CN107602601A - A kind of boron-containing multi-element heterocyclic organic compounds and its application in organic electroluminescence device - Google Patents
A kind of boron-containing multi-element heterocyclic organic compounds and its application in organic electroluminescence device Download PDFInfo
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- CN107602601A CN107602601A CN201710908903.3A CN201710908903A CN107602601A CN 107602601 A CN107602601 A CN 107602601A CN 201710908903 A CN201710908903 A CN 201710908903A CN 107602601 A CN107602601 A CN 107602601A
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- -1 heterocyclic organic compounds Chemical class 0.000 title claims abstract description 21
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 13
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 13
- 238000006467 substitution reaction Methods 0.000 claims description 32
- 150000002894 organic compounds Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- YRFKHKBUMKFMAU-UHFFFAOYSA-N 1,2-diphenylacridine Chemical class C1=CC=CC=C1C1=CC=C(N=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 YRFKHKBUMKFMAU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- WZHKCFDUDKJGBA-UHFFFAOYSA-N N1CCNCC1.S1C=CC=C1 Chemical compound N1CCNCC1.S1C=CC=C1 WZHKCFDUDKJGBA-UHFFFAOYSA-N 0.000 claims 1
- 150000001251 acridines Chemical class 0.000 claims 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 1
- 238000006664 bond formation reaction Methods 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 69
- 239000000463 material Substances 0.000 abstract description 53
- 125000005605 benzo group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000010410 layer Substances 0.000 description 67
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 47
- 238000003756 stirring Methods 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 230000015572 biosynthetic process Effects 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 32
- 239000000741 silica gel Substances 0.000 description 32
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical class [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 18
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical class CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 18
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
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- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical group O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 241000209094 Oryza Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- UQWQCMSYGMAGKF-UHFFFAOYSA-N hexane;lithium Chemical compound [Li].CCCCCC UQWQCMSYGMAGKF-UHFFFAOYSA-N 0.000 description 7
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- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 5
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical class FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical group [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229940125810 compound 20 Drugs 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
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- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
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- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a kind of boron-containing multi-element heterocyclic organic compounds and its application in organic electroluminescence device, the compound is using benzo hexatomic ring as core, on the centrally located hexatomic ring of boron element；The compound with it is intermolecular be not easy to crystallize, be not easy to assemble, with good filming the characteristics of.The compounds of this invention as organic electroluminescence device emitting layer material in use, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile for device lifetime lifting clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of boron-containing multi-element heterocyclic organic compounds, Yi Jiqi
As application of the emitting layer material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make
New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is quite varied.
OLED luminescent devices just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together.
As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, that is, produces OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton to be formed is electrically excited, device
The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big
Gap.Although phosphor material because the strong SO coupling in heavy atom center enhances intersystem crossing, can effectively utilize electricity
The singlet exciton to be formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material is present
Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits its application in OLEDs.
Hot activation delayed fluorescence (TADF) material is the 3 developed after organic fluorescence materials and organic phosphorescent material
For luminous organic material.Such material typically has that small singlet-triplet is poor (△ EST), and triplet excitons can be with
It is transformed into singlet exciton by anti-intersystem crossing to light.This can make full use of the singlet exciton for being electrically excited lower formation and three
Line state exciton, the internal quantum efficiency of device can reach 100%.Meanwhile material structure is controllable, property is stable, cheap nothing
Precious metal is needed, in having a extensive future for OLEDs fields.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem there are in fact：(1)
T1 the and S1 states of design molecule have strong CT features, very small S1-T1 state energy gaps, although can be realized by TADF processes
High T1 → S1 states exciton conversion ratio, but low S1 state radiation transistion speed is also resulted in, consequently it is difficult to have (or realizing) concurrently simultaneously
High exciton utilization rate and high fluorescent radiation efficiency；(2) even if mitigating T exciton concentration quenching effects using doping device, greatly
Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand that current OLED shows Lighting Industry, the development of OLED material is also far from enough at present, falls
After the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
The content of the invention
In view of the above-mentioned problems existing in the prior art, this application provides a kind of boron-containing multi-element heterocyclic organic compounds and its
Application in organic electroluminescence device.The compounds of this invention is based on TADF mechanism, is applied to as emitting layer material organic
Electroluminescent device, the device that the present invention makes have good photoelectric properties, disclosure satisfy that the requirement of panel manufacturing enterprise.
