CN116082372A - Boron-nitrogen compound and preparation method and application thereof - Google Patents
Boron-nitrogen compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN116082372A CN116082372A CN202111273572.3A CN202111273572A CN116082372A CN 116082372 A CN116082372 A CN 116082372A CN 202111273572 A CN202111273572 A CN 202111273572A CN 116082372 A CN116082372 A CN 116082372A
- Authority
- CN
- China
- Prior art keywords
- substituted
- alkyl
- aryl
- alkoxy
- organic electroluminescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229910017464 nitrogen compound Inorganic materials 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 91
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 45
- -1 boron nitride compound Chemical class 0.000 claims description 43
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000006617 triphenylamine group Chemical group 0.000 claims description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 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 14
- 102100039856 Histone H1.1 Human genes 0.000 claims description 14
- 101001035402 Homo sapiens Histone H1.1 Proteins 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052582 BN Inorganic materials 0.000 claims description 11
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000012153 distilled water Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 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
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 150000001716 carbazoles Chemical class 0.000 claims description 4
- 229940125904 compound 1 Drugs 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 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
- 125000002496 methyl group Chemical group [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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- 230000035484 reaction time Effects 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
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000004641 (C1-C12) haloalkyl 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- 230000005281 excited state Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 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 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
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract description 16
- 239000010410 layer Substances 0.000 description 92
- 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
- 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
- 238000004440 column chromatography Methods 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
- 230000000694 effects Effects 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000002346 layers by function Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 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
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KTYAQHYBYRVCGD-UHFFFAOYSA-N [Ir].COC1=CC=CCCCC1 Chemical class [Ir].COC1=CC=CCCCC1 KTYAQHYBYRVCGD-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- KARUMYWDGQTPFL-UHFFFAOYSA-N 1,3-dibromo-5-iodobenzene Chemical compound BrC1=CC(Br)=CC(I)=C1 KARUMYWDGQTPFL-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 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 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FXORZKOZOQWVMQ-UHFFFAOYSA-L dichloropalladium;triphenylphosphane Chemical compound Cl[Pd]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FXORZKOZOQWVMQ-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- 229910052697 platinum Inorganic materials 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
- 230000002285 radioactive effect 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
- 238000010189 synthetic method Methods 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
- 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 230000004382 visual function Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a boron nitrogen compound, a preparation method and application thereof, wherein the boron nitrogen compound is a binuclear boron nitrogen derivative containing carbazole skeletons and has a narrow spectrum, the effective red shift of BN derivative spectra is realized by constructing a binuclear strategy, and the binuclear boron nitrogen compound containing carbazole skeletons is used 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.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to a boron-nitrogen compound and a preparation method 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 by Bernanose et al in 1953 (see Papkovski D.B.sens. Ankarato 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 obtains brightness of up to 1000cd/m under 10V driving voltage 2 Is 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 single layer devices with high luminous efficiency (see burrouges j.h., bradley D.D.C., brownA.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, the phosphorescent material is generally made of noble metals such as iridium and platinum, and is expensive, and on the other hand, the phosphorescent material still has chemical instability, and the device has the problems of large efficiency roll-off under high current density, 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 The requirement is that.
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, a preparation method and application thereof, wherein the boron nitrogen compound is a binuclear boron nitrogen derivative containing carbazole skeletons, has a narrow spectrum, aims at solving the defects of TADF luminescent molecules, and realizes the effective red shift of BN derivative spectra by constructing a binuclear strategy.
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 formula I:
wherein R is m1 And R is m2 Each occurrence is independently H, D (deuterium), fluorine, 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, or 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, 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, or 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, 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, or substituted with one or more R c Substituted diAnilino, triphenylamino, or substituted with one or more R c Substituted triphenylamine groups;
R c 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, 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, or 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 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 m1 And R is m2 Each occurrence is independently 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 aromaticA radical, a diphenylamino radical, and at least one C 1 -C 12 Alkyl-substituted diphenylamino, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, triphenylamine, substituted with at least one C 1 -C 12 An alkyl-substituted triphenylamine group, substituted with 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 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with at least one C 1 -C 12 Alkyl-substituted carbazolyl.
