CN109553620A - General formula compound and organic electroluminescence device - Google Patents
General formula compound and organic electroluminescence device Download PDFInfo
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Abstract
The present invention relates to a kind of general formula compounds as shown in following formula (I):In formula (I), R is selected from lower formula (II) or (III):In formula (II): P and Q is separately selected from C or N, and at least 1 is N；Ra indicate mono-, di-, three, it is four substituted or unsubstituted, and any adjacent Ra is optionally connected, and R1The optional connection with adjacent Ra；Ra and R1It is respectively and independently selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.In formula (III): X, Y and Z are separately selected from C or N, and wherein at least having 1 is N；R2And R3Separately it is selected from hydrogen, C1~C10Alkyl, halogen, C6~C30Aryl amine, C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.The invention further relates to a kind of organic electroluminescence devices using above-mentioned general formula compound.
Description
Technical field
The present invention relates to a kind of organic compounds, may be used as organic electroluminescence device luminescent layer material of main part；This
Invention further relates to application of the compound in organic electroluminescence device.
Background technique
Now with OLED technology in the continuous propulsion for illuminating and showing two big fields, people grind for its core material
Study carefully and focus more on, the excellent in efficiency service life organic electroluminescence device of length is usually device architecture and various organic materials
Optimize arranging in pairs or groups as a result, this functionalization material for just designing and developing various structures for chemists provides greatly opportunity and chooses
War.Common functionalization organic material has: hole-injecting material, hole mobile material, hole barrier materials, electron injection material
Material, electron transport material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..More for processability
Good luminescent device, industry have been devoted to develop luminous efficiency of the new electroluminescent organic material to further increase device
And the service life.
Organic electroluminescence device has low driving voltage, fast response time, angular field of view wide and can be tied by chemistry
Structure fine tuning change luminescent properties make it is rich in color, the advantages that high resolution easy to accomplish, light-weight, large-area flat-plate display, at
For the hot spot of the subjects such as material, information, physics and flat display field research.Efficient commercialization Organic Light Emitting Diode will very
Organic metal phosphor may be contained, because they can capture singlet and triplet excitons, to realize 100%
Internal quantum efficiency.However, the excitation state exciton lifetime due to transient metal complex is relatively too long, lead to-three line of triplet state
State (T1-T1) is quenched in device real work.In order to overcome this problem, triplet emission object is often doped to by researchers
In organic host material.Therefore, for efficient Organic Light Emitting Diode, high performance material of main part and guest materials are developed
It is most important.As one of three primary colours, feux rouges is very crucial for panchromatic colour developing and solid-state lighting.However efficient red device
But seldom, main cause is a lack of suitable material of main part.
Currently, be widely used in red phosphorescent device material of main part be CBP, it require that driving voltage it is higher,
Tg=62 DEG C, it is easy to crystallize.In addition, CBP is a kind of p-type material, hole mobility is much higher than electron mobility, is unfavorable for carrying
The injection of stream and transmission balance.
The leeway however, existing electroluminescent organic material is also improved in terms of luminescent properties, industry need out
The electroluminescent organic material for sending out new.
Summary of the invention
The purpose of the present invention is to propose to a kind of novel general formula compounds of good performance.It provides simultaneously a kind of using such new
The organic electroluminescence device of type compound.
The present invention provides a kind of general formula compounds, have the structural formula as shown in formula (I):
In formula (I), R is selected from lower formula (II) or (III):
In formula (II): P and Q is separately selected from C or N, and at least 1 is N；
Ra indicate mono-, di-, three, it is four substituted or unsubstituted, and any adjacent Ra is optionally connected, and R1With adjacent Ra
Optional connection；
Ra and R1It is respectively and independently selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30It is substituted or unsubstituted
Aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
In formula (III): X, Y and Z are separately selected from C or N, and wherein at least having 1 is N；
R2And R3Separately it is selected from hydrogen, C1~C10Alkyl, halogen, C6~C30Aryl amine, C6~C30Substitution or
Unsubstituted aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
It is above-mentioned to work as Ra, R1、R2And R3It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring virtue
When hydrocarbyl group, the substituent group thereon is independently selected from cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, C1~C6
Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S,
The hetero atom and C of Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group, or be selected from Si (R4)3, the R4Selected from C1~C6Alkane
Base.
Specifically, as definition above-mentioned Ra, R1、R2And R3When being respectively and independently selected from aryl or arlydene, refer to selected from one
The aromatics ring system, including single ring architecture substituent group such as phenyl etc. of fixed number mesh ring skeleton carbon atom also include being covalently attached knot
The aromatic ring substituents of structure are rolled into a ball such as xenyl, terphenyl.
