CN106749198A - A kind of compound containing pyridine groups and the organic luminescent device using the compound - Google Patents

A kind of compound containing pyridine groups and the organic luminescent device using the compound Download PDF

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CN106749198A
CN106749198A CN201611028176.3A CN201611028176A CN106749198A CN 106749198 A CN106749198 A CN 106749198A CN 201611028176 A CN201611028176 A CN 201611028176A CN 106749198 A CN106749198 A CN 106749198A
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compound
containing pyridine
compound containing
pyridine groups
substituted
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郭建华
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Pyridine Compounds (AREA)

Abstract

The present invention provides a kind of compound containing pyridine groups and the organic luminescent device using the compound, belongs to organic photoelectrical material technical field.The compound containing pyridine groups has structure shown in formula (I), compound containing pyridine groups of the present invention has good heat endurance and excellent hole transport performance, can be used to prepare organic electroluminescence device, especially as the material in organic electroluminescence device hole-transporting layer, the luminous efficiency and service life of organic luminescent device can be effectively improved.Organic luminescent device prepared by the compound containing pyridine groups provided using the present invention, with luminous efficiency higher, luminous efficiency is up to 7.0~7.9cd/A, and driving voltage is low, long service life, is a kind of excellent OLED material.

Description

A kind of compound containing pyridine groups and the organic luminescent device using the compound
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of compound and use containing pyridine groups should The organic luminescent device of compound.
Background technology
At present, display screen is based on TFT (Thin Film Transistor, TFT)-LCD, due to It is non-spontaneous optical display unit, it is therefore necessary to passes through backlight throw light, and sequentially penetrates the polarisation in TFT-LCD panels The correlation spare part such as plate, glass substrate, liquid crystal layer, colored filter, glass substrate, Polarizer, finally enter the eyes of people into Picture, can be only achieved the function of display.Just because of above-mentioned complicated display process, its display screen occurs in actual application Reaction rate is slow, power consumption, narrow viewing angle the shortcomings of, be not enough to turn into perfect display screen.
Organic electroluminescent LED (OLEDs) possesses existing aobvious as a kind of brand-new Display Technique in each performance Show the unmatched advantage of technology, such as have it is all solid state, from main light emission, brightness high, high-resolution, visual angle (more than 170 degree) wide, Fast response time, thickness of thin, small volume, it is lightweight, can be used flexible base board, low-voltage direct-current drive (3-10V), it is low in energy consumption, Operating temperature range is wide etc. so that its application market is quite varied, such as illuminator, communication system, car-mounted display, portable Electronic equipment, fine definition show even military field.
At present, the research of electroluminescent organic material is carried out extensively in academia and industrial quarters, wherein, hole transport Material is the important component of organic electroluminescence device, and stability and transmission performance on hole mobile material are still suffered from Very big room for improvement, governs the industrialization of luminescent device.Therefore, design and a kind of compound of searching, new as OLED Material occurs to overcome the shortcomings of it in actual application, is the emphasis in OLED material research work and research and development from now on Trend.
The content of the invention
It is an object of the invention to provide a kind of compound containing pyridine groups and the organic illuminator using the compound Part, the compound heat endurance is good, and the luminescent device prepared using the compound has luminous efficiency and service life higher.
The invention provides a kind of compound containing pyridine groups, shown in its general structure such as formula (I)：
Wherein, X is S or O；R1、R2It is independent selected from substituted or unsubstituted aromatic hydrocarbyl or substituted or unsubstituted Aromatic heterocycle.
Preferably, the R1、R2It is independent selected from the aromatic hydrocarbyl of substituted or unsubstituted C6~C50 or substitution or not The aromatic heterocycle of substituted C4~C50.
Preferably, the R1、R2It is independent selected from the aromatic hydrocarbyl of substituted or unsubstituted C6~C30 or substitution or not The aromatic heterocycle of substituted C4~C30.
Preferably, the aromatic hydrocarbyl is selected from phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenes Base, pyrenyl, perylene base, fluoranthene base or benzo phenanthryl.
Preferably, the hetero atom in the aromatic heterocycle is nitrogen.
