CN108203403A - Luminescent material with thermotropic delayed fluorescence, its application and electroluminescent device - Google Patents

Luminescent material with thermotropic delayed fluorescence, its application and electroluminescent device Download PDF

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CN108203403A
CN108203403A CN201611187513.3A CN201611187513A CN108203403A CN 108203403 A CN108203403 A CN 108203403A CN 201611187513 A CN201611187513 A CN 201611187513A CN 108203403 A CN108203403 A CN 108203403A
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delayed fluorescence
luminescent material
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穆广园
吕夏蕾
庄少卿
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WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd
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WUHAN SHANGSAI PHOTOELECTRIC TECHNOLOGY Co Ltd
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Abstract

The invention belongs to organic photoelectrical material preparation and applicating technology fields, and in particular to have luminescent material, its application and the electroluminescent device of thermotropic delayed fluorescence.Luminescent material provided by the present invention with thermotropic delayed fluorescence is using carbazole derivates as donor groups, smaller single triplet energy gap is realized by molecular distortion, jump is worn between inverse system so as to fulfill triplet exciton to singlet excitons, improve exciton utilization rate and promotes device efficiency.Using the luminescent material provided by the present invention with thermotropic delayed fluorescence as main body luminescent material, the efficiency roll-off of device can be reduced, as guest emitting material, luminescent layer brightness is high, and stability is good, and luminous efficiency is high, and service life is long.Using the luminescent material provided by the present invention with thermotropic delayed fluorescence as organic light emitting medium, the efficiency roll-off of device is low, and luminous efficiency is high, and service life is long.

Description

Luminescent material with thermotropic delayed fluorescence, its application and electroluminescent device
Technical field
The invention belongs to organic photoelectrical material preparation and applicating technology fields, and in particular to have the hair of thermotropic delayed fluorescence Luminescent material, its application and electroluminescent device.
Background technology
In recent years, Organic Light Emitting Diode (Organic Light Emitting Diode, abbreviation OLED) display and Lighting area is a dark horse, and is increasingly becoming the new industry being concerned.Compared to current main flow display-liquid crystal display (LCD), OLEDs has that self-luminous, visual angle be wide, fast response time under high temperature cryogenic conditions, color is true to nature, clarity is high, bendable The prominent advantages such as potentiality that are bent and having low cost, therefore be considered as next-generation flat panel display.2008, Japanese rope Buddhist nun company releases 11 inches of full color electro-luminescent flat TVs, it has milestone in electroluminescent industrialization process Meaning.Therefore, the electroluminescent organic material of R and D reality efficient stable causes the pole of lot of domestic and foreign research institution Big concern.
The development of electroluminescent organic material substantially experienced three phases.The conventional fluorescent material of first stage, due to The ratio of singlet excitons and triplet exciton is 1 under electroluminescent:3, and conventional fluorescent material can only utilize 25% substance State exciton, it is difficult breakthrough 5% to lead to external quantum efficiency.Second stage is phosphorescent light-emitting materials.1998, Forrest, Thompson and Ma etc. introduces the luminescent layer of OLED using phosphorescent complexes as luminescent material, due to can simultaneously using substance and The energy of triplet excited state makes the theoretical maximum internal quantum efficiency of device be increased to 100% by 25%, is pushed away in organic light emission field Into major step.Phase III is thermotropic delayed fluorescence material.2009, Adachi seminars reported glimmering with thermotropic delay The molecule of light (thermally activated delayed fluorescence, TADF) phenomenon, they have smaller list Weight state-triplet energy gap.Under the support of environment's heat, reversed intersystem transition (reverse of the triplet to singlet state can be made Intersystem-crossing, RISC) it forms singlet excitons and shines, reach so as to fulfill theoretical internal quantum efficiency 100%.TADF materials are designed the precious metal material avoided using high cost, and its outer quantum using traditional organic material Efficiency also reaches the level to compare favourably with phosphorescence.Adachi seminars have gone out internal quantum efficiency using TADF material preparations and have reached 100% external quantum efficiency reach 41.5% high performance OLED device (Nat.Commun., 2015,6,8476, DOI: 10.1038/ncomms9476).So TADF materials are expected to the commercial application material as great potential.
However at present, the MOLECULE DESIGN of thermotropic delayed fluorescence material is difficult, alternative electron-donating group and Electron withdrawing group is seldom.The present invention provides a kind of new electron-donating groups, prepare simply, stability is good, can be used for designing The TADF materials of different photochromic efficient stables.
