CN111689985B - Containing SO2Compound with multi-heterocyclic structure and application thereof - Google Patents
Containing SO2Compound with multi-heterocyclic structure and application thereof Download PDFInfo
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a SO-containing organic electroluminescent display2The organic material of the compound with the multi-heterocyclic structure also discloses the application of the compound in an organic electroluminescent device. The invention provides a process for preparing a compound containing SO2The compound with a multi-heterocyclic structure is shown as a general formula (I), and can be applied to the field of organic electroluminescence and used as an electron transport material. The structural compound provided by the invention is applied to an OLED device, can reduce the driving voltage of the device and improve the luminous efficiency of the device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, and particularly discloses a novel SO-containing material2The compound of multi-heterocyclic structure and its applicationIts application in organic electroluminescent devices.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). Compared with liquid crystal display devices, OLEDs do not need backlight sources, have wider viewing angles and low power consumption, and have response speed 1000 times that of the liquid crystal display devices, so the OLEDs have wider application prospects.
Since the first time high efficiency Organic Light Emitting Diodes (OLEDs) were reported, many researchers have been working on improving the performance of OLED devices. Organic charge transport materials are an important material for OLED devices. The organic charge transport material is an organic semiconductor material which can realize the controllable directional ordered movement of carriers under the action of an electric field when the carriers (electrons or holes) are injected, thereby carrying out charge transport. The organic charge transport material mainly transports holes and is called a hole type transport material, and the organic charge transport material mainly transports electrons and is called an electron type transport material or an electron transport material for short. Organic charge transport materials have been developed to date, in which hole transport materials are more diverse and have better performance, and electron transport materials are less diverse and have poorer performance. For example, the currently commonly used electron transport material Alq3 has low electron mobility, which results in higher operating voltage of the device and serious power consumption; part of electron transport materials such as LG201 triplet level is not high, and when a phosphorescent light emitting material is used as a light emitting layer, an exciton blocking layer needs to be added, otherwise the efficiency is reduced; still other materials, such as Bphen, tend to crystallize, resulting in reduced lifetimes. These problems with electron transport materials are bottlenecks that affect the development of organic electroluminescent display devices. Therefore, the development of new electron transport materials with better performance has important practical application value.
Disclosure of Invention
The invention aims to develop an electron transport material of an organic electroluminescent device, which is applied to an OLED device, can reduce driving voltage and improve the luminous efficiency of the device.
In particular, in a first aspect, the present invention provides a composition comprising SO2A compound with a multi-heterocyclic structure, which has a structure shown as a general formula (I):
wherein:
R1～R12optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, and R1～R12At least one of which is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties, and is linked to the parent nucleus represented by the general formula (I) through a C atom on the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties.
As a preferred embodiment of the present invention, in the general formula (I), R1～R12Optionally selected from H, substituted or unsubstituted heteroatom-containing aromatic groups having electron withdrawing properties, and R1～R12Not H at the same time;
the aromatic group is monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group, the polycyclic aromatic hydrocarbon group is optionally selected from poly-phenylated aliphatic hydrocarbon group, biphenyl type polycyclic aromatic hydrocarbon group and fused ring aromatic hydrocarbon group, the number of contained heteroatoms is 1-6, and the heteroatoms are optionally selected from N, O, S.
As a preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties is optionally selected from: substituted or unsubstituted benzodiazine group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted benzoxazolyl or naphthoxazolyl group, substituted or unsubstituted benzothiazolyl or naphthothiazolyl group, substituted or unsubstituted benzimidazolyl or naphthoimidazolyl group, aromatic group containing at least one benzene ring substituted by one or more pyridyl groups, substituted or unsubstituted pyridyl group, substituted or unsubstituted bipyridyl group, substituted or unsubstituted phenanthroline group, substituted or unsubstituted benzophenanthroline group, substituted or unsubstituted pyridophenanthroline group, substituted or unsubstituted pyrrolophenanthroline group, substituted or unsubstituted imidazophenanthroline group, substituted or unsubstituted pyrazoloanthroline group, substituted or unsubstituted diazinoanthroline group, One or more triazinyl-substituted aromatic group containing at least one benzene ring, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted isoquinolyl group; the diazine may be a pyridazine, pyrimidine or pyrazine;
the substituted substituents may be 1 to 5, said substituents being optionally selected from: alkyl, phenyl, alkylphenyl, naphthyl, biphenyl, benzo, naphtho, pyridyl, pyrrolyl, imidazolyl, pyrazolyl, diazinyl, quinolyl, isoquinolyl, fluorenyl, oxyfluorenyl, dibenzothiophenyl, carbazolyl; the substitution position of the substituent may be on a carbon atom or on a hetero atom.
