CN106800533B - A kind of naphthoquinones class electroluminescent organic material and its preparation method and application - Google Patents
A kind of naphthoquinones class electroluminescent organic material and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of naphthoquinones class electroluminescent organic material and its preparation method and application, the structural formula of above-mentioned electroluminescent organic material isOrNaphthoquinones class electroluminescent organic material provided by the invention has suitable HOMO and lumo energy and D-A structure, can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduces the efficiency roll-off under high current density；Using the device of naphthoquinones class electroluminescent organic material provided by the invention, current efficiency, power efficiency and the external quantum efficiency of device are greatly improved.Naphthoquinones class electroluminescent organic material provided by the invention has good application effect in OLED luminescent device, has good industrialization prospect.
Description
Technical field
The present invention relates to field of organic electroluminescent materials more particularly to a kind of naphthoquinones class electroluminescent organic material and its
Preparation method and application.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity
Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency of OLED device, use
The performances such as service life also need further to be promoted.
Proposing high performance research for OLED luminescent device includes: the driving voltage for reducing device, improves shining for device
Efficiency improves the service life etc. of device.In order to realize OLED device performance continuous promotion, not only need from OLED device
The innovation of structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance OLED
Functional material.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes, i.e. charge injection transmission from purposes
Material and luminescent material further can also inject charge into transmission material and be divided into electron injection transmission material, electronic blocking material
Luminescent material, can also be divided into main body luminescent material and dopant material by material, hole injection transmission material and hole barrier materials.
The different function film layer of industry application requirement and OLED device for current OLED device, the photoelectricity of device
Property requirements, it is necessary to which selection is more suitable for, and OLED functional material or combination of materials with high performance are just able to achieve the efficient of device
Rate, the overall characteristic of long-life and low-voltage.For current OLED shows the actual demand of Lighting Industry, OLED material at present
Development it is also far from enough, lag behind the requirement of panel manufacturing enterprise, the organic functions as material enterprise development higher performance
The exploitation of material is particularly important.
Summary of the invention
For the above problem existing for existing OLED material, now provide a kind of naphthoquinones class electroluminescent organic material and its
Preparation method and application, it is desirable to provide a kind of to have with good photoelectric properties, the requirement that can satisfy panel manufacturing enterprise
Electroluminescent material.
Specific technical solution is as follows:
The first aspect of the invention is to provide a kind of naphthoquinones class electroluminescent organic material, has the feature that, on
State the structural formula of electroluminescent organic material as shown in formula (i) or formula (ii):
Wherein, R2Selected from one of hydrogen, alkyl or aromatic radical；
Wherein, Ar is selected from C6-30Aryl；
Wherein, R1Selected from containing substituent group or without substituent groupOr containing substituent group or without substituent groupWherein, X1Selected from oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) replace season alkyl (or tertiary alkyl),
Two (C1-10Branched alkyl) the season alkyl (or tertiary alkyl), alkyl-substituted that replaces of the season alkyl (or tertiary alkyl), the aryl that replace
One of the tertiary amine groups that tertiary amine groups or aryl replace.
Above-mentioned electroluminescent organic material, also has the feature that, R2Selected from hydrogen, C1-10Alkyl, phenyl, naphthalene,
One of anthryl, dibiphenylyl, terphenyl, 9,9- dialkyl group acridinyl, carbazyl, phenazinyl or phenothiazinyl.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituent groupReplace with containing
BaseFor quilt in any phenyl ring or each phenyl ring Ortho position unitary replaces, i.e., above-mentioned substituent group passes through C1-C2、C2-C3、C3-C4、C1'-C2'、C2'-
C3'Or C3'-C4'Key connection, wherein X2、X3、X4Separately it is selected from oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) replace
Season alkyl (or tertiary alkyl), two (C1-10Branched alkyl) replace season alkyl (or tertiary alkyl), aryl replace season alkyl (or
Tertiary alkyl), one of the tertiary amine groups that replace of alkyl-substituted tertiary amine groups or aryl.
Above-mentioned electroluminescent organic material, also has the feature that, X1、X2、X3And X4It is separately former selected from oxygen
Son, sulphur atom, selenium atom, two (C1-10Straight chained alkyl) replace quaternary carbon, two (C1-10Branched alkyl) replace quaternary carbon, aryl takes
One of the tertiary amine groups that the quaternary carbon in generation, methyl substituted tertiary amine groups or aryl replace.
