CN111253377A - Compound, display panel and display device - Google Patents

Compound, display panel and display device Download PDF

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CN111253377A
CN111253377A CN202010131505.7A CN202010131505A CN111253377A CN 111253377 A CN111253377 A CN 111253377A CN 202010131505 A CN202010131505 A CN 202010131505A CN 111253377 A CN111253377 A CN 111253377A
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CN111253377B (en
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张磊
高威
牛晶华
代文朋
李侠
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Wuhan Tianma Microelectronics Co Ltd
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Shanghai Tianma AM OLED Co Ltd
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Abstract

The present invention belongs to the technical field of OLED and provides a compound used as a hole transport material and an electron blocking material, wherein the compound has a chemical formula 1]The general structure shown in [ chemical formula 1]]In, L1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene, or a substituted or unsubstituted C4-C40 heteroarylene; ar (Ar)1And Ar2Each independently selected from [ chemical formula 2]]And [ chemical formula 3]A group represented by, and Ar1And Ar2Are different from each other. The compound contains carbazole and diarylamine structures, has good hole transport capability, and the addition of dibenzothiophene or dibenzofuran groups can effectively adjust the HOMO energy level of molecules so as to be matched with materials of other light-emitting functional layers. The invention also provides a display panel and a display device.

Description

Compound, display panel and display device
Technical Field
The invention belongs to the technical field of OLED (organic light emitting diode), and particularly relates to a compound mainly used as a hole transport material and an electron blocking material, a display panel comprising the compound and a display device comprising the compound.
Background
The R, G, B sub-pixel display mode is adopted by small and medium-sized OLED screens such as mobile phone consumer products. In order to improve the production yield, some functional layers are designed as a common layer, which can reduce the use of FMM (fine metal mask), and the hole transport layer is often a common layer, which can be a commercially available material.
There are several problems with existing hole transport material technology. Firstly, the poor solubility of the material can cause the poor cleaning effect of the evaporation mask in mass production; secondly, the mobility of the material is too slow, which can cause the integral voltage of the device to be too high; thirdly, the mobility of the material is too fast, especially the lateral mobility of the material is too fast, so that crosstalk occurs between adjacent pixels; fourthly, the LUMO energy level of the material is too deep to effectively block the electron migration which may cross the light-emitting layer; fifthly, the triplet state energy level of the material is low, and effective transmission of holes in RGB three colors cannot be realized simultaneously, so that the use number of masks is increased and the process difficulty is improved.
Therefore, there is a need to design and develop hole transport materials with better performance.
Disclosure of Invention
The present invention provides a compound having a general structure represented by [ chemical formula 1 ]:
Figure BDA0002395883070000011
wherein, in [ chemical formula 1]In, L1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene group, or a substituted or unsubstitutedSubstituted C4-C40 heteroarylene;
Ar1and Ar2Each independently selected from [ chemical formula 2]]And [ chemical formula 3]A group represented by, and Ar1And Ar2Are different from each other;
Figure BDA0002395883070000021
in [ chemical formula 2]]In, R1And R2Each independently selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C40 fused aryl, substituted or unsubstituted C4-C40 heteroaryl;
in [ chemical formula 3], Cy represents a fused C6-C20 aromatic ring, and X is selected from an O atom or an S atom;
the heteroatoms in the heteroaryl or heteroarylene group are selected from one or more of P, S, N, O, B, Si;
denotes the connection position.
The compound provided by the invention contains a hole transport material of fused ring oxafluorene/thiafluorene, carbazole group and diarylamine group. The compound molecules of the material have a shallow LUMO value and a proper HOMO value, so that the transmission capability of holes can be effectively improved, and the transition of electrons can be effectively blocked. The compounds of the invention also have a relatively high triplet energy level ETThe organic electroluminescent material can effectively block the transmission of excitons, limit the excitons in the light-emitting layer and improve the transmission of holes. In addition, the compound provided by the invention has high hole mobility, excellent thermal stability and film stability, and is beneficial to improving the luminous efficiency and prolonging the service life of devices.
