CN111377955A - Boron-containing compound and preparation method and application thereof - Google Patents
Boron-containing compound and preparation method and application thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 105
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000463 material Substances 0.000 claims abstract description 65
- 239000002346 layers by function Substances 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 60
- -1 biphenylyl Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 12
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 10
- 229910052722 tritium Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 241000720974 Protium Species 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 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
- 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 150000001975 deuterium Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 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 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002019 doping agent Substances 0.000 claims 1
- 125000005561 phenanthryl group Chemical group 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 12
- 230000002035 prolonged effect Effects 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 2
- 230000002776 aggregation Effects 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000002994 raw material Substances 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 22
- 238000000921 elemental analysis Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 16
- 229910001868 water Inorganic materials 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 238000002390 rotary evaporation Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Substances BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000008204 material by function Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229910015845 BBr3 Inorganic materials 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- H10K85/658—Organoboranes
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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Abstract
The invention discloses a boron-containing compound and application thereof, belonging to the technical field of semiconductors, wherein the structure of the compound provided by the invention is shown as a general formula (1):
the invention also discloses application of the compound. The compound provided by the invention contains a boron atom structure, has strong rigidity, and has the characteristics of difficult crystallization and aggregation among molecules, and good film-forming property; the compound has the TADF characteristic, and because the electron donating abilities of the groups are different, the HOMO energy levels of the material are different, and the material can be used as different functional layer materials; in addition, the present inventionThe compound has high fluorescence quantum efficiency and can effectively generate radiation transition. Therefore, after the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged.
Description
Technical Field
The invention relates to a boron-containing compound, a preparation method and application thereof, belonging to the technical field of semiconductors.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
At present, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, but compared with actual product application requirements, the light emitting efficiency, the service life, and other performances of the OLED device need to be further improved. The research on the improvement of the performance of the OLED light emitting device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the OLED photoelectric functional material are needed to create the functional material of the OLED with higher performance. The photoelectric functional materials of the OLED applied to the OLED device can be divided into two broad categories from the application, i.e., charge injection transport materials and light emitting materials, and further, the charge injection transport materials can be further divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light emitting materials can be further divided into main light emitting materials and doping materials. In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, and as a host material of a light-emitting layer, a material having good bipolar property, appropriate HOMO/LUMO energy level, etc. is required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in the devices with different structures can also be completely different. Therefore, aiming at the industrial application requirements of the current OLED device, different functional film layers of the OLED device and the photoelectric characteristic requirements of the device, a more suitable OLED functional material or material combination with high performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display illumination industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and the development of organic functional materials with higher performance is very important as a material enterprise.
Disclosure of Invention
An object of the present invention is to provide a boron-containing compound. The compound contains a boron structure, has higher glass transition temperature and molecular thermal stability, and appropriate HOMO and LUMO energy levels, and can effectively improve the luminous efficiency of the device and prolong the service life of the OLED device after being applied to the manufacture of the OLED device.
The technical scheme for solving the technical problems is as follows: a boron-containing compound having a structure represented by the general formula (1):
in the general formula (1), W1、W2、W3Each independently represents a nitrogen atom or a boron atom, and W1、W2、W3And only one of them is represented as a nitrogen atom;
a. b, c, d and e are respectively and independently 0 or 1, and a + b + c + d + e is more than or equal to 1;
X1、X2、X3、X4、X5independently represent a single bond, a sulfur atom, an oxygen atom,
N(R6)、B(R7)、C(R8)(R9) Or Si (R)10)(R11) (ii) a Wherein R is8And R9、R10And R11Can be connected with each other to form a ring;
X1、X2、X3、X4、X5at least one of which is not represented by a single bond;
α, β, γ, η, θ are each independently represented as 1, 2 or 3;
when a, b, c, d and e are respectively and independently 0, Y1To Y21Each independently represents a nitrogen atom or CH; when a, b, c, d and e are respectively and independently represented as 1, Y21、Y1，Y16、Y17、Y13、Y14、Y8、Y9、Y4、Y5Only carbon atoms, and the others may be independently nitrogen atoms or CH;
