CN116082374A - Boron nitride compound, composition containing boron nitride compound and application of boron nitride compound - Google Patents
Boron nitride compound, composition containing boron nitride compound and application of boron nitride compound Download PDFInfo
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- CN116082374A CN116082374A CN202111274998.0A CN202111274998A CN116082374A CN 116082374 A CN116082374 A CN 116082374A CN 202111274998 A CN202111274998 A CN 202111274998A CN 116082374 A CN116082374 A CN 116082374A
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- substituted
- alkyl
- aryl
- alkoxy
- diphenylamino
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- 239000000203 mixture Substances 0.000 title claims abstract description 59
- -1 Boron nitride compound Chemical class 0.000 title claims description 85
- 229910052582 BN Inorganic materials 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910017464 nitrogen compound Inorganic materials 0.000 claims abstract description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 229910052805 deuterium Inorganic materials 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 42
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 38
- 239000011737 fluorine Substances 0.000 claims description 38
- 238000002347 injection Methods 0.000 claims description 35
- 239000007924 injection Substances 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical class C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 claims description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 16
- 125000006617 triphenylamine group Chemical group 0.000 claims description 16
- 102100039856 Histone H1.1 Human genes 0.000 claims description 14
- 101001035402 Homo sapiens Histone H1.1 Proteins 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 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 5
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- 239000004305 biphenyl Substances 0.000 claims description 5
- 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 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 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
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 150000001716 carbazoles Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- 230000005281 excited state Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([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
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 abstract description 15
- 239000010410 layer Substances 0.000 description 100
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920000144 PEDOT:PSS Polymers 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
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- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 3
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- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 description 2
- YGCHFJAJGMSFEP-UHFFFAOYSA-N 3,6-bis(4-tert-butylphenyl)-9h-carbazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(NC=2C3=CC(=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C3=C1 YGCHFJAJGMSFEP-UHFFFAOYSA-N 0.000 description 2
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- HHVGZHHLRBNWAD-UHFFFAOYSA-N 4,6-diphenyltriazine Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=NN=N1 HHVGZHHLRBNWAD-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical compound [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000004382 visual function Effects 0.000 description 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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Abstract
The invention provides a boron nitrogen compound, a composition containing the same and application thereof. The boron-nitrogen compound is a binuclear BN compound containing carbazole skeletons, effective red shift of BN derivative spectra can be achieved by constructing a binuclear strategy, and efficient narrow spectrum TADF emission is achieved by the organic electroluminescent device prepared from the compound and the composition thereof.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to a boron-nitrogen compound, a composition containing the same and application thereof.
Background
The organic photoelectric material (Organic Optoelectronic Materials) is an organic material having the characteristics of generation, conversion, transmission and the like of photons and electrons. Currently, controllable photoelectric properties of Organic photoelectric materials have been applied to Organic Light-Emitting diodes (OLEDs), organic solar cells (Organic Photovoltage, OPVs), organic field effect transistors (Organic Field Effect Transistor, OFETs), and even Organic lasers. In recent years, OLEDs have become a very popular new flat display product at home and abroad. The OLED display has the characteristics of self-luminescence, wide viewing angle, short reaction time, high luminous efficiency, wide color gamut, low working voltage, thin panel, capability of manufacturing a large-size flexible panel and low cost, and is known as a star flat display product in the 21 st century.
The history of organic electroluminescence can be traced back to the report of Bernanose et al in 1953 (see Papkovski D.B.Sens. And achuotors B.,1995,29,213.). After about 10 years, as compared with 1963, pope et al, new York university, applied a voltage across the crystals of anthracene, fluorescence emission of anthracene could be observed. (see M.Pope, H.Kallmann and P.Magnante, J.Chem.Phys.,1963,38,2042). In 1987, C.W.Tang et al, kodak, U.S. used an ultrathin film technique to prepare a light-emitting device with an aromatic amine having a good hole transport effect as a hole transport layer, an aluminum complex of 8-hydroxyquinoline as a light-emitting layer, and an Indium Tin Oxide (ITO) film and a metal alloy as an anode and a cathode, respectively. The device gave green emission at a 10V drive voltage with a luminance of up to 1000cd/m2, the efficiency of the device being 1.5lm/W (see c.w. tang and S.A.VanSlyke, appl.Phys.Lett.,1987, 51, 913). This breakthrough progress has led to rapid and intensive research into organic electroluminescence worldwide. In 1990, burroughes et al, university of Cambridge, proposed the first polymer (PPV) based light emitting diode. PPV has been shown to be highly fluorescent as an emissive material in a single layer device with high luminous efficiency (see burrouges j.h., bradley d.d. c., brown a.r., marks r.n., mackay k., friend R.H, burns p.l., holmes a.b., nature,1990,347,539.). Baldo, forrest et al, university of Princeton 1998, reported the first electroluminescent-based phosphorescent device, which in principle can have an internal quantum yield of 100%. (see M.A.Baldo, D.F.O' Briiental, nature,1998, 395, 151.) however, on the one hand, noble metals such as iridium platinum are commonly used as phosphorescent materials, and on the other hand, chemical instability still exists for deep blue phosphorescent materials, and the problem that the efficiency of the device drops greatly under high current density is solved, so that it is very important to develop an OLED device which uses cheap and stable organic small molecular materials and can realize high-efficiency luminescence.
In 2012, the Adachi research group at university of ninety reported a highly efficient fully fluorescent OLED device based on a Thermally Activated Delayed Fluorescence (TADF) mechanism. (Uoyama H, goushi K, shizu K, et al Highly efficient organic light-emitting diodes from delayed fluorescence [ J ]. Nature,2012,492 (7428):234-238.) when the S1 and T1 energy levels of the molecule differ sufficiently, triplet excitons can absorb thermal energy and return to the singlet state through the RISC process, thereby emitting fluorescence. The Internal Quantum Efficiency (IQE) of the device can reach 100% in theory, and the External Quantum Efficiency (EQE) can reach 30% or more, compared with the level of a shoulder phosphorescence device. As a next-generation light-emitting material, a TADF material is being studied.