Drawings
FIG. 1 shows the chemical structure of one exemplary compound of the invention HT 001;
FIG. 2 is a schematic structural diagram of an OLED device provided by an embodiment of the present invention;
fig. 3 is a schematic diagram of a display device according to an embodiment of the present invention.
Detailed Description
The present invention is further illustrated by the following examples and comparative examples, which are intended to be illustrative only and are not to be construed as limiting the invention. The technical scheme of the invention is to be modified or replaced equivalently without departing from the scope of the technical scheme of the invention, and the technical scheme of the invention is covered by the protection scope of the invention.
One aspect of the present invention provides a compound having a general structure represented by [ chemical formula 1 ]:
Figure BDA0002395883070000031
wherein, in [ chemical formula 1]In, L1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene, or a substituted or unsubstituted C4-C40 heteroarylene;
Ar1and Ar2Each independently selected from [ chemical formula 2]]And [ chemical formula 3]A group represented by, and Ar1And Ar2Are different from each other;
Figure BDA0002395883070000032
in [ chemical formula 2]]In, R1And R2Each independently selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C40 fused aryl, substituted or unsubstituted C4-C40 heteroaryl;
in [ chemical formula 3], Cy represents a fused C6-C20 aromatic ring, and X is selected from an O atom or an S atom;
the heteroatoms in the heteroaryl or heteroarylene group are selected from one or more of P, S, N, O, B, Si;
denotes the connection position.
The compound has carbazole and arylamine structures and good hole transmission capability, and the addition of dibenzothiophene or dibenzofuran groups can effectively adjust the HOMO energy level of molecules so as to be matched with materials of other light-emitting functional layers.
According to one embodiment of the compounds of the present invention, L1And L2Selected from single bonds, Ar1Selected from [ chemical formula 2]Group of，Ar2Selected from [ chemical formula 3]The group shown. The molecule synthesis of this example is simple and does not increase the length of the conjugated chain of the molecule itself, and thus does not cause deterioration in the absorption of the hole transport material.
According to one embodiment of the compound of the present invention, in [ chemical formula 2]]In, R1And R2Selected from phenyl. [ chemical formula 2]R in the group of1And R2When the compound is selected from phenyl, the solubility of molecules is not deteriorated, so that the difficulty of cleaning a mask is not increased, and the length of a conjugated chain of the molecules is not increased, so that the absorption of a hole-transport material is not deteriorated.
According to one embodiment of the compound of the present invention, in [ chemical formula 3], Cy represents a condensed benzene ring.
According to one embodiment of the compounds of the present invention, L1And L2Each independently selected from any one of the groups shown below:
Figure BDA0002395883070000051
Z1and Z2Each independently selected from a hydrogen atom, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 fused aryl group, a substituted or unsubstituted C6-C30 fused heteroaryl group, a substituted or unsubstituted C1-C16 alkyl group, and a substituted or unsubstituted C1-C16 alkoxy group;
p and q are each independently selected from 1,2, 3;
# denotes the ligation site.
According to one embodiment of the compounds of the present invention, L1And L2Each independently selected from any one of the groups shown below:
Figure BDA0002395883070000061
according to one embodiment of the compound of the present invention, the compound is selected from any one of the following compounds:
Figure BDA0002395883070000071
Figure BDA0002395883070000081
Figure BDA0002395883070000091
Figure BDA0002395883070000101
according to one embodiment of the compound of the invention, the triplet level E of said compoundTIs 2.6eV or more. The compound has high triplet state energy level, can effectively block the transmission of excitons, limits the excitons in the light-emitting layer and prevents the loss of the excitons, thereby improving the light-emitting efficiency of the device.
According to one embodiment of the compound of the present invention, the compound has a glass transition temperature TgIs above 120 ℃.
The invention also provides a display panel comprising an organic light-emitting device, wherein the organic light-emitting device comprises an anode and a cathode which are oppositely arranged, and a hole transport layer and a light-emitting layer which are arranged between the anode and the cathode, wherein the material of the hole transport layer comprises one or more compounds disclosed by the invention.