Technical scheme is as follows：
A kind of boron-containing multi-element heterocyclic organic compounds, shown in the structure such as formula (1) of the organic compound：
In formula (1), X represents oxygen atom or sulphur atom；
R1* substitution or unsubstituted C are expressed as6-30Aromatic radical or heteroaryl；
R2*-R5* expression hydrogen atom or C independently1-6Alkyl, C2-6Unsaturated alkyl, cycloalkyl, substitution or not
Substituted C6-30Aromatic radical or heteroaryl；Wherein R2*-R5* can also be independently be expressed as-Ar-R or-R, Ar table
Show C6-20Arlydene；R2* with R3*、R3* with R4*、R4* with R5* can mutually be bonded to form cyclic structure or not be bonded shape mutually
Circlewise structure；
R6*-R9* expression hydrogen atom or C independently1-6Alkyl, cycloalkyl, substitution or unsubstituted C6-30Fragrance
Base or heteroaryl, wherein R6* with R7*、R7* with R8*、R8* with R9* it is at least one set of to be bonded into structure shown in formula (2)；
B is selected fromX1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl substitution,
One kind in the imido grpup that alkylidene, alkyl-substituted imido grpup or the aryl of aryl substitution substitute；
R, structure shown in the expression hydrogen atoms or formula (3) of R ' independently：
In formula (3), R1、R2Selection hydrogen, C independently1-10Alkyl, the C of straight or branched5-20Cycloalkyl, C6-20
Aryl, C6-20Heteroaryl or formula (4) shown in structure；
In formula (4), R3、R4Selection C independently1-10Straight or branched alkyl, C5-20Cycloalkyl, C6-20Aryl
Or C6-20Heteroaryl.
R in the formula (3)1、R2Selection formula (5) independently, formula (6) or structure shown in formula (7)：
Wherein, formula (6), X is expressed as oxygen atom, sulphur atom, C described in formula (7)1-10Straight or branched alkyl substitutes
Alkylidene, aryl substitution alkylidene, alkyl-substituted imido grpup or aryl substitution imido grpup in one kind.
The R2*-R5* at least one be expressed as-Ar-R or-R, Ar represent C6-20Arlydene, R is expressed as formula
(3) structure shown in；R6* with R7*、R7* with R8*、R8* with R9* it is at least one set of to be bonded into structure shown in formula (2), its formula of (2)
In R ' be expressed as hydrogen atom.
The R2* with R3*、R3* with R4*、R4* with R5* at least one set of mutually bond forms cyclic structure, R2*-R5* at least one
It is individual be expressed as-Ar-R or-R, Ar represent C6-20Arlydene, R is expressed as structure shown in formula (3)；R6* with R7*、R7* with
R8*、R8* with R9* at least one set of bond into structure shown in formula (2), the R ' in its formula of (2) is expressed as hydrogen atom.
The R2* with R3*、R3* with R4*、R4* with R5* at least one set of mutually bond forms cyclic structure；R6* with R7*、R7*
With R8*、R8* with R9* at least one set of bond into structure shown in formula (2), the R ' in its formula of (2) is expressed as hydrogen atom.
The R2* with R3*、R3* with R4*、R4* with R5* at least one set of mutually bond forms cyclic structure；R6* with R7*、R7*
With R8*、R8* with R9* at least one set of bond represents structure shown in formula (3), formula (3) into structure shown in formula (2), wherein R '
In R1、R2Expression hydrogen that can be independent, methyl, isopropyl, the tert-butyl group, substitution unsubstituted phenyl, substitution or do not take either
The xenyl in generation, substitution either unsubstituted carbazyl, substitution or unsubstituted dibenzofuran group, substitution or unsubstituted
9,9- dimethyl fluorenyl, substitution either unsubstituted acridinyl, substitution or unsubstituted diphenylacridine base, substitution or
Unsubstituted phenoxazine base, substitution or unsubstituted phenothiazinyl.
Described R, R ' being expressed as independently：
Any of.
The concrete structure formula of the organic compound is：
Any of.
A kind of application of described boracic organic compound, the boracic organic compound are used to prepare organic electroluminescent
Device.
A kind of organic electroluminescence device for including the boron-containing multi-element heterocyclic organic compounds, including luminescent layer, it is described
The luminescent layer of organic electroluminescence device includes the boron-containing multi-element heterocyclic organic compounds.
The organic electroluminescence device also includes substrate layer, anode layer, hole injection layer, hole transmission layer, electronics resistance
At least one layer of or multiple layer combination in barrier, hole blocking layer, electron transfer layer, electron injecting layer and cathode layer.
