CN108059644A - The electroluminescent organic material of a kind of naphthalene azepine dibenzo substitution as ligand and application thereof - Google Patents
The electroluminescent organic material of a kind of naphthalene azepine dibenzo substitution as ligand and application thereof Download PDFInfo
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
It is a kind of to be substituted using naphthalene azepine dibenzo as compound of ligand and application thereof.The compound has structure shown in Formulas I.Compound provided by the invention has the advantages that thermal stability is good, and luminous efficiency is high, long lifespan, can be used in organic luminescent device, especially as emitting red light doping body, has the possibility applied to AMOLED industries.
Description
Technical field
It is more particularly to a kind of using the substitution of naphthalene azepine dibenzo as ligand the invention belongs to electroluminescent material field
Electroluminescent organic material and application thereof.
Background technology
Organic electroluminescent refers to that the thin-film device being prepared by organic photoelectric functional material excitation on the scene issues
The phenomenon that light.Difference according to luminescent material used by function film is prepared can be divided into organic electroluminescent LED (OLED)
With polymer electroluminescence diode (PLED).
OLED possesses the unmatched advantage of existing display technology as a kind of brand-new display technology in each performance,
Such as have it is all solid state, from main light emission, brightness height, high-resolution, visual angle wide (170 degree or more), fast response time, thickness is thin, body
Product is small, light-weight, flexible base board, low-voltage direct-current driving (3-10V) can be used, low in energy consumption, operating temperature range is wide etc. so that
Its application market is very extensive, as lighting system, communication system, car-mounted display, portable electric appts, fine definition are shown
Even military field.
The luminescence process of OLED device is as follows, the injection of (1) carrier：Under the action of extra electric field, electronics and hole
Respectively the organic functional thin film layer of folder between the electrodes is injected into from cathode and anode；(2) migration of carrier：Injected electrons
It is migrated respectively from electron transfer layer hole transmission layer to luminescent layer with hole；(3) carrier is compound：Electronics and hole combine production
Raw exciton；(4) migration of exciton：Exciton migrates under electric field action, transfers energy to optical molecule, and excites electronics from ground state
Transit to excitation state；(5) electroluminescent：Excited energy is generated photon, is released energy by Radiation-induced deactivation.When electronics and sky
Cave in conjunction with rear, because the difference of electron spin symmetric mode, can generate the form of two kinds of excitation state in organic molecule, a kind of
25% is accounted for for singlet state, one kind is triplet 75%.
Electroluminescent organic material is the core component of organic electroluminescence device, the thermal stability of material, photochemical
It learns stability, quantum efficiency, film forming and crystallinity etc. all to have a great impact to the performance of making devices, may include fluorescence
Material and phosphor material.
It is generally believed that fluorescent material is usually organic small molecule material, the limit of internal quantum is 25%, such as CN
105418582A discloses a series of high fluorescent material comprising single (n=0) or (n=1,2 etc.) benzoheterocyclic systems.And phosphorus
Luminescent material can utilize the energy of 75% triplet exciton, institute due to Effect of Spin-orbit Coupling caused by heavy atoms effect
Luminous efficiency is improved with unquestionable.Compared with fluorescent material, phosphor material is not only started late, and with thermal stability
The problems such as difference, luminous efficiency is low, short life, and color saturation is low are the problem of a great challenge so far.
The content of the invention
One of the objects of the present invention is to provide a kind of miscellaneous co-ordination complex using the substitution of naphthalene azepine dibenzo as ligand
The noval chemical compound of object, such luminescent material have the advantages that thermal stability is good, and luminous efficiency is high, long lifespan, can be used for organic
In luminescent device, especially as emitting red light doping body, there is the possibility applied to AMOLED industries.
