CN110128416A - A kind of general formula compound and its application - Google Patents
A kind of general formula compound and its application Download PDFInfo
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- CN110128416A CN110128416A CN201810105112.1A CN201810105112A CN110128416A CN 110128416 A CN110128416 A CN 110128416A CN 201810105112 A CN201810105112 A CN 201810105112A CN 110128416 A CN110128416 A CN 110128416A
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Abstract
The invention discloses the general formula compounds of formula:Wherein: Z is selected from O, S or Se；L is selected from singly-bound, or is selected from C1‑C12Alkyl, C1‑C8Alkoxy, C5‑C30Substitution or unsubstituted arlydene, C3‑C30Substitution or unsubstituted heteroarylene；Ar1Selected from following formula (1) or formula (2):Ar2Selected from following formula (3):Wherein: X1~X8It is independently selected from CR3Or N, and X1~X4In at least one be N, X5~X8In at least one be N, R3Selected from hydrogen, C1‑C12Alkyl, C6‑C30Aryl or fused ring aryl, C3‑C30Heterocyclic aryl or fused ring heteroaryl；R1~R2It is respectively and independently selected from hydrogen, C1‑C12Alkyl, C6‑C30Substitution or unsubstituted aryl or fused ring aryl, C3‑C30Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl.The present invention protects the organic electroluminescence device using above-mentioned general formula compound simultaneously.When the compound of the present invention is as material of main part in OLED luminescent layer, excellent device performance and stability are shown.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, a kind of novel general formula compound is in particulard relate to and using should
The organic electroluminescence device of class general formula compound.
Background technique
It is aobvious that Organic Light Emitting Diode (Organic Light-Emitting Diodes, OLEDs) is also known as organic electric laser
Show, organic luminous semiconductor.Deng Qingyun (Ching W.Tang) is taught by Chinese descendant in America to find in the lab in 1979.
OLED display technology has many advantages, such as that self-luminous, wide viewing angle, high contrast, power consumption be low, fast response time.But as high-end
Display screen, also can be more expensive than LCD TV in price.Wherein, OLED itself has using organic film, and voltage is imposed on it
The inherent characteristic to shine on composed device, so developing the research weight that suitable organic film material is always OLED industry
Point is conducive to accelerate industrialization process of the OLED in display technology.
Whether on the market display full color is to examine display competitive important symbol, wherein phosphor material
It is most commonly used for one of organic material of full color display.Professional standard for this display needs to be suitable for hair
Penetrate the higher pixel of excitation purity.Specifically, these standards need the red, green and blue color pixel being saturated.This field can be used
In known CIE coordinate measure colour.
As described herein, in full color display, wherein an example of green phosphorescent material is three [2- phenylpyridines-
C2, N] and iridium (III), it is expressed as Ir (ppy)3.Phosphor material since its lifetime of excited state is longer and T-T annihilation,
Self can occurs in higher molecular concentration to be quenched, therefore generally phosphor material is entrained in material of main part, to increase phosphorus
Optical molecule spacing.From this, the selection of material of main part for improve organic electroluminescence device performance have it is vital
Effect.Since most phosphor materials generally only have unidirectional carrier transport ability, it is multiple in luminescent layer that this can reduce carrier
The balance of conjunction, therefore, developing the material of main part with good carrier transmission performance is one of the main task in industry.
As used herein, and as persons skilled in the art understand, T-T annihilation is two and is in
Interaction (usually mutually collision) can often occur for the atom or molecular entity of triplet so that one of atom or
Molecular entity is in excitation singlet, another is then in base singlet.In general, but be not it is inevitable, can then generate delay it is glimmering
Light.
