CN113929709A - Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same - Google Patents
Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same Download PDFInfo
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- CN113929709A CN113929709A CN202010602453.7A CN202010602453A CN113929709A CN 113929709 A CN113929709 A CN 113929709A CN 202010602453 A CN202010602453 A CN 202010602453A CN 113929709 A CN113929709 A CN 113929709A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 26
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 70
- 239000010410 layer Substances 0.000 claims description 54
- -1 N-phenylcarbazolyl group Chemical group 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052722 tritium Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 241000720974 Protium Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 150000001975 deuterium Chemical group 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
- 229960005222 phenazone Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 8
- 230000009477 glass transition Effects 0.000 abstract description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 5
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 239000002994 raw material Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 description 5
- 238000013375 chromatographic separation Methods 0.000 description 5
- 238000011097 chromatography purification Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000008055 phosphate buffer solution Substances 0.000 description 5
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- CDEASXIPDPAOGW-UHFFFAOYSA-N bis[4-(9,9-dimethylacridin-10-yl)phenyl]methanone Chemical compound C12=CC=CC=C2N(C2=C(C1(C)C)C=CC=C2)C1=CC=C(C(=O)C2=CC=C(N3C4=CC=CC=C4C(C4=C3C=CC=C4)(C)C)C=C2)C=C1 CDEASXIPDPAOGW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Abstract
The invention discloses a boron-nitrogen-containing organic compound and an organic electroluminescent device comprising the same, and belongs to the technical field of semiconductors. The structure of the organic compound provided by the invention is shown as a general formula (1):
the compound has narrow half-peak width, high fluorescence quantum yield, high glass transition temperature and molecular thermal stability, and appropriate HOMO and LUMO energy levels, and can be used as doping in a light-emitting layer material of an OLED light-emitting deviceWhen the material is used, the current efficiency and the external quantum efficiency of a device are remarkably improved, the luminous color purity and the service life of the device are greatly improved, and the boron-nitrogen-containing organic compound is used as a green light doping material of a luminous layer to ensure that the device has good photoelectric property.
Description
Technical Field
The invention relates to a boron-nitrogen-containing organic compound and an organic electroluminescent device comprising the same, belonging to the technical field of semiconductors.
Background
The traditional fluorescent doping material is limited by the early technology, only 25% singlet excitons formed by electric excitation can emit light, the internal quantum efficiency of the device is low (the highest is 25%), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is far from that of a phosphorescence device. The phosphorescence material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, most phosphorescent materials are limited in application in OLEDs due to problems of high price, poor material stability, poor color purity, severe device efficiency roll-off and the like.
With the advent of the 5G era, higher requirements are put on color development standards, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doped material can realize high fluorescence quantum and narrow half-peak width through molecular engineering, the blue fluorescent doped material has obtained a stepwise breakthrough, and the half-peak width of the boron material can be reduced to below 30 nm; the human eye is a more sensitive green light region, and research is mainly focused on phosphorescent doped materials, but the luminescence peak shape of the phosphorescent doped materials is difficult to narrow by a simple method, so that the research on the high-efficiency green fluorescent doped materials with narrow half-peak width has important significance for meeting higher color development standards.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides an organic compound containing boron and nitrogen and the application thereof. The organic compound emits green light, has narrow half-peak width, high fluorescence quantum yield, high glass transition temperature, high molecular thermal stability and proper HOMO and LUMO energy levels, and can be used as a green light doping material of a light emitting layer of an organic electroluminescent device, so that the light emitting color purity of the device is improved, and the service life of the device is prolonged.