Preferably, R1It is preferably one of following:
Preferably, above-mentioned electroluminescent organic material is preferably one in following compound C1-C153 in the present invention:
The above are some specific structure types, but naphthoquinones class electroluminescent organic material provided in the present invention does not limit to
All based on formula (I) or formula (II) in these listed chemical structures, substituent group is group in all ranges of definition
The compound of simple transformation should be all included.
The second aspect of the invention is to provide the preparation method of above-mentioned electroluminescent organic material, has such spy
Sign, includes the following steps:
1) using the bromo compound of naphthoquinones as raw material, intermediate is prepared through coupling reaction, reaction equation is as follows:
2) it is raw material by the intermediate prepared in step 1, electroluminescent organic material is prepared through coupling reaction,
Reaction equation is as follows:
Above-mentioned preparation method, also has the feature that, in step 1, the bromo compound and amine compound of naphthoquinones
The molar ratio of (or boronic acid compounds) is 1.0-2.0:1, and catalyst is selected from Pd (dppf) Cl2, one of palladium acetate, catalyst
Molar ratio with amine compound (or boronic acid compounds) is 0.003-0.01:1；Alkali is selected from sodium tert-butoxide, potassium tert-butoxide, carbonic acid
One of sodium, potassium carbonate, the molar ratio of alkali and amine compound (or boronic acid compounds) are 1.0-3.0:1.
Above-mentioned preparation method, also has the feature that, in step 2, intermediate and boronic acid compounds (or grignard is tried
Agent, amine compound) molar ratio be 1:1.0-2.0, catalyst be selected from Pd (dppf) Cl2, palladium acetate or Pd (PPh3)4In
One kind, catalyst and amine compound (or the molar ratio of boronic acid compounds i) is 0.003-0.01:1；Alkali be selected from sodium tert-butoxide,
The molar ratio of one of potassium tert-butoxide, sodium carbonate, potassium carbonate, alkali and amine compound (or boronic acid compounds) is 1.0-3.0:
1。
The third aspect of the invention is to provide above-mentioned electroluminescent organic material in preparing organic electroluminescence device
Application.
The fourth aspect of the invention is to provide a kind of organic electroluminescence device, contains in the organic electroluminescence device
Multiple functional layers, also have the feature that, at least one functional layer contains above-mentioned electroluminescent organic material.
Prepared organic electroluminescence device generally comprises the ITO Conducting Glass being sequentially overlapped, sky in the present invention
Cave transport layer, luminescent layer (being related to naphthoquinones class electroluminescent organic material provided in the present invention), electron transfer layer, electron injection
Layer (LiF) and cathode layer (Al), all functional layers are all made of vacuum evaporation process and are made.
It should be appreciated that making the purpose of OLED device in the present invention, it is intended merely to be better described, it is provided in the present invention
Electroluminescent ability possessed by naphthoquinones class electroluminescent organic material, and sent out organic electroluminescence provided by the present invention
The limitation of the application range of luminescent material.
The beneficial effect of above scheme is:
Naphthoquinones class electroluminescent organic material provided by the invention has suitable HOMO and lumo energy and D-A structure,
Exciton utilization rate and high fluorescent radiation efficiency can be effectively improved, the efficiency roll-off under high current density is reduced；It is mentioned using the present invention
The device of the naphthoquinones class electroluminescent organic material of confession, current efficiency, power efficiency and the external quantum efficiency of device obtain very
It is big to improve.Naphthoquinones class electroluminescent organic material provided by the invention has good application effect in OLED luminescent device,
With good industrialization prospect.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic electroluminescence device provided in the embodiment of the present invention, by lower layer to upper layer,
It is followed successively by transparent substrate layer (1), transparent electrode layer (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), electronics
Transport layer (6), electron injecting layer (7), cathode reflection electrode layer (8), wherein luminescent layer (5) is related to provided in the present invention
Naphthoquinones class electroluminescent organic material.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, those of ordinary skill in the art without creative labor it is obtained it is all its
His embodiment, shall fall within the protection scope of the present invention.
It should be noted that in the absence of conflict, the feature in embodiment and embodiment in the present invention can phase
Mutually combination.
The present invention will be further explained below with reference to the attached drawings and specific examples, but not as the limitation of the invention.
