CN111164182B - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN111164182B CN111164182B CN201980004773.8A CN201980004773A CN111164182B CN 111164182 B CN111164182 B CN 111164182B CN 201980004773 A CN201980004773 A CN 201980004773A CN 111164182 B CN111164182 B CN 111164182B
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 150000001616 biphenylenes Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 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
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 238000005036 potential barrier Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium 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
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification provides an organic light-emitting device including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes a first host represented by chemical formula 1, a second host represented by chemical formula 1-1 or chemical formula 1-2, and a dopant, and wherein a layer including a compound represented by chemical formula 2 is included between the anode and the light-emitting layer.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2018-0010561 filed to the korean patent office on 29 th month 1 of 2018, the entire contents of which are included in the present specification.
The present specification relates to organic light emitting devices.
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 the organic thin film to quench and emit light after pairing. 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 complex compound composed of a pure organic substance or a complex of an organic substance and a metal 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 electrochemically has a stable state at the time of reduction is mainly used. In addition, as the light-emitting layer material, a material having a stable form in both an oxidized state and a reduced state is preferable, and when excitons (exiton) generated by recombination of holes and electrons in the light-emitting layer are formed, a material having high light emission efficiency is preferable.
(patent document 1) Korean patent laid-open publication No. 10-2014-001568
Disclosure of Invention
Technical problem
An object of the present specification is to provide an organic light emitting device having high light emitting efficiency, low driving voltage, and long lifetime.
Solution to the problem
An embodiment of the present invention provides an organic light-emitting device including an anode, a cathode, and at least one organic layer including a light-emitting layer provided between the anode and the cathode,
the light emitting layer includes a first host represented by chemical formula 1 below, a second host represented by chemical formula 1-1 or chemical formula 1-2 below, and a dopant,
a layer containing a compound represented by the following chemical formula 2 is included between the anode and the light-emitting layer.
[ chemical formula 1]
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formula 2]
In the above chemical formulas 1, 1-2 and 2,
x1 is O or S, and the total number of the components is equal to or greater than zero,
x2 is O, S or N (Ra),
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
l1 to L6 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N,
ar4 to Ar7 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
ar8 and Ra are the same or different from each other and are each independently a substituted or unsubstituted aryl group,
a. b and e are each integers from 0 to 6,
c and d are each integers from 0 to 7,
a. b, c, d and e are each 2 or more, the substituents in parentheses are the same or different from each other.
In addition, according to an embodiment of the present invention, there is provided an organic light emitting device, wherein the layer including the compound represented by the above chemical formula 2 is a hole transporting layer.
Effects of the invention
Embodiments of the present invention provide an organic light emitting device having excellent efficiency, a low driving voltage, and long life characteristics by including a first host, a second host, and a dopant in a light emitting layer of the organic light emitting device, and including a compound represented by chemical formula 2 in an organic layer between an anode and the light emitting layer.
Drawings
Fig. 1 is a diagram illustrating an organic light emitting device of the present invention.
1: substrate board
2: anode
3: hole injection layer
4: hole transport layer
5: electron suppression layer
6: light-emitting layer
7: hole blocking layer
8: layer for simultaneous electron injection and electron transport
9: cathode electrode
Detailed Description
The present specification will be described in more detail below.
The present invention provides an organic light-emitting device including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes a first host represented by chemical formula 1, a second host represented by chemical formula 1-1 or chemical formula 1-2, and a dopant, and wherein a layer including a compound represented by chemical formula 2 is included between the anode and the light-emitting layer.
[ chemical formula 1]
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formula 2]
In the above chemical formulas 1, 1-2 and 2,
X1 is O or S, and the total number of the components is equal to or greater than zero,
x2 is O, S or N (Ra),
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
l1 to L6 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group containing one or more of S, O and N,
ar4 to Ar7 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
ar8 and Ra are the same or different from each other and are each independently a substituted or unsubstituted aryl group,
a. b and e are each integers from 0 to 6,
c and d are each integers from 0 to 7,
a. b, c, d and e are each 2 or more, the substituents in parentheses are the same or different from each other.
The present invention can manufacture an organic light emitting device having not only a low driving voltage, excellent lifetime characteristics, but also high efficiency by including a first host represented by the above chemical formula 1, a second host represented by the above chemical formula 1-1 or 1-2, and a dopant in a light emitting layer of the organic light emitting device and including a layer containing a compound represented by the above chemical formula 2 between an anode and the light emitting layer.
