CN106008574A - Multi-functional triarylborane derivative for body materials of organic electrophosphorescence devices and thermotropic delayed fluorescence material - Google Patents
Multi-functional triarylborane derivative for body materials of organic electrophosphorescence devices and thermotropic delayed fluorescence material Download PDFInfo
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Abstract
The invention provides a multi-functional triarylborane derivative for body materials of electrophosphorescence devices and a thermotropic delayed fluorescence material. Researches find that the emission wavelength of o,o'-BP-NPh2 is short, light emitted from the o,o'-BP-NPh2 can be distinguished from blue light, and besides, the delta EST is smaller. Therefore, the multi-functional triarylborane derivative has TADF characteristics and high ET. The characteristic of high triple state energy level of a compound is used, and the compound is used as the body material for preparing blue light PhOLED and green light PhOLED, the external quantum efficiency of the blue light PhOLED devices is as high as 15%, and the external quantum efficiency of the green light PhOLED devices is as high as 22%. Besides, the TADF characteristic of the compound is used, and the compound is used as a luminescent material for preparing blue light TADF OLED, and the external quantum efficiency of the devices is as high as 8%. The o,o'-BP-NPh2 is a multi-functional organic photoelectronic material. The multi-functional triarylborane derivative is simple in preparation steps, convenient to operate and high in practicality.
Description
Technical field
The invention belongs to field of organic electroluminescence, particularly to one be used as organic electro phosphorescent device material of main part and
The multifunction triaryl boron derivatives of thermic delayed fluorescence material.
Background technology
Organic electroluminescence device (OLED) is owing to having energy active illuminating, glow color continuously adjustabe, being easily achieved greatly
The features such as screen shows, visual angle width, technique simple, low cost, have become as the focus of current flat panel display, have tempting
Application prospect.In order to realize the commercialization of organic electroluminescence device, it is capable of total colouring, monochrome except needs meet
Outside the requirements such as purity is high, thermo-chemical stability is good, it is also desirable to device has high luminous efficiency.According to photochemistry principle, owing to being subject to
The restriction of spin statistics, Carrier recombination forms the probability of singlet exciton and only has 25%, and Organic Electricity based on fluorescent material
Electroluminescence device sends fluorescence just with singlet exciton attenuation, and the external quantum efficiency of device is the highest by only 5%.If
The energy of singletstate and triplet excitons can be fully exploited, it would be possible to breaks through the restriction of electroluminescent fluorescent luminous efficiency, because of
How this utilizes the attenuation of triplet excitons to be the key improving organic electroluminescence device.One of them important side
Method is to replace fluorescent material with the phosphor material of precious metals complex, for the suppression concentration quenching of phosphor material and triplet state-
Triplet state buries in oblivion (TTA) effect, it usually needs be doped in material of main part as object by phosphor material.As organic electroluminescence phosphorus
The material of main part of optical device (PhOLED), it usually needs there is good carrier transmission performance and higher triplet
(ET) so that energy can be transferred to guest materials effectively.In addition, hot activation delayed fluorescence material (TADF) can also
Making full use of the singletstate-triplet excitons being electrically excited lower formation, such material typically has little singletstate-triplet
(ΔEST), triplet excitons can be changed into singlet exciton luminescence by passing through between anti-system.
Triarylboron is that the class received much concern in recent years is organic due to structure and the photoelectric properties of its uniqueness
Photoelectric functional material, due to the impact of boron atom overhead p track, boron substituent group can as an effective electron acceptor, because of
When there is electron donor such as amino in this, system easily shows molecule charge transfer characteristic (ICT) in system.There is ICT special
The triarylboron of property has been used successfully as in nonlinear optical material, two-photon absorption and luminescent material, OLED
Electric transmission and luminescent material, but about organic electrophosphorescenpolymer (PhOLED) device main body material and blue TADF luminescent material
Reporting the most very limited, wherein main cause is the energy gap that ICT characteristic would generally reduce system so that launch wavelength long,
Singletstate and triplet are smaller.
