WO2015012618A1 - Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé - Google Patents
Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé Download PDFInfo
- Publication number
- WO2015012618A1 WO2015012618A1 PCT/KR2014/006754 KR2014006754W WO2015012618A1 WO 2015012618 A1 WO2015012618 A1 WO 2015012618A1 KR 2014006754 W KR2014006754 W KR 2014006754W WO 2015012618 A1 WO2015012618 A1 WO 2015012618A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- aryl
- alkyl
- membered
- Prior art date
Links
- 0 *C(*)(C(C=C)(c(c-1c2O)c(*)c(*)c2O)I)*(c(*)c2*)c-1c(N1CC1)c2N Chemical compound *C(*)(C(C=C)(c(c-1c2O)c(*)c(*)c2O)I)*(c(*)c2*)c-1c(N1CC1)c2N 0.000 description 3
- PITGIMTUWJAYTI-UHFFFAOYSA-N C(C1C2(c(c(cccc3)c3cc3)c3-c3cc(N(c4ccccc4)c4ccccc4)c4)c3c4N(c3ccccc3)c3ccccc3)=CC=CC1c1c2cccc1 Chemical compound C(C1C2(c(c(cccc3)c3cc3)c3-c3cc(N(c4ccccc4)c4ccccc4)c4)c3c4N(c3ccccc3)c3ccccc3)=CC=CC1c1c2cccc1 PITGIMTUWJAYTI-UHFFFAOYSA-N 0.000 description 1
- QYRFCXDNGPHHBI-UHFFFAOYSA-N C1C(c2c3-c4ccccc4C4(c(cccc5)c5-c5c4cccc5)c3ccc2)=CC(N(c2ccccc2)c2ccccc2)=CC1N(c1ccccc1)c1ccccc1 Chemical compound C1C(c2c3-c4ccccc4C4(c(cccc5)c5-c5c4cccc5)c3ccc2)=CC(N(c2ccccc2)c2ccccc2)=CC1N(c1ccccc1)c1ccccc1 QYRFCXDNGPHHBI-UHFFFAOYSA-N 0.000 description 1
- AQEWLEYQZUWYDX-UHFFFAOYSA-N C1C=CC(N(c2ccccc2)c2cc(-c3ccc(C4(c(cccc5)c5-c5c4cccc5)c4ccccc4-4)c-4c3)cc(N(c3ccccc3)c3ccccc3)c2)=CC1 Chemical compound C1C=CC(N(c2ccccc2)c2cc(-c3ccc(C4(c(cccc5)c5-c5c4cccc5)c4ccccc4-4)c-4c3)cc(N(c3ccccc3)c3ccccc3)c2)=CC1 AQEWLEYQZUWYDX-UHFFFAOYSA-N 0.000 description 1
- RHXRXGOBRDLWOK-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c(cc2)ccc2-c2ccccc2)c2-c3ccccc3C(c3ccccc3-c3c4c5c6cccc5)(c3ccc4[n]6-c3ccccc3)c2c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c(cc2)ccc2-c2ccccc2)c2-c3ccccc3C(c3ccccc3-c3c4c5c6cccc5)(c3ccc4[n]6-c3ccccc3)c2c1 RHXRXGOBRDLWOK-UHFFFAOYSA-N 0.000 description 1
- DZKMQDALNBVTME-UHFFFAOYSA-N c(cc1)ccc1N(c1cc(N(c2ccccc2)c2c(cccc3)c3ccc2)c2-c3ccccc3C(c3ccccc3-c3c4)(c3cc3c4c4ccccc4[o]3)c2c1)c1c(cccc2)c2ccc1 Chemical compound c(cc1)ccc1N(c1cc(N(c2ccccc2)c2c(cccc3)c3ccc2)c2-c3ccccc3C(c3ccccc3-c3c4)(c3cc3c4c4ccccc4[o]3)c2c1)c1c(cccc2)c2ccc1 DZKMQDALNBVTME-UHFFFAOYSA-N 0.000 description 1
- ALQXBLIPRBIGAB-UHFFFAOYSA-N c(cc1)ccc1N(c1cc2ccccc2cc1)c1cc(N(c2ccccc2)c2cc(cccc3)c3cc2)c2-c3ccccc3C3(c4ccc5[o]c(cccc6)c6c5c4-c4ccccc34)c2c1 Chemical compound c(cc1)ccc1N(c1cc2ccccc2cc1)c1cc(N(c2ccccc2)c2cc(cccc3)c3cc2)c2-c3ccccc3C3(c4ccc5[o]c(cccc6)c6c5c4-c4ccccc34)c2c1 ALQXBLIPRBIGAB-UHFFFAOYSA-N 0.000 description 1
- HJHSKBLMXJXCGG-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc12)cc(N(c3ccccc3)c3ccccc3)c1-c1ccccc1C21c(c(cccc2)c2cc2)c2-c2c1cccc2 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc12)cc(N(c3ccccc3)c3ccccc3)c1-c1ccccc1C21c(c(cccc2)c2cc2)c2-c2c1cccc2 HJHSKBLMXJXCGG-UHFFFAOYSA-N 0.000 description 1
