CN108774212A - 2,5 pyridine compounds replaced and its application - Google Patents

2,5 pyridine compounds replaced and its application Download PDF

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CN108774212A
CN108774212A CN201810872274.8A CN201810872274A CN108774212A CN 108774212 A CN108774212 A CN 108774212A CN 201810872274 A CN201810872274 A CN 201810872274A CN 108774212 A CN108774212 A CN 108774212A
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aryl
heteroaryls
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马腾达
黄达
曹辰辉
孙晓媛
陈少海
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ACC Acoustic Technologies Shenzhen Co Ltd
AAC Technologies Holdings Nanjing Co Ltd
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Abstract

The invention belongs to field of organic electroluminescent materials, disclose the pyridine compounds and its application of 2,5 substitutions of one kind.Compound disclosed in this invention has structure shown in logical formula (I).Such compound passes through pyridine groups combination nested with carbazole group, improve transmission performance of the electrons and holes inside compound, additionally in carbazole or 2 or 7 introducing substituent groups of carboline, thus glass transition temperature, triplet energy level and thermal stability are high, it is suitable as the material of main part of blue emitting material, the especially material of main part of navy blue phosphorescent light-emitting materials.

Description

2,5 pyridine compounds replaced and its application
Technical field
The invention belongs to field of organic electroluminescent materials, more particularly to the pyridine compounds of a kind of 2,5 substitutions and its Using.
Background technology
In organic electroluminescence device technical field, can be realized by different modes efficiently, the high life shine, for The luminescent layer of emission spectrum, one way in which are exactly to use the form of host-guest system into the promotion of line efficiency and service life.
It is efficient luminous in order to realize, reverse energy passback of the energy from guest materials to material of main part is avoided, simultaneously Triplet exciton is limited to luminescent layer, the triplet energy level of material of main part should be more than the triplet energy level of dopant material.When When the triplet energy level of material of main part is less than the triplet energies of dopant material, it will occur from dopant material to material of main part energy It the phenomenon that grade anti-transition, is reduced so as to cause luminous efficiency.Therefore, it for luminous material layer, needs high thermal stability and is higher than The material of main part of dopant material triplet energies.
In the prior art, most of material of main part is hole-transporting type material of main part or electron-transporting type material of main part.By In the imbalance of carrier transmission performance, this unipolar material of main part is easy to form unfavorable narrow recombination region.In general, When using hole-transporting type material of main part, charge recombination zone is will produce in luminescent layer and electron-transport bed boundary, and working as makes When with electron-transporting type material of main part, charge recombination zone will produce in luminescent layer and hole transport bed boundary.However weak load It is unfavorable to the luminous efficiency of organic luminescent device to flow unbalanced charge in transport factor and luminescent layer.Meanwhile organic electroluminescence is sent out This narrow charge recombination zone of optical device, can accelerate T-T annihilation process, decline so as to cause luminous efficiency, Especially under current density condition.In order to avoid this effect, the strategy of generally use is：(1) two luminescent layers are used, In one layer use hole-transporting type material of main part, another luminescent layer use electron-transporting type material of main part；(2) by hole transport Type and the mixing of electron-transporting type material of main part are placed in single luminescent layer.However, both strategies are so that the preparation of device becomes Complexity, and mixed material of main part can cause phase separation the problem of.
Therefore, in order to reach efficient electroluminescence, load hole and stream transporting of the development with balance are needed The material of main part of energy, to widen charge recombination zone.
Invention content
The purpose of the present invention is to provide a kind of pyridine compounds of 2,5 substitutions and its application, 2,5 substitutions of this kind Pyridine compounds are a kind of preferable blue phosphorescent material of main parts.
