CN106749330A - A kind of Hete rocyclic derivatives and the organic luminescent device using the Hete rocyclic derivatives - Google Patents
A kind of Hete rocyclic derivatives and the organic luminescent device using the Hete rocyclic derivatives Download PDFInfo
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- CN106749330A CN106749330A CN201611242392.8A CN201611242392A CN106749330A CN 106749330 A CN106749330 A CN 106749330A CN 201611242392 A CN201611242392 A CN 201611242392A CN 106749330 A CN106749330 A CN 106749330A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- 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
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- H10K2102/301—Details of OLEDs
Abstract
The present invention provides a kind of Hete rocyclic derivatives and the organic luminescent device using the Hete rocyclic derivatives, belongs to organic photoelectrical material technical field.Hete rocyclic derivatives of the present invention pass through Molecular Design, have selected spiro-compound, effective molecular configuration is caused to distort by volution, so as to reduce the spatial orientation of material after film forming, its performance in the devices is further improved, by changing the group of connection, can further improve its physical characteristic, the Hete rocyclic derivatives for obtaining is had the advantages that good big band gap, heat endurance, filming performance and anti-crystallization are good, and then improve the characteristics of luminescence of organic luminescent device.The Hete rocyclic derivatives provided using the present invention prepare organic luminescent device, the larger luminous efficiency that improve device and device lifetime, are luminous organic materials of good performance.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of Hete rocyclic derivatives and use the heterocyclic derivatives
The organic luminescent device of thing.
Background technology
Organic electroluminescent refers to the phenomenon that organic material lights under electric current or electric field excitation.Organic electroluminescent
Device has the advantages that self-luminous, visual angle are wide, driving voltage is low, lightweight, has huge application in display and lighting field
Prospect.
According to the difference of the organic material for being used, the device that people will be generally made using organic molecule for luminescent material
Part is referred to as organic electroluminescence device, abbreviation OLED.The research of organic electroluminescent phenomenon starts from the sixties in 20th century.1963
Pope of New York Univ USA etc. observes electro optical phenomenon on anthracene single crystal first, but because monocrystalline thickness is excessive, drives
Voltage is up to 400V, lacks practical value.It is follow-up again studies have reported that a series of main body organic materials containing conjugated structure
Electro optical phenomenon, due to device technology problem, luminous efficiency is undesirable.Until the report such as Tang of Kodak Company in 1987
Road is made high-quality thin film using 8-hydroxyquinoline aluminium with the aromatic diamine with hole transport performance, and is made organic hair
Optical device, this material has the excellent properties such as high-luminous-efficiency, high brightness, and this research indicates organic electroluminescent research
Into practical stage.Nineteen ninety Friend etc. reports high molecule electroluminescent phenomenon under low-voltage, has opened macromolecule electricity
The frontier of electroluminescent material research.Forrest of Princeton university in 1998 et al. is found that electrophosphorescence
Phenomenon, breaches theoretical limit of the electroluminescent organic material luminous quantum efficiency less than 25% so that organic electroluminescence
Part research enters new period.
Organic electroluminescence device is generally over the transparent substrate according to anode/hole injection layer/hole transmission layer/luminous
The order of layer/electron transfer layer/electron injecting layer/negative electrode prepares sandwich construction.Wherein hole mobile material is mainly used in improving
Electron hole pair combined efficiency, requirement to material is high except hole transport rate, outside electric transmission rate is low, also requires that its can band
Gap and ionization potential, electron affinity energy have appropriate numerical value, so as to effectively reduce the hole injection barrier to luminescent layer, improve hair
Light efficiency.Most of preferable hole mobile material of report is aromatic triamine class compound at present, but common aromatic series
There is recrystallization behavior after triamine compound film forming, cause device performance to decay.The present invention be namely based on the application of this respect and
It is simultaneously realized application in the devices for the new material system of design synthesis.
