CN108707136A - A kind of pyridine triphenylene compound and its application - Google Patents

A kind of pyridine triphenylene compound and its application Download PDF

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CN108707136A
CN108707136A CN201810873148.4A CN201810873148A CN108707136A CN 108707136 A CN108707136 A CN 108707136A CN 201810873148 A CN201810873148 A CN 201810873148A CN 108707136 A CN108707136 A CN 108707136A
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pyridine
aryl
compound
triphenylene
triphenylene compound
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刘九州
李小军
马腾达
黄达
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, a kind of pyridine triphenylene compound and its application are disclosed.Compound disclosed in this invention has structure shown in logical formula (I), this kind of pyridine triphenylene compound contains the pyridine groups with good electron transport ability and the carbazole with good cavity transmission ability/carboline group simultaneously, plays the role of while adjusting electrons and holes transmittability；In addition, the triphenylene structure being connected with carbazole/carboline group further has adjusted the electrons and holes transmittability of compound, thus the hole performance and electronic transmission performance of the compound more balance.In addition, the synthetic route of the compounds of this invention is easy, it is suitable for industrial mass production.

Description

A kind of pyridine triphenylene compound and its application
Technical field
The invention belongs to field of organic electroluminescent materials, more particularly to a kind of pyridine triphenylene compound and its application.
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 phosphorus 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, it in order to reach efficient electroluminescence, needs to develop stable structure and being capable of balancing charge transmission The material of main part of performance.
Invention content
The purpose of the present invention is to provide a kind of pyridine triphenylene compound, this kind of compound is a kind of letter of synthesis step Just, stable structure and it is capable of the material of main part of balancing charge transmission performance.
Pyridine triphenylene compound provided by the present invention has structure shown in logical formula (I)：
Wherein,
N1、N2、N3、N4Each independently represent N atoms or CRx, and the Rx indicate hydrogen, deuterium, halogen, alkyl, aryl or Heteroaryl；
L indicates that C6-C72 aryl or C3-C72 heteroaryls or L are not present；
R1For hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
Optionally, in the presence of L, the compound that embodiments of the present invention are provided has shown in logical formula (II) Structure：
Wherein,
N1、N2、N3、N4N atoms or CRx are each independently represented, and the Rx indicates hydrogen, deuterium, halogen, alkyl or aryl；
L indicates C6-C72 aryl or C3-C72 heteroaryls.
Optionally, one or several combinations of the L in substituted or unsubstituted following group：Phenyl, naphthalene, Anthryl, phenanthryl, pyrenyl, triphenylene, base, fluorenyl, Spirofluorene-based, carbazyl, pyridyl group, pyrazinyl, pyrimidine, triazine radical, quinoline Quinoline base, acridinyl, indyl, benzofuranyl and benzothienyl.
Optionally, the substituent group of the L is selected from C1-C12 alkyl, C6-C2 aryl or C3-C24 heteroaryls.
Optionally, in the presence of L, the pyridine triphenylene compound that embodiments of the present invention are provided has Selected from one of following structure：
Optionally, in the case that L is not present, the pyridine triphenylene compound that embodiments of the present invention are provided, There can be structure shown in logical formula (III)：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl,
R2For hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
Optionally, work as R2Also in the case of being not present, the pyridine triphenylene compound that embodiments of the present invention are provided, With structure shown in logical formula (IV)：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl.
Optionally, in the case that L is not present, the pyridine triphenylene compound that embodiments of the present invention are provided, tool Have selected from one of following structure：
Embodiments of the present invention also provide application of the above-mentioned pyridine triphenylene compound in organic electroluminescence device. The present invention pyridine triphenylene compound can be used between organic electroluminescence device cathode and anode, as material of main part, Guest materials or auxiliary material use.The material of main part can be phosphorescent light body material, or fluorescent host material； 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 are hole Transmission material, hole-injecting material, hole barrier materials, electron transport material, electron injection material, electron-blocking materials and electricity Lotus generates material.The pyridine triphenylene compound of the present invention can also be used in except organic electroluminescence device cathode and anode, It is used as covering layer material.Wherein, pyridine triphenylene compound of the invention is particularly suitable as organic electroluminescence device In phosphorescent light body material.
The pyridine triphenylene compound that embodiments of the present invention are provided, contain has good electron transport ability simultaneously Pyridine groups and carbazole/carboline group with good cavity transmission ability, play while adjusting electrons and holes transmission The effect of ability, the triphenylene structure being connected with carbazole/carboline group further have adjusted the electrons and holes transmission of compound Ability, thus the hole performance and electronic transmission performance of the compound more balance.In addition, the synthetic route of the compounds of this invention Simplicity is suitble to industrial mass production.