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 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 a substituent selected from deuterium, halogen group, cyano (-CN), nitro (-NO) 2 ) Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and 1 or 2 or more substituents in the substituted or unsubstituted heterocyclic group, or a substituent bonded by 2 or more substituents in the above-exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) and iodine (I).
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, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, 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, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
In the case where the above fluorenyl group is substituted, it may beAn isospirofluorenyl group,(9, 9-dimethylfluorenyl), and +.>(9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more hetero atoms of N, O, P, S, si and Se, 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, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carbazolyl.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto.
The organic light emitting device of the present invention includes a first host represented by the above chemical formula 1, a second host represented by the above chemical formula 1-1 or 1-2, and a dopant in a light emitting layer.
The second body may include 25 to 400 parts by weight based on 100 parts by weight of the first body, and according to another example, may include 100 to 200 parts by weight. When the second body is included in the above range to manufacture an organic light emitting device, an organic light emitting device having high light emitting efficiency, low driving voltage, and long life can be obtained.
The dopant may be contained in an amount of 6 to 20 parts by weight based on 100 parts by weight of the host substance in the light emitting layer.
L1 and L2 of the above chemical formula 1 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present invention, L1 and L2 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.
In another embodiment, L1 and L2 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to another embodiment, the above-mentioned L1 and L2 are identical to or different from each other and are each independently an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted by a heteroaryl group having 2 to 30 carbon atoms.
In another embodiment, L1 and L2 are the same or different from each other and are each independently a directly bonded, a phenylene group substituted or unsubstituted with a heteroaryl group having 2 to 30 carbon atoms, a biphenylene group substituted or unsubstituted with a heteroaryl group having 2 to 30 carbon atoms, or a naphthylene group substituted or unsubstituted with a heteroaryl group having 2 to 30 carbon atoms.
According to another embodiment, the above-mentioned L1 and L2 are the same or different from each other, and are each independently a directly bonded, a phenylene group substituted or unsubstituted with a carbazolyl group, a biphenylene group substituted or unsubstituted with a carbazolyl group, a terphenylene group substituted or unsubstituted with a carbazolyl group, or a naphthylene group substituted or unsubstituted with a carbazolyl group.
In another embodiment, L1 and L2 are the same or different from each other, and each is independently a phenylene group which is directly bonded, substituted with a carbazolyl group, or unsubstituted.
According to an embodiment of the present invention, R1 of the above chemical formula 1 is hydrogen, deuterium, a halogen group, cyano (-CN), a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 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.
In another embodiment, R1 is hydrogen.
According to an embodiment of the present invention, a is an integer of 0 to 2.
In another embodiment, a is 0 or 1.
According to an embodiment of the present invention, ar2 of the above chemical formula 1 is 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 containing 1 or more of S, O and N.
In another embodiment, ar2 of the above chemical formula 1 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing 1 or more of S, O and N.
According to another embodiment, ar2 of the above chemical formula 1 is a substituted or unsubstituted heterocyclic group containing 1 or more carbon atoms of 2 to 30 in S, O and N.
In another embodiment, ar2 is a substituted or unsubstituted heterocyclic group having 1 or more N and having 2 to 30 carbon atoms.
According to an embodiment of the present invention, ar2 described above may be represented by any one of the following chemical formulas 1-A to 1-J.
[ chemical formula 1-A ]
[ chemical formula 1-B ]
[ chemical formula 1-C ]
[ chemical formula 1-D ]
[ chemical formula 1-E ]
[ chemical formula 1-F ]
[ chemical formula 1-G ]
[ chemical formula 1-H ]
[ chemical formula 1-I ]
[ chemical formula 1-J ]
In the above chemical formulas 1-a to 1-J,
x3 to X10 are identical to or different from each other and are each, independently of one another, O, S, N (Rb) or C (Rc) (Rd),
rb, rc, rd, R11 to R21, R and R', equal to or different from each other, are each independently hydrogen, deuterium, a halogen group, cyano (-CN), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
n1 is an integer of 0 to 8,
n2 is an integer of 0 to 7,
n3 is an integer of 0 to 5,
n4, n6 to n9 and n11 are each integers of 0 to 10,
n5 and n10 are each integers from 0 to 9,
when n1 to n11 are each 2 or more, substituents in brackets are the same or different from each other,
* Refers to the position of binding to L2.
According to an embodiment of the present invention, n1 is an integer of 0 to 2.