As a preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties is optionally selected from: a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group;
the substituted substituents may be 1 to 5, said substituents being optionally selected from: alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyridyl, pyrido, pyrrolyl, pyrrolo, imidazolyl, imidazo, pyrazolyl, pyrazolo, diazinyl, diazino, 1, 10-phenanthroline, s-triazinyl, fluorenyl, oxyfluorenyl, thiofluorenyl, quinolyl, isoquinolyl, carbazolyl;
the hydrogen on the substituent can be further substituted by any of the following groups of 1-3: alkyl, phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzimidazolyl, fluorenyl, oxyfluorenyl, and dibenzothiophenyl.
As a further preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties is optionally selected from: a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted pyrimidyl group;
the substituted substituents may be 1 to 3, said substituents being optionally selected from: c1～C5Alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyrazinylPyridyl, 1, 10-phenanthroline-o-group, pyrazino-group, s-triazinyl, fluorenyl, oxyfluorenyl, dibenzoyl and quinolyl;
the hydrogen on the substituent can be further substituted by any of the following groups of 1-2: c1～C5Alkyl, phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, fluorenyl, oxyfluorenyl, or thiofluorenyl.
As a preferred embodiment of the present invention, in the general formula (I), R1～R12Each independently selected from H or the following groups:
and R is1～R12Not H at the same time.
Further preferably, in the general formula (I), R is1～R12Each independently selected from H or the following groups:
and R is1～R12Not H at the same time.
More preferably, in the general formula (I), R is1～R12Each independently selected from H or the following groups:
and R is1～R12Not H at the same time.
In each of the above-mentioned substituent groups, "- - -" represents a substitution position.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above1～R12At least one is selected from the group consisting of radicals other than H, preferably the R1～R12Wherein 1 to 5 groups are selected from groups other than H, and more preferably R1～R121 to 3 groups selected from the group other than H; when said R is1～R12When two or more groups other than H are selected, the groups other than H may be the same or different.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above1～R12One of them is selected from groups other than H, and the others are all H; preferably R1、R2、R3、R7、R10Or R11Is a group other than H, more preferably R2、R7Or R10Is a group other than H. For example, R1～R12In R2Is a group other than H, and the others are all H; or R1～R12In R7Is a group other than H, and the others are all H; or R1～R12In R10The radicals other than H are all H.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above1～R12Two of them are selected from groups other than H, and the others are both H. Preferably R1And R3、R2And R7、R7And R10、R2And R10The radicals other than H are all H. For example, R1～R12In R1And R3Is a group other than H, the others are all H, and R1And R3The groups other than H may be the same or different; or R1～R12In R2And R7Is a group other than H, the others are all H, and R2And R7The groups other than H may be the same or different; or R1～R12In R7And R10Is a group other than H, the others are all H, and R7And R10The groups other than H may be the same or different; or R1～R12In R2And R10Is a group other than H, the others are all H, and R2And R10The groups other than H may be the same or different.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above1～R12Three of (1) are selected from groups other than H, and the others are all H; preferably R1～R4Wherein one is selected from the group consisting of radicals other than H, R5～R8Wherein one is selected from the group consisting of radicals other than H, R9～R12One of them is selected from the group other than H, and the others are all H; more preferably, R2、R7、R10Is selected from groups other than H, and all others are H.
As a preferred embodiment of the present invention, the compound represented by the general formula (I) is preferably selected from compounds represented by the following structural formulae:
second partyThe invention also provides the SO-containing2Application of a compound with a multi-heterocyclic structure in preparing an organic electroluminescent device.
Preferably, said SO-containing2The compound with a multi-heterocyclic structure is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising an electron transport layer, wherein the material of the electron transport layer contains the SO-containing material2A compound of a polyheterocyclic structure.
Specifically, the invention provides an organic electroluminescent device, which sequentially comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top, wherein an electron transport material of the electron transport layer comprises the compound shown in the general formula (I), namely the compound containing SO provided by the invention2A compound of a polyheterocyclic structure.
In a preferred embodiment, the thickness of the electron transport layer may be 10 to 50nm, preferably 20 to 40 nm.
