CN116891440A - Compound containing triazine structure and application of compound in organic electroluminescent device - Google Patents
Compound containing triazine structure and application of compound in organic electroluminescent device Download PDFInfo
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- CN116891440A CN116891440A CN202310310604.5A CN202310310604A CN116891440A CN 116891440 A CN116891440 A CN 116891440A CN 202310310604 A CN202310310604 A CN 202310310604A CN 116891440 A CN116891440 A CN 116891440A
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 230000000903 blocking effect Effects 0.000 claims abstract description 53
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 23
- 239000010409 thin film Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 86
- 238000002347 injection Methods 0.000 abstract description 32
- 239000007924 injection Substances 0.000 abstract description 32
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 180
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
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- 238000000034 method Methods 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 50
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- 229940125782 compound 2 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UVEAFTFQMHUWEY-UHFFFAOYSA-N methane;1,2,4,5-tetrafluoro-3,6-dioxocyclohexane-1,2,4,5-tetracarbonitrile Chemical compound C.C.N#CC1(F)C(=O)C(F)(C#N)C(F)(C#N)C(=O)C1(F)C#N UVEAFTFQMHUWEY-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a compound containing a triazine structure and application thereof in an organic electroluminescent device, and belongs to the technical field of semiconductor materials. The structure of the compound is shown as a general formula (1-1) or a general formula (1-2), the compound has good stability and electron tolerance, and simultaneously has good electron injection and hole blocking capabilities.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to a compound containing a triazine structure and application thereof in an organic electroluminescent device.
Background
The organic electroluminescent device (OLED: organic Light Emission Diodes) technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED device has a sandwich-like structure and comprises electrode material film layers and organic functional materials clamped between different electrode material film layers, and various organic functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to the electrodes at the two ends of the OLED light-emitting device serving as a current device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and thus OLED electroluminescence is generated.
Currently, the OLED display technology has been applied in the fields of smart phones, tablet computers and the like, and further will expand to the large-size application fields of televisions and the like. However, the performance of the OLED device, such as the luminous efficiency and the service life, needs to be further improved compared to the actual product application requirements. In order to realize the continuous improvement of the performance of the OLED device, the OLED photoelectric functional material is required to be continuously researched and innovated, and an OLED functional material with higher performance is created.
The OLED photoelectric functional materials applied to OLED devices can be divided into two main categories in terms of application, namely charge injection transport materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and as the charge transport material, it is required to have good carrier mobility, high glass transition temperature, and the like, and for an OLED device, electrons are injected from a cathode and then transferred to a host material through a hole blocking layer, and holes are recombined in the host material, thereby generating excitons. Therefore, the injection capability and the transmission capability of the hole blocking layer are improved, the device driving voltage is reduced, and meanwhile, the high-efficiency electron-hole recombination efficiency is obtained. Therefore, the hole blocking layer is very important, and it is required to have high electron injection capability, transport capability, and high durability of electrons.
With the remarkable progress of OLED devices, the performance requirements for materials are increasing, not only are they required to have good material stability, but also to achieve good efficiency and lifetime at low driving voltages. However, the current hole blocking materials have insufficient electron injection and hole blocking capability and heat resistance stability, and meanwhile, the electron tolerance of the materials has defects, so that the materials are separated or decomposed in phase state when the device works.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a compound containing a triazine structure and application thereof to an organic electroluminescent device, the compound is bridged by phenyl with a specific structure, and a substituent group is phenyl, biphenyl or naphthyl substituted fluorene derivative with a specific site, so that the compound has excellent electron injection and hole blocking capability, good electron durability and material stability, and can be applied to the organic electroluminescent device, effectively reduce the working voltage of the device, improve the luminous efficiency of the device and prolong the service life of the device.
The technical scheme of the invention is as follows:
a triazine structure-containing compound, the structure of which is shown as a general formula (1-1) or a general formula (1-2):
In the general formula (1-1) and the general formula (1-2), R 2 Represented by phenyl, biphenyl or naphthyl; l (L) 1 Represented by a single bond or phenylene;
r is represented by a structure shown in a general formula a, a general formula b or a general formula c;
R 1 represented by phenyl, biphenyl or naphthyl; x represents O, S, a single bond or a dimethyl-substituted methylene group.
Preferably, the structure of the triazine structure-containing compound is shown as any one of the general formulas (2-1) to (2-4):
r, R in the general formulae (2-1) to (2-4) 2 Is as defined above.
Preferably, the structure of the triazine structure-containing compound is shown as any one of the general formulas (3-1) to (3-4):
r, R in the general formulae (3-1) to (3-4) 2 Is as defined above.
Preferably, said R 1 、R 2 Each independently represented by any one of the structures shown below:
preferably, said R 2 Represented as phenyl.
Preferably, said R 2 Represented as biphenyl.
Preferably, said R 2 Represented as naphthyl.
Preferably, said R 1 Represented asPhenyl.
Further preferably, the specific structure of the triazine structure-containing compound is any one of the following structures:
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an organic electroluminescent device comprising a first electrode and a second electrode, wherein a plurality of organic thin film layers are arranged between the first electrode and the second electrode of the organic electroluminescent device, and at least one organic thin film layer contains the compound containing a triazine structure.
Preferably, the multi-layer organic thin film layer includes a hole blocking layer containing the triazine structure-containing compound.
A display element comprising the organic electroluminescent device.
