CN115141207A - Anthracene derivative, organic electroluminescent device and display device - Google Patents
Anthracene derivative, organic electroluminescent device and display device Download PDFInfo
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- CN115141207A CN115141207A CN202210762914.6A CN202210762914A CN115141207A CN 115141207 A CN115141207 A CN 115141207A CN 202210762914 A CN202210762914 A CN 202210762914A CN 115141207 A CN115141207 A CN 115141207A
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- 150000001454 anthracenes Chemical class 0.000 title claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 150000003918 triazines Chemical class 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 230000000694 effects Effects 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 169
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- 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 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000005577 anthracene group Chemical group 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 9
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- BBXQYOQXGGJUFK-UHFFFAOYSA-N 6-bromo-1-benzofuran Chemical compound BrC1=CC=C2C=COC2=C1 BBXQYOQXGGJUFK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- IZYQYWHHPQRWFX-UHFFFAOYSA-N [3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 IZYQYWHHPQRWFX-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- ASQXKNXJNDLXQV-UHFFFAOYSA-N (10-naphthalen-1-ylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 ASQXKNXJNDLXQV-UHFFFAOYSA-N 0.000 description 1
- YGVDBZMVEURVOW-UHFFFAOYSA-N (10-naphthalen-2-ylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 YGVDBZMVEURVOW-UHFFFAOYSA-N 0.000 description 1
- -1 1-bromo-10-phenylpyrene Chemical compound 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- MTFXKOSTROHADA-UHFFFAOYSA-N BrC=1C=CC2=CC=C3C=CC=C4C=C(C=1C2=C43)C Chemical compound BrC=1C=CC2=CC=C3C=CC=C4C=C(C=1C2=C43)C MTFXKOSTROHADA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group 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 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- NKVDKFWRVDHWGC-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical compound [Ir+3].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NKVDKFWRVDHWGC-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 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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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an anthracene derivative, an organic electroluminescent device and a display device, wherein the anthracene derivative has a structure shown in a formula 1, in the formula 1,z is a structure represented by the following formula 2, formula 3 or formula 4. The invention can reduce the problem of luminous crosstalk between the sub-pixels and improve the display effect.
Description
Technical Field
The invention relates to an anthracene derivative, an organic electroluminescent device and a display device, and belongs to the technical field of organic electroluminescence.
Background
An Organic Light Emitting Diode (OLED) is a self-Light Emitting device, does not need a backlight, has the advantages of a wide viewing angle, high contrast, high brightness, high response speed and the like, and is gradually applied to devices such as mobile phones, computers, televisions, wearable devices and the like.
In an organic electroluminescent device, functional material layers such as a hole injection layer and a hole transport layer are generally used as common layers to connect red, green, and blue (RGB) sub-pixels in series. In the using process, the universal layer can cause cross talk due to transverse electric leakage, namely, the screen body is under an R, G or B monochromatic picture, the sub-pixels of other colors will be slightly bright, affecting the display effect.
Disclosure of Invention
The invention provides an anthracene derivative, an organic electroluminescent device and a display device, which aim to reduce the problem of luminous crosstalk between sub-pixels and improve the display effect.
In one aspect of the present invention, there is provided an anthracene derivative having a structure represented by formula 1 below:
in the formula 1, R 11 ～R 20 At least one of is with L 1 The remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms;
L 1 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 1 to 3;
z is a structure represented by the following formula 2, formula 3 or formula 4:
in the formula 2, R 101 ～R 110 At least one of is represented by 1 Each of the others is independently selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 3, R 201 ～R 210 At least one of is represented by and L 1 Each of the others is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 4, R 301 ～R 310 At least one of is represented by 1 And the remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
Alternatively, the anthracene derivative has a structure represented by the following formula 1-1:
alternatively, the anthracene derivative may be selected from the following compounds:
in another aspect of the present invention, there is provided a triazine derivative having a structure represented by the following formula 5:
in the formula 5, R 1 、R 2 Each independently selected from substituted or unsubstituted aryl with 6-50 ring carbon atoms and substituted or unsubstituted heteroaryl with 6-50 ring carbon atoms;
L 2 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
Ar 1 is a structure shown in the following formula 6:
in the formula 6, R 401 ～R 410 One of them represents and L 2 The attachment site(s) of (a), the rest is independently selected from hydrogen, deuterium, halogen atom, cyano, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-50 ring carbon atoms and substituted or unsubstituted heteroaryl with 6-50 ring carbon atoms.