In order to solve the above technical problems, the present invention provides the following technical solutions: an organic compound containing boron and nitrogen, wherein the structure of the organic compound is shown as a general formula (1):
in the general formula (1), W1、W2Each independently represents a nitrogen atom or a boron atom, and W1、W2At least one is represented by a boron atom;
X1-X4represented by-O-, -S-, -C (R)1)(R2) -or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is represented by a nitrogen atom or C-R4；
R4Expressed as hydrogen atom, protium, deuterium, tritium, cyano, halogen, C1-20Alkyl, substituted or unsubstituted C6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
R1，R2or R3Can be connected with adjacent R4 to form a ring;
i is 0 or 1;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the present invention, the structure represented by the general formula (1) may be represented by general formula (1-1) -general formula (1-4):
wherein, X2-X4Represented by-O-, -S-, -C (R)1)(R2)-or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is represented by a nitrogen atom or C-R4；
R4、R5Represented by hydrogen atom, deuterium, tritium, cyano group, fluorine atom, C1-20Alkyl of (C)6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
R4and R5Can be connected with each other to form a five-membered ring, a six-membered ring or a seven-membered ring;
m and n are 1,2, 3, 4 or 5;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the present invention, the structure represented by the general formula (1) may be represented by general formulae (1 to 5):
wherein, X5-X8Is represented by a single bond, -carbonyl, -O-, -S-, -C (R)1)(R2) -or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is represented by a nitrogen atom or C-R4；
R4、R5Represented by hydrogen atom, deuterium, tritium, cyano group, fluorine atom, C1-20Alkyl of (C)6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
m and n are 1,2, 3, 4 or 5;
a. b, c and d are 0 or 1;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further development of the invention, X is1-X4At least two of which are represented by-N (R)3)-。
As a further improvement of the invention, R is1-R4Each independently represents a methyl group, a deuterated methyl group, a tritiated methyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuryl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted phenyl group, a tritiated phenyl group, a, Ethyl substituted biphenylyl, isopropyl substituted biphenylyl, tert-butyl substituted biphenylyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenylyl, deuterated ethyl substituted biphenylylOne of biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiomethyl-substituted phenyl, tritioethyl-substituted phenyl, tritiomethyl-substituted biphenyl, tritioethyl-substituted biphenyl, tritiomethyl-substituted biphenyl, or tritiomethyl-substituted biphenyl.
As a further improvement of the invention, said C6-C30The aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
said C is2-30Heteroaryl is represented by pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, dibenzofuryl, 9-dimethylfluorenyl, N-phenylcarbazolyl, quinolyl, isoquinolyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl;
C1-C20the alkyl group of (a) is represented by methyl, ethyl, propyl, isopropyl, tert-butyl;
the substituent is deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, quinoxalyl group, quinazolinyl group, cinnolinyl group, naphthyridinyl group, fluorenyl group, dibenzofuranyl group, N-phenylcarbazolyl group or dibenzothiophenyl group.
As a further improvement of the present invention, the specific structure of the organic compound is any one of the following structures:
an organic electroluminescent device comprising an anode, a cathode and organic functional layers, said organic functional layers being located between said cathode and anode, at least one layer of said organic functional layers containing said organic compound containing boron and nitrogen.
As a further improvement of the invention, the organic functional layer of the organic electroluminescent device comprises a light-emitting layer containing the organic compound containing boron and nitrogen.
As a further improvement of the present invention, the light-emitting layer includes a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-nitrogen-containing organic compound.
A lighting or display element comprising any of the organic electroluminescent devices described.
TADF sensitized fluorescent Technology (TSF) combines TADF material and fluorescent doping material, TADF material is used as exciton sensitization medium, triplet excitons formed by electric excitation are converted into singlet excitons, energy is transferred to the fluorescent doping material through the singlet exciton long-range energy transfer, the quantum efficiency in the device can reach 100%, the technology can make up the defect of insufficient utilization rate of the fluorescent doping material excitons in the green light direction, the characteristics of high fluorescent quantum yield, high device stability, high color purity and low price of the fluorescent doping material are effectively exerted, and the technology has wide prospect in OLEDs application.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound is applied to OLED devices, can be used as a green light doping material of a light-emitting layer material, can emit green fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display;
(2) the compound has higher fluorescence quantum efficiency as a green light doped material, and the fluorescence quantum efficiency of the material is close to 100 percent;
(3) the compound is used as a green light doping material, and a TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved;