The purpose of the present invention is achieved through the following technical solutions：
Embodiments of the present invention provide a kind of pyridine compounds of 2,5 substitutions, have and are tied shown in logical formula (I) Structure：
Wherein,
X1、X2、Y1、Y2、Z1、Z2N atoms or CRx are each independently represented, and the Rx indicates hydrogen atom, D-atom, halogen Plain atom, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 virtues Oxygroup, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amidos；
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1- C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3- C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
Optionally, the pyridine compounds for 2,5 substitutions that embodiments of the present invention are provided, have shown in logical formula (II) Structure：
Wherein,
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1- C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3- C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
Optionally, 2 provided in embodiments of the present invention, 5 substitution pyridine compounds in, the G1、G2For phase Same substituent group.
Optionally, 2 provided in embodiments of the present invention, 5 substitution pyridine compounds in, the G1、G2Respectively Independently there is structure shown in formula (III-1) or (III-2)：
Wherein,
Ar1、Ar2Each independently represent C1-C24 alkyl, C6-C72 aryl, C3-C72 heteroaryls；Ar1And Ar2It is not attached to Or Ar1And Ar2It is connected by singly-bound, double bond, carbon atom or hetero atom；
M1、M2、M3、M4N atoms or CRz are each independently represented, and Rz indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
Z indicates oxygen atom, sulphur atom, sulfuryl, sulfoxide group, NRm, CRnRo, SiRpRq or BRr,
Rm, Rn, Ro, Rp, Rq, Rr each independently represent C1-C24 alkyl, C6-C72 aryl or C3-C72 heteroaryls.
Optionally, the connection Ar1And Ar2Carbon atom be one or two, the carbon atom by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or the substitution of C3-C36 heteroaryls；The hetero atom is oxygen atom, sulphur atom, silicon atom, nitrogen original Son or boron atom, the sulphur atom is not substituted or replaced by one or two oxygen atom, the silicon atom, nitrogen-atoms or boron Atom is replaced by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or C3-C36 heteroaryls.
Optionally, G1, G2, Rx, Ry, Rz have each independently selected from one of following structure：
Wherein,
R1-R16Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 Aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R21-R26Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 The heteroaryloxy of aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18；
R31-R34Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 Aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R101-R106Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls；
R201-R205Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls.
Optionally, G1, G2, Rx, Ry, Rz have one of following structure each independently：
Wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340Each independently represent hydrogen atom, D-atom, methyl, Ethyl, propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group, naphthalene, carbazyl or carboline base；
R2010Indicate methyl, ethyl, propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group or Naphthalene.
Optionally, the pyridine compounds for 2,5 substitutions that embodiments of the present invention are provided, have selected from one of following Structure：
Embodiments of the present invention also provide above-mentioned 2, and the pyridine compounds of 5 substitutions are in organic electroluminescence device Using.The pyridine compounds of 2,5 substitutions of the present invention can be used between organic electroluminescence device cathode and anode, as Material of main part, guest materials or auxiliary material use, and the material of main part can be phosphorescent light body material, or fluorescence Material of main part；The material of main part can be Blue-light emitting host material, or green light or feux rouges material of main part；The auxiliary material Material can be hole mobile material, hole-injecting material, hole barrier materials, electron transport material, electron injection material, electronics Barrier material or charge generating material.The pyridine compounds for 2,5 substitutions that embodiments of the present invention are provided can also be used Except organic electroluminescence device cathode and anode, used as covering layer material.Preferably, embodiments of the present invention institute The pyridine compounds of 2,5 substitutions provided are the blue phosphorescent material of main part in organic electroluminescence device.
The pyridine compounds for 2,5 substitutions that embodiments of the present invention are provided, pass through pyridine groups and carbazole group Nested combination, improve transmission performance of the electrons and holes inside compound.Embodiments of the present invention provided 2,5 The pyridine compounds of position substitution, by introducing substituent group, glass transition temperature, triplet energy at 2 of carbazole or carboline or 7 Grade and thermal stability are high, are suitable as the material of main part of blue emitting material, the especially main body of navy blue phosphorescent light-emitting materials Material.