In order to achieve the above object, the present invention adopts the following technical scheme that：
A kind of compound using the substitution of naphthalene azepine dibenzo as ligand, structure is shown in Formulas I：
Wherein,
R1, R2, R3It is each independently selected from hydrogen, alkyl, miscellaneous alkyl, aryl or heteroaryl；
Z in Rc is selected from O, S, CR2, NR or Se, and wherein R is alkyl, miscellaneous alkyl, aryl or heteroaryl etc.；
X in Rc structures1, X2, X3, X4It independently is C or N；
M is metal；
X-Y is monoanionic bidentate ligand；
A and b's and for metal ion valence state.
Preferably, the compound has with Formula Il structure：
Preferably, R1, R3Hydrogen, monosubstituted, disubstituted or polysubstituted is each independently, it is preferably monosubstituted.
Preferably, R2Hydrogen, monosubstituted, disubstituted or polysubstituted independently is, is preferably hydrogen.
Preferably, R2, R3Independently be substituent group or with parent formed and ring structure.
Preferably, R1, R2, R3The alkyl or miscellaneous alkyl of the supplied for electronic no more than four carbon atom independently are, is preferably
The alkyl of the collateralization of supplied for electronic containing no more than 4 carbon atoms.
Preferably, R1The position of substitution be metal-nitrogen key adjacent position.
Preferably, R1The position of substitution be metal-nitrogen key relative position.
Preferably, R2The position of substitution be metal-carbon key adjacent position.
Preferably, the X in Rc structures1, X2, X3, X4In not more than 3 be N, preferably not more than 2 be N, further
It is N to be preferably not more than 1.
Preferably, M is the metal that atomic is more than 40, it is preferably Cu, Pt, Pd, Os or Ir, further preferably Pt
Or Ir, particularly preferably Ir.
X-Y can be identical with the ligand on the left side, can not also be same, preferably, X-Y is different from the ligand on the left side.Work as X-Y
During with the main ligand difference on the left side, X-Y is preferably 1,3- diketone class formations.
Preferably, the compound is with lower structure：
Preferably, the compound is with lower structure：
An object of the present invention, which also resides in, provides a kind of OLED phosphorescent guest materials containing above-claimed cpd.
An object of the present invention, which also resides in, provides a kind of OLED device containing compound described above.
The material of the present invention not only has higher luminous efficiency, and has the red colour code of more saturation, while device
Part lasts a long time.The metal complex of the present invention is as guest materials, because triplet excitation can be converted into light,
Applied to display devices such as organic electroluminescents, device light emitting efficiency can be improved, it is thus possible to reduce energy consumption.Meanwhile this hair
Bright complex has many advantages, such as that good stability, long lifespan, color saturation are high, has in the display devices industry such as OLED good
Application prospect.
Specific embodiment
Of the invention for ease of understanding, it is as follows that the present invention enumerates embodiment.Those skilled in the art are it will be clearly understood that the implementation
Example is used only for helping to understand the present invention, is not construed as the concrete restriction to the present invention.
Raw material, acid base catalysator and solvent in the present invention involved in compound synthesis be purchased from lark prestige science and technology,
The supplier well known to those skilled in the art such as Sigma.
Embodiment：
The shared intermediate synthesis of Formula VIII：
The synthesis of compound 2：
By compound 1 (20.29g, 0.1mol, 1.0eq), duplex frequency that borate (38.2g, 0.15mol, 1.5eq) and
One 3L's of K2CO3 (41.4g, 0.3mol, 3.0eq) and Pd (dppf) Cl2 (3.655g, 0.005mmol, 0.05eq) loadings
In round-bottomed flask, add in the anhydrous THF of 1L, nitrogen protection is lower be stirred at reflux at 80 DEG C 16 it is small when.Room temperature is then cooled to, uses rotation
Turn evaporimeter to be concentrated in vacuo to remove organic solvent, residue 1L dichloromethane dissolves, and is slowly added into 500ml unsaturated carbonates
Sodium water solution stirs, and layering, organic phase uses saturated sodium carbonate (300ml*3), H2O (300ml*3) and saturated sodium-chloride successively
(300ml*3) is washed, and is filtered after sodium sulphate drying, filtrate is concentrated in vacuo to remove organic solvent simultaneously using Rotary Evaporators
Crude product is obtained, (volume ratio is 1 using ethyl acetate/petroleum ether:2) gained crude product is subjected to column chromatography purification for mobile phase,
Compound 2 (22.3g, yield are obtained after being dried in vacuo at 50 DEG C：88.85%).Result:Yield:88.85%.MS:m/z
=252.1 (M+H+)；1HNMR(400M,d6-DMSO):6.06(s,1H),2.37(s,1H),1.26(s,12H).
