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US 9,000,169 B2Granted
Compounds and organic electronic device using the same
AssigneeLG Chem, Ltd.
InventorsDong Hoon Lee, Tae Yoon Park, Jungi Jang, Song Kil Hong, Seong So Kim, Boonjae Jang, Sangbin Lee, Kidong Koo
Life of this patent
Estimating the term…
Abstract
The present invention provides a new compound and an organic electronic device using the same. The organic electronic device according to the present invention exhibits excellent properties in views of efficiency, driving voltage and a life span.
Claims22
A compound represented by the following Formula 1:
- wherein,
- X1 is N or CR3, X2 is N or CR4, X3 is N or CR5, X4 is N or CR6, and all of X1 to X4 are not simultaneously N,
- R3 to R6 are each independently -(L1)p-(Y1)q where p is an integer of 0 to 10, q is an integer of 1 to 10, two or more adjacent groups of R3 to R6 may form a monocycle or a polycycle,
- L1 is oxygen;
- sulfur;
- substituted or unsubstituted nitrogen;
- substituted or unsubstituted phosphorus;
- a substituted or unsubstituted arylene group;
- a substituted or unsubstituted alkenylene group;
- a substituted or unsubstituted fluorenylene group;
- a substituted or unsubstituted carbazolylene group;
- or a substituted or unsubstituted heteroarylene group comprising one or more of N, O and S atoms,
- Y1 is hydrogen;
- heavy hydrogen;
- a halogen group;
- a nitrile group;
- a nitro group;
- a hydroxy group;
- a substituted or unsubstituted alkyl group;
- a substituted or unsubstituted cycloalkyl group;
- a substituted or unsubstituted alkoxy group;
- a substituted or unsubstituted aryloxy group;
- a substituted or unsubstituted alkylthioxy group;
- a substituted or unsubstituted arylthioxy group;
- a substituted or unsubstituted alkylsulfoxy group;
- a substituted or unsubstituted arylsulfoxy group;
- a substituted or unsubstituted alkenyl group;
- a substituted or unsubstituted silyl group;
- a substituted or unsubstituted boron group;
- a substituted or unsubstituted alkylamine group;
- a substituted or unsubstituted aralkylamine group;
- a substituted or unsubstituted arylamine group;
- a substituted or unsubstituted heteroarylamine group;
- a substituted or unsubstituted aryl group;
- a substituted or unsubstituted fluorenyl group;
- a substituted or unsubstituted carbazole group;
- or a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S atoms,
- R1 and R2 may be connected to each other to form or not to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocycle or polycycle, and in the case where R1 and R2 do not form a cycle, R1 and R2 are the same as or different from each other, and each independently hydrogen;
- heavy hydrogen;
- a halogen group;
- a nitrile group;
- a nitro group;
- a hydroxy group;
- a substituted or unsubstituted alkyl group;
- a substituted or unsubstituted cycloalkyl group;
- a substituted or unsubstituted alkoxy group;
- a substituted or unsubstituted aryloxy group;
- a substituted or unsubstituted alkylthioxy group;
- a substituted or unsubstituted arylthioxy group;
- a substituted or unsubstituted alkylsulfoxy group;
- a substituted or unsubstituted arylsulfoxy group;
- a substituted or unsubstituted alkenyl group;
- a substituted or unsubstituted silyl group;
- a substituted or unsubstituted boron group;
- a substituted or unsubstituted alkylamine group;
- a substituted or unsubstituted aralkylamine group;
- a substituted or unsubstituted arylamine group;
- a substituted or unsubstituted heteroarylamine group;
- a substituted or unsubstituted aryl group;
- a substituted or unsubstituted fluorenyl group;
- a substituted or unsubstituted carbazole group;
- or a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S atoms,
- the aromatic or heteroaromatic monocycle and polycycle formed by connecting R1, R2, and R1 and R2 to each other may be each independently substituted by -(L1)p-(Y1)q,
- in the case where two or more L1 and two or more Y1 are present in Formula 1, L1 and Y1 are each independently the same as or different from each other,
- a A1 cycle is represented by Formula 2,
- wherein,
- R7 and R8, R8 and R9, or R9 and R10 are groups connected to Formula 1, the group that is not used in connection to Formula 1 among R7 to R10, R11, R12, R13 and R14 are each independently -(L2)r-(Y2)s where r is an integer of 0 to 10, s is an integer of 1 to 10, and two or more adjacent groups of the group that is not used in connection to Formula 1 among R7 to R10, R11, R12, R13 and R14 may form a monocycle or a polycycle,
- L2 is oxygen;
- sulfur;
- substituted or unsubstituted nitrogen;
- substituted or unsubstituted P;
- a substituted or unsubstituted arylene group;
- a substituted or unsubstituted alkenylene group;
- a substituted or unsubstituted fluorenylene group;
- a substituted or unsubstituted carbazolylene group;
- or a substituted or unsubstituted heteroarylene group comprising one or more of N, O and S atoms,