R1to R5Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, or C1-C20Alkyl radical, C1-C20Alkyl substituted silyl, substituted or unsubstituted C6-C20Aryl, substituted or unsubstitutedHeteroaryl containing one or more hetero atoms, C6-C20One of an aryl or 5-to 30-membered heteroaryl substituted amine group of (a); r1To R5The connection mode with the general formula (1) comprises two connection modes of ring merging and substitution;
the R is6-R11Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms; r6、R7Are linked to adjacent groups and form a ring structure;
the substituent of the substitutable group is selected from protium, deuterium, tritium, cyano, fluorine atom, C1-C20Alkyl of (C)6-C20One or more of an aryl group, a 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, when R is1To R5When the substituted group is connected with the general formula (1), the substituted group and the substituted group are respectively and independently represented by a hydrogen atom, protium, deuterium, tritium, cyano, fluorine atom, methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted pyrenyl or a structure shown in the general formula (2); when said R is1To R5When the compounds are connected with the general formula (1) in a ring-parallel mode, the compounds are respectively and independently represented as one of structures shown in general formula (3) or general formula (4);
the L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene pyridyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, or a substituted or unsubstituted diphenylfluorenyl group;
Ar1、Ar2each independently represents substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms;
X6、X7each independently represents an oxygen atom, a sulfur atom, -N (R)12)-、-C(R13)(R14) -or-Si (R)15)(R16) -; wherein X6May also represent a single bond;
Z1to Z4Each independently represents a nitrogen atom or C-R17；
The R is12-R16Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms;
the R is17Are selected, identically or differently, from hydrogen atoms, protium atoms, deuterium atoms, tritium atoms, fluorine atoms, cyano groups, C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms; wherein two or more R9The groups may be linked to each other and may form a ring structure;
the general formula (3) or the general formula (4) is connected with the general formula (1) in a ring-merging mode, wherein the connecting sites are represented as connecting sites, and when the rings are merged, only two adjacent sites can be taken;
the substituent of the substitutable group is selected from protium, deuterium, tritium, cyano, fluorine atom, C1-C20Alkyl of (C)6-C20One or more of an aryl group, a 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the invention, R is6-R16Each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted azabenzophenanthrenyl group, a substituted or unsubstituted azabenzofuranyl group, or a substituted or unsubstituted benzocarbazolyl group;
ar is1、Ar2Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted azacarbazolyl group;
the R is17Is selected from hydrogen atom, protium atom, deuterium atom, tritium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, substituted or unsubstitutedSubstituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl;
the substituent of the substitutable group is one or more selected from fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, furyl group, dibenzofuryl group, carbazolyl group, fluorenyl group, naphthyridinyl group or pyridyl group.
As a further development of the invention, a, b, c, d or e is 0 or 1, and a + b + c + d + e is 2. As a further improvement of the invention, Y is1To Y21The number of nitrogen atoms is 0, 1 or 2.
Further, the general formula (1) is preferably one of the following structures, but not limited thereto:
one kind of (1).
Note: l is1To L21Is represented by R1、R2、R3、R4Or R5A site of attachment to the mother nucleus A-1 to A-141.
Further, R is1-R5The following structure is preferable, but not limited thereto:
Further, the specific structure of the compound is one of the following structures:
When W is1、W2Expressed as boron atoms, the reaction equation is:
the specific reaction process of the above reaction equation is:
step 1: under the protection of inert gas, dissolving an intermediate G-I by using tert-butyl benzene, wherein the ratio of the intermediate G-I to the tert-butyl benzene is 20mL-40mL for every 1G of the intermediate G-I;
step 2: slowly adding tert-butyl lithium into the reaction system in the step 1, and stirring the mixed solution; wherein the molar ratio of the tert-butyl lithium to the intermediate G-I is (1.0-2.0): 1;
and step 3: reacting the mixed solution obtained in the step 2 at the temperature of 50-70 ℃ for 2-4 h, naturally cooling to room temperature, and then slowly dropwise adding BBr3And diisopropylethylamine are stirred and reacted for 1h-4h at room temperature; the BBr3The molar ratio of the diisopropylethylamine to the intermediate G-1 is (1.0-2.0):1, and the molar ratio of the diisopropylethylamine to the intermediate G-1 is (2.0-3.0): 1;
4) and after the reaction is finished, adding water and dichloromethane for extraction and liquid separation, taking an organic phase, adding anhydrous magnesium sulfate for dewatering, filtering, performing rotary evaporation on the filtrate until no solvent exists, and passing through a neutral silica gel column to obtain the target compound.
When W is1、W3Expressed as boron atoms, the reaction equation is:
the specific reaction process of the above reaction equation is:
step 1: under the protection of inert gas, dissolving an intermediate G-II by using tert-butyl benzene, wherein the ratio of the intermediate G-II to the tert-butyl benzene is 20mL-40mL for every 1G of the intermediate G-I;
step 2: slowly adding tert-butyl lithium into the reaction system in the step 1, and stirring the mixed solution; wherein the molar ratio of the tert-butyl lithium to the intermediate G-II is (1.0-2.0): 1;
and step 3: reacting the mixed solution obtained in the step 2 at the temperature of 50-70 ℃ for 2-4 h, naturally cooling to room temperature, and then slowly dropwise adding BBr3And diisopropylethylamine are stirred and reacted for 1h-4h at room temperature; the BBr3The molar ratio of the diisopropylethylamine to the intermediate G-1 is (1.0-2.0):1, and the molar ratio of the diisopropylethylamine to the intermediate G-1 is (2.0-3.0): 1;
and 4, step 4: and after the reaction is finished, adding water and dichloromethane for extraction and liquid separation, taking an organic phase, adding anhydrous magnesium sulfate for dewatering, filtering, performing rotary evaporation on the filtrate until no solvent exists, and passing through a neutral silica gel column to obtain the target compound.