Preferably, the aromatic heterocycle is selected from pyridine radicals or carbazyl.
Preferably, the compound containing pyridine groups is as shown in any one of formula 1~22：
The present invention also provides a kind of organic luminescent device, and the organic luminescent device includes the chemical combination containing pyridine groups Thing.
Preferably, the organic luminescent device includes first electrode, second electrode and is arranged at the first electrode and the Organic matter layer between two electrodes；The organic matter layer includes the described compound containing pyridine groups.
Preferably, the organic matter layer includes hole transmission layer, and the compound containing pyridine groups is passed as hole The constituent material of defeated layer.
Beneficial effects of the present invention：
Compared with prior art, the present invention provides a kind of compound containing pyridine groups and the organic hair using the compound Optical device, the compound for containing pyridine groups has structure shown in formula (I), and the compound containing pyridine groups of the present invention has Good heat endurance and excellent hole transport performance, can be used to prepare organic electroluminescence device, especially as organic Material in electroluminescent device hole-transporting layer, can effectively improve the luminous efficiency of organic luminescent device and use the longevity Life.
Test result indicate that, organic luminescent device prepared by the compound containing pyridine groups provided using the present invention, tool There is a luminous efficiency higher, luminous efficiency is up to 7.0~7.9cd/A, and driving voltage is low, long service life, is a kind of excellent Different OLED material.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, but It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art The implication that member is generally understood is identical.
Aromatic hydrocarbyl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, to be left monad radical Group general name, its can be monocyclic aryl or fused ring aryl, for example may be selected from phenyl, xenyl, terphenyl, naphthyl, anthryl, Phenanthryl, fluorenyl, the fluorenyl of spiral shell two or pyrenyl etc., but not limited to this.
Aromatic heterocycle of the present invention refers to that one or more the aromatic core carbon in aryl are obtained by hetero atom replacement The general name of group, the hetero atom includes but is not limited to oxygen, sulphur and nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or thick Ring heteroaryl, for example may be selected from pyridine radicals, quinolyl, carbazyl, thienyl, benzothienyl, pyrimidine radicals, benzo pyrimidine radicals, Imidazole radicals or benzimidazolyl etc., but not limited to this.
Present invention firstly provides a kind of compound containing pyridine groups, shown in its general structure such as formula (I)：
Wherein, X is S or O；R1、R2It is independent selected from substituted or unsubstituted aromatic hydrocarbyl or substituted or unsubstituted Aromatic heterocycle.
According to the present invention, the R1、R2It is preferred that independent aromatic hydrocarbyl selected from substituted or unsubstituted C6~C50 or The aromatic heterocycle of substituted or unsubstituted 46~C50；The further preferably independent virtue selected from substituted or unsubstituted C6~C30 The aromatic heterocycle of fragrant race's alkyl or substituted or unsubstituted C4~C30.
According to the present invention, the aromatic hydrocarbyl in the substituted or unsubstituted aromatic hydrocarbyl, more specifically, preferably It is phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylene base, fluoranthene base or benzo phenanthryl, more Preferably xenyl, terphenyl or fluorenyl；Aromatic heterocycle in the substituted or unsubstituted aromatic heterocycle, its In hetero atom be preferably nitrogen, more specifically, preferably pyridine radicals or carbazyl, more preferably carbazyl.
According to the present invention, the substitution base in the aromatic heterocycle of the substituted aromatic hydrocarbyl or substitution may be selected from The heteroaryl of the alkyl of C1~C10, the alkoxy of C1~C10, the cycloalkyl of C3~C20, the aryl of C6~C20 or C4~C20, These substitution bases are optionally further selected from the substitution base substitution of this kind of group.
According to the present invention, the compound containing pyridine groups is not particularly limited, and is preferably as follows shown：
It is enumerated above some specific structure types of the compound containing pyridine groups of the present invention, but institute of the present invention State the compound containing pyridine groups and be not limited to these listed chemical constitutions, it is every based on structure shown in formula (I), R1、R2, X should be included for group as defined above.
The preparation method of the compound containing pyridine groups of the present invention, including by the compound shown in formula (A) and formula (B) Shown compound carries out reacting the compound containing pyridine groups shown in the formula of obtaining (I).
