CN109369644A - A kind of substituted pyridine compounds and its application - Google Patents

A kind of substituted pyridine compounds and its application Download PDF

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CN109369644A
CN109369644A CN201811183693.7A CN201811183693A CN109369644A CN 109369644 A CN109369644 A CN 109369644A CN 201811183693 A CN201811183693 A CN 201811183693A CN 109369644 A CN109369644 A CN 109369644A
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刘九州
黄达
马腾达
曹辰辉
陈少海
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ACC Acoustic Technologies Shenzhen Co Ltd
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Abstract

The invention belongs to field of organic electroluminescent materials, a kind of substituted pyridine compounds and its application are disclosed.Presently disclosed compound has structure shown in logical formula (I).Such compound improves transmission performance of the electrons and holes inside compound by pyridine groups combination nested with carbazole/carboline group.Simultaneously, due to introducing steric group on pyridine substituents, so that the angle of the substituent group and pyridine groups that are connected with pyridine becomes larger, reduce the conjugated degree of intramolecular, so that compound has high triplet energy level and glass transition temperature, thus it is highly suitable for blue light and deep Blue-light emitting host material.

Description

Substituted pyridine compound and application thereof
Technical Field
The invention belongs to the field of organic electroluminescent materials, and particularly relates to a substituted pyridine compound and application thereof.
Background
In the technical field of organic electroluminescent devices, high-efficiency and long-life luminescence can be realized in different modes, and for a luminescent layer of an emission spectrum, one mode is to improve the efficiency and the service life by adopting a host-guest doping mode.
In order to achieve high efficiency of light emission, avoid energy from a guest material to a host material from being transferred back, and confine triplet excitons in a light emitting layer, a triplet energy level of the host material should be greater than a triplet energy level of a dopant material. When the triplet energy level of the host material is less than the triplet energy of the dopant material, a phenomenon of reverse transition from the dopant material to the host material energy level will occur, resulting in a decrease in light emission efficiency. Therefore, for the light emitting material layer, a host material having high thermal stability and higher triplet energy than a dopant material is required.
In the prior art, most of the host materials are hole transport type host materials or electron transport type host materials. Such a unipolar host material tends to form an unfavorably narrow recombination region due to imbalance in carrier transport properties. In general, when a hole transport type host material is used, a charge recombination region is generated at an interface between a light emitting layer and an electron transport layer, and when an electron transport type host material is used, a charge recombination region is generated at an interface between a light emitting layer and a hole transport layer. However, the weak carrier mobility and the unbalanced charge in the emission layer are disadvantageous to the light emission efficiency of the organic light emitting device. Meanwhile, the narrow charge recombination region of the organic electrophosphorescent device accelerates the triplet-triplet annihilation process, thereby reducing the luminous efficiency, especially under the current density condition. To avoid this effect, the strategies generally adopted are: (1) using two light emitting layers, one of which uses a hole transport type host material and the other of which uses an electron transport type host material; (2) hole-transporting and electron-transporting host materials are mixed in a single light-emitting layer. However, both strategies complicate the fabrication of the device and the mixed host materials can lead to phase separation problems.
Therefore, in order to achieve a high electroluminescent effect, it is necessary to develop a host material having balanced hole-carrying and electron-transporting properties to widen a charge recombination region.
Disclosure of Invention
The invention aims to provide a substituted pyridine compound and application thereof, wherein the compound is extremely suitable for blue light and deep blue light host materials.
The purpose of the invention is realized by the following technical scheme:
embodiments of the present invention provide a substituted pyridine compound having a structure represented by general formula (I):
wherein,
X1-X8each independently represents an N atom or CRx, and the Rx represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
N1-N8each independently represents an N atom orCRy, and said Ry represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamine group;
AR represents a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C3-C72 heteroaryl group or a C3-C72 heteroaryloxy group; and the number of said AR groups is 1-3.