The beneficial technical effects of the invention are as follows:
the compound is based on a triazine structure, wherein the triazine group is connected through a specific phenyl bridging group, and the substituent is aryl substituted fluorenyl, in particular to 9, 9-dimethylfluorene, 9-diphenylfluorene, spirofluorene, dimethyl spiroanthracene fluorene, spirofluorene xanthene or spirofluorene thioxanthene which are substituted by phenyl, biphenyl or naphthyl at specific positions, and the compound has good electron tolerance and stability and good electron injection and hole blocking capability. Therefore, when the organic light emitting diode is used as a hole blocking material of an OLED functional layer, the device driving voltage can be effectively reduced, and the photoelectric performance and the service life of an OLED device are improved.
The triazine structure compound can further delocalize the LUMO electron cloud distribution of the material, so that the electron tolerance of the material can be improved, and the electron stability of the material can be effectively improved. In addition, the aryl-substituted fluorenyl derivative group is introduced, so that the aryl-substituted fluorenyl derivative group has a good steric hindrance structure, pi-pi accumulation among molecules can be inhibited, the electron injection capability is obviously improved, and the driving voltage of a device is reduced. In addition, due to the existence of the aryl substituted fluorenyl derivative group, the electron tolerance and stability of the material are effectively improved. Therefore, the driving voltage of the device can be effectively reduced, and the service life of the device is prolonged.
Drawings
Fig. 1 is a schematic diagram of the structure of the materials listed in the present application applied to an OLED device.
In the figure, 1 is a transparent substrate layer, and 2 is an anode layer; 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
The technical aspects of the present application will be described in detail hereinafter with reference to the accompanying drawings and embodiments.
In the present application, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule unless otherwise specified. Furthermore, in the present application, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitudes of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
In the drawings, the size of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present application, in describing the electrodes and the organic electroluminescent device, and other structures, words such as "upper" and "lower" used to indicate orientations are merely indicative of orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present application, the "lower" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "upper" side.
Organic electroluminescent device
In another embodiment of the present application, there is provided an organic electroluminescent device comprising a first electrode (anode), a second electrode (cathode), and a plurality of organic thin film layers between the first electrode and the second electrode, wherein at least one organic thin film layer contains the triazine structure-containing compound.
In a preferred embodiment of the present application, the organic thin film layer comprises a hole blocking layer, wherein the hole blocking layer comprises the triazine structure-containing compound according to the present application.
In a preferred embodiment of the present application, the organic electroluminescent device according to the present application comprises a substrate, a first electrode layer (anode layer), an organic thin film layer, a second electrode layer (cathode layer), wherein the organic thin film layer includes, but is not limited to, a light emitting layer and a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, a second electrode (cathode) and a CPL layer
The preferred device structure of the present invention takes the form of top emission (topemitting). Preferably, the anode of the organic electroluminescent device of the present invention employs an electrode having high reflectivity, preferably ITO/Ag/ITO; the cathode adopts a transparent electrode, preferably adopts a mixed electrode of Mg and Ag=1:9, thereby forming a microcavity resonance effect, and the light emitted by the device is emitted from the side of the Mg and Ag electrode.
In a preferred embodiment of the present invention, an organic electroluminescent device is provided comprising a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode layer, and a CPL layer, wherein the anode is above the substrate, the hole injection layer is above the anode, the hole transport layer is above the hole injection layer, the electron blocking layer is above the hole transport layer, the light emitting layer is above the hole transport layer, the hole blocking layer is above the light emitting layer, the electron transport layer is above the hole blocking layer, the electron injection layer is above the electron transport layer, the cathode layer is above the electron injection layer, and the CPL layer is above the cathode layer.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may be used. Examples are transparent substrates, such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode (anode) is formed on the substrate, and the anode material is preferably a material having a high work function so that holes are easily injected into the organic functional material layer. Non-limiting examples of anode materials include, but are not limited to, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2 ) Zinc oxide (ZnO), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The first electrode may have a single-layer structure or a multi-layer structure including two or more layers. For example, the anode may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. In addition, the thickness of the anode depends on the material used, and is usually 50 to 500nm, preferably 70 to 300nm and more preferably 100 to 200nm.
A hole injection layer 3, a hole transport layer 4, and an electron blocking layer 5 may be disposed between the anode 2 and the light emitting layer 6.
The hole injection layer structure is such that a hole injection layer material, which may be, for example, a P dopant, is uniformly or non-uniformly dispersed in the hole transport layer. The P-dopant may be selected from at least one compound selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; or cyano-containing compounds, such as compounds P1, NDP and F4-TCNQ shown below:
According to the invention, P1 is preferably used as P dopant. The ratio of the hole transport layer to the P dopant used in the present invention is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the hole injection layer of the present invention may be 1 to 100nm, preferably 2 to 50nm and more preferably 5 to 20nm.