The present invention does not have particular/special requirement to the condition of above-mentioned reaction, with the normal of such reaction well known to those skilled in the art Rule condition.The present invention has no particular limits to the source of the raw material employed in above-mentioned reaction, can be commercially available prod Or prepared using preparation method well-known to those skilled in the art.Wherein, the R1、R2, X selection it is same as above, This is repeated no more.
The present invention also provides a kind of organic luminescent device, including the compound containing pyridine groups.The organic light emission The organic luminescent device that device is well known to those skilled in the art, organic luminescent device of the present invention preferably includes One electrode, second electrode and the organic matter layer being arranged between the first electrode and second electrode；The organic matter layer is included The described compound containing pyridine groups.The organic matter layer can include hole injection layer, hole transmission layer, electronic blocking At least one of which in layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, it is preferably described containing pyridine groups Compound is used as the hole transport layer material in organic matter layer.
The present invention has no particular limits to the source of the raw material employed in following examples, can for commercially available prod or Prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The synthesis of intermediate A 1
The tetrahydrochysene of 0.1mol p-aminodiphenyls, 0.1mol 3- bromine-N-phenylcarbazoles and 600mL is added toward reaction bulb Furans and 100ml water, and the potassium carbonate of 0.2mol is added thereto to, and 0.5g tetra- (triphenyl) phosphine palladium is added, in nitrogen protection Lower normal temperature 12 hours；Then, to addition distilled water terminating reaction in reaction solution, and extracted with ethanol/dichloromethane, salt solution Wash, separate organic layer, revolving removes organic solvent, crude product crosses post, then purified with dichloromethane and ethyl alcohol recrystallization and obtain 30.4g intermediate As 1, yield 84%.
Following midbody compound is obtained in a similar fashion：
Embodiment 2：The synthesis of intermediate B 1-1
16.9g (1) is dissolved in 180ml glacial acetic acid, the mixed liquor of 15ml bromines and 110ml glacial acetic acid is slowly added dropwise, About 5h completion of dropping.There are a large amount of solids to separate out.LC tracks to reactant disappearance, stops reaction.Frozen water, suction filtration is added to obtain 29.5g yellow solids powder (2), yield 91%.
By 32.4g yellow solids powder (2), and 133.8g NH4Cl is dissolved in 500ml methyl alcohol and 500ml water, room temperature After stirring 1h, the Fe powder 56g after activation are added, after the mixture was stirred overnight, be filtered to remove unnecessary Fe powder.Ethyl acetate extracts Water intaking phase, anhydrous Na2SO4Dry, concentration obtains 23.52g intermediates (3), yield 80%.
29.5g intermediates (3) are added into 300ml absolute ethyl alcohols, then the 30ml concentrated sulfuric acids are added dropwise, be heated to dissolving.Add 25.5g natrium nitrosums, 90 DEG C of stirrings of constant temperature, LC tracking reaction to raw material disappears, and solvent is spin-dried for, and adds mixture of ice and water, thick to produce Product are separated out, and are recrystallized with glacial acetic acid-water, obtain 26.6g products (4).Yield 90%.
1.36g anhydrous zinc chlorides, 3.8g DBU, 27.9g product (4), 200ml methyl alcohol are added in autoclave, stirring 0.5h, adds the hydrogen peroxide of 50g 30%, 80 DEG C of reaction 10h.Concentrated solvent after the completion of reaction, the crude product for obtaining crosses silicagel column, Solvent is made with petrol ether/ethyl acetate, 11.8g products (5) are obtained.Yield 40%.
29.5g products (5) are taken, 20g is to bromobenzeneboronic acid, 41.4g K2CO3, 150ml water, 150ml ethanol, 900ml toluene, Dissolving is mixed to, Ar gas is replaced three times, adds four triphenyl phosphorus palladium 1.2g, and Ar gas is replaced three times again.Back flow reaction is extremely Raw material disappears.Solvent is spin-dried for, and the crude product for obtaining crosses silicagel column, and petrol ether/ethyl acetate makees solvent, obtains 25.9g products (6).Yield 79%.