The synthesis of compound 3：
By compound 2 (30.13g, 0.12mol, 1.2eq), 1,2- dibromobenzenes (23.39g, 0.1mol, 1.0eq) and
Cs2CO3 (97.5g, 0.3mol, 3.0eq) and Pd (dppf) Cl2 (3.655g, 0.005mmol, 0.05eq) is packed into a 3L
Round-bottomed flask in, add in 1L dry toluenes, nitrogen protection is lower be stirred at reflux at 110 DEG C 16 it is small when.Room temperature is then cooled to, is made
It is concentrated in vacuo to remove organic solvent with Rotary Evaporators, residue 1L dichloromethane dissolves, and is slowly added into 500ml saturations
Aqueous sodium carbonate stirs, and layering, organic phase uses saturated sodium carbonate (300ml*3), H2O (300ml*3) and saturation chlorine successively
Change sodium (300ml*3) to wash, be filtered after sodium sulphate drying, filtrate is concentrated in vacuo to remove organic molten using Rotary Evaporators
Agent simultaneously obtains crude product, and using ethyl acetate/petroleum ether, (volume ratio is 1:2) gained crude product progress column chromatography is carried for mobile phase
It is pure, obtain compound 3 (21.5g, yield after being dried in vacuo at 50 DEG C：77.06%).Result:Yield:77.06%.MS:
M/z=279.9 (M+H+)；1HNMR(400M,d6-DMSO):7.49(dd,1H),7.37(dd,1H),7.26(dd,1H),7.11
(dd,1H),6.08(s,1H),2.37(s,1H).Anal.Calcd for C12H10BrNO2:C,51.45；H,3.60；N,
5.00.Found:C,51.45；H,3.60；N,5.00.
The synthesis of compound 4：
By compound 3 (55.8g, 0.2mol, 1.0eq) and Pd (OAc) 2 (2.24g, 0.01mol, 0.05eq), Binap
(12.45g, 0.02mol, 0.1eq) is dissolved in dry 2L toluene, and obtained mixed liquor is in the lower reaction 16 of 110 DEG C of nitrogen protections
After hour, it is cooled to room temperature.Substance in above-mentioned flask after cooling is spin-dried for, and 600mL deionizations are added in into residue
Water and 600mL ethyl acetate after stirring 30 minutes at 30 DEG C, stand, after organic phase is mutually layered with water, the two are separated.
Organic phase washed with water after separation is washed into 3 times (every time with water 600mL), saturated common salt water washing (uses saline solution 3 times every time
600mL).Washed organic phase is dried with anhydrous sodium sulfate, filtering is spin-dried for, obtained material using ethyl acetate/petroleum ether as
Mobile phase carries out column chromatography purification, and compound 4 (30.5g, yield are obtained after purification products therefrom is dried in vacuo at 50 DEG C：
76.6%).Result:Yield:76.6%.MS:M/z=200.1 (M+H+)；1HNMR(400M,d6-DMSO):7.49(dd,
1H),7.42(dd,1H),7.19(dd,1H),7.11(dd,1H),6.58(s,1H),2.37(s,1H)。Anal.Calcd for
C12H9NO2:C,72.35；H,4.55；N,7.03.Found:C,72.35；H,4.55；N,7.03.