In a fourth aspect, the present invention provides a display device comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The SO-containing compound with the structure shown as the general formula (I) provided by the invention2A compound of polyheterocyclic structure, wherein R1～R12Optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, and R1～R12At least one of which is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties, through the C atom on the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties and the parent compound of the general formula (I)The cores are connected.
Specifically, the substituted or unsubstituted aromatic group containing a heteroatom optionally selected from the group consisting of an N atom, an S atom and an O atom and having an electron-withdrawing property contains at least one heteroatom. The substituted or unsubstituted aromatic group containing heteroatoms and having electron withdrawing property can be monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon; the polycyclic aromatic hydrocarbon can be poly-benzene aliphatic hydrocarbon, biphenyl polycyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon. The substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property may contain no five-membered ring or at least one five-membered ring.
In a preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having an electron-withdrawing property contains a benzene ring and a five-membered ring, and contains one heteroatom, specifically, a N atom, an S atom or an O atom, and the heteroatom may be on the five-membered ring or on the benzene ring.
When the substituted or unsubstituted heteroatom-containing aromatic group having an electron-withdrawing property contains two heteroatoms, the two heteroatoms may be the same or different. Specifically, the two heteroatoms are both N atoms, or both S atoms, or both O atoms, or both N atoms and S atoms, or both N atoms and O atoms, or both S atoms and O atoms. The two heteroatoms may be on the same five-membered ring, may be on two different five-membered rings, may be on the same benzene ring, may be on two different benzene rings, or may be one on the five-membered ring and the other on the benzene ring.
When the substituted or unsubstituted heteroatom-containing aromatic group having an electron-withdrawing property contains three heteroatoms, the three heteroatoms may be the same, any two of the heteroatoms may be the same, or may be different from each other. Specifically, the three heteroatoms are all N atoms, or all S atoms, or all O atoms, or two N atoms and the other S atom, or two N atoms and the other O atom, or two S atoms and the other N atom, or two S atoms and the other O atom, or two O atoms and the other N atom, or two O atoms and the other S atom, or N atom, S atom and O atom, respectively. The three heteroatoms may all be on the same five-membered ring, may all be on the same benzene ring, may be any two of the other on the same five-membered ring on another five-membered ring, may be any two of the other on the same five-membered ring on a benzene ring, may be any two of the other on the same benzene ring on a five-membered ring, may be any two of the other on the same benzene ring on another benzene ring, may be any two of the other on different five-membered rings on a benzene ring, may be any two of the other on different benzene rings on five-membered rings, may be on three different five-membered rings, or may be on three different benzene rings, respectively.
The invention provides a novel SO-containing2The compound with a multi-heterocyclic structure is shown as a general formula (I) and contains SO2The multi-heterocyclic structure is a mother nucleus which has stronger electron-withdrawing capability and good thermal stability; the compounds of this structure have suitable HOMO and LUMO energy levels and Eg; further by introducing an electron-withdrawing group R into the parent ring structure1～R12The electron injection capability can be effectively enhanced, and the electron transmission performance is improved.
The invention provides novel OLED materials containing SO2The compound with a multi-heterocyclic structure is used as a matrix, the matrix structure has strong electron-withdrawing capability, and a novel OLED material is obtained by introducing an electron-withdrawing group into the matrix structure. The material has high electron transport performance, good film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, is used as an electron transport material of an OLED device, is a stable and efficient electron transport material, can effectively reduce the driving voltage of the device, improves the luminous efficiency of the device and improves the photoelectric performance of the device. The invention provides a process for preparing a compound containing SO2The novel OLED material of the compound with the multi-heterocyclic structure can be well applied to OLED devices and has important practical application value. The device can be applied in the fields of display and illumination.
Detailed Description
The technical solution of the present invention will be described in detail by specific examples. The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
Synthesizing intermediate M1-M10
Synthesis of intermediate M1
The synthetic route is as follows:
the specific operation steps are as follows:
(1) adding 4-chloro-1-fluoro-2-nitrobenzene (17.5g, 0.1mol) and 2-bromo-4-chloroaniline (30.8g, 0.15mol) into a 2L three-necked bottle with mechanical stirring, protecting with argon, heating to 180 ℃, keeping the temperature for reaction for more than 30 hours, wherein the color of the reaction solution gradually becomes red in the reaction process, and finally gradually becomes deep red. After the reaction is finished, an organic phase is separated, extracted, dried, subjected to column chromatography, and subjected to spin-drying to obtain 30g of orange-red solid M-01 with the yield of 83%.