Summary of the invention
The present invention provides a kind of general formula compound as shown in formula (1):
Wherein: Z is selected from O, S or Se；
L is selected from singly-bound, or is selected from C1-C12Alkyl, C1-C8Alkoxy, C5-C30Substitution or unsubstituted sub- virtue
Base, C3-C30Substitution or unsubstituted heteroarylene；
Ar1Selected from following formula (1) or formula (2):
Ar2Selected from following formula (3):
In above-mentioned formula (1), (2) and (3):
X1~X8It is independently selected from CR3Or N, and X1~X4In at least one be N, X5~X8In at least one be
N, R3Selected from hydrogen, C1-C12Alkyl, C6-C30Aryl or fused ring aryl, C3-C30Heterocyclic aryl or fused ring heteroaryl；
R1~R2It is respectively and independently selected from hydrogen, C1-C12Alkyl, C6-C30Substitution or unsubstituted aryl or condensed ring virtue
Base, C3-C30Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
Above-mentioned L and R1~R2On substituent group be respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, alkenyl, C1
~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30Monocycle heteroaryl
Hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
Further, above-mentioned formula (I) preferably is selected from following formula (II) or formula (III):
In formula (II) and formula (III), Z is selected from O, S or Se；L is selected from singly-bound, or is selected from C5-C15Substitution or unsubstituted
Arlydene, C3-C15Substitution or unsubstituted heteroarylene.
X1~X8Definition with the definition in formula (1) and formula (2), and work as X1~X8It is independently selected from CR3When, R3Choosing
From hydrogen, C1-C8Alkyl, C6-C15Aryl or fused ring aryl, C3-C15Heterocyclic aryl or fused ring heteroaryl.
R1And R2It is respectively and independently selected from hydrogen, C1-C8Alkyl, C6-C15Substitution or unsubstituted aryl or condensed ring virtue
Base, C3-C15Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl.
The L and R1And R2On substituent group be respectively and independently selected from halogen, C1~C6Alkyl or cycloalkyl, alkenyl, C1
~C6Alkoxy or thio alkoxy group, C6~C10Mononuclear aromatics or condensed-nuclei aromatics group, C3~C10Monocycle heteroaryl
Hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
Further, in the general formula compound of above-mentioned structure, the X1~X8It is independently selected from CR3Or N,
And preferably X1~X4In at least there are two be N, preferably X5~X8In at least there are two be N.
Further, above-mentioned formula (II) and formula (III) are respectively following formula (IV) and formula (V):
Wherein, Z, L, X1~X8And R1And R2Definition with the definition in formula (II) and formula (III).
Further, in above-mentioned Formula, L is preferably singly-bound, or preferably with the group of flowering structure:
Further, in above-mentioned Formula, R1~R2Independently be preferably hydrogen, phenyl, xenyl, naphthalene,
Fluorenyl, Spirofluorene-based, pyridyl group, bipyridyl, pyrimidine radicals, pyrrole radicals, phenylpyridyl, pyrazinyl, quinolyl carbazyl, 9- benzene
Base carbazyl, 9- naphthyl carbazole and carbazyl.
Further, in general formula compound of the present invention preferred following 1-44 structural compounds:
General formula compound of the invention can be applied in organic electroluminescence device, organic solar batteries, organic film
Transistor or organic sensor.It is preferred that can apply in the luminescent layer of organic electroluminescence device as material of main part.
The present invention also provides a kind of organic electroluminescence device, which includes first electrode, second electrode and insertion
One or more layers organic layer between the first electrode and second electrode, which is characterized in that include at least in the organic layer
The compound that one kind is indicated by general formula (I):
Wherein: Z is selected from O, S or Se；L is selected from singly-bound, or is selected from C1-C12Alkyl, C1-C8Alkoxy, C5-C30Take
Generation or unsubstituted arlydene, C3-C30Substitution or unsubstituted heteroarylene；
Ar1Selected from following formula (1) or formula (2):
Ar2Selected from following formula (3):
In above-mentioned formula (1), (2) and (3):
X1~X8It is independently selected from CR3Or N, and X1~X4In at least one be N, X5~X8In at least one be
N, R3Selected from hydrogen, C1-C12Alkyl, C6-C30Aryl or fused ring aryl, C3-C30Heterocyclic aryl or fused ring heteroaryl；
R1~R2It is respectively and independently selected from hydrogen, C1-C12Alkyl, C6-C30Substitution or unsubstituted aryl or condensed ring virtue
Base, C3-C30Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
Above-mentioned L and R1~R2On substituent group be respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, alkenyl, C1
~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30Monocycle heteroaryl
Hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
Further, above-mentioned formula (I) preferably is selected from following formula (II) or formula (III):
In formula (II) and formula (III), Z is selected from O, S or Se；L is selected from singly-bound, or is selected from C5-C15Substitution or unsubstituted
Arlydene, C3-C15Substitution or unsubstituted heteroarylene.