The TADF molecules are primarily doped as guest materials in a wide bandgap host material to achieve high efficiency thermally activated delayed fluorescence (see Q.Zhang, J.Li, K.Shizu, S.Huang, S.Hirata, H.Miyazaki, C.Adachi, J.Am.Chem.Soc.2012,134,14706; H.Uoyama, K.Goushi, K.Shizu, H.Nomura, C.Adachi, nature,2012,492, 234; t. Nishimoto, t. Yasuda, s.y. Lee, r. Kondo, c. Adachi, mater. Horiz.,2014,1,264). Unlike traditional fluorescent molecular Localized (LE) state luminescence, TADF emission is mainly derived from transitions in ICT state, and is therefore susceptible to interdonor-acceptor vibration and rotational movement, resulting in a broader spectrum. The broad spectrum, while advantageous for illumination applications, does not meet the high color purity requirements of the display field. While the most important use of OLEDs is in display, narrow spectral designs (i.e., smaller full width at half maximum, FWHM) of TADF materials are necessary.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a boron nitrogen compound and application thereof. The invention aims to overcome the defect of TADF luminescent molecules, realizes effective red shift of BN derivative spectra by constructing a binuclear strategy, and relates to a binuclear boron-nitrogen compound based on carbazole skeleton as a narrow spectrum luminescent material for preparing a luminescent layer of an organic electroluminescent device, so that the prepared organic electroluminescent device realizes narrow spectrum TADF emission.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in one aspect, the present invention provides a boron nitrogen compound having a structure represented by the following formula a:
wherein X is 1 、X 2 、X 3 Independently selected from N or CH;
r is independently selected from H, D (deuterium), fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C30 aryl or C5-C30 heteroaryl;
q is an integer from 0 to 4 (e.g., 0, 1, 2, 3, or 4); n is 1 or 2;
R m each occurrence is independently H, D (deuterium), fluorine, CN, C 1 ～C 20 Alkyl, C 1 ～C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R a Substituted diphenylamino, triphenylamine, or substituted with one or more R a Substituted triphenylamine groups;
R a each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R b Substituted diphenylamino, triphenylamine, or substituted with one or more R b Substituted triphenylamine groups;
R b each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R c Substituted diphenylamino, triphenylamine, or substituted with one or more R c Substituted triphenylamine groups;
R c each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R d Substituted diphenylamino, triphenylamine, or substituted with one or more R d Substituted triphenylamine groups;
R d each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl radicals being optionally substituted by one or more R e Substituted C 6 ～C 14 An aryl group;
R e each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the above alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, C 1 -C 12 Haloalkyl, C 2 -C 6 Alkenyl, C 3 -C 10 Cycloalkyl, C 6 -C 14 Aryl and 5-to 18-membered heteroaryl.
In a preferred embodiment, the boron nitrogen compound is a compound having a structure represented by formula I, formula II or formula III:
X 1 、X 2 is independently N or CH, and X 1 And X 2 At least one of which is N.
X 3 Is N or CH.
R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 H, D, F, CN, C independently 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 6 ～C 30 Aryl or C 5 -C 30 Heteroaryl (including diphenyltriazine).
R m Each occurrence is independently H, D (deuterium), fluorine, CN, C 1 ～C 20 Alkyl, C 1 ～C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R a Substituted diphenylamino, triphenylamine, or substituted with one or more R a Substituted triphenylamine groups;
R a each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R b Substituted diphenylamino, triphenylamine, or substituted with one or more R b Substituted triphenylamine groups;
R b each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R c Substituted diphenylamino, triphenylamine, or substituted with one or more R c Substituted triphenylamine groups;
R c each occurrence is independently D (deuterium), fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R d Substituted diphenylamino, triphenylamine, or substituted with one or more R d Substituted triphenylamine groups;
R d each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl radicals being optionally substituted by one or more R e Substituted C 6 ～C 14 An aryl group;
R e each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the above alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, C 1 -C 12 Haloalkyl, C 2 -C 6 Alkenyl, C 3 -C 10 Cycloalkyl, C 6 -C 14 Aryl and 5-to 18-membered heteroaryl.
In one embodiment, the R m H, D (deuterium), fluorine, C1-C12 alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, phenyl, substituted with at least one C 1 -C 12 Aryl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted aryl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R a Each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R b Each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R c Each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Alkyl groupSubstituted phenyl, substituted with at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R d Each occurrence is independently D (deuterium), fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R m H, D (deuterium), fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl,
Methoxy, ethoxy, butoxy, hexyloxy, < >>
Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,/->
/>
Wherein the wavy line represents the attachment site of the group.
In some preferred embodiments, the R m Is H, methyl,
Phenyl group,/->
Wherein the wavy line represents the attachment site of the group.
In one embodiment, R is selected from H, F, -CN, C1-C6 alkyl substituted with at least one halogen, C1-C6 alkoxy, C6-C20 aryl substituted with at least one-CN, C6-C20 aryl substituted with a 5-to 18-membered heteroaryl, or C5-C20 heteroaryl.
In one embodiment, R is selected from H, F, CN, methyl, trifluoromethyl, methoxy, phenyl, pyridyl, biphenyl, terphenyl, cyano-substituted phenyl, diphenyltriazinyl,
In one embodiment R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Independently is H, F, CN, methyl, trifluoromethyl, methoxy, phenyl, pyridyl, biphenyl, terphenyl, cyano-substituted phenyl, diphenyltriazinyl, 
In a preferred embodiment, the boron nitrogen compound is any one of the following compounds:
the compounds of formulas I, II and III of the present invention can be prepared according to chemical synthesis methods conventional in the art, and the procedures and conditions can be referred to in the art as analogous procedures and conditions.
