CN110272422A - 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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- CN110272422A CN110272422A CN201810219039.0A CN201810219039A CN110272422A CN 110272422 A CN110272422 A CN 110272422A CN 201810219039 A CN201810219039 A CN 201810219039A CN 110272422 A CN110272422 A CN 110272422A
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Abstract
The invention discloses the general formula compounds of following formula (I):In formula (I): X1‑X10It is independently selected from CR3Or N；A and B at least one of the structure shown in formula (II), another is selected from arlydene or sub- fused ring aryl, heteroarylene or condensed hetero ring arlydene:L in formula (II)1Selected from arlydene, heteroarylene；R1、R2And R3It is respectively and independently selected from hydrogen, alkyl, aryl or fused ring aryl, heteroaryl or condensed hetero ring aryl.When the compound of the present invention is as material of main part in OLED luminescent layer, excellent device performance and stability are shown.The present invention protects the organic electroluminescence device using above-mentioned general formula compound simultaneously.
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
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, view
The a series of advantages such as angular width, light-weight, composition and simple process, compared with liquid crystal display, display of organic electroluminescence
Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but lower than response speed
The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance
The research of efficient organic material focuses more on, an excellent in efficiency service life long organic electroluminescence device be usually device architecture with
The result of the optimization collocation of various organic materials.In the most common OLED device structure, the organic of following type is generally included
Material: hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor
Body material) and corresponding material of main part etc..The phosphorescent light body material applied at present is all often to transmit energy with single carrier
Power, such as hole class transmit main body and electrical type transmits main body.Single carrier transport ability will cause electric in luminescent layer
The mismatch of son and hole, to cause serious efficiency roll-off and the lost of life.At present in the use process of main body, adopt
Solve the problems, such as that single material of main part carrier is unbalanced with the form of the either double material of main part collocation of bipolar materials.It is bipolar
Property material contains the segment of electron-transport and hole transport in single structure system, and structure is more complex；Double main bodys are to use
Two kinds of materials are respectively acting on electron-transport and hole transport, and double material of main part sources are more extensive, can take different materials
Combination realize better device performance.
Summary of the invention
The shortcomings that in order to overcome the above material of convention body in the prior art, the present invention provide a kind of novel for Organic Electricity
The compound of electroluminescence device.
The compound of the present invention is by shown in following general formula (I):
In formula (I): X1-X10It is each independently selected from CR3Or N；A and B at least one of shown in formula (II)
Structure, another is selected from substituted or unsubstituted C6-C20Arlydene or sub- fused ring aryl, substituted or unsubstituted C3-C30It is miscellaneous
Ring arlydene or condensed hetero ring arlydene:
L in formula (II)1Selected from substituted or unsubstituted C6-C30Arlydene or condensed ring arlydene, substituted or unsubstituted
C3-C30Heteroarylene or condensed hetero ring arlydene；
R1、R2And R3It is respectively and independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C6-C30
Aryl or fused ring aryl, substituted or unsubstituted C3-C30Heteroaryl or condensed hetero ring aryl；
Above-mentioned substituent group is respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, C2~C10Alkenyl, 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.
Specifically, as the above-mentioned A of definition and B, L1、R1To R3When being respectively and independently selected from aryl or arlydene, referring to be selected from has
Aromatics ring system of certain amount ring skeleton carbon atom, including single ring architecture substituent group such as phenyl etc. also include being covalently attached
The aromatic ring substituents of structure are rolled into a ball such as xenyl, terphenyl.
Specifically, as the above-mentioned A of definition and B, L1、R1To R3When being respectively and independently selected from fused ring aryl or sub- fused ring aryl, refer to
Selected from aromatics ring system with certain amount ring skeleton carbon atom, including condensed cyclic structure substituent group such as naphthalene, anthryl etc.,
Building stone such as the benzene binaphthyl, naphthalene xenyl, biphenyl being connected including condensed cyclic structure substituent group with single ring architecture aryl
Dianthranide base etc. further includes being covalently attached the thick aromatic ring substituents group of structure such as binaphthyl.