X1~X8Definition with the definition in formula (1) and formula (2), and work as X1~X8It is independently selected from CR3When, R3Choosing
From hydrogen, C1-C8Alkyl, C6-C15Aryl or fused ring aryl, C3-C15Heterocyclic aryl or fused ring heteroaryl.
R1And R2It is respectively and independently selected from hydrogen, C1-C8Alkyl, C6-C15Substitution or unsubstituted aryl or condensed ring virtue
Base, C3-C15Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl.
The L and R1And R2On substituent group be respectively and independently selected from halogen, C1~C6Alkyl or cycloalkyl, alkenyl, C1
~C6Alkoxy or thio alkoxy group, C6~C10Mononuclear aromatics or condensed-nuclei aromatics group, C3~C10Monocycle heteroaryl
Hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
Further, in the general formula compound of above-mentioned structure, the X1~X8It is independently selected from CR3Or N,
And preferably X1~X4In at least there are two be N, preferably X5~X8In at least there are two be N.
Further, above-mentioned formula (II) and formula (III) are respectively following formula (IV) and formula (V):
Wherein, Z, L, X1~X8And R1And R2Definition with the definition in formula (II) and formula (III).
Further, in above-mentioned Formula, L is preferably singly-bound, or preferably with the group of flowering structure:
Further, in above-mentioned Formula, R1~R2Independently be preferably hydrogen, phenyl, xenyl, naphthalene,
Fluorenyl, Spirofluorene-based, pyridyl group, bipyridyl, pyrimidine radicals, pyrrole radicals, phenylpyridyl, pyrazinyl, quinolyl carbazyl, 9- benzene
Base carbazyl, 9- naphthyl carbazole and carbazyl.
The novel general formula compound that the present invention designs, with this kind of stable rigidity knot of dibenzothiophenes (or furans or selenophen)
Structure is the basis of parent nucleus, and then designs the heteroaromatic group Ar containing N atom in connection1, bridged group L and contain triazine knot
The group Ar of structure2。
Group containing triazine structure is a good electron transporting groups, and triazine group and dibenzothiophenes (or
Furans or selenophen) it is the group of high triplet energy level, therefore the electron cloud between compound molecule HOMO/LUMO can be improved
Degree of overlapping, so that the luminous efficiency of compound is improved, simultaneously as band caused by the raising of the electric charge transfer (ICT) of intramolecular
Gap reduces, and charge is easy to be spilled over in dopant, and luminous efficiency is caused to reduce；However the introducing of electron-withdrawing group makes entire molecule
's.The problem of HOMO energy level is dragged down, caused hence for ICT makes moderate progress.
Meanwhile in the general formula compound that designs of the present invention, in the heteroaromatic group Ar containing N atom1On, be in meta position or
It is separately connected dibenzothiophenes (or furans or selenophen) group and bridged group L in contraposition, designs the connection in meta or para position
On site, it can be ensured that appropriate distortion molecular structure is obtained, to ensure that compound has higher triplet, simultaneously
Bond dissociation energy can also be increased, reduce the risk that molecule decomposes in the devices.Further, pass through specific this hair of optimization design
Ar in bright compound1Group and L group, such as it regard the strong electron-withdrawing groups such as pyrimidine group, pyridine groups group as azepine aromatic hydrocarbons
The Ar of bridging1Group, it can be ensured that should class new compound have extraordinary intramolecular transmittability.
