CN109956965A - Compound, organic light emitting display panel and display device - Google Patents

Compound, organic light emitting display panel and display device Download PDF

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CN109956965A
CN109956965A CN201910363188.9A CN201910363188A CN109956965A CN 109956965 A CN109956965 A CN 109956965A CN 201910363188 A CN201910363188 A CN 201910363188A CN 109956965 A CN109956965 A CN 109956965A
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CN109956965B (en
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高威
张磊
代文朋
朱红岩
牛晶华
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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 invention belongs to OLED technology domain variabilities to provide a kind of compound with D- σ-A type chemical structure, and the compound has structure shown in chemical formula 1；Wherein, D is electron donating group, and m is selected from 1,2,3；A is electron-accepting group, and n is selected from 1,2,3；D is mainly selected from the diphenylamine group of the carbazoles group of substituted or unsubstituted C12-C40, the acridine group of substituted or unsubstituted C13-C40, substituted or unsubstituted C12-C40；Any one of A in aryl boron class substituent group, Benzophenone class substituent group, heteroaromatic ketone class substituent group, sulfone class substituent group.The present invention forms non-conjugated connection, has D- σ-A type molecular structure by connecting electron donating group and electron-accepting group on silicon tetraphenyl parent nucleus.Particularly, the introducing of electron-accepting group A can make entire compound molecule have bipolarity, be conducive to the transmission of two kinds of carriers of electrons and holes.

Description

Compound, organic light emitting display panel and display device
Technical field
The present invention relates to electroluminescent organic material technical fields, have D- σ-A type chemical structure more particularly to one kind Compound and organic light emitting display panel and display device including the compound.
Background technique
With the development of electronic display technology, organic luminescent device (OLED) is widely used in various display equipment, right The research and application of the luminescent material of OLED are also increasing.
According to luminous mechanism, the material for OLED luminescent layer is specifically included that
(1) fluorescent material；(2) phosphor material.
For fluorescent material, according to spin statistics, the ratio of singlet and triplet excitons is 1:3 in exciton, so glimmering Luminescent material most imperial palace quantum yield is no more than 25%.According to lambert's light-emitting mode, light extraction efficiency is 20% or so, therefore is based on The outer quantum effect (EQE) of the OLED of fluorescent material is no more than 5%.
For phosphor material, phosphor material can be acted on due to heavy atoms effect by spin coupling, reinforce intramolecule Intersystem crossing can directly utilize 75% triplet excitons, thus realize the transmitting that S1 and T1 are participated in jointly at room temperature, reason By most imperial palace quantum yield up to 100%.According to lambert's light-emitting mode, light extraction efficiency is 20% or so, therefore is based on phosphorescence The outer quantum effect of the OLED of material can achieve 20%.But at higher current densities, there are serious efficiency for phosphor material It roll-offs phenomenon, while the stability of phosphorescent devices and bad.
The luminescent layer of OLED device includes guest materials and material of main part at present, the selection of material of main part and the efficiency of device It is close with service life connection.
Therefore, exploitation can increase hole and electron mobility, have high electrochemical stability, have high triplet energy level Material of main part, facilitate Organic Light Emitting Diode be applied to display panel mass production.
Summary of the invention
In consideration of it, the present invention provides a kind of compound with D- σ-A type structure, the compound has 1 institute of chemical formula The structure shown:
Wherein, D indicates that electron donating group, m are selected from 1,2,3；A indicates that electron-accepting group, n are selected from 1,2,3；
Electron donating group D is selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, takes The thick heteroaryl, substituted or unsubstituted of generation or the thick aryl of unsubstituted C10-C60, substituted or unsubstituted C10-C60 The carbazoles group of C12-C40, the acridine group of substituted or unsubstituted C13-C40, substituted or unsubstituted C12-C40 One of diphenylamine group；
Electron-accepting group A is selected from aryl boron class substituent group, Benzophenone class substituent group, heteroaromatic ketone class substituent group, sulfone class Any one in substituent group.
The present invention forms non-conjugated connection by connection electron donating group and electron-accepting group on silicon tetraphenyl parent nucleus, With D- σ-A type molecular structure.Particularly, the D- σ-A type molecular structure of formation, the especially non-conjugated company containing silicon atom It connects, available higher triplet, broader optical band gap, efficient energy can be formed with doping body material and turned It moves, inhibits the nonradiative transition process of triplet excitons, to improve luminous efficiency.In addition, the introducing of electron-accepting group A can be with Make entire compound molecule that there is bipolarity, is conducive to the transmission of two kinds of carriers of electrons and holes.
The present invention also provides a kind of display panels and a kind of display device.
Detailed description of the invention
Fig. 1 is the chemical general formula of compound provided in an embodiment of the present invention；
Fig. 2 is the structural schematic diagram of OLED provided in an embodiment of the present invention a kind of；
Fig. 3 is a kind of schematic diagram of display device provided in an embodiment of the present invention.
Specific embodiment
Further illustrate that the present invention, these embodiments are only intended to illustrate the present invention below by embodiment and comparative example, The present invention is not limited to following embodiments.