Description of the drawings
The hydrogen spectrum that Fig. 1 is the compound H1 prepared in specific implementation mode；
The hydrogen spectrum that Fig. 2 is the compound H2 prepared in specific implementation mode；
The hydrogen spectrum that Fig. 3 is the compound H3 prepared in specific implementation mode.
Specific implementation mode
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with embodiment to each of the present invention Specific implementation mode is explained in detail.However, it will be understood by those skilled in the art that in each embodiment party of the present invention In formula, many technical details are proposed in order to make reader more fully understand the present invention.But even if without these technical details And various changes and modifications based on the following respective embodiments, it can also realize each claim skill claimed of the present invention Art scheme.
Compound
In certain specific embodiments of the invention, a kind of pyridine compounds of 2,5 substitutions are provided, are had logical Structure shown in formula (I)：
Wherein,
X1、X2、Y1、Y2、Z1、Z2N atoms or CRx are each independently represented, and the Rx indicates hydrogen atom, D-atom, halogen Plain atom, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 virtues Oxygroup, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amidos；
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1- C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3- C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
In certain specific embodiments of the invention, 2 provided, the pyridine compounds of 5 substitutions have general formula (II) structure shown in：
Wherein,
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1- C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3- C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
In certain specific embodiments of the invention, the G1、G2For identical substituent group.
In certain specific embodiments of the invention, the G1、G2There is formula (III-1) or (III-2) each independently Shown in structure：
Wherein,
Ar1、Ar2Each independently represent C1-C24 alkyl, C6-C72 aryl, C3-C72 heteroaryls；Ar1And Ar2It is not attached to Or Ar1And Ar2It is connected by singly-bound, double bond, carbon atom or hetero atom；
M1、M2、M3、M4N atoms or CRz are each independently represented, and Rz indicates hydrogen atom, D-atom, halogen atom, C1- C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 Arylthio, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amine Base；
Z indicates oxygen atom, sulphur atom, sulfuryl, 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 heteroaryls.
In certain specific embodiments of the invention, the connection Ar1And Ar2Carbon atom be one or two, it is described Carbon atom is replaced by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or C3-C36 heteroaryls；The hetero atom is oxygen Atom, sulphur atom, silicon atom, nitrogen-atoms or boron atom, the sulphur atom is not substituted or taken by one or two oxygen atom In generation, the silicon atom, nitrogen-atoms or boron atom are by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or C3-C36 heteroaryls Base replaces.
In certain specific embodiments of the invention, G1、G2, Rx, Ry, Rz have each independently selected from one of following Structure：
Wherein,
R1-R16Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 Aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R21-R26Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 The heteroaryloxy of aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18；
R31-R34Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 Aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R101-R106Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls；
R201-R205Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls.
In certain specific embodiments of the invention, G1、G2, Rx, Ry, Rz there is one of following knot each independently Structure：
Wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340Each independently represent hydrogen atom, D-atom, methyl, Ethyl, propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group, naphthalene, carbazyl or carboline base；
R2010Indicate methyl, ethyl, propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group or Naphthalene.
In certain specific embodiments of the invention, the pyridine compounds of 2 provided, 5 substitutions have selected from such as One of lower structure：
General synthetic routes：
Specific embodiments of the present invention also provide above-mentioned 2, the preparation method of the pyridine compounds of 5 substitutions, such chemical combination Object can be synthesized by the general synthetic routes as shown in following formula (Syn-1) or (Syn-2)：
Wherein, S1、S2Each independently represent reaction leaving group, reaction leaving group be it is diversified, citing without It is restricted, fluorine atom, chlorine atom, bromine atom, iodine atom, boric acid base group, borate group may be selected；Other groups define with The logical formula (I) of the application is identical.Above-mentioned reaction leaving group, when leaving away during the reaction, it may be possible to it is electrically charged, such as fluorine Atom is mostly left away in the form of anion when leaving away.