Above-mentioned hole injection layer can be MoO3(molybdenum trioxide), thickness 10nm, the material of hole transport can be
TAPC, thickness can be 60nm；MCP is used as dopant material as material of main part, the compounds of this invention, and it is in MCP
It can be 9% to adulterate mass percent, and thickness can be 30nm；The material of electric transmission can be TPBI, and thickness can be
30nm；The material of the electron injecting layer can be LiF, and thickness can be 1nm；Negative electrode reflection electrode layer can be aluminium.
The present invention is beneficial to be had technical effect that：
Group comprising electron donor (donor, D) with electron acceptor (acceptor, A) in the compounds of this invention structural molecule
Conjunction can increase Orbital Overlap, improve luminous efficiency, while connect what aromatic heterocycle group was spatially separating to obtain HOMO, LUMO
Charge transfer state material, boracic heterocyclic system have strong electron attraction so that between connected electron donor
Frontier orbit is overlapping smaller, realizes the energy level difference of small S1 states and T1 states, so as to be altered between inverse system is realized under the conditions of thermostimulation
More；The boron-containing compound, because D-A forms certain dihedral angle, while other aromatic structures are connected, be capable of saboteur's
Crystallinity, intermolecular aggtegation is avoided, the film forming and fluorescence quantum efficiency having had, be suitable as luminescent layer doping
Materials'use；
Compound of the present invention can be used as luminescent layer dopant material to be made applied to OLED luminescent devices, obtain good
Device performance, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile for the device longevity
Life lifting is clearly.Compound-material of the present invention has good application effect in OLED luminescent devices, has good
Good industrialization prospect.
Brief description of the drawings
Fig. 1 is the device architecture schematic diagram of the compounds of this invention application；Wherein, 1 is transparent substrate layer, and 2 be ito anode
Layer, 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminescent layer, and 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be negative electrode
Reflection electrode layer；
Fig. 2 is the effect of visualization figure of the HOMO energy levels of compound 10；
Fig. 3 is the effect of visualization figure of the lumo energy of compound 10；
Fig. 4 is the effect of visualization figure of the HOMO energy levels of compound 33；
Fig. 5 is the effect of visualization figure of the lumo energy of compound 33；
Fig. 6 is the effect of visualization figure of the HOMO energy levels of compound 73；
Fig. 7 is the effect of visualization figure of the lumo energy of compound 73；
Fig. 8 is the effect of visualization figure of compound GD-19 HOMO energy levels；
Fig. 9 is the effect of visualization figure of compound GD-19 lumo energy.
Embodiment
The synthesis of the compound 5 of embodiment 1
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol 2, the bromofluoro benzenes of 5- bis-, 0.012mol M1,0.02mol sodium carbonate and
10ml glycol dimethyl ethers, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.It is subsequently cooled to room temperature,
Pour into beaker, add 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains among white
Body 1a, purity 98.60%, yield 80.5%.HRMS(m/z)：[M+H]+, theoretical value 523.06, measured value 523.10.
In 200ml three-necked flasks, 0.01mol intermediate 1a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 1b, purity
98.20%, yield 40.2%.HRMS(m/z)：[M+H]+, theoretical value 577.40, measured value 577.32.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 1b, 0.011mol compound D1 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.2%,
Yield 58.0%.HRMS(m/z)：[M+H]+, theoretical value 775.91, measured value 775.87.
The synthesis of the compound 10 of embodiment 2
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol E1,0.012mol M1,0.02mol sodium carbonate and 10ml ethylene glycol two
Methyl ether, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.Room temperature is subsequently cooled to, is poured into beaker, is added
Enter 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains white intermediate 2a, purity
97.60%, yield 65.8%.HRMS(m/z)：[M+H]+, theoretical value 573.11, measured value 573.07.
In 200ml three-necked flasks, 0.01mol intermediate 2a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 2b, purity
98.40%, yield 36.4%.HRMS(m/z)：[M+H]+, theoretical value 627.46, measured value 627.41.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 2b, 0.011mol compound D2 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.8%,
Yield 66.5%.HRMS(m/z)：[M+H]+, theoretical value 880.96, measured value 880.92.
The synthesis of the compound 20 of embodiment 3
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol 2, the bromofluoro benzenes of 5- bis-, 0.012mol M2,0.02mol sodium carbonate and
10ml glycol dimethyl ethers, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.It is subsequently cooled to room temperature,
Pour into beaker, add 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains among white
Body 3a, purity 98.10%, yield 77.5%.HRMS(m/z)：[M+H]+, theoretical value 496.89, measured value 496.84.
In 200ml three-necked flasks, 0.01mol intermediate 3a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 3b, purity
98.40%, yield 37.2%.HRMS(m/z)：[M+H]+, theoretical value 551.33, measured value 551.36.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 3b, 0.011mol compound D2 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.5%,
Yield 68.1%.HRMS(m/z)：[M+H]+, theoretical value 804.82, measured value 804.78.