The material of the hole transport layer is preferably a material having high hole mobility, which enables holes to be transferred from the anode or the hole injection layer to the light emitting layer. The hole transporting material may be a styrene compound such as a phthalocyanine derivative, a triazole derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, an oxadiazole derivative, a hydrazone derivative, a stilbene derivative, a pyridinine derivative, a polysilane derivative, an imidazole derivative, a phenylenediamine derivative, an amino-substituted quininone derivative, a styrylanthracene derivative, a styrylamine derivative, a fluorene derivative, a spirofluorene derivative, a silazane derivative, an aniline copolymer, a porphyrin compound, a carbazole derivative, a polyarylalkane derivative, a polyphenyleneethylene and a derivative thereof, a polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, a conductive polymer such as a thiophene oligomer, an aromatic tertiary amine compound, a styrylamine compound, a triamine, a tetramine, a biphenylamine, a propyne derivative, a p-phenylenediamine derivative, a m-phenylenediamine derivative, a 1,1' -bis (4-diarylaminophenyl) cyclohexane, a 4,4' -bis (diarylamino) biphenyl, a bis [4- (diarylamino) phenyl ] methane, a 4,4' -bis (diarylamino) terphenyl, a 4,4' -bis (diarylamino) terphenyl) biphenyl, a 4' -bis (diarylamino) diaryl ether, a bis (4 ' -diarylamino) biphenyl, a bis (4 ' -diarylamino) diaryl ether, a bis (4 ' -diarylmethane) sulfide, a bis (4 ' -diarylamino) methane, a, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes or 2, 2-diphenylvinyl compounds, etc.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 180nm and more preferably 20 to 150nm.
The electron blocking layer requires that the triplet state (T1) energy level of the material is higher than the T1 energy level of the main body material in the light emitting layer, and can play a role in blocking the energy loss of the light emitting layer material; the HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the luminescent layer main body material, so that holes are injected into the luminescent layer from the positive electrode, and meanwhile, the electron blocking layer material is required to have high hole mobility, hole transport is facilitated, and the application power of the device is reduced; the LUMO energy level of the electron blocking layer material is higher than that of the host material of the light emitting layer, and plays a role in blocking electrons, that is, the electron blocking layer material is required to have a wide forbidden bandwidth (Eg). The electron blocking layer material satisfying the above conditions may be a triarylamine derivative, a fluorene derivative, a spirofluorene derivative, a dibenzofuran derivative, a carbazole derivative, or the like. Among them, triarylamine derivatives such as N4, N4-bis ([ 1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1,1':4',1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine; spirofluorene derivatives such as N- ([ 1,1 '-diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluorene-2-amine; dibenzofuran derivatives such as, but not limited to, N-di ([ 1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine.
According to the invention, the thickness of the electron blocking layer may be 1 to 200nm, preferably 5 to 150nm and more preferably 10 to 100nm.
According to the invention, the light emitting layer is located between the first electrode and the second electrode. The material of the light emitting layer is a material capable of emitting visible light by receiving holes from the hole transporting region and electrons from the electron transporting region, respectively, and combining the received holes and electrons. The light emitting layer may include a host material and a dopant material. The host material and the guest material of the light-emitting layer of the organic electroluminescent device can be one or two of anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives and pyrimidine derivatives. The guest material can be pyrene derivative, boron derivative, flexo derivative, spirofluorene derivative, iridium complex or platinum complex.
The hole blocking layer may be disposed over the light emitting layer. The triplet state (T1) energy level of the hole blocking layer material is higher than the T1 energy level of the luminescent layer main body material, so that the effect of blocking the energy loss of the luminescent layer material can be achieved; the HOMO energy level of the material is lower than that of the main body material of the luminescent layer, so that the hole blocking effect is achieved, and meanwhile, the hole blocking layer material is required to have high electron injection and hole blocking capabilities, so that electron transmission is facilitated, and the application power of the device is reduced.
The hole blocking layer of the present invention may have a thickness of 2 to 200nm, preferably 5 to 150nm, and more preferably 10 to 100nm, but the thickness is not limited to this range.
An electron transport layer may be disposed over the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer.
The electron injection layer material is preferably a material metal Yb having a low work function so that electrons are easily injected into the organic functional material layer. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, more preferably 0.8 to 1.5nm.
The second electrode may be a cathode and the material used to form the cathode may be a material having a low work function, such as a metal, an alloy, a conductive compound, or a mixture thereof. Non-limiting examples of cathode materials may include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), and aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode is generally 5 to 100nm, preferably 7 to 50nm and more preferably 10 to 25nm, depending on the material used.
Optionally, in order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e. CPL layer) may be further added on top of the second electrode (i.e. cathode) of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL layer material is, the better the CPL layer material is, and the smaller the light absorption coefficient is, the better the CPL layer material is. Any material known in the art may be used as the CPL layer material, e.g., alq 3 . The CPL layer typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
Optionally, the organic electroluminescent device may further comprise an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
Method for preparing organic electroluminescent device
The present invention also relates to a method of manufacturing the above organic electroluminescent device, comprising sequentially laminating a first electrode, a plurality of organic thin film layers, and a second electrode on a substrate. Wherein the multi-layered organic thin film layer is formed by sequentially laminating a hole transporting region, a light emitting layer, and a hole blocking region on the first electrode from bottom to top, i.e., sequentially laminating a hole injecting layer, a hole transporting layer, and an electron blocking layer on the first electrode from bottom to top, i.e., sequentially laminating a hole blocking layer, an electron transporting layer, and an electron injecting layer on the light emitting layer from bottom to top. In addition, optionally, a CPL layer may also be laminated on the second electrode to increase the light extraction efficiency of the organic electroluminescent device.
As for lamination, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. Wherein vacuum evaporation means heating and plating a material onto a substrate in a vacuum environment.
In the present invention, the respective layers are preferably formed using a vacuum evaporation method, whichCan be at a temperature of about 100-500 deg.c, at about 10 -8 -10 -2 Vacuum level of the tray and the likeVacuum evaporation was performed at a rate of (2). The vacuum degree is preferably 10 -6 -10 -2 Torr, more preferably 10 -5 -10 -3 Torr。
The rate is aboutMore preferably about->
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, or may be used as a single layer by forming a film after mixing with another material, or may be a laminated structure between layers formed by forming a film alone, a laminated structure between layers formed by mixing, or a laminated structure between layers formed by forming a film alone and layers formed by mixing.
