Novel multifunctional compound and organic light-emitting diode comprising same

Abstract

A novel multifunctional compound and an organic light emitting diode including a light emitting layer including the same are provided.

Description

Technical Field

[0001] The present invention relates to a novel multifunctional compound and an organic light-emitting diode comprising the same. Background Art

[0002] An organic light-emitting diode (OLED) is a device in which holes injected from an anode and electrons injected from a cathode combine in a light-emitting layer to form excitons and emit light, and was first reported by C.W. Tang in Appl. Phys. Lett 51, 913 in 1987. There are two electrons with different spins in the HOMO wave function of the host of the light-emitting layer. In an OLED, electrons directly enter and exit from an organic substance, specifically, electrons escape from the highest occupied molecular orbital (HOMO) energy level and are injected into the lowest unoccupied molecular orbital (LUMO) energy level. At this time, since the spin directions of the electrons entering and exiting are not fixed, the formed excitons are a triplet state with the same spin direction and a singlet state with different spin directions. In an organic substance, due to the exchange energy and the electron-electron repulsion energy, the triplet energy is usually as small as 0.5 eV to 1 eV. The theoretical ratios of the singlet state and the triplet state are 25% and 75% respectively. The singlet state emits light in the form of light, while the triplet state dissipates heat in the form of heat. In order to improve the internal quantum efficiency of an OLED device, it is necessary to induce triplet state emission. Mark E. Thompson reported in the patent (US6303238B1) applied for in 1997 a technique of emitting the triplet state in the form of light by increasing the spin-orbit coupling by using heavy metals such as Pt. Chihaya Adachi proposed in Nature, 2012, 492, 234-238 to minimize the wave function overlap between HOMO and LUMO within a molecule through molecular design. In this way, the efficiency is improved by delayed fluorescence (TADF; thermally activated delayed fluorescence) in which the energy of the triplet state is transferred to the singlet state and emits light. However, in the method using heavy metals, Pt, Ir, etc. are very expensive, and the triplet state needs to emit blue light, resulting in a relatively high HOMO-LUMO energy gap energy of the singlet state, which may cause problems with the stability of the substance. In the method using delayed fluorescence, since the wave function overlap between HOMO and LUMO is small, the full width at half maximum (FWHM) of the emission spectrum becomes wide, making it difficult to achieve deep blue, and there are also problems with the stability of the substance.

[0003] After research, another method for reducing the energy difference between singlet and triplet states is to form an excited-state complex between an electron donor molecule relatively rich in electrons and an electron acceptor molecule lacking electrons. When the electron donor (or electron acceptor) molecule absorbs light and is in an excited state, the two substances form an excited-state complex (exciplex) through Coulombic interaction with the ground-state electron acceptor (or electron donor) molecule (Valeur, B, Berberan-santos, M.N, Wiley-VCH Verlag GmbH&co.KGaA, 2nd edition, 2012). In this state, the energy difference between the triplet and singlet states is small, so the luminescence efficiency can be improved. However, even when such an excited-state complex is formed, there is a problem that it is difficult to achieve deep blue due to the too wide full width at half maximum of the luminescence spectrum, and when doped with a dopant to obtain deep blue, the efficiency of energy transfer from the excited-state complex to the dopant is not high, so a high quantum efficiency cannot be obtained. Summary of the Invention

[0004] Technical Problem

[0005] The object of the present invention is to provide a novel multifunctional compound capable of efficiently transferring energy.

[0006] The object of the present invention is to provide an organic light-emitting diode that uses the multifunctional compound to efficiently transfer energy to improve the quantum efficiency.

[0007] The object of the present invention is not limited to the above objects. Other objects and advantages not mentioned in the present invention can be understood through the following description and can be more clearly understood through the embodiments of the present invention. In addition, it is easy to understand that the objects and advantages of the present invention can be achieved by the means described in the claims and their combinations.

[0008] Technical Solution

[0009] In one example of the present invention, a multifunctional compound represented by the following Chemical Formula 1 is provided.

[0010] Chemical Formula 1:

[0011]

[0012] In the Chemical Formula 1,

[0013] Ring A is a fused ring represented by the following Chemical Formula 2, the following Chemical Formula 3 or the following Chemical Formula 4,

[0014] L represents a connecting site on the ring A, and the L is connected to Q; or when Q does not exist, it is connected to Y 1 connected,

[0015] J represents another connecting site on the ring A, and the J is connected to X,

[0016] X is C, Si, Ge, Sn or Pb,

[0017] Q does not exist, or represents a single bond, or is an atom selected from the group consisting of elements of Group IIIA, Group IVA, Group VA and Group VIA,

[0018] When the Q does not exist, the L on the ring A is not connected to Y 1 connected,

[0019] When the Q is a single bond, the L on the ring A is directly connected to Y 1 to form a single bond, thereby forming a 5-membered ring containing the X,

[0020] When the Q is any one of the atoms as defined above, a 6-membered ring containing the X is formed. In terms of stoichiometry, the atom can have a substituent selected from the group consisting of C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a first additional substituent, C2-30 heteroaryl substituted or unsubstituted with a first additional substituent, and combinations thereof. The substituent can be connected to Y 2 or Y 2 connected to the R to form a fused ring, or connected to the ring A to form a fused ring,

[0021] Y 1 to Y 15 each independently is boron, carbon, nitrogen, oxygen, sulfur, Se or Te,

[0022] Z does not exist, or is a single bond, boron, oxygen, sulfur, -S(O2)-, Se, C-(Ar 1 )2, POAr 1 or N-Ar 1 , at this time, the Ar 1 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent. The Ar 1 can be connected to Y 7 , Y 12 , Y 7 connected to the R or Y 12 connected to the R to form a fused ring,

[0023] When Z does not exist, Y 6 is not connected to Y 11 and,

[0024] when Z is a single bond, Y 6 is connected to Y 11 via the single bond,

[0025] provided that when X is Si, the existence of Z is defined as above,

[0026] m, n, and o are each independently an integer from 0 to 5,

[0027] Each R is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy optionally substituted with a second additional substituent, C6-30 aryloxy, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio optionally substituted with a second additional substituent, or C6-30 arylphosphine oxide optionally substituted with a second additional substituent. When m, n, or o is 2 or more, at least two Rs present can be connected to each other to form a ring.

[0028] p, q, and r each independently represent 0 or 1. When p, q, or r is 0, it represents the formation of a 5-membered ring, and when p, q, or r is 1, it represents the formation of a 6-membered ring.

[0029]

[0030] In Chemical Formulas 2, 3, and 4,

[0031] Y is each independently carbon, nitrogen, oxygen, sulfur, Se or Te, provided that Y at the position corresponding to J in Chemical Formula 1 is carbon,

[0032] W is each independently oxygen, sulfur, Se, POAr 2 、or N-Ar 2 ,wherein Ar 2 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl optionally substituted with a second additional substituent or C2-30 heteroaryl optionally substituted with a second additional substituent, and the Ar 2 is capable of connecting to a ring fused to the ring containing the W to form a fused ring,

[0033] R 16 to R 45 each independently represents a bond formed with the X such that the Y to which it is attached corresponds to J in Chemical Formula 1; or represents a bond formed with the Q such that the Y to which it is attached corresponds to L in Chemical Formula 1; or is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 allyl, C6-30 aryl optionally substituted with a second additional substituent or C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent or C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent or C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent or C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent or C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the R 16 to R 45 can be connected to each other to form a ring,

[0034] The first additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, halogen, cyano, C6-30 aryl, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino, C2-30 heteroaryl, C1-30 alkoxy, C6-30 aryloxy, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine oxide, and combinations thereof.

[0035] The second additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C1-30 alkoxy, halogen, cyano, carboxyl, carbonyl, amino, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, nitro, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C1-30 alkoxysilyl, C6-30 arylsilyl, C6-30 aryl, C6-30 arylamino, C2-30 heteroaryl, C6-30 arylphosphine oxide, C6-30 arylphosphonyl, C1-30 alkylphosphine oxide, C3-30 cycloalkylphosphine oxide, C2-30 heterocycloalkylphosphine oxide, C1-30 alkylsulfonyl, C3-30 cycloalkylsulfonyl, C2-30 heterocycloalkylsulfonyl, and combinations thereof.

[0036] The positions of L and J in Formula 1 are as follows (i) or (ii):

[0037] (i) The Y connected to any one of R 16 to R 45 corresponds to J in Formula 1, and the other Y adjacent to the Y corresponding to J corresponds to L in Formula 1; or,

[0038] (ii) Any one of W is N-Ar 2 , where Ar 2 is C6-30 aryl optionally substituted with a second additional substituent or C2-30 heteroaryl optionally substituted with a second additional substituent, and the reduction of any one of the aryl or heteroaryl of Ar 2 to carbon corresponds to J in Formula 1, and the adjacent other reduction corresponds to L in Formula 1.

[0039] Provided that in Formula 1, when both Z and Q are single bonds, the following cases (a) or (b) are excluded:

[0040] (a) Ring A in Formula 1 is Formula 3 or Formula 4, and any one of R 34 to R 36 and R 40 to R 45 in them corresponds to L in Formula 1, and both Ws in Ring A are N-Ar 2 ,

[0041] (b) A 5-membered ring in which at least one of p and q in Formula 1 is 0 is formed, and two Rs connected to the 5-membered ring are connected to each other to form an unsubstituted 6-membered fused ring.

[0042] In another example of the present invention, an organic light-emitting diode is provided, which includes a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, and may or may not include an organic layer adjacent to one or both sides of the light-emitting layer. The light-emitting layer contains the multifunctional compound, and the light-emitting layer or the adjacent organic layer contains an excited-state complex-forming compound.

[0043] Effects of the Invention

[0044] The multifunctional compound can reduce the energy difference between the singlet state and the triplet state, and at the same time achieve effective energy transfer between parts of the multifunctional compound, and it is easy to achieve dark blue with high energy transfer efficiency. Therefore, an organic light-emitting diode using it can obtain a high quantum efficiency.

[0045] In addition to the above effects, the specific effects of the present invention will be described below in combination with specific embodiments. Description of the Drawings

[0046] Figure 1 It is a diagram schematically showing the action mechanism of the multifunctional compound.

[0047] Figure 2 It schematically shows the mechanism of realizing luminescence by the transfer of the excitation energy of the excited-state complex in the organic light-emitting diode according to an example of the present invention between parts of the multifunctional compound.

[0048] Figure 3 It is a graph showing the PL (Photoluminescence) phenomenon observed by depositing HOST-1:HOST-3 at a ratio of 1:1 and exciting each deposited glass with an absorption wavelength of 350 nm.

[0049] Figure 4It is a graph showing the PL (Photoluminescence) phenomenon observed by depositing HOST-2 and HOST-4 at a ratio of 1:1 and exciting each deposited glass with an absorption wavelength (350 nm).

[0050] Figure 5 It is a graph showing the PL (Photoluminescence) phenomenon observed by dissolving Comparative Compound 1 and Compound 2 in toluene at 2 micromoles respectively and exciting with the absorption wavelength (max). Detailed Description of the Invention

[0051] Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily implement it. The present invention can be implemented in various different forms and is not limited to the embodiments described herein.

