CN110642820A - Electron blocking material and organic electroluminescent device - Google Patents
Electron blocking material and organic electroluminescent device Download PDFInfo
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- CN110642820A CN110642820A CN201910831187.2A CN201910831187A CN110642820A CN 110642820 A CN110642820 A CN 110642820A CN 201910831187 A CN201910831187 A CN 201910831187A CN 110642820 A CN110642820 A CN 110642820A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
An electron blocking material has the characteristics of high hole mobility and low electron mobility, and has good electron blocking capability. The electron blocking material is applied to the manufacture of organic electroluminescent devices, 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 organic electroluminescent device is obviously prolonged.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an electronic barrier material and an organic electroluminescent device.
Background
Organic light-emitting diodes (OLEDs) attract the attention of many researchers due to the advantages of no need of backlight source for active light emission, high light-emitting efficiency, large visual angle, fast response speed, large temperature adaptation range, relatively simple production and processing technology, low driving voltage, low energy consumption, lightness, thinness, flexible display and the like, and huge application prospects. In OLEDs, the dominant emissive guest material is of critical importance. The light-emitting guest material used in the early OLED is a fluorescent material, and since the exciton ratio of singlet state to triplet state in the OLED is 1:3, the quantum efficiency in the theory of the OLED based on the fluorescent material can only reach 25%, which greatly limits the application of the fluorescent electroluminescent device. The heavy metal complex phosphorescent material enables 100% IQE (internal quantum efficiency) to be achieved by simultaneously using singlet and triplet excitons due to the spin-orbit coupling effect of heavy atoms. However, the commonly used heavy metals are precious metals such as Ir and Pt, and the heavy metal complex phosphorescent materials have yet to be broken through in the aspect of blue light materials.
In summary, in the conventional organic electroluminescent device, the electron blocking layer material cannot satisfy the characteristics of high hole mobility and low electron mobility, which further affects the performance of the organic electroluminescent device.
Disclosure of Invention
The invention provides an electron blocking material and an organic electroluminescent device, which can realize the preparation of a high-efficiency organic electroluminescent device and solve the technical problem that the performance of the organic electroluminescent device is further influenced because the electron blocking material cannot meet the characteristics of high hole mobility and low electron mobility in the conventional organic electroluminescent device.
In order to solve the above problems, the technical scheme provided by the invention is as follows:
the invention provides an electron blocking material, wherein the molecular structure of a compound in the electron blocking material is shown as a general formula (1):
in the general formula (1), R1、R2Respectively as follows:
According to a preferred embodiment of the present invention, the electron blocking material comprises a first target compound, and the specific structural formula of the first target compound is:
according to a preferred embodiment of the present invention, the highest occupied orbital electrochemical energy level of the first target compound is-5.55 ev, and the lowest unoccupied orbital electrochemical energy level of the first target compound is-2.54 ev.
According to a preferred embodiment of the present invention, the electron blocking material comprises a second target compound, and the specific structural formula of the second target compound is:
according to a preferred embodiment of the present invention, the highest occupied orbital electrochemical level of the second target compound is-5.51 ev and the lowest unoccupied orbital electrochemical level of the second target compound is-2.59 ev.
According to a preferred embodiment of the present invention, the electron blocking material comprises a third target compound, and the specific structural formula of the third target compound is:
according to a preferred embodiment of the present invention, the electrochemical energy level of the highest occupied orbital of the third target compound is-5.57 ev, and the electrochemical energy level of the lowest unoccupied orbital of the third target compound is-2.53 ev.
The invention also provides an organic electroluminescent device which comprises an electron blocking layer and is characterized in that the electron blocking layer is made of the electron blocking material.
According to a preferred embodiment of the present invention, the light emitting device further includes a transparent substrate layer, an anode layer, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a semi-transparent electrode layer, and a light coupling-out layer, where the transparent substrate layer, the anode layer, the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer, the semi-transparent electrode layer, and the light coupling-out layer are sequentially stacked from bottom to top.
According to a preferred embodiment of the present invention, the anode layer includes a first ITO layer, a silver metal layer, and a second ITO layer, which are stacked.
The invention has the beneficial effects that: the electronic blocking material based on the dibenzofuran structure is applied to the manufacturing of the organic electroluminescent device, can realize the preparation of the organic electroluminescent device with high efficiency, and further prolongs the service life of the organic electroluminescent device.
Drawings
In order to illustrate the embodiments or the technical solutions in the prior art more clearly, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the invention, and it is obvious for a person skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
Fig. 1 is a schematic cross-sectional structure diagram of an organic electroluminescent device according to a first embodiment of the present invention.
