CN111448679B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN111448679B CN111448679B CN201980006180.5A CN201980006180A CN111448679B CN 111448679 B CN111448679 B CN 111448679B CN 201980006180 A CN201980006180 A CN 201980006180A CN 111448679 B CN111448679 B CN 111448679B
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- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 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
- 239000011248 coating agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 238000005314 correlation function Methods 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
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000001941 electron spectroscopy Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 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
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 238000007429 general method Methods 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
- 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000002513 implantation Methods 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 239000011133 lead Substances 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 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
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—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
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Abstract
The present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer and a hole-transporting layer, the light-emitting layer includes a compound represented by chemical formula 1, a compound represented by chemical formula 3 or 4, and the hole-transporting layer includes a compound represented by chemical formula 2.
Description
Technical Field
The present specification relates to organic light emitting devices.
The present application claims priority from korean patent application No. 10-2018-0096216, filed in the korean patent office on 8-17 of 2018, the entire contents of which are incorporated herein.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. If a voltage is applied to the organic light emitting device of such a structure, electrons and holes injected from 2 electrodes are combined in an organic thin film to be quenched and emitted light in pairs. The organic thin film may be formed of a single layer or a plurality of layers as required.
As the substance used in the organic light-emitting device, a pure organic substance or a complex compound of an organic substance and a metal constituting a complex is largely classified into a hole-injecting substance, a hole-transporting substance, a light-emitting substance, an electron-transporting substance, an electron-injecting substance, and the like depending on the application. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. As the light-emitting layer substance, a substance having both p-type property and n-type property, that is, a substance having a stable state in both of an oxidized state and a reduced state is preferable, and a substance having high light emission efficiency for converting excitons (exiton) generated by recombination of holes and electrons in the light-emitting layer into light is preferable.
In order to improve the performance, lifetime, or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.
Disclosure of Invention
Technical problem
An organic light emitting device having characteristics of low driving voltage, high efficiency, and long life is described in the present specification.
Solution to the problem
The present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer and a hole-transporting layer, the light-emitting layer includes a compound represented by the following chemical formula 1, further includes a compound represented by the following chemical formula 3 or 4, and the hole-transporting layer includes a compound represented by the following chemical formula 2.
[ chemical formula 1]
[ chemical formula 2]
In the above-mentioned chemical formulas 1 and 2,
x is O or S, and the X is O or S,
ar is a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent group to form a substituted or unsubstituted ring,
L1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar3 to Ar5 are the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or a heterocyclic group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group,
k1 to k3 are each integers of 0 to 2, and when k1 to k3 are 2, substituents in the brackets of 2 are each the same or different from each other,
n1 is an integer of 4 in 0, and when n1 is 2 or more, 2 or more Ar1 s are the same or different from each other,
n2 is an integer of 0 to 8, and when n2 is 2 or more, 2 or more Ar2 s are the same or different from each other,
[ chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
cy1 and Cy2 are the same or different from each other and each independently is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic group,
l101, L102 and L11 to L14 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r101 to R104 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
Y1 to Y13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
y4 and Y5 may combine to form a five-membered ring,
m and n are integers of 0 or 1,
at least one of m and n is an integer of 1,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
q1 and Q2 are the same or different from each other and are each, independently, O, S or C (Rf) (Rg),
r201 to R206, rf and Rg are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
cy3 and Cy4 are identical to or different from each other and are each independently a single-or multi-ring substituted or unsubstituted ring,
m1 and m2 are each an integer of 0 to 2, and when m1 and m2 are each 2, substituents in brackets are the same or different from each other.
Effects of the invention
The organic light emitting device of the present invention can obtain an organic light emitting device having a low driving voltage, high efficiency and long lifetime by including the compound represented by chemical formula 1 and the compound represented by chemical formula 3 or 4 in the light emitting layer and the compound represented by chemical formula 2 in the hole transporting layer. Specifically, by including a compound having a heteroaryl derivative such as dibenzofuran or dibenzothiophene as a substituent on anthracene as in the compound represented by chemical formula 1 in the light-emitting layer, the flow of electrons in the light-emitting layer can be made smooth. Meanwhile, when the compound represented by chemical formula 2 is used in the hole transport layer at the same time, the flow of holes in the organic light emitting device is smoothed, and thus charges of electrons and holes in the light emitting layer can be equalized. Thus, an organic light emitting device having a low driving voltage, high efficiency, and long life can be manufactured.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron injection and transport layer 7, and a cathode 4.
[ description of the symbols ]
1: substrate board
2: anode
3: light-emitting layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
The organic light emitting device of the present invention includes: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer and a hole-transporting layer, the light-emitting layer includes a compound represented by the following chemical formula 1, further includes a compound represented by the following chemical formula 3 or 4, and the hole-transporting layer includes a compound represented by the following chemical formula 2.
The above organic light emitting device has a compound represented by the following chemical formula 1 contained in a light emitting layer and a compound represented by the following chemical formula 2 contained in a hole transporting layer, so that the organic light emitting device has a low driving voltage and has an effect of improving the lifetime of the device.
[ chemical formula 1]
[ chemical formula 2]
In the above-mentioned chemical formulas 1 and 2,
x is O or S, and the X is O or S,
ar is a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent group to form a substituted or unsubstituted ring,
l1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar3 to Ar5 are the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or a heterocyclic group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group,
k1 to k3 are each integers of 0 to 2, and when k1 to k3 are 2, substituents in the brackets of 2 are each the same or different from each other,
n1 is an integer of 0 to 4, and when n1 is 2 or more, 2 or more Ar1 s are the same or different from each other,
n2 is an integer of 0 to 8, and when n2 is 2 or more, 2 or more Ar2 s are the same or different from each other,
[ chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
cy1 and Cy2 are the same or different from each other and each independently is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
l101, L102 and L11 to L14 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r101 to R104 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
y1 to Y13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
y4 and Y5 may combine to form a five-membered ring,
m and n are integers of 0 or 1,
at least one of m and n is an integer of 1,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
q1 and Q2 are the same or different from each other and are each, independently, O, S or C (Rf) (Rg),
R201 to R206, rf and Rg are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
cy3 and Cy4 are identical to or different from each other and are each independently a single-or multi-ring substituted or unsubstituted ring,
m1 and m2 are each an integer of 0 to 2, and when m1 and m2 are each 2, substituents in brackets are the same or different from each other.
In the present specification, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, it means that other components may be further included, and not excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, examples of the substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same 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 deuterium, halogen group, cyano (-CN), nitro, hydroxyl, silyl, boron group, alkyl, amino, cycloalkyl, phosphine oxide group, aryl, and heterocyclic group, or substituted with 2 or more substituents selected from the above exemplified substituents, or does not have any substituent. For example, a substituent in which 2 or more substituents are bonded may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be represented BY-BY d Y e The chemical formula of (A) is shown in the specification, Y is shown in the specification d And Y e Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,A group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
In the case where the fluorenyl group is substituted, it may be thatIsospirofluorenyl, < >>(9, 9-dimethylfluorenyl), and +.>Substituted fluorenyl such as (9, 9-diphenylfluorenyl), but not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more hetero atoms of N, O, S and Si, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarzolyl, and the like.