The content of the invention
In view of this, it is an object of the invention to provide a kind of Hete rocyclic derivatives and the organic hair using the Hete rocyclic derivatives
Optical device, the present invention is synthesized by MOLECULE DESIGN has big band gap, good heat endurance, filming performance and anti-crystallization good
Novel organic compound, and organic electroluminescence device is prepared as hole transport layer material, the hair of device can be significantly improved
Light characteristic.
Present invention firstly provides a kind of Hete rocyclic derivatives, with the structural formula as described in formula (I)：
Wherein, Ar1、Ar2It is each independently selected from the aromatic hydrocarbyl of substituted or unsubstituted C6-C50.
Preferably, the Ar1、Ar2It is each independently selected from the aromatic hydrocarbyl of substituted or unsubstituted C6-C20.
Preferably, the Ar2Substituted or unsubstituted condensed ring is formed with the five-ring heterocycles at place.
Preferably, the Ar1、Ar2It is each independently selected from any one in following structure：
Wherein, Ra is hydrogen, alkyl, halogen or cyano group.
Preferably, the Ar1、Ar2It is each independently selected from phenyl, xenyl, naphthyl or anthryl.
The present invention also provides a kind of organic luminescent device, and the organic luminescent device includes Hete rocyclic derivatives of the present invention.
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 Hete rocyclic derivatives of the present invention.
Beneficial effects of the present invention：
Hete rocyclic derivatives of the present invention have selected spiro-compound by Molecular Design, caused by volution
The molecular configuration distortion of effect, so as to reduce the spatial orientation of material after film forming, further improves its performance in the devices, passes through
Change connection group, can further improve its physical characteristic, so as to get Hete rocyclic derivatives there is big band gap, heat endurance
Good, filming performance and the good advantage of anti-crystallization energy, and then improve the characteristics of luminescence of organic luminescent device.There is provided using the present invention
Hete rocyclic derivatives prepare organic luminescent device, the larger luminous efficiency that improve device and device lifetime, be functional
Luminous organic 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.
Present invention firstly provides a kind of Hete rocyclic derivatives, with the structural formula as described in formula (I)：
Wherein, Ar1、Ar2It is each independently selected from the aromatic hydrocarbyl of substituted or unsubstituted C6-C50.
According to the present invention, the aromatic hydrocarbyl refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, to be left
The general name of univalent perssad, it can be monocyclic aryl or fused ring aryl, for example, may be selected from phenyl, xenyl, terphenyl, naphthalene
Base, anthryl, phenanthryl or pyrenyl etc., but not limited to this.
According to the present invention, in the substituted aromatic hydrocarbyl, the substitution base preferably is selected from halogen, cyano group, C1-C10
One or more in the aromatic hydrocarbyl of alkyl or C6-C20, the more preferably alkyl of cyano group or C1-C4, the substitution base
Number is preferably 0~3.
According to the present invention, preferably described Ar1、Ar2It is each independently selected from the aromatic hydrocarbon of substituted or unsubstituted C6-C20
Base, further preferably described Ar2Substituted or unsubstituted condensed ring is formed with the five-ring heterocycles at place, further preferably described Ar1、Ar2Selected from such as
Any one in lower structure：
Wherein, Ra is hydrogen, alkyl, halogen or cyano group.Connecting key is represented, Ra- represents fragrance where being connected to
The optional position of ring.Ra is preferably hydrogen, C1~C4 alkyl, halogen or cyano group, for example, may be selected from hydrogen, methyl, ethyl, propyl group, different
Propyl group, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group, F or cyano group, more preferably hydrogen, methyl or cyano group.The number of Ra is preferably
0~3.
As an example, the Hete rocyclic derivatives, are not particularly limited, and are preferably as follows shown：
Some specific structure types of Hete rocyclic derivatives of the present invention are enumerated above, but heterocycle of the present invention spreads out
Biology is not limited to these listed chemical constitutions, every based on structure shown in formula (I), Ar1、Ar2For as defined above
Group should all be included.
