CN115521301A - Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device - Google Patents
Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device Download PDFInfo
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- CN115521301A CN115521301A CN202210168895.4A CN202210168895A CN115521301A CN 115521301 A CN115521301 A CN 115521301A CN 202210168895 A CN202210168895 A CN 202210168895A CN 115521301 A CN115521301 A CN 115521301A
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- unsubstituted
- nitrogen
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 154
- 239000010410 layer Substances 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 239000004305 biphenyl Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 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 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 51
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 56
- 239000000543 intermediate Substances 0.000 description 38
- 230000005525 hole transport Effects 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000003107 substituted aryl group Chemical group 0.000 description 7
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- NLBSIKDIYFCCQL-UHFFFAOYSA-N 7-bromo-2-phenyl-1,3-benzoxazole Chemical compound O1C=2C(Br)=CC=CC=2N=C1C1=CC=CC=C1 NLBSIKDIYFCCQL-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 2
- JOXBFDPBVQGJOJ-UHFFFAOYSA-N 2,5-dichloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(Cl)=NC2=C1 JOXBFDPBVQGJOJ-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-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
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940125900 compound 59 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 125000006606 n-butoxy group Chemical group 0.000 description 1
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- 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
- 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 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 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
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- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/1018—Heterocyclic compounds
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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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Abstract
The application relates to the field of organic electroluminescence, in particular to a nitrogen-containing compound, and an organic electroluminescent device and an electronic device comprising the same, wherein the nitrogen-containing compound has a structure shown in a formula 1. The application also provides an organic electroluminescent device and an electronic device containing the nitrogen-containing compound. When the nitrogen-containing compound is used as a main material of an organic light-emitting layer of an organic light-emitting device, the efficiency and the service life of the device can be improved, and the working voltage can be reduced.
Description
Technical Field
The present application relates to the field of organic electroluminescence, and in particular, to a nitrogen-containing compound, and an organic electroluminescent device and an electronic apparatus comprising the same.
Background
Organic electroluminescent materials (OLEDs), as a new generation display technology, have the advantages of being ultra-thin, self-luminescent, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, and the like, and have been widely used in the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display, and the like.
The organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is generally formed in a multi-layered structure composed of different materials to improve the luminance, efficiency and lifetime of the organic electroluminescent device, and may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the organic light emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected from an anode and a cathode into an organic material layer, respectively, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons return to a ground state. The most important problems of the conventional organic electroluminescent device are lifetime and efficiency, and as the driving voltage is increased with the increase of the area of the display, the luminous efficiency and the power efficiency are also increased, and a certain lifetime is ensured, therefore, the organic material must solve the efficiency or lifetime problems, and a new material for the organic electroluminescent device, which has high efficiency and long lifetime, and is suitable for mass production, needs to be continuously developed.
Disclosure of Invention
An object of the present application is to provide a nitrogen-containing compound which is used in an organic electroluminescent device and can improve the performance of the device, and an organic electroluminescent device and an electronic apparatus including the same.
In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound having a structure represented by the following formula 1:
wherein L is 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atomsGroup consisting of;
Ar 1 and Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
the ring A is selected from aryl with 6-12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;
L 1 、L 2 、L 3 、Ar 1 and Ar 2 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R 5 selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms;
optionally, in Ar 1 And Ar 2 Wherein two substituents attached to the same atom form a ring with the atom to which they are both attached;
n 1 represents R 1 Number of (2), n 1 Selected from 0, 1,2, 3 or 4, when n is 1 When greater than 1, any two R 1 The same or different;
n 2 represents R 2 Number of (2), n 2 Selected from 0, 1,2 or 3, when n is 2 When greater than 1, any two R 2 The same or different;
n 3 represents R 3 Number of (2), n 3 Selected from 0, 1,2 or 3, when n 3 When greater than 1, any two R 3 The same or different;
n 4 represents R 4 Number of (2), n 4 Selected from 0, 1,2, 3 or 4, when n is 4 When greater than 1, any two R 4 The same or different;
n 5 represents R 5 Number of (2), n 5 Is selected from 0, 1,2, 3,4, 5 or 6, when n is 5 When greater than 1, any two R 5 The same or different.