Specifically, as the above-mentioned A of definition and B, L1、R1To R3It is when being respectively and independently selected from heteroaryl or condensed hetero ring aryl group
Refer to include that one or more is selected from B, N, O, S, P (=O), the hetero atom of Si and P and monocycle or condensed ring virtue with ring carbon atom
Base.
Further, X1-X10Among preferred X1With X5In at least one be N.
Further, when A or B are separately selected from arlydene, sub- fused ring aryl, heteroarylene or the sub- virtue of condensed hetero ring
When base, preferably are as follows: phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl -3-
Base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene
Base, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl,
9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,
Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, dibenzothiophene, dibenzofuran group,
Dibenzo selenophen base, carbazyl, phenyl carbazole base.
Further, R1To R3Separately preferably are as follows: methyl, ethyl, phenyl, 2- xenyl, 3- xenyl, 4- connection
It is phenyl, p- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m-
Terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl,
1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, three
Phenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, hexichol
And thiophene coughs up base, dibenzothiophene, dibenzofuran group, dibenzo selenophen base, carbazyl, phenyl carbazole base.
Further, L1Preferably phenylene, naphthylene.
Further, it is following specific can to enumerate selection for the preferred example as novel logical formula (I) compound of the invention
Structural compounds A1-A45, these compounds are only representative:
The compound that logical formula (I) of the invention indicates can be, but not limited to be used as luminescent layer in organic electroluminescence device
Material.
The present invention also provides a kind of organic electroluminescence device, including first electrode, second electrode and it is located at described the
One or more layers organic layer between one electrode and second electrode includes at least luminescent layer, the luminescent layer in the organic layer
In comprising at least one by shown in following general formula (I):
In formula (I): X1-X10It is each independently selected from CR3Or N；At least one in A and B is selected from lower formula (II), another choosing
From substituted or unsubstituted C6-C20Arlydene or sub- fused ring aryl, substituted or unsubstituted C3-C30Heteroarylene is thick miscellaneous
Ring arlydene；
L in formula (II)1Selected from substituted or unsubstituted C6-C30Arlydene or condensed ring arlydene, substituted or unsubstituted
C3-C30Heteroarylene or condensed hetero ring arlydene；
R1、R2And R3It is respectively and independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C6-C30
Aryl or fused ring aryl, substituted or unsubstituted C3-C30Heteroaryl or condensed hetero ring aryl.
For above-mentioned group there are when substituent group, substituent group is respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, C2~
C10Alkenyl, C1~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30's
Monocycle heteroaryl hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
Further, X1-X10Among preferred X1With X5In at least one be N.
Further, when A or B are separately selected from arlydene, sub- fused ring aryl, heteroarylene or the sub- virtue of condensed hetero ring
When base, preferably are as follows: phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl -3-
Base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene
Base, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl,
9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,
Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, dibenzothiophene, dibenzofuran group,
Dibenzo selenophen base, carbazyl, phenyl carbazole base.
Further, R1To R3Separately preferably are as follows: methyl, ethyl, phenyl, 2- xenyl, 3- xenyl, 4- connection
It is phenyl, p- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m-
Terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl,
1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, three
Phenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, hexichol
And thiophene coughs up base, dibenzothiophene, dibenzofuran group, dibenzo selenophen base, carbazyl, phenyl carbazole base.
Further, L1Preferably phenylene, naphthylene.
Present invention design is using indolocarbazole as precursor structure, the in this way extension of guarantee conjugated system, intermolecular work
It is firmly stronger, be conducive to intermolecular solid-state accumulation, improve the service life of material.Then design uses the structure fragment of disubstituted fluorene
It is connect with the parent segment of indolocarbazole by the segment of a bridging, improves the structure fragment and Yin of disubstituted fluorene in this way
The transmitting of charge between diindyl and carbazole and transfer ability, so that the efficiency of carrier transport in device is improved, it is final to show
For the luminous efficiency for promoting organic electroluminescence device.In general formula compound of the invention, key point is design disubstituted fluorene piece
The substitution site of section is 4 substitutions, may insure that molecule obtains biggish steric hindrance in this way, to have to centre of luminescence parent nucleus
There is good protective effect, it finally can be in the service life for ensuring to improve organic electroluminescence device.
