CN107325076B - A kind of compound and its luminescent device and display device - Google Patents

A kind of compound and its luminescent device and display device Download PDF

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CN107325076B
CN107325076B CN201710515829.9A CN201710515829A CN107325076B CN 107325076 B CN107325076 B CN 107325076B CN 201710515829 A CN201710515829 A CN 201710515829A CN 107325076 B CN107325076 B CN 107325076B
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CN107325076A (en
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代好
张正川
叶添昇
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Wuhan Tianma Microelectronics Co Ltd
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Shanghai Tianma AM OLED Co Ltd
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Abstract

The present invention relates to technical field of organic luminescence materials, and in particular to a kind of compound and its luminescent device and display device.The structural formula of the compound is as shown in general formula I.The present invention proposes a kind of TADF material based on tetraphenyl ethylene structure, have TADF and AIE effect concurrently, it can use the triplet excitons that conventional fluorescent molecular transition is prohibited not only to shine, moreover it is possible to the Exciton quenching under high current density and doping concentration is avoided, to be remarkably improved the efficiency of device.

Description

A kind of compound and its luminescent device and display device
Technical field
The present invention relates to technical field of organic luminescence materials, and in particular to a kind of compound and its luminescent device and display dress It sets.
Background technique
Organic electroluminescence device (OLEDs) can be divided into fluorescent device and phosphorescent devices according to the classification of luminescent excitons. Compared with the conventional fluorescent device for being only capable of shining using singlet exciton energy (25%), phosphorescent devices are because theoretically can achieve 100% internal quantum efficiency and have more extensive application prospect.But phosphorescent devices are also because lead to cost containing heavy metal Excessively high (almost in terms of the several times of fluorescent material), stability poor (lifetime is short) and endure to the fullest extent and denounce.
Most over the past two years, a kind of completely new luminescent material --- thermotropic delayed fluorescence (Thermally Activated Delayed Fluorescence, TADF) material, using the principle for converting (E-type up conversion) in E type, energy is same The energy of Shi Liyong singlet and triplet excitons possesses higher internal quantum efficiency；Since it is as conventional fluorescent material Without heavy metal, cost can be substantially reduced and improve stability and attract attention.Currently, being measured outside the device based on such material Sub- efficiency can mutually be equal to completely with phosphorescent devices.
Delayed fluorescence in order to inversely altered using triplet state to singlet energy level more (RISC) to radioluminescence, it is necessary to will be single Line state and triplet difference, which are reduced to, can satisfy value (under normal circumstances, the Δ E inversely altered moreST≤0.2ev).That is Δ EST It is positively correlated with the overlapping degree of HOMO, LUMO, such as to reduce Δ EST, need as much as possible to separate HOMO, LUMO.
In OLED device, luminescent material exists in the form of solid film, since luminous organic material is big pi-conjugated System, aggregation inducing fluorescent quenching (Aggregation Caused caused by being easy to happen because of " π-π " sedimentation Quenching, ACQ), so as to cause inefficiency.Tetraphenyl ethylene (TPE) is the blue light AIE being more early found (Aggregation Induced Emission) material, but the blue-light device constructed based on TPE only has the efficiency of 0.45cd/A, Therefore how TPE is modified, design high efficiency AIE material is still a challenge.
Since the AIE material currently based on tetraphenyl ethylene is pure p-type, the material of rare bipolarity (bipolar) type Design, reduces the potential barrier of device and carrier injection transmission is unfavorable, to influence efficiency and the service life of device.
In consideration of it, special propose the application.
Summary of the invention
The primary goal of the invention of the application is to propose a kind of compound.
The second goal of the invention of the application is to propose a kind of luminescent device.
The third goal of the invention of the application is to propose a kind of display device.
In order to complete the purpose of the application, the technical solution of use are as follows:
To complete first invention purpose of the invention, the present invention proposes that a kind of compound, the structural formula of the compound are such as logical Shown in Formulas I:
Wherein,
Ra、Rb、Rc、RdIt is independently selected from electron-donating group；
R1Selected from electron-withdrawing group；
R2、R3It is independently selected from hydrogen atom or electron-withdrawing group；
M, n, p, q are independently selected from 1~5 integer；
R, s is independently selected from 1~4 integer.