Display element
The invention also relates to a display device, in particular a flat panel display device, comprising the organic electroluminescent device. In a preferred embodiment, the display apparatus may comprise one or more of the above-described organic electroluminescent devices, and in the case of comprising a plurality of devices, the devices are combined in a stacked manner, either laterally or longitudinally. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to a first electrode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Examples
I. Preparation of Compounds example
The starting materials involved in the synthetic examples of the present invention are all commercially available or are prepared by methods conventional in the art;
the preparation route and the synthesis process of the intermediate F-1 are shown as follows:
under the protection of nitrogen, 30mmol of raw material A-1 is dissolved in 150ml of THF in a 500ml round bottom flask, the temperature is kept at minus 78 ℃ by using a dry ice-acetone bath, 33mmol of tertiary butyl lithium solution is slowly added dropwise, after the reaction is kept for 1 hour, 36mmol of tetramethyl biphenyl diamine is slowly added dropwise, after the reaction is kept for 3 hours, the reaction of the raw material A-1 is completed, and then the temperature is raised to room temperature. Pouring the reaction liquid into a separating funnel, vibrating, standing for layering, extracting the water phase with 200ml of water and 200ml of ethyl acetate after separating, mixing the organic phases, adding anhydrous magnesium sulfate for drying, filtering, and removing the solvent by rotary evaporation to obtain an intermediate A-1.LC-MS: measurement value: 239.30 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 238.12.
under the protection of nitrogen, 30mmol of intermediate A-1, 15mmol of ferric trichloride, 60mmol of TEMPO (2, 6-tetramethylpiperidine oxide), 30mmol of sodium hydroxide and 200mol of DMF are added into a 500ml round bottom flask under the protection of nitrogen, the reaction is stirred at room temperature for 1 hour, after the reaction is finished, the reaction solution is poured into a beaker containing 500ml of water and is mechanically stirred for 20 minutes, then the reaction solution is poured into a separating funnel, is shaken and is then kept stand for layering, after the separation, the aqueous phase is extracted by 200ml of water and 200ml of ethyl acetate, the organic phases are combined, anhydrous magnesium sulfate is added for drying, the filtrate is filtered, and the solvent is removed by spin evaporation to obtain the intermediate B-1.LC-MS: measurement value: 211.20 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 210.10.
30mmol of intermediate B-1 was dissolved in 200ml of DMF under nitrogen protection in a 500ml round bottom flask, the reaction temperature was kept at-15℃with an ethanol bath, then 33mmol of NBS was slowly added dropwise in portions, after incubation for 4 hours, the reaction of starting material B-1 was completed and then warmed to room temperature. Pouring the reaction solution into a beaker containing 500ml of 10% diluted hydrochloric acid, stirring for 30min, and pouring the reaction solution into a liquid-separating funnelShaking after the bucket, standing for layering, extracting the aqueous phase with 300ml of ethyl acetate after separating, mixing the organic phases, adding anhydrous magnesium sulfate for drying, filtering, and removing the solvent by rotary evaporation of the filtrate to obtain an intermediate C-1.LC-MS: measurement value: 289.18 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 288.01.
in a 500ml round bottom flask under nitrogen protection, adding the intermediate C-1 (20 mmol), the raw material B-1 (22 mmol) and K in sequence 2 CO 3 (60 mmol), tetrahydrofuran (150 mL), water (50 mL), and nitrogen for 30min to replace air, pd (PPh) was added 3 ) 4 (0.4 mmol) was heated under reflux under nitrogen for 10h. Taking the TCL of the reaction liquid to detect that the reaction of the intermediate C-1 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 120ml of dichloromethane to the residue for dissolution, adding 80ml of water for washing, pouring into a separating funnel, vibrating, standing for delamination, extracting the water phase with dichloromethane (30 ml x 3) after liquid separation, merging the organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing the dichloromethane by rotary evaporation to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain the intermediate D-1.LC-MS: measurement value: 287.26 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 286.14.
in a 500ml round bottom flask under nitrogen protection, 20mmol of intermediate D-1, 200ml of anhydrous dichloromethane are added and cooled to 0℃and then 50mmol of triethylamine, 30mmol of perfluorobutylsulphonyl fluoride are added. The reaction mixture was warmed to room temperature and stirred for 3 hours at room temperature. After the reaction, pouring the reaction liquid into a beaker, adding 200ml of dichloromethane and 100ml of water, pouring the reaction liquid into a separating funnel, vibrating, standing for layering, extracting an aqueous phase with dichloromethane (60 ml is 3) after separating, merging organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing the dichloromethane from the filtrate by rotary evaporation to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain an intermediate E-1.LC-MS: measurement value: 569.14 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 568.08.
