CN113735878A - Organic compound and electroluminescent application thereof - Google Patents

Organic compound and electroluminescent application thereof Download PDF

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CN113735878A
CN113735878A CN202111243728.3A CN202111243728A CN113735878A CN 113735878 A CN113735878 A CN 113735878A CN 202111243728 A CN202111243728 A CN 202111243728A CN 113735878 A CN113735878 A CN 113735878A
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deuterium
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CN113735878B (en
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过宇阳
刘营
邓东阳
张磊
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Wuhan Tianma Microelectronics Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract

The invention provides an organic compound, which has a structure shown in a formula (I). The invention provides an electron transport material containing S and O and having a spiro-like structure, which has a proper HOMO and a lower LUMO value and can improve the electron injection and transport capacity; meanwhile, the organic compound has higher triplet state energy level, high electron mobility, excellent thermal stability and film stability, and is favorable for improving the luminous efficiency when used for an organic light-emitting device.
Figure DDA0003320182350000011

Description

Organic compound and electroluminescent application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
The electron transport material used in the traditional electroluminescent device is 8-hydroxyquinoline aluminum (Alq3), but the electron mobility ratio of Alq3 is low (about l 0-6 cm)2Vs) such that electron transport and hole transport of the device are not balanced. With the commercialization and practicability of electroluminescent devices, it is desirable to obtain ETL materials with higher transmission efficiency and better usability, and researchers have done a great deal of exploratory work in this field.
Patent No. WO2007/011170Al and chinese patent publication No. CN101003508A in LG chemistry disclose a series of naphthoimidazole and pyrene derivatives, respectively, as electron transporting and injecting materials in electroluminescent devices, which improve the luminous efficiency of the devices.
Kodak, in U.S. patent nos. US2006/0204784 and US2007/0048545, disclose organic electroluminescent devices of mixed electron transport materials doped with: (a) a first compound having a lowest LUMO level in the layer, (b) a second compound having a LUMO level higher than that of the first compound and having a low turn-on voltage; a metal material having a work function of less than 4.2 eV. However, the electron transport material has a planar molecular structure and a large intermolecular attraction, which is not favorable for vapor deposition and application; in addition, the electron transport material also has the defects of low mobility, poor energy level matching, poor thermal stability, short service life, doping property and the like, and further development of the OLED display device is limited.
Therefore, the electron transport material and/or the electron injection material which are stably and efficiently designed and developed, have high electron mobility and high glass transition temperature, and are effectively doped with metal Yb or Liq are/is designed, the threshold voltage is reduced, the device efficiency is improved, the service life of the device is prolonged, and the method has important practical application value.
Most of the electron transport materials currently used in the market, such as batho-phenanthroline (BPhen), Bathocuproine (BCP) and TmPyPB, can substantially meet the market demand of organic electroluminescent panels, but their glass transition temperature is low, generally less than 85 ℃, and the generated joule heat during device operation can cause molecular degradation and change of molecular structure, resulting in low panel efficiency and poor thermal stability. Meanwhile, the molecular structure is symmetrical regularly, and the crystal is easy to crystallize after a long time. Once the electron transport material is crystallized, the charge transition mechanism between molecules is different from the amorphous thin film mechanism in normal operation, resulting in the decrease of electron transport performance, the imbalance of electron and hole mobility of the whole device, the exciton formation efficiency is greatly reduced, and the exciton formation is concentrated at the interface of the electron transport layer and the light emitting layer, resulting in the severe decrease of device efficiency and lifetime.
Therefore, there is a need in the art to develop a wider variety of electron transport materials with higher performance to meet the application requirements of OLED display devices.
Disclosure of Invention
In view of the above, the present invention is to provide an organic compound and its electroluminescent application, wherein the organic compound has a suitable HOMO and a low LUMO value as an electron transport material, and can improve the electron injection and transport capability.
The invention provides an organic compound, which has a structure shown in a formula (I),
Figure BDA0003320182330000021
wherein X is S or O; y is S or O; and X is different from Y;
the R is1And R2Each independently selected from hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl; and R is1And R2Not hydrogen or deuterium at the same time;
the substituent groups in the substituted C1-C20 alkyl, the substituted amino, the substituted C6-C40 aryl and the substituted C2-C40 heteroaryl are respectively and independently selected from one or more of deuterium, cyano, carbonyl, substituted amino, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C2-C40 heterocyclic groups.