Invention content
To solve the deficiencies in the prior art, the present invention provides a kind of luminescent material with thermotropic delayed fluorescence, its should With and electroluminescent device.Luminescent material provided by the present invention with thermotropic delayed fluorescence is as carbazole derivates donor base Group, small single triplet energy gap is realized by molecular distortion, so as to fulfill the promotion of device efficiency.
It is another object of the present invention to provide the luminescent materials provided by the present invention with thermotropic delayed fluorescence Application as electroluminescent layer material.
It is another object of the present invention to provide a kind of electroluminescent devices.
Technical solution provided by the present invention is as follows：
Luminescent material with thermotropic delayed fluorescence has the general structure of following formula (I) or formula (II)：
Wherein：
R1For electron withdrawing group, R2、R3、R4、R5、R6And R7It is independently electron-donating group or hydrogen, R2、R3、R4、R5、 R6And R7It is identical or different.
Specifically, R1It is selected from：
The aromatic group of cyano substitution；
Alternatively, the carbon atom number containing at least one miscellaneous aromatic rings is 5~30 non-substituted electron withdrawing group, each virtue Fragrant ring is connected or condensed by singly-bound, and miscellaneous aromatic rings is miscellaneous five-membered ring or miscellaneous hexatomic ring, heteroatomic quantity in miscellaneous aromatic rings It is 1,2,3 or 4, each hetero atom is respectively nitrogen, oxygen, phosphorus or sulphur, and each hetero atom is identical or different；
Alternatively, the carbon atom number containing at least one miscellaneous aromatic rings is 5~53 substituted electron withdrawing group of hydrogen, respectively Aromatic rings is connected or condensed by singly-bound, and miscellaneous aromatic rings is miscellaneous five-membered ring or miscellaneous hexatomic ring, heteroatomic number in miscellaneous aromatic rings It is 1,2,3 or 4 to measure, and each hetero atom is respectively nitrogen, oxygen, phosphorus or sulphur, and each hetero atom is identical or different, and substituent group is that carbon atom number is The alkyl of 1-20 or silane alkyl；
Alternatively, carbon atom number be 5-10 alkyl aromatic group, carbon atom number be 5-10 halogenated alkyl aromatic group or Halogenated aromatic group, alkyl-substituted biphenyl group, the biphenyl group of alkoxy substitution, alkyl-substituted naphthylene group, alkoxy Substituted naphthylene group；
Preferably：
The aromatic group of cyano substitution is cyano-phenyl, cyanonaphthyl or cyanobiphenyl base；
The non-substituted electron withdrawing group that carbon atom number containing at least one miscellaneous aromatic rings is 5~30 is thienyl Group, benzothiophene group, pyridine groups, pyrrole group, oxazole group, thiazolyl group, thiadiazoles group, triazine group, hexichol Base phosphorus-oxygen groups, imidazole group, to phenyl benzimidazole groups group, phenyl benzimidazole groups group, carbazole group, indolyl radical, Quinoline group or isoquinolin group；
The alkyl aromatic group that carbon atom number is 5-10 is toluene, ethylo benzene, o- cumenyl, m- cumenyl, p- Cumenyl or methyl naphthalene；
The halogenated alkyl aromatic group or halogenated aromatic group that carbon atom number is 5-10 are ortho-fluorophenyl, m- fluorobenzene, p- fluorine Benzene, fluorination naphthalene or trifluoromethylbenzene.
It is furthermore preferred that R1Selected from following structural formula：
Wherein, * is the position of substitution.
Specifically, R2、R3、R4、R5、R6And R7Be independently selected from hydrogen, phenyl, naphthalene, tertiary butyl,OrWherein * be the position of substitution, R2、R3、R4、 R5、R6And R7It is identical or different.
Partly preferably the structural formula of the luminescent material with thermotropic delayed fluorescence is as follows：
Above-mentioned each specific substituent group or compound are enumerating under the design of the present invention, are mainly showed by enumerating Technical concept is not the design to the present invention or the limitation or restriction of claims.
Luminescent material provided by the present invention with thermotropic delayed fluorescence is by introducing different electron withdrawing groups and change It changes on-link mode (OLM) and the photochromic of final product, thermal stability and luminous efficiency etc. is adjusted.