Illustratively, the basic process route for synthesizing the compounds of the present invention is as follows:
wherein: x is halogen;
in another aspect, the present invention provides an organic electroluminescent material comprising a boron nitrogen compound as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer comprising a light emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron injection layer, wherein at least one of the light emitting layer, the electron injection layer, the electron transport layer, the hole injection layer comprises a boron nitride compound as described above.
In the invention, the boron nitride compound with the structure shown in the formula I, the formula II or the formula III can be used as a functional material in at least one layer of a light-emitting layer, an electron injection layer, an electron transport layer, a hole transport layer and a hole injection layer of an organic electroluminescent device.
In one embodiment, the organic electroluminescent device of the present invention may further comprise an optional hole blocking layer, an optional electron blocking layer, an optional capping layer, and the like.
In one embodiment, the organic electroluminescent device has a structure as shown in fig. 4, in which 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a metal cathode.
In one embodiment, the boron nitrogen compound with the structure shown in the formula I, the formula II or the formula III is used for preparing a light-emitting layer in an organic electroluminescent device.
In one embodiment, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer containing the boron-nitrogen compound, and can further comprise any one or a combination of a plurality of hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.
In another aspect, the present invention provides an organic electroluminescent composition comprising a boron nitride compound as described above as a doping material and a host material;
Preferably, the host material is a material having an electron transport ability and/or a hole transport ability and having a triplet excited state energy higher than or equal to that of the dopant material.
In one embodiment of the present invention, the host material in the organic electroluminescent composition is a carbazole derivative and/or carboline derivative represented by the formulas (H-1) to (H-6).
Wherein X is 1 、Y 1 And Z 1 Is CH or N, and X 1 、Y 1 And Z 1 At most one of which is N.
Wherein R is 1H And R is 2H Independently any of the following groups:
wherein X is 1 、Y 1 And Z 1 Is CH or N, and X 1 、Y 1 And Z 1 At most one of them is N;
wherein R is aH And R is bH H, C independently 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 6 -C 20 Aryl, C 1 -C 20 Alkyl substituted C 6 -C 20 Aryl or C 1 -C 20 Alkoxy substituted C 6 -C 20 Aryl groups.
In one embodiment of the present invention, the organic electroluminescent composition preferably contains 0.3 to 30.0wt% of the boron-nitrogen compound having the structure represented by formula I or formula II as described above as a doping material, and the remaining 99.7 to 70.0wt% of the host material composed of 1 to 2 compounds of formulae (H-1) to (H-6).
In one embodiment, the host material contains 2 compounds of formulae (H-1) to (H-6) in a weight ratio of 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.
In one embodiment of the present invention, the host material in the organic electroluminescent composition is 1-2 of the compounds H1-1 to H1-427.
In a preferred embodiment of the present invention, the organic electroluminescent composition comprises 0.3 to 30.0wt% of any one of the compounds represented by formula I, formula II or formula III, and the remaining 99.7 to 70.0wt% of the composition is 1 to 2 of the compounds H1-1 to H1-427.
In a preferred embodiment of the present invention, the organic electroluminescent composition comprises 2 compounds of the formulae H1-1 to H1-427 as host materials in a weight ratio of 1:5 to 5:1, for example 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.
In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the compounds shown in formula I, formula II or formula III (the content is 0.3 wt% to 30.0 wt%); the main body material (the content is 99.7wt% -70.0wt%) is composed of any one of the compounds shown as the formula Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A and any one of the compounds shown as the formulas H-1 to H-6.
In a preferred embodiment, the weight ratio between the compound indicated by Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A and the compound indicated by H-1, H-2, H-3, H-4, H-5 or H-6 in the host material is from 1:5 to 5:1, such as 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.
Wherein R is 1a 、R 1b 、R 2a 、R 2b 、R 3a And R is 3b Wherein 1 or 2 are independently R Tz The remainder being the same or different and independently hydrogen, deuterium, C 1 -C 8 Alkyl, C 1 -C 8 Alkoxy, C 6 -C 18 Aryl, C 1 -C 8 Alkyl substituted C 6 -C 18 Aryl or C 1 -C 8 Alkoxy substituted C 6 -C 18 Aryl of (a); r is R Tz Is any one of substituent groups shown in the following formula:
wherein asterisks indicate the attachment site of the group.
In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the compounds shown in formula I, formula II or formula III (the content is 0.3 wt% to 30.0 wt%); the main material (content of 99.7wt% -70.0wt%) is composed of any one of compounds shown as formulas TRZ-1 to TRZ-76 and any one of carbazole or carboline derivatives shown as formulas H1-1 to H1-427.
In a preferred embodiment, the weight ratio between the compound of formulae TRZ-1 to TRZ-76 and the carbazole or carboline derivative in the host material is 1:5 to 5:1, e.g. 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, etc.
In another aspect, the present invention provides an organic electroluminescent material comprising an organic electroluminescent composition as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer comprising a light emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron injection layer, wherein at least one of the light emitting layer, the electron injection layer, the electron transport layer, the hole injection layer comprises the organic electroluminescent composition as described above.
In the present invention, the organic electroluminescent composition may be used as a functional material in at least one of a light emitting layer, an electron injection layer, an electron transport layer, a hole transport layer, and a hole injection layer of an organic electroluminescent device.
In a certain embodiment of the invention, the material of the light emitting layer in the organic electroluminescent device comprises an organic electroluminescent composition as described above.
In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on energy transfer from a host material to any one of the compounds represented by formula I, formula II or formula III or carrier capture of the light-emitting material itself.
In one embodiment of the invention, the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition may be a carbazole derivative and/or a carboline derivative as shown in formulae (H-1) to (H-6). In a preferred embodiment, the organic electroluminescent composition comprises 0.3 to 30.0wt% of any one of the compounds of formula I, formula II or formula III, and the remaining 99.7 to 70.0wt% of the composition is a host composed of 1 to 2 compounds of formulae (H-1) to (H-6). For example, when the host contains 2 compounds of formulas (H-1) to (H-6), the weight ratio of the two compounds is 1:5 to 5:1.
