Organic light emitting diode

Abstract

Provided is an organic light-emitting diode including a first electrode, a second electrode, and a light-emitting layer between the first electrode and the second electrode, the light-emitting layer including a novel composite light-emitting compound represented by Chemical Formula 1 described in the detailed description.

Description

Technical Field

[0001] The present invention relates to an organic light-emitting diode (OLED) comprising a long-life organic light-emitting material. More specifically, the present invention relates to an organic light-emitting diode (OLED) capable of minimizing the brightness of light even during long-term driving by improving the light-emitting stability of the luminous body. Background Art

[0002] OLEDs (Organic Light Emitting Diodes) are devices in which holes injected from the anode and electrons injected from the cathode combine in the light-emitting layer through a charge transport layer, forming excitons and emitting light. They were first reported by CW Tang in 1987 in Appl. Phys. Lett. 51, 913. At the time, the light-emitting layer consisted of a single substance, Alq3. However, in 1989, in J. Appl. Phys., Vol. 65, 3610, they reported that by doping Alq3 with small amounts of the red-emitting compound DCM and the green-emitting compound Coumarine 540, the emission wavelength was adjusted and efficiency was improved. Summary of the Invention

[0003] Technical issues

[0004] An object of the present invention is to provide an organic light emitting diode that can minimize the brightness of light even when driven for a long time by improving the light emission stability of the light emitting body.

[0005] The purpose of the present invention is not limited to the purpose described above, and other purposes 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 purposes and advantages of the present invention can be achieved by the means described in the scope of the invention claims and their combinations.

[0006] Technical Solution

[0007] In one embodiment of the present invention, an organic light emitting diode is provided.

[0008] comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode,

[0009] The light-emitting layer includes a composite light-emitting compound represented by the following chemical formula 1:

[0010] The composite light-emitting compound comprises a light-emitting portion and a charge stabilizing portion, wherein the light-emitting portion and the charge stabilizing portion are connected via an atom X, wherein the atom X is X shown in the following chemical formula 1:

[0011] The light emitting portion comprises A in the following chemical formula 1,1 ~Y 5 The conjugated ring and Q,

[0012] The charge stabilizing portion comprises the following chemical formula 1 wherein Y 6 ~Y 10 The ring composed of Y 11 ~Y 15 The ring and Z,

[0013] The charge stabilizing moiety comprises at least one atom having an unshared electron pair,

[0014] Chemical formula 1:

[0015]

[0016] In the chemical formula 1,

[0017] A is a structure represented by the following chemical formula 2, and is connected through the first connection position in A, or through the first connection position and the second connection position in A,

[0018] X is C, Si, Ge, Sn or Pb, the first connecting position in A is connected to X,

[0019] Q does not exist, or is a single bond, -B(Ar 1 )-、-C(Ar 1 )(Ar 2 )-、-Si(Ar 1 )(Ar 2 )-、-Ge(Ar 1 )(Ar 2 )-、-N(Ar 1 )-、-P(Ar 1 )-、-PO(Ar 1 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 1 and Ar 2 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 1 and Ar 2 can be connected to each other to form a ring, or by respectively with Y2 , and Y 2 The connected R or A are connected to form a fused ring,

[0020] When Q is absent, A is not directly connected to Y at the second connection position in A. 1 connect,

[0021] When Q is a single bond, A is connected to Y at the second connecting position in A through a single bond. 1 connect,

[0022] When Q is not a single bond and is present as any one of the above definitions, A is linked to Q at the second linking position in A,

[0023] When Q is not a single bond and exists as any one of the above definitions, Q is respectively connected to A and Y through a single bond. 1 connect,

[0024] Y 1 To Y 15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se or Te,

[0025] Z does not exist, or is a single bond, -B(Ar 3 )-、-C(Ar 3 )(Ar 4 )-、-Si(Ar 3 )(Ar 4 )-、-Ge(Ar 3 )(Ar 4 )-、-N(Ar 3 )-、-P(Ar 4 )-、-PO(Ar 3 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 3 and Ar 4 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 3 and Ar 4 can be connected to each other to form a ring, or by respectively with Y 7 、Y 12 , and Y 7 Connect R or Y12 Any of the connected R's are connected to form a condensed ring,

[0026] When Z does not exist, Y 6 Not directly with Y 11 connect,

[0027] When Z is a single bond, Y 6 By single bond with Y 11 connect,

[0028] When Z is not a single bond and exists as any one of the above definitions, Z is respectively connected to Y by a single bond. 6 and Y 11 connect,

[0029] m, n and o are each independently an integer from 0 to 5,

[0030] R is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 101 )(R 102 )、-C(R 103 )(R 104 )(R 105 )、-Si(R 106 )(R 107 )(R 108 )、-Ge(R 109 )(R 110 )(R 111 )、-N(R 112 )(R 113 )、-P(R 114 )(R 115 )、-PO(R 116 )(R 117 )、-O(R 118 )、-S(R 119 )、-SO(R 120 )、-SO2(R 121 )、Se(R 122)、-SeO(R 123 )、-SeO2(R 124 ) and combinations thereof,

[0031] R 101 to R 124 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 101 to R 124 At least two atoms connected to each other can be connected to form a ring,

[0032] When m, n or o is 2 or more, at least two R present can be linked to each other to form a ring,

[0033] 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.

[0034] The condition is that Y 6 To Y 15 and at least one atom in Z is an atom containing an unshared electron pair, or R in combination thereof contains at least one atom containing an unshared electron pair,

[0035] Chemical formula 2:

[0036]

[0037] In the chemical formula 2,

[0038] M is a transition metal,

[0039] V 1 、V 2 、V 3 and V 4 Each independently does not exist, or is a single bond, -B(Ar 5 )-、-C(Ar 5 )(Ar 6 )-、-Si(Ar 5 )(Ar 6 )-、-Ge(Ar 5 )(Ar 6 )-、-N(Ar 5 )-、-P(Ar 5 )-、-PO(Ar5 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 5 and Ar 6 Can connect to each other to form a ring, or connect to adjacent E 1 、E 2 、E 3 or E 4 Connected to form a fused ring,

[0040] The condition is that V 1 、V 2 、V 3 and V 4 At least one of is a single bond,

[0041] When V 1 、V 2 、V 3 and V 4 When it does not exist, its adjacent E 1 、E 2 、E 3 and E 4 The two are not directly connected,

[0042] When V 1 、V 2 、V 3 and V 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 and E 4 The two are directly connected by a single bond. When V 1 、V 2 、V 3 and V 4 When it is not a single bond and exists as any one of the above definitions, it can be adjacent to E 1 、E 2 、E 3 and E 4 The two of them are connected by a single bond, or the adjacent E 1、E 2 、E 3 and E 4 The two connected bonds in the form a conjugated structure together.