In the present specification, the amine group may be represented by-NY f Y g The chemical formula of (A) is shown in the specification, Y is shown in the specification f And Y g Each may be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. The amine group may be selected from an alkylamino group, an aralkylamino group, an arylamino group, an arylheteroarylamino group, an alkylheteroarylamino group, and a heteroarylamino group, and more specifically, may be a dimethylamino group, a diphenylamino group, a dicyclohexylamino group, or the like, but is not limited thereto.
In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the cycloalkyl group or the aryl group, in addition to the 2-valent group.
In the present specification, the aromatic hydrocarbon ring is a 2-valent group, and the above description of the aryl group can be applied.
In this specification, the heterocyclic ring is not limited to 2, and the above description of the heterocyclic group can be applied.
In the present specification, the above description of heteroaryl groups can be applied to aromatic heterocyclic rings other than 2-valent aromatic heterocyclic rings.
In this specification, unless the arylene group is a valence 2, the description of the aryl group may be applied.
In this specification, unless the heteroarylene group is 2-valent, the description of the heterocyclic group may be applied.
According to an embodiment of the present specification, ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to another embodiment, ar as described above is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, ar is an aryl group having 3 to 60 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.
In another embodiment, ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted phenanthryl group.
According to another embodiment, ar is phenyl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by phenyl, naphthyl or phenanthryl; biphenyl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; or phenanthryl substituted or unsubstituted with phenyl, naphthyl or phenanthryl.
According to another embodiment, ar is phenyl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by phenyl; a biphenyl group; or phenanthryl.
In another embodiment, ar is phenyl substituted or unsubstituted with naphthyl, naphthyl substituted or unsubstituted with phenyl, biphenyl, or phenanthryl.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group, 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, or a substituted or unsubstituted ring having 2 to 60 carbon atoms formed by bonding adjacent groups to each other.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, 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 ring having 2 to 30 carbon atoms, which is bonded to each other with an adjacent group.
According to an embodiment of the present specification, ar1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, 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, or when n1 is 2 or more, 2 or more Ar1 groups are bonded to each other to form a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
In another embodiment, ar1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, 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, or when n1 is 2 or more, 2 or more Ar1 groups are bonded to each other to form benzofuran, benzothiophene, dihydrobenzofuran, or dihydrobenzothiophene.
In one embodiment of the present specification, the above chemical formula 1 may be represented by the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
ar, ar2, n2 and X are as defined in chemical formula 1,
Y is O or S.
In one embodiment of the present specification, n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more Ar1 s are the same or different from each other.
According to an embodiment of the present specification, ar2 is hydrogen.
In one embodiment of the present specification, n2 is an integer of 0 to 2, and when n2 is 2 or more, 2 Ar2 are the same or different from each other.
In another embodiment, n2 is 0 or 1.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a directly bonded or substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
According to another embodiment, the above-mentioned L1 to L3 are the same or different from each other, and are each independently a directly bonded, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In another embodiment, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.
According to another embodiment, the above-mentioned L1 to L3 are identical to or different from each other and are each independently a direct bond, phenylene, biphenylene, terphenylene or naphthylene.
According to another embodiment, the above-mentioned L1 to L3 are identical to or different from each other and are each independently a directly bonded or monocyclic arylene group.
According to another embodiment, the above-mentioned L1 to L3 are identical to or different from each other and are each independently a direct bond, phenylene, biphenylene or terphenylene.
According to another embodiment, the above-mentioned L1 to L3 are identical to or different from each other and are each independently a direct bond, phenylene or biphenylene.
According to an embodiment of the present specification, when k1 is an integer of 0 to 2 and k1 is 2 or more, 2L 1 are the same or different from each other.
According to an embodiment of the present specification, when k2 is an integer of 0 to 2 and k2 is 2 or more, 2L 2 are the same or different from each other.
According to an embodiment of the present specification, when k3 is an integer of 0 to 2 and k3 is 2 or more, 2L 3 are the same or different from each other.
According to an embodiment of the present specification, the above Ar3 to Ar5 are the same or different from each other, each independently being an aryl group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or heteroaryl substituted or unsubstituted with alkyl, aryl or heterocyclyl.
According to an embodiment of the present specification, the above Ar3 to Ar5 are the same or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group, or a heteroaryl group.
According to an embodiment of the present specification, the above Ar3 to Ar5 are the same or different from each other, and each is independently an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or heteroaryl having 2 to 60 carbon atoms substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group.
According to another embodiment, the above Ar3 to Ar5 are the same or different from each other, each independently being an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or heteroaryl having 2 to 30 carbon atoms substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group.
In another embodiment, ar3 to Ar5 are the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment, the above Ar3 to Ar5 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
According to another embodiment, the above Ar3 to Ar5 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group unsubstituted with a methyl group or a phenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group substituted with a phenyl group or unsubstituted with a phenyl group, a dibenzofuranyl group, or a dibenzothienyl group.
According to another embodiment, ar3 to Ar5 mentioned above are the same as or different from each other, and are each independently phenyl, biphenyl, terphenyl, naphthyl, 9-dimethylfluorenyl, phenanthryl, triphenylenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl.
According to an embodiment of the present specification, 1 or more of Ar3 to Ar5 are aryl groups substituted with a heterocyclic group, or heterocyclic groups. In the case where 1 or more of Ar3 to Ar5 are substituents containing a heterocyclic ring, the dipole moment (dipole moment) is large, and thus when contained in the hole transport layer, the hole transport ability is excellent, and the efficiency of the device can be increased.
In one embodiment of the present specification, the above- (L1) k1 -Ar3、-(L2) k2 Ar4 and- (L3) k3 More than 2 of Ar5 may have the same structure. In this case, there is an advantage that the synthesis of the compound is easy, and since the stacked structure between molecules is compact and hole transfer between molecules is easy, there is an effect that hole transport ability is improved and device efficiency is increased.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following compounds.
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In one embodiment of the present specification, the chemical formula 2 is represented by any one of the following compounds.
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According to an embodiment of the present specification, m and n are 1.
According to an embodiment of the present specification, the triplet energy value of the compound represented by the above chemical formula 2 is equal to or greater than the triplet energy value of the compound represented by the above chemical formula 1.
According to an embodiment of the present specification, when the compound represented by chemical formula 1 is used as a host material of a light-emitting layer, excitons (exiton) are generated based on the combination of holes and electrons injected from a hole injection layer and an electron injection layer. At this time, singlet excitons (single excitons) and triplet excitons (triplet excitons) are formed at a ratio of 1:3. After energy transfer from excitons formed in the host to the dopant species is achieved by an energy transfer process, the excited dopant species return to the ground state and release energy in the process. In general, in the case of an organic compound, transfer from a triplet excited state to a singlet ground state requires a directional transition of spin orbitals (spin orbitals), and is therefore limited. However, another singlet exciton may be generated by triplet-triplet annihilation of the host species (triplet-triplet annihilation), which may contribute to an improvement in device efficiency.