Hete rocyclic derivatives of the present invention have selected spiro-compound by Molecular Design, caused by volution
The molecular configuration distortion of effect, so as to reduce the spatial orientation of material after film forming, further improves its performance in the devices, passes through
Change connection group, can further improve its physical characteristic, so as to get Hete rocyclic derivatives there is big band gap, heat endurance
Good, filming performance and the good advantage of anti-crystallization energy, and then improve the characteristics of luminescence of organic luminescent device.
The preparation method of Hete rocyclic derivatives shown in formula (I) of the present invention, first, imdazole derivatives shown in formula (II) are to rise
Begin, the compound described in formula (III) is obtained after first benzyl protection, then through the addition of lithiumation and derivative of piperidone (IV), hydrogenation is de-
Intermediate (V) is obtained after benzyl protection, then obtains miscellaneous shown in the formula (I) of the present invention of imidazo spirane structure by alkylation
Ring derivatives.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, can
Think commercially available prod or prepared using preparation method well-known to those skilled in the art.Wherein, the Ar1、Ar2Choosing
Select same as above, will not be repeated here.
The present invention also provides a kind of organic luminescent device, including the Hete rocyclic derivatives.The organic luminescent device is this
Organic luminescent device known to art personnel, using the preparation method of traditional organic luminescent device, the present invention
The method film forming of middle use vacuum evaporation.Organic luminescent device of the present invention preferably includes first electrode, second electrode and sets
The organic matter layer being placed between the first electrode and second electrode, contains Hete rocyclic derivatives of the present invention in the organic matter layer.
The organic matter layer preferably includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics and passes
At least one of which in defeated layer and electron injecting layer.It is preferred that the Hete rocyclic derivatives are used as hole transport layer material.
Organic luminescent device of the present invention can be used for the application fields such as flat-panel monitor, lighting source, direction board, signal lamp.
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 compound TM-1
1st, in dry there-necked flask, addition 500ml dry DMFs, then it is dividedly in some parts 60% sodium hydride 4.4g, cryosel
Bath is cooled to 0 DEG C.After being sufficiently stirred for 5 minutes, the DMF solution of 6g benzimidazoles is added dropwise at low temperature, is warmed naturally to after dropwise addition
Room temperature, and it is sufficiently stirred for half an hour.0 DEG C is cooled to ice salt bath again, then is slowly added dropwise cylite 15g, after adding, whole body
After system is warmed to room temperature and is sufficiently stirred for 4 hours naturally again, reaction solution is slowly poured into 1500 milliliters of frozen water in stirring.
It is extracted with ethyl acetate three times, merges organic layer respectively with twice of substantial amounts of distilled water and salt water washing, anhydrous sodium sulfate drying.
It is concentrated under reduced pressure, obtain pale yellowish oil compound.
2nd, nitrogen protection under, by step 1 product 5g add 500ml anhydrous tetrahydro furans in, dry ice-propanone bath be cooled to-
78 DEG C, the hexane solution 30ml of n-BuLi is added dropwise, -78 DEG C is maintained at after dripping off and is stirred 1 hour.By N Phenylpiperidine ketone 11g
It is dissolved in 250 milliliters of anhydrous tetrahydro furans, is slowly dropped to above-mentioned reaction solution, reaction 3 hours is continued at -78 DEG C after dripping off.Instead
After answering completely, dry ice-propanone bath is removed, after being warming up to -10 DEG C, reaction is quenched with 200 milliliters of saturated aqueous ammonium chlorides, there is solid
Body precipitation generation.After organic solvent is concentrated under reduced pressure, solids of sedimentation is filtered and collected.Solids of sedimentation is washed with distilled water and ether respectively
Wash twice, dry compound as white solid.Compound 5g, methyl alcohol 500mL and 10% palladium carbon 5g are added separately to hydrogenation
In bottle, in reaction 4 hours under room temperature 50psi.After reaction terminates, palladium carbon, methyl alcohol washing filter cake two are fallen with diatomite careful filtration
After secondary, merge organic layer and be concentrated under reduced pressure, obtain compound as white solid.