Specifically, as definition above-mentioned Ra, R1、R2And R3It is when being respectively and independently selected from condensed-nuclei aromatics or sub- condensed-nuclei aromatics group
Refer to the aromatics ring system, including condensed cyclic structure substituent group such as naphthalene, anthryl etc. with certain amount ring skeleton carbon atom, also wraps
Include building stone such as benzene binaphthyl, naphthalene xenyl, the biphenyl connection that condensed cyclic structure substituent group is connected with single ring architecture aryl
Anthryl etc. further includes being covalently attached the thick aromatic ring substituents group of structure such as binaphthyl.
Specifically, as definition above-mentioned Ra, R1、R2And R3Refer to when being respectively and independently selected from heteroaryl or condensed hetero ring aromatic hydrocarbon group
Comprising one or more selected from B, N, O, S, P (=O), the hetero atom of Si and P and with the monocycle or fused ring aryl of ring carbon atom.
Further, in formula (II) and formula (III), Ra, R1、R2And R3It is respectively and independently selected from C1~C5Alkyl, C6~C10's
Aryl amine, C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heteroaryl
Or condensed hetero ring aromatic hydrocarbon group；
As Ra, R1、R2And R3When selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, institute
The substituent group stated thereon preferably independently is selected from cyano, or is selected from C1~C5Alkyl or cycloalkyl, Si (CH3)3, alkenyl, alkoxy or
Thio alkoxy group, or it is selected from C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, contain be selected from N or O hetero atom and C6
~C15Mononuclear aromatics or condensed-nuclei aromatics group.
Further, in formula (II) and formula (III), Ra, R1、R2And R3Selected from substituted aryl, condensed-nuclei aromatics group, miscellaneous
When aryl or condensed hetero ring aromatic hydrocarbon group, the substituent group thereon preferably independently is selected from cyano, methyl, ethyl, isopropyl, alcoxyl
Base, phenyl, naphthalene, pyridyl group, pyrrole radicals.
Further, in formula (II) and formula (III), Ra, R1、R2And R3Selected from following aryl or fused ring aryl group: benzene
Base, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, three
Phenylene, pyrenyl, base,Base or aphthacene base；The phenyl replaced by furyl, thienyl, pyrrole radicals and/or pyridyl group.
Above-mentioned xenyl is preferably 2- xenyl, 3- xenyl and 4- xenyl, and above-mentioned terphenyl is preferably p- three
Phenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base
With m- terphenyl -2- base；Above-mentioned naphthalene is preferably 1- naphthalene and/or 2- naphthalene；Above-mentioned anthryl is preferably 1- anthryl, 2- anthracene
Base or 9- anthryl；Above-mentioned pyrenyl is preferably 1- pyrenyl, 2- pyrenyl or 4- pyrenyl；Above-mentioned aphthacene base be preferably 1- aphthacene base,
2- aphthacene base or 9- aphthacene base.
Further, in formula (II) and formula (III), Ra, R1、R2And R3Selected from following heteroaryls or thick heteroaryl groups:
Furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazine
Base, quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzene
And quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, phenyl replace two
At least one of azoles, coffee quinoline base, coffee quinoline benzothiazolyl and benzodioxole group, wherein the carbazyl is derivative
Object can include but is not limited in 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole and indolocarbazole extremely
Few one kind.
Further, the preferred example as novel general formula compound of the invention can be enumerated and select following representativenesses
Compound P1-P90:
The luminescent layer that can be used as organic electroluminescence device containing carbazole-fluoranthene class feux rouges main body class compound of the invention
Material of main part also can be used as the material of hole injection layer, be alternatively arranged as the material of hole transmission layer.
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 formula (I) compound represented:
In formula (I), R is selected from lower formula (II) or (III):
In formula (II): P and Q is separately selected from C or N, and at least 1 is N；
Ra indicate mono-, di-, three, it is four substituted or unsubstituted, and any adjacent Ra is optionally connected, and R1With adjacent Ra
Optional connection；
Ra and R1It is respectively and independently selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30It is substituted or unsubstituted
Aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
In formula (III): X, Y and Z are separately selected from C or N, and wherein at least having 1 is N；
R2And R3Separately it is selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30Substitution or do not take
The aryl or condensed-nuclei aromatics group, C in generation3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
It is above-mentioned to work as Ra, R1、R2And R3It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring virtue
When hydrocarbyl group, the substituent group thereon is independently selected from cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, C1~C6
Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S,
The hetero atom and C of Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group, or be selected from Si (R4)3, the R4Selected from C1~C6Alkane
Base.