Optionally, the structural formula of the compound is as shown in general formula IA:
Wherein, R1Selected from electron-withdrawing group；
R2、R3It is independently selected from hydrogen atom or electron-withdrawing group.
Optionally, R1Selected from substituted or unsubstituted C6~C48Aryl, substituted or unsubstituted C3~C48Heteroaryl；R2、R3 It is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, halogen replace C1~C6Alkyl, substituted or unsubstituted C6~ C48Aryl, substituted or unsubstituted C3~C48Heteroaryl；Substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen The C that element replaces1~C6Alkyl.
Optionally, the hetero atom in the heteroaryl is nitrogen-atoms.
Optionally, R1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted naphthalene It is base, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted Quinolyl, the substituent group that indicates of substituted or unsubstituted isoquinolyl or following structural formula:
Wherein, substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~ C6Alkyl；
Ra、Rb、RcIt is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1 ~C6Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T, u, v are independently selected from 1~5 integer.
Optionally, R2、R3It is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen take The C in generation1~C6Alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted naphthalene, substitution Or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted quinoline The substituent group that base, substituted or unsubstituted isoquinolyl or following structural formula indicate:
Wherein, substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~ C6Alkyl；
Ra、Rb、RcIt is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1 ~C6Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T, u, v are independently selected from 1~5 integer.
Optionally, R2And R3For identical substituent group.
Optionally, R1、R2And R3It is identical substituent group.
Optionally, one of which of the compound in following compound:
To complete the second goal of the invention of the invention, the present invention proposes a kind of luminescent device, which includes first Electrode, the second electrode relative to first electrode and at least one organic layer for being set between first electrode and second electrode, Organic layer includes the compound of the present invention.
To complete third goal of the invention of the invention, the present invention proposes a kind of display device, which includes this hair Bright luminescent device.
Technical solution of the present invention at least has following beneficial effect:
The present invention proposes a kind of TADF material based on tetraphenyl ethylene structure, using tetraphenyl ethylene structure as TADF material P-type chromophore (donor unit), passes through acridine SP3The linkage connection acceptor groups (acceptor unit) of hydridization, no Conjugate length can only be shortened, energy level is improved, molecular thermodynamics stability can also be improved；Meanwhile short axle conjugation weakens point Electric charge transfer in son, can narrow luminescent spectrum to a certain extent.
The compound of the present invention has lesser Δ EST, can satisfy triplet energy state and inversely alter more (RISC) to singlet To improve radioluminescence efficiency.Therefore, luminescent material of the invention has TADF and AIE effect concurrently, not only can use tradition The triplet excitons that fluorescent molecule transition is prohibited shine, moreover it is possible to avoid the Exciton quenching under high current density and doping concentration, To be remarkably improved the efficiency of device.
TADF material proposed by the present invention based on tetraphenyl ethylene structure has bipolarity (bipolar) characteristic, conduct Luminescent layer can significantly improve the injection and transmission of two kinds of carriers, so as to reduce the starting voltage of device.Meanwhile using this hair The luminescent layer of the luminescent device of bright compound preparation is free of precious metal, can substantially reduce cost.
Detailed description of the invention
Fig. 1 is the emission spectrum of compound M1；
Fig. 2 is the emission spectrum of compound M2；
Fig. 3 is the HOMO-LOMO track schematic diagram of compound M1；
Fig. 4 is the HOMO-LOMO track schematic diagram of compound M2；
Fig. 5 is compound M1 in THF:H2Fluorescence intensity curves in O dicyandiamide solution；
Fig. 6 is compound M2 in THF:H2Fluorescence intensity curves in O dicyandiamide solution；
Fig. 7 is the structural schematic diagram of luminescent device in the embodiment of the present invention；
Fig. 8 is the structural schematic diagram of display device in the embodiment of the present invention；
Fig. 9 is the current density plot of device 1#；
Figure 10 is the current density plot of device 2#；
Wherein:
10- luminescent device；
11- anode；
12- hole transmission layer；
13- luminescent layer；
14- electron transfer layer；
15- cathode.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention Rather than it limits the scope of the invention.
As the embodiment of the present invention in a first aspect, the embodiment of the present invention proposes a kind of compound, structural formula such as general formula I It is shown:
Wherein, Ra、Rb、Rc、RdIt is independently selected from hydrogen atom or electron-donating group；
R1Selected from electron-withdrawing group；
R2、R3It is independently selected from hydrogen atom or electron-withdrawing group；
M, n, p, q are independently selected from 1~5 integer；R, s is independently selected from 1~4 integer.