FIG. 2 is a schematic cross-sectional view of a second embodiment of an organic electroluminescent device according to the present invention.
Fig. 3 is a schematic cross-sectional structure diagram of a third embodiment of an organic electroluminescent device according to the present invention.
Detailed Description
The following description of the various embodiments refers to the accompanying drawings that illustrate specific embodiments in which the invention may be practiced. The directional terms mentioned in the present invention, such as [ upper ], [ lower ], [ front ], [ rear ], [ left ], [ right ], [ inner ], [ outer ], [ side ], are only referring to the directions of the attached drawings. Accordingly, the directional terms used are used for explanation and understanding of the present invention, and are not used for limiting the present invention. In the drawings, elements having similar structures are denoted by the same reference numerals.
The invention aims at the technical problem that the performance of the organic electroluminescent device is further influenced because the electron blocking layer material of the existing organic electroluminescent device cannot meet the characteristics of high hole mobility and low electron mobility, and the embodiment can solve the defect.
The invention provides an electron blocking material, wherein the molecular structure of a compound in the electron blocking material is shown as a general formula (1):
in the general formula (1), R1、R2Respectively as follows:
Preferably, R1Group and R2The groups are the same; preferably, R1Group and R2The radicals are not identical.
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
The first embodiment is as follows:
the electron blocking material comprises a first target compound, and the specific structural formula of the first target compound is as follows:
the synthetic route for the first target compound is as follows:
the specific synthesis steps are as follows:
first, 2,8-Dibromo-4, 6-di-tert-butyldibenzofuran (2,8-Dibromo-4,6-di-tert-butyl-dibenzofuran, 2.18g, 5mmol), 3,6-Dimethylcarbazole (3,6-Dimethylcarbazole, 2.34g, 12mmol), palladium acetate (Pd (OAc))20.18g, 0.8mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF40.68g, 2.4mmol), then sodium tert-butoxide (NaOt-Bu, 1.16g, 12mmol) was added in a glove box, 100mL of toluene which had been previously dehydrated and deoxygenated were added under an argon atmosphere, and the reaction was carried out at 120 ℃ for 24 hours. Cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting with dichloromethane for three times, combining organic phases, spinning into silica gel, and separating and purifying by column chromatography (the volume ratio of dichloromethane to n-hexane is 1:5) to obtain 2.8g of white powder, namely the first target compound, wherein the yield is 81%.
Using MS (EI) to identify the first target compound having a molecular formula of C48H46N2O, detection value [ M ]]+666.20, calculated 666.36.
The application of the first target compound in an organic electroluminescent device can be used as an electron blocking layer material, and the HOMO energy level test and the LUMO energy level test are respectively carried out on the first target compound, so that the following results are obtained:
the highest occupied orbital (HOMO) of the first target compound has an electrochemical energy level of-5.55 eV, and the lowest unoccupied orbital (LUMO) of the first target compound has an electrochemical energy level of-2.54 eV. Wherein, the HOMO energy level and the LUMO energy level are both tested by an ionization energy testing system (IPS3), and the testing environment is an atmospheric environment. It is thus found that the first target compound satisfies the characteristics of high hole mobility and low electron mobility.
As shown in fig. 1, is a schematic view of a cross-sectional structure of an embodiment of an organic electroluminescent device obtained by the first target compound. The organic electroluminescent device according to embodiment one 10 includes, from bottom to top, a transparent substrate layer 11, an anode layer 12, a hole injection layer 13, a hole transport layer 14, an electron blocking layer 15, a light emitting layer 16, a hole blocking layer 17, an electron transport layer 18, an electron injection layer 19, a semi-transparent electrode layer 110, and a light coupling-out layer 111 that are sequentially stacked.
Specifically, the anode layer 12 includes a first ITO (indium tin oxide) layer, a silver metal layer, and a second ITO layer (ITO/Ag/ITO) that are stacked. The material of the electron blocking layer 15 is the first target compound, and the translucent electrode layer 110 serves as a cathode.
The preparation process of the organic electroluminescent device in the first embodiment 10 is as follows:
first, the anode layer 12 on the transparent substrate layer 11 is cleaned; then, the hole injection layer 13, the hole transport layer 14, the electron blocking layer 15, the light emitting layer 16, the hole blocking layer 17, the electron transport layer 18, the electron injection layer 19, the translucent electrode layer 110, and the light coupling-out layer 111 are sequentially vacuum-deposited on the anode layer 12.