Alternatively, the triazine derivative has a structure represented by formula 5-1 or formula 5-2 below:
wherein, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from N or-CR, R is selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
Alternatively, the triazine derivative is selected from the following compounds:
in still another aspect of the present invention, there is provided an organic electroluminescent device comprising an organic light-emitting layer including the anthracene derivative having the structure represented by formula 1.
Alternatively, the organic light emitting layer includes a blue light emitting layer including the anthracene derivative.
Optionally, the blue light emitting layer contains a host material including the anthracene derivative.
In still another aspect of the present invention, there is provided an organic electroluminescent device comprising an electron transport layer comprising the triazine derivative having the structure represented by formula 5 described above.
In still another aspect of the present invention, there is provided a display apparatus including the above organic electroluminescent device.
The anthracene derivative can reduce the electron injection and transmission energy barrier of the blue light-emitting layer, so that the lighting voltage of the blue light-emitting layer is reduced, the lighting voltage difference between the blue light-emitting layer and the red/green light-emitting layer can be reduced, the red light-emitting layer and the green light-emitting layer are prevented from being lighted when the blue light-emitting layer is lighted, the problem of light-emitting crosstalk caused by improper light emission of the red light-emitting layer and the green light-emitting layer is further avoided, and the display effect is improved.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention.
Description of reference numerals: 1: a substrate; 2: an anode; 31: a hole injection layer; 32: a hole transport layer; 33: an electron blocking layer; 41: a red light emitting layer; 42: a green light emitting layer; 43 a blue light-emitting layer; 51: a hole blocking layer; 52: an electron transport layer; 53: an electron injection layer; 6: a cathode; 7: a pixel definition layer.
Detailed Description
At present, the problem of light emitting crosstalk generally exists between red, green and blue (RGB) sub-pixels of an organic electroluminescent device, which affects the display effect, on one hand, functional material layers such as a hole injection layer and a hole transport layer, which are used as common layers, generally have strong electrical conductivity, and can generate lateral electric leakage, so that when a certain sub-pixel is lit, current is laterally transported to an adjacent sub-pixel, which causes the lighting of the adjacent sub-pixel, which causes the problem of lateral crosstalk, at present, common layer materials such as a hole injection layer with poor lateral electrical conductivity are generally adopted to reduce crosstalk, but this can also cause the longitudinal electrical conductivity to be poor, which causes the driving voltage of the OLED to be increased, reduces the light emitting efficiency, and is limited in application; on the other hand, the difference between the on-voltage of the blue sub-pixel and the on-voltage of the red/green sub-pixel is usually large, and when the blue sub-pixel is turned on, the driving voltage is higher than the on-voltage of the red/green sub-pixel, so that the red/green sub-pixel is also turned on to emit light, thereby generating crosstalk.
In view of the above, the present invention provides an anthracene derivative having a structure represented by formula 1 below:
in the formula 1, R 11 ～R 20 At least one of is with L 1 The remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms;
L 1 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 1 to 3;
z is a structure represented by formula 2, formula 3 or formula 4 below:
in the formula 2, R 101 ～R 110 At least one of is represented by 1 Each of the others is independently selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 3, R 201 ～R 210 At least one of is represented by and L 1 Each of the others is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 4, R 301 ～R 310 At least one of is represented by 1 And the remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
The halogen atom may be fluorine (F), chlorine (Cl), bromine (Br), iodine (I), or the like.
In formula 1, a represents a linkage to L 1 The number of anthracene groups on, b represents the linkage to L 1 The number of Z groups, a, may be 1, 2 or 3, b may be 1, 2 or 3.
In formula 1, when L 1 And a is a single bond, which means that the anthracene group is bonded to the Z group by a single bond, in which case a and b are each independently 1. When L is 1 Selected from substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, having a anthracene groups substituted to L 1 Above, b Z groups are substituted to L 1 The above.
c represents a bond to an anthracene group
Number of radicals, i.e. R 11 ～R 20 C in each case are represented by 1 In particular, when c =1, R 11 ～R 20 One of is with L 1 The attachment site of (1), i.e. R 11 ～R 20 One and one of
Group attachment; when c =2, R 11 ～R 20 Are with L 1 Of (b) are each linked to one
A group; when c =3, R 11 ～R 20 Three of (A) and (B) are 1 Of (a) each of which is linked to one
A group.
In general, in the anthracene group, R 13 Or R 18 Is and L 1 Thus, structural stability of the anthracene derivative is facilitated.