(4) the compound has a narrow spectrum FWHM, and can effectively improve the color gamut of a device and improve the luminous efficiency of the device;
(5) the compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, and effectively prolongs the service life of devices.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Preparation example 1:
adding 0.01mol of raw material C1, 0.048mol of raw material B1 and 150ml of toluene into a 250ml three-necked bottle under the protection of nitrogen, stirring and mixing, and then adding 0.1mol of sodium tert-butoxide and 4.0 multiplied by 10-4mol Pd2(dba)3，4.0×10-4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no raw material C1 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate D1, wherein the HPLC purity is 99.21% and the yield is 67.39%;
adding 0.01mol of intermediate D1, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 1, wherein the HPLC purity is 98.65 percent, and the yield is 32.61 percent;
preparation example 2:
adding 0.01mol of raw material into a 250ml three-mouth bottle under the protection of nitrogenFeed C1, 0.048mol of feed B2 and 150ml of toluene were mixed with stirring and 0.1mol of sodium tert-butoxide, 4.0X 10-4mol Pd2(dba)3，4.0×10-4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no raw material C1 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate D2, wherein the HPLC purity is 98.75%, and the yield is 50.73%;
adding 0.01mol of intermediate D2, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 4, wherein the HPLC purity is 99.04 percent, and the yield is 27.38 percent;
preparation example 3:
in a 250ml three-necked flask, 0.01mol of the starting material C2, 0.024mol of the starting material H1, 0.024mol of potassium carbonate and 100ml of N, N-Dimethylformamide (DMF) were charged under an atmosphere of nitrogen gas. The mixed solution was heated to 120 ℃ and mixed and stirred for 2 hours, and a sampling point plate was used to check whether the reaction of the raw material C2 was complete. After the reaction was complete, the reaction was allowed to cool naturally, 200mL of dichloromethane was added, the organic phase was washed five times with 100mL × 5 water, the organic phase was taken up with anhydrous sodium sulfate and stirred, filtered, the filtrate was taken and the filtrate was evaporated on a rotary evaporator. The target product intermediate M3 is obtained by adopting column chromatography (silica gel column) for chromatographic separation and purification, the HPLC purity is 98.84%, and the yield is 62.31%.
Adding 0.01mol of intermediate M3, 0.024mol of raw material B1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 0.06mol of sodium tert-butoxide, 2.0 multiplied by 10-4mol Pd2(dba)3，2.0×10-4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and taking a sample, wherein no intermediate M3 is left, and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate D3, wherein the HPLC purity is 99.14% and the yield is 51.27%;
adding 0.01mol of intermediate D3, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 27 with HPLC purity of 98.75% and yield of 30.44%;
preparation example 4:
adding 0.01mol of raw material C3 and 100ml of dimethyl sulfoxide (DMSO) into a 250ml three-necked bottle under the protection of nitrogen, stirring and mixing, and heating to 190 ℃; dissolving 0.024mol of raw material H2 in 20mL of DMSO, slowly dripping into the mixed solution by using a syringe, refluxing the mixed solution for reaction for 4H, and taking a sample, wherein no raw material C3 remains and the reaction is complete; naturally cooling to room temperature, adding 150mL of dichloromethane and 150mL of multiplied by 5 pure water to wash the organic phase for 5 times, separating liquid, taking the organic phase, adding anhydrous sodium sulfate, stirring, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate M4, wherein the HPLC purity is 98.69%, and the yield is 43.82%;
adding 0.01mol of intermediate M4, 0.024mol of raw material B3 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 0.06mol of sodium tert-butoxide, 2.0 multiplied by 10-4mol Pd2(dba)3，2.0×10-4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and taking a sample, wherein no intermediate M4 is left, and the reaction is complete; naturally cooling to room temperature, filtering, and filteringCarrying out reduced pressure rotary evaporation on the solution, and purifying the solution by a neutral silica gel column to obtain a target product intermediate D4, wherein the HPLC purity is 98.87%, and the yield is 49.71%;
adding 0.01mol of intermediate D4, 0.05mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, and 200mL of a phosphate buffer solution (pH 7) was added thereto, and the mixture was extracted with dichloromethane (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 77 with HPLC purity of 98.89% and yield of 27.64%;
preparation example 5:
1) in a 250ml three-necked flask, 0.01mol of the starting material C2, 0.012mol of 1- (chloromethyl) -4-fluoro-1, 4-diazobicyclo [2.2.2] octane bis (tetrafluoroborate) salt (selective fluorine reagent), 0.02mol of trifluoroacetic acid and 100ml of Tetrahydrofuran (THF) were charged under an atmosphere of nitrogen gas. The mixed solution was heated to 40-50 ℃ and mixed and stirred for 12 hours, and a sampling point plate was used to check whether the reaction of the raw material C2 was complete. After the reaction was complete, the reaction was allowed to cool naturally, 200mL of ethyl acetate was added, the organic phase was washed five times with 150mL × 5 water, the organic phase was taken over anhydrous sodium sulfate and stirred, filtered, the filtrate was taken and the filtrate was evaporated on a rotary evaporator. The target product intermediate S5-1 is obtained by adopting column chromatography (silica gel column) for chromatographic separation and purification, the HPLC purity is 98.75%, and the yield is 29.48%.