The invention provides a display panel, comprising an organic light emitting device; the organic light emitting device includes an anode, a cathode, at least one organic compound layer between the anode and the cathode; the organic compound layer includes at least one organic compound represented by formula (1).
The invention provides a display device which comprises the display panel.
Compared with the prior art, the organic compound shown in the formula (I) is an electron transport material with a S and O-containing spiro-like structure, has a proper HOMO and a lower LUMO value, and can improve the electron injection and transport capacity; meanwhile, the organic compound has higher triplet state energy level, high electron mobility, excellent thermal stability and film stability, and is favorable for improving the luminous efficiency when used for an organic light-emitting device.
Drawings
Fig. 1 is a schematic structural view of an organic light emitting device provided by the present invention;
fig. 2 is a schematic view of a display device provided in the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides an organic compound, which has a structure shown in a formula (I):
Figure BDA0003320182330000031
wherein X is S or O; y is S or O; and X is different from Y;
the R is1And R2Each independently is hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, and R1And R2Not hydrogen or deuterium at the same time; preferably hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and R1And R2Not hydrogen or deuterium at the same time; more preferably hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or substituted
Figure BDA0003320182330000041
A group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or substituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted anthronyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrazinyl, or substituted or unsubstituted or substituted or unsubstituted pyrazinyl, or substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted pyrazinyl, or substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted pyrazinyl, or substituted orSubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted indolocarbafuranyl, substituted or unsubstituted indolocarbathiophenyl, substituted or unsubstituted benzofuranpyrimidinyl, substituted or unsubstituted benzothiophenpyrimidinyl, and R1And R2Not hydrogen or deuterium at the same time; more preferably hydrogen, deuterium, phenylamino, diphenylamino, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, anthracenyl, triphenylenyl, pyrenyl, phenanthrenyl, and the like,
Figure BDA0003320182330000042
A group selected from the group consisting of a phenyl group, a fluorenyl group, a spirobifluorenyl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a pyrazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, an indolyl group, a benzofuranyl group, a benzimidazolyl group, a benzothienyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, an anthracenyl group, a fluoranthenyl group, an indenocarbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, an indolocarbazolyl group, an indolophenylfuranyl group, an indolophenylthienyl group, a benzofuranyl group, a benzothiophenyl group, a pyrimidinyl group, a combination of the above groups, and a group in which R is fused1And R2Not hydrogen or deuterium at the same time.
The substituents in the substituted C1-C20 alkyl group, the substituted amino group, the substituted C6-C40 aryl group and the substituted C2-C40 heteroaryl group are independently one or more of deuterium, cyano group, carbonyl group, substituted amino group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C6-C40 aryl group and substituted and unsubstituted C2-C40 heterocyclic group, preferably one or more of deuterium, cyano group, carbonyl group, substituted amino group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C6-C30 aryl group and substituted and unsubstituted C2-C30 heterocyclic group, more preferably deuterium, cyano group, carbonyl group, substituted amino group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C6-C20 aryl group, substituted and unsubstituted C2-C30 heterocyclic group, and preferably one or more of deuterium, cyano group and substituted or unsubstituted C30 heterocyclic group, One or more of carbonyl, C1-C10 alkyl, C6-C20 aryl and C2-C20 heterocyclic group, more preferably one or more of deuterium, cyano, carbonyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl and substituted or unsubstituted triazinyl, and most preferably one or more of deuterium, cyano, carbonyl, phenyl, pyridyl and triazinyl. Wherein, the heteroatom in the heterocyclic group is preferably one or more of O, S and N.
According to the invention, more preferably, said R1Or R2Is hydrogen.