The feeding sequence of reaction is not limited, citing, and (S-A) and (S-B) can first be added, and (S- is then added C)；(S-B) and (S-C) can also first be added, (S-A) then is added；Can also three be added simultaneously.
Wherein, S1、S2、Sy1、Sy2Each independently represent reaction leaving group, reaction leaving group be it is diversified, It illustrates and unrestricted, optional fluorine atom, chlorine atom, bromine atom, iodine atom, boric acid base group, borate group；S3Also table Show reaction leaving group, illustrates and unrestricted, optional hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, boric acid Group, borate group；GG indicates G1Or G2Group；Other groups define identical as the logical formula (I) of the application.Above-mentioned reaction from Group is removed, when leaving away during the reaction, it may be possible to it is electrically charged, as fluorine atom when leaving away mostly in the form of anion from It goes.
The feeding sequence of reaction is not limited, citing, and (Sy-A) and (S-B) can first be added, and is then added (Sy-C), it adds (Sy-D)；(S-B) and (Sy-C) can also first be added, (Sy-D) then is added, adds (Sy-A)；? (Sy-C) and (Sy-D) can first be added, (S-B) then is added, (Sy-A) then is added.
Those skilled in the art will readily recognize that, the X in (Sy-A)1、Y1、Z1、N1、N2、N3、N4It is selected as CR bases Group, the R are D-atom, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 virtues Base, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 When heteroarylthio or C4-C72 heteroaryl amidos, general synthetic route is similar.
Specific reaction condition is not limited, citing as temperature, the type of solvent and dosage, the type of catalyst and The rate of charge of dosage, the type of co-catalyst and dosage, the type of alkali and dosage, the dosage of water, reaction substrate, in the industry general skill Art personnel readily can reasonably be promoted from the embodiment in the embodiment of the present invention, and the general foundation of selection can refer to Pertinent literature, patent and the books of organic synthesis.It is related to coupling reaction, preferentially can refers to suzuki reaction and Liv Ullmann is anti- The related data answered.It is related to alkylated reaction, can preferentially refers to and pay gram alkylated related data.
Synthesize example：
The preparation method of disclosed compound of present invention provided below.But present disclosure is not intended to be limited to institute herein The method of narration it is any.Those skilled in the art can easily change described method or utilize different sides Method prepares the one or more of disclosed compound.Following aspect is merely exemplary, and is not intended to limit in the disclosure The range of appearance.Temperature, catalyst, concentration, reactant composition and other process conditions are changeable, and match for desired Object is closed, present disclosure those skilled in the art can readily select suitable reactant and condition.
Abbreviation meaning in the embodiment of the present invention：PE：Petroleum ether；DCM：Dichloromethane；EA：Ethyl acetate；DMSO-d6, Deuterated dimethyl sulfoxide；CDCl3, deuterochloroform；MeTHF：Methyltetrahydrofuran；Pb(dba)2：Three (dibenzalacetones) two Palladium；S-Phos：2- dicyclohexyl phosphine -2', 6'- dimethoxy-biphenyls.
Embodiment 1:The synthesis of 2- [2- (carbazole -9- bases)-carbazole -9- bases] -5- (carbazole -9- bases)-pyridine (H1)
2- (2- bromine carbazole -9- bases) -5- bromopyridine 375mg, carbazole 326mg is added into reaction bulb, opens stirring, successively Cuprous iodide 18mg, Trans- cyclohexanediamine 22mg, anhydrous phosphoric acid potassium 492mg, toluene 10ml is added.Nitrogen replaces system 3 times Afterwards, system is warming up to 130 degree, after heat preservation for 24 hours, and 10ml purified waters, liquid separation is added in cooling, and water phase is gathered around DCM20ml*2 extraction, closed And organic phase is dried, organic phase concentration is dry after drying, crosses silicagel column, eluant, eluent DCM:PE=1:40~1:10, eluent concentration It is dry, obtain white solid 597.2mg, yield 68%.1H NMR(400MHz,Solvent：CDCl3)δppm:7.27~7.34 (m, 5H), 7.36~7.48 (m, 9H), 7.52~7.58 (m, 2H), 7.88~7.93 (dd, 1H), 8.03~8.06 (m, 1H), 8.09 ~8.21 (m, 6H), 8.21~8.24 (m, 1H), 8.33~8.37 (dd, 1H), 8.88~8.92 (dd, 1H).Mass spectroscopy molecular from Sub- peak：M+=574.2.