3rd, step 2 product 5g, dry DMF 60ml are separately added into dry there-necked flask, after ice salt bath is cooled to 0 DEG C, point
Criticize the sodium hydride 0.5g for adding 60%.Remove ice salt bath, be warmed up to naturally room temperature and stir 30 minutes after, 0 DEG C is cooled to again.
Take 7g Bromofumes to be dissolved in 10mlDMF, be added drop-wise in above-mentioned reactant.After dripping, ice salt bath is removed, room is warmed up to naturally
Temperature is simultaneously stirred overnight.After reaction terminates, reaction solution is poured into saturated ammonium chloride solution (50mL), aqueous layer with ethyl acetate extraction
Three times.Merge organic layer, washed with a large amount of distillation water washings, salt, anhydrous sodium sulfate drying.After filtering, mesh is concentrated under reduced pressure to give
Mark compound.Yield 78%.Mass spectrum m/z：319.22.Actual measurement constituent content (%) C20H21N3O：C,75.23；H,6.64；N,
13.15；O,5.00；The above results confirm that it is target compound TM-1 to obtain product.
Embodiment 2：The synthesis of compound TM-2
1st, experimental procedure is similar with the step 1 of embodiment 1, using the benzimidazole in 2,3- naphtho-s imidazoles substitution embodiment 1.
2 is similar to the step of embodiment 1.
3 is similar to the step of embodiment 1.Yield 72%.Mass spectrum m/z：369.14.Actual measurement constituent content (%) C24H23N3O：
C,78.00；H,6.26；N,11.38；O,4.33；The above results confirm that it is target compound TM-2 to obtain product.
Embodiment 3：The synthesis of compound TM-3
1st, the step 1 of experimental procedure embodiment 1 is similar to, using the benzimidazole in 1,2- naphtho-s imidazoles substitution embodiment 1.
2 is similar to the step of embodiment 1.
3 is similar to the step of embodiment 1.Yield 68%.Mass spectrum m/z：369.15.Actual measurement constituent content (%) C24H23N3O：
C,78.00；H,6.25；N,11.37；O,4.34；The above results confirm that it is target compound TM-3 to obtain product.
Embodiment 4：The synthesis of compound TM-4
1st, the step 1 of experimental procedure embodiment 1 is similar to, using the benzimidazole in 2,3- naphtho-s imidazoles substitution embodiment 1.
2 is similar to the step of embodiment 1.Using the N- Phenylpiperidine ketone in N- naphthyl piperidones alternate embodiment 1.
3 is similar to the step of embodiment 1.Yield 66%.Mass spectrum m/z：419.14.Actual measurement constituent content (%) C28H25N3O：
C,80.14；H,6.00；N,10.03；O,3.80；The above results confirm that it is target compound TM-4 to obtain product.
Embodiment 5：The preparation of luminescent device
Selection ito glass is anode, in being dried as vacuum chamber after ultrasonic cleaning, is evacuated to 5 × 10-5Pa, above-mentioned
Spin coating PEDOT in anode grid substrate:PSS layer is used as hole injection layer, thickness 30nm.Compound prepared by the vacuum evaporation present invention
Used as hole transmission layer, evaporation rate is 0.15nm/s to TM-1, and evaporation thickness is 20nm.The vacuum evaporation Ir on hole transmission layer
(mppy)3It is object luminescent layer, by the use of Bepp2 as main body luminescent layer, guest materials doping is 6%, and thickness degree is 50nm.