Further preferably, in the present invention, X may be O or S, Y may be O or S, and X and Y may be different elements. When X is S and Y is O, the organic compound is selected from one or more of structures shown in formulas (1) to (36):
Figure BDA0003320182330000051
Figure BDA0003320182330000061
when X is O and Y is S, the organic compound is selected from one or more of structures shown in formulas (37) to (72):
Figure BDA0003320182330000071
Figure BDA0003320182330000081
the invention provides an electron transport material containing S and O and having a spiro-like structure, which has a proper HOMO and a lower LUMO value, and heteroatoms in a five-membered heterocycle can increase the overlapping of molecular orbitals among molecules to a certain extent due to small atomic radius and large electronegativity, thereby being beneficial to improving the electron injection and transport capability; meanwhile, the organic compound has higher triplet state energy level, high electron mobility, excellent thermal stability and film stability, and is favorable for improving the luminous efficiency when used for an organic light-emitting device.
Further preferably, the organic compound provided by the invention comprises a rigid planar structure and an electron-deficient planar group, wherein the rigid planar structure is favorable for improving the glass transition temperature of the compound, the tendency planarity of the rigid planar structure and the electron-deficient planar group is favorable for stacking and electron coupling of molecules, the electron mobility of the compound is improved, and the compound is further used as an electron transport material for an organic electroluminescent device so as to improve the efficiency.
The organic compound provided by the invention is obtained by carrying out Suzuki coupling reaction on the compound shown in the formula (II) and the compound shown in the formula (III) and/or the formula (IV).
Figure BDA0003320182330000091
Wherein X1And X2Each independently is halogen or hydrogen, and is not simultaneously hydrogen; further, X1And X2Each independently is chlorine or hydrogen.
The invention also provides application of the organic compound shown in the formula (I) as an electron transport material.
The invention also provides an organic light-emitting device comprising the organic compound shown in the formula (I).
The invention also provides a display panel comprising an organic light emitting device; the organic light emitting device includes an anode, a cathode, at least one organic compound layer between the anode and the cathode; the organic compound layer includes at least one organic compound represented by the above formula (I).
In the display panel provided by the present invention, the anode material of the organic light emitting device may be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof. The anode material may also be selected from metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; the anode material may also be selected from conductive polymers such as polyaniline, polypyrrole, poly (3-methylthiophene), and the like. In addition, the anode material may also be selected from materials that facilitate hole injection in addition to the anode materials listed above, and combinations thereof, including known materials suitable for use as anodes.
In the display panel provided by the present invention, the cathode material of the organic light emitting device may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof. The cathode material may also be selected from multi-layered metallic materials such as LiF/Al, LiO2/Al、BaF2Al, etc. In addition to the cathode materials listed above, the cathode materials can also be materials that facilitate electron injection and combinations thereof, including materials known to be suitable as cathodes.
At least one organic compound layer is arranged between the anode and the cathode; according to the present invention, the organic compound layer preferably includes an electron transport layer; the electron transport layer preferably comprises at least one compound of formula (I) above.
According to one embodiment of the display panel of the present invention, the organic compound layer in the organic light emitting device includes at least a light emitting layer and an electron transport layer, and preferably further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an electron injection layer.
The organic electroluminescent device may be fabricated according to a method known in the art and will not be described in detail herein. In the present invention, the organic electroluminescent device can be fabricated by: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. The organic thin layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like.
Specifically, referring to fig. 1, fig. 1 is a schematic structural diagram of an organic light emitting device provided by the present invention, which includes a substrate 1, an anode 2, a first hole transport layer 3, a second hole transport layer 4, a light emitting layer 5, a first electron transport layer 6, a second electron transport layer 7, a cathode 8, and a cap 9, which are sequentially stacked.
The invention also provides a display device comprising the display panel. In the invention, the display device can be a mobile phone display screen, a computer display screen, a television display screen, an intelligent watch display screen, an intelligent automobile display screen, a VR or AR helmet display screen, display screens of various intelligent devices and the like.
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Examples of intermediate Synthesis
Figure BDA0003320182330000101
Synthesis of intermediate 1-2
Adding the compound 1-1(80mmol), the compound a (90mmol), potassium carbonate (0.3mol), tetrahydrofuran (250mL), water (120mL) and tetratriphenylphosphine palladium (0.6g) in sequence into a three-neck flask, heating and refluxing for 12h under the protection of nitrogen, cooling, extracting with dichloromethane, concentrating, and purifying a crude product by column chromatography to obtain an intermediate 1-2.