[0052] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom in a compound is replaced by another substituent. The position where substitution occurs refers to the position where the hydrogen atom is replaced. The position is not limited as long as the hydrogen at that position can be replaced by a substituent. When two or more substitutions occur, the two or more substituents may be the same or different.

[0053] In this specification, unless otherwise mentioned, the substituent in the case of "substituted" may be selected from the group consisting of, for example, deuterium, C1-20 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C1-30 alkoxy, halogen, cyano, carboxyl, carbonyl, amine, C1-30 alkylamine, C3-30 cycloalkylamine, C2-30 heterocycloalkylamine, nitro, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C1-30 alkoxysilyl, C6-30 arylsilyl, C6-30 aryl, C6-30 arylamine, C2-30 heteroaryl, C6-30 aryloxyphosphinyl, C6-30 arylphosphonyl, C1-30 alkyloxyphosphinyl, C3-30 cycloalkyloxyphosphinyl, C2-30 heterocycloalkyloxyphosphinyl, C1-30 alkylsulfonyl, C3-30 cycloalkylsulfonyl, C2-30 heterocycloalkylsulfonyl, and combinations thereof, but is not limited thereto.

[0054] In this specification, unless otherwise defined, "combinations thereof" in the definition of substituents means that there are two or more substituents, or two or more divalent substituents are connected or fused together.

[0055] In this specification, the case where two substituents are connected to form a ring includes the case where one of the two substituents is hydrogen and connection occurs when the hydrogen is removed.

[0056] In this specification, unless otherwise mentioned, alkyl includes cycloalkyl and heterocycloalkyl. Additionally, for example, unless otherwise mentioned, alkylamino includes cycloalkylamino and heterocycloalkylamino.

[0057] In this specification, unless otherwise defined, "hetero" means that a compound or substituent contains a heteroatom, and the heteroatom refers to an atom other than carbon and hydrogen among the atoms forming a heterocyclic compound. For example, it can be N, O, Si, Ge, S, P, B, Se, Te, etc., but is not limited thereto. When a compound or substituent contains two or more heteroatoms, the same or different heteroatoms can be included. For example, one or two or more heteroatoms can be included. For example, heteroaryl or heterocycloalkyl contains at least one heteroatom as a ring-forming atom.

[0058] In this specification, unless otherwise mentioned, a ring includes a fused ring.

[0059] In one example of the present invention,

[0060] A multifunctional compound represented by the following Chemical Formula 1 is provided.

[0061] Chemical Formula 1:

[0062]

[0063] In the Chemical Formula 1,

[0064] Ring A is a fused ring represented by the following Chemical Formula 2, the following Chemical Formula 3, or the following Chemical Formula 4,

[0065] L represents a connecting site on Ring A, and L is connected to Q; or when Q does not exist, it is connected to Y 1 connected,

[0066] J represents another connecting site on Ring A, and J is connected to X,

[0067] X is C, Si, Ge, Sn, or Pb,

[0068] Q does not exist, or represents a single bond, or is an atom selected from the group consisting of elements of Group IIIA, Group IVA, Group VA, and Group VIA,

[0069] When Q does not exist, L on Ring A is not connected to Y 1 connected,

[0070] When Q is a single bond, L on Ring A is directly connected to Y 1 to form a single bond, thereby forming a 5-membered ring containing X,

[0071] When Q is any atom among the elements defined above, a 6-membered ring containing X is formed, and stoichiometrically, the atom can have a substituent selected from the group consisting of C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a first additional substituent, C2-30 heteroaryl substituted or unsubstituted with a first additional substituent, and combinations thereof, and the substituent can be connected to Y 2 or Y 2 to form a fused ring with the R to which it is connected, or to form a fused ring with ring A

[0072] Y 1 to Y 15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se or Te

[0073] Z is absent, or is a single bond, boron, oxygen, sulfur, -S(O2)-, Se, C-(Ar 1 )2, POAr 1 or N-Ar 1 , whereupon, the Ar 1 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent, and the Ar 1 can be connected to Y 7 , Y 12 , Y 7 to form a fused ring with the R to which it is connected or with any one of the R to which Y 12 is connected

[0074] When Z is absent, the Y 6 is not connected to Y 11

[0075] When Z is a single bond, the Y 6 is connected to Y 11 through the single bond

[0076] Provided that when X is Si, the presence of Z is as defined above

[0077] m, n and o are each independently an integer from 0 to 5

[0078] ​Each R is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy optionally substituted with a second additional substituent, C6-30 aryloxy, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio optionally substituted with a second additional substituent or C6-30 arylphosphine oxide optionally substituted with a second additional substituent. When m, n or o is 2 or more, at least two Rs present can be connected to each other to form a ring.

[0079] p, q and r each independently represent 0 or 1. When p, q or r is 0, it represents the formation of a 5-membered ring. When p, q or r is 1, it represents the formation of a 6-membered ring.

[0080]

[0081] In the Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4,

[0082] Each Y is independently carbon, nitrogen, oxygen, sulfur, Se or Te, provided that Y at the position corresponding to J in Chemical Formula 1 is carbon.

[0083] Each W is independently oxygen, sulfur, Se, POAr 2 , or N-Ar 2 , Ar 2 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl optionally substituted with a second additional substituent or C2-30 heteroaryl optionally substituted with a second additional substituent. The Ar 2 can be connected to a ring fused to the ring containing the W to form a fused ring.

[0084] R16 to R 45 each independently represents a bond formed with the said X such that the Y to which it is attached corresponds to J in Chemical Formula 1; or represents a bond formed with the said Q such that the Y to which it is attached corresponds to L in Chemical Formula 1; or is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, C2-30 heteroaryl substituted or unsubstituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino substituted or unsubstituted with a second additional substituent, C7-30 alkylarylamino substituted or unsubstituted with a second additional substituent, C9-30 cycloalkylarylamino substituted or unsubstituted with a second additional substituent, C8-30 heterocycloalkylarylamino substituted or unsubstituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy substituted or unsubstituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl substituted or unsubstituted with a second additional substituent, C7-30 alkylarylsilyl substituted or unsubstituted with a second additional substituent, C9-30 cycloalkylarylsilyl substituted or unsubstituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl substituted or unsubstituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, the said R 16 to R 45 at least two of which are capable of connecting to each other to form a ring,

[0085] the said first additional substituent is selected from the group consisting of: deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, halogen, cyano, C6-30 aryl, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino, C2-30 heteroaryl, C1-30 alkoxy, C6-30 aryloxy, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine oxide and combinations thereof,

[0086] The second additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C1-30 alkoxy, halogen, cyano, carboxyl, carbonyl, amino, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, nitro, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C1-30 alkoxysilyl, C6-30 arylsilyl, C6-30 aryl, C6-30 arylamino, C2-30 heteroaryl, C6-30 arylphosphine oxide, C6-30 arylphosphonyl, C1-30 alkylphosphine oxide, C3-30 cycloalkylphosphine oxide, C2-30 heterocycloalkylphosphine oxide, C1-30 alkylsulfonyl, C3-30 cycloalkylsulfonyl, C2-30 heterocycloalkylsulfonyl, and combinations thereof.

[0087] The positions of L and J in Formula 1 are as follows (i) or (ii):

[0088] (i) Y connected to any one of R 16 to R 45 corresponds to J in Formula 1, and the other Y adjacent to the Y corresponding to J corresponds to L in Formula 1; or,

[0089] (ii) Any one of the Ws is N-Ar 2 , where Ar 2 is a C6-30 aryl or a C2-30 heteroaryl which is substituted or unsubstituted by the second additional substituent. Reduction of any one of the aryl or heteroaryl of Ar 2 to carbon corresponds to J in Formula 1, and the adjacent other reduction corresponds to L in Formula 1.

[0090] Provided that, in Formula 1, when both Z and Q are single bonds, the following cases (a) or (b) are excluded.

[0091] (a) Ring A in Formula 1 is Formula 3 or Formula 4, and any one of R 34 to R 36 and R 40 to R 45 in Formula 3 or Formula 4 corresponds to L in Formula 1, and both Ws in Ring A are N-Ar 2 .

[0092] (b) A 5-membered ring in which at least one of p and q in Formula 1 is 0 is formed, and two Rs connected to the 5-membered ring are connected to each other to form an unsubstituted 6-membered fused ring.

[0093] In the definition of Chemical Formula 1, the substituent connected to Q and Y 2 or Y 2 where the R groups they are connected to form a fused ring include the case where: when the R connected to Y 2 is hydrogen and this hydrogen (i.e., R) detaches, the substituent connected to Q and Y 2 are connected.

[0094] In the definition of Chemical Formula 1, Ar 1 and Y 7 or Y 12 or Y 7 where the R groups they are connected to or the R group connected to Y 12 form a fused ring include the case where: when the R connected to Y 7 or the R group connected to Y 12 is hydrogen and this hydrogen (i.e., R) detaches, Ar 1 and Y 7 or Y 12 are connected.

[0095] In Chemical Formula 1, when at least two R groups are connected to form a ring, such a ring includes a fused ring. Moreover, the case where two R groups are connected includes the situation where any one of the two connected R groups is hydrogen, and when this hydrogen (i.e., R) detaches, any one of the Y 1 to Y 15 connected to this hydrogen is directly connected to the other of the two connected R groups.

[0096] In Chemical Formulas 2 to 4, when at least two of the R 16 to R 45 are connected to form a ring, such a ring includes a fused ring. Moreover, the case where two of the R 16 to R 45 are connected includes the situation where any one of the two connected ones is hydrogen, and when this hydrogen detaches, the Y connected to this hydrogen is directly connected to the other of the two connected ones.

[0097] The multifunctional compound is the compound shown in Chemical Formula 1, and its chemical structure is designed to have a relatively high rate constant value related to the energy transfer rate, which can improve the luminous efficiency of the organic light-emitting diode.

[0098] The multifunctional compound can achieve deep blue color and at the same time can also improve the quantum efficiency of the organic light-emitting diode.

[0099] The multifunctional compound represented by the chemical formula 1 is designed to include an atom represented by X, a light-emitting part, and an excited-state complex-forming part: the light-emitting part and the excited-state complex-forming part are connected by the atom represented by X, and the atom represented by X is the X shown in the chemical formula 1. The light-emitting part includes ring A in the chemical formula 1, a conjugated ring composed of Y 1 ~Y 5 and Q. The excited-state complex-forming part includes a conjugated ring composed of Y 6 ~Y 10 in the chemical formula 1, a conjugated ring composed of Y 11 ~Y 15 and Z.

[0100] The excited-state complex-forming part can form an excited-state complex with the following excited-state complex-forming compound.

[0101] The multifunctional compound is a compound in which the light-emitting part is combined with the excited-state complex-forming part capable of forming an excited-state complex with an excited-state complex-forming compound through the atom represented by X.