It is said on ordinary meaning, after hydrogen on substituent group substituted benzene ring, electron density on phenyl ring is caused to increase originally relatively Be electron-donating group；Conversely, causing what electron density on phenyl ring reduced originally relatively to be electron-withdrawing group.The embodiment of the present invention Electron-withdrawing group is arranged in acridine moiety in the molecular structure, so as to which HOMO and LUMO to be arranged in different structure lists respectively It in member, realizes HOMO-LUMO and is totally separated from, facilitate the poor Δ E of energy between reduction gapST, to alter more ability between improving inverse gap. Further, electron-donating group is further set in tetraphenyl ethylene part, can further promotes the separation of HOMO-LUMO.
Work as Ra、Rb、Rc、RdWhen being hydrogen atom, the compound of the embodiment of the present invention is selected from general formula IA compound represented:
Wherein, R1Selected from electron-withdrawing group；
R2、R3It is independently selected from hydrogen atom or electron-withdrawing group.
In general formula I, general formula IA, R1It can be selected from substituted or unsubstituted C6~C48Aryl, substituted or unsubstituted C3~ C48Heteroaryl；
R2、R3It is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, halogen replace C1~C6Alkyl, substitution or Unsubstituted C6~C48Aryl, substituted or unsubstituted C3~C48Heteroaryl；
Substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl.
Wherein, C6~C48Aryl includes phenyl and is connected by multiple phenyl or condensed obtained group；C3~C48Heteroaryl Including containing at least one heteroatomic heteroaryl and heteroaryl and aryl-condensed obtained substituent group.
In the heteroaryl of the embodiment of the present invention, hetero atom can be selected from nitrogen-atoms, oxygen atom, sulphur atom etc., further excellent It is selected as nitrogen-atoms, forms azepine aryl.
In general formula I, general formula IA, R1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substitution or Unsubstituted naphthalene, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, takes substituted or unsubstituted fluorenyl The substituent group that generation or unsubstituted quinolines base, substituted or unsubstituted isoquinolyl or following structural formula indicate:
Wherein,
Substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~C6Alkane Base；
Ra、Rb、RcIt is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1 ~C6Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T, u, v are independently selected from 1~5 integer.
In general formula I, general formula IA, R2、R3It is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or The C that part halogen replaces1~C6It is alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted Naphthalene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or not The substituent group that substituted quinolyl, substituted or unsubstituted isoquinolyl or following structural formula indicates:
Wherein,
Substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~C6Alkane Base；
Ra、Rb、RcIt is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1 ~C6Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T, u, v are independently selected from 1~5 integer.
It is further alternative, R1、R2、R3It is independently selected from the substituent group that following structural formula indicates:
Wherein, the integer of a, b, c expression 1~5 independent.
In the compound of the embodiment of the present invention, R2And R3It can be identical substituent group, symmetrical structure easily facilitates synthesis.
In the compound of the embodiment of the present invention, R1、R2And R3It is identical substituent group.
In the above-mentioned general formula of the embodiment of the present invention,
" heteroaryl " refers to that one or more aromatic core carbon in aryl substitute gained by hetero atom (such as O, N and S atom) To monovalent organic group comprising five yuan or hexa-atomic of monocyclic heteroaryl and thick and heteroaryl comprising replace or do not take The heteroaryl in generation.The example of unsubstituted heteroaryl include pyridyl group, pyrimidine radicals, thienyl, furyl, pyranose, pyrrole radicals, Triazolyl, tetrazole radical, indyl, pyridazinyl, pyrazinyl, triazine radical, quinolyl, isoquinolyl, thiazolyl, carbazyl, imidazoles Base, pyrazolyl, oxazolyl, oxadiazoles base, thiadiazolyl group, 1,2,3- triazolyl, 1,2,4- triazolyl, benzothiazolyl, benzo Oxazolyl, benzimidazolyl, but not limited to this.
Any monovalent organic radical obtained by one or more aromatic core carbon in " azepine aryl " i.e. above-mentioned " aryl " are substituted by N atom Group.