The second object of the present invention is to provide the application of the boron-containing compound in the preparation of organic electroluminescent devices. The boron-containing compound can be used for preparing organic electroluminescent devices, has good application effect and good industrialization prospect.
It is a further object of the present invention to provide an organic electroluminescent device. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
The technical scheme for solving the technical problems is as follows: an organic electroluminescent device comprising at least one functional layer containing the above boron-containing compound.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the boron-containing compound is used as a host material or a doping material of the luminescent layer and is used for manufacturing an organic electroluminescent device.
The fourth objective of the present invention is to provide an illumination or display device. The organic electroluminescent device can be applied to display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a lighting or display element comprising an organic electroluminescent device as described above.
The invention has the beneficial effects that:
1. the compound takes boron as a framework and is connected with a long branched chain structure, and because the electron-donating capability of the branched chain groups is different, the HOMO energy level of the whole structure of the compound can be freely adjusted, and the compound with shallow HOMO energy level can be used as a doping material; the material with deep HOMO energy level can be used as the host material of the hole bias type light-emitting layer.
In addition, the boron group is a bipolar group, the branched chain is a long-chain structure, the symmetry of the molecular structure is damaged, and the aggregation effect among molecules is avoided; the branched chain group of the compound also has strong rigidity, so that molecules are not easy to aggregate and crystallize, and the compound has good film forming property, high glass transition temperature and thermal stability.
2. The compound has high triplet state energy level, can effectively block energy loss and is beneficial to energy transfer. Therefore, after the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
in the drawings: 1 is a transparent substrate layer, 2 is an ITO 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 or an electron transport layer, 8 is an electron injection layer, and 9 is a cathode reflection electrode layer.
FIG. 2 is a graph of efficiency measured at different temperatures for a device made according to the present invention and a comparative device.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
R used below1-R5，X1-X5The meanings of the symbols a-e and the like are the same as those in the summary of the invention.
When W is1、W2Expressed as boron atom, W3Synthesis of intermediate G, when represented as a nitrogen atom:
(1) weighing raw material B and raw material C, dissolving in toluene under nitrogen atmosphere, and then dissolving Pd2(dba)3Adding tri-tert-butylphosphine, stirring the mixture, adding sodium tert-butoxide, heating and refluxing the mixed solution of the reactants at the reaction temperature of 90-120 ℃ for 10-24 h, cooling to room temperature after the reaction is finished, filtering the reaction solution, performing rotary evaporation on the filtrate until no solvent exists, and passing through a neutral silica gel column to obtain an intermediate S; wherein the molar ratio of the raw material C to the raw material B is (1.0-2.0):1, and the Pd is2(dba)3The molar ratio of the sodium tert-butoxide to the raw material B is (0.005-0.01):1, the molar ratio of the tri-tert-butylphosphine to the raw material B is (0.005-0.02):1, and the molar ratio of the sodium tert-butoxide to the raw material B is (1.5-3.0): 1;
(2) weighing an intermediate S and an intermediate F, dissolving the intermediate S and the intermediate F in tert-butyl benzene, stirring and mixing in a 250ml three-necked bottle under the protection of nitrogen, slowly dripping tert-butyl lithium, heating to 50-70 ℃, and stirring for reacting for 2-4 h; after the reaction is finished, naturally cooling to room temperature, and slowly dropwise adding BBr3And diisopropylethylamine, continuously stirring and reacting for 1-3 h, and after the reaction is finished, adding water and dichloromethane for extraction and liquid separation; adding anhydrous magnesium sulfate into an organic phase to remove water, filtering, performing reduced pressure rotary evaporation on the filtrate, and passing through a neutral silica gel column to obtain a target product G-I; wherein the molar ratio of the intermediate F to the intermediate S is (1.2-2.0):1, the molar ratio of the tert-butyllithium to the intermediate S is (1.2-2.0):1, and the trisThe molar ratio of boron bromide to the intermediate S is (1.2-2.0):1, and the molar ratio of diisopropylethylamine to the intermediate S is (2.0-3.0): 1.