The synthesis of compound 5：
Compound 4 (19.9g, 0.1mol, 1.0eq) and triethylamine (20.2g, 0.2mol, 2.0eq) are dissolved in dry 1L
In anhydrous methylene chloride, be slowly added into be dissolved in anhydrous methylene chloride Trifluoromethanesulfonic anhydride (33.84g, 0.12mol,
1.2eq), the mixed liquor obtained is when the lower reaction 16 of 30 DEG C of nitrogen protections is small.The addition 600mL deionized waters into reaction solution, 30
After being stirred 30 minutes at DEG C, stand, after organic phase is mutually layered with water, the two is separated.Organic phase after separation is used successively
Water washing 3 times (using water 600mL every time), saturated common salt water washing 3 times (using saline solution 600mL every time).It will be washed organic
Mutually to be dried with anhydrous sodium sulfate, filtering is spin-dried for, and obtained material carries out column chromatography purification by mobile phase of ethyl acetate/petroleum ether,
Compound 5 (28.6g, yield are obtained after purification products therefrom is dried in vacuo at 50 DEG C：86.4%).Result:Yield:
86.4%.MS:M/z=332.1 (M+H+).
The synthesis of compound 6：
By compound 5 (33.1g, 0.1mol, 1.0eq), 3- methyl -5- isobutyl group -1- naphthalene boronic acids (29.1g, 0.12mol,
1.2eq) filled with Cs2CO3 (97.5g, 0.3mol, 3.0eq) and Pd (dppf) Cl2 (3.655g, 0.005mmol, 0.05eq)
In the round-bottomed flask for entering a 3L, add in 1L dry toluenes, nitrogen protection is lower be stirred at reflux at 110 DEG C 16 it is small when.With postcooling
To room temperature, it is concentrated in vacuo to remove organic solvent using Rotary Evaporators, residue 1L dichloromethane is dissolved, is slowly added into
500ml saturated aqueous sodium carbonates stir, layering, and organic phase is successively with saturated sodium carbonate (300ml*3), H2O (300ml*3)
And saturated sodium-chloride (300ml*3) washing, sodium sulphate drying after filter, filtrate using Rotary Evaporators be concentrated in vacuo with
Removal organic solvent simultaneously obtains crude product, and using ethyl acetate/petroleum ether, (volume ratio is 1:3) for mobile phase by gained crude product into
Row column chromatography purifies, and compound 6 (26.38g, yield are obtained after being dried in vacuo at 50 DEG C：69.6%).Result:Yield:
69.6%.MS:M/z=380.2 (M+H+)；1HNMR(400M,d6-DMSO):7.88(s,1H),,7.58(s,1H),7.52
(dd,1H),7.49(dd,1H),7.45(dd,1H),7.42(dd,1H),7.09-7.19(m,4H),2.95(d,2H),2.46
(s,3H),2.37(s,3H),2.22(m,1H),1.01(d,6H).Anal.Calcd for C27H25NO:C,85.45；H,
6.64；N,3.69.Found:C,85.42；H,6.65；N,3.71.
