WO2015199493A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant - Google Patents
Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant Download PDFInfo
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- WO2015199493A1 WO2015199493A1 PCT/KR2015/006574 KR2015006574W WO2015199493A1 WO 2015199493 A1 WO2015199493 A1 WO 2015199493A1 KR 2015006574 W KR2015006574 W KR 2015006574W WO 2015199493 A1 WO2015199493 A1 WO 2015199493A1
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- unsubstituted
- organic electroluminescent
- alkyl
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- RMXPBEQLHFJWIL-UHFFFAOYSA-O CC(C)(c1ccccc1-c1c2)c1ccc2-c(cc1c2c3ccc4c2[o]c2ccccc42)cc2c1[n]3c1c2[NH2+]C(C=CC=C2)C2=N1 Chemical compound CC(C)(c1ccccc1-c1c2)c1ccc2-c(cc1c2c3ccc4c2[o]c2ccccc42)cc2c1[n]3c1c2[NH2+]C(C=CC=C2)C2=N1 RMXPBEQLHFJWIL-UHFFFAOYSA-O 0.000 description 1
- AMLVYEUEPNHDBA-UHFFFAOYSA-N CC(CC=C(C=CC=C1)C1=C1)c2c1c1c3[n]2c2c4[o]c(ccc(-c5cc(cccc6)c6cc5)c5)c5c4ccc2c3ccc1 Chemical compound CC(CC=C(C=CC=C1)C1=C1)c2c1c1c3[n]2c2c4[o]c(ccc(-c5cc(cccc6)c6cc5)c5)c5c4ccc2c3ccc1 AMLVYEUEPNHDBA-UHFFFAOYSA-N 0.000 description 1
- 0 CC1(C(c2ccccc22)=CC(c3ccc4[s]c(c5c(c(c6c7cccc6)c6)[n]7c7c5NC5C=CC=C*5N7)c6c4c3)=CC1)N2c1ccccc1 Chemical compound CC1(C(c2ccccc22)=CC(c3ccc4[s]c(c5c(c(c6c7cccc6)c6)[n]7c7c5NC5C=CC=C*5N7)c6c4c3)=CC1)N2c1ccccc1 0.000 description 1
- KYFIXDRYRIRQBB-UHFFFAOYSA-N CC1C=CC2c3cc(-c(cc4c5c6ccc7c5[o]c5ccccc75)cc5c4[n]6c4nc(cccc6)c6cc54)ccc3SC2C1 Chemical compound CC1C=CC2c3cc(-c(cc4c5c6ccc7c5[o]c5ccccc75)cc5c4[n]6c4nc(cccc6)c6cc54)ccc3SC2C1 KYFIXDRYRIRQBB-UHFFFAOYSA-N 0.000 description 1
- SSWUGFOJSXEMTB-UHFFFAOYSA-N CCC(C)c1c(NC2C=CC=CC2)[n]2c(c3c(cc4)[o]c5ccccc35)c4c3cc(-c(cc4)cc(c5c6cccc5)c4[n]6-c4ccccc4)cc1c23 Chemical compound CCC(C)c1c(NC2C=CC=CC2)[n]2c(c3c(cc4)[o]c5ccccc35)c4c3cc(-c(cc4)cc(c5c6cccc5)c4[n]6-c4ccccc4)cc1c23 SSWUGFOJSXEMTB-UHFFFAOYSA-N 0.000 description 1
- GNOYEJCAUKARQD-UHFFFAOYSA-N CN(C(C=CC=C1)C1=C1)c2c1c(cccc13)c1[n]2c(cc1)c3c2c1[o]c1c2ccc(-c2c(cccc3)c3ccc2)c1 Chemical compound CN(C(C=CC=C1)C1=C1)c2c1c(cccc13)c1[n]2c(cc1)c3c2c1[o]c1c2ccc(-c2c(cccc3)c3ccc2)c1 GNOYEJCAUKARQD-UHFFFAOYSA-N 0.000 description 1
- WBWLKTVJTXYWAJ-UHFFFAOYSA-N CN1c([n](c(cc2)c(c3c4)c5c2[o]c2c5cccc2)c3c2cc4-c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3)c2N=C2C=CC=CC12 Chemical compound CN1c([n](c(cc2)c(c3c4)c5c2[o]c2c5cccc2)c3c2cc4-c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3)c2N=C2C=CC=CC12 WBWLKTVJTXYWAJ-UHFFFAOYSA-N 0.000 description 1
- KDQRGZOMPREQPL-UHFFFAOYSA-N c(cc1)cc(c2c3)c1[s]c2cc1c3c2cccc3c2[n]1c1nc2cc4ccccc4cc2nc31 Chemical compound c(cc1)cc(c2c3)c1[s]c2cc1c3c2cccc3c2[n]1c1nc2cc4ccccc4cc2nc31 KDQRGZOMPREQPL-UHFFFAOYSA-N 0.000 description 1
- GTCDLNRVUNCNEQ-UHFFFAOYSA-N c(cc1)cc(cc2)c1c(c1c3)c2[o]c1cc1c3c2cccc3c2[n]1c1c3nc(cccc2)c2n1 Chemical compound c(cc1)cc(cc2)c1c(c1c3)c2[o]c1cc1c3c2cccc3c2[n]1c1c3nc(cccc2)c2n1 GTCDLNRVUNCNEQ-UHFFFAOYSA-N 0.000 description 1
- UDVNEQXERUMMKM-UHFFFAOYSA-N c(cc1)cc(cc2)c1cc2-c(cc1)cc2c1[o]c1c(c3c4[n]5c6nc7ccccc7nc6c4ccc3)c5ccc21 Chemical compound c(cc1)cc(cc2)c1cc2-c(cc1)cc2c1[o]c1c(c3c4[n]5c6nc7ccccc7nc6c4ccc3)c5ccc21 UDVNEQXERUMMKM-UHFFFAOYSA-N 0.000 description 1
- JKGXCHFFWLBLFD-UHFFFAOYSA-N c(cc1)cc2c1[o]c(cc1)c2c2c1c(cccc13)c1[n]2c(NC12)c3N=C1C=Cc1c2cccc1 Chemical compound c(cc1)cc2c1[o]c(cc1)c2c2c1c(cccc13)c1[n]2c(NC12)c3N=C1C=Cc1c2cccc1 JKGXCHFFWLBLFD-UHFFFAOYSA-N 0.000 description 1