Optionally, Rx, Ry each independently has a structure represented by formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently represents an N atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr,
and Rm, Rn, Ro, Rp, Rq, Rr each independently represent C1-C24 alkyl, C6-C72 aryl, or C3-C72 heteroaryl.
Optionally, the connection Ar1And Ar2Is one orTwo, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
Optionally, Rx, Ry, Rz each independently has a structure selected from one of:
wherein,
R1-R16each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
Optionally, Rx, Ry, Rz each independently has the structure of one of:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridyl or naphthyl.
Alternatively, an embodiment of the present invention provides a substituted pyridine compound having a structure in which AR is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
Further optionally, AR is selected from methyl, ethyl, propyl, butyl, trifluoromethyl, deuterated methyl, phenyl, tolyl, xylyl, biphenyl, pyridyl, methylpyridyl, or phenylpyridyl.
Still further alternatively, AR is methyl.
Alternatively, embodiments of the present invention provide substituted pyridine compounds having a structure selected from one of the following:
embodiments of the present invention also provide applications of the substituted pyridine compounds in organic electroluminescent devices. The 2, 5-substituted pyridine compound can be used between a cathode and an anode of an organic electroluminescent device and used as a host material, an object material or an auxiliary material, wherein the host material can be a phosphorescent host material or a fluorescent host material; the host material can be a blue light host material, and can also be a green light or red light host material; the auxiliary material is a hole transport material, a hole injection material, a hole blocking material, an electron transport material, an electron injection material, an electron blocking material and a charge generation material; the 2, 5-substituted pyridine compound of the present invention can also be used as a capping layer material in addition to the cathode and anode of an organic electroluminescent device. Preferably, the 2, 5-substituted pyridine compound is a blue or deep blue phosphorescent host material in an organic electroluminescent device.
The substituted pyridine compound provided by the embodiment of the invention improves the transmission performance of electrons and holes in the compound through the nested combination of the pyridine group and the carbazole/carboline group. Meanwhile, due to the introduction of the steric hindrance group on the pyridine substituent, the angle between the substituent connected with the pyridine and the pyridine group is enlarged, the conjugation degree in molecules is reduced, and the compound has extremely high triplet state energy level and glass transition temperature, so that the compound is very suitable for being used as a blue light and deep blue light host material.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of Compound H1, prepared in accordance with an embodiment;
FIG. 2 is a nuclear magnetic hydrogen spectrum of Compound H2, prepared in accordance with an embodiment;
FIG. 3 is a nuclear magnetic hydrogen spectrum of Compound H3 prepared in the example;
fig. 4 is a nuclear magnetic hydrogen spectrum of compound H4 prepared in the embodiment.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention will be described in detail with reference to the following examples. However, it will be appreciated by those of ordinary skill in the art that numerous technical details are set forth in order to provide a better understanding of the present invention in its various embodiments. However, the technical solutions claimed in the claims of the present invention can be implemented without these technical details and with various changes and modifications based on the following embodiments. Compound (I)
In some embodiments of the present invention, there is provided a substituted pyridine compound having a structure represented by the general formula (I):
wherein,
X1-X8each independently represents an N atom or CRx, and the Rx represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
N1-N8each independently represents an N atom or CRy, and the Ry represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
AR represents a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C3-C72 heteroaryl group or a C3-C72 heteroaryloxy group; and the number of said AR groups is 1-3.
In some embodiments of the invention, Rx, Ry each independently has a structure according to formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently represents an N atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr, and Rm, Rn, Ro, Rp, Rq, Rr each independently represents a C1-C24 alkyl group, a C6-C72 aryl group or a C3-C72 heteroaryl group.
In some embodiments of the invention, the linkage Ar1And Ar2Is one or two, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
In some embodiments of the invention, Rx, Ry, Rz each independently has a structure selected from one of:
wherein,
R1-R16each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy, C6-C18 aryl, C3-C18 heteroaryl, C7-C18 arylamine, C4-C18 heteroarylamine, C6-C18 aryloxy or C3-C18 heteroaryloxy;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
In some embodiments of the invention, Rx, Ry, Rz each independently has the structure of one of:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridyl or naphthyl.
