CN114075228A - Boron-containing organic compound and application thereof - Google Patents
Boron-containing organic compound and application thereof Download PDFInfo
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- CN114075228A CN114075228A CN202010843416.5A CN202010843416A CN114075228A CN 114075228 A CN114075228 A CN 114075228A CN 202010843416 A CN202010843416 A CN 202010843416A CN 114075228 A CN114075228 A CN 114075228A
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- substituted
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- deuterated
- boron
- phenyl
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- 229910052796 boron Inorganic materials 0.000 title claims abstract description 32
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 74
- -1 cyano, adamantyl Chemical group 0.000 claims description 88
- 239000010410 layer Substances 0.000 claims description 73
- 125000006413 ring segment Chemical group 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 229910052722 tritium Inorganic materials 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 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 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 238000006862 quantum yield reaction 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
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 20
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 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
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 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
- 239000012043 crude product Substances 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
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Abstract
The invention discloses a boron-containing organic compound and application thereof, belonging to the technical field of semiconductor materials. The boron-containing organic compound has a structure shown in a general formula (1), 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 a light-emitting layer doping material of an organic electroluminescent device, so that the light-emitting color purity and the service life of the device are improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a boron-containing organic compound and application thereof.
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.
The green fluorescent boron-containing organic compound (CN110417859A) invented by the subject group of the exercise professor of Qinghua university realizes the characteristics of narrow half-peak width, higher fluorescence quantum yield and the like. The stable boron conjugated large plane skeleton in the structure has stable structure and no flexible characteristic, so that the half-peak width, the fluorescence quantum yield and the service life of a device are not influenced. However, the R40 substituent group combined with the parent nucleus in the structure has relatively high vibration freedom, so that the nonradiative rate is high, and the fluorescence quantum yield is reduced.
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, 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 the application of OLEDs.
The boron compound with the resonance structure can easily realize narrow half-peak-width luminescence, and the material can be applied to the TADF sensitized fluorescence technology to realize the preparation of devices with high efficiency and narrow half-peak-width emission. For example, CN107507921B discloses a technique of combining a light-emitting layer mainly composed of a TADF material having a difference between the lowest singlet level and the lowest triplet level of 0.2eV or less and doped with a boron-containing material; CN110492005A discloses a light-emitting layer composition scheme using exciplex as the main body and boron-containing material as the dopant; can realize the efficiency which is comparable with phosphorescence and has relatively narrow half-peak width. Therefore, the TADF sensitized fluorescent technology based on the narrow half-peak width boron luminescent material is developed, and has unique advantages and strong potential in the aspect of displaying indexes facing BT.2020.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides a boron-containing organic compound and applications thereof. The compound has narrow half-peak width, high fluorescence quantum yield, high glass transition temperature, high molecular thermal stability and appropriate HOMO and LUMO energy levels, and can be used as a luminescent layer doping material of an organic electroluminescent device, so that the luminescent color purity and the service life of the device are improved.
The technical scheme of the invention is as follows:
a boron-containing organic compound having a structure represented by general formula (1):
wherein R is1Expressed as F atom, or C consisting of two or more of C, H, O, N, S, B, P, F elements1-C30Any one of the electron-withdrawing groups of (a);
R2、R3simultaneously represents substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C3-C20Any one of the heteroaryl groups of (a);
R4、R5、R6、R7simultaneously represents a hydrogen atom, deuterium, tritium, halogen, cyano, adamantyl, substituted or unsubstituted C1～C10Straight chain alkyl, substituted or unsubstituted C1～C10Branched alkyl, substituted or unsubstituted C3～C10Any one of cycloalkyl, substituted or unsubstituted aryl with 6-30 ring atoms, and substituted or unsubstituted heteroaryl with 5-30 ring atoms;
the substituents of the substituent groups being optionally selected from deuterium, tritium, adamantyl, C1～C10Alkyl, deuterium or tritium substituted C1～C10Alkyl radical, C3～C10A cycloalkyl group, wherein the number of ring atoms is 6-30 aryl, the number of deuterium or tritium substituted ring atoms is 6-30 aryl, the number of ring atoms is 5-30 heteroaryl, and the number of deuterium or tritium substituted ring atoms is any one of 5-30 heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Preferably, the structure of the boron-containing organic compound is shown as the general formula (2):
in the general formula (2), R1、R2、R3The definitions of (a) are the same as those in the above description.
