CN116969928B - Compound with nitrogen-containing heterocyclic structure and application thereof in organic electroluminescent device - Google Patents
Compound with nitrogen-containing heterocyclic structure and application thereof in organic electroluminescent device Download PDFInfo
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- CN116969928B CN116969928B CN202310732676.9A CN202310732676A CN116969928B CN 116969928 B CN116969928 B CN 116969928B CN 202310732676 A CN202310732676 A CN 202310732676A CN 116969928 B CN116969928 B CN 116969928B
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
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- 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
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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract
The invention discloses a compound with a nitrogen-containing heterocyclic 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), the compound has good stability and electron tolerance, and simultaneously has good electron injection and hole blocking capabilities, and when the compound is used as a material of an organic electroluminescent device, the driving voltage and the service life of the device are obviously improved.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to a compound with a nitrogen-containing heterocyclic 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, compared with the actual product application requirements, the performance of the OLED device, such as luminous efficiency and service life, needs to be further improved. 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 a phase state when the device works, and the service life of the device is poor.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a compound with a nitrogen heterocyclic structure and application thereof in an organic electroluminescent device, wherein the nitrogen heterocyclic structure is a triazine group, and the compound bridges the nitrogen heterocyclic structure and a spiro group through a specific bridging structure, 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 and prolong the service life.
The technical scheme of the invention is as follows: a compound with a nitrogen-containing heterocyclic structure, wherein the structure of the compound is shown as a general formula (1):
In the general formula (1), R 1 represents phenyl, biphenyl or naphthyl;
R 2 represents phenyl or naphthyl;
m1 and M2 are the same or different and are represented as benzene rings or naphthalene rings;
X 1、X2 and X 3 are independently represented as CH or N, at least 2 of which are represented as N;
l 1 represents a single bond or phenylene;
X represents an oxygen atom or a sulfur atom;
asterisks indicate the ligatable sites.
Preferably, the structure of the compound is shown as a general formula (1-1), a general formula (1-2), a general formula (1-3) or a general formula (1-4):
In the general formula (1-1), the general formula (1-2), the general formula (1-3) and the general formula (1-4), R 1 is phenyl, biphenyl or naphthyl;
x 1、X2 and X 3 are independently represented as C or N, at least 2 of which are represented as N;
l 1 represents 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;
In the general formulae a, b and c, X represents an oxygen atom or a sulfur atom.
Preferably, the structure of the compound is shown as any one of the general formulas (2-1) to (2-8):
In the general formulae (2-1) to (2-8), X 1、X2、X3、R、R1 has the meaning as defined above. Preferably, the structure of the compound is shown as any one of the general formulas (3-1) to (3-2):
in the general formulae (3-1) to (3-2), X 1、X2、X3、R、R1 has the meaning as defined above. Preferably, the R is any one of the following structures:
preferably, the R is any one of the following structures:
X represents an oxygen atom or a sulfur atom.
Preferably, the R 1 is any one of the following structures:
Preferably, the L 1 is any one of the following structures
A single bond,Preferably, the X 1、X2 and X 3 are denoted as N at the same time.
Preferably, R 1 represents phenyl.
Preferably, R 1 is biphenyl.
Preferably, R 1 is naphthyl.
Preferably, the specific structure of the compound is any one of the following structures:
The invention also provides an organic electroluminescent device, which comprises a first electrode and a second electrode, wherein a plurality of organic film layers are arranged between the first electrode and the second electrode of the organic electroluminescent device, and at least one organic film layer contains the compound.
Preferably, the multi-layer organic thin film layer includes a hole transport region, a light emitting region, and an electron transport region, and the electron transport region contains the compound.
Preferably, the electron transport region comprises an electron injection layer, an electron transport layer and a hole blocking layer, and the hole blocking layer contains the compound.
Preferably, the multi-layer organic thin film layer includes a hole blocking layer containing the compound.
The invention also provides a display element, which comprises the organic electroluminescent device.
The beneficial technical effects of the invention are as follows:
the compound is based on a triazine structure, is connected through a specific phenyl bridging group, and has good electron tolerance and stability, and good electron injection and hole blocking capability, wherein the substituent is a spiro [ fluorene-9, 9 '-xanthene ] derivative group or a spiro [ fluorene-9, 9' -thioxanthene ] derivative group. 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 invention introduces the spiro [ fluorene-9, 9 '-xanthene ] derivative group or the spiro [ fluorene-9, 9' -thioxanthene ] derivative group, and the group has a good steric hindrance structure, can inhibit pi-pi accumulation among molecules, obviously improves the electron injection capability and reduces the driving voltage of the device. In addition, due to the existence of the spiro [ fluorene-9, 9 '-xanthene ] derivative group or the spiro [ fluorene-9, 9' -thioxanthene ] 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 invention 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.