Luminescent material provided by the present invention with thermotropic delayed fluorescence can be prepared by the following method to obtain, with R2、 R3、R4、R5、R6And R7For being hydrogen：
1) Suzuki cross-coupling reactions：
3- carbazoles pinacol borate and o-dibromobenzene occur Suzuki cross-coupling reactions and obtain intermediate product III；
2) the intermediate product III that is obtained with step 1) is reactant, and n,N-Dimethylformamide (DMF) is reacts molten Agent pulls out hydrogen with sodium hydride, then adds in p-methyl benzene sulfonic chloride, intermediate product IV is obtained by the reaction at room temperature；
3) intermediate product IV that step 2) obtains is dissolved into tetrahydrofuran, is cooled down with liquid nitrogen, then add in normal-butyl Lithium generating negative ionsization are reacted, and the benzophenone that tetrahydrofuran dissolving is added after the reaction was complete carries out substitution reaction, then, with Acetic acid is reaction dissolvent, and hydrochloric acid cyclization obtains intermediate product V；
4) it with the obtained intermediate product V of step 3) for raw material, adds in excess base and reaction is hydrolyzed, obtain intermediate production Object VI；
5) intermediate product VI is obtained as raw material with step 4), adds in the R of single fluorine substitution1Replaced, obtain I chemical combination of formula Object；
Alternatively, obtaining intermediate product VI as raw material with step 4), the R of difluoro substitution is added in1Replaced, obtain formula II and change Close object.
Wherein：
The structural formula of intermediate product III is
The structural formula of intermediate product IV is
The structural formula of intermediate product V is
The structural formula of intermediate product VI is
And preparation method is generally：
A, with above-mentioned steps 1) it is prepared respectively comprising R to step 4)2、R3、R4The first monomer and/or include R5、R6And R7 The first monomer；
B, the R of single fluorine substitution1Replace with the first monomer, alternatively, the R of single fluorine substitution1Replace with second comonomer, alternatively, double fluorine Substituted R1Replace with the first monomer, alternatively, the R of double fluorine substitution1With the R of second comonomer substitution or the substitution of double fluorine1With first Monomer and second comonomer substitution, obtain the luminescent material with thermotropic delayed fluorescence.
This is simple for process, and yield is high, and passes through and introduce different electron withdrawing groups and transformation on-link mode (OLM) adjusting final product Photochromic, thermal stability and luminous efficiency etc..
The present invention also provides the application of the luminescent material provided by the present invention with thermotropic delayed fluorescence, as organic Electroluminescent layer material in electroluminescent device, the electroluminescent layer material is fluorescence radiation guest materials, phosphorescence host Material or fluorescent host material.
Using the luminescent material provided by the present invention with thermotropic delayed fluorescence as main body luminescent material, device can be reduced The efficiency roll-off of part.As guest emitting material, luminescent layer brightness is high, and stability is good, and luminous efficiency is high, and service life is long.
The present invention also provides a kind of electroluminescent device, the electroluminescent device includes a pair of electrodes and is arranged on Organic light emitting medium between electrode at least has the thermotropic delay glimmering in the organic light emitting medium containing provided by the present invention The luminescent material of light.
Using the luminescent material provided by the present invention with thermotropic delayed fluorescence as organic light emitting medium, the efficiency of device It roll-offs low, luminous efficiency is high, and service life is long.
In general, by the above technical scheme conceived by the present invention compared with prior art, it can obtain down and show Beneficial effect.
(1) the carbazole analog derivative donor groups have rigid structure, so thermal stability is good, are prepared for vacuum evaporation high The stable device of effect provides possibility.
(2) the carbazole analog derivative has high triplet, by bonded different acceptor groups or changes bridging side Formula, can adjust the hot property of material, luminous efficiency and photochromic, can be designing synthesis blue light emitting material in short supply at present Material is, it can be achieved that dark blue light emitting.
(3) there is the carbazole analog derivative very strong effect of steric hindrance can realize that intramolecular distorts, and not only reduce point It can make the highest occupied molecular orbital of molecule and the electronics of lowest unoccupied molecular orbital when assembling between son, and combining another electron withdrawing group Single triplet energy level that cloud relative separation obtains very little is poor, so as to luminous with thermotropic delayed fluorescence property to prepare Molecule.Material with thermotropic delayed fluorescence property can reduce efficiency roll-off as the main body of phosphor material, be sent out as object Luminescent material can realize high efficiency and good stability.Therefore before such material has application well in organic light emission field Scape.
(4) the present invention provides a kind of synthetic schemes of simple possible, and yield is higher.
Description of the drawings
Fig. 1 is the energy diagram of electroluminescent device provided by the present invention.
Fig. 2 is the life time decay figure of compound 13.
Fig. 3 is the life time decay figure of compound 14.
The life time decay figure of Fig. 4 compounds 15.