Specifically, R in formula 1/formula 1-1 18 Is and L 1 When the above anthracene derivative has a structure represented by the following formula 1-1:
illustratively, L1 is a single bond, when the above anthracene derivative has a structure represented by the following formula 1-1-1:
alternatively, L1 is an aryl group or a heteroaryl group, and the above anthracene derivative may specifically have a structure represented by the following formula 1-1-2 or formula 1-1-3:
wherein, Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 Each independently selected from N or-CR 5 ，R 5 Specifically, the compound may be selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.
Illustratively, in formula 2, R 105 Or R 110 Is represented by the formula 1 The attachment site of (a); in the formula 3, R 202 、R 206 、R 204 、R 208 、R 203 、R 207 、R 204 、R 208 、R 209 Or R 210 Is represented by the formula 1 The attachment site of (a); in the formula 4, R 305 Or R 310 Is represented by the formula 1 The attachment site of (a).
For example, in formula 1-1, Z is a structure represented by formula 3, R in formula 3 210 Is represented by the formula 1 When the above anthracene derivative has a structure as shown in the following formula 1-1 a:
in the present invention, the aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, and the like.
In some embodiments, the anthracene derivative is selected from the following compounds:
in the specific implementation process, the first-stage reactor,when L is 1 When the compound is a single bond, the compound with anthracene group (shown as formula 7) can react with the compound with z group (shown as formula 8-1) to bond anthracene group and z group together to generate anthracene derivative shown as formula 1; when L is 1 When not a single bond, a compound having an anthracene group (e.g. formula 7) may be bonded to the substrate with a bond L 1 Reacting the compound of the group z (formula 8) (equivalent to first reacting L) 1 Bonded to a z group followed by bonding to an anthracene group), or will carry a bond L 1 With a compound having a z group (corresponding to the anthracene group and L first) 1 And then bonded with a z group) to produce an anthracene derivative represented by formula 1.
In one embodiment, the anthracene derivative of formula 1 may be prepared from a compound of formula 7 and a compound of formula 8.
In the formula 7, R 11 ～R 20 At least one of is
Attachment site for a group (the attachment site is formed with L in the prepared formula 1) 1 The linking site(s) and the remainder are identical to the prepared substituent(s) in formula 1, and will not be described in detail.
In formula 7, c represents a substituent substituted on the anthracene group
Number of radicals, i.e. R 11 ～R 20 Wherein c are represented by
Attachment sites for groups, e.g. when c =1, the anthracene group is substituted by one
Radical, i.e. R 11 ～R 20 One of which is
The attachment site of the group; when c =2, two are substituted on the anthracene group
Radical, i.e. R 11 ～R 20 Two of (1) are
The attachment site of a group, each of which is attached to one
A group.
Exemplarily, c =1,r in formula 7 18 Is and is
At the attachment site of the group, formula 7 is a structure represented by the following formula 7-1:
in formula 8, x 1 Is a halogen atom, for example selected from fluorine (F), chlorine (Cl), bromine (Br) or iodine (I), etc., a represents and L 1 X of connection 1 B represents the same as L 1 The number of attached z groups (consistent with b in formula 1).
In some embodiments, L 1 When the structure is a single bond, the compound shown in the formula 8 is shown as the following formula 8-1: x is the number of 1 Z (formula 8-1), i.e. x 1 Attached to the z group by a single bond.
After the compound represented by formula 7 is reacted with the compound represented by formula 8, that in formula 7
Radical quilt
And substituting the group to generate the anthracene derivative shown in the formula 1.
Illustratively, the reaction formula for preparing formula 1-1 is as follows:
to improve the reaction efficiency, the reaction of the compound represented by formula 7 with the compound represented by formula 8 may be performed under the action of a first catalyst, and the first catalyst used may include tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 )。
Further, the reaction of the compound represented by formula 7 with the compound represented by formula 8 may be performed under an inert atmosphere including, for example, a nitrogen atmosphere.
In addition, the reaction of the compound represented by formula 7 with the compound represented by formula 8 may be performed in a refluxing state, that is, the compound represented by formula 7 and the compound represented by formula 8 are placed in a first solvent, and then heated to reflux, and the reaction is performed in a refluxing state to produce the compound represented by formula 1. The first solvent used may specifically include an organic solvent, including, for example, tetrahydrofuran (THF).