Used as electric transmission, evaporation rate is 0.01nm/s to vacuum evaporation Bphen on luminescent layer, and evaporation thickness is 20nm.In electronics
Used as negative electrode, thickness is respectively 1.5nm and 200nm for LiF and Al layer of vacuum evaporation in transport layer.Measure the internal quantum of the device
Efficiency and device lifetime.Respectively with the TM-2 of present invention synthesis, TM-3, TM-4 compound prepare luminescent device as stated above,
And device is prepared as hole transmission layer as reference compound by the use of 3DTAPBP, each device luminescent properties testing result is shown in Table
1。
Table 1.
| Compound | External quantum efficiency | Device lifetime (hour) |
| TM-1 | 41.2% | 12000 |
| TM-2 | 40.5% | 12000 |
| TM-3 | 42.6% | 12000 |
| TM-4 | 44.1% | 12000 |
| 3DTAPBP | 33.2% | 3500 |
Result above shows, Hete rocyclic derivatives of the invention as hole mobile material in electroluminescent device should
It is luminous organic material of good performance with, the larger luminous efficiency that improve device and device lifetime.
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 (7)
1. a kind of Hete rocyclic derivatives, with the structural formula as described in formula (I)：
Wherein, Ar1、Ar2It is each independently selected from the aromatic hydrocarbyl of substituted or unsubstituted C6-C50.
2. Hete rocyclic derivatives according to claim 1, it is characterised in that the Ar1、Ar2Be each independently selected from substitution or
The aromatic hydrocarbyl of unsubstituted C6-C20.
3. Hete rocyclic derivatives according to claim 1, it is characterised in that the Ar2Five-ring heterocycles with place form substitution
Or unsubstituted condensed ring.
4. Hete rocyclic derivatives according to claim 1, it is characterised in that the Ar1、Ar2It is each independently selected from following knot
Any one in structure：
Wherein, Ra is hydrogen, alkyl, halogen or cyano group.
5. Hete rocyclic derivatives according to claim 1, it is characterised in that the Ar1、Ar2Be each independently selected from phenyl,
Xenyl, naphthyl or anthryl.
6. a kind of organic luminescent device, it is characterised in that the organic luminescent device is included described in any one of Claims 1 to 5
Hete rocyclic derivatives.
7. a kind of organic luminescent device according to claim 6, it is characterised in that the organic luminescent device includes first
Electrode, second electrode and the organic matter layer being arranged between the first electrode and second electrode；The organic matter layer includes power
Profit requires the Hete rocyclic derivatives described in 1~5 any one.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023154310A1 (en) * | 2022-02-08 | 2023-08-17 | Vertex Pharmaceuticals Incorporated | 2-methyl-4-phenylpiperidin-4-ol derivatives as inhibitors of apol1 and methods of using same |
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|---|---|---|---|---|
| WO2011140425A1 (en) * | 2010-05-06 | 2011-11-10 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| WO2013067248A1 (en) * | 2011-11-04 | 2013-05-10 | Vertex Pharmaceuticals Incorporated | Benzoxazines as modulators of ion channels |
| CN106008504A (en) * | 2011-02-02 | 2016-10-12 | 沃泰克斯药物股份有限公司 | Pyrrolopyrazine-spirocyclic piperidine amides as modulators of ion channels |
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2016
- 2016-12-29 CN CN201611242392.8A patent/CN106749330A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011140425A1 (en) * | 2010-05-06 | 2011-11-10 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| CN106008504A (en) * | 2011-02-02 | 2016-10-12 | 沃泰克斯药物股份有限公司 | Pyrrolopyrazine-spirocyclic piperidine amides as modulators of ion channels |
| WO2013067248A1 (en) * | 2011-11-04 | 2013-05-10 | Vertex Pharmaceuticals Incorporated | Benzoxazines as modulators of ion channels |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023154310A1 (en) * | 2022-02-08 | 2023-08-17 | Vertex Pharmaceuticals Incorporated | 2-methyl-4-phenylpiperidin-4-ol derivatives as inhibitors of apol1 and methods of using same |
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