When W is1、W3Expressed as boron atom, W2Synthesis of intermediate G, when represented as a nitrogen atom:
(1) weighing raw materials D and E and dissolving the raw materials D and E in toluene under the nitrogen atmosphere, and then dissolving Pd2(dba)3Adding tri-tert-butylphosphine, stirring the mixture, adding sodium tert-butoxide, heating and refluxing the mixed solution of the reactants at the reaction temperature of 95-110 ℃ for 10-24 h, cooling to room temperature after the reaction is finished, filtering the reaction solution, performing rotary evaporation on the filtrate until no solvent exists, and passing through a neutral silica gel column to obtain an intermediate F; wherein the molar ratio of the raw material E to the raw material D is (0.005-0.01):1, and the Pd2(dba)3The molar ratio of the tert-butyl phosphine to the raw material D is (0.005-0.01):1, the molar ratio of the tri-tert-butyl phosphine to the raw material D is (0.005-0.02):1, and the molar ratio of the sodium tert-butoxide to the raw material D is (1.5-3.0): 1;
(2) weighing intermediate F and raw material B, dissolving in toluene under nitrogen atmosphere, and dissolving Pd2(dba)3Adding tri-tert-butylphosphine, stirring the mixture, adding sodium tert-butoxide, heating and refluxing the mixed solution of the reactants at the reaction temperature of 95-110 ℃ for 10-24 h, cooling to room temperature after the reaction is finished, filtering the reaction solution, performing rotary evaporation on the filtrate until no solvent exists, and passing through a neutral silica gel column to obtain an intermediate G-II; wherein the molar ratio of the raw material E to the raw material D is (1.0-2.0):1, and the Pd2(dba)3The molar ratio of the compound to the raw material D is (0.005-0.01):1, the molar ratio of the tri-tert-butylphosphine to the raw material B is (0.005-0.02):1, and the molar ratio of the sodium tert-butoxide to the raw material B is (1.5-3.0): 1.
Synthesis example of intermediate G1:
(1) adding 0.02mol of raw material B1, 0.024mol of raw material C1, 0.04mol of sodium tert-butoxide and 1 × 10 into a 250ml three-neck flask under the protection of nitrogen-4mol Pd2(dba)3、1×10-4Heating and refluxing the tri-tert-butylphosphine and 150ml of toluene for 24 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and performing column chromatography to obtain an intermediate S1 with HPLC purity of 99.1% and yield of 65.1%;
(2) adding 0.01mol of intermediate S1, 0.012mol of tert-butyl lithium and 150ml of tert-butyl benzene into a 250ml three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 60 ℃, and stirring and reacting for 2 hours; then naturally cooled to room temperature, and 0.012mol of BBr is added dropwise3And 0.05mol of diisopropylethylamine, stirring and reacting for 1h, taking a sample point plate, and displaying that no intermediate S1 remains and the reaction is complete; naturally cooling to room temperature, adding water and dichloromethane for extraction and liquid separation; adding anhydrous magnesium sulfate into an organic phase to remove water, filtering, performing reduced pressure rotary evaporation on the filtrate at (-0.09MPa, 25 ℃) to obtain a target product, wherein the HPLC purity is 99.0%, and the yield is 47.1%;
elemental analysis Structure (molecular formula C)41H43BClNO): theoretical value C, 80.46; h, 7.08; b, 1.77; cl, 5.79; n, 2.29; o, 2.61; test values are: c, 80.47; h, 7.06; b, 1.81; cl,5.80, N, 2.27; o, 2.59. ESI-MS (M/z) (M)+): theoretical value is 611.31, found 611.46.
Synthesis example of intermediate G3:
(1) adding 0.01mol of raw material D1, 0.012mol of raw material E1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, then adding 0.02mol of sodium tert-butoxide and 5 × 10-5mol Pd2(dba)3And 5 × 10-5Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and sampling a sample point plate to show that no raw material B2 remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), passing through a neutral silica gel column to obtain a target product,HPLC purity 98.8%, yield 58.2%;
(2) adding 0.01mol of intermediate F3, 0.012mol of raw material B3 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, then adding 0.02mol of sodium tert-butoxide and 5 × 10-5mol Pd2(dba)3And 5 × 10-5Heating the mol of tri-tert-butylphosphine to 110 ℃, carrying out reflux reaction for 24 hours, and taking a sample, wherein no intermediate F3 is left, and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain a target product, wherein the HPLC purity is 99.0%, and the yield is 55.7%;
elemental analysis Structure (molecular formula C)30H21Cl2NO2): theoretical value C, 72.30; h, 4.25; cl, 14.23; n, 2.81; o, 6.42; test values are: c, 72.31; h, 4.23; cl, 14.25; n, 2.82; o, 6.39. ESI-MS (M/z) (M)+): theoretical value is 497.09, found 497.20.
Intermediate G was prepared by the synthetic method of intermediates G1 and G3, the specific structures are shown in Table 1.
