150ml of tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and carrying out column chromatography to obtain a target product, wherein the purity of HP L C is 99.1%, and the yield is 62.8%;
elemental analysis Structure (molecular formula C)59H43NS): theoretical value C, 88.80; h, 5.43; n, 1.76; s, 4.02; test values are: c, 88.82; h, 5.42; n, 1.75; and S, 4.01.
HP L C-MS material molecular weight 798.04, found molecular weight 798.39.
Example 15: synthesis of compound 44:
the synthetic route is as follows:
Figure BDA0001093433920000292
prepared according to the synthetic method for compound 10 in example 8, except that intermediate E4 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)52H35NO2): theoretical value C, 88.48; h, 5.00; n, 1.98; o, 4.53; test values are: c, 88.49; h, 5.01; n, 1.99; o, 4.51.
HP L C-MS material molecular weight 705.84, found molecular weight 706.05.
Example 16: synthesis of compound 51:
the synthetic route is as follows:
Figure BDA0001093433920000293
prepared according to the synthetic method for compound 10 in example 8, except that intermediate E5 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)58H47N): theoretical value C, 91.90; h, 6.25; n, 1.85; test values are: c, 91.90; h, 6.26; n, 1.84.
HP L C-MS material molecular weight 758.00, found molecular weight 758.39.
Example 17: synthesis of compound 54:
the synthetic route is as follows:
Figure BDA0001093433920000301
adding 0.01mol of intermediate A4, 0.012mol of intermediate E6, 0.03mol of sodium tert-butoxide and 5 × 10 into a 250ml three-neck flask under the protection of nitrogen-5mol pd2(dba)3，5×10-5Heating and refluxing 150ml of tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and carrying out column chromatography to obtain a target product, wherein the purity of HP L C is 98.8%, and the yield is 65.6%;
elemental analysis Structure (molecular formula C)53H38N2Se): theoretical value C, 81.42; h, 4.90; n, 3.58; se, 10.10; test values are: c, 81.41; h, 4.89; n, 3.59; se, 10.11.
HP L C-MS material molecular weight 781.84, found molecular weight 782.03.
Example 18: synthesis of compound 66:
the synthetic route is as follows:
Figure BDA0001093433920000302
prepared according to the synthetic method for compound 10 in example 8, except that intermediate F1 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)49H39NO): theoretical value C, 89.46; h, 5.98; n, 2.13; o, 2.43; test values are: c, 89.47; h, 5.99; n, 2.12; o, 2.42.
HP L C-MS material molecular weight 657.84, found molecular weight 658.04.
Example 19: synthesis of compound 70:
the synthetic route is as follows:
Figure BDA0001093433920000311
prepared according to the synthetic method for compound 10 in example 8, except that intermediate F2 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)55H44N2): theoretical value C, 90.13; h, 6.05; n, 3.82; test values are: c, 90.15; h, 6.04; and N, 3.81.
HP L C-MS material molecular weight 732.95, found molecular weight 733.21.
Example 20: synthesis of compound 84:
the synthetic route is as follows:
Figure BDA0001093433920000312
prepared according to the synthetic method for compound 10 in example 8, except that intermediate F3 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)52H38N2O): theoretical value C, 88.36; h, 5.42;n, 3.96; o, 2.26; test values are: c, 88.37; h, 5.43; n, 3.95; o, 2.25.
HP L C-MS material molecular weight 706.87, found molecular weight 707.05.
Example 21: synthesis of compound 86:
the synthetic route is as follows:
Figure BDA0001093433920000313
prepared according to the synthetic method for compound 10 in example 8, except that intermediate F4 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)49H39NO): theoretical value C, 89.46; h, 5.98; n, 2.13; o, 2.43; test values are: c, 89.46; h, 5.97; n, 2.14; o, 2.43.
HP L C-MS material molecular weight 657.84, found molecular weight 658.07.
Example 22: synthesis of compound 91:
the synthetic route is as follows:
Figure BDA0001093433920000321
prepared according to the synthetic method for compound 10 in example 8, except that intermediate G1 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)58H47NO2): theoretical value C, 88.18; h, 6.00; n, 1.77; o, 4.05; test values are: c, 88.23; h, 5.97; n, 1.76; and O, 4.04.
HP L C-MS material molecular weight 790.00, found molecular weight 790.28.