In a second aspect, the present application provides an organic electroluminescent device comprising a cathode and an anode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the nitrogen-containing compound of the first aspect.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
Through the technical scheme, the nitrogen-containing compound combines benzoxazolyl/naphthoxazole with electronic property and biscarbazole with hole property, and aromatic groups are connected to five-membered rings of the benzoxazolyl/naphthoxazole, so that the combined connection enables molecules to have unique twisted configuration, the crystallinity of the material is reduced, the film-forming property of the material is better, and the service life of the material is prolonged. The compound has a higher T1 energy level, can remarkably improve the electron injection property of the material, and further improves the exciton recombination efficiency, thereby improving the luminous efficiency of the organic electroluminescent device. When the material is used as the main material of the organic light-emitting layer of the organic light-emitting device, the efficiency and the service life of the device can be improved, and the working voltage can be reduced; the nitrogen-containing compounds of the present application are suitable for use as organic light emitting layer materials for OLED devices.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. Anode 200, cathode 300, functional layer 310, hole injection layer
320. Hole transport layer 321, first hole transport layer 322, second hole transport layer 330, organic light emitting layer
340. Electron transport layer 350, electron injection layer 400, and electronic device
Detailed Description
The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are given by way of illustration and explanation only, not limitation.
A first aspect of the present application provides a nitrogen-containing compound having a structure represented by the following formula 1:
wherein L is 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
the ring A is selected from aryl with 6-12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;
L 1 、L 2 、L 3 、Ar 1 and Ar 2 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R 5 selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms;
optionally, in Ar 1 And Ar 2 Wherein two substituents attached to the same atom form a ring with the atom to which they are both attached;
n 1 represents R 1 Number of (2), n 1 Selected from 0, 1,2, 3 or 4, when n is 1 When greater than 1, any two R 1 The same or different;
n 2 represents R 2 Number of (2), n 2 Selected from 0, 1,2 or 3, when n is 2 When greater than 1, any two R 2 The same or different;
n 3 represents R 3 Number of (2), n 3 Selected from 0, 1,2 or 3 when n is 3 When greater than 1, any two R 3 The same or different;
n 4 represents R 4 Number of (2), n 4 Selected from 0, 1,2, 3 or 4, when n is 4 When greater than 1, any two R 4 The same or different;
n 5 represents R 5 Number of (2), n 5 Is selected from 0, 1,2, 3,4, 5 or 6, when n is 5 When greater than 1, any two R 5 The same or different.
In the present application, the ring refers to a saturated or unsaturated ring such as cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, phenanthrene ring, fluorene ring, etc., but is not limited thereto.
In this application, the terms "optionally" or "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not occur. For example, "optionally, at Ar 1 And Ar 2 In (1), two substituents attached to the same atom form a ring with the atom to which they are attached together "means that in Ar 1 And Ar 2 In (1), two substituents attached to the same atom and the atom to which they are attached together may form a ring but need not form a ring, and a case of forming a ring and a case of not forming a ring are illustrated.
In the present application, the description "… … is independently" … … is independently "and" … … is independently selected "should be used interchangeably to be understood broadly, which means that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same group do not affect each other.
For example,') "
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents a structure having Q substituents R ' on the benzene ring, each R ' may be the same or different, and each R ' represents a substituentThe options of the R' are not affected mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc, which is the substituent, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a phosphono group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a triarylsilyl group having 18 to 24 carbon atoms. In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the number of carbon atoms in the functional group and the substituents thereon. For example, if Ar 2 Selected from substituted aryl with 30 carbon atoms, all the carbon atoms of the aryl and the substituent groups on the aryl are 30; as another example, if L 1 And is selected from substituted arylene having 18 carbon atoms, all of the carbon atoms of the arylene and the substituents thereon are 18 carbon atoms.
In the present application, the number of carbon atoms refers to all the number of carbon atoms. For example: l is 1 Is a substituted arylene group having 12 carbon atoms,all the carbon atoms of the arylene group and the substituents therein are 12. For example: ar (Ar) 1 Is composed of
The number of carbon atoms is 7; l is 2 Is composed of
The number of carbon atoms is 12. In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring.
In the present application, an aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, an aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups and fused-ring aryl groups joined by carbon-carbon bond conjugation, two or more fused-ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. In the present application, examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, spirobifluorenyl, indenyl, anthracenyl, phenanthryl, biphenylyl, terphenylyl, quaterphenylyl, pentabiphenylyl, benzo [9,10]Phenanthryl, pyrenyl, fluoranthenyl, benzofluoranthenyl,
Perylene groups, and the like. In the present application, the substituted aryl group may be an aryl group in which one or two or more hydrogen atoms are substituted with a group such as a deuterium atom, a halogen group, a cyano group (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, or the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms of the aryl group and the substituents thereon of 18.