- RAFMPSTXTMCDGI-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(cc(cc2)-c(cc3c4c5ccc6c4[o]c4ccccc64)cc4c3[n]5c3nc(cccc5)c5nc43)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(cc(cc2)-c(cc3c4c5ccc6c4[o]c4ccccc64)cc4c3[n]5c3nc(cccc5)c5nc43)c2c2ccccc12 RAFMPSTXTMCDGI-UHFFFAOYSA-N 0.000 description 1
- VELDBSQBXAQJLE-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(ccc(-c(cc2c3c4ccc5c3c(cccc3)c3[o]5)cc3c2[n]4c2nc4ccccc4nc32)c2)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(ccc(-c(cc2c3c4ccc5c3c(cccc3)c3[o]5)cc3c2[n]4c2nc4ccccc4nc32)c2)c2c2ccccc12 VELDBSQBXAQJLE-UHFFFAOYSA-N 0.000 description 1
- AJQVJDDTQCSGNN-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1cc(c1c3[n]4c(cc5[s]c(cccc6)c6c5c5)c5c3ccc1)c4n2 Chemical compound c(cc1)ccc1-c(cc1)cc2c1cc(c1c3[n]4c(cc5[s]c(cccc6)c6c5c5)c5c3ccc1)c4n2 AJQVJDDTQCSGNN-UHFFFAOYSA-N 0.000 description 1
- CPGDJNULIGXOMX-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1nc(c1cccc3c1[n]1c4c(c5ccccc5[o]5)c5ccc34)c1n2 Chemical compound c(cc1)ccc1-c(cc1)cc2c1nc(c1cccc3c1[n]1c4c(c5ccccc5[o]5)c5ccc34)c1n2 CPGDJNULIGXOMX-UHFFFAOYSA-N 0.000 description 1
- NIFYRYIKMGSCNT-UHFFFAOYSA-N c(cc1)ccc1-c1ccc2c3c(c4c5[n]6c7nc8ccccc8nc7c5ccc4)c6ccc3[o]c2c1 Chemical compound c(cc1)ccc1-c1ccc2c3c(c4c5[n]6c7nc8ccccc8nc7c5ccc4)c6ccc3[o]c2c1 NIFYRYIKMGSCNT-UHFFFAOYSA-N 0.000 description 1
- HVAAZODEMJBCRT-UHFFFAOYSA-N c(cc1c2c3)ccc1[o]c2cc1c3[n]2c3nc(cccc4)c4nc3c3c2c1ccc3 Chemical compound c(cc1c2c3)ccc1[o]c2cc1c3[n]2c3nc(cccc4)c4nc3c3c2c1ccc3 HVAAZODEMJBCRT-UHFFFAOYSA-N 0.000 description 1
- NJUQBOKDEQWGRF-UHFFFAOYSA-N c(cc1c2ccc3c4c5c6ccc4)ccc1[s]c2c3[n]5c1c6nc(ccc2c3cccc2)c3n1 Chemical compound c(cc1c2ccc3c4c5c6ccc4)ccc1[s]c2c3[n]5c1c6nc(ccc2c3cccc2)c3n1 NJUQBOKDEQWGRF-UHFFFAOYSA-N 0.000 description 1
- RWSJJAIMCCMTGS-UHFFFAOYSA-N c1cc2cccc(-c(cc3)cc([o]c4c56)c3c4ccc5[n]3c4nc(cccc5)c5nc4c4c3c6ccc4)c2cc1 Chemical compound c1cc2cccc(-c(cc3)cc([o]c4c56)c3c4ccc5[n]3c4nc(cccc5)c5nc4c4c3c6ccc4)c2cc1 RWSJJAIMCCMTGS-UHFFFAOYSA-N 0.000 description 1
- GKKWUSBBMJGOMF-UHFFFAOYSA-N c1ccc2[o]c(c3c(cc4)[n]5c6nc(cccc7)c7nc6c6c5c3cc(-c(cc3)cc5c3[o]c3c5cccc3)c6)c4c2c1 Chemical compound c1ccc2[o]c(c3c(cc4)[n]5c6nc(cccc7)c7nc6c6c5c3cc(-c(cc3)cc5c3[o]c3c5cccc3)c6)c4c2c1 GKKWUSBBMJGOMF-UHFFFAOYSA-N 0.000 description 1
- JYKKFWCVDATNBN-UHFFFAOYSA-N c1ccc2[o]c(ccc(-c(cc3c4c5ccc6c4c4ccccc4[o]6)cc4c3[n]5c3nc5ccccc5nc43)c3)c3c2c1 Chemical compound c1ccc2[o]c(ccc(-c(cc3c4c5ccc6c4c4ccccc4[o]6)cc4c3[n]5c3nc5ccccc5nc43)c3)c3c2c1 JYKKFWCVDATNBN-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- 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
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
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- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
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- 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
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- 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
- H10K50/156—Hole transporting layers comprising a multilayered structure
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device with the advantages of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
- the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).
- An organic EL device changes electric energy into light by the application of electric current to an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