The preparation of 1 compound 2 of embodiment
0.011mol (3.47g) 2,7 dibromo naphthoquinones is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.01mol (2.58g) compound M1,0.03mol (2.88g) sodium tert-butoxide, 10-4mol (0.073g) Pd (dppf) Cl2,
180ml toluene is heated to reflux 10 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving carry out filtrate
Column chromatography, obtains target product 3.06g, purity 99.3%, yield 62%；
250mL there-necked flask separately is taken, 0.006mol (2.96g) intermediate A 1 is added under the atmosphere for being passed through nitrogen,
0.0072mol (1.24g) 1- naphthalene boronic acids, 0.12mol (1.66g) potassium carbonate, 6 × 10-5mol (0.072g) Pd (PPh3) 4,
100mL toluene, 60mL water are heated to reflux 8h, sample contact plate, fully reacting；Natural cooling, filtering, by filtrate liquid separation, washing has
Machine mutually to neutrality, collects organic phase revolving, and organic phase is carried out column chromatography, obtains target product, purity 99.2, yield 77%.
Elemental analysis structure (molecular formula C38H24N2O2): theoretical value C, 84.42；H,4.47；N,5.18；O,5.92；Test
Value: C, 84.40；H,4.42；N,5.21；O,5.97；
HPLC-MS: materials theory value is 540.61, actual value 540.65.
The preparation of 2 compound 9 of embodiment
0.011mol (3.47g) 2,7- dibromo naphthoquinones is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.01mol (4.19g) compound M2,0.3mol (4.15g) potassium carbonate, 10-4mol (0.0224g) palladium acetate, 10-4mol
(0.0202g) tert-butyl phosphine, 100mL toluene, 60mL water are heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling,
Filtrate liquid separation is washed organic phase to neutrality, collects organic phase revolving, organic phase is carried out column chromatography, obtain target production by filtering
Object 3.66g, purity 99.1%, yield 60%；
Separately take 250mL there-necked flask, under the atmosphere for being passed through nitrogen be added 0.006mol (3.66g) intermediate A 2,1.2 ×
10-4Pd (dppf) Cl2,150mL tetrahydrofuran is heated to 50-55 DEG C of heat preservation, 0.024mol (3.54g) bromine is added dropwise into system
The Grignard Reagent (being added drop-wise in reaction system after can diluting it with THF) of propane, about 1h drop finish, and are warming up to reflux 4-6h,
Sample contact plate, fully reacting；Filtrate is carried out column chromatography, obtains target product, purity by natural cooling, filtering, filtrate revolving
99.6, yield 85%.
Elemental analysis structure (molecular formula C40H31NO3): theoretical value C, 83.75；H,5.45；N,2.44；O,8.36；Test
Value: C, 83.77；H,5.43；N,2.45；O,8.35；
HPLC-MS: materials theory value is 573.68, actual value 573.69.
The preparation of 3 compound 11 of embodiment
0.011mol (3.47g) 2,3- dibromo naphthoquinones is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.01mol (4.39g) compound M4,0.3mol (4.15g) potassium carbonate, 10-4mol (0.0224g) palladium acetate, 10-4mol
(0.0202g) tert-butyl phosphine, 100mL toluene, 60mL water are heated to reflux 12 hours, sample contact plate, fully reacting；Natural cooling,
Filtrate liquid separation is washed organic phase to neutrality, collects organic phase revolving, organic phase is carried out column chromatography, obtains intermediate by filtering
A4, purity 99.2%, yield 51%；
0.01mol (6.30g) intermediate A is added under the atmosphere for being passed through nitrogen in the there-necked flask for separately taking 250ml,
0.012mol (1.46g) phenyl boric acid, 0.3mol (4.15g) potassium carbonate, 10-4mol (0.12g) Pd (PPh3) 4,100mL toluene,
60mL water is heated to reflux 8 hours, samples contact plate, fully reacting；Filtrate liquid separation is washed organic phase extremely by natural cooling, filtering
Neutrality, collects organic phase revolving, and organic phase is carried out column chromatography, obtains target product, purity 99.7%, yield 74%；
Elemental analysis structure (molecular formula C46H29NO2): theoretical value C, 88.01；H,4.66；N,2.23；O,5.10；Test
Value: C, 88.05；H,4.67；N,2.20；O,5.08；
HPLC-MS: materials theory value is 627.22, actual value 627.25.