2) In a 250ml three-necked flask, 0.01mol of intermediate S5-1, 0.012mol of raw material H1, 0.02mol of potassium carbonate and 100ml of N, N-Dimethylformamide (DMF) were charged under an atmosphere of nitrogen gas. The mixed solution was heated to 120 ℃ and mixed and stirred for 2 hours, and the sample point plate was checked to see if the intermediate S5-1 was completely reacted. After the reaction was complete, the reaction was allowed to cool naturally, 200mL of dichloromethane were added, the organic phase was washed five times with 150mL × 5 water, the organic phase was taken up with anhydrous sodium sulfate and stirred, filtered, the filtrate was taken and the filtrate was evaporated on a rotary evaporator. The target product intermediate S5-2 is obtained by adopting column chromatography (silica gel column) for chromatographic separation and purification, the HPLC purity is 99.37%, and the yield is 67.27%.
3) In a 250ml three-necked flask, 0.01mol of intermediate S5-2, 0.012mol of raw material H5, 0.02mol of potassium carbonate and 100ml of N, N-Dimethylformamide (DMF) were charged under an atmosphere of nitrogen gas. The mixed solution was heated to 120 ℃ and mixed and stirred for 2 hours, and the sample point plate was checked to see if the intermediate S5-2 was completely reacted. After the reaction was complete, the reaction was allowed to cool naturally, 200mL of dichloromethane were added, the organic phase was washed five times with 150mL × 5 water, the organic phase was taken up with anhydrous sodium sulfate and stirred, filtered, the filtrate was taken and the filtrate was evaporated on a rotary evaporator. The target product intermediate S5-3 is obtained by adopting column chromatography (silica gel column) for chromatographic separation and purification, the HPLC purity is 98.92%, and the yield is 57.42%.
4) Adding 0.01mol of intermediate S5-3, 0.012mol of raw material B1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 0.02mol of sodium tert-butoxide, 1.0 multiplied by 10-4mol Pd2(dba)3，1.0×10- 4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no intermediate S5-3 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate S5-4, wherein the HPLC purity is 98.81%, and the yield is 52.37%;
5) adding 0.01mol of intermediate S5-4, 0.012mol of raw material B5 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 0.02mol of sodium tert-butoxide, 1.0 multiplied by 10-4mol Pd2(dba)3，1.0×10- 4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and taking a sample of a point plate to show that no intermediate S5-4 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate S5-5, wherein the HPLC purity is 99.06% and the yield is 55.17%;
6) in a 250ml three-necked flask, 0.01mol of intermediate S5-5 was charged under an atmosphere of nitrogen gas,0.03mol SnCl20.001mol of HCl and 100ml of ethanol. The mixed solution was heated to 80 ℃ and mixed and stirred for 2 hours, and the sample point plate was checked to see if the intermediate S5-5 was completely reacted. After the reaction was complete, the reaction was allowed to cool to room temperature, 200mL of ethyl acetate was added, the organic phase was washed five times with 150mL × 5 water, the organic phase was taken over anhydrous sodium sulfate and stirred, filtered, the filtrate was taken and concentrated on a rotary evaporator. The target product intermediate S5-6 is obtained by adopting column chromatography (silica gel column) for chromatographic separation and purification, the HPLC purity is 98.61%, and the yield is 80.73%.