Therefore, if triplet excitons of the host substance are trapped in the light-emitting layer and the possibility of triplet-triplet annihilation is increased, the device efficiency improvement can be greatly improved. When the triplet energy of the compound represented by the above chemical formula 2 is equal to or higher than the triplet energy of the host substance represented by the above chemical formula 1, the triplet energy is reduced from flowing out into the hole transport layer containing the compound represented by the above chemical formula 2, and therefore the efficiency of the device can be improved.
In one embodiment of the present disclosure, the light emitting layer includes a compound represented by the above chemical formula 1, and further includes a compound represented by the following chemical formula 3 or 4, and the absolute value of the LUMO level of the compound represented by the above chemical formulas 3 and 4 is equal to or less than the absolute value of the LUMO level of the compound represented by the above chemical formula 1.
In the present specification, "energy level" refers to the amount of energy. Therefore, even in the case where the energy level is expressed from the vacuum energy level to the negative (-) direction, the energy level is interpreted as an absolute value representing the energy value. For example, HOMO (highest occupied molecular orbital ) energy level refers to the distance from the vacuum energy level to the highest occupied molecular orbital. In addition, LUMO (lowest unoccupied molecular orbital ) energy level refers to the distance from the vacuum energy level to the lowest unoccupied molecular orbital.
In this specification, HOMO (highest occupied molecular orbital ) energy levels and LUMO (lowest unoccupied molecular orbital, lowest Unoccupied Molecular Orbital) energy level values were measured as follows.
To determine the molecular structure of a chemical, the structure of the input is optimized using density functional theory (density function al theory, DFT). For the DFT calculation, BPW91 calculation (beck exchange function and Perdew correlation function, becke exchange and Perde w correlation-correlation functional) and DNP (double-valued basis set of polarization functions, d ouble numerical basis set including polarization functional) basis set (basic set) were used. BPW91 calculation is disclosed in papers "A.D.Becke, phys.Rev.A,38,3098 (1988)" and "j.p. perdew and Y.Wang, phys.Rev.B,45,13244 (1992)", and DNP basis set is disclosed in papers "B.Delley, J.Chem.Phys.,92,508 (1990)".
To perform the calculations using density functional theory, the Biovia company "DMol3" package (package) may be used. When the optimum molecular structure is determined by the method given above, as a result, the electron-occupiable energy level can be obtained. The HOMO energy is the orbital energy of the highest energy level among the electron-filled molecular orbitals when the energy of the neutral state is obtained, and the LUMO energy corresponds to the orbital energy of the lowest energy level among the electron-non-filled molecular orbitals.
* HOMO/LUMO calculation
Experimentally, the HOMO level uses an IP (ionization potential ) value (formula-1 below) measured by UPS (ultraviolet electron spectroscopy, ultraviolet photoemission spectroscopy) or the like, and the LUMO level generally uses a value obtained by subtracting an Optical Gap (Optical Gap) from the HOMO level (formula-2 below).
[ 1]
Homo=ip (ionization potential)
[ 2]
Lumo=ip-optical gap
The values actually measured in the experiment are calculated together with the HOMO and LUMO in the theoretical neutral state (neutral state), and calculated by the following two methods are provided.
Method 1) method utilizing IP and optical gap
The IP and optical gap of the X molecule were determined by the calculation method in the experiment using the following formulas-3 and-4.
[ 3]
IP (ionization potential) =e X+ Cations (cationic) -E x Neutral
[ 4]
Optical gap = E S1 S0 -E S0 S0
In the above-mentioned-3, the above-mentioned,refers to geometry (geometry) optimized with cation (cation), anion (anion) or neutral (neutral) of structure with charge (charge) of 0, X + Or X - Is a function of the energy of the (c). That is, electron affinity refers to the difference between the most safe energy of the neutral structure and the most safe energy of the anion, and may refer to the energy released when one electron is added in the neutral state.
In the above formula-4, S0 is a singlet state of the ground state (ground state), S1 is a singlet state of the first excited state (excited state), E S1 S0 Refers to the difference between the singlet energy of the ground state and the singlet energy of the first excited state, E S0 S0 Refers to the difference in energy inside the singlet state of the ground state. At this time E S0 S0 Refers to the difference in energy caused by a geometrical change inside the singlet state of the ground state. Further, assuming that the structural changes of S0 and S1 are not large, the energy absorbed (absorption) is similar to the fluorescence (fluorescence) value. Thus, the optical gap corresponds to the S0-S1 gap (gap). The energy of the ground state and the excited state is based on a value calculated by the density functional theory.
Method 2) method of utilizing Solid state (Solid state) IP and optical gap
Since the layer is in a solid state (solid state) rather than a single molecule, the effect at that time is corrected in consideration of the molecular shape and the like as shown in the following formula-5, and a HOMO calculated (calc.) value can be obtained, and the LUMO energy level can be obtained by substituting the value into the IP value of the above formula-2. But cannot calculate the transition metal.
[ 5]
HOMO calc=ip+ [ delta ] (solid/molecule)
In the above formula-5, Δ (solid/molecule) means the difference between energies in a single-molecule state (Molecular state) and a solid state (solid state), and may affect the Asphericity (Asphericity), radius of gyration (Radius of gyration), molecular weight (Molecular weight), and the like.
In the present specification, the triplet energy can also be calculated using the density functional theory. The triplet energy can be obtained from the difference between the energies of SO-T1, where T1 is the triplet state of the first excited state.
The organic light emitting device of the present invention includes a compound represented by the above chemical formula 1 as a host of a light emitting layer, and a compound represented by the above chemical formula 3 or chemical formula 4 as a dopant of the light emitting layer. At this time, the content of the dopant is contained in an amount of 0.5 to 10 parts by weight, preferably 1 to 5 parts by weight, based on 100 parts by weight of the main body. When the dopant is contained in the light-emitting layer in the above-described content range, the organic light-emitting device to be manufactured has advantages of low driving voltage, long life and excellent light-emitting efficiency.
According to an embodiment of the present specification, cy1 and Cy2 are the same or different from each other, and each is independently a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to another embodiment, cy1 and Cy2 are the same or different from each other and each is independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.
In another embodiment, cy1 and Cy2 are the same or different from each other, and each is independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
In one embodiment of the present specification, cy1 and Cy2 may be the same or different from each other, and each may be independently selected from any one of the following structural formulas, and the following structure may be substituted with 1 or more substituents selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 60 carbon atoms.
According to an embodiment of the present specification, the above L101, L102 and L11 to L14 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
In another embodiment, L101, L102 and L11 to L14 are directly bonded.
According to an embodiment of the present specification, R101 to R104 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or are combined with each other to form a substituted or unsubstituted heterocyclic ring.
According to another embodiment, the above R101 to R104 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or are combined with each other with an adjacent group to form a substituted or unsubstituted heterocyclic ring.