The synthesis of the compound 23 of embodiment 4
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol E1,0.012mol M2,0.02mol sodium carbonate and 10ml ethylene glycol two
Methyl ether, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.Room temperature is subsequently cooled to, is poured into beaker, is added
Enter 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains white intermediate 4a, purity
98.30%, yield 74.5%.HRMS(m/z)：[M+H]+, theoretical value 547.04, measured value 547.08.
In 200ml three-necked flasks, 0.01mol intermediate 4a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 4b, purity
98.70%, yield 36.4%.HRMS(m/z)：[M+H]+, theoretical value 601.39, measured value 601.35.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D2 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.7%,
Yield 64.5%.HRMS(m/z)：[M+H]+, theoretical value 854.88, measured value 854.91.
The synthesis of the compound 33 of embodiment 5
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D3 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.3%,
Yield 57.40%.HRMS(m/z)：[M+H]+, theoretical value 852.86, measured value 852.90.
The synthesis of the compound 41 of embodiment 6
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D4 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.8%,
Yield 64.6 0%.HRMS(m/z)：[M+H]+, theoretical value 944.96, measured value 944.92.
The synthesis of the compound 50 of embodiment 7
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 3b, 0.011mol compound D5 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.5%,
Yield 64.2%.HRMS(m/z)：[M+H]+, theoretical value 858.91, measured value 858.79.
The synthesis of the compound 54 of embodiment 8
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol 2, the bromofluoro benzenes of 5- bis-, 0.012mol M3,0.02mol sodium carbonate and
10ml glycol dimethyl ethers, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.It is subsequently cooled to room temperature,
Pour into beaker, add 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains among white
Body 5a, purity 98.40%, yield 63.5%.HRMS(m/z)：[M+H]+, theoretical value 513.04, measured value 513.08.
In 200ml three-necked flasks, 0.01mol intermediate 5a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 5b, purity
98.0%, yield 34.5%.HRMS(m/z)：[M+H]+, theoretical value 567.39, measured value 567.35.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 5b, 0.011mol compound D5 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.3%,
Yield 67.2%.HRMS(m/z)：[M+H]+, theoretical value 874.98, measured value 874.91.
The synthesis of the compound 73 of embodiment 9
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 3b, 0.011mol compound D6 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.0%,
Yield 63.5%.HRMS(m/z)：[M+H]+, theoretical value 972.03, measured value 972.10
The synthesis of the compound 91 of embodiment 10
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 1b, 0.011mol compound D7 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.2%,
Yield 61.5%.HRMS(m/z)：[M+H]+, theoretical value 1125.36, measured value 1125.50.
The synthesis of the compound 107 of embodiment 11
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D8 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.1%,
Yield 68.2%.HRMS(m/z)：[M+H]+, theoretical value 928.96, measured value 928.87.
The synthesis of the compound 122 of embodiment 12
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 1b, 0.011mol compound D9 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.3%,
Yield 58.5%.HRMS(m/z)：[M+H]+, theoretical value 996.09, measured value 996.17.
The compound 136 of embodiment 13
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D9 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.2%,
Yield 62.1%.HRMS(m/z)：[M+H]+, theoretical value 1018.06, measured value 1017.96.
The compound 141 of embodiment 14
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 1b, 0.011mol compound D10 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.7%.
Yield 61.3%.HRMS(m/z)：[M+H]+, theoretical value 920.00, measured value 920.18
The synthesis of the compound 155 of embodiment 15
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 5b, 0.011mol compound D11 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.1%,
Yield 57.7%.HRMS(m/z)：[M+H]+, theoretical value 985.09, measured value 985.21.
The synthesis of the compound 163 of embodiment 16
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol 2, the bromofluoro benzenes of 5- bis-, 0.012mol M4,0.02mol sodium carbonate and
10ml glycol dimethyl ethers, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.It is subsequently cooled to room temperature,
Pour into beaker, add 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains among white
Body 6a, purity 98.20%, yield 61.9%.HRMS(m/z)：[M+H]+, theoretical value 523.06, measured value 523.11.
In 200ml three-necked flasks, 0.01mol intermediate 6a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 6b, purity
98.6%, yield 40.1%.HRMS(m/z)：[M+H]+, theoretical value 577.41, measured value 577.38.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 6b, 0.011mol compound D12 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.1%,
Yield 65.4%.HRMS(m/z)：[M+H]+, theoretical value 1128.25, measured value 1128.34.