When the material of main part being used as novel general formula compound of the invention in the luminescent layer of organic electroluminescence device,
Can effectively in suppression device luminescent layer exciton diffusion, electronics not only can be improved in the luminescent layer of organic electroluminescence device
In mobility, moreover it is possible to improve the luminous efficiency of device, increase device stability, to obtain the organic electroluminescent of high life
Device.
In addition, being done by introducing different electron donating group and electron-withdrawing group on the mother nucleus structure of the compounds of this invention
Modification, can also obtain some bipolar host materials of good performance or electron-transporting type material of main part.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention；
Wherein 110 glass substrate is represented, 120 represent anode, and 130 represent hole injection layer, and 140 represent hole transmission layer,
150 represent luminescent layer, and 160 represent electron transfer layer, and 170 represent electron injecting layer, and 180 represent cathode.
Fig. 2 is the highest occupied molecular orbital (HOMO) of the compound of the present invention 2；
Fig. 3 is the lowest unoccupied molecular orbital (LUMO) of the compound of the present invention 2.
Specific embodiment
In order to make those skilled in the art more fully understand the present invention, With reference to embodiment to the present invention make into
One step is described in detail.
The compound for the synthetic method that do not mention in embodiment is all the raw produce being obtained through commercial channels.Implement
Example used in various chemicals for example petroleum ether, ethyl acetate, toluene, tetrahydrofuran, methylene chloride, potassium phosphate, butyl lithium,
Tris(dibenzylideneacetone) dipalladium, tetrakis triphenylphosphine palladium, dibenzothiophenes -4- boric acid；The bromo- 2- iodine pyridine of 5-；2 (3- bromobenzenes
Base) -4,6- diphenyl -1,3,5- triazine；2- dicyclohexyl phosphine -2', 6'- dimethoxy-biphenyl (Sphos)；It is bis- (pinacol combined)
Two boron tripotassium phosphates；Sodium carbonate；The basic chemical industries such as 1,4- dioxane raw material chemical products can be commercially available at home.
The analysis detection of intermediate and compound in the present invention uses ABSCIEX mass spectrograph (4000QTRAP) He Bulu
Gram Nuclear Magnetic Resonance (400M).
The present invention is more specifically described referring to the following examples, but the invention is not limited to these embodiments.
The compound that the general formula of the present invention (Ι) of hole transmission layer for organic electroluminescence device indicates, can be used two
Benzofuran or oil-source rock correlation and azepine aromatic hydrocarbons synthesize to obtain centre by the Suzuki coupling reaction of palladium chtalyst
Then body carries out Suzuki coupling with compound in triazine class again.Representative synthetic route is as follows:
Wherein, X1~X5In at least one N, and N is not in connection site；(L)m、R1~R2With meaning phase of the Z in general formula
Together.
The synthetic example of particular compound:
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1；
Under nitrogen protection, in equipped in churned mechanically four-hole bottle, dibenzo thiophene is added in the 500mL four-hole bottle of condenser pipe
Pheno -4- boric acid (20g, 87.7mmol, 1eq), the bromo- 2- iodine pyridine (29.8g, 105.2mmol, 1.2eq) of 5-, tetra-triphenylphosphine palladium
(2g, 1.75mmol, 2%eq), sodium carbonate (28g, 263.1mmol, 3eq), toluene 300mL, ethyl alcohol 100mL, water 100mL reaction
Mixture back flow reaction is for 24 hours.It being cooled to room temperature, is directly added into 250mL moisture liquid, water phase 200mL methylene chloride extracts three times,
Merge organic phase and is concentrated to give crude product.Crude product is boiled in petroleum ether and is washed, and yellow powder 23g, yield 80% are filtered to obtain.