- Y2 is hydrogen;
- heavy hydrogen;
- a halogen group;
- a nitrile group;
- a nitro group;
- a hydroxy group;
- a substituted or unsubstituted alkyl group;
- a substituted or unsubstituted cycloalkyl group;
- a substituted or unsubstituted alkoxy group;
- a substituted or unsubstituted aryloxy group;
- a substituted or unsubstituted alkylthioxy group;
- a substituted or unsubstituted arylthioxy group;
- a substituted or unsubstituted alkylsulfoxy group;
- a substituted or unsubstituted arylsulfoxy group;
- a substituted or unsubstituted alkenyl group;
- a substituted or unsubstituted silyl group;
- a substituted or unsubstituted boron group;
- a substituted or unsubstituted alkylamine group;
- a substituted or unsubstituted aralkylamine group;
- a substituted or unsubstituted arylamine group;
- a substituted or unsubstituted heteroarylamine group;
- a substituted or unsubstituted aryl group;
- a substituted or unsubstituted fluorenyl group;
- a substituted or unsubstituted carbazole group;
- or a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S atoms,
- aromatic or hetero aromatic monocycle and polycycle formed by connecting two or more adjacent groups of the group that is not used in connection to Formula 1 among R7 to R10, R11, R12, R13 and R14 to each other may be each independently substituted by -(L2)r-(Y2)s,
- in the case where two or more L2 and two or more Y2 are present in Formula 2, L2 and Y2 are each independently the same as or different from each other,
- B1 is an aryl group where one or more carbons constituting a cycle may be further replaced by nitrogen, and B2 is an aryl group where one or more carbons constituting a cycle may be replaced by nitrogen,
- in the case where R1 and R2 form a cycle, Formula 1 is represented by any one of the following Formulas 1-1 to 1-4:
- in the Formulas 1-2 to 1-4, R1a to R4a are the same as definitions of R1 to R2 of Formula 1, and A1, and X1 to X4 are the same as definitions of Formula 1,
- Formula 1-1 is represented by any one of the following Formulas 3-1 to 3-4, 3-6- to 3-18:
- in the Formulas 3-1 to 3-4 and 3-6 to 3-18,
- R7 to R14 are the same as definitions of Formula 2, and R1a to R4a and R3 to R6 are each independently -(L1)p-(Y1)q where p is an integer of 0 to 10, q is an integer of 1 to 10, two or more adjacent groups of R3 to R6 may form a monocycle or a polycycle,
- L1 is oxygen;
- sulfur;
- substituted or unsubstituted nitrogen;
- substituted or unsubstituted phosphorus;
- a substituted or unsubstituted phenylene group;
- a substituted or unsubstituted biphenylene group;
- a substituted or unsubstituted terphenylene group;
- a substituted or unsubstituted naphthylene group;
- a substituted or unsubstituted pyrenylene group;
- a substituted or unsubstituted phenanthrenylene group;
- a substituted or unsubstituted perylenylene group;
- a substituted or unsubstituted tetracenylene group;
- a substituted or unsubstituted triphenylene group;
- a substituted or unsubstituted fluoranthenylene group;
- a substituted or unsubstituted alkenylene group;
- a substituted or unsubstituted fluorenylene group;
- a substituted or unsubstituted carbazolylene group;
- or a substituted or unsubstituted heteroarylene group comprising one or more of N, O and S atoms,
- Y1 is hydrogen;
- heavy hydrogen;
- a halogen group;
- a nitrile group;
- a nitro group;
- a hydroxy group;
- a substituted or unsubstituted alkyl group;
- a substituted or unsubstituted cycloalkyl group;
- a substituted or unsubstituted alkoxy group;
- a substituted or unsubstituted aryloxy group;
- a substituted or unsubstituted alkylthioxy group;
- a substituted or unsubstituted arylthioxy group;
- a substituted or unsubstituted alkylsulfoxy group;
- a substituted or unsubstituted arylsulfoxy group;
- a substituted or unsubstituted alkenyl group;
- a substituted or unsubstituted silyl group;
- a substituted or unsubstituted boron group;
- a substituted or unsubstituted alkylamine group;
- a substituted or unsubstituted aralkylamine group;
- a substituted or unsubstituted arylamine group;
- a substituted or unsubstituted heteroarylamine group;
- a substituted or unsubstituted phenyl group;
- a substituted or unsubstituted biphenyl group;
- a substituted or unsubstituted terphenyl group;
- a substituted or unsubstituted naphthyl group;
- a substituted or unsubstituted fluorenyl group;
- a substituted or unsubstituted pyrenyl group;
- a substituted or unsubstituted phenanthrenyl group;
- a substituted or unsubstituted perylenyl group;
- a substituted or unsubstituted tetracenyl group;
- a substituted or unsubstituted triphenylene group;
- a substituted or unsubstituted fluoranthenyl group;
- a substituted or unsubstituted fluorenyl group;
- a substituted or unsubstituted carbazole group;
- or a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S atoms.
159 more elements
Dependencies are inferred from the claim text.