7) Adding 0.01mol of intermediate S5-6 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 0.06mol of sodium tert-butoxide and 2.0X 10-4mol Pd2(dba)3，2.0×10-4Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no intermediate S5-6 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and purifying by a neutral silica gel column to obtain a target product intermediate D5, wherein the HPLC purity is 98.68%, and the yield is 47.15%;
8) adding 0.01mol of intermediate D5, 0.02mol of boron triiodide, 0.02mol of triphenylborane and 100mL of 1,2, 4-trichlorobenzene into a 250mL three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 200 ℃, and stirring for reacting for 20 hours; then, the mixture was naturally cooled to room temperature, 200mL of a phosphate buffer solution (pH 7) was added, and the mixture was extracted with ethyl acetate (200mL × 3, three times). The combined organic layers were concentrated in vacuo. Passing through a neutral silica gel column to obtain a target product compound 129 with HPLC purity of 98.97% and yield of 28.72%;
the preparation methods of other objective compounds were similar to those of preparation examples 1 to 5, and the specific structures of the starting materials and intermediate D used in the present invention are shown in Table 1. All raw materials or intermediates were purchased at midrange energy-saving million shares, inc.
TABLE 1
The structural characterization of the compounds obtained in the preparation examples is shown in table 2:
TABLE 2
The compound is used in a light-emitting device, has high glass transition temperature (Tg) and proper HOMO and LUMO energy levels, and can be used as a doping material of a light-emitting layer. The compounds prepared in the above examples of the present invention were subjected to thermal property, HOMO and LUMO level tests, respectively, and the results are shown in table 3.
TABLE 3
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg was measured by a two-beam uv-vis spectrophotometer (model: TU-1901), LUMO being HOMO + Eg; PLQY and FWHM were tested in the thin film state by the Fluorolog-3 series fluorescence spectrometer from Horiba.
As can be seen from the data in the above table, the compound of the present invention has higher glass transition temperature and decomposition temperature than the conventional materials ref-1 and ref-2. The luminescent layer is used as a doping material of the luminescent layer, and can inhibit the crystallization and the film phase separation of the material; meanwhile, the decomposition of the material under high brightness can be inhibited, and the service life of the device is prolonged. In addition, the compound has a shallow HOMO energy level, is doped in a host material as a doping material, is favorable for inhibiting generation of carrier traps, and improves the energy transfer efficiency of a host and an object, so that the luminous efficiency of a device is improved.
The compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; meanwhile, the spectrum FWHM of the material is narrow, so that the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; and finally, the evaporation decomposition temperature of the material is higher, so that the evaporation decomposition of the material can be inhibited, and the service life of the device is effectively prolonged.
The effect of the synthesized OLED material of the present invention in the application of the device is detailed below by device examples 1-22 and device comparative examples 1-4. Compared with the device example 1, the device examples 2 to 22 and the device comparative examples 1 to 4 of the invention have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device embodiments are shown in tables 4 and 5, respectively.
Device example 1
As shown in FIG. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (having a film thickness of 150nm) is washed, i.e., washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO layer. On the ITO anode layer 2 after the above washing, HT-1 and P-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 9): 3. Then, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, CBP is used as a main material in the light emitting layer 6, a compound 1 is used as a doping material, the mass ratio of the CBP to the compound 1 is 9):3, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer). The hole-blocking layer described above), ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 30nm, which was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9. The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device were measured. Devices examples 2-20 and comparative examples 1-2 were prepared in the same manner.
Specific device structures are shown in table 4; the results of the current efficiency, external quantum efficiency and lifetime tests of the resulting devices are shown in table 6.
TABLE 4
Device examples 11 to 20 and comparative examples 1 to 2 were similar to device example 1 in material and film thickness of the other functional layers except for the light-emitting layer 6, and therefore device examples 11 to 20 and comparative examples 1 to 2 only written the material combination pattern in the light-emitting layer 6, and the other functional layers were omitted.
In addition, device example 21 was produced in the same manner as device example 1 except that the light-emitting layer 6 was used for the remaining functional layers. In device example 21, the light-emitting layer 6 was prepared by using CBP and DMAC-BP as the dual host materials, compound 1 as the dopant material, the mass ratio of CBP, DMAC-BP and compound 1 was 6):30:3, and the light-emitting layer film thickness was 30 nm. Device examples 22-40 and comparative examples 3-4 were prepared in the same manner.