In some embodiments of the present invention, there is provided a substituted pyridine compound having a structure wherein AR is selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having from C1 to C6, an aryl group having from C6 to C18, or a heteroaryl group having from C3 to C18.
In some embodiments of the invention, AR is selected from methyl, ethyl, propyl, butyl, trifluoromethyl, deuterated methyl, phenyl, tolyl, xylyl, biphenyl, pyridyl, methylpyridyl, or phenylpyridyl.
In some embodiments of the invention, AR is methyl.
In some embodiments of the invention, provided substituted pyridine compounds have a structure selected from one of:
general synthetic route:
the specific embodiments of the present invention also provide methods for preparing the above substituted pyridine compounds, which can be synthesized by the following general synthetic routes:
wherein S is1、S2Each independently represents a reactive leaving group, which is various, by way of example and without limitation, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a boric acid group, a borate group; the other groups are as defined for the general formula (I) herein. The above-mentioned reactive leaving group, which leaves during the reaction, may be charged, for example, fluorine atom leaves in the form of a negative ion in many cases.
The charging order of the reaction is not limited, and for example, (S-A) and (S-B) may be charged first, followed by (S-C); it is also possible to add (S-B) and (S-C) first and then (S-A); three may also be added simultaneously.
The specific reaction conditions are not limited, such as temperature, the kind and amount of solvent, the kind and amount of catalyst, the kind and amount of cocatalyst, the kind and amount of alkali, the amount of water, and the feeding ratio of the reaction substrate, and those skilled in the art can easily and reasonably generalize from the examples in the examples of the present invention, and the general basis for selection can refer to relevant documents, patents and books of organic synthesis reactions. Reference may be made to the coupling reaction, preferably to the Suzuki and Ullmann reactions, to the alkylation, preferably to the parkinsonation. Further, the synthesis of the starting materials (S-A) and (S-B) can be easily carried out by those skilled in the art by the examples of the present invention and the published synthetic datA.
Synthesis example:
the following provides methods for preparing the compounds disclosed in the present invention. The present disclosure is not intended to be limited to any one of the methods recited herein. One skilled in the art can readily modify the methods described or utilize different methods to prepare one or more of the disclosed compounds. The following aspects are merely exemplary and are not intended to limit the scope of the present disclosure. The temperature, catalyst, concentration, reactant composition, and other process conditions may be varied, and appropriate reactants and conditions for the desired complex may be readily selected by one skilled in the art to which the present disclosure pertains.
Abbreviations in the examples of the present invention mean: PE: petroleum ether; DCM: dichloromethane; EA: ethyl acetate; DMSO-d6, deuterated dimethyl sulfoxide; CDCl3, deuterated chloroform; MeTHF: methyl tetrahydrofuran; pb (dba)2: tris (dibenzylideneacetone) dipalladium; S-Phos: 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl.
EXAMPLE 1 Synthesis of H-1 Compound
Step 1: synthesis of 9- (3-methyl-5-bromopyridin-2-yl) -9H-pyrido [2,3-b ] indole
9- (3-methyl-5-bromopyridin-2-yl) -9H-pyridine [2,3-b ] indole was synthesized by the following reaction scheme 1:
2, 5-dibromo-3-methylpyridine (2.51g, 10.0mmol), carboline (1.82g, 11.0mmol), CuI (381mg, 2.0mmol), 1-methylimidazole (246mg, 3.0mmol), potassium carbonate (2.76g, 20.0mmol) and toluene (25mL) are placed in a 38mL sealed tube, nitrogen is bubbled for 5min, the temperature is raised to 120 ℃, and the reaction is refluxed for 48 h. After the reaction was completed, filtration was carried out, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was subjected to distillation under the reduced pressure to remove the solvent, and the resultant was purified by silica gel column (petroleum ether: ethyl acetate: 10: 1 → 5: 1) to obtain 9- (3-methyl-5-bromopyridin-2-yl) -9H-pyridin [2,3-b ] indole (1.75g, yield 52%) as a white solid.