In one embodiment of the invention, the organic electroluminescent composition is a light-emitting layer; the main materials in the composition are 1-2 of the compounds H1-1 to H1-427. In a preferred embodiment, the organic electroluminescent composition comprises 0.3-30.0wt% of any one of the compounds of formula I, formula II or formula III, and the remaining 99.7-70.0wt% of the composition is 1-2 of the compounds H1-1 to H1-427. For example, when 2 compounds of formulas H1-1 to H1-427 are included in the composition, the weight ratio of the two compounds is 1:5 to 5:1.
In one embodiment of the invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one compound shown in the formula I, the formula II or the formula III (the content is 0.3-30.0 wt%); the main body material (content of 99.7wt% -70.0wt%) is composed of any one of the compounds shown as the formula Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A and any one of the compounds shown as the formulas H-1 to H-6. For example, in the host material, the weight ratio of Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A compound to the compound of H-1, H-2, H-3, H-4, H-5 or H-6 is 1:5 to 5:1.
In one embodiment of the invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one compound shown in the formula I, the formula II or the formula III (the content is 0.3-30.0 wt%); the main material (content of 99.7wt% -70.0wt%) is composed of any one of 1,3, 5-triazine derivatives shown in formulas TRZ-1 to TRZ-76 and any one of carbazole or carboline derivatives shown in formulas H1-1 to H1-427. For example, in the host material, the weight ratio between the 1,3, 5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.
In one embodiment of the invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any one compound (the content is 0.3-30.0 wt%) shown in the formulas BN 1-BN 396; the main body material (the content is 99.7wt% -70.0wt%) is composed of any one of the compounds shown as the formula Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A and Trz6-A and any one of carbazole or carboline derivatives shown as the formulas H1-1 to H1-427. For example, in the host materials, the weight ratio between the compounds of formulae Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A, and Trz6-A, and carbazole or carboline derivatives of formulae H1-1 to H1-427 is 1:5 to 5:1.
In one embodiment of the present invention, the organic electroluminescent device further comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer comprises a light-emitting layer containing the organic electroluminescent composition, and can also comprise any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.
In another aspect, the invention provides an application of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent illumination source.
Description of the terms
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
As used herein, the term "comprising" or "including" can be open, semi-closed, and closed. In other words, the term also includes "consisting essentially of …," or "consisting of ….
Definition of groups
In this specification, groups and substituents thereof can be selected by one skilled in the art to provide stable moieties and compounds. When substituents are described by conventional formulas written from left to right, the substituents also include chemically equivalent substituents obtained when writing formulas from right to left.
The section headings used in this specification are for organizational purposes only and are not to be construed as limiting the subject matter described. All documents or portions of documents cited in this disclosure, including but not limited to patents, patent applications, articles, books, operating manuals, and treatises, are hereby incorporated by reference in their entirety.
Unless otherwise specified, all technical and scientific terms used herein have the standard meaning of the art to which the claimed subject matter belongs. In case there are multiple definitions for a term, the definitions herein control.
As used herein, the singular forms "a", "an", and "the" are understood to include plural referents unless the context clearly dictates otherwise. Furthermore, the term "comprising" is an open-ended limitation and does not exclude other aspects, i.e. it includes the content indicated by the invention.
Unless otherwise indicated, the present invention employs conventional methods of mass spectrometry, elemental analysis, and the various steps and conditions are referred to in the art by conventional procedures and conditions.
The present invention employs, unless otherwise indicated, standard nomenclature for analytical chemistry, organic synthetic chemistry and optics, and standard laboratory procedures and techniques. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and light emitting device performance detection.
The compounds of the present invention may contain non-natural proportions of atomic isotopes on one or more of the atoms comprising the compounds. For example, compounds such as deuterium (2H) may be labeled with a radioisotope. All isotopic variations of the compounds of the present invention are intended to be encompassed within the scope of the present invention.
In the present invention, the number of "substitutions" may be one or more unless otherwise specified; when plural, it means two or more, for example, may be 2, 3 or 4. In addition, when the number of "substitutions" is plural, the "substitutions" may be the same or different. In the present invention, the "substituted" position may be any position unless otherwise specified.
In the present invention, as part of a group or other groups (e.g., as used in halogen-substituted alkyl groups and the like), the term "alkyl" is meant to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the indicated number of carbon atoms. For example, C 1 ～C 20 Alkyl groups include straight or branched chain alkyl groups having 1 to 20 carbon atoms. As in "C 1 ～C 6 Alkyl "is defined to include groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched chain structure. For example, in the present invention, the C1-C6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein propyl is C3 alkyl (including isomers such as n-propyl or isopropyl); butyl is C4 alkyl (including isomers such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is C5 alkyl (including isomers such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, t-pentyl or neopentyl); hexyl is C6 alkyl (including isomers such as n-hexyl or isohexyl).
The term "alkoxy" as used herein refers to an alkyl group as defined above, each attached via an oxygen bond (-O-).
In the present invention, the term "Cn-m aryl" as part of a group or other group refers to a monocyclic or polycyclic aromatic group having n to m ring carbon atoms (the ring atoms being carbon atoms only) having at least one carbocyclic ring with a conjugated pi-electron system. Examples of the above aryl unit include phenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthracyl. In one embodiment, the aryl group is preferably a C6-14 aryl group, such as phenyl and naphthyl, more preferably phenyl.
In the present invention, the term "n-m membered heteroaryl" as part of a group or other group means an aromatic group having one or more (e.g., 1, 2, 3 and 4) heteroatoms selected from nitrogen, oxygen and sulfur, having from n to m ring atoms, said heteroaryl being a monocyclic, bicyclic, tricyclic or tetracyclic ring system, wherein at least one ring is an aromatic ring. Heteroaryl groups within the scope of this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazole, furanyl, thienyl, benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinolinyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purinyl, pteridinyl, naphthyridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolopyridinyl, thienopyridinyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, as preferable examples of the "5-to 18-membered heteroaryl group", furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridyl, pyrimidinyl and carbazolyl groups are cited, and carbazolyl groups are more preferable.