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of compound 73 in deuterated chloroform;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of compound 405 in deuterated chloroform;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of compound 9 in deuterated chloroform;
Detailed Description
The technical aspects of the present invention 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 of the organic thin film layers contains the nitrogen-containing heterocyclic 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 nitrogen-containing heterocyclic structure compound according to the present application.
In a preferred embodiment of the present invention, the organic electroluminescent device according to the present invention 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 (top emission). 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, a1, 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 5 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, such as 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 layers are preferably formed using a vacuum evaporation process, wherein the layers may be formed at a temperature of about 100-500 ℃ and a vacuum of about 10 -8-10-2 torr and a vacuum of aboutVacuum 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 procedure of intermediate A1 are shown below:
Under the protection of nitrogen, raw material O1 (30 mmol), raw material P1 (35 mmol), K 2CO3 (90 mmol) and tetrahydrofuran (180 mL) are sequentially added into a round bottom flask, water (60 mL) is introduced into the flask to replace air, pd (PPh 3)4 (0.6 mmol) is added, heating reflux is carried out for 10H under the protection of nitrogen, the reaction solution TCL is taken to detect that the raw material O1 is completely reacted, after the reaction is completed, the reaction system is naturally cooled to room temperature, the solvent is removed by rotary evaporation, the remainder is added into dichloromethane to be dissolved, 120mL of water is added for washing, the mixture is poured into a separating funnel for shaking and then is placed for layering, after the liquid separation, the aqueous phase is extracted by dichloromethane (60 mL of 3), anhydrous magnesium sulfate is added for drying after the organic phases are combined, filtering is carried out, the filtrate is subjected to rotary evaporation to remove dichloromethane to obtain a crude product, and the crude product is purified by a silica gel chromatographic column to obtain an intermediate Q1.LC-MS: 266.87 ([ M+H ] +), and the accurate quality is 265.95.
Raw material R1 (30 mmol) and diethyl ether (150 mL) were added in sequence to a round bottom flask under the protection of nitrogen, cooled to-78 ℃, introduced with nitrogen for 30min to replace air, 1.6mol/L of n-butyllithium hexane solution (40 mmol) was slowly added, and after reaction at-78 ℃ for 3h, trimethyl borate (40 mmol) was added, and after reaction at-78 ℃ for 1h, the mixture was reacted at room temperature for 16h. Taking the reaction solution TCL to detect that the reaction of the raw material R1 is complete, adding a dilute solution (50 ml) of hydrochloric acid into the reaction system after the reaction is completed, removing the organic solvent by rotary evaporation, and filtering the residue to obtain a white solid intermediate S1.LC-MS: measurement value: 278.19 ([ M+H ] +); accurate quality: 277.10.
Under the protection of nitrogen, sequentially adding an intermediate Q1 (15 mmol), an intermediate S1 (20 mmol), K 2CO3 (45 mmol) and tetrahydrofuran (200 mL) into a round-bottom flask, replacing air by water (70 mL), introducing nitrogen for 40min, adding Pd (PPh 3)4 (0.3 mmol), heating and refluxing for 15H under the protection of nitrogen, taking a reaction liquid TCL, detecting the reaction liquid TCL to find that the intermediate Q1 is completely reacted, naturally cooling the reaction system to room temperature after the reaction is completed, removing a solvent by rotary evaporation, adding 200mL of dichloromethane into residues for dissolution, adding 120mL of water for washing, pouring into a separating funnel, shaking and standing for layering, extracting an aqueous phase with dichloromethane (50 mL of x 3) after separating, merging organic phases, adding anhydrous magnesium sulfate for drying, filtering, removing 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 A1 LC-MS: measured value 420.35 ([ M+H ] +), wherein the accurate mass is 419.12.