According to an embodiment of the present invention, R11 is hydrogen, deuterium, a halogen group, cyano (-CN), 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 heteroaryl group having 2 to 30 carbon atoms.
In another embodiment, R11 is hydrogen, deuterium, 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, R11 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted carbazolyl.
In another embodiment, R11 is hydrogen, deuterium, 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 aryl group having 6 to 30 carbon atoms.
According to another embodiment, R11 is hydrogen, deuterium, phenyl, biphenyl, naphthyl, or carbazolyl substituted or unsubstituted with phenyl.
According to an embodiment of the present invention, n2 and n3 are each integers of 0 to 2.
In one embodiment of the present invention, R12 and R13 are the same or different and each is independently hydrogen, deuterium, a halogen group, cyano (-CN), 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 heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present invention, R12 and R13 are hydrogen.
In an embodiment of the invention, n4 to n11 are integers from 0 to 2.
According to an embodiment of the present invention, R14 to R21 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), 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 heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present invention, R14 to R21 are the same or different from each other and each is independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above-mentioned R14 to R21 are the same or different from each other and are each independently hydrogen or phenylene.
According to an embodiment of the present specification, the above R and R' are the same or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, R and R' are the same or different from each other and are each independently a substituted or unsubstituted phenyl group.
According to an embodiment of the present invention, X3 to X10 are the same or different from each other, and each is independently O, S, N (Rb) or C (Rc) (Rd).
According to an embodiment of the present invention, rb is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, rb mentioned above is a substituted or unsubstituted phenyl group.
According to an embodiment of the present invention, rc and Rd are the same or different from each other and each independently is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
In another embodiment, rc and Rd are substituted or unsubstituted methyl groups.
According to an embodiment of the present invention, ar1 of the above chemical formula 1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group containing 1 or more of S, O and N.
In another embodiment, ar1 is 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 containing 1 or more of S, O and N.
According to another embodiment, ar1 is a substituted or unsubstituted heterocyclic group containing 1 or more carbon atoms of 2 to 30 in S, O and N.
In another embodiment, ar1 is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenanthroline group, or a substituted or unsubstituted benzimidazolyl group.
According to an embodiment of the present invention, ar1 described above may be represented by any one of the following chemical formulas Ar-1 to Ar-5.
[ chemical formula Ar-1]
[ chemical formula Ar-2]
[ chemical formula Ar-3]
[ chemical formula Ar-4]
[ chemical formula Ar-5]
In the chemical formulas Ar-1 to Ar-5,
w1 to W12 are identical to or different from each other and are each independently C (Re) or N,
re, rf and A1 to A4 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
p1 and p2 are each integers from 0 to 5,
p3 is an integer of 0 to 4,
p4 is an integer of 0 to 7,
when p1 to p4 are each 2 or more, substituents in brackets are the same or different from each other,
* Refers to the position where L1 binds.
According to an embodiment of the present invention, W1 to W12 are the same as or different from each other, and are each independently C (Re) or N.
In one embodiment of the present invention, re, rf and A1 to A4 are the same or different from each other and are each independently hydrogen, deuterium, 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.
According to an embodiment of the present invention, rf is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In another embodiment, rf is a substituted or unsubstituted phenyl group.
According to another embodiment, re and A1 to A4 described above are the same as or different from each other, each independently is 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, re and A1 to A4 are the same or different from each other, and each is independently hydrogen; deuterium; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted aryl groups having 6 to 30 carbon atoms in the alkyl group having 1 to 20 carbon atoms; or is selected from cyano (-CN), nitro (-NO) 2 ) And a heteroaryl group having 2 to 30 carbon atoms, which is substituted or unsubstituted by 1 or more of alkyl groups having 1 to 20 carbon atoms.
According to another embodiment, re and A1 to A4 described above are the same as each otherOr, differently, each independently hydrogen; deuterium; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted phenyl groups in the methyl group; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted biphenyl groups in the methyl group; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted naphthyl groups in the methyl group; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted terphenyl groups in the methyl group; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted fluorenyl groups in the methyl group; is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted dibenzofuranyl groups in the methyl group; or is selected from cyano (-CN), nitro (-NO) 2 ) And 1 or more substituted or unsubstituted dibenzothienyl groups in the methyl group.
According to an embodiment of the present invention, each of p1 to p4 is an integer of 0 to 2.