An aspect of of the present present invention provides a kind of compound, and the compound has structure shown in chemical formula 1:
Wherein, D indicates that electron donating group, m are selected from 1,2,3；A indicates that electron-accepting group, n are selected from 1,2,3；
The electron donating group is selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl Base, the thick aryl of substituted or unsubstituted C10-C60, substituted or unsubstituted C10-C60 thick heteroaryl, substituted or unsubstituted The carbazoles group of C12-C40, the acridine group of substituted or unsubstituted C13-C40, substituted or unsubstituted C12-C40 One of diphenylamine group；
The electron-accepting group is selected from aryl boron class substituent group, Benzophenone class substituent group, heteroaromatic ketone class substituent group, sulfone Any one in class substituent group.
An embodiment of the compound according to the present invention, the compound have structure shown in chemical formula 1-1:
An embodiment of the compound, the electron donating group D contain nitrogen-atoms and pass through according to the present invention Nitrogen-atoms is connected on the phenyl ring of chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
Wherein, Y, Y1And Y2It is each independently selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or silicon atom；
X and y is each independently selected from 0,1,2 or 3；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1；
R1、R2、R3、R4It is each independently selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, the carbazoles group of substituted or unsubstituted C12-C40, substitution Or the azines group of the diphenylamine group of unsubstituted C12-C40, substituted or unsubstituted C3-C40；
When Y is oxygen atom or sulphur atom, R3It is not present；Work as Y1When for oxygen atom or sulphur atom, R3It is not present；Work as Y2For When oxygen atom or sulphur atom, R4It is not present.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1, and R indicates C1-C20 alkyl, C1-C20 alcoxyl One of base, C2-C20 alkenyl, C2-C20 alkynyl, C6-C40 aromatic radical, C4-C40 heteroaryl perfume base.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
Wherein, Y, Y1、Y2It is each independently selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or silicon atom；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1；
R, s is each independently selected from 0,1,2 or 3；P, q is each independently selected from 0,1 or 2；R1、R2、R3、R4It is respectively independent Ground is selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, the carbazoles group of substituted or unsubstituted C12-C40, substituted or unsubstituted C12-C40 diphenylamines Class group, the acridine group of substituted or unsubstituted C13-C40, substituted or unsubstituted C3-C40 azines group in It is a kind of；
As Y, Y1Or Y2When for oxygen atom or sulphur atom, p=0 or q=0；As Y, Y1Or Y2When for nitrogen-atoms, p, q are respectively only On the spot it is selected from 0 or 1；As Y, Y1Or Y2When for carbon atom or silicon atom, p, q are each independently selected from 0,1 or 2.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
U, v is each independently selected from 0,1,2 or 3；
R1、R2It is each independently selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 Aryl, substituted or unsubstituted C4-C40 heteroaryl, the carbazoles group of substituted or unsubstituted C12-C40, substitution do not take One of the diphenylamine group of the C12-C40 in generation, azines group of substituted or unsubstituted C3-C40；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
An embodiment of the compound according to the present invention, D in following group any one or it is a kind of with It is upper:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, electron-accepting group A have following chemical formula (2-1) and change Any structure shown in formula (2-2):
R15-R23It is each independently selected from one of hydrogen atom, alkyl, alkoxy, aryl or heterocyclic base；It is former that X is selected from boron One of son, oxygen atom, sulphur atom, nitrogen-atoms, when X is oxygen atom or sulphur atom, R23It is not present.
According to the compound that this embodiment indicates, it is used as bipolar host material, is conducive to two kinds of both hole and electron The transmission of carrier, the group containing boron atom are conducive to obtain the narrower spectrum of half-peak breadth (FWHM), realize better Forster Energy transfer process, obtain it is purer shine it is photochromic；Non-conjugated positive tetrahedron connects electron donor D and electron acceptor A, partition The electric charge transfer of intramolecular, may be implemented higher triplet, and broader optical band gap is more suitable for as main body material Material.In addition, working as R15And R22When for alkyl and/or alkoxy, it can protect boron atom and attacked from water and oxygen.
An embodiment of the compound according to the present invention, the aryl boron class substituent group is in following group It is any one or more than one:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, the Benzophenone class substituent group and heteroaromatic ketone class take Dai Ji is any one or more than one in following group:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1, and R indicates C1-C20 alkyl, C1-C20 alcoxyl One of base, C2-C20 alkenyl, C2-C20 alkynyl, C4-C8 naphthenic base, C6-C40 aromatic radical, C4-C40 heteroaryl.
An embodiment of the compound according to the present invention, the sulfone class substituent group are selected from one of following group Or more than one:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, the electron donating group D in following group one Kind:
Wherein, U1And U2It is each independently selected from C1-C3 alkyl, C6-C12 aryl；M and n be each independently selected from 0,1 or 2；
Z is selected from C atom, N atom, O atom or S atom, p 0,1 or 2；When Z is oxygen atom or sulphur atom, p 0；
Electron-accepting group A has one of following group:
R23Selected from phenyl；X is selected from one of boron atom, oxygen atom, sulphur atom, nitrogen-atoms, when X is that oxygen atom or sulphur are former The period of the day from 11 p.m. to 1 a.m, R23It is not present；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1.
An embodiment of the compound according to the present invention, the compound are selected from following compounds:
Compound according to the present invention may be used as the material of main part of OLED luminescent layer.
The present invention provides the preparation method of several exemplary compounds P1, P8, P14, P15, P23, following exemplary reality It applies described in example 1 to embodiment 5.