[0102] The mechanism of the excited-state complex is a phenomenon that occurs between two molecules. First, one molecule absorbs light corresponding to the HOMO-LUMO energy gap and enters the excited state, and then interacts with other nearby molecules to form an excited-state complex. After the excited-state complex emits light, the two molecules return to their original states.

[0103] If the excited-state complex is narrowly defined, when the two molecules are the same molecule, it is called an excited dimer or excimer, and when the two molecules are different molecules, it is called an excited complex or exciplex. Alternatively, the excited-state complex is also called an electroplex. An electroplex refers to the situation where an excited-state complex or an excited dimer is formed when an electric field is applied inside an organic light-emitting diode (OLED) device. In this specification, the term "excited-state complex" is defined broadly and should be understood to include concepts such as excited dimer, excimer, excited complex, exciplex, and electroplex.

[0104] The excited-state complex-forming moiety is designed to be a moiety derived from either of the two molecules that form the excited-state complex, and the other of the two molecules that form the excited-state complex becomes the aforementioned excited-state complex-forming compound. For ease of distinction, when the two molecules that form the excited-state complex are respectively referred to as the first excited-state complex-forming compound and the second excited-state complex-forming compound, the excited-state complex-forming moiety is derived from the first excited-state complex-forming compound and is capable of forming an excited-state complex with the second excited-state complex-forming compound.

[0105] In an organic light-emitting diode device, if a low ionization energy substance and a high electron affinity substance are used simultaneously in the light-emitting layer, an excited-state complex will be formed during the electron transfer process. If a luminescent compound is mixed into this excited-state complex as a dopant, the dopant can absorb the exciton energy of the excited-state complex and cause luminescence. To achieve such luminescence, the energy transfer efficiency from the excited-state complex to the dopant must be very high. The energy transfer methods include the light-based method (FRET, Resonance Energy transfer) of the following mathematical formula 1 and the electron-based method (Dexter Electron Transfer) of the following mathematical formula 2.

[0106] FRET( [[ID=##**WARN**##10]]Resonance Energy transfer)

[0107] Mathematical formula 1:

[0108]

[0109] Dexter Electron Transfer

[0110] Mathematical formula 2:

[0111]

[0112] k ET : Rate constant

[0113] r: Distance between the energy donor and the energy acceptor

[0114] τ D : PL decay time of the energy donor

[0115] κ: Orientation factor

[0116] Q D : PL quantum efficiency of the energy donor Note: There seems to be an issue with the formatting of the original text where "Resonance Energy transfer" is split in an odd way. I've tried to make the translation as accurate as possible while maintaining the structure. If this is a specific formatting requirement for patent text that I'm not aware of, please let me know.

[0117] N A : Avogadro's constant

[0118] n: refractive index

[0119] J: defined by the following Mathematical Formula 3

[0120] Mathematical Formula 3:

[0121] J = ∫f D (λ)ε A (λ)λ 4 dλ

[0122] f D : emission spectrum of the energy donor

[0123] ε A : extinction coefficient of the energy acceptor as a function of wavelength

[0124] L: the sum of Van der Waals radii

[0125] λ: wavelength

[0126] The present inventors have derived the multifunctional compound, which, as a novel compound, makes r in the above Mathematical Formula 1 and Mathematical Formula 2 approach 0. The present inventors have inferred the advantages when r approaches 0 as follows.

[0127] Regardless of whether the energy transfer method is the light-based method of Mathematical Formula 1 or the electron-based method of Mathematical Formula 2, what matters is the distance r between the energy donor (excited state complex) and the energy acceptor (dopant). In Mathematical Formula 1 for light-based energy transfer, when the distance r approaches 0, the quantum (excited state complex) efficiency and decay time of the energy donor become unimportant, and theoretically the energy transfer rate approaches infinity. On the other hand, in Mathematical Formula 2 for the energy transfer method based on electron transfer, when the distance r between the two substances approaches 0, the energy transfer rate is only affected by the degree of overlap J between the emission spectrum and absorption spectrum of the two substances.

[0128] The multifunctional compound is designed as a compound that binds either of the two molecules that will form an excited state complex (corresponding to the first excited state complex-forming compound) to a dopant (corresponding to the compound that induces the luminescence of the luminescent portion). If the concepts of Mathematical Formula 1 and Mathematical Formula 2 are applied to the multifunctional compound, in the multifunctional compound, when either of the two molecules that form an excited state complex binds to the dopant, the distance is fixed and minimized, and the exciton energy formed in the excited state complex moves rapidly to the dopant, achieving luminescence.

[0129] Since the excited-state complex-forming moiety in the multifunctional compound is derived from (or originates from) the first excited-state complex-forming compound, it can form an excited-state complex with the second excited-state complex-forming compound.

[0130] Figure 1 A diagram for schematically illustrating the mechanism of action of the multifunctional compound.

[0131] Figure 1 The figure shows a multifunctional compound formed by chemically bonding a first excited-state complex-forming compound with a relatively large HOMO-LUMO energy gap and a luminescent compound with a relatively small HOMO-LUMO energy gap. When the excited-state complex-forming moiety derived from the first excited-state complex-forming compound in the multifunctional compound is excited, energy is transferred to the luminescent moiety derived from the luminescent compound. This can be confirmed by comparing Figure 3 the absorption spectra and emission spectra of Compound 1 (i.e., the excited-state complex-forming compound), Compound 2 (i.e., the luminescent compound), and Compound 3 (i.e., the multifunctional compound) in

[0132] The phenomenon that the energy of the excited-state complex is transferred from the excited-state complex formed by the interaction of the excited-state complex-forming moiety with the (second) excited-state complex-forming compound to the luminescent moiety can be confirmed by fabricating an organic light-emitting diode. That is, when charges are injected into the light-emitting layer of the organic light-emitting diode, first, the excited-state complex-forming moiety inside the multifunctional compound forms an excited-state complex with the (second) excited-state complex-forming compound, and the energy of this excited-state complex is transferred to the luminescent moiety through the excited-state complex moiety. When the energy of the excited-state complex formed in the excited-state complex is greater than the energy of the luminescent moiety, the energy of the excited-state complex is transferred to the luminescent moiety.

[0133] Figure 2 The figure schematically shows the mechanism of luminescence achieved by the transfer of the excitation energy of the excited-state complex in the multifunctional compound between moieties in an organic light-emitting diode according to an example of the present invention.

[0134] The excited-state complex-forming moiety or the (second) excited-state complex-forming compound absorbs energy from the outside to form an excited-state complex, and the excitation energy of this excited-state complex is transferred to the luminescent moiety connected by chemical bonding, and the luminescent moiety exhibits a luminescence phenomenon.

[0135] More specifically, when charge is injected into the light-emitting layer including the excited-state complex formation part containing the multifunctional compound inside the organic light-emitting diode, the excited-state complex formation part interacts with the adjacent (second) excited-state complex formation compound in the organic light-emitting diode to form an excited-state complex, and the energy of the formed excited-state complex is transferred to the light-emitting part very close to one molecule of the multifunctional compound. This energy transfer between parts of the multifunctional compound makes the rate constant very large due to the distance r approaching 0 in the aforementioned mathematical formulas 1 and 2, thus achieving efficient and high-speed energy transfer. Since the energy of the excited-state complex is transferred to the light-emitting part, and the light-emitting part can emit light with minimal energy loss, the multifunctional compound can ultimately achieve a mechanism of efficiently emitting light using the energy of the excited-state complex, thereby obtaining the effect of improving energy efficiency.

[0136] The advantages of the organic light-emitting diode containing the multifunctional compound are that, by utilizing the excited-state complex, the energy difference between the singlet state and the triplet state is reduced, and at the same time, effective energy transfer between parts of the multifunctional compound is achieved. And since it includes a light-emitting part, it is easy to achieve dark blue, has a high energy transfer efficiency, and thus can obtain a high quantum efficiency.

[0137] The multifunctional compound is not limited to achieving blue light emission, but can also be applied to the light emission of green, red, and near-infrared light.

[0138] The light-emitting part can be derived from a light-emitting material (referred to as a light-emitting compound in this specification) that can emit light through the movement of electrons in the organic light-emitting diode.

[0139] The light-emitting compound (light-emitting material) can be a compound commonly used as a dopant in the organic light-emitting diode. A dopant capable of achieving the desired color can be selected according to the purpose as the light-emitting compound, and thereby the light-emitting part can be induced.

[0140] In one example, the light-emitting part has a conjugated structure and its quantum efficiency is 50% or more in the visible light wavelength range of 400 nm to 700 nm.

[0141] In one example, the light-emitting part has a conjugated structure and its quantum efficiency is 0.5% or more in the near-infrared wavelength range of 700 nm to 2500 nm.

[0142] In one example, in the multifunctional compound, the ring A can be represented by any one of the following C-1 to C-24. Provided that, in Chemical Formula 1, when Z and Q are single bonds, the ring A is not C-8, C-10, C-11, C-17, C-20, C-22, and C-23.

[0143]

[0144]

[0145] Among C-1 to C-24,

[0146] #Two adjacent ones of the # indicated positions correspond to J or L on ring A of formula 1,

[0147] R 1 to R 11 Each independently is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, C2-30 heteroaryl substituted or unsubstituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino substituted or unsubstituted with a second additional substituent, C7-30 alkylarylamino substituted or unsubstituted with a second additional substituent, C9-30 cycloalkylarylamino substituted or unsubstituted with a second additional substituent, C8-30 heterocycloalkylarylamino substituted or unsubstituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy substituted or unsubstituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl substituted or unsubstituted with a second additional substituent, C7-30 alkylarylsilyl substituted or unsubstituted with a second additional substituent, C9-30 cycloalkylarylsilyl substituted or unsubstituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl substituted or unsubstituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the R 1 to R 11 can be connected to each other to form a ring,

[0148] X' each independently is O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2 or N-Ar 3 , and the Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent. When multiple Ar 3 are present, multiple Ar can be connected to each other to form a ring,

[0149] X is independently N, O, S, or Se,

[0150] The second additional substituent is defined as the second additional substituent defined in Chemical Formula 1 above.

[0151] Among C-1 to C-24, when at least two of R 1 to R 11 are connected to each other to form a ring, such a ring includes a fused ring. Further, in the case where two of R 1 to R 11 are connected, it includes the case where any one of the two connected ones is hydrogen, and when this hydrogen is removed, by reducing the ring to which this hydrogen is connected, it is directly connected to the other of the two connected ones.

[0152] The light emission mechanism of the light emitting part may include fluorescence emitted from a singlet state, phosphorescence emitted from a triplet state, and delayed fluorescence emitted by energy transfer from a triplet state to a singlet state.

[0153] In one example, the compound forming the second excited state complex may not form an excited state complex with the light emitting part. If the light emitting part can form an excited state complex with the compound forming the second excited state complex, it can affect the emission wavelength of the light emitting part. If the emission wavelength of the light emitting part changes, it may be difficult to apply the characteristics of known light emitting compounds to the light emitting part when designing color realization, or when attempting to use a specific light emitting compound to achieve a specific color, it may be difficult to achieve the desired color due to the change in the emission wavelength of the light emitting part.

