CN114685538B - Boron-nitrogen compound and organic light-emitting device prepared from same - Google Patents
Boron-nitrogen compound and organic light-emitting device prepared from same Download PDFInfo
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- CN114685538B CN114685538B CN202011631413.1A CN202011631413A CN114685538B CN 114685538 B CN114685538 B CN 114685538B CN 202011631413 A CN202011631413 A CN 202011631413A CN 114685538 B CN114685538 B CN 114685538B
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- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims description 16
- 229910017464 nitrogen compound Inorganic materials 0.000 title claims description 16
- 239000000463 material Substances 0.000 claims abstract description 82
- 239000010410 layer Substances 0.000 claims description 68
- 239000002346 layers by function Substances 0.000 claims description 7
- -1 boron-nitrogen organic compound Chemical class 0.000 abstract description 82
- 150000001875 compounds Chemical class 0.000 abstract description 27
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 29
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052722 tritium Inorganic materials 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 9
- 229910052805 deuterium Inorganic materials 0.000 description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 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 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- 229940127007 Compound 39 Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- GWFCYDIAPRIMLA-UHFFFAOYSA-N 10,10-dimethylanthracen-9-one Chemical group C1=CC=C2C(C)(C)C3=CC=CC=C3C(=O)C2=C1 GWFCYDIAPRIMLA-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 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 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 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
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- GDLYCTKVUHXJBM-UHFFFAOYSA-N diphenylborane Chemical group C=1C=CC=CC=1BC1=CC=CC=C1 GDLYCTKVUHXJBM-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Abstract
The invention relates to a boron-nitrogen organic compound and an organic electroluminescent device containing the same, belonging to the technical field of semiconductors, wherein the structure of the compound 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 proper HOMO and LUMO energy levels, when the compound is used as a doping material in a luminescent layer material of an OLED luminescent device, the current efficiency and external quantum efficiency of the device are obviously improved, and simultaneously, the luminescent color purity and the service life of the device are also greatly improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a boron-nitrogen compound and an organic light-emitting device prepared from the same.
Background
The traditional fluorescent doping material is limited by early technology, only 25% of singlet excitons formed by electric excitation can be used for emitting light, the internal quantum efficiency of the device is low (25% at maximum), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is quite different from that of a phosphorescent device. The phosphorescent 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 expensive, the stability of the materials is poor, the color purity is poor, and the problems of serious roll-off of the device efficiency and the like limit the application of the phosphorescent materials in OLED.
With the advent of the 5G age, higher requirements are put on the color development standard, 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 fluorescence doped material can realize high fluorescence quanta and narrow half-peak width through molecular engineering, the blue fluorescence doped material has obtained a staged breakthrough, the half-peak width of the boron material can be reduced to below 30nm, as disclosed in the publication CN107417715A, the boron material with narrower half-wave width (31 nm) is used as the blue fluorescence doped material, and the device performance is slightly lower than that of the classical blue light TADF material 2 CZPN; in the green light region where human eyes are more sensitive, research is mainly focused on phosphorescent doped materials, but the light-emitting peak of the material is difficult to narrow by a simple method, so that the research on efficient green fluorescent doped materials with narrow half-peak width is of great significance for meeting higher color development standards.
In addition, the TADF sensitized fluorescence Technology (TSF) combines the TADF material with the fluorescence doped material, the TADF material is used as an exciton sensitization medium, the triplet state exciton formed by electric excitation is converted into the singlet state exciton, and the energy is transferred to the fluorescence doped material through the long-range energy transfer of the singlet state exciton, so that the device internal quantum efficiency of 100% can be achieved, the defect of insufficient utilization rate of the exciton of the fluorescence doped material can be overcome, the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of the fluorescence doped material can be effectively exerted, and the technology has wide prospect in the application of OLEDs.
The boron compound with a resonance structure can easily realize narrow half-peak width luminescence, and the material is applied to the TADF sensitized fluorescent technology, so that the device preparation with high efficiency and narrow half-peak width emission can be realized. As in CN 107507921B and CN 110492006a, a light emitting layer composition technique is disclosed in which TADF material with the lowest singlet and lowest triplet energy level difference of 0.2eV or less is used as the main body and boron-containing material is doped; CN110492005A and CN 110492009a disclose a luminescent layer composition scheme using exciplex as main body and boron-containing material as doping; can realize efficiency comparable to phosphorescence and relatively narrow half-width. Therefore, the development of the TADF sensitized fluorescence technology based on the narrow half-peak width boron luminescent material has unique advantages and strong potential on the index display facing BT.2020.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides a boron nitrogen compound and an organic light emitting device prepared therefrom. The organic compound has narrow half-width, high fluorescence quantum yield, high glass transition temperature and 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, thereby improving the luminous color purity and the service life of the device.
