Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same

1. An organic electroluminescent compound represented by at least one of the following formulas 1-11 to 1-13:

wherein

R 11 to R 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent to form a ring, with a proviso that at least one of R 11 to R 14 is neither hydrogen nor deuterium;

R 1 to R 8 each independently represent hydrogen, deuterium, or -L-Ar, or may be linked to an adjacent substituent to form a ring, with a proviso that at least one pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 is linked to each other to be fused as the following formula a;

wherein

X represents NR 31 , O, S, CR 32 R 33 , or —CR 34 ═CR 35 —;

R 31 represents -L 1 -Ar 1 ;

R 32 and R 33 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent to form a ring;

R 34 and R 35 each independently represent hydrogen, deuterium, or -L 5 -Ar 5 ;

R 21 to R 24 each independently represent hydrogen, deuterium, or -L 2 -Ar 2 , or may be linked to an adjacent substituent to form a ring:

L, L 1 , L 2 , and L 5 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;

Ar, Ar 1 , Ar 2 , and Ar 5 each independently represent a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C1-C30)alkoxy, or are represented by the following formula b or c;

wherein

R a1 , R a2 , R b1 , R b2 , and R b3 each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;

in formula a represents a bonding site with R 1 to R 8 ; and

in formulas b and c represents a bonding site with L, L 1 , L 2 , or L 5 , respectively;

R 41 to R 44 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L 3 -N(Ar 3 )(Ar 4 ):

L 3 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and

Ar 3 and Ar 4 each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.

2. The organic electroluminescent compound according to claim 1 , wherein formula a is represented by at least one of the following formulas a-1 to a-3:

wherein

R 21 to R 24 and X are as defined in claim 1 ;

R 51 to R 54 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L 3 ′-N(Ar 3 ′)(Ar 4 ′);

L 3 ′ each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and

Ar 3 ′ and Ar 4 ′ each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.

3. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted aryl, the substituted arylene, the substituted heteroaryl, and the substituted heteroarylene in R 11 to R 14 , R 32 , R 33 , L, L 1 , L 2 , L 5 , Ar, Ar 1 , Ar 2 , Ar 5 , R a1 , R a2 , and R b1 to R b3 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 at least one of a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s) and a (3- to 30-membered)heteroaryl(s); 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-(C2-C30)alkenylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a mono- or di-(3- to 30-membered)heteroarylamino; a (C1-C30)alkyl(C2-C30)alkenylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkyl(3- to 30-membered)heteroarylamino; a (C2-C30)alkenyl(C6-C30)arylamino; a (C2-C30)alkenyl (3- to 30-membered)heteroarylamino; a (C6-C30)aryl(3- to 30-membered)heteroarylamino; 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 the compound represented by formulas 1-11 to 1-13 is selected from the following compounds:

5. A plurality of host materials comprising a first host material comprising the organic electroluminescent compound represented by the following formula 1 and a second host material different from the first host material:

wherein

R 11 to R 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent to form a ring, with a proviso that at least one of R 11 to R 14 is neither hydrogen nor deuterium;

R 1 to R 8 each independently represent hydrogen, deuterium, or -L-Ar, or may be linked to an adjacent substituent to form a ring, with a proviso that at least one pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 is linked to each other to be fused as the following formula a;

wherein

X represents NR 31 , O, S, CR 32 R 33 , or —CR 34 ═CR 35 —;

R 31 represents -L 1 -Ar 1 ;

R 32 and R 33 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent to form a ring;

R 34 and R 35 each independently represent hydrogen, deuterium, or -L 5 -Ar 5 ;

R 21 to R 24 each independently represent hydrogen, deuterium, or -L 2 -Ar 2 , or may be linked to an adjacent substituent to form a ring:

L, L 1 , L 2 , and L 5 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered) heteroary lene, or a substituted or unsubstituted (C3-C30)cycloalkylene;

Ar, Ar 1 , Ar 2 , and Ar 5 each independently represent a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C1-C30)alkoxy, or are represented by the following formula b or c;

wherein

R a1 , R a2 , R b1 , R b2 , and R b3 each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;

in formula a represents a bonding site with R 1 to R 8 ; and

in formulas b and c represents a bonding site with L, L 1 , L 2 , or L 5 , respectively.

6. The plurality of host materials according to claim 5 , wherein the second host material comprises the compound represented by the following formula 2:

wherein

X 1 and Y 1 each independently represent —N═, —NR 67 —, —O—, or —S—, with a proviso that any one of X 1 and Y 1 represents —N═, and the other one of X 1 and Y 1 represents —NR 67 —, —O—, or —S—;

R 61 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl:

R 62 to R 64 and R 67 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L 3 ″-N(Ar 3 ″)(Ar 4 ″); or may be linked to an adjacent substituent to form a ring:

L 3 ″ each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene:

Ar 3 ″ and Ar 4 ″ each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl:

R 65 and R 66 each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl:

L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and

a represents 1, b and c each independently represent 1 or 2, d represents an integer of 1 to 4, and when b to d are an integer of 2 or more, each of R 62 to each of R 64 may be the same or different from each other.

7. The plurality of host materials according to claim 6 , wherein the compound represented by formula 2 is at least one selected from the following compounds:

8. The plurality of host materials according to claim 5 , wherein the second host material comprises the compound represented by the following formula 3:

wherein

L a and L b each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

Ar a and Ar b each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 301 to R 304 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L 3 ″′-N(Ar 4 ″′)(Ar 4 ″′); or may be linked to an adjacent substituent to form a ring;

L 3 ′″ each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

Ar 3 ″′ and Ar 4 ″′ each independently represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and

f and i each independently represent an integer of 1 to 4, g and h each independently represent an integer of 1 to 3, and when f to i are an integer of 2 or more, each of R 301 to each of R 304 may be the same or different from each other.

9. The plurality of host materials according to claim 8 , wherein the compound represented by formula 3 is at least one selected from the following compounds:

10. The plurality of host materials according to claim 5 , wherein the second host material comprises the compound represented by the following formula 4:

wherein

T represents —O— or —S—:

HAr represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered)heteroaryl:

L 51 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene:

R 71 and R 72 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent to form a ring; and

a 11 represents an integer of 1 to 4, b 12 represents an integer of 1 to 3, and when a 11 and b 12 each represent an integer of 2 or more, each of R 71 and each of R 72 may be the same or different from each other.

11. The plurality of host materials according to claim 10 , wherein the compound represented by formula 4 is at least one selected from the following compounds:

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

13. The organic electroluminescent device according to claim 12 , wherein the organic electroluminescent compound is comprised in a light-emitting layer.

14. An organic electroluminescent device comprising an anode: a cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises the plurality of host materials according to claim 5 .