Further, the reaction of the compound of formula 7 with the compound of formula 8 may be carried out in a basic environment, which may be provided by a first weak base, for example comprising a carbonate and/or bicarbonate, such as potassium carbonate (K) 2 CO 3 ) And so on. In particular embodiments, the weak base may be dissolved in water to form a first weak base solution, which is mixed with a reaction system containing reactants to provide an alkaline environment.
In some embodiments, the process for preparing the anthracene derivative represented by formula 1 includes: mixing a compound shown as a formula 7, a compound shown as a formula 8, a first catalyst, a first weak base solution and a first solvent in an inert atmosphere, heating to reflux, reacting in a reflux state, cooling after reaction contact, and extracting a product by using an organic solvent such as dichloromethane to obtain an organic phase; the organic phase is dried with a drying agent such as anhydrous magnesium sulfate, filtered, and then subjected to reduced pressure distillation to remove an organic solvent such as dichloromethane, and the obtained crude product is subjected to column chromatography to obtain the anthracene derivative represented by formula 1.
The anthracene derivative with the structure shown in the formula 1 can be used as a blue light-emitting layer material, and can reduce the lighting voltage of the blue light-emitting layer, so that the lighting voltage difference between the blue light-emitting layer and the red/green light-emitting layer is reduced, and the light-emitting crosstalk is avoided.
The invention also provides a triazine derivative which is a triazine derivative with a structure shown in the following formula 5.
In the formula 5, R 1 、R 2 Each independently selected from substituted or unsubstituted aryl with 6-50 ring carbon atoms and substituted or unsubstituted heteroaryl with 6-50 ring carbon atoms;
L 2 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
Ar 1 is a structure shown in the following formula 6:
in the formula 6, R 401 ～R 410 One of them represents and L 2 The remaining are independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms.
In formula 5, when L 2 When it is a single bond, it means that the triazine group is bonded to Ar through a single bond 1 And (4) connecting. Illustratively, R 410 Is and L 2 The attachment site of (3), L 2 Is a single bond, the triazine derivative of formula 5 has a structure represented by the following formula 5-1:
or, in formula 5, L 2 The triazine derivative may specifically have a structure represented by the following formula 5-2, which is an aryl group or a heteroaryl group:
wherein, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from N or-CR, R is selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
In some embodiments, the triazine derivative represented by formula 5 is specifically selected from the following compounds:
when embodied, L is 2 When the compound is a single bond, a compound having a triazine group (formula 9) and Ar 1 Reacting a compound of the group (as in formula 10-1) to react the triazine group with Ar 1 The groups are bonded together to form the triazine derivative shown in the formula 5; when L is 2 When not a single bond, a compound having a triazine group (e.g., formula 9) may be bonded to the compound having a linkage L 2 Ar of (2) 1 Reacting a compound of the group (formula 10) (equivalent to first reacting L) 2 And Ar 1 Group bonding followed by triazine group) or will carry a bond L 2 With compounds having a triazine group with Ar 1 Reacting the compound of the group (corresponding to the first reaction of the triazine group with L 2 Bonding and then bonding Ar 1 Group) to produce a triazine derivative represented by formula 5.
In one embodiment, the triazine derivative represented by formula 5 may be prepared by reacting a compound represented by formula 9 with a compound represented by formula 10.
In formula 10, x 2 Is a halogen atom, e.g. selected from fluorine (F), chlorine (Cl), bromine (Br) or iodine (I), etc., when L is 2 When the group is a single bond, the compound represented by formula 10 has a structure represented by the following formula 10-1: x is the number of 2 -Ar 1 (formula 10-1), i.e., x 2 By a single bond with Ar 1 And (4) connecting.
After the compound represented by formula 9 is reacted with the compound represented by formula 10, that in formula 9
Radical quilt
And (3) carrying out group substitution to generate the triazine derivative shown in the formula 5.
Illustratively, the reaction formula for preparing formula 5-1 is as follows:
to improve the reaction efficiency, the reaction of the compound of formula 9 with the compound of formula 10 may be carried out under the action of a second catalyst, and the second catalyst used may include tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 )。
Further, the reaction of the compound represented by formula 9 with the compound represented by formula 10 may be performed under an inert atmosphere, including, for example, a nitrogen atmosphere.
In addition, the reaction of the compound represented by formula 9 with the compound represented by formula 10 may be performed in a reflux state, that is, the compound represented by formula 9 and the compound represented by formula 10 are placed in a second solvent, and then heated to reflux, and the reaction is performed in a reflux state to produce the triazine derivative represented by formula 5. Among them, the solvent used may specifically include an organic solvent, including, for example, tetrahydrofuran (THF).