" alkyl " refers to saturated hydrocarbyl made of minusing a hydrogen atom in alkane molecule comprising straight or branched structure Alkyl comprising substituted or unsubstituted alkyl.The example of alkyl includes methyl, ethyl, propyl, isopropyl, isobutyl group, secondary Butyl, amyl, isopentyl, hexyl, but not limited to this.
The example of " halogen " includes fluorine, chlorine, bromine, iodine.
The compound of the improvement of compound as the embodiment of the present invention, the embodiment of the present invention is selected from shown in following structural formula One of which in compound:
The synthetic route of compound of the embodiment of the present invention are as follows:
One, the synthetic route of compound shown in Formulas I are as follows:
The general synthetic method of compound shown in Formulas I are as follows:
1, under nitrogen atmosphere, anhydrous tetrahydrofuran solution stirring and dissolving is added in precursor substance A, is delayed at -76 DEG C~-80 DEG C The slow n-BuLi that is added dropwise reacts certain time, and the tetrahydrofuran solution dissolved with precursor substance B is slowly added dropwise, warms naturally to room temperature simultaneously Reaction is overnight.Reaction is quenched with water after reaction, organic phase is then extracted with dichloromethane, in triplicate or more, evaporation Toluene washs and filters to obtain alcohol of formula crude intermediate after solvent.
2, crude intermediate is added to mixed solution 1~3h of reflux of dense HCl and AcOH, is cooled to room temperature, extraction, purifying Obtain compound shown in Formulas I.
Two, the synthetic route of precursor substance A are as follows:
The conventional method of precursor substance A are as follows:
Zn powder after activation is added in tetrahydrofuran solvent, -12 DEG C~8 DEG C is cooled to, TiCl is added under nitrogen protection4 And the certain time that flows back, it is down to room temperature and precursor substance A-S1 and A-S2 is added, flow back 18~22h.Near room temperature after reaction, Saturation K is added2CO3Solution, extraction, dry, purifying are to get precursor substance A.
Three, the synthetic route of precursor substance B are as follows:
Wherein, X indicates bromine or iodine.
Synthetic example 1
The synthesis and characterization of compound M1:
(1) synthesis of precursor substance A
Zn powder 6.5g (0.1mol) after activation is added in 100mL tetrahydrofuran solvent, is cooled to -10 DEG C, nitrogen is protected Under shield, it is slowly added to 9.5g (50mmol) TiCl4, flow back 2h, and it is down to room temperature and 2.6g (10mmol) 2- bromine benzophenone is added, 1.8g (10mmol) benzophenone, flow back 20h.Near room temperature after reaction is added 100mL and is saturated K2CO3Solution, dichloromethane Alkane (30mL × 3) extracts organic phase, rotates after dry and evaporates solvent, is purified and produced with column chromatography method (the pure petroleum ether of mobile phase) Object obtains white solid 1.5g, yield 37%.
HRMS(ESI):m/z:410.29。
1H NMR(400MHz,CDCl3): δ/ppm, 7.54 (d, 1H), 7.27-7.46 (m, 18H)
(2) synthesis of precursor substance B:
Under nitrogen atmosphere, 30mL anhydrous tetrahydrofuran solution stirring and dissolving is added in 2g (10mmol) acridone, under ice bath 1.6M n-BuLi 7.5mL (12mmol) reaction 30min is slowly added dropwise, then is slowly added dropwise to the yellow suspension of generation dissolved with 3g (11mmol) diphenyl triazine, the 20mL tetrahydrofuran solution of four triphenyl phosphorus palladium of 0.1g (0.1mmol), 80 DEG C of heating were reacted Night.It is cooled to room temperature after reaction, 100mL is added and is saturated NaCl solution, methylene chloride (30mL × 3) extracts organic phase, does Rotation evaporates solvent after dry, and 100mL re crystallization from toluene obtains white solid 2.8g, yield 66%.
MALDI-TOF:m/z:426.03；
1H NMR(CDCl3, 400MHz): δ=8.36 (m, 4H)；7.70(d,2H)；7.48-7.50(m,8H)；7.28(D, 2H)；7.18(t,2H).