(2) In a 1L three-necked flask equipped with a mechanical stirrer, M-01(36.0g, 0.1mol), sodium sulfide nonahydrate (96g, 0.4mol), ethanol (200mL), and water (100mL) were added, and the mixture was heated to reflux under nitrogen protection, and the reaction was terminated after refluxing for 3 hours. Separating organic phase, extracting, drying, column chromatography and spin-drying solvent to obtain 26.5g white solid M-02 with yield of 80%.
(3) In a 1L three-necked flask with mechanical stirring, adding M-02(33.0g, 0.1mol) and 300mL of acetone for complete dissolution, adding a solution of KOH (11.2g,0.2mol) dissolved in water (50mL), slowly dropwise adding 2-bromo-4-chlorobenzoyl chloride (25.2g, 0.1mol) into the reaction flask, gradually precipitating solids in the reaction flask, reacting at normal temperature for 2 hours after the dropwise adding is finished, and finishing the reaction. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 43.8g of white solid M-03 with the yield of 79%.
(4) Adding M-03(54.8g, 0.1mol) and 200mL of glycol ether into a 1L three-necked flask, gradually heating to reflux under the protection of nitrogen, gradually dissolving the solid, magnetically stirring, keeping the temperature and reacting for 3 hours, and finishing the reaction. The organic phase was separated, extracted, dried, column chromatographed, and the solvent was spin-dried to give 40g of M-04 as a pale red solid in 76% yield.
(5) Under the protection of nitrogen, M-04(53.0g, 0.1mol) and THF 800mL are added into a 2L three-necked flask, the mixture is cooled to-78 ℃, n-butyllithium (100mL, 0.25mol) is slowly added dropwise under stirring for about 30mins, 50mL of THF is used for flushing a dropping funnel after dropping, and the temperature is kept for 1.5 hours after dropping to obtain a reaction solution of M-05. Slowly dropwise adding sulfur dichloride (16mL, 0.25mol) into a low-temperature system at-78 ℃, then flushing a dropping funnel with a small amount of THF, preserving the temperature for 1 hour after the addition is finished, slowly heating to room temperature, stirring at room temperature for reacting for 4 hours, and finishing the reaction. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 26.6g of a white solid intermediate M-06 with a yield of 66%.
(6) Adding M-06(40.2g, 0.1mol) and 600mL of dichloromethane into a 2L three-necked bottle, starting stirring, slowly dropwise adding (40mL, 0.4mol, 30%) aqueous hydrogen peroxide, reacting at room temperature for 2 hours, finishing the reaction, adding 100mL of saturated aqueous sodium bicarbonate, stirring, separating, performing rotary drying to obtain a white solid, performing dichloromethane column chromatography, performing column chromatography, and performing column liquid rotary drying to obtain 39.1g of the white solid, namely the mother nucleus intermediate M1, wherein the yield is 90%.
Product MS (m/e): 433.95, respectively; elemental analysis (C)19H9Cl3N2O2S): theoretical value C: 52.38%, H: 2.08%, N: 6.43 percent; found value C: 52.14%, H: 1.96%, N: 6.21 percent.
Synthesis of intermediate M2
Reference to the Synthesis of intermediate M1, using
Respectively replace
And selecting a proper material ratio, and obtaining an intermediate M2 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 399.98, respectively; elemental analysis (C)19H10Cl2N2O2S): theoretical value C: 56.87%, H: 2.51%, N: 6.98 percent; found value C: 56.66%, H: 2.27%, N: 6.74 percent.
Synthesis of intermediate M3
Reference to the Synthesis of intermediate M1, using
Instead of the former
And selecting a proper material ratio, and obtaining an intermediate M3 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 399.98, respectively; elemental analysis (C)19H10Cl2N2O2S): theoretical value C: 56.87%, H: 2.51%, N: 6.98 percent; found value C: 56.63%, H: 2.28%, N: 6.72 percent.
Synthesis of intermediate M4
Reference to the Synthesis of intermediate M1, using
Instead of
And selecting a proper material ratio, and obtaining an intermediate M4 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 399.98, respectively; elemental analysis (C)19H10Cl2N2O2S): theoretical value C: 56.87%, H: 2.51%, N: 6.98 percent; found value C: 56.63%, H: 2.28%, N: 6.72 percent.