Take in 18.6g products (6) addition 250ml TFMSs, 24h is stirred at room temperature.Then reaction solution is poured into 1L (9 in water-pyridine mixtures:1v:v).Heating is overall to flowing back, and keeps 30min.After cooling, reaction solution is extracted with dichloromethane. With anhydrous sodium sulfate drying, concentration, crude product silicagel column, with being that petroleum ether makees solvent, obtain 15g white products (7).Receive Rate 81%.
Take 33.9g white products (7), 13.5g neighbour's pyridine boronic acids, 41.4g K2CO3, 150ml water, 150ml ethanol, 900ml Toluene, mixes to dissolving, and Ar gas is replaced three times, adds four triphenyl phosphorus palladium 1.2g, and Ar gas is replaced three times again.Backflow is anti- Should be disappeared to raw material.Solvent is spin-dried for, and the crude product for obtaining crosses silicagel column, with being that petrol ether/ethyl acetate makees solvent, obtains 27.2g products B1-1.Yield 80%.Total recovery 13.4%.
Following midbody compound is obtained in a similar fashion：
Embodiment 3：The synthesis of intermediate B 2-1
Take 32.3g raw materials (8), 13.53g neighbour's pyridine boronic acids, 41.4g K2CO3, 150ml water, 150ml ethanol, 900ml first Benzene, mixes to dissolving, and Ar gas is replaced three times, adds four triphenyl phosphorus palladium 1.2g, and Ar gas is replaced three times again.Back flow reaction Disappeared to raw material.Solvent is spin-dried for, and the crude product for obtaining crosses silicagel column, with being that petrol ether/ethyl acetate makees solvent, obtains 22.6g white products B2-1.
Following midbody compound is obtained in a similar fashion：
Embodiment 4：The synthesis of compound 19
Take 4.1g raw material As 1,3.2g raw materials B2-1,2.24g potassium tert-butoxide, 40ml toluene, stirring and dissolving, Ar gas displacement three It is secondary, add catalyst Pd2(dba)30.0234g, tri-butyl phosphine 0.08g, replace Ar gas three times again, are heated to backflow tracking Reaction is to terminating.Solvent is spin-dried for, crude product re crystallization from toluene, obtains product 5g.Yield 76%.
Mass spectrum m/z：653.70 (calculated values：653.77).Theoretical elemental content (%) C47H31N3O：C,86.35；H,4.78； N,6.43；O,2.45.Actual measurement constituent content (%)：C,86.30；H,4.78；N,6.42；O,2.45.The above results confirm to obtain Product is target product.
Embodiment 5：The synthesis of compound 1
A1 in embodiment 4 is replaced with into A3, B2-1 replaces with B2-2, other steps are same as Example 4, changed Compound 1.
Mass spectrum m/z：564.68 (calculated values：564.67).Theoretical elemental content (%) C41H28N2O：C,87.21；H,5.00； N,4.96；O,2.83.Actual measurement constituent content (%)：C,87.23；H,5.01；N,4.96；O,2.83.The above results confirm to obtain Product is target product.
Embodiment 6：The synthesis of compound 2
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B2-2, other steps are same as Example 4, changed Compound 2.
Mass spectrum m/z：604.78 (calculated values：604.74).Theoretical elemental content (%) C44H32N2O：C,87.39；H,5.33； N,4.63；O,2.65.Actual measurement constituent content (%)：C,87.42；H,5.33；N,4.66；O,2.63.The above results confirm to obtain Product is target product.
Embodiment 7：The synthesis of compound 3
A1 in embodiment 4 is replaced with into A4, B2-1 replaces with B2-2, other steps are same as Example 4, changed Compound 3.
Mass spectrum m/z：644.75 (calculated values：644.80).Theoretical elemental content (%) C47H36N2O：C,87.55；H,5.63； N,4.34；O,2.48.Actual measurement constituent content (%)：C,87.52；H,5.63；N,4.34；O,2.48.The above results confirm to obtain Product is target product.
Embodiment 8：The synthesis of compound 4
A1 in embodiment 4 is replaced with into A5, B2-1 replaces with B2-2, other steps are same as Example 4, changed Compound 4.