The term Cn-Cm cycloalkyl as used herein refers to mono-or multicyclic alkyls having from n to m carbon atoms, such as 3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and bicycloheptyl. In one embodiment, the C3-C10 cycloalkyl is preferably adamantyl or cyclohexyl.
The definition of a carbon number range for a group as described in the present invention means that any integer included in the definition, such as C, of carbon atoms 1 ～C 20 Means that the number of carbon atoms of the radicals may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17C, 18, 19 or 20 3 -C 10 It is meant that the number of carbon atoms of the group may be 3, 4, 5, 6, 7, 8, 9 or 10, and so on for the other groups.
The above preferred conditions can be arbitrarily combined on the basis of not deviating from the common knowledge in the art, and thus, each preferred embodiment of the present invention can be obtained.
The reagents and materials used in the present invention are commercially available.
Compared with the prior art, the invention has the following beneficial effects:
the boron nitride compound adopts a binuclear strategy to realize effective red shift of a BN derivative spectrum, has a narrow spectrum, is used as a narrow spectrum luminescent material for preparing a luminescent layer of an organic electroluminescent device, realizes narrow spectrum TADF emission, and ensures that the electroluminescent external quantum efficiency of the device is up to more than 24 percent.
Drawings
FIG. 1 shows the result of the reaction of Compound BN91 in toluene (concentration: 1X 10) -5 M) photoluminescence spectrum in the sample.
FIG. 2 shows the result of the reaction of Compound BN110 in toluene (concentration: 1X 10) -5 M) photoluminescence spectrum in the sample.
FIG. 3 shows the result of the reaction of Compound BN131 in toluene (concentration: 1X 10) -5 M) photoluminescence spectrum in the sample.
Fig. 4 is a schematic view of a device structure used in effect example 2, in which 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a metal cathode.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
In one embodiment of the invention, the compounds of formulas I, II and III are synthesized using the following starting materials in addition to the substrate 2-bromo-1, 3-difluorobenzene:
in the invention, molecular Mass spectrum data (Mass Spectra: MS) with the relative molecular weight below 1000 is measured by an ITQ1100 ion trap gas chromatograph-Mass spectrometer of Thermo Fisher company, and molecular Mass spectrum data with the relative molecular weight above 1000 is measured by an Autoflex Speed matrix auxiliary laser analysis time-of-flight Mass spectrometer of Bruker company. The elemental analysis of the final product was performed using a machine from company Elemental analysis, flash EA1112.
The fluorescence spectrum was measured by an RF-5301PC fluorescence photometer of Shimadzu corporation, japan, and the excitation wavelength selected at the time of the test was the maximum absorption wavelength.
Synthetic examples
In the first step, 35.2mmol of starting material (i.e. 3, 6-bis (4- (tert-butyl) phenyl) -9H-carbazole or its derivatives (A1 to A9), 10.24g of cesium carbonate (52.8 mmol), 3.26g of 2-bromo-1, 3-difluorobenzene (17.0 mmol) were added to a 250ml of two-necked round bottom flask, to which 80ml of anhydrous DMF solution was added the reaction system was stirred at 160℃for 24 hours, then cooled to room temperature, poured into ice water (2L) and the white solid was filtered off with suction, dried in vacuo and then further purified by column chromatography using a mixed eluent of dichloromethane/petroleum ether to give intermediate 1a as a white solid.
In the second step, 19.4mL of a solution of t-butyllithium in n-hexane (25.2 mmol) was slowly added to 100mL of a solution of t-butylbenzene containing 12.6mmol of intermediate 1a (-30 ℃ C.) under nitrogen atmosphere. Slowly heating to 60 ℃, stirring for 2 hours, cooling to-30 ℃, adding 2.4mL boron tribromide (6.3 mmol) and putting the reaction mixture inStirring was carried out at room temperature for 1 hour. 15.6mL of N, N-diisopropylethylamine (91.1 mmol) was then added at 0deg.C, and the reaction mixture was allowed to cool to room temperature after stirring for an additional 5 hours at 130deg.C. To the reaction mixture was added 5ml of methanol to quench the residual BBr 3 . The reaction system was concentrated in vacuo and purified by column chromatography with an eluent of a mixture of dichloromethane/petroleum ether to give intermediate 1b.
In a third step, intermediate 1b (6.5 mmol), 1.7g of pinacol diboronate (13 mmol) were added to tetrahydrofuran (60 mL) at room temperature, the mixture was bubbled with nitrogen for 10 minutes, and 34.9mg of 4,4 '-di-tert-butyl-2, 2' -bipyridine (0.13 mmol) and 43.1mg of methoxy (cyclooctadiene) iridium dimer (0.065 mmol) were added under high flow of nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system is cooled to room temperature, the reaction system is directly concentrated under reduced pressure and purified by column chromatography to obtain an intermediate 1c.
Fourth step, intermediate 1c (6 mmol), raw material BXX (2.5 mmol), potassium carbonate (15 mmol) was added to tetrahydrofuran solution (50 ml), and 8ml of distilled water was further added, bubbled with nitrogen for 5 minutes, and 207.9mg of palladium tetraphenylphosphine (0.18 mmol) was added under high nitrogen flow, the mixture was heated to reflux and stirred for 24 hours, after the system was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography to give final product BNn, the reaction yield in this step was 28-37. The data obtained for the target compounds are shown in Table 1.