- the organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML) (containing host and dopant materials), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc., depending on functions.
- the organic EL device In the organic EL device, holes from an anode and electrons from a cathode are injected into a light-emitting layer by the application of electric voltage, and an exciton having high energy is produced by the recombination of holes and electrons.
- the organic light-emitting compound moves into an excited state by the energy and emits light from energy when the organic light-emitting compound returns to the ground state from the excited state.
- the most important factor determining luminous efficiency in an organic EL device is light-emitting materials.
- the light-emitting materials are required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, and formability of a uniform and stable layer.
- the light-emitting materials are classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials according to the light-emitting color, and further include yellow light-emitting materials or orange light-emitting materials.
- the light-emitting material is classified into a host material and a dopant material in a functional aspect. Recently, an urgent task is the development of an organic EL device having high efficiency and long lifespan.
- a host material should have high purity and a suitable molecular weight in order to be deposited under vacuum. Furthermore, a host material is required to have high glass transition temperature and pyrolysis temperature for guaranteeing thermal stability, high electrochemical stability for long lifespan, easy formability of an amorphous thin film, good adhesion with adjacent layers, and no movement between layers.
- Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ), and bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium (Firpic) as red, green, and blue light-emitting materials, respectively.
- a mixed system of dopant/host materials can be used as light-emitting materials to improve color purity, luminous efficiency, and stability. If the dopant/host material system is used, the selection of the host materials is important since the host materials greatly influence the efficiency and performance of a light-emitting device.
- 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known phosphorescent host material.
- Pioneer (Japan) et al. currently developed a high performance organic EL device by employing bathocuproine (BCP), aluminum(III) bis(2-methyl-8-quinolinato)(4-phenylphenolate) (BAlq), etc., which were used in a hole blocking layer, as host materials.
- Korean Patent Application Laying-open Nos. 10-2012-0087935 and 10-2012-0095997 disclose fused heterocyclic compounds used as a matrix material, a hole transport or an electron blocking material, an exiton blocking material, or an electron transport or a hole blocking material of a phosphorescent OLED.
- 2011-0303901 discloses indole-quinoline derivatives used as a host or dopant material, a hole transport material, an electron transport material, a hole blocking material, an electron blocking material, a hole injection material, or an electron injection material.
- the organic EL devices comprising the compounds recited in the above publications still do not satisfy power efficiency, luminous efficiency, lifespan, etc.