In one embodiment, the R m1 And R is m2 Each occurrence is independently H, D (deuterium), fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-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 position of attachment of the groupAnd (5) a dot.
In one embodiment of the present invention, the boron nitrogen compound is any one of the following compounds:
in another aspect, the present invention provides a method for preparing a boron nitrogen compound as described above, comprising the steps of:
the compound 1c reacts in toluene under the protection of nitrogen in the presence of catalyst iodobenzene and bis-triphenylphosphine palladium dichloride under the weak alkaline condition to obtain the boron-nitrogen compound shown in the formula I, wherein the reaction formula is as follows:
In the preparation method of the boron nitrogen compound, the addition of the catalyst iodobenzene has great influence on the reaction effect, and the yield of the same reaction is only 12-15% if the catalyst iodobenzene is not added. The use of the catalyst iodobenzene can ensure that the synthesis yield of the compound related to the invention is obviously improved.
Preferably, the amount of the material of the catalyst iodobenzene is 2% -20% of the amount of the material of the compound 1 c;
preferably, the amount of the substance of the ditriphenylphosphine palladium dichloride is 5% -25% of the amount of the substance of the compound 1 c;
preferably, the weakly alkaline condition is a weakly alkaline environment in the presence of potassium carbonate;
preferably, the ratio of the amounts of the substances of the compound 1c to potassium carbonate is 1:1-2;
preferably, the potassium carbonate is provided by an aqueous potassium carbonate solution, the concentration of which is 1-3mol/L;
preferably, distilled water is added in the reaction, and the volume ratio of the distilled water to toluene is 1:1-4;
preferably, the reaction is carried out in a reflux state, the reaction time being 8-48 hours.
The compound 1c used in the present invention can be prepared according to a chemical synthesis method conventional in the art, and the procedure and conditions thereof can be referred to those of similar reactions in the art.
For example, the basic process route for the synthesis of compound 1c according to the present invention is as follows:
wherein:
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 present invention, the boron nitride compound having the structure represented by the formula (I) 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 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. 1, wherein 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) 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.
The invention provides an organic electroluminescent composition, which comprises boron nitride compound with the structure shown in the formula I 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.
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 shown in formula I 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 of the invention, 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 one embodiment of the present invention, the organic electroluminescent composition comprises 0.3-30.0wt% (wt%) of boron-nitrogen compound having the structure shown in formula I as described above, and the rest 99.7-70.0wt% of the composition is 1-2 compounds 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 invention, the doping material in the organic electroluminescent composition is any one of boron-nitrogen compounds with a structure shown in a formula I (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 boron-nitrogen compounds (the content is 0.3 wt% to 30.0 wt%) with the structure shown in the formula I; the main material (the content is 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.
The invention provides an application of the organic electroluminescent composition as an organic electroluminescent material.
In one embodiment of the invention, the organic electroluminescent composition is used for preparing a light-emitting layer in an organic electroluminescent device.
The present invention also provides an organic electroluminescent device comprising an anode, a light emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron injection layer, and a cathode, 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 a preferred embodiment, the light-emitting layer of the organic electroluminescent device comprises an organic electroluminescent composition as described above.
In one embodiment of the present invention, the organic electroluminescent composition is used as a material of a light emitting layer of an organic electroluminescent device, and the light emitting principle of the light emitting layer is based on energy transfer from a host material to any boron-nitrogen compound shown in formula I or carrier capture of the light emitting material itself.
In one embodiment of the present invention, the organic electroluminescent composition is used as a material of a light emitting layer of an organic electroluminescent device; 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 contains 0.3 to 30.0wt% of the boron nitrogen compound having the structure shown in formula I 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). For example, when the host material contains 2 compounds of formulae (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), 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 present invention, the organic electroluminescent composition is used as a material of a light emitting layer of an organic electroluminescent device; the doping material in the organic electroluminescent composition is boron-nitrogen compound (the content is 0.3 wt% to 30.0 wt%) with the structure shown in the formula I; 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 present invention, the organic electroluminescent composition is used as a material of a light emitting layer of an organic electroluminescent device; the doping material in the organic electroluminescent composition is boron-nitrogen compound (the content is 0.3 wt% to 30.0 wt%) with the structure shown in the formula I; 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 present invention, the organic electroluminescent composition is used as a material of a light emitting layer of an organic electroluminescent device; the doping material in the organic electroluminescent composition is any compound shown in the formula I (the content is 0.3-30.0 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 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 a combination of at least two 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.