Embodiment 1
The synthesis of compound P1
Weigh S1 (4.00mmol), S2 (2.00mmol), CuI (0.20mmol), trans- 1,2- diaminocyclohexane (0.4mmol), anhydrous K3PO4(4.20mmol), under nitrogen atmosphere the toluene of 16mL, is added, is reacted for 24 hours at 110 DEG C.Instead Mixture is answered to be cooled to room temperature.Suitable aqueous ammonium chloride solution quenching reaction mixture is added.It is extracted with methylene chloride (50mL) Organic phase 3 times, organic phase is collected, and use anhydrous Na2SO4It is dried.Solution after filtration drying, is removed with Rotary Evaporators Solvent obtains crude product.Crude product is used as eluant, eluent by silica gel chromatograph column purification, using n-hexane/methylene chloride (3/1), Final purification obtains solid S3 (1.2mmol, 60%).
MALDI-TOF MS:m/z calculated value: C36H26BrNSi:579.1；Measured value: 579.4
Under conditions of nitrogen protection, S is weighed4The acetic acid of 60mL is added in (30mmol), under stirring conditions, dropwise 36mmol bromine is added dropwise, resulting mixed solution is stirred into 5h at 80 DEG C.Use NaHSO3Extra bromine simple substance is quenched in aqueous solution, It is extracted with dichloromethane (100mL × 3), collects organic phase, use anhydrous Na2SO4It is dried.Filtering, is depressurized with Rotary Evaporators Solvent is distilled off, obtains crude product.Crude product is purified by silica gel column chromatography gradient elution, is finally recrystallized using n-hexane Purifying obtains solid powder S5 (25.2mmol, 84%).
MALDI-TOF MS:m/z calculated value: C12H7BrS2:293.9；Measured value: 293.8
At room temperature, 40mL glacial acetic acid and 20mL methylene chloride are added into the single-necked flask of 50mL, is added among raw material Body S5 (6mmol), the hydrogen peroxide of 5 times of equivalents 30%, 55-60 DEG C of stirring 20-24h, after being cooled to room temperature, methylene chloride extraction, It crosses column and obtains white solid S6 (5.1mmol, 85%).
MALDI-TOF MS:m/z calculated value: C12H7BrO4S2:357.9；Measured value: 358.0
In 250ml three-necked flask, first by S6 (30mmol), connection boric acid pinacol ester (36mmol), (1,1 '-bis- (two Phenylphosphine) ferrocene) dichloro palladium (II) (0.3mmol) and potassium acetate (75mmol) be separately added into, stir on one side, on one side rapidly 3 degassings and nitrogen displacement repeatedly, are added 100mL tetrahydrofuran by syringe.It is stirred under certain revolving speed, it will be resulting mixed It closes solution reaction object and is heated to reflux 5h at 80 DEG C of reaction temperature；To after reaction, be cooled to room temperature and be added 100ml water, It is extracted with ether, gained organic phase is dry with anhydrous sodium sulfate, solvent is distilled and is removed, and carries out essence using column chromatography System, obtains intermediate S7 (21.6mmol, 72%).
MALDI-TOF MS:m/z calculated value: C18H19BO6S2:406.1；Measured value: 406.5.
Under nitrogen protection, Weigh Compound S3 (25mmol), S7 (25mmol), [Pd2(dba)3]·CHCl3 (0.5mmol) and HP (tBu)3·BF4(1.0mmol), is added in the two mouth flask of 250mL.It is injected into two mouth flask 100mL toluene (leads to N in advance215min removes oxygen), the K that 12mL concentration is 1M is then added dropwise again2CO3Aqueous solution (leads in advance N215min removes oxygen), it is stirred overnight at room temperature.After reaction, 100mL deionized water is added, then instills a few drop 2M HCl.With Methylene chloride extraction, collects organic phase, and use anhydrous Na2SO4It is dried.Solution after filtration drying, is removed with Rotary Evaporators Solvent is removed, crude product is obtained.Crude product obtains solid P1 (17.0mmol, 68%) by silica gel chromatograph column purification, final purification.
MALDI-TOF MS:m/z calculated value: C48H33NO4S2Si:779.2；Measured value: 779.3
Elemental analysis calculated value: C, 73.91；H,4.26；N,1.80；O,8.20；S,8.22；Si,3.60；Measured value: C, 73.94；H,4.29；N,1.78；O,8.19；S,8.21；Si,3.58.
Embodiment 2
The synthesis of compound P8
Weigh S1 (8.0mmol), S8 (4.0mmol), CuI (0.4mmol), trans- 1,2- diaminocyclohexane (0.48mmol), anhydrous K3PO4The toluene of 40mL is added under nitrogen atmosphere in (8.0mmol), reacts for 24 hours at 110 DEG C.Instead Mixture is answered to be cooled to room temperature.Suitable aqueous ammonium chloride solution quenching reaction mixture is added.It is extracted with methylene chloride (80mL) Organic phase 3 times, organic phase is collected, and use anhydrous Na2SO4It is dried.Solution after filtration drying, is removed with Rotary Evaporators Solvent obtains crude product.Crude product is used as eluant, eluent by silica gel chromatograph column purification, using n-hexane/methylene chloride (3/1), Final purification obtains solid S9 (2.4mmol, 60%).
MALDI-TOF MS:m/z calculated value: C39H32BrNSi (S9): 621.2；Measured value: 621.3.