Intermediate Q was prepared by a synthetic method similar to intermediate Q1 using starting materials O and P as shown in Table 1;
intermediate S was prepared by a synthetic method similar to intermediate S1 using starting material R shown in Table 1;
Intermediate a was prepared by a synthetic method similar to intermediate A1, using intermediate Q and intermediate S as shown in table 1;
TABLE 1
Synthesis of intermediate 1-1
Raw materials 1-1 (30 mmol), rose bengal (3 mmol) and acetonitrile (100 mL) were added to a quartz tube. The solution was saturated with oxygen for 40 minutes and then irradiated with a high pressure mercury lamp (500W) through the filtered solution (1, 3, 5-trimethylbenzene/EtOH 1:1) for 100 hours. Finally, the reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as eluent. Intermediate 1-1 was prepared. LC-MS: measurement value: 281.21 ([ M+H ] +); accurate quality: 280.03.
The preparation route and the synthesis process of the intermediate B1 are as follows:
Under the protection of nitrogen, sequentially adding a raw material T1 (17 mmol), a raw material U1 (15 mmol), K 2CO3 (45 mmol) and tetrahydrofuran (150 mL) into a round-bottom flask, introducing nitrogen for 40min to replace air, adding Pd (PPh 3)4 (0.3 mmol), heating and refluxing for 12H under the protection of nitrogen, taking a reaction liquid TCL, detecting to find that the raw material U1 is completely reacted, naturally cooling the reaction system to room temperature, removing a solvent by rotary evaporation, adding 180mL of dichloromethane into residues to dissolve, adding 100mL of water to wash, pouring into a separating funnel, shaking, standing for layering, extracting an aqueous phase with dichloromethane (50 mL of x 3) after separating, adding anhydrous magnesium sulfate for drying, filtering, removing dichloromethane by rotary evaporation from filtrate to obtain a crude product, and purifying the crude product by a silica gel chromatographic column to obtain an intermediate V1.LC-MS: a measured value of 316.92 ([ M+H ] +), wherein the accurate quality is 315.97.
Intermediate V1 (60 mmol) was dissolved in 200mL of tetrahydrofuran solution, and a hexane solution of n-butyllithium (60 mmol) was added dropwise at-78℃followed by stirring for about 1 hour. After the addition of raw material W1 (50 mmol), it was stirred at room temperature for 2 hours. After extraction with ethyl acetate, concentration was carried out to prepare intermediate X1.LC-MS: measurement value: 435.25 ([ M+H ] +); accurate quality: 434.11.
Intermediate X1 (45 mmol) was added to 200mL of acetic acid in a round bottom flask under nitrogen and refluxed for 4 hours after the addition of 2mL of concentrated sulfuric acid at 80 ℃. After the temperature was lowered to room temperature and the reaction was terminated, the solid obtained by filtration was washed twice with THF and ethyl acetate, respectively, to obtain intermediate Y1.LC-MS: measurement value: 417.16 ([ M+H ] +); accurate quality: 416.10.
Under the protection of nitrogen, 10mmol of intermediate Y1, 12mmol of pinacol diboronate, KOAC (40 mmol) and dioxane (120 ml) are sequentially added into a round bottom flask, nitrogen is introduced for 30min to replace air, pd (PPh 3)4 (0.2 mmol) is added, heating reflux is performed under the protection of nitrogen for 10H, reaction liquid TCL is taken to detect that the intermediate Y1 is completely reacted, after the reaction is completed, the reaction system is naturally cooled to room temperature, poured into a separating funnel, oscillated and then kept stand for layering, after separation, aqueous phase is extracted by dichloromethane (50 ml of x 3), organic phases are combined, anhydrous magnesium sulfate is added for drying, filtration is performed, and filtrate is subjected to rotary evaporation to remove dichloromethane to obtain intermediate B.LC-MS: measured value 509.16 ([ M+H ] +), and accurate mass is 508.22.
Intermediate V was prepared by a synthetic method similar to intermediate V1 using starting materials T and U as shown in Table 2;
intermediate X was prepared by a synthetic method similar to intermediate X1 using intermediate V as shown in table 2; the raw materials W are all raw materials W1;
intermediate Y was prepared by a synthetic method similar to intermediate Y1, using intermediate X as shown in table 2;
Intermediate B was prepared by a synthetic method similar to intermediate B1, using intermediate Y as shown in table 2;
TABLE 2
The intermediate B6 is prepared by synthesizing an intermediate X6 similar to the intermediate X1, and replacing the intermediate V1 and the intermediate W1 with a raw material V6 and a raw material W6 respectively.