- HVCLFMMJHRWTBO-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1C23c4cc5ccccc5cc4-c4ccccc24)cc(N(c2ccccc2)c2ccccc2)c1-c1c3cccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1C23c4cc5ccccc5cc4-c4ccccc24)cc(N(c2ccccc2)c2ccccc2)c1-c1c3cccc1 HVCLFMMJHRWTBO-UHFFFAOYSA-N 0.000 description 1
- WEOYUMGERXRSSY-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c1cc(-c(cc2)cc(C34c(cccc5)c5-c5c3cccc5)c2-c2c4cccc2)cc(N(c2ccccc2)c2ccccc2)c1 Chemical compound c(cc1)ccc1N(c1ccccc1)c1cc(-c(cc2)cc(C34c(cccc5)c5-c5c3cccc5)c2-c2c4cccc2)cc(N(c2ccccc2)c2ccccc2)c1 WEOYUMGERXRSSY-UHFFFAOYSA-N 0.000 description 1
- XRWBVKQNYYLUGM-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c2ccccc2)c(C2(c3ccccc3-3)c(c(cccc4)c4cc4)c4-c4ccccc24)c-3c1 Chemical compound c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c2ccccc2)c(C2(c3ccccc3-3)c(c(cccc4)c4cc4)c4-c4ccccc24)c-3c1 XRWBVKQNYYLUGM-UHFFFAOYSA-N 0.000 description 1
- QFZMQOBCTIGMLM-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c2ccccc2)c2-c3ccccc3C(c3ccccc3-3)(c(cc4)c-3c3c4[s]c4ccccc34)c2c1 Chemical compound c(cc1)ccc1N(c1ccccc1)c1cc(N(c2ccccc2)c2ccccc2)c2-c3ccccc3C(c3ccccc3-3)(c(cc4)c-3c3c4[s]c4ccccc34)c2c1 QFZMQOBCTIGMLM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
-
- 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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—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
-
- 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
Definitions
- the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
- fluorescent materials have been widely used as light-emitting material.
- phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, phosphorescent light-emitting materials have been widely being researched.
- Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- BCP bathocuproine
- BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
- the organic EL device may be manufactured with a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised.
- a compound for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
- CuPc copper phthalocyanine
- NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
- TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
- MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
- WO 2012/034627 discloses compounds for an organic EL device, in which only one substituent selected from a diarylamine, a heteroarylamine, and a nitrogen-containing heteroaryl group is bonded, directly or via a linker such as aryl, to a benzene ring of spirofluorene.
- this reference fails to specifically disclose a compound in which two substituents are bonded to a linker or a benzene ring of spirofluorene, and an organic electroluminescent device employing the same for a hole transport layer.
- the objective of the present disclosure is to provide an organic electroluminescent compound showing excellence in current efficiency and thermal stability due to high glass transition temperature.
