CN105837392B - A kind of electroluminescent organic material and the electroluminescent device comprising the material - Google Patents
A kind of electroluminescent organic material and the electroluminescent device comprising the material Download PDFInfo
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Abstract
The present invention provides a kind of electroluminescent organic materials, which is characterized in that its small molecule for the structure centered on 9,9 dimethyl fluorene of naphtho-, general structure areWherein R1And R2It is identical, and selected from alkyl, aromatic group, nitrogen heterocyclic ring group, R3Selected from hydrogen, aromatic group.The present invention also provides the electroluminescent devices comprising above-mentioned material.New small molecule electroluminescent organic material provided by the invention has appropriate molecular mass, good thin film stability, suitable molecular entergy level, such material can be as the functional layer of small molecule OLED device, applied in field of organic electroluminescence.The OLED device made using such material as luminescent layer can send out navy blue fluorescence, 1300 4200cd/m of maximum brightness of device2, 1.0 1.8cd/A of maximum current efficiency, device efficiency is excellent.
Description
Technical field
The present invention relates to field of light emitting materials, more specifically it relates to a kind of electroluminescent organic material and include the material
The electroluminescent device of material.
Background technology
Organic electroluminescent diode (OLED) results from the eighties in last century, should by the continuous development of more than two decades
Item technology gradually moves to maturity, and there are many commodity based on OLED display technologies, have been carried out industrialization.With liquid crystal type
Display technology is compared, and OLED display technologies have self-luminous, wide viewing angle, wide colour gamut, fast response time, Flexible Displays etc. can be achieved
Plurality of advantages, therefore, OLED display technologies are obtaining people more and more concern and corresponding Technical investment.
OLED device is divided into two kinds of small molecule devices and macromolecule device, wherein, small molecule devices have sandwich style more
Interlayer structure, various different types of functional layers in a certain order, in the form of solid amorphous film, are produced
Between two electrodes, this be small molecule OLED device grown form.
In small molecule devices, different types of functional layer shares different types of function, as hole transmission layer is responsible for biography
Hole is led, luminescent layer is responsible for sending out the visible ray of different colours, and electron transfer layer is responsible for conducting electronics etc., excellent in order to obtain performance
Good small molecule OLED device not only needs each functional layer material self performance good, but also between requiring different function layer,
Also good matching can be carried out.
Naphthalene has stable closed loop configuration, and simple in structure, affordable, is in small molecule electroluminescent organic material,
Relatively conventional minor structure unit.The chemical property of 9,9- dimethyl fluorene structural units is stablized, and conjugate length is moderate, modifiability
By force, in small molecule OLED materials, the structural unit is also relatively conventional.Naphthalene and 9,9- dimethyl fluorenes are fabricated to simultaneously ring by inventor
Structure has obtained, with the molecule for stablizing chemical constitution and suitable molecule energy level, on this basis, repairing by appropriate chemistry
Decorations obtain the electroluminescent organic material of a kind of function admirable.
Invention content
The technical solution that the present invention solves above-mentioned technical problem is as follows：
A kind of electroluminescent organic material, which is characterized in that it is with naphtho- 9, and structure is small centered on 9- dimethyl fluorenes
Molecule, shown in general structure such as formula (I)：
Wherein R1And R2It is identical, and selected from alkyl, aromatic group, nitrogen heterocyclic ring group, R3Selected from hydrogen, aromatic group.
R1And R2Preferably C1-2 alkyl, unsubstituted phenyl and monocyclic aryl, polyaromatic, fused ring aryl or miscellaneous
The phenyl of cyclophane base substitution；More preferably：Methyl, ethyl, phenyl, 4- xenyls, to (naphthalene) phenyl, to (pyridyl group) benzene
Base, to (9,9- dimethyl fluorenyl) phenyl, to (carbazyl) phenyl or to (N, N- hexichol amido) phenyl.
R3Preferably hydrogen, unsubstituted or the phenyl, fused ring aryl, the fluorenyl that are replaced by fluorine；More preferably：Hydrogen, phenyl, list
Fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluoro phenyl, pentafluorophenyl group, 1- naphthalenes, 2- naphthalenes, phenanthryl, 9,9- dimethyl fluorenyls.
Preferably, the structural formula of the electroluminescent organic material is：
The present invention also provides a kind of electroluminescent device, including anode, hole transmission layer, luminescent layer, electron-transport
Layer, electron injecting layer and cathode, wherein luminescent layer are made of electroluminescent organic material of the present invention.