Example 23: synthesis of compound 96:
the synthetic route is as follows:
Figure BDA0001093433920000322
prepared according to the synthetic method for compound 10 in example 8, except that intermediate G2 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)61H46N2O): theoretical value C, 89.02; h, 5.63; n, 3.40; o, 1.94; test values are: c, 89.02; h, 5.62; n, 3.41; o, 1.95.
HP L C-MS material molecular weight 823.03, found molecular weight 823.35.
Example 24: synthesis of compound 104:
the synthetic route is as follows:
Figure BDA0001093433920000323
prepared according to the synthetic method for compound 10 in example 8, except that intermediate H1 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)54H40N2): theoretical value C, 90.47; h, 5.62; n, 3.91; test values are: c, 90.49; h, 5.61; and N, 3.90.
HP L C-MS material molecular weight 716.91, found molecular weight 717.22.
Example 25: synthesis of compound 112:
the synthetic route is as follows:
Figure BDA0001093433920000331
prepared according to the synthetic method for compound 10 in example 8, except that intermediate G3 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)70H57N3): theoretical value C, 89.42; h, 6.11; n, 4.47; test values are: c, 89.45; h, 6.10; and N, 4.45.
HP L C-MS material molecular weight 940.22, found molecular weight 940.56.
Example 26: synthesis of compound 119:
the synthetic route is as follows:
Figure BDA0001093433920000332
prepared according to the synthetic method for compound 10 in example 8, except that intermediate G4 is used instead of intermediate C1;
elemental analysis Structure (molecular formula C)67H51N3O): theoretical value C, 88.03; h, 5.62; n, 4.60; o, 1.75; test values are: c, 88.04; h, 5.63; n,4.59O, 1.74.
HP L C-MS material molecular weight 914.14, found molecular weight 914.53.
The compound of the invention can be used in a luminescent device, can be used as a hole transport/electron barrier layer material, and can also be used as a host-guest material of a luminescent layer. The compound has high operability and practicability when being applied, and is mainly reflected by high glass transition temperature, low sublimation temperature, high decomposition temperature and film forming stability.
The compound 10, the compound 55, the compound 66 and the existing material CBP are respectively tested for thermal performance and HOMO level, and the test results are shown in table 1.
TABLE 1
Figure BDA0001093433920000341
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 evaporation temperature is SUNIC evaporation equipment, the vacuum degree is less than 1E-5Pa, and the material rate is
Figure BDA0001093433920000342
The evaporation temperature, the thermal weight loss temperature Td is the temperature of 1 percent weight loss in a nitrogen atmosphere, the nitrogen flow is 20m L/min, the film forming stability is that a SUNIC evaporation machine is used to evaporate the material onto a glass substrate to form a film with the thickness of 100nm, the film is packaged in a glove box environment (the water and oxygen content is less than 1PPm), the packaged glass sample is placed and tested for 240 hours under the double 80 conditions (the humidity is 80 percent and the temperature is 80 ℃), the crystallization performance of the sample film is observed by a microscope, the highest occupied molecular orbital HOMO energy level and the lowest occupied molecular orbital L UMO energy level are determined by the weight loss temperature of 1 percent in a TGA-50H thermogravimetric analyzer of Shimadzu corporation in JapanAnd testing by a photoelectron emission spectrometer (AC-2 type PESA), wherein the testing is in an atmospheric environment.
The data in the table show that the compound has adjustable HOMO energy level, is suitable for being used as materials of different functional layers, can reduce the influence of thermal radiation on Fine-mask deformation in an evaporation machine table when the material is applied to industry at low evaporation temperature, improves PPI level of an O L ED device, improves yield of a production line, has high film forming stability, can ensure that the material keeps a film form and does not form local crystallization in the use process after being applied to the O L ED device, causes short circuit of a device electrode, and prolongs the service life of the O L ED device.
The following describes in detail the application effect of the synthesized O L ED material in the device through device examples 1 to 10 and comparative example 1. the device of the device examples 2 to 10 and comparative example 1 has the same manufacturing process as the device of the device example 1, and the same substrate material and electrode material are used, the film thickness of the electrode material is also kept consistent, except that the device 2 to 9 changes the host material of the light-emitting layer 5 in the device, the device 10 uses the material of the invention as the hole transport/electron blocking layer, and the performance test results of the device obtained in each example are shown in table 2.