Mass spectrum m/z：680.85 (calculated values：680.83).Theoretical elemental content (%) C50H36N2O：C,88.21；H,5.33； N,4.11；O,2.35.Actual measurement constituent content (%)：C,88.22；H,5.33；N,4.11；O,2.35.The above results confirm to obtain Product is target product.
Embodiment 9：The synthesis of compound 5
A1 in embodiment 4 is replaced with into A6, B2-1 replaces with B2-2, other steps are same as Example 4, changed Compound 5.
Mass spectrum m/z：640.78 (calculated values：640.77).Theoretical elemental content (%) C47H32N2O：C,88.10；H,5.03； N,4.37；O,2.50.Actual measurement constituent content (%)：C,88.12；H,5.03；N,4.37；O,2.50.The above results confirm to obtain Product is target product.
Embodiment 10：The synthesis of compound 6
A1 in embodiment 4 is replaced with into A3, B2-1 replaces with B1-1, other steps are same as Example 4, changed Compound 6.
Mass spectrum m/z：580.78 (calculated values：580.74).Theoretical elemental content (%) C41H28N2S：C,84.80；H,4.86； N,4.82；S,5.52.Actual measurement constituent content (%)：C,84.82；H,4.86；N,4.82；S,5.53.The above results confirm to obtain Product is target product.
Embodiment 11：The synthesis of compound 7
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B1-1, other steps are same as Example 4, changed Compound 7.
Mass spectrum m/z：620.84 (calculated values：620.80).Theoretical elemental content (%) C44H32N2S：C,85.13；H,5.20； N,4.51；S,5.17.Actual measurement constituent content (%)：C,85.15；H,5.21；N,4.52；S,5.17.The above results confirm to obtain Product is target product.
Embodiment 12：The synthesis of compound 8
A1 in embodiment 4 is replaced with into A4, B2-1 replaces with B1-1, other steps are same as Example 4, changed Compound 8.
Mass spectrum m/z：660.84 (calculated values：660.87).Theoretical elemental content (%) C47H36N2S：C,85.42；H,5.49； N,4.24；S,4.85.Actual measurement constituent content (%)：C,85.39；H,5.51；N,4.22；S,4.87.The above results confirm to obtain Product is target product.
Embodiment 13：The synthesis of compound 9
A1 in embodiment 4 is replaced with into A5, B2-1 replaces with B1-1, other steps are same as Example 4, changed Compound 9.
Mass spectrum m/z：696.94 (calculated values：696.90).Theoretical elemental content (%) C50H36N2S：C,86.17；H,5.21； N,4.02；S,4.60.Actual measurement constituent content (%)：C,86.19；H,5.21；N,4.02；S,4.60.The above results confirm to obtain Product is target product.
Embodiment 14：The synthesis of compound 10
A1 in embodiment 4 is replaced with into A6, B2-1 replaces with B1-1, other steps are same as Example 4, changed Compound 10.
Mass spectrum m/z：656.88 (calculated values：656.84).Theoretical elemental content (%) C47H32N2S：C,85.94；H,4.91； N,4.26；S,4.88.Actual measurement constituent content (%)：C,85.99；H,4.91；N,4.25；S,4.89.The above results confirm to obtain Product is target product.
Embodiment 15：The synthesis of compound 11
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B2-3, other steps are same as Example 4, changed Compound 11.
Mass spectrum m/z：604.78 (calculated values：604.74).Theoretical elemental content (%) C44H32N2O：C,87.39；H,5.33； N,4.63；O,2.65.Actual measurement constituent content (%)：C,87.42；H,5.31；N,4.65；O,2.65.The above results confirm to obtain Product is target product.
Embodiment 16：The synthesis of compound 12
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B2-4, other steps are same as Example 4, changed Compound 12.
Mass spectrum m/z：604.77 (calculated values：604.74).Theoretical elemental content (%) C44H32N2O：C,87.39；H,5.33； N,4.63；O,2.65.Actual measurement constituent content (%)：C,87.41；H,5.32；N,4.65；O,2.65.The above results confirm to obtain Product is target product.
Embodiment 17：The synthesis of compound 13
A1 in embodiment 4 is replaced with into A2, other steps are same as Example 4, obtain compound 13.