In one embodiment of the present invention, the chemical formula 1 may be represented by any one of the following structures.
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The organic layer of the organic light emitting device of the present invention includes a second host represented by the above chemical formula 1-1 or 1-2.
In one embodiment of the present invention, L3 is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to another embodiment, L3 is a direct bond.
According to an embodiment of the present invention, ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms containing 1 or more of S, O and N.
In one embodiment of the present invention, ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present invention, ar3 is an aryl group having 6 to 60 carbon atoms, which is substituted or unsubstituted with a methyl group.
In another embodiment, ar3 mentioned above is phenyl substituted or unsubstituted with methyl, biphenyl substituted or unsubstituted with methyl, naphthyl substituted or unsubstituted with methyl, fluorenyl substituted or unsubstituted with methyl.
According to another embodiment, ar3 mentioned above is phenyl, biphenyl, naphthyl or 9, 9-dimethylfluorenyl.
According to an embodiment of the present invention, X1 is O or S, and X2 is O, S or N (Ra).
According to an embodiment of the present invention, ra is a substituted or unsubstituted aryl group.
According to another embodiment, ra is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, ra is a substituted or unsubstituted phenyl group.
According to an embodiment of the present invention, L4 is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to another embodiment, L4 is a substituted or unsubstituted phenylene group.
According to an embodiment of the present invention, b, c and d are each integers of 0 to 2.
According to an embodiment of the present invention, the above R2 to R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), 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.
In another embodiment, R2 to R4 are hydrogen.
According to an embodiment of the present invention, the chemical formula 1-1 may be any one of the following structures.
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According to an embodiment of the present invention, the above chemical formula 1-2 may be any one of the following structures.
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The organic light emitting device of the present invention includes a dopant in a light emitting layer. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The organic light emitting device of the present invention includes a layer containing a compound represented by the above chemical formula 2 between an anode and a light emitting layer.
In one example of the present invention, the compound represented by the above chemical formula 2 contains 2 amine groups in the compound, and the layer containing the compound represented by the above chemical formula 2 may be a hole transport layer. When the hole transport layer contains a compound having 3 or more amine groups, the HOMO level of the compound having 3 or more amine groups is about-5.2 eV, and the level is too high, so that the potential barrier with the electron-suppressing layer and the light-emitting layer becomes large, and the Charge balance (Charge balance) is unbalanced, and the device characteristics are degraded.
An organic light emitting device manufactured to include the compound of chemical formula 2 described above may have excellent efficiency compared to an organic light emitting device manufactured to include a compound having 3 or more amine groups.
According to an embodiment of the present invention, ar8 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, ar8 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, ar8 mentioned above is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
In another embodiment, ar8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted fluorenyl group.
According to another embodiment, ar8 is phenyl, biphenyl, naphthyl, terphenyl, or 9, 9-dimethylfluorenyl.
According to an embodiment of the present invention, L5 and L6 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 L5 and L6 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
In another embodiment, the above-mentioned L5 and L6 are the same or different from each other, and each is independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.
According to an embodiment of the present invention, ar4 to Ar7 are the same 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, ar4 to Ar7 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.
According to another embodiment, the above Ar4 to Ar7 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, or a substituted or unsubstituted naphthyl group.
According to an embodiment of the present invention, R5 is hydrogen.
According to an embodiment of the present invention, e is an integer of 0 to 2.
In one embodiment of the present invention, the chemical formula 2 may be represented by any one of the following structures.
The compounds of chemical formulas 1, 1-2 and 2 according to one embodiment of the present specification may be manufactured as in the manufacturing examples described below, and the compounds of chemical formulas 1, 1-2 and 2 may manufacture core structures as in the manufacturing examples described below. The substituents may be bonded according to a method known in the art, and the kinds, positions or number of the substituents may be changed according to a technique known in the art.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a hole adjustment layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, an electron suppression layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic light emitting device of the present invention may include the compound represented by chemical formula 2 described above in the hole transport layer.
The organic light emitting device according to an embodiment of the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers including a light emitting layer, and a cathode are sequentially stacked on a substrate.
The organic light emitting device according to another embodiment may be an organic light emitting device having a structure (inverted type) in which a cathode, one or more organic layers including a light emitting layer, and an anode are sequentially stacked on a substrate.
The above-described organic light emitting device may have, for example, a stacked structure as described below, 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 injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/electron suppressing layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/electron suppressing layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/electron suppression layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/cathode for simultaneous electron injection and electron transport
(19) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/cathode for simultaneous electron injection and electron transport
(20) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1.