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be 6 (phenyl), 10 (naphthyl), 12 (biphenyl, for example), 14, 15 (dimethylfluorenyl), 16, 18, 20, 24, 25, or the like.
In the present application, the number of carbon atoms of the substituted or unsubstituted arylene group having 6 to 30 carbon atoms is, for example, 6, 12, 18, 24, 30 or the like.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, the fluorenyl group may be substituted and two substituents may be combined with each other to form a spiro structure, specific examples including, but not limited to, the following structures:
specific examples of aryl groups as substituents in the present application include, but are not limited to: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, and the like.
In the present application, "arylene" refers to a group formed by an aryl group further deprived of a hydrogen atom. In the present application, an arylene group includes a group formed by further losing one or two or more hydrogen atoms to an aryl group.
In the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, 6, or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se, and S, or derivatives thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silicon, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. It is understood that a "heteroaryl" group may have one, two, or more bonds to the rest of the molecule.
In the present application, a heteroarylene group refers to a group formed by a heteroaryl group further deprived of a hydrogen atom. In the present application, a heteroarylene group is a group formed by a heteroaryl group further lacking one or two or more hydrogen atoms. In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms in a substituted heteroaryl refers to the total number of carbon atoms in the heteroaryl and the substituent on the heteroaryl.
Specific examples of heteroaryl groups as substituents in the present application include, but are not limited to: pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, furanyl, thienyl, pyrimidinyl, and the like.
In the present application, the halogen group may be fluorine, chlorine, bromine, iodine.
In the present application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. Pyridyl is 6-membered heteroaryl.
For connecting keys in this application
And (4) showing.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the dibenzofuranyl group represented by formula (X '-1) to formula (X' -4) includes any of the possible attachment means shown in formulas (X '-1) to (X' -4).
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms may be 3,4, 5, 8, 9, 12, 15, 18, 24, or the like.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms is, for example, 3,4, 5, 8, 9, 12, 15, 18, 24, or the like.
Specific examples of heteroaryl groups as substituents in the present application include, but are not limited to: phenanthroline, furyl, thienyl, pyridyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, and the like.
In the present application, specific examples of triarylsilyl groups having 18 to 24 carbon atoms include, but are not limited to, triphenylsilyl groups.
In the present application, "alkyl" refers to a saturated straight or branched chain monovalent hydrocarbon radical, wherein the alkyl radical may be optionally substituted with one or more substituents described herein. Specifically, the alkyl group having 1 to 10 carbon atoms may be a straight-chain alkyl group having 1 to 10 carbon atoms or a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 2-methylpentyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl, tert-octyl, n-nonyl, decyl, and the like. Examples of alkyl groups of 1 to 5 carbon atoms in the present application include, but are not limited to: methyl (Me, -CH) 3 ) Ethyl (Et, -CH) 2 CH 3 ) N-propyl (n-Pr, -CH) 2 CH 2 CH 3 ) Isopropyl group (i-Pr, -CH (CH) 3 ) 2 ) N-butyl (n-Bu, -CH) 2 CH 2 CH 2 CH), tert-butyl (t-Bu, -C (CH) 3 ) 3 ) And the like.
In this application, "alkoxy" means an alkyl group attached to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein. Unless otherwise specified, the alkanesThe number of carbon atoms of the oxy group may be 1,2, 3,4, 5, 6, 7, 8, 9,10, and examples of alkoxy groups include, but are not limited to, methoxy (MeO, -OCH) 3 ) Ethoxy (EtO, -OCH) 2 CH 3 ) 1-propoxy (n-PrO, n-propoxy, -OCH) 2 CH 2 CH 3 ) 2-propoxy (i-PrO, i-propoxy, -OCH (CH) 3 ) 2 ) 1-butoxy (n-BuO, n-butoxy, -OCH) 2 CH 2 CH 2 CH 3), 2-methyl-l-propoxy (i-BuO, i-butoxy, -OCH 2 CH(CH 3 ) 2 ) 2-butoxy (s-BuO, s-butoxy, -OCH (CH) 3 )CH 2 CH 3 ) 2-methyl-2-propoxy (t-BuO, t-butoxy, -OC (CH) 3 ) 3 ) And so on.