The advantages of novel general formula compound of the invention, is:
The present invention is by being parent nucleus by carbazole-fluoranthene skeleton compound, with scarce pi-electron type nitrogen-containing hetero aromatic ring atom group
(quinoline group, triazine group, pyrimidine group) connection is formed.Molecular skeleton, which passes through, introduces supplied for electronic and electron-withdrawing group, so that
Compound energy simultaneous transmission electrons and holes, have bipolar transmission performance, and then can widen charge recombination zone, can be used as
Bipolar transmission material.In addition, carbazole-fluoranthene group further expansion conjugated structure and rigid nature of compound, more has
Conducive to the transmission of charge and the raising of stability, to provide the organic electroluminescence with high efficiency and high stability
Part.The parent nucleus group of the compounds of this invention is carbazole-fluoranthene group, and molecular weight is smaller, can realize at a lower temperature
The sublimation purification and element manufacturing of material, are conducive to the stability of material；And mother nucleus structure has coplanarity well,
Derivative carrier transport with higher, so as to significantly reduce the operating voltage of the device using such material.
Detailed description of the invention
From the detailed description with reference to the accompanying drawing to the embodiment of the present invention, these and/or other aspects of the invention and
Advantage will become clearer and be easier to understand, in which:
Fig. 1 is highest occupied molecular orbital (HOMO) energy diagram of the compounds of this invention P1；
Fig. 2 is lowest unoccupied molecular orbital (LUMO) energy diagram of the compounds of this invention P1.
Specific embodiment
In order to make those skilled in the art more fully understand the present invention, with reference to the accompanying drawings and detailed description to this hair
It is bright to be described in further detail.
The compound for the synthetic method that do not mention in the present invention is all the raw produce being obtained through commercial channels.Implement
Various chemicals such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, methylene chloride, four chlorinations used in example
Bis- (bromomethyl) benzene of carbon, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans--diamino
Hexamethylene, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, sodium tert-butoxide, Loprazolam, 1-
Bromo- 2- methyl naphthalene, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1- (2- bromophenyl) -2- first
Base naphthalene, N- bromo-succinimide, methoxyl methyl San Jia Ji phosphonium chloride, tris(dibenzylideneacetone) dipalladium, four (triphenylphosphines)
Palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- di-t-butyl carbazole, N- phenyl carbazole -3- bromine, 2- bromine Fluorenone,
The basic chemical industries raw materials such as 2- (4- bromobenzene) -4,6- diphenyl triazine 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).
Brief description is carried out to the synthetic method of the compounds of this invention below.
The synthetic example of compound:
Listed compound P1-P90 presses following synthetic schemes and obtains in the present invention.
As described above, intermediate M1 and specific chemical combination is described in detail with synthesis example 1-5 below in the meaning of R in the present embodiment
The synthesis step of object.
Synthesis example 1: the synthesis of intermediate M1
In 250 milliliters of there-necked flasks, compound A 1.0g, compound B 1.2g, Pd is added2(dba)30.04g, sodium tert-butoxide
0.75g, three tertiary butyl phosphine tetrafluoroborate 0.02g and 30ml dimethylbenzene, pumping are filled 3 nitrogen, are warming up to back under nitrogen protection
Stream temperature is cooled to room temperature after reaction overnight, and with silicagel column is crossed after dilution with toluene, again with toluene is recrystallized to give yellow solid
1.4g, yield 80%.MS (m/e): 456,1H NMR(300MHz,CDCl3): 8.56 (1H), 8.43 (2H), 8.11 (2H), 8.13
(1H),8.00(2H),7.95(1H),7.90(1H),7.64(2H),7.61(2H),7.57(1H),7.34(1H),7.32(1H),
7.30 (1H), 7.28 (1H), elemental analysis: C (89.5%), N (6.2%), H (4.3%).
Synthesis example 2: the synthesis of compound P1
In 250 milliliters of there-necked flasks, compound M1 1.0g, compound C 0.58g, potassium carbonate 0.91g and 30ml is added
DMF, pumping fill 3 nitrogen, are warming up to 130 DEG C under nitrogen protection, after reaction overnight, are cooled to room temperature, reaction solution is poured into
Precipitating is precipitated into water, filter cake is dissolved in toluene by filtering precipitating, crosses silicagel column, it is solid that again with toluene is recrystallized to give glassy yellow
Body 1.2g, MS (m/e): 660, yield 80%.MS (m/e): 456,1H NMR(300MHz,CDCl3): 8.56 (2H), 8.43
(2H),8.16(1H),8.11(2H),8.06(2H),7.95(4H),7.80(4H),7.64(1H),7.61(2H),7.52(2H),
7.42 (1H), 7.34 (2H), 7.32 (1H), 7.28 (2H), elemental analysis: C (87.3%), N (8.5%), H (4.2%).