Description of the drawings
The hydrogen spectrum that Fig. 1 is the compound H1 that in the specific embodiment of the invention prepared by embodiment 1；
The hydrogen spectrum that Fig. 2 is the compound H2 that in the specific embodiment of the invention prepared by embodiment 2.
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 triphenylene compound is provided, there is logical formula (I) Shown in structure：
Wherein,
N1、N2、N3、N4Each independently represent N atoms or CRx, and the Rx indicate hydrogen, deuterium, halogen, alkyl, aryl or Heteroaryl；
L indicates that C6-C72 aryl or C3-C72 heteroaryls or L are not present；
R1For hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
In certain specific embodiments of the invention, L exists, then provided compound has and tied shown in logical formula (II) Structure：
Wherein,
N1、N2、N3、N4N atoms or CRx are each independently represented, and the Rx indicates hydrogen, deuterium, halogen, alkyl or aryl；
L indicates C6-C72 aryl or C3-C72 heteroaryls.
In certain specific embodiments of the invention, one or several in substituted or unsubstituted following group of L A combination：Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, triphenylene, base, fluorenyl, Spirofluorene-based, carbazyl, pyridyl group, pyrrole Piperazine base, pyrimidine, triazine radical, quinolyl, acridinyl, indyl, benzofuranyl and benzothienyl.
In certain specific embodiments of the invention, the substituent group of the L be selected from C1-C12 alkyl, C6-C2 aryl or C3-C24 heteroaryls.
In certain specific embodiments of the invention, the pyridine triphenylene compound provided has selected from one of following Structure：
In other specific implementation modes of the present invention, L is not present, then the pyridine triphenylene compound provided also may be used With structure shown in logical formula (III)：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl,
R2For hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
In other specific implementation modes of the present invention, the pyridine triphenylene compound provided has logical formula (IV) institute The structure shown：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl.
In other specific implementation modes of the present invention, the pyridine triphenylene compound provided has selected from as follows One of structure：
General synthetic routes：
Specific embodiments of the present invention also provide the preparation method of above-mentioned pyridine triphenylene compound, can be by leading to as follows It is synthesized with synthetic route (Syn-1)：
Wherein, S1、S2、S3Reaction leaving group is each independently represented, reaction leaving group is diversified, citing And it is unrestricted, fluorine atom, chlorine atom, bromine atom, iodine atom, boric acid base group, borate group may be selected；Other groups are fixed Justice is identical as the logical formula (I) of the application.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.
Specific reaction condition is not limited, citing as temperature, the type of solvent and dosage, the type of catalyst and Dosage, the type of co-catalyst and dosage, the type of alkali and dosage, the dosage of water, the rate of charge of reaction substrate and sequence, in the industry Those skilled in the art easily can reasonably be promoted from the embodiment in the embodiment of the present invention, and the general foundation of selection can With pertinent literature, patent and the books with reference to organic synthesis.It is related to coupling reaction, can preferentially refers to suzuki reaction and crow The related data of Germania reaction；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 for desiredization 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；CDCl3, deuterium For chloroform；MeTHF：Methyltetrahydrofuran；CuI：Cuprous iodide；DMSO：Dimethyl sulfoxide (DMSO)；HPLC：High performance liquid chromatography.
Embodiment 1:Synthesize compound H1
100ml (60vol) toluene, 10ml (6vol) ethyl alcohol are added into 350ml tube sealings, 10ml (6vol) purified water is opened Stirring is opened, the bromo- 9- of 2- (pyridyl group -2- bases) carbazole 1.62g (1.0eq), 2- borate triphenylenes 2.13g is sequentially added (1.2eq) potassium carbonate 1.38g (2.0eq), tetra-triphenylphosphine palladium 289mg (0.05eq), nitrogen are bubbled 30min, thoroughly after degassing, 120 DEG C are warming up to, 48h is kept the temperature.System cools down, and 100ml purified waters, liquid separation, water phase 100ml*3 extraction of ethyl acetate is added It takes, merges organic phase, anhydrous sodium sulfate drying is added, system concentrates after drying, column chromatography, eluant, eluent EA：PE=1：2, elution Liquid is concentrated to give white solid 1.98g (yields：85%), HPLC:99%.
