# US 2014/0197384 A1 · Condensed cyclic compound and organic light-emitting diode comprising the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0197384 A1 - Document ID: US20140197384A1 - Status: Published application - Kind: A1 - Application number: 14/012,073 - Filed: 2013-08-28 - Published: 2014-07-17 - Earliest claimed: 2013-01-16 - Assignees: Samsung Display Co., Ltd.; Duk San Neolux Co., Ltd. - Applicants: Duksan High Metal Co., Ltd.; Samsung Display Co., Ltd. - Inventors: Seul-Ong Kim; O-Hyun Kwon; Dong-Woo Shin; Mie-Hwa Park; Bum-Sung Lee - Web page: https://patentgrep.com/patent/US20140197384A1 ## CPC - H10K 85/622: {containing four rings, e.g. pyrene} - C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles - C09K 11/06: containing organic luminescent materials - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - C09K 2211/1416: Condensed systems - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 2102/103: {comprising indium oxides, e.g. ITO} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A condensed cyclic compound represented by Formula 1 below and an organic light-emitting device (OLED) including the condensed cyclic compound are presented. Ar1 and Ar2 in Formula 1 are each independently one of a hydrogen atom, an aryl or heteroaryl group and an arylamino group, at least one of Ar1 and Ar2 being a substituted or unsubstituted 1,2.4-triazol-4-yl group; L1 and L2 in Formula 1 are linking groups, each independently one of a cyclic or noncyclic, saturated or unsaturated hydrocarbon group and a heteroarylene group; a and b in Formula 1 are each independently one of 0 or 1; and R1 to R8 in Formula 1 being each independently one of a variety of inorganic and organic substituents including cyclic or noncyclic, saturated or unsaturated and aromatic, nonaromatic or heteraromatic groups. The OLED may have a low driving voltage, a high emission efficiency and long lifespan characteristics. ## Claims ### Claim 1 A condensed cyclic compound of Formula 1 below: Formula 1 Ar1 and Ar2 in Formula 1 being each independently one of a hydrogen atom, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, and a substituted or unsubstituted C1-C60 arylamino group, at least one of Ar1 and Ar2 being a substituent represented by Formula 2F below: Formula 2F, Z11 being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group, a plurality of Z11s being identical to or different from each other; p being an integer selected from 1 to 4; indicating a binding site; L1 and L2 in Formula 1 being each independently one of a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 alkenylene group, a substituted or unsubstituted C5-C60 cycloalkenylene group, a substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C5-C60 cycloalkynylene group, a substituted or unsubstituted C6-C60 arylene group and a substituted or unsubstituted C5-C60 heteroarylene group; a and b in Formula 1 being each independently 0 or 1; and R1 to R8 in Formula 1 being each independently one of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, —N(Q1)(Q2) and —Si(Q3)(Q4)(Q5) (where Q1 to Q5 are each independently one of a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, and a C2-C60 heteroaryl group). ### Claim 2 (depends on 1) The condensed cyclic compound of claim 1, Ar1 and Ar2 being each independently one of a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted a pyridyl group, a substituted or unsubstituted a pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted isobenzofuryl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzisoxazolyl group, a substituted or unsubstituted imidazopyridyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridoindolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted phenazinyl group, and a substituted or unsubstituted dibenzothiophenyl group. ### Claim 3 (depends on 1) The condensed cyclic compound of claim 1, Ar1 and Ar2 being each independently one of a hydrogen atom and a substituent represented by one of Formulae 2A to 2G below: Z11 being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group, a plurality of Z11s being identical to or different from each other; p being an integer selected from 1 to 7; and * indicates a binding site. ### Claim 4 (depends on 1) The condensed cyclic compound of claim 1, Ar1 and Ar2 being each independently a group represented by one of Formulae 3A to 3J, at least one of Ar1 and Ar2 being a group represented by Formula 3J: * in Formulae 3A to 3J indicating a binding site. ### Claim 5 (depends on 1) The condensed cyclic compound of claim 1, L1 and L2 being each independently one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pentaphenylene group, a substituted or unsubstituted a naphthyl group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted an anthryl group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted picenylene group, a substituted or unsubstituted hexacenylene group, a substituted or unsubstituted