The synthesis of intermediate 1-2；
Under nitrogen protection, in equipped in churned mechanically four-hole bottle, intermediate 2 is added in the 500mL four-hole bottle of condenser pipe
(3- bromophenyl) -4,6- diphenyl -1,3,5- triazine (30g, 77mmol, 1eq), connection boric acid pinacol ester (39g, 22mmol,
2eq), three (dibenzylidene indenes acetone) two palladiums (2.2g, 2.3mmol, 3%eq), 2- dicyclohexyl phosphine -2', 6'- dimethoxy connection
Benzene (Sphos, 3.8g, 9.2mmol, 12%eq), tripotassium phosphate (49g, 231mmol, 3eq), dioxane 300mL reaction mixing
Object back flow reaction is for 24 hours.It is cooled to room temperature, is directly added into 250mL moisture liquid, water phase 200mL methylene chloride extracts three times, merges
Organic phase is concentrated to give crude product.Crude product is boiled in petroleum ether and is washed, and white powder 27g, yield 80% are filtered to obtain.
The synthesis of compound 1；
Under nitrogen protection, in equipped be added in churned mechanically four-hole bottle, in the 500mL four-hole bottle of condenser pipe 1-1 (15g,
44mmol, 1eq), 1-2 (20g, 53mmol, 1.2eq), three (dibenzylidene indenes acetone) two palladiums (1.2g, 1.3mmol, 3%eq),
2- dicyclohexyl phosphine -2', 6'- dimethoxy-biphenyl (Sphos, 4.9g, 5.2mmol, 12%eq), tripotassium phosphate (28g,
132mmol, 3eq), dioxane 200mL reaction mixture back flow reaction is for 24 hours.It is cooled to room temperature, is directly added into 250mL moisture
Liquid, water phase 200mL methylene chloride extract three times, merge organic phase and be concentrated to give crude product.Crude product is boiled in petroleum ether and is washed, mistake
Filter to obtain white powder 9g, yield 40%.The mass spectrometric data of compound 1: MS (MALDI-TOF, m/z) calcd for Chemical
Formula:C38H24N4S:568.7.Found:568.6[M]+；
Similarly, with similar approach, we synthesize compound as shown in the table:
Device embodiments:
Embodiment
Organic Light Emitting Diode includes first electrode and second electrode on the substrate, and is located at first electrode and the
Organic layer between two electrodes.The organic layer at least has one layer of luminescent layer, it is possible to have hole injection layer, hole transport
The layer employed in organic EL element such as layer, electron injecting layer, electron transfer layer, hole blocking layer, electronic barrier layer.
Preferably, the organic layer include hole injection layer and/or hole transmission layer, luminescent layer, electron transfer layer and/or
Electron injecting layer.The first electrode is anode, and the second electrode is cathode；Or the first electrode be cathode, second
Electrode is anode.
Substrate using substrate used in organic light emitting display, such as: glass, polymer material and have TFT member device
Glass and polymer material of part etc..
Anode material can be using indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO) etc.
Transparent conductive material is also possible to the metal materials such as silver and its alloy, aluminium and its alloy, is also possible to the organic conductives such as PEDOT
The multilayered structure of material and above-mentioned material.
Cathode is metals, metal mixture, the oxide such as magnesium silver mixture, LiF/Al, ITO
The hole transmission layer or hole injection layer material can be selected from but not limited to following enumerated HT1-HT31.
It should be noted that above-mentioned " luminescent layer " refers to the organic layer with light-emitting function, when using doping system, contain
There are material of main part and dopant material.At this point, material of main part, which mainly has, promotes the compound of electronics and hole, shine exciton is enclosed
Function in layer, dopant material have the function of that the exciton as obtained from compound is made effectively to shine.In the feelings of phosphorescent element
Under condition, material of main part mainly has the function of enclosing the exciton generated by dopant in luminescent layer.
Luminescent layer material of main part can be selected from the one or more of general formula (1) compound, or be selected from general formula (1) describedization
Close the combination of material listed by object and GPH1-GPH80:
The dopant material, which can be selected from, can be, but not limited to following enumerated GPD1-GPD57:
Electron transfer layer can be, but not limited to following enumerated ET1-ET57 etc.
