CN112778312A - Organic material containing indoloquinazolinedione heterocyclic structure and application thereof - Google Patents
Organic material containing indoloquinazolinedione heterocyclic structure and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic material containing an indoloquinazolinedione heterocyclic structure, and also discloses an application of the organic material in an organic electroluminescent device. The organic material containing the indole quinazoline diketone heterocyclic ring 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, and the device has the advantages of low driving voltage and high luminous efficiency.
Description
Technical Field
The invention relates to the technical field of materials for organic electroluminescence, and particularly discloses a novel organic material containing an indoloquinazolinedione heterocyclic structure, and also discloses application of the organic material in an organic electroluminescent device.
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 and has the advantages of low driving voltage and high luminous efficiency.
Specifically, in a first aspect, the present invention provides an organic material containing an indoloquinazolinedione heterocyclic structure, having a structure represented by general formula (i):
wherein:
R1～R8optionally 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～R8At 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; r1～R8May be the same or different.
The halogen atom is F, Cl, Br or I.
Straight chain alkyl refers to the general formula CnH2n+1Straight chain alkyl of (E) -including but not limited to methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like.
Branched chain-containing alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like.
Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
Alkylamino refers to a group in which at least one H on the amino group is substituted with an alkyl group.
The substituted or unsubstituted aromatic group containing a heteroatom optionally selected from the group consisting of N atom, S atom and O atom and having 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.
Preferably, the substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property contains a benzene ring and a five-membered ring, and contains at least 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.
As a preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing property is a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, the polycyclic aromatic hydrocarbon group is optionally selected from a polyphenylaliphatic hydrocarbon group, a biphenyl-type polycyclic aromatic hydrocarbon group, a fused ring aromatic hydrocarbon group, the number of heteroatoms contained is 1 to 6, and the heteroatom is optionally selected from N, O, S.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property is selected from the group consisting of 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-phenanthroline group, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzopyrazinyl, substituted or unsubstituted s-triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl;
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, in the general formula (I), the substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property is 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-phenanthroline 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;
wherein, the substituted substituent can be 1-3, and the substituent is selected from the following groups: c1～C5Alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyridyl, 1, 10-phenanthrolinoA group selected from the group consisting of a pyrazinyl group, an s-triazinyl group, a fluorenyl group, an oxyfluorenyl group, a thiophenenyl group, and a quinolyl group;
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 further preferred embodiment, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
further preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
wherein "- -" represents a substituted bit.
As a further preferred embodiment, said R1～R8Any one of the groups is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties;
or, R1～R8Any two groups are substituted or unsubstituted heteroatom-containing aromatic groups with electron-withdrawing properties, and the two groups are positioned on different benzene rings or on the same benzene ring, preferably on different benzene rings; the two groups may be the same or different from each other.
As a further preferred embodiment, said R1～R8In (b), in addition to representing a substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property, the remaining group is selected from any one of a hydrogen atom, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group.
In a preferred embodiment of the present invention, R is1～R8In, R1、R6Is a group other than a hydrogen atom; or, R1、R7Is a group other than a hydrogen atom; or, R2、R6Is a group other than a hydrogen atom; or, R2、R7Is a group other than a hydrogen atom; or, R3、R6Is a group other than a hydrogen atom; or, R3、R7Is a group other than a hydrogen atom; or, R3、R8Is a group other than a hydrogen atom; or, R4、R6Is a group other than a hydrogen atom; or, R4、R7Is a group other than a hydrogen atom; r1～R8Wherein the others each represent a hydrogen atom.
Further preferably, R1～R8In, R1、R6Is a group other than a hydrogen atom; or, R2、R6Is a group other than a hydrogen atom; or, R2、R7Is a group other than a hydrogen atom; or, R3、R6Is a group other than a hydrogen atom; or, R3、R7Is a group other than a hydrogen atom; or, R4、R7Is a group other than a hydrogen atom; r1～R8Wherein the others each represent a hydrogen atom.
As a preferred embodiment of the present invention, the organic material is selected from compounds represented by the following structural formula:
in a second aspect, the invention provides an application of the organic material containing the indole quinazoline diketone heterocyclic structure in preparing an organic electroluminescent device.
Preferably, the organic material containing the indole quinazoline diketone heterocyclic ring structure is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the invention provides an organic electroluminescent device, which comprises an electron transport layer, wherein the material of the electron transport layer contains the organic material containing the indole quinazoline diketone heterocyclic ring 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) provided by the invention.