LC-MS: measurement value: 509.11 ([ M+H ] +); accurate quality: 508.22
The intermediate B8 is prepared by synthesizing an intermediate X8 similar to the intermediate X1, and replacing the intermediate V1 and the intermediate W1 with a raw material V8 and a raw material W8 respectively.
LC-MS: measurement value: 509.17 ([ M+H ] +); accurate quality: 508.22
LC-MS: measurement value: 509.29 ([ M+H ] +); accurate quality: 508.22
Example 1: synthesis of Compound 1
Under the protection of nitrogen, intermediate A1 (20 mmol), raw material C1 (25 mmol), K 2CO3 (60 mmol) and tetrahydrofuran (100 mL) are sequentially added into a round bottom flask, water (50 mL) is introduced into the flask, air is replaced by nitrogen for 40min, palladium acetate (0.20 mmol) is added, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.40 mmol) is added, and the mixture is heated and refluxed for 15h under the protection of nitrogen. Taking the TCL of the reaction liquid to detect that the reaction of the intermediate A1 is complete, naturally cooling the reaction system to room temperature after the reaction is completed, removing the solvent by rotary evaporation, adding 180ml of dichloromethane to dissolve residues, adding 180ml of water for washing, pouring into a separating funnel, vibrating, standing for layering, extracting the water phase with dichloromethane (100 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, and purifying the crude product by a silica gel chromatographic column to obtain the compound 1.
Other compounds were prepared by synthesis of similar compound 1 using starting materials or intermediates as shown in table 3;
TABLE 3 Table 3
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 35 and device comparative examples 1 to 14. Device examples 2-35 and device comparative examples 1-14 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 in the device was changed. The device stack structure is shown in Table 4, and the performance test results of each device are shown in Table 5
The molecular structural formula of the related material is shown as follows:
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, HB-13, and HB-14 are 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 clean 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 2-35 and device comparative examples 1-14 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 4 below were used.
TABLE 4 Table 4
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 (fresco 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 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 5 below.
TABLE 5
As can be seen from the device test data results of Table 5 above, the device driving voltage prepared using the compound of the present invention as a hole blocking layer material is significantly reduced and the device lifetime is prolonged, for example, by substantially 1.15 times or more the lifetime of the comparative device 1-9, 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, HB-13, HB-14 as a hole blocking layer material.
Compared with 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, HB-13 and HB-14 used in the comparative examples, the compound of the invention can obtain better technical effect as a hole blocking material than the comparative compounds by changing the intermediate bridging group or the substituent.
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. The compound with the nitrogen-containing heterocyclic structure is characterized in that the structure of the compound is shown as a general formula (1):
In the general formula (1), R 1 represents phenyl, biphenyl or naphthyl;
R 2 represents phenyl or naphthyl;
m1 and M2 are the same or different and are represented as benzene rings or naphthalene rings;
X 1、X2 and X 3 are independently represented as N;
l 1 represents a single bond or phenylene;
X represents an oxygen atom or a sulfur atom;
asterisks indicate the ligatable sites.
2. The compound according to claim 1, wherein the structure of the compound is represented by general formula (1-1), general formula (1-2), general formula (1-3) or general formula (1-4):
In the general formula (1-1), the general formula (1-2), the general formula (1-3) and the general formula (1-4), R 1 is phenyl, biphenyl or naphthyl;
X 1、X2 and X 3 are independently represented as N;
l 1 represents 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;
In the general formulae a, b and c, X represents an oxygen atom or a sulfur atom.
3. The compound according to claim 2, wherein the structure of the compound is represented by any one of the general formulae (2-1) to (2-8):
In the general formulae (2-1) to (2-8), X 1、X2、X3、R、R1 has the meaning as defined in claim 2.
4. The compound according to claim 2, wherein the structure of the compound is represented by any one of the general formulae (3-1) to (3-2):
In the general formulae (3-1) to (3-2), X 1、X2、X3、R、R1 has the meaning as defined in claim 2.
5. The compound of claim 2, wherein R is any one of the following structures:
6. The compound of claim 2, wherein R is any one of the following structures:
X represents an oxygen atom or a sulfur atom.
7. The compound of claim 1, wherein R 1 is any one of the following structures:
8. The compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
9. An organic electroluminescent device comprising a first electrode and a second electrode, with a plurality of organic thin film layers between the first electrode and the second electrode, characterized in that at least one organic thin film layer contains the compound according to 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 compound according to any one of claims 1 to 8.
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