The synthesis of the compound 167 of embodiment 17
The synthesis step of compound is as follows：
50ml three-necked flask, add 0.01mol 2, the bromofluoro benzenes of 5- bis-, 0.012mol M5,0.02mol sodium carbonate and
10ml glycol dimethyl ethers, nitrogen protection is passed through, is heated to 190 degrees Celsius, stirring reaction 48 hours.It is subsequently cooled to room temperature,
Pour into beaker, add 50ml toluene and 50ml water stirs 20 minutes.Filtering, filtrate revolving, crosses silicagel column, obtains among white
Body 7a, purity 98.10%, yield 70.5%.HRMS(m/z)：[M+H]+, theoretical value 496.98, measured value 496.95.
In 200ml three-necked flasks, 0.01mol intermediate 7a and 50ml ether is added, stirring and dissolving leads to nitrogen, and system is cold
But to -10 DEG C, under nitrogen atmosphere, 0.02mol lithium hexane solution, after instillation, stirring reaction is slowly added dropwise
30 minutes；Then the diethyl ether solution that 50ml contains C1 (0.01mol) is slowly dropped into, stirring reaction 1 hour, room temperature is warming up to, stirs
Mix reaction 20 hours.Product is rotated, and adds 200ml toluene and 200ml water is diluted, and liquid separation removes water layer.It is organic
Layer is dried using anhydrous magnesium sulfate, is filtered and is rotated, and is crossed silicagel column, is obtained rice white intermediate 7b, purity
98.40%, yield 35.8%.HRMS(m/z)：[M+H]+, theoretical value 551.33, measured value 551.28.
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 7b, 0.011mol compound D13 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.1%,
Yield 60.4%.HRMS(m/z)：[M+H]+, theoretical value 1034.06, measured value 1034.22.
The synthesis of the compound 173 of embodiment 18
The synthesis step of compound is as follows：
150ml four-hole bottle, under the atmosphere for being passed through nitrogen, 0.01mol 4b, 0.011mol compound D14 are added,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 50ml toluene, it is small to be heated to reflux 24
When, sample point plate, reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 98.6%,
Yield 61.7%.HRMS(m/z)：[M+H]+, theoretical value 1052.16, measured value 1052.30.
The compounds of this invention can use as luminescent layer dopant material, to the compounds of this invention 10, compound 20, chemical combination
Thing 23, compound 33, compound 50, compound 73, compound 136 and current material GD-19 carry out hot property, fluorescence volume respectively
The measure of sub- efficiency, singlet-triplet poor (△ Est), testing result are as shown in table 1.
Table 1
| Compound | Td(℃) | PLQY | △Est(eV) | HOMO(eV) | Cyclic voltammetric stability |
| Compound 10 | 405 | 68 | 0.12 | -5.57 | It is excellent |
| Compound 20 | 400 | 82 | 0.10 | -5.54 | It is excellent |
| Compound 23 | 412 | 84 | 0.17 | -5.52 | It is excellent |
| Compound 33 | 422 | 80 | 0.20 | -5.62 | It is excellent |
| Compound 50 | 418 | 79 | 0.18 | -5.69 | It is excellent |
| Compound 73 | 430 | 86 | 0.12 | -5.50 | It is excellent |
| Compound 136 | 425 | 82 | 0.24 | -5.61 | It is excellent |
| GD-19 | 375 | 80 | 0.65 | Typically |
Note：Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan
SR-3 spectroradiometers determine；Φ f are that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics
Fiber spectrometer, the test solid fluorescence amount of C-701 integrating spheres and marine optics LLS-LED the light sources composition of Lan Fei companies of the U.S.
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Cyclic voltammetric stability
It is to be identified by the redox characteristic of cyclic voltammetry observation material；Test condition：Test sample is dissolved in volume ratio
For 2:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electrolyte are 0.1M tetrabutyl ammonium tetrafluoroborates or hexafluoro
The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrodes, is titanium plate to electrode, and working electrode is ITO electrode, is followed
Ring number is 20 times.
From upper table data, the compounds of this invention has higher heat endurance, less singlet-triplet
Difference, higher Φ f so that got a promotion using the compounds of this invention as the OLED efficiency of dopant material and life-span.
MCP steams altogether as material of main part, the compounds of this invention as doped luminescent material (doping mass concentration is 9%)
It is fabricated to organic film.Excited with 365nm ultraviolet light, measure organic film fluorescence intensity is led to test angle distribution situation
Cross optics fitting software and determine its anisotropy factor α.α is smaller, shows that the luminous subconstiuent of level of organic film dopant material is got over
More, the utilization rate of dopant material radioluminescence is higher.As TADF materials (thermal excitation delayed fluorescence material), the longevity of delayed fluorescence
Life is shorter, and triplet state returns singlet easily by transition between anti-gap, is quenched so as to avoid triplet state, can lift the effect of device
Rate and life-span.As a result it is as shown in table 2.