The organic electroluminescent device prepared by using the first target compound as the electron barrier layer material has higher efficiency and longer service life than the organic electroluminescent device prepared by using the known electron barrier layer material.
Example two:
the electron blocking material comprises a second target compound, and the specific structural formula of the second target compound is as follows:
the synthetic route for the second target compound is as follows:
the specific synthesis steps are as follows:
first, 2,8-Dibromo-4, 6-Di-tert-butyldibenzofuran (2,8-Dibromo-4, 6-Di-t-butyl-dibenzofuran, 2.18g, 5mmol), 4, 4-dimethyldiphenylamine (Di-p-tolyalamine, 2.37g, 12mmol), palladium acetate (Pd (OAc))20.18g, 0.8mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF40.68g, 2.4mmol), then sodium tert-butoxide (NaOt-Bu, 1.16g, 12mmol) was added in a glove box, 100mL of toluene which had been previously dehydrated and deoxygenated were added under an argon atmosphere, and the reaction was carried out at 120 ℃ for 24 hours. Cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting with dichloromethane for three times, combining organic phases, spinning into silica gel, and separating and purifying by column chromatography (the volume ratio of dichloromethane to n-hexane is 1:5) to obtain 2.6g of white powder, namely the second target compound, with the yield of 78%.
Using MS (EI) to identify the second target compound having a molecular formula of C48H50N2O, detection value [ M ]]+670.26, calculated 670.39.
The application of the second target compound in the organic electroluminescent device can be used as an electron blocking layer material, and the HOMO energy level test and the LUMO energy level test are respectively carried out on the second target compound, so that the following results are obtained:
the highest occupied orbital (HOMO) of the second target compound has an electrochemical energy level of-5.51 eV, and the lowest unoccupied orbital (LUMO) of the second target compound has an electrochemical energy level of-2.59 eV. Wherein, the HOMO energy level and the LUMO energy level are both tested by an ionization energy testing system (IPS3), and the testing environment is an atmospheric environment. It is thus found that the second target compound satisfies the characteristics of high hole mobility and low electron mobility.
As shown in fig. 2, is a schematic cross-sectional structure diagram of an embodiment of an organic electroluminescent device obtained by the second target compound. The second organic electroluminescent device embodiment 20 includes, from bottom to top, a transparent substrate layer 21, an anode layer 22, a hole injection layer 23, a hole transport layer 24, an electron blocking layer 25, a light emitting layer 26, a hole blocking layer 27, an electron transport layer 28, an electron injection layer 29, a semitransparent electrode layer 210, and a light coupling-out layer 211, which are sequentially stacked.
Specifically, the anode layer 22 includes a first ITO (indium tin oxide) layer, a silver metal layer, and a second ITO layer (ITO/Ag/ITO) that are stacked. The material of the electron blocking layer 25 is the second target compound, and the translucent electrode layer 210 serves as a cathode.
The preparation process of the second organic electroluminescent device example 20 is as follows:
first, the anode layer 22 on the transparent substrate layer 21 is cleaned; then, the hole injection layer 23, the hole transport layer 24, the electron blocking layer 25, the light emitting layer 26, the hole blocking layer 27, the electron transport layer 28, the electron injection layer 29, the translucent electrode layer 210, and the light coupling-out layer 211 are sequentially vacuum-deposited on the anode layer 22.
The organic electroluminescent device prepared by using the second target compound as the electron blocking layer material has higher efficiency and longer service life than the organic electroluminescent device prepared by using the known electron blocking layer material.
Example three:
the electron blocking material comprises a third target compound, and the specific structural formula of the third target compound is as follows:
the synthetic route of the third target compound is as follows:
the specific synthesis steps are as follows:
first, 2,8-dibromo-4, 6-di-tert-butyldibenzofuran was added to a 250mL two-necked flaskPyran (2,8-Dibromo-4,6-di-tert-butyl-dibenzofuran, 2.18g, 5mmol), 9, 9' -dimethylacridine (9, 9-dimethylacridine, 2.50g, 12mmol), palladium acetate (Pd (OAc))20.18g, 0.8mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF40.68g, 2.4mmol), then sodium tert-butoxide (NaOt-Bu, 1.16g, 12mmol) was added in a glove box, 100mL of toluene which had been previously dehydrated and deoxygenated were added under an argon atmosphere, and the reaction was carried out at 120 ℃ for 24 hours. Cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting with dichloromethane for three times, combining organic phases, spinning into silica gel, and separating and purifying by column chromatography (the volume ratio of dichloromethane to n-hexane is 1:5) to obtain 2.1g of white powder, namely the third target compound, wherein the yield is 61%.