New small molecule electroluminescent organic material provided by the invention is steady with appropriate molecular mass, good film
Qualitative, suitable molecular entergy level, such material can be as the functional layer of small molecule OLED device, applied to organic electroluminescent
In field.The OLED device made using such material as luminescent layer can send out navy blue fluorescence, the maximum brightness of device
1300-4200cd/m2, maximum current efficiency 1.0-1.8cd/A, device efficiency is excellent.
Description of the drawings
Fig. 1 is the schematic diagram of the electroluminescent device of the present invention.
In attached drawing, parts list represented by the reference numerals are as follows：
101st, anode, 102, hole transmission layer, 103, luminescent layer, 104, electron transfer layer, 105, electron injecting layer, 106,
Cathode.
Specific embodiment
The principle and features of the present invention will be described below with reference to the accompanying drawings, and the given examples are served only to explain the present invention, and
It is non-to be used to limit the scope of the present invention.
The preparation of compound 1：In 500mL there-necked flasks, 1,8- dibromine naphthalenes (24.9g, 0.087mol), 9,9- diformazans are added in
Base -4- fluorenes boric acid (23.8g, 0.10mol), potassium carbonate (30g, 0.22mol), toluene (150g), ethyl alcohol (50g), deionized water
(65g) under nitrogen protection, adds in Pd (PPh3)4(0.5g) is warming up to reflux, and insulation reaction 10h is cooled to 40 DEG C, and liquid separation has
Machine is mutually after the drying of 50g anhydrous magnesium sulfates, and the quick silicagel column for crossing 15cm thickness crosses column liquid desolventizing, and gained crude product uses
Ethyl acetate/absolute ethyl alcohol is solvent recrystallization, obtains compound 1, white solid 30g, yield 86.5%, MS (m/s)：
399.3。
The preparation of compound 2：Compound 1 (3.99g, 0.01mol) is dissolved in the tetrahydrofuran of 100mL dryings, turned
Enter in the 500mL there-necked flasks equipped with constant pressure funnel, under nitrogen protection, when temperature drop is to -75 DEG C in system, be slowly added dropwise
The hexane solution (2.5mol/L) of 5.2mL n-BuLis, drop finish, and -75 DEG C of insulation reaction 2h, heat preservation is finished, and drying is added dropwise in equality of temperature
Acetone (0.58g, 0.01mol), 5min is added dropwise, equality of temperature insulation reaction 2h, heat preservation finish, room temperature continue insulation reaction 2h,
The dilute hydrochloric acid of 70g mass concentrations 10% is instilled later, stirs 1h, and liquid separation collects organic phase, sloughs solvent, obtain compound 2
Crude product 5g, the crude product of gained compound 2, is no longer refined, and is directly used in reacting in next step.
The preparation of compound 3：In 500mL there-necked flasks, the crude product (5g) of the obtained compound 2 of previous step is added in,
Glacial acetic acid 60g is added in, mass concentration is 36.5% concentrated hydrochloric acid 0.4g, is warming up to reflux, and insulation reaction 10h is cooled to 25 DEG C,
Addition 100g toluene and 200g water, liquid separation, organic phase precipitation, crude oil cross silicagel column, and petroleum ether elution is collected containing single production
Object ingredient crosses column liquid, and petroleum ether is beaten after precipitation, is filtered, and is collected filter cake, is obtained compound 3, white solid 1.22g, yield
33.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C28H24, theoretical value 360.19, test value 360.35.Member
Element analysis (C28H24), theoretical value C：93.29 H：6.71, measured value C：93.33 H：6.67.
Synthesis flow is as follows：
The preparation of 1 compound C01 of embodiment
Compound 3 (36.0g, 0.1mol) is dissolved in the DMF of 500g dryings, be transferred in L there-necked flasks, nitrogen protection
Under, dissolving is stirred at room temperature, slowly in batches add in NBS solid powders (18.69g, 0.105mol), 120 DEG C of insulation reaction 10h,
System is quickly turned to the transparent system of claret, keeps the temperature and finishes cooled to room temperature, adds in 600g toluene and 800g water, stirring
0.5h, liquid separation collect organic phase, slough solvent, obtain the crude product 58g of compound 4, and gained crude product uses equal proportion first
Benzene/ethyl alcohol/petroleum ether be solvent recrystallization, the compound 4 purified, white solid 31.77g, yield 72.3%, MS (m/
s)：438.1.