The synthesis of compound 7：
By compound 6 (11.38g, 0.03mol, 3.0eq) and three hydrated iridium trichlorides (3.52g, 0.01mol,
It 1.0eq) is placed in three-necked flask, adds in cellosolvo (66.7ml) and deionized water (33.3ml), obtained mixing
Liquid is in the lower reaction 16hrs of 110 DEG C or so nitrogen protections.It is cooled to room temperature, filters, skim filtrate, filter residue uses methanol (50ml successively
× 3) n-hexane (50ml × 3) are dried to obtain gray solid compound 7 (5.2g, yield：52.8%).Obtained compound 7 is not
It is purified to be directly used in next step.1969.8
The synthesis of 1 compound CPD3 of embodiment
Dichloro bridge cooperation compounds 7 (4.93g, 2.5mmol, 1.0eq) are dissolved in cellosolvo (25ml), successively
Natrium carbonicum calcinatum (6.9g, 50mmol, 20.0eq) and acetylacetone,2,4-pentanedione (2.5g, 25mmol, 10.0eq) are added in, after addition,
Under nitrogen protection, room temperature is cooled to after reacting 16hrs at 30 DEG C.1g celites and 200ml dichloromethane are added in into reaction solution
With lysate, then mixed liquor is filtered by celite bed, filtrate is filtered again by short silicagel column, and obtained filtrate rotation is except big
Part methylene chloride adds in isopropanol 30ml thereto, and red solid, filtering is precipitated.Solid is obtained by column chromatography for separation
Objective complex CPD3.(2.35g, yield：44.8%).Result of CPD3:Yield:44.8%.MS:M/z=1049.4
(M+H+)。
The synthesis of 2 compound CPD4 of embodiment
Dichloro bridge cooperation compounds 7 (4.23g, 2.5mmol, 1.0eq) are dissolved in cellosolvo (25ml), successively
Add in natrium carbonicum calcinatum (6.9g, 50mmol, 20.0eq) and 2,8- dimethylnonane -4,6- diketone (4.6g, 25mmol,
10.0eq), after addition, under nitrogen protection, room temperature is cooled to after reacting 16hrs at 30 DEG C.1g is added in into reaction solution
Then celite and 200ml dichloromethane are filtered mixed liquor by celite bed, filtrate passes through short silicagel column mistake again with lysate
Filter, obtained filtrate rotation add in isopropanol 30ml, red solid, filtering are precipitated thereto except most of dichloromethane.Solid exists
Objective complex CPD4 is obtained by column chromatography for separation.(2.15g, yield：37.9%).Result of CPD4:Yield:
37.9%.MS:M/z=1133.5 (M+H+).
The synthesis of 3 compound CPD5 of embodiment
Dichloro bridge cooperation compounds 7 (4.23g, 2.5mmol, 1.0eq) are dissolved in cellosolvo (25ml), successively
Addition natrium carbonicum calcinatum (6.9g, 50mmol, 20.0eq) and 2,2,6,6- tetramethyl base heptane -3,5- diketone (4.6g, 25mmol,
10.0eq), after addition, under nitrogen protection, room temperature is cooled to after reacting 16hrs at 30 DEG C.1g is added in into reaction solution
Then celite and 200ml dichloromethane are filtered mixed liquor by celite bed, filtrate passes through short silicagel column mistake again with lysate
Filter, obtained filtrate rotation add in isopropanol 30ml, red solid, filtering are precipitated thereto except most of dichloromethane.Solid exists
Objective complex CPD5 is obtained by column chromatography for separation.(2.01g, yield：35.4%).Result of CPD5:Yield:
35.4%.MS:M/z=1133.5 (M+H+).
The synthesis of 4 compound CPD6 of embodiment
The first step：The synthesis of fluoroform sulphonate
Dimer compound 7 (39.39g, 0.02mol, 1.0eq) is dissolved in 1L dichloromethane, is added successively thereto
Enter trifluoro-methane sulfonic acid silver (10.5g, 0.04mol, 2.0eq) and isopropanol (75ml).The mixture is stirred overnight at room temperature.
Silver chlorate is filtered to remove, filtrate is spin-dried for, and obtains 47g products, and obtained product is directly used in without purifying to react in next step.
Second step：The synthesis of compound 8
By the product (24.37g, 0.02mol, 1.0eq) of the first step and 2- phenylpyridines (9.3g, 0.06mol, 3.0eq)
Be dissolved in 200ml absolute ethyl alcohols, by mixture under nitrogen atmosphere heated overnight at reflux.After reaction solution is cooled to room temperature,
Precipitation is filtered and is washed 3 times with methanol, n-hexane successively.Target compound CPD6 is obtained after being dried in vacuo at 50 DEG C
(14.1g, yield 63.9%).Result of CPD6:Yield:63.9%.MS:M/z=1104.4 (M+H+).
