CN114728947A - Novel compound and organic light emitting device using the same - Google Patents
Novel compound and organic light emitting device using the same Download PDFInfo
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- CN114728947A CN114728947A CN202080077208.7A CN202080077208A CN114728947A CN 114728947 A CN114728947 A CN 114728947A CN 202080077208 A CN202080077208 A CN 202080077208A CN 114728947 A CN114728947 A CN 114728947A
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- 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
- 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
- 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
- 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
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 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
- 150000002503 iridium Chemical class 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 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
- 125000004433 nitrogen atom Chemical group N* 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- 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
- 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 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
- 229910052710 silicon Inorganic materials 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
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [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
- 150000003852 triazoles Chemical class 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
- 238000007738 vacuum evaporation 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
- 238000007740 vapor deposition Methods 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
- 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
Images
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-
- 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
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- Chemical & Material Sciences (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The 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 and 0017590 at 13/2020 and korean patent application No. 10-2020 and 0175628 at 12/15/2020, the entire contents disclosed in the documents of the korean patent application are included as a part of the present specification.
The present invention relates to a novel compound and an organic light emitting device 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, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An 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 the 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, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic substances used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
ar is C13-60Aryl, Ar is unsubstituted or substituted by at least one deuterium, C1-18Alkyl, or C6-18The substitution of aryl groups is carried out,
R1to R4Each independently hydrogen, deuterium, substituted or unsubstituted C1-60Alkyl, or substituted or unsubstituted C6-60An aryl group, or two adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic ring structure,
R5to R8Each independently is hydrogen; deuterium; halogen; a nitrile group; a silyl group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C2-60An alkenyl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
m is an integer of 0 to 3,
n is an integer of 0 to 8,
p and q are each independently an integer of 0 to 4.
In addition, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers include 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 for an organic layer of an organic light emitting device in which an improvement in efficiency, a low driving voltage, and/or an improvement in 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 composed of 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 composed of 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
The following description is made in more detail to help understanding of the present invention.
In the context of the present specification,
or
Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent 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 alkylsulfoxy group; an arylsulfenoxy group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents being bonded. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group 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, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms; or aryl having 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 in 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, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, 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 alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a1, 1-dimethyl-propyl group, a 1-propyl group, a, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.
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 a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may be
And the like. But is not limited thereto.
In the present 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,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned aryl group. 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 the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is exemplified by the same alkenyl groups as described above. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In this specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the aryl group or the cycloalkyl group can be applied. In this specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and in addition to this, the above description on the heterocyclic group can be applied.
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、R1to R8M, n, p and q are as defined above.
In addition, in the above chemical formula 1, preferably, Ar is terphenyl, (phenyl) naphthyl, (naphthyl) phenyl, (naphthyl) biphenyl, (phenylnaphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, triphenylenyl, phenanthrenyl, or (phenanthryl) phenyl,
ar as defined above may be unsubstituted or substituted with at least one deuterium, C1-18Alkyl, or C6-18Aryl substitution.
More preferably, Ar may be any one selected from the following chemical formulae:
in each of the above-mentioned chemical formulas,
R11identical or different, are each hydrogen, deuterium, C1-18Alkyl, or C6-18Aryl, preferably, the above R11Identical or different, are each hydrogen, deuterium, methyl or phenyl,
the dotted lines indicate the bonding position.
In addition, in the above chemical formula 1, R1To R4May each independently be hydrogen, deuterium or phenyl.
Preferably, R1To R4Both may be hydrogen or both may be deuterium.
Preferably, R1To R4One of which is phenyl and the others may be hydrogen or deuterium.
Preferably, R1And R2、R2And R3And R3And R4Either of which are bound to each other to form a substituted or unsubstituted phenyl structure, or R1And R2And R3And R4Two of which are each bound to each other to form a substituted or unsubstituted phenyl structure, the remainder may be hydrogen. Further, in the case where the above-mentioned phenyl structure is substituted, it may be substituted with at least one hydrogen or deuterium.