TABLE 1
Example 1: synthesis of compound H2:
adding 0.01 ml of the mixture into a 250ml three-mouth bottle under the protection of nitrogenStirring and mixing mol of intermediate G1, 0.012mol of tert-butyl lithium and 150ml of tert-butyl benzene, heating to 60 ℃, and stirring for reaction for 2 hours; then naturally cooled to room temperature, and 0.012mol BBr is added dropwise3And 0.05mol of diisopropylethylamine, stirring at room temperature for 1 hour for reaction, taking a sample, and displaying that no intermediate G1 remains and the reaction is complete; adding water and dichloromethane for extraction and liquid separation; adding anhydrous magnesium sulfate into an organic phase to remove water, filtering, performing reduced pressure rotary evaporation on the filtrate at (-0.09MPa, 25 ℃) to obtain a target product, wherein the HPLC purity is 99.1%, and the yield is 45.7%;
elemental analysis Structure (molecular formula C)41H41B2NO): theoretical value C, 84.12; h, 7.06; b, 3.69; n, 2.39; o, 2.73; test values are: c, 84.13; h, 7.05; b, 3.68; n, 2.40; o, 2.74. ESI-MS (M/z) (M)+): theoretical value is 585.34, found 585.45.
Example 2: synthesis of compound H4:
compound H4 was prepared as in example 1, except intermediate G2 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)36H24B2N2): theoretical value C, 85.42; h, 4.78; b, 4.27; n, 5.53; test values are: c, 85.43; h, 4.76; b, 4.28; n, 5.54. ESI-MS (M/z) (M)+): theoretical value is 506.21, found 506.22.
Example 3: synthesis of compound H13:
adding 0.01mol of intermediate G3, 0.024mol of tert-butyl lithium and 150ml of tert-butyl benzene into a 250ml three-necked bottle under the protection of nitrogen, stirring and mixing, heating to 60 ℃, and stirring and reacting for 2 hours; then naturally cooled to room temperature, and 0.024mol BBr is dripped3And 0.1mol of diisopropylethylamine were stirred at room temperature for 1 hour, and a sample was taken from the reaction flask, indicating that no intermediate G3 remainedThe reaction is complete; adding water and dichloromethane for extraction and liquid separation; adding anhydrous magnesium sulfate into an organic phase to remove water, filtering, performing reduced pressure rotary evaporation on the filtrate at (-0.09MPa, 25 ℃) to obtain a target product, wherein the HPLC purity is 99.2%, and the yield is 41.8%;
elemental analysis Structure (molecular formula C)30H17B2NO2): theoretical value C, 80.96; h, 3.85; b, 4.86; n, 3.15; o, 7.19; test values are: c, 80.97; h, 3.87; b, 4.84; n, 3.14; and O, 7.18. ESI-MS (M/z) (M)+): theoretical value is 445.14, found 445.29.
Example 4: synthesis of compound H20:
compound H20 was prepared as in example 3, except intermediate G4 was used in place of intermediate G3.
Elemental analysis Structure (molecular formula C)42H27B2N3): theoretical value C, 84.74; h, 4.57; b, 3.63; n, 7.06; test values are: c, 84.72; h, 4.56; b, 3.62; and N, 7.08. ESI-MS (M/z) (M)+): theoretical value is 595.24, found 595.33.
Example 5: synthesis of compound H39:
compound H39 was prepared as in example 1, except intermediate G5 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)44H28B2N2): theoretical value C, 87.16; h, 4.65; b, 3.57; n, 4.62; test values are: c, 87.17; h, 4.67; b, 3.55; and N, 4.63. ESI-MS (M/z) (M)+): theoretical value is 606.24, found 606.36.
Example 6: synthesis of compound H48:
compound H48 was prepared as in example 1, except intermediate G6 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)44H28B2N2): theoretical value C, 87.16; h, 4.65; b, 3.57; n, 4.62; test values are: c, 87.17; h, 4.66; b, 3.56; and N, 4.64. ESI-MS (M/z) (M)+): theoretical value is 606.24, found 606.35.
Example 7: synthesis of compound H60:
compound H60 was prepared as in example 1, except intermediate G7 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)36H82B2N2O): theoretical value C, 87.16; h, 4.65; b, 3.57; n, 4.62; test values are: c, 87.17; h, 4.66; b, 3.56; and N, 4.64. ESI-MS (M/z) (M)+): theoretical value is 580.66, found 580.75.
Example 8: synthesis of compound H75:
compound H75 was prepared as in example 1, except intermediate G8 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)29H18B2N2O): theoretical value C, 80.61; h, 4.20; b, 5.00; n, 6.48; o, 3.70; test values are: c, 80.63; h, 4.23; b, 4.98; n, 6.47; and O, 3.69. ESI-MS (M/z) (M)+): theoretical value is 432.16, found 432.35.
Example 9: synthesis of compound H76:
compound H76 was prepared as in example 1, except intermediate G9 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)29H18B2N2O): theoretical value C, 80.61; h, 4.20; b, 5.00; n, 6.48; o, 3.70; test values are: c, 80.62; h, 4.21; b, 4.97; n, 6.47; and O, 3.73. ESI-MS (M/z) (M)+): theoretical value is 432.16, found 432.27.
Example 10: synthesis of compound H81:
compound H81 was prepared as in example 1, except intermediate G10 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)30H17B2NO): theoretical value C, 83.97; h, 3.99; b, 5.04; n, 3.26; o, 3.73; test values are: c, 83.98; h, 3.96; b, 5.06; n, 3.24; and O, 3.76. ESI-MS (M/z) (M)+): theoretical value is 429.15, found 429.33.