Embodiment 2：The conjunction of 2- [2- (1-N- carboline -9- bases)-carbazole -9- bases] -5- (1-N carboline -9- bases)-pyridine (H2) At
2- (2- bromine carbazole -9- bases) -5- bromopyridines 403mg, 1-N carboline 336mg is added into reaction bulb, opens stirring, Sequentially add cuprous iodide 19mg, Trans- cyclohexanediamine 45mg, anhydrous phosphoric acid potassium 811mg, toluene 16ml.Nitrogen replaces system After 3 times, system is warming up to 130 degree, and after keeping the temperature 72h, 10ml purified waters, liquid separation is added in cooling, and water phase gathers around DCM20ml*2 extraction Take, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA：PE=1：3, eluent concentration is dry, Obtain white solid 467mg, yield 63%.1H NMR(400MHz,Solvent：CDCl3)δppm:7.27~7.29 (m, 2H), 7.31~7.44 (m, 3H), 7.44~7.58 (m, 6H), 7.93~7.96 (dd, 1H), 8.05~8.08 (dd, 1H), 8.10~ 8.16 (m, 2H), 8.16~8.29 (m, 3H), 8.32~8.36 (m, 1H), 8.37~8.44 (m, 2H), 8.44~8.51 (m, 2H), 8.98~9.03 (dd, 1H).Mass spectral molecular ion peak：M+=576.2.
Embodiment 3:2- [2- (3,6- di-t-butyl carbazole -9- bases)-carbazole -9- bases] -5- (3,6- di-t-butyls carbazoles - 9- yls)-pyridine (H3) synthesis
2- (2- bromine carbazole -9- bases) -5- bromopyridines 315mg, 3,6- di-t-butyl carbazole 458mg are added into reaction bulb, Stirring is opened, cuprous iodide 30mg, Trans- cyclohexanediamine 27mg, anhydrous phosphoric acid potassium 500mg, toluene 10ml are sequentially added.Nitrogen After gas displacement system 3 times, system is warming up to 130 degree, after heat preservation for 24 hours, and 10ml purified waters, liquid separation is added in cooling, and water phase is gathered around DCM20ml*2 extraction, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA:PE=1:40, Eluent concentration is dry, obtains white solid 374mg, yield 60%.1H NMR(400MHz,Solvent：CDCl3)δppm:1.48(s, 18H), 1.49 (s, 18H), 7.27~7.34 (m, 4H), 7.35~7.52 (m, 4H), 7.52~7.63 (m, 4H), 7.63~ 7.67 (dd, 1H), 7.92~8.05 (m, 2H), 8.07~8.13 (, m, 1H), 8.12~8.21 (m, 6H), 8.23~8.30 (m, 1H), 9.01~9.03 (dd, 1H).Mass spectral molecular ion peak：M+=798.5.
Embodiment 4：The synthesis of 2,5- [2- (carbazole -9- bases)-carbazole -9- bases]-pyridine (H4)
2,5- bis- (2- bromine carbazole -9- bases)-pyridine 290mg, carbazole 340mg is added into reaction bulb, opens stirring, successively Cuprous iodide 60mg, Trans- cyclohexanediamine 70mg, anhydrous phosphoric acid potassium 1622mg, toluene 20ml is added.Nitrogen replaces system 3 times Afterwards, system is warming up to 130 degree, after heat preservation for 24 hours, and 30ml purified waters, liquid separation is added in cooling, and water phase is extracted for 50ml*2 times with DCM, Merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent DCM:PE=1:40~1:10, eluent is dense Contracting is dry, obtains white solid 330mg.Mass spectral molecular ion peak：M+=739.3.