In the general formula compound that the present invention designs, when the substituent group on precursor structure is preferably designed for inhaling the heterocycle virtue of electricity
When fragrant class substituent group, the efficiency of transmission of compound electronics can be effectively improved, thus is suitable for being used as bipolar materials, this
Sample can be improved the balance of exciton transfer in organic electroluminescence device, to promote the luminous efficiency of material of main part in device.
In general formula compound of the invention, when the substituent group on precursor structure is preferably designed for the aromatics substituent group of power supply,
The hole injection efficiency of the compounds of this invention can be effectively improved, realizes the effect for reducing voltage well, thus is suitable for conduct
Cavity type material of main part uses, and arranges in pairs or groups when with electron type material of main part in use, the luminous efficiency of material can be effectively improved, from
And extend the service life of organic electroluminescence device.
Specific embodiment
The specific preparation method of above-mentioned noval chemical compound of the invention will be described in detail by taking multiple synthetic examples as an example below, but
Preparation method of the invention is not limited to this multiple synthetic example, and those skilled in the art can not depart from its basis
Any modification, equivalent substitution, improvement and etc. are carried out under the premise of principle of the present invention, and this method is expanded into right of the invention and is wanted
Within the scope of seeking the claimed technical solution of book.
Synthetic example
Representative synthesis path 1:
By replacing different Ar-X2Different target compounds can be obtained.It should be noted that above-mentioned synthetic method
Middle to be coupled using Buchwald, but be not restricted to that the coupling method, those skilled in the art can also choose other methods, example
The method as known to Ullman coupling method etc., but these methods are not limited to, it can select as needed.
More specifically, the synthetic method of representative compound of the invention is given below.
Synthesis example 1: the synthesis of compound A2
In reaction flask, indoles simultaneously (3,2-A) carbazole 25.6g (100mmol), 4- (4- bromophenyl) -9 is added in nitrogen protection,
9- dimethyl fluorene 38.2g (110mmol), Pd2(dba)30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide
43.3g (314mmol), heating reflux reaction 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration, institute
Obtained solid obtains white powder M1 by recrystallization purifying in toluene.
Nitrogen protection in reaction flask, is added intermediate M1 10.4g (20mmol), 4- bromo biphenyl 26.2g (110mmol),
Pd2 (dba) 30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide 43.3g (314mmol) are heated to reflux anti-
Answer 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration, obtained solid in toluene by recrystallizing
Purifying, obtains white powder A1.
Synthesis example 2: the synthesis of compound A13
In reaction flask, indoles simultaneously (3,2-A) carbazole 25.6g (100mmol), 4- (4- bromophenyl) -9 is added in nitrogen protection,
9- dimethyl fluorene 38.2g (110mmol), Pd2(dba)30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide
43.3g (314mmol), heating reflux reaction 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration, institute
Obtained solid obtains white powder M1 by recrystallization purifying in toluene.
Nitrogen protection in reaction flask, is added intermediate M1 10.4g (20mmol), 4- bromobenzene-diphenylamine 34.6g
(110mmol), Pd2(dba)30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide 43.3g (314mmol),
Heating reflux reaction 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration, obtained solid passes through first
Recrystallization purifying in benzene obtains white powder A13.
Synthesis example 3: the synthesis of compound A-13 9
In reaction flask, indoles simultaneously (3,2-A) carbazole 25.6g (100mmol), chloro- 4, the 6- diphenyl of 2- is added in nitrogen protection
Triazine 29.4g (110mmol), Pd2(dba)30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide 43.3g
(314mmol), heating reflux reaction 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration is obtained
Solid obtains white powder M1 by recrystallization purifying in toluene.
Nitrogen protection in reaction flask, is added intermediate M1 10.4g (20mmol), 4 (3- bromophenyl) -9,9- dimethyl fluorenes
34.6g (110mmol), Pd2(dba)30.9g (0.785mmol, 0.5%), dimethylbenzene 1500mL, sodium tert-butoxide 43.3g
(314mmol), heating reflux reaction 12h.End of reaction stops reacting.It is cooled to room temperature, washes, organic phase concentration is obtained
Solid obtains white powder A39 by recrystallization purifying in toluene.