Device examples 22 to 40 and comparative examples 3 to 4 were similar to device example 21 in material and film thickness of the other functional layers except for the light-emitting layer 6, and therefore device examples 22 to 40 and comparative examples 3 to 4 only written the material combination pattern in the light-emitting layer 6, and the other functional layers were omitted.
The specific material combinations in the light emitting layers in device examples 11 to 40 and comparative examples 1 to 4 are shown in table 5.
TABLE 5
TABLE 6
Note: voltage, current efficiency, luminescence peak using IVL (current-voltage-brightness) test system (frastd scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device brightness to decay to 95%. All test data are 10mA/cm2Measured under the conditions.
As can be seen from the device data results in table 6, compared with comparative device examples 1 to 4, the current efficiency, external quantum efficiency and device lifetime of the organic light emitting device of the present invention are greatly improved compared with the OLED device of the known material in both single-host system and dual-host system; when the TADF material is used as the second body, the efficiency of the device is obviously improved compared with that of a single body.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An organic compound containing boron and nitrogen, which is characterized in that the structure of the organic compound is shown as a general formula (1):
in the general formula (1), W1、W2Each independently represents a nitrogen atom or a boron atom, and W1、W2At least one is represented by a boron atom;
X1-X4represented by-O-, -S-, -C (R)1)(R2) -or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is denoted nitrogenAtom or C-R4；
R4Expressed as hydrogen atom, protium, deuterium, tritium, cyano, halogen, C1-20Alkyl, substituted or unsubstituted C6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
R1，R2or R3Can be connected with adjacent R4 to form a ring;
i is 0 or 1;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The organic compound according to claim 1, wherein the structure represented by the general formula (1) can be represented by general formula (1-1) -general formula (1-4):
wherein, X2-X4Represented by-O-, -S-, -C (R)1)(R2) -or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is represented by a nitrogen atom or C-R4；
R4、R5To representIs hydrogen atom, deuterium, tritium, cyano, fluorine atom, C1-20Alkyl of (C)6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
R4and R5Can be connected with each other to form a five-membered ring, a six-membered ring or a seven-membered ring;
m and n are 1,2, 3, 4 or 5;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
3. The organic compound according to claim 1, wherein the structure represented by the general formula (1) can be represented by general formulae (1 to 5):
wherein, X5-X8Is represented by a single bond, -carbonyl, -O-, -S-, -C (R)1)(R2) -or-N (R)3)-，R1-R3Are each independently represented by C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30A heteroaryl group;
z, identical or different at each occurrence, is represented by a nitrogen atom or C-R4；
R4、R5Represented by hydrogen atom, deuterium, tritium, cyano group, fluorine atom, C1-20Alkyl of (C)6-30Aryl, C containing one or more hetero atoms2-30A heteroaryl group;
m and n are 1,2, 3, 4 or 5;
a. b, c and d are 0 or 1;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: deuterium, tritium, halogen, cyano, halogen atom, C1-C20Alkyl of (C)6-C30Aryl radical, C2-C30A heteroaryl group;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
4. The organic compound of claim 1, wherein X is1-X4At least two of which are represented by-N (R)3)-。
5. An organic compound according to claim 1, characterized in that: the R is1-R4Each independently represents a methyl group, a deuterated methyl group, a tritiated methyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuryl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, a methyl-substituted phenyl group, a tritiated phenyl group, a, Ethyl substituted biphenylyl, isopropyl substituted biphenylyl, tert-butyl substituted biphenylyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted biphenylyl, deuterated ethyl substituted biphenylyl, deuterated isopropyl substituted biphenylyl, deuterated tert-butyl substituted biphenylyl, tritiomethyl substituted phenyl, tritio tert-butyl substituted phenyl, tritio substituted phenylOne of a group, a tritiated methyl-substituted biphenylyl group, a tritiated ethyl-substituted biphenylyl group, a tritiated isopropyl-substituted biphenylyl group, or a tritiated t-butyl-substituted biphenylyl group.