(3) synthesis of compound M1:
Under nitrogen atmosphere, 0.41g (1mmol) precursor substance A (2-BrTPE) addition 10mL anhydrous tetrahydrofuran solution is stirred Dissolution is mixed, 1.6M n-BuLi 0.7mL (1.1mmol) reaction 30min is slowly added dropwise at -78 DEG C, is slowly added dropwise dissolved with 0.42g The 5mL tetrahydrofuran solution of (0.98mmol) precursor substance B warms naturally to room temperature and reacts overnight.
Organic phase is extracted with methylene chloride (30mL × 3) with after 100mL water quenching reaction after reaction, rotary evaporation falls Solvent, 10mL toluene wash and filter to obtain alcohol of formula crude intermediate；The mixing for being added into 5mL dense HCl and 50mLAcOH is molten Liquid flow back 2h, be cooled to room temperature, add water 100mL, with methylene chloride (10mL × 3) extract organic phase, and be saturated NaHCO3It is molten Liquid is adjusted to neutrality, turns to evaporate solvent, with column chromatography method (mobile phase n-hexane: methylene chloride=10:1) purified product, obtain To white solid (M1) 0.4g, yield 56%.
M1:MALDI-TOF:m/z:740.14；
1H NMR(CDCl3, 400MHz): δ=8.36 (D, 4H)；7.30-7.50(m,20H)；7.14-7.19(m,10H)； 6.95(m,2H).
The emission spectrum of M1 compound is as shown in Figure 1.Transmitting map as shown in Figure 1 is it is found that M1 compound is typical Blue emission, transmitting main peak are 476nm, and spectrum shape is relatively narrow, comparable to traditional blue fluorescent material.
Synthetic example 2
The synthesis and characterization of compound M2:
(1) synthesis of precursor substance A (2-BrTPE) is the same as synthetic example 1；
(2) synthesis of precursor substance B (dicyano acridone)
Acridone 2g (9.9mmol) is dissolved in 50mL methylene chloride, is added potassium carbonate 4.1g (30mmol), nitrogen atmosphere Under, 2.5mL bromine is slowly added dropwise, stirring at normal temperature is reacted for 24 hours.Saturated sodium bisulfite solution 50mL is slowly added to after reaction to remove Fall the complete bromine of unreacted.Organic layer drying is concentrated to get faint yellow crude product after liquid separation.
Crude product obtains white solid 2.85g, yield 81% with recrystallizing methanol.By this bromination product 2g (5.6mmol), Cuprous cyanide 3g (34mmol) is added 50mL DMF and is stirred at reflux reaction for 24 hours.After reaction, it is cooled to room temperature and by reaction solution Pour into 100mL iron chloride salt acid solution (15g iron chloride and 9mL mixed in hydrochloric acid be dissolved in 100mL water), after be warming up to 60 DEG C of stirrings 30min is reacted, room temperature is cooled to, extracts organic phase using methylene chloride (100mL × 3), the product after dry concentration uses Column chromatography for separation (methylene chloride: petroleum ether=1:1) obtains white solid 0.48g, yield 35%.
HRMS(ESI):m/z:244.96。
1H NMR(400MHz,CDCl3): δ/ppm, 8.19 (s, 2H), 7.67 (d, 2H), 7.46 (d, 2H), 7.2 (s, 1H)
(3) synthesis of compound M2
Specific experiment condition is the same as synthetic example 1.
M2:MALDI-TOF:m/z:635.29；
1H NMR(CDCl3, 400MHz): δ=7.70 (s, 2H)；7.45-7.50(m,8H)；7.38(d,2H)；7.20- 7.30(m,10H)；7.18(m,2H)；6.81(t,1H)；6.69(d,2H),6.63(d,2H).
M2 compound emission spectrum is as shown in Figure 2: transmitting map as shown in Figure 2 is it is found that M2 compound is typical blue Green emission, transmitting main peak are 501nm.
The performance evaluation of compound of the embodiment of the present invention:
One, energy level and Δ ESTTest
Compound of embodiment of the present invention M1~compound M4 HOMO-LOMO track is simulated by gaussian09 software, And test Δ EST。
Compound M1, the HOMO-LOMO track schematic diagram difference of compound M2 are as shown in Figure 3 and Figure 4.It can by Fig. 3 and Fig. 4 Finding out, compound M1, the HOMO of compound M2 and LUMO are arranged in respectively on different units, and it realizes and is totally separated from, this Helping to reduce between gap can poor Δ EST, to alter more ability between improving inverse gap.