[0043] J 1 、J 2 、J 3 and J 4 are single bonds, O or S, respectively,

[0044] When J 1 、J 2 、J 3 and J 4 When it is a single bond, the connected E 1 、E 2 、E 3 and E 4 Any one of them is directly bound to M through a coordination bond or a covalent bond,

[0045] When J 1 、J 2 、J 3 and J 4 When it is O or S, the bond formed with M is a coordination bond or a covalent bond.

[0046] E 1 、E 2 、E 3 and E 4 are each independently a monovalent, divalent or trivalent group and are defined as follows, provided that when E 1 、E 2 、E 3 and E 4 When V is a monovalent group, 1 、V 2 、V 3 and V 4 The two adjacent ones do not exist; when E 1 、E 2 、E 3 and E 4 When V is a divalent group, 1 、V 2 、V 3 and V 4 In which any of the two adjacent ones does not exist; when E 1 、E 2 、E 3 and E 4 When it is a trivalent group, V 1 、V 2 、V 3 and V 4 In which both adjacent ones exist,

[0047] E 1 、E 2 、E 3 and E 4 each independently a monovalent group that is a halogen or cyano group, or a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C5-50 aromatic carbocyclic ring that is substituted or unsubstituted with an additional substituent; a C2-50 aromatic heterocyclic ring that is substituted or unsubstituted with an additional substituent; a C3-50 saturated or unsaturated alicyclic carbocyclic ring that is substituted or unsubstituted with an additional substituent; or a C2-50 saturated or unsaturated alicyclic heterocyclic ring that is substituted or unsubstituted with an additional substituent,

[0048] E 1 、E 2 、E 3 and E 4 At least two additional substituents contained therein can be linked to form a ring,

[0049] The condition is that when J 1 、J 2 、J 3 or J 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 or E 4 The atom at the position where it is connected to M is carbon, nitrogen, oxygen, sulfur or phosphorus; or, when J 1 、J 2 、J 3 or J 4 When it is O or S, its adjacent E 1 、E 2 、E 3 or E 4 With J 1 、J 2 、J 3 or J 4 The atom at the O or S bonding position is carbon;

[0050] E 1 、E 2 、E 3 and E 4 Any one of the J adjacent to it 1 、J 2 、J 3 or J 4 The connection position and the adjacent V 1 、V 2 、V 3 or V 4 The connection positions are adjacent,

[0051] E1 、E 2 、E 3 and E 4 Any one of the adjacent V 1 、V 2 、V 3 and V 4 The connection positions of the two are different.

[0052] In the chemical formula 2, in addition to M, atoms capable of bonding in a stoichiometric ratio may serve as the first bonding position or the second bonding position in A of the chemical formula 1, provided that the first bonding position and the second bonding position are each different from (i) E 1 、E 2 、E 3 and E 4 Any one of the J adjacent to it 1 、J 2 、J 3 、J 4 、V 1 、V 2 、V 3 or V 4 The connection position of V 1 、V 2 、V 3 and V 4 Any one of the adjacent E 1 、E 2 、E 3 or E 4 The connection location,

[0053] The first connection position and the second connection position are adjacent to each other,

[0054] The additional substituents may be present in an amount capable of being combined in a stoichiometric ratio and are each independently selected from the group consisting of deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211)、-N(R 212 )(R 213 )、-P(R 214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 Each is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl or C2-30 heteroaryl.

[0055] Effects of the Invention

[0056] The organic light-emitting diode comprising the novel composite light-emitting compound can minimize the brightness under long-term driving by improving the light-emitting stability of the device.

[0057] In addition to the above effects, the specific effects of the present invention will be described below in conjunction with specific embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0058] Figure 1 is a graph comparing the device characteristics of Example 1 and Comparative Example 1. DETAILED DESCRIPTION

[0059] 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 the present invention. The present invention can be implemented in various forms and is not limited to the embodiments described herein.

[0060] As used herein, the term "substituted" refers to the replacement of a hydrogen atom bonded to a carbon atom in a compound with another substituent. The position where the substitution occurs refers to the position where the hydrogen atom is replaced. The position is not limited, as long as the hydrogen at the position can be replaced by a substituent. When two or more substitutions occur, the two or more substituents may be the same or different.

[0061] In the present specification, unless otherwise mentioned, the substituent in the case of "substituted" may be selected from the following groups: for example, deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211 )、-N(R 212 )(R 213 )、-P(R 214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 Each may be independently one selected from the following group: hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl, C2-30 heteroaryl and combinations thereof, but is not limited thereto.

[0062] In this specification, unless otherwise defined, "a combination thereof" in the definition of a substituent means the presence of two or more substituents, or two or more divalent substituents that are linked or condensed.

[0063] In the present specification, the case where two substituents are linked to form a ring includes the case where one of the two substituents is hydrogen and the linking occurs when the hydrogen is removed.

[0064] In this specification, unless otherwise specified, "alkyl" includes straight or branched chains, and unless otherwise specified, the term is intended to include "cycloalkyl and heterocycloalkyl". In this specification, unless otherwise specified, "alkenyl" includes straight or branched chains, and unless otherwise specified, the term is intended to include "cycloalkenyl and heterocycloalkenyl". For example, unless otherwise specified, alkylamino is intended to include cycloalkylamino and heterocycloalkylamino.