Table 2
| Organic film (40nm) | α (degree) | Delayed fluorescence life-span τ |
| MCP:Compound 10 (9wt%) | 10.4 | 10.1 |
| MCP:Compound 20 (9wt%) | 12.5 | 8.9 |
| MCP:Compound 23 (9wt%) | 8.8 | 14.4 |
| MCP:Compound 33 (9wt%) | 13.0 | 20.1 |
| MCP:Compound 33 (9wt%) | 15.1 | 12.5 |
| MCP:Compound 50 (9wt%) | 18.3 | 14.9 |
| MCP:Compound 73 (9wt%) | 21.4 | 35.1 |
| MCP:GD-19 (9wt%) | 35 | Nothing |
Note：Organic film carries out double source by ANS evaporated devices and steamed altogether, and evaporation substrate is high saturating quartz glass, and object is mixed
Impurity level concentration is 8%.After evaporation, it is packaged in glove box (concentration of water and oxygen is less than 1ppm).Sample leads to
Superrefraction rate matching fluid is positioned in molten silicon semicolumn prism, changes lighting angle by turntable, spectrum test uses
Sphere Optics SMS-500 type spectrometers.The delayed fluorescence life-span is tested by the FLS980 transient lifetimes of Edinburg instrument
Instrument obtains.
As can be seen from Table 2 relative to Traditional dopant material GD-19, the luminous sub- anisotropy factor of the compounds of this invention
It is small, therefore the light extraction efficiency of organic layer can be improved, lift OLED efficiency.Meanwhile it effectively can be swashed using triplet state
The energy of son, improve device efficiency.
Calculating is carried out by quantum-mechanical effects software ORCA to HOMO, the lumo energy of the compounds of this invention to go forward side by side
Row visualization, computational methods use B3LYP hydridization functionals, base group 6-31g (d).HOMO effect of visualization such as Fig. 2 of compound 10
It is shown；The LUMO effect of visualization of compound 10 is as shown in Figure 3；The HOMO effect of visualization of compound 50 is as shown in figure 4, chemical combination
The LUMO effect of visualization of thing 50 is as shown in Figure 5；The HOMO effect of visualization of compound 73 is as shown in fig. 6, compound 73
LUMO effect of visualization is as shown in Figure 7；Compound GD-19 HOMO effect of visualization is as shown in figure 8, compound GD-19
HOMO effect of visualization is as shown in Figure 9.
It can be seen greatly from the spatial distribution of HOMO, LUMO in the molecule, at the HOMO and lumo energy of the compounds of this invention
In the state that is spatially separating, HOMO, LUMO degree of overlapping are small, so as to cause singlet-triplet difference small, are advantageous to triplet state and swash
Son is converted into singlet exciton by thermal excitation, in theory device internal quantum efficiency can be made to reach 100%.
19-36 and comparative example 1 describe the compound that the present invention synthesizes in detail and are used as hair in the devices by the following examples
The application effect of photosphere dopant material.For embodiment 19-36 compared with comparative example 1, the manufacture craft of the device is identical, and
And employed identical baseplate material and electrode material, the thickness of electrode material are also consistent, except that in device
Emitting layer material is changed, using the compounds of this invention.The structure composition of each embodiment obtained device such as institute of table 3
Show.The performance test results of each device are as shown in table 4.