Experimental details of the synthesis examples are illustrated with regard to the compound BN 91:
In the first step, 60ml of a solution containing 15.2g of 3, 6-bis (4- (tert-butyl) phenyl) -9H-carbazole (35.2 mmol) 10.24g of cesium carbonate (52.8 mmol), 3.26g of 2-bromo-1, 3-difluorobenzene (17.0 mmol) was added to a 250ml double neck round bottom flask, to which was added 80ml of anhydrous DMF solution. The reaction was stirred at 160℃for 24 hours, then cooled to room temperature and poured into ice water (2L). The white solid was filtered off with suction, dried in vacuo and then further purified by column chromatography using a mixed eluent of dichloromethane/petroleum ether (1:3) to give 13g of intermediate 1a as a white solid. (yield 79%)
Second, 19.4mL of the mixture is subjected to tertiary reaction under the protection of nitrogen atmosphereA solution of butyllithium in n-hexane (25.2 mmol) was slowly added to a solution of 100mL of t-butylbenzene (-30 ℃ C.) containing 12.8g of intermediate 1a (12.6 mmol). After slowly heating to 60℃and stirring for 2 hours, n-hexane was removed in vacuo, then cooled to-30℃and 2.4mL of boron tribromide (6.3 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour. 15.6mL of N, N-diisopropylethylamine (91.1 mmol) was then added at 0deg.C, and the reaction mixture was allowed to cool to room temperature after stirring for an additional 5 hours at 130deg.C. To the reaction mixture was added 5ml of methanol to quench the residual BBr 3 . The reaction was concentrated in vacuo and purified by column chromatography with a dichloromethane/petroleum ether (1:2) mixture eluent to give 4.2 g of intermediate 1b as a bright green solid (34% yield).
In a third step, 4.1g of intermediate 1b (6.5 mmol), 1.7g of pinacol diboronate (13 mmol) were added to tetrahydrofuran (60 mL), the mixture was bubbled with nitrogen for 10 minutes and 34.9mg of 4,4 '-di-tert-butyl-2, 2' -bipyridine (0.13 mmol) and 43.1mg of methoxy (cyclooctadiene) iridium dimer (0.065 mmol) were added under high flow of nitrogen. After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was concentrated under reduced pressure, and purified by column chromatography to give 4.17g of intermediate 1c (yield 85%).
Fourth, 4.5g of intermediate 1c (6 mmol), 2.0g of potassium carbonate (15 mmol), 0.76g of B3 (2.5 mmol) were added to tetrahydrofuran (50 ml), 8ml of distilled water was further added, bubbling was performed for 5 minutes with nitrogen, and 207.9mg of tetra-triphenylphosphine palladium (0.18 mmol) was added under a high nitrogen flow, and the mixture was heated to reflux and stirred for 36 hours, and after the system was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography to give 1.2g of final product BN. (yield 33%)
TABLE 1
FIG. 1 shows the presence of Compound BN91 in toluene (concentration: 1X 10) -5 M), fig. 2 is a fluorescence spectrum of the compound BN110 in toluene solution (concentration: 1X 10 -5 M), fig. 3 is a fluorescence spectrum of compound BN131 in toluene solution (concentration: 1X 10 -5 M), it can be seen from fig. 1-3 that the luminescence of such compounds has a very narrow half-width.
Electroluminescent device embodiment
Some representative electroluminescent device embodiments are given below, and some of the material molecular structures involved in the device embodiments are as follows:
the following embodiment of electroluminescent devices prepared by using the material of the present invention, the specific device preparation process is as follows:
(1) And (3) substrate processing: the transparent ITO glass is used as a substrate material for preparing devices, is subjected to ultrasonic treatment for 30min by using 5% ITO washing liquid, is sequentially subjected to ultrasonic washing by using distilled water (2 times), acetone (2 times) and isopropanol (2 times), and is finally stored in isopropanol. Before each use, the surface of the ITO glass is carefully wiped by acetone cotton balls and isopropanol cotton balls, and after the isopropanol is washed, the ITO glass is dried, and then is treated by plasma for 5min for standby. The preparation of the device is completed by combining spin coating and vacuum evaporation process.
(2) Hole injection lamination hole transport layer preparation: a layer of 20nm thick PEDOT PSS (Poly 3, 4-ethylenedioxythiophene) polystyrene sulfonate, which is commercially available from Heraeus Corp. Germany, was first spin-coated on the ITO surface as a hole injection layer, then a 50nm thick Poly-HTL was spin-coated on the hole injection layer as a hole transport layer, and then the ITO glass with the hole injection layer and the hole transport layer was annealed at 200℃for 30 minutes in a nitrogen-protected glove box (cross-linking the Poly-HTL).
(3) Preparing a light-emitting layer: the main material and the luminescent material are dissolved in dimethylbenzene according to the proportion of 97wt% (weight percent concentration) to prepare a solution with the concentration of 2wt%, and the prepared solution is used for preparing the luminescent layer by spin coating, wherein the thickness of the luminescent layer is 50nm.
(4) Preparation of an electron transport layer, an electron injection layer and a metal electrode: an electron transport layer, an electron injection layer and a metal electrode are prepared by adopting an evaporation process, and when the vacuum degree of a vacuum evaporation system reaches 5 multiplied by 10 -4 And starting evaporation when Pa is lower, wherein the deposition rate is equal to or lower than that of the Sien film thickness meter, and sequentially depositing an organic electronic transmission layer, a LiF electron injection layer and a metal Al electrode on the light-emitting layer by utilizing a vacuum evaporation process (the specific device structure is shown in the following effect example). Wherein the deposition rate of the organic material is
Deposition rate of LiF->
The deposition rate of Al is->
Device examples A1 to A135
In the organic electroluminescent device (structure shown in FIG. 4) in device examples A1-A135, PEDOT: PSS was used as a hole injection layer, poly-HTL was used as a hole transport layer, H1-48 was used as a host material in a light emitting layer, BNn was used as a doped light emitting material (doping concentration was 2 wt%), TRZ-8 was used as an electron transport material, liF was used as an electron injection layer, and Al was used as a metal cathode, respectively. Effect example the organic electroluminescent device structure was [ ITO/PEDOT: PSS (20 nm)/Poly-HTL (50 nm)// H1-33+3wt% bnn/TRZ-8 (50 nm)/LiF (1 nm)/Al (100 nm) ].