- the organic electroluminescent compound represented by formula 1, of the present disclosure includes a spirofluorene structure as a mother nucleus, which provides high glass transition temperature and excellent thermal stability.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- Ar 5 to Ar 8 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- n and n each independently, represent an integer of 0 to 2; where m or n is 2, each of -N(Ar 1 )(Ar 2 ) or each of -N(Ar 3 )(Ar 4 ) may be the same or different;
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; where m is 0, L 1 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
- L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; where n is 0, L 2 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
- o 1 or 2; where o is 2, each of Ar 5 may be the same or different;
- p, q, and r each independently, represent an integer of 1 to 4; where p, q, or r is an integer of 2 or more, each of Ar 6 , each of Ar 7 , or each of Ar 8 may be the same or different;
- R 1 to R 3 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or R 1 and R 2 may be linked to each other to
- the compound of formula 1 may be preferably represented by the following formula 2 or 3.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl
- L 1 , L 2 , Ar 5 to Ar 8 , and o to r are as defined in formula 1.
- the compound of formula 1 may be preferably represented by the following formula 4.
- Ar 1 and Ar 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl
- L 1 ' represents a substituted or unsubstituted (C6-C30)arylene
- Ar 5 to Ar 8 , and o to r are as defined in formula 1.
- the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device showing excellence in current efficienty and thermal stability due to its high glass transition temperature (Tg).
- the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
- (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 10, and more preferably 1 to 6 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (C6-C30)aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, 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, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene) and the substituted heteroaryl(ene) in Ar 1 to Ar 8 , R 1 to R 3 , L 1 , and L 2 , each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl, a (3- to
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably, represent a substituted or unsubstituted (C6-C20)aryl; and more preferably, represent a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C15)aryl, or a di(C1-C6)alkyl(C6-C15)aryl.
- Ar 1 to Ar 4 each independently, may be phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, phenanthrenyl, triphenylenyl, or fluoranthenyl.
- Ar 1 and Ar 2 may be the same as Ar 3 or Ar 4 , wherein Ar 3 and Ar 4 may be the same or different.
- Ar 5 to Ar 8 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; preferably represent hydrogen, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 20-membered), mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and more preferably represent hydrogen, or may be linked to an adjacent substituent(
- Ar 5 may be hydrogen; and one of Ar 6 to Ar 8 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring.
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably represents a single bond, or an unsubstituted (C6-C20)arylene; more preferably represents a single bond, or an unsubstituted (C6-C15)arylene; and specifically represents phenylene, biphenylene, or naphthylene.
- L 1 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and specifically represents hydrogen.
- L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably represents a single bond, or an unsubstituted (C6-C20)arylene; more preferably represents a single bond, or an unsubstituted (C6-C15)arylene; and specifically represents phenylene, biphenylene, or naphthylene.
- L 2 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and specifically represents hydrogen.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C20)aryl
- Ar 5 to Ar 8 each independently, represet hydrogen, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 20-membered), mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur
- m is 1 or 2
- L 1 represents a single bond or an unsubstituted (C6-C20)arylene
- where m represents hydrogen
- n is 1 or 2
- L 2 represents a single bond or an unsubstituted (C6-C20)arylene
- n 0, L 2 represents hydrogen
- Ar 1 to Ar 4 each independently, represent a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C15)aryl, or a di(C1-C6)alkyl(C6-C15)aryl;
- Ar 5 to Ar 8 each independently, represent hydrogen, or may be linked to an adjacent substituent(s) to form a (3- to 15-membered), mono- or polycyclic aromatic ring unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C15)aryl, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- m is 1 or 2
- L 1 represents a single bond or an unsubstituted (C6-C15)arylene; where m is 0, L 1 represents hydrogen; where n is 1 or 2, L 2 represents a single bond
- organic electroluminescent compound of formula 1 includes the following, but is not limited thereto:
- the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to one skilled in the art. For example, it can be prepared according to the following reaction scheme 1.
- Ar 1 to Ar 8 , L 1 , L 2 , m, n, and o to r are as defined in formula 1 above, and Hal represents a halogen.
- aryl amine and aryl halide are reacted with each other under a basic condition (e.g. by sodium t-butoxide) to form a carbon-nitrogen bond.