[0065] In the present specification, "heteroalkyl" or "heteroalkylene" means that at least one carbon atom in an alkyl group or an alkylene group is substituted by a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding heteroatoms.

[0066] In the present specification, "heteroalkenyl" means an alkenyl group in which at least one non-double-bond carbon atom is substituted by a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0067] In the present specification, "heterocycloalkyl" means that at least one carbon atom in a cycloalkyl group is substituted by a heteroatom, and the number of carbon atoms means the number of carbon atoms excluding the heteroatom.

[0068] In the present specification, "heterocycloalkenyl" refers to a cycloalkenyl group in which at least one non-double-bond carbon atom is substituted by a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0069] In this specification, unless otherwise defined, "hetero" means that a compound or substituent contains a heteroatom, which refers to an atom other than carbon and hydrogen, such as 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, they may contain the same or different heteroatoms, for example, one or more heteroatoms. For example, a heteroaryl group or a heterocycloalkyl group contains at least one heteroatom as a ring atom.

[0070] In this specification, "aryl", "arylene" or "aromatic" may be a monocyclic or polycyclic ring according to commonly known definitions, and part or all of them may include a conjugated structure. The polycyclic ring may be a fused ring or a linked ring. For example, aryl or aromatic carbocyclic rings include biphenyl.

[0071] Among the substituents mentioned in this specification, substituents other than the substituents defined above are defined in accordance with known substituents.

[0072] In the present specification, when substituents or bonding positions in a chemical formula are adjacent, it means that the atoms to which the substituents are bonded or the atoms at the bonding positions are directly bonded.

[0073] In this specification, unless otherwise mentioned, when the definition of a substituent includes the case where an additional substituent is substituted, the additional substituent falls within the scope of the defined substituent. For example, when Z in Chemical Formula 1 is -N(Ar 1 )-,Ar 1 When the phenyl group is substituted with a methyl group as an additional substituent, the methyl group as the additional substituent belongs to Z. That is, the scope of Z here includes the methyl group as an additional substituent. It should be understood that Z is described only as an example, but for all substituents defined in the chemical formulas in this specification, when the additional substituent can be substituted, the additional substituent is included in the scope of the defined substituent. For another example, in Chemical Formula 1, the first connection position or the second connection position of A can be located on the additional substituent within the scope of A. Similarly, in Chemical Formula 2, E 1 The connection position of the E 1 on additional substituents within the scope of .

[0074] In the present specification, unless otherwise mentioned, the number of the additional substituents substituted may be present in an amount capable of being combined in a stoichiometric ratio.

[0075] In the present specification, unless otherwise mentioned, a ring includes a fused ring.

[0076] In this specification, when two entities (substituents, etc.) are linked, this includes the case where one of the entities is hydrogen and the link occurs when the hydrogen is removed.

[0077] In this specification, unless otherwise mentioned, a dotted line in a chemical structural formula indicates that a dot may be present or absent.

[0078] In this specification, coordination bonds and single bonds in chemical structural formulas are represented by straight lines without distinction, but include all structures that can be combined in a stoichiometric ratio.

[0079] In one embodiment of the present invention,

[0080] comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode,

[0081] The light-emitting layer includes a composite light-emitting compound represented by the following chemical formula 1:

[0082] The composite light-emitting compound comprises a light-emitting portion and a charge stabilizing portion, wherein the light-emitting portion and the charge stabilizing portion are connected via an atom X, wherein the atom X is X shown in the following chemical formula 1:

[0083] The light emitting portion comprises A in the following chemical formula 1, 1 ~Y 5 The conjugated ring and Q,

[0084] The charge stabilizing portion comprises the following chemical formula 1 wherein Y 6 ~Y 10 The ring composed of Y 11 ~Y 15 The ring and Z,

[0085] The charge stabilizing moiety comprises at least one atom having an unshared electron pair.

[0086] Chemical formula 1:

[0087]

[0088] In the chemical formula 1,

[0089] A is a structure represented by the following chemical formula 2, and is connected through the first connection position in A, or through the first connection position and the second connection position in A,

[0090] X is C, Si, Ge, Sn or Pb, the first connecting position in A is connected to X,

[0091] Q does not exist, or is a single bond, -B(Ar 1 )-、-C(Ar 1 )(Ar 2 )-、-Si(Ar 1 )(Ar 2 )-、-Ge(Ar 1 )(Ar 2 )-、-N(Ar 1 )-、-P(Ar 1 )-、-PO(Ar 1 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 1 and Ar 2 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 1 and Ar 2 can be connected to each other to form a ring, or by respectively with Y 2 , and Y 2 The connected R or A are connected to form a fused ring,

[0092] When Q is absent, A is not directly connected to Y at the second connection position in A. 1 connect,

[0093] When Q is a single bond, A is connected to Y at the second connecting position in A through a single bond. 1 connect,

[0094] When Q is not a single bond and is present as any one of the above definitions, A is linked to Q at the second linking position in A,

[0095] When Q is not a single bond and exists as any one of the above definitions, Q is respectively connected to A and Y through a single bond. 1 connect,

[0096] Y 1 To Y 15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se or Te,

[0097] Z does not exist, or is a single bond, -B(Ar 3 )-、-C(Ar 3 )(Ar 4 )-、-Si(Ar 3 )(Ar 4 )-、-Ge(Ar 3 )(Ar 4 )-、-N(Ar 3 )-、-P(Ar 4 )-、-PO(Ar 3 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 3 and Ar 4 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 3 and Ar 4 can be connected to each other to form a ring, or by respectively with Y 7 、Y 12 , and Y 7 Connect R or Y 12 Any of the connected R's are connected to form a condensed ring,

[0098] When Z does not exist, Y6 Not directly with Y 11 connect,

[0099] When Z is a single bond, Y 6 By single bond with Y 11 connect,

[0100] When Z is not a single bond and exists as any one of the above definitions, Z is respectively connected to Y by a single bond. 6 and Y 11 connect,

[0101] m, n and o are each independently an integer from 0 to 5,

[0102] R is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 101 )(R 102 )、-C(R 103 )(R 104 )(R 105 )、-Si(R 106 )(R 107 )(R 108 )、-Ge(R 109 )(R 110 )(R 111 )、-N(R 112 )(R 113 )、-P(R 114 )(R 115 )、-PO(R 116 )(R 117 )、-O(R 118 )、-S(R 119 )、-SO(R 120 )、-SO2(R 121 )、Se(R 122 )、-SeO(R 123 )、-SeO2(R 124 ) and combinations thereof,

[0103] R 101 to R 124 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 101 to R 124 At least two atoms connected to each other can be connected to form a ring,

[0104] When m, n or o is 2 or more, at least two R present can be linked to each other to form a ring,

[0105] 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.