The invention provides a specific technical scheme as follows:
The structure of the boron-nitrogen compound serving as an OLED doping material is shown as a general formula (1):
In the general formula (1), Y 1-Y20 is independently represented as N or C-R a;
Each occurrence of R a is independently represented by hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, or an electron withdrawing group of C 1-C18 containing at least one heteroatom of O, N, S, B, P, F, and adjacent R a groups on the same aromatic ring may be linked to each other to form a ring;
When Y 11 and Y 12 are CH, Y 11 and Y 12 are connected or not connected by one of a single bond, an oxygen atom, a sulfur atom, N-R b, a substituted or unsubstituted alkylene group and a substituted or unsubstituted alkenylene group;
Y 16 and Y 17 are CH, Y 16 is connected or disconnected with Y 17 through one of an oxygen atom, a sulfur atom, N-R b, a substituted or unsubstituted alkylene group and a substituted or unsubstituted alkenylene group; and Y 11 is connected with Y 12、Y16 and Y 17 at least at one position;
Each occurrence of R b is independently represented as substituted or unsubstituted alkyl, substituted or unsubstituted C 6～C30 aryl, substituted or unsubstituted C 2～C30 heteroaryl;
the broken line represents five-membered rings or no connection through single bond connection, and at least one broken line forms five-membered rings through single bond connection;
The substituent of the "substituted or unsubstituted" is optionally one or more selected from deuterium, tritium, C 1～C10 alkyl, deuterium or tritium substituted C 1～C10 alkyl, aryl with 6 to 30 ring atoms substituted by deuterium or tritium, heteroaryl with 5 to 30 ring atoms, deuterium or tritium substituted ring atoms and heteroaryl with 5 to 30 ring atoms;
The hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur and nitrogen.
Preferably, the structure of the boron nitrogen compound is shown as any one of the general formulas (2-1) to (2-3):
in the general formulae (2-1) to (2-3), X 1、X2 is each independently represented by a dimethyl-substituted methylene group, a fluorenyl-substituted methylene group, an oxygen atom, a sulfur atom, or N-R b;
R b represents one of a substituted or unsubstituted C 6～C30 aryl, a substituted or unsubstituted C 2～C30 heteroaryl;
The substituents of the "substituted or unsubstituted" above groups are optionally selected from: one or more of deuterium, tritium, cyano, halogen, C 1-20 alkyl, C 2-20 alkenyl, C 6-30 aryl, heteroaryl of C 2-30.
Preferably, the structure of the boron nitrogen compound is shown as a general formula (3-1) or a general formula (3-2):
Z 1-Z16 is a nitrogen atom or C (R c), and adjacent R c can be bonded to form a ring;
Each occurrence of R c is independently represented as one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen, a cyano group, an alkyl group of C 1-10, an aryl group of C 6-30 which may be substituted or unsubstituted, a heteroaryl group of C 2-30 which may be substituted or unsubstituted;
The substituents of the "substituted or unsubstituted" above groups are optionally selected from: one or more of deuterium atoms, tritium atoms, cyano groups, halogens, C 1-20 alkyl groups, C 2-20 alkenyl groups, C 6-30 aryl groups, C 2-30 heteroaryl groups;
the hetero atom in the heteroaryl is one or more selected from oxygen atom, sulfur atom and nitrogen atom.
In a preferred embodiment of the present invention, the R a is hydrogen, deuterium, tritium, methyl, deuteromethyl, tritium methyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuteroethyl, tritium ethyl, isopropyl, phenyl substituted isopropyl, deuterated isopropyl, tritium isopropyl, tert-butyl, deuterated tert-butyl, tritium tert-butyl, deuterated cyclopentyl, tritium cyclopentyl, adamantyl, cyclohexenyl, phenoxy, phenylthio, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridinyl, quinolinyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl substituted phenyl ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiated methyl-substituted phenyl, tritiated ethyl-substituted phenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, tritiated tert-butyl-substituted biphenyl, fluorine atom, fluorine atom-substituted pyridyl group, cyano group, xanthonyl group, cyano-substituted phenyl group, cyano-substituted pyridyl group, trifluoromethyl-substituted aryl group, trifluoromethyl-substituted pyridyl group, phenyl-substituted triazinyl group, nitrogen atom-substituted terphenyl group, aryl-substituted carbonyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, azadibenzofuranyl group, azadimethylfluorenyl group, azadiphenylfluorenyl group, dimethylanthrone group, benzophenone group, azabenzophenone group, 9-fluorenone group, anthraquinone group, diphenylsulfone group derivative, diphenylborane group;
R b represents phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiated methyl-substituted phenyl, tritiated ethyl-substituted phenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl, or tritiated tert-butyl-substituted biphenyl.