In the present application, the haloalkyl group having 1 to 10 carbon atoms may be a chain-, cyclic-or branched-chain haloalkyl group. The number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, including but not limited to trifluoromethyl, and the like.
In the present application, cycloalkyl groups may have 3-10 carbon atoms, and numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "3 to 10 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Cycloalkyl groups in some embodiments are 5 to 10 membered cycloalkyl groups, for example, cycloalkyl groups may be exemplified by, but not limited to: cyclopentyl, cyclohexyl, adamantyl, and the like.
In some embodiments of the present application, ring a is a phenyl ring or a naphthyl ring.
In a further embodiment of the method according to the invention,
selected from the group consisting of:
wherein is represented by
The radicals being used in combination with in formula 1
A bond to which the group is attached;
is shown in
The radicals being used in combination with in formula 1
The bond to which the group is attached.
In some embodiments of the present application, L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.
For example, L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms.
Alternatively, L 1 、L 2 And L 3 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
In some embodiments of the present application, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted group Q, the unsubstituted group Q being selected from the group consisting of:
the substituted group Q has one or more substituents, the substituents in the substituted group Q are each independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, and tert-butyl, and when the number of substituents on the group Q is greater than 1, each substituent is the same or different.
In some embodiments of the present application, L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
In particular, L 1 、L 2 And L 3 Wherein the substituents are independently selected from the group consisting of deuterium, fluoro, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In some embodiments of the present application, L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond or the following groups:
in some embodiments of the present application, ar 1 And Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms. For example, ar 1 And Ar 2 Each independently selected from the group consisting of 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atomsSubstituted or unsubstituted aryl, substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Alternatively, ar 1 And Ar 2 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;
optionally, in Ar 1 And Ar 2 Wherein two substituents attached to the same atom form a 5-13 membered ring with the atom to which they are both attached. For example, in Ar 1 In which two substituents attached to the same atom form a cyclopentane with the atom to which they are both attached
Cyclohexane
Or a fluorene ring
In some embodiments of the present application, ar 1 And Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
the substituted group W has one or more substituents independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, naphthyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.
In some embodiments of the present application, ar 1 And Ar 2 Each independently selected from substituted or unsubstituted benzeneA phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, and a substituted or unsubstituted triphenylene group.
Specifically, ar 1 And Ar 2 Wherein the substituents are independently selected from the group consisting of deuterium, fluoro, cyano, phenyl, naphthyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and biphenyl;
optionally, at Ar 1 And Ar 2 In which two substituents attached to the same atom form a cyclopentane with the atom to which they are both attached
Cyclohexane
Or a fluorene ring
In some embodiments of the present application, ar 1 And Ar 2 Each independently selected from the group consisting of:
in some embodiments of the present application, R 1 、R 2 、R 3 And R 4 Each independently selected from deuterium, halogen group, cyano group, C1-5 alkyl group, C3-6 alkyl groupA substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms;
in particular, R 1 、R 2 、R 3 And R 4 Wherein the substituents are each independently selected from the group consisting of deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, R 1 、R 2 、R 3 And R 4 Each independently selected from the group consisting of deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, cyclohexyl, dibenzofuranyl, cyclopentyl, and pyridyl.
In some embodiments of the present application, R 1 、R 2 、R 3 And R 4 Each independently selected from the group consisting of:
in some embodiments of the present application, n 5 Is 0.
In some embodiments of the present application, n 1 、n 2 、n 3 、n 4 Are all 0.
In some embodiments of the present application, the nitrogen-containing compound is selected from the group consisting of:
the synthesis method of the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the organic compound of the present invention in combination with the preparation methods provided in the preparation examples section. All organic compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the organic compounds will not be described in detail herein, and those skilled in the art should not be construed as limiting the present application.
In a second aspect, there is provided an organic electroluminescent device comprising a cathode and an anode, and a functional layer disposed between the cathode and the anode, the functional layer comprising a nitrogen-containing compound as described in the first aspect of the present application.
For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains a nitrogen-containing compound as provided in the first aspect of the present application.
According to some embodiments, the organic electroluminescent device may be, for example, a green organic electroluminescent device.
In one embodiment of the present application, the functional layer includes an organic light emitting layer including the nitrogen-containing compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The nitrogen-containing compound provided by the application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device, can effectively improve the light-emitting efficiency and the service life of the organic electroluminescent device, and can reduce the driving voltage of the organic electroluminescent device. The hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer 321 is closer to the anode than the second hole transport layer 322.