Synthesis of intermediate M5
Reference to the Synthesis of intermediate M1, using
Respectively replace
And selecting a proper material ratio, and obtaining an intermediate M5 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 366.02, respectively; elemental analysis (C)19H11ClN2O2S): theoretical value C: 62.21%, H: 3.02%, N: 7.64 percent; found value C: 62.01%, H: 2.87%, N: 7.40 percent.
Synthesis of intermediate M6
Reference to the Synthesis of intermediate M1, using
Respectively replace
And selecting a proper material ratio, and obtaining an intermediate M6 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 366.02, respectively; elemental analysis (C)19H11ClN2O2S): theoretical value C: 62.21%, H: 3.02%, N: 7.64 percent; found value C: 62.01%, H: 2.87%, N: 7.41 percent.
Synthesis of intermediate M7
Reference to the Synthesis of intermediate M1, using
Respectively replace
And selecting a proper material ratio, and obtaining an intermediate M7 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 366.02, respectively; elemental analysis (C)19H11ClN2O2S): theoretical value C: 62.21%, H: 3.02%, N: 7.64 percent; found value C: 62.03%, H: 2.89%, N: 7.42 percent.
Synthesis of intermediate M8
Reference to the Synthesis of intermediate M1, using
Instead of the former
And selecting a proper material ratio, and obtaining an intermediate M8 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 399.98, respectively; elemental analysis (C)19H10Cl2N2O2S): theoretical value C: 56.87%, H: 2.51%, N: 6.98 percent; found value C: 56.63%, H: 2.28%, N: 6.72 percent.
Synthesis of intermediate M9
The synthetic route is as follows:
the specific operation steps are as follows:
(1) synthesis of intermediate M9-04:
by using
Respectively replace
Selecting proper material ratio, other raw materials and stepsThe synthesis method of the intermediate M1 is the same as the step of synthesis, and M9-04 is obtained firstly.
(2) Synthesis of intermediate M9-06:
in N2Under protection, M9-04(58.8g,0.1mol) and 500ml of anhydrous THF were added into a 2L three-necked flask, the reaction system was cooled to-78 ℃ with stirring by a liquid nitrogen ethanol bath, 70ml of a 1.6M hexane solution of n-butyllithium (0.11mol) was slowly added at this temperature, after completion of the dropwise addition, the temperature was maintained at this temperature for 15 minutes, sublimed sulfur powder (3.2g,0.1mol) was then added, after completion of the addition, the reaction system was stirred at-78 ℃ for 1 hour, and then the reaction system was slowly heated to-20 ℃ and kept at this temperature for 30 minutes. The reaction was then cooled further to-78 ℃ and CuCl (10g, 0.1mol) was added, the temperature was held at this temperature for 30 minutes, then the cold bath was removed, the reaction was allowed to warm to room temperature naturally, stirred for 2h, then the reaction was heated to reflux and reacted for 2 h. Cooling to room temperature, slowly adding saturated ammonium chloride solution, adding 250ml of ethyl acetate, separating the organic phase, extracting the aqueous phase with ethyl acetate for 3 times, combining the organic phases, drying the anhydrous magnesium chloride, spin-drying the solvent, and separating by column chromatography to obtain 19.0g of intermediate M9-06 in total, which is a white solid with a yield of about 46%.
(3) Synthesis of intermediate M9:
adding M9-06(41.2g, 0.1mol) and 300mL of dichloromethane into a 1L three-necked bottle, starting stirring, slowly dropwise adding (40mL, 0.4mol, 30%) aqueous hydrogen peroxide, reacting at room temperature for 2 hours, finishing the reaction, adding 100mL of saturated aqueous sodium bicarbonate, stirring, separating, performing rotary drying to obtain a white solid, performing dichloromethane column chromatography, performing column chromatography, and performing rotary drying on a column solution to obtain 40.0g of the white solid, namely an intermediate M9, wherein the yield is 90%.
Product MS (m/e): 443.93, respectively; elemental analysis (C)19H10BrClN2O2S): theoretical value C: 51.20%, H: 2.26%, N: 6.29 percent; found value C: 50.99%, H: 2.06%, N: 6.01 percent.
Synthesis of intermediate M10
Reference to the Synthesis of intermediate M9, using
Respectively replace
And selecting a proper material ratio, and obtaining an intermediate M10 by the same synthesis method of the intermediate M9 and other raw materials and steps.