20mmol of intermediate E-1, 22mmol of bisboronic acid pinacol ester, KOAC (60 mmol) and dioxane (150 mL) are added in sequence in a 500mL round bottom flask under the protection of nitrogen, nitrogen is introduced for 30min to replace air, pd (PPh) 3 ) 4 (0.4 mmol) was heated under reflux under nitrogen for 11h. Taking the TCL of the reaction liquid to detect that the reaction of the intermediate E-1 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, pouring the reaction system into a separating funnel, vibrating, standing for layering, extracting an aqueous phase with dichloromethane (30 ml x 3) after liquid separation, mixing organic phases, adding anhydrous magnesium sulfate for drying, filtering, and removing the dichloromethane from the filtrate by rotary evaporation to obtain the intermediate F-1.LC-MS: measurement value: 397.31 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 396.23.
intermediate F-2 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
LC-MS of intermediate F-2: measurement value: 521.36 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 520.26.
intermediate F-3 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
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LC-MS of intermediate F-3: measurement value: 519.31 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 518.24.
intermediate F-4 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
LC-MS of intermediate F-4: measurement value: 561.23 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 560.29.
intermediate F-5 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
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LC-MS of intermediate F-5: measurement value: 535.17 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 534.24.
intermediate F-6 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
LC-MS of intermediate F-6: measurement value: 551.33 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 550.21.
intermediate F-7 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
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LC-MS of intermediate F-7: measurement value: 569.32 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 568.26.
intermediate F-8 was prepared by a synthetic method similar to intermediate F-1 using the following starting materials and reaction schemes:
LC-MS of intermediate F-8: measurement value：595.16([M+H] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 594.27.
intermediate L-1 and intermediate L-2 were prepared as follows:
in a 250ml round bottom flask under nitrogen protection, intermediate F-1 (20 mmol), m-bromoiodobenzene (22 mmol) and K are added in sequence 2 CO 3 (60 mmol), tetrahydrofuran (100 Ml), water (50 Ml), nitrogen for 30min to replace air, palladium acetate (0.20 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.40 mmol) were added, and the mixture was heated under reflux for 10h under nitrogen protection. Taking the TCL of the reaction liquid to detect that the reaction of the intermediate F-1 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 200ml of dichloromethane to the residue for dissolution, adding 150ml of water for washing, pouring into a separating funnel, vibrating, standing for delamination, extracting the water phase with dichloromethane (80 ml x 3) after separating, merging the organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing the dichloromethane by rotary evaporation from the filtrate to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain the intermediate M-1.LC-MS: measurement value: 425.19 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 424.08.
20mmol of intermediate M-1, 22mmol of bisboronic acid pinacol ester, KOAC (60 mmol) and dioxane (150 Ml) are added in sequence in a 500Ml round bottom flask under the protection of nitrogen, the air is replaced by introducing nitrogen for 30min, and Pd (PPh) 3 ) 4 (0.4 mmol) was heated under reflux under nitrogen for 8h. Taking the TCL of the reaction liquid to detect that the intermediate M-1 is completely reacted, naturally cooling the reaction system to room temperature after the reaction is completed, pouring the reaction system into a separating funnel, vibrating, standing for layering, extracting a water phase with dichloromethane (30 ml x 3) after liquid separation, mixing organic phases, adding anhydrous magnesium sulfate for drying, filtering, and removing the dichloromethane from filtrate by rotary evaporation to obtain the intermediate L-1.LC-MS: measurement value: 473.33 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 472.26.
in a 250ml round bottom flask under nitrogen protection, intermediate F-3 (20 mmol), m-bromoiodobenzene (22 mmol) and K are added in sequence 2 CO 3 (60 mmol), tetrahydrofuran (100 Ml), water (50 Ml), nitrogen for 30min to replace air, palladium acetate (0.20 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.40 mmol) were added, and the mixture was heated under reflux for 14h under nitrogen protection. Taking the TCL of the reaction liquid to detect that the reaction of the intermediate F-3 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 200ml of dichloromethane to the residue to dissolve, adding 150ml of water to wash, pouring into a separating funnel, vibrating, standing for layering, extracting the water phase with dichloromethane (80 ml x 3) after separating, merging the organic phases, adding anhydrous magnesium sulfate to dry, filtering, removing the dichloromethane by rotary evaporation from the filtrate to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain the intermediate M-2.LC-MS: measurement value: 547.22 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 546.10.
20mmol of intermediate M-2, 22mmol of bisboronic acid pinacol ester, KOAC (60 mmol) and dioxane (150 Ml) are added in sequence in a 500Ml round bottom flask under the protection of nitrogen, the air is replaced by introducing nitrogen for 30min, and Pd (PPh) 3 ) 4 (0.4 mmol) was heated under reflux under nitrogen for 12h. Taking the TCL of the reaction liquid to detect that the intermediate M-2 is completely reacted, naturally cooling the reaction system to room temperature after the reaction is completed, pouring the reaction system into a separating funnel, vibrating, standing for layering, extracting a water phase with dichloromethane (30 ml x 3) after liquid separation, mixing organic phases, adding anhydrous magnesium sulfate for drying, filtering, and removing the dichloromethane from filtrate by rotary evaporation to obtain the intermediate L-2.LC-MS: measurement value: 595.39 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 594.27.
preparation of intermediate G1, intermediate H1, intermediate J1:
under the protection of nitrogen, raw materials C1 (30 mmol), raw materials B1 (30 mmol) and K are sequentially added into a 500ml round bottom flask 2 CO 3 (90 mmol), tetrahydrofuran (180 mL), water (60 mL), and nitrogen for 30min to replace air, pd (PPh) was added 3 ) 4 (0.6 mmol) was heated under reflux under nitrogen for 12h. Taking a reaction liquid TCL to detect that the reaction of a raw material C1 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, removing a solvent by rotary evaporation, adding 150ml of dichloromethane into residues to dissolve, adding 100ml of water to wash, pouring into a separating funnel, vibrating, standing for layering, extracting a water phase with dichloromethane (50 ml of x 3) after liquid separation, merging organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing dichloromethane from filtrate by rotary evaporation to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain an intermediate G1.LC-MS: measurement value: 266.91 ([ M+H) ] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 265.95.