The invention provides an application of the organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent illumination source.
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. All other embodiments, which can be made by a person skilled in the art without creative efforts, based on the described embodiments of the present invention fall within the protection scope of the present invention.
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, whether radioactive or not, 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 disclosure, the "substituted" position may be any position unless otherwise specified.
In the present invention, as part of a group or other group (e.g., alkyl substituted with halogenIn the group, etc.), 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 disclosure, 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 It is meant that the number of carbon atoms of the radical may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, C 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 is a schematic structural diagram of an electroluminescent device according to the present invention, wherein 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.
FIG. 2 shows the result of the reaction of Compound BN7 in toluene (concentration: 1X 10) -5 M) photoluminescence spectrum in the sample.
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.
The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
Molecular Mass spectrum data (Mass Spectra: MS) with a relative molecular weight below 1000 were measured by ITQ1100 ion trap gas chromatograph-Mass spectrometer (ITQ) from Thermo Fisher, and molecular Mass spectrum data with a relative molecular weight above 1000 were measured by Autoflex Speed matrix assisted laser desorption time-of-flight Mass spectrometer (Bruker). 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.
The synthesis of the compounds of formula I, except for the substrates 2-bromo-1, 3-difluorobenzene and 1, 3-dibromo-5-iodobenzene, the following raw materials were used:
wherein the reference is made to C n H 2n+1 The radicals indicated are all linear alkyl radicals, e.g. C 4 H 9 Represents n-butyl.
Synthetic examples
The specific preparation method of the compound comprises the following steps:
in the first step, 35.2mmol of carbazole derivative C-1 to C-100), 10.24g of cesium carbonate (52.8 mmol), 3.26g of 2-bromo-1, 3-difluorobenzene (17.0 mmol) were added to a 250ml two-neck round bottom flask, to which 80ml of anhydrous DMF solution was added. 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 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. After slowly heating to 60℃and stirring for 2 hours, cooling to-30℃and adding 2.4mL of boron tribromide (6.3 mmol), the reaction mixture was stirred at room temperature for 1 hour. Then 15.6mLN, N-diisopropylethylamine (91.1 mmol) was added at 0deg.C, and the reaction mixture was cooled to room temperature after stirring continued for 5 hours at 130deg.C. To the reaction mixture was added 5ml of methanol to quench the residual B Br 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 1 (6 mmol), catalyst iodobenzene (0.6 mmol), potassium carbonate (15 mmol) was added to toluene (35 ml), 8ml distilled water was further added, bubbling with nitrogen for 5 min, and 126.18mg bis triphenylphosphine palladium dichloride (0.18 mmol) was added under high nitrogen flow, the mixture was heated to reflux and stirred for 24 hours, after the system cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography to give final product BNn (n=1-100), the reaction yield in this step was between 26-37%. The data obtained for the target compounds are shown in Table 1.
Experimental details of the synthetic examples are illustrated by compound BN 7:
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%)
In the second step, 19.4mL of a solution of t-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) under nitrogen atmosphere. Slowly heating to 60 ℃, stirring for 2 hours, removing normal hexane in vacuum, and then cooling to2.4mL of boron tribromide (6.3 mmol) was added at-30℃and the reaction mixture was stirred at room temperature for 1 hour. Then 15.6mLN, N-diisopropylethylamine (91.1 mmol) was added at 0deg.C, and the reaction mixture was cooled to room temperature after stirring continued for 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 step, 4.5g of intermediate 1c (6 mmol), catalyst iodobenzene (0.6 mmol), 2.0g of potassium carbonate (15 mmol) were added to toluene (35 ml), and 8ml of distilled water was further added, bubbled with nitrogen for 5 minutes, and 126.18mg of ditriphenylphosphine palladium dichloride (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 1.33g of the final product BN7 (yield 35%).