R c is hydrogen, deuterium, tritium, methyl, deuteromethyl, tritiated methyl, trifluoromethyl, ethyl, tert-butyl substituted ethyl, deuteroethyl, tritiated ethyl, isopropyl, phenyl substituted isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, adamantyl, cyclohexenyl, phenoxy, adamantyl, or the like phenylthio, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridinyl, quinolinyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, t-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, t-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated t-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated t-butyl-substituted biphenyl, tritium-methyl-substituted phenyl, tritium-substituted isopropyl-substituted phenyl, tritium-substituted t-butyl-substituted phenyl, tritium-methyl-substituted biphenyl, tritium-substituted ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl or tritiated tert-butyl-substituted biphenyl.
Preferably, the specific structure of the boron nitrogen compound is any one of the following structures:
an organic light-emitting device comprises a cathode, an anode and a functional layer, wherein the functional layer is positioned between the cathode and the anode, and the functional layer of the organic light-emitting device comprises the boron-nitrogen compound.
Preferably, the functional layer comprises a light emitting layer, and the doping material of the light emitting layer is the boron-nitrogen compound.
Preferably, the light emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-nitrogen compound.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) The compound disclosed by the invention is applied to an OLED device, can be used as a green light doping material of a luminescent 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 provided by the invention has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(3) The compound is used as a doping material, and the TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved;
(4) The spectrum FWHM of the compound is narrower, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved;
(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 diagram of the structure of an OLED device using the materials of 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 present invention will be described in detail below with reference to the drawings and examples.
The following description of the embodiments of the present invention will clearly and fully describe the embodiments of the present invention, and all other embodiments that can be made by those skilled in the art without making any inventive effort are intended to fall within the scope of the present invention.
The starting materials involved in the synthetic examples of the present invention are commercially available. For example, it is available from Miao energy saving Wanchun Co., ltd., national medicine group chemical reagent Co., ltd.
For structural analysis of the compounds prepared in the examples, the molecular weight was measured by MS.
Example 1: synthesis of Compound 1:
Adding 0.012mol of raw material A1,0.01mol of raw material B1 and 150ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5mol Pd2(dba)3,5×10-5mol P(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 110 ℃, and carrying out reflux reaction for 24 hours; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate, and passing through a neutral silica gel column to obtain a target product intermediate M1; LC-MS: theoretical 559.21, found 560.26 ([ M+H ] +);
adding 0.037mol of intermediate M1 into a three-necked flask at-30 ℃ under the protection of nitrogen, then adding 150ml of tert-butylbenzene, slowly dropwise adding 28.5ml of 1.6mol/L of tert-butyllithium pentane solution, heating to 60 ℃ after the dropwise adding is finished, stirring for 1 hour, and distilling off components with boiling points lower than those of tert-butylbenzene under reduced pressure; then cooling to-30 ℃, slowly adding 3.7ml of boron tribromide, heating to room temperature and stirring for 0.5 hour. Cooling to 0 deg.c again, adding 10.6ml of N, N-diisopropylethylamine, stirring at room temperature until heating is completed, heating to 120 deg.c and further reaction for 2 hr. Cooling to room temperature and separating with sodium acetate water solution and ethyl acetate in turn; passing through silica gel column (developing agent: heated chlorobenzene), cleaning, and reprecipitating to obtain compound 1; elemental analysis structure (molecular formula C 40H28 BN): theoretical value C,90.06; h,5.29; n,2.63; test value: c,90.04; h,5.28; n,2.65.LC-MS: theoretical value 533.23, found 534.39 ([ M+H ] +).
The preparation of other target compounds was similar to that of preparation example 1, and the specific structures of the starting materials and intermediates used in the present invention are shown in table 1. All raw materials or intermediates were purchased from medium energy saving ten thousand parts limited.
TABLE 1
Example 11: synthesis of Compound 39:
Compound 39 was prepared as in example 1, except that E1 was used instead of A1 and intermediate N1 was used instead of starting material B1; elemental analysis structure (formula C 38H21BN2) of compound 39: theoretical value C,88.38; h,4.10; n,5.42; test value: c,88.39; h,4.10; n,5.40.LC-MS: theoretical value 516.18, found 517.22 ([ M+H ] +). LC-MS of intermediate G1: theoretical value 542.15, found 543.19 ([ M+H ] +).