1H NMR(400MHz,CHLOROFORM-d)δppm 7.31-7.41(m,2H)7.43-7.52(m,1H)7.61- 7.71(m,4H)7.71-7.80(m,2H)7.83-7.89(m,1H)7.93-8.01(m,2H)8.13-8.19(m,1H)8.19- 8.23 (m, 1H) 8.23-8.28 (m, 1H) 8.63-8.70 (m, 3H) 8.72 (d, J=8.69Hz, 1H) 8.74-8.79 (m, 2H) 8.88-8.93(m,1H)。
Embodiment 2：Synthesize compound H2
50ml (60vol) toluene, 5ml (6vol) ethyl alcohol are added into 150ml tube sealings, 10ml (6vol) purified water is opened Stirring, sequentially adds the bromo- 9- of 3- (pyridine -2- bases) carbazole 0.81g (1.0eq), 2- borate triphenylene 1.56g (1.2eq), carbon Sour potassium 0.7g (2.0eq), tetra-triphenylphosphine palladium 150mg (0.05eq), nitrogen are bubbled 30min, thoroughly after degassing, are warming up to 120 DEG C, keep the temperature 48h.System cools down, and 100ml purified waters, liquid separation is added, and water phase 100ml*3 extraction of ethyl acetate merges organic Anhydrous sodium sulfate drying is added in phase, and system concentrates after drying, column chromatography, eluant, eluent EA：PE=1：2, eluent is concentrated to give white Solid 1.03g (yields：88%), HPLC:99%.
1H NMR(400MHz,DMSO-d6)δppm 7.34-7.40(m,1H)7.45-7.52(m,2H)7.69-7.75(m, 4H)7.82-7.86(m,2H)7.92-7.96(m,1H)8.05-8.11(m,1H)8.11-8.19(m,2H)8.42-8.48(m, 1H)8.72-8.77(m,1H)8.79-8.86(m,3H)8.88-8.93(m,2H)9.04-9.09(m,1H)9.14-9.19(m, 1H)。
Embodiment 3：Synthesize compound H3
By 2- (Ben Bing [9,10]Phenanthrene -2- bases) -6- tertiary butyl -9H- carbazoles (449mg, 1.0mmol), 4- (pyridin-3-yl) Bromobenzene (234mg, 1.0mmol), CuI (38mg, 0.2mmol), anti-form-1,2- cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), toluene (3mL) are placed in 38mL tube sealings, and nitrogen is warming up to 120 DEG C after being bubbled 5min, reaction reflux 48h.After the completion of reaction, pad diatomite filtering elutes filter cake with ethyl acetate.It is molten that vacuum distillation removing is carried out to gained filtrate Then gains are crossed silicagel column (petroleum ether by agent：Ethyl acetate=20：1→10：1) it is purified, obtains white solid (297mg, yield 49%).Mass spectral molecular ion peak：602.
Embodiment 4：Synthesize compound H4
By 2- (Ben Bing [9,10]Phenanthrene -2- bases) -9H- carbazoles (393mg, 1.0mmol), the bromo- 7- of 2- (pyridin-3-yl) -9, 9 '-spiral shell, two fluorenes (472mg, 1.0mmol), CuI (38mg, 0.2mmol), anti-form-1,2- cyclohexanediamine (22mg, 0.2mmol), phosphorus Sour potassium (424mg, 2.0mmol), toluene (3mL) are placed in 38mL tube sealings, and nitrogen is warming up to 120 DEG C after being bubbled 5min, reacts back Flow 48h.After the completion of reaction, pad diatomite filtering elutes filter cake with ethyl acetate.It is molten that vacuum distillation removing is carried out to gained filtrate Then gains are crossed silicagel column (petroleum ether by agent：Ethyl acetate=10：1) it is purified, obtaining white solid, (550mg is received Rate 70%).Mass spectral molecular ion peak：784.
Embodiment 5：Synthesize compound H5
By 2- (Ben Bing [9,10]Phenanthrene -2- bases) -9H- carbazoles (393mg, 1.0mmol), 2,3,5,6- tetraphenyl -4- (pyrroles Pyridine -2- bases) bromobenzene (538mg, 1.0mmol), CuI (38mg, 0.2mmol), anti-form-1,2- cyclohexanediamine (22mg, 0.2mmol), potassium phosphate (424mg, 2.0mmol), DMSO (3mL) are placed in 38mL tube sealings, and nitrogen is warming up to after being bubbled 5min 130 DEG C, reaction reflux 48h.After the completion of reaction, pad diatomite filtering elutes filter cake with ethyl acetate.Gained filtrate is subtracted Solvent is distilled off in pressure, and gains are then crossed silicagel column (petroleum ether：Ethyl acetate=20：1→10：1) it is purified, is obtained White solid (180mg, yield 21%).Mass spectral molecular ion peak：850.