Synthesis of intermediates 1 to 3
In a three-necked flask, the intermediate 1-2(50mmol) and dry tetrahydrofuran (120mL) were sequentially charged, cooled to-70 ℃ under nitrogen, 3.0M n-butyllithium (20mL) was slowly added thereto, and the reaction was completed by dropwise addition for 1 hour, followed by addition of 70mL of a tetrahydrofuran solution containing the compound b (53 mmol). After the addition, slowly raising the temperature to room temperature, reacting for 3h, adding dichloromethane for extraction, concentrating, adding acetic acid (120mL) and concentrated hydrochloric acid (3mL), heating and refluxing for 8h, cooling, removing the solvent, using dichloromethane as a solvent for the crude product, washing with water, drying and concentrating an organic layer, and purifying the crude product by column chromatography to obtain an intermediate 1-3.
Figure BDA0003320182330000111
Synthesis of intermediate 2-2
Adding a compound 2-1(75mmol), a compound c (85mmol), potassium carbonate (0.3mol), tetrahydrofuran (250mL), water (120mL) and tetratriphenylphosphine palladium (0.6g) in sequence into a three-neck flask, heating and refluxing for 12h under the protection of nitrogen, cooling, extracting with dichloromethane, concentrating, and purifying a crude product by column chromatography to obtain an intermediate 2-2.
Synthesis of intermediates 2-3
In a three-necked flask, the intermediate 2-2(50mmol) and dry tetrahydrofuran (120mL) were sequentially added, cooled to-70 ℃ under nitrogen, 3.0M n-butyllithium (20mL) was slowly added thereto, and the reaction was completed by dropwise addition for 1 hour, followed by addition of 70mL of a tetrahydrofuran solution containing the compound d (55 mmol). After the addition, slowly raising the temperature to room temperature, reacting for 3h, adding dichloromethane for extraction, concentrating, adding acetic acid (120mL) and concentrated hydrochloric acid (3mL), heating and refluxing for 8h, cooling, removing the solvent, using dichloromethane as a solvent for the crude product, washing with water, drying and concentrating an organic layer, and purifying the crude product by column chromatography to obtain an intermediate 2-3.
Example 1: synthesis of Compound represented by the formula (7)
Figure BDA0003320182330000112
In a round-bottomed flask, intermediate 1-3(4mmol), compound e (6mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (180 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (7).
Characterization of the compound of formula (7): molecular formula C40H21N3O2S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 640.11, test value 639.95;
elemental analysis results: theoretical value: c75.10, H3.31, N6.57, O5.00, S10.02; test values are: c75.10, H3.35, N6.52, O5.03, S10.00.
Example 2: synthesis of Compound represented by the formula (11)
Figure BDA0003320182330000121
In a round-bottomed flask, intermediate 1-3(4mmol), compound f (6mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (200 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (11).
Characterization of the compound of formula (11): molecular formula C46H25N3O2S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 716.14, test value 716.19;
elemental analysis results: theoretical value: c77.18, H3.52, N5.87, O4.47, S8.96; test values are: c77.15, H3.55, N5.90, O4.44, S8.89.
Example 3: synthesis of Compound represented by the formula (19)
Figure BDA0003320182330000122
In a round-bottomed flask, intermediate 1-3(4mmol), compound g (6mmol) and Pd (PPh)3)4(0.4mmol) was added to a solution of toluene (180 mL)/ethanol (150mL) and potassium carbonate (15mmol) in waterThe mixture of liquids (12mL) was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (19).
Characterization of the compound of formula (19): molecular formula C45H24N2O2S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 689.13, test value 689.10;
elemental analysis results: theoretical value: c78.47, H3.51, N4.07, O4.65, S9.31; test values are: c78.50, H3.49, N4.06, O4.63, S9.33.
Example 4: synthesis of Compound represented by the formula (27)
Figure BDA0003320182330000131
In a round-bottomed flask, intermediate 1-3(5mmol), compound h (8mmol) and Pd (PPh)3)4(0.4mmol) was added to a mixture of toluene (200 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (12mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (27).
Characterization of the compound of formula (27): molecular formula C51H28O3S2；
ESI-MS (M/z) [ M +1] +, by liquid phase mass spectrometry analysis: theoretical value 753.15, test value 753.10;
elemental analysis results: theoretical value: c81.36, H3.75, O6.38, S8.52; test values are: c81.30, H3.80, O6.35, S8.54.