With density functional theory (DFT), existed for compound M1~compound M4 using Gaussian09 program bag B3LYP/6-31G (d) is calculated under level, is optimized and has been calculated the distribution situation of molecule frontier orbit, chemical combination is calculated Object M1~compound M4 HOMO-LUMO energy level, Δ ESTTest result is specifically as shown in table 1.
Table 1:
In table 1, HOMO is indicated: highest occupied molecular orbital；
LUMO is indicated: lowest unoccupied molecular orbital；
Eg is indicated: forbidden bandwidth.
ES1It indicates: excited singlet energy；
ET1It indicates: excited triplet state energy；
ΔESTIt indicates: the energy differences between triplet energy state and singlet energy.
Data as shown in Table 1 are it is found that the compound of the present invention M1~compound M4 all has lesser Δ EST, therefore have The characteristic of standby TADF material.
Two, fluorescence lifetime
Test or calculation method are as follows: be based on time-depentent DFT (TDDFT), by Einstein Spontaneous Emission formula Calculate compound of embodiment of the present invention M1~compound M4 fluorescence lifetime.
Calculated result is specifically as shown in table 2.
Table 2:
Compound Rate of irradiation constant τ(μS)
M1 1.42×105 7.0
M2 5.26×105 1.9
M3 1.92×105 5.2
M4 3.70×105 2.7
In table 2, τ is indicated: fluorescence lifetime.
Data as shown in Table 2 are it is found that the compound of the present invention M1~compound M4 fluorescence lifetime is compared with conventional fluorescent The fluorescence lifetime that nS grades of material is higher by 3 magnitudes, shows that molecule has typical delayed fluorescence property.
Three, AIE effect
Test the AIE effect of compound of embodiment of the present invention M1, compound M2, test method are as follows:
Compound M1 is prepared respectively, compound M2 solubility is 10-5The THF:H of mol/L2(solvent burden ratio is respectively O solution 75:25,50:50,25:75,0:100), its fluorescence intensity is tested using sepectrophotofluorometer.
Experimental result difference is as shown in Figure 5 and Figure 6.
Compare compound M1, compound M2 in the THF:H of various concentration2Fluorescence intensity in O dicyandiamide solution, can be obvious Find out, with the decline of THF ratio, H2The fluorescence intensity of the rising of O ratio, material is significantly increased, and has apparent AIE effect It answers.
The embodiment of the present invention further relates to a kind of luminescent device, specially Organic Light Emitting Diode (OLED).Including anode, yin Pole and at least one organic layer being set between anode and cathode, organic layer include the compound of the present invention.
The number of plies of organic layer can be 1 layer, or multilayer.In organic layer include material of main part and guest materials, The compound of the present invention can be used as material of main part, also can be used as guest materials.
Fig. 7 is the structural schematic diagram of the luminescent device of the embodiment of the present invention, as shown in figure 9, luminescent device 10 includes successively Deposit anode 11, hole transmission layer 12, luminescent layer 13, electron transfer layer 14 and the cathode 15 formed.Its hole-transporting layer 12, Luminescent layer 13, electron transfer layer 14 are organic layer, anode 11 and cathode 15 be electrically connected.The luminescent device is formed in substrate (substrate) on, substrate is the transparent sun such as ITO or IGZO using glass or other suitable material (such as plastics), anode 11 Pole；Cathode 15 is metallic cathode.
The embodiment of the present invention further relates to a kind of display device, as shown in figure 8, including luminescent device 10 of the invention.
Four, compound of the embodiment of the present invention is used for the Performance Evaluation of OLED device
The preparation of OLED device: preparation TFT substrate；Anode is formed on the tft substrate；It is formed on the electrode comprising the present invention The organic layer of embodiment compound；Form cathode.
(1), by taking compound M1 as an example, the OLED device of doping volume is prepared as fluorescent dopants (dopant), Design number is the structure of the OLED device of 1# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:M1 (25nm, 5%)/TmPyPb (35nm)/ LiF(1nm)/Al(100nm)。
In order to compare the performance of the compound in the embodiment of the present invention, using the reference of classical blue light emitting material BCzVBi Device (reference), design number are the OLED device structure of the reference device of D1# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:BCzVBi (25nm, 5%)/TmPyPb (35nm)/LiF(1nm)/Al(100nm)。
Sample after the completion of preparation is tested for the property, using 705 spectrometer of Spectroscan PR and Keithley 236 Current Voltage source measuring systems detect the performance of the device.Test data is as shown in table 3.Current density plot is as shown in Figure 9 (wherein C.E. indicates current efficiency, and EQE indicates highest external quantum efficiency).