- the reaction is carried out in an aromatic organic solvent such as toluene or xylene; and is usually performed under reflux by using palladium complex such as a combination of palladium acetate and S-Phos (2-dicyclophosphino-2’,6’-dimethoxyphenyl) as a catalyst.
- the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
- the material may consist of the organic electroluminescent compound of the present disclosure. Otherwise, the material may further comprise a conventional compound(s) which has been comprised for an organic electroluminescent device, in addition to the compound of the present disclosure.
- the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- the organic layer may comprise at least one compound of formula 1.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
- the organic electroluminescent compound of the present disclosure may be comprised in at least one of the light-emitting layer and the hole transport layer.
- the organic electroluminescent compound of the present disclosure may be comprised as a hole transport material.
- the organic electroluminescent compound of the present disclosure may be comprised as a host material.
- the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure may further comprise at least one compound other than the organic electroluminescent compound of the present disclosure, as a host material. Furthermore, the organic electroluminescent device may further comprise at least one dopant.
- organic electroluminescent compound of the present disclosure is comprised as a host material (a first host material) in a light-emitting layer
- another compound may be comprised as a second host material.
- the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
- the second host material may be from any of the known phosphorescent host materials. Specifically, the compound selected from the group consisting of the compounds of formulae 11 to 13 below is preferable as the second host material in view of luminous efficiency.
- R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl or R 25 R 26 R 27 Si-;
- R 25 to R 27 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
- L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
- M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered
- the second host material includes the following:
- the dopant for the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
- the phosphorescent dopant for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
- the phosphorescent dopant may be preferably selected from the group consisting of compounds represented by the following formulae 101 to 103.
- L is selected from the following structures:
- R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl
- R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, or a substituted or unsubstituted (C3-C30)cycloalkyl
- R 120 to R 123 may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, e.g.
- R 124 to R 127 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; where R 124 to R 127 are aryl, they may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, e.g.
- R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, or a (C1-C30)alkyl unsubstituted or substituted with a halogen;
- c and d each independently, represent an integer of 1 to 3; where c or d is an integer of 2 or more, each of R 100 may be the same or different; and e represents an integer of 1 to 3.
- the phosphorescent dopant material includes the following:
- a mixture or composition for preparing an organic electroluminescent device comprises the compound of the present disclosure, as a host material or a hole transport material.
- the mixture or composition may be a mixture or composition for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device.
- the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- the organic layer may comprise a light-emitting layer, which may comprise the mixture or composition for the organic electroluminescent device of the present disclosure.
- the organic electroluminescent device of the present disclosure may further comprise, in addition to the compound of formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise, in addition to the compound of formula 1, 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic layer may further comprise a light-emitting layer and a charge generating layer.
- the organic electroluminescent device of the present disclosure 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 known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
- at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
- a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
- a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- 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 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 an electroluminescent 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 the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds
- 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 electroluminescent device having two or more light-emitting layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
- a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
- OLED was produced using the compound of the present disclosure as follows.
- a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and was then stored in isopropanol.
- the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
- N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- Compound C-2 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, 9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole was introduced into one cell of the vacuum vapor depositing apparatus as a host material, and compound D-1 was introduced into another cell as a dopant.
- the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
- the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- An OLED was produced. All the materials used for producing the OLED were those purified by vacuum sublimation at 10 -6 torr. The produced OLED showed green emission having a luminance of 1,100 cd/m 2 and a current density of 2.4 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-29 was used to form a hole transport layer having a thickness of 20 nm; and after introducing 7-(4-([1,1'-biphenyl]-4-yl)quinazolin-2-yl)-7H-benzo[c]carbazole as a host material and compound D-87 as a dopant into the two cells of the vacuum vapor depositing apparatus, respectively, the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- the produced OLED showed red emission having a luminance of 1,880 cd/m 2 and a current density of 13.2 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-8 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 1,400 cd/m 2 and a current density of 2.9 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-49 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 2,100 cd/m 2 and a current density of 4.4 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 2, except that compound C-40 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed red emission having a luminance of 2,500 cd/m 2 and a current density of 18.0 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 8,000 cd/m 2 and a current density of 20.9 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 2, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed red emission having a luminance of 6,000 cd/m 2 and a current density of 80.0 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound-1 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 9,000 cd/m 2 and a current density of 21.5 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 2, except that compound-1 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed red emission having a luminance of 7,000 cd/m 2 and a current density of 62.5 mA/cm 2 .