Step 2: synthesis of H-1 Compounds
The H-1 compound is synthesized by the following reaction formula 2:
reacting 9- (3-methyl-5-bromopyridin-2-yl) -9H-pyridine [2,3-b ]]Indole (101mg, 0.30mmol), carbazole (55mg, 0.33mmol), cuprous iodide (11mg, 0.06mmol), trans-1, 2-cyclohexanediamine (7mg, 0.06mmol), potassium phosphate (191mg, 0.90mmol), toluene (3mL) were placed in a 38mL sealed tube, nitrogen was bubbled for 5min, then the temperature was raised to 120 ℃, and the reaction was refluxed for 45 h. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain an off-white solid (126mg, yield 99%).1H-NMR(400MHz,DMSO-d6) δ: 8.87(dd, J ═ 2.6,0.7Hz,1H),8.72(dd, J ═ 7.7,1.6Hz,1H),8.49(dd, J ═ 4.8,1.6Hz,1H),8.42(dd, J ═ 2.6,0.8Hz,1H), 8.39-8.28 (m,3H),7.64(dt, J ═ 8.2,0.9Hz,2H),7.54(tdd, J ═ 8.2,7.1,1.3Hz,3H),7.47(dt, J ═ 8.2,1.0Hz,1H), 7.45-7.33 (m,4H),2.21(d, J ═ 0.7Hz, 3H). Mass spectrum: 425(M + H). Melting point 309 ℃ and glass transition temperature 124 ℃.
Example 2: synthesis of H-2 Compounds
H-2 compound is synthesized by the following reaction formula 3
Reacting 9- (3-methyl-5-bromopyridin-2-yl) -9H-pyridine [2,3-b ]]Indole (109mg, 0.32mmol), 3, 6-di-tert-butylcarbazole (99mg, 0.35mmol), Pb (dba)2(59mg, 0.06mmol), S-Phos (26mg, 0.06mmol), sodium tert-butoxide (61mg, 0.64mmol), toluene (3mL) were placed in a 38mL sealed tube, sparged with nitrogen for 5min and warmed to 120 deg.C and the reaction refluxed for 28 h. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was subjected to distillation under the reduced pressure to remove the solvent, and the resultant was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a pale yellow solid (158mg, yield 92%).1H-NMR(400MHz,DMSO-d6)δ：8.86(d,J＝2.7Hz,1H),8.71(dd,J＝7.7,1.6Hz,1H),8.48(dd,J＝4.8,1.6Hz,1H),8.42–8.38(m,1H),8.38–8.33(m,3H),7.55(dd,J＝6.2,1.3Hz,5H),7.45–7.38(m,3H),2.20(d,J＝0.7Hz,3H),1.45(s,18H)。
EXAMPLE 3 Synthesis of H-3 Compound
Step 1: synthesis of 9- (9H-carbazol-2-yl) -9H-pyridine [2,3-b ] indole
9- (9H-carbazol-2-yl) -9H-pyridine [2,3-b ] indole is synthesized by the following reaction scheme 4:
2-bromocarbazole (123mg, 0.5mmol), carboline (252mg, 1.5mmol), CuI (19mg, 0.1mmol), trans-1, 2-cyclohexanediamine (11mg, 0.1mmol), potassium phosphate (212mg, 1.0mmol), and toluene (3mL) were placed in a 38mL sealed tube, and after bubbling with nitrogen for 5min, the temperature was raised to 120 ℃ and the reaction was refluxed for 28 h. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was subjected to distillation under the reduced pressure to remove the solvent, and the resultant was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1 → 5: 1) to obtain 9- (9H-carbazol-2-yl) -9H-pyridine [2,3-b ] indole (50mg, yield 30%) as an off-white solid.