Table 3
In table 3, Vturn-onIndicate starting voltage；
EL(max)It indicates: maximum current efficiency；
It indicates: current density 10mA/cm2When current efficiency；
hp(max)It indicates: maximum power efficiency；
EQE(max)It indicates: external quantum efficiency (External Quantum Efficiency)；
CIE (x, y) is indicated: chromaticity coordinate.
The external quantum efficiency (EQE) that can be seen that device 1# from table 3 and Fig. 9 has mentioning for highly significant compared with reference device It is high.Meanwhile starting voltage and significantly lowering, advantageously reduce power consumption；CIE (x, y) is (0.13,0.14), is a kind of blue light material. The performance of above-mentioned organic luminescent device is mostly derived from the TADF characteristic and AIE effect of the compound M1 in luminescent layer itself, utilizes Triplet excitons that conventional fluorescent molecule (such as BCzVBi) transition is prohibited shine, to improve device efficiency.
(2), by taking compound M2 as an example, the OLED device of doping volume is prepared as fluorescent dopants (dopant), Design number is the structure of the OLED device of 2# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:M2 (25nm, 5%)/TmPyPb (35nm)/ LiF(1nm)/Al(100nm)。
In order to compare the performance of the compound in the embodiment of the present invention, using the reference of classical blue light emitting material BCzVBi Device (reference), design number are the OLED device structure of the reference device of D2# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:BCzVBi (25nm, 5%)/TmPyPb (35nm)/LiF(1nm)/Al(100nm)。
Sample after the completion of preparation is tested for the property, using 705 spectrometer of Spectroscan PR and Keithley 236 Current Voltage source measuring systems detect the performance of the device.Test data is as shown in table 4.Current density plot such as Figure 10 institute Show (wherein C.E. indicates current efficiency, and EQE indicates highest external quantum efficiency).
Table 4
In table 4, Vturn-onIndicate starting voltage；
EL(max)It indicates: maximum current efficiency；
It indicates: current density 10mA/cm2When current efficiency；
hp(max)It indicates: maximum power efficiency；
EQE(max)It indicates: external quantum efficiency (External Quantum Efficiency)；
CIE (x, y) is indicated: chromaticity coordinate.
The external quantum efficiency (EQE) that can be seen that device 2# from table 4 and Figure 10 has mentioning for highly significant compared with reference device It is high.Meanwhile starting voltage and significantly lowering, advantageously reduce power consumption；CIE (x, y) is (0.12,0.52), is a kind of bluish-green finish Material.The performance of above-mentioned organic luminescent device is mostly derived from the TADF characteristic and AIE effect of the compound M2 in luminescent layer itself, benefit It is shone with the triplet excitons that conventional fluorescent molecule (such as BCzVBi) transition is prohibited, to improve device efficiency.
The performance of comparator device 1# and device 2# are more pure it is found that two devices are neck and neck in CIE performance Blue emission.Though compound M2 is bluish-green light emitting, more excellent device performance is also showed.
(3), by taking compound M3 as an example, the OLED device of doping volume is prepared as fluorescent dopants (dopant), Design number is the structure of the OLED device of 3# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:M3 (25nm, 5%)/TmPyPb (35nm)/ LiF(1nm)/Al(100nm)。
In order to compare the performance of the compound in the embodiment of the present invention, using the reference of classical blue light emitting material BCzVBi Device (reference), design number are the OLED device structure of the reference device of D3# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:BCzVBi (25nm, 5%)/TmPyPb (35nm)/LiF(1nm)/Al(100nm)。
The device is detected using 705 spectrometer of Spectroscan PR and 236 Current Voltage source measuring system of Keithley The performance of part.Test data is as shown in table 5.
Table 5
In table 5, Vturn-onIndicate starting voltage；
EL(max)It indicates: maximum current efficiency；
It indicates: current density 10mA/cm2When current efficiency；
hp(max)It indicates: maximum power efficiency；
EQE(max)It indicates: external quantum efficiency (External Quantum Efficiency)；
CIE (x, y) is indicated: chromaticity coordinate.