The preparation of 4 compound 14 of embodiment
0.011mol (3.47g) 2,7- dibromo naphthoquinones is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.01mol (3.15g) compound M5,0.03mol (2.88g) sodium tert-butoxide, 10-4mol (0.073g) Pd (dppf) Cl2,
180ml toluene is heated to reflux 10 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving carry out filtrate
Column chromatography, obtains intermediate A 53.06g, purity 99.3%, yield 62%；
250mL there-necked flask separately is taken, under the atmosphere for being passed through nitrogen, 0.01mol (3.47g) intermediate A 5 is added,
0.012mol (2.39g) phenthazine, 0.03mol (2.88g) sodium tert-butoxide, 10-4mol (0.092g) Pd2 (dba) 3,100mL first
Benzene is heated to reflux 10 hours, samples contact plate, fully reacting；Filtrate is carried out column chromatography by natural cooling, filtering, filtrate revolving,
Obtain target product, purity 99.1%, yield 72%；
Elemental analysis structure (molecular formula C43H28N2O2S2): theoretical value C, 77.22；H,4.22；N,4.19；O,4.78；S,
9.59；Test value: C, 77.23；H,4.23；N,4.20；O,4.76；S,9.58；
HPLC-MS: materials theory value is 668.16, actual value 668.20.
The preparation of 5 compound 31 of embodiment
The first step coupling reaction during the preparation method is the same as that of Example 1 of compound 31, the difference is that being replaced using raw material M6
Change M1；2- bromonaphthalene quinone replaces 2,7 dibromo naphthoquinones；
Elemental analysis structure (molecular formula C37H26N2O2): theoretical value C, 83.75；H,4.94；N,5.28；O,6.03；Test
Value: C, 83.77；H,4.92；N,5.26；O,2.55；S,6.05；
HPLC-MS: materials theory value is 530.20, actual value 530.26.
The preparation of 6 compound 63 of embodiment
The first step coupling reaction during the preparation method is the same as that of Example 1 of compound 63, the difference is that being replaced using raw material M7
Change M1；2- bromonaphthalene quinone replaces 2,7- dibromo naphthoquinones；
Elemental analysis structure (molecular formula C36H22N2O2): theoretical value C, 84.03；H,4.31；N,5.44；O,6.22；Test
Value: C, 84.02；H,4.32；N,5.45；O,6.21；
HPLC-MS: materials theory value is 514.17, actual value 514.25.
The preparation of 7 compound 90 of embodiment
0.011mol (3.47g) 2,7- dibromo naphthoquinones is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.01mol (3.93g) compound M8,0.3mol (4.15g) potassium carbonate, 10-4mol (0.0224g) palladium acetate, 10-4mol
(0.0202g) tert-butyl phosphine, 180mL toluene, 60mL water are heated to reflux 8 hours, sample contact plate, fully reacting；Natural cooling,
Filtrate liquid separation is washed organic phase to neutrality, collects organic phase revolving, organic phase is carried out column chromatography, obtain target production by filtering
Object, purity 98.9%, yield 57%；
250mL there-necked flask separately is taken, under the atmosphere for being passed through nitrogen, 0.01mol (3.47g) intermediate A 8 is added,
0.012mol (2.01g) carbazole, 0.03mol (2.88g) sodium tert-butoxide, 10-4mol (0.0224g) palladium acetate, 100mL toluene,
It is heated to reflux 6 hours, samples contact plate, fully reacting；Filtrate is carried out column chromatography, obtained by natural cooling, filtering, filtrate revolving
Target product, purity 99.5%, yield 79%；
Elemental analysis structure (molecular formula C46H26N2O4): theoretical value C, 82.37；H,3.91；N,4.18；O,9.54；Test
Value: C, 82.35H, 3.93；N,4.19；O,9.53；
HPLC-MS: materials theory value is 670.19, actual value 670.29.
The preparation of 8 compound 102 of embodiment
The preparation method of compound 102 is with embodiment 3, the difference is that replacing M4 using raw material M9；Elemental analysis knot
Structure (molecular formula C43H29NO3): theoretical value C, 84.99；H,4.81；N,2.30；O,7.90；Test value: C, 84.97；H,4.82；N,
2.31；O,7.90；
HPLC-MS: materials theory value is 607.21, actual value 607.32.
The preparation of 9 compound 116 of embodiment
The preparation method of compound 116 is with embodiment 3, the difference is that replacing M4 using raw material M10；2,8- dibromine naphthalenes
Quinone replaces 2,3- dibromo naphthoquinones
Elemental analysis structure (molecular formula C52H33N3O2): theoretical value C, 85.34；H,4.55；N,5.74；O,4.37；Test
Value: C, 85.35；H,4.54；N,5.75；O,4.36；
HPLC-MS: materials theory value is 731.26, actual value 731.36.