In another embodiment, R101 to R104 are the same or different from each other and each is independently a phenyl group substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; biphenyl substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; a terphenyl group substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms; naphthyl substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; a fluorenyl group substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms; or a naphthobenzofuranyl group substituted or unsubstituted with deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms, or a carbazolyl group substituted or unsubstituted with alkyl having 1 to 20 carbon atoms is formed by bonding adjacent groups to each other.
According to an embodiment of the present specification, the above Y1 to Y13 are the same or different from each other, each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Y4 and Y5 may be combined to form a five-membered ring.
According to an embodiment of the present specification, the above Y1 to Y13 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.
According to another embodiment, the above Y1 to Y13 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
According to another embodiment, the above Y1 to Y13 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted tert-butyl group.
In one embodiment of the present specification, Y1 to Y13 are the same or different from each other, and each is independently hydrogen, deuterium, or tert-butyl.
In one embodiment of the present disclosure, Y4 and Y5 may be combined to form a five-membered ring.
According to an embodiment of the present specification, the above chemical formula 3 is represented by the following chemical formula 3-1 or 3-2.
[ chemical formula 3-1]
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[ chemical formula 3-2]
In the above chemical formulas 3-1 and 3-2,
l101, L102, L11 to L14, R101 to R104, Y1 to Y13, m and n are as defined in the above chemical formula 3,
either X11 or X12 is a direct bond, the remainder being O, S, C (R31) (R32) or Si (R33) (R34),
either of X13 and X14 is a direct bond, the remainder being O, S, C (R35) (R36) or Si (R37) (R38),
w1 to W4 are the same as or different from each other, each independently is N or C (R39), one or more of W1 to W4 is N,
r21 to R39 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, any one of X11 and X12 is directly bonded, and the remainder is O, S, C (R31) (R32) or Si (R33) (R34).
In one embodiment of the present specification, X11 is O, and X12 is a direct bond.
In one embodiment of the present disclosure, X11 is S and X12 is a direct bond.
In one embodiment of the present specification, X11 is C (R31) (R32), and X12 is a direct bond.
In one embodiment of the present specification, X11 is Si (R33) (R34), and X12 is a direct bond.
In one embodiment of the present specification, X11 is a direct bond, and X12 is O.
In one embodiment of the present disclosure, X11 is a direct bond, and X12 is S.
In one embodiment of the present specification, X11 is a direct bond, and X12 is C (R31) (R32).
In one embodiment of the present specification, X11 is a direct bond, and X12 is Si (R33) (R34).
In one embodiment of the present specification, any one of X13 and X14 is directly bonded, and the remainder is O, S, C (R35) (R36) or Si (R37) (R38).
In one embodiment of the present specification, X13 is O, and X14 is a direct bond.
In one embodiment of the present specification, X13 is S and X14 is a direct bond.
In one embodiment of the present specification, X13 is C (R35) (R36), and X14 is a direct bond.
In one embodiment of the present specification, X13 is Si (R37) (R38), and X14 is a direct bond.
In one embodiment of the present specification, X13 is a direct bond, and X14 is O.
In one embodiment of the present specification, X13 is a direct bond, and X14 is S.
In one embodiment of the present specification, X13 is a direct bond, and X14 is C (R35) (R36).
In one embodiment of the present specification, X13 is a direct bond, and X14 is Si (R37) (R38).
In one embodiment of the present specification, R39 is hydrogen.
In one embodiment of the present specification, R31 and R32 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R31 and R32 are the same or different from each other, and each is independently methyl.
In one embodiment of the present specification, R35 and R36 are the same or different from each other and each independently is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R35 and R36 are the same or different from each other, and each is independently methyl.
In one embodiment of the present specification, R33 and R34 are the same or different from each other and each independently is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R33 and R34 are the same or different from each other, and each is independently methyl.
In one embodiment of the present specification, R37 and R38 are the same or different from each other and each independently is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R37 and R38 are the same or different from each other, and each is independently methyl.
In one embodiment of the present specification, R21 to R30 are the same or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
In another embodiment, R21 to R30 are the same or different and each is independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or are bonded to each other with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
In one embodiment of the present specification, R21 to R30 are hydrogen or are bonded to each other with an adjacent group to form a benzene ring.
According to an embodiment of the present specification, the above chemical formula 3 is represented by any one of the following compounds.
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According to an embodiment of the present specification, Q1 and Q2 are the same or different from each other, and each is independently O, S or C (Rf) (Rg).
According to an embodiment of the present specification, rf and Rg are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
In another embodiment, rf and Rg are the same or different from each other, and each independently is a substituted or unsubstituted methyl group.
In one embodiment of the present specification, R201 to R204 are the same or different from each other and each is independently hydrogen, a halogen group, cyano (-CN), a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to another embodiment, the above-mentioned R201 to R204 are the same as or different from each other, and are each independently hydrogen, a halogen group, a cyano group (-CN), a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, R201 to R204 are the same or different from each other and each independently is hydrogen, a halogen group, a cyano group (-CN), a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above-mentioned R201 to R204 are the same as or different from each other, and are each independently hydrogen, a halogen group, a cyano group (-CN), an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, R201 to R204 are the same or different from each other and are each independently hydrogen, a halogen group, cyano (-CN), methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, or naphthyl.
According to an embodiment of the present disclosure, R201 to R204 are hydrogen or cyano.
In one embodiment of the present specification, R205 and R206 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano (-CN), a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, R205 and R206 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to another embodiment, R205 and R206 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, R205 and R206 are the same or different and each is independently hydrogen, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment, R205 and R206 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
In another embodiment, R205 and R206 are the same or different and are each independently hydrogen, an arylamine group substituted or unsubstituted with an alkyl group, an arylheteroarylamine group substituted or unsubstituted with an alkyl group, an aryl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or a heteroaryl group substituted or unsubstituted with an alkyl group having 2 to 30 carbon atoms.
In another embodiment, R205 and R206 are the same or different from each other and are each independently hydrogen, an arylamine group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, an arylheteroarylamine group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, an aryl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
According to another embodiment, R205 and R206 described above are the same or different from each other, and are each independently hydrogen, a diphenylamino group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, a phenylnaphthylamino group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, a biphenylphenylamine group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, a fluorenylphenylamino group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, a dibenzofuran phenylamino group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, a phenyl group substituted or unsubstituted by an aryl group having 6 to 30 carbon atoms, a naphthyl group substituted or unsubstituted by an aryl group having 6 to 30 carbon atoms, an anthryl group substituted or unsubstituted by an aryl group having 6 to 30 carbon atoms, a phenanthryl group substituted or unsubstituted by an aryl group having 6 to 30 carbon atoms, or a carbazolyl group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms.