Step 2: synthesis of H-3 Compounds
The H-3 compound is synthesized by the following reaction formula 5:
reacting 9- (9H-carbazol-2-yl) -9H-pyridine [2,3-b]Indole (50mg, 0.15mmol), carboline (56mg, 0.17mmol), CuI (6mg, 0.03mmol), trans-1, 2-cyclohexanediamine (3mg, 0.03mmol), potassium phosphate (95mg, 0.45mmol), toluene (3mL) were placed in a 38mL sealed tube, nitrogen was bubbled for 5min, then the temperature was raised to 120 ℃, and the reaction was refluxed for 18 h. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was distilled under reduced pressure to remove the solvent, and the resultant was purified by silica gel column (petroleum ether: ethyl acetate ═ 5: 1 → 3: 1) to obtain an off-white solid (76mg, yield 85%).1H-NMR(400MHz,DMSO-d6) δ: 8.56(d, J ═ 9.1Hz,1H),8.48(s,1H), 8.46-8.41 (m,3H),8.31(d, J ═ 8.8Hz,2H),7.89(s,1H),7.71(d, J ═ 8.4Hz,1H),7.60(d, J ═ 7.9Hz,3H), 7.56-7.43 (m,3H), 7.42-7.33 (m,5H),2.16(s, 3H). Mass spectrum: 591(M + H), 613(M + Na).
Example 4 Synthesis of H-4 Compound
Step 1: synthesis of 2- (9H-pyridine [2,3-b ] indol-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-carbazole
2- (9H-pyridine [2,3-b ] indol-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-carbazole was synthesized by the following reaction scheme 6:
9- (9H-carbazol-2-yl) -9H-pyridine [2,3-b ] indole (72mg, 0.22mmol), 2, 5-dibromo-3-methylpyridine (65mg, 0.26mmol), CuI (8mg, 0.04mmol), 1-methylimidazole (4mg, 0.04mmol), potassium carbonate (61mg, 0.44mmol), toluene (3mL) were placed in a 38mL sealed tube, the temperature was raised to 120 ℃ after bubbling nitrogen for 5min, and the reaction was refluxed for 16H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (100mg, yield 90%).
Step 2: synthesis of H-4 Compounds
The H-4 compound is synthesized by the following reaction formula 7:
2- (9H-pyridine [2,3-b ]]Indol-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-carbazole (100mg, 0.20mmol), 3, 6-di-tert-butylcarbazole (67mg, 0.24mmol), CuI (8mg, 0.04mmol), trans-1, 2-cyclohexanediamine (4mg, 0.04mmol), potassium phosphate (127mg, 0.60mmol), toluene (3mL) were placed in a 38mL sealed tube, the temperature was raised to 120 ℃ after bubbling nitrogen for 5min, and the reaction was refluxed for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (96mg, yield 69%).1H-NMR(400MHz,DMSO-d6)δ：8.83(dd,J＝2.6,0.7Hz,1H),8.66(dd,J＝7.7,1.6Hz,1H),8.54(dd,J＝8.2,0.6Hz,1H),8.46–8.40(m,2H),8.38–8.34(m,1H),8.34–8.28(m,3H),7.60(dd,J＝1.8,0.6Hz,1H),7.58–7.46(m,8H),7.46–7.39(m,2H),7.38–7.30(m,2H),2.27(t,J＝0.7Hz,3H),1.41(s,18H)。
EXAMPLE 5 Synthesis of H-5 Compound
3- (dibenzofuran-4-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-pyridine [3,4-b ] indole (504mg, 1.0mmol), carbazole (167mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) were placed in a 38mL sealed tube, the temperature was raised to 120 ℃ after bubbling nitrogen for 5min, and the reaction was refluxed for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (450mg, yield 76%). Mass spectrum: 591(M + H).
EXAMPLE 6 Synthesis of H-6 Compound
3,6- (dicarbazolyl-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-pyridine [2,3-b ] indole (668mg, 1.0mmol), carbazole (167mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) were placed in a 38mL sealed tube, the temperature was raised to 120 ℃ after bubbling nitrogen for 5min, and the reaction was refluxed for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (469mg, yield 62%). Mass spectrum: 777(M + Na).