Product MS (m/e): 443.93, respectively; elemental analysis (C)19H10BrClN2O2S): theoretical value C: 51.20%, H: 2.26%, N: 6.29 percent; found value C: 50.96%, H: 2.02%, N: 6.03 percent.
Example 1
The synthetic route is as follows:
the synthesis of the compound I-6 comprises the following specific steps:
A2L three-necked flask was taken, stirred with magnetic force, and after nitrogen substitution, M1(43.4g, 0.1mol), (4-phenylquinazolin-2-yl) boronic acid (75.0g, 0.3mol), cesium carbonate (117g, 0.36mol) and dioxane 800ml were added in this order, followed by stirring. After nitrogen replacement again, (2.2g, 11mmol) tri-tert-butylphosphine and (4.1g, 4.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 71.7g of pale yellow solid with the yield of about 76%.
Product MS (m/e): 944.27, respectively; elemental analysis (C)61H36N8O2S): theoretical value C: 77.53%, H: 3.84%, N: 11.85 percent; found value C: 77.26%, H: 3.61%, N: 11.62 percent.
Example 2
The synthetic route is as follows:
synthesis of Compound I-14: using M2 instead of M1 and (benzo [ d ] thiazol-2-yl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other raw materials and procedures were the same as in example 1, selecting the appropriate material ratios, 47.2g of a pale yellow solid was obtained with a yield of about 79%.
Product MS (m/e): 598.06, respectively; elemental analysis (C)33H18N4O2S3): theoretical value C: 66.20%, H: 3.03%, N: 9.36 percent; found value C: 66.01%, H: 2.83%, N: 9.14 percent.
Example 3
The synthetic route is as follows:
synthesis of Compounds I-17: m3 was used instead of M1 and naphtho [2,3-d ] oxazol-2-ylboronic acid was used instead of (4-phenylquinazolin-2-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 1 to give 49.3g of a pale yellow solid with a yield of about 74%.
Product MS (m/e): 666.14, respectively; elemental analysis (C)41H22N4O4S): theoretical value C: 73.86%, H: 3.33%, N: 8.40 percent; found value C: 73.64%, H: 3.10%, N: 8.16 percent.
Example 4
The synthetic route is as follows:
synthesis of Compound I-34: using M4 instead of M1, (4- (dibenzo [ b, d ] furan-3-yl) -6-phenyl-1, 3, 5-triazin-2-yl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 1 to give 80.8g of a pale yellow solid with a yield of about 83%.
Product MS (m/e): 974.24, respectively; elemental analysis (C)61H34N8O4S): theoretical value C: 75.14%, H: 3.52%, N: 11.49 percent; found value C: 74.93%, H: 3.26%, N: 11.22 percent.
Example 5
The synthetic route is as follows:
synthesis of Compounds I-47: using M5 instead of M1 and (3, 5-bis (pyridin-4-yl) phenyl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 1 to give 47.8g of a pale yellow solid with a yield of about 85%.
Product MS (m/e): 562.15, respectively; elemental analysis (C)35H22N4O2S): theoretical value C: 74.72%, H: 3.94%, N: 9.96 percent; found value C: 74.48%, H: 3.71%, N: 9.73 percent.
Example 6
The synthetic route is as follows:
synthesis of Compound I-53: m6 was used in place of M1, and (1, 10-phenanthrolin-5-yl) boronic acid was used in place of (4-phenylquinazolin-2-yl) boronic acid, and the other raw materials and procedures were the same as in example 1, except that the appropriate material ratio was selected, whereby 43.9g of a pale yellow solid was obtained with a yield of about 86%.
Product MS (m/e): 510.12, respectively; elemental analysis (C)31H18N4O2S): theoretical value C: 72.93%, H: 3.55%, N: 10.97 percent; found value C: 72.69%, H: 3.32%, N: 10.73 percent.
Example 7
The synthetic route is as follows:
synthesis of Compounds I-56: m7 is used for replacing M1, benzo [ f ] [1,10] phenanthroline-6-yl boric acid is used for replacing (4-phenylquinazolin-2-yl) boric acid, a proper material ratio is selected, other raw materials and steps are the same as those in example 1, 45.4g of light yellow solid is obtained, and the yield is about 81%.
Product MS (m/e): 560.13, respectively; elemental analysis (C)35H20N4O2S): theoretical value C: 74.98%, H: 3.60%, N: 9.99 percent; found value C: 74.76%, H: 3.38%, N: 9.73 percent.