Example 5: synthesis of Compound represented by the formula (43)
Figure BDA0003320182330000141
In a round-bottomed flask, intermediate 2-3(4mmol), compound e (6mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (180 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (43).
Characterization of the compound of formula (43): molecular formula C40H21N3O2S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 640.11, test value 639.95;
elemental analysis results: theoretical value: c75.10, H3.31, N6.57, O5.00, S10.02; test values are: c75.08, H3.34, N6.56, O5.04, S9.98.
Example 6: synthesis of Compound represented by the formula (47)
Figure BDA0003320182330000142
In a round-bottomed flask, intermediate 2-3(4mmol), compound f (6mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (200 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. Cooling the resulting mixture to room temperature, adding water, filtering through a pad of celite, extracting the filtrate with dichloromethane, washing with water, drying over anhydrous magnesium sulfate, filtering and evaporating, and purifying the crude product by silica gel column chromatographyTo obtain the target product, the compound shown in formula (47).
Characterization of the compound of formula (47): molecular formula C46H25N3O2S2；
ESI-MS (M/z) [ M +1] +, by liquid phase mass spectrometry analysis: theoretical value 716.14, test value 716.20;
elemental analysis results: theoretical value: c77.18, H3.52, N5.87, O4.47, S8.96; test values are: c77.15, H3.58, N5.84, O4.45 and S8.88.
Example 7: synthesis of Compound represented by the formula (55)
Figure BDA0003320182330000151
In a round-bottomed flask, intermediate 2-3(4mmol), compound g (6mmol) and Pd (PPh)3)4(0.4mmol) was added to a mixture of toluene (180 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (12mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (55).
Characterization of the compound of formula (55): molecular formula C45H24N2O2S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 689.13, test value 689.10;
elemental analysis results: theoretical value: c78.47, H3.51, N4.07, O4.65, S9.31; test values are: c78.50, H3.55, N4.00, O4.63, S9.33.
Example 8: synthesis of Compound represented by the formula (63)
Figure BDA0003320182330000152
In a round-bottomed flask, intermediate 2-3(5mmol), compound h (9mmol) and Pd (PPh)3)4(0.4mmol) was added to a mixture of toluene (200 mL)/ethanol (150mL) and aqueous potassium carbonate (15mmol) (12mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective compound represented by formula (63).
Characterization of the compound of formula (63): molecular formula C51H28O3S2；
ESI-MS (M/z) [ M +1] obtained by liquid-phase mass spectrometry]+: theoretical value 753.15, test value 753.69;
elemental analysis results: theoretical value: c81.36, H3.75, O6.38, S8.52; test values are: c81.32, H3.79, O6.36, S8.54.
By using the Density Functional Theory (DFT), the distribution of the molecular front line orbitals HOMO and LUMO is optimized and calculated by the Guassian 09 package (Guassian Inc.) under the calculation level of B3LYP/6-31G (d), and the band gap E is obtained according to the energy levels of the HOMO and LUMO for the organic compounds provided by the embodiments 1-8 of the inventiongMeanwhile, the triplet state energy level E of the compound molecule is calculated based on time-density functional theory (TD-DFT) simulationTThe calculation results are shown in table 1.
TABLE 1 Gaussian simulation calculation results for organic compounds
Figure BDA0003320182330000161
As can be seen from Table 1, the compounds provided by the invention have deeper LUMO energy level (-1.856-1.999 eV), can reduce the potential barrier of electron transport, improve the injection capability of electrons, and effectively reduce the voltage of OLED devices; the compounds all have deep HOMO levels (-5.382 to-5.579 eV), which can effectively block holes, allow more holes-electrons to recombine in the light emitting region, and can achieve higher light emitting efficiency.
Device example 1 blue organic light emitting device (Compound of the present invention used as an Electron transport layer Material)
The present embodiment provides an organic light emitting device. As shown in fig. 1, the organic light emitting device includes: the structure of the organic electroluminescent device comprises a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9 (a magnesium-silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL)10, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the electron blocking layer 5 is 30nm, the thickness of the light emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 30nm, the thickness of the second electron transport layer 8 is 5nm, the thickness of the magnesium-silver electrode 9 is 15nm and the thickness of the cap layer (CPL)10 is 100 nm.