Fig. 5 is the electroluminescent light spectrogram of compound 13,14 and 15.
Specific embodiment
The principles and features of the present invention are described below, and illustrated embodiment is served only for explaining the present invention, is not intended to Limit the scope of the present invention.
The carbazole analog derivative that the present invention is prepared prepares device, and its performance is tested as light-emitting guest Card and analysis.
It is embodiment below：
Embodiment 1：
Two fluorenes diindyl analog derivative 13 of spiral shell of the present invention (5- (4,6- diphenyl -1,3,5- triazines) -5H spiro fluorenes - 9,8- indenes carbazole) it can be synthesized by following method.
(1) in the twoport flask of dry 500mL, by 3- carbazoles pinacol borate (15g, 51mmol), adjacent dibromo Benzene (14.5g, 61.2mmol), toluene (120mL), ethyl alcohol (60mL) and 2mol/L solution of potassium carbonate (60mL) add in, first ultrasound, Then quick mixing drum nitrogen is rapidly added catalyst four (triphenylphosphine) and changes palladium (1.8g, 1.53mmol), largely leads to nitrogen. 90 DEG C are heated to, is stirred overnight.It during processing, first extracts, is spin-dried for, it is solid to obtain white with petroleum ether and dichloromethane column chromatography Body product 3- (2- bromophenyls) -9H- carbazoles, yield 93%.C18H12BrN, mass spectrum theoretical value 321.0153, APCI (atmospheric pressure Learn ionization pattern) it measures：321.0198.
(2) the intermediate product I (14g, 43.47mmol) that step (1) obtains first is added in, is dissolved with DMF (70mL), ice bath, Be gradually added into sodium hydride (3.5g, 86.94mmol), after 10 minutes by the p-methyl benzene sulfonic chloride of DMF dissolvings (12.4g, It 65.2mmol) is added dropwise, clear solution becomes cloudy, and last yellow disappears.After reacting 4h, first adding in a large amount of water analyses product Go out, filter, rinsed with a large amount of water, to remove DMF.Dichloromethane dissolution extraction is used again.Next, petroleum ether and dichloro can be used Methane carries out column chromatography and obtains white solid product (2- bromophenyls) -9H- tosyl -9H- clicks, intermediate product II. yields 90%.C25H18BrNO2S, mass spectrum theoretical value 475.0242, APCI (atmospheric pressure chemical ionization pattern) are measured：475.0302.
(3) by two mouthfuls of 250mL round-bottomed flasks of drying, magneton and constant pressure funnel are ready to, and then add step Vacuum state in round-bottomed flask is led to nitrogen, added immediately by the intermediate product II (6.5g, 13.66mmol) that (2) obtain suddenly again Enter dry tetrahydrofuran (80mL), after stirring and dissolving, the cooling of liquid feeding nitrogen, be added dropwise after ten minutes n-BuLi (6.8mL, 16.39mmol), it adds within 15 minutes.After adding reaction 1h, the benzophenone (2.7g, 15.02mmol) of THF dissolvings is added dropwise, Reaction 2h removes low temperature pot later, is warming up to room temperature naturally.Add a small amount of water quenching after reacting 12h.It is spin-dried for removing water and THF. It is thick solid to be spin-dried for 100mL single port bottles.Acetic acid (100mL) is added to do solvent, hydrochloric acid (25mL) cyclization.120 DEG C are heated to, It is refluxed 12h.After reaction plus elutriation goes out solid, filters.Intermediate product is obtained with petroleum ether and ethyl acetate column chromatography III, 12,12- diphenyl -5- tosyls -5,12- dihydros indeno [1,2-b] carbazole.Yield 85%.C38H27NO2S, mass spectrum Theoretical value 561.1762, APCI (atmospheric pressure chemical ionization pattern) are measured：561.1793.
(4) the intermediate product III and sodium hydroxide obtained step (3) presses 1:10 molar ratio feeds intake, and takes THF (40mL) can be molten 12,12- diphenyl -5- tosyl -5,12- dihydros indeno [1,2-b] carbazoles (4.2g, 7.5mmol) Solution, then add ethyl alcohol (100mL), with 20mL water dissolutions NaOH.80 DEG C are heated to, is stirred at reflux 12h.First solvent is revolved during processing It is dry, then add in a small amount of hydrochloric acid and a large amount of water and potassium hydroxide, product are precipitated, it filters, is extracted with dichloromethane, dry method loading mistake Column.Intermediate product IV, 12,12- diphenyl -5,12- dihydros indeno [1,2-b] click is obtained with petroleum ether and dichloromethane column chromatography Azoles, yield 91%.C31H21N, mass spectrum theoretical value 407.1674, APCI (atmospheric pressure chemical ionization pattern) are measured：407.1726.