[0106] The condition is that Y 6 To Y 15 and at least one atom in Z is an atom containing an unshared electron pair, or R in combination thereof contains at least one atom containing an unshared electron pair,

[0107] Chemical formula 2:

[0108]

[0109] In the chemical formula 2,

[0110] M is a transition metal,

[0111] V 1 、V 2 、V 3 and V 4 Each independently does not exist, or is a single bond, -B(Ar 5 )-、-C(Ar 5 )(Ar 6 )-、-Si(Ar 5 )(Ar 6 )-、-Ge(Ar 5 )(Ar 6 )-、-N(Ar 5 )-、-P(Ar 5 )-、-PO(Ar 5)-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 5 and Ar 6 Can connect to each other to form a ring, or connect to adjacent E 1 、E 2 、E 3 or E 4 Connected to form a fused ring,

[0112] The condition is that V 1 、V 2 、V 3 and V 4 At least one of is a single bond,

[0113] When V 1 、V 2 、V 3 and V 4 When it does not exist, its adjacent E 1 、E 2 、E 3 and E 4 The two are not directly connected,

[0114] When V 1 、V 2 、V 3 and V 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 and E 4 The two are directly connected by a single bond. When V 1 、V 2 、V 3 and V 4 When it is not a single bond and exists as any one of the above definitions, it can be adjacent to E 1 、E 2 、E 3 and E 4 The two of them are connected by a single bond, or the adjacent E 1 、E2 、E 3 and E 4 The two connected bonds in the form a conjugated structure together.

[0115] J 1 、J 2 、J 3 and J 4 are single bonds, O or S, respectively,

[0116] When J 1 、J 2 、J 3 and J 4 When it is a single bond, the connected E 1 、E 2 、E 3 and E 4 Any one of them is directly bound to M through a coordination bond or a covalent bond,

[0117] When J 1 、J 2 、J 3 and J 4 When it is O or S, the bond formed with M is a coordination bond or a covalent bond.

[0118] E 1 、E 2 、E 3 and E 4 are each independently a monovalent, divalent or trivalent group and are defined as follows, provided that when E 1 、E 2 、E 3 and E 4 When V is a monovalent group, 1 、V 2 、V 3 and V 4 The two adjacent ones do not exist; when E 1 、E 2 、E 3 and E 4 When V is a divalent group, 1 、V 2 、V 3 and V 4 In which any of the two adjacent ones does not exist; when E 1 、E 2 、E 3 and E 4 When it is a trivalent group, V 1 、V 2 、V 3 and V 4 In which both adjacent ones exist,

[0119] E1 、E 2 、E 3 and E 4 each independently a monovalent group that is a halogen or cyano group, or a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C5-50 aromatic carbocyclic ring that is substituted or unsubstituted with an additional substituent; a C2-50 aromatic heterocyclic ring that is substituted or unsubstituted with an additional substituent; a C3-50 saturated or unsaturated alicyclic carbocyclic ring that is substituted or unsubstituted with an additional substituent; or a C2-50 saturated or unsaturated alicyclic heterocyclic ring that is substituted or unsubstituted with an additional substituent,

[0120] E 1 、E 2 、E 3 and E 4 At least two additional substituents contained therein can be linked to form a ring,

[0121] The condition is that when J 1 、J 2 、J 3 or J 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 or E 4 The atom at the position where it is connected to M is carbon, nitrogen, oxygen, sulfur or phosphorus; or, when J 1 、J 2 、J 3 or J 4 When it is O or S, its adjacent E 1 、E 2 、E 3 or E 4 With J 1 、J 2 、J 3 or J 4 The atom at the O or S bonding position is carbon;

[0122] E 1 、E 2 、E 3 and E 4 Any one of the J adjacent to it 1 、J 2 、J 3 or J 4 The connection position and the adjacent V 1 、V 2 、V 3 or V 4 The connection positions are adjacent,

[0123] E1 、E 2 、E 3 and E 4 Any one of the adjacent V 1 、V 2 、V 3 and V 4 The connection positions of the two are different.

[0124] In the chemical formula 2, in addition to M, atoms capable of bonding in a stoichiometric ratio may serve as the first bonding position or the second bonding position in A of the chemical formula 1, provided that the first bonding position and the second bonding position are each different from (i) E 1 、E 2 、E 3 and E 4 Any one of the J adjacent to it 1 、J 2 、J 3 、J 4 、V 1 、V 2 、V 3 or V 4 The connection position of V 1 、V 2 、V 3 and V 4 Any one of the adjacent E 1 、E 2 、E 3 or E 4 The connection location,

[0125] The first connection position and the second connection position are adjacent to each other,

[0126] The additional substituents may be present in an amount capable of being combined in a stoichiometric ratio and are each independently selected from the group consisting of deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211)、-N(R 212 )(R 213 )、-P(R 214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 Each is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl or C2-30 heteroaryl.

[0127] In the definition of the chemical formula 1, Q is not hydrogen or deuterium Ar 1 or Ar 2 With Y 2 or Y 2 The cases where the connected R is connected to form a condensed ring include: 2 The R connected is hydrogen. When the hydrogen (ie, R) is removed, Ar 1 or Ar 2 With Y 2 Connection status.

[0128] In the definition of Chemical Formula 1, Ar in Z 3 or Ar 4 With Y 7 、Y 12 、Y 7 Connected R or Y 12 The case where any one of the connected R is connected to form a condensed ring includes: Y 7 Connected R or Y 12 The R connected is hydrogen. When the hydrogen (ie, R) is removed, Ar 3 or Ar 4 With Y 7 or Y 12 Connection status.