Furthermore, the reaction of the compound of formula 9 with the compound of formula 10 may be carried out in a basic environment, which may be provided by a second weak base, for example comprising a carbonate and/or bicarbonate, such as potassium carbonate (K) 2 CO 3 ) And the like. In particular embodiments, the weak base may be dissolved in water to form a second weak base solution, which is mixed with the reaction system containing the reactants to provide an alkaline environment.
In some embodiments, the triazine derivative represented by formula 5 is prepared by a process comprising: mixing a compound shown as a formula 9, a compound shown as a formula 10, a second catalyst, a second weak base solution and a second solvent in an inert atmosphere, heating to reflux, reacting in a reflux state, cooling after reaction contact, and extracting a product by using an organic solvent such as dichloromethane to obtain an organic phase; the organic phase is dried, for example, with a drying agent such as anhydrous magnesium sulfate, filtered, and then subjected to reduced pressure distillation to remove an organic solvent such as dichloromethane, and the obtained crude product is subjected to column chromatography to obtain the triazine derivative represented by formula 5.
The triazine derivative with the structure shown in the formula 5 can be used as an electron transport layer material, can reduce the starting voltage of a blue light-emitting layer, and can improve the starting voltage of a red/green light-emitting layer, so that the starting voltage difference between the blue light-emitting layer and the red/green light-emitting layer is reduced, and the light-emitting crosstalk is avoided.
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention, and as shown in fig. 1, the organic electroluminescent device includes an anode 2, a hole transport region, an organic light emitting Layer, an electron transport region, and a cathode 6, which are sequentially stacked on a substrate 1, wherein the organic light emitting Layer includes a red light emitting Layer 41, a green light emitting Layer 42, and a blue light emitting Layer 43, the functional material layers such as the hole transport region are used as a common Layer to connect the red light emitting Layer 41, the green light emitting Layer 42, and the blue light emitting Layer 43 in series, and the anodes corresponding to different organic light emitting layers are respectively separated by a Pixel Definition Layer (PDL) 7.
Specifically, the substrate 1 may be made of glass or a polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. A Thin Film Transistor (TFT) may be provided on the substrate 1 for display.
The anode 2 may be formed by sputtering or depositing an anode material on the substrate 1, wherein the anode material may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), or tin dioxide (SnO) 2 ) One or a combination of a plurality of oxide transparent conductive materials such as zinc oxide (ZnO); the cathode 6 may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
Organic material layers such as a hole transport region, an organic light emitting layer, an electron transport region, and a cathode 6 may be sequentially formed on the anode 2 by vacuum thermal evaporation, spin coating, printing, and the like. Among them, the compound used as the organic material layer may be small organic molecules, large organic molecules, and polymers, and combinations thereof.
Here, the blue light emitting layer 43 includes an anthracene derivative represented by formula 1. By introducing the anthracene derivative represented by formula 1 into the blue light-emitting layer 43, the turn-on voltage of the blue light-emitting layer can be reduced, so that the difference between the turn-on voltages of the blue light-emitting layer 43 and the red light-emitting layer 41/green light-emitting layer 42 can be reduced, and the occurrence of light emission crosstalk can be avoided by turning on the red light-emitting layer 41 and the green light-emitting layer 42 at the same time as turning on the blue light-emitting layer.
Specifically, the blue light emitting layer 43 contains a host material including an anthracene derivative represented by formula 1, that is, the anthracene derivative represented by formula 1 is a host material of the blue light emitting layer 43.
The blue light emitting layer 43 may include one kind of anthracene derivative having a structure shown in formula 1, or at least two kinds of anthracene derivatives having a structure shown in formula 1, for example, at least one of the compounds a-1, a-2, a-3, a-4, a-5, a-6, a-7, a-8, a-9, a-10, a-11, a-12, a-13, a-14, and a-15.
In addition, the blue light-emitting layer 43 may further include a dopant material, including, for example, DSA-Ph (4, 4' - [1, 4-phenylenedi- (1E) -2, 1-ethenediyl ] bis [ N, N-diphenylaniline ]), but is not limited thereto.
