Heteroaromatic cycle-containing compound, method of preparing the same and organic light emitting device comprising the same

1 . A heteroaromatic cycle-containing compound represented by Formula 1:

wherein X is N or C;

Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group; and

Ar 2 , Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

2 . The heteroaromatic cycle-containing compound of claim 1 , wherein the compound is represented by Formula 2 below:

wherein X is N or C;

Ar 1 ′ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group; and

Ar 2 , Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

3 . The heteroaromatic cycle-containing compound of claim 2 , wherein Ar 1 ′ is one of compounds represented by Formulas 3 and 4:

4 . The heteroaromatic cycle-containing compound of claim 2 , wherein Ar 2 is a hydrogen atom, methyl or phenyl.

5 . The heteroaromatic cycle-containing compound of claim 2 , wherein X is N, Ar 3 is hydrogen atom, and A 4 is a lone electron pair.

6 . The heteroaromatic cycle-containing compound of claim 2 , wherein X is C, Ar 3 and A 4 are hydrogen atoms or phenyl ortho-fused to the heteroaromatic cycle.

7 . The heteroaromatic cycle-containing compound of claim 1 , wherein the compound is one of Compounds represented by Formulas 5 through 16:

8 . An organic light emitting device comprising at least one organic layer comprised of the heteroaromatic cycle-containing compound of claim 1 .

9 . A method of preparing a heteroaromatic cycle-containing compound represented by Formula 1, the method comprising:

reacting an imidazole derivative (B′) and a boronic acid derivative (C′):

wherein X is N or C;

X′ is a halogen atom;

Ar 1 ′ and Ar 1 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group; and

Ar 2 , Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

10 . The method of claim 9 , wherein Ar 2 of the imidazole derivative (B′) is prepared by a reaction of an imidazole derivative (D′) and a boronic acid derivative (E′):

wherein X is N or C;

X′ is a halogen atom, wherein each X′ of D′ is the same halogen atom or different halogen atoms; and

Ar 2 , Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

11 . The method of claim 10 , wherein the imidazole derivative (D′) is prepared by a reaction of an imidazole derivative (F′) and N-halosuccinimide:

wherein X is N or C;

X′ is a halogen atom, wherein each X′ of D′ is the same halogen atom or different halogen atoms;

Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring; and

N-halosuccinimide is N-iodosuccinimide, N-bromosuccinimide, or N-chlorosuccinimide.

12 . The method of claim 11 , wherein the imidazole derivative (F′) is prepared by a reaction of α-halo ketone derivative (H′) and a heteroarylamine derivative (G′):

wherein X is N or C;

X′ is a halogen atom, wherein each X′ of H′ is the same halogen atom or different halogen atoms; and

Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

13 . The method of claim 9 , wherein the reaction is performed in the presence of Pd(PPh 3 ) 4 and a base, and the reaction temperature is in the range of 50 to 120° C.

14 . The method of claim 10 , wherein the reaction is performed in the presence of Pd(PPh 3 ) 4 and a base, and the reaction temperature is in the range of 50 to 120° C.

15 . An organometallic complex prepared from the method of claim 9 .

16 . An organic light emitting diode comprising:

a first substrate;

a second substrate facing to the first substrate; and

at least one organic layer disposed between the first electrode and the second electrode, the at least one organic layer comprising an organic layer comprised of a heteroaromatic cycle-containing compound represented by Formula 1:

wherein X is N or C;

Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group; and

Ar 2 , Ar 3 and Ar 4 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 alkylalkoxy group, a substituted or unsubstituted C 7 -C 20 arylalkoxy group, a substituted or unsubstituted C 6 -C 20 arylamino group, a substituted or unsubstituted C 1 -C 20 alkylamino group, a substituted or unsubstituted C 6 -C 20 heteroarylamino group, or a substituted or unsubstituted C 2 -C 20 hetero ring group, wherein, when X is N, Ar 4 refers to a lone electron pair, and when X is C, Ar 3 and Ar 4 are alternatively bound to each other to form a saturated or unsaturated carbon ring.

17 . The organic light emitting diode of claim 16 , wherein the organic layer comprised of the heteroaromatic cycle-containing compound is an electron transport layer or an electron injection layer.

18 . The organic light emitting diode of claim 16 , wherein the organic layer comprised of the heteroaromatic cycle-containing compound is an emissive layer.

19 . The organic light emitting diode of claim 16 , wherein the at least one organic layer comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an emissive layer, a hole blocking layer, an electron transport layer and an electron injection layer.

20 . The organic light emitting diode of claim 14 , wherein Ar 1 ′ is one of compounds represented by Formulas 3 and 4:

Ar 2 is a hydrogen atom, methyl or phenyl;

X is C or N;

when X is N, Ar 3 is hydrogen atom, and A 4 is a lone electron pair; and

when X is C, Ar 3 and A 4 are hydrogen atoms or phenyl ortho-fused to the heteroaromatic cycle.