Novel multifunctional compound and organic light-emitting diode comprising same

A multifunctional compound represented by the following Chemical Formula 1:

• wherein, in Chemical Formula 1,
• ring A is a fused ring represented by the following Chemical Formula 2, the following Chemical Formula 3 or the following Chemical Formula 4;
• L represents a linking site in ring A, and L is linked to Q;
• or Y1 when Q is not present;
• J represents another linking site in ring A, and J is linked to X;
• X is C, Si, Ge, Sn or Pb;
• Q is not present, represents a single bond, or is one atom selected from the group consisting of Group IIIA, Group IVA, Group VA and Group VIA elements;
• when Q is not present, L in ring A is not linked to Y1;
• when Q is a single bond, a single bond directly linking L in ring A and Y1 is formed to form a 5-membered ring including X;
• when Q is any one atom of the elements defined above, a 6-membered ring including X is formed, and the atom optionally has a substituent selected from the group consisting of alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, aryl having 6 to 30 carbon atoms unsubstituted or substituted with a first additional substituent, heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a first additional substituent, and combinations thereof according to a stoichiometric ratio, and the substituent are optionally linked to Y2 or R that is linked to Y2 to form a fused ring or linked to ring A to form a fused ring;
• Y1 to Y15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se or Te;
• Z is not present, or a single bond, boron, oxygen, sulfur, —S(O2)—, Se, C—(Ar1)2, POAr1 or N—Ar1, and herein, Ar1 is alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, aryl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, or heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, and Ar1 is optionally linked to any one of Y7, Y12, R linked to Y7 and R linked to Y12 to form a fused ring;
• when Z is not present, Y6 and Y11 are not linked;
• when Z is a single bond, Y6 and Y11 are linked through the single bond;
• however, when X is Si, Z is present as defined above;
• m, n and o are each independently an integer of 0 to 5;
• Rs are each independently hydrogen, deuterium, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, ally having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl amine having 1 to 30 carbon atoms, cycloalkyl amine having 3 to 30 carbon atoms, heterocycloalkyl amine having 2 to 30 carbon atoms, aryl amine having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl aryl amine having 7 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, cycloalkyl aryl amine having 9 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heterocycloalkyl aryl amine having 8 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, halogen, CN, alkoxy having 1 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, aryloxy having 6 to 30 carbon atoms, alkyl silyl having 1 to 30 carbon atoms, cycloalkyl silyl having 3 to 30 carbon atoms, heterocycloalkyl silyl having 2 to 30 carbon atoms, aryl silyl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl aryl silyl having 7 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, cycloalkyl aryl silyl having 9 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heterocycloalkyl aryl silyl having 8 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl thiol having 1 to 30 carbon atoms, cycloalkyl thiol having 3 to 30 carbon atoms, heterocycloalkyl thiol having 2 to 30 carbon atoms, aryl thiol having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, or aryl phosphine oxide having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, and at least two Rs present when m, n or o is 2 or greater are optionally linked to each other to form a ring;
• and
• p, q and r each independently represent 0 or 1, and when p, q or r is 0, it means that a 5-membered ring is formed, and when p, q or r is 1, it means that a 6-membered ring is formed,
• in Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4,
• Ys are each independently carbon, nitrogen, oxygen, sulfur, Se or Te, however, Y at the position corresponding to J in Chemical Formula 1 is carbon;
• Ws are each independently oxygen, sulfur, Se, POAr2 or N—Ar2, Ar2 is alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, aryl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, or heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, and Ar2 is optionally linked to a ring fused to the fused ring including W to form a fused ring;
• R16 to R45 each independently represent a bond with X such that Y linked thereto corresponds to J in Chemical Formula 1;
• or a bond with Q such that Y linked thereto corresponds to L in Chemical Formula 1;