[0154] In one example, the band gap energy of the excited state complex forming part may be from 1 eV to 4.7 eV, and the band gap energy of the light emitting part may be from 0.5 eV to 3.5 eV.

[0155] In one example, the difference in band gap energy between the excited state complex forming part and the light emitting part may be within 2 eV.

[0156] In one example, the difference in HOMO energy level between the excited state complex forming part and the light emitting part may be within 1.9 eV.

[0157] In one example, the energy difference between the LUMO energy of the excited state complex forming part and the LUMO energy of the light emitting part may be within 1.9 eV.

[0158] The HOMO energy can be measured by methods such as cyclic voltammetry (CV), ultraviolet photoelectron spectroscopy (UPS), and AC2, while the LUMO energy can be measured by ultraviolet absorption spectroscopy or cyclic voltammetry (CV).

[0159] In one example, the chemical formula 1 is any one of the chemical formulas represented by the following B-1 to B-32:

[0160]

[0161]

[0162] Among the B-1 to B-32,

[0163] Ring A is as defined in the chemical formula 1,

[0164] X is C, Si, Ge, Sn, or Pb,

[0165] X' are each independently O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2, or N-Ar 3 , where the Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, a C6-30 aryl optionally substituted with a second additional substituent or a C2-30 heteroaryl optionally substituted with a second additional substituent. When multiple Ar 3 are present, the multiple Ar can be connected to each other to form a ring,

[0166] The number of R's depends on the stoichiometric ratio and is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the R's are capable of connecting to each other to form a ring.

[0167] The definition of the second additional substituent is as defined for the second additional substituent in Formula 1 above.

[0168] Among B-1 to B-32, when at least two of the R's connect to each other to form a ring, such a ring includes a fused ring. Also, the case where two of the R's are connected includes the case where any one of the two connected is hydrogen, and when this hydrogen is removed, by reducing the ring to which the hydrogen is attached, it is directly connected to the other R' of the two connected above.

[0169] As described above, the first excited state complex-forming compound (from which the excited state complex-forming moiety in the multifunctional compound is derived) and the second excited state complex-forming compound are compounds capable of forming an excited state complex. As a result, the excited state complex-forming moiety forms an excited state complex with the second excited state complex-forming compound. An excited state complex can be formed between an electron donor molecule having a low ionization energy and an electron acceptor molecule having a high electron affinity.

[0170] Therefore, the excited state complex forming moiety (or the first excited state complex forming compound) and the second excited state complex forming compound can be in the relationship of a pair of electron donor molecules and electron acceptor molecules. For example, the excited state complex forming moiety (or the first excited state complex forming compound) and the second excited state complex forming compound can each be an electron donor molecule and an electron acceptor molecule, and vice versa.

[0171] In one example, the excited state complex forming moiety can be an electron donor or an electron acceptor containing at least one atom with a non-bonding electron pair.

[0172] In one example, in the multifunctional compound, the Y 6 to Y 15 and at least one of Z is an atom having a non-bonding electron pair contained in the HOMO or LUMO wave function of the excited state complex forming moiety; or

[0173] Y 6 to Y 15 at least one of them has R represented by the following Chemical Formula 5 or the following Chemical Formula 6.

[0174] Chemical Formula 5:

[0175]

[0176] Chemical Formula 6:

[0177]

[0178] In the Chemical Formula 5 or Chemical Formula 6,

[0179] L' is a single bond or a divalent group selected from the group consisting of C1-30 alkylene, C3-30 cycloalkylene, C2-30 heterocycloalkylene, C1-30 alkylmethylsilylene, C3-30 cycloalkylmethylsilylene, C2-30 heterocycloalkylmethylsilylene, C1-30 arylmethylsilylene, C7-30 alkylarylmethylsilylene, C9-30 cycloalkylarylmethylsilylene, C8-30 heterocycloalkylarylmethylsilylene, oxygen, sulfur, a divalent group of C6-30 arylphosphine, a divalent group of C6-30 arylphosphine oxide, C6-30 arylene, C2-30 heteroarylene, and combinations thereof.

[0180] Z' does not exist, represents a single bond, or is an atom selected from the group consisting of Group IIIA, Group IVA, Group VA, and Group VIA elements. When the Z' is an atom, it can have substituents selected from hydrogen, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, and combinations thereof, in a stoichiometric ratio.

[0181] Ar 2 and Ar 3 are each independently C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, and the Ar 2 and Ar 3 can each independently connect to the L' or the second additional substituent to form a fused ring.

[0182] t is an integer from 0 to 5.

[0183] v is 0 or 1.

[0184] Each independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a third additional substituent, C2-30 heteroaryl optionally substituted with a third additional substituent, C1-30 alkylamino, C3-3o cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a third additional substituent, C7-30 alkylarylamino optionally substituted with a third additional substituent, C9-30 cycloalkylarylamino optionally substituted with a third additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a third additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a third additional substituent, C1-30 alkylsilyl optionally substituted with a third additional substituent, C3-30 cycloalkylsilyl optionally substituted with a third additional substituent, C2-30 heterocycloalkylsilyl optionally substituted with a third additional substituent, C6-30 arylsilyl optionally substituted with a third additional substituent, C7-30 alkylarylsilyl optionally substituted with a third additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a third additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a third additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine, C6-30 arylphosphine oxide, and combinations thereof, provided that at least two of said R" can be connected to each other to form a ring,

[0185] The third additional substituent is selected from C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl, C2-30 heteroaryl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C7-30 alkylarylamino, C9-30 cycloalkylarylamino, C8-30 heterocycloalkylarylamino, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C7-30 alkylarylsilyl, C9-30 cycloalkylarylsilyl, C8-30 heterocycloalkylarylsilyl, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, and combinations thereof,

[0186] Each Y is independently nitrogen, oxygen, sulfur, or carbon,

[0187] Represents a connecting site,

[0188] Provided that, in the Chemical Formula 6, L' or R" includes at least one atom having a non-bonding electron pair included in the HOMO or LUMO wave function of the excited state complex forming moiety, or at least one of Y is nitrogen, oxygen or sulfur.

[0189] In one example, the multifunctional compound may include at least one deuterium.

[0190] In one example of the present invention, there is provided an organic light emitting diode,

[0191] including a first electrode, a second electrode, and a light emitting layer located between the first electrode and the second electrode,

[0192] further including or not including an organic layer adjacent to one or both surfaces of the light emitting layer,

[0193] the light emitting layer includes the multifunctional compound,

[0194] the light emitting layer or the adjacent organic layer includes an excited state complex forming compound.

[0195] The organic light emitting diode improves the light emitting efficiency by using the multifunctional compound capable of increasing the rate constant value related to the energy transfer rate.

[0196] The organic light emitting diode achieves dark blue color and also exhibits a high quantum efficiency.

[0197] The detailed description of the multifunctional compound is as described above.

[0198] The multifunctional compound is represented by the following Chemical Formula 1.

[0199] Chemical Formula 1:

[0200]

[0201] In the Chemical Formula 1,

[0202] Ring A is a fused ring represented by the following Chemical Formula 2, the following Chemical Formula 3, or the following Chemical Formula 4,

[0203] L represents a connecting site on Ring A, and L is connected to Q; or when Q does not exist, it is connected to Y 1 connected,

[0204] J represents another connecting site on Ring A, and J is connected to X,

[0205] X is C, Si, Ge, Sn or Pb,

[0206] Q is absent, or represents a single bond, or is an atom selected from the group consisting of elements of Group IIIA, Group IVA, Group VA, and Group VIA,

[0207] When Q is absent, L on ring A is not connected to Y 1 connected,

[0208] When Q is a single bond, L on ring A is directly connected to Y 1 to form a single bond, thereby forming a 5-membered ring containing X,

[0209] When Q is any one of the atoms among the elements as defined above, a 6-membered ring containing X is formed. In terms of stoichiometry, the atom can have a substituent selected from the group consisting of C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a first additional substituent, C2-30 heteroaryl substituted or unsubstituted with a first additional substituent, and combinations thereof. The substituent can be connected to Y 2 or Y 2 connected to the R to form a fused ring, or connected to ring A to form a fused ring,

[0210] Y 1 to Y 15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se, or Te,

[0211] Z is absent, or is a single bond, boron, oxygen, sulfur, -S(O2)-, Se, C-(Ar 1 )2, POAr 1 or N-Ar 1 , whereupon, the Ar 1 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent. The Ar 1 can be connected to Y 7 , Y 12 , Y 7 connected to the R or Y 12 connected to the R to form a fused ring,

[0212] When Z is absent, the Y 6 is not connected to Y 11 connected,

[0213] When Z is a single bond, the Y 6 is connected to Y 11 through the single bond,

[0214] Provided that when X is Si, the presence of Z is as defined above,

[0215] m, n, and o are each independently an integer from 0 to 5,

[0216] Each R is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy optionally substituted with a second additional substituent, C6-30 aryloxy, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio optionally substituted with a second additional substituent, or C6-30 aryloxyphosphine optionally substituted with a second additional substituent. When m, n, or o is 2 or more, at least two Rs present can be connected to each other to form a ring.

[0217] p, q, and r each independently represent 0 or 1. When p, q, or r is 0, it represents forming a 5-membered ring, and when p, q, or r is 1, it represents forming a 6-membered ring.

[0218]

[0219] In the Chemical Formula 2, Chemical Formula 3, and Chemical Formula 4,

[0220] Each Y is independently carbon, nitrogen, oxygen, sulfur, Se, or Te, provided that Y at the position corresponding to J in Chemical Formula 1 is carbon.

[0221] Each W is independently oxygen, sulfur, Se, POAr 2 、or N-Ar 2 ,Ar 2is a C1-30 alkyl group, C3-30 cycloalkyl group, C2-30 heterocycloalkyl group, C6-30 aryl group substituted or unsubstituted by a second additional substituent, or C2-30 heteroaryl group substituted or unsubstituted by a second additional substituent, and said Ar 2 is capable of forming a fused ring by connecting with a ring fused to the ring containing said W

[0222] R 16 to R 45 each independently represents a bond formed with said X such that the Y to which it is attached corresponds to J in Chemical Formula 1; or represents a bond formed with said Q such that the Y to which it is attached corresponds to L in Chemical Formula 1; or is hydrogen, deuterium, C1-30 alkyl group, C3-30 cycloalkyl group, C2-30 heterocycloalkyl group, C3-30 allyl group, C6-30 aryl group substituted or unsubstituted by a second additional substituent, C2-30 heteroaryl group substituted or unsubstituted by a second additional substituent, C1-30 alkylamino group, C3-30 cycloalkylamino group, C2-30 heterocycloalkylamino group, C6-30 arylamino group substituted or unsubstituted by a second additional substituent, C7-30 alkylarylamino group substituted or unsubstituted by a second additional substituent, C9-30 cycloalkylarylamino group substituted or unsubstituted by a second additional substituent, C8-30 heterocycloalkylarylamino group substituted or unsubstituted by a second additional substituent, halogen, CN, C1-30 alkoxy group, C6-30 aryloxy group substituted or unsubstituted by a second additional substituent, C1-30 alkylsilyl group, C3-30 cycloalkylsilyl group, C2-30 heterocycloalkylsilyl group, C6-30 arylsilyl group substituted or unsubstituted by a second additional substituent, C7-30 alkylarylsilyl group substituted or unsubstituted by a second additional substituent, C9-30 cycloalkylarylsilyl group substituted or unsubstituted by a second additional substituent, C8-30 heterocycloalkylarylsilyl group substituted or unsubstituted by a second additional substituent, C1-30 alkylthio group, C3-30 cycloalkylthio group, C2-30 heterocycloalkylthio group, C6-30 arylthio group or C6-30 arylphosphine oxide, and at least two of said R 16 to R 45 can be connected to each other to form a ring

[0223] The first additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, halogen, cyano, C6-30 aryl, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino, C2-30 heteroaryl, C1-30 alkoxy, C6-30 aryloxy, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine oxide, and combinations thereof.