It can also include the electron injecting layer between electron transfer layer and cathode, electron injecting layer material packet in device
It includes but is not limited to the following one or more combinations enumerated.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The compound of the present invention may be used as the material of main part in the luminescent layer of organic electroluminescence device, following compounds
The material of main part also acted as in luminescent layer in comparative example that R1, R2 and R3 are designed as the present invention, structure are (as follows
Figure):
Organic electroluminescence device preparation process is as follows in this comparative example 1:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water,
In acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, clear with ultraviolet light and ozone
It washes, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation HI-1 is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-2 as device on hole injection layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit
The method steamed altogether with multi-source, adjusting material of main part R1 evaporation rate are 0.1nm/s, and 3% ratio of dyestuff GPD-12 evaporation rate is set
Fixed, vapor deposition total film thickness is 30nm；
The electron transport layer materials ET-29 of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer steam
Plating total film thickness is 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of 150nm
Cathode of the Al layer as device.
Comparative example 2
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound R 2 synthesized in the present invention.
Comparative example 3
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound R 3 synthesized in the present invention.
Inventive embodiments 1
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 1 synthesized in the present invention
Inventive embodiments 2
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 2 synthesized in the present invention.
Inventive embodiments 3
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 3 synthesized in the present invention.
Inventive embodiments 4
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 11 synthesized in the present invention.
Inventive embodiments 5
The compounds of this invention is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 13 synthesized in the present invention.
6 the compounds of this invention of inventive embodiments is as light emitting host material.
Organic electroluminescence device is prepared using method identical with comparative example, difference is, R1 is replaced
For the compound 25 synthesized in the present invention.
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, is measured in Examples 1 to 6 and comparative example 1~3 and made using digital sourcemeter and luminance meter
The driving voltage of standby obtained organic electroluminescence device and the service life of current efficiency and device.Specifically, with per second
The rate of 0.1V promotes voltage, and measurement reaches 10000cd/m when the brightness of organic electroluminescence device2When voltage, survey simultaneously
Current density at this time out；The ratio of brightness and current density is current efficiency.
Concrete preferred structure compound disclosed in device embodiments of the present invention is applied in organic electroluminescence device
Device performance detection data is detailed in following table:
| Device example | Host | Voltage(V) | CE(cd/A) |
| Comparative example 1 | Compound R 1 | 5.2 | 33 |
| Comparative example 2 | Compound R 2 | 5.5 | 26 |
| Comparative example 3 | Compound R 3 | 5.0 | 28 |
| Device embodiments 1 | Compound 1 | 4.0 | 65 |
| Device embodiments 2 | Compound 2 | 4.1 | 53 |
| Device embodiments 3 | Compound 3 | 4.0 | 68 |
| Device embodiments 4 | Compound 11 | 4.3 | 50 |
| Device embodiments 5 | Compound 13 | 4.6 | 51 |
| Device embodiments 6 | Compound 25 | 5.1 | 46 |
In organic electroluminescence device structure in the identical situation of other materials, using this kind of general formula chemical combination of the invention
Object replaces compound R in the prior art 1, R2 and R3 in comparative device Examples 1 to 3 as luminescent layer material of main part, hair
The operating voltage of prepared device is compared to control compounds as device prepared by light emitting host material in bright embodiment 1-6
Part voltage value decreases, at the same in embodiment 1-6 prepared device in 10000cd/m2The current efficiency measured under brightness
Also have compared to the current efficiency value of device prepared by comparative example and obviously promoted.
It can be seen that when such general formula compound of the invention is applied in organic electroluminescence device, it is prepared
From the point of view of OLED device is relative to device prepared by material in the prior art is used, the property of two aspects of service life and luminous efficiency
Extraordinary promotion effect can be all achieved, thus organic electroluminescence device has more excellent performance.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can
No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (14)
1. a kind of general formula compound, as shown in following formula (I):
Wherein: Z is selected from O, S or Se；
L is selected from singly-bound, or is selected from C1-C12Alkyl, C1-C8Alkoxy, C5-C30Substitution or unsubstituted arlydene,
C3-C30Substitution or unsubstituted heteroarylene；
Ar1Selected from following formula (1) or formula (2):
Ar2Selected from following formula (3):
In above-mentioned formula (1), (2) and (3):
X1~X8It is independently selected from CR3Or N, and X1~X4In at least one be N, X5~X8In at least one be N, R3
Selected from hydrogen, C1-C12Alkyl, C6-C30Aryl or fused ring aryl, C3-C30Heterocyclic aryl or fused ring heteroaryl；
R1~R2It is respectively and independently selected from hydrogen, C1-C12Alkyl, C6-C30Substitution or unsubstituted aryl or fused ring aryl, C3-
C30Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
Above-mentioned L and R1~R2On substituent group be respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30Monocycle heteroaryl hydrocarbon or
Condensed ring heteroaryl hydrocarbyl group.