According to one embodiment of the display panel, the display panel further comprises an electron blocking layer between the anode and the cathode, the electron blocking layer comprising one or more of the compounds of the present invention.
In the display panel provided by the present invention, the anode material of the organic light emitting device may be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof. The anode material may also be selected from metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; the anode material may also be selected from conductive polymers such as polyaniline, polypyrrole, poly (3-methylthiophene), and the like. In addition, the anode material may also be selected from materials that facilitate hole injection in addition to the anode materials listed above, and combinations thereof, including known materials suitable for use as anodes.
In the display panel provided by the present invention, the cathode material of the organic light emitting device may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof. The cathode material may also be selected from multi-layered metallic materials such as LiF/Al, LiO2/Al、BaF2Al, etc. In addition to the cathode materials listed above, the cathode materials can also be materials that facilitate electron injection and combinations thereof, including materials known to be suitable as cathodes.
In the embodiment of the present invention, the manufacturing process of the organic light emitting device is as follows: an anode is formed on a transparent or opaque smooth substrate, an organic thin film layer is formed on the anode, and a cathode is formed on the organic thin film layer. The organic thin film layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like. The organic thin film layer at least comprises a hole transport layer and a light-emitting layer, and the material of the hole transport layer is the compound disclosed by the invention. The organic thin film layer can also comprise an electron blocking layer, and the material of the electron blocking layer is the compound disclosed by the invention.
Another aspect of the invention illustratively describes the synthesis of compounds HT001, HT015, HT017, HT021, HT028, and HT 031.
Example 1
Synthesis of Compound HT001
Figure BDA0002395883070000111
In a 250ml round bottom flask 4-bromo-9H-carbazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and 8-chloro-benzofuronaphthalene (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Refluxing for 48 hours under an atmosphere, the resulting intermediate was cooled to room temperature, added to water, then filtered through a pad of celite while extracting with dichloromethane,then, washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then, the crude product was purified by silica gel column chromatography to obtain an intermediate HT 001-1.
In a 250ml round-bottom flask, the intermediate HT001-1(12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and diphenylamine (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux under ambient conditions for 48 hours, the resulting intermediate was cooled to room temperature, added to water, then filtered through a pad of celite while extracting with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give the final product HT 001.
Elemental analysis result of Compound HT001 (formula C)40H26N2O): theoretical value: c, 87.25; h, 4.76; n, 5.09; o, 2.91. Test values are: c, 87.25; h, 4.75; n, 5.10; o, 2.91. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 550.20 and the test value is 550.65.
Example 2
Synthesis of Compound HT015
Figure BDA0002395883070000121
In a 250ml round bottom flask 4-bromo-9H-carbazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and 6-chloro-benzothiophenaphthalene (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux was carried out under an atmosphere for 48 hours, and the resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate HT 015-1.
In a 250ml round-bottom flask, the intermediate HT015-1(12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and biphenyl-4-phenylamine (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux was carried out under an atmosphere for 48 hours, and the resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain a final product HT 015.
Elemental analysis result of Compound HT015 (formula C)46H30N2S): theoretical value: c, 85.95; h, 4.70; n, 4.36; and S, 4.99. Test values are: c, 85.88; h, 4.71; n, 4.37; and S, 5.01. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 642.23 and the test value is 642.81.
Example 3
Synthesis of Compound HT017
Figure BDA0002395883070000131
In a 250ml round bottom flask 4-bromo-9H-carbazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and 6-chloro-benzofuronaphthalene (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux was carried out under an atmosphere for 48 hours, and the resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, followed by washing with water, and drying with anhydrous magnesium sulfate, filtration and evaporation, and then the crude product was purified by silica gel column chromatography to obtain intermediate HT 017-1.
In a 250ml round-bottom flask, the intermediate HT017-1(12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and diphenylamine (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux was carried out under an atmosphere for 48 hours, and the resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, followed by washing with water, and drying with anhydrous magnesium sulfate, filtration and evaporation, and then the crude product was purified by silica gel column chromatography to obtain the final product HT 017.