The current, voltage, brightness, luminescence spectrum and other characteristics of the device were synchronously tested using a Photo Research PR 655 spectral scanning luminance meter and a Keithley K2400 digital source meter system. The performance test of the device was performed at room temperature under ambient atmosphere. The External Quantum Efficiency (EQE) of the device is calculated from the current density, brightness and electro-spectral combined with the visual function in the case of the light emission as a langerhans distribution.
The test results are shown in Table 2.
TABLE 2
The electroluminescent device effect implementation data listed in table 2 prove that the luminescent material provided by the present disclosure can be used for preparing high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has narrow band characteristics, the half-peak width of the electroluminescent spectrum is less than 60nm, and the electroluminescent external quantum efficiency is as high as more than 24.6%.
Device examples B1 to B135
In the organic electroluminescent device in device examples B1 to B135, in the organic electroluminescent device (structure shown in FIG. 4) in effect example 2, PEDOT: PSS was used as a hole injection layer, poly-HTL was used as a hole transport layer, a mixture of H1-33 and TRZ-8 in a light emitting layer was used as a host material (weight mixing ratio of H1-33 to TRZ-1 was 1:1), BN-1 to BN-100 were used as doped light emitting materials (doping concentration was 3 wt%), TRZ-8 was used as an electron transport material, liF was used as an electron injection layer, and Al was used as a metal cathode, respectively. Effect example the organic electroluminescent device structure was [ ITO/PEDOT: PSS (20 nm)/Poly-HTL (50 nm)/H1-33:trz-8+3wt% bnn/TRZ-8 (50 nm)/LiF (1 nm)/Al (100 nm) ].
The effect of the device was also tested, the peak position and half-width of the electroluminescent spectrum, and the electroluminescent external quantum efficiency were tested, and the test results are shown in table 3.
TABLE 3 Table 3
The electroluminescent device implementation data listed in table 3 prove that the luminescent material provided by the invention can be used for preparing high-efficiency organic electroluminescent devices, and the electroluminescent spectrum has narrow band characteristics, the half-peak width of the electroluminescent spectrum is less than 60nm, and the electroluminescent external quantum efficiency is as high as more than 26.4%.
The applicant states that the present invention is illustrated by the above examples of compositions comprising the boron nitride compounds of the present invention and their use, but the present invention is not limited to, i.e. does not mean that the present invention must be practiced in dependence upon, the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (10)
1. A boron nitride compound, characterized in that the boron nitride compound is a compound having a structure represented by the following formula a:
wherein X is 1 、X 2 、X 3 Independently selected from N or CH;
R is independently selected from H, deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C30 aryl or C5-C30 heteroaryl;
q is an integer from 0 to 4; n is 1 or 2;
R m each occurrence is independently H, deuterium, fluorine, CN, C 1 ～C 20 Alkyl, C 1 ～C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R a Substituted diphenylamino, triphenylamine, or substituted with one or more R a Substituted triphenylamine groups;
R a each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R b Substituted diphenylamino, triphenylamine, or substituted with one or more R b Substituted triphenylamine groups;
R b each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R c Substituted diphenylamino, triphenylamine, or substituted with one or more R c Substituted triphenylamine groups;
R c each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R d Substituted diphenylamino, triphenylamine, or substituted with one or more R d Substituted triphenylamine groups;
R d each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl radicals being optionally substituted by one or more R e Substituted C 6 ～C 14 An aryl group;
R e each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, C 1 -C 12 Haloalkyl, C 2 -C 6 Alkenyl, C 3 -C 10 Cycloalkyl, C 6 -C 14 Aryl and 5-to 18-membered heteroaryl.
2. The boron nitride compound according to claim 1, wherein the boron nitride compound is a compound having a structure represented by the following formula I, formula II or formula III:
X 1 、X 2 Is independently N or CH, and X 1 And X 2 At least one of which is N;
X 3 is N or CH;
R 1 、R 2 、R 3 、R 4 、R 5 and R is 6 H, D, F, CN, C independently 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 6 ～C 30 Aryl or C 5 -C 30 Heteroaryl;
R m each occurrence is independently H, deuterium, fluorine, CN, C 1 ～C 20 Alkyl, C 1 ～C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, by one or moreMultiple R' s a Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R a Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R a Substituted diphenylamino, triphenylamine, or substituted with one or more R a Substituted triphenylamine groups;
R a each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R b Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R b Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R b Substituted diphenylamino, triphenylamine, or substituted with one or more R b Substituted triphenylamine groups;
R b each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R c Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R c Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R c Substituted diphenylamino, triphenylamine, or substituted with one or more R c Substituted triphenylamine groups;
R c each occurrence is independently deuterium, fluorine, CN, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl, substituted by one or more R d Substituted C 6 ～C 14 Aryl, 5-to 18-membered heteroaryl, substituted with one or more R d Substituted 5-to 18-membered heteroaryl, diphenylamino, substituted with one or more R d Substituted diphenylamino, triphenylamine, or substituted with one or more R d Substituted triphenylamine groups;
R d at each occurrence independentlyThe standing site is deuterium, fluorine and C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 ～C 14 Aryl radicals being optionally substituted by one or more R e Substituted C 6 ～C 14 An aryl group;
R e independently for each occurrence; deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, or C 6 ～C 14 An aryl group;
the above alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of: halogen, -CN, C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, C 1 -C 12 Haloalkyl, C 2 -C 6 Alkenyl, C 3 -C 10 Cycloalkyl, C 6 -C 14 Aryl and 5-to 18-membered heteroaryl.