Example 8
The synthetic route is as follows:
synthesis of Compound I-58: the appropriate material ratios were chosen using M8 instead of M1, 6-isopropylquinolin-2-boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid and the other starting materials and procedures were the same as in example 1 to give 47.6g of a pale yellow solid with a yield of about 71%.
Product MS (m/e): 670.24, respectively; elemental analysis (C)43H34N4O2S): theoretical value C: 76.99%, H: 5.11%, N: 8.35 percent; found value C: 76.72%, H: 4.93%, N: 8.12 percent.
Example 9
The synthetic route is as follows:
the synthesis of the compound I-39 comprises the following specific steps:
into a 1L three-necked flask, M9(44.4g, 0.1mol), (2, 4-diphenylquinazolin-6-yl) boronic acid (32.6g, 0.1mol), sodium carbonate (21.2g,0.2mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is distilled off under reduced pressure, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried by spinning, ethyl acetate is pulped, and 53.0 light yellow solid I-39-1 is obtained by filtration, and the yield is about 82%.
A1L three-necked flask was taken, stirred with magnetic force, and then replaced with nitrogen, followed by sequentially adding I-39-1(64.6g, 0.1mol), (4- (1- (naphthalen-2-yl) -1H-benzo [ d ] imidazol-2-yl) phenyl) boronic acid (36.4g, 0.1mol), cesium carbonate (39g, 0.12mol), and dioxane 400ml, and stirring was started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 69.8g pale yellow solid, i.e. I-39, with yield of about 75%.
Product MS (m/e): 930.28, respectively; elemental analysis (C)62H38N6O2S): theoretical value C: 79.98%, H: 4.11%, N: 9.03 percent; found value C: 79.73%, H: 3.96%, N: 8.81 percent.
Example 10
The synthetic route is as follows:
synthesis of Compound I-60: m10 was used to replace M9, (3, 5-bis (pyridin-4-yl) phenyl) boronic acid was used to replace (2, 4-diphenylquinazolin-6-yl) boronic acid, (1, 10-phenanthroline-5-yl) boronic acid was used to replace (4- (1- (naphthalen-2-yl) -1H-benzo [ d ] imidazol-2-yl) phenyl) boronic acid, the appropriate material ratios were chosen, the other materials and procedures were the same as in example 9, 53.3g of a pale yellow solid, i.e., I-60, was obtained with a yield of about 72%.
Product MS (m/e): 740.20, respectively; elemental analysis (C)47H28N6O2S): theoretical value C: 76.20%, H: 3.81%, N: 11.34 percent; found value C: 75.98%, H: 3.56%, N: 11.11 percent.
According to the synthesis schemes of the above examples 1 to 10, other compounds in I-1 to I-60 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 11
The embodiment provides a group of OLED green light devices, and the device structure is as follows: ITO/HATCN (1nm)/HT01(40nm)/NPB (20nm)/EML (30 nm)/any of the compounds (40nm)/LiF (1nm)/Al provided in examples 1 to 10, the preparation process comprising:
(1) ultrasonically cleaning a glass substrate coated with an ITO transparent conductive thin film layer in cleaning solution, ultrasonically treating the glass substrate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass substrate in a clean environment until the water is completely removed, carrying out etching and ozone treatment by using an ultraviolet lamp, and bombarding the surface by using low-energy cation beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then, evaporating and plating a layer of NPB (N-propyl bromide) on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
(3) vacuum evaporating EML (electron emission layer) on the hole transport layer to serve as a light emitting layer of the device, wherein the EML comprises a main material and a dye material, placing the main material serving as the light emitting layer in a chamber of a vacuum vapor deposition device by using a multi-source co-evaporation method, and adding Ir (ppy) serving as a dopant3Placing in another chamber of vacuum vapor deposition equipment, adjusting evaporation rate of CBP as main material to 0.1nm/s, and adjusting Ir (ppy) as dye material3The concentration of (2) is 10%, and the total film thickness of evaporation plating is 30 nm; wherein CBP, Ir (ppy)3The structural formula of (A) is as follows:
(4) taking any one of the compounds provided in the embodiments 1 to 10 as an electron transport material of an electron transport layer of a device for evaporation, wherein the evaporation rate is 0.1nm/s, and the total thickness of the evaporation film is 40 nm;
(5) sequentially vacuum evaporating LiF with the thickness of 1nm on the electron transport layer to serve as an electron injection layer of the device, continuously evaporating a layer of Al on the electron injection layer to serve as a cathode of the device, and evaporating the film with the thickness of 150 nm; obtaining a series of OLED-1-OLED-10 devices provided by the invention.