[0224] The second additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C1-30 alkoxy, halogen, cyano, carboxyl, carbonyl, amino, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, nitro, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C1-30 alkoxysilyl, C6-30 arylsilyl, C6-30 aryl, C6-30 arylamino, C2-30 heteroaryl, C6-30 arylphosphine oxide, C6-30 arylphosphonyl, C1-30 alkylphosphine oxide, C3-30 cycloalkylphosphine oxide, C2-30 heterocycloalkylphosphine oxide, C1-30 alkylsulfonyl, C3-30 cycloalkylsulfonyl, C2-30 heterocycloalkylsulfonyl, and combinations thereof.

[0225] The positions of L and J in Formula 1 are as follows (i) or (ii):

[0226] (i) The Y connected to any one of R 16 to R 45 corresponds to J in Formula 1, and the other Y adjacent to the Y corresponding to J corresponds to L in Formula 1; or,

[0227] (ii) Any one of the W is N-Ar 2 , where Ar 2 is C6-30 aryl or C2-30 heteroaryl which is substituted or unsubstituted by a second additional substituent, and the reduction of any one of the aryl or heteroaryl of Ar 2 to carbon corresponds to J in Formula 1, and the other adjacent reduction corresponds to L in Formula 1.

[0228] Provided that in Formula 1, when both Z and Q are single bonds, the following cases (a) or (b) are excluded.

[0229] (a) Ring A in Formula 1 is Formula 3 or Formula 4, and any one of R 34 to R 36 and R 40 to R 45 corresponds to L in Formula 1, and both Ws in Ring A are N-Ar 2 ,

[0230] (b) A 5-membered ring in which at least one of p and q in Formula 1 is 0 is formed, and two Rs connected to the 5-membered ring are connected to form an unsubstituted 6-membered fused ring.

[0231] In the definition of Formula 1, the case where the substituent connected to Q is connected to R connected to Y 2 or Y 2 to form a fused ring includes: when R connected to Y 2 is hydrogen and this hydrogen (i.e., R) detaches, the case where the substituent connected to Q is connected to Y 2 .

[0232] In the definition of Formula 1, the case where Ar 1 is connected to any one of R connected to Y 7 , Y 12 , Y 7 or R connected to Y 12 to form a fused ring includes: when R connected to Y 7 or R connected to Y 12 is hydrogen and this hydrogen (i.e., R) detaches, the case where Ar 1 is connected to Y 7 or Y 12 .

[0233] In Formula 1, when at least two Rs are connected to form a ring, such a ring includes a fused ring. And the case where two Rs are connected includes: when any one of the two connected Rs is hydrogen and this hydrogen (i.e., R) detaches, any one of Y 1 to Y 15 connected to this hydrogen (i.e., R) is directly connected to the other of the two above-connected Rs.

[0234] In Formulas 2 to 4, when at least two of R 16 to R 45 are connected to each other to form a ring, such a ring includes a fused ring. And the case where two of R 16 to R 45 are connected includes: when any one of the two connected ones is hydrogen and this hydrogen detaches, the Y connected to this hydrogen is directly connected to the other of the two above-connected ones.

[0235] The multifunctional compound represented by Chemical Formula 1 is divided into an atom represented by X, a light-emitting part, and an excited-state complex-forming part. The light-emitting part and the excited-state complex-forming part are connected by the atom represented by X, and the atom represented by X is the X shown in Chemical Formula 1.

[0236] The light-emitting part includes ring A in Chemical Formula 1, a conjugated ring composed of Y 1 ~Y 5 and Q.

[0237] The excited-state complex-forming part includes a conjugated ring composed of Y 6 ~Y 10 in Chemical Formula 1, a conjugated ring composed of Y 11 ~Y 15 and Z.

[0238] The excited-state complex-forming part forms an excited-state complex with the excited-state complex-forming compound.

[0239] The light-emitting part emits light by receiving the excitation energy of the excited-state complex.

[0240] In one example, in the organic light-emitting diode, Chemical Formula 1 is any one of the chemical formulas represented by the following B-1 to B-32:

[0241]

[0242]

[0243] Among B-1 to B-32,

[0244] Ring A is as defined in Chemical Formula 1.

[0245] X is C, Si, Ge, Sn, or Pb.

[0246] Each X' is independently O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2, or N-Ar 3 , and the Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent. When multiple Ar 3 are present, multiple Ar can be connected to each other to form a ring.

[0247] The number of R's depends on the stoichiometric ratio and each independently is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted by a second additional substituent, C2-30 heteroaryl substituted or unsubstituted by a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino substituted or unsubstituted by a second additional substituent, C7-30 alkylarylamino substituted or unsubstituted by a second additional substituent, C9-30 cycloalkylarylamino substituted or unsubstituted by a second additional substituent, C8-30 heterocycloalkylarylamino substituted or unsubstituted by a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy substituted or unsubstituted by a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl substituted or unsubstituted by a second additional substituent, C7-30 alkylarylsilyl substituted or unsubstituted by a second additional substituent, C9-30 cycloalkylarylsilyl substituted or unsubstituted by a second additional substituent, C8-30 heterocycloalkylarylsilyl substituted or unsubstituted by a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the R's can be connected to each other to form a ring.

[0248] The definition of the second additional substituent is the same as the second additional substituent defined in the chemical formula 1.

[0249] Among B-1 to B-32, when at least two of the R's are connected to each other to form a ring, such a ring includes a fused ring. And, the case where two of the R's are connected includes: either one of the two connected is hydrogen, and when this hydrogen is removed, by reducing the ring to which this hydrogen is connected, it is directly connected to the other R' among the two connected above.

[0250] In one example, in the multifunctional compound represented by the chemical formula 1 contained in the light-emitting layer of the organic light-emitting diode, the ring A is represented by any one of C-1 to C-24 below, provided that in the chemical formula 1, when Z and Q are single bonds, the ring A is not C-8, C-10, C-11, C-17, C-20, C-22 and C-23.

[0251]

[0252] Among C-1 to C-24,

[0253] Two adjacent #'s at the positions shown # correspond to J or L on the ring A in the chemical formula 1, R 1to R 11 Each of R is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the Rs 1 to R 11 can be connected to each other to form a ring,

[0254] Each of X' is independently O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2 or N-Ar 3 , and Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl optionally substituted with a second additional substituent or C2-30 heteroaryl optionally substituted with a second additional substituent. When multiple Ars 3 are present, the multiple Ars can be connected to each other to form a ring,

[0255] Each of X" is independently N, O, S or Se,

[0256] The definition of the second additional substituent is the same as the second additional substituent defined in Chemical Formula 1.

[0257] In C-1 to C-24, when at least two of the Rs 1 to R 11 are connected to each other to form a ring, such a ring includes a fused ring. And, Rs 1 to R 11The case of two connections among them includes: either of the two connected ones is hydrogen, and when this hydrogen is detached, by reducing the ring to which this hydrogen is connected, it is directly connected to the other of the two connected ones above.

[0258] In one example, in the multifunctional compound contained in the light-emitting layer of the organic light-emitting diode, the excited-state complex-forming part contains at least one atom having a non-bonding electron pair.

[0259] In one example, in the multifunctional compound represented by Chemical Formula 1 contained in the light-emitting layer of the organic light-emitting diode,

[0260] the Y 6 to Y 15 and at least one of Z is an atom having a non-bonding electron pair contained in the HOMO or LUMO wave function of the excited-state complex-forming part; or

[0261] Y 6 to Y 15 at least one of them has R represented by the following Chemical Formula 5 or the following Chemical Formula 6.

[0262] Chemical Formula 5:

[0263]

[0264] Chemical Formula 6:

[0265]

[0266] In Chemical Formula 5 or Chemical Formula 6,

[0267] L' is a single bond or a divalent group selected from the group consisting of: C1-30 alkylene, C3-30 cycloalkylene, C2-30 heteroalkylene, C1-30 alkylmethylsilylene, C3-30 cycloalkylmethylsilylene, C2-30 heteroalkylmethylsilylene, C1-30 arylmethylsilylene, C7-30 alkylarylmethylsilylene, C9-30 cycloalkylarylmethylsilylene, C8-30 heteroalkylarylmethylsilylene, oxygen, sulfur, a divalent group of C6-30 arylphosphine, a divalent group of C6-30 arylphosphine oxide, C6-30 arylene, C2-30 heteroarylene, and combinations thereof.

[0268] Z' does not exist, represents a single bond, or is an atom selected from the group consisting of Group IIIA, Group IVA, Group VA, and Group VIA elements. When the Z' is an atom, it can have substituents selected from hydrogen, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, and combinations thereof, in a stoichiometric ratio.

[0269] Ar 2 and Ar 3 each independently is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, and the Ar 2 and Ar 3 can each independently connect with the L' or the second additional substituent to form a fused ring.

[0270] t is an integer from 0 to 5.

[0271] v is 0 or 1.

[0272] R" are each independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a third additional substituent, C2-30 heteroaryl optionally substituted with a third additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a third additional substituent, C7-30 alkylarylamino optionally substituted with a third additional substituent, C9-30 cycloalkylarylamino optionally substituted with a third additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a third additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a third additional substituent, C1-30 alkylsilyl optionally substituted with a third additional substituent, C3-30 cycloalkylsilyl optionally substituted with a third additional substituent, C2-30 heterocycloalkylsilyl optionally substituted with a third additional substituent, C6-30 arylsilyl optionally substituted with a third additional substituent, C7-30 alkylarylsilyl optionally substituted with a third additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a third additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a third additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine, C6-30 arylphosphine oxide, and combinations thereof, provided that at least two of the R" can be connected to each other to form a ring,

[0273] The third additional substituent is selected from C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl, C2-30 heteroaryl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C7-30 alkylarylamino, C9-30 cycloalkylarylamino, C8-30 heterocycloalkylarylamino, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C7-30 alkylarylsilyl, C9-30 cycloalkylarylsilyl, C8-30 heterocycloalkylarylsilyl, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, and combinations thereof,

[0274] Y are each independently nitrogen, oxygen, sulfur, or carbon,

[0275] represents a connecting site,

[0276] Provided that, in the chemical formula 6, L' or R" contains at least one atom having a non-bonding electron pair included in the HOMO or LUMO wave function of the excited state complex forming moiety, or at least one of Y is nitrogen, oxygen, or sulfur.