- the organic electroluminescent compound of the present disclosure has high glass transition temperature, and provides higher current efficiency than conventional compounds.
- the organic electroluminescent device shows excellent luminous efficiency, especially current efficienty by using the organic electroluminescent compound of the present disclosure.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention porte sur un nouveau composé électroluminescent organique et sur un dispositif électroluminescent organique le comprenant. Le composé électroluminescent organique selon l'invention possède une température de transition vitreuse élevée, et présente par conséquent une bonne stabilité thermique. L'utilisation du composé électroluminescent organique selon l'invention permet de fournir un dispositif électroluminescent organique présentant un excellent rendement électrique.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201480038815.7A CN105358654B (zh) | 2013-07-25 | 2014-07-24 | 有机电致发光化合物和包含所述化合物的有机电致发光装置 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2013-0088044 | 2013-07-25 | ||
KR1020130088044A KR102157998B1 (ko) | 2013-07-25 | 2013-07-25 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015012618A1 true WO2015012618A1 (fr) | 2015-01-29 |
Family
ID=52393562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2014/006754 WO2015012618A1 (fr) | 2013-07-25 | 2014-07-24 | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé |
Country Status (4)
Country | Link |
---|---|
KR (1) | KR102157998B1 (fr) |
CN (1) | CN105358654B (fr) |
TW (1) | TW201520307A (fr) |
WO (1) | WO2015012618A1 (fr) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016078738A1 (fr) * | 2014-11-18 | 2016-05-26 | Merck Patent Gmbh | Matières pour dispositifs électroluminescents organiques |
WO2016131521A1 (fr) * | 2015-02-16 | 2016-08-25 | Merck Patent Gmbh | Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques |
WO2016199784A1 (fr) * | 2015-06-08 | 2016-12-15 | 出光興産株式会社 | Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique |
WO2017061785A1 (fr) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Composé de type spiro et diode électroluminescente organique comprenant celui-ci |
WO2017061779A1 (fr) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Composé amine et dispositif électroluminescent organique le comprenant |
WO2017111544A1 (fr) * | 2015-12-24 | 2017-06-29 | 주식회사 두산 | Composé organique et dispositif électroluminescent organique le comprenant |
WO2017133829A1 (fr) * | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Matériaux pour dispositifs électroniques |
CN107922310A (zh) * | 2015-09-04 | 2018-04-17 | 株式会社Lg化学 | 基于胺的化合物及包含其的有机发光器件 |
WO2018095389A1 (fr) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Composé cyclique hétérocyclique fusionné contenant de l'azote et son application |
JP2018531232A (ja) * | 2015-10-06 | 2018-10-25 | エルジー・ケム・リミテッド | アミン化合物およびこれを含む有機発光素子 |
CN109804045A (zh) * | 2016-10-14 | 2019-05-24 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光装置 |
JP2020019748A (ja) * | 2018-08-03 | 2020-02-06 | 東ソー株式会社 | トリフェニレン化合物及びその用途 |
US10738034B2 (en) | 2015-10-06 | 2020-08-11 | Lg Chem, Ltd. | Spiro compound and organic light-emitting device comprising same |
US10781366B2 (en) | 2015-10-06 | 2020-09-22 | Lg Chem, Ltd. | Spiro compound and organic light-emitting device comprising same |
JP2020533324A (ja) * | 2017-09-08 | 2020-11-19 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
US11075342B2 (en) | 2015-10-06 | 2021-07-27 | Lg Chem, Ltd. | Spiro-type compound and organic light emitting diode comprising same |
US11871661B2 (en) | 2015-12-17 | 2024-01-09 | Samsung Display Co., Ltd. | Organic light-emitting device |