Mass spectrum m/z：604.75 (calculated values：604.74).Theoretical elemental content (%) C44H32N2O：C,87.39；H,5.33； N,4.63；O,2.65.Actual measurement constituent content (%)：C,87.40；H,5.33；N,4.65；O,2.65.The above results confirm to obtain Product is target product.
Embodiment 18：The synthesis of compound 14
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B1-4, other steps are same as Example 4, changed Compound 14.
Mass spectrum m/z：620.83 (calculated values：620.80).Theoretical elemental content (%) C44H32N2S：C,85.13；H,5.20； N,4.51；S,5.17.Actual measurement constituent content (%)：C,85.14；H,5.21；N,4.51；S,5.19.The above results confirm to obtain Product is target product.
Embodiment 19：The synthesis of compound 15
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B1-2, other steps are same as Example 4, changed Compound 15.
Mass spectrum m/z：620.83 (calculated values：620.80).Theoretical elemental content (%) C44H32N2S：C,85.13；H,5.20； N,4.51；S,5.17.Actual measurement constituent content (%)：C,85.14；H,5.21；N,4.51；S,5.19.The above results confirm to obtain Product is target product.
Embodiment 20：The synthesis of compound 16
A1 in embodiment 4 is replaced with into A2, B2-1 replaces with B1-3, other steps are same as Example 4, changed Compound 16.
Mass spectrum m/z：620.82 (calculated values：620.80).Theoretical elemental content (%) C44H32N2S：C,85.13；H,5.20； N,4.51；S,5.17.Actual measurement constituent content (%)：C,85.15；H,5.20；N,4.51；S,5.18.The above results confirm to obtain Product is target product.
Embodiment 21：The synthesis of compound 17
B2-1 in embodiment 4 is replaced with into B2-3, other steps are same as Example 4, obtain compound 17.
Mass spectrum m/z：653.73 (calculated values：653.77).Theoretical elemental content (%) C47H31N3O：C,86.35；H,4.78； N,6.43；O,2.45.Actual measurement constituent content (%)：C,86.31；H,4.79；N,6.45；O,2.45.The above results confirm to obtain Product is target product.
Embodiment 22：The synthesis of compound 18
B2-1 in embodiment 4 is replaced with into B2-2, other steps are same as Example 4, obtain compound 18.
Mass spectrum m/z：653.76 (calculated values：653.77).Theoretical elemental content (%) C47H31N3O：C,86.35；H,4.78； N,6.43；O,2.45.Actual measurement constituent content (%)：C,86.33；H,4.79；N,6.45；O,2.45.The above results confirm to obtain Product is target product.
Embodiment 23：The synthesis of compound 20
B2-1 in embodiment 4 is replaced with into B1-4, other steps are same as Example 4, obtain compound 20.
Mass spectrum m/z：669.87 (calculated values：669.83).Theoretical elemental content (%) C47H31N3S：C,84.28；H,4.66； N,6.27；S,4.79.Actual measurement constituent content (%)：C,84.30；H,4.65；N,6.26；S,4.79.The above results confirm to obtain Product is target product.
Embodiment 24：The synthesis of compound 21
B2-1 in embodiment 4 is replaced with into B1-1, other steps are same as Example 4, obtain compound 21.
Mass spectrum m/z：669.87 (calculated values：669.83).Theoretical elemental content (%) C47H31N3S：C,84.28；H,4.66； N,6.27；S,4.79.Actual measurement constituent content (%)：C,84.30；H,4.65；N,6.26；S,4.79.The above results confirm to obtain Product is target product.
Embodiment 25：The synthesis of compound 22
B2-1 in embodiment 4 is replaced with into B1-3, other steps are same as Example 4, obtain compound 22.
Mass spectrum m/z：669.80 (calculated values：669.83).Theoretical elemental content (%) C47H31N3S：C,84.28；H,4.66； N,6.27；S,4.79.Actual measurement constituent content (%)：C,84.26；H,4.65；N,6.28；S,4.79.The above results confirm to obtain Product is target product.