Summary of the invention
In order to prepare, luminous efficiency is high, brightness is big, the organic electro phosphorescent device of good stability, and the present invention provides a kind of use
Make organic electro phosphorescent device material of main part and the multifunction triaryl boron derivatives of thermic delayed fluorescence material.Research is sent out
Existing: to use o, o '-BP-NPh2(i.e. referring to compounds I hereinafter described in the present invention) organic as organic electro phosphorescent device
During luminescent layer material of main part, it is possible to obtain higher device external quantum efficiency.
First the present invention selects o, o '-BP-NPh2With its position isomer, p, p '-BP-NPh2(compound II) is as having
The material of main part of machine luminescent layer, to obtaining high external quantum efficiency.But test result indicate that: use p, p '-BP-NPh2As
During material of main part, do not obtain intended illumination effect.This is possibly due to the special steric hindrance effect of dimesitylboryl and diphenylamino
O, o '-BP-NPh should be made2Having the molecular structure distorted very much, the dihedral angle between two phenyl ring is up to 88 °, not only limit
Conjugation, and make highest occupied molecular orbital (HOMO) and the minimum track (LUMO) that do not occupies substantially there is no overlap, o, o '-BP-
NPh2There is less Δ EST, so o, o '-BP-NPh2Have blue TADF fluorescent emission properties and relatively high triplet energy level concurrently.
For achieving the above object, the present invention uses following scheme:
Based on o, o '-BP-NPh2Have the blue TADF characteristics of luminescence and the performance characteristics of relatively high triplet energy level, the present invention concurrently
Provide compounds I and derivant thereof as blue light TADF luminescent material, the application of organic electro phosphorescent device main body material, describedization
The structural formula of compound I and II is as follows:
Preferably, in the phenylbenzene moiety of described compounds I, the dihedral angle between two phenyl ring reaches more than 88 °.
Preferably, described compounds I maximum absorption band in hexamethylene is 363nm, maximum emission peak 429nm.
Preferably, the mono-crystalline structures figure of described compounds I is as shown in Figure 1.
Present invention also offers a kind of blue light TADF OLED, the luminescent material of described blue light TADF OLED is compounds I.
Present invention also offers a kind of green glow organic electro phosphorescent device PhOLED, described organic electro phosphorescent device
The material of main part of PhOLED is compounds I.
Present invention also offers a kind of blue light organic phosphorescent electroluminescent device PhOLED, described organic electro phosphorescent device
The material of main part of PhOLED is compounds I.
Present invention also offers a kind of blue light organic phosphorescent electroluminescent device, this device include successively transparent substrate, anode layer,
Hole transmission layer, organic luminous layer, electron transfer layer and cathode layer, described organic luminous layer includes material of main part and phosphorescence dye
Material；Described material of main part is compounds I.
Preferably, the average doping concentration of described phosphorescent coloring is 1～30wt%.
Preferably, described phosphorescent coloring is two [2-(4,6-difluorophenyl) pyridine radicals-N, C2’] picolinic acid iridium (III),
Two (1-phenyl-isoquinolyl) (acetylacetone,2,4-pentanedione) iridium (III), octaethylporphyrin platinum or three (2-phenylpyridine) iridium (III) or two
(2-phenylpyridine) (acetylacetone,2,4-pentanedione) iridium (III).
The action principle of the present invention and beneficial effect:
In the present invention, we are by being incorporated into biphenyl structural by electron acceptor dimesitylboryl and electron donor diphenylamino
O, o '-position, obtained having concurrently the blue TADF characteristics of luminescence and relatively high triplet energy level triarylboron (o, o '-BP-
NPh2).In this compound, due to dimesitylboryl and the impact of diphenylamino steric effect, phenylbenzene moiety distorts very much, two
Dihedral angle between phenyl ring is up to 88 °, not only reduces the conjugated degree of system, and make highest occupied molecular orbital (HOMO) and
The minimum track (LUMO) that do not occupies does not has overlap, therefore this compound transmitted wave length substantially, can distribute light in blue light region, with
Time Δ ESTSmaller, the most also there is TADF characteristic and high ET(Fig. 2).Utilize the spy that this compound triplet is high
Point, can make blue light and green glow PhOLED using it as material of main part preparation, and the external quantum efficiency of blue light PhOLED device is the highest
Can be with 15%, the external quantum efficiency of green glow PhOLED device reaches as high as 22%；Utilize the TADF characteristic of this compound simultaneously,
As luminescent material, it can also be prepared blue light TADF OLED, device external quantum efficiency is up to 8%, o, o '-BP-NPh2It is
The organic optoelectronic material of one multifunction.