6. The organic compound according to any one of claims 1 to 3, wherein C is6-C30The aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, benzophenanthrene, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
said C is2-30Heteroaryl is represented by pyridyl, carbazolyl, furyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, dibenzofuryl, 9-dimethylfluorenyl, N-phenylcarbazolyl, quinolyl, isoquinolyl, naphthyridinyl, oxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl;
C1-C20the alkyl group of (a) is represented by methyl, ethyl, propyl, isopropyl, tert-butyl;
the substituent is deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, quinoxalyl group, quinazolinyl group, cinnolinyl group, naphthyridinyl group, fluorenyl group, dibenzofuranyl group, N-phenylcarbazolyl group or dibenzothiophenyl group.
7. The organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
8. an organic electroluminescent device comprising an anode, a cathode and an organic functional layer, the organic functional layer being located between the cathode and the anode, characterized in that at least one layer of the organic functional layer contains the boron nitrogen containing organic compound according to any one of claims 1 to 6.
9. An organic electroluminescent device according to claim 7, wherein the organic functional layer comprises a light-emitting layer, and wherein the light-emitting layer contains the boron-nitrogen-containing organic compound according to any one of claims 1 to 6.
10. The organic light-emitting device according to claim 7, the light-emitting layer comprising a first host material, a second host material, and a dopant material, wherein: at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-nitrogen-containing organic compound according to any one of claims 1 to 5.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072568A (en) * | 2020-01-04 | 2021-07-06 | 江苏三月光电科技有限公司 | Organic electroluminescent material containing double boron and application thereof |
| WO2023035820A1 (en) * | 2021-09-13 | 2023-03-16 | 广东阿格蕾雅光电材料有限公司 | B-n-containing organic electroluminescent material and use thereof in electroluminescent device |
| WO2023155913A1 (en) * | 2022-02-21 | 2023-08-24 | 华为技术有限公司 | Boron-containing compound, light-emitting device and display apparatus |
| WO2024005118A1 (en) * | 2022-07-01 | 2024-01-04 | 東ソー株式会社 | Organic electroluminescent element |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106467554A (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 |
| US20180069182A1 (en) * | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
| US20190211038A1 (en) * | 2018-01-05 | 2019-07-11 | Chuanjun Xia | Boron and nitrogen containing heterocyclic compounds |
| CN110872316A (en) * | 2019-11-29 | 2020-03-10 | 清华大学 | Novel compound, application thereof and organic electroluminescent device using compound |
| CN111233904A (en) * | 2018-11-29 | 2020-06-05 | 江苏三月光电科技有限公司 | Organic electroluminescent material containing boron and application thereof in organic electroluminescent device |
-
2020
- 2020-06-29 CN CN202010602453.7A patent/CN113929709A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106467554A (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 |
| US20180069182A1 (en) * | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
| US20190211038A1 (en) * | 2018-01-05 | 2019-07-11 | Chuanjun Xia | Boron and nitrogen containing heterocyclic compounds |
| US20190214564A1 (en) * | 2018-01-05 | 2019-07-11 | Chuanjun Xia | Boron and nitrogen containing heterocyclic compounds |
| CN111233904A (en) * | 2018-11-29 | 2020-06-05 | 江苏三月光电科技有限公司 | Organic electroluminescent material containing boron and application thereof in organic electroluminescent device |
| CN110872316A (en) * | 2019-11-29 | 2020-03-10 | 清华大学 | Novel compound, application thereof and organic electroluminescent device using compound |
Non-Patent Citations (1)
| Title |
|---|
| JULIA MERZ ET AL., 《CHEM. EUR. J.》, vol. 23, no. 53, pages 13164 - 13180 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072568A (en) * | 2020-01-04 | 2021-07-06 | 江苏三月光电科技有限公司 | Organic electroluminescent material containing double boron and application thereof |
| WO2023035820A1 (en) * | 2021-09-13 | 2023-03-16 | 广东阿格蕾雅光电材料有限公司 | B-n-containing organic electroluminescent material and use thereof in electroluminescent device |
| WO2023155913A1 (en) * | 2022-02-21 | 2023-08-24 | 华为技术有限公司 | Boron-containing compound, light-emitting device and display apparatus |
| WO2024005118A1 (en) * | 2022-07-01 | 2024-01-04 | 東ソー株式会社 | Organic electroluminescent element |
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