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US 9,288,869 B2Granted
Styryl-based compound, composition containing styryl-based compound, and organic light emitting diode including styryl-based compound
AssigneeSamsung Display Co., Ltd.
InventorsSang-Hyun Han, Seok-Hwan Hwang, Young-Kook Kim, Hye-Jin Jung, Jin-O Lim, Soo-Yon Kim, Dae-Yup Shin, Jong-Hyuk Lee
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Abstract
A styryl-based compound represented by Formula 1, a composition containing the styryl-based compound, and an organic light-emitting diode (OLED) including the styryl-based compound: The styryl-based compound may exhibit high heat resistance and thus an OLED including the same may have low driving voltage, high brightness, high efficiency, and long lifetime.
Claims17
A styryl-based compound represented by any one of Formulae 1A through 1I below:
- wherein Z1 through Z3 are each independently selected from the group consisting of hydrogen;
- deuterium;
- a halogen atom;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- an amino group;
- an amidino group;
- hydrazine;
- hydrazone;
- a carboxyl group or a salt thereof;
- a sulfonic acid group or a salt thereof;
- a phosphoric acid or a salt thereof;
- a C1-C10 alkyl group;
- a C1-C10 alkoxy group;
- a phenyl group;
- a naphthyl group;
- a fluorenyl group;
- a phenanthrenyl group;
- an anthryl group;
- an triphenylenyl group;
- a pyrenyl group;
- a chrysenyl group;
- an imidazolyl group:
- an imidazolynyl group;
- an imidazopyridinyl group;
- an imidazopyrimidinyl group;
- a pyridinyl group;
- a pyrazinyl group;
- a pyrimidinyl group;
- an indolyl group;
- and a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, an triphenylenyl group, a pyrenyl group, a chrysenyl group, an imidazolyl group, an imidazolynyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, and an indolyl group that are substituted with at least one of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1-C10 alkyl group, and a C1-C10 alkoxy group;
- two or more neighboring substituents from among Z1 through Z3 are optionally fused with each other or are optionally connected by a single bond;
- T1 is O or S;
- p is an integer of 1 to 7;
- and
- q is an integer of 1 to 4;
- Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C2-C60 heteroaryl group;
- L1 and L2 are each independently a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 heteroarylene group;
- and
- a and b are each independently an integer of 0 to 5.
38 more elements
A composition, comprising:
- a styryl-based compound represented by Formula 1:
- and
- at least one of a styryl-based compound represented by Formula 1-1H-1, a styryl-based compound represented by Formula 1-1H-2, and a styryl-based compound represented by Formula 1-2H:
- wherein Ar3 is a substituted or unsubstituted C8-C20 aryl group having two ore more rings fused with each other, or a substituted, or unsubstituted C2-C20 heteroaryl group having two or more rings fused with each other;
- Ar1 and Ar2 are each independently a substituted or unsubstituted C5-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group;
- L1 and L2 are each independently a substituted or unsubstituted C5-C60 arylene group or a substituted or unsubstituted C2-C60 heteroarylene group;
- and
- a and b are each independently an integer of 0 to 5, wherein
- a deuterium substitution rate represented by Equation 1 below is 70% or more:
- deuterium substitution rate(%)=ND/ND+H×100 (1)
- wherein ND is the number of deuterium atoms bonded to carbon atoms of the styryl group in Formulae 1, 1-1H-1, and 1-1H-2 above;
- and
- ND+H is the total number of deuterium atoms and hydrogen atoms that are bonded to carbon atoms of the styryl group in Formulae 1, 1-1H-1, 1-1H-2, and 1-2H above.
10 more elements
Dependencies are inferred from the claim text.