Fig. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron suppression layer 5, a light-emitting layer 6, a hole blocking layer 7, a layer 8 for simultaneously injecting and transporting electrons, and a cathode 9 are stacked in this order. In the structure described above, the compound represented by the above chemical formula 1 and the compound represented by the chemical formula 1-1 or 1-2 may be contained in the light-emitting layer 6, and the compound represented by the above chemical formula 2 may be contained in the hole-transporting layer 4. The light emitting layer may emit green light.
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, in addition to forming one or more organic layers using the above-described compound.
In the case of producing an organic light-emitting device, the compound may be used to form an organic layer not only by vacuum vapor deposition but also by solution coating. 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.
For example, the organic light emitting device according to the present invention 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), an organic layer including a hole injection layer, a hole transport layer, a hole adjustment layer, a light emitting layer, an electron transport layer, or the like is formed on the anode by vacuum vapor deposition or solution coating, and then a substance that can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. 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); 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.
The hole injection layer is a layer that functions to smoothly inject holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can favorably 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 metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, polythiophene-based conductive polymer, and the like, but not limited thereto, and may be doped with benzonitrile-based organic substance at a concentration of 0.1 to 10 wt%. 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 capable of receiving holes from the anode or the hole-injecting layer and transferring them to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples thereof include, but are not limited to, the compound represented by chemical formula 2, an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and non-conjugated portions. The thickness of the hole transport layer may be 1 to 100nm.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron-suppressing layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-inhibiting layer may be formed using the spiro compound, the arylamine-based organic compound, or a material known in the art.
The light emitting layer may emit red, green or blue light, and may include a host and a dopant. The main body may include 1 or more, and chemical formula 1 of the present invention may be included as a first main body, and chemical formula 1-1 or 1-2 may be included as a second main body. Further, a compound that can be included as a dopant of the light-emitting layer is as described above.
At the electron transport layerA hole-suppressing layer may be provided between the light-emitting layer and the light-emitting layer, and the hole-suppressing layer is a layer that blocks holes from reaching the cathode and can be formed under the same conditions as the hole-injecting layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
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 reduction of the electron transport property can be prevented, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the increase of the driving voltage for improving the movement of electrons can be prevented.
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,/->Diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylmethylene +.>Anthrone and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives and the like, but are not limited thereto.
The electron injection and electron transport layer may be formed to contain an electron injection substance and/or an electron transport substance.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
In the following, examples are described in detail for the purpose of specifically explaining the present specification. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the specification to those skilled in the art.
< production example >
Production example 1-1: production of Compound 1-1
After the compound 1-a (13.05 g,23.69 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4, 6-diphenoyl-1, 3, 5-triazine) (5.50 g,20.60 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.71 g,0.62 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran to give Compound 1-1 (8.75 g, 65%).
MS:[M+H] + ＝657
Production examples 1 to 2: production of Compounds 1-2
After complete dissolution of compound 1-a (8.31 g,15.09 mmol), 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3,5-triazine (4.50 g,13.12 mmol) in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (100 ml) was added, tetrakis (triphenylphosphine) palladium (0.45 g,0.39 mmol) was added and heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 180ml of tetrahydrofuran to give Compound 1-2 (7.59 g, 79%).
MS:[M+H] + ＝733
Production examples 1 to 3: production of Compounds 1-3
After complete dissolution of compound 1-b (13.50 g,21.54 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (5.00 g,18.73 mmol) in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added and tetrakis (triphenylphosphine) palladium (0.65 g,0.56 mmol) was added and heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 150ml of tetrahydrofuran to give Compound 1-3 (9.76 g, 71%).
MS:[M+H] + ＝733
Production example 2-1: production of Compound 2-1
After the compound 2-a (9.50 g,18.89 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (6.23 g,21.72 mmol) was completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.65 g,0.57 mmol) was added, and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 190ml of tetrahydrofuran to give compound 2-1 (8.16 g, 65%).
MS:[M+H] + ＝667
Production example 2-2: production of Compound 2-2
After complete dissolution of compound 2-b (8.50 g,14.68 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (4.85 g,16.88 mmol) in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (100 ml) was added and tetrakis (triphenylphosphine) palladium (0.51 g,0.44 mmol) was added followed by stirring with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 170ml of tetrahydrofuran, whereby Compound 2-2 (6.61 g, 61%) was produced.