Synthesis example 3: the synthesis of compound P11
The same P1 of preparation method, only changes compound C into compound D, obtains bright yellow solid product 1.0g, yield
81%.MS (m/s): 584,1H NMR(300MHz,CDCl3): 9.75 (1H), 8.56 (2H), 8.43 (2H), 8.16 (1H), 8.11
(2H),8.06(2H),7.95(4H),7.80(2H),7.64(1H),7.61(2H),7.34(2H),7.32(1H),7.28(2H),
Elemental analysis: C (86.3%), N (9.6%), H (4.1%).
Synthesis example 4: the synthesis of compound P13
The same P1 of preparation method, only changes compound C into compound E, obtains bright yellow solid product 1.3g, MS (m/s):
687, yield 85%.1H NMR(300MHz,CDCl3): 8.56 (2H), 8.43 (2H), 8.29 (4H), 8.11 (2H), 7.95
(4H),7.80(1H),7.64(1H),7.61(2H),7.51(4H),7.41(2H),7.34(2H),7.32(1H),7.28(2H),
Elemental analysis: C (85.6%), N (10.2%), H (4.2%).
Synthesis example 5: the synthesis of compound P28
The same P1 of preparation method, only changes compound C into compound F, obtains bright yellow solid product 1.3g, MS (m/s):
686, yield 85%.1H NMR(300MHz,CDCl3): 8.56 (2H), 8.43 (2H), 8.29 (4H), 8.11 (2H), 7.95
(4H),7.80(3H),7.64(1H),7.61(2H),7.51(4H),7.41(2H),7.34(2H),7.33(1H),7.32(1H),
7.28 (2H), elemental analysis: C (87.4%), N (8.2%), H (4.4%).
Synthetic route and thinking based on the glimmering anthracene compound containing carbazole-above, those skilled in the art can obtain substitution not
Same compound.Organic electroluminescence device of the invention is illustrated below.
The structure of organic electroluminescence device of the invention and well known device have no difference, including cathode, anode and have
Machine functional layer, wherein including more than one luminescent layer in the organic function layer.The feature of organic luminescent device of the invention
It is, includes the glimmering anthracene compound of the present invention containing carbazole-in organic function layer.
In general, organic function layer is mainly hole injection layer, hole transmission layer, luminescent layer, electron transfer layer etc..This
The material of main part, hole mobile material, hole-injecting material that the glimmering anthracene compound containing carbazole-of invention can be used as luminescent layer come
It uses.
It is described in detail below by way of technical effect of the device embodiments to the compounds of this invention.
Device embodiments
The typical structure of the OLED organic electroluminescence device prepared in embodiment are as follows:
Substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/cathode
Above-mentioned "/" indicates to be laminated in order between different function layer.
The substrate in conventional organic luminescence organic electroluminescence device can be used in substrate, such as: glass or plastics.Anode
Material can use transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), oxygen
Change zinc (ZnO) etc..Glass substrate is selected in the organic electroluminescence device production of embodiment, ITO makees anode material.The present invention
Several electroluminescent organic material specific structures used in the device of embodiment are as follows.
Above-mentioned electroluminescent organic material, those skilled in the art, which are based on known method, can voluntarily prepare or purchase from Chemical market
It buys.
Device embodiments:
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence device, organic electroluminescence hair
Optical device structure, on substrate, according to " anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/
The sequence of cathode " is laminated.Organic electroluminescence device preparation process is as follows:
The glass plate for being coated with ITO (150nm) transparency conducting layer is ultrasonically treated in commercial detergent, in deionized water
Middle flushing, in acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) is baked under clean environment and completely removes water
Part, with ultraviolet light and ozone clean, 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 NPB is as hole transmission layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 40nm；
Vacuum evaporation the compounds of this invention and control compounds CBP are as in device luminescent layer on hole transmission layer
Material of main part, while co-evaporation phosphorescent coloring Ir (piq)3(its mass percent being respectively added is as follows in each device architecture
It is shown), evaporation rate 0.1nm/s, vapor deposition total film thickness is 30nm；
Electron transfer layer of the vacuum evaporation Bphen as device on luminescent layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 20nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer and with a thickness of the Al layer conduct of 150nm on the electron transport layer
The cathode of device.