[0129] In the chemical formula 1, when at least two Rs are connected to form a ring, such a ring includes a condensed ring. In addition, the case where two Rs are connected includes: any one of the two Rs connected is hydrogen, and when the hydrogen (i.e., R) is detached, the Y connected to the hydrogen (i.e., R) is 1 To Y 15The case where either one is directly connected to the other of the two Rs.

[0130] In the chemical formula 2, when E 1 、E 2 、E 3 and E 4 When at least two additional substituents included in the ring are connected to form a ring, the ring includes a condensed ring. The two additional substituents forming the ring can be E 1 、E 2 、E 3 and E 4 In addition, the case where two additional substituents are connected includes the case where any one of the two connected substituents is a hydrogen atom, and the connection occurs when the hydrogen atom (ie, R) is removed.

[0131] In the definition of Chemical Formula 2, E 1 、E 2 、E 3 and E 4 Middle and J 1 、J 2 、J 3 、J 4 Or the atom at the connection position of M can be E 1 、E 2 、E 3 and E 4 The atoms contained in the defined aliphatic hydrocarbon, aliphatic hydrocarbon containing heteroatoms, aromatic carbocycle, aromatic heterocycle, alicyclic carbocycle or alicyclic heterocycle, or the atoms contained in the attached substituents thereof.

[0132] The organic light emitting diode utilizes the novel composite light emitting compound represented by Chemical Formula 1 to improve the light emitting stability of the device, thereby realizing an organic light emitting diode capable of minimizing the brightness even under long-term driving.

[0133] In addition to the wavelength and efficiency of organic light-emitting diodes (OLEDs), dopants play a crucial role in determining the device's brightness decay over time. This composite luminescent compound was developed by improving the dopant's degradation mechanism and energy transfer process, enabling the device to exhibit stable brightness even under long-term driving.

[0134] The process in which electrons and holes injected into the light-emitting layer combine in the host in the light-emitting layer to form excitons and their energy is transferred to the dopant can be expressed by the light-based method (FRET, Resonance Energy transfer) and the electron-based method (Dexter Electron Transfer) of the following mathematical formula 2 are used to explain it.

[0135] FRET( Resonance Energy transfer)

[0136] Mathematical formula 1:

[0137]

[0138] Dexter Electron Transfer

[0139] Mathematical formula 2:

[0140]

[0141] k ET : rate constant

[0142] r: distance between energy donor and energy acceptor

[0143] τ D : PL decay time of energy donor

[0144] κ: orientation factor

[0145] Q D : PL quantum efficiency of energy donor

[0146] N A : Avogadro's constant

[0147] n: refractive index

[0148] J: is defined by the following mathematical formula 3.

[0149] Mathematical formula 3:

[0150] J = ∫f D (λ)ε A (λ)λ 4 dλ

[0151] f D : Luminescence spectrum of energy donor

[0152] ε A : wavelength-dependent absorption coefficient of the energy acceptor

[0153] L: the sum of Van der Waals radii

[0154] λ: wavelength

[0155] Once the dopant receives energy from the host, it enters an excited state. This is the same state as when one of the two electrons in the dopant's HOMO (Highest Occupied Molecular Orbital) energy level moves to the LUMO (Lowest Unoccupied Molecular Orbital) energy level. The time required for an electron to transition from the LUMO energy level to the HOMO energy level and restabilize can range from a few nanoseconds to several milliseconds, depending on the electron's spin state. Considering that the vibrational motion time of a molecule is on the order of picoseconds, the excited dopant will continue to interact with surrounding molecules before being relaxed by light. It will form new energy levels, trigger chemical reactions, or decompose. This series of processes accelerates the decline in the luminous intensity of the organic light-emitting diode with driving time.

[0156] The HOMO-LUMO energy gap of the dopant is always smaller than the HOMO-LUMO energy gap of the host substance, but the energy level position between the two substances is not always constant and can appear in two forms as shown in the figure below. HOMO Indicates the HOMO energy level of each substance, E LUMO Indicates the LUMO energy level of each substance.

[0157]

[0158] Type 1 is when the HOMO energy level of the dopant is higher than that of the host, and Type 2 is when the LUMO energy level of the dopant is lower than that of the host. Holes are directly injected into the light-emitting layer through the hole transport layer, and electrons are injected into the light-emitting layer from the other side through the electron transport layer. Holes and electrons are injected into the light-emitting layer from the thickness of The dopant is injected from both sides of the light-emitting layer, so that holes (type 1) or electrons (type 2) are captured by the dopant before the two charges meet to form excitons.

[0159] When charges are trapped by a dopant, the ionized dopant becomes unstable and seeks stability until an opposite charge arrives. It may interact with other excitons already formed in the surrounding environment, undergo chemical reactions with surrounding compounds, or decompose. This series of processes accelerates the decrease in OLED luminescence intensity over time.

[0160] The novel composite light-emitting compound represented by Chemical Formula 1 has a charge stabilizing portion that stabilizes the light-emitting portion at a very close distance in an excited state or an ionized state, and can maintain stable brightness even when the organic light-emitting device is driven for a long time.

[0161] The light-emitting part and the charge stabilizing part of the composite light-emitting compound are as defined in Chemical Formula 1.

[0162] Specifically, the charge stabilizing portion comprises Y in the chemical formula 1. 6 ~Y 10 The conjugated ring composed of Y 11 ~Y 15 The conjugated ring and Z are formed.

[0163] The first function of the charge stabilizing portion is to stabilize the light-emitting portion when charges are captured by the light-emitting portion and ionized or in an excited state.

[0164] The second function of the charge stabilizing moiety is to sterically protect a specific portion of the luminescent moiety, thereby reducing the probability of the excited or ionized luminescent moiety interacting with other surrounding molecules.

[0165] The third function of the charge stabilizing portion is to spatially protect a specific portion of the light emitting portion, thereby reducing the probability of charge being directly captured by the light emitting portion.