(5) the chloro- 4,6- diphenyl -1,3,5- triazines (1.34g, 5.00mmol) of 2- and (2- fluorophenyls) boric acid (0.70g, It 5.00mmol) is dissolved in dry tetrahydrofuran (30ml), then rouses nitrogen potassium carbonate (2.07g, 15.01mmol) dissolving Above-mentioned solution is added in distilled water (10ml).After drum nitrogen 20min, catalyst Pd (PPh3) 4 is added in, then and in nitrogen is protected It is refluxed under conditions of shield 8 hours.Reaction solution is cooled to room temperature, is extracted with water and dichloromethane, dry, is spin-dried for, into Row column chromatography, leacheate are n-hexane and ethyl acetate, obtain white powder intermediate product V, 2- (2- fluorophenyls) -4,6- bis- Phenyl -1,3,5- triazines.Yield 82%.C21H14FN3, mass spectrum theoretical value 327.1172, APCI (atmospheric pressure chemical ionization pattern) It measures:327.1196.
(6) synthesis of compound 13.By intermediate product IV (12,12- diphenyl -5,12- dihydros indeno [1,2-b] carbazole) (0.43g, 1.68mmol) is dissolved in dry DMF (10ml), is then slowly added drop-wise under nitrogen protection equipped with dissolving In the DMF solution of NaH (0.07g, 3.06mmol), stirring.After half an hour, 2- (2- fluorophenyls) -4,6- hexichol Base -1,3,5-triazines (0.50g, 1.53mmol), which is dissolved in the DMF of 10mL, to be added dropwise in above-mentioned reaction bulb, is refluxed 8 Hour.First cooling reaction, then adds in a large amount of water, and product is precipitated.By extraction, column chromatography can obtain pale yellow eventually crude product Color product 5- (2- (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5,12- dihydro indenos [1,2- C] carbazole.Yield 65%.C52H34N4, mass spectrum theoretical value 714.2783, APCI (atmospheric pressure chemical ionization pattern) measures: 714.2811。
It is 13 compound represented of formula by above-mentioned mass spectral results it is found that the light yellow solid product structure is correct.
Embodiment 2：
The carbazole analog derivative formula 13 that embodiment 1 is prepared, 5- (2- (4,6- diphenyl -1,3,5-triazines -2- bases) Phenyl) -12,12- diphenyl -5,12- dihydros indeno [1,2-c] carbazole prepares device as light-emitting guest.
This embodiment illustrates the performance verification of 13 electroluminescent devices prepared as guest emitting material.ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then it is dried in vacuo 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted in vacuum chamber and makes Standby organic film and metal electrode then prepare the hole-injecting material molybdenum trioxide of one layer of 10nm by the method for vacuum evaporation, Then the hole mobile material of 70nm thickness is deposited:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- biphenyl] -4, 4'- diamines (NPB), is then deposited the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm, then passes through vacuum evaporation one The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of 25nm:10% compound 13, Ran Houzheng One layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm is plated, the Al of the LiF and 100nm of one layer of 1nm are finally deposited again.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.15,0.21), opens bright voltage 3.5V, maximum external quantum efficiency 19.1%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:The compound 13 (25nm) of 10wt%/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/ Al(100nm)。
Embodiment 3：
Of the present invention 14 (5- (3- (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5, 12- dihydros indeno [1,2-c] carbazole) it can be synthesized by following method.
14 (5- (3- (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5,12- dihydro indenos [1,2-c] carbazole) synthesis.12,12- diphenyl -5,12- the dihydros first obtained according to 1 step of embodiment (1)~(4) synthesis Indeno [1,2-b] carbazole (1g, 2.466mmol), 2,4- diphenyl -6 (3- bromophenyls) triazines (1.15g, 2.95mmol), iodate Cuprous (0.28g, 1.47mmol), K2CO3(2.04g, 14.7mmol) and 18- crown-s 6 (0.378g, 1.47mmol) are dissolved into In 3mLDMPU solution.Under the protection of N2,175 DEG C are warming up to, reacts 36h.It after reaction terminating, is cooled to room temperature, extracts, It is spin-dried for, column chromatography.Yellow solid product 1.2g, yield 71% are obtained with petroleum ether and dichloromethane column chromatography.C52H34N4, mass spectrum Theoretical value 714.2783, APCI (atmospheric pressure chemical ionization pattern) are measured:714.2824.