In 100ml three-necked flask, first by S9 (8.0mmol), connection boric acid pinacol ester (9.6mmol), (1,1 '-is bis- (diphenylphosphine) ferrocene) dichloro palladium (II) (0.1mmol) and potassium acetate (20mmol) be separately added into, stir on one side, on one side 3 degassings and nitrogen displacement repeatedly rapidly, is added 30mL tetrahydrofuran by syringe.It is stirred under certain revolving speed, by gained Mixed solution reactant be heated to reflux 5h at 80 DEG C of reaction temperature；To after reaction, be cooled to room temperature and 25ml is added Water is extracted with ether, and gained organic phase is dry with anhydrous sodium sulfate, and solvent is distilled and is removed, and is carried out using column chromatography Purification, obtains intermediate S10 (6.6mmol, 82%).
Under nitrogen protection, Weigh Compound S11 (12mmol), S10 (12.5mmol), [Pd2(dba)3]·CHCl3 (0.25mmol) and HP (tBu)3·BF4(0.5mmol), is added in the two mouth flask of 250mL.It is injected into two mouth flask 80mL toluene (leads to N in advance215min removes oxygen), the K that 6mL concentration is 1M is then added dropwise again2CO3Aqueous solution (leads to N in advance2 15min removes oxygen), it is stirred overnight at room temperature.After reaction, 30mL deionized water is added, then instills a few drop 2M HCl.Use dichloro Methane extraction, collects organic phase, and use anhydrous Na2SO4It is dried.Solution after filtration drying is removed molten with Rotary Evaporators Agent obtains crude product.Crude product obtains solid P8 (8.8mmol, 73%) by silica gel chromatograph column purification, final purification.
MALDI-TOF MS:m/z calculated value: C51H40BNOSi:721.3；Measured value: 721.5.
Elemental analysis calculated value: C, 84.87；H,5.59；B,1.50；N,1.94；O,2.22；Si,3.89；Measured value: C, 84.90；H,5.62；B,1.48；N,1.93；O,2.21；Si,3.87.
Embodiment 3
The synthesis of compound P14
Weigh S1 (6.0mmol), S12 (3.0mmol), CuI (0.3mmol), trans- 1,2- diaminocyclohexane (0.35mmol), anhydrous K3PO4The toluene of 40mL is added under nitrogen atmosphere in (6.0mmol), reacts for 24 hours at 110 DEG C.Instead Mixture is answered to be cooled to room temperature.Suitable aqueous ammonium chloride solution quenching reaction mixture is added.It is extracted with methylene chloride (80mL) Organic phase 3 times, organic phase is collected, and use anhydrous Na2SO4It is dried.Solution after filtration drying, is removed with Rotary Evaporators Solvent obtains crude product.Crude product is used as eluant, eluent by silica gel chromatograph column purification, using n-hexane/methylene chloride (3/1), Final purification obtains solid S13 (1.95mmol, 65%).MALDI-TOF MS:m/z, calculated value: C48H36BrNSi2:761.2； Measured value: 761.4.
In 100ml three-necked flask, first by S13 (8.4mmol), connection boric acid pinacol ester (10.0mmol), (1,1 '- Bis- (diphenylphosphine) ferrocene) dichloro palladium (II) (0.1mmol) and potassium acetate (22.0mmol) be separately added into, stir on one side, 3 degassings and nitrogen displacement repeatedly rapidly on one side, is added 35mL tetrahydrofuran by syringe.It is stirred under certain revolving speed, it will Resulting mixed solution reactant is heated to reflux 5h at 80 DEG C of reaction temperature；To after reaction, be cooled to room temperature and be added 25ml water, is extracted with ether, and gained organic phase is dry with anhydrous sodium sulfate, and solvent is distilled and is removed, and uses column chromatography It is refined, obtains intermediate S14 (6.5mmol, 77%).
MALDI-TOF MS:m/z, calculated value: C54H48BNO2Si2:809.3；Measured value: 809.7.
Under nitrogen protection, Weigh Compound S14 (4.2mmol), S15 (4.0mmol), [Pd2(dba)3]·CHCl3 (0.1mmol) and HP (tBu)3·BF4(0.2mmol), is added in the two mouth flask of 100mL.40mL is injected into two mouth flask Toluene (leads to N in advance215min removes oxygen), the K that 2mL concentration is 1M is then added dropwise again2CO3Aqueous solution (leads to N in advance2 15min removes oxygen), it is stirred overnight at room temperature.After reaction, 10mL deionized water is added, then instills a few drop 2M HCl.Use dichloro Methane extraction, collects organic phase, and use anhydrous Na2SO4It is dried.Solution after filtration drying is removed molten with Rotary Evaporators Agent obtains crude product.Crude product obtains solid P14 (3.2mmol, 80%) by silica gel chromatograph column purification, final purification.
MALDI-TOF MS:m/z, calculated value: C66H49B2NSi2:933.4；Measured value: 933.5
Elemental analysis calculated value: C, 84.88；H,5.29；B,2.32；N,1.50；Si,6.01；Measured value: C, 84.91；H, 5.32；B,2.30；N,1.48；Si,5.99.