In addition, in the above chemical formula 1, R5To R8May each independently be hydrogen or deuterium, preferably, R5To R8Both may be hydrogen or both may be deuterium.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
in addition, the present invention provides, as an example, a method for producing the compound represented by the above chemical formula 1, as shown in the following reaction formula 1.
[ reaction formula 1]
In the above reaction scheme 1, Ar and R1To R8M, n, p and q are the same as defined in the above chemical formula 1, and X is halogen, preferably, X is chlorine or bromine.
The above reaction formula 1 is an amine substitution reaction, preferably in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction may be modified according to a technique known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers include 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 simultaneously, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a light emitting layer including the compound represented by the 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 including the compound represented by the above chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer including the compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device of a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted (inverted type) organic light emitting device 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 composed of 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 composed of 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 include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
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 produced as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) to form an anode, forming 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 on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes 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); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject 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; LiF/Al or LiO2And a multi-layer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrins (porphyrins), oligothiophenes, arylamine-based organic substances, hexanenitrile-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline-and polythiophene-based conductive polymers, and the like.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron-suppressing layer is a layer including: and a layer which is formed on the hole transport layer, is preferably provided in contact with the light-emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and thus improving the efficiency of the organic light-emitting device. The electron-inhibiting layer contains an electron-blocking substance, and examples of such electron-blocking substances include, but are not limited to, compounds represented by the above chemical formula 1, arylamine-based organic substances, and the like.
The luminescent material can receive holes from the hole transport layer and the electron transport layer respectivelyAnd a substance that emits light in the visible light region by combining electrons, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative, a heterocyclic ring-containing compound, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and the styrylamine compound is a compound having at least 1 arylvinyl group substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole-blocking layer isRefers to the following layers: and a layer which is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and which serves to prevent excessive hole migration by adjusting the electron mobility, thereby increasing the probability of hole-electron combination, thereby improving the efficiency of the organic light-emitting layer device. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include triazine derivatives, triazole derivatives, and the like,
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
The electron injection and transport layer is a layer that injects electrons from the electrode, transports the received electrons to the 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 injecting and transporting substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having a high mobility to electrons. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material 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 manufacture 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 provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
Production example 1
After completely dissolving compound A (7.49g, 21.22mmol) and compound a1(10.03g, 24.40mmol) in 280mL of Xylene (XYLENE) in a 500mL round-bottomed flask under a nitrogen atmosphere, NaOtBu (2.65g, 27.58mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.24g, 0.48mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate, thereby producing Compound 1(8.16g, yield: 53%) having the above structure.
MS[M+H]+＝729
Production example 2
After completely dissolving compound A (6.85g, 19.41mmol) and compound a2(10.29g, 22.32mmol) in 240mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (2.42g, 25.23mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.20g, 0.39mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of ethyl acetate, thereby producing Compound 2(6.77g, yield: 45%) having the above structure.
MS[M+H]+＝779
Production example 3
After completely dissolving compound A (7.11g, 20.14mmol) and compound a3(8.31g, 22.16mmol) in 230mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (2.52g, 26.18mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.21g, 0.40mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, thereby producing Compound 3(8.49g, yield: 61%) having the above structure.
MS[M+H]+＝693
Production example 4
After completely dissolving compound A (6.82g, 19.32mmol) and compound a4(9.24g, 21.25mmol) in 250mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (2.41g, 25.12mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.18g, 0.36mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate, thereby producing Compound 4(6.98g, yield: 54%) having the above structure.
MS[M+H]+＝753
Production example 5
In a 500mL round bottom flask under nitrogen atmosphere, after completely dissolving Compound A (7.53g, 21.33mmol) and Compound a5(10.21g, 23.46mmol) in 260mL of xylene, NaOtBu (2.66g, 27.73mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.22g, 0.43mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to normal temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, thereby producing Compound 5(7.61g, yield: 49%) having the above structure.
MS[M+H]+＝729
Production example 6
After completely dissolving compound A (7.34g, 20.79mmol) and compound a6(11.09g, 22.87mmol) in 240mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (3.31g, 34.45mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.21g, 0.42mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate, thereby producing Compound 6(8.62g, yield: 53%) having the above structure.
MS[M+H]+＝779
Production example 7
In a 500mL round bottom flask under nitrogen atmosphere, after completely dissolving compound A (7.55g, 21.39mmol) and compound a7(9.69g, 23.53mmol) in 230mL of xylene, NaOtBu (2.67g, 27.80mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.22g, 0.43mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing Compound 7(9.11g, yield: 61%) having the above structure.
MS[M+H]+＝703
Production example 8
After completely dissolving compound A (7.78g, 14.34mmol) and compound a8(7.44g, 16.49mmol) in 250mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (2.07g, 21.51mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.15g, 0.29mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to normal temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate, thereby producing Compound 8(6.79g, yield: 58%) having the above structure.
MS[M+H]+＝803
Production example 9
After completely dissolving compound A (7.62g, 21.59mmol) and compound a9(12.11g, 23.75mmol) in 230mL of xylene in a 500mL round-bottomed flask under nitrogen atmosphere, NaOtBu (2.70g, 28.06mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.22g, 0.43mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to normal temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of tetrahydrofuran, thereby producing Compound 9(10.57g, yield: 61%) having the above structure.
MS[M+H]+＝818
Example 1
Indium Tin Oxide (ITO) and a process for producing the same
Is covered withThe glass substrate coated in a thin film was put in distilled water in which a detergent was dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared as an anode, the compound HI1 and the compound HI2 were added in such a ratio that the molar ratio was 98:2 (molar ratio)
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, the following compound HT1 was added
Vacuum evaporation is performed to form a hole transport layer. Then, on the hole transport layer, the film thickness
The compound (1) of production example 1 was vacuum-deposited to form an electron-inhibiting layer. Next, the electron inhibiting layer is formed on the substrate to a film thickness
The 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 thickness of the film
The following compound HB1 was vacuum-evaporated to form a hole-blocking layer. Next, on the hole-blocking layer, the following compound ET1 and the following compounds were addedThe LiQ compound was vacuum-deposited at a weight ratio of 1:1 to obtain a film
The thickness of (a) forms an electron injection and transport layer. On the above electron injecting and transporting layer, lithium fluoride (LiF) is sequentially added
Thickness of aluminum and
is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Examples 2 to 9
An organic light-emitting device was produced in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of compound 1 of production example 1.
Comparative examples 1 to 7
An organic light-emitting device was produced 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 production example 1. EB1, EB2, EB3, EB4, EB5, EB6, and EB7 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the 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 nits) to 95%.
[ Table 1]
As shown in the above table 1, the organic light emitting devices of examples 1 to 9 using the compound of the present invention as an electron inhibiting layer showed excellent characteristics in terms of efficiency, driving voltage and stability. Specifically, the organic light emitting devices of examples 1 to 9 exhibited low voltage, high efficiency, and long life by using an amine substance directly substituted with dibenzothiophene attached to the ortho position of biphenyl group as an electron inhibiting layer.
In contrast, the organic light emitting devices of comparative examples 1 and 3 using the compounds EB1 and EB3 in which an amine-based substituent is attached to the para-position of biphenyl group showed deteriorated characteristics in terms of voltage increase, efficiency decrease, and particularly stability, as compared to the examples. Further, comparative example 2 in which compound EB2 containing 2 functional groups in which carbazolyl groups are attached to the ortho position to biphenyl groups was used as an electron-suppressing layer; comparative example 4 in which a compound EB4 in which the bonding position of the carbazolyl group to the biphenyl group is a meta-position was used as the electron suppression layer; and comparative example 5 in which a compound in which a dibenzofuranyl group is bonded not directly to an amino group but via a linking group such as a phenylene group is used as an electron-suppressing layer; and the organic light emitting devices of comparative examples 6 and 7 using the compounds EB6 and EB7 containing a biphenyl group at the Ar position in chemical formula 1 without satisfying the carbon number condition as an electron inhibiting layer also showed deteriorated characteristics in efficiency, driving voltage, and stability compared to the examples.
The preferred embodiment (electron suppression layer) of the present invention has been described above, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and the scope of the present invention is included.
[ description of symbols ]
1: substrate 2: anode
3: organic material layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: luminescent layer
9: hole-blocking layer 10: an electron injection and transport layer.
Claims (11)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
ar is C13-60Aryl, said Ar being unsubstituted or substituted by at least one deuterium, C1-18Alkyl, or C6-18The substitution of aryl groups is carried out,
R1to R4Each independently hydrogen, deuterium, substituted or unsubstituted C1-60Alkyl, or substituted or unsubstituted C6-60An aryl group, or two adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic ring structure,
R5to R8Each independently is hydrogen; deuterium; a halogen; a nitrile group; a silyl group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C2-60An alkenyl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
m is an integer of 0 to 3,
n is an integer of 0 to 8,
p and q are each independently integers of 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、R1to R8M, n, p and q are as defined in claim 1.
3. The compound of claim 1, wherein Ar is terphenyl, (phenyl) naphthyl, (naphthyl) phenyl, (naphthyl) biphenyl, (phenylnaphthyl) phenyl, dimethylfluorenyl, diphenylfluorenyl, triphenylenyl, phenanthrenyl, or (phenanthryl) phenyl,
ar is unsubstituted or substituted by at least one deuterium, C1-18Alkyl, or C6-18Aryl substitution.
4. The compound of claim 1, wherein Ar is any one selected from the following formulas:
in the respective chemical formulae, the following are mentioned,
R11the same or different, each independently is hydrogen, deuterium, C1-18Alkyl, or C6-18Aryl, and the dotted line indicates the binding site.
5. The compound of claim 1, wherein R1To R4Both hydrogen or both deuterium.
6. The compound of claim 1, wherein R1To R4One of them is phenyl and the others are hydrogen or deuterium.
7. The compound of claim 1, wherein R1And R2、R2And R3And R3And R4Are combined with each other to form a substituted or unsubstituted phenyl structure, or R1And R2And R3And R4Two of which are each bound to one another to form a substituted or unsubstituted phenyl structure,
the remainder being hydrogen.
8. The compound of claim 1, wherein R5To R8Both hydrogen or both deuterium.
9. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
10. an organic light emitting device, comprising: a first electrode, a second electrode disposed opposite the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers comprising the compound of any one of claims 1 to 9.
11. The organic light emitting device of claim 10, wherein the organic layer is an electron inhibiting layer.
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| KR1020200175628A KR102465242B1 (en) | 2020-02-13 | 2020-12-15 | Novel compound and organic light emitting device comprising the same |
| KR10-2020-0175628 | 2020-12-15 | ||
| PCT/KR2020/018434 WO2021162227A1 (en) | 2020-02-13 | 2020-12-16 | Novel compound and organic light-emitting device using same |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016072690A1 (en) * | 2014-11-04 | 2016-05-12 | 덕산네오룩스 주식회사 | Organic electronic device and display device using composition for organic electronic device |
| 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 |
| CN109476597A (en) * | 2017-02-24 | 2019-03-15 | 株式会社Lg化学 | New compound and the organic illuminating element for utilizing it |
Family Cites Families (5)
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| KR102292572B1 (en) * | 2014-11-07 | 2021-08-24 | 덕산네오룩스 주식회사 | Display device using a composition for organic electronic element, and an organic electronic element thereof |
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| JP2020093979A (en) * | 2017-03-08 | 2020-06-18 | 出光興産株式会社 | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
| WO2020111253A1 (en) * | 2018-11-30 | 2020-06-04 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016072690A1 (en) * | 2014-11-04 | 2016-05-12 | 덕산네오룩스 주식회사 | Organic electronic device and display device using composition for organic electronic device |
| CN109476597A (en) * | 2017-02-24 | 2019-03-15 | 株式会社Lg化学 | New compound and the organic illuminating element for utilizing it |
| 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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| CN116535345A (en) * | 2023-01-10 | 2023-08-04 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device comprising same |
| CN116535345B (en) * | 2023-01-10 | 2024-03-22 | 江苏三月科技股份有限公司 | Aromatic amine compound and organic electroluminescent device comprising same |
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