Embodiment 5：The conjunction of 2- [2- (4-N- carboline -9- bases)-carbazole -9- bases] -5- (4-N carboline -9- bases)-pyridine (H5) At
2- (2- bromine carbazole -9- bases) -5- bromopyridines 600mg, 4- carboline 525mg is added into reaction bulb, opens stirring, according to Secondary addition cuprous iodide 38mg, Trans- cyclohexanediamine 90mg, anhydrous phosphoric acid potassium 750mg, toluene 30ml.Nitrogen replaces system 3 After secondary, system is warming up to 130 degree, after heat preservation for 24 hours, and 10ml purified waters, liquid separation is added in cooling, and water phase is extracted with DCM50ml*2 times, Merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA：PE=1：3, eluent concentration is dry, obtains white Color solid 272mg.Mass spectral molecular ion peak：[M+H] +=577.2.
Embodiment 6：The synthesis of 2,5- [2- (4-N- carboline -9- bases)-carbazole -9- bases]-pyridine (H6)
2,5- bis- (2- bromine carbazole -9- bases)-pyridine 438mg, 4-N- carboline 540mg is added into reaction bulb, opens stirring, Sequentially add cuprous iodide 45mg, Trans- cyclohexanediamine 60mg, anhydrous phosphoric acid potassium 1200mg, toluene 30ml.Nitrogen replacement It is that system is warming up to 130 degree, after heat preservation for 24 hours after 3 times, cooling is added 30ml purified waters, liquid separation, water phase DCM 50ml*2 times Extraction, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA:PE=1:40~1:10, elution Liquid concentration is dry, obtains white solid 200mg.Mass spectral molecular ion peak：[M+H] +=742.3.
Embodiment 7：The synthesis of 2,5- [2- (1-N- carboline -9- bases)-carbazole -9- bases]-pyridine (H7)
2,5- bis- (2- bromine carbazole -9- bases)-pyridine 600mg, 1-N- carboline 800mg is added into reaction bulb, opens stirring, Sequentially add cuprous iodide 90mg, Trans- cyclohexanediamine 90mg, anhydrous phosphoric acid potassium 1800mg, toluene 30ml.Nitrogen replacement It is that system is warming up to 130 degree, after heat preservation for 24 hours after 3 times, cooling is added 20ml purified waters, liquid separation, water phase DCM 50ml*2 times Extraction, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA:PE=1:40~1:10, elution Liquid concentration is dry, obtains white solid 280mg.Mass spectral molecular ion peak：M+=741.3.
Embodiment 8：The synthesis of 2,5- [2- (1-N- phenoxazine groups)-carbazole -9- bases]-pyridine (H8)
2,5- bis- (2- bromine carbazole -9- bases)-pyridine 350mg , phenoxazine 320mg are added into reaction bulb, open stirring, according to Secondary addition cuprous iodide 45mg, Trans- cyclohexanediamine 60mg, anhydrous phosphoric acid potassium 800mg, toluene 30ml.Nitrogen replaces system 3 After secondary, system is warming up to 130 degree, after heat preservation for 24 hours, and 20ml purified waters, liquid separation, water phase 50ml*2 extraction of DCM is added in cooling Take, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent EA:PE=1:40~1:10, eluent Concentration is dry, obtains white solid 260mg.Mass spectral molecular ion peak：M+=771.3.