Example 11: synthesis of compound H84:
compound H84 was prepared as in example 1, except intermediate G11 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)33H23B2NO): theoretical value C, 84.12; h, 4.92; b, 4.59; n, 2.97; o, 3.40; test values are: c, 84.13; h, 4.94; b, 4.57; n, 2.98; and O, 3.38. ESI-MS (M/z) (M)+): theoretical value is 471.20, found 471.33.
Example 12: synthesis of compound H94:
compound H94 was prepared as in example 1, except intermediate G12 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)29H16B2N2O): theoretical value C, 80.99; h, 3.75; b, 5.03; n, 6.51; o, 3.72; test values are: c, 80.97; h, 3.74; b, 5.04; n, 6.53; and O, 3.72. ESI-MS (M/z) (M)+): theoretical value is 430.14, found 430.27.
Example 13: synthesis of compound H99:
compound H99 was prepared as in example 1, except intermediate G13 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)32H22B2N2O): theoretical value C, 81.40; h, 4.70; b, 4.58; n, 5.93; o, 3.39; test values are: c, 81.41; h, 4.68; b, 4.57; n, 5.95; and O, 3.39. ESI-MS (M/z) (M)+): theoretical value is 472.19, found 472.28.
Example 14: synthesis of compound H101:
compound H101 was prepared as in example 1, except intermediate G14 was used instead of intermediate G1.
Elemental analysis Structure (molecular formula C)39H37B2NO): theoretical value C, 84.05; h, 6.69; b, 3.88; n, 2.51; o, 2.87; test values are: c, 84.01; h, 6.70; b, 3.89; n, 2.53; o, 2.87. ESI-MS (M/z) (M)+): theoretical value is 557.31, found 557.45.
Example 15: synthesis of compound H105:
compound H105 was prepared as in example 1, except intermediate G15 was used instead of intermediate G1.
Elemental analysis Structure (molecular formula C)41H39B2NO): theoretical value C, 84.41; h, 6.74; b, 3.71; n, 2.40; o, 2.74; test values are: c, 84.43; h, 6.73; b, 3.72; n, 2.38; o, 2.74. ESI-MS (M/z) (M)+): theoretical value is 583.32, found 583.47.
Example 16: synthesis of compound H109:
compound H109 was prepared as in example 1, except intermediate G16 was used instead of intermediate G1.
Elemental analysis Structure (molecular formula C)43H45B2NO): theoretical value C, 84.19; h, 7.39; b, 3.52; n, 2.28; o, 2.61; test values are: c, 84.18; h, 7.37; b, 3.54; n, 2.29; o, 2.62. ESI-MS (M/z) (M)+): theoretical value is 613.37, found 613.45.
Example 17: synthesis of compound H114:
compound H114 was prepared as in example 1, except intermediate G17 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)45H47B2NO): theoretical value C, 84.52; h, 7.41; b, 3.38; n, 2.19; o, 2.50; test values are: c, 84.53; h, 7.43; b, 3.37; and N, 2.19. ESI-MS (M/z) (M)+): theoretical value is 639.38, found 639.47.
Example 18: synthesis of compound H118:
compound H118 was prepared as in example 1, except intermediate G18 was used instead of intermediate G1.
Elemental analysis Structure (molecular formula C)36H32B2N2O): theoretical value C, 81.54; h, 6.08; b, 4.08; n,5.28, O, 3.02; test values are: c, 81.53; h, 6.09; b, 4.09; n, 5.26; and O, 3.03. ESI-MS (M/z) (M)+): theoretical value is 530.27, found 530.37.
Example 19: synthesis of compound H120:
compound H120 was prepared as in example 1, except intermediate G19 was used instead of intermediate G1.
Elemental analysis Structure (molecular formula C)47H53B2NO): theoretical value C, 84.31; h, 7.98; b, 3.23; n, 2.09; o, 2.39; test values are: c, 84.33; h, 7.97; b, 3.26; n, 2.07; o, 2.37. ESI-MS (M/z) (M)+): theoretical value is 669.43, found 669.57.
Example 20: synthesis of compound H124:
compound H124 was prepared as in example 1, except intermediate G20 was used in place of intermediate G1.
Elemental analysis Structure (molecular formula C)38H36B2N2O): theoretical value C, 81.75; h, 6.50; b, 3.87; n, 5.02; o, 2.87; test values are: c, 81.74; h, 6.52; b, 3.86; n, 5.04; o, 2.84. ESI-MS (M/z) (M)+): theoretical value is 558.30, found 558.39.