MS:[M+H] + ＝743
Production example 2-3: production of Compounds 2-3
After complete dissolution of compound 2-b (7.00 g,13.92 mmol), (9- ([ 1,1' -biphenyl ] -3-yl) -9H-carbazol-3-yl) boronic acid (5.81 g,16.00 mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100 ml) was added and tetrakis (triphenylphosphine) palladium (0.48 g,0.42 mmol) was added to the flask under nitrogen atmosphere, followed by stirring with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 150ml of tetrahydrofuran to give compound 2-3 (5.67 g, 55%).
MS:[M+H] + ＝743
Production example 3-1: production of Compound 3-1
/>
After the compound 3-a (4.50 g,11.28 mmol) and (4- (diphenylamino) phenyl) boronic acid (7.17 g,24.81 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (110 ml) was added, and tetrakis (triphenylphosphine) palladium (0.39 g,0.34 mmol) was added thereto and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 180ml of tetrahydrofuran to give compound 3-1 (5.78 g, 70%).
MS:[M+H] + ＝730
Production example 3-2: production of Compound 3-2
Compound 3-2 was produced by the same method as that for compound 3-1 except that 3, 6-dibromo-9- (naphthalen-2-yl) -9H-carbazole was used instead of 3-a.
MS:[M+H] + ＝780
Production example 3-3: production of Compound 3-3
Compound 3-3 was produced by the same method as that for compound 3-1, except that 9- ([ 1,1' -biphenyl ] -4-yl) -3, 6-dibromo-9H-carbazole was used instead of 3-a.
MS:[M+H] + ＝806
< example >
Example 1: fabrication of organic light emitting devices
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI1 compound was usedAnd p-doping the following a-1 compound at a concentration of 2%. On the hole injection layer, the following compound 3-1 was vacuum-evaporated to give a film thickness +. >A hole transport layer is formed. Next, on the hole transport layer, the film thickness is +.>The electron-inhibiting layer was formed by vacuum evaporation of the EB1 compound described below.
Next, on the electron-inhibiting layer, a mixture of compounds 1 to 1 and 2 in a weight ratio of 4:6 (compound 1 to 1-1) a host composition obtained by mixing the compound 1-1 and the following compound 2-1 and the following YGD-1 compound as a phosphorescent dopant in an amount of 6 wt% relative to the host composition were vacuum-evaporated to formGreen light emitting layer of thickness.
On the light-emitting layer, the following HB1 compound was formed in a film thicknessVacuum evaporation is performed to form a hole blocking layer. Next, on the hole blocking layer, the following ET1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1 to form ∈1>Forms a layer that performs electron injection and electron transport simultaneously. Lithium fluoride (LiF) is sequentially added to the electron injection and transport layer>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathode>Is 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.
Examples 2 to 10 and comparative examples 1 to 13: fabrication of organic light emitting devices
Organic light-emitting devices of examples 2 to 10 and comparative examples 1 to 13 were fabricated by the same method as in example 1, except that the compounds described in table 1 below were used instead of the compound 3-1 of the hole transport layer and the compounds 1-1 and 2-1 of the green light-emitting layer, respectively. In this case, HT1, YGH-1 and YGH-2 described in Table 1 below are the compounds represented by the above.
Experimental example: performance evaluation of organic light emitting device
For the organic light emitting devices fabricated in examples 1 to 10 and comparative examples 1 to 13 described above, the temperature was set at 10mA/cm 2 Voltage and efficiency were measured at a current density of 20mA/cm 2 The time required for a reduction of 95% with respect to the initial brightness (6000 nit), i.e. Lifetime (LT) 95 ) The results are shown in table 1 below.
TABLE 1
The basic characteristics of an organic light-emitting device using a conventional compound (comparative example 13) are shown in the above table 1; an organic light emitting device using the compound represented by the above chemical formula 2 as a hole transport layer, but using a conventional compound as a green light emitting layer material (comparative examples 7 to 9); and organic light emitting devices using the compounds represented by the above chemical formula 1 and the above chemical formula 1-1 or 1-2 as a light emitting layer material, but using a conventional compound as a hole transporting layer material (comparative examples 1 to 6 and comparative examples 10 to 12).