[0277] In one example, in the organic light-emitting diode, the multifunctional compound may contain at least one deuterium.

[0278] In one example, the multifunctional compound may be any of the compounds represented by the following structural formulas:

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286] The organic light-emitting diode may contain the multifunctional compound at a level higher than the conventional dopant content level. This means that the content of the light-emitting moiety may be higher than the dopant content level. For example, in order to increase the ratio of the formation of the excited state complex between the excited state complex forming moiety of the multifunctional compound and the second excited state complex forming compound, the content of the multifunctional compound may be higher than the conventional dopant content level. Since the excited state complex forming moiety of the multifunctional compound can effectively prevent the concentration quenching phenomenon caused by the interaction between the light-emitting moieties, even if the doping amount of the multifunctional compound increases, the efficiency and hue are not likely to be significantly affected. The ratio of the multifunctional compound in the light-emitting layer may be, for example, 1 to 50 mol% of the total substances constituting the light-emitting layer, and may even be higher depending on the use.

[0287] In one example, the light-emitting layer may contain at least two of the multifunctional compounds.

[0288] In one example, the multifunctional compound may be used as the excited state complex forming compound.

[0289] Specifically, when a multifunctional compound in which an electron donor moiety serves as an excited-state complex-forming moiety and is combined with a light-emitting moiety is referred to as a first multifunctional compound, and a multifunctional compound in which an electron acceptor moiety serves as an excited-state complex-forming moiety and is combined with a light-emitting moiety is referred to as a second multifunctional compound, the first multifunctional compound and the second multifunctional compound contained in the light-emitting layer can form an excited-state complex between their respective electron acceptor moieties and electron donor moieties and transfer energy to the light-emitting moiety. In this case, among the first multifunctional compound and the second multifunctional compound, the light-emitting one corresponds to the multifunctional compound, and the rest corresponds to the excited-state complex-forming compound.

[0290] The proportion of the excited-state complex-forming compound in the light-emitting layer can be, for example, 5 to 95 mol% of the total substances constituting the light-emitting layer, and can even be higher depending on the use.

[0291] In one example, the light-emitting layer may further contain at least one selected from the group consisting of a host, an additional dopant, and a combination thereof.

[0292] The host may be a known substance, that is, a host substance that can generally form a light-emitting layer.

[0293] The additional dopant may be a known substance, that is, a light-emitting substance or a dopant that is generally doped into the light-emitting layer as a light-emitting substance. The role of the additional dopant is to absorb the light energy of the light-emitting moiety and re-emit it. Therefore, the maximum emission wavelength energy of the additional dopant may be less than the maximum emission wavelength energy of the light-emitting moiety. By using the additional dopant, low-energy light emission can be obtained.

[0294] The maximum emission wavelength energy refers to the wavelength with the maximum photon energy in the emission spectrum. The maximum emission wavelength is calculated from the onset value at the start position of light emission, and the maximum emission wavelength is calculated from the wavelength with the maximum emission intensity.

[0295] To further improve the light emission efficiency of the light-emitting layer, the light-emitting layer may further contain a phosphorescent substance.

[0296] In one example, the light-emitting layer may further contain a phosphorescent substance containing Pt or Ir.

[0297] The compound represented by the following structural formula is an example of an organometallic complex that is commonly used as a phosphorescent substance.

[0298]

[0299] In the formula, R may be a C1-20 alkyl group, a C3-20 cycloalkyl group, a C2-20 heterocycloalkyl group, a C6-30 aryl group, etc.

[0300] In order to further improve the luminescence efficiency of the light-emitting layer, the light-emitting layer may further contain a delayed fluorescence material.

[0301] In one example, the light-emitting layer may further contain a delayed fluorescence material with an energy difference between the singlet state and the triplet state of 0.3 eV or more.

[0302] Compounds represented by the following structural formulas are examples of commonly used delayed fluorescence materials.

[0303]

[0304] In the formula, Ar may be a C1-20 alkyl group, a C3-20 cycloalkyl group, a C2-20 heterocycloalkyl group, a C6-30 aryl group, etc.

[0305] The organic light-emitting diode may include one selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and combinations thereof as the organic layer.

[0306] In one example, the organic light-emitting diode may sequentially include an anode, a hole injection layer (HIL: hole injection layer), a hole transport layer (HTL: hole transport layer), a light-emitting layer (EML, light emitting layer), an electron transport layer (ETL: electron transport layer), and a cathode.

[0307] The organic light-emitting diode may form a light-emitting layer containing the multifunctional compound through a deposition process or a solution process.

[0308] The organic light-emitting diode may be a tandem organic light-emitting diode including a plurality of organic light-emitting units. One organic light-emitting unit may include a light-emitting layer and may further include at least one organic layer. The organic layer may include one selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and combinations thereof.

[0309] A plurality of organic light-emitting units may be sequentially stacked, and a charge generation layer (charge generation layer, CGL) may be included between the organic light-emitting units. The charge generation layer is located between the organic light-emitting units to evenly distribute charges to the light-emitting layers of the respective organic light-emitting units.

[0310] The tandem organic light-emitting diode includes a light-emitting layer, wherein at least one organic light-emitting unit contains the multifunctional compound.

[0311] It further includes or does not include an organic layer adjacent to one or both sides of the light-emitting layer containing the multifunctional compound.

[0312] The light-emitting layer containing the multifunctional compound or the adjacent organic layer contains an exciplex-forming compound.

[0313] The multifunctional compound contains an exciplex-forming moiety and a light-emitting moiety.

[0314] The exciplex-forming moiety forms an exciplex with the exciplex-forming compound.

[0315] The light-emitting moiety emits light by receiving the excitation energy of the exciplex.

[0316] In the tandem organic light-emitting diode, the detailed descriptions of the multifunctional compound and the exciplex-forming compound are as described above.

[0317] Examples:

[0318] Synthesis Example

[0319] Synthesis of Comparative Compound 1

[0320]

[0321] Dissolve 8.48 g of Comparative Compound 1-1 (10.0 mmol) in tert-butylbenzene (32 ml) and cool to 0 °C. Under a nitrogen atmosphere, add 8.0 mL (20.0 mmol) of 2.5 M n-butyllithium solution (in hexane) and stir at room temperature for 3 hours.

[0322] Then, cool the reaction mixture to 0 °C again, add 1.90 mL of boron tribromide (20.0 mmol), and stir at room temperature for 0.5 hour. Cool the reaction mixture to 0 °C again, add 3.51 mL of N,N-diisopropylethylamine (20.0 mmol), and then stir at 60 - 70 °C for 2 hours.

[0323] Cool the reaction solution to room temperature and extract the organic layer with ethyl acetate. Dry the solvent of the extracted organic layer with MgSO4 and filter. Concentrate the filtrate under reduced pressure and purify it by silica gel column chromatography (DCM / hexane).

[0324] Then, recrystallize with a DCM / acetone mixed solvent to obtain 1.05 g of the Comparative Compound 1 with a yield of 12%.

[0325] MS(ACPI) m / z: 779 [M + H]

[0326] NMR: δH (500 MHz; CDCl3; Me4Si) 8.94 (s, 1H), 8.84 (d, J = 10 Hz, 1H), 7.69 (d, 2H), 7.66 - 7.56 (m, 2H), 7.51 - 7.45 (d, 1H), 7.42 (s, 1H), 7.34 - 7.28 (m, 3H), 7.19 (d, 1H), 6.67 (s, J = 8 Hz, 2H), 6.15 (d, 1H), 6.06 (s, 1H), 1.89 (s, 3H), 1.64 (d, 4H), 1.46 (s, 20H), 1.37 (s, 11H), 1.25 (s, 3H), 1.22 (s, 10H).

[0327] Synthesis of Compound 2

[0328]

[0329] Compound 2 - 1 (11.41 g, 10.0 mmol) was dissolved in mesitylene (45 ml) and cooled to -30 °C. Under a nitrogen atmosphere, 2.5 M n-butyllithium solution (in hexane) (8.0 mL, 20.0 mmol) was added, and the mixture was stirred at -30 °C for 30 hours.

[0330] Then, the reaction mixture was cooled to -30 °C again, boron tribromide (1.90 mL, 20.0 mmol) was added, and the mixture was stirred at room temperature for 2 hours. 2,6-Di-tert-butylpyridine (2.18 mL, 10.0 mmol) was added at room temperature and the mixture was stirred at 170 °C for 8 hours.

[0331] The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The solvent of the extracted organic layer was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0332] Then, recrystallization was carried out with a DCM / acetone mixed solvent to obtain 0.75 g of the said compound 2, with a yield of 7%.

[0333] MS (ACPI) m / z: 1071 [M + H]

[0334] NMR: δH (400 MHz; CDCl3; Me4Si) 9.20 (dd, J = 7.7, 2.7 Hz, 1H), 9.00 - 8.81 (m, 2H), 8.74 - 8.63 (m, 3H), 7.97 (dddd, J = 41.1, 34.8, 16.0, 4.6 Hz, 4H), 7.77 - 7.63 (m, 3H), 7.62 - 7.28 (m, 12H), 7.17 - 6.85 (m, 10H), 6.83 - 6.34 (m, 8H), 6.04 - 5.83 (m, 3H), 2.36 (s, 3H), 2.13 (s, 3H).

[0335] Synthesis of Compound 3

[0336]

[0337] Synthesis was carried out in the same manner as Compound 2 above, except that Compound 3-1 was used in the same molar ratio instead of Comparative Compound 2-1.

[0338] Thereafter, 0.54 g of Compound 3 was obtained, and the yield was 5%.

[0339] MS (ACPI) m / z: 1071 [M+H]

[0340] NMR: δH (400 MHz; CDCl3; Me4Si) 9.25 - 9.07 (m, 2H), 8.93 - 8.77 (m, 5H), 8.62 - 8.43 (m, 1H), 8.10 - 7.87 (m, 2H), 7.81 - 7.56 (m, 10H), 7.54 - 7.27 (m, 6H), 7.17 - 6.59 (m, 15H), 6.46 (ddd, J = 7.1, 5.6, 4.2 Hz, 2H), 6.07 - 5.95 (m, 2H), 5.96 - 5.87 (m, 1H), 2.36 (s, 3H), 2.15 (d, J = 2.1 Hz, 3H).

[0341] Experimental Example 1. Measurement of Exciplex HOST Flim PL

[0342] HOST-1, HOST-2, HOST-3, and HOST-4 were respectively fabricated in the form of thin films on bare glass using a vacuum deposition apparatus. In order to observe the exciplex spectrum, HOST-1:HOST-3 and HOSt-2:HOST-4 were deposited in a 1:1 ratio. Each deposited glass was excited with an absorption wavelength (350 nm), and the PL (Photoluminescence) phenomenon was observed. The results are as Figure 3 and Figure 4 shown.