• or are hydrogen, deuterium, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, ally having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl amine having 1 to 30 carbon atoms, cycloalkyl amine having 3 to 30 carbon atoms, heterocycloalkyl amine having 2 to 30 carbon atoms, aryl amine having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl aryl amine having 7 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, cycloalkyl aryl amine having 9 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heterocycloalkyl aryl amine having 8 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, halogen, CN, alkoxy having 1 to 30 carbon atoms, aryloxy having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl silyl having 1 to 30 carbon atoms, cycloalkyl silyl having 3 to 30 carbon atoms, heterocycloalkyl silyl having 2 to 30 carbon atoms, aryl silyl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl aryl silyl having 7 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, cycloalkyl aryl silyl having 9 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, heterocycloalkyl aryl silyl having 8 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, alkyl thiol having 1 to 30 carbon atoms, cycloalkyl thiol having 3 to 30 carbon atoms, heterocycloalkyl thiol having 2 to 30 carbon atoms, aryl thiol having 6 to 30 carbon atoms or aryl phosphine oxide having 6 to 30 carbon atoms, and at least two of R16 to R45 are optionally linked to each other to form a ring;
• the first additional substituent is selected from the group consisting of deuterium, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, ally having 3 to 30 carbon atoms, halogen, cyano, aryl having 6 to 30 carbon atoms, alkyl silyl having 1 to 30 carbon atoms, cycloalkyl silyl having 3 to 30 carbon atoms, heterocycloalkyl silyl having 2 to 30 carbon atoms, aryl silyl having 6 to 30 carbon atoms, alkyl amine having 1 to 30 carbon atoms, cycloalkyl amine having 3 to 30 carbon atoms, heterocycloalkyl amine having 2 to 30 carbon atoms, aryl amine having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkyl thiol having 1 to 30 carbon atoms, cycloalkyl thiol having 3 to 30 carbon atoms, heterocycloalkyl thiol having 2 to 30 carbon atoms, aryl thiol having 6 to 30 carbon atoms, aryl phosphine oxide having 6 to 30 carbon atoms, and combinations thereof;
• the second additional substituent is selected from the group consisting of deuterium, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, ally having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, halogen, cyano, carboxyl, carbonyl, amine, alkyl amine having 1 to 30 carbon atoms, cycloalkyl amine having 3 to 30 carbon atoms, heterocycloalkyl amine having 2 to 30 carbon atoms, nitro, alkyl silyl having 1 to 30 carbon atoms, cycloalkyl silyl having 3 to 30 carbon atoms, heterocycloalkyl silyl having 2 to 30 carbon atoms, alkoxy silyl having 1 to 30 carbon atoms, aryl silyl having 6 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, aryl amine having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, aryl phosphine oxide having 6 to 30 carbon atoms, aryl phosphinyl having 6 to 30 carbon atoms, alkyl phosphine oxide having 1 to 30 carbon atoms, cycloalkyl phosphine oxide having 3 to 30 carbon atoms, heterocycloalkyl phosphine oxide having 2 to 30 carbon atoms, alkyl sulfonyl having 1 to 30 carbon atoms, cycloalkyl sulfonyl having 3 to 30 carbon atoms, heterocycloalkyl sulfonyl having 2 to 30 carbon atoms, and combinations thereof;
• positions of L and J in Chemical Formula 1 are according to the following (i) or (ii):
• (i) Y linked to any one of R16 to R45 corresponds to J in Chemical Formula 1, and another Y adjacent to Y corresponding to J corresponds to L in Chemical Formula 1;
• or,
• (ii) any one of Ws is N—Ar2, Ar2 is aryl having 6 to 30 carbon atoms unsubstituted or substituted with a second additional substituent or heteroaryl having 2 to 30 carbon atoms unsubstituted or substituted with a second additional substituent, any one reduction of aryl or heteroaryl of Ar2 is carbon and corresponds to J in Chemical Formula 1, and another reduction adjacent thereto corresponds to L in Chemical Formula 1;
• however, in Chemical Formula 1, when Z and Q are both a single bond, the following case (a) or (b) is excluded:
• (a) ring A in Chemical Formula 1 is Chemical Formula 3 or Chemical Formula 4, any one of R34 to R36 and R40 to R45 in Chemical Formula 3 or Chemical Formula 4 corresponds to L in Chemical Formula 1, and two Ws in ring A are both N—Ar2;
• (b) a 5-membered ring is formed in which at least one of p and q in Chemical Formula 1 is 0, and two Rs linked to the 5-membered ring are linked to each other to form an unsubstituted 6-membered fused ring.