raw material E1 (30 mmol) and diethyl ether (150 mL) were added in sequence to a 500mL round bottom flask under nitrogen protection, cooled to-78 ℃, purged with nitrogen for 30min to replace air, 1.6mol/L of n-butyllithium in hexane (40 mmol) was slowly added, and after 3h of reaction at-78 ℃, trimethyl borate (40 mmol) was added, and after 1h of reaction at-78 ℃, the mixture was reacted at room temperature for 16h. Taking the reaction liquid TCL to detect that the reaction of the raw material E1 is complete, adding a dilute solution (50 ml) of hydrochloric acid into a reaction system after the reaction is completed, removing the organic solvent by rotary evaporation, and filtering residues to obtain a white solid intermediate H1.LC-MS: measurement value: 278.21 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 277.10.
in a 500ml round bottom flask under nitrogen protection, intermediate G1 (15 mmol), intermediate H1 (15 mmol), K were added sequentially 2 CO 3 (45 mmol), tetrahydrofuran (180 mL), water (60 mL), and nitrogen for 30min to replace air, pd (PPh) was added 3 ) 4 (0.3 mmol) was heated under reflux under nitrogen for 12h. Taking the TCL of the reaction liquid to detect that the intermediate G1 is completely reacted, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 150ml of dichloromethane into the residue to dissolve, adding 100ml of water for washing, pouring into a separating funnel, vibrating, standing for layering, extracting the water phase with dichloromethane (50 ml of 3) after separating, merging the organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing the dichloromethane by rotary evaporation to obtain a crude product, purifying the crude product by a silica gel chromatographic column to obtain the product To intermediate J1.LC-MS: measurement value: 420.20 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 419.12.
intermediate G was prepared by a synthetic method similar to intermediate G1 using starting materials C and B as shown in Table 1;
intermediate H was prepared by a synthetic method similar to intermediate H1 using starting material E as shown in Table 1;
intermediate J was prepared by a synthetic method similar to intermediate J1, using intermediate G and intermediate H as shown in Table 1;
TABLE 1
Example 1: synthesis of Compound 1
In a 250ml round bottom flask under nitrogen protection, intermediate J2 (20 mmol), intermediate F-1 (22 mmol), K were added sequentially 2 CO 3 (60 mmol) and tetrahydrofuran (100 mL), water (50 mL), nitrogen was introduced for 30min to replace air, palladium acetate (0.20 mmol) was added, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.40 mmol) was heated under reflux for 13h under nitrogen protection. Taking the TCL of the reaction liquid to detect that the intermediate J2 is completely reacted, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 200ml of dichloromethane to the residue for dissolution, adding 150ml of water for washing, pouring into a separating funnel, vibrating, standing for delamination, extracting the water phase with dichloromethane (80 ml x 3) after liquid separation, merging the organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing the dichloromethane by rotary evaporation to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain the compound 1. Elemental analysis: c (C) 48 H 35 N 3 Theoretical value: c,88.18; h,5.40; n,6.43; test value: c,88.34; h,5.37; n,6.33.LC-MS: measurement value: 654.47 ([ M+H)] + ) Accurate quality: 653.28.
example 2: synthesis of Compound 2
Compound 2 was prepared according to the procedure for the synthesis of compound 1 in example 1, except that intermediate J3 was selected instead of intermediate J2. Elemental analysis: c (C) 54 H 39 N 3 Theoretical value: c,88.86; h,5.39; n,5.76; test value: c,88.68; h,5.52; n,5.90.LC-MS: measurement value: 730.49 ([ M+H)] + ) Accurate quality: 729.31.
example 3: synthesis of Compound 7
Compound 7 was prepared according to the procedure for the synthesis of compound 1, example 1, except that intermediate F-2 was selected instead of intermediate F-1. Elemental analysis: c (C) 58 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,89.55; h,5.05; n,5.40; test value: c,89.57; h,5.05; n,5.43.LC-MS: measurement value: 778.25 ([ M+H)] + ) Accurate quality: 777.31.
example 4: synthesis of Compound 14
Compound 14 was prepared according to the procedure for the synthesis of compound 1, example 1, except that intermediate F-3 was selected for use in place of intermediate F-1. Elemental analysis: c (C) 58 H 37 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,89.78; h,4.81; n,5.42; test value: c,89.72; h,4.93; n,5.41.LC-MS: measurement value: 776.21 ([ M+H) ] + ) Accurate quality: 775.30.
example 5: synthesis of Compound 17
Compound 17 was prepared according to the procedure for the synthesis of compound 1, example 1, except intermediate J6 was selected to replace intermediate J2 and intermediate F-3 was selected to replace intermediate F-1. Elemental analysis: c (C) 64 H 41 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.22; h,4.85; n,4.93; test value: c,90.19; h,4.82; n,4.88.LC-MS: measurement value: 852.69 ([ M+H)] + ) Accurate quality: 851.33.
example 6: synthesis of Compound 18
Compound 18 is prepared according to the procedure for the synthesis of compound 1 of example 1, except intermediate J5 is selected to replace intermediate J2 and intermediate F-3 is selected to replace intermediate F-1. Elemental analysis: c (C) 62 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.15; h,4.76; n,5.09; test value: c,90.25; h,4.69; n,5.03.LC-MS: measurement value: 826.51 ([ M+H)] + ) Accurate quality: 825.31.
example 7: synthesis of Compound 19
Compound 19 was prepared according to the procedure for the synthesis of compound 1, example 1, except intermediate J4 was selected to replace intermediate J2 and intermediate F-3 was selected to replace intermediate F-1. Elemental analysis: c (C) 62 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.15; h,4.76; n,5.09; test value: c,90.25; h,4.65; n,5.10.LC-MS: measurement value: 826.30 ([ M+H)] + ) Accurate quality: 825.31.