- the present inventors have tried to find organic electroluminescent compounds that can provide an organic EL device with properties superior to the compounds recited in the above publications and have found compounds providing a device with high luminous efficiency and excellent device properties.
- the object of the present invention is to provide organic electroluminescent compounds which can provide an organic EL device with long lifespan and improved luminous efficiency.
- X and Y each independently represent -CR 13 - or -N-, with the proviso that X and Y do not simultaneously represent -CR 13 -;
- W and V each independently represent a single bond, O or S;
- R 1 to R 13 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri
- the organic electroluminescent compounds according to the present invention have better luminous efficiency than that of conventional compounds.
- an organic EL device comprising the organic electroluminescent compounds of the present invention as a host material for light-emitting has long operating lifespan, provides improved current efficiency and power efficiency, reduces electric power consumption, and gives colors having high purity.
- the present invention relates to an organic electroluminescent compound represented by formula 1 or 2 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic EL device comprising the material.
- each of R 1 to R 13 may preferably represent hydrogen, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group; and more preferably, hydrogen, or a substituted or unsubstituted (C6-C12)aryl group.
- (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- Substituents of the substituted alkyl group, the substituted cycloalkyl group, the substituted aryl group, the substituted heteroaryl group, the substituted alkoxy group, the substituted alkylsilyl group, the substituted arylsilyl group, the substituted alkylamino group, the substituted arylamino group, or the substituted mono- or polycyclic (C3-C30) alicyclic or aromatic ring in formulae 1 and 2 above are each independently at least one selected from the group consisting of deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C
- the compound of formula 1 or 2 above may be selected from the group consisting of the following compounds, but is not limited thereto:
- organic electroluminescent compounds according to the present invention can be prepared by known methods to one skilled in the art, and can be prepared, for example, according to the following reaction scheme 1:
- R 1 to R 9 , X, Y, V, and W are as defined in formula 1.
- the present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 or 2, and an organic EL device comprising the material.
- the material can be comprised of the organic electroluminescent compound of formula 1 or 2 of the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
- the organic EL device of the present invention may comprise an anode, a cathode, and at least one organic layer disposed between the two electrodes, wherein the organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron buffer layer, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.
- HIL hole injection layer
- HTL hole transport layer
- EBL electron blocking layer
- HBL hole buffer layer
- HBL hole blocking layer
- ETL electron transport layer
- EIL electron injection layer
- the organic electroluminescent compound of formula 1 or 2 according to the present invention may be included in a light-emitting layer. If used in a light-emitting layer, the organic electroluminescent compound of formula 1 or 2 of the present invention may be included as a host material.
- the light-emitting layer may preferably comprise at least one dopant and further comprise other compounds as the second host material, in addition to the organic electroluminescent compound of formula 1 or 2 of the present invention.
- the second host material can be any of the known phosphorescent hosts and preferably, is selected from the group consisting of the compounds of the following formulae 3 to 7 in view of luminous efficiency:
- A represents O or S
- R 21 to R 24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group, or R 25 R 26 R 27 Si-; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C5-C30) alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- R 25 to R 27 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group;
- L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- or 30-membered heteroarylene group;
- M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- or 30-membered heteroaryl group;
- Y 1 and Y 2 each independently represent -O-, -S-, -N(R 31 )-, or -C(R 32 )(R 33 )-; and Y 1 and Y 2 are not simultaneously present;
- R 31 to R 33 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- or 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C5-C30) alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and R 32 and R 33 may be the same or different;
- h and i each independently represent an integer of 1 to 3;
- j, k, l, and m each independently represent an integer of 0 to 4.
- each (Cz-L 4 ), each (Cz), each R 21 , each R 22 , each R 23 , or each R 24 may be the same or different.
- the second host material preferably includes the following:
- TPS represents a triphenylsilyl group.
- the dopants included in the organic EL device of the present invention may be selected from the group consisting of the compounds represented by the following formulae 8 to 10:
- L is selected from the following structures:
- R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
- R 101 to R 109 and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group which is unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, a cyano group, a substituted or unsubstituted (C1-C30)alkoxy group, or a substituted or unsubstituted (C6-C30)aryl group;
- R 120 to R 123 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, quinoline;
- R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; when R 124 to R 127 are aryl groups, they may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, fluorene, benzofuran, or benzothiophene;
- R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group which is unsubstituted or substituted with a halogen(s), or a substituted or unsubstituted (C6-C30)aryl group;
- R 208 to R 211 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30) alicyclic, aromatic, or heteroaromatic ring, for example, fluorene, dibenzothiophene, or dibenzofuran;
- f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R 100 may be the same or different; and
- n an integer of 1 to 3.