Embodiment 4
The synthesis of compound P15
Weigh S1 (9.0mmol), S16 (4.5mmol), CuI (0.45mmol), trans- 1,2- diaminocyclohexane (0.52mmol), anhydrous K3PO4The toluene of 60mL is added under nitrogen atmosphere in (9.0mmol), reacts for 24 hours at 110 DEG C.Instead Mixture is answered to be cooled to room temperature.Suitable aqueous ammonium chloride solution quenching reaction mixture is added.It is extracted with methylene chloride (50mL) Organic phase 3 times, organic phase is collected, and use anhydrous Na2SO4It is dried.Solution after filtration drying, is removed with Rotary Evaporators Solvent obtains crude product.Crude product is used as eluant, eluent by silica gel chromatograph column purification, using n-hexane/methylene chloride (5/2), Final purification obtains solid S17 (2.7mmol, 60%).MALDI-TOF MS:m/z, calculated value: C55H39BrN2Si:834.2；It surveys Magnitude: 834.5.
In 100ml three-necked flask, first by S17 (7.4mmol), connection boric acid pinacol ester (8.9mmol), (1,1 '-is bis- (diphenylphosphine) ferrocene) dichloro palladium (II) (0.1mmol) and potassium acetate (20mmol) be separately added into, stir on one side, on one side 3 degassings and nitrogen displacement repeatedly rapidly, is added 30mL tetrahydrofuran by syringe.It is stirred under certain revolving speed, by gained Mixed solution reactant be heated to reflux 5h at 80 DEG C of reaction temperature；To after reaction, be cooled to room temperature and 25ml is added Water is extracted with ether, and gained organic phase is dry with anhydrous sodium sulfate, and solvent is distilled and is removed, and is carried out using column chromatography Purification, obtains intermediate S18 (6.1mmol, 82%).
MALDI-TOF MS:m/z, calculated value: C61H51BN2O2Si:882.4；Measured value: 882.5.
Under nitrogen protection, Weigh Compound S19 (8.1mmol), S18 (7.8mmol), [Pd2(dba)3]·CHCl3 (0.16mmol) and HP (tBu)3·BF4(0.32mmol), is added in the two mouth flask of 250mL.It is injected into two mouth flask 52mL toluene (leads to N in advance215min removes oxygen), the K that 4mL concentration is 1M is then added dropwise again2CO3Aqueous solution (leads to N in advance2 15min removes oxygen), it is stirred overnight at room temperature.After reaction, 25mL deionized water is added, then instills a few drop 2M HCl.Use dichloro Methane extraction, collects organic phase, and use anhydrous Na2SO4It is dried.Solution after filtration drying is removed molten with Rotary Evaporators Agent obtains crude product.Crude product obtains solid P15 (5.0mmol, 64%) by silica gel chromatograph column purification, final purification.
MALDI-TOF MS:m/z, calculated value: C67H47BN2Si:918.4；Measured value: 918.7
Elemental analysis calculated value: C, 87.56；H,5.15；B,1.18；N,3.05；Si,3.06；Measured value: C, 87.60；H, 5.18；B,1.16；N,3.03；Si,3.03.
Embodiment 5
The synthesis of compound P23
Under nitrogen protection, Weigh Compound S20 (5.6mmol), S3 (5.4mmol), [Pd2(dba)3]·CHCl3 (0.1mmol) and HP (tBu)3·BF4(0.2mmol), is added in the two mouth flask of 100mL.35mL is injected into two mouth flask Toluene (leads to N in advance215min removes oxygen), the K that 2.7mL concentration is 1M is then added dropwise again2CO3Aqueous solution (leads to N in advance2 15min removes oxygen), it is stirred overnight at room temperature.After reaction, 20mL deionized water is added, then instills a few drop 2M HCl.Use dichloro Methane extraction, collects organic phase, and use anhydrous Na2SO4It is dried.Solution after filtration drying is removed molten with Rotary Evaporators Agent obtains crude product.Crude product obtains solid P23 (4.1mmol, 76%) by silica gel chromatograph column purification, final purification.
MALDI-TOF MS:m/z, calculated value: C50H33NO2Si:707.2；Measured value: 707.5
Elemental analysis calculated value: C, 84.83；H,4.70；N,1.98；O,4.52；Si,3.97；Measured value: C, 84.86；H, 4.73；N,1.96；O,4.50；Si,3.95.
Compounds property test
(1) compound mimics calculate
With density functional theory (DFT), using 09 program bag of Gaussian in B3LYP/6-31G (d) calculates horizontal Under, optimize and be calculated the distribution feelings of the molecule frontier orbit of the compound of the present invention P1, P3, P7, P8, P16, P22 and P24 Condition；It is based on time-depentent DFT (TD-DFT) simultaneously, simulation calculates each chemical combination of P1, P3, P7, P8, P16, P22 and P24 The singlet energy level S1 and triplet T1 of object molecule, the results are shown in Table 1, wherein △ EST=S1-T1, Eg=HOMO- LUMO, EgNumerical value take absolute value.
The parameter characterization of 1 compound of table
Compound HOMO(eV) LUMO(eV) S1(eV) T1(eV) Eg(eV)
P1 -5.66 -2.56 3.73 3.26 3.10
P3 -5.65 -2.97 3.25 2.97 2.68
P7 -5.23 -2.82 2.98 2.72 2.41
P8 -5.23 -2.03 3.64 3.21 3.20
P16 -5.64 -2.32 3.35 2.80 3.32
P22 -5.58 -2.84 3.45 2.95 2.74
P24 -5.72 -2.68 3.12 2.71 3.04
As it can be seen from table 1 the compound of the present invention all has high triplet, high optical band gap, this is main From electron donating group and electron-accepting group is connected on silicon tetraphenyl parent nucleus, non-conjugated connection is formed, there is D- σ-A type point Minor structure, available higher triplet, broader optical band gap.