Accompanying drawing explanation
Fig. 1: o, o '-BP-NPh2Molecular structure and mono-crystalline structures；
Fig. 2: o, o '-BP-NPh2Absorption (solid line), fluorescence (dotted line) and phosphorescence (imaginary point line) spectrum.Absorb and fluorescence
Spectrum measures in room temperature hexamethylene, and phosphorescence spectrum measures at 2-methyltetrahydrofuran 77K；
Fig. 3: assembly of the invention structure chart；
EL spectrogram after Fig. 4: embodiment 21 normalization；
Fig. 5: embodiment 21 brightness and electric current density are with the change curve of voltage；
Fig. 6: embodiment 21 current efficiency, power efficiency and EQE are with the change curve of brightness.
Detailed description of the invention
By the following examples feature of present invention and other correlated characteristic are described in further detail, in order to of the same trade
The understanding of technical staff:
1. a kind of structure of organic electro phosphorescent device is as it is shown on figure 3, wherein:
1) being transparent substrate, can be glass or flexible substrate, flexible substrate uses polyesters, polyimide chemical combination
A kind of material in thing；
2) be anode layer, inorganic material or organic conductive polymer can be used, inorganic material be generally ITO, zinc oxide,
The metal that the work functions such as the metal-oxides such as zinc tin oxide or gold, copper, silver are higher, the optimized ITO that is chosen as, organic conductive gathers
A kind of material that compound is preferably in PEDOT:PSS, PANI；
3) it is hole transmission layer, uses the p-type organic semiconductor material that cavity transmission ability is stronger, generally triphen amine
Compound, such as the one in the materials such as NPB, TPD, MTDATA, the present invention is preferably NPB；
4) it is organic luminous layer, uses o, o '-BP-NPh2As material of main part, the phosphorescence being entrained in material of main part contaminates
The doping content of material is gradually increasing along hole transmission layer to the direction of electron transfer layer along with the increase of organic light emission layer thickness
Or it is gradually reduced formation grade doping structure, generally metal organic complex, such as FIrpic (blue), Ir (piq) 2 (acac)
One in the material such as (red), PtOEP (red), Ir (ppy) 3 (green), Ir (ppy) 2 (acac) (green), it average
Doping content is 0.05～50wt%, and preferred average doping concentration is 1～30wt%；
5) being electron transfer layer, generally metal organic complex is (such as Alq3, BAlq, Gaq3, Al (Saph-q) or Ga
(Saph-q)), aromatic condensed ring class (as pentacene), o-phenanthroline class (such as Bphen, BCP) or diazoles (such as PBD)
A kind of material in compound；
6) be cathode layer (metal level), typically use the relatively low metal of the work functions such as lithium, magnesium, calcium, strontium, aluminum, indium or they
With copper, the alloy of gold, silver, the present invention is preferably Mg:Ag alloy-layer, Ag layer or LiF layer successively, Al layer successively.
The organic electro phosphorescent device that the present invention proposes may also include anode buffer layer (not showing in Fig. 1), anode buffer layer
Between anode layer and hole transmission layer, typically use phthalocyanines, polyacrylate, polyimide, fluoropolymer,
A kind of material in inorganic fluoriding salt, inorganic oxide or diamond, such as CuPc etc..