In another embodiment, R205 and R206 are the same or different from each other and are each independently hydrogen, a diphenylamino group substituted or unsubstituted by 1 or more of methyl and t-butyl, a phenylnaphthylamino group substituted or unsubstituted by 1 or more of methyl and t-butyl, a biphenylphenylamino group substituted or unsubstituted by 1 or more of methyl and t-butyl, a fluorenylphenylamino group substituted or unsubstituted by 1 or more of methyl and t-butyl, a dibenzofuranphenylamino group substituted or unsubstituted by 1 or more of methyl and t-butyl, a phenyl group, a naphthyl group, an anthracenyl group substituted or unsubstituted by phenyl group, a phenanthrenyl group substituted or unsubstituted by phenyl group, or a carbazolyl group substituted or unsubstituted by phenyl group.
According to an embodiment of the present disclosure, each of m1 and m2 is 1 or 2, R205 is the same as or different from each other when m1 is 2, and R206 is the same as or different from each other when m2 is 2.
According to an embodiment of the present specification, cy3 and Cy4 are the same or different from each other, and each is independently a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring or a monocyclic or polycyclic substituted or unsubstituted heterocyclic ring.
According to another embodiment, cy3 and Cy4 are the same or different from each other and are each independently a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a monocyclic or polycyclic substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.
In another embodiment, cy3 and Cy4 are the same or different from each other, and each is independently a monocyclic or polycyclic substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
According to another embodiment, cy3 and Cy4 described above form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indene (indene) ring.
In another embodiment, cy3 and Cy4 form a benzene ring, naphthalene ring, benzofuran ring, benzothiophene ring, or an indene (indene) ring substituted with an alkyl group.
According to another embodiment, cy3 and Cy4 described above form a benzene ring, a naphthalene ring, a benzofuran ring, a benzothiophene ring, or an indene (indene) ring substituted with methyl.
According to an embodiment of the present specification, the above chemical formula 4 is represented by the following chemical formula 4-1 or 4-2.
[ chemical formula 4-1]
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[ chemical formula 4-2]
In the above chemical formulas 4-1 and 4-2,
q1, Q2, R201 to R204, cy1 and Cy2 are as defined in chemical formula 4,
r301, R302, and Ar11 to Ar14 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, R301 and R302 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, R301 and R302 are the same or different and each is independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment, R301 and R302 are the same as or different from each other, and each is independently hydrogen, an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with an alkyl group.
In another embodiment, R301 and R302 are the same or different from each other, and each is independently hydrogen, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
According to another embodiment, R301 and R302 described above are the same or different from each other, and are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, or a carbazolyl group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms.
In another embodiment, R301 and R302 are the same or different and each is independently hydrogen, phenyl, biphenyl, naphthyl, phenyl-substituted anthryl, phenanthryl, carbazolyl, or di-tert-butylcarbazolyl.
According to an embodiment of the present specification, the above-mentioned Ar11 to Ar14 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to another embodiment, ar11 to Ar14 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
In another embodiment, ar11 to Ar14 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment, ar11 to Ar14 are the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with an alkyl group.
In another embodiment, ar11 to Ar14 are the same or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
According to another embodiment, ar11 to Ar14 described above are the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 1 or more of a methyl group and a tert-butyl group, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with one or more of a methyl group and a tert-butyl group.
According to another embodiment, ar11 to Ar14 described above are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with 1 or more of methyl and tert-butyl, a biphenyl group substituted or unsubstituted with 1 or more of methyl and tert-butyl, a naphthyl group substituted or unsubstituted with 1 or more of methyl and tert-butyl, a fluorenyl group substituted or unsubstituted with 1 or more of methyl and tert-butyl, or a dibenzofuranyl group substituted or unsubstituted with 1 or more of methyl and tert-butyl.
In one embodiment of the present specification, the chemical formula 4 may be represented by any one of the following structures.
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In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structures of the above chemical formula 1 and chemical formula 2. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the above structure.
The organic light-emitting device of the present specification can be manufactured by a general method and materials for manufacturing an organic light-emitting device, except that the light-emitting layer is formed by using the compound represented by the above chemical formula 1 and the hole-transporting layer is formed by using the compound represented by the above chemical formula 2.
In the case of manufacturing an organic light-emitting device in which a light-emitting layer containing a compound represented by the above chemical formula 1 and a hole-transporting layer containing a compound represented by the above chemical formula 2 are formed, the organic layer may be formed not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic light emitting device of the present specification may further include 1 or more of a hole injection layer, an electron blocking layer, a layer that performs hole transport and hole injection simultaneously, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron injection and transport layer, in addition to the light emitting layer and the hole transport layer. However, the structure of the organic light emitting device of the present specification is not limited thereto, and may include more organic layers.
In the organic light emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use materials known in the art.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
The organic light emitting device may have, for example, the following stacked structure, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(12) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(15) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection and transport layer/cathode
The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7, and a cathode 4 are sequentially stacked on a substrate 1. The light-emitting layer 3 contains a compound represented by the chemical formula 1, and the hole-transporting layer 6 contains a compound represented by the chemical formula 2.
The organic light emitting device according to the present specification may be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then a material which can be used as a cathode is vapor deposited on the organic material layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, a hole blocking layer, or the like, but the organic layer is not limited thereto and may have a single-layer structure.
The anode is an electrode for injecting holes, and is usually used as an anode material for smoothly injecting holes into an organic layerThe implantation is preferably performed with a substance having a large work function. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO: al or SnO 2 : a 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 not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto. In addition, the cathode may be formed of 1 layer or 2 layers.
The hole transport layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can smoothly inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the movement of holes can be prevented.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance that receives holes from the anode or the hole-injecting layer and transfers the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. The compound represented by the above chemical formula 2 may be contained. The thickness of the hole transport layer may be 1 to 150nm. And may preferably be 30 to 50nm.
An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may use materials known in the art.
The light-emitting layer may emit blue light, may be composed of the compound represented by chemical formula 1, and may further include the compound represented by chemical formula 3 or 4. The material of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light range, and corresponds to a substance having high quantum efficiency for fluorescence or phosphorescence. The thickness of the light emitting layer may be 1 to 150nm. And may preferably be 20 to 50nm.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting material is a material that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a material having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for improving the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be provided between the electron transport layer and the light emitting layer, and may be formed under the same conditions as the hole injection layer. Specifically, there areThe diazole derivative or triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), or the like may include a compound represented by the above chemical formula 2.
The organic light emitting device according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the application
In the following, examples are given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various different forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. Embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
As an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1.
[ reaction type 1]
In the above reaction scheme 1, pair X, ar 1 、Ar 2 And Ar is as defined in the above chemical formula 1, Y is a halogen group, preferably a bromine group or a chlorine group. The above reaction is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst, and the reactive groups for the suzuki coupling reaction may be varied according to techniques known in the art. The above-described production method may be further embodied in a production example described later.
Production example 1: production of Compound 1-1
10g (1 equivalent) of the above compound A1-1 and 5.53g (1 equivalent) of the above compound B1-1 were charged into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 1-1 (9.8 g, yield 80%) was produced.