Method as described above prepares following device, makes it have with flowering structure:
Comparative example 1-1:
ITO (150nm)/NPB (40nm)/CBP: 5%Ir (piq)3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al
(150nm)
Wherein 5% indicate Ir (piq)3Weight ratio relative to CBP is 5%, and following embodiment is also expressed in this way.
Embodiment 1-1:
ITO (150nm)/NPB (40nm)/P1: 5%Ir (piq)3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al
(150nm)
Embodiment 1-2:
ITO (150nm)/NPB (40nm)/P11: 5%Ir (piq)3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al
(150nm)
Embodiment 1-3:
ITO (150nm)/NPB (40nm)/P13: 5%Ir (piq)3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al
(150nm)
Embodiment 1-4:
ITO (150nm)/NPB (40nm)/P28: 5%Ir (piq)3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al
(150nm)
Driving voltage and current efficiency under same brightness are measured to made organic electroluminescence device, compare its property
Energy.It the results are shown in Table 1.
Table 1
| Device embodiments | Material of main part | It is required that brightness (cd/m2) | Driving voltage (V) | Current efficiency (cd/A) |
| Comparative example 1-1 | CBP | 10000 | 6.23 | 7.4 |
| Embodiment 1-1 | P1 | 10000 | 5.45 | 14.6 |
| Embodiment 1-2 | P11 | 10000 | 5.55 | 16.6 |
| Embodiment 1-3 | P13 | 10000 | 5.44 | 15.0 |
| Embodiment 1-4 | P28 | 10000 | 5.52 | 14.8 |
It can be seen that by upper table data
Using the compounds of this invention as the material of main part in red phosphorescent OLED organic electroluminescence device relative to adopting
The organic electroluminescence device for using CBP as main body obtains preferable effect, obtains higher current efficiency and lower
Driving voltage；To be introduced into organic electroluminescence device containing carbazole-fluoranthene class material of main part can be substantially reduced driving electricity
Pressure and the advantage for improving luminous efficiency.
Thus it proves, this kind of Typical Representative compound containing in carbazole-fluoranthene class general formula compound of the invention and comparison are real
The material for applying example use is compared, and the stability of the compounds of this invention and carrier transmission performance when as material of main part all have
It is extremely obviously improved effect, so the compounds of this invention has practical value.
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 (8)
1. a kind of general formula compound has the structure as shown in following formula (I):
In formula (I), R is selected from lower formula (II) or (III):
In formula (II): P and Q is separately selected from C or N, and at least 1 is N；
Ra indicate mono-, di-, three, it is four substituted or unsubstituted, and any adjacent Ra is optionally connected, and R1It is optional with adjacent Ra
Connection；
Ra and R1It is respectively and independently selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30Substituted or unsubstituted virtue
Base or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
In formula (III): X, Y and Z are separately selected from C or N, and wherein at least having 1 is N；
R2And R3Separately it is selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30It is substituted or unsubstituted
Aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
It is above-mentioned to work as Ra, R1、R2And R3It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aryl
When group, the substituent group thereon is independently selected from cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, C1~C6Alkane
Oxygroup or thio alkoxy group, or it is selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S, Si
Hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, or be selected from Si (R4)3, the R4Selected from C1~C6Alkyl.
2. general formula compound according to claim 1, in the formula (II) and formula (III):
Ra、R1、R2And R3It is respectively and independently selected from C1~C5Alkyl, C6~C10Aryl amine, C6~C15It is substituted or unsubstituted
Aryl or condensed-nuclei aromatics group, C4~C15Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
As Ra, R1、R2And R3When selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, it is described its
On substituent group preferably independently be selected from cyano, or be selected from C1~C5Alkyl or cycloalkyl, Si (CH3)3, alkenyl, alkoxy or thio
Alkoxy base, or it is selected from C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, contain be selected from N or O hetero atom and C6~C15
Mononuclear aromatics or condensed-nuclei aromatics group.