Embodiment 1
Preferably a kind of phosphorescent OLED s of said structure has a following structural formula (1):
Glass/ITO/NPB/ organic luminous layer 1/Bphen/Mg:Ag/Ag (1)
2. preparation method is as follows:
Transparent conduction base sheet ito glass is carried out clearly by the ultrasonic detergent and the ultrasonic method of deionized water that 1. utilize heat
Wash, place it in after cleaning under infrared lamp dry, then to dry ito glass carry out UV ozone cleaning and mental retardation oxygen from
The pretreatment of son bundle bombardment, wherein the ito film above conductive substrate is as the anode layer of device, and the square resistance of ito film is 5 Ω
～100 Ω, thickness is 80～280nm；
2. it is placed in vacuum chamber by above-mentioned cleaning, drying and through the ito glass of pretreatment, is evacuated to 1 × 10-5～9 ×
10-3Pa, is then deposited with the one layer of NPB hole transmission layer as device in above-mentioned ito film, and the evaporation rate of NPB thin film is
0.01～0.5nm/s, thickness is 20～80nm；
3. keep above-mentioned vacuum cavity pressure constant, above-mentioned NPB hole transmission layer continues to steam in grade doping mode
Plate the organic luminous layer doped with phosphorescent coloring FIrpic, use the method for double source evaporation to carry out grade doping, respectively by main body
Material o, o '-BP-NPh2It is placed in different evaporation sources with FIrpic, at evaporation the most respectively with two film thickness monitoring instrument probes
The evaporation rate of two evaporation sources is monitored, by control two evaporation sources evaporation rate, make FIrpic o, o '-
BP-NPh2In doping content be gradually increasing, o, o '-BP-NPh along with the increase of organic luminous layer evaporation thickness2、FIrpic
Evaporation rate ratio be 1000: 1～1: 1000, FIrpic is at o, o '-BP-NPh2In average doping concentration be 1～30wt%,
Being deposited with total speed is 0.02～0.6nm/s, and total film thickness is 20～100nm；
4. keep above-mentioned vacuum cavity pressure constant, on above-mentioned organic luminous layer, continue one layer of Bphen conduct of evaporation
The electron transfer layer of device, the evaporation rate of Bphen thin film is 0.01～0.5nm/s, and thickness is 20～80nm；
5. keep above-mentioned vacuum cavity pressure constant, on above-mentioned Bphen electron transfer layer, be deposited with Mg:Ag alloy successively
Layer, Ag layer are as the cathode layer of device, and wherein alloy-layer uses the method for double source evaporation to be doped, and in alloy-layer, Mg, Ag steam
Plating speed ratio is 10: 1, and being deposited with total speed is 0.6～2nm/s, and evaporation gross thickness is 50～200nm, and the evaporation rate of Ag layer is
0.3～0.8nm/s, thickness is 40～200nm.
Embodiment 2
A kind of phosphorescent OLED s has a following structural formula (2):
Glass/IT0/NPB/ organic luminous layer 1/BAlq/LiF/Al (2)
In structure above (2), the material of main part of organic luminous layer 1 is o, o '-BP-NPh2, with grade doping side in this layer
Formula is doped with phosphorescent coloring FIrpic.
According to structure above (2), the preparation process detailed embodiment in conjunction with device is described below:
1.～in the most same structure above (1) preparation process 1.～3.；
4. keep above-mentioned vacuum cavity pressure constant, on above-mentioned organic luminous layer, continue one layer of BAlq of evaporation as device
The electron transfer layer of part, the evaporation rate of BAlq thin film is 0.01～0.5nm/s, and thickness is 20～80nm；
5. keep above-mentioned vacuum cavity pressure constant, on above-mentioned BAlq electron transfer layer, be deposited with LiF layer, Al layer successively
As the cathode layer of device, wherein the thickness of LiF layer is 0.2～2nm, and evaporation rate is 0.01～0.1nm/s, the thickness of Al layer
Being 40～200nm, evaporation rate is 0.01～0.5nm/s.
Embodiment 3
The present invention propose have transparent substrate, anode, organic luminous layer, electric transmission Rotating fields device be preferably with
Lower structural formula (3):
Glass/ITO/teflon/ organic luminous layer 1/BAlq/LiF/Al (3)
In structure above (3), the material of main part of organic luminous layer 1 is o, o '-BP-NPh2, with grade doping side in this layer
Formula is doped with phosphorescent coloring FIrpic.
According to structure above (3), the preparation process detailed embodiment in conjunction with device is described below:
In the most same structure above (1) preparation process 1.
2. it is placed in vacuum chamber by above-mentioned cleaning, drying and through the ito glass of pretreatment, is evacuated to 1 × 10-5～9 ×
10-3Pa, is then deposited with the one layer of teflon anode modification layer as device in above-mentioned ito film, the evaporation speed of teflon thin film
Rate is 0.001～0.1nm/s, and thickness is 2～20nm；
3.～in the most same structure above (2) preparation process 3.～5.