The organic light-emitting device of the present invention is prepared by the following steps:
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically treated in isopropanol and deionized water, respectively, for 30 minutes, and then exposed to ozone for about 10 minutes to perform cleaning; mounting the glass substrate having the ITO anode 2 obtained by magnetron sputtering on a vacuum deposition apparatus;
2) evaporating a hole buffer layer material compound HT-1: HAT-CN on an ITO anode 2 in a vacuum evaporation mode, wherein the mass ratio of the compound HT1 to the HAT-CN is 98:2 to obtain a layer with the thickness of 10nm, and the layer is used as a first hole transmission layer 3;
3) vacuum evaporating a material compound HT-1 of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with the thickness of 95nm, wherein the layer is used as the second hole transport layer 4;
4) evaporating a material Prime-1 on the second hole transport layer 4 to obtain a layer with the thickness of 30nm, wherein the layer is used as an electron blocking layer 5;
5) co-depositing a light-emitting layer 6 on the electron blocking layer 5, wherein a compound BH is used as a main material, a compound BD is used as a doping material, the mass ratio of the compound BH to the compound BD is 97:3, and the thickness of the light-emitting layer 6 is 30 nm;
6) a first electron transport layer 7, which is a compound represented by the formula (1) prepared in example 1, was vacuum-evaporated on the light-emitting layer 6 to obtain a first electron transport layer 7 having a thickness of 30 nm;
7) evaporating LiF material of the second electron transport layer 8 on the first electron transport layer 7 in vacuum to obtain the second electron transport layer 8 with the thickness of 5 nm;
8) performing vacuum evaporation on the second electron transport layer 8 to obtain a cathode 9 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9: 1;
9) a hole-type material CPL-1 having a high refractive index was vacuum-deposited on the cathode 9 to a thickness of 100nm, and used as a cathode cover layer (cap layer or CPL) 10.
The structural formulas of the materials HAT-CN, HT-1, Prime-1, BH, BD and CPL-1 mentioned in the steps are respectively shown as follows:
Figure BDA0003320182330000181
device example 2
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equivalent amount of the organic compound represented by formula (11) provided by the present invention; the other preparation steps are the same.
Device example 3
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equivalent amount of the organic compound represented by formula (9) provided by the present invention; the other preparation steps are the same.
Device example 4
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equal amount of the organic compound represented by formula (27) provided by the present invention; the other preparation steps are the same.
Device example 5
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equivalent amount of the organic compound represented by formula (43) provided by the present invention; the other preparation steps are the same.
Device example 6
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equal amount of the organic compound represented by formula (47) provided by the present invention; the other preparation steps are the same.
Device example 7
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equal amount of the organic compound represented by formula (55) provided by the present invention; the other preparation steps are the same.
Device example 8
This device example differs from device example 1 only in that the organic compound represented by formula (7) in step (6) is replaced with an equivalent amount of the organic compound represented by formula (63) provided by the present invention; the other preparation steps are the same.
Comparative device example 1
Comparative device example differs from device example 1 only in that the organic compound of formula (7) in step (6) was used in the same amount of comparative compound M1
Figure BDA0003320182330000191
Replacement; the other preparation steps are the same.
Comparative device example 2
Comparative device example differs from device example 1 only in that the organic compound of formula (7) in step (6) was used in the same amount of comparative compound M2
Figure BDA0003320182330000192
Replacement; the other preparation steps are the same.
Performance evaluation of OLED devices:
testing the current of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and then dividing the current by the light-emitting area to obtain the current density of the OLED device under different voltagesDegree; testing the brightness and radiant energy flux density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and the brightness of the OLED device under different voltages, the current density (10 mA/cm) is obtained under the same current density2) Von is the luminance 1Cd/m2A lower turn-on voltage; the lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance2Under test conditions); specific data are shown in table 2.
TABLE 2OLED device Performance test results
Figure BDA0003320182330000201
Note: E/CIEy represents the ratio of efficiency (E) to CIEy
As can be seen from the data in table 2, the electroluminescent device using the organic compound according to the present invention has a lighting voltage of not higher than 3.85V, a lower lighting voltage, which is decreased by about 9%, compared to the devices in comparative examples 1 and 2, and thus can effectively reduce the power consumption of the device; the device using the organic compound has higher current efficiency, the E/CIEy of some examples reaches 151.6-152.4 Cd/A, and is improved by about 14% compared with comparative examples 1 and 2; the device using the organic compound of the present invention has a longer lifetime, and the lifetime of LT95 of some examples reaches more than 64h, which is about 19% longer than that of comparative examples 1 and 2.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.