According to the same procedure as above, only the electron transport material in the step (4) was replaced with the following comparative compound, the structural formula of which is shown below, to obtain a comparative device OLED-11.
The performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
TABLE 1
As can be seen from the results in the table above, the current efficiency of the devices OLED-1 to OLED-10 prepared by using the compound provided by the invention is higher, and the working voltage is obviously lower than that of the device OLED-11 using the comparative compound Bphen as an electron transport material under the condition of the same brightness. As described above, the organic material represented by the general formula (I) provided by the invention is a novel electron transport material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. Containing SO2A compound of polyheterocyclic structure having a structure represented by general formula (i):
wherein:
R1～R12optionally selected from H, substituted or unsubstituted heteroatom-containing aromatic groups having electron withdrawing properties, and R1～R12At least one of which is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties and is linked to the parent nucleus represented by the general formula (I) through the C atom on the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties;
the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties is optionally selected from: a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted pyrimidyl group;
the substituted substituents may be 1 to 3, said substituents being optionally selected from: c1～C5Alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyridyl, 1, 10-phenanthrolino, pyrazino, s-triazinyl, fluorenyl, oxyfluorenyl, thiofluorenyl, quinolyl;
the hydrogen on the substituent can be further substituted by any of the following groups of 1-2: c1～C5Alkyl, phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, fluorenyl, oxyfluorenyl, or thiofluorenyl.
2. A compound of claim 1, wherein R is1～R12Each independently selected from H or the following groups:
and R is1～R12Not H at the same time.
3. A compound according to claim 1 or 2, wherein R is1～R12When said R is selected from the group consisting of1～R12When two or more groups other than H are selected, the groups other than H may be the same or different.
4. A compound of claim 3, wherein R is1～R12One of them is selected from groups other than H, and the others are all H; wherein R is1、R2、R3、R7、R10Or R11Is a group other than H;
or, said R1～R12Two of which are selected from groups other than H, whichIt is all H; wherein R is1And R3、R2And R7、R7And R10、R2And R10Is a group other than H, and the others are all H;
or, said R1～R12Three of (1) are selected from groups other than H, and the others are all H; wherein R is1～R4Wherein one is selected from the group consisting of radicals other than H, R5～R8Wherein one is selected from the group consisting of radicals other than H, R9～R12One of them is selected from the group consisting of radicals other than H, and the others are all H.
5. The compound of claim 1, wherein the compound is selected from the group consisting of compounds represented by the following structural formulae:
6. the SO-containing composition according to any one of claims 1 to 52Application of a compound with a multi-heterocyclic structure in preparing an organic electroluminescent device.
7. Use according to claim 6, wherein said SO comprises2The compound with a multi-heterocyclic structure is used as an electron transport material in an organic electroluminescent device.
8. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises electron transportA layer comprising the SO-containing layer according to any one of claims 1 to 5 as a material for the electron transport layer2A compound of a polyheterocyclic structure.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170237015A1 (en) * | 2016-02-11 | 2017-08-17 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| WO2017210206A1 (en) * | 2016-05-31 | 2017-12-07 | The Scripps Research Institute | Ultra-potent vina alkaloids: added molecular complexity further disrupts the tublin dimer-dimer interface |
| CN111039954A (en) * | 2019-11-28 | 2020-04-21 | 北京燕化集联光电技术有限公司 | Novel organic material and application thereof in device |
-
2020
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170237015A1 (en) * | 2016-02-11 | 2017-08-17 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| WO2017210206A1 (en) * | 2016-05-31 | 2017-12-07 | The Scripps Research Institute | Ultra-potent vina alkaloids: added molecular complexity further disrupts the tublin dimer-dimer interface |
| CN111039954A (en) * | 2019-11-28 | 2020-04-21 | 北京燕化集联光电技术有限公司 | Novel organic material and application thereof in device |
Non-Patent Citations (2)
| Title |
|---|
| Highly regioselective synthesis of fused seven-membered rings through copper-catalyzed cross-coupling;Peng Sang等;《ChemComm》;20121203;第49卷(第7期);全文 * |
| Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement;Fangdong Hu等;《Org. Biomol. Chem》;20161108;第14卷(第47期);全文 * |
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