[0343] Refer to Figure 3 and Figure 4 Upon this, the unique spectrum of each HOST used disappeared, and a new dotted spectrum was observed. This means that a new Exciplex HOST can be created by mixing two HOSTs with different properties.

[0344] The equipment was measured using SHIMADZU RF5301PC and SHIMADZU UV 2550.

[0345] Experimental Example 2. Measurement of Dopant Solution PL

[0346] 1,2-Dimethylnaphthalene (Compound 1) and 2,3-Dimethylnaphthalene (Compound 2) were each dissolved in toluene at 2 μmol, excited to the absorption wavelength (max), and the PL (Photoluminescence) phenomenon was observed. The results are as Figure 5 shown.

[0347] Figure 5 The graph of

[0348] [[ID=No. 24]]shows the emission spectra of two compounds used as dopants, indicating that the two dopants have different unique emission wavelengths.

[0349] Fabrication of Organic Light-Emitting Diode

[0350] The ITO surface was treated with ultraviolet ozone for 3 minutes under atmospheric pressure.

[0351] The device was processed in a 10 -7 torr vacuum chamber in the following order.

[0352]

[0353] Comparative Example 1 (Device 1)

[0354] HATCN was deposited as a hole injection material to a thickness of

[0355] Compound A was deposited as a hole transport material to a thickness of

[0356] Compound B was deposited as an electron blocking layer to a thickness of

[0357] Using HOST-1 as the light-emitting layer, doped with 1,2-Dimethylnaphthalene (5 mol%), deposited to a thickness of ​

[0358] Deposit compound C as a hole blocking layer to a thickness of

[0359] Deposit a 1:1 ratio of compound D and LiQ as an electron transport layer to a thickness of

[0360] Deposit LiQ as an electron injection layer to a thickness of

[0361] Deposit Al as an electrode to a thickness of

[0362] Comparative Example 2 (Device 2)

[0363] Fabricated in the same manner as Comparative Example 1, except that Comparative Compound 1 (10 mol%) was doped in the light-emitting layer of Device 1.

[0364] Comparative Example 3 (Device 3)

[0365] Fabricated in the same manner as Comparative Example 1, except that HOST-2 was used instead of HOST-1 in the light-emitting layer of Device 1.

[0366] Comparative Example 4 (Device 4)

[0367] Fabricated in the same manner as Comparative Example 2, except that HOST-2 was used instead of HOST-1 in the light-emitting layer of Device 2.

[0368] Example 1 (Device 5)

[0369] Fabricated in the same manner as Comparative Example 1, except that Comparative Compound 2 (10 mol%) was doped in the light-emitting layer of Device 1.

[0370] Example 2 (Device 6)

[0371] Fabricated in the same manner as Comparative Example 4, except that Compound 3 (10 mol%) was doped in the light-emitting layer of Device 4.

[0372] Hereinafter, a table was made based on the maximum luminous efficiency of the doping percentage (%) of each device.

[0373] Table 1

[0374]

[0375] As can be seen from the above table, the performance of the comparative device was measured, and it was confirmed that the energy transfer efficiency from the host to the dopant was low, resulting in a low external quantum efficiency of the light-emitting device. When 10 mol% of Comparative Compound 1 was doped in Device 2 and Device 4, the external quantum efficiencies were 3.82% and 6.61%, respectively. However, for Compounds 2 and 3 containing an excited-state complex-forming moiety in the dopant of the present invention, since an excited-state complex was formed with the host material and the energy was effectively transferred, the maximum quantum efficiencies of 11.26% and 9.16% were obtained, respectively.

[0376] Although the present invention has been described with reference to the above exemplary drawings, the present invention is not limited to the embodiments and drawings disclosed in the present specification. Obviously, those skilled in the art can make various modifications within the technical concept scope of the present invention. At the same time, although the effects based on the configuration of the present invention are not explicitly described when the embodiments of the present invention are described, the effects predictable by the configuration should also be recognized.

Claims

1. A multifunctional compound represented by the following Chemical Formula 1, characterized in that, Chemical Formula 1: In the 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 the connecting part on the ring A, and L is connected to Q; or when Q does not exist, it is connected to Y 1 connected J represents other connecting sites on the Ring A, and the J is connected to X, X is C, Si, Ge, Sn or Pb, Q does not exist, or represents a single bond, or is an atom selected from the group consisting of elements of Group IIIA, Group IVA, Group VA and Group VIA, When the Q does not exist, the L on the ring A is not connected to Y 1 connected When Q is a single bond, L and Y on ring A 1 are directly connected to form a single bond, thereby forming a 5-membered ring containing X. When the Q is any atom among the elements as defined above, a 6-membered ring containing the X is formed, and in terms of stoichiometry, the atom can have substituents selected from the group consisting of C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a first additional substituent, C2-30 heteroaryl substituted or unsubstituted with a first additional substituent, and combinations thereof, and the substituents can be linked with the R linked to Y 2 or Y 2 to form a fused ring, or form a fused ring with the ring A Y 1 to Y 15 each independently is boron, carbon, nitrogen, oxygen, sulfur, Se or Te, Z is absent, or is a single bond, boron, oxygen, sulfur, -S(O2)-, selenium, C-(Ar 1 )2, POAr 1 or N-Ar 1 , in which case, said Ar 1 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted by a second additional substituent or C2-30 heteroaryl substituted or unsubstituted by a second additional substituent, and said Ar 1 is capable of forming a fused ring with any one of Y 7 , Y 12 , Y 7 -connected R or Y 12 -connected R When the Z does not exist, the Y 6 is not connected to Y 11 ​ When Z is a single bond, Y 6 and Y 11 are connected by the single bond, Provided that when the X is Si, the presence of the Z is as defined above, m, n and o are each independently an integer from 0 to 5, Each R is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy optionally substituted with a second additional substituent, C6-30 aryloxy, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio optionally substituted with a second additional substituent or C6-30 arylphosphine oxide optionally substituted with a second additional substituent. When m, n or o is 2 or more, at least two Rs present can be connected to each other to form a ring, p, q and r each independently represent 0 or 1. When p, q or r is 0, it represents the formation of a 5-membered ring. When p, q or r is 1, it represents the formation of a 6-membered ring, Chemical Formula 2: Chemical Formula 3: Chemical Formula 4: In the Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4, Each Y is independently carbon, nitrogen, oxygen, sulfur, Se or Te, provided that Y at the position corresponding to J in Chemical Formula 1 is carbon, Each of W is independently oxygen, sulfur, Se, POAr 2 , or N-Ar 2 , where Ar 2 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent, and the Ar 2 is capable of being linked to a ring fused to the ring containing the W to form a fused ring R 16 to R 45 each independently represents a bond formed with the said X such that the Y to which it is attached corresponds to J in Chemical Formula 1; or represents a bond formed with the said Q such that the Y to which it is attached corresponds to L in Chemical Formula 1; or is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, the R 16 to R 45 in which at least two of them can be connected to each other to form a ring The first additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, halogen, cyano, C6-30 aryl, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino, C2-30 heteroaryl, C1-30 alkoxy, C6-30 aryloxy, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine oxide, and combinations thereof. The second additional substituent is selected from the group consisting of deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C1-30 alkoxy, halogen, cyano, carboxyl, carbonyl, amino, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, nitro, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C1-30 alkoxysilyl, C6-30 arylsilyl, C6-30 aryl, C6-30 arylamino, C2-30 heteroaryl, C6-30 arylphosphine oxide, C6-30 arylphosphonyl, C1-30 alkylphosphine oxide, C3-30 cycloalkylphosphine oxide, C2-30 heterocycloalkylphosphine oxide, C1-30 alkylsulfonyl, C3-30 cycloalkylsulfonyl, C2-30 heterocycloalkylsulfonyl, and combinations thereof. The positions of L and J in Formula 1 are as follows (i) or (ii): (i) Y linked to any one of R 16 to R 45 corresponds to J in Chemical Formula 1, and the other Y adjacent to the Y corresponding to said J corresponds to L in Chemical Formula 1; or, (ii) Any one of the Ws is N-Ar 2 , where the Ar 2 is a C6-30 aryl group which is substituted or unsubstituted by a second additional substituent or a C2-30 heteroaryl group which is substituted or unsubstituted by a second additional substituent. The reduction of any one of the aryl group or heteroaryl group of the Ar 2 to carbon corresponds to J in Chemical Formula 1, and the reduction of the other adjacent ones corresponds to L in Chemical Formula 1 Provided that in Formula 1, when both Z and Q are single bonds, the following cases (a) or (b) are excluded: (a) Ring A in Chemical Formula 1 is Chemical Formula 3 or Chemical Formula 4, and any one of R 34 to R 36 and R 40 to R 45 corresponds to L in Chemical Formula 1, and both Ws in Ring A are N-Ar 2 , (b) A 5-membered ring in which at least one of p and q in Formula 1 is 0 is formed, and the two Rs connected to the 5-membered ring are connected to each other to form an unsubstituted 6-membered fused ring.

2. The multifunctional compound according to claim 1, wherein Formula 1 is any one of the formulas represented by B-1 to B-32 below, In B-1 to B-32, Ring A is as defined in Formula 1, X is C, Si, Ge, Sn, or Pb. X' is independently O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2 or N-Ar 3 , where Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted by a second additional substituent, or C2-30 heteroaryl substituted or unsubstituted by a second additional substituent. When multiple Ar 3 are present, the multiple Ar can be connected to each other to form a ring. The number of R' depends on the stoichiometric ratio and is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the R' can be connected to each other to form a ring. The definition of the second additional substituent is the same as the second additional substituent defined in Chemical Formula 1.

3. The multifunctional compound according to claim 1, wherein Ring A is represented by any one of C-1 to C-24 below, provided that in Chemical Formula 1, when Z and Q are single bonds, Ring A is not C-8, C-10, C-11, C-17, C-20, C-22, and C-23. Among C-1 to C-24, Two adjacent ones of the #s shown in the # positions correspond to J or L on ring A in Formula 1, R 1 to R 11 Each independently is hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl optionally substituted with a second additional substituent, C2-30 heteroaryl optionally substituted with a second additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino optionally substituted with a second additional substituent, C7-30 alkylarylamino optionally substituted with a second additional substituent, C9-30 cycloalkylarylamino optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylamino optionally substituted with a second additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy optionally substituted with a second additional substituent, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl optionally substituted with a second additional substituent, C7-30 alkylarylsilyl optionally substituted with a second additional substituent, C9-30 cycloalkylarylsilyl optionally substituted with a second additional substituent, C8-30 heterocycloalkylarylsilyl optionally substituted with a second additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio or C6-30 arylphosphine oxide, and at least two of the Rs 1 to R 11 are capable of connecting to each other to form a ring X' is independently O, S, Se, C, Si, C-(Ar 3 )2, Si-(Ar 3 )2 or N-Ar 3 , where Ar 3 is C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a second additional substituent, or C2-30 heteroaryl substituted or unsubstituted with a second additional substituent. When multiple Ars 3 are present, the multiple Ars can be connected to each other to form a ring. X" is independently N, O, S, or Se. The definition of the second additional substituent is the same as the second additional substituent defined in Chemical Formula 1.