Using MS (EI) to identify the third target compound having a molecular formula of C50H50N2O, detection value [ M ]]+694.25, calculated 694.39.
The third target compound is applied to an organic electroluminescent device, and can be used as an electron blocking layer material to perform HOMO level test and LUMO level test on the third target compound respectively, and the following results are obtained:
the electrochemical energy level of the highest occupied orbital (HOMO) of the third target compound is-5.57 eV, and the electrochemical energy level of the lowest unoccupied orbital (LUMO) of the third target compound is-2.53 eV. Wherein, the HOMO energy level and the LUMO energy level are both tested by an ionization energy testing system (IPS3), and the testing environment is an atmospheric environment. It is thus found that the third target compound satisfies the characteristics of high hole mobility and low electron mobility.
As shown in fig. 3, is a schematic diagram of a three-section structure of an embodiment of an organic electroluminescent device obtained by the third target compound. The third organic electroluminescent device embodiment 30 includes, from bottom to top, a transparent substrate layer 31, an anode layer 32, a hole injection layer 33, a hole transport layer 34, an electron blocking layer 35, a light emitting layer 36, a hole blocking layer 37, an electron transport layer 38, an electron injection layer 39, a semi-transparent electrode layer 310, and a light coupling-out layer 311, which are sequentially stacked.
Specifically, the anode layer 32 includes a first ITO (indium tin oxide) layer, a silver metal layer, and a second ITO layer (ITO/Ag/ITO) that are stacked. The material of the electron blocking layer 35 is the third target compound, and the translucent electrode layer 310 serves as a cathode.
The preparation process of the organic electroluminescent device in example three 30 is as follows:
first, the anode layer 32 on the transparent substrate layer 31 is washed; then, the hole injection layer 33, the hole transport layer 34, the electron blocking layer 35, the light emitting layer 36, the hole blocking layer 37, the electron transport layer 38, the electron injection layer 39, the translucent electrode layer 310, and the light coupling-out layer 311 are sequentially vacuum-deposited on the anode layer 32.
The organic electroluminescent device prepared by using the third target compound as the electron blocking layer material has higher efficiency and longer service life than the organic electroluminescent device prepared by using the known electron blocking layer material.
The invention has the beneficial effects that: the electronic barrier material prepared based on the dibenzofuran structure is applied to the preparation of an organic electroluminescent device, can realize the preparation of the organic electroluminescent device with high efficiency, and further prolongs the service life of the organic electroluminescent device.
In summary, although the present invention has been described with reference to the preferred embodiments, the above-described preferred embodiments are not intended to limit the present invention, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention, therefore, the scope of the present invention shall be determined by the appended claims.
Claims (10)
1. An electron blocking material, wherein a molecular structure of a compound in the electron blocking material is represented by general formula (1):
in the general formula (1), R1、R2Respectively as follows:
2. The electron blocking material of claim 1, wherein the electron blocking material comprises a first target compound having a specific structural formula:
3. the electron blocking material according to claim 2, wherein the electrochemical energy level of the highest occupied orbital of the first target compound is-5.55 ev, and the electrochemical energy level of the lowest unoccupied orbital of the first target compound is-2.54 ev.
4. The electron blocking material of claim 1, wherein the electron blocking material comprises a second target compound having a specific structural formula:
5. the electron blocking material according to claim 4, wherein the electrochemical energy level of the highest occupied orbital of the second target compound is-5.51 ev, and the electrochemical energy level of the lowest unoccupied orbital of the second target compound is-2.59 ev.
6. The electron blocking material of claim 1, wherein the electron blocking material comprises a third target compound having a specific structural formula:
7. the electron blocking material according to claim 6, wherein the electrochemical energy level of the highest occupied orbital of the third target compound is-5.57 ev, and the electrochemical energy level of the lowest unoccupied orbital of the third target compound is-2.53 ev.
8. An organic electroluminescent device comprising an electron blocking layer, characterized in that the electron blocking layer is made of the electron blocking material of any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, further comprising a transparent substrate layer, an anode layer, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a semi-transparent electrode layer, and a light coupling-out layer, wherein the transparent substrate layer, the anode layer, the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer, the semi-transparent electrode layer, and the light coupling-out layer are sequentially stacked from bottom to top.
10. The organic electroluminescent device of claim 9, wherein the anode layer comprises a first ITO layer, a silver metal layer, and a second ITO layer in a stacked arrangement.
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