Elemental analysis result of Compound HT017 (formula C017)52H34N2O): theoretical value: c, 88.86; h, 4.88; n, 3.99; o, 2.28. Test values are: c, 88.86; h, 4.90; n, 3.98; o, 2.28. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 702.27 and the test value is 702.84.
Example 4
Synthesis of Compound HT021
Figure BDA0002395883070000141
In a 250ml round bottom flask 4-bromo-9H-carbazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and 7-chloro-benzofuronaphthalene (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux under ambient conditions for 48 hours, the resulting intermediate was cooled to room temperature, added to water, then filtered through a pad of celite while extracting with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate HT 021-1.
In a 250mL round-bottom flask, intermediate HT021-1(12mmol), (4-boronic acid-naphthyl) -diphenylamine (12mmol) and Na2CO3(80mmol) were added to toluene/EtOH (absolute ethanol)/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the intermediate obtained by the reflux reaction under a nitrogen atmosphere for 20 hours was cooled to room temperature, added to water, and then filtered through a celite pad while being extracted with dichloromethane, then washed with water, and dried with anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product HT 021.
Elemental analysis result of Compound HT021 (formula C)50H32N2O): theoretical value: c, 88.73; h, 4.77; n, 4.14; o, 2.36. Test values are: c, 88.73; h, 4.79; n, 4.13; o, 2.36. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 676.25 and the test value is 676.80.
Example 5
Synthesis of Compound HT028
Figure BDA0002395883070000151
In a 250ml round bottom flask 4-bromo-9H-carbazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and (4-chloro-phenyl) -diphenylamine (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux for 48 hours under ambient. The resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, and then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate HT 028-1.
In a 250mL round-bottom flask, intermediate HT028-1(12mmol), 6-boronic acid-benzofuronaphthalene (12mmol) and Na2CO3(80mmol) were added to toluene/EtOH (absolute ethanol)/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution. The intermediate obtained by performing the reflux reaction for 20 hours under a nitrogen atmosphere was cooled to room temperature, added to water, and then filtered through a celite pad while being extracted with dichloromethane, and then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain a final product HT 028.
Elemental analysis result of Compound HT028 (formula C)46H30N2O): theoretical value: c, 88.15; h, 4.82; n, 4.47; o, 2.55. Test values are: c, 88.15; h, 4.81; n, 4.48; o, 2.55. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 626.24 and the test value is 626.74.
Example 6
Synthesis of Compound HT031
Figure BDA0002395883070000152
In a 250ml round-bottom flask, 4-bromo-9H-carboOxazole (12mmol), copper iodide (15mmol), potassium tert-butoxide (65mmol), 1, 2-diaminocyclohexane (12mmol) and (4-chloro-phenyl) -bis (4-pyridyl) -amine (12mmol) were added to dry 1, 4-dioxane (100ml) in N2Reflux was carried out under an atmosphere for 48 hours, and the resulting intermediate was cooled to room temperature, added to water, and then filtered through a celite pad while extracting with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain intermediate HT 031-1.
In a 250mL round-bottom flask, intermediate HT031-1(12mmol), 6-boronic acid-benzofuronaphthalene (12mmol) and Na2CO3(80mmol) were added to toluene/EtOH (absolute ethanol)/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the intermediate obtained by the reflux reaction under a nitrogen atmosphere for 20 hours was cooled to room temperature, added to water, and then filtered through a celite pad while being extracted with dichloromethane, followed by washing with water, and drying with anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product HT 031.
Elemental analysis result of Compound HT031 (formula C)44H28N4O): theoretical value: c, 84.06; h, 4.49; n, 8.91; o, 2.54. Test values are: c, 84.06; h, 4.50; n, 8.90; o, 2.54. ESI-MS (M/z) (M +) by liquid mass spectrometry: the theoretical value is 628.23 and the test value is 628.72.