Device embodiments
Embodiment
Organic Light Emitting Diode includes the first electrode and second electrode on substrate, and having between electrode
Machine material includes hole transmission layer, luminescent layer, electron transfer layer between first electrode and second electrode.
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
Hole transmission layer can be, but not limited to one or more combinations of following enumerated HT1-HT31.
Phosphorescent light body material includes but is not limited to one of GPH1-GPH80 or a variety of combinations:
Phosphorescent dopants can be, but not limited to one or more combinations of following enumerated GPD1-GPD57.
Electron transfer layer can be, but not limited to one or more combinations of following enumerated ET1-ET57.
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。
Embodiment 1:
Organic electroluminescence device preparation process is as follows:
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 HT-11 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-5 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 A2 evaporation rate are 0.1nm/s, and 3% ratio of dyestuff GPD-1 evaporation rate is set
Fixed, vapor deposition total film thickness is 30nm；
The electron transport layer materials ET42 of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer, vapor deposition
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.
The embodiment 1 that the specific preparation process of comparative example 1,2 and embodiment 2-4 are same as above, difference will only be led
Body materials A 2 replaces with material R-1, R-2 in the prior art and the compound of the present invention A13 and A39 respectively.
The embodiment 1 that the specific preparation process of comparative example 3 and 4 and the embodiment of the present invention 4 and 5 is same as above,
Difference is designed as the first material of main part GPH29 and arranges in pairs or groups respectively now only in the luminescent layer of device using double material of main part structures
There are material R-1, R-2 and the compound of the present invention A2 and A13 in technology to use as the second material of main part, two main body materials
The usage ratio of material is 1:1.
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, it is prepared using digital sourcemeter and luminance meter measurement Examples 1 to 7 and comparative example 1~2
The driving voltage and current efficiency of organic electroluminescence device and the service life of device.Specifically, with the rate of 0.1V per second
Voltage is promoted, measurement reaches 10000cd/m when the brightness of organic electroluminescence device2When voltage, that is, driving voltage, survey simultaneously
Current density at this time out；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows: using brightness
Meter is in 10000cd/m2Under brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to 9500cd/m2's
Time, unit are hour.
The specific performance of organic electroluminescence device prepared by each embodiment see the table below 1.
Table 1:
The above result shows that in organic electroluminescence device structure in the identical situation of other materials, using the present invention
This kind of general formula compound replace the compound in the prior art in comparative device embodiment as light emitting host material, can be with
The landing voltage of device is effectively reduced, current efficiency is improved, extends device lifetime.
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 (10)
1. a kind of general formula compound, as shown in following formula (I):
In formula (I):
X1-X10It is independently selected from CR3Or N；
At least one in A and B is selected from lower formula (II), another is selected from substituted or unsubstituted C6-C20Arlydene or sub- condensed ring
Aryl, substituted or unsubstituted C3-C30Heteroarylene or condensed hetero ring arlydene；
In formula (II): L1Selected from substituted or unsubstituted C6-C30Arlydene or sub- fused ring aryl, substituted or unsubstituted C3-C30
Heteroarylene or condensed hetero ring arlydene；
R1、R2And R3It is respectively and independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C6-C30Virtue
Base or fused ring aryl, substituted or unsubstituted C3-C30Heteroaryl or condensed hetero ring aryl；
Above-mentioned group is there are when substituent group, and substituent group is independently selected from halogen, C1~C10Alkyl or cycloalkyl, C2~C10Alkene
Base, C1~C6Alkoxy 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, in the formula (I), X1-X10Among X1With X5In at least one
A is N.
3. general formula compound according to claim 1 or 2, in the general formula:
When A or B are separately selected from arlydene, sub- fused ring aryl, heteroarylene or condensed hetero ring arlydene, it is selected from:
Phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl
Base -2- base, m- terphenyl -4- base, m- terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthracene
Base, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes,
9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base,
2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, dibenzothiophene, dibenzofuran group, dibenzo selenophen base, click
Oxazolyl, phenyl carbazole base；
R1、R2And R3It is separately selected from: hydrogen, methyl, ethyl, phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- three
Xenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3-
Base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenes
Base, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrene
Base, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, two
Benzothienyl, dibenzofuran group, dibenzo selenophen base, carbazyl, phenyl carbazole base；
L1Selected from phenylene or naphthylene.