Embodiment 19：(the molybdenum trioxide MoO of 2/ hole injection layer of ito anode layer 33, thickness 10nm) and/hole transmission layer 4
(MCP and compound 5 are according to 100 for (TAPC, thickness 60nm)/luminescent layer 5:9 weight is than blending, thickness 40nm))/electric transmission
Layer (LiF, thickness the 1nm)/negative electrode layer 8 (Al) of 6 (TPBI, thickness 30nm)/electron injecting layer 7.The molecule knot of each compound
Structure formula is as follows：
Specific preparation process is as follows：Transparent substrate layer 1 uses transparent material, such as glass；To ito anode layer 2, (thickness is
150nm) washed, i.e., carry out ultraviolet-ozone washing again after carrying out neutralizing treatment, pure water, drying successively to remove
The organic residue on bright ITO surfaces.On the ito anode layer 2 after having carried out above-mentioned washing, using vacuum deposition apparatus, steam
Plate the molybdenum trioxide MoO that thickness is 10nm3Used as hole injection layer 3.And then the TAPC of 60nm thickness is deposited as empty
Cave transport layer 4.After above-mentioned hole mobile material evaporation terminates, the luminescent layer 5 of OLED luminescent devices is made, its structure includes OLED
Luminescent layer 5 uses material MCP as material of main part, and compound 10 is used as dopant material, and dopant material doping ratio is 9% weight
Ratio is measured, luminescent layer thickness is 40nm.After above-mentioned luminescent layer 5, it is TPBI to continue vacuum evaporation electron transport layer materials, the material
The vacuum evaporation thickness of material is 30nm, and this layer is electron transfer layer 6.On electron transfer layer 6, pass through vacuum deposition apparatus, system
Make lithium fluoride (LiF) layer that thickness is 1nm, this layer is electron injecting layer 7.On electron injecting layer 7, filled by vacuum evaporation
Put, make aluminium (Al) layer that thickness is 80nm, this layer is that negative electrode reflection electrode layer 8 uses.OLED is completed as described above to light
After device, anode and negative electrode are connected with known drive circuit, the luminous efficiency of measurement device, luminescent spectrum and device
The I-E characteristic of part.
Table 3
Table 4
Note：For device detection performance using comparative example 1 as reference, the device property indices of comparative example 1 are set to 1.0.Compare
The external quantum efficiency of example 1 is 4.0% (@3000cd/m2)；It is 200 to drive the life-span (luminosity is the 90% of original intensity)
Hour.Life-span test system is the owner of the present invention and the OLED life-span tester of Shanghai University's joint development.
Compound of the present invention can be applied as luminescent layer dopant material and lighted with OLED from the results shown in Table 4
Element manufacturing, and compared with comparative example 1, either efficiency or life-span obtain larger improvement than known OLED material, special
It is not the larger lifting of the efficiency acquisition of device.
Although the present invention is disclosed by embodiment and preferred embodiment, it should be appreciated that public the invention is not restricted to institute
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
The scope of attached claim should be consistent with most wide explanation to cover all such modifications and similar arrangement.
Claims (11)
1. a kind of boron-containing multi-element heterocyclic organic compounds, it is characterised in that shown in the structure of the organic compound such as formula (1)：
In formula (1), X represents oxygen atom or sulphur atom；
R1* substitution or unsubstituted C are expressed as6-30Aromatic radical or heteroaryl；
R2*-R5* expression hydrogen atom or C independently1-6Alkyl, C2-6Unsaturated alkyl, cycloalkyl, substitution or unsubstituted
C6-30Aromatic radical or heteroaryl；Wherein R2*-R5* can also be independently be expressed as-Ar-R or-R, Ar represent
C6-20Arlydene；R2* with R3*、R3* with R4*、R4* with R5* can mutually be bonded to form cyclic structure or not mutually bond formation
Cyclic structure；
R6*-R9* expression hydrogen atom or C independently1-6Alkyl, cycloalkyl, substitution or unsubstituted C6-30Aromatic radical or
Person's heteroaryl, wherein R6* with R7*、R7* with R8*、R8* with R9* it is at least one set of to be bonded into structure shown in formula (2)；
B is selected fromX1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of straight or branched alkyl substitution
One kind in the imido grpup that substituted alkylidene, alkyl-substituted imido grpup or aryl substitutes；
R, structure shown in the expression hydrogen atoms or formula (3) of R ' independently：
In formula (3), R1、R2Selection hydrogen, C independently1-10Alkyl, the C of straight or branched5-20Cycloalkyl, C6-20Virtue
Base, C6-20Heteroaryl or formula (4) shown in structure；
In formula (4), R3、R4Selection C independently1-10Straight or branched alkyl, C5-20Cycloalkyl, C6-20Aryl or
C6-20Heteroaryl.
2. organic compound according to claim 1, it is characterised in that R in the formula (3)1、R2Selection independently
Formula (5), formula (6) or structure shown in formula (7)：
Wherein, formula (6), X is expressed as oxygen atom, sulphur atom, C described in formula (7)1-10The Asia of straight or branched alkyl substitution
One kind in alkyl, the alkylidene of aryl substitution, alkyl-substituted imido grpup or the imido grpup of aryl substitution.
3. organic compound according to claim 1, it is characterised in that the R2*-R5* at least one be expressed as-
Ar-R or-R, Ar represent C6-20Arlydene, R is expressed as structure shown in formula (3)；R6* with R7*、R7* with R8*、R8* with R9*
For at least one set bond into structure shown in formula (2), the R ' in its formula of (2) is expressed as hydrogen atom.