Other compounds were prepared according to the synthetic methods described above, using the raw materials specifically, and elemental analysis (C, H and N% in the compounds), mass spectrometry molecular weight, and synthetic reaction yield data shown in table 1.
TABLE 1
Electroluminescent device embodiment
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 A100
In the organic electroluminescent device (structure shown in FIG. 1) in device examples A1 to A100, 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. Device 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 example data listed in table 2 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 24%.
And wherein the compound BN7 is present in a toluene solution (concentration: 1X 10 -5 The photoluminescence spectrum (i.e., fluorescence spectrum) in M) is shown in FIG. 2, and as can be seen from FIG. 2, the luminescence peak position is 501nm and the half-width is 35nm.
Device examples B1 to B100
In the organic electroluminescent device of device examples B1 to B100, the structure was as shown in FIG. 1, 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 was used as a host material in a light emitting layer (the weight mixing ratio of H1-33 and TRZ-1 was 1:1), BNn was used as a doped light emitting material (the 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 effect 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%.
The applicant states that the boron nitrogen compounds of the present invention, and their preparation methods and applications, are illustrated by the above examples, 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 has a structure represented by formula I:
wherein R is m1 And R is m2 Each occurrence is independently H, deuterium, fluorine, 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 Substitution of5-to 18-membered heteroaryl, diphenylamino, or substituted with one or more R a Substituted diphenylamino, triphenylamine, or substituted with one or more R a Substituted triphenylamine groups, carbazolyl groups, or substituted with one or more R a A substituted carbazolyl group;
R a 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, 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, or substituted with one or more R b Substituted diphenylamino, triphenylamine, or substituted with one or more R b Substituted triphenylamine groups, carbazolyl groups, or substituted with one or more R b A substituted carbazolyl group;
R b 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, 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, or substituted with one or more R c Substituted diphenylamino, triphenylamine, or substituted with one or more R c Substituted triphenylamine groups, carbazolyl groups, or substituted with one or more R c A substituted carbazolyl group;
R c 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, 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, or substituted with one or more R d Substituted diphenylamino, triphenylamine, or substituted with one or more R d Substituted triphenylamine groups, carbazolyl groups, or substituted with one or more R d A substituted carbazolyl group;
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 according to claim 1, wherein said R m1 And R is m2 Independently at each occurrence 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, triphenylamino, substituted with at least one C 1 -C 12 An alkyl-substituted triphenylamine group, substituted with at least one C 1 -C 12 Alkyl-substituted diphenylamino, carbazolyl or 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 NaphtheneA radical, 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, triphenylamine, and substituted with at least one C 1 -C 12 Alkyl-substituted triphenylamine groups, carbazolyl groups, substituted with 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, C 6 ～C 14 Aryl, at least one C 1 -C 12 Alkyl substituted C 6 ～C 14 Aryl, at least one C 1 -C 12 Alkoxy substituted C 6 ～C 14 Aryl groups.
3. The boron nitride compound according to claim 1 or 2, wherein R m1 And R is m2 Independently at each occurrence H, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-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,/->
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. The method for producing a boron nitrogen compound according to any one of claims 1 to 4, comprising the steps of:
the compound 1c reacts in toluene under the protection of nitrogen in the presence of catalyst iodobenzene and bis-triphenylphosphine palladium dichloride under the weak alkaline condition to obtain the boron-nitrogen compound shown in the formula I, wherein the reaction formula is as follows:
preferably, the amount of the material of the catalyst iodobenzene is 2% -20% of the amount of the material of the compound 1 c;
preferably, the amount of the substance of the ditriphenylphosphine palladium dichloride is 5% -25% of the amount of the substance of the compound 1 c;
preferably, the weakly alkaline condition is a weakly alkaline environment in the presence of potassium carbonate;
preferably, the ratio of the amounts of the substances of the compound 1c to potassium carbonate is 1:1-2;
preferably, the potassium carbonate is provided by an aqueous potassium carbonate solution, the concentration of which is 1-3mol/L;
preferably, distilled water is added in the reaction, and the volume ratio of the distilled water to toluene is 1:1-4;
preferably, the reaction is carried out in a reflux state, the reaction time being 8-48 hours.