[0166] In order for the charge stabilizing moiety to play this role, it needs to have polarity (dipole moment). Specifically, the charge stabilizing moiety contains at least one atom having an unshared electron pair and has a polarity greater than 0 Debye.

[0167] Examples of elements with non-shared electron pairs can include nitrogen, phosphorus, arsenic, antimony, oxygen, sulfur, selenium (Se), fluorine, chlorine, bromine, and the like. The element with non-shared electron pairs contained in the charge stabilizing portion can act as an electron donor or electron acceptor according to the bonding mode, or can stabilize the luminescent portion by making the charge stabilizing portion polar. In addition, the atoms containing non-shared electron pairs must form a wave function of HOMO or LUMO. That is, they must be included in the wave function representing the HOMO and LUMO electron distributions. For example, in the HOMO wave function of the charge stabilizing portion, when a higher electron density is formed in the atoms with the non-shared electron pairs, when the luminescent portion is positively charged, the stabilizing effect is enhanced. On the other hand, in the LUMO wave function of the charge stabilizing portion, when a higher electron density is formed in the atoms with the non-shared electron pairs, when the luminescent portion is negatively charged, a stabilizing effect can be expected. Quantum calculations can be performed using DFT B3LYP 6-31G* as a basis set. The definition standard of the HOMO and LUMO wave functions of the charge stabilizing part is obtained by DFT calculation based on the structure in which the connection between the light-emitting part and X is disconnected and the connection position is replaced by hydrogen or -CH3.

[0168] In one example, in the chemical formula 1,

[0169] (i) the Y 6 To Y 15 and Y 6 and Y 11 At least one atom of the attached Z is an atom having an unshared electron pair contained in the HOMO or LUMO wave function of the charge stabilizing moiety; or

[0170] (ii)Y 6 To Y 15 At least one of them has R represented by the following Chemical Formula 9 or the following Chemical Formula 10.

[0171] Chemical formula 9:

[0172]

[0173] Chemical formula 10:

[0174]

[0175] In the Chemical Formula 9 or Chemical Formula 10,

[0176] L is a single bond, or a divalent group selected from the group consisting of C1-20 alkylene, C3-20 cycloalkylene, C3-20 cycloalkenylene, C1-20 heteroalkylene, C2-20 heterocycloalkylene, C2-20 heterocycloalkenylene, C2-20 alkenylene, -O-, -S-, -P(R 401 )-、-PO(R 402 )-, C6-20 arylene, C5-20 heteroarylene and combinations thereof,

[0177] Ar 11 and Ar 12 Each is independently a C1-20 saturated or unsaturated aliphatic hydrocarbon substituted or unsubstituted with an additional substituent; a C1-20 saturated or unsaturated aliphatic hydrocarbon containing a heteroatom substituted or unsubstituted with an additional substituent; a C5-20 aromatic carbocyclic ring substituted or unsubstituted with an additional substituent; a C2-20 aromatic heterocyclic ring substituted or unsubstituted with an additional substituent; a C3-20 saturated or unsaturated alicyclic carbocyclic ring substituted or unsubstituted with an additional substituent; or a monovalent or divalent group of a C2-20 saturated or unsaturated alicyclic heterocyclic ring substituted or unsubstituted with an additional substituent,

[0178] Z' does not exist, or is a single bond, -B(Ar 13 )-、-C(Ar 13 )(Ar 14 )-、-Si(Ar 13 )(Ar 14 )-、-Ge(Ar 13 )(Ar14 )-、-N(Ar 13 )-、-P(Ar 13 )-、-PO(Ar 13 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 13 and Ar 14 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 13 and Ar 14 can be connected to each other to form a ring, or respectively with Ar 11 and Ar 12 Any one of them is connected to form a condensed ring,

[0179] When Z' does not exist, Ar 11 and Ar 12 No direct connection,

[0180] When Z' is a single bond, Ar 11 and Ar 12 Connect with one click.

[0181] t is an integer from 0 to 5,

[0182] v is 0 or 1,

[0183] R'" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl, C1-30 heteroalkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 501 )(R 502 )、-C(R 503 )(R 504 )(R 505 )、-Si(R 506 )(R 507 )(R 508 )、-Ge(R 509 )(R 510 )(R 511 )、-N(R512 )(R 513 )、-P(R 514 )(R 515 )、-PO(R 516 )(R 517 )、-O(R 518 )、-S(R 519 )、-SO(R 520 )、-SO2(R 521 )、Se(R 522 )、-SeO(R 523 )、-SeO2(R 524 ) and combinations thereof, in which case at least two of the R'" can be connected to each other to form a ring,

[0184] R 401 to R 402 and R 501 to R 524 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C6-30 aryl or C2-30 heteroaryl, and R 401 to R 402 and R 501 to R 524 At least two atoms connected to each other can be connected to form a ring,

[0185] Y is each independently nitrogen, oxygen, sulfur or carbon,

[0186] Indicates the connection part,

[0187] The additional substituents may be present in an amount capable of being combined in a stoichiometric ratio and are each independently selected from the group consisting of deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211 )、-N(R 212 )(R 213 )、-P(R214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 are each independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl or C2-30 heteroaryl,

[0188] Provided that, in the Chemical Formula 10, L or R'" includes at least one atom having an unshared electron pair included in the HOMO or LUMO wave function of the charge stabilizing portion, or at least one of Y is nitrogen, oxygen, or sulfur.

[0189] In the chemical formula 10, when at least two R'" are connected to form a ring, such a ring includes a condensed ring. In addition, the case where two R'" are connected includes the case where either of the two connected R'" is hydrogen, and when the hydrogen (i.e., R'") is detached, the Y connected to the hydrogen (i.e., R'") is directly connected to another R'".

[0190] In the chemical formula 10, when at least two R'" are connected to form a ring, such a ring includes a condensed ring. In addition, the case where two R'" are connected includes the case where either of the two connected R'" is hydrogen, and when the hydrogen (i.e., R'") is detached, the Y connected to the hydrogen (i.e., R'") is directly connected to another R'".

