CN114728947B - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- CN114728947B CN114728947B CN202080077208.7A CN202080077208A CN114728947B CN 114728947 B CN114728947 B CN 114728947B CN 202080077208 A CN202080077208 A CN 202080077208A CN 114728947 B CN114728947 B CN 114728947B
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 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
- 238000004140 cleaning Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 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
- 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 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
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane 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-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000001771 vacuum deposition Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2020-0017590 of 13 d of 2 months in 2020 and korean patent application No. 10-2020-0175628 of 15 d of 12 months in 2020, the entire contents of the disclosures of the korean patent application are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exciton) are formed, and light is emitted when the excitons re-transition to the ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(Patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
Ar is C 13-60 aryl, which is unsubstituted or substituted by at least one deuterium, C 1-18 alkyl, or C 6-18 aryl,
R 1 to R 4 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, or substituted or unsubstituted C 6-60 aryl, or adjacent two groups combine with each other to form a substituted or unsubstituted aromatic ring structure,
R 5 to R 8 are each independently hydrogen; deuterium; halogen; a nitrile group; a silyl group; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 6-60 aryl group; a substituted or unsubstituted C 2-60 alkenyl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
M is an integer of 0 to 3,
N is an integer of 0 to 8,
P and q are each independently integers from 0 to 4.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light emitting device constituted by a substrate 1, an anode 2, an organic layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,Or (b)Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; aryl thioxy; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing N, O and 1 or more of heterocyclic groups of 1 or more of S atoms, or a substituent linked by 2 or more of the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms; or aryl substitution of 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be thatEtc. However, the present invention is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,An azolyl group,Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl quinoxalinyl, phthalazinyl, pyridopyrimidinyl, and pyridopyrazinyl radical pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, and benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, and the like dibenzothienyl, benzofuranyl, phenanthroline (phenanthrine), isolOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of a heterocyclic group can be applied thereto.
Preferably, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1a to 1 d:
[ chemical formula 1a ]
[ Chemical formula 1b ]
[ Chemical formula 1c ]
[ Chemical formula 1d ]
In the above chemical formulas 1a to 1d,
Ar, R 1 to R 8, m, n, p and q are as defined above.
In addition, in the above chemical formula 1, ar is preferably a terphenyl group, a (phenyl) naphthyl group, a (naphthyl) phenyl group, a (naphthyl) biphenyl group, a (phenyl-naphthyl) phenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a triphenylenyl group, a phenanthrenyl group or a (phenanthrenyl) phenyl group,
Ar as described above may be unsubstituted or substituted with at least one deuterium, C 1-18 alkyl, or C 6-18 aryl group.
More preferably, ar may be any one selected from the following formulas:
in each of the above-mentioned chemical formulas,
R 11 are identical or different and are each hydrogen, deuterium, C 1-18 alkyl or C 6-18 aryl, preferably R 11 are identical or different and are each hydrogen, deuterium, methyl or phenyl,
The dashed lines indicate the binding sites.
In addition, in the above chemical formula 1, R 1 to R 4 may each be independently hydrogen, deuterium, or phenyl.
Preferably, R 1 to R 4 may all be hydrogen or all be deuterium.
Preferably, one of R 1 to R 4 is phenyl, the remainder may be hydrogen or deuterium.
Preferably, any one of R 1 and R 2、R2 and R 3, and R 3 and R 4 are combined with each other to form a substituted or unsubstituted phenyl structure, or two of R 1 and R 2, and R 3 and R 4 are each combined with each other to form a substituted or unsubstituted phenyl structure, the remainder may be hydrogen. In addition, in the case where the above phenyl structure is substituted, it may be substituted with at least one hydrogen or deuterium.
In addition, in the above chemical formula 1, R 5 to R 8 may each be independently hydrogen or deuterium, and preferably, R 5 to R 8 may be each hydrogen or each deuterium.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
in addition, as an example, the present invention provides a method for producing a compound represented by the above chemical formula 1 as shown in the following reaction formula 1.
[ Reaction type 1]
In the above reaction formula 1, ar, R 1 to R 8, m, n, p and q are the same as defined in the above chemical formula 1, X is halogen, preferably X is chlorine or bromine.
The above reaction formula 1 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction may be changed according to a technique known in the art. The above-described production method can be more specifically described in the production example described later.
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, but may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron suppression layer, an electron injection and transport layer that performs electron injection and electron transport at the same time, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer containing the compound represented by the chemical formula 1.