Table 1 below lists HOMO, LUMO and energy level difference E of compounds HT001, HT015, HT017, HT021, HT028, HT031 and comparative examples NPB, Prime-1gAnd triplet energy level (E)T)。
TABLE 1
Figure BDA0002395883070000161
Figure BDA0002395883070000171
As can be seen from table 1 above, compared with the comparative material NPB, the HT001, HT015, HT017, HT021, HT028, and HT031 materials of the present invention have lower HOMO levels and higher LUMO levels, which are both favorable for injection and transport of holes and for blocking electrons passing through the light emitting layer, and confine the holes and the electrons in the light emitting layer, and increase the recombination probability of the holes and the electrons, the compound of the present invention has higher triplet level, which is favorable for restricting the backflow of excitons in the light emitting layer, effectively restricts the excitons in the light emitting layer, effectively reduces the generation of non-radiative energy, and increases the light emitting efficiency and the device lifetime.
Fabrication of organic light emitting devices
Device example 1 blue organic light-emitting device (the compound of the present invention was used as a hole transport layer material)
The present embodiment provides an organic light emitting device. As shown in fig. 2, the organic light emitting device includes: the structure of the organic electroluminescent device comprises a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9 (a magnesium-silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL)10, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the electron blocking layer 5 is 30nm, the thickness of the light emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 30nm, the thickness of the second electron transport layer 8 is 5nm, the thickness of the magnesium-silver electrode 9 is 15nm and the thickness of the cap layer (CPL)10 is 100 nm.
The organic light-emitting device of the present invention is prepared by the following steps:
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically treated in isopropanol and deionized water, respectively, for 30 minutes, and then exposed to ozone for about 10 minutes to perform cleaning; mounting the resulting glass substrate with the ITO anode 2 on a vacuum deposition apparatus;
2) evaporating a hole buffer layer material, namely HT 001: HAT-CN obtained in example 1, on the ITO anode 2 in a vacuum evaporation mode, wherein a layer with the thickness of 10nm is obtained by the mass ratio of a compound HT1 to the HAT-CN being 98:2, and the layer is used as a first hole transmission layer 3;
3) vacuum evaporating a material HT001 of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with the thickness of 95nm, wherein the layer is used as the second hole transport layer 4;
4) evaporating a material Prime-1 on the second hole transport layer 4 to obtain a layer with the thickness of 30nm, wherein the layer is used as an electron blocking layer 5;
5) co-depositing a light-emitting layer 6 on the electron blocking layer 5, wherein BH is used as a main body material, BD is used as a doping material, the mass ratio of BH to BD is 97:3, and the thickness of the light-emitting layer 6 is 30 nm;
6) vacuum evaporation is carried out on the material ET-1 of the first electron transport layer 7 on the luminous layer 6 to obtain the first electron transport layer 7 with the thickness of 30 nm;
7) evaporating LiF material of the second electron transport layer 8 on the first electron transport layer 7 in vacuum to obtain the second electron transport layer 8 with the thickness of 5 nm;
8) performing vacuum evaporation on the second electron transport layer 8 to obtain a cathode 9 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9: 1;
9) a hole-type material CPL-1 having a high refractive index was vacuum-deposited on the cathode 9 to a thickness of 100nm, and used as a cathode cover layer (cap layer or CPL) 10.
The structural formulas of the materials HAT-CN, HT001, BH, BD, Prime-1, NPB, ET-1 and CPL-1 mentioned in the steps are respectively shown as follows:
Figure BDA0002395883070000181
Figure BDA0002395883070000191
device example 2
In comparison with [ device example 1], the manufacturing process of [ device example 2] is the same for each layer of material and the manufacturing steps except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 is replaced with HT 015.
Device example 3
Compared with [ device example 1], the manufacturing process of [ device example 3] is the same for each layer of material and the manufacturing steps except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 is replaced with HT 017.
Device example 4
In comparison with [ device example 1], the manufacturing process of [ device example 4] is the same for each layer of materials and manufacturing steps except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 is replaced with HT 021.