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 10 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light, Then processed 8 minutes with plasma.The ito substrate after treatment is then put into evaporated device.One layer of NPB of 35nm is deposited with first As hole transmission layer, followed by luminescent layer evaporation, mixing evaporation, BH1, and 5% BD1, then evaporation 30nm Alq3 is then deposited with 1nmLiF again as electron transfer layer, then the metal Al of evaporation 150nm.
Application Example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 10 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light, Then processed 8 minutes with plasma.The ito substrate after treatment is then put into evaporated device.One layer of change of 35nm is deposited with first Compound 19 as hole transmission layer, followed by luminescent layer evaporation, mixing evaporation, BH1, and 5% BD1, subsequent evaporation The Alq3 of 30nm is then deposited with 1nmLiF again as electron transfer layer, then the metal Al of evaporation 150nm.
Application Example 2
Change the compound 19 in Application Example 1 into compound 2
Application Example 3
Change the compound 19 in Application Example 1 into compound 7
Wherein：
OLED is produced as follows：
Contrast Application Example：ITO/NPB/BH1：BD1/Alq3/LiF/Al；
Application Example 1：ITO/ compounds 19/BH1：BD1/Alq3/LiF/Al；
Application Example 2：ITO/ compounds 2/BH1：BD1)/Alq3/LiF/Al；
Application Example 3：ITO/ compounds 7/BH1：BD1)/Alq3/LiF/Al；
Under 1000nits, Nan dian Yao device result is as follows：
Device Cd/A DriverVoltage Life-span (T80)
Contrast Application Example 6cd/A 4.7V 35hours
Application Example 1 7.2cd/A 4.5V 87hours
Application Example 2 7.9cd/A 4.5V 145hours
Application Example 3 7cd/A 4.6V 123hours
As can be seen that the organic electroluminescence device prepared using the compound containing pyridine groups that the present invention is provided, tool There is luminous efficiency higher, luminous efficiency is up to 7.0~7.9cd/A, and luminosity is high, be a kind of excellent OLED materials Material.
Obviously, the explanation of above example is only intended to help and understands the method for the present invention and its core concept.Should refer to Go out, for the those of ordinary skill of the technical field, under the premise without departing from the principles of the invention, can also be to this hair Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (10)

1. a kind of compound containing pyridine groups, shown in its general structure such as formula (I)：
Wherein, X is S or O；R1、R2It is independent selected from substituted or unsubstituted aromatic hydrocarbyl or substituted or unsubstituted fragrance Race's heterocyclic radical.
2. a kind of compound containing pyridine groups according to claim 1, it is characterised in that the R1、R2Independent is selected from The aromatic heterocycle of the aromatic hydrocarbyl of substituted or unsubstituted C6~C50 or substituted or unsubstituted C4~C50.
3. a kind of compound containing pyridine groups according to claim 1, it is characterised in that the R1、R2Independent is selected from The aromatic heterocycle of the aromatic hydrocarbyl of substituted or unsubstituted C6~C30 or substituted or unsubstituted C4~C30.
4. a kind of compound containing pyridine groups according to claim 1, it is characterised in that the aromatic hydrocarbyl is selected from Phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylene base, fluoranthene base or benzo phenanthryl.
5. a kind of compound containing pyridine groups according to claim 1, it is characterised in that in the aromatic heterocycle Hetero atom be nitrogen.
6. a kind of compound containing pyridine groups according to claim 1, it is characterised in that the aromatic heterocycle choosing From pyridine radicals or carbazyl.
7. a kind of compound containing pyridine groups according to claim 1, it is characterised in that such as any one institute of formula 1~22 Show：
8. a kind of organic luminescent device, it is characterised in that including the change containing pyridine groups described in any one of claim 1~7 Compound.
9. organic luminescent device according to claim 8, it is characterised in that including first electrode, second electrode and setting Organic matter layer between the first electrode and second electrode；The organic matter layer is included described in any one of claim 1~7 The compound containing pyridine groups.
10. organic luminescent device according to claim 9, it is characterised in that the organic matter layer includes hole transport Layer, the compound containing pyridine groups is used as the constituent material of hole transmission layer.
CN201611028176.3A 2016-11-22 2016-11-22 A kind of compound containing pyridine groups and the organic luminescent device using the compound Pending CN106749198A (en)

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