The organic layer may include an electron-inhibiting layer including a compound represented by chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted (INVERTED TYPE)) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light emitting device constituted by a substrate 1, an anode 2, an organic layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer 3.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer 5, hole transport layer 6, electron suppression layer 7, light emitting layer 8, hole blocking layer 9, and electron injection and transport layer 10.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the above organic layers contains the compound represented by chemical formula 1 above. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; a multilayer structure such as LiF/Al or LiO 2/Al, but not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. Specific examples thereof include an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and unconjugated portions, but are not limited thereto.
The electron suppression layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and improving the probability of hole-electron bonding. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, a compound represented by the above chemical formula 1, an organic compound of an arylamine group, or the like can be used, but the present invention is not limited thereto.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq 3); carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The hole blocking layer refers to the following layer: the organic light-emitting layer is preferably formed on the light-emitting layer, and is preferably provided in contact with the light-emitting layer, and serves to improve the efficiency of the organic light-emitting layer device by adjusting the electron mobility, thereby preventing excessive migration of holes and improving the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance, and as examples of such a hole blocking substance, azine derivatives including triazines, triazole derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from an electrode and transports the received electrons to a light emitting layer and functions as an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high electron mobility. Examples of the specific electron injection and transport substance include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole (S),The compounds are used together with a derivative thereof, a metal complex, a nitrogen-containing five-membered ring derivative, or the like, but are not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Production example 1
After complete dissolution of compound a (7.49 g,21.22 mmol) and compound a1 (10.03 g,24.40 mmol) in 280mL of xylene (Xylene) in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.65 g,27.58 mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (Bis (tris-tert-butylphosphine) palladium (0)) (0.24 g,0.48 mmol) was added and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate, whereby compound 1 having the above-described structure was produced (8.16 g, yield: 53%).
MS[M+H]+＝729
Production example 2
After compound a (6.85 g,19.41 mmol) and compound a2 (10.29 g,22.32 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.42 g,25.23 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.20 g,0.39 mmol) was added, followed by stirring with heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of ethyl acetate to give Compound 2 (6.77 g, yield: 45%) having the above-mentioned structure.
MS[M+H]+＝779
Production example 3
After compound a (7.11 g,20.14 mmol) and compound a3 (8.31 g,22.16 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.52 g,26.18 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.40 mmol) was added, followed by stirring with heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, whereby compound 3 having the above-described structure was produced (8.49 g, yield: 61%).
MS[M+H]+＝693
Production example 4
After compound A (6.82 g,19.32 mmol) and compound a4 (9.24 g,21.25 mmol) were completely dissolved in 250mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (2.41 g,25.12 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.18 g,0.36 mmol) was added and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate to give Compound 4 (6.98 g, yield: 54%) having the above-mentioned structure.
MS[M+H]+＝753
Production example 5
After compound a (7.53 g,21.33 mmol) and compound a5 (10.21 g,23.46 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.66 g,27.73 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.22 g,0.43 mmol) was added, followed by stirring with heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, whereby compound 5 having the above-described structure was produced (7.61 g, yield: 49%).
MS[M+H]+＝729
Production example 6
After compound a (7.34 g,20.79 mmol) and compound a6 (11.09 g,22.87 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.31 g,34.45 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.42 mmol) was added, followed by stirring with heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate, whereby Compound 6 having the above-described structure was produced (8.62 g, yield: 53%).
MS[M+H]+＝779
PREPARATION EXAMPLE 7
After compound a (7.55 g,21.39 mmol) and compound a7 (9.69 g,23.53 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.67 g,27.80 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.22 g,0.43 mmol) was added, followed by stirring with heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, whereby Compound 7 having the above-described structure was produced (9.11 g, yield: 61%).
MS[M+H]+＝703
Production example 8
After complete dissolution of compound a (7.78 g,14.34 mmol) and compound a8 (7.44 g,16.49 mmol) in 250mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (2.07 g,21.51 mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.15 g,0.29 mmol) was added, followed by stirring with heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate, whereby compound 8 (6.79 g, yield: 58%) having the above-mentioned structure was produced.
MS[M+H]+＝803
Production example 9
After compound A (7.62 g,21.59 mmol) and compound a9 (12.11 g,23.75 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.70 g,28.06 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.22 g,0.43 mmol) was added and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of tetrahydrofuran, thereby producing Compound 9 (10.57 g, yield: 61%) having the above-mentioned structure.