The synthesis procedure of intermediate N1 is as follows:
Adding 0.05mol of raw material C1, 0.06mol of raw material D1 and 100ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, adding 0.0025mol of Pd (PPh 3)4, 0.075mol of potassium carbonate, 50ml of water and ethanol 1:1 mixed solution, stirring and heating to 110 ℃, carrying out reflux reaction for 24 hours, naturally cooling to room temperature, filtering, layering the filtrate, taking an organic phase, carrying out reduced pressure rotary evaporation until no fraction exists, passing through a neutral silica gel column, and obtaining an intermediate Q1, wherein the theoretical value of LC-MS is 464.15, and the actual measurement value of LC-MS is 465.41 ([ M+H ] +).
Adding 0.04mol of intermediate Q1, 0.05mol of triphenylphosphine and 100ml of o-dichlorobenzene into a three-port bottle under the protection of nitrogen, stirring and mixing, heating to 180 ℃, and reacting for 12 hours; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate N1, LC-MS: theoretical value 432.16, found 433.33 ([ M+H ] +).
Example 12: synthesis of Compound 132:
Compound 132 was prepared as in example 1, except that E1 was used instead of A1 and intermediate N2 was used instead of starting material B1; elemental analysis structure (formula C 36H21BN2) of compound 132: theoretical value C,87.82; h,4.30; n,5.69; test value: c,87.84; h,4.30; n,5.67.LC-MS: theoretical value 492.18, found 493.10 ([ M+H ] +). LC-MS of intermediate G2: theoretical value 518.15, found 519.19 ([ M+H ] +).
Intermediate N2 was prepared in the same manner as in example 13, except D2 was used instead of D1. LC-MS of intermediate Q2: theoretical 440.15, found 441.29 ([ M+H ] +); LC-MS of intermediate N2: theoretical value 408.16, found 409.39 ([ M+H ] +).
Example 13: synthesis of compound 137:
the procedure for the preparation of compound 137 was as in example 1, except that E1 was used instead of A1 and intermediate N3 was used instead of starting material B1; elemental analysis structure (formula C 40H28 BN) of compound 137: theoretical value C,90.06; h,5.29; n,2.63; test value: c,90.08; h,5.27; n,2.63.LC-MS: theoretical value 533.23, found 534.20 ([ M+H ] +). LC-MS of intermediate G3: theoretical value 559.21, found 560.34 ([ M+H ] +).
Intermediate N3 was prepared in the same manner as in example 13 except D3 was used instead of D1. LC-MS of intermediate Q3: theoretical 481.20, found 482.01 ([ M+H ] +); LC-MS of intermediate N3: theoretical value 449.21, found 450.23 ([ M+H ] +).
Example 14: synthesis of Compound 140:
Compound 140 was prepared as in example 1, except that E1 was used instead of A1 and intermediate N4 was used instead of starting material B1; elemental analysis structure (formula C 46H32 BN) of compound 140: theoretical value C,90.64; h,5.29; n,2.30; test value: c,90.63; h,5.27; n,2.32.LC-MS: theoretical value 609.26, found 610.29 ([ M+H ] +).
LC-MS of intermediate G4: theoretical value is 636.34 ([ M+H ] +).
Intermediate N4 was prepared in the same manner as in example 13 except that D4 was used in place of D1. LC-MS of intermediate Q4: theoretical 557.24, found 558.06 ([ M+H ] +); LC-MS of intermediate N4: theoretical value 525.25, found 526.20 ([ M+H ] +).
Example 15: synthesis of Compound 84:
Compound 84 was prepared as in example 1, except that intermediate E1 was used in place of A1, and the elemental analysis structure of compound 84 (formula C 49H28 BNO): theoretical value C,89.50; h,4.29; n,2.13; test value: c,89.53; h,4.27; n,2.13.LC-MS: theoretical value 657.23, found 658.11 ([ M+H ] +). LC-MS of intermediate G5: theoretical value 683.20, found 684.22 ([ M+H ] +).
Intermediate N5 was prepared in the same manner as in example 13 except that D5 was used in place of D1. LC-MS of intermediate N5: theoretical value 573.21, found 574.29 ([ M+H ] +).
The structural formula of the ref-1 compound isCommercially available.
The structural formula of the ref-2 compound isCompound 4 was numbered from the structure in publication CN109476682 a. Ref-2 was prepared by the synthesis method described in this patent.