4. general formula compound according to claim 1 or 2 is selected from following specific structure compounds:
5. the application of general formula compound of any of claims 1 or 2, the application is the luminescent layer in organic electroluminescence device
It is middle to be used as material of main part.
6. the application of structural compounds according to claim 4, the application is shining in organic electroluminescence device
Material of main part is used as in layer.
7. 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:
In formula (I):
X1-X10It is each independently selected from CR3Or N；
At least one in A and B is selected from lower formula (II), another is selected from substituted or unsubstituted C6-C20Arlydene or sub- condensed ring
Aryl, substituted or unsubstituted C3-C30Heteroarylene or condensed hetero ring arlydene；
In formula (II): L1Selected from substituted or unsubstituted C6-C30Arlydene or condensed ring arlydene, substituted or unsubstituted C3-C30
Heteroarylene or condensed hetero ring arlydene；
R1、R2And R3It is respectively and independently selected from hydrogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C6-C30Virtue
Base or fused ring aryl, substituted or unsubstituted C3-C30Heteroaryl or condensed hetero ring aryl；
When above-mentioned group is there are when substituent group, substituent group is respectively and independently selected from halogen, C1~C10Alkyl or cycloalkyl, C2~C10
Alkenyl, C1~C6Alkoxy or thio alkoxy group, C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, C3~C30List
Ring heteroaryl hydrocarbon or condensed ring heteroaryl hydrocarbyl group.
8. a kind of organic electroluminescence device according to claim 7, which is characterized in that include in the organic layer by
In the general formula compound that formula (I) indicates, wherein X1-X10Among X1With X5In at least one be N.
9. a kind of organic electroluminescence device according to claim 7 or 8, which is characterized in that include in the organic layer
By formula (I) indicate general formula compound in, in which:
When A or B are separately selected from arlydene, sub- fused ring aryl, heteroarylene or condensed hetero ring arlydene, it is selected from:
Phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl
Base -2- base, m- terphenyl -4- base, m- terphenyl -3- base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthracene
Base, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes,
9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base,
2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, dibenzothiophene, dibenzofuran group, dibenzo selenophen base, click
Oxazolyl, phenyl carbazole base；
R1To R3It is separately selected from: hydrogen, methyl, ethyl, phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- three
Phenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3-
Base, m- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, 1- fluorenyl, 2- fluorenes
Base, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenes, indenofluorene, fluoranthene base, triphenylene, 1- pyrene
Base, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base, 2- aphthacene base and 9- aphthacene base, dibenzo thiophene cough up base, two
Benzothienyl, dibenzofuran group, dibenzo selenophen base, carbazyl, phenyl carbazole base；
L1Selected from phenylene or naphthylene.
10. a kind of organic electroluminescence device according to claim 7 or 8, which is characterized in that include in the organic layer
By formula (I) indicate general formula compound, be selected from following specific structure compounds:
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| WO2021075895A1 (en) * | 2019-10-18 | 2021-04-22 | 주식회사 엘지화학 | Organic light-emitting device |
| CN114008810A (en) * | 2019-10-18 | 2022-02-01 | 株式会社Lg化学 | Organic light emitting device |
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| CN103189469A (en) * | 2010-08-27 | 2013-07-03 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| WO2014030921A1 (en) * | 2012-08-21 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| KR20150116337A (en) * | 2014-04-07 | 2015-10-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103189469A (en) * | 2010-08-27 | 2013-07-03 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| WO2014030921A1 (en) * | 2012-08-21 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| KR20150116337A (en) * | 2014-04-07 | 2015-10-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2021075895A1 (en) * | 2019-10-18 | 2021-04-22 | 주식회사 엘지화학 | Organic light-emitting device |
| CN114008810A (en) * | 2019-10-18 | 2022-02-01 | 株式会社Lg化学 | Organic light emitting device |
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