Embodiment 4
What the present invention proposed have transparent substrate, anode, organic luminous layer, the device of cathode construction are preferably following structure
Formula (4):
Glass/ITO/teflon/ organic luminous layer 1/Mg:Ag/Ag (4)
According to structure above (4), the preparation process detailed embodiment in conjunction with device is described below:
1.～in the most same structure above (3) preparation process 1.～2.
In the most same structure above (3) preparation process 3.
4. keep above-mentioned vacuum cavity pressure constant, on above-mentioned luminescent layer, be deposited with Mg:Ag alloy-layer, Ag layer work successively
For the cathode layer of device, wherein alloy-layer uses the method for double source evaporation to be doped, and in alloy-layer, Mg, Ag evaporation rate ratio is
10: 1, being deposited with total speed is 0.6～2nm/s, and evaporation gross thickness is 50～200nm, and the evaporation rate of Ag layer is 0.3～0.8nm/
S, thickness is 40～200nm.
Embodiment 5
The present invention propose have transparent substrate, anode, hole transmission layer, organic luminous layer, cathode construction device excellent
Elect following structural formula as:
Glass/ITO/NPB/ organic luminous layer 1/Mg:Ag/Ag (5)
According to structure above (5), the preparation process detailed embodiment in conjunction with device is described below:
1.～in the most same structure above (1) preparation process 1.～3.
4. keep above-mentioned vacuum cavity pressure constant, on above-mentioned luminescent layer, be deposited with Mg:Ag alloy-layer, Ag layer work successively
For the cathode layer of device, wherein alloy-layer uses the method for double source evaporation to be doped, and in alloy-layer, Mg, Ag evaporation rate ratio is
10: 1, being deposited with total speed is 0.6～2nm/s, and evaporation gross thickness is 50～200nm, and the evaporation rate of Ag layer is 0.3～0.8nm/
S, thickness is 40～200nm.
Embodiment 6 (device number OLED1)
OLED1 is prepared with the above-mentioned method preparing device shown in structural formula (1) identical.
Comparative example 1 (device number OLED to 1)
Preparing OLED to 1 by the method same with embodiment 1, wherein the material of main part of the organic luminous layer 1 of device is o,
o’-BP-NMe2。
Embodiment 7 (device number OLED2)
OLED2 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (1) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses Ir (ppy) 3, makes by controlling the evaporation rate ratio of double source evaporation
Ir (ppy) 3 is at o, o '-BP-NPh2In doping content be gradually reduced along with the increase of organic luminous layer evaporation thickness.
Comparative example 2 (device number OLED to 2)
Preparing OLED to 2 by the method same with embodiment 2, wherein the material of main part of the organic luminous layer 1 of device is DCB
(N, N '-two carbazyl-1,4-dimethylene benzene).
Embodiment 8 (device number OLED3)
OLED3 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (1) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses Ir (piq) 2 (acac), by controlling the evaporation speed of double source evaporation
Rate ratio makes Ir (piq) 2 (acac) at o, o '-BP-NPh2In doping content along with organic luminous layer evaporation thickness increase and
It is gradually reduced.
Comparative example 3 (device number OLED to 3)
Preparing OLED to 3 by the method same with embodiment 3, wherein the material of main part of the organic luminous layer 1 of device is
CPF, it may be assumed that 9,9-bis-(4-bis-carbazoles-phenyl) fluorenes.
Result shows: the brightness of the device OLED of the organic luminous layer grade doping phosphorescent coloring of embodiment 6-8 and luminescence
Efficiency is better than the device OLED (the carrying out that device glow color is identical contrasts) of the phosphorescent coloring of comparative example 2-3 respectively, to device
Performance be greatly improved；The device OLED of the phosphorescent coloring of comparative example 1 cannot be carried out effective luminescence.
Embodiment 9 (device number OLED4)
OLED4 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (1) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses FIrpic, makes by controlling the evaporation rate ratio of double source evaporation
FIrpic is at o, o '-BP-NPh2In doping content be gradually increasing along with the increase of organic luminous layer evaporation thickness.