Another aspect provides a kind of organic light emitting display panel, the organic light emitting display panel includes Machine luminescent device, the organic luminescent device include the anode being oppositely arranged, cathode and be located at the anode and the cathode Between luminescent layer, wherein the luminescent material of the luminescent layer includes material of main part and guest materials, and the material of main part is this One of described compound of invention or more than one.
An embodiment of the organic light emitting display panel according to the present invention, when the luminescent material of the luminescent layer is When red emitting material, the singlet level of the red emitting material is 1.61-1.99eV；
When the luminescent material of the luminescent layer is green light luminescent material, the singlet level of the green light luminescent material is 2.15-2.52eV；
When the luminescent material of the luminescent layer is blue light emitting material, the singlet level of the blue light emitting material is 2.52-2.73eV。
An embodiment of the display panel according to the present invention, the singlet level of the material of main part are higher than described The singlet level of guest materials, and the difference of the singlet level of the singlet level and guest materials of material of main part is less than 1.0eV。
An embodiment of the organic light emitting display panel, the luminescent material of the luminescent layer include according to the present invention Material of main part and guest materials, material of main part be selected from one of compound of the present invention or more than one, guest materials Selected from fluorescent material, thermal activation delayed fluorescence material or phosphorescent light-emitting materials；The HOMO energy level of the material of main part and the visitor The difference of the HOMO energy level of body material is less than the lumo energy of 0.6eV or the material of main part and the LUMO energy of the guest materials The difference of grade is less than 0.6eV.
An embodiment of the organic light emitting display panel, the luminescent material of the luminescent layer include according to the present invention Material of main part and guest materials, material of main part be selected from one of compound of the present invention or more than one, guest materials Selected from fluorescent material or thermal activation delayed fluorescence material, the singlet level of the guest materials is less than the list of the material of main part Weight state energy level, and the difference of the singlet level of the singlet level and guest materials of material of main part is less than 1.0eV.
An embodiment of the organic light emitting display panel, the luminescent material of the luminescent layer include according to the present invention Material of main part and guest materials, material of main part be selected from one of compound of the present invention or more than one, guest materials Selected from phosphor material, the triplet energy level of the guest materials is less than the triplet energy level of the material of main part, and material of main part Triplet energy level and guest materials triplet energy level difference be less than 1.0eV.
An embodiment of the organic light emitting display panel according to the present invention, the organic luminescent device further includes sky One layer or more in cave implanted layer, hole transmission layer, electronic barrier layer, hole blocking layer, electron transfer layer or electron injecting layer Layer.
In an embodiment of organic light emitting display panel of the present invention, the structure of organic luminescent device (OLED) As shown in Figure 2.Wherein, 1 is glass or other substrates (substrate) for being suitble to material (such as plastics) to be made into；2 for ITO or The transparent anodes such as IGZO；3 be organic film (including luminescent layer)；4 be metallic cathode, collectively forms a complete OLED device Part.Two electrodes 2 and 4 can be interchanged.
In organic light emitting display panel provided by the invention, the anode material of organic luminescent device can be selected from metal example Such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and their alloy.Anode material can also be selected from metal oxide as aoxidized Indium, zinc oxide, tin indium oxide (ITO), indium zinc oxide (IZO) etc.；It is for example poly- that anode material is also selected from electric conductive polymer Aniline, polypyrrole, poly- (3 methyl thiophene) etc..In addition, anode material is also selected from divided by other than the anode material enumerated Facilitate the material and combinations thereof of hole injection comprising the known material for being suitble to do anode.
In organic light emitting display panel provided by the invention, the cathode material of organic luminescent device can be selected from metal example Such as aluminium, magnesium, silver, indium, tin, titanium and their alloy.Cathode material can also selected from multiple layer metal material such as LiF/Al, LiO2/Al、BaF2/ Al etc..Other than cathode material listed above, cathode material, which can also be, facilitates electron injection Material and combinations thereof, including the known material for being suitble to do cathode.
Organic luminescent device in organic light emitting display panel of the present invention can according to method well known in the art into Row production.In the present invention, organic luminescent device can make in this way: sun is formed on transparent or opaque smooth substrate Pole forms the organic thin layer including compound of the present invention on anode, forms cathode on organic thin layer.Organic thin layer Formation can use the film build method as known to vapor deposition, sputtering, spin coating, dipping, ion plating etc..
The following examples 8 provide exemplary embodiment, for illustrating that the compound of the present invention is aobvious in organic light emission Show the practical application in panel.