[0191] In one example, at least one R contained in the chemical formula 1 can be represented by any one of the following chemical formulas D-1 to D-38:

[0192]

[0193]

[0194]

[0195] In the chemical formulas D-1 to D-38,

[0196] Y is each independently carbon or nitrogen,

[0197] X'" are each independently oxygen, nitrogen, sulfur or selenium,

[0198] R"" are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 601 )(R 602 )、-C(R 603 )(R 604 )(R 605 )、-Si(R 606 )(R 607 )(R 608 )、-Ge(R 609 )(R 610 )(R 611 )、-N(R 612 )(R 613 )、-P(R 614 )(R 615 )、-PO(R 616 )(R 617 )、-O(R 618 )、-S(R 619 )、-SO(R 620 )、-SO2(R 621 )、Se(R 622 )、-SeO(R 623 )、-SeO2(R 624 ) and their combinations, R 601 to R 624 are each independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl, C2-30 heteroaryl, and combinations thereof,

[0199] u are each independently an integer from 0 to 20,

[0200] Dashed lines indicate connection sites.

[0201] In the composite light-emitting compound represented by Chemical Formula 1, the charge stabilizing portion and the light-emitting portion are combined via the atom X. When Z is present, a spiro bond is formed via the spiro atom X.

[0202] The first function of the connecting portion of the atom X is to ensure a certain distance and spacing between the charge-stabilizing portion and the light-emitting portion. Thus, if the charge-stabilizing portion is positioned and angled so as to prevent chemical interaction with the light-emitting portion, it can protect a specific portion of the light-emitting portion, thereby significantly reducing the probability of chemical and Coulombic interactions with other surrounding dopants, host materials, and excitons.

[0203] The second function of the linking portion of the atom X is to minimize spatial overlap of the HOMO or LUMO wave functions between the charge stabilizing moiety and the luminescent moiety. This is because if the wave functions overlap significantly due to the overlapping conjugated structures of the charge stabilizing moiety and the luminescent moiety, the emission wavelength of the luminescent moiety may shift to a longer wavelength or reduce the luminescence efficiency.

[0204] The connecting portion of the atom X may be formed by connecting the charge stabilizing portion and the light emitting portion via a spiro bond, or may be a connecting group. The connecting portion of the atom X is formed as a connecting group when Q or Z in Chemical Formula 1 is absent, resulting in no spiro bond being formed.

[0205] Specifically, the light emitting portion includes A in the chemical formula 1, Y 1 ~Y 5 The conjugated ring and Q are formed.

[0206] The light-emitting portion may be derived from a light-emitting material (referred to as a light-emitting compound in this specification) that can emit light by electron movement in an organic light-emitting diode.

[0207] The light-emitting compound (light-emitting material) may be a compound generally used as a dopant in an organic light-emitting diode. A dopant capable of achieving a desired color may be selected as the light-emitting compound according to the purpose, thereby inducing the light-emitting portion.

[0208] In one example, in Chemical Formula 2, M may be Rh, Ir, Pd, Pt, Ni, Rh, Co, or Au.

[0209] In one example, the A can be represented by the following Chemical Formula 3.

[0210] Chemical formula 3:

[0211]

[0212] In the chemical formula 3,

[0213] M is Pt,

[0214] V 1 、V 2and V 3 As defined in Chemical Formula 2,

[0215] s', p', q' and r' are 0 or 1 respectively,

[0216] m1, m2, m3 and m4 are integers from 1 to 5, respectively.

[0217] Y 21 To Y 44 are each independently B, N, C, O, P, Si, S, Ge or Se, and the ring containing the circle represented by the dotted line may not be a conjugated structure, or may have a partially or completely conjugated structure,

[0218] R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R 318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof,

[0219] R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324 At least two atoms connected to each other can be connected to form a ring,

[0220] The additional substituents are as defined in Chemical Formula 1.

[0221] In one example, the A can be represented by any one of the following Chemical Formulas 4 to 8.

[0222] Chemical formula 4:

[0223]

[0224] Chemical formula 5:

[0225]

[0226] Chemical formula 6:

[0227] Chemical formula 7:

[0228] Chemical formula 8:

[0229]

[0230] In the Chemical Formula 4 to the Chemical Formula 8,

[0231] M is Pt,

[0232] V 2 and V 3 Each independently does not exist, or is a single bond, -B(Ar 5 )-、-N(Ar 5 )-, -O-, -S- or -Se-, Ar 5each independently represents a C6-30 aryl group which may be substituted or unsubstituted by an additional substituent, a C2-30 heteroaryl group which may be substituted or unsubstituted by an additional substituent, a C1-30 alkyl group which may be substituted or unsubstituted by an additional substituent, a C3-30 cycloalkyl group which may be substituted or unsubstituted by an additional substituent, a C2-30 heterocycloalkyl group which may be substituted or unsubstituted by an additional substituent, a C3-30 cycloalkenyl group which may be substituted or unsubstituted by an additional substituent, or a C2-30 heterocycloalkenyl group which may be substituted or unsubstituted by an additional substituent,

[0233] m5, m6, m8, m10, m12, m13, m14, m18, m21, m22, and m24 are each an integer from 1 to 4,

[0234] m15, m16, m19 and m20 are integers from 1 to 5, respectively.

[0235] m7, m11 and m23 are integers from 1 to 7, respectively.

[0236] m9 and m17 are integers from 1 to 3 respectively,

[0237] Y 45 To Y 74 、Y 80 To Y 127 、Y 133 To Y 150 and Y 156 To Y 183 are each independently B, N or C,

[0238] Y 75 To Y 79 、Y 128 To Y 132 and Y 151 To Y 155 are each independently B, N, C, O, S, Se, Te, Si, Ge or Sn,

[0239] In Chemical Formula 5, Chemical Formula 7, and Chemical Formula 8, the ring including the circle indicated by the dotted line may not be a conjugated structure, or may have a partially or completely conjugated structure.

[0240] R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R 318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof,

[0241] R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324At least two atoms connected to each other can be connected to form a ring,

[0242] The additional substituents are as defined in Chemical Formula 1.