spiro-fluorenylene group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted a pyridyl group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted pyranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinylene group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted isobenzofuryl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzisoxazolyl group, a substituted or unsubstituted imidazopyridyl group, a substituted or unsubstituted purinylene group, a substituted or unsubstituted a quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinylene group, a substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted a carbazolyl group, a substituted or unsubstituted pyridoindolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted phenanthridinylene group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted phenazinylene group, and a substituted or unsubstituted dibenzothiophenylene group. ### Claim 6 (depends on 1) The condensed cyclic compound of claim 1, L1 and L2 being each independently one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, and a substituted or unsubstituted pyridazinylene group. ### Claim 7 (depends on 1) The condensed cyclic compound of claim 1, R1 to R8 being each independently one of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group that are substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof. ### Claim 8 (depends on 1) The condensed cyclic compound of claim 1, R1 to R8 being each independently one of a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group. ### Claim 9 (depends on 1) The condensed cyclic compound of claim 1, Ar1 and Ar2 being each independently one of a hydrogen atom and a substituent represented by one of Formulae 2A to 2G below: Z11 in Formulae 2A to 2G being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group, a plurality of Z11s being identical to or different from each other; p being an integer from 1 to 7; and * indicating a binding site; L1 and L2 being each independently one of a phenylene group and a naphthyl group; and a phenylene group and a naphthyl group that are substituted with one of a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group and an ethoxy group; and R1 to R8 being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group. ### Claim 10 (depends on 1) The condensed cyclic compound of claim 1, Ar1 and Ar2 being each independently a group represented by one of Formulae 3A to 3J, at least one of Ar1 and Ar2 being a group represented by Formula 3J: L1 and L2 being each independently one of a phenylene group and a naphthylene group; and R1 to R8 being hydrogen atoms. ### Claim 11 (depends on 1) The condensed cyclic compound of claim 1, the condensed cyclic compound being one of Compounds 1, 4 and 8 to 21 below: ### Claim 12 (depends on 1) An organic light-emitting device comprising: a substrate; a first electrode disposed on the substrate; a second electrode disposed opposite to the first electrode; and an organic layer disposed between the first electrode and the second electrode, the organic layer comprising at least one of the condensed cyclic compounds of claim 1. ### Claim 13 (depends on 12) The organic light-emitting device of claim 12, the organic layer comprising at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer having both hole injection and hole transport capabilities, an emission layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer having both electron injection and electron transport capabilities. ### Claim 14 (depends on 13) The organic light-emitting device of claim 13, the organic layer comprising at least one of the emission layer, the electron injection layer, the electron transport layer, and the electron injection and transport layer, at least one of the emission layer, the electron injection layer, the electron transport layer, and the electron injection and transport layer comprising the condensed cyclic compound. ### Claim 15 (depends on 14) The organic light-emitting device of claim 14, the organic layer comprising the emission layer, the emission layer comprising the condensed cyclic compound. ### Claim 16 (depends on 15) The organic light-emitting device of claim 15, the organic layer comprising the emission layer, the emission layer comprising an organometallic compound including at least one of iridium (Ir), platinum (Pt), osmium (Os), rhenium (Re), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm). ### Claim 17 (depends on 13) The organic light-emitting device of claim 13, at least one of the hole injection layer, the hole transport layer and the hole injection and transport layer disposed between the first electrode and the organic layer, at least one of the hole injection layer, the hole transport layer and the hole injection and transport layer further comprising a charge-generating material. ### Claim 18 (depends on 17) The organic light-emitting device of claim 17, the charge-generating material being a p-type dopant.