MS[M+H]+＝818
Example 1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following compound HT1 is usedVacuum evaporation is performed to form a hole transport layer. Then, on the hole transport layer, the film thickness is set to beThe compound (1) of production example 1 was vacuum-evaporated to form an electron-inhibiting layer. Then, on the electron suppression layer, the film thickness is set to beThe following compound BH and the following compound BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. On the light-emitting layer, the film thickness is set toThe hole blocking layer was formed by vacuum evaporation of the following compound HB 1. Next, on the hole blocking layer, the following compound ET1 and the following compound LiQ were vacuum-evaporated at a weight ratio of 1:1, thereby forming a hole blocking layerForm an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added toTo the thickness of aluminumAnd vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs maintained by aluminumDuring vapor deposition, the vacuum degree was maintained at 2×10 -7～5×10-6 torr, thereby manufacturing an organic light-emitting device.
Examples 2 to 9
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of the compound 1 of manufacturing example 1.
Comparative examples 1 to 7
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of the compound of manufacturing example 1. EB1, EB2, EB3, EB4, EB5, EB6 and EB7 used in table 1 below are as follows.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting devices of examples 1 to 9 using the compound of the present invention as an electron suppression layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability. Specifically, the organic light emitting devices of examples 1 to 9 exhibited characteristics of low voltage, high efficiency, and long lifetime by using an amine substance directly substituted with dibenzothiophene attached to the ortho position of the biphenyl as an electron suppression layer.
In contrast, the organic light emitting devices of comparative examples 1 and 3 using the compounds EB1 and EB3 having amine-based substituents attached to the para-position of the biphenyl group exhibited deteriorated characteristics compared to the examples in terms of voltage increase, efficiency decrease, and particularly stability. Further, a compound EB2 containing 2 functional groups to which carbazole groups are attached at the ortho position of the biphenyl group was used as comparative example 2 of the electron-inhibiting layer; comparative example 4 in which compound EB4 having a carbazolyl group at the meta position to the biphenyl group was used as the electron-inhibiting layer; and comparative example 5 in which a compound in which dibenzofuranyl group is not directly bonded to amino group but bonded via a linking group such as phenylene group is used as an electron-inhibiting layer; and organic light emitting devices of comparative examples 6 and 7, in which compounds EB6 and EB7 containing biphenyl groups at Ar positions in chemical formula 1 without satisfying the carbon number condition were used as electron suppression layers, exhibited deteriorated characteristics in efficiency, driving voltage, and stability as compared with the examples.
While the preferred embodiment (electron suppression layer) of the present invention has been described above, the present invention is not limited thereto, and it is also within the scope of the present invention to be modified and implemented in various forms within the scope of the invention as claimed and the detailed description of the invention.
[ Description of the symbols ]
1: Substrate 2: anode
3: Organic layer 4: cathode electrode
5: Hole injection layer 6: hole transport layer
7: Electron suppression layer 8: light-emitting layer
9: Hole blocking layer 10: electron injection and transport layers.
Claims (9)
1. A compound represented by the following chemical formula 1:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
Ar is terphenyl, (phenyl) naphthyl, (naphthyl) phenyl, (naphthyl) biphenyl, (phenyl naphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, triphenylenyl, phenanthrenyl, or (phenanthrenyl) phenyl, said Ar being unsubstituted or substituted with at least one deuterium or C 1-18 alkyl group,
R 1 to R 4 are each independently hydrogen, deuterium, C 1-10 alkyl, or C 6-20 aryl,
R 5 to R 8 are each independently hydrogen; or deuterium, or both,
M is an integer of 0 to 3,
N is an integer of 0 to 8,
P and q are each independently integers from 0 to 4.
2. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1a to 1 d:
Chemical formula 1a
Chemical formula 1b
Chemical formula 1c
Chemical formula 1d
In the chemical formulas 1a to 1d,
Ar, R 1 to R 8, m, n, p and q are as defined in claim 1.
3. The compound of claim 1, wherein Ar is any one selected from the following formulas:
In the respective formulae described above, the chemical formula,
R 11 are identical and are each methyl or phenyl,
The dashed lines indicate the binding sites.
4. The compound of claim 1, wherein R 1 to R 4 are each hydrogen or are each deuterium.
5. The compound of claim 1, wherein one of R 1 to R 4 is phenyl,
The balance being hydrogen or deuterium.
6. The compound of claim 1, wherein R 5 to R 8 are all hydrogen.
7. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
8. An organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, one or more of the organic layers comprising the compound according to any one of claims 1 to 7.
9. The organic light-emitting device of claim 8, wherein the organic layer is an electron-inhibiting layer.
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| KR10-2020-0175628 | 2020-12-15 | ||
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| CN109096268A (en) * | 2018-09-11 | 2018-12-28 | 长春海谱润斯科技有限公司 | A kind of organic electroluminescent compounds and its organic electroluminescence device |
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