Embodiment 10 (device number OLED5)
OLED5 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (1) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses FIrpic, makes by controlling the evaporation rate ratio of double source evaporation
FIrpic is at o, o '-BP-NPh2In doping content be gradually increasing along with the increase of organic luminous layer evaporation thickness.
Embodiment 11 (device number OLED6)
OLED6 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (2) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses Ir (ppy) 2 (acac), by controlling the evaporation speed of double source evaporation
Rate ratio makes Ir (ppy) 2 (acac) at o, o '-BP-NPh2In doping content along with organic luminous layer evaporation thickness increase and
It is gradually reduced.
Embodiment 12 (device number OLED7)
OLED7 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (2) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses PtOEP, makes by controlling the evaporation rate ratio of double source evaporation
PtOEP is at o, o '-BP-NPh2In doping content be gradually reduced along with the increase of organic luminous layer evaporation thickness.
Embodiment 13 (device number OLED8)
OLED8 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (2) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses Ir (piq) 2 (acac), by controlling the evaporation speed of double source evaporation
Rate ratio makes Ir (piq) 2 (acac) at o, o '-BP-NPh2In doping content along with organic luminous layer evaporation thickness increase and
It is gradually reduced.
Embodiment 14 (device number OLED9)
OLED9 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (3) identical
Material of main part uses o, o '-BP-NPh2, phosphorescent coloring uses FIrpic, makes by controlling the evaporation rate ratio of double source evaporation
FIrpic is at o, o '-BP-NPh2In doping content be gradually increasing along with the increase of organic luminous layer evaporation thickness.
Embodiment 15 (device number OLED10)
OLED10 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (4) identical
Material of main part use o, o '-BP-NPh2, phosphorescent coloring uses FIrpic, makes by controlling the evaporation rate ratio of double source evaporation
FIrpic is at o, o '-BP-NPh2In doping content be gradually increasing along with the increase of organic luminous layer evaporation thickness.
Embodiment 16 (device number OLED11)
OLED11 is prepared, wherein device organic luminous layer with the above-mentioned method preparing device shown in structural formula (5) identical
Material of main part use o, o '-BP-NPh2, phosphorescent coloring uses FIrpic, makes by controlling the evaporation rate ratio of double source evaporation
FIrpic is at o, o '-BP-NPh2In doping content be gradually increasing along with the increase of organic luminous layer evaporation thickness.
Embodiment 17:TADF luminescent device
[ITO/NPB/mCP/o,o’-BP-NPh2: 0.5%DFDB-QA/BCP/BePP2/LiF/Al]
The ITO conducting glass substrate ITO cleanout fluid ultrasonic cleaning 5 minute thick by 15mm × 15mm × 1mm, deionized water
Ultrasonic cleaning 5 minutes, acetone ultrasonic cleaning 20 minutes, isopropanol ultrasonic cleaning 20 minutes.After drying, plasma (plasma)
Process 5 minutes.In fine vacuum 5 × 10-5Being sequentially depositing hole transmission layer NPB under Pa, thickness is 35nm；First exciton barrier-layer
MCP, thickness is 5nm；The method depositing light emitting layer that double source steams altogether, wherein material of main part is o, o '-BP-NPh2, object doping material
Material is DFDB-QA, and doping content is 0.5% (weight percentage), and thickness is 30nm；Second exciton barrier-layer BCP, thickness is
5nm；Electron transfer layer BePP2, thickness is 40nm.Redeposited electron injecting layer LiF, thickness is 1nm；Metallic cathode Al, thickness
100nm.This device cut-in voltage is 2.7V, high-high brightness 113100cd/m2, maximum power efficiency 53.4lm/W.
Comparative example 4: device architecture [ITO/NPB/mCP/4CzIPN:0.5%DFDB-QA/BCP/BePP2/LiF/Al]。
Embodiment 18:TADF luminescent device
[ITO/NPB/mCP/o,o’-BP-NPh2: 0.5%TCF3DB-QA/BCP/BePP2/LiF/Al]
The ITO conducting glass substrate ITO cleanout fluid ultrasonic cleaning 5 minute thick by 15mm × 15mm × 1mm, deionized water
Ultrasonic cleaning 5 minutes, acetone ultrasonic cleaning 20 minutes, isopropanol ultrasonic cleaning 20 minutes.After drying, plasma processes 5 minutes.