Embodiment 9：The synthesis of 2,5- [2- (2- dibenzofuran groups)-carbazole -9- bases]-pyridine (H9)
2,5- bis- (2- bromine carbazole -9- bases)-pyridine 300mg, 2- dibenzofurans boric acid 350mg is added into reaction bulb, Stirring is opened, tetrakis triphenylphosphine palladium 40mg, anhydrous phosphoric acid potassium 600mg, toluene 30ml, purified water 3ml are sequentially added.Nitrogen is set After changing system 3 times, system is warming up to 110 degree, after heat preservation for 24 hours, and 20ml purified waters, liquid separation, water phase DCM 50ml* is added in cooling 2 extractions, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent DCM:PE=1:40~1:10, Eluent concentration is dry, obtains white solid 420mg.Mass spectral molecular ion peak：M+=741.2.
Embodiment 10：2,-[2- (2- dibenzofuran groups)-carbazole -9- bases] -5- (carbazole -9- bases)-pyridine (H10) Synthesis
2- (2- (2- dibenzofuran groups)-carbazole -9- bases) -5- bromopyridine 560mg, carbazole are added into reaction bulb 260mg opens stirring, sequentially adds cuprous iodide 28mg, Trans- cyclohexanediamine 60mg, anhydrous phosphoric acid potassium 500mg, toluene 30ml.After nitrogen displacement system 3 times, system is warming up to 130 degree, after heat preservation for 24 hours, and 10ml purified waters, liquid separation, water phase is added in cooling Extracted with DCM20ml*2 times, merge it is organic relevant dry, it is dry after organic phase concentration it is dry, cross silicagel column, eluant, eluent DCM：PE=1： 3, eluent concentration is dry, obtains white solid 420mg.Mass spectral molecular ion peak：M+=575.2.
Luminescent properties detect example
Above compound H1-H3 is dissolved in MeTHF, phosphorescence luminescent spectrum is measured in low temperature 77K, it is triple to obtain first State energy level T1 energy levels.Fluorescence emission spectra is measured, the first singlet state S1 energy levels are obtained.
With 10K/min heating rates, the differential scanning calorimetry DSC data of compound is measured, obtains glass transition temperature (Tg).
HOMO and LUMO values are measured using the electrochemical method of industry routine, by the oxidizing potential Eox for measuring organic matter Directly to calculate HOMO energy level numerical value, calculation formula HOMO=Eox+4.74.In conjunction with the band gap Eg that spectroscopic methodology measures, calculate Formula is Eg=hc/ λ abs=1240/ λ abs, calculates lumo energy numerical value, calculation formula LUMO=HOMO-Eg indirectly.
The optics and thermodynamic data of related compound are as shown in table 1.
The optics and thermodynamic data of 1 compound of table
Compound S1(eV) T1(eV) Tg(℃) HOMO LUMO Eg
H1 3.52 2.90 130 5.50 1.98 3.52
H2 3.57 2.93 133 6.15 2.62 3.55
H3 3.46 2.97 154 5.46 2.02 3.44
It will be understood by those skilled in the art that the respective embodiments described above are to realize specific embodiments of the present invention, And in practical applications, can to it, various changes can be made in the form and details, without departing from the spirit and scope of the present invention.

Claims (10)

1. the pyridine compounds of 2,5 substitutions of one kind having structure shown in logical formula (I)：
Wherein,
X1、X2、Y1、Y2、Z1、Z2N atoms or CRx are each independently represented, and the Rx indicates that hydrogen atom, D-atom, halogen are former Son, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 Heteroaryl amido；
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1-C24 alkane Base, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 virtue sulphur Base, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amidos；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkane Sulfenyl, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 are miscellaneous Aryl, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 Aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
2. according to claim 12, the pyridine compounds of 5 substitutions, which is characterized in that have shown in logical formula (II) Structure：
Wherein,
N1-N8N atoms or CRy are each independently represented, and the Ry indicates hydrogen atom, D-atom, halogen atom, C1-C24 alkane Base, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 virtue sulphur Base, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amidos；
G1、G2Each independently represent hydrogen atom, D-atom, halogen atom, C1-C24 alkyl, C1-C24 alkoxies, C1-C24 alkane Sulfenyl, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 arylthios, C7-C72 aryl amines, C3-C72 are miscellaneous Aryl, C3-C72 heteroaryloxies, C3-C72 heteroarylthios, C4-C72 heteroaryl amidos, and G1、G2In at least one be C6-C72 Aryl, C2-C24 alkylamino radicals, C3-C72 heteroaryls or C4-C72 heteroaryl amidos.