In one embodiment, anode 100 comprises an anode material, preferably a material having a large work function that facilitates hole injection into the functional layer. The anode material specifically includes: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides such as ZnO: al and SnO 2 : sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene](PEDT), polypyrrole and polyaniline, but are not limited thereto. Also, indium Tin Oxide (ITO) is preferably included as a transparent electrode of the anode.
In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. Specifically, the first hole transporting layer 321 is composed of the compound HT-1.
In one embodiment, the second hole transport layer 322 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers or other types of compounds, which are not specifically limited in this application. In one embodiment, the second hole transport layer 322 is comprised of the compound HT-19.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 may specifically be selected from one or a combination of any two or more of compounds shown below:
in the present application, the organic light emitting layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be recombined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. For example: specific examples of green host materials include but are not limited to,
specifically, the host material of the organic light emitting layer 330 is the nitrogen-containing compound of the present application, and may be composed of the nitrogen-containing compound of the present application and other compounds. In one embodiment of the present application, the host material of the organic light emitting layer includes the nitrogen-containing compound of the present application and H37.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. Specific examples of guest materials for the organic light-emitting layer include, but are not limited to,
In a specific embodiment, the cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. Specifically, specific examples of the cathode material include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; multilayer materials such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is used as the cathode.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:
for example, in some embodiments of the present application, electron transport layer 340 may be comprised of ET-01 and LiQ.
In the present application, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example: the hole injection layer 310 may specifically include, but is not limited to, the following compounds:
in some embodiments of the present application, the hole injection layer 310 may be composed of HAT-CN.
In a specific embodiment, optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 includes the organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The method for synthesizing the nitrogen-containing compound of the present application will be specifically described below with reference to the synthesis examples, but the present application is not limited thereto.
Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
Synthesis of Compound 4
3-bromocarbazole (50.0g, 203.1mmol), 4-iodobiphenyl (58.0g, 207.2mmol), cuprous iodide (CuI) (7.7g, 40.6mmol) and potassium carbonate K 2 CO 3 (61.7g, 446.9mmol) and 18-crown-6 (5.4g, 20.3mmol) are added into a three-neck flask, and dried DMF (500 mL) solvent is added, the temperature is raised to 150 ℃ under the protection of nitrogen, and the mixture is kept at the temperature and stirred for 18 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave the product sub I-A1 as intermediate (42.8g, 53%) as a white solid.
Adding an intermediate sub I-A1 (30.0g, 75.3mmol) into a round-bottom flask, adding 300mL of THF into the flask after removing water, cooling the system to-80 ℃ to-90 ℃ by using liquid nitrogen, starting dropwise adding n-butyllithium (5.3g, 82.8mmol), and preserving heat for 1h after dropwise adding. Dropwise adding trimethyl borate (9.4g, 90.4mmol), keeping the temperature between minus 80 ℃ and minus 90 ℃, after finishing dripping, keeping the temperature for 1h, naturally heating to room temperature, after the reaction is finished, adding HCl aqueous solution, and stirring for 0.5h. Adding dichloromethane and water, extracting, washing organic phase to neutral pH =7, mixing organic phases, and using anhydrous MgSO as organic phase 4 After drying for 10min, filtration, spin-drying of the filtrate and slurrying with n-heptane 2 times gave the intermediate sub A-1 as a white solid (15.0g, 55%).
3-bromocarbazole (50.0g, 203.1mmol), 7-bromo-2-phenylbenzoxazole (61.2g, 223.4mmol) and Pd 2 (dba) 3 (1.8g, 2.0mmol), tri-tert-butylphosphine (0.8g, 4.1mmol), sodium tert-butoxide (39.0g, 406.3mmol) and xylene (500 mL) were charged in a three-necked flask, and the temperature was raised to 130 ℃ under the protection of nitrogen, and the mixture was heated back toThe stream was stirred for 7h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give a solid compound, sub B-1 (49.9g, 56%)
Intermediate sub A-1 (8.4 g, 23.2mmol), intermediate sub B-1 (10.0g, 22.7mmol), tetrakis (triphenylphosphine) palladium (0.3g, 0.2mmol), potassium carbonate (6.3g, 45.5mmol) and tetrabutylammonium bromide (0.07g, 0.2mmol) were charged into a three-necked flask, and toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to the three-necked flask, heated to 76 ℃ under nitrogen, and stirred under reflux for 18 hours. Cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase gave compound 4 as a white product (9.4 g, 61%). Mass spectrum: m/z =678.21 (M + H) + 。
Preparation of intermediate sub I-AX and intermediate sub A-X
Intermediates sub I-AX and intermediates sub a-X shown in table 1 below were synthesized in a similar manner to the preparation of intermediates sub I-A1 and sub a-1, except that the following raw material 1 was used instead of the raw material 3-bromocarbazole in preparation example 1, and the raw material 2 was used instead of 4-iodobiphenyl. The structures of feed 1 and feed 2, as well as the structures and yields of the intermediates, are listed in table 1.