In fine vacuum 5 × 10-5Being sequentially depositing hole transmission layer NPB under Pa, thickness is 35nm；First exciton barrier-layer mCP, thickness is
5nm；The method depositing light emitting layer that double source steams altogether, wherein material of main part is o, o '-BP-NPh2, object dopant material is TCF3DB-
QA, doping content is 0.5% (weight percentage), and thickness is 30nm；Second exciton barrier-layer BCP, thickness is 5nm；Electronics
Transport layer BePP2, thickness is 40nm.Redeposited electron injecting layer LiF, thickness is 1nm and metallic cathode Al, thickness 100nm.
Comparative example 5: device architecture [ITO/NPB/mCP/4CzIPN:0.5%TCF3DB-QA/BCP/BePP2/LiF/Al]。
Embodiment 19:TADF luminescent device
[ITO/NPB/mCP/4CzIPN:0.5%DCF3DB-QA/BCP/BePP2/LiF/Al]
The ITO conducting glass substrate ITO cleanout fluid ultrasonic cleaning 5 minute thick by 15mm × 15mm × 1mm, deionized water
Ultrasonic cleaning 5 minutes, acetone ultrasonic cleaning 20 minutes, isopropanol ultrasonic cleaning 20 minutes.After drying, plasma processes 5 minutes.
In fine vacuum 5 × 10-5Being sequentially depositing hole transmission layer NPB under Pa, thickness is 35nm；First exciton barrier-layer mCP, thickness is
5nm；The method depositing light emitting layer that double source steams altogether, wherein material of main part is o, o '-BP-NPh2, object dopant material is DCF3DB-
QA, doping content is 0.5% (weight percentage), and thickness is 30nm；Second exciton barrier-layer BCP, thickness is 5nm；Electronics
Transport layer BePP2, thickness is 40nm.Redeposited electron injecting layer LiF, thickness is 1nm and metallic cathode Al, thickness 100nm.
Comparative example 6: device architecture [ITO/NPB/mCP/4CzIPN:0.5%DCF3DB-QA/BCP/BePP2/LiF/Al]。
Embodiment 20:TADF luminescent device
[ITO/NPB/mCP/4CzIPN:0.5%TFDB-QA/BCP/BePP2/LiF/Al]
The ITO conducting glass substrate ITO cleanout fluid ultrasonic cleaning 5 minute thick by 15mm × 15mm × 1mm, deionized water
Ultrasonic cleaning 5 minutes, acetone ultrasonic cleaning 20 minutes, isopropanol ultrasonic cleaning 20 minutes.After drying, plasma process minute.
In fine vacuum 5 × 10-5Being sequentially depositing hole transmission layer NPB under Pa, thickness is 35nm；First exciton barrier-layer mCP, thickness is
5nm；The method depositing light emitting layer that double source steams altogether, wherein material of main part is o, o '-BP-NPh2, object dopant material is TFDB-
QA, doping content is 0.5% (weight percentage), and thickness is 30nm；Second exciton barrier-layer BCP, thickness is 5nm；Electronics
Transport layer BePP2, thickness is 40nm.Redeposited electron injecting layer LiF, thickness is 1nm and metallic cathode Al, thickness 100nm.
Comparative device structure [ITO/NPB/mCP/4CzIPN:0.5%TFDB-QA/BCP/BePP2/ LiF/Al] device
Result shows: the cut-in voltage of device TADF, brightness and the power efficiency of embodiment 17-20 are better than comparative example respectively
The device TADF (the carrying out that device glow color is identical contrasts) of 4-6, is greatly improved to the performance of device.