Claims (12)

1. An organic compound having a structure represented by formula (I),
Figure FDA0003320182320000011
wherein X is S or O; y is S or O; and X is different from Y;
the R is1And R2Each independently selected from hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl; and R is1And R2Not hydrogen or deuterium at the same time;
the substituent groups in the substituted C1-C20 alkyl, the substituted amino, the substituted C6-C40 aryl and the substituted C2-C40 heteroaryl are respectively and independently selected from one or more of deuterium, cyano, carbonyl, substituted amino, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C2-C40 heterocyclic groups.
2. The organic compound of claim 1, wherein R is1And R2Each independently selected from hydrogen, deuterium, cyano, substituted amino, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or substituted
Figure FDA0003320182320000012
A group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or substituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted pyridyl group, a substituted or substituted pyridyl group, a substituted or unsubstituted pyridyl group, a substituted or substituted pyridyl groupSubstituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted pyrrolidyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted anthronyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted indoaminobenzofuranyl, Substituted or unsubstituted indolophenylthienyl, substituted or unsubstituted benzofuran pyrimidinyl, and substituted or unsubstituted benzothiophenyl.
3. The organic compound of claim 1, wherein the substituents of the substituted C1-C20 alkyl group, the substituted amino group, the substituted C6-C40 aryl group and the substituted C2-C40 heteroaryl group are each independently selected from one or more of deuterium, cyano group, carbonyl group, C1-C10 alkyl group, C6-C20 aryl group and C2-C20 heterocyclic group; the heteroatom in the heterocyclic group is selected from one or more of O, S and N.
4. The organic compound of claim 1, wherein the substituents of the substituted C1-C20 alkyl group, the substituted amino group, the substituted C6-C40 aryl group, and the substituted C2-C40 heteroaryl group are each independently selected from one or more of deuterium, cyano group, carbonyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted pyridyl group, and substituted or unsubstituted triazinyl group.
5. The organic compound of claim 4, wherein the substituents of the substituted phenyl, substituted pyridyl and substituted triazinyl are each independently selected from one or more of deuterium, cyano, carbonyl, phenyl, pyridyl and triazinyl.
6. The organic compound of claim 1, wherein R is1And R2Each independently selected from hydrogen, deuterium, phenylamino, diphenylamino, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, anthracenyl, triphenylene, pyrenyl, and mixtures thereof,
Figure FDA0003320182320000021
A group selected from the group consisting of a phenyl group, a fluorenyl group, a spirobifluorenyl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a pyrazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, an indolyl group, a benzofuranyl group, a benzimidazolyl group, a benzothienyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, an anthracenyl group, a fluoranthenyl group, an indenocarbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, an indolocarbazolyl group, an indolophenylfuranyl group, an indolophenylthienyl group, a benzofuranyl group, a benzothienyl group, a benzofuranyl group, a combination thereof, and a mixture thereof.
7. An organic compound according to claim 1, wherein R is1Or R2Is hydrogen.
8. The organic compound according to claim 1, wherein X is S, Y is O, and the organic compound is one or more selected from the group consisting of structures represented by formulas (1) to (36):
Figure FDA0003320182320000031
Figure FDA0003320182320000041
9. the organic compound according to claim 1, wherein X is O, Y is S, and the organic compound is one or more selected from the group consisting of those having structures represented by formulas (37) to (72):
Figure FDA0003320182320000051
Figure FDA0003320182320000061
10. a display panel includes an organic light emitting device; the organic light emitting device includes an anode, a cathode, at least one organic compound layer between the anode and the cathode; the organic compound layer includes at least one organic compound according to any one of claims 1 to 9.
11. A display panel according to claim 10, wherein the organic compound layer comprises an electron transport layer containing at least one organic compound according to any one of claims 1 to 9.
12. A display device characterized by comprising the display panel according to claim 10 or claim 11.
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