Preferably, the structure of the boron-containing organic compound is shown as the general formula (3):
in the general formula (3), R1、R2、R3、R4、R5、R6、R7The definition of (a) is the same as that described above.
R4、R5、R6、R7Simultaneously expressed as deuterium, tritium, halogen, cyanoAdamantyl, substituted or unsubstituted C1～C10Straight chain alkyl, substituted or unsubstituted C1～C10Branched alkyl, substituted or unsubstituted C3～C10Any one of cycloalkyl, substituted or unsubstituted aryl with 6-30 ring atoms, or substituted or unsubstituted heteroaryl with 5-30 ring atoms;
the substituents of the substituent groups being optionally selected from deuterium, tritium, adamantyl, C1～C10Alkyl, deuterium or tritium substituted C1～C10Alkyl radical, C3～C10A cycloalkyl group, wherein the number of ring atoms is 6-30 aryl, the number of deuterium or tritium substituted ring atoms is 6-30 aryl, the number of ring atoms is 5-30 heteroaryl, and the number of deuterium or tritium substituted ring atoms is any one of 5-30 heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
In a preferred embodiment, the R group1Represents one of fluorine atom, fluorine atom substituted pyridyl group, cyano group, xanthenone group, cyano group substituted phenyl group, cyano group substituted pyridyl group, trifluoromethyl group substituted aryl group, trifluoromethyl group substituted pyridyl group, phenyl group substituted triazinyl group, nitrogen atom substituted terphenyl group, aryl group substituted carbonyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, azabenzofuran group, azabicyclohexyl fluorenyl group, azabiphenylfluorenyl group, dimethylanthrenonyl group, benzophenone group, azabenzophenonyl group, 9-fluorenone group, anthraquinone group, diphenylsulfone group derivative and diphenylboryl group;
R2、R3and are represented by phenyl, deuterated phenyl, tritiated phenyl, biphenylyl, deuterated biphenylyl, tritiated biphenylyl, deuterated terphenylyl, tritiated terphenylyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, tert-substituted phenyl, ethyl-substituted phenyl, tert-substituted phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, ethyl-substituted phenyl, ethyl-substituted phenyl, ethyl-substituted phenyl, ethyl-substitutedOne of group-substituted biphenylyl, 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, tritimethyl-substituted phenyl, tritiethyl-substituted phenyl, tritium-tert-butyl-substituted phenyl, tritimethyl-substituted biphenylyl, tritiethyl-substituted biphenylyl, tritiisopropyl-substituted biphenylyl, trititert-butyl-substituted biphenylyl, tritimethyl-substituted biphenylyl, tritide-ethyl-substituted biphenylyl, tritide-isopropyl-substituted biphenylyl, and tritide-tert-butyl-substituted biphenylyl;
R4、R5、R6、R7and is represented by one of hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, pentyl, hexyl, methyl-substituted cyclobutyl, ethyl-substituted cyclobutyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, heptyl, deuterated cyclohexyl, tritiated cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, phenyl, thienyl, furyl and pyridyl.
Preferably, the specific structural formula of the boron-containing organic compound is any one of the following structures:
an organic light-emitting device comprising a cathode, an anode and a functional layer, said functional layer being located between the cathode and the anode, said boron-containing organic compound being comprised in the functional layer of the organic light-emitting device.
Preferably, the functional layer includes a light-emitting layer, and the doping material of the light-emitting layer is the boron-containing organic compound.
Preferably, 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-containing organic compound.
The beneficial technical effects of the invention are as follows:
(1) the compound is applied to OLED devices, can be used as a doping material of a luminescent layer material, can emit fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display; the compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(2) the compound is used as a doping material, and a TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved; 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; 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 present invention will be described in detail with reference to the accompanying drawings and examples.
The raw materials involved in the synthesis examples of the present invention were purchased from Zhongjieyanwang Limited.
Example 1: synthesis of Compound 4
(1) A three-necked flask was charged with a mixture of 0.01mol of starting material I-2 and 0.012mol of starting material I-1 to 120mL of toluene: to a mixed solvent of 2:1, 0.02mol of potassium carbonate was added, and 0.0002mol of pd (PPh) was added after oxygen removal3)4Reacting at 110 ℃ for 48 hours in the atmosphere of nitrogen, sampling a sample, cooling and filtering after reactants react completely, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain an intermediate II-1.