4. the boracic organic compound according to claim 1 or 3, it is characterised in that the R2* with R3*、R3* with R4*、R4*
With R5* at least one set of mutually bond forms cyclic structure, R2*-R5* it is at least one be expressed as-Ar-R or-R, Ar represent C6-20
Arlydene, R is expressed as structure shown in formula (3)；R6* with R7*、R7* with R8*、R8* with R9* it is at least one set of to be bonded into formula (2)
Shown structure, the R ' in its formula of (2) are expressed as hydrogen atom.
5. organic compound according to claim 1, it is characterised in that the R2* with R3*、R3* with R4*、R4* with R5* extremely
Few one group mutually is bonded to form cyclic structure；R6* with R7*、R7* with R8*、R8* with R9* at least one set of bond is into formula (2) Suo Shi
Structure, the R ' in its formula of (2) are expressed as hydrogen atom.
6. organic compound according to claim 1, it is characterised in that the R2* with R3*、R3* with R4*、R4* with R5* extremely
Few one group mutually is bonded to form cyclic structure；R6* with R7*、R7* with R8*、R8* with R9* at least one set of bond is into formula (2) Suo Shi
Structure, wherein R ' represent structure shown in formula (3), the R in formula (3)1、R2Expression hydrogen that can be independent, methyl, isopropyl, uncle
Butyl, substitution either unsubstituted phenyl, substitution or unsubstituted xenyl, substitution or unsubstituted carbazyl, substitution
Either unsubstituted dibenzofuran group, substitution or unsubstituted 9,9- dimethyl fluorenyl, substitution or unsubstituted acridine
Base, substitution either unsubstituted diphenylacridine base, substitution or unsubstituted phenoxazine base, substitution or unsubstituted fen thiophene
Piperazine base.
7. organic compound according to claim 1, it is characterised in that described R, R ' being expressed as independently：
Any of.
8. organic compound according to claim 1, it is characterised in that the concrete structure formula of the organic compound is：
Any of.
9. the application of the boracic organic compound described in a kind of any one of claim 1~8, it is characterised in that the boracic is organic
Compound is used to prepare organic electroluminescence device.
A kind of 10. organic electroluminescence for including any one of the claim 1~8 boron-containing multi-element heterocyclic organic compounds
Part, including luminescent layer, it is characterised in that it is organic that the luminescent layer of the organic electroluminescence device includes the boron-containing multi-element heterocycle
Compound.
11. organic electroluminescence device according to claim 10, it is characterised in that the organic electroluminescence device is also
Including substrate layer, anode layer, hole injection layer, hole transmission layer, electronic barrier layer, hole blocking layer, electron transfer layer, electronics
At least one layer of or multiple layer combination in implanted layer and cathode layer.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108774258A (en) * | 2018-09-10 | 2018-11-09 | 西安瑞联新材料股份有限公司 | A kind of Heterocyclic Compound Containing Boron and its application in organic electro-optic device |
| WO2019062684A1 (en) * | 2017-09-29 | 2019-04-04 | 江苏三月光电科技有限公司 | Boron-containing organic compound and application thereof in organic electroluminescent device |
| CN109575057A (en) * | 2017-09-29 | 2019-04-05 | 江苏三月光电科技有限公司 | Boron-containing hexa-heterocyclic compound and application thereof in organic electroluminescent device |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106467553A (en) * | 2016-07-29 | 2017-03-01 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescent compounds and its application in OLED |
| KR20170044821A (en) * | 2015-10-16 | 2017-04-26 | 성균관대학교산학협력단 | Organic light emitting material and organic light emitting device having the organic light emitting material |
| WO2017092508A1 (en) * | 2015-12-04 | 2017-06-08 | 广州华睿光电材料有限公司 | D-a type compound and application thereof |
-
2017
- 2017-09-29 CN CN201710908903.3A patent/CN107602601B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170044821A (en) * | 2015-10-16 | 2017-04-26 | 성균관대학교산학협력단 | Organic light emitting material and organic light emitting device having the organic light emitting material |
| WO2017092508A1 (en) * | 2015-12-04 | 2017-06-08 | 广州华睿光电材料有限公司 | D-a type compound and application thereof |
| CN106467553A (en) * | 2016-07-29 | 2017-03-01 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescent compounds and its application in OLED |
Non-Patent Citations (1)
| Title |
|---|
| MASAKI NUMATA, ET AL: "High efficiency pure blue thermally activated delayed fluorescence molecules having 10H-phenoxaborin and acridan units", 《CHEM. COMMUN.》 * |
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