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 invention provides a novel compound containing an indole quinazoline diketone heterocyclic structure, which is specifically shown as a general formula (I), wherein the indole quinazoline diketone heterocyclic structure is taken as a parent nucleus, the parent nucleus of the series of compounds has strong electron-withdrawing capability and good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; the organic light emitting diode is connected with the electron-withdrawing group, so that the electron injection capability can be effectively enhanced, the electron transmission performance is improved, the organic light emitting diode can be well applied to an OLED device and used as an electron transmission material, and the photoelectric performance of the device can be effectively improved.
The organic material containing the indole quinazoline diketone heterocyclic structure provided by the invention can be used as an electron transport material, has higher electron transport performance, better film stability and suitable molecular energy level, can be applied to the field of organic electroluminescence, and can effectively improve the photoelectric performance of devices. Meanwhile, the organic light emitting diode has the advantages of good thermal stability, stability and high efficiency, and can be well applied to OLED devices. Therefore, the driving voltage can be reduced, the luminous efficiency of the device can be improved, and the method has important practical application value. The organic electroluminescent device made of the organic material has the characteristics of low driving voltage and high luminous efficiency. 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.
Synthesis of intermediates
Synthesis of intermediate M1
The synthetic route is as follows:
the specific operation steps are as follows:
in DMSO, I2(1.5 equiv.), CuI (0.3 equiv.), K2CO3(1 eq) 2-amino-5-chlorobenzamide was reacted with 1- (2-bromo-5-chlorophenyl) ethan-1-one at 100 ℃ for 6 hours to give intermediate M1 in 70% yield. (production method reference: International Journal of Pharma Research and Health Sciences, 2018; 6(6): 2865-68).
With reference to the literature and to the method of synthesis of intermediate M1, further desired intermediates M2 to M8 were synthesized.
EXAMPLE 1 Synthesis of Compound I-1
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was taken, stirred with magnetic force, and then, after nitrogen substitution, M1(31.6g, 0.1mol), (4-phenylquinazolin-2-yl) boronic acid (50.0g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml were sequentially added thereto, followed by stirring. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 51.9g of light yellow solid with the yield of about 79%.
Product MS (m/e): 656.20, respectively; elemental analysis (C)43H24N6O2): theoretical value C: 78.65%, H: 3.68%, N: 12.80 percent; found value C: 78.70%, H: 3.73%, N: 12.65 percent.
EXAMPLE 2 Synthesis of Compound I-13
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was taken, and magnetic stirring was carried out, then M2(31.6g, 0.1mol), benzo [ d ] thiazol-2-ylboronic acid (35.8g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were sequentially added after nitrogen substitution, and stirring was started. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 34.4g of pale yellow solid with the yield of about 67%.
Product MS (m/e): 514.06, respectively; elemental analysis (C)29H14N4O2S2): theoretical value C: 67.69%, H: 2.74%, N: 10.89 percent; found value C: 67.74%, H: 2.79%, N: 10.73 percent.
EXAMPLE 3 Synthesis of Compound I-22
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was taken, stirred with magnetic force, and then, after nitrogen substitution, M3(31.6g, 0.1mol), (1-phenyl-1H-naphthalene [2,3-d ] imidazol-2-yl) boronic acid (57.6g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml were sequentially added thereto, followed by stirring. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 47.6g of pale yellow solid with the yield of about 65%.
Product MS (m/e): 732.23, respectively; elemental analysis (C)49H28N6O2): theoretical value C: 80.31%, H: 3.85%, N: 11.47 percent; found value C: 80.38%, H: 3.90%, N: 11.30 percent.
EXAMPLE 4 Synthesis of Compound I-36
The synthetic route is as follows:
the preparation process comprises the following steps: into a 1L three-necked flask, M4(36.0g, 0.1mol), (9, 9-dimethyl-9H-fluoren-2-yl) boronic acid (23.8g, 0.1mol), sodium carbonate (15.9g,0.15mol), 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 evaporated, 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 in a rotating mode, the ethyl acetate is pulped, and 40.3g of light yellow solid I-36-1 is obtained through filtration, and the yield is about 85%.
A1L three-necked flask was taken, and magnetic stirring was carried out, then, after nitrogen substitution, I-36-1(47.4g, 0.1mol), (3, 5-bis (pyridin-4-yl) phenyl) boronic acid (27.6g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane (400 ml) were added in this order, 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 an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 54.9g of pale yellow solid with the yield of about 82%.
Product MS (m/e): 670.24, respectively; elemental analysis (C)46H30N4O2): theoretical value C: 82.37%, H: 4.51%, N: 8.35 percent; found value C: 82.43%, H: 4.55%, N: 8.21 percent.