Embodiment 8
Anode grid substrate distilled water, acetone, isopropyl alcohol with the ito thin film that film thickness is 100nm are cleaned by ultrasonic and are put Enter oven drying, surface is handled 30 minutes by UV, is then moved in vacuum evaporation chamber.It is 2 × 10 in vacuum degree-6Start under Pa Each layer film is deposited, the HATCN of vapor deposition 5nm thickness forms hole injection layer, the N, N'- diphenyl-N, N'- (1- of 40nm thickness is deposited Naphthalene) -1,1'- biphenyl -4,4'- diamines (α-NPD), 4,4', 4 "-three (carbazole -9- base) triphenylamines of 10nm thickness are then deposited (TCTA) hole transmission layer (HTL) is formed.On the hole transport layer, with the compound of the present invention P1, P3, P7, P8, P16, P22 Material of main part with P24 as luminescent layer, doping body material of the Ir (ppy) 3 as luminescent layer, while be deposited the dopant material and Material of main part forms the luminescent layer of 30nm thickness.Then diphenyl [4- (tri-phenyl-silane base) phenyl] oxygen is deposited on the light-emitting layer The hole blocking layer (HBL) of phosphine (TSPO1) formation 5nm thickness.(1- phenyl -1H- the benzo of 1,3,5- tri- is deposited on the hole blocking layer Imidazoles -2- base) benzene (TPBi) to be to form the electron transfer layer (ETL) of 30nm.2.5nm thickness is successively deposited on the electron transport layer LiF and the Al of 100nm thickness are as electron injecting layer (EIL) and cathode, so that organic light-emitting display device be made.
Table 2
As can be seen from Table 2, material, Ir based on the compound of the present invention P1, P3, P7, P8, P16, P22, P24 (ppy) 3 be that the doping device of dopant material achieves the maximum external quantum efficiency of 13.4%-16.3%, is illustrated in the present invention Compound can be used as the material of main part of phosphor material.
The result of table 1 is also shown that the compound of the present invention can form efficient energy transfer with dopant material, inhibits three The nonradiative transition process of line state exciton, while the introducing of electron donating group D and electron-accepting group A can make entire compound point Son has bipolarity, is conducive to the transmission of two kinds of carriers of electrons and holes.To improve luminous efficiency.
The present invention also provides a kind of display devices comprising organic light emitting display panel as described above.In this hair In bright, organic luminescent device can be OLED, can be used in organic light-emitting display device, wherein organic light-emitting display device It can be mobile phone display screen, computer display screen, TV display screen, smartwatch display screen, intelligent automobile display panel, VR Or AR helmet display screen, display screen of various smart machines etc..Fig. 3 is a kind of display device provided according to embodiments of the present invention Schematic diagram.In Fig. 3,10 indicate mobile phone display panel, and 20 indicate display device.
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 (23)

1. a kind of compound, the compound has structure shown in chemical formula 1:
Wherein, D indicates that electron donating group, m are selected from 1,2,3；A indicates that electron-accepting group, n are selected from 1,2,3；
The electron donating group is selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, takes The thick heteroaryl, substituted or unsubstituted of generation or the thick aryl of unsubstituted C10-C60, substituted or unsubstituted C10-C60 The carbazoles group of C12-C40, the acridine group of substituted or unsubstituted C13-C40, substituted or unsubstituted C12-C40 One of diphenylamine group；
The electron-accepting group is selected from aryl boron class substituent group, Benzophenone class substituent group, heteroaromatic ketone class substituent group, sulfone class and takes Any one of Dai Jizhong.
2. compound according to claim 1, which is characterized in that the compound has structure shown in chemical formula 1-1:
3. compound according to claim 1 or 2, which is characterized in that the electron donating group contains nitrogen-atoms and leads to Nitrogen-atoms is crossed to be connected on the phenyl ring of chemical formula 1 or chemical formula 1-1.
4. compound according to claim 1 or 2, which is characterized in that D in following group any one or it is a kind of More than:
Wherein, Y, Y1And Y2It is each independently selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or silicon atom；
X and y is each independently selected from 0,1,2 or 3；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1；
R1、R2、R3、R4It is each independently selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6- C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C12-C40 carbazoles group, replace or not The azines group of the diphenylamine group of substituted C12-C40, substituted or unsubstituted C3-C40；
When Y is oxygen atom or sulphur atom, R3It is not present；Work as Y1When for oxygen atom or sulphur atom, R3It is not present；Work as Y2For oxygen atom Or when sulphur atom, R4It is not present.
5. compound according to claim 4, which is characterized in that D in following group any one or it is a kind of with It is upper:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1, and R indicates C1-C20 alkyl, C1-C20 alkoxy, C2- One of C20 alkenyl, C2-C20 alkynyl, C6-C40 aromatic radical, C4-C40 heteroaryl perfume base.
6. compound according to claim 1 or 2, which is characterized in that D in following group any one or it is a kind of More than:
Wherein, Y, Y1、Y2It is each independently selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or silicon atom；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1；
R, s is each independently selected from 0,1,2 or 3；P, q is each independently selected from 0,1 or 2；R1、R2、R3、R4It is each independently selected from Hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 Heteroaryl, the carbazoles group of substituted or unsubstituted C12-C40, substituted or unsubstituted C12-C40 diphenylamine group, One of the acridine group of substituted or unsubstituted C13-C40, azines group of substituted or unsubstituted C3-C40；
As Y, Y1Or Y2When for oxygen atom or sulphur atom, p=0 or q=0；As Y, Y1Or Y2When for nitrogen-atoms, p, q are each independently Selected from 0 or 1；As Y, Y1Or Y2When for carbon atom or silicon atom, p, q are each independently selected from 0,1 or 2.