US11884836B2 (en) | 2018-02-28 | 2024-01-30 | Lg Chem, Ltd. | Polymer, coating composition comprising same, and organic light emitting element using same |
US11937502B2 (en) * | 2015-04-14 | 2024-03-19 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device comprising the same |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102283231B1 (ko) * | 2015-03-16 | 2021-07-30 | 덕산네오룩스 주식회사 | 유기전기소자용 신규 화합물, 이를 이용한 유기전기소자 및 그 전자장치 |
WO2018026197A1 (fr) * | 2016-08-03 | 2018-02-08 | 덕산네오룩스 주식회사 | Composé pour élément électrique organique, élément électrique organique l'utilisant, et appareil électronique le comprenant |
CN109689618B (zh) * | 2016-09-23 | 2022-01-04 | 株式会社Lg化学 | 基于胺的化合物和包含其的有机发光器件 |
KR102010893B1 (ko) | 2016-09-23 | 2019-08-14 | 주식회사 엘지화학 | 아민계 화합물 및 이를 포함하는 유기 발광 소자 |
KR102668890B1 (ko) * | 2017-04-03 | 2024-05-27 | 듀폰스페셜티머터리얼스코리아 유한회사 | 유기 전계 발광 소자 |
KR102575687B1 (ko) * | 2017-06-30 | 2023-09-07 | 주식회사 동진쎄미켐 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
KR102274796B1 (ko) * | 2018-07-05 | 2021-07-08 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
KR20200089885A (ko) * | 2019-01-18 | 2020-07-28 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN111056960A (zh) * | 2019-11-04 | 2020-04-24 | 苏州久显新材料有限公司 | 芴类衍生物和电子器件 |
CN112239475B (zh) * | 2020-01-22 | 2023-03-24 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件和电子装置 |
CN111423330B (zh) * | 2020-03-31 | 2023-03-07 | 吉林省元合电子材料有限公司 | 一种基于并螺芴的芳香胺衍生物及其应用 |
CN114106003B (zh) * | 2020-08-31 | 2023-05-16 | 上海和辉光电股份有限公司 | 一种化合物及其应用 |
CN112375054B (zh) * | 2021-01-13 | 2021-05-25 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
CN112390768B (zh) * | 2021-01-19 | 2021-04-13 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
KR20220114252A (ko) * | 2021-02-08 | 2022-08-17 | 주식회사 엘지화학 | 아민계 화합물 및 이를 포함하는 유기 발광 소자 |
CN115322189B (zh) * | 2021-09-28 | 2023-11-28 | 四川阿格瑞新材料有限公司 | 一种螺环化合物及其应用 |
CN113845431B (zh) * | 2021-10-20 | 2024-03-29 | 上海钥熠电子科技有限公司 | 螺芴衍生物类胺化合物和包含其的有机电致发光器件 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20090041999A (ko) * | 2007-10-25 | 2009-04-29 | 주식회사 하나화인켐 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
EP2096108A1 (fr) * | 2008-02-29 | 2009-09-02 | Gracel Display Inc. | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant |
EP2108690A1 (fr) * | 2008-04-02 | 2009-10-14 | Gracel Display Inc. | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant |
KR20090117326A (ko) * | 2008-05-09 | 2009-11-12 | 주식회사 하나화인켐 | 유기 발광 소자 및 이에 사용되는 유기 발광 화합물 |
WO2012034627A1 (fr) * | 2010-09-15 | 2012-03-22 | Merck Patent Gmbh | Matériaux pour dispositifs électroluminescents organiques |
-
2013
- 2013-07-25 KR KR1020130088044A patent/KR102157998B1/ko active IP Right Grant
-
2014
- 2014-07-24 WO PCT/KR2014/006754 patent/WO2015012618A1/fr active Application Filing
- 2014-07-24 CN CN201480038815.7A patent/CN105358654B/zh active Active
- 2014-07-25 TW TW103125449A patent/TW201520307A/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20090041999A (ko) * | 2007-10-25 | 2009-04-29 | 주식회사 하나화인켐 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
EP2096108A1 (fr) * | 2008-02-29 | 2009-09-02 | Gracel Display Inc. | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant |
EP2108690A1 (fr) * | 2008-04-02 | 2009-10-14 | Gracel Display Inc. | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant |
KR20090117326A (ko) * | 2008-05-09 | 2009-11-12 | 주식회사 하나화인켐 | 유기 발광 소자 및 이에 사용되는 유기 발광 화합물 |
WO2012034627A1 (fr) * | 2010-09-15 | 2012-03-22 | Merck Patent Gmbh | Matériaux pour dispositifs électroluminescents organiques |
Non-Patent Citations (1)
Title |
---|