3. general formula compound according to claim 1, in the formula (II) and formula (III):
Ra、R1、R2And R3It is respectively and independently selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, three
Phenylene, pyrenyl, base,Base or aphthacene base；The phenyl replaced by furyl, thienyl, pyrrole radicals and/or pyridyl group；
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, benzene binaphthyl, 4- naphthylphenyl, 6-
Phenyl napthyl, 7- phenyl phenanthryl, 9,9 '-dimethyl fluorenes, 9,9 '-spiral shell, two fluorenes, benzfluorene；
Or Ra, R1、R2And R3It is respectively and independently selected from furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, benzene
Base pyrrole radicals, pyridyl group, phenylpyridyl, pyrazinyl, fluorenyl, indeno fluorenyl, quinoline, triazine radical, benzofuranyl, benzo thiophene
Pheno base, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzoquinoline, dibenzofuran group, dibenzothiophenes
Diazole, the coffee quinoline base, coffee quinoline benzothiazolyl, benzodioxole that base, dibenzopyrrole base, carbazyl, phenyl replace
Base, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole and indolocarbazole.
4. general formula compound according to claim 1 is selected from following concrete structure formulas:
5. application of the general formula compound according to claim 1 in organic electroluminescence device.
6. application of the structural compounds according to claim 4 in organic electroluminescence device.
7. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the 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), R is selected from lower formula (II) or (III):
In formula (II): P and Q is separately selected from C or N, and at least 1 is N；
Ra indicate mono-, di-, three, it is four substituted or unsubstituted, and any adjacent Ra is optionally connected, and R1It is optional with adjacent Ra
Connection；
Ra and R1It is respectively and independently selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30Substituted or unsubstituted virtue
Base or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
In formula (III): X, Y and Z are separately selected from C or N, and wherein at least having 1 is N；
R2And R3Separately it is selected from hydrogen, C1~C10Alkyl, C6~C30Aryl amine, C6~C30It is substituted or unsubstituted
Aryl or condensed-nuclei aromatics group, C3~C30Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
It is above-mentioned to work as Ra, R1、R2And R3It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aryl
When group, the substituent group thereon is independently selected from cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, C1~C6Alkane
Oxygroup or thio alkoxy group, or it is selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing selected from N, O, S, Si
Hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, or be selected from Si (R4)3, the R4Selected from C1~C6Alkyl.
8. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the
One or more layers organic layer between two electrodes, which is characterized in that include at least one following structure chemical combination in the organic layer
Object:
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109776542A (en) * | 2017-11-10 | 2019-05-21 | 北京鼎材科技有限公司 | A kind of electroluminescent organic material and its application |
| CN112028912A (en) * | 2019-06-03 | 2020-12-04 | 北京鼎材科技有限公司 | Novel boron-containing organic electroluminescent material and application thereof |
| CN112094169A (en) * | 2019-06-18 | 2020-12-18 | 北京鼎材科技有限公司 | Organic electroluminescent material and application thereof |
| CN113444112A (en) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | Heterocyclic compounds and their use in organic electroluminescent devices |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103857673A (en) * | 2011-09-01 | 2014-06-11 | 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 |
| CN104918915A (en) * | 2013-05-02 | 2015-09-16 | 出光兴产株式会社 | Compound, material for organic electroluminescent element, and electronic device |
| CN105669467A (en) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | Compound based on fluoranthene and organic electroluminescence device |
| KR20170063394A (en) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | Hrtrro-cyclic compound and organic light emitting device comprising the same |
| US20170271598A1 (en) * | 2016-03-16 | 2017-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2017
- 2017-09-25 CN CN201710871455.4A patent/CN109553620A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103857673A (en) * | 2011-09-01 | 2014-06-11 | 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 |
| CN104918915A (en) * | 2013-05-02 | 2015-09-16 | 出光兴产株式会社 | Compound, material for organic electroluminescent element, and electronic device |
| KR20170063394A (en) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | Hrtrro-cyclic compound and organic light emitting device comprising the same |
| CN105669467A (en) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | Compound based on fluoranthene and organic electroluminescence device |
| US20170271598A1 (en) * | 2016-03-16 | 2017-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109776542A (en) * | 2017-11-10 | 2019-05-21 | 北京鼎材科技有限公司 | A kind of electroluminescent organic material and its application |
| CN112028912A (en) * | 2019-06-03 | 2020-12-04 | 北京鼎材科技有限公司 | Novel boron-containing organic electroluminescent material and application thereof |
| CN112094169A (en) * | 2019-06-18 | 2020-12-18 | 北京鼎材科技有限公司 | Organic electroluminescent material and application thereof |
| CN112094169B (en) * | 2019-06-18 | 2024-03-26 | 北京鼎材科技有限公司 | Organic electroluminescent material and application thereof |
| CN113444112A (en) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | Heterocyclic compounds and their use in organic electroluminescent devices |
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