3. The boron nitride compound according to claim 1 or 2, wherein R m Is H, deuterium, fluorine, C1-C12 alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, phenyl, substituted with at least one C 1 -C 12 Aryl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted aryl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl;
preferably, said R a Each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl;
preferably, said R b Each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl;
preferably, said R c Each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl;
preferably, said R d Each occurrence is independently deuterium, fluorine, C 1 ～C 12 Alkyl, C 1 ～C 12 Alkoxy, C 3 -C 10 Cycloalkyl, at least one C 1 -C 12 Phenyl substituted by alkyl, substituted by at least one C 1 -C 12 Alkoxy-substituted phenyl, diphenylamino, substituted by at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl, substituted by at least one C 1 -C 12 Alkyl-substituted carbazolyl;
preferably, said R m H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl,
Methoxy, ethoxy, butoxy, hexyloxy, < >>
Cyclohexyl, adamantyl, phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl,
Preferably, said R m Is H, methyl,
Phenyl group,/->
Wherein the wavy line represents the attachment site of the group;
preferably, R is selected from H, F, -CN, C1-C6 alkyl substituted with at least one halogen, C1-C6 alkoxy, C6-C20 aryl substituted with at least one-CN, C6-C20 aryl substituted with 5-to 18-membered heteroaryl, or C5-C20 heteroaryl;
Preferably, R is selected from H, F, CN, methyl, trifluoromethyl, methoxy, phenyl, pyridyl, biphenyl, terphenyl, cyano-substituted phenyl, diphenyltriazinyl,
Preferably, R 1 、R 2 、R 3 And R is 4 Is independently H, F, CN, methyl, trifluoromethyl, methoxy, phenylPyridyl, biphenyl, terphenyl, cyano-substituted phenyl, diphenyltriazinyl,
Preferably, R 5 And R is 6 Independently H, F, CN, methyl, trifluoromethyl, methoxy, phenyl, pyridyl, biphenyl, terphenyl, cyano-substituted phenyl, diphenyltriazinyl,
4. A boron nitride compound according to any one of claims 1 to 3, wherein the boron nitride compound is any one of the following compounds:
5. an organic electroluminescent composition, characterized in that it comprises the boron nitride compound according to any one of claims 1 to 4 and a host material as doping materials;
preferably, the host material is a material having an electron transport ability and/or a hole transport ability and having a triplet excited state energy higher than or equal to that of the dopant material;
preferably, the host material in the organic electroluminescent composition is a carbazole derivative and/or carboline derivative represented by formulae (H-1) to (H-6):
Wherein X is 1 、Y 1 And Z 1 Is CH or N, and X 1 、Y 1 And Z 1 At most one of them is N;
wherein R is 1H And R is 2H Independently any of the following groups:
wherein X is 1 、Y 1 And Z 1 Is CH or N, and X 1 、Y 1 And Z 1 At most one of them is N;
wherein R is aH And R is bH H, C independently 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 6 -C 20 Aryl, C 1 -C 20 Alkyl substituted C 6 -C 20 Aryl or C 1 -C 20 Alkoxy substituted C 6 -C 20 An aryl group;
preferably, the organic electroluminescent composition preferably contains 0.3 to 30.0wt% of the boron-nitrogen compound as defined in any one of claims 1 to 4 as a doping material, and the remaining 99.7 to 70.0wt% of the host material composed of 1 to 2 compounds of formulae (H-1) to (H-6).
Preferably, the host material contains 2 compounds of formulae (H-1) to (H-6) in a weight ratio of 1:5 to 5:1;
preferably, the host material in the organic electroluminescent composition is 1-2 of the compounds H1-1 to H1-427;
preferably, the organic electroluminescent composition comprises 0.3-30.0wt% of the boron-nitrogen compound according to any one of claims 1-4, and the remaining 99.7-70.0wt% of the boron-nitrogen compound is 1-2 compounds from compounds H1-1 to H1-427.
Preferably, the organic electroluminescent composition contains 2 compounds in the formulas H1-1 to H1-427 as a main material, wherein the weight ratio of the two compounds is 1:5 to 5:1;
6. The organic electroluminescent composition according to claim 5, wherein the doping material in the organic electroluminescent composition is any one of boron-nitrogen compounds having a structure represented by formula I or formula II; the main material is composed of any one of compounds shown as the formula Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A and any one of compounds shown as the formulas H-1 to H-6;
wherein R is 1a 、R 1b 、R 2a 、R 2b 、R 3a And R is 3b Wherein 1 or 2 are independently R Tz The remainder being the same or different and independently hydrogen, deuterium, C 1 -C 8 Alkyl, C 1 -C 8 Alkoxy, C 6 -C 18 Aryl, C 1 -C 8 Alkyl substituted C 6 -C 18 Aryl or C 1 -C 8 Alkoxy substituted C 6 -C 18 Aryl of (a); r is R Tz Is any one of substituent groups shown in the following formula:
wherein asterisks represent the attachment site of the group;
preferably, the weight ratio of the Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A compound to the H-1, H-2, H-3, H-4, H-5 or H-6 compound in the main material is 1:5-5:1;
7. the organic electroluminescent composition as claimed in claim 5 or 6, wherein the doping material in the organic electroluminescent composition is any one of the boron-nitrogen compounds as claimed in any one of claims 1 to 4; the main material is composed of any one of compounds shown as formulas TRZ-1 to TRZ-76 and any one of carbazole or carboline derivatives shown as formulas H1-1 to H1-427;
Preferably, the weight ratio between the compound represented by the formulas TRZ-1 to TRZ-76 and the carbazole or carboline derivative in the host material is 1:5 to 5:1.
8. An organic electroluminescent material, characterized in that it comprises a boron nitrogen compound according to any one of claims 1 to 4 or an organic electroluminescent composition according to any one of claims 5 to 7.
9. An organic electroluminescent device comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising a light emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron injection layer, wherein at least one of the light emitting layer, the electron injection layer, the electron transport layer, the hole injection layer comprises the boron-nitrogen compound of any one of claims 1-4 or the organic electroluminescent composition of any one of claims 5-7;
preferably, the light-emitting layer comprises the boron nitrogen compound according to any one of claims 1 to 4 or the organic electroluminescent composition according to any one of claims 5 to 7;
Preferably, the organic electroluminescent device further comprises an optional hole blocking layer, an optional electron blocking layer and an optional capping layer.
10. Use of an organic electroluminescent device according to claim 9 in an organic electroluminescent display or an organic electroluminescent illumination source.
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