The organic compound is used in a light-emitting device, has high glass transition temperature (Tg) and triplet state energy level (T1), and suitable HOMO and LUMO energy levels, and can be used as a host material of a light-emitting layer and a doping material of the light-emitting layer. The compound prepared in the example of the present invention and the existing material were respectively tested for thermal performance, T1 energy level and HOMO energy level, and the results are shown in table 2.
TABLE 2
| Compound (I) | T1(ev) | Tg(℃) | △Est | HOMO energy level (ev) |
| Compound H2 | 2.61 | 143 | 0.13 | -5.75 |
| Compound H4 | 2.59 | 141 | 0.15 | -5.80 |
| Compound H13 | 2.55 | 134 | 0.11 | -5.85 |
| Compound H20 | 2.51 | 132 | 0.12 | -5.87 |
| Compound H39 | 2.49 | 148 | 0.10 | -5.73 |
| Compound H48 | 2.41 | 149 | 0.09 | -5.80 |
| Compound H60 | 2.53 | 153 | 0.08 | -5.83 |
| Compound H75 | 2.51 | 147 | 0.13 | -5.88 |
| Compound H76 | 2.45 | 147 | 0.11 | -5.77 |
| Compound H81 | 2.61 | 152 | 0.12 | -5.85 |
| Compound H84 | 2.60 | 150 | 0.13 | -5.87 |
| Compound H94 | 2.61 | 151 | 0.14 | -5.76 |
| Compound H99 | 2.59 | 147 | 0.11 | -5.84 |
| Compound H101 | 2.63 | 146 | 0.13 | -5.76 |
| Compound H105 | 2.57 | 143 | 0.12 | -5.89 |
| Compound H109 | 2.62 | 145 | 0.09 | -5.83 |
| Compound H114 | 2.46 | 147 | 0.12 | -5.74 |
| Compound H118 | 2.49 | 152 | 0.11 | -5.75 |
| Compound H120 | 2.48 | 149 | 0.09 | -5.77 |
| Compound H124 | 2.50 | 151 | 0.13 | -5.83 |
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of (4); the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy test system (IPS-3), which is an atmospheric environment.
The organic compound prepared by the invention has high glass transition temperature, can improve the phase state stability of a material film, further prolongs the service life of a device, has a high triplet state energy level (T1) and a smaller △ Est while having a similar HOMO energy level as the existing application material, and can block the energy loss of a light-emitting layer, thereby improving the light-emitting efficiency of the device.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-20 and device comparative example 1. The device examples 2 to 20 and the device comparative example 1 of the present invention are completely the same as the device example 1 in the manufacturing process of the device, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, except that the device examples 2 to 20 change the doping material of the light emitting layer, the laminated structure of each device is shown in table 3, and the performance test results of the devices obtained in each example are shown in table 4.
Device example 1:
as shown in fig. 1, an electroluminescent device is prepared by the steps of:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
c) evaporating a hole transport material HT-1 with the thickness of 60nm on the hole injection layer 3 in a vacuum evaporation mode, wherein the layer is a hole transport layer 4;
d) evaporating an electron blocking material EB-1 on the hole transmission layer 4 in a vacuum evaporation mode, wherein the thickness of the electron blocking material EB-1 is 20nm, and the electron blocking layer 5 is formed on the hole transmission layer;
e) and a light-emitting layer 6 is evaporated on the electron blocking layer 5, the host materials are compounds GH-1 and GH-2 prepared in the embodiment of the invention, the doping material is H2, and the mass ratio of the compounds GH-1, GH-2 and H2 is 45: 45:10, thickness of 30 nm;
f) evaporating electron transport materials ET-1 and Liq on the light emitting layer 6 in a vacuum evaporation mode, wherein the mass ratio of the electron transport materials ET-1 to Liq is 1:1, the thickness of the electron transport materials ET-1 to Liq is 40nm, and the organic material of the layer is used as a hole blocking/electron transport layer 7;
g) vacuum evaporating an electron injection layer LiF with the thickness of 1nm on the hole blocking/electron transport layer 7, wherein the layer is an electron injection layer 8;
h) vacuum evaporating cathode Al (100nm) on the electron injection layer 8, which is a cathode reflection electrode layer 9;
after the electroluminescent device was fabricated according to the above procedure, the results of measuring the device properties are shown in table 4. The molecular structural formula of the related material is shown as follows:
TABLE 3
TABLE 4
From the results in table 4, it can be seen that the organic compound prepared by the present invention can be applied to the fabrication of OLED light emitting devices, and compared with comparative device examples 1 and 2, the efficiency and lifetime of the organic compound are greatly improved compared with those of known OLED materials, and especially the lifetime of the organic compound is greatly prolonged.
Further experimental study shows that the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature or high temperature, and the results of efficiency tests of the device examples 4, 9 and 27, the device comparative example 1 and the device comparative example 2 at the temperature range of-10 to 80 ℃ are shown in Table 5.