It is 14 compound represented of formula (5- (3- by above-mentioned mass spectral results it is found that the light yellow solid product structure is correct (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5,12- dihydros indeno [1,2-c] carbazole).
Embodiment 4：
(5- (3- (4,6- diphenyl -1,3,5- triazine -2- bases) benzene of carbazole analog derivative 14 that embodiment 3 is prepared Base) -12,12- diphenyl -5,12- dihydros indeno [1,2-c] carbazole) as light-emitting guest prepare device.
This example illustrates the performance verification of electroluminescent device that formula 14 is prepared as guest emitting material.ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then it is dried in vacuo 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted in vacuum chamber and makes Standby organic film and metal electrode then prepare the hole-injecting material molybdenum trioxide of one layer of 10nm by the method for vacuum evaporation, Then the hole mobile material of 70nm thickness is deposited:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- biphenyl] -4, 4'- diamines (NPB), is then deposited the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm, then passes through vacuum evaporation one The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of 25nm:10% compound 14, Ran Houzheng One layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm is plated, the Al of the LiF and 100nm of one layer of 1nm are finally deposited again.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.18), opens bright voltage 3.6V, maximum external quantum efficiency 14.2%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:The compound 14 (25nm) of 10wt%/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/ Al(100nm)。
Embodiment 5：
Of the present invention 15 can be synthesized by following method.
15 5- (4- (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5,12- dihydro indenos The synthesis of [1,2-c] carbazole.By 2- (4- bromophenyls) -4,6- diphenyl -1,3,5- triazines (1.054g, 2.72mmol), 12, 12- diphenyl -5,12- dihydros indeno [1,2-b] carbazole (1g, 2.47mmol), Pd (OAc)2(0.011g,0.0494mmol), Tetrafluoro boric acid tri-tert-butylphosphine (0.043g, 0.148mmo), NaOtBu (0.593g, 6.175mmol), dry toluene 50mL, N2Protection, is refluxed 8h.Post-reaction treatment obtains light yellow solid final product 15 with petroleum ether and dichloromethane column chromatography. Yield 72%.C52H34N4, mass spectrum theoretical value 714.2783, APCI (atmospheric pressure chemical ionization pattern) measures:714.2797.
It is 15 compound represented 5- (4- of formula by above-mentioned mass spectral results it is found that the light yellow solid product structure is correct (4,6- diphenyl -1,3,5- triazine -2- bases) phenyl) -12,12- diphenyl -5,12- dihydros indeno [1,2-c] carbazole.
Embodiment 6：
15 5- of carbazole analog derivative (4- (4,6- diphenyl -1,3,5- triazine -2- bases) benzene that embodiment 5 is prepared Base) -12,12- diphenyl -5,12- dihydros indeno [1,2-c] carbazole prepares device as light-emitting guest.
This example illustrates the performance verification of 15 electroluminescent devices prepared as guest emitting material.ITO (oxygen Change indium tin) glass is in succession in cleaning agent and deionized water with ultrasonic cleaning 30 minutes.Then it is dried in vacuo 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, being transmitted to prepare in vacuum chamber has Machine film and metal electrode then prepare the hole-injecting material molybdenum trioxide of one layer of 10nm, then by the method for vacuum evaporation The hole mobile material of 70nm thickness is deposited:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- biphenyl] -4,4'- bis- Amine (NPB), is then deposited the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm, then passes through one 25nm's of vacuum evaporation Luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO):Then 10% compound 15 is deposited one layer The Al of the LiF and 100nm of one layer of 1nm is finally deposited in 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm again.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.16), opens bright voltage 3.0V, maximum external quantum efficiency 17.8%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 15 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Analytic explanation is carried out to attached drawing and table below：
Fig. 1 is that the compound 13,14 and 15 that embodiment 1,3 and 5 provides is shown respectively as guest emitting material device architecture It is intended to, wherein HIL is MoO3, HTL NPB, HBL mCP, Host are DPEPO, and ETL is Bphen.
Fig. 2 is transient service life of the compound 13 of the offer of embodiment 1 to be measured in 10% doped in concentrations profiled to DPEPO Figure has the delay service life under being protected in air with nitrogen, and the service life surveyed in air is significantly than the delay longevity under nitrogen protection Life it is short, illustrate oxygen quenched a part of luminous triplet exciton namely in luminescence process there are triplet exciton to The process to shine after appearing vividly is worn between singlet excitons inverse system.It can illustrate that the material has thermotropic delayed fluorescence property.