Example 8: synthesis of Compound 20
Compound 20 was prepared according to the procedure for the synthesis of compound 1 in example 1,except that intermediate F-4 was selected to replace intermediate F-1. Elemental analysis: c (C) 61 H 43 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,89.56; h,5.30; n,5.14; test value: c,89.51; h,5.38; n,4.99.LC-MS: measurement value: 818.67 ([ M+H)] + ) Accurate quality: 817.35.
example 9: synthesis of Compound 26
Compound 26 was prepared according to the procedure for the synthesis of compound 1, example 1, except that intermediate F-5 was used instead of intermediate F-1. Elemental analysis: c (C) 58 H 37 N 3 O; theoretical value: c,87.96; h,4.71; n,5.31; test value: c,88.17; h,4.82; n,5.02.LC-MS: measurement value: 792.68 ([ M+H)] + ) Accurate quality: 791.29.
example 10: synthesis of Compound 31
Compound 31 was prepared according to the procedure for the synthesis of compound 1 in example 1, except that intermediate F-6 was selected for use in place of intermediate F-1. Elemental analysis: c (C) 58 H 37 N 3 S, S; theoretical value: c,86.22; h,4.62; n,5.20; s,3.97; test value: c,86.35; h,4.51; n,5.25; s,3.95.LC-MS: measurement value: 808.35 ([ M+H)] + ) Accurate quality: 807.27.
example 11: synthesis of Compound 38
Compound 38 is prepared according to the procedure for the synthesis of compound 1 of example 1, except that intermediate L-1 is selected for use in place of intermediate F-1. Elemental analysis: c (C) 54 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,88.86; h,5.39; n,5.76; test value: c,88.79; h,5.36; n,5.79.LC-MS: measurement value: 730.64 ([ M+H)] + ) Accurate quality: 729.31.
example 12: synthesis of Compound 44
Compound 44 was prepared according to the procedure for the synthesis of compound 1, example 1, except that intermediate L-2 was used instead of intermediate F-1. Elemental analysis: c (C) 64 H 41 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.22; h,4.85; n,4.93; test value: c,90.26; h,4.90; n,4.77.LC-MS: measurement value: 852.47 ([ M+H)] + ) Accurate quality: 851.33.
example 13: synthesis of Compound 145
Compound 145 was prepared following the procedure for the synthesis of compound 1 of example 1, except intermediate J1 was selected instead of intermediate J2. Elemental analysis: c (C) 48 H 35 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,88.18; h,5.40; n,6.43; test value: c,88.06; h,5.47; n,6.50.LC-MS: measurement value: 654.71 ([ M+H)] + ) Accurate quality: 653.28.
example 14: synthesis of Compound 147
Compound 147 was prepared according to the procedure for the synthesis of compound 1, example 1, except that intermediate J1 was selected to replace intermediate J2 and intermediate F-3 was selected to replace intermediate F-1. Elemental analysis: c (C) 58 H 37 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,89.78; h,4.81; n,5.42; test value: c,89.70; h,5.09; n,5.41.LC-MS: measurement value: 776.32 ([ M+H) ] + ) Accurate quality: 775.30.
example 15: synthesis of Compound 149
Compound 149 is prepared according to the method for the synthesis of compound 1 of example 1, except intermediate J1 is selected to replace intermediate J2 and intermediate F-5 is selected to replace intermediate F-1. Elemental analysis: c (C) 58 H 37 N 3 O; theoretical value: c,87.96; h,4.71; n,5.31; test value: c,88.11; h,4.90; n,5.07.LC-MS: measurement value: 792.23 ([ M+H)] + ) Accurate quality: 791.29.
example 16: synthesis of Compound 182
Compound 182 was prepared according to the procedure for the synthesis of compound 1, example 1, except intermediate J1 was selected to replace intermediate J2 and intermediate L-1 was selected to replace intermediate F-1. Elemental analysis: c (C) 54 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,88.86; h,5.39; n,5.76; test value: c,89.03; h,5.19; n,5.74.LC-MS: measurement value: 730.76 ([ M+H)] + ) Accurate quality: 729.31.
example 17: synthesis of Compound 218
Compound 218 was prepared according to the procedure for the synthesis of compound 1, example 1, except intermediate J1 was selected to replace intermediate J2 and intermediate L-2 was selected to replace intermediate F-1. Elemental analysis: c (C) 64 H 41 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.22; h,4.85; n,4.93; test value: c,90.01; h,5.02; n,4.95.LC-MS: measurement value: 852.76 ([ M+H) ] + ) Accurate quality: 851.33.
example 18: synthesis of Compound 290
Compound 290 was prepared according to the procedure for the synthesis of compound 1 of example 1, except intermediate F-7 was selected instead of intermediate F-1. Elemental analysis: c (C) 62 H 39 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.15; h,4.76; n,5.09; test value: c,90.22; h,4.81; n,5.03.LC-MS: measurement value: 826.68 ([ M+H)] + ) Accurate quality: 825.31.
example 19: synthesis of Compound 322
Compound 322 was prepared according to the procedure for the synthesis of compound 1 of example 1, except intermediate J1 was selected to replace intermediate J2 and intermediate F-8 was selected to replace intermediate F-1. Elemental analysis: c (C) 64 H 41 N 3 The method comprises the steps of carrying out a first treatment on the surface of the Theoretical value: c,90.22; h,4.85; n,4.93; test value: c,90.17; h,4.78; n,5.10.LC-MS: measurement value: 852.72 ([ M+H)] + ) Accurate quality: 851.33.