In general, the reason for generating the light emitting crosstalk mainly includes two aspects, namely, the lateral leakage of the common layers such as the hole injection layer and the hole transport layer, and the difference between the lighting voltages of the blue light emitting layer and the red/green light emitting layer is large, the invention introduces a novel anthracene derivative with the structure shown in formula 1 into the blue light emitting layer from the angle of reducing the lighting voltage difference between the blue sub-pixel and the red/green sub-pixel, according to the research and analysis of the inventor, the anthracene derivative shown in formula 1 simultaneously contains an anthracene group and a benzofuran group, and the anthracene derivative and the benzofuran group have synergistic effect, so that the electron injection and transmission energy barrier of the blue light emitting layer can be reduced, the lighting voltage of the blue light emitting layer is reduced, the lighting voltage difference between the blue light emitting layer and the red/green light emitting layer is reduced, and the problem of the light emitting crosstalk caused by improper light emitting of the red/green light emitting layer is relieved.
Specifically, the electron transport layer 5 may include a triazine derivative having a structure represented by formula 5, and specifically may include one triazine derivative having a structure represented by formula 5, or at least two triazine derivatives having a structure represented by formula 5, for example, at least one of T-1, T-2, T-3, T-4, T-5, T-6, T-7, T-8, T-9, T-10, T-11, and T-12 is included.
In order to avoid the problem of light emission crosstalk, the present invention introduces a novel triazine derivative having a structure shown in formula 5 into the electron transport layer 5 from the viewpoint of reducing the lighting voltage difference between the blue sub-pixel and the red/green sub-pixel, and according to the research and analysis of the inventors, the triazine derivative shown in formula 5 has a triazine group and a pyrene group, and the LUMO energy level thereof is shallow, so that the LUMO energy levels of the cathode 6, the electron transport layer 5 and the blue light emitting layer 43 become gradually shallow, and the electron transport layer 5 acts as a step, thereby reducing the electron transport barrier and reducing the lighting voltage of the blue light emitting layer 43. In contrast, for the red light-emitting layer 41 and the green light-emitting layer 42, the band gap of the red/green light material is small, the LUMO level is deep, and the LUMO level of the electron transport layer 5 is shallower than the LUMO levels of the red light-emitting layer 41 and the green light-emitting layer 42, that is, the LUMO levels of the red light-emitting layer 41 and the green light-emitting layer 42 are lower with respect to the electron transport layer 5, which is unfavorable for electron transport from the electron transport layer 5 to the red light-emitting layer 41 and the green light-emitting layer 42, so that the electron injection and transport energy barriers of the red light-emitting layer 54 and the green light-emitting layer 42 are increased, and the turn-on voltage of the red light-emitting layer 41 and the green light-emitting layer 42 is increased.
Thus, by introducing the triazine derivative represented by formula 5 into the electron transport layer 5, the on-voltage of the blue light-emitting layer 43 can be reduced, the on-voltages of the red light-emitting layers 41 and the green light-emitting layers 42 can be increased, the difference in on-voltages between the blue light-emitting layer 43 and the red light-emitting layers 41 and the green light-emitting layers 42 can be reduced, and the problem of light emission crosstalk can be avoided.
Specifically, the red light emitting layer 41 includes a host material including a carbazole derivative, including 4,4' -bis (9-Carbazolyl) Biphenyl (CBP), for example, and a dopant material including tris (1-phenyl-isoquinoline) iridium (III) (Ir (piq), for example 3 )。
In addition, the green light emitting layer 42 includes a host material including a carbazole derivative, for example, CBP, and a dopant material including tris (2-phenylpyridine) iridium (Ir (ppy), for example 3 )。
The hole transport region is located at the anode 2 and an organic light emitting layer. The hole transport region may include at least one of a Hole Injection Layer (HIL) 31, a Hole Transport Layer (HTL) 32, and an Electron Blocking Layer (EBL) 33, which may be a single-layer structure of the Hole Transport Layer (HTL), include a single-layer hole transport layer containing only one compound or a single-layer hole transport layer containing a plurality of compounds, or may also be a multi-layer structure including at least one of the Hole Injection Layer (HIL) 31, the Hole Transport Layer (HTL) 32, and the Electron Blocking Layer (EBL) 33.
In some embodiments, as shown in fig. 1, the hole transport region 3 includes a hole injection layer 31, a hole transport layer 32, and an electron blocking layer 33, which are sequentially stacked, wherein the electron blocking layer 33 is divided into 3 portions, one portion is located between the red light-emitting layer 41 and the hole transport layer 32, the other portion is located between the green light-emitting layer 42 and the hole transport layer 32, and the other portion is located between the blue light-emitting layer 43 and the hole transport layer 32.