Fig. 3 is transient service life of the compound 14 of the offer of embodiment 3 to be measured in 10% doped in concentrations profiled to DPEPO Figure has the delay service life under being protected in air with nitrogen, and the service life surveyed in air is significantly than the delay longevity under nitrogen protection Life it is short, illustrate oxygen quenched a part of luminous triplet exciton namely in luminescence process there are triplet exciton to The process to shine after appearing vividly is worn between singlet excitons inverse system.It can illustrate that the material has thermotropic delayed fluorescence property.
Fig. 4 is transient service life of the compound 15 of the offer of embodiment 5 to be measured in 10% doped in concentrations profiled to DPEPO Figure has the delay service life under being protected in air with nitrogen, and the service life surveyed in air is significantly than the delay longevity under nitrogen protection Life it is short, illustrate oxygen quenched a part of luminous triplet exciton namely in luminescence process there are triplet exciton to The process to shine after appearing vividly is worn between singlet excitons inverse system.It can illustrate that the material has thermotropic delayed fluorescence property.
Fig. 5 is the electroluminescent light spectrogram for 13,14 and 15 device of compound that embodiment 1,3 and 5 provides.It is supplied by changing Connection mode between body group and acceptor groups can adjust photochromic to the dark blue light that shines of molecule.
Table 1 lists the fundamental property of part of compounds 13-15 provided by the present invention, of the invention as can be seen from Table I The carbazole derivative material being related to has higher triplet, can design blue light emitting material.Three kinds shown in table Single triplet energy level difference of material is smaller, can build the luminescent material with thermotropic delayed fluorescence property.From solution state Fluorescence quantum yield from the point of view of, the fluorescence quantum yield of molecule can be significantly improved up to 95% by rational MOLECULE DESIGN.
The fundamental property of 1. part of compounds of table
Compound 1-40 is grouped, each group has identical R1, substitution site is different in each group：
Embodiment 7
Compound 1-9 is one group, and by taking compound 1 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 1, one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm is then deposited, the LiF and 100nm of one layer of 1nm are finally deposited again Al.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.29), opens bright voltage 3.0V, maximum external quantum efficiency 18.2%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 1 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Embodiment 8
Compound 10-12 is one group, and by taking compound 12 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 12, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.18), opens bright voltage 3.7V, maximum external quantum efficiency 16.0%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 12 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Embodiment 9
Compound 16-18 is one group, and by taking compound 18 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 18, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.15), opens bright voltage 3.6V maximum external quantum efficiency 19.3%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 18 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Embodiment 10
Compound 19-21 is one group, and by taking compound 21 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 21, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.15,0.22), opens bright voltage 3.8V, maximum external quantum efficiency 20.1%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 21 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Compound 22-24 is one group, and by taking compound 24 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 24, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.15,0.29), opens bright voltage 3.2V maximum external quantum efficiency 17.2%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 24 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Compound 25-27 is one group, and by taking compound 27 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 27, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.23), opens bright voltage 3.5V, maximum external quantum efficiency 19.6%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 27 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Compound 28-30 is one group, and by taking compound 30 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 30, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.32), opens bright voltage 3.6V, maximum external quantum efficiency 15.9%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 30 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Compound 33-35 is one group, and by taking compound 34 as an example, preparing for device is as follows：
ITO (tin indium oxide) glass is in succession with ultrasonic cleaning 30 minutes in cleaning agent and deionized water.Then vacuum Dry 2 hours (105 DEG C), then ito glass is put into the oxygen plasma treatment carried out in plasma reactor 5 minutes, it is transmitted to Organic film and metal electrode are prepared in vacuum chamber, the hole-injecting material of one layer of 10nm is then prepared by the method for vacuum evaporation The hole mobile material of 70nm thickness is then deposited in molybdenum trioxide:N4, N4'- bis- (naphthalene -1- bases)-N4, N4'- diphenyl-[1,1'- Biphenyl] -4,4'- diamines (NPB), the electronic barrier layer of 1,3- bis- (9- carbazyls) benzene (mCP) 5nm is then deposited, then by true The luminescent layer (oxygroup is bis- (2,1- phenylenes)) bis- (diphenyl phosphine oxides) (DPEPO) of one 25nm of sky vapor deposition:10% compound 34, then be deposited one layer of 4,7- diphenyl -1,10- phenanthroline (Bphen) 30nm, be finally deposited again one layer of 1nm LiF and The Al of 100nm.