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device preparation examples
The effect of the compounds synthesized according to the present invention in the use as hole blocking layers in devices is described in detail below with respect to device examples 1 to 19 and device comparative examples 1 to 13. Device examples 1-19 and device comparative examples 1-13 were identical in the fabrication process to device example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the hole blocking material was changed in the device. The device stack structure is shown in table 2, and the performance test results of each device are shown in table 3.
The molecular structural formula of the related material is shown as follows:
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the structures of the comparative compounds HB-1, HB-2, HB-3, HB-4, HB-5, HB-6, HB-7, HB-8, HB-9, HB-10, HB-11, HB-12 and HB-13 are as described above. The above materials are commercially available or are obtained by conventional synthetic methods in the art.
Device example 1
The preparation process comprises the following steps:
as shown in FIG. 1, the transparent substrate layer 1 was transparent glass, the anode layer 2 was Ag (100 nm), and HT-1 and P-1 having a film thickness of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus on the anode layer 2, and the mass ratio of HT-1 to P-1 was 97:3. Next, HT-1 was evaporated to a thickness of 117nm as a hole transport layer 4. Subsequently EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping material doping ratio is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the light-emitting layer 6, the compound 1 was continuously deposited to a thickness of 8nm as a hole blocking layer 7. And (3) continuously evaporating ET-1 and Liq on the hole blocking layer 7, wherein the mass ratio of the ET-1 to the Liq is 1:1. The vacuum deposition film thickness of the material is 30nm, and the layer is an electron transport layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10. On the cathode layer 10, 65nm of CP-1 was vacuum-deposited as CPL layer 11.
Device examples 2-19 and device comparative examples 1-13 were prepared in a similar manner to device example 1, and the substrates were each made of transparent glass, and the anodes were each made of Ag (100 nm), except that the parameters in table 2 below were used.
TABLE 2
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Device test examples
The devices prepared in II were tested for driving voltage, current efficiency, CIEy and LT95 lifetime. Voltage, current efficiency, CIEy were tested using an IVL (current-voltage-brightness) test system (freda scientific instruments, su) with a current density of 10mA/cm 2 . LT95 refers to the time taken for the device brightness to decay to 95% of the initial brightness, and the current density at the time of testing is 50mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the The life test system is an EAS-62C OLED device life tester of Japanese system technical research company; the high temperature lifetime test temperature is 85 ℃, LT80 refers to the time taken for the device brightness to decay to 80% at a particular brightness. The test results are shown in Table 3 below.
TABLE 3 Table 3
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As can be seen from the device test data results of Table 3 above, the device driving voltage prepared using the compounds of the present invention as hole blocking layer materials was significantly reduced while at the same time the current efficiency was improved, and the device lifetime was prolonged, for example, by substantially 1.15 times or more the lifetime of the comparative device 1-13, as compared to the comparative device using HB-1, HB-2, HB-3, HB-4, HB-5, HB-6, HB-7, HB-8, HB-9, HB-10, HB-11, HB-12 and HB-13 as hole blocking layer materials.
The structural formulas of the comparative compounds HB-1, HB-2, HB-3, HB-4, HB-5, HB-6, HB-7, HB-8, HB-9, HB-10, HB-11, HB-12 and HB-13 used in the comparative examples are close to the present invention, however, unexpectedly, the compounds of the present invention have a better technical effect as hole blocking materials than the comparative compounds.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (10)
1. A compound containing a triazine structure is characterized in that the structure of the compound is shown as a general formula (1-1) or a general formula (1-2):
in the general formula (1-1) and the general formula (1-2), R 2 Represented by phenyl, biphenyl or naphthyl; l (L) 1 Represented by a single bond or phenylene;
r is represented by a structure shown in a general formula a, a general formula b or a general formula c;
R 1 represented by phenyl, biphenyl or naphthyl; x represents O, S, a single bond or a dimethyl-substituted methylene group.
2. The triazine structure-containing compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (2-1) to (2-4):
r, R in the general formulae (2-1) to (2-4) 2 Is as defined in claim 1.
3. The triazine structure-containing compound according to claim 1, wherein the triazine structure-containing compound has a structure represented by any one of the general formulae (3-1) to (3-4):
r, R in the general formulae (3-1) to (3-4) 2 Is as defined in claim 1.
4. The triazine structure-containing compound of claim 1 wherein R 2 Represented as phenyl.
5. The triazine structure-containing compound of claim 1 wherein R 2 Represented as biphenyl.
6. The triazine structure-containing compound of claim 1 wherein R 2 Represented as naphthyl.
7. The triazine structure-containing compound of claim 1 wherein R 1 Represented as phenyl.
8. The triazine structure-containing compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
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9. an organic electroluminescent device comprising a first electrode and a second electrode, wherein a plurality of organic thin film layers are provided between the first electrode and the second electrode of the organic electroluminescent device, characterized in that at least one organic thin film layer comprises the triazine structure-containing compound of any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the multi-layered organic thin film layer comprises a hole blocking layer containing the triazine structure-containing compound of any one of claims 1 to 8.
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