Further, the electron transport region may include at least one of an Electron Injection Layer (EIL) 53, an Electron Transport Layer (ETL) 52, and a Hole Blocking Layer (HBL) 51, which may be a single-layer structure of the Electron Transport Layer (ETL) 52, including a single-layer electron transport layer containing only one compound or a single-layer electron transport layer 52 containing a plurality of compounds, or may also be a multi-layer structure including at least one of the Electron Injection Layer (EIL) 53, the Electron Transport Layer (ETL) 52, and the Hole Blocking Layer (HBL) 51.
The materials for the above layers may be those conventional in the art, and may be commercially available or self-made, and the thickness of each layer may be those conventional in the art, unless otherwise specified.
Illustratively, the hole injection layer 31 comprises 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-Hexaazatriphenylene (HATCN), the hole transport layer 32 comprises N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), the electron blocking layer 33 comprises 4,4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), and the electron injection layer 53 comprises lithium fluoride (LiF).
The display device of the embodiment of the invention comprises the organic electroluminescent device. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
In the following examples, the synthesis of A-1 is as follows:
to the flask, 3.48g of 10- (2-naphthyl) anthracene-9-boronic acid, 3.36g of 6-bromo-benzofuran [2,3-c ] were added in this order under a nitrogen atmosphere]Dibenzofuran, 0.1g tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) Potassium carbonate aqueous solution (5.52g, 20mmol of K 2 CO 3 20mL of water),60mL of tetrahydrofuran was heated under reflux for 12 hours. After the reaction was completed, cooling was performed, and after cooling, the product was extracted with dichloromethane, the dichloromethane phase was dried over anhydrous magnesium sulfate, filtered and the dichloromethane was evaporated under reduced pressure, and the obtained crude product was subjected to column chromatography to obtain a-1 product (white solid powder), about 5.1g, yield 91%. Mass spectrometry of the product showed the target product (i.e., compound A-1) with a relative molecular mass of 560.18, [ M + H ]] + ＝561。
The synthesis process of A-2 is as follows:
to the flask, 3.48g of 10- (1-naphthyl) anthracene-9-boronic acid, 3.36g of 6-bromo-benzofuran [2,3-c ] were added in this order under a nitrogen atmosphere]Dibenzofuran, 0.1g tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) Potassium carbonate aqueous solution (5.52g, 20mmol of K) 2 CO 3 20mL of water), 60mL of tetrahydrofuran, and the reaction was heated under reflux for 12 hours. After the reaction was completed, cooling was performed, and after cooling, the product was extracted with dichloromethane, the dichloromethane phase was dried over anhydrous magnesium sulfate, filtered and the dichloromethane was evaporated under reduced pressure, and the obtained crude product was subjected to column chromatography to obtain an a-2 product (white solid powder) in an amount of about 5.0g, with a yield of 89%. Mass spectrometry of the product showed the target product (i.e., compound A-2) with a relative molecular mass of 560.18, [ M + H ]] + ＝561。
In addition, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14 and A-15 are all prepared according to the preparation processes of A-1 and A-2, and are measured to have corresponding structures through nuclear magnetic resonance hydrogen spectrum and mass spectrum analysis, and are not repeated.
The synthesis process of T-1 is as follows:
3.53g of 3- (4, 6-diphenyl-1, 3,5-Triazin-2-yl) -phenylboronic acid, 2.94g 1-bromo-10-methylpyrene, 0.1g tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) Potassium carbonate aqueous solution (5.52g, 20mmol of K) 2 CO 3 20mL of water), 60mL of tetrahydrofuran, and heating to reflux for 12 hours. After the reaction, the reaction product was cooled, and after cooling, the product was extracted with dichloromethane, the dichloromethane phase was dried over anhydrous magnesium sulfate, filtered and the dichloromethane was evaporated under reduced pressure, and the crude product obtained was subjected to column chromatography to obtain a T-1 product (white solid powder) in an amount of about 4.8g, with a yield of 92%. Mass spectrometry of the product showed that the target product (i.e., compound T-1) had a relative molecular mass of 523.20, [ M + H ]] + ＝524。
The synthesis process of T-2 is as follows:
to the flask were added 3.53g of 3- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -phenylboronic acid, 3.56g of 1-bromo-10-phenylpyrene, 0.1g of tetrakis (triphenylphosphine) palladium (Pd (PPh) in that order under a nitrogen atmosphere 3 ) 4 ) Potassium carbonate aqueous solution (5.52g, 20mmol of K) 2 CO 3 20mL of water), 60mL of tetrahydrofuran, and the reaction was heated under reflux for 12 hours. After the reaction, the reaction product was cooled, and after cooling, the product was extracted with dichloromethane, the dichloromethane phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness under reduced pressure, and the resulting crude product was subjected to column chromatography to obtain a T-2 product (white solid powder) in an amount of about 5.1g, with a yield of 87%. Mass spectrometry of the product showed that the target product (i.e., compound T-2) had a relative molecular mass of 585.22, [ M + H ]] + ＝586。
In addition, T-3, T-4, T-5, T-6, T-7, T-8, T-9, T-10, T-11 and T-12 are all prepared by referring to the preparation processes of T-1 and T-2, and have corresponding structures through nuclear magnetic resonance hydrogen spectrum and mass spectrum analysis, and are not repeated.