The preparation of 10 compound 129 of embodiment
The preparation method of compound 129 is with embodiment 3, the difference is that replacing M4 using raw material M11；4- xenyl boron
Acid replacement phenyl boric acid；
Elemental analysis structure (molecular formula C49H33NO2S): theoretical value C, 84.09；H,4.75；N,2.00；O,4.57；S,
4.58；Test value: C, 84.07；H,4.76；N,2.01；O,4.59；S, 4.56；
HPLC-MS: materials theory value is 699.22, actual value 699.27.
The preparation of 11 compound 138 of embodiment
The preparation method of compound 138 is with embodiment 7, the difference is that replacing M8 using raw material M12；2,6- dibromine naphthalenes
Quinone replaces 2,7- dibromo naphthoquinones；Acridine replaces carbazole；
Elemental analysis structure (molecular formula C52H38N2O4): theoretical value C, 82.74；H,5.07；N,3.71O,8.48；Test
Value: C, 82.75；H,5.08；N,3.70；O,8.47；
HPLC-MS: materials theory value is 754.28, actual value 754.32.
The preparation of 12 compound 144 of embodiment
The preparation method of compound 144 is with embodiment 3, the difference is that replacing M4 using raw material M13；
Elemental analysis structure (molecular formula C42H25NO3): theoretical value C, 85.26；H,4.26；N,2.37；O,8.11；Test
Value: C, 85.27；H,4.25；N,2.35；O,8.13；
HPLC-MS: materials theory value is 591.45, actual value 591.58.
The preparation of 13 compound 147 of embodiment
The preparation method of compound 147 is with embodiment 3, the difference is that replacing M4 using raw material M14；
Elemental analysis structure (molecular formula C50H37NO3): theoretical value C, 85.81；H,5.33；N,2.00；O,6.86；Test
Value: C, 85.82；H,5.34；N,2.01；O,6.89；
HPLC-MS: materials theory value is 699.27, actual value 699.40.
The preparation of 14 compound 148 of embodiment
The preparation method of compound 148 is with embodiment 2, the difference is that replacing M2 using raw material M15；
Elemental analysis structure (molecular formula C49H39NO3): theoretical value C, 85.31；H,5.70；N,2.03；O,6.96；Test
Value: C, 85.33；H,5.71；N,2.02；O,6.94；
HPLC-MS: materials theory value is 689.29, actual value 689.37.
The preparation of 15 compound 149 of embodiment
250mL there-necked flask is taken, 0.01mol (2.37g) M16,0.015mol (6.80g) is added under the atmosphere for being passed through nitrogen
1- naphthalene boronic acids, 0.02mol (2.76g) potassium carbonate, 5 × 10-5mol (0.0055g) Pd (PPh3) 4,100mL toluene, 60mL water,
It is heated to reflux 8h, samples contact plate, fully reacting；Filtrate liquid separation is washed organic phase to neutrality, collection has by natural cooling, filtering
Machine mutually rotates, and organic phase is carried out column chromatography, obtains target product, purity 99.2, yield 77%.
Elemental analysis structure (molecular formula C41H27NO2): theoretical value C, 87.06；H,4.81；N,2.48；O,5.65；Test
Value: C, 87.10；H,4.80；N,2.44；O,5.66；
HPLC-MS: materials theory value is 565.20, actual value 565.35.
The preparation of 16 compound 151 of embodiment
The preparation method is the same as that of Example 15 for compound 151, the difference is that replacing M16 using raw material M17；
Elemental analysis structure (molecular formula C37H25NO3): theoretical value C, 83.60；H,4.74；N,2.63；O,9.03；Test
Value: C, 83.66；H,4.71；N,2.60；O,9.03；
HPLC-MS: materials theory value is 531.18, actual value 531.37.
Organic electroluminescence device embodiment
Device 1-7 is prepared with the above-mentioned electroluminescent organic material in part in the embodiment of the present invention 17-23, should be managed
Solution, device implementation process with as a result, being intended merely to preferably explain the present invention, not limitation of the present invention, above-mentioned Organic Electricity
Electroluminescence device the preparation method is as follows:
A) neutralizing treatment, pure water, drying are successively carried out to ito anode layer (film thickness 150nm), then carries out ultraviolet light-
Ozone washing is to remove the organic residue on 2 surface of transparent ITO-anode layer.