The compound of the invention is used in a light-emitting device 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 tested for physicochemical properties, and the test results are shown in table 2:
TABLE 2
Note that: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the thermal weight loss temperature Td is a temperature at which the weight loss is 1% in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), which was tested in a nitrogen atmosphere; eg was tested by a double beam uv-vis spectrophotometer (model: TU-1901), LUMO = HOMO + Eg; PLQY and FWHM were measured in a film state by a Fluorolog-3 series fluorescence spectrometer of Horiba.
As can be seen from the above table data, the compounds of the present application have higher glass transition temperatures and decomposition temperatures than conventional green-doped ref-1. The material can be used as a doping material of the light-emitting layer, so that crystallization and film phase separation of the material can be inhibited; meanwhile, the decomposition of the material under high brightness can be restrained, and the service life of the device is prolonged. In addition, the compound disclosed by the application has a shallower HOMO energy level, is used as a doping material to be doped in a main material, is favorable for inhibiting the generation of carrier traps, and improves the energy transfer efficiency of main and guest bodies, so that the luminous efficiency of the device is improved.
Compared with the existing material ref-2, the compound disclosed by the invention has a narrower half-peak width and a higher PLQY.
The compound provided by the invention 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 narrower, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; finally, the vapor deposition decomposition temperature of the material is higher, the vapor deposition decomposition of the material can be restrained, and the service life of the device is effectively prolonged.
The effect of the OLED materials synthesized according to the present invention in the device will be described in detail below with reference to device examples 1 to 15 and device comparative examples 1 to 2. The device examples 2 to 15 and the device comparative examples 1 to 2 of the present invention were identical in the manufacturing process of the device as compared with the device example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the light-emitting layer material in the device was replaced. The layer structure and test results for each device example are shown in tables 3-1 and 4, 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 (film thickness 150 nm) is washed, that is, washed with a cleaning agent (SEMICLEAN M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, 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 electron blocking material was evaporated, a light emitting layer 6 of an OLED light emitting device was fabricated, using CBP as a host material, compound 1 as a dopant material, and the mass ratio of CBP to compound 1 was 97:3, with a light emitting layer film thickness of 30nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to be carried out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 30nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 80nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10.
The effect of the OLED materials synthesized according to the present invention in the device will be described in detail below with reference to device examples 16 to 26 and device comparative example 3. The device of the invention examples 16-26 and the device comparative example 3 were identical in the manufacturing process of the device as compared with the device of example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the light-emitting layer material in the device was replaced. The layer structure and test results for each device example are shown in tables 3-2 and 4, respectively
Device example 16
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150 nm) is washed, namely, washed by a cleaning agent (SEMICLEANM-L20), washed by pure water and dried in sequence, and then washed by ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, 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 luminescent layer 6 of the OLED luminescent device is manufactured, the structure of the luminescent layer comprises CBP and DMAC-BP used by the OLED luminescent layer 6 as double main materials, a compound 61 as a doping material, the mass ratio of the CBP, the DMAC-BP and the compound 61 is 67:30:3, and the thickness of the luminescent layer is 30nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to be carried out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 30nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 80nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10.
The molecular structural formula of the related material is shown as follows:
after completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the current efficiency, external quantum efficiency and lifetime of the device were measured. Examples of devices prepared in the same manner and comparisons such as shown in tables 3-1 and 3-2; the test results of the current efficiency, external quantum efficiency and lifetime of the obtained device are shown in table 4.
TABLE 3-1
TABLE 3-2
TABLE 4 Table 4
Note that: voltage, current efficiency, luminescence peak using an IVL (current-voltage-brightness) test system (fresco scientific instruments, su-state); the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95%; all data were tested at 10mA/cm 2.
As can be seen from the device data results of table 4, compared with the device comparative examples 1 to 3, the current efficiency, external quantum efficiency and device lifetime of the organic light emitting device of the present invention are improved greatly compared with those of the OLED device of the known material, both in the single-host system and the dual-host system; when using TADF material as the second body, device efficiency is significantly improved over that of a single body.
In summary, the above embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention, but any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (4)
1. The boron-nitrogen compound used as the OLED doping material is characterized in that the specific structure of the boron-nitrogen compound is any one of the following structures:
2. an organic light-emitting device comprising a cathode, an anode, and a functional layer between the cathode and the anode, wherein the functional layer of the organic light-emitting device comprises the boron-nitrogen compound of claim 1.
3. The organic light-emitting device according to claim 2, wherein the functional layer comprises a light-emitting layer, and wherein the doping material of the light-emitting layer is the boron-nitrogen compound according to claim 1.
4. The organic light-emitting device according to claim 3, wherein the light-emitting layer comprises a first host material, a second host material, and a doping material, wherein at least one of the first host material and the second host material is a TADF material, and wherein the doping material is the boron-nitrogen compound according to claim 1.
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