Device example 5
In comparison with [ device example 1], the manufacturing process of [ device example 5] is the same for each layer of materials and preparation steps except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 is replaced with HT 028.
Device example 6
In comparison with [ device example 1], the manufacturing process of [ device example 6] is the same for each layer except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 is replaced with HT031, and the materials and the manufacturing steps are the same.
Comparative device example 1
In comparison with [ device example 1], the fabrication process of [ device comparative example 1] was the same for each layer of material and fabrication steps except that HT001 in the first hole transport layer 3 and the second hole transport layer 4 was replaced with NPB.
Figure BDA0002395883070000201
TABLE 2 test result tables of device example and device comparative example 1
Figure BDA0002395883070000202
Figure BDA0002395883070000211
Note: E/CIEy represents the ratio of efficiency (E) to CIEy.
As can be seen from table 2, the devices using the compounds of the present invention HT001, HT015, HT017, HT021, HT028, and HT031 had lower driving voltages, higher device efficiencies, and longer device lifetimes than the comparative device examples. The material has the HOMO and LUMO energy level values which are more matched with those of adjacent layers, and can effectively inject and transmit holes, improve the recombination probability of the holes and electrons, and further effectively improve the efficiency and the service life of a device.
Fabrication of organic light emitting devices
Device example 7 blue organic light-emitting device (Compound of the present invention used as a Material for an Electron blocking layer)
The present embodiment provides an organic light emitting device. The organic light emitting device of this example was the same in structure as device example 1 except for the materials in the respective functional layers. As shown in fig. 2, the organic light emitting device includes: the structure of the organic electroluminescent device comprises a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9 (a magnesium-silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL)10, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the electron blocking layer 5 is 90nm, the thickness of the light emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 30nm, the thickness of the second electron transport layer 8 is 5nm, the thickness of the magnesium-silver electrode 9 is 15nm and the thickness of the cap layer (CPL)10 is 100 nm.
The organic light-emitting device of the present invention is prepared by the following steps:
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically treated in isopropanol and deionized water, respectively, for 30 minutes, and then exposed to ozone for about 10 minutes to perform cleaning; mounting the resulting glass substrate with the ITO anode 2 on a vacuum deposition apparatus;
2) on the ITO anode 2, a hole buffer layer material NPB is evaporated in a vacuum evaporation mode: HAT-CN, resulting in a layer with a thickness of 10nm as the first hole transport layer 3;
3) vacuum evaporating a material NPB of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with the thickness of 95nm, wherein the layer is used as the second hole transport layer 4;
4) the material HT001 obtained in example 1 was vapor-deposited on the hole transport layer 4 to obtain a layer having a thickness of 90nm, which served as the electron blocking layer 5;
5) co-depositing a light-emitting layer 6 on the electron blocking layer 5, wherein BH is used as a main body material, BD is used as a doping material, the mass ratio of BH to BD is 97:3, and the thickness of the light-emitting layer 6 is 30 nm;
6) vacuum evaporation is carried out on the material ET-1 of the first electron transport layer 7 on the luminous layer 6 to obtain the first electron transport layer 7 with the thickness of 30 nm;
7) evaporating LiF material of the second electron transport layer 8 on the first electron transport layer 7 in vacuum to obtain the second electron transport layer 8 with the thickness of 5 nm;
8) performing vacuum evaporation on the second electron transport layer 8 to obtain a cathode 9 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9: 1;
9) a hole-type material CPL-1 having a high refractive index was vacuum-deposited on the cathode 9 to a thickness of 100nm, and used as a cathode cover layer 10 (cap layer or CPL).
The structural formulas of the materials HAT-CN, NPB, HT001, BH, BD, ET-1 and CPL-1 mentioned in the steps are respectively shown as follows:
Figure BDA0002395883070000221
Figure BDA0002395883070000231
device example 8
In comparison with [ device example 7], the manufacturing process of [ device example 8] is the same for each layer of material and the manufacturing steps except that HT001 in the electron blocking layer 5 is replaced with HT 015.