- the dopant material includes the following:
- the organic EL device of the present invention may comprise the organic electroluminescent compound of formula 1 or 2 in an organic layer and further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
- the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal, in addition to the organic electroluminescent compound of formula 1 or 2.
- the organic EL device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound of the present invention; and may further include a yellow or orange light-emitting layer, if necessary.
- a surface layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
- a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of a light-emitting medium layer.
- the surface layer provides operating stability for the organic EL device.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a hole injection layer, a hole transport layer, an electron blocking layer, or their combinations can be used between an anode and a light-emitting layer.
- the hole injection layer may be multi-layers in order to lower a hole injection barrier (or hole injection voltage) from an anode to a hole transport layer or electron blocking layer, wherein each of the multi-layers simultaneously may use two compounds.
- the hole transport layer or the electron blocking layer may also be multi-layers.
- An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or their combinations can be used between a light-emitting layer and a cathode.
- the electron buffer layer may be multi-layers in order to control the injection of an electron and improve interface properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers simultaneously may use two compounds.
- the hole blocking layer or the electron transport layer may also be multi-layers, wherein each of the multi-layers may use a multi-component of compounds.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to a light-emitting medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to a light-emitting medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge-generating layer to prepare an organic EL device having two or more light-emitting layers and emitting white light.
- dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc.
- wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
- a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents and the solvents do not cause any problems in forming a layer.
- An OLED device comprising the organic electroluminescent compound of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
- ITO indium tin oxide
- N 4 ,N 4' -Diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate.
- Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile was then introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
- N-([1,1'-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine was introduced into a cell of the vacuum vapor depositing apparatus.
- Compound A-333 as a host was introduced into a cell of the vacuum vapor depositing apparatus and compound D-96 was introduced into another cell.
- the two materials were evaporated at a different rate, and the dopant was deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
- the produced OLED device showed red emission having an efficiency of 27.3 cd/A at 3.7 V, CIE color coordinate (X,Y) at 1000 cd/m 2 of (0.670, 0.330), and the time taken for the light-emission to be reduced from 100% to 90% at a luminance of 5,000 nit of 17 hrs or more.
- Comparative Example 1 Production of an OLED device by using conventional organic electroluminescent compound
- An OLED device was produced in the same manner as in Device Example 1, except that compound B-1 below was used as a host in a light-emitting material.
- the produced OLED device showed red emission having an efficiency of 7.7 cd/A at 9.6 V, CIE color coordinate (X,Y) at 1000 cd/m 2 of (0.657, 0.336), and the time taken for the light-emission to be reduced from 100% to 90% at a luminance of 5,000 nit of 1 hr or more.
- the organic electroluminescent compounds according to the present invention have high luminous efficiency, in particular current efficiency and power efficiency compared with conventional compounds, and give colors having high purity.
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Abstract
Cette invention concerne un nouveau composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. Le composé électroluminescent organique selon l'invention a un rendement lumineux élevé, et peut par conséquent être utilisé comme couche électroluminescente hôte ; et le dispositif électroluminescent organique comprenant les composés électroluminescents organiques selon l'invention a une longue durée de vie en fonctionnement, permet d'obtenir de meilleurs rendement en courant et rendement énergétique, et génère des couleurs de pureté élevée.
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US15/318,099 US9698355B2 (en) | 2014-06-27 | 2015-06-26 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
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WO2017191896A1 (fr) * | 2016-05-03 | 2017-11-09 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique et dispositif électroluminescent organique le comportant |
EP3166947A4 (fr) * | 2014-07-09 | 2017-12-20 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé |
CN109071413A (zh) * | 2016-05-03 | 2018-12-21 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
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JP2014073965A (ja) * | 2012-10-02 | 2014-04-24 | Canon Inc | 新規ベンゾインドロカルバゾール化合物、これを有する有機発光素子、表示装置、画像情報処理装置、照明装置、画像形成装置 |
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JP2014073965A (ja) * | 2012-10-02 | 2014-04-24 | Canon Inc | 新規ベンゾインドロカルバゾール化合物、これを有する有機発光素子、表示装置、画像情報処理装置、照明装置、画像形成装置 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3166947A4 (fr) * | 2014-07-09 | 2017-12-20 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé |
WO2017191896A1 (fr) * | 2016-05-03 | 2017-11-09 | Rohm And Haas Electronic Materials Korea Ltd. | Composé électroluminescent organique et dispositif électroluminescent organique le comportant |
CN109071413A (zh) * | 2016-05-03 | 2018-12-21 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
CN109071413B (zh) * | 2016-05-03 | 2023-04-04 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
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