MS:[M+H] + ＝471
Production example 2: production of Compounds 1-2
10g (1 eq) of the above compound A1-2 and 4.62g (1 eq) of the above compound B1-2 were charged into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g) and tetracyclohexylphosphinePCy 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 1-2 (9.3 g, yield 78%) was produced.
MS:[M+H] + ＝547
Production example 3: production of Compounds 1-3
10g (1 eq) of the above compound A1-3 and 4.15g (1 eq) of the above compound B1-3 were charged into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 1-3 (7.37 g, yield 72%) was produced.
MS:[M+H] + ＝563
Production example 4: production of Compounds 1-4
10g (1 eq) of the above-mentioned compounds A1-4 and 9.07g (1 eq) of the above-mentioned compounds B1-4 were introduced into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 1-4 (13.18 g, yield 86%) was produced.
MS:[M+H] + ＝511
Production example 5: production of Compounds 1-5
10g (1 eq) of the above-mentioned compounds A1-5 and 7.28g (1 eq) of the above-mentioned compounds B1-5 were introduced into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compounds 1 to 5 (11.21 g, yield 77%) were produced.
MS:[M+H] + ＝669
Production example 6: production of Compounds 1-6
10g (1 eq) of the above-mentioned compounds A1-6 and 7.77g (1 eq) of the above-mentioned compounds B1-6 were introduced into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compounds 1 to 6 (10.16 g, yield 69%) were produced.
MS:[M+H] + ＝603
Production example 7: production of Compounds 1-7
10g (1 eq) of the above-mentioned compounds A1-7 and 8.3g (1 eq) of the above-mentioned compounds B1-7 were introduced into tetrahydrofuran (150 mL). K put into 2M 2 CO 3 (100 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd (dba) 2 0.6 g), tetracyclohexylphosphine (PCy) 3 0.6 g) was stirred and refluxed for 5 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compounds 1 to 7 (12.63 g, yield 84%) were produced.
MS:[M+H] + ＝577
[ reaction type 2]
In the above reaction scheme 2, the reaction scheme is as follows 1 To L 2 、Ar 1 、Ar 2 And A is as defined in chemical formula 2 above, Y is a halogen group, preferably a bromine group or a chlorine group. The above reaction is a Buchwald reaction, preferably carried out in the presence of a palladium catalyst, and the reactive groups for the Buchwald reaction may be varied according to techniques known in the art. The above-described production method may be more specifically described in production examples described later.
Production example 8: production of Compound 2-1
10g (1 eq) of the above compound A2-1 and 4.47g (1 eq) of the above compound B2-1 were charged into toluene (150 mL). After 3.68g (2 equivalents) of sodium t-butoxide and 0.01g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-1 (10.0 g, yield 78%) was produced.
MS:[M+H] + ＝674
Production example 9: production of Compound 2-2
10g (1 eq) of the above compound A2-2 and 3.33g (1 eq) of the above compound B2-2 were charged into toluene (150 mL). After 3.09g (2 equivalents) of sodium t-butoxide and 0.08g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-2 (10.0 g, yield 83%) was produced.
MS:[M+H] + ＝748
Production example 10: production of Compounds 2-3
10g (1 eq) of the above compound A2-3 and 23.4g (1 eq) of the above compound B2-3 were charged into toluene (150 mL). After 11.36g (2 equivalents) of sodium t-butoxide and 0.30g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resultant solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-3 was produced (19.8 g, yield 69%).
MS:[M+H] + ＝487
Production example 11: production of Compounds 2-4
/>
10g (1 eq) of the above compound A2-4 and 8.9g (1 eq) of the above compound B2-4 were charged into toluene (150 mL). After 4.83g (2 equivalents) of sodium t-butoxide and 0.13g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-4 (15.3 g, yield 85%) was produced.
MS:[M+H] + ＝715
Production example 12: production of Compounds 2-5
10g (1 eq) of the above compound A2-5 and 10.06g (1 eq) of the above compound B2-5 were charged into toluene (150 mL). After 5.98g (2 equivalents) of sodium t-butoxide and 0.16g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-5 (12.98 g, yield 74%) was produced.
MS:[M+H] + ＝564
Production example 13: production of Compounds 2-6
10g (1 eq) of the above compound A2-6 and 8.16g (1 eq) of the above compound B2-6 were charged into toluene (150 mL). After 5.32g (2 equivalents) of sodium t-butoxide and 0.14g (0.01 equivalents) of bis (tri-t-butylphosphine) palladium (0) were charged, the mixture was stirred and refluxed for 2 hours. After cooling to room temperature, filtration was performed, and the resulting solid was recrystallized from chloroform and ethanol, whereby the above-mentioned compound 2-6 (11.66 g, yield 68%) was produced.
MS:[M+H] + ＝620
Production example 14: production of Compound 3-1
2.9g (1 eq., 3.90 mmol) of A3-1, 2.23g (2.2 eq.) of B3-1, 1.87g (5 eq.) of sodium tert-butoxide, 0.20g (0.1 eq.) of bis (tri-tert-butylphosphine) palladium (0) are added to 50mL of toluene under nitrogen in a 0.1L flask and stirred under reflux. After cooling to room temperature at the end of the reaction, the aqueous layer was removed by extraction with toluene and water. After treatment with anhydrous magnesium sulfate, filtration and concentration under reduced pressure were carried out. The resultant was separated and purified by column chromatography and recrystallized from toluene and n-hexane to give compound 3-1 (2.1 g, yield 49%).
Mass [ m+1] =1100
Production example 15: production of Compound 3-2
By using B3-2 in place of B3-1, the same procedure as in production example 14 was carried out to synthesize Compound 3-2.
Mass [ m+1] =1032
Production example 16: production of Compound 3-3
7.2g,75.3mmol of sodium t-butoxide was added to 80mL of toluene, 16.2g (2.2 equivalents) of B3-3 was added thereto, and 12.0g (1 equivalent) of A3-2 and 0.22g (0.02 equivalent) of bis (tri-t-butylphosphine) palladium (0) were added thereto with stirring, and the mixture was refluxed and stirred. After cooling to room temperature, extraction was performed with ethyl acetate [ EtOAc ] and water, and the obtained organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified by column chromatography (n-Hexane: etOAc) to give compound 3-3 (12.5 g, yield 50%).
MS:[M+H] + ＝1169
Production example 17: production of Compounds 3-4
Compounds 3 to 4 were synthesized according to the following reaction scheme.
8.05g (4 equivalents) of sodium t-butoxide was added to 100mL of toluene, 12.7g (2.2 equivalents) of B3-4 was added thereto, and 10.0g (1 equivalent) of A3-3 and 0.21g (0.02 equivalent) of bis (tri-t-butylphosphine) palladium (0) were added thereto with stirring, and the mixture was refluxed with stirring. After cooling to room temperature, extraction was performed with ethyl acetate [ EtOAc ] and water, and the obtained organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified by column chromatography (n-Hexane: etOAc) to give compound 3-4 (9.4 g, yield 47%).
MS:[M+H] + ＝956
Production example 18: production of Compounds 3-5
Compounds 3 to 5 were synthesized according to the following reaction scheme.