2. general formula compound according to claim 1, the formula (I) is selected from following formula (II) or formula (III):
Wherein, Z is selected from O, S or Se；
L is selected from singly-bound, or is selected from C5-C15Substitution or unsubstituted arlydene, C3-C15Substitution or unsubstituted heterocycle
Arlydene；
X1~X8Definition with the definition in formula (1) and formula (2), and work as X1~X8It is independently selected from CR3When, R3It is selected from
Hydrogen, C1-C8Alkyl, C6-C15Aryl or fused ring aryl, C3-C15Heterocyclic aryl or fused ring heteroaryl；
R1And R2It is respectively and independently selected from hydrogen, C1-C8Alkyl, C6-C15Substitution or unsubstituted aryl or fused ring aryl, C3-
C15Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
The L and R1And R2On substituent group be respectively and independently selected from halogen, C1~C6Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, C6~C10Mononuclear aromatics or condensed-nuclei aromatics group, C3~C10Monocycle heteroaryl hydrocarbon or
Condensed ring heteroaryl hydrocarbyl group.
3. general formula compound according to claim 1 or 2, the X1~X8It is independently selected from CR3Or N, and X1~
X4In at least there are two be N, X5~X8In at least there are two be N.
4. general formula compound according to claim 2, the formula (II) and formula (III) are respectively following formula (IV) and formula
(V):
Wherein, Z, L, X1~X8And R1And R2Definition with the definition in formula (II) and formula (III).
5. according to claim 1, general formula compound described at least one of 2 or 4, in which:
L is selected from singly-bound, or selected from the group of flowering structure:
6. according to claim 1, general formula compound described at least one of 2 or 4, in which:
R1~R2Be respectively and independently selected from hydrogen, phenyl, xenyl, naphthalene, fluorenyl, Spirofluorene-based, pyridyl group, bipyridyl, pyrimidine radicals,
Pyrrole radicals, phenylpyridyl, pyrazinyl, quinolyl carbazyl, 9- phenyl carbazole base, 9- naphthyl carbazole and carbazyl.
7. according to claim 1, general formula compound described at least one of 2 or 4 is selected from following concrete structure formulas:
8. the application of general formula compound described in claim 1,2 or 4, the application is shining in organic electroluminescence device
Material of main part is used as in layer.
9. the application of structural compounds according to claim 7, the application is shining in organic electroluminescence device
Material of main part is used as in layer.
10. a kind of organic electroluminescence device, which includes first electrode, second electrode and the insertion first electrode and the
One or more layers organic layer between two electrodes, which is characterized in that include at least one in the organic layer by general formula (I) expression
Compound:
Wherein: Z is selected from O, S or Se；
L is selected from singly-bound, or is selected from C1-C12Alkyl, C1-C8Alkoxy, C5-C30Substitution or unsubstituted arlydene,
C3-C30Substitution or unsubstituted heteroarylene；
Ar1Selected from following formula (1) or formula (2):
Ar2Selected from following formula (3):
In above-mentioned formula (1), (2) and (3):
X1~X8It is independently selected from CR3Or N, and X1~X4In at least one be N, X5~X8In at least one be N, R3
Selected from hydrogen, C1-C12Alkyl, C6-C30Aryl or fused ring aryl, C3-C30Heterocyclic aryl or fused ring heteroaryl；
R1~R2It is respectively and independently selected from hydrogen, C1-C12Alkyl, C6-C30Substitution or unsubstituted aryl or fused ring aryl, C3-
C30Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
Above-mentioned L and R1~R2On substituent group be respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30Monocycle heteroaryl hydrocarbon or
Condensed ring heteroaryl hydrocarbyl group.