3. according to claim 22, the pyridine compounds of 5 substitutions, which is characterized in that the G1、G2For identical substitution Base.
4. according to claim 22, the pyridine compounds of 5 substitutions, which is characterized in that the G1、G2Each independently With structure shown in formula (III-1) or (III-2)：
Wherein,
Ar1、Ar2Each independently represent C1-C24 alkyl, C6-C72 aryl, C3-C72 heteroaryls；Ar1And Ar2Be not attached to or Ar1And Ar2It is connected by singly-bound, double bond, carbon atom or hetero atom；
M1、M2、M3、M4N atoms or CRz are each independently represented, and Rz indicates hydrogen atom, D-atom, halogen atom, C1-C24 alkane Base, C1-C24 alkoxies, C1-C24 alkylthio groups, C2-C24 alkylamino radicals, C6-C72 aryl, C6-C72 aryloxy group, C6-C72 virtue sulphur Base, C7-C72 aryl amines, C3-C72 heteroaryls, C3-C72 heteroaryloxies, C3-C72 heteroarylthios or C4-C72 heteroaryl amidos；
Z indicates oxygen atom, sulphur atom, sulfuryl, 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 heteroaryls.
5. according to claim 42, the pyridine compounds of 5 substitutions, which is characterized in that the connection Ar1And Ar2Carbon Atom is one or two, and the carbon atom is by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or C3-C36 heteroaryls Base replaces；The hetero atom is oxygen atom, sulphur atom, silicon atom, nitrogen-atoms or boron atom, the sulphur atom it is not substituted or Replaced by one or two oxygen atom, the silicon atom, nitrogen-atoms or boron atom by hydrogen atom, D-atom, C1-C12 alkyl, C6-C36 aryl or the substitution of C3-C36 heteroaryls.
6. according to claim 42, the pyridine compounds of 5 substitutions, which is characterized in that G1、G2, Rx, Ry, Rz it is respectively only On the spot have selected from one of following structure：
Wherein,
R1-R16Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R21-R26Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 aryl, The heteroaryloxy of C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18；
R31-R34Each independently represent hydrogen atom, D-atom, fluorine atom, C1-C6 alkyl, C1-C6 alkoxies, C6-C18 aryl, C3-C18 heteroaryls, C7-C18 aryl amines, C4-C18 heteroaryls amido, C6-C18 aryloxy group or C3-C18 heteroaryloxies；
R101-R106Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls；
R201-R205Each independently represent C1-C12 alkyl, C6-C18 aryl or C3-C18 heteroaryls.
7. according to claim 62, the pyridine compounds of 5 substitutions, which is characterized in that G1、G2, Rx, Ry, Rz it is respectively only On the spot there is one of following structure：
Wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340Each independently represent hydrogen atom, D-atom, methyl, ethyl, Propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group, naphthalene, carbazyl or carboline base；
R2010Indicate methyl, ethyl, propyl, butyl, amyl, hexyl, phenyl, tolyl, 3,5-dimethylphenyl, pyridyl group or naphthalene.
8. according to claim 12, the pyridine compounds of 5 substitutions, which is characterized in that have selected from one of following Structure：
9. 2 described in any one of claim 1-8, pyridine compounds the answering in organic electroluminescence device of 5 substitutions With.
10. application according to claim 9, which is characterized in that described 2, the pyridine compounds of 5 substitutions are the organic electroluminescence Blue phosphorescent material of main part in luminescent device.
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