When the compounds represented by the chemical formulas 1, 1-2 and 2 are used in combination as materials for the green light emitting layer and the hole transport layer in comparison with the examples and the comparative examples, respectively, a low driving voltage, high efficiency and long life are exhibited as compared with the conventional organic light emitting device. In particular, when the above compound 3-2 is used as a hole transport layer material, the driving voltage is the lowest, the efficiency is the highest, and when 1-1 and 2-1 are used as light emitting layer materials, the lifetime is the longest.
On the other hand, when comparing comparative examples 1 to 13, in comparative examples 7 to 9 in which the hole transport layer material was changed to the compound represented by the above chemical formula 2, the driving voltage was lowered, the light emitting efficiency was improved, and in comparative examples 1 to 6 and comparative examples 10 to 12 in which the green light emitting layer material was changed to the compound represented by the above chemical formula 1 and/or any one of chemical formulas 1-1 and 1-2, the lifetime was improved. However, the efficiency and lifetime at the level of the examples are not shown.
From this, it was confirmed that the organic light emitting device of the present invention uses a compound having a structure in which arylamines including a linking group are substituted at both sides of the 3, 6 positions of carbazole as shown in the above chemical formula 2, in a hole transport layer between an anode and a light emitting layer, thereby exhibiting a low driving voltage, uses a compound having a structure in which triazine having an electron injecting ability and very excellent thermal stability is substituted at the 4 position of dibenzothiophene as shown in the above chemical formula 1, as an n-type (n-type) substance of a green light emitting layer, and uses a compound having a structure in which carbazole and aryl are substituted at the 4, 2 positions of dibenzothiophene as shown in the above chemical formulas 1-1 and 1-2, as a p-type (p-type) substance of a green light emitting layer, thereby exhibiting a low driving voltage and improved efficiency, and simultaneously exhibiting a long lifetime.
Claims (5)
1. An organic light-emitting device comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode,
the light emitting layer includes a first host represented by chemical formula 1 below, a second host represented by chemical formula 1-1 or chemical formula 1-2 below, and a dopant,
a layer containing a compound represented by the following chemical formula 2 is included between the anode and the light-emitting layer:
chemical formula 1
Chemical formula 1-1
Chemical formula 1-2
Chemical formula 2
In the chemical formulas 1, 1-2 and 2,
x1 is O or S, and the total number of the components is equal to or greater than zero,
x2 is NRa, and X is a number,
r1 to R5 are hydrogen,
l1 and L2 are identical to or different from each other and are each independently a direct bond, phenylene, biphenylene, terphenylene, or naphthylene,
l3 is a direct bond and is bonded directly to the substrate,
l4 is a direct bond, or phenylene,
l5 and L6 are identical to or different from each other and are each independently a direct bond, phenylene, biphenylene, or terphenylene,
ar1 is a pyridyl group substituted or unsubstituted with a phenyl group or a biphenyl group, a pyrimidinyl group substituted or unsubstituted with a phenyl group or a biphenyl group, or a triazinyl group substituted or unsubstituted with a phenyl group or a biphenyl group,
ar2 is represented by the following chemical formula 1-A or 1-B:
Chemical formula 1-A
Chemical formula 1-B
In the chemical formulas 1-a and 1-B,
r11 is hydrogen, phenyl, biphenyl, or naphthyl,
r12 and R13 are hydrogen,
n1 is an integer of 0 to 8,
n2 is a number of times greater than 7,
n3 is a number of times which is 5,
when n1 is 2 or more, the substituents in brackets are the same or different from each other,
* Refers to the position where it binds to L2,
ar3 is phenyl, biphenyl, naphthyl or 9, 9-dimethylfluorenyl,
ar4 to Ar7 are the same as or different from each other and are each independently a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,
ar8 is phenyl, biphenyl, naphthyl, terphenyl or 9, 9-dimethylfluorenyl,
ra is a phenyl group or a biphenyl group,
a. b and e are each integers from 0 to 6,
c and d are each integers from 0 to 7,
a. b, c, d and e are each 2 or more, the substituents in parentheses are the same or different from each other,
wherein the layer containing the compound represented by the chemical formula 2 is a hole transport layer.
2. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is any one of the following structures:
。
3. the organic light-emitting device according to claim 1, wherein the chemical formula 1-1 is any one of the following structures:
/>
4. the organic light-emitting device according to claim 1, wherein the chemical formula 1-2 is any one of the following structures:
/>
5. The organic light-emitting device according to claim 1, wherein the chemical formula 2 is any one of the following structures:
/>
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