Compounds property detects
H1, H2 compound of above-mentioned preparation are dissolved in MeTHF, room temperature measures photoluminescence spectra, and it is single to obtain first Weight state energy level S1 energy levels measure photoluminescence spectra in low temperature 77K, obtain the first triplet energy level T1 energy levels.Compound is existed It is heated up with 10K/min speed under condition of nitrogen gas, obtains glass transition temperature Tg.As a result it see the table below 1：
The optics and thermodynamic data of 1 compound of table
Compound name S1(eV) T1(eV) Tg(℃)
H1 3.51 2.67 96.21
H2 3.49 2.71 95.86
Device preparation example
Good characteristic of the compound provided in order to further illustrate the present invention in luminescent device, using different structure Compound makes luminescent device respectively with this field conventional fabrication process and condition.Prepared photophore in present embodiment The structure of part is ITO/HAT-CN/NPB/TCTA/Host:Irppy3/BAlq/Mg:Then Ag tests the property of corresponding luminescent device Energy (structural formula of related compound is seen below).Wherein, Host indicates material of main part.Material of main part can select chemical combination of the present invention Object can also select other compounds, in the specific implementation mode of the present invention, with compound C2 compounds as a comparison.Change It is 3- (2- triphenylenes) -9- (4- xenyls)-carbazole to close object C2.The following table 2 is device performance data.
2 device performance data of table
Device embodiments Material of main part EQE1 EQE2
No.1 H1 18.1 16.4
No.2 H2 17.3 15.3
CC.1 C2 10.3 8.5
In upper table 2, EQE1 is maximum external quantum efficiency, and EQE2 is in 10000cd/m2Under the conditions of external quantum efficiency.
As can be seen from Table 2, opposite since the hole performance and electronic transmission performance of the compounds of this invention more balance Unbalanced compound C2 is transmitted in charge, in the material of main part as luminescent layer in application, improvement in external quantum efficiency Clearly, when the luminance is increased, external quantum efficiency is still higher.
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 (9)

1. a kind of pyridine triphenylene compound has structure shown in logical formula (I)：
Wherein,
N1、N2、N3、N4N atoms or CRx are each independently represented, and the Rx indicates hydrogen, deuterium, halogen, alkyl, aryl or heteroaryl Base；
L indicates that C6-C72 aryl or C3-C72 heteroaryls or L are not present；
R1Indicate hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
2. pyridine triphenylene compound according to claim 1, which is characterized in that have structure shown in logical formula (II)：
Wherein,
N1、N2、N3、N4N atoms or CRx are each independently represented, and the Rx indicates hydrogen, deuterium, halogen, alkyl or aryl；
L indicates C6-C72 aryl or C3-C72 heteroaryls.
3. pyridine triphenylene compound according to claim 2, which is characterized in that L is selected from substituted or unsubstituted as follows One or several combinations in group：Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, triphenylene, base, fluorenyl, it is Spirofluorene-based, Carbazyl, pyridyl group, pyrazinyl, pyrimidine, triazine radical, quinolyl, acridinyl, indyl, benzofuranyl and benzothienyl.
4. pyridine triphenylene compound according to claim 3, which is characterized in that the substituent group of the L is selected from C1-C12 Alkyl, C6-C2 aryl or C3-C24 heteroaryls.
5. pyridine triphenylene compound according to claim 4, which is characterized in that have selected from one of following structure：
6. pyridine triphenylene compound according to claim 1, which is characterized in that have structure shown in logical formula (III)：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl,
R2Indicate hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
7. pyridine triphenylene compound according to claim 6, which is characterized in that have structure shown in logical formula (IV)：
Wherein,
M1、M2、M3、M4N atoms or CRy are each independently represented, the Ry indicates hydrogen, deuterium, halogen, alkyl or aryl.
8. pyridine triphenylene compound according to claim 7, which is characterized in that have selected from one of following structure：
9. application of the pyridine triphenylene compound in organic electroluminescence device described in any one of claim 1-8.
CN201810873148.4A 2018-08-02 2018-08-02 A kind of pyridine triphenylene compound and its application Withdrawn CN108707136A (en)

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Application publication date: 20181026