6. 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.
7. The organic electroluminescent composition according to claim 6, wherein the host material 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 Aryl, asterisks represent the attachment site of the group;
preferably, the organic electroluminescent composition comprises 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 of the formulae H1-1 to H1-427 as host materials in a weight ratio of 1:5 to 5:1.
Preferably, the doping material in the organic electroluminescent composition is any one of the boron-nitrogen compounds as described in any one of claims 1 to 4; 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 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 boron-nitrogen compounds (the content is 0.3 wt% to 30.0 wt%) with the structure shown in the formula I; the main material (the content is 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.
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 the boron-nitrogen compound according to any one of claims 1 to 4 or the organic electroluminescent composition according to claim 6 or 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 claim 6 or 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 claim 6 or 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111273572.3A CN116082372A (en) | 2021-10-29 | 2021-10-29 | Boron-nitrogen compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111273572.3A CN116082372A (en) | 2021-10-29 | 2021-10-29 | Boron-nitrogen compound and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116082372A true CN116082372A (en) | 2023-05-09 |
Family
ID=86204966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111273572.3A Pending CN116082372A (en) | 2021-10-29 | 2021-10-29 | Boron-nitrogen compound and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116082372A (en) |
-
2021
- 2021-10-29 CN CN202111273572.3A patent/CN116082372A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI782115B (en) | Materials for organic electroluminescent devices | |
| CN106221691B (en) | Organic electroluminescent device containing aza-phenyl compounds and application thereof | |
| CN116120349B (en) | Boron-nitrogen compound and preparation method and application thereof | |
| CN107068880A (en) | A kind of organic electroluminescence device containing diaryl ketone compounds and its application | |
| CN111662190A (en) | Organic compound containing pyrene or aza-pyrene and application thereof | |
| CN116514859B (en) | Narrow-emission luminescent compound and application thereof in electronic device | |
| CN113004292A (en) | Main luminescent material based on triazolotriazine and application thereof | |
| CN114249759B (en) | Boron-doped Z-acene derivative and preparation method and application thereof | |
| CN116836193A (en) | Organic compound, application thereof and organic electroluminescent device comprising same | |
| CN110256439B (en) | Organic electroluminescent material and device | |
| CN116023402B (en) | Boron-nitrogen compound and preparation method and application thereof | |
| CN116120350B (en) | Boron-nitrogen compound and preparation method and application thereof | |
| CN116903648A (en) | Boron nitride compound and application thereof | |
| CN110183361B (en) | Construction and application of cross-shaped thermal activity delay fluorescent material | |
| CN110002946B (en) | Pyrenyl blue aggregation-induced luminescent material and preparation method and application thereof | |
| CN114478588B (en) | Organic compound based on pyrene and indolocarbazole, organic electroluminescent composition and organic electroluminescent device | |
| CN113861206B (en) | Blue electroluminescent material and synthesis method and application thereof | |
| CN114621272B (en) | Boron nitride compound, organic electroluminescent composition and organic electroluminescent device comprising same | |
| CN116082372A (en) | Boron-nitrogen compound and preparation method and application thereof | |
| CN116082375A (en) | Boron nitride compound and application thereof | |
| CN116082374A (en) | Boron nitride compound, composition containing boron nitride compound and application of boron nitride compound | |
| Tong et al. | Synthesis and electroluminescent properties of red emissive iridium (III) complexes with ester-substituted phenylquinoline ligands | |
| CN116082373A (en) | Boron nitride compound, composition containing boron nitride compound and application of boron nitride compound | |
| CN116925113A (en) | Boron nitrogen heterocyclic compound, composition containing same and application thereof | |
| CN116120351A (en) | Boron-nitrogen compound and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |