CN112074962A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN112074962A CN112074962A CN201980027405.5A CN201980027405A CN112074962A CN 112074962 A CN112074962 A CN 112074962A CN 201980027405 A CN201980027405 A CN 201980027405A CN 112074962 A CN112074962 A CN 112074962A
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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
- 230000008021 deposition Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 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
- 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
- 125000005241 heteroarylamino 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
- 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
- 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
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([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
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 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
- 125000002560 nitrile group Chemical group 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
- 125000001715 oxadiazolyl group Chemical group 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
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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]
- H10K50/18—Carrier blocking layers
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification relates to an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and a first organic layer and a second organic layer provided between the first electrode and the second electrode, wherein the first organic layer includes a compound represented by chemical formula 1, and the second organic layer includes a compound represented by chemical formula 3.
Description
Technical Field
The present application claims priority of korean patent application No. 10-2018-0104684, which was filed on 3.9.2018 from the korean patent office, the entire contents of which are incorporated in the present specification.
The present description relates to organic light emitting devices.
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 generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed 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 two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.
Conventionally, as a hole transport material used for an organic EL device, an aromatic diamine derivative or an aromatic condensed-ring diamine derivative is known. However, in this case, since the applied voltage is mostly high, there are problems such as a reduction in the lifetime of the device and an increase in power consumption. As a method for solving the above-mentioned problems, a method of doping an electron-accepting compound such as a lewis acid in a hole injection layer of an organic EL device or using it alone has been proposed. However, the above method has a limitation in injecting and transporting holes, and therefore, it is desired to induce the effects of low voltage, high efficiency and long life with a combination of substances between the hole transport layer and the hole adjusting layer or a combination of a hole transport layer and a plurality of hole adjusting layers. Typical hole transport layers are tertiary amines substituted with aromatic groups, and the device characteristics that can be found in this combination of materials each show various results. Therefore, there is a continuous demand for the development of new materials for improving the device characteristics by the transport of holes and carrier modulation.
Disclosure of Invention
Technical subject
The present specification provides an organic light emitting device.
Means for solving the problems
The organic light emitting device of the present specification includes: a first electrode, a second electrode provided so as to face the first electrode, and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,
the first organic layer includes a compound represented by the following chemical formula 1,
the second organic layer includes a compound represented by the following chemical formula 3:
[ chemical formula 1]
In the chemical formula 1, the first and second,
x is O or S, and X is O or S,
r1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
at least one of R1 to R4 is represented by the following chemical formula 2A or 2B,
n1 to n4 are each independently an integer of 1 to 4,
n1 to n4 are each independently 2 or more, the substituents in parentheses may be the same or different from each other,
[ chemical formula 2A ]
[ chemical formula 2B ]
In the chemical formulae 2A and 2B,
at least one of A1 to A3 is N, and the others are CH or combine with adjacent groups of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,
l1 to L3, which are the same as or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
ar4 and Ar5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
ar6 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, a is an integer of 0 to 5,
[ chemical formula 3]
In the chemical formula 3, the first and second,
x1 is N or CH,
ar1 to Ar3, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
Effects of the invention
An organic light emitting device using the compound according to an embodiment of the present specification for a hole blocking layer, an electron adjusting layer, an electron transporting layer, or an electron injecting and transporting layer, respectively, can achieve a low driving voltage, high light emitting efficiency, or a long life.
Drawings
Fig. 1,3 and 4 show examples of organic light emitting devices in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or electron regulating layer 6, an electron injection and transport layer 7, and a cathode 4 are sequentially stacked.
[ description of symbols ]
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole transport layer
6: hole blocking layer or electron regulating layer
7: electron injection and transport layer
Detailed Description
The present specification will be described in more detail below.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
The present specification provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and a first organic layer and a second organic layer provided between the first electrode and the second electrode, wherein the first organic layer includes a compound represented by chemical formula 1, and the second organic layer includes a compound represented by chemical formula 3.
According to one embodiment of the present specification, the compound represented by the above chemical formula 1 has an advantage that triplet energy can be adjusted by having the core structure as described above, and can exhibit characteristics of long life and high efficiency.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 has a lower absolute value of LUMO level than the compound represented by the above chemical formula 3 to smoothly transfer electrons to a light emitting layer, and thus an organic light emitting device including the above chemical formulas 1 and 3 has an excellent effect in efficiency and/or lifetime.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from the group consisting of hydrogen, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. 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, 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 60. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a3, 4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is 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. 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 amine group may be selected from-NH2The number of carbon atoms of the alkylamino group, the N-alkylarylamino group, the arylamine group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group, and the heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrylfluorenylamino group, and an N-biphenylfluorenylamino group.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 60. Specifically, the polycyclic aryl 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 adjacent substituents may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted,can be made into
And the like, but is not limited thereto.
In the present specification, the heterocyclic group contains 1 or more heteroatoms other than carbon atoms, specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthridinyl, phenanthrolinyl, isoquinoyl
Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiapyrrolyl, thiophenyl
Thienyl (phenoxathiine), thiophen
Examples of the oxazine group include, but are not limited to, an oxazine group, a phenothiazine group, a dihydroindenocarbazolyl group, a spirofluorenylxanthenyl group, and a spirofluorenylthioxanthyl group. Etc., but are not limited thereto. In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon, an aliphatic hydrocarbon, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the number of the hydrocarbon ring is not 1.
In the present specification, the aromatic hydrocarbon ring may be monocyclic or polycyclic, and may be selected from the above-mentioned examples of aryl groups except that it is not 1-valent.
In the present specification, the heterocyclic ring contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the heterocyclic group except that it has a valence of 1.
In the present specification, the 2-or 3-valent aryl group may be monocyclic or polycyclic, and means a group having 2 or 3 binding sites on the above aryl group, that is, a 2-or 3-valent group. The above description of aryl groups applies in addition to each being a 2-or 3-valent group.
In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.
In the present specification, a 2-valent heterocyclic group means a group having two binding sites on the heterocyclic group, that is, a 2-valent group. The above description of the heterocyclic group can be applied to each of them except that they are each a 2-valent group.
According to an embodiment of the present specification, the above R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, R1 to R4 are the same or different and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present disclosure, R1 to R4 are the same or different and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present disclosure, R1 to R4 are the same or different and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to an embodiment of the present specification, R1 to R4 are the same or different and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to an embodiment of the present disclosure, R1 to R4 are the same or different and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present disclosure, the group other than the following chemical formula 2A or 2B among the above R1 to R4 is hydrogen or deuterium.
According to an embodiment of the present disclosure, at least one of the groups other than the groups of the following chemical formula 2A or 2B among the groups R1 to R4 is an alkyl group, an aryl group, or an aryl group substituted with an alkyl group, and the remainder is hydrogen or deuterium.
According to an embodiment of the present disclosure, at least one of the groups other than the group of the following chemical formula 2A or 2B among the groups R1 to R4 is a methyl group; n-butyl; a tertiary butyl group; phenyl unsubstituted or substituted by methyl or tert-butyl; a naphthyl group; or fluorenyl substituted with methyl, the remainder being hydrogen or deuterium.
According to an embodiment of the present disclosure, n1 is 2, and the adjacent R1 are bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, n1 is 2, and the adjacent R1 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, n1 is 2, and the adjacent R1 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
According to an embodiment of the present disclosure, n1 is 2, and the adjacent R1 are bonded to each other to form a substituted or unsubstituted benzene ring.
According to an embodiment of the present disclosure, n1 is 2, and the adjacent R1 are bonded to each other to form a benzene ring.
According to an embodiment of the present disclosure, n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
According to an embodiment of the present disclosure, n2 is 2, and the adjacent R2 are bonded to each other to form a substituted or unsubstituted benzene ring.
According to an embodiment of the present disclosure, n2 is 2, and the adjacent R2 are bonded to each other to form a benzene ring.
According to an embodiment of the present disclosure, the n1 is 2, the adjacent R1 are bonded to each other to form a substituted or unsubstituted ring, the n2 is 2, and the adjacent R2 are bonded to each other to form a benzene ring.
According to an embodiment of the present disclosure, at least one of R1 to R4 is represented by the following chemical formula 2A or 2B.
[ chemical formula 2A ]
[ chemical formula 2B ]
In chemical formulas 2A and 2B, L1 to L3, Ar4 to Ar6, a1 to A3, and a are defined as above.
According to an embodiment of the present disclosure, one of the R1 to R4 is represented by the chemical formula 2A or 2B.
According to an embodiment of the present disclosure, 2 of the R1 to R4 are represented by the chemical formula 2A or 2B.
According to an embodiment of the present disclosure, one of the R2 and one of the R3 are represented by the chemical formula 2A or 2B.
According to an embodiment of the present disclosure, at least one of a1 to A3 is N, and the others are CH, or may be bonded to an adjacent group of L1, L2, L3, Ar4, and Ar5 to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, each of L1 to L3, which may be the same or different, is independently a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by bonding to an adjacent group of a1 to A3.
According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a phenylene group, or a biphenylene group.
According to one embodiment of the present disclosure, L3 represents a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a thienyl group having a valence of 2, a furyl group having a valence of 2, a dibenzothienyl group having a valence of 2, a carbazolyl group having a valence of 2 which is substituted or unsubstituted with an aryl or alkylaryl group, a benzocarbazolyl group having a valence of 2 which is substituted or unsubstituted with an aryl or alkylaryl group, a dibenzosilolyl group having a valence of 2 which is substituted or unsubstituted with an alkyl group, a thiophene group having a valence of 2
Thienyl (phenoxathiine), 2-valent thiophenes
A 2-valent pyridyl group, a 2-valent indanocarbazolyl group substituted or unsubstituted with an alkyl group, a 2-valent group in which dibenzothiophene and a phenyl group are linked, or a 2-valent group in which carbazole and a phenyl group are linked.
According to one embodiment of the present disclosure, L3 represents a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a thienyl group having a valence of 2, a furyl group having a valence of 2, a dibenzothienyl group having a valence of 2, a carbazolyl group having a valence of 2 which is substituted or unsubstituted with a phenyl or methylphenyl group, a benzocarbazolyl group having a valence of 2 which is substituted or unsubstituted with a phenyl or methylphenyl group, a dibenzosilolyl group having a valence of 2 which is substituted or unsubstituted with a methyl group, or a thiophene group having a valence of 2
Thienyl (phenoxathiine), 2-valent thiophenes
Azinyl (phenoxazine), phenothiazinyl (phenothiazine) having a valence of 2, pyridinyl having a valence of 2, substituted by a methyl group orUnsubstituted 2-valent indanocarbazolyl, a 2-valent group in which dibenzothiophene and phenyl are linked, or a 2-valent group in which carbazole and phenyl are linked.
According to one embodiment of the present disclosure, Ar4 and Ar5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with an adjacent group of a1 to A3 to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms bonded to an adjacent group from a1 to A3.
According to one embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted benzene ring formed by bonding to an adjacent group of a1 to A3.
According to one embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or a substituted or unsubstituted benzene ring formed by bonding to an adjacent group of a1 to A3.
According to one embodiment of the present disclosure, Ar4 and Ar5 are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms, or a substituted or unsubstituted benzene ring formed by bonding to an adjacent group of a1 to A3.
According to an embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with CN, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylsilyl group, an aryl group, an alkylaryl group, or a heterocyclic group; or a heterocyclic group having 2 to 15 carbon atoms which may be unsubstituted or substituted with CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylsilyl, aryl or a heterocyclic group, or may be bonded to an adjacent group of a1 to A3 to form a benzene ring.
According to an embodiment of the present disclosure, Ar4 and Ar5 are the same or different and each independently selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylene, phenanthrenyl, fluoranthenyl, phenalene, carbazolyl, benzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiapyrrolyl, thiophenyl
Thienyl (phenoxathiine), thiophen
Examples of the substituent group include a group in which one or more groups selected from the group consisting of an oxazinyl group, a phenothiazinyl group, a pyridyl group, a dihydroindenocarbazolyl group, an arylsilyl group, an alkylsilyl group, a spirofluorene xanthyl group and a spirofluorene thioxanthyl group are bonded, and these groups may be substituted with CN, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylsilyl group, an aryl group, an alkylaryl group or a heterocyclic group. Here, the heterocyclic group may be, as a substituent, a carbazolyl group, a benzocarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzothiapyrrolyl group, or a thiophene
Thienyl (phenoxathiine), thiophen
An oxazinyl group, a phenothiazinyl group, a pyridyl group, or an indanocarbazolyl group, as a substituent, the aryl group may be a phenyl group, a biphenyl group, a naphthyl group, or a triphenylene group. The alkyl group may be a methyl group or a tert-butyl group, the alkoxy group may be a methoxy group, the haloalkyl group may be a trifluoromethyl group, or the haloalkoxy groupMay be a trifluoromethoxy group, and the above-mentioned alkylsilyl group may be a methylsilyl group.
According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-5.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
[ chemical formulas 1 to 5]
In the above chemical formulas 1-1 to 1-5,
x, R1 to R4, L1 to L3, a1 to A3, Ar4, Ar5 and n1 to n4 are as defined above, and L1', L2', L3', a1', a2', A3', Ar4 'and Ar5' are as defined above for L1, L2, L3, a1, a2, A3, Ar4 and Ar5, respectively.
According to an embodiment of the present disclosure, 2 of a1 to A3 of the above chemical formula 2A are N.
According to an embodiment of the present disclosure, a1 to A3 of the above chemical formula 2A are N.
According to an embodiment of the present disclosure, the chemical formula 2A may be selected from the following structural formulae.
In the above structural formulae, L1 to L3, Ar4 and Ar5 are defined as above.
According to an embodiment of the present disclosure, Ar6 in chemical formula 2B is hydrogen.
According to an embodiment of the present specification, X1 is CH.
According to an embodiment of the present specification, X1 is N.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 60 carbon atoms out of 6 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 15 carbon atoms out of 6 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 15 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms; a biphenyl group; a naphthyl group; an anthracene group; phenanthryl; or a pyrenyl group.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a tert-butyl group or a phenyl group; a biphenyl group; a naphthyl group; an anthracene group; or phenanthryl.
According to an embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to one embodiment of the present specification, Ar3 denotes an aryl group having 6 to 20 carbon atoms, which is substituted with 1 or more carbon atoms selected from an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
According to one embodiment of the present specification, Ar3 denotes a phenyl group substituted with 1 or more selected from an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; a biphenyl group substituted with 1 or more selected from an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a terphenyl group substituted by 1 or more selected from an aryl group having 6 to 20 carbon atoms and a heterocyclic group having 2 to 20 carbon atoms.
According to one embodiment of the present specification, Ar3 is a phenyl group substituted with 1 or more groups selected from pyridyl groups substituted or unsubstituted with methyl or phenyl groups, dibenzothienyl groups substituted or unsubstituted with pyridyl groups, pyrimidinyl groups, pyrazinyl groups, quinolyl groups, phenanthrolinyl groups, benzothienyl groups, thienyl groups substituted or unsubstituted with thienyl groups, phenanthryl groups, pyrenyl groups, biphenyl groups, naphthyl groups, and anthracenyl groups; biphenyl substituted with 1 or more selected from pyridyl substituted or unsubstituted with methyl, pyrimidinyl substituted or unsubstituted with methyl, pyrazinyl, benzothienyl, dibenzothienyl, phenyl, naphthyl, phenanthryl, anthracyl, and pyrenyl; or a terphenyl group substituted by 1 or more selected from a pyridyl group and a phenanthryl group.
According to an embodiment of the present disclosure, the chemical formula 3 may be represented by the following chemical formula 3-1.
[ chemical formula 3-1]
In the chemical formula 3-1,
x1' is N or CH,
ar1 'and Ar2', which are the same or different from each other, are each independently a substituted or unsubstituted aryl group,
l is a direct bond, or a substituted or unsubstituted 2-or 3-valent aryl group,
ar3' is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
when n5 is 1 or 2 and n5 is 2, the substituents in parentheses are the same as or different from each other.
According to an embodiment of the present disclosure, X1' is CH.
According to an embodiment of the present disclosure, X1' is N.
According to an embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present specification, Ar1 'and Ar2', which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to one embodiment of the present specification, Ar1 'and Ar2', which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to one embodiment of the present specification, Ar1 'and Ar2', which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently represents an aryl group having 6 to 15 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms; a biphenyl group; a naphthyl group; an anthracene group; phenanthryl; or a pyrenyl group.
According to an embodiment of the present specification, Ar1 'and Ar2' are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a tert-butyl group or a phenyl group; a biphenyl group; a naphthyl group; an anthracene group; or phenanthryl.
According to an embodiment of the present specification, L is a direct bond.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 2 and having 6 to 60 carbon atoms.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 2 and having 6 to 30 carbon atoms.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 2 and having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L is a 2-valent aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L is phenylene.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 3 having 6 to 60 carbon atoms.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 3 and having 6 to 30 carbon atoms.
According to an embodiment of the present specification, L is a substituted or unsubstituted aryl group having a valence of 3 and having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L is a 3-valent phenyl group, a 3-valent biphenyl group, or a 3-valent terphenyl group.
According to an embodiment of the present specification, n5 is 1.
According to an embodiment of the present disclosure, when n5 is 2 and n5 is 2,2 or more Ar 3's are the same or different from each other.
According to an embodiment of the present disclosure, Ar3' is an aryl group having 6 to 60 carbon atoms; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heterocyclic group having 2 to 60 carbon atoms.
According to an embodiment of the present disclosure, Ar3' is an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms.
According to an embodiment of the present disclosure, Ar3' is an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 60 carbon atoms.
According to an embodiment of the present specification, Ar3' is a pyridyl group substituted or unsubstituted with a methyl group or a phenyl group; dibenzothienyl substituted or unsubstituted with pyridyl; a pyrimidinyl group; a pyrazinyl group; a quinolyl group; phenanthroline group; benzothienyl; thienyl substituted or unsubstituted with thienyl; phenanthryl; pyrenyl; a phenyl group; a biphenyl group; a naphthyl group; or an anthracene group.
According to an embodiment of the present specification, the chemical formula 3 is represented by any one of the following chemical formulas 3-2 to 3-5.
[ chemical formula 3-2]
[ chemical formulas 3-3]
[ chemical formulas 3-4]
[ chemical formulas 3-5]
In the above chemical formulas 3-2 to 3-5, Ar1 and Ar2 are defined as in chemical formula 3, at least one of Ar31 and Ar32, at least one of Ar34 and Ar35, and at least one of Ar36 and Ar37 are a substituted or unsubstituted heterocyclic group or an aryl group substituted with a heterocyclic group, and the remainder are a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and Ar33 is a substituted or unsubstituted heterocyclic group or an aryl group substituted with a heterocyclic group.
According to an embodiment, at least one of Ar31 and Ar32, at least one of Ar34 and Ar35, and at least one of Ar36 and Ar37 described above is a pyridyl group substituted or unsubstituted with methyl or phenyl; dibenzothienyl substituted or unsubstituted with pyridyl; a pyrimidinyl group; a pyrazinyl group; a quinolyl group; phenanthroline group; benzothienyl; or thienyl substituted or unsubstituted with thienyl.
According to one embodiment, Ar33 is pyridinyl or pyrimidinyl.
In addition, according to an embodiment of the present specification, the chemical formula 1 is selected from the following structural formulae.
In addition, according to an embodiment of the present specification, the chemical formula 3 is selected from the following structural formulae.
The first and second organic layers of the organic light-emitting device of the present specification may be formed of a single layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the first organic layer of the present specification may be composed of 1 to 3 layers. Further, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, or the like as an organic layer, or a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection and transport layer, or the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a greater or lesser number of organic layers may be included.
According to one embodiment of the present specification, the organic light-emitting device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.
In one embodiment of the present specification, the organic light-emitting device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, and a hole blocking layer.
In one embodiment of the present specification, the organic light emitting device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, an electron injection and transport layer, a hole adjusting layer, and an electron adjusting layer.
In addition, the organic light emitting device may further include an electron charge generation layer.
According to an embodiment of the present specification, the organic light emitting device includes: a first electrode; a second electrode provided to face the first electrode; and a light-emitting layer having 2 or more layers between the first electrode and the second electrode; and 2 or more first and second organic layers between the 2 or more light-emitting layers and the first electrode, or between the 2 or more light-emitting layers and the second electrode, wherein the 2 or more first and second organic layers each contain a compound represented by the chemical formula 1 or a compound represented by the chemical formula 3.
According to one embodiment of the present disclosure, the first organic layer includes a hole blocking layer or an electron adjusting layer, the second organic layer includes an electron transporting layer, the hole blocking layer or the electron adjusting layer includes the compound represented by chemical formula 1, and the electron transporting layer may include the compound represented by chemical formula 3.
According to an embodiment of the present disclosure, the first organic layer includes a hole blocking layer or an electron adjusting layer, the second organic layer includes an electron injecting and transporting layer, the hole blocking layer or the electron adjusting layer includes the compound represented by chemical formula 1, and the electron injecting and transporting layer may include the compound represented by chemical formula 3.
According to one embodiment of the present specification, the first and second organic layers include a hole injection layer or a hole transport layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.
In another embodiment, the organic light emitting device 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.
In another embodiment, the organic light emitting device 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, the structure of an organic light emitting device according to an embodiment of the present specification is illustrated in fig. 1 to 4.
Fig. 4 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In addition, if referring to fig. 1 and 3, the organic light emitting device according to an embodiment of the present specification may include 2 or more light emitting layers. In addition, each light emitting layer may independently include a fluorescent dopant or a phosphorescent dopant. When the light emitting layer is 2 layers, one light emitting layer may contain a fluorescent dopant and the other light emitting layer may contain a phosphorescent dopant.
According to one example, the organic light emitting device may include 2 or more light emitting layers emitting light in different wavelength ranges from each other between the first electrode and the second electrode.
In addition, according to one embodiment of the present specification, the 2 or more light-emitting layers may be arranged in a vertical direction from the first electrode to the second electrode, or may be arranged in a horizontal direction.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, a hole blocking layer or electron adjusting layer 6, an electron injecting and transporting layer 7, and a cathode 4 are sequentially stacked. If referring to fig. 2, the organic light emitting device according to an embodiment of the present specification may include 3 or more light emitting layers. Further, between each light emitting layer and the light emitting layer, other layers may be further disposed. When the above light emitting layers are arranged in 3 layers or more, each light emitting layer may include a blue fluorescent light emitting layer. Further, in the structure as shown in fig. 3, the compound represented by the above chemical formula 1 may be contained in the above hole blocking layer or electron adjusting layer 6, and the compound represented by the above chemical formula 3 may be contained in the electron injecting and transporting layer 7.
In addition, according to one embodiment of the present specification, the 3 or more light emitting layers may be arranged in a vertical direction from the first electrode to the second electrode, or may be arranged in a horizontal direction. More specifically, it may be arranged in a horizontal direction from the first electrode to the second electrode.
According to one embodiment of the present disclosure, the blue fluorescent light-emitting layer includes a host and a dopant, and the host may have any one structure selected from the following structures.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the first or second organic layers contains the compound of the present specification, i.e., the compounds represented by the above chemical formulas 1 and 3.
When the organic light emitting device includes a plurality of first or second organic layers, the organic layers may be formed of the same substance or different substances.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the first or second organic layers contains the above compound, i.e., the compound represented by any one of the above chemical formulas 1 and 3.
For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, first and second organic layers, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display 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) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron 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, an organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compounds of chemical formulas 1 and 3 may form an organic layer not only by a vacuum evaporation method but also by a solution coating method in manufacturing 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 may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.
According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, 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. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or 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-dioxy) thiophene]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. 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 multilayer structure material such as Al, but not limited thereto.
The hole injection material is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection material: 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, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
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 substance is a substance 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 substance 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 light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline 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 electron transporting material is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer.
The electron injection layer is injected from electricityThe layer of the polar electrons is preferably a compound of the formula: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are 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 hole-blocking layer is a layer that blocks holes from reaching the cathode, is a layer that regulates electrons reaching the light-emitting layer, and can serve as an electron-regulating layer. Further, the electron charge generation layer is a layer that generates an electron charge.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
The fabrication of the organic light emitting device comprising the compounds represented by the above chemical formulas 1 and 3 is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.
Production example 1: preparation of Compound EC1
The above-mentioned compound EC1-A (10g, 26.6mmol) and the above-mentioned compound EC1-B (12.3g, 26.6mmol) were completely dissolved in tetrahydrofuran (100mL), and then potassium carbonate (11.0g, 79.7mmol) was dissolved in 50mL of water and added. Tetrakis (triphenylphosphine) palladium (0.92g, 0.797mmol) was added, followed by stirring with heating for 8 hours. After the reaction was completed by cooling the temperature to normal temperature, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce compound EC1(15.4g, yield 81%).
MS[M+H]+＝716
Production example 2: preparation of Compound EC2
A compound represented by the above chemical formula EC2 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝553
Production example 3: preparation of Compound EC3
A compound represented by the above chemical formula EC3 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝640
Production example 4: preparation of Compound EC4
A compound represented by the above chemical formula EC4 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝640
Production example 5: preparation of Compound EC5
The above-mentioned compound EC5-A (10g, 17.1mmol) and the above-mentioned compound EC5-B (9.2g, 34.2mmol) were completely dissolved in tetrahydrofuran (100mL), and then potassium carbonate (7.1g, 51.3mmol) was dissolved in 50mL of water and added. Tetrakis (triphenylphosphine) palladium (0.59g, 0.513mmol) was added, followed by stirring with heating for 8 hours. After the reaction was completed by cooling the temperature to normal temperature, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce compound EC5(9.5g, yield 70%).
MS[M+H]+＝795
Production example 6: preparation of Compound EC6
A compound represented by the above chemical formula EC6 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝807
Production example 7: preparation of Compound EC7
A compound represented by the above chemical formula EC7 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝654
Production example 8: preparation of Compound EC8
A compound represented by the above chemical formula EC8 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝821
Production example 9: preparation of Compound EC9
A compound represented by the above chemical formula EC9 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝848
Production example 10: preparation of Compound EC10
A compound represented by the above chemical formula EC10 was produced in the same manner as in the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝537
Production example 11: preparation of Compound ET1
A compound represented by the above chemical formula ET1 was produced by the same method as the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝757
Production example 12: preparation of Compound ET2
A compound represented by the above chemical formula ET2 was produced by the same method as the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝591
Production example 13: preparation of Compound ET3
A compound represented by the above chemical formula ET3 was produced by the same method as the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝586
Production example 14: preparation of Compound ET4
A compound represented by the above chemical formula ET4 was produced by the same method as the production method of EC1 of production example 1, except that each starting material was used as in the above reaction formula.
MS[M+H]+＝487
Examples 1 to 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is 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, the following HI-A compound was added
The hole injection layer is formed by thermal vacuum deposition. Sequentially vacuum-depositing the HAT compound on the hole injection layer
And the following HT-A compounds
Thereby forming a hole transport layer.
Then, on the hole transport layer, the film thickness
The light-emitting layer was formed by vacuum evaporation of a BH compound and the following BD compound at a weight ratio of 25: 1.
The compound EC1 was vacuum-deposited on the light-emitting layer to form a layer
Forming a hole blocking layer. On the hole-blocking layer, the compound ET1 and the LiQ compound described below were vacuum-evaporated at a weight ratio of 1:1 to obtain a positive hole-blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Sec, maintenance of lithium fluoride at the cathode
Evaporation Rate,/sec, aluminum maintenance
A vapor deposition rate of/sec, and a degree of vacuum maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 1-2 to 1-20 and comparative examples 1-1 to 1-15
An organic light-emitting device was produced in the same manner as in example 1-1, except that compounds in table 1 below were used instead of the compounds EC1 and ET1 in example 1-1.
For the organic light emitting devices manufactured in the above examples 1-1 to 1-20 and comparative examples 1-1 to 1-15, at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time required for 90% to the initial brightness was measured at the current density of (1) (T90). The results are shown in table 1 below.
[ Table 1]
In table 1 above, comparing examples 1-1 to 1-20 with comparative examples 1-1 to 1-15, the organic light emitting devices using chemical formulas 1 and 3 according to the present specification are significantly superior in terms of lifetime compared to the organic light emitting device using only chemical formula 1 or chemical formula 3.
Example 2-1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is 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, the following HI-A compound was added
The first hole injection layer is formed by thermal vacuum deposition. Sequentially vacuum evaporating on the first hole injection layerPlating with the following HAT Compound
And the following HT-A compounds
Thereby forming a first hole transport layer.
Then, on the first hole transport layer, the film thickness
The first light-emitting layer was formed by vacuum evaporation of a BH compound and the following BD compound at a weight ratio of 25: 1.
Vacuum vapor-depositing the compound EC1 on the first light-emitting layer to form a layer
Forming a first hole blocking layer. On the first hole-blocking layer, the compound ET1 and the LiQ compound described below were vacuum-deposited at a weight ratio of 1:1 to form a hole-blocking layer
Forming a first electron injection and transport layer.
On the above-mentioned first electron injection and transport layer, in a film thickness
The compound ET-C and the lithium compound were vacuum-evaporated at a weight ratio of 100:2 to form an electron charge generation layer. On the above electron charge generation layer, a HI-A compound is added
The second hole injection layer is formed by thermal vacuum evaporation.
Sequentially vacuum-depositing the HAT compound on the second hole injection layer
And the following HT-A compounds
And a second hole transport layer is formed.
Then, on the second hole transport layer, the film thickness
The second light-emitting layer was formed by vacuum evaporation of a BH compound and the following BD compound at a weight ratio of 25: 1.
On the second light-emitting layer, a compound EC1 was added
The hole blocking layer is formed by vacuum evaporation. On the second hole-blocking layer, the compound ET1 and the LiQ compound described below were vacuum-evaporated at a weight ratio of 1:1 to obtain a positive hole-blocking layer
Forming the second electron injection and transport layer. On the above-mentioned second electron injecting and transporting layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Sec, maintenance of lithium fluoride at the cathode
Evaporation Rate,/sec, aluminum maintenance
(sec) ofVapor deposition speed, vacuum degree maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 2-2 to 2-20 and comparative examples 2-1 to 2-15
An organic light-emitting device was produced in the same manner as in example 2-1, except that compounds in table 1 below were used instead of the compounds EC1 and ET1 in example 2-1.
For the organic light emitting devices manufactured in the above examples 2-2 to 2-20 and comparative examples 2-1 to 2-15, at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time required for 90% to the initial brightness was measured at the current density of (1) (T90). The results are shown in table 2 below.
[ Table 2]
In table 2 described above, comparing examples 2-1 to 2-20 with comparative examples 2-1 to 2-15, the organic light emitting devices using chemical formulas 1 and 3 according to the present specification are significantly superior in terms of lifetime compared to the organic light emitting device using only chemical formula 1 or chemical formula 3.
Claims (13)
1. An organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode,
wherein the first organic layer includes a compound represented by the following chemical formula 1, and
the second organic layer includes a compound represented by the following chemical formula 3:
chemical formula 1
In the chemical formula 1, the first and second,
x is O or S, and X is O or S,
r1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,
at least one of R1 to R4 is represented by the following chemical formula 2A or 2B,
n1 to n4 are each independently an integer of 1 to 4,
n1 to n4 are each independently 2 or more, the substituents in parentheses may be the same or different from each other,
chemical formula 2A
Chemical formula 2B
In the chemical formulae 2A and 2B,
at least one of A1 to A3 is N, and the others are CH or combine with adjacent groups of L1, L2, L3, Ar4 and Ar5 to form a substituted or unsubstituted ring,
l1 to L3 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
ar4 and Ar5 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group of A1 to A3 to form a substituted or unsubstituted ring,
ar6 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, a is an integer of 0 to 5,
chemical formula 3
In the chemical formula 3, the first and second,
x1 is N or CH, and
ar1 to Ar3 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-5:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1 to 3
Chemical formulas 1 to 4
Chemical formulas 1 to 5
In the chemical formulas 1-1 to 1-5,
x, R1 to R4, L1 to L3, a1 to A3, Ar4, Ar5 and n1 to n4 are as defined in said claim 1, and L1', L2', L3', a1', a2', A3', Ar4 'and Ar5' are as defined for L1, L2, L3, a1, a2, A3, Ar4 and Ar5, respectively.
3. The organic light emitting device according to claim 1, wherein the chemical formula 3 is represented by the following chemical formula 3-1:
chemical formula 3-1
In the chemical formula 3-1,
x1' is N or CH,
ar1 'and Ar2' are the same or different from each other and each independently is a substituted or unsubstituted aryl group,
l is a direct bond, or a substituted or unsubstituted 2-or 3-valent aryl group,
ar3' is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
when n5 is 1 or 2 and n5 is 2, the substituents in parentheses are the same as or different from each other.
4. The organic light emitting device according to claim 1, wherein at least one of Ar1 to Ar3 of chemical formula 3 is an aryl group substituted with a heterocyclic group, or a substituted or unsubstituted heterocyclic group.
5. The organic light emitting device according to claim 1, wherein the chemical formula 1 is selected from the following structural formulae:
6. the organic light emitting device according to claim 1, wherein the chemical formula 3 is selected from the following structural formulae:
7. the organic light emitting device of claim 1, wherein the first organic layer is a hole blocking layer or an electron modulating layer.
8. The organic light emitting device of claim 1, wherein the second organic layer is an electron injection and transport layer.
9. The organic light-emitting device according to claim 1, wherein the organic light-emitting device comprises 2 or more light-emitting layers that emit light of wavelength ranges different from each other between the first electrode and the second electrode.
10. The organic light-emitting device according to claim 1, wherein the organic light-emitting device comprises 2 or more light-emitting layers between the first electrode and the second electrode,
each of the light emitting layers independently includes a fluorescent dopant or a phosphorescent dopant.
11. The organic light-emitting device according to claim 1, wherein the organic light-emitting device comprises 2 or more light-emitting layers between the first electrode and the second electrode,
either of the light-emitting layers contains a fluorescent dopant and the other of the light-emitting layers contains a phosphorescent dopant.
12. The organic light-emitting device according to claim 1, wherein the organic light-emitting device comprises 3 or more light-emitting layers between the first electrode and the second electrode,
each of the light emitting layers includes a blue fluorescent light emitting layer.
13. The organic light-emitting device according to claim 12, wherein the 3 or more light-emitting layers are arranged in order in a direction from the first electrode to the second electrode.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006120689A (en) * | 2004-10-19 | 2006-05-11 | Konica Minolta Holdings Inc | Organic electroluminescence element, display device and illumination device |
| CN105308035A (en) * | 2013-06-28 | 2016-02-03 | 株式会社Lg化学 | Hetero ring compound and organic light emitting diode comprising same |
| KR20170049440A (en) * | 2015-10-27 | 2017-05-10 | 주식회사 엘지화학 | Organic light emitting device |
| WO2017146466A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting element comprising same |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10135513B4 (en) | 2001-07-20 | 2005-02-24 | Novaled Gmbh | Light-emitting component with organic layers |
| JP2015074649A (en) * | 2013-10-11 | 2015-04-20 | 東ソー株式会社 | Triazine compounds having 4-pyridyl groups, and organic electroluminescent elements containing the same |
| CN111312912B (en) * | 2015-03-16 | 2023-01-06 | 株式会社Lg化学 | Organic light emitting device |
| KR101593368B1 (en) * | 2015-04-22 | 2016-02-11 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting diode comprising the same |
| KR101921377B1 (en) * | 2015-12-15 | 2018-11-22 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| KR102044427B1 (en) * | 2016-12-14 | 2019-11-14 | 주식회사 엘지화학 | Organic light emitting device |
| KR102055979B1 (en) * | 2017-05-29 | 2019-12-13 | 주식회사 엘지화학 | Organic light emitting device |
-
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006120689A (en) * | 2004-10-19 | 2006-05-11 | Konica Minolta Holdings Inc | Organic electroluminescence element, display device and illumination device |
| CN105308035A (en) * | 2013-06-28 | 2016-02-03 | 株式会社Lg化学 | Hetero ring compound and organic light emitting diode comprising same |
| KR20170049440A (en) * | 2015-10-27 | 2017-05-10 | 주식회사 엘지화학 | Organic light emitting device |
| WO2017146466A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting element comprising same |
| CN108336239A (en) * | 2017-01-04 | 2018-07-27 | 株式会社Lg化学 | Organic illuminating element |
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| KR102218349B1 (en) | 2021-02-22 |
| CN112074962B (en) | 2024-05-24 |
| KR20200026752A (en) | 2020-03-11 |
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