4. The multifunctional compound according to any one of claims 1 to 3, wherein The multifunctional compound represented by Chemical Formula 1 is divided into an atom represented by X, a light-emitting part, and an excited-state complex-forming part. The light-emitting part is connected to the excited-state complex-forming part through the atom represented by X, and the atom represented by X is X shown in Chemical Formula 1. The light-emitting part includes ring A in Chemical Formula 1, a conjugated ring composed of Y 1 ~Y 5 and Q The excited state complex forming moiety includes the conjugated ring formed by Y 6 ~Y 10 in Chemical Formula 1, the conjugated ring formed by Y 11 ~Y 15 and Z The excited-state complex-forming part contains at least one atom having a non-bonding electron pair.

5. The multifunctional compound according to claim 4, wherein Said Y 6 to Y 15 and at least one of Z is an atom having a non-bonding electron pair included in the wave function of the HOMO or LUMO having the excited state complex forming moiety; or Y 6 to Y 15 at least one of which has an R represented by the following Chemical Formula 5 or the following Chemical Formula 6 Chemical Formula 5: Chemical Formula 6: In Chemical Formula 5 or Chemical Formula 6, L' is a single bond or a divalent group selected from the group consisting of C1-30 alkylene, C3-30 cycloalkylene, C2-30 heteroalkylene, C1-30 alkylmethylsilylene, C3-30 cycloalkylmethylsilylene, C2-30 heteroalkylmethylsilylene, C1-30 arylmethylsilylene, C7-30 alkylarylmethylsilylene, C9-30 cycloalkylarylmethylsilylene, C8-30 heteroalkylarylmethylsilylene, oxygen, sulfur, a divalent group of C6-30 arylphosphine, a divalent group of C6-30 arylphosphine oxide, C6-30 arylene, C2-30 heteroarylene and combinations thereof, Z' is absent, or represents a single bond, or is an atom selected from the group consisting of elements of Group IIIA, Group IVA, Group VA and Group VIA. When the Z' is an atom, it can have substituents selected from hydrogen, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heteroalkyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent and combinations thereof in a stoichiometric ratio, Ar 2 and Ar 3 each independently is a C1-30 alkyl group, a C3-30 cycloalkyl group, a C2-30 heterocycloalkyl group, a C3-30 alkenyl group, an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted by a third additional substituent, or a heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted by a third additional substituent, and the Ar 2 and Ar 3 can each independently be linked to the L' or the second additional substituent to form a fused ring, t is an integer from 0 to 5, v is 0 or 1, Each R" is independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heteroalkyl, C3-30 allyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heteroalkylamino, C6-30 arylamino substituted or unsubstituted with a third additional substituent, C7-30 alkylarylamino substituted or unsubstituted with a third additional substituent, C9-30 cycloalkylarylamino substituted or unsubstituted with a third additional substituent, C8-30 heteroalkylarylamino substituted or unsubstituted with a third additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy substituted or unsubstituted with a third additional substituent, C1-30 alkylsilyl substituted or unsubstituted with a third additional substituent, C3-30 cycloalkylsilyl substituted or unsubstituted with a third additional substituent, C2-30 heteroalkylsilyl substituted or unsubstituted with a third additional substituent, C6-30 arylsilyl substituted or unsubstituted with a third additional substituent, C7-30 alkylarylsilyl substituted or unsubstituted with a third additional substituent, C9-30 cycloalkylarylsilyl substituted or unsubstituted with a third additional substituent, C8-30 heteroalkylarylsilyl substituted or unsubstituted with a third additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heteroalkylthio, C6-30 arylthio, C6-30 arylphosphine, C6-30 arylphosphine oxide and combinations thereof. At this time, at least two of the R" can be connected to each other to form a ring, The third additional substituent is selected from C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl, C2-30 heteroaryl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C7-30 alkylarylamino, C9-30 cycloalkylarylamino, C8-30 heterocycloalkylarylamino, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C7-30 alkylarylsilyl, C9-30 cycloalkylarylsilyl, C8-30 heterocycloalkylarylsilyl, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, and combinations thereof, Y is each independently nitrogen, oxygen, sulfur, or carbon, Indicates the connection part, provided that in Formula 6, L' or R" contains at least one atom having a non-bonding electron pair included in the HOMO or LUMO wave function of the excited state complex-forming moiety, or at least one of Y is nitrogen, oxygen, or sulfur.

6. The multifunctional compound according to any one of claims 1 to 3, characterized in that, The multifunctional compound contains at least one deuterium.

7. The multifunctional compound according to claim 1, wherein The multifunctional compound represented by Formula 1 is any one of the following compounds:

8. An organic light-emitting diode, characterized in that, it includes a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, optionally including an organic layer adjacent to one or both sides of the light-emitting layer, the light-emitting layer contains the multifunctional compound according to any one of claims 1 to 3, the light-emitting layer or the adjacent organic layer contains an excited state complex-forming compound.

9. The organic light-emitting diode according to claim 8, characterized in that, the multifunctional compound represented by Formula 1 is divided into an atom represented by X, a light-emitting moiety, and an excited state complex-forming moiety, the light-emitting moiety is connected to the excited state complex-forming moiety through the atom represented by X, and the atom represented by X is X shown in Formula 1, The light-emitting part includes ring A in Chemical Formula 1, a conjugated ring composed of Y 1 ~Y 5 and Q The excited-state complex-forming moiety contains the conjugated ring formed by Y 6 ~Y 10 in Formula 1, the conjugated ring formed by Y 11 ~Y 15 and Z the excited state complex-forming moiety contains at least one atom having a non-bonding electron pair.

10. The organic light-emitting diode according to claim 9, characterized in that, Said Y 6 to Y 15 and at least one of Z is an atom having a non - shared electron pair contained in the wave function of the HOMO or LUMO having the excited - state complex - forming moiety; or Y 6 to Y 15 at least one of which has an R represented by the following Chemical Formula 5 or the following Chemical Formula 6 Formula 5: Formula 6: In Formula 5 or Formula 6, L' is a single bond or a divalent group selected from the group consisting of C1-30 alkylene, C3-30 cycloalkylene, C2-30 heterocycloalkylene, C1-30 alkylmethylsilylene, C3-30 cycloalkylmethylsilylene, C2-30 heterocycloalkylmethylsilylene, C1-30 arylmethylsilylene, C7-30 alkylarylmethylsilylene, C9-30 cycloalkylarylmethylsilylene, C8-30 heterocycloalkylarylmethylsilylene, oxygen, sulfur, a divalent group of C6-30 arylphosphine, a divalent group of C6-30 arylphosphine oxide, C6-30 arylene, C2-30 heteroarylene, and combinations thereof, Z' does not exist, represents a single bond, or is an atom selected from the group consisting of Group IIIA, Group IVA, Group VA, and Group VIA elements. When the Z' is an atom, it can have substituents selected from hydrogen, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, and combinations thereof, in a stoichiometric ratio. Ar 2 and Ar 3 each independently is a C1-30 alkyl group, a C3-30 cycloalkyl group, a C2-30 heterocycloalkyl group, a C3-30 alkenyl group, an aryl group of C6-30 substituted or unsubstituted with a third additional substituent or a heteroaryl group of C2-30 substituted or unsubstituted with a third additional substituent, and the Ar 2 and Ar 3 can each independently connect with the L' or the second additional substituent to form a fused ring, t is an integer from 0 to 5. v is 0 or 1. Each R" is independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl substituted or unsubstituted with a third additional substituent, C2-30 heteroaryl substituted or unsubstituted with a third additional substituent, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C6-30 arylamino substituted or unsubstituted with a third additional substituent, C7-30 alkylarylamino substituted or unsubstituted with a third additional substituent, C9-30 cycloalkylarylamino substituted or unsubstituted with a third additional substituent, C8-30 heterocycloalkylarylamino substituted or unsubstituted with a third additional substituent, halogen, CN, C1-30 alkoxy, C6-30 aryloxy substituted or unsubstituted with a third additional substituent, C1-30 alkylsilyl substituted or unsubstituted with a third additional substituent, C3-30 cycloalkylsilyl substituted or unsubstituted with a third additional substituent, C2-30 heterocycloalkylsilyl substituted or unsubstituted with a third additional substituent, C6-30 arylsilyl substituted or unsubstituted with a third additional substituent, C7-30 alkylarylsilyl substituted or unsubstituted with a third additional substituent, C9-30 cycloalkylarylsilyl substituted or unsubstituted with a third additional substituent, C8-30 heterocycloalkylarylsilyl substituted or unsubstituted with a third additional substituent, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio, C6-30 arylphosphine, C6-30 arylphosphine oxide, and combinations thereof. At this time, at least two of the R" can be connected to each other to form a ring. The third additional substituent is selected from C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C3-30 alkenyl, C6-30 aryl, C2-30 heteroaryl, C1-30 alkylamino, C3-30 cycloalkylamino, C2-30 heterocycloalkylamino, C7-30 alkylaryl amino, C9-30 cycloalkylaryl amino, C8-30 heterocycloalkylaryl amino, C1-30 alkylsilyl, C3-30 cycloalkylsilyl, C2-30 heterocycloalkylsilyl, C6-30 arylsilyl, C7-30 alkylarylsilyl, C9-30 cycloalkylarylsilyl, C8-30 heterocycloalkylarylsilyl, C1-30 alkylthio, C3-30 cycloalkylthio, C2-30 heterocycloalkylthio, C6-30 arylthio and combinations thereof, Y is independently nitrogen, oxygen, sulfur or carbon, Indicates the connection part, provided that in the formula 6, L' or R" contains at least one atom having a non-bonding electron pair included in the HOMO or LUMO wave function of the excited state complex forming moiety, or at least one of Y is nitrogen, oxygen or sulfur.

11. The organic light emitting diode according to claim 9, characterized in that, the excited state complex forming moiety forms an excited state complex with the excited state complex forming compound, the light emitting moiety emits light by receiving the excitation energy of the excited state complex.

12. The organic light emitting diode according to claim 8, wherein, The multifunctional compound contains at least one deuterium.

13. The organic light-emitting diode according to claim 8, wherein The light emitting layer contains at least two of the multifunctional compounds.

14. The organic light-emitting diode according to claim 8, wherein The light emitting layer further contains at least one selected from the group consisting of a host, an additional dopant and combinations thereof.

15. The organic light-emitting diode according to claim 8, wherein The light emitting layer further contains a phosphorescent substance containing Ir or Pt.

16. The organic light-emitting diode according to claim 8, characterized in that, The light emitting layer further contains a delayed fluorescence substance having a singlet-triplet energy difference of 0.3 eV or more.

17. The organic light emitting diode according to claim 8, characterized in that, the organic light emitting diode is a tandem organic light emitting diode including a plurality of organic light emitting units, at least one of the plurality of organic light emitting units includes the light emitting layer.

Images