TABLE 5
As can be seen from the data in table 5, device examples 4, 9, and 27 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1 and device comparative example 2, the efficiency is high at low temperature, and the efficiency is steadily increased during the temperature increase process.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A boron-containing compound having the structure represented by the general formula (1):
in the general formula (1), W1、W2、W3Each independently represents a nitrogen atom or a boron atom, and W1、W2、W3And only one of them is represented as a nitrogen atom;
a. b, c, d and e are respectively and independently 0 or 1, and a + b + c + d + e is more than or equal to 1;
X1、X2、X3、X4、X5independently represent a single bond, a sulfur atom, an oxygen atom,
N(R6)、B(R7)、C(R8)(R9) Or Si (R)10)(R11) (ii) a Wherein R is8And R9、R10And R11Can be connected with each other to form a ring;
X1、X2、X3、X4、X5at least one of which is not represented by a single bond;
α, β, γ, η, θ are each independently represented as 1, 2 or 3;
when a, b, c, d and e are respectively and independently 0, Y1To Y21Each independently represents a nitrogen atom or CH; when a, b, c, d and e are respectively and independently represented as 1, Y21、Y1，Y16、Y17、Y13、Y14、Y8、Y9、Y4、Y5Represents a carbon atom, and the rest can be independently represented as a nitrogen atom or CH;
R1to R5Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, or C1-C20Alkyl radical, C1-C20Alkyl substituted silyl, substituted or unsubstituted C6-C20Substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, C6-C20One of an aryl or 5-to 30-membered heteroaryl substituted amine group of (a); r1To R5The connection mode with the general formula (1) includes two modes of ring merging and substitution;
the R is6-R11Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms; r6、R7May be linked to an adjacent group and form a ring structure;
the substituent of the substitutable group is selected from protium, deuterium, tritium, cyano, fluorine atom, C1-C20Alkyl of (C)6-C20One or more of an aryl group, a 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The boron-containing compound according to claim 1, wherein when R is1To R5When the substituted group is connected with the general formula (1), the substituted group and the substituted group are respectively and independently represented by a hydrogen atom, protium, deuterium, tritium, cyano, fluorine atom, methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted pyrenyl or a structure shown in the general formula (2); when said R is1To R5When the compounds are connected with the general formula (1) in a ring-parallel mode, the compounds are respectively and independently represented as one of structures shown in general formula (3) or general formula (4);
the L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene pyridyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, or a substituted or unsubstituted diphenylfluorenyl group;
Ar1、Ar2each independently represents substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms;
X6、X7each independently represents an oxygen atom, a sulfur atom, -N (R)12)-、-C(R13)(R14) -or-Si (R)15)(R16) -; wherein X6May also represent a single bond;
Z1to Z4Each independently represents a nitrogen atom or C-R17；
The R is12-R16Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms;
the R is17Are selected, identically or differently, from hydrogen atoms, protium atoms, deuterium atoms, tritium atoms, fluorine atoms, cyano groups, C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C20One of substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms; wherein two or more R9The groups may be linked to each other and may form a ring structure;
the general formula (3) or the general formula (4) is connected with the general formula (1) in a ring-merging mode, wherein the connecting sites are represented as connecting sites, and when the rings are merged, only two adjacent sites can be taken;
the substituent of the substitutable group is selected from protium, deuterium, tritium, cyano, fluorine atom, C1-C20Alkyl of (C)6-C20One or more of an aryl group, a 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
3. The boron-containing compound of claim 1, wherein R is6-R16Each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a,Substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted azabenzophenanthryl, substituted or unsubstituted azabenzofuranyl, substituted or unsubstituted benzocarbazolyl;
ar is1、Ar2Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted azacarbazolyl group;
the R is17Identically or differently selected from a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group;
the substituent of the substitutable group is one or more selected from fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, furyl group, dibenzofuryl group, carbazolyl group, fluorenyl group, naphthyridinyl group or pyridyl group.
4. The boron-containing compound according to claim 1, wherein a, b, c, d or e represents 0 or 1, and a + b + c + d + e is 2.
5. The boron-containing compound of claim 1, wherein Y is1To Y21The number of nitrogen atoms is 0, 1 or 2.
6. The boron-containing compound according to claim 1, wherein the specific structure of the compound is one of the following structures:
7. Use of a boron-containing compound according to any one of claims 1 to 6 for the preparation of an organic electroluminescent device.
8. An organic electroluminescent device comprising at least one functional layer comprising a boron-containing compound according to any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 7, comprising a light-emitting layer, wherein the boron-containing compound according to claims 1 to 6 is used as a host material or a dopant material of the light-emitting layer for fabricating the organic electroluminescent device.
10. A lighting or display element comprising an organic electroluminescent device as claimed in claims 7 to 8.
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| CN111377957A (en) * | 2018-12-29 | 2020-07-07 | 江苏三月光电科技有限公司 | Boron-containing compound and application thereof in organic electroluminescent device |
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Application publication date: 20200707 |