In 250mL there-necked flasks, compound 4 (4.39g, 0.01mol), phenyl boric acid (1.34g, 0.011mol), carbon are added in
Sour potassium (3g, 0.022mol), toluene (150g), ethyl alcohol (50g), deionized water (65g) under nitrogen protection, add in Pd (PPh3)4
(0.116g), Xantphos (0.116g) are warming up to reflux, insulation reaction 8h, are cooled to 40 DEG C, liquid separation, organic phase 150g
Washing is primary, liquid separation, and for organic phase after the drying of 50g anhydrous magnesium sulfates, the quick silicagel column for crossing 25cm thickness crosses column liquid desolventizing
Faint yellow solid crude product is obtained, crude product crosses silicagel column, and petroleum ether elution collects and crosses column liquid, precipitation containing single product component
Petroleum ether is beaten afterwards, is filtered, and is collected filter cake, is obtained compound C01, white solid 2.91g, yield 66.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H28, theoretical value 436.22, test value 436.10.Member
Element analysis (C34H28), theoretical value C：93.54 H：6.46, measured value C：93.55 H：6.45.
The preparation of 2 compound C03 of embodiment
In 250mL there-necked flasks, addition compound 4 (4.39g, 0.01mol), pentafluorophenyl boric acid (2.33g,
0.011mol), potassium carbonate (3g, 0.022mol), toluene (150g), ethyl alcohol (50g), deionized water (65g), under nitrogen protection,
Add in Pd (PPh3)4(0.116g), Xantphos (0.116g) are warming up to reflux, insulation reaction 8h, are cooled to 40 DEG C, liquid separation,
Organic phase washes primary, liquid separation with 150g, and organic phase is after the drying of 50g anhydrous magnesium sulfates, the quick silicagel column for crossing 25cm thickness,
It crosses column liquid desolventizing and obtains faint yellow solid crude product, crude product crosses silicagel column, and petroleum ether elution collects and crosses column containing single product component
Liquid, petroleum ether is beaten after precipitation, is filtered, and is collected filter cake, is obtained compound C03, white solid 3.75g, yield 71.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H23F5, theoretical value 526.17, test value 526.02.Member
Element analysis (C34H23F5), theoretical value C：77.56 H：4.40 F：18.04 measured value C：77.52 H：4.41,F：18.07.
The preparation of 3 compound C04 of embodiment
Replace acetone as raw material using pentanone, according to the preparation method of compound 2, put into 0.69g (0.008mol, 0.8
Equivalent) pentanone, 5 crude product of compound is obtained, is no longer refined, is directly used in reacting in next step.
Compound 2 is replaced, according to 1 the method for embodiment (preparation of compound 3), to be thrown as raw material using compound 5
Enter 0.008mol (theoretical value) compound 5, obtain compound C04, white solid 1.85g, yield 59.4%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C30H28, theoretical value 388.22, test value 388.41.Member
Element analysis (C30H28), theoretical value C：92.74 H：7.26, measured value C：92.76 H：7.24.
The preparation of 4 compound C05 of embodiment
Compound C04 (38.9g, 0.1mol) is dissolved in the DMF of 500g dryings, be transferred in 2L there-necked flasks, nitrogen is protected
Under shield, dissolving is stirred at room temperature, slowly adds in NBS solid powders (18.69g, 0.105mol), 120 DEG C of isothermal reactions in batches
10h, system are quickly turned to the transparent system of claret, keep the temperature and finish cooled to room temperature, add in 600g toluene and 800g water, stirring
0.5h, liquid separation collect organic phase, slough solvent, obtain the crude product 62g of compound 6, and gained crude product uses equal proportion first
Benzene/ethyl alcohol/petroleum ether be solvent recrystallization, the compound 6 purified, white solid 34.17g, yield 73.1%, MS (m/
s)：466.1.
In 250mL there-necked flasks, compound 6 (4.67g, 0.01mol), phenyl boric acid (1.34g, 0.011mol), carbon are added in
Sour potassium (3g, 0.022mol), toluene (150g), ethyl alcohol (50g), deionized water (65g) under nitrogen protection, add in Pd (PPh3)4
(0.116g), Xantphos (0.116g) are warming up to reflux, insulation reaction 8h, are cooled to 40 DEG C, liquid separation, organic phase 150g
Washing is primary, liquid separation, and for organic phase after the drying of 50g anhydrous magnesium sulfates, the quick silicagel column for crossing 25cm thickness crosses column liquid desolventizing
Faint yellow solid crude product is obtained, crude product crosses silicagel column, and petroleum ether elution collects and crosses column liquid, precipitation containing single product component
Petroleum ether is beaten afterwards, is filtered, and is collected filter cake, is obtained compound C05, white solid 3.50g, yield 75.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C36H32, theoretical value 464.25, test value 464.43.Member
Element analysis (C36H32), theoretical value C：93.06 H：6.94, measured value C：93.03 H：6.97.