Example 7 Synthesis of H-7 Compound
3,6- (dicarbazolyl-9-yl) -9- (5-bromo-4-methylpyridin-2-yl) -9H-pyridine [3,2-b ] indole (668mg, 1.0mmol), carbazole (167mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) were placed in a 38mL sealed tube, the temperature was raised to 120 ℃ after bubbling nitrogen for 5min, and the reaction was refluxed for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was subjected to distillation under the reduced pressure to remove the solvent, and the resultant was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (275mg, yield 36%). Mass spectrum: 755(M + H).
EXAMPLE 8 Synthesis of H-8 Compound
3- (9H-pyridine [3,2-b ] indol-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-carbazole (503mg, 1.0mmol), 3- (9H-pyridine [3,2-b ] indol-9-yl) -9H-carbazole (333mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) were placed in a 38mL sealed tube, and after bubbling with nitrogen for 5min, the temperature was raised to 120 ℃ to react under reflux for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was subjected to distillation under the reduced pressure to remove the solvent, and the resultant was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (609mg, yield 81%). Mass spectrum: 756(M + H).
EXAMPLE 9 Synthesis of H-9 Compound
3- (dibenzofuran-4-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-pyrido [2,3-b ] indole (504mg, 1.0mmol), 3- (dibenzofuran-4-yl) -9H-pyrido [2,3-b ] indole (334mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) was placed in a 38mL lock, and after bubbling nitrogen for 5min, the temperature was raised to 120 ℃ and the reaction refluxed for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the obtained filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (550mg, yield 73%). Mass spectrum: 774(M + H).
EXAMPLE 10 Synthesis of H-10 Compound
3,6- (dicarbazolyl-9-yl) -9- (5-bromo-3-methylpyridin-2-yl) -9H-pyridine [2,3-b ] indole (668mg, 1.0mmol), 3,6- (dicarbazolyl-9-yl) -9H-carbazole (497mg, 1.0mmol), CuI (38mg, 0.2mmol), trans-1, 2-cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (5mL) were placed in a 38mL sealed tube, warmed to 120 ℃ after bubbling nitrogen for 5min, and reacted under reflux for 48H. After completion of the reaction, the pad was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvent was removed from the filtrate by distillation under the reduced pressure, and the obtained product was purified by column chromatography on silica gel (petroleum ether: ethyl acetate: 10: 1) to obtain a white solid (748mg, yield 69%). Mass spectrum: 1085(M + H).
Compound performance detection
The compound H1-H4 was dissolved in MeTHF, and the phosphorescence emission spectrum was measured at a low temperature of 77K to obtain a first triplet level T1 level, and the triplet level data of the compound are shown in Table 1:
table 1 triplet energy level data for compounds
As can be seen from the data in Table 1, the triplet energy level of the compounds of the examples of the invention is greater than 2.90eV, whether calculated using the Onset Peak (Onstet) or the First emission Peak height (First Peak).