(2) Adding 0.01mol of intermediate II-1, 0.022mol of raw material I-3 and 150ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5molPd2(dba)3，5×10-5molP(t-Bu)3The reaction was heated to 110 ℃ and refluxed for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate II-2.
(3) Under nitrogen atmosphere, 0.01mol of intermediate II-2 was added to a three-necked flask, followed by addition of 200ml of 1,2, 4-trichlorobenzene to dissolve it, and addition of 0.02mol of BI3And 0.1molPh3B, then raising the temperature to 200 ℃ for reaction for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and after adding a 20mL of a phosphorus buffer solution having a ph of 7 to the reaction mixture, the aqueous layer was separated and extracted with dichloromethane (60mL, three times). The solvent was dried by vacuum spin-drying to give compound 4.
Examples 2 to 21:
the synthesis of the compounds of examples 2-21 is similar to that of example 1, except that the starting materials which may be used are different, the intermediate and product structures are shown in Table 1 below, and the results are also shown in the Table below.
TABLE 1
For structural analysis of the compounds prepared in examples 1 to 21, the molecular weight was measured using LC-MS, and the molecular weight was measured by dissolving the prepared compound in deuterated chloroform solvent and measuring using 400MHz NMR apparatus1H-NMR。
TABLE 2
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 physicochemical properties of the compounds prepared in the above examples of the present invention were measured, 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 single component film state by the Fluorolog-3 series fluorescence spectrometer from Horiba, and the film thickness was 80 nm.
As can be seen from the data in the table above, the compound of the present invention has higher glass transition temperature and decomposition temperature compared to the conventional green light doping ref-1 and the existing materials ref-2 to ref-4. 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 application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-42 and device comparative examples 1-8.
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 (SemicleanM-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 HI-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 HI-1 was 97: 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, and the structure of the OLED light-emitting device comprises that CBP used by the OLED light-emitting layer 6 is used as a main material, a compound 4 is used as a doping material, the mass ratio of the CBP to the compound 4 is 97:3, 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 7. After the hole-blocking layer 7, 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, and this layer 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.
Compared with the device example 1, the device examples 2 to 21 and the device comparative examples 1 to 4 of the present 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 examples are shown in tables 4-1 and 5, respectively.
Device example 22
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, that is, washed with a cleaning agent (SemicleanM-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. On the ITO anode layer 2 after the above washing, HT-1 and HI-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 HI-1 was 97: 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, and the structure of the OLED light emitting device comprises that CBP and DMAC-BP used by the OLED light emitting layer 6 are used as double main body materials, a compound 4 is used as a doping material, the mass ratio of the CBP to the DMAC-BP to the compound 4 is 67:30:3, 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 7. After the hole-blocking layer 7, 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, and this layer 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.
Compared with device example 22, the device examples 23 to 42 and the device comparative examples 5 to 8 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is kept consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device examples are shown in tables 4-2 and 5, respectively.
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. Device examples and comparisons prepared in the same manner are shown in tables 4-1 and 4-2; the results of the current efficiency, external quantum efficiency and lifetime tests of the resulting devices are shown in table 5.
TABLE 4-1
TABLE 4-2
TABLE 5
Note: voltage, current efficiency, and peak luminescence were measured using an IVL (Current-Voltage-Brightness) test system (Fushida scientific instruments, Suzhou) at a current density of 10mA/cm2(ii) a 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 luminance to decay to 95% at 10000 nits.
As can be seen from the device data results in table 5, 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 (8)
1. A boron-containing organic compound having a structure represented by general formula (1):
wherein R is1Expressed as F atom, or C consisting of two or more of C, H, O, N, S, B, P, F elements1-C30Any one of the electron-withdrawing groups of (a);
R2、R3simultaneously represents substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C3-C20Any one of the heteroaryl groups of (a);
R4、R5、R6、R7simultaneously represents a hydrogen atom, deuterium, tritium, halogen, cyano, adamantyl, substituted or unsubstituted C1～C10Straight chain alkyl, substituted or unsubstituted C1～C10Branched alkyl, substituted or unsubstituted C3～C10Any one of cycloalkyl, substituted or unsubstituted aryl with 6-30 ring atoms, and substituted or unsubstituted heteroaryl with 5-30 ring atoms;
the substituents of the substituent groups being optionally selected from deuterium, tritium, adamantyl, C1～C10Alkyl, deuterium or tritium substituted C1～C10Alkyl radical, C3～C10A cycloalkyl group, wherein the number of ring atoms is 6-30 aryl, the number of deuterium or tritium substituted ring atoms is 6-30 aryl, the number of ring atoms is 5-30 heteroaryl, and the number of deuterium or tritium substituted ring atoms is any one of 5-30 heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
2. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by general formula (2):
in the general formula (2), R1、R2、R3Is as defined in claim 1.
3. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by general formula (3):
in the general formula (3), R1、R2、R3Is as defined in claim 1.
R4、R5、R6、R7Simultaneously represents deuterium, tritium, halogen, cyano, adamantyl, substituted or unsubstituted C1～C10Straight chain alkyl, substituted or unsubstituted C1～C10Branched alkyl, substituted or unsubstituted C3～C10Any one of cycloalkyl, substituted or unsubstituted aryl with 6-30 ring atoms, or substituted or unsubstituted heteroaryl with 5-30 ring atoms;
the substituents of the substituent groups being optionally selected from deuterium, tritium, adamantyl, C1～C10Alkyl, deuterium or tritium substituted C1～C10Alkyl radical, C3～C10A cycloalkyl group, wherein the number of ring atoms is 6-30 aryl, the number of deuterium or tritium substituted ring atoms is 6-30 aryl, the number of ring atoms is 5-30 heteroaryl, and the number of deuterium or tritium substituted ring atoms is any one of 5-30 heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
4. The boron-containing organic compound of claim 1, wherein R is1Represents one of fluorine atom, fluorine atom substituted pyridyl group, cyano group, xanthenone group, cyano group substituted phenyl group, cyano group substituted pyridyl group, trifluoromethyl group substituted aryl group, trifluoromethyl group substituted pyridyl group, phenyl group substituted triazinyl group, nitrogen atom substituted terphenyl group, aryl group substituted carbonyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, azabenzofuran group, azabicyclohexyl fluorenyl group, azabiphenylfluorenyl group, dimethylanthrenonyl group, benzophenone group, azabenzophenonyl group, 9-fluorenone group, anthraquinone group, diphenylsulfone group derivative and diphenylboryl group;
R2、R3and are represented by phenyl, deuterated phenyl, tritiated phenyl, biphenylyl, deuterated biphenylyl, tritiated biphenylyl, deuterated terphenyl, tritiated terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, 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, One of deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiomethyl-substituted phenyl, tritioethyl-substituted phenyl, tritiomethyl-tert-butyl-substituted phenyl, tritiomethyl-substituted biphenyl, and tritiomethyl-tert-butyl-substituted biphenyl;
R4、R5、R6、R7and is represented by one of hydrogen, deuterium, tritium, methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, pentyl, hexyl, methyl-substituted cyclobutyl, ethyl-substituted cyclobutyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, heptyl, deuterated cyclohexyl, tritiated cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, phenyl, thienyl, furyl and pyridyl.
5. The boron-containing organic compound according to claim 1, wherein the specific structural formula of the boron-containing organic compound is any one of the following structures:
6. an organic light-emitting device comprising a cathode, an anode and a functional layer disposed between the cathode and the anode, wherein the boron-containing organic compound according to any one of claims 1 to 5 is contained in the functional layer of the organic light-emitting device.
7. The organic light-emitting device according to claim 6, wherein the functional layer comprises a light-emitting layer, and wherein the dopant material of the light-emitting layer is the boron-containing organic compound according to any one of claims 1 to 5.
8. The organic light-emitting device according to claim 7, wherein the light-emitting layer comprises 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-containing organic compound according to any one of claims 1 to 5.
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| CN116925114A (en) * | 2022-04-22 | 2023-10-24 | 江苏三月科技股份有限公司 | Boron-containing organic compound and organic electroluminescent device prepared from same |
| WO2024125652A1 (en) * | 2022-12-15 | 2024-06-20 | 华为技术有限公司 | Boron-containing organic compounds and organic electroluminescent device prepared from same |
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| CN115557979A (en) * | 2022-10-27 | 2023-01-03 | 深圳大学 | Boron-nitrogen hybrid compound, preparation method thereof and organic electroluminescent device |
| WO2024125652A1 (en) * | 2022-12-15 | 2024-06-20 | 华为技术有限公司 | Boron-containing organic compounds and organic electroluminescent device prepared from same |
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