7. compound according to claim 6, which is characterized in that D in following group any one or it is a kind of with It is upper:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
8. compound according to claim 1 or 2, which is characterized in that D in following group any one or it is a kind of More than:
U, v is each independently selected from 0,1,2 or 3；
R1、R2It is each independently selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 virtue Base, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C12-C40 carbazoles group, substituted or unsubstituted The diphenylamine group of C12-C40, one of the azines group of substituted or unsubstituted C3-C40；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1.
9. compound according to claim 8, which is characterized in that D in following group any one or it is a kind of with It is upper:
10. compound according to claim 1 or 2, which is characterized in that D in following group any one or one Kind or more:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
11. compound according to claim 1 or 2, which is characterized in that the electron-accepting group has following chemical formula Any structure shown in (2-1) and chemical formula (2-2):
R15-R23It is each independently selected from one of hydrogen atom, alkyl, alkoxy, aryl or heterocyclic base；X is selected from boron atom, oxygen One of atom, sulphur atom, nitrogen-atoms, when X is oxygen atom or sulphur atom, R23It is not present；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1.
12. compound according to claim 1 or 2, which is characterized in that the aryl boron class substituent group is selected from following group In it is any one or more than one:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
13. compound according to claim 1 or 2, which is characterized in that the Benzophenone class substituent group and heteroaromatic ketone Class substituent group is any one or more than one in following group:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1, and R indicates C1-C20 alkyl, C1-C20 alkoxy, C2- One of C20 alkenyl, C2-C20 alkynyl, C4-C8 naphthenic base, C6-C40 aromatic radical, C4-C40 heteroaryl.
14. compound according to claim 1 or 2, which is characterized in that the sulfone class substituent group is in following group It is one or more kinds of:
Wherein, # indicates the position connecting with chemical formula 1 or chemical formula 1-1.
15. compound according to claim 1 or 2, which is characterized in that the electron donating group is in following group It is a kind of:
Wherein, U1And U2It is each independently selected from C1-C3 alkyl, C6-C12 aryl；M and n is each independently selected from 0,1 or 2；
Z is selected from C atom, N atom, O atom or S atom, p 0,1 or 2；When Z is oxygen atom or sulphur atom, p 0；
The electron-accepting group has one of following group:
R23Selected from phenyl；X is selected from one of boron atom, oxygen atom, sulphur atom, nitrogen-atoms, when X is oxygen atom or sulphur atom When, R23It is not present；
# indicates the position connecting with chemical formula 1 or chemical formula 1-1.
16. compound according to claim 1 or 2, which is characterized in that the compound is selected from following compounds:
17. a kind of organic light emitting display panel, which is characterized in that the organic light emitting display panel includes organic luminescent device, Wherein organic luminescent device includes the anode being oppositely arranged, cathode and shining between the anode and the cathode Layer, wherein the luminescent material of the luminescent layer includes material of main part and guest materials, the material of main part be claim 1 to One of 16 described in any item compounds or more than one.
18. organic light emitting display panel according to claim 17, which is characterized in that when the luminescent material of the luminescent layer When for red emitting material, the singlet level of the red emitting material is 1.61-1.99eV；
When the luminescent material of the luminescent layer is green light luminescent material, the singlet level of the green light luminescent material is 2.15-2.52eV；
When the luminescent material of the luminescent layer is blue light emitting material, the singlet level of the blue light emitting material is 2.52-2.73eV。
19. organic light emitting display panel according to claim 17, which is characterized in that the singlet state energy of the material of main part Grade be higher than the guest materials singlet level, and the singlet level of the singlet level of material of main part and guest materials it Difference is less than 1.0eV.
20. organic light emitting display panel according to claim 17, which is characterized in that the luminescent material packet of the luminescent layer Material of main part and guest materials are included, material of main part is selected from one of described in any item compounds of claim 1 to 16 or one Kind or more, guest materials is selected from fluorescent material, thermal activation delayed fluorescence material or phosphorescent light-emitting materials；The material of main part The difference of the HOMO energy level of HOMO energy level and the guest materials be less than the lumo energy of 0.6eV or the material of main part with it is described The difference of the lumo energy of guest materials is less than 0.6eV.
21. organic light emitting display panel according to claim 20, which is characterized in that the luminescent material packet of the luminescent layer Material of main part and guest materials are included, material of main part is selected from one of described in any item compounds of claim 1 to 16 or one Kind or more, guest materials is selected from fluorescent material or thermal activation delayed fluorescence material, the singlet level of the guest materials are less than The singlet level of the material of main part, and the difference of the singlet level of the singlet level and guest materials of material of main part is less than 1.0eV。
22. organic light emitting display panel according to claim 20, which is characterized in that the luminescent material packet of the luminescent layer Material of main part and guest materials are included, material of main part is selected from one of described in any item compounds of claim 1 to 16 or one Kind or more, guest materials is selected from phosphor material, and the triplet energy level of the guest materials is less than the triplet of the material of main part Energy level, and the difference of the triplet energy level of the triplet energy level and guest materials of material of main part is less than 1.0eV.
23. a kind of organic light-emitting display device, including the described in any item organic light emitting display panels of claim 17 to 22.
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CN110615809A (en) * 2019-09-30 2019-12-27 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN110615809B (en) * 2019-09-30 2023-07-28 武汉天马微电子有限公司 Compound, display panel and display device
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CN115850317A (en) * 2022-12-13 2023-03-28 常州大学 MR-HLCT near ultraviolet luminescent material and application thereof in OLEDs
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