Using A3-4 in place of A3-1 and B3-5 in place of B3-1, the same procedure as in production example 14 was carried out to synthesize Compound 3-5.
Mass [ m+1] =977
The core structures and substituents of the above production examples 14 to 18 may be changed to synthesize compounds satisfying chemical formula 3 or 4.
Experimental example 1]
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, hexanitrile hexaazabenzophenanthrene (hexanitrile hexaazatriphenylene, HATCN) was used as a substrateAnd performing thermal vacuum evaporation to form a hole injection layer. Vacuum evaporating compound 2-6 as the compound to be produced on the hole injection layer to give +.>A hole transport layer is formed by the thickness of host compound 1-2 and dopant compound 3-1, which are manufactured as the hosts of the light-emitting layer>Vacuum evaporation was performed (the weight ratio of host to dopant was 25:1). On the light-emitting layer, alq 3 Substances and LiQ (Lithium Quinolate, 8-hydroxyquinoline)Lithium) was vacuum evaporated at a weight ratio of 1:1 to give +.>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode. Thereby manufacturing an organic light emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device.
< Experimental examples 2 to 30>
An organic light-emitting device was produced in the same manner as in experimental example 1 above, except that the compounds described in table 1 below were used as the host, dopant, and hole transport layer materials in example 1 above.
TABLE 1
| Experimental example | Hole transport layer | Main body | Dopant(s) |
| 1 | Compounds 2-6 | Compounds 1-2 | Compound 3-1 |
| 2 | Compounds 2-5 | Compounds 1-1 | Compound 3-1 |
| 3 | Compounds 2-4 | Compounds 1-3 | Compound 3-2 |
| 4 | Compounds 2-3 | Compounds 1-5 | Compound 3-2 |
| 5 | Compound 2-2 | Compounds 1-4 | Compound 3-3 |
| 6 | Compound 2-1 | Compounds 1-7 | Compound 3-3 |
| 7 | Compound 2-1 | Compounds 1-6 | Compound 3-1 |
| 8 | Compounds 2-5 | Compounds 1-1 | Compound 3-2 |
| 9 | Compounds 2-6 | Compounds 1-2 | Compound 3-2 |
| 10 | Compounds 2-3 | Compounds 1-3 | Compound 3-3 |
| l1 | Compounds 2-4 | Compounds 1-4 | Compound 3-1 |
| 12 | Compound 2-1 | Compounds 1-5 | Compound 3-2 |
| 13 | Compound 2-2 | Compounds 1-6 | Compound 3-1 |
| 14 | Compounds 2-5 | Compounds 1-7 | Compound 3-2 |
| 15 | Compounds 2-6 | Compounds 1-1 | Compound 3-3 |
| 16 | Compounds 2-5 | Compounds 1-3 | Compound 3-1 |
| 17 | Compounds 2-3 | Compounds 1-6 | Compound 3-2 |
| 18 | Compound 2-2 | Compounds 1-5 | Compound 3-3 |
| 19 | Compound 2-1 | Compounds 1-5 | Compound 3-1 |
| 20 | Compounds 2-4 | Compounds 1-7 | Compound 3-2 |
| 21 | Compound 2-1 | Compounds 1-1 | Compounds 3-4 |
| 22 | Compound 2-2 | Compounds 1-3 | Compounds 3-5 |
| 23 | Compounds 2-3 | Compounds 1-5 | Compounds 3-4 |
| 24 | Compounds 2-4 | Compounds 1-7 | Compounds 3-5 |
| 25 | Compounds 2-5 | Compounds 1-2 | Compounds 3-4 |
| 26 | Compounds 2-6 | Compounds 1-4 | Compounds 3-5 |
| 27 | Compound 2-2 | Compounds 1-6 | Compounds 3-4 |
| 28 | Compounds 2-4 | Compounds 1-1 | Compounds 3-4 |
| 29 | Compounds 2-3 | Compounds 1-3 | Compounds 3-5 |
| 30 | Compounds 2-5 | Compounds 1-5 | Compounds 3-5 |
Comparative examples 1 to 29 ]
An organic light-emitting device was produced in the same manner as in experimental example 1 above, except that the compounds described in table 2 below were used as the host, dopant, and hole transport layer materials in example 1 above.
TABLE 2
| Comparative example | Hole transport layer | Main body | Dopant(s) |
| 1 | HT-01 | Compounds 1-1 | Compound 3-1 |
| 2 | HT-01 | Compounds 1-2 | Compound 3-1 |
| 3 | HT-01 | Compounds 1-3 | Compound 3-2 |
| 4 | HT-01 | Compounds 1-4 | Compound 3-2 |
| 5 | HT-01 | Compounds 1-5 | Compound 3-3 |
| 6 | HT-01 | Compounds 1-6 | Compound 3-3 |
| 7 | HT-01 | Compounds 1-7 | Compound 3-1 |
| 8 | Compounds 2-4 | BH-01 | Compound 3-1 |
| 9 | Compound 2-1 | BH-01 | Compound 3-2 |
| 10 | Compound 2-2 | BH-01 | Compound 3-1 |
| 11 | Compounds 2-5 | BH-01 | Compound 3-2 |
| 12 | Compounds 2-6 | BH-01 | Compound 3-3 |
| 13 | Compounds 2-3 | BH-01 | Compound 3-1 |
| 14 | Compound 2-2 | BH-01 | Compound 3-3 |
| 15 | Compounds 2-6 | BH-01 | Compound 3-2 |
| 16 | Compound 2-1 | BH-01 | Compound 3-1 |
| 17 | Compounds 2-4 | BH-01 | Compound 3-2 |
| 18 | Compounds 2-5 | BH-01 | Compound 3-3 |
| 19 | Compounds 2-3 | BH-01 | Compound 3-2 |
| 20 | HT-01 | Compounds 1-1 | BD-01 |
| 21 | HT-01 | Compounds 1-2 | BD-02 |
| 22 | HT-01 | Compounds 1-3 | BD-03 |
| 23 | HT-01 | Compounds 1-4 | BD-04 |
| 24 | HT-01 | Compounds 1-5 | BD-05 |
| 25 | Compounds 2-3 | BH-01 | BD-04 |
| 26 | Compound 2-2 | BH-01 | BD-05 |
| 27 | Compound 2-1 | BH-01 | BD-02 |
| 28 | Compounds 2-4 | BH-01 | BD-03 |
| 29 | Compounds 2-6 | BH-01 | BD-01 |
The organic light-emitting devices manufactured using the respective compounds as in the above experimental examples 1 to 20 and comparative examples 1 to 19 were manufactured at 10mA/cm 2 The driving voltage and luminous efficiency were measured at a current density of 20mA/cm 2 The time required for the initial luminance to be 98% (LT 98) was measured at the current density of (a), and the results are shown in table 3 below.