TABLE 1
Preparation of intermediate sub B-X
Intermediates sub B-X shown in the following table were synthesized in a similar manner to the preparation of intermediate sub B-1, except that starting material 1 was used instead of 3-bromocarbazole and starting material 3 was used instead of 7-bromo-2-phenylbenzoxazole, and the structures of starting materials 1 and 3 and the structures and yields of intermediates sub B-X are shown in table 2.
TABLE 2
Preparation of intermediate sub B-6
7-bromo-2-phenylbenzoxazole (35.0g, 128.6 mmol), p-chlorobenzeneboronic acid (20.5g, 131.1mmol), tetrakis (triphenylphosphine) palladium (2.9g, 2.5mmol), potassium carbonate (35.5g, 25.7mmol), tetrabutylammonium bromide (0.4g, 1.3mmol), toluene (280 mL), ethanol (70 mL) and deionized water (70 mL) were added to a three-necked flask, warmed to 76 ℃ under nitrogen protection, and stirred under reflux for 16h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by using anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography to obtain sub 1-I-B1 (27.5g, 70%) as a solid compound.
3-bromocarbazole (40.0g, 162.5mmol), sub 1-I-B1 (49.7g, 162.5mmol) and Pd 2 (dba) 3 (1.5g, 1.6 mmol), tri-tert-butylphosphine (0.6g, 3.2mmol), sodium tert-butoxide (31.2g, 325.0mmol) and xylene (600 mL) were charged in a three-necked flask, and the mixture was heated to 140 ℃ under nitrogen protection, and stirred under reflux for 8 hours. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give the solid compound sub B-6 (51.9g, 62%).
Preparation of intermediate sub1-I-BY and intermediate sub B-Y
Intermediates sub1-I-BY and sub B-Y shown in the following table were synthesized in a similar manner to the preparation of intermediates sub 1-I-B1 and sub B-6, except that starting material 4 was used instead of p-chlorobenzeneboronic acid, and the structure of starting material 4 and the structures and yields of intermediates sub1-I-BY and sub B-Y are shown in table 3.
TABLE 3
Preparation of Compound X
Compound X shown in table 4 below was synthesized using a similar method to that used to prepare compound 4, except that the following intermediates sub a-X were used instead of intermediate sub a-1, intermediate sub B-X/intermediate sub B-Y were used instead of intermediate sub B-1, and the intermediate structures, structure and yield of compound X are listed in table 4.
TABLE 4
Preparation of intermediate sub B-13
2,5-dichlorobenzoxazole (35.0g, 186.1mmol), 2-naphthalene boronic acid (32.0g, 186.1mmol), tetrakis (triphenylphosphine) palladium (4.3g, 3.7mmol), potassium carbonate (64.3g, 465.4 mmol), tetrabutylammonium bromide (1.2g, 3.72mmol), toluene (280 mL), ethanol (70 mL), and deionized water (70 mL) were charged to a three-necked flask, warmed to 76 ℃ under nitrogen, heated to reflux, and stirred for 15h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to obtain sub1-I-B (31.7g, 61%) as a solid intermediate.
3-bromocarbazole (30.0g, 121.8mmol), sub1-I-B (34.1g, 121.8mmol) and Pd 2 (dba) 3 (1.1g, 1.2mmol), tri-tert-butylphosphine (0.5g, 2.4mmol), sodium tert-butoxide (23.4g, 243.7mmol) and xylene (300 mL) were charged in a three-necked flask, and the mixture was heated to 140 ℃ under nitrogen protection, and stirred under reflux for 6 hours. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give sub B-13 (30.4g, 51%) as a solid intermediate.
Preparation of intermediate sub B-Z
An intermediate sub B-Z shown in table 5 below was synthesized in a similar manner to intermediate sub B-13, except that raw material 5 was used in place of 2,5-dichlorobenzoxazole and raw material 6 was used in place of 2-naphthalene boronic acid. The structures of starting materials 5 and 6 and the yields and structures of intermediates sub B-Z are shown in Table 5.