The preparation of 5 compound C07 of embodiment
Acetone is replaced, according to the preparation method of compound 2, to put into 1.46g as raw material using benzophenone
(0.008mol, 0.8 equivalent) benzophenone, obtains 7 crude product of compound, is no longer refined, and is directly used in and reacts in next step
In.
Compound 2 is replaced as raw material using compound 7, according to the preparation of compound 3, input 0.008mol (theoretical value)
Compound 7 obtains compound C07, white solid 2.20g, yield 56.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C38H28, theoretical value 484.22, test value 484.43.Member
Element analysis (C38H28), theoretical value C：94.18 H：5.82, measured value C：94.12 H：5.88.
The preparation of 6 compound C09 of embodiment
Compound 3 is replaced, according to the preparation method of compound 4, to put into 4.85g as raw material using compound C07
(0.01mol) compound C07, the compound 8 purified, faint yellow solid 4.23g, yield 75.1%, MS (m/s)：
562.1。
4,2,4- difluoro phenyl boric acid of compound is replaced to replace phenyl boric acid as raw material using compound 8, according to compound C01
Preparation method, put into 2.82g (0.005mol) compound 8,0.87g (0.0055mol) 2,4- difluoro phenyl boric acids obtain chemical combination
Object C09, white solid 1.93g, yield 64.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C44H30F2, theoretical value 596.23, test value 596.31.Member
Element analysis (C44H30F2), theoretical value C：88.56 H：5.07 F:6.37, measured value C：88.53 H：5.08 F:6.39.
The preparation of 7 compound C12 of embodiment
2,4- difluoros phenyl boric acid is replaced as raw material using 1- naphthalene boronic acids, according to the preparation method of compound C09, inputization
Object 8 (5.64g, 0.01mol) is closed, obtains compound C12, white solid 4.93g, yield 80.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C48H34, theoretical value 610.27, test value 610.10.Member
Element analysis (C48H34), theoretical value C：94.39 H：5.61, measured value C：94.41 H：5.59.
The preparation of 8 compound C15 of embodiment
The preparation of compound C15：2,4- difluoros phenyl boric acid is replaced as raw material using 9,9- dimethyl -2- boric acid, according to
The preparation method of compound C09, input compound 8 (5.64g, 0.01mol), obtains compound C15, white solid 5.62g, receives
Rate 83.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H40, theoretical value 676.31, test value 676.45.Member
Element analysis (C53H40), theoretical value C：94.04 H：5.96, measured value C：94.06 H：5.94.
The preparation of 9 compound C17 of embodiment
Acetone is replaced, according to the preparation method of compound 2, to put into 30.6g as raw material using 4,4 '-dibromobenzo-phenone
(0.09mol, 0.9 equivalent) 4,4 '-dibromobenzo-phenone obtain 9 crude product of compound, are no longer refined, be directly used in down
In single step reaction.
Replacing compound 2 using compound 9, according to the preparation method of compound 3, input 0.09mol is (theoretical as raw material
Value) compound 9, obtain compound 10, white solid 25.3g, yield 43.7%, MS (m/s)：642.0.
Compound 4 is replaced, according to the preparation method of compound C01, to put into 6.42g as raw material using compound 10
(0.01mol) compound 10 obtains compound C17, white solid 5.37g, yield 84.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C50H36, theoretical value 636.28, test value 636.44.Member
Element analysis (C50H36), theoretical value C：94.30 H：5.70, measured value C：94.28 H：5.72.
The preparation of 10 compound C18 of embodiment
Compound 3 is replaced, according to the preparation method of compound 4, to put into 12.74g as raw material using compound C17
(0.02mol) compound C17, the compound 11 purified, faint yellow solid 10.41g, yield 72.7%, MS (m/s)：
714.19。
Compound 4 is replaced using compound 11, according to the preparation method of compound C01, input 3.58g (0.005mol) changes
Object 11 is closed, 0.67g (0.0055mol) phenyl boric acid obtains compound C18, white solid 2.86g, yield 80.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C56H40, theoretical value 712.31, test value 712.09.Member
Element analysis (C56H40), theoretical value C：94.34 H：5.66, measured value C：94.35 H：5.65.
The preparation of 11 compound C19 of embodiment
Phenyl boric acid is replaced as raw material using 3,4,5- trifluoro phenyl boric acids, according to the preparation method of compound C18, inputization
Object 11 (7.16g, 0.01mol) is closed, obtains compound C19, white solid 6.19g, yield 80.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C56H37F3, theoretical value 766.28, test value 766.11.Member
Element analysis (C56H37F3), theoretical value C：87.70 H：4.86 F：7.44, measured value C：87.65 H：4.88 F：7.47.
The preparation of 12 compound C22 of embodiment
In 250mL there-necked flasks, addition compound 10 (6.42g, 0.01mol), 2- naphthalene boronic acids (3.78g, 0.022mol),
Potassium carbonate (4.14g, 0.03mol), toluene (150g), ethyl alcohol (50g), deionized water (65g) under nitrogen protection, add in Pd
(OAc)2(0.025g), Xantphos (0.116g) are warming up to reflux, insulation reaction 8h, are cooled to 30 DEG C, liquid separation, organic phase
Primary, the liquid separation with 150g washings, for organic phase after the drying of 40g anhydrous magnesium sulfates, the quick silicagel column for crossing 20cm thickness crosses column liquid
Desolventizing obtains faint yellow solid crude product, and crude product crosses silicagel column, and petroleum ether elution collects and crosses column liquid containing single product component, takes off
Petroleum ether mashing after molten, filters, and collects filter cake, obtains compound C22, white solid 6.06g, yield 82.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C58H40, theoretical value 736.31, test value 736.15.Member
Element analysis (C58H40), theoretical value C：94.53 H：5.47, measured value C：94.59 H：5.41.
The preparation of 13 compound C26 of embodiment
2- naphthalene boronic acids is replaced, according to the preparation method of compound C22, to put into compound as raw material using 3- pyridine boronic acids
10 (6.42g, 0.01mol) obtain compound C26, white solid 5.31g, yield 83.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C48H34N2, theoretical value 638.27, test value 638.44.Member
Element analysis (C48H34N2), theoretical value C：90.25 H：5.36 N：4.39, measured value C：90.28 H：5.34,N：4.38.
The preparation of 14 compound C27 of embodiment
2- naphthalene boronic acids is replaced, according to the preparation method of compound C22, to put into compound as raw material using 3- pyridine boronic acids
10 (6.42g, 0.01mol) obtain compound C27, white solid 5.40g, yield 84.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C48H34N2, theoretical value 638.27, test value 638.36.Member
Element analysis (C48H34N2), theoretical value C：90.25 H：5.36 N：4.39, measured value C：90.27 H：5.33,N：4.40.
The preparation of 15 compound C28 of embodiment
Compound C17 is replaced, according to the preparation method of compound 11, to put into compound as raw material using compound C26
C26 (6.39g, 0.01mol) obtains 12 fine work of compound, faint yellow solid 3.27g, yield 45.5%, MS (m/s)：
716.18。
Compound 11 is replaced, according to the preparation method of compound C18, to put into compound 12 as raw material using compound 12
(7.18g, 0.01mol) obtains compound C28, white solid 4.01g, yield 56.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C54H38N2, theoretical value 714.30, test value 714.12.Member
Element analysis (C54H38N2), theoretical value C：90.72 H：5.36 N：3.92, measured value C：90.71 H：5.38,N：3.91.
The preparation of 16 compound C31 of embodiment
In 250mL there-necked flasks, compound 10 (6.42g, 0.01mol), carbazole (3.68g, 0.022mol), tertiary fourth are added in
Sodium alkoxide (2.88g, 0.03mol), palladium (0.246g), Xantphos (1.161g), dimethylbenzene (120g), under nitrogen protection,
It is warming up to reflux, insulation reaction 8h is cooled to 30 DEG C, adds in 60mL deionized waters, stirs 5min, liquid separation, organic phase desolventizing,
Gained 10g crude products are purified using silica gel column chromatography, and eluant, eluent is petroleum ether：Toluene=6:1 (V/V) merges simultaneously precipitation, remaining
The reflux mashing of object petroleum ether, room temperature filter, the compound C31 purified, white solid 5.12g, yield 62.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C62H42N2, 814.33 test value 814.10 of theoretical value.Member
Element analysis (C62H42N2), theoretical value C：91.37 H：5.19 N：3.44, measured value C：91.39 H：5.19 N：3.42.
The preparation of 17 compound C33 of embodiment
Carbazole is replaced, according to the preparation method of compound C31, to put into compound 10 as raw material using diphenylamines
(6.42g, 0.01mol) obtains compound C33, white solid 5.99g, yield 73.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C62H46N2, theoretical value 818.37, test value 818.11.Member
Element analysis (C62H46N2), theoretical value C：90.92 H：5.66 N：3.42, measured value C：90.91 H：5.65,N：3.44.
Organic electroluminescence device embodiment：
The present invention chooses compound C03, compound C04, compound C07, compound C12, compound C15, compound
C22, compound C26, compound C31, compound C33 make organic electroluminescence device, should manage as emitting layer material
Solution, device implementation process with as a result, being intended merely to preferably explain the present invention, not limitation of the present invention.
The preparation of 18 organic electroluminescence device 1 of embodiment
The present embodiment prepares organic electroluminescence device 1 by the following method：
A) ITO (tin indium oxide) glass is cleaned：Respectively each 30 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate
Then clock is handled 5 minutes in plasma cleaner；
B) the vacuum evaporation hole transmission layer NPB on anode ito glass, thickness 50nm；
C) on hole transmission layer NPB, vacuum evaporation luminescent layer compound C03, thickness 30nm；
D) on luminescent layer, the vacuum evaporation TPBI as electron transfer layer, thickness 30nm；
E) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness 1nm；
F) on electron injecting layer, vacuum evaporation cathode Al, thickness 100nm.
The structure of organic electroluminescence device 1 is ITO/NPB (50nm)/compound C03 (30nm)/TPBI (30nm)/LiF
(1nm)/Al (100nm), during vacuum evaporation, pressure<1.0X 10-3Pa, device one open bright voltage, maximum current efficiency,
The photooptical datas such as excitation purity are listed in Table 1 below.
The preparation of 27 organic electroluminescence device 2-9 of embodiment 20- embodiments
Respectively with compound C04, compound C07, compound C12, compound C15, compound C22, compound C26, change
It closes object C31, compound C33 and replaces compound C03, according to 19 the method for embodiment, make organic electroluminescence device 2-9.
Organic electroluminescence device 1-9's opens the photoelectric parameters such as bright voltage, maximum current efficiency, excitation purity such as the following table 1 institute
Show.
The photoelectric parameter of 1 organic electroluminescence device 1-9 of table
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.
Claims (3)
1. a kind of electroluminescent organic material, which is characterized in that it is small point of structure centered on 9- dimethyl fluorenes with naphtho- 9
Son, shown in general structure such as formula (I)：
R1And R2Selected from methyl, ethyl, phenyl, 4- xenyls, to (naphthalene) phenyl, to (pyridyl group) phenyl, to (9,9- diformazans
Base fluorenyl) phenyl, to (carbazyl) phenyl, to (N, N- hexichol amido) phenyl；
R3Selected from hydrogen, phenyl, single fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluoro phenyl, pentafluorophenyl group, 1- naphthalenes, 2- naphthalenes,
Phenanthryl, 9,9- dimethyl fluorenyls.
2. electroluminescent organic material according to claim 1, which is characterized in that the knot of the electroluminescent organic material
Structure formula is：
3. a kind of electroluminescent device, which is characterized in that including anode, hole transmission layer, luminescent layer, electron transfer layer, electronics
Implanted layer and cathode, wherein the luminescent layer is made of the electroluminescent organic material described in any one of claim 1-2.
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| CN103221406A (en) * | 2010-09-17 | 2013-07-24 | 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 |
| KR20130135516A (en) * | 2012-06-01 | 2013-12-11 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| CN105418357A (en) * | 2015-11-20 | 2016-03-23 | 江苏三月光电科技有限公司 | Benzo spirofluorene compound and application thereof in OLED |
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| CN103221406A (en) * | 2010-09-17 | 2013-07-24 | 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 |
| KR20130135516A (en) * | 2012-06-01 | 2013-12-11 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| CN105418357A (en) * | 2015-11-20 | 2016-03-23 | 江苏三月光电科技有限公司 | Benzo spirofluorene compound and application thereof in OLED |
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