Example 1
The structure of the electroluminescent device and the materials of the layers of the present example are shown in table 1:
TABLE 1
Comparative example 1: the difference from example 1 is that the host material of the blue light-emitting layer was 9, 10-bis- (2-naphthyl) Anthracene (ADN), and the material of the electron transport layer was tris (8-hydroxyquinoline) aluminum (III) (Alq) 3 ) Otherwise, the same procedure as in example 1 was repeated.
Comparative example 2: the difference from embodiment 1 is that, unlike the host material of only the blue light-emitting layer, the host material of the blue light-emitting layer is ADN.
Example 2 to example 28: the difference from example 1 is that the blue light emitting layer material and/or the electron transport layer material are different, specifically see table 2, and the conditions are the same except for the differences shown in table 2.
The light-on voltages of the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer in examples 1 to 28, comparative example 1, and comparative example 2 were measured and are shown in table 2.
TABLE 2
* : Δ V represents the difference between the on-voltage of the blue light-emitting layer and the on-voltage of the red light-emitting layer.
It can be seen that, compared to comparative examples 1 and 2, examples 1 to 28 significantly reduce the on-state voltage of the blue light emitting layer, thereby reducing the on-state voltage difference between the blue light emitting layer and the red/green light emitting layer and avoiding the problem of light emission crosstalk.
In addition, compared with embodiment 2, in embodiments 1 and 3 to 28, the turn-on voltage of the blue light emitting layer is reduced, and the turn-on voltage of the red/green light emitting layer is increased, so that the turn-on voltage difference between the blue light emitting layer and the red/green light emitting layer is reduced to a greater extent, and the effect of reducing the light emitting crosstalk can be more remarkably achieved.
Claims (10)
1. An anthracene derivative having a structure represented by formula 1 below:
in the formula 1, R 11 ～R 20 At least one of is with L 1 The remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms;
L 1 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 1 to 3;
z is a structure represented by the following formula 2, formula 3 or formula 4:
in the formula 2, R 101 ～R 110 At least one of is represented by 1 Each of the others is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 3, R 201 ～R 210 At least one of is represented by 1 Each of the others being independently selected fromHydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms;
in the formula 4, R 301 ～R 310 At least one of is represented by 1 The remaining are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
2. The anthracene derivative according to claim 1, which has a structure represented by the following formula 1 to 1:
3. the anthracene derivative according to claim 1 or 2, wherein the anthracene derivative is selected from the following compounds:
4. a triazine derivative having a structure represented by the following formula 5:
in the formula 5, R 1 、R 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms;
L 2 selected from the group consisting of a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
Ar 1 is a structure represented by the following formula 6:
in the formula 6, R 401 ～R 410 One of them represents and L 2 The remaining sites are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 50 ring-forming carbon atoms.
5. The organic electroluminescent device according to claim 4, wherein the triazine derivative has a structure represented by the following formula 5-1 or formula 5-2:
wherein, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from N or-CR, R is selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
6. The organic electroluminescent device according to claim 4 or 5, characterized in that the triazine derivative is selected from the following compounds:
7. an organic electroluminescent element comprising an organic light-emitting layer containing the anthracene derivative according to any one of claims 1 to 3.
8. The organic electroluminescent device according to claim 7, wherein the organic light-emitting layer comprises a blue light-emitting layer containing the anthracene derivative;
optionally, the blue light emitting layer contains a host material including the anthracene derivative.
9. An organic electroluminescent device comprising an electron transport layer comprising the triazine derivative according to any one of claims 4 to 6.
10. A display device comprising the organic electroluminescent element as claimed in any one of claims 7 to 9.
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