The anode of direct current is added on ITO (tin indium oxide) layer, cathode is added on metal layer by cathode of the aluminium as device, The i.e. available bright uniform light sent out from ITO (tin indium oxide) layer, CIE chromaticity coordinates is (0.16,0.25), opens bright voltage 3.4V, maximum external quantum efficiency 16.8%.This experiment apparatus structure is：ITO (tin indium oxide)/MoO3(10nm)/NPB (70nm)/mCP(5nm)/DPEPO:10wt% compounds 34 (25nm)/DPEPO (5nm)/Bphen (30nm)/LiF (1nm)/Al (100nm)。
Compound 1,12,18,21,24,27,30,34 prepares isostructural device respectively, and device performance see the table below 2.Table 2 It is being showed in organic electroluminescence device for part of compounds, such material is as fluorescence visitor as can be seen from the table It has outstanding performance during body, is a kind of very promising luminescent material.
The device fundamental property of 2. part of compounds of table
The organic luminescent device prepared as from the foregoing with the luminescent material provided by the invention with thermotropic delayed fluorescence has Have that cut-in voltage is low, external quantum efficiency is high, and it is photochromic be adjustable to dark blue light, have on structure blue light organic luminescent material important Application value.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.

Claims (8)

1. the luminescent material with thermotropic delayed fluorescence, which is characterized in that there is the general structure of following formula (I) or formula (II)：
Wherein：
R1For electron withdrawing group, R2、R3、R4、R5、R6And R7It is independently electron-donating group or hydrogen, R2、R3、R4、R5、R6And R7 It is identical or different.
2. the luminescent material according to claim 1 with thermotropic delayed fluorescence, which is characterized in that R1It is selected from：
The aromatic group of cyano substitution；
Alternatively, the carbon atom number containing at least one miscellaneous aromatic rings is 5~30 non-substituted electron withdrawing group, each aromatic rings Connected by singly-bound or condensed, miscellaneous aromatic rings is miscellaneous five-membered ring or miscellaneous hexatomic ring, in miscellaneous aromatic rings heteroatomic quantity be 1, 2nd, 3 or 4, each hetero atom is respectively nitrogen, oxygen, phosphorus or sulphur, and each hetero atom is identical or different；
Alternatively, the carbon atom number containing at least one miscellaneous aromatic rings is 5~53 substituted electron withdrawing group of hydrogen, each fragrance Ring is connected or condensed by singly-bound, and miscellaneous aromatic rings is miscellaneous five-membered ring or miscellaneous hexatomic ring, and heteroatomic quantity is in miscellaneous aromatic rings 1st, 2,3 or 4, each hetero atom is respectively nitrogen, oxygen, phosphorus or sulphur, and each hetero atom is identical or different, and substituent group is that carbon atom number is 1-20 Alkyl or silane alkyl.
3. the luminescent material according to claim 2 with thermotropic delayed fluorescence, it is characterised in that：
The aromatic group of cyano substitution is cyano-phenyl, cyanonaphthyl or cyanobiphenyl base；
The non-substituted electron withdrawing group that carbon atom number containing at least one miscellaneous aromatic rings is 5-30 is thienyl group, benzo Thienyl group, pyridine groups, pyrrole group, oxazole group, thiazolyl group, thiadiazoles group, triazine group, diphenylphosphine oxygroup Group, imidazole group, to phenyl benzimidazole groups group, phenyl benzimidazole groups group, carbazole group, indolyl radical, quinoline group Or isoquinolin group.
4. the luminescent material according to claim 3 with thermotropic delayed fluorescence, which is characterized in that R1Selected from lower structure Formula：
Wherein, * is the position of substitution.
5. the luminescent material according to claim 4 with thermotropic delayed fluorescence, which is characterized in that R2、R3、R4、R5、R6With R7Be independently selected from hydrogen, phenyl, naphthalene, tertiary butyl, Wherein * be the position of substitution, R2、R3、R4、R5、R6And R7It is identical or different.
6. the luminescent material according to claim 5 with thermotropic delayed fluorescence, which is characterized in that structural formula is as follows：
7. a kind of application of the luminescent material according to any one of claims 1 to 6 with thermotropic delayed fluorescence, feature exist In as the electroluminescent layer material in organic electroluminescence device, the electroluminescent layer material is fluorescence radiation object material Material, phosphorescent light body material or fluorescent host material.
8. a kind of electroluminescent device, the electroluminescent device includes the organic hair of a pair of electrodes and setting between the electrodes Optical medium, which is characterized in that at least contain a kind of tool according to any one of claims 1 to 6 in the organic light emitting medium There is the luminescent material of thermotropic delayed fluorescence.
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