SARAGI T.P.I. ET AL.: "Light responsive amorphous organic field-effect transistor based on spiro-linked compound", OPTICAL MATERIALS, vol. 29, 2007, pages 879 - 884, XP005836004, DOI: doi:10.1016/j.optmat.2006.01.013 * |
Cited By (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20170338414A1 (en) * | 2014-11-18 | 2017-11-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US10510960B2 (en) | 2014-11-18 | 2019-12-17 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2016078738A1 (fr) * | 2014-11-18 | 2016-05-26 | Merck Patent Gmbh | Matières pour dispositifs électroluminescents organiques |
WO2016131521A1 (fr) * | 2015-02-16 | 2016-08-25 | Merck Patent Gmbh | Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques |
TWI713491B (zh) * | 2015-02-16 | 2020-12-21 | 德商麥克專利有限公司 | 電子裝置用材料 |
US10032989B2 (en) | 2015-02-16 | 2018-07-24 | Merck Patent Gmbh | Spirobifluorene derivative-based materials for electronic devices |
JP2018507909A (ja) * | 2015-02-16 | 2018-03-22 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN107223122A (zh) * | 2015-02-16 | 2017-09-29 | 默克专利有限公司 | 用于电子器件的基于螺二芴衍生物的材料 |
US11937502B2 (en) * | 2015-04-14 | 2024-03-19 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device comprising the same |
US10243148B2 (en) | 2015-06-08 | 2019-03-26 | Idemitsu Kosan Co., Ltd. | Aromatic amine compound, and organic electroluminescent elements including the compound |
JP2017001979A (ja) * | 2015-06-08 | 2017-01-05 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
WO2016199784A1 (fr) * | 2015-06-08 | 2016-12-15 | 出光興産株式会社 | Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique |
CN107922310B (zh) * | 2015-09-04 | 2020-10-02 | 株式会社Lg化学 | 基于胺的化合物及包含其的有机发光器件 |
EP3330249A4 (fr) * | 2015-09-04 | 2018-08-01 | LG Chem, Ltd. | Composé à base d'amine et dispositif électroluminescent organique contenant ce composé |
JP2018531903A (ja) * | 2015-09-04 | 2018-11-01 | エルジー・ケム・リミテッド | アミン系化合物およびこれを含む有機発光素子 |
US10991886B2 (en) | 2015-09-04 | 2021-04-27 | Lg Chem, Ltd. | Amine-based compound and organic light emitting device comprising same |
CN107922310A (zh) * | 2015-09-04 | 2018-04-17 | 株式会社Lg化学 | 基于胺的化合物及包含其的有机发光器件 |
US11075342B2 (en) | 2015-10-06 | 2021-07-27 | Lg Chem, Ltd. | Spiro-type compound and organic light emitting diode comprising same |
JP2018531232A (ja) * | 2015-10-06 | 2018-10-25 | エルジー・ケム・リミテッド | アミン化合物およびこれを含む有機発光素子 |
WO2017061779A1 (fr) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Composé amine et dispositif électroluminescent organique le comprenant |
US10991887B2 (en) | 2015-10-06 | 2021-04-27 | Lg Chem, Ltd. | Amine compound and organic light-emitting device comprising same |
WO2017061785A1 (fr) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Composé de type spiro et diode électroluminescente organique comprenant celui-ci |
US10738034B2 (en) | 2015-10-06 | 2020-08-11 | Lg Chem, Ltd. | Spiro compound and organic light-emitting device comprising same |
US10781366B2 (en) | 2015-10-06 | 2020-09-22 | Lg Chem, Ltd. | Spiro compound and organic light-emitting device comprising same |
US11871661B2 (en) | 2015-12-17 | 2024-01-09 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN108349931B (zh) * | 2015-12-24 | 2022-08-05 | 斗山索如始株式会社 | 有机化合物及包含其的有机电致发光元件 |
CN108349931A (zh) * | 2015-12-24 | 2018-07-31 | 株式会社斗山 | 有机化合物及包含其的有机电致发光元件 |
US11066382B2 (en) | 2015-12-24 | 2021-07-20 | Solus Advanced Materials Co., Ltd. | Organic compound and organic electroluminescent device comprising same |
WO2017111544A1 (fr) * | 2015-12-24 | 2017-06-29 | 주식회사 두산 | Composé organique et dispositif électroluminescent organique le comprenant |
WO2017133829A1 (fr) * | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Matériaux pour dispositifs électroniques |