Device example 9
Compared with [ device example 7], the manufacturing process of [ device example 9] is the same for each layer of material and the manufacturing steps except that HT001 in the electron blocking layer 5 is replaced with HT 017.
Device example 10
In comparison with [ device example 7], the fabrication process of [ device example 10] is the same for each layer of material and fabrication steps except that HT001 in the electron blocking layer 5 is replaced with HT 021.
Device example 11
In comparison with [ device example 7], the fabrication process of [ device example 11] was the same for each layer of material and fabrication steps except that HT001 in the electron blocking layer 5 was replaced with HT 028.
Device example 12
In comparison with [ device example 7], the manufacturing process of [ device example 12] is the same for each layer of material and the manufacturing steps except that HT001 in the electron blocking layer 5 is replaced with HT 031.
Comparative device example 2
In comparison with [ device example 7], the fabrication process of [ device comparative example 2] was the same for each layer of material and fabrication steps except that HT001 in the electron blocking layer 5 was replaced with Prime-1.
TABLE 3 test result tables of device example and device comparative example 2
Figure BDA0002395883070000232
Figure BDA0002395883070000241
As can be seen from table 3, the devices using the compounds of the present invention HT001, HT015, HT017, HT021, HT028, and HT031 had lower driving voltages, higher device efficiencies, and longer device lifetimes than the device comparative examples. This is due to the fact that the material of the present invention has a more matched HOMO to adjacent layers, and a higher LUMO energy level, which effectively blocks electrons from passing through the light emitting layer, confining the electrons within the light emitting layer and recombining with holes. The material of the invention has higher triplet state energy level, can effectively limit exciton reflux in the luminescent layer, limit excitons in the luminescent layer, improve the utilization rate of the excitons, effectively reduce the generation of non-radiative energy, and thus effectively improve the efficiency and the service life of the device.
Yet another aspect of the present invention also provides a display device comprising the display panel as described above.
In the present invention, the organic light emitting device may be an OLED, which may be used in an organic light emitting display device, wherein the organic light emitting display device may be a display screen of a mobile phone, a display screen of a computer, a display screen of a television, a display screen of a smart watch, a display panel of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like. Fig. 3 is a schematic diagram of a display device according to an embodiment of the present invention. In fig. 3, 20 denotes a display panel of a cellular phone, and 30 denotes a display device.
Although the present application has been described with reference to preferred embodiments, it is not intended to limit the scope of the claims, and many possible variations and modifications may be made by one skilled in the art without departing from the spirit of the application.

Claims (12)

1. A compound having a general structure represented by [ chemical formula 1 ]:
Figure FDA0002395883060000011
wherein, in [ chemical formula 1]In, L1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene, or a substituted or unsubstituted C4-C40 heteroarylene;
Ar1and Ar2Each independently selected from [ chemical formula 2]]And [ chemical formula 3]A group represented by, and Ar1And Ar2Are different from each other;
Figure FDA0002395883060000012
in [ chemical formula 2]]In, R1And R2Each independently selected from substituted or unsubstitutedA C6-C40 aryl group, a substituted or unsubstituted C12-C40 fused aryl group, a substituted or unsubstituted C4-C40 heteroaryl group;
in [ chemical formula 3], Cy represents a fused C6-C20 aromatic ring, and X is selected from an O atom or an S atom;
the heteroatoms in the heteroaryl or heteroarylene group are selected from one or more of P, S, N, O, B, Si;
denotes the connection position.
2. The compound of claim 1, wherein L is1And L2Selected from single bonds, Ar1Selected from [ chemical formula 2]Group of formula (I), Ar2Selected from [ chemical formula 3]The group shown.