TABLE 3
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As shown in table 3 above, experimental examples 1 to 30 show characteristics of devices in which the compound of chemical formula 1 of the present invention was used as a host of a light emitting layer, the compound of chemical formula 2 was used in a hole transporting layer, and the compound of chemical formula 3 or 4 was used as a dopant of the light emitting layer. Comparative examples 1 to 7 show characteristics of devices using the compounds of chemical formula 2 and chemical formula 3 or 4, comparative examples 8 to 19 show characteristics of devices using the compounds of chemical formula 1 and chemical formula 3 or 4, comparative examples 20 to 24 show characteristics of devices using only the compound of chemical formula 1, and comparative examples 25 to 29 show characteristics of devices using only the compound of chemical formula 2.
The organic light emitting devices of experimental examples 1 to 30 basically exhibited characteristics of low driving voltage, high efficiency, and long life, relative to comparative examples 1 to 29.
Claims (9)
1. An organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer and a hole-transporting layer,
the light emitting layer includes a compound represented by the following chemical formula 1, and further includes a compound represented by the following chemical formula 4,
the hole transport layer contains a compound represented by the following chemical formula 2:
chemical formula 1
Chemical formula 2
In the chemical formulas 1 and 2 described above,
x is O or S, and the X is O or S,
ar is a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent group to form a substituted or unsubstituted ring,
l1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar3 to Ar5 are the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group; or a heterocyclic group substituted or unsubstituted with an alkyl group, an aryl group or a heterocyclic group,
k1 to k3 are each integers of 0 to 2, and when k1 to k3 are 2, substituents in the brackets of 2 are each the same or different from each other,
n1 is an integer of 0 to 4, and when n1 is 2 or more, 2 or more Ar1 s are the same or different from each other,
n2 is an integer of 0 to 8, and when n2 is 2 or more, 2 or more Ar2 s are the same or different from each other,
chemical formula 4
In the chemical formula 4 described above, the chemical formula,
q1 and Q2 are the same or different from each other and are each, independently, O, S or C (Rf) (Rg),
r201 to R206, rf and Rg are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
cy3 and Cy4 are the same or different from each other and are each independently a substituted or unsubstituted single ring or a substituted or unsubstituted multiple ring,
m1 and m2 are each an integer of 0 to 2, and when m1 and m2 are each 2, substituents in brackets are the same or different from each other.
2. The organic light-emitting device according to claim 1, wherein 1 or more of Ar3 to Ar5 is an aryl group substituted with a heterocyclic group, or a heterocyclic group.
3. The organic light-emitting device according to claim 1, wherein the- (L1) k1 -Ar3、-(L2) k2 Ar4 and- (L3) k3 More than 2 of Ar5 are the same structure.
4. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
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5. the organic light-emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following compounds:
/>
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/>
/>
/>
/>
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6. the organic light-emitting device according to claim 1, wherein the chemical formula 4 is represented by any one of the following compounds:
/>
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7. the organic light-emitting device according to claim 1, wherein an absolute value of a LUMO level of the compound represented by the chemical formula 4 is equal to or less than an absolute value of a LUMO level of the compound represented by the chemical formula 1.
8. The organic light-emitting device according to claim 1, wherein a triplet energy value of the compound represented by the chemical formula 2 is equal to or larger than a triplet energy value of the compound represented by the chemical formula 1.
9. The organic light-emitting device according to claim 1, wherein the organic layer further comprises 1 or more of a hole injection layer, an electron blocking layer, a layer that performs hole transport and hole injection simultaneously, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron injection and transport layer.
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Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014082479A (en) * | 2012-09-27 | 2014-05-08 | Jnc Corp | Organic electroluminescent element |
| KR20150034612A (en) * | 2013-09-26 | 2015-04-03 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| WO2016032066A1 (en) * | 2014-08-26 | 2016-03-03 | 삼성에스디아이 주식회사 | Organic optoelectronic element and display device |
| WO2016068460A1 (en) * | 2014-10-31 | 2016-05-06 | 삼성에스디아이 주식회사 | Organic optoelectronic element and display device |
| KR20170093273A (en) * | 2016-02-03 | 2017-08-16 | 주식회사 동진쎄미켐 | organic light emitting device |
| WO2018004315A2 (en) * | 2016-07-01 | 2018-01-04 | 주식회사 엘지화학 | Compound and organic electronic element comprising same |
| KR20180028948A (en) * | 2016-09-09 | 2018-03-19 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| KR20180037695A (en) * | 2016-10-05 | 2018-04-13 | 에스에프씨 주식회사 | Organic light-emitting diode with long lifetime, low voltage and high efficiency |
| CN108349878A (en) * | 2015-11-17 | 2018-07-31 | 株式会社Lg化学 | Compound and organic electronic element comprising it |
| CN108352456A (en) * | 2015-09-28 | 2018-07-31 | 诺瓦尔德股份有限公司 | Organic electroluminescence device |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101742971B1 (en) * | 2008-05-16 | 2017-06-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Triarylamine derivative, light-emitting substance, light-emitting element, light-emitting device, and electronic device |
| KR20160030435A (en) * | 2014-09-09 | 2016-03-18 | 삼성디스플레이 주식회사 | Organic electroluminescent device |
| KR20170039020A (en) * | 2015-09-30 | 2017-04-10 | 주식회사 스킨앤스킨 | Organic electroluminescent compound and organic electroluminescent device |
| KR101956425B1 (en) | 2016-03-25 | 2019-03-11 | 단국대학교 산학협력단 | TADF Material and OLED Having the Same |
| KR102176862B1 (en) * | 2017-11-06 | 2020-11-10 | 주식회사 엘지화학 | Multicyclic compound and organic light emitting device comprising the same |
-
2019
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- 2019-08-16 CN CN201980006180.5A patent/CN111448679B/en active Active
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Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014082479A (en) * | 2012-09-27 | 2014-05-08 | Jnc Corp | Organic electroluminescent element |
| KR20150034612A (en) * | 2013-09-26 | 2015-04-03 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| WO2016032066A1 (en) * | 2014-08-26 | 2016-03-03 | 삼성에스디아이 주식회사 | Organic optoelectronic element and display device |
| WO2016068460A1 (en) * | 2014-10-31 | 2016-05-06 | 삼성에스디아이 주식회사 | Organic optoelectronic element and display device |
| CN108352456A (en) * | 2015-09-28 | 2018-07-31 | 诺瓦尔德股份有限公司 | Organic electroluminescence device |
| CN108349878A (en) * | 2015-11-17 | 2018-07-31 | 株式会社Lg化学 | Compound and organic electronic element comprising it |
| KR20170093273A (en) * | 2016-02-03 | 2017-08-16 | 주식회사 동진쎄미켐 | organic light emitting device |
| WO2018004315A2 (en) * | 2016-07-01 | 2018-01-04 | 주식회사 엘지화학 | Compound and organic electronic element comprising same |
| KR20180028948A (en) * | 2016-09-09 | 2018-03-19 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| KR20180037695A (en) * | 2016-10-05 | 2018-04-13 | 에스에프씨 주식회사 | Organic light-emitting diode with long lifetime, low voltage and high efficiency |
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