As can be seen from Table 5, the external quantum efficiency (EQE) of device 3# has the raising of highly significant compared with reference device.Together When, starting voltage significantly lowers, and advantageously reduces power consumption；CIE (x, y) is (0.13,0.13), is a kind of blue light material.
(4), by taking compound M4 as an example, the OLED device of doping volume is prepared as fluorescent dopants (dopant), Design number is the structure of the OLED device of 4# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:M4 (25nm, 5%)/TmPyPb (35nm)/ LiF(1nm)/Al(100nm)。
In order to compare the performance of the compound in the embodiment of the present invention, using the reference of classical blue light emitting material BCzVBi Device (reference), design number are the OLED device structure of the reference device of D4# are as follows:
ITO (100nm)/PEDOT:PSS (40nm)/TAPC (20nm)/ADN:BCzVBi (25nm, 5%)/TmPyPb (35nm)/LiF(1nm)/Al(100nm)。
The device is detected using 705 spectrometer of Spectroscan PR and 236 Current Voltage source measuring system of Keithley The performance of part.Test data is as shown in table 6.
Table 6
In table 6, Vturn-onIndicate starting voltage；
EL(max)It indicates: maximum current efficiency；
It indicates: current density 10mA/cm2When current efficiency；
hp(max)It indicates: maximum power efficiency；
EQE(max)It indicates: external quantum efficiency (External Quantum Efficiency)；
CIE (x, y) is indicated: chromaticity coordinate.
As can be seen from Table 6, the external quantum efficiency (EQE) of device 4# has the raising of highly significant compared with reference device.Together When, starting voltage significantly lowers, and advantageously reduces power consumption；CIE (x, y) is (0.14,0.48), is a kind of bluish-green luminescent material.
It is not for limiting claim, any this field skill although the application is disclosed as above with preferred embodiment Art personnel without departing from the concept of this application, can make several possible variations and modification, therefore the application Protection scope should be subject to the range that the claim of this application is defined.

Claims (8)

1. a kind of compound, which is characterized in that the structural formula of the compound is as shown in general formula I:
R1Selected from electron-withdrawing group and selected from substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted Naphthalene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or not The substituent group that substituted quinolyl, substituted or unsubstituted isoquinolyl or following structural formula indicates:
Wherein, substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~C6Alkane Base；
Ra、Rb、RcIt is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6 Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T, u, v are independently selected from 1~5 integer；
R2、R3It is independently selected from hydrogen atom or electron-withdrawing group and the electron-withdrawing group is selected from halogen atom ,-NO2、- The C that CN, perhalogeno element or part halogen replace1~C6Alkyl, substituted or unsubstituted xenyl, takes substituted or unsubstituted phenyl Generation or unsubstituted naphthalene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine The substituent group that base, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl or following structural formula indicate:
Wherein, substituent group is selected from halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~C6Alkyl, C1~C6Alkane Base；
Ra’、Rb’、Rc’It is independently selected from hydrogen atom, halogen atom ,-NO2,-CN, perhalogeno element or part halogen replace C1~ C6Alkyl, C1~C6Alkyl；
R4Selected from C1~C6Alkyl, R5Selected from C6~C12Aryl；
T ', u ', v ' are independently selected from 1~5 integer；
R, s is independently selected from 1~4 integer.
2. compound according to claim 1, which is characterized in that the structural formula of the compound is as shown in general formula IA:
3. compound according to claim 1 or 2, which is characterized in that R2And R3For identical substituent group.
4. compound according to claim 1 or 2, which is characterized in that R1、R2And R3It is identical substituent group.
5. compound according to claim 1, which is characterized in that the compound in following compound wherein one Kind:
6. a kind of luminescent device, which is characterized in that the luminescent device includes first electrode, relative to the of the first electrode Two electrodes and at least one organic layer being set between the first electrode and the second electrode, the organic layer include power Benefit requires 1 to 5 described in any item compounds.
7. luminescent device according to claim 6, which is characterized in that the organic layer includes material of main part and object material Material, the material of main part or the guest materials are selected from the compound.
8. a kind of display device, which is characterized in that including luminescent device as claimed in claims 6 or 7.
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