3. The compound of claim 1, wherein [ chemical formula 2]]In, R1And R2Selected from phenyl.
4. The compound according to claim 1, wherein in [ chemical formula 3], Cy represents a fused benzene ring.
5. The compound of claim 1, wherein L is1And L2Each independently selected from any one of the groups shown below:
Figure FDA0002395883060000021
Z1and Z2Each independently selected from a hydrogen atom, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 fused aryl group, a substituted or unsubstituted C6-C30 fused heteroaryl group, a substituted or unsubstituted C1-C16 alkyl group, and a substituted or unsubstituted C1-C16 alkoxy group;
p and q are each independently selected from 1,2, 3;
# denotes the ligation site.
6. The compound of claim 5, whereinIn that L1And L2Each independently selected from any one of the groups shown below:
Figure FDA0002395883060000031
7. the compound of claim 1, wherein the compound is selected from any one of the following compounds:
Figure FDA0002395883060000041
Figure FDA0002395883060000051
Figure FDA0002395883060000061
Figure FDA0002395883060000071
8. the compound of claim 1, wherein the triplet energy level E of said compoundTIs 2.6eV or more.
9. The compound of claim 1, wherein the compound has a glass transition temperature TgIs above 120 ℃.
10. A display panel comprising an organic light emitting device, wherein the organic light emitting device comprises an anode, a cathode disposed opposite to each other, a hole transport layer and a light emitting layer disposed between the anode and the cathode, wherein a material of the hole transport layer comprises one or more compounds according to any one of claims 1 to 19.
11. The display panel of claim 10, further comprising an electron blocking layer between the anode and the cathode, the electron blocking layer comprising one or more of the compounds of any of claims 1 to 11.
12. A display device comprising the display panel of claim 11 or 12.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112159406A (en) * 2020-10-14 2021-01-01 上海天马有机发光显示技术有限公司 Compound, display panel and display device
JPWO2022009999A1 (en) * 2020-11-05 2022-01-13
KR102438159B1 (en) * 2021-05-24 2022-08-30 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160172597A1 (en) * 2014-12-15 2016-06-16 Samsung Display Co., Ltd. Carbazole compound, material for organic electroluminescent device, and organic electroluminescent device
KR20180060277A (en) * 2016-11-28 2018-06-07 원광대학교산학협력단 Compound for hole transporting material and preparing method thereof
CN109232382A (en) * 2018-11-15 2019-01-18 长春海谱润斯科技有限公司 A kind of carbazole derivates and its organic electroluminescence device
CN110577488A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound with carbazole as core and application thereof in organic electroluminescent device
CN110669040A (en) * 2019-09-26 2020-01-10 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN110746391A (en) * 2019-10-28 2020-02-04 上海天马有机发光显示技术有限公司 Compound, organic electroluminescent device and display device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160172597A1 (en) * 2014-12-15 2016-06-16 Samsung Display Co., Ltd. Carbazole compound, material for organic electroluminescent device, and organic electroluminescent device
KR20180060277A (en) * 2016-11-28 2018-06-07 원광대학교산학협력단 Compound for hole transporting material and preparing method thereof
CN110577488A (en) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 Compound with carbazole as core and application thereof in organic electroluminescent device
CN109232382A (en) * 2018-11-15 2019-01-18 长春海谱润斯科技有限公司 A kind of carbazole derivates and its organic electroluminescence device
CN110669040A (en) * 2019-09-26 2020-01-10 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN110746391A (en) * 2019-10-28 2020-02-04 上海天马有机发光显示技术有限公司 Compound, organic electroluminescent device and display device

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
薛小利: "浅谈OLED显示技术进展", 《科技与创新》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112159406A (en) * 2020-10-14 2021-01-01 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN112159406B (en) * 2020-10-14 2021-11-05 上海天马有机发光显示技术有限公司 Compound, display panel and display device
JPWO2022009999A1 (en) * 2020-11-05 2022-01-13
JP7196363B2 (en) 2020-11-05 2022-12-26 出光興産株式会社 Compounds, materials for organic electroluminescence devices, organic electroluminescence devices and electronic devices
US11795155B2 (en) 2020-11-05 2023-10-24 Idemitsu Kosan Co., Ltd. Compound having naphthobenzofuranyl structure, material for organic electroluminescence device, organic electroluminescence device, and electronic instrument
KR102438159B1 (en) * 2021-05-24 2022-08-30 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

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