B) hole injection layer (MoO3) is deposited on ito anode layer, film thickness 10nm；
C) hole transmission layer (TAPC) is deposited on hole injection layer, film thickness 140nm；
D) on the hole transport layer be deposited luminescent layer (compound provided by the invention: Ir (pq) 2acac=100:5 (wt:
Wt), film thickness 30nm；
E) electron transfer layer (TPBI) is deposited on the light-emitting layer, film thickness 50nm；
F) electron injecting layer device (LiF) is deposited on the electron transport layer, film thickness 1nm；
G) evaporation cathode reflection electrode layer (Al) on electron injecting layer, film thickness 80nm.
In the preparation method of above-mentioned organic electroluminescence device, the structural formula of TAPC, Ir (pq) 2acac, TPBI, CBP is such as
Shown in lower:
As above after completing device 1-7 and comparative device, anode and cathode is connected with well known driving circuit, is measured
The principal structural layer and test result of the service life of the current efficiency of device, luminescent spectrum and device, device 1-7 and comparative device
It is as shown in the table:
| Embodiment | Device | Luminous layer structure | Current efficiency | Color | The LT9 service life |
| 17 | 1 | Compound 9:Ir (pq) 2acac=100:5 | 1.2 | Feux rouges | 1.9 |
| 18 | 2 | Compound 11:Ir (pq) 2acac=100:5 | 1.5 | Feux rouges | 2.5 |
| 19 | 3 | Compound 31:Ir (pq) 2acac=100:5 | 1.3 | Feux rouges | 2.0 |
| 20 | 4 | Compound 102:Ir (pq) 2acac=100:5 | 1.8 | Feux rouges | 2.6 |
| 21 | 5 | Compound 148:Ir (pq) 2acac=100:5 | 1.5 | Feux rouges | 2.6 |
| 22 | 6 | Compound 149:Ir (pq) 2acac=100:5 | 1.4 | Feux rouges | 1.6 |
| 23 | 7 | Compound 151:Ir (pq) 2acac=100:5 | 1.4 | Feux rouges | 1.5 |
| Comparative example | Comparative device | CBP:Ir (pq) 2acac=100:5 | 1.0 | Feux rouges | 1.0 |
In above-mentioned test, using comparative example as reference, comparative example device performance indexes is set as device detection performance
1.0.The current efficiency of comparative example is 14.8cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.66,0.33)；Under 3000 brightness
LT95 life time decay is 11Hr.Life-span test system is the OLED device of owner of the invention and Shanghai University's joint development
Life-span tester.
From upper table analysis: naphthoquinones class electroluminescent organic material provided by the present invention is as luminescent layer material of main part
It can be applied to the production of OLED luminescent device, and compared with comparative example, either efficiency or service life are than known OLED material
The driving service life for obtaining larger change, especially device obtains biggish promotion.Naphthoquinones class organic electroluminescence provided by the present invention
Luminescent material has good application effect as emitting layer material in OLED luminescent device, before having good industrialization
Scape.
The above is only preferred embodiments of the present invention, are not intended to limit the implementation manners and the protection scope of the present invention, right
For those skilled in the art, it should can appreciate that and all replace with being equal made by description of the invention and diagramatic content
It changes and obviously changes obtained scheme, should all be included within the scope of the present invention.
Claims (3)
1. a kind of naphthoquinones class electroluminescent organic material, which is characterized in that the electroluminescent organic material is using naphthoquinones as parent nucleus
Structure, structural formula as shown in formula (i) or formula (ii):
Wherein, R2Selected from hydrogen, C1-10Alkyl, phenyl, naphthalene, anthryl, dibiphenylyl, terphenyl, 9,9- dialkyl group acridine
One of base, carbazyl, phenazinyl or phenothiazinyl；
Wherein, Ar is selected from C6-30Aryl；
Wherein, R1Selected from containing substituent group or without substituent groupContaining substituent group or without substituent group
It is described containing substituent groupWith described containing substituent groupFor any phenyl ring or each phenyl ring quiltIt is condensed to replace,
Condensed site is the asterisk site of foregoing substituents, wherein the X1、X2、X3And X4Separately it is selected from oxygen atom, sulphur
Atom, two (C1-10Straight chained alkyl) replace season alkyl, two (C1-10Branched alkyl) replace season alkyl, aryl replace season alkane
One of the tertiary amine groups that base, methyl substituted tertiary amine groups or aryl replace.
2. a kind of naphthoquinones class electroluminescent organic material according to claim 1 is in preparing organic electroluminescence device
Using.
3. a kind of organic electroluminescence device, including multiple functional layers, which is characterized in that at least one described functional layer contains
Naphthoquinones class electroluminescent organic material described in claim 1.
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