Thermogravimetric TGA and differential scanning calorimetry DSC data of the compounds were measured at a temperature rise rate of 10K/min, as shown in table 2 below:
thermodynamic data for the compounds of Table 2
The HOMO and LUMO values are measured by an electrochemical method which is conventional in the industry, the HOMO energy level value is directly calculated by measuring the oxidation potential Eox of an organic matter, and the calculation formula is that the HOMO is equal to Eox + 4.74. Combining the band gap Eg measured by the spectrum method, the calculation formula is Eg-hc/lambda abs-1240/lambda abs, the LUMO energy level value is indirectly calculated, and the calculation formula is LUMO-HOMO-Eg. The HOMO and LUMO measurements for the compounds are shown in Table 3:
table 3HOMO and LUMO measurement data:
sample name Abs(nm) Eg(eV) Eox(V vs.Fc/Fc+) HOMO(eV) LUMO(eV)
H-1 349 3.553 0.910 5.650 2.097
H-2 353 3.513 0.795 5.535 2.022
H-3 351 3.533 0.870 5.610 2.077
Preparation of organic light emitting diode
The device is manufactured by adopting an industry conventional preparation method, and the following modes can be selected: firstly, a proper anode is selected for introducing holes, other materials can be evaporated on the surface of the anode to change the work function of the anode, then an organic layer is evaporated, and then a cathode is evaporated to play a role in introducing electrons. Examples are as follows:
placing the cleaned ITO glass substrate in a vacuum chamber, and vacuumizing to 10 DEG-5Pa, evaporating a layer of 10nm 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), and continuing to evaporate a layer of 20nm 4, 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline](TAPC), continuing to evaporate a layer of 10nm 9,9- (1, 3-phenyl) dicarbazole (mCP); continuously carrying out co-evaporation on a luminescent layer of 30nm iridium bis (2, 4-difluorophenylpyridine) -tetrakis (1-pyrazolyl) borate (FIr6) and one of the compounds H1-H4 prepared by the embodiment of the invention, wherein the doping concentration is 8 wt%; continuously evaporating a 50nm TmPyPB layer as an electron transport layer; and continuously evaporating a layer of lithium fluoride with the thickness of 1nm, and continuously evaporating a layer of aluminum electrode with the thickness of 100 nm. The host material adopted by the comparative device C1 is 2, 6-dicarbazole pyridine.
The External Quantum Efficiency (EQE), the turn-on voltage (Von) of each device was measured and the data is shown in table 4 below:
TABLE 4 device Performance data
EQE Von
H1 16.5 3.2
H2 16.7 3.5
H3 17.3 3.3
H4 17.6 3.6
C1 15.2 3.9
As can be seen from table 4 above, the efficiency of the device manufactured by using the H1-H4 compound prepared in the embodiment of the present invention is improved by 8% compared with that of the reference device C1, and the turn-on voltage is also improved by a relatively large margin.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the invention, and that various changes in form and details may be made therein without departing from the spirit and scope of the invention in practice.

Claims (10)

1. A substituted pyridine compound having the structure shown in formula (I):
wherein,
X1-X8each independently represents a N atom or CRx, and Rx represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C7 alkylamino group2 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino;
N1-N8each independently represents an N atom or CRy, and the Ry represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
AR represents a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C3-C72 heteroaryl group or a C3-C72 heteroaryloxy group; and the number of said AR groups is 1-3.
2. The substituted pyridine compound according to claim 1, wherein Rx, Ry each independently has a structure represented by formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently represents an N atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr, and Rm, Rn, Ro, Rp, Rq, Rr each independently represents a C1-C24 alkyl group, a C6-C72 aryl group or a C3-C72 heteroaryl group.
3. The substituted pyridine compound according to claim 2, wherein the linkage Ar is Ar1And Ar2Is one or two, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
4. A substituted pyridine compound according to claim 3, characterized in that Rx, Ry, Rz each independently has a structure selected from one of the following:
wherein,
R1-R16each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
5. A substituted pyridine compound according to claim 4, characterized in that Rx, Ry, Rz each independently has the structure of one of the following:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridyl or naphthyl.
6. Substituted pyridine compound according to claim 1, characterized in that AR is selected from the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, C1-C6 alkyl groups, C6-C18 aryl groups or C3-C18 heteroaryl groups.
7. The substituted pyridine compound according to claim 6, wherein AR is selected from methyl, ethyl, propyl, butyl, trifluoromethyl, deuterated methyl, phenyl, tolyl, xylyl, biphenyl, pyridyl, methylpyridyl, and phenylpyridyl.
8. The substituted pyridine compound according to claim 1, wherein AR is methyl.
9. The substituted pyridine compound according to claim 1, having a structure selected from one of the following:
10. use of the substituted pyridine compound according to any one of claims 1 to 9 in an organic electroluminescent device.
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JP2014101275A (en) * 2011-10-26 2014-06-05 Tosoh Corp 4-aminocarbazole compound and use of the same
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Application publication date: 20190222