CN109804045A (zh) * | 2016-10-14 | 2019-05-24 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光装置 |
WO2018095389A1 (fr) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Composé cyclique hétérocyclique fusionné contenant de l'azote et son application |
US11447496B2 (en) | 2016-11-23 | 2022-09-20 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Nitrogen-containing fused heterocyclic ring compound and application thereof |
JP7250773B2 (ja) | 2017-09-08 | 2023-04-03 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
JP2020533324A (ja) * | 2017-09-08 | 2020-11-19 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
US11884836B2 (en) | 2018-02-28 | 2024-01-30 | Lg Chem, Ltd. | Polymer, coating composition comprising same, and organic light emitting element using same |
JP2020019748A (ja) * | 2018-08-03 | 2020-02-06 | 東ソー株式会社 | トリフェニレン化合物及びその用途 |
JP7143670B2 (ja) | 2018-08-03 | 2022-09-29 | 東ソー株式会社 | トリフェニレン化合物及びその用途 |
Also Published As
Publication number | Publication date |
---|---|
CN105358654A (zh) | 2016-02-24 |
KR20150012488A (ko) | 2015-02-04 |
KR102157998B1 (ko) | 2020-09-22 |
CN105358654B (zh) | 2019-05-07 |
TW201520307A (zh) | 2015-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2015012618A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé | |
WO2015099485A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé | |
WO2015084114A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé | |
WO2014196805A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique le comprenant | |
WO2015099486A1 (fr) | Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant | |
WO2015084021A1 (fr) | Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant | |
WO2015037965A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant | |
EP2831197A1 (fr) | Nouveaux composés à électroluminescence organique et dispositif à électroluminescence organique les contenant | |
WO2012121561A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant lesdits composés | |
WO2014042420A1 (fr) | Nouveau composé à électroluminescence organique et dispositif à électroluminescence organique le comprenant | |
WO2013109045A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant | |
WO2013165189A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant | |
WO2015046955A1 (fr) | Nouveau composé organique électroluminescent et dispositif organique électroluminescent le contenant | |
EP2694619A1 (fr) | Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant | |
WO2012015265A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés | |
WO2013081416A1 (fr) | Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés | |
EP3583097A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique le comprenant | |
WO2013162284A1 (fr) | Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique les comprenant | |
WO2014129846A1 (fr) | Composés électroluminescents organiques et dispositif électroluminescent organique comprenant ces composés | |
EP3189035A1 (fr) | Matériau de transport de trous et dispositif électroluminescent organique comprenant celui-ci | |
WO2014200244A1 (fr) | Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant | |
WO2016006925A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé | |
WO2014104720A1 (fr) | Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant | |
WO2014088290A1 (fr) | Composés électroluminescents organiques et dispositif électroluminescent organique comprenant ceux-ci | |
EP3166947A1 (fr) | Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201480038815.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14828810 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 14828810 Country of ref document: EP Kind code of ref document: A1 |