Embodiment 21:TADF luminescent device
[TO/ α-NPD/mCP/DPEPO:10wt%NPh2/TmPyPB(TPBi)/LiF/Al]
Preparation method is with embodiment 17.
| Numbering | α-NPD | mCP | EML | TmPyPB | TPBi | Total |
| 1 | 30 | 10 | 30 | 50 | 120 | |
| 2 | 30 | 10 | 30 | 30 | 100 |
Testing result is as follows:
| Numbering | VT | EQEmax | ηp(lm/W) | ηI(cd/A) | Lmax |
| 1 | 4.25 | 6.90 | 6.73 | 9.10 | 322 |
| 2 | 4 | 5.79 | 7.92 | 10.72 | 335 |
Finally should be noted that and the foregoing is only the preferred embodiments of the present invention, be not limited to this
Bright, although being described in detail the present invention with reference to previous embodiment, for a person skilled in the art, it is still
Technical scheme described in previous embodiment can be modified, or wherein part is carried out equivalent.All at this
Within bright spirit and principle, any modification, equivalent substitution and improvement etc. made, should be included in protection scope of the present invention
Within.Although the detailed description of the invention of the present invention is described by the above-mentioned accompanying drawing that combines, but not to scope
Restriction, one of ordinary skill in the art should be understood that, on the basis of technical scheme, those skilled in the art are not required to
Various amendments that creative work to be paid can be made or deformation are still within protection scope of the present invention.
Claims (10)
1. compounds I and derivant thereof postpone glimmering as blue light emitting material, organic electro phosphorescent device material of main part or thermic
The application of luminescent material, it is characterised in that the structural formula of described compounds I is as follows:
Apply the most as claimed in claim 1, it is characterised in that in the phenylbenzene moiety of described compounds I, between two phenyl ring
Dihedral angle reaches more than 88 °.
Apply the most as claimed in claim 1, it is characterised in that described compounds I maximum absorption band in hexamethylene is
363nm, maximum emission peak 429nm.
Apply the most as claimed in claim 1, it is characterised in that the mono-crystalline structures figure of described compounds I is as shown in Figure 1.
5. a blue light TADF OLED, it is characterised in that the material of main part of described blue light TADF OLED is compounds I.
6. a green glow organic electro phosphorescent device PhOLED, it is characterised in that described organic electro phosphorescent device PhOLED's
Material of main part is compounds I.
7. a blue light organic phosphorescent electroluminescent device PhOLED, it is characterised in that described organic electro phosphorescent device PhOLED's
Material of main part is compounds I.
8. a blue light organic phosphorescent electroluminescent device, it is characterised in that this device includes transparent substrate, anode layer, hole successively
Transport layer, organic luminous layer, electron transfer layer and cathode layer, described organic luminous layer includes material of main part and phosphorescent coloring；
Described material of main part is compounds I.
9. blue light organic phosphorescent electroluminescent device as claimed in claim 8, it is characterised in that averagely mixing of described phosphorescent coloring
Miscellaneous concentration is 1～30wt%.
10. blue light organic phosphorescent electroluminescent device as claimed in claim 8, it is characterised in that described phosphorescence fuel is two [2-
(4,6-difluorophenyl) pyridine radicals-N, C2’] picolinic acid iridium (III), two (1-phenyl-isoquinolyl) (acetylacetone,2,4-pentanedione) iridium
(III), octaethylporphyrin platinum or three (2-phenylpyridine) iridium (III) or two (2-phenylpyridine) (acetylacetone,2,4-pentanedione) iridium (III).
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| CN110818731A (en) * | 2018-08-09 | 2020-02-21 | 上海和辉光电有限公司 | Triaryl boron derivative organic luminescent material, preparation method and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106410053A (en) * | 2016-10-31 | 2017-02-15 | 昆山工研院新型平板显示技术中心有限公司 | White light organic light emitting device |
| CN106410053B (en) * | 2016-10-31 | 2019-01-18 | 昆山工研院新型平板显示技术中心有限公司 | A kind of white light organic electroluminescent device |
| CN110818731A (en) * | 2018-08-09 | 2020-02-21 | 上海和辉光电有限公司 | Triaryl boron derivative organic luminescent material, preparation method and application thereof |
| CN110818731B (en) * | 2018-08-09 | 2023-04-07 | 上海和辉光电股份有限公司 | Triaryl boron derivative organic luminescent material, preparation method and application thereof |
| CN110305149A (en) * | 2019-06-28 | 2019-10-08 | 武汉天马微电子有限公司 | A kind of hot activation delayed fluorescence material and its application |
| CN110305149B (en) * | 2019-06-28 | 2022-03-15 | 武汉天马微电子有限公司 | Thermal activation delayed fluorescent material and application thereof |
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