EXAMPLE 5 Synthesis of Compound I-39
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask is taken, magnetic stirring is carried out, M2(31.6g, 0.1mol), (1, 10-phenanthroline-5-yl) boric acid (44.8g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml are sequentially added after nitrogen replacement, and stirring is started. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 39.3g of light yellow solid with the yield of about 65%.
Product MS (m/e): 604.16, respectively; elemental analysis (C)39H20N6O2): theoretical value C: 77.47%, H: 3.33%, N: 13.90 percent; found value C: 77.53%, H: 3.39%, N: 13.73 percent.
EXAMPLE 6 Synthesis of Compound I-43
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was taken, magnetic stirring was carried out, and after nitrogen substitution, M5(31.6g, 0.1mol), (4, 6-diphenyl-1, 3, 5-triazin-2-yl) boronic acid (55.4g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were sequentially added, followed by stirring. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 39.3g pale yellow solid with yield about 80%.
Product MS (m/e): 710.22, respectively; elemental analysis (C)45H26N8O2): theoretical value C: 76.04%, H: 3.69%, N: 15.77 percent; found value C: 76.09%, H: 3.55%, N: 15.61 percent.
EXAMPLE 7 Synthesis of Compound I-50
The synthetic route is as follows:
the preparation process comprises the following steps: into a 1L three-necked flask, M6(36.0g, 0.1mol), (4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid (35.3g, 0.1mol), sodium carbonate (15.9g,0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and after the reaction system was purged with nitrogen, Pd (PPh) was added3)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 evaporated off, 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 in a rotating mode, the ethyl acetate is pulped, and 45.9g of light yellow solid I-50-1 is obtained through filtration, and the yield is about 78%.
A1L three-necked flask is taken, magnetic stirring is carried out, after nitrogen replacement, I-50-1(58.9g, 0.1mol), 2-naphthalene boric acid (17.2g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml are sequentially added, and stirring is 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 an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 61.3g of pale yellow solid with the yield of about 90%.
Product MS (m/e): 681.22, respectively; elemental analysis (C)47H27N5O2): theoretical value C: 81.04%, H: 3.99%, N: 10.27 percent; found value C: 81.09%, H: 4.06%, N: 10.08 percent.
EXAMPLE 8 Synthesis of Compound I-54
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was taken, and magnetic stirring was carried out, and after nitrogen substitution, M5(31.6g, 0.1mol), (4- (dibenzo [ b, d ] furan-3-yl) -6-phenyl-1, 3, 5-triazin-2-yl) boronic acid (73.4g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml were sequentially added, followed by stirring. After nitrogen replacement again, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 66.8g of pale yellow solid with the yield of about 75%.
Product MS (m/e): 890.24, respectively; elemental analysis (C)57H30N8O4): theoretical value C: 76.85%, H: 3.39%, N: 12.58 percent; found value C: 76.89%, H: 3.45%, N: 12.42 percent.
EXAMPLE 9 Synthesis of Compound I-56
The synthetic route is as follows:
the preparation process comprises the following steps: A1L three-necked flask was charged with M7(36.0g, 0.1mol), (4, 6-bis (quinolin-3-yl) -1,3, 5-triazin-2-yl) boronic acid (37.9g, 0.1mol), sodium carbonate (15.9g,0.15mol), toluene 150mL, ethanol 150mL, and water 150mL, and the reaction system was purged with nitrogen and then protected with Pd (PPh)3)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. Distilling off solvent, extracting with dichloromethane, drying with anhydrous magnesium sulfate, and filteringFiltering, performing petroleum ether/ethyl acetate (2:1) column chromatography, spin-drying the solvent, pulping the ethyl acetate, and filtering to obtain 46.7g of light yellow solid I-56-1 with the yield of about 76%.
A1L three-necked flask was taken, stirred with magnetic force, and then replaced with nitrogen, followed by sequentially adding I-56-1(61.5g, 0.1mol), (4-cyclohexylphenyl) boronic acid (20.4g, 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 an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 62.1g of pale yellow solid with the yield of about 84%.
Product MS (m/e): 739.27, respectively; elemental analysis (C)48H33N7O2): theoretical value C: 77.93%, H: 4.50%, N: 13.25 percent; found value C: 77.99%, H: 4.55%, N: 13.08 percent.
