Organic electroluminescent compound and organic electroluminescent device comprising the same

1. An organic electroluminescent compound of the following formula 1:

wherein

Ar 1 to Ar 6 each independently are selected from the group consisting of a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, and a substituted or unsubstituted spiro[fluorene-(C3-C30)cycloalkane]yl; or Ar 1 and Ar 2 , Ar 3 and Ar 4 , and Ar 5 and Ar 6 may be linked to each other to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

L 1 is selected from the group consisting of a single bond, a substituted or unsubstituted (C6-C30)arylene, and a substituted or unsubstituted 5- to 30-membered heteroarylene;

L 2 is selected from the group consisting of a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, and a substituted or unsubstituted 5- to 30-membered heteroarylene, with a proviso that where n is 0, L 2 does not exist;

R 1 and R 2 each independently are selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, —NR 11 R 12 , —SiR 13 R 14 R 15 , —SR 16 , —OR 17 , a cyano, a nitro, and a hydroxyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

R 11 to R 17 each independently are selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, and a substituted or unsubstituted (C3-C30)cycloalkyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

m represents an integer of 1 to 2, where m is 2, each of NAr 1 Ar 2 may be the same or different;

n represents an integer of 0 to 2, where n is 2, each of NAr 3 Ar 4 may be the same or different;

a represents an integer of 1 to 5, where a is an integer of 2 or more, each of R 1 may be the same or different;

b represents an integer of 1 to 4, where b is an integer of 2 or more, each of R 2 may be the same or different;

the heteroaryl(ene) contains at least one hetero atom selected from B, N, O, S, Si, and P; and

the heterocycloalkyl contains at least one hetero atom selected from O, S, and N.

2. The organic electroluminescent compound according to claim 1 , wherein the compound of formula 1 is selected from the group consisting of formula 2 and formula 3:

wherein

Ar 1 to Ar 6 , L 1 , L 2 , R 1 , R 2 , a, b, m, and n are as defined in claim 1 .

3. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, the substituted arylalkyl, and the substituted spiro[fluorene-(C3-C30)cycloalkane]yl in Ar 1 to Ar 6 , L 1 , L 2 , R 1 , R 2 , and R 11 to R 17 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 3- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl.

4. The organic electroluminescent compound according to claim 1 , wherein

Ar 1 to Ar 4 each independently are selected from the group consisting of a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted 5- to 15-membered heteroaryl, and a substituted or unsubstituted spiro[fluorene-(C5-C8)cycloalkane]yl;

Ar 5 and Ar 6 each independently are selected from the group consisting of a substituted or unsubstituted (C1-C6)alkyl, and a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a mono- or polycyclic, 5- to 15-membered alicyclic or aromatic ring;

L 1 is selected from the group consisting of a single bond, a substituted or unsubstituted (C6-C20)arylene, and a substituted or unsubstituted 5- to 15-membered heteroarylene;

L 2 is selected from the group consisting of a single bond, and a substituted or unsubstituted (C6-C12)arylene, with a proviso that where n is 0, L 2 does not exist; and

R 1 and R 2 each independently represent hydrogen.

5. The organic electroluminescent compound according to claim 1 , wherein

Ar 1 to Ar 4 each independently are selected from the group consisting of a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C20)aryl; a 5- to 15-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C12)aryl; an unsubstituted spiro[fluorene-cyclopentane]yl; and an unsubstituted spiro[fluorene-cyclohexane]yl;

Ar 5 and Ar 6 each independently are selected from the group consisting of an unsubstituted (C1-C6)alkyl, and an unsubstituted (C6-C12)aryl; or may be linked to each other to form a monocyclic, 5- to 15-membered alicyclic ring;

L 1 is selected from the group consisting of a single bond, an unsubstituted (C6-C20)arylene, and an unsubstituted 5- to 15-membered heteroarylene;

L 2 is selected from the group consisting of a single bond, and an unsubstituted (C6-C12)arylene, with a proviso that where n is 0, L 2 does not exist; and

R 1 and R 2 each independently represent hydrogen.

6. The organic electroluminescent compound according to claim 1 , wherein the compound of formula 1 is selected from the group consisting of:

7. A hole transport material comprising the organic electroluminescent compound according to claim 1 .

8. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

9. The organic electroluminescent device according to claim 8 , wherein the organic electroluminescent compound is comprised in at least one layer of a light-emitting layer and a hole transport layer.

10. A display device comprising the organic electroluminescent compound according to claim 1 .