Device example 1
An electroluminescent device, which is prepared by the steps comprising:
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 HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
c) evaporating a hole transport material NPB (N-propyl bromide) on the hole injection layer 3 in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 80nm, and the hole transport layer/electron blocking layer 4 is formed;
d) depositing a light-emitting layer 5 on the hole transporting/electron blocking layer 4 by vapor deposition using the compound 7 of the present invention as a host material, Ir (ppy)3As the doping material, the material is 10% thick by doping amountThe degree is 30 nm;
e) an electron transport material TPBI is evaporated on the light-emitting layer 5 in a vacuum evaporation mode, the thickness of the TPBI is 40nm, and the organic material of the TPBI layer is used as a hole blocking/electron transport layer 6;
f) an electron injection layer L iF is vacuum-evaporated on the hole blocking/electron transporting layer 6, with a thickness of 1nm, and the layer is an electron injection layer 7;
g) a cathode Mg/Ag layer is vacuum-evaporated on the electron injection layer 7, the doping ratio of Mg to Ag is 9:1, the thickness of the cathode Mg/Ag layer is 15nm, the thickness of Ag is 3nm, and the cathode Mg/Ag layer is a cathode reflection electrode layer 8;
after the electroluminescent device was fabricated according to the above procedure, the current efficiency and lifetime of the device were measured, and the results are shown in table 2.
The molecular mechanism formula of the related material is as follows:
Figure BDA0001093433920000351
device example 2
This embodiment differs from device embodiment 1 in that: the main material of the light-emitting layer of the electroluminescent device is changed into the compound 10 of the invention, and the doping material is Ir (ppy)3The doping ratio was 10%, and the inspection data of the obtained electroluminescent device are shown in table 2.
Device example 3
This embodiment differs from device embodiment 1 in that: the host material of the luminescent layer of the electroluminescent device is changed into the compound 13 of the invention, and the doping material is Ir (ppy)3The doping ratio was 10%, and the inspection data of the obtained electroluminescent device are shown in table 2.
Device example 4
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 10 and the compound GHN of the invention, and the doping material is Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 5
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 66 and the compound GHN of the invention, and the doping material is Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 6
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 72 and the compound GHN of the invention, and the doping material is Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 7
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 81 and the compound GHN of the invention, and the doping material is Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 8
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 86 and the compound GHN of the invention, and the doping material Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 9
This embodiment differs from device embodiment 1 in that: the host material of the light emitting layer of the electroluminescent device is changed into the compound 91 and the compound GHN, and the doping material is Ir (ppy)3The mixing mass ratio of the three materials is 60:30:10, and the detection data of the obtained electroluminescent device is shown in Table 2.
Device example 10
This embodiment differs from device embodiment 1 in that: the material of the hole transport/electron blocking layer 4 of the electroluminescent device is changed into the compound 40 of the invention, the host material of the luminescent layer 5 is the known compound CBP, and the doping materialIs Ir (ppy)3The doping ratio was 10%, and the inspection data of the obtained electroluminescent device are shown in table 2.
Device comparative example 1
This embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the electroluminescent device was changed to the known compound CBP, and the detection data of the obtained electroluminescent device are shown in table 2.
TABLE 2
Figure BDA0001093433920000371
Note that the device test performance was evaluated by referring to comparative device example 1, each performance index of the device of comparative example 1 was 1.0, the current efficiency of comparative example 1 was 28cd/A (@10mA/cm2), the CIE color coordinates were (0.33,0.63), and the lifetime attenuation of L T95 at 5000 luminance was 2.5 Hr.
From the results of table 2, it can be seen that the organic compound containing a dimethylanthracene structure of the present invention can be applied to the fabrication of an O L ED light emitting device, and compared with the comparative example, the efficiency and lifetime of the organic compound are greatly improved compared with those of the known O L ED material, and particularly, the lifetime decay of the device is greatly improved.
Therefore, the above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the invention, and any modifications, equivalents, improvements and the like that are within the spirit and principle of the present invention should be included in the scope of the present invention.

Claims (2)

1. An organic compound containing dimethylanthracene, characterized in that the specific structural formula of the compound is:
Figure FDA0002523548480000011
Figure FDA0002523548480000021
Figure FDA0002523548480000022
any one of them.
2. An organic electroluminescent device comprising at least one functional layer containing the organic compound containing dimethylanthracene of claim 1.
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