11. organic electroluminescence device according to claim 10, wherein the compound of general formula (I) statement is selected from
Following formula (II) or formula (III):
Wherein, Z is selected from O, S or Se；
L is selected from singly-bound, or is selected from C5-C15Substitution or unsubstituted arlydene, C3-C15Substitution or unsubstituted heterocycle
Arlydene；
X1~X8Definition with the definition in formula (1) and formula (2), and work as X1~X8It is independently selected from CR3When, R3It is selected from
Hydrogen, C1-C8Alkyl, C6-C15Aryl or fused ring aryl, C3-C15Heterocyclic aryl or fused ring heteroaryl；
R1And R2It is respectively and independently selected from hydrogen, C1-C8Alkyl, C6-C15Substitution or unsubstituted aryl or fused ring aryl, C3-
C15Substitution or unsubstituted heterocyclic aryl or fused ring heteroaryl；
The L and R1And R2On substituent group be respectively and independently selected from halogen, C1~C6Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, C6~C10Mononuclear aromatics or condensed-nuclei aromatics group, C3~C10Monocycle heteroaryl hydrocarbon or
Condensed ring heteroaryl hydrocarbyl group.
12. organic electroluminescence device described in 0 or 11 according to claim 1, in general formula compound therein, the X1~
X8It is independently selected from CR3Or N, and X1~X4In at least there are two be N, X5~X8In at least there are two be N.
13. organic electroluminescence device according to claim 11, wherein being stated by the formula (II) and formula (III) logical
Formula compound is respectively following formula (IV) and formula (V):
Wherein, Z, L, X1~X8And R1And R2Definition with the definition in formula (II) and formula (III).
14. organic electroluminescence device described at least one of 0,11 or 13 according to claim 1, general formula compound therein
Selected from following concrete structure formulas:
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140028640A (en) * | 2012-08-30 | 2014-03-10 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| CN105315219A (en) * | 2014-05-27 | 2016-02-10 | 环球展览公司 | Organic electroluminescent materials and uses thereof |
| US20160329502A1 (en) * | 2015-05-07 | 2016-11-10 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| KR20170076426A (en) * | 2015-12-24 | 2017-07-04 | 에스케이케미칼주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| WO2017221974A1 (en) * | 2016-06-24 | 2017-12-28 | 東ソー株式会社 | Triazine compound, method for producing same, and organic electroluminescent element which comprises same as constituent |
| WO2018021663A1 (en) * | 2016-07-29 | 2018-02-01 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic element, organic optoelectronic element, and display device |
-
2018
- 2018-02-02 CN CN201810105112.1A patent/CN110128416B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140028640A (en) * | 2012-08-30 | 2014-03-10 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| CN105315219A (en) * | 2014-05-27 | 2016-02-10 | 环球展览公司 | Organic electroluminescent materials and uses thereof |
| US20160329502A1 (en) * | 2015-05-07 | 2016-11-10 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| KR20170076426A (en) * | 2015-12-24 | 2017-07-04 | 에스케이케미칼주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| WO2017221974A1 (en) * | 2016-06-24 | 2017-12-28 | 東ソー株式会社 | Triazine compound, method for producing same, and organic electroluminescent element which comprises same as constituent |
| WO2018021663A1 (en) * | 2016-07-29 | 2018-02-01 | 삼성에스디아이 주식회사 | Composition for organic optoelectronic element, organic optoelectronic element, and display device |
Non-Patent Citations (1)
| Title |
|---|
| REG: "2108676-53-3等", 《STN》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112018255A (en) * | 2020-09-07 | 2020-12-01 | 中国科学院长春应用化学研究所 | Quantum dot light-emitting device |
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