TABLE 5
Preparation of Compound Y
The compound Y shown in table 6 below was synthesized in a similar manner to the synthesis of preparation example 1, except that the following intermediates sub a-X were used instead of sub a-1 in example 1 and intermediates sub B-Z instead of intermediate sub B-1. The intermediate structures, the structure and the yields of compound Y are listed in table 6.
TABLE 6
Mass spectral data of the above prepared compounds are shown in table 7 below.
TABLE 7
| Compound 4 | m/z＝678.25(M+H) + | Compound 313 | m/z＝768.26(M+H) + |
| Compound 5 | m/z＝678.25(M+H) + | Compound 162 | m/z＝830.31(M+H) + |
| Compound 66 | m/z＝602.22(M+H) + | Compound 96 | m/z＝768.26(M+H) + |
| Compound 59 | m/z＝602.22(M+H) + | Compound 108 | m/z＝804.29(M+H) + |
| Compound 70 | m/z＝603.21(M+H) + | Compound 264 | m/z＝830.31(M+H) + |
| Compound 204 | m/z＝728.26(M+H) + | Compound 144 | m/z＝692.26(M+H) + |
| Compound 3 | m/z＝652.23(M+H) + | Compound 124 | m/z＝696.24(M+H) + |
| Compound 89 | m/z＝678.25(M+H) + | Compound 127 | m/z＝703.24(M+H) + |
| Compound 92 | m/z＝754.28(M+H) + | Compound 279 | m/z＝678.25(M+H) + |
| Compound 145 | m/z＝678.25(M+H) + | Compound 314 | m/z＝754.28(M+H) + |
| Compound 149 | m/z＝754.28(M+H) + | Compound 315 | m/z＝692.22(M+H) + |
| Compound 111 | m/z＝830.31(M+H) + | Compound 290 | m/z＝754.28(M+H) + |
| Compound 289 | m/z＝728.26(M+H) + | Compound 311 | m/z＝754.28(M+H) + |
| Compound 287 | m/z＝728.26(M+H) + |
The nuclear magnetic data for some of the compounds are shown in table 8 below.
TABLE 8
Example 1: preparation of green organic electroluminescent device
The anode was prepared by the following procedure: an ITO substrate (manufactured by Corning) having a thickness of 130nm was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O 2 ：N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of
And HT-1 is vapor-deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of
The first hole transport layer of (1).
Vacuum evaporating HT-19 on the first hole transport layer to a thickness of
The second hole transport layer of (1).
On the second hole transport layer, compounds 4: H37: ir (ppy) 2 (acac) was formed at a thickness of 55%: 40%: 5% by co-evaporation
Green organic light emitting layer (EML).
ET-01 and LiQ are mixed and evaporated at a weight ratio of 1:1 to form
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
And then magnesium (Mg) and silver (Ag) were vacuum-evaporated onto the electron injection layer at a deposition rate of 1: 10 to form an Electron Injection Layer (EIL) having a thickness of
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Forming an organic capping layer (CPL) to complete the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.
Examples 2 to 27
An organic electroluminescent device was fabricated by the same method as example 1, except that the compound shown in the table above was substituted for the compound 4 in forming the organic light-emitting layer.
Comparative examples 1 to 5
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound 4 was replaced with the compound I, the compound II, the compound III, the compound iv, and the compound v in forming the organic light-emitting layer.
The material structures used in the above examples and comparative examples are shown in table 9 below:
TABLE 9
For the organic electroluminescent device prepared as above, at 20mA/cm 2 The device performance was analyzed under the conditions of (1), and the results are shown in the following table 10:
watch 10
From the data in table 10, it can be seen that the nitrogen-containing compounds of examples 1 to 27, which are used as the hole-type host material in the mixed host material of the green organic light-emitting layer, significantly improved the device voltage, the light-emitting efficiency and the lifetime compared to comparative examples 1 to 5. Compared with comparative examples 1-5, the organic electroluminescent devices prepared by using the nitrogen-containing compounds of the application have the advantages that the current efficiency is improved by at least 12%, and the service life is improved by at least 12.9%.