With similary similar method can synthesize other general formulas for example formula III, formula IV, Formula V, Formula IV, Formula VII it is corresponding
Compound, it is only necessary to choose corresponding raw material.
Application examples：
The preparation of organic electroluminescence device
The glass substrate with ito transparent electrode of 25mm × 75mm × 1.1mm thickness is subjected to 5 minutes ultrasounds in isopropanol
After washing, 30 minutes ozone washings are carried out.The film thickness of ITO is set as 100nm.By the glass base with transparent electrode lines after washing
Plate is installed on the substrate holder of vacuum deposition apparatus, first according to covering transparent electrode on the face for having transparent electrode lines one side
Mode compound HATCN is deposited, formed film thickness be 10nm compound HATCN films, the tunic be used as hole injection layer, this
Outside, the function of ITO is also planarized.And then HIL2 is deposited on HATCN, forms film thickness and injects material as hole for 125nm
Material has been deposited after HIL2 and the film thickness of HTM formation 25nm is and then being deposited above, as hole mobile material.On HTM films altogether
Host and doped compound (comparative Cpd, Cpd-3, Cpd-4, Cpd-5, Cpd-6) is deposited, forms film thickness as 25nm
Luminescent layer, dopant material concentration be 10%.ETL of the vapor deposition as electron transport material over the light-emitting layer forms film thickness
For the electron transfer layer of 20nm.LiF is deposited on the electron transport layer, forms the LiF layers that film thickness is 1nm.The evaporation metal on LiF
Al forms the metallic cathode that film thickness is 80nm.Organic electroluminescence device structure is expressed as with skeleton symbol：ITO(100nm)/HATCN
(10nm)/HIL2(125nm)/HTM(25nm)/EML(Host:Dopant=90:10,25nm)/ETL(20nm)/LiF(1nm)/
Al(80nm)。
The device of above-mentioned manufacture is subjected to performance detection, shown in the following table 1.
Table 1
| Guest materials | Voltage/V | Cd/A | Lm/W | CIEx | CIEy | LT90@1000nits |
| Cpd3 | 4.5 | 19 | 13.26 | 0.662 | 0.312 | 162 |
| Cpd4 | 4.2 | 23 | 17.19 | 0.664 | 0.309 | 177 |
| Cpd5 | 4.3 | 21 | 15.35 | 0.663 | 0.308 | 168 |
| Cpd6 | 4.4 | 22 | 15.70 | 0.665 | 0.306 | 187 |
| Comparative Cpd | 5.3 | 14 | 8.29 | 0.660 | 0.330 | 108 |
It can be seen that from the testing result in table 1 compared with comparative example, the material in the present invention not only has higher
Luminous efficiency, and the red colour code with more saturation, while device lifetime is superior compared with comparative example.
The above results show present invention design metal complex as guest materials, because triplet excitation can be turned
It changes into luminous, so applied to the display devices such as organic electroluminescent, device light emitting efficiency can be improved, it is thus possible to reduce energy
Consumption, meanwhile, complex of the invention has many advantages, such as that good stability, long lifespan, color saturation are high, is produced in display devices such as OLED
It has a good application prospect in industry.
Applicant states that the present invention illustrates the detailed process equipment of the present invention and technological process by above-described embodiment,
But the invention is not limited in above-mentioned detailed process equipment and technological processes, that is, it is above-mentioned detailed not mean that the present invention has to rely on
Process equipment and technological process could be implemented.Person of ordinary skill in the field it will be clearly understood that any improvement in the present invention,
The addition of equivalence replacement and auxiliary element to each raw material of product of the present invention, selection of concrete mode etc. all fall within the present invention's
Within protection domain and the open scope.
Claims (17)
1. a kind of compound using the substitution of naphthalene azepine dibenzo as ligand, structure is shown in Formulas I：
Wherein,
R1, R2, R3It is each independently selected from hydrogen, alkyl, miscellaneous alkyl, aryl or heteroaryl；
Z in Rc is selected from O, S, CR2, NR or Se, and wherein R is alkyl, miscellaneous alkyl, aryl or heteroaryl；
X in Rc structures1, X2, X3, X4It independently is C or N；
M is metal；
X-Y is monoanionic bidentate ligand；
A and b's and for metal ion valence state.
2. compound according to claim 1, which is characterized in that the compound has with Formula Il structure：
3. compound according to claim 1 or 2, which is characterized in that R1, R3It is each independently hydrogen, monosubstituted, double takes
In generation, is polysubstituted, preferably monosubstituted.
4. compound according to claim 1 or 2, which is characterized in that R2It independently is hydrogen, monosubstituted, disubstituted or more take
Generation is preferably hydrogen.
5. compound according to claim 1 or 2, which is characterized in that R2, R3Independently be substituent group or with parent shape
Into and ring structure.
6. compound according to claim 1 or 2, which is characterized in that R1, R2, R3It independently is no more than four carbon atom
Supplied for electronic alkyl or miscellaneous alkyl, preferably contain the alkyl of the collateralization for the supplied for electronic for being no more than 4 carbon atoms.
7. compound according to claim 1 or 2, which is characterized in that R1The position of substitution be metal-nitrogen key adjacent bit
It puts.
8. compound according to claim 1 or 2, which is characterized in that R1The position of substitution be metal-nitrogen key opposite position
It puts.
9. compound according to claim 1 or 2, which is characterized in that R2The position of substitution be metal-carbon key adjacent bit
It puts.
10. compound according to claim 1 or 2, which is characterized in that the X in Rc structures1, X2, X3, X4In not more than 3
For N, preferably not more than 2 are N, and further preferably not more than 1 is N.
11. compound according to claim 1 or 2, which is characterized in that M is the metal that atomic is more than 40, is preferably
Cu, Pt, Pd, Os or Ir, further preferably Pt or Ir, particularly preferably Ir.
12. compound according to claim 1 or 2, which is characterized in that X-Y is different from the ligand on the left side.
13. compound according to claim 1 or 2, which is characterized in that X-Y 1,3- diones.
14. compound according to claim 1 or 2, which is characterized in that the compound is with lower structure：
15. compound according to claim 1 or 2, which is characterized in that the compound is with lower structure：
16. a kind of OLED phosphorescent guest materials containing any one of the claim 1-15 compounds.
17. a kind of OLED device containing any one of the claim 1-15 compounds.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610983989.1A CN108059644A (en) | 2016-11-09 | 2016-11-09 | The electroluminescent organic material of a kind of naphthalene azepine dibenzo substitution as ligand and application thereof |
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| CN201610983989.1A CN108059644A (en) | 2016-11-09 | 2016-11-09 | The electroluminescent organic material of a kind of naphthalene azepine dibenzo substitution as ligand and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112830943A (en) * | 2019-11-25 | 2021-05-25 | 广东阿格蕾雅光电材料有限公司 | Compound and application thereof |
| US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104447880A (en) * | 2014-12-11 | 2015-03-25 | 石家庄诚志永华显示材料有限公司 | Aza-carbazole OLED phosphor material as well as preparation method and application thereof |
| US20160155963A1 (en) * | 2014-11-28 | 2016-06-02 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
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| US20160155963A1 (en) * | 2014-11-28 | 2016-06-02 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
| CN104447880A (en) * | 2014-12-11 | 2015-03-25 | 石家庄诚志永华显示材料有限公司 | Aza-carbazole OLED phosphor material as well as preparation method and application thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11711969B2 (en) | 2016-10-03 | 2023-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN112830943A (en) * | 2019-11-25 | 2021-05-25 | 广东阿格蕾雅光电材料有限公司 | Compound and application thereof |
| CN112830943B (en) * | 2019-11-25 | 2022-12-23 | 广东阿格蕾雅光电材料有限公司 | Compound and application thereof |
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