EXAMPLE 10 Synthesis of Compound I-59
The synthetic route is as follows:
the preparation process comprises the following steps: into a 1L three-necked flask, M8(36.0g, 0.1mol), (4, 6-diphenyl-1, 3, 5-triazin-2-yl) boronic acid (27.7g, 0.1mol), sodium carbonate (15.9g,0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and after the reaction system was purged with nitrogen, Pd (PPh) was added3)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 evaporated off, 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 in a rotating mode, ethyl acetate is pulped, and filtration is carried out to obtain 44.6g of light yellow solid I-59-1 with the yield of about 87%.
A1L three-necked flask is taken, magnetic stirring is carried out, after nitrogen replacement, I-59-1(51.3g, 0.1mol), (4-phenylquinazolin-2-yl) boronic acid (25.0g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml are sequentially added, and stirring is 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 56.0g pale yellow solid with yield about 82%.
Product MS (m/e): 683.21, respectively; elemental analysis (C)44H25N7O2): theoretical value C: 77.29%, H: 3.69%, N: 14.34 percent; found value C: 77.35%, H: 3.74%, N: 14.18 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 blue light fluorescent 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) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic 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 HATCN, HT01, NThe formula of PB is as follows:
(3) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material ADN is adjusted to be 0.1nm/s, the concentration of the dye material BD01 is adjusted to be 5%, and the total thickness of the evaporation film is 30nm by using a multi-source co-evaporation method; the structural formulas of ADN and BD01 are as follows:
(4) vacuum evaporation is carried out on the electron transport layer material of the device on the luminescent layer, and any compound provided in the embodiment 1 to the embodiment 10 is taken as the electron transport material of the electron transport layer of the device for evaporation, 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; respectively 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 a comparative compound, the structural formula of which is shown below, to obtain a comparative example 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
The results in table 1 show that the novel organic material of the present invention is used for organic electroluminescent devices, the current efficiency of the manufactured devices is high, the working voltage is obviously superior to that of the comparative devices under the condition of the same brightness, and the organic material is an 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. An organic material containing an indoloquinazolinedione heterocyclic structure, which is characterized by having a structure shown as a general formula (I):
wherein:
R1～R8optionally 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～R8At 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; r1～R8May be the same or different.
2. The organic material as claimed in claim 1, wherein the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing property is a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, the polycyclic aromatic hydrocarbon group is optionally selected from a polyphenylalkyl group, a biphenyl polycyclic aromatic hydrocarbon group and a fused-ring aromatic hydrocarbon group, the number of heteroatoms contained in the polycyclic aromatic hydrocarbon group is 1-6, and the heteroatoms are optionally selected from N, O, S.
3. The organic material according to claim 1 or 2, wherein the substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property is selected from the group consisting of 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-phenanthroline group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted symtriazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenyl group, Substituted or unsubstituted biphenyl;
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.
4. The organic material according to any one of claims 1 to 3, wherein the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties is selected from the group consisting of:
preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
further preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
wherein "- -" represents a substituted bit.
5. The organic material according to any one of claims 1 to 4, wherein R is1～R8Any one of the groups is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties;
or, R1～R8Any two groups are substituted or unsubstituted heteroatom-containing aromatic groups with electron-withdrawing property, and the two groups are positioned on different benzene rings or on the same benzene ring; the two groups are the same or different from each other;
the R is1～R8In (b), in addition to representing a substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property, the remaining group is selected from any one of a hydrogen atom, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group.
6. The organic material according to any one of claims 1 to 5, wherein the compound is selected from compounds represented by the following structural formulae:
7. use of the organic material containing an indoloquinazolinedione heterocyclic structure according to any one of claims 1 to 6 for the preparation of an organic electroluminescent device;
preferably, the organic material containing the indole quinazoline diketone heterocyclic ring 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 an electron transport layer, and the material of the electron transport layer contains the organic material containing the indole quinazoline dione heterocyclic structure according to any one of claims 1 to 6.
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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| CN114605433A (en) * | 2022-03-31 | 2022-06-10 | 北京燕化集联光电技术有限公司 | Organic material containing indenothiophene dioxide structure and application thereof |
| WO2022122682A3 (en) * | 2020-12-10 | 2022-07-28 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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| WO2004087164A1 (en) * | 2003-04-04 | 2004-10-14 | Universitätsklinikum Charité Der Humboldt-Universität Zu Berlin | 8-nitro-tryptanthrin and other tryptanthrin derivatives used for the treatment of diseases caused by highly proliferating cells |
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| CN114605433A (en) * | 2022-03-31 | 2022-06-10 | 北京燕化集联光电技术有限公司 | Organic material containing indenothiophene dioxide structure and application thereof |
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