Compared with comparative example 4, the nitrogen-containing compound combines benzoxazolyl/naphthoxazole with electronic property and biscarbazole with hole property, and aromatic groups are connected to the five-membered ring of the benzoxazolyl/naphthoxazole, so that the combined connection enables molecules to have unique distorted configuration, the crystallinity of the material is reduced, the film forming property of the material is better, and the service life of the material is prolonged. Compared with comparative example 5, the compound has higher T1 energy level, can remarkably improve the electron injection property of the material, and further improves the exciton recombination efficiency, thereby improving the luminous efficiency of the organic electroluminescent device. When the organic light emitting material is used as an organic light emitting layer main body material of a green organic light emitting device, the efficiency and the service life of the device can be improved, and the working voltage can be reduced. The nitrogen-containing compounds of the present application are suitable for use as organic light emitting layer materials for OLED devices. Especially when the material is connected with benzoxazole, the device performance is better.
Therefore, when the novel nitrogen-containing compound is used for preparing a green organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved, and the service life of the organic electroluminescent device can be prolonged.
The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application.
It should be noted that the various features described in the above embodiments may be combined in any suitable manner without departing from the scope of the invention. In order to avoid unnecessary repetition, various possible combinations are not described separately.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.
Claims (13)
1. A nitrogen-containing compound, characterized in that the nitrogen-containing compound has a structure represented by the following formula 1:
wherein L is 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar 2 Each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
the ring A is selected from aryl with 6-12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms;
R 1 、R 2 、R 3 and R 4 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;
L 1 、L 2 、L 3 、Ar 1 and Ar 2 In (1)The substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R 5 selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms;
optionally, in Ar 1 And Ar 2 Wherein two substituents attached to the same atom form a ring with the atom to which they are both attached;
n 1 represents R 1 Number of (2), n 1 Selected from 0, 1,2, 3 or 4, when n is 1 When greater than 1, any two R 1 The same or different;
n 2 represents R 2 Number of (2), n 2 Selected from 0, 1,2 or 3, when n is 2 When greater than 1, any two R 2 The same or different;
n 3 represents R 3 Number of (2), n 3 Selected from 0, 1,2 or 3, when n 3 When greater than 1, any two R 3 The same or different;
n 4 represents R 4 Number of (2), n 4 Selected from 0, 1,2, 3 or 4, when n is 4 When greater than 1, any two R 4 The same or different;
n 5 represents R 5 Number of (2), n 5 Selected from 0, 1,2, 3,4, 5 or 6, when n 5 When greater than 1, any two R 5 The same or different.
2. The nitrogen-containing compound according to claim 1, wherein ring a is a benzene ring or a naphthalene ring.
3. The nitrogen-containing compound according to claim 1,
selected from the group consisting of:
wherein is represented by
The radicals being used in combination with in formula 1
A bond to which the group is attached;
is shown in
The radicals being used in combination with in formula 1
The bond to which the group is attached.
4. The nitrogen-containing compound according to claim 1, wherein L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;
alternatively, L 1 、L 2 And L 3 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
5. The nitrogen-containing compound according to claim 1, wherein L 1 、L 2 And L 3 Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted naphthylene groupA biphenyl group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group;
alternatively, L 1 、L 2 And L 3 Wherein the substituents are independently selected from the group consisting of deuterium, fluoro, cyano, phenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar 1 And Ar 2 Each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms;
alternatively, ar 1 And Ar 2 Wherein the substituents are independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;
optionally, in Ar 1 And Ar 2 Wherein two substituents attached to the same atom form a 5-13 membered ring with the atom to which they are both attached.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar 1 And Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
the substituted group W has one or more substituents independently selected from the group consisting of deuterium, fluorine, cyano, phenyl, naphthyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.
8. The nitrogen-containing compound according to claim 1, wherein R 1 、R 2 、R 3 And R 4 Each independently selected from the group consisting of deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, cyclohexyl, dibenzofuranyl, cyclopentyl, pyridyl;
preferably, R 1 、R 2 、R 3 And R 4 Wherein the substituents are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
9. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
10. an organic electroluminescent device comprising a cathode and an anode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the nitrogen-containing compound according to any one of claims 1 to 9.
11. The organic electroluminescent device according to claim 10, wherein the functional layer comprises an organic light-emitting layer including the nitrogen-containing compound.
12. The organic electroluminescent device according to claim 10 or 11, wherein the organic electroluminescent device is a green organic electroluminescent device.
13. An electronic device, characterized in that it comprises an organic electroluminescent device according to any one of claims 10 to 12.
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