[0243] In one embodiment, A can be represented by any one of the following structural formulas A-1 to A-27:

[0244]

[0245]

[0246]

[0247] In the above A-1 to A-27,

[0248] Y is each independently B, N, C, O, P, Si, S, Ge or Se,

[0249] m is an integer from 0 to the maximum number that can be obtained according to the stoichiometric ratio,

[0250] R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof,

[0251] R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324 At least two atoms connected to each other can be connected to form a ring,

[0252] The additional substituents are as defined in Chemical Formula 1.

[0253] In A-1 to A-27, when at least two of the R"s are connected to each other to form a ring, such a ring includes a condensed ring. Furthermore, the case where two of the R"s are connected includes the case where either of the two R"s is hydrogen, and when the hydrogen is detached, the ring to which the hydrogen is connected is reduced to directly connect to the other R".

[0254] The light emission mechanism of the light emitting portion may include fluorescence emitting light from a singlet state, phosphorescence emitting light from a triplet state, and delayed fluorescence emitting light by energy transfer from a triplet state to a singlet state.

[0255] In one embodiment, the chemical formula 1 is any one of the chemical formulas represented by the following B-1 to B-28:

[0256]

[0257]

[0258] In said B-1 to B-28,

[0259] A and X are as defined in Chemical Formula 1,

[0260] Each X' linked by =X'- is independently =C(Ar 7 )-, =N- or =B-,

[0261] Each of the X's connected by -X'- is independently -O-, -S-, -Se-, -C(Ar 7 )(Ar 8 )-、-Si(Ar 7 )(Ar 8 ) or -N(Ar 7 )-,

[0262] In the definition of X', Ar 7 and Ar 8 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 7 and Ar 8 can be connected to each other to form a ring, or connected to adjacent rings to form a condensed ring,

[0263] R' may be present in an amount capable of being combined in a stoichiometric ratio, and each is independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 101 )(R 102 )、-C(R 103 )(R 104 )(R 105 )、-Si(R 106 )(R 107 )(R 108 )、-Ge(R 109 )(R 110 )(R 111 )、-N(R 112 )(R 113 )、-P(R 114)(R 115 )、-PO(R 116 )(R 117 )、-O(R 118 )、-S(R 119 )、-SO(R 120 )、-SO2(R 121 )、Se(R 122 )、-SeO(R 123 )、-SeO2(R 124 ) and combinations thereof,

[0264] R 101 to R 124 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 101 to R 124 At least two atoms connected to each other can be connected to form a ring,

[0265] The additional substituents are as defined in Chemical Formula 1.

[0266] In one embodiment, the complex luminescent compound may include at least one deuterium.

[0267] In one embodiment, the composite luminescent compound may be any one of the following compounds:

[0268]

[0269]

[0270]

[0271]

[0272] The charge-stabilizing moiety of the composite luminescent compound does not significantly affect the inherent luminescent properties of the luminescent moiety, while stabilizing the luminescent moiety at close range when charges are captured by the luminescent moiety and exist in an ionized or excited state. Furthermore, the charge-stabilizing moiety maintains a spatial position and angle that prevents chemical interaction with the luminescent moiety, while protecting specific portions of the luminescent moiety, thereby significantly reducing the probability of chemical and Coulombic interactions with other surrounding dopant substances, host substances, and excitons.

[0273] Based on the above reasons, the composite light-emitting compound can improve the light emission stability when driving the organic light-emitting diode device.

[0274] In one example, the light-emitting layer may include at least two composite light-emitting compounds.

[0275] The organic light-emitting diode may contain the composite light-emitting compound at a higher level than conventional dopant content. This means that the content of the light-emitting portion may be higher than the dopant content. For example, the content of the composite light-emitting compound in the light-emitting layer may be 0.1 to 100 mol% of the total material constituting the light-emitting layer. This content can be adjusted appropriately depending on the intended use.

[0276] In one example, the light-emitting layer may further include at least one selected from the group consisting of a host, an additional dopant, and a combination thereof.

[0277] The host may be a known substance, that is, a host substance that can generally form a light-emitting layer.

[0278] The additional dopant can be a known substance, namely, a luminescent substance or a dopant commonly added to the light-emitting layer as a luminescent substance. The additional dopant absorbs the luminescent energy of the light-emitting portion and re-emit it. Therefore, the maximum emission wavelength energy of the additional dopant may be lower than the maximum emission wavelength energy of the light-emitting portion. By using the additional dopant, low-energy luminescence can be achieved.

[0279] The maximum emission wavelength energy is the wavelength with the highest photon energy in the emission spectrum. The maximum emission wavelength is calculated from the onset value of the emission start position. The maximum emission wavelength is calculated from the wavelength with the highest emission intensity.

[0280] In the organic light emitting diode, the light emitting layer may further include phosphorescent materials to further improve the light emitting efficiency of the light emitting layer.

[0281] In one example, the light-emitting layer may further include a phosphorescent material containing Pt or Ir.

[0282] The compound represented by the following structural formula is an example of an organic metal complex generally used as a phosphorescent substance.

[0283]

[0284] In the formula, R can be C1-20 alkyl, C3-20 cycloalkyl, C2-20 heterocycloalkyl, C6-30 aryl, etc.

[0285] In the organic light emitting diode, the light emitting layer may further include a delayed fluorescent substance to further improve the light emitting efficiency of the light emitting layer.

[0286] In one embodiment, the light-emitting layer may further include a delayed fluorescent substance having an energy difference between a singlet state and a triplet state of 0.3 eV or more.

[0287] The compound represented by the following structural formula is an example of a commonly used delayed fluorescent substance.

[0288]

[0289] In the formula, Ar can be a C1-20 alkyl group, a C3-20 cycloalkyl group, a C2-20 heterocycloalkyl group, a C6-30 aryl group, etc.

[0290] 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 a combination thereof as the organic layer.

[0291] In one example, the organic light emitting diode may include an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and a cathode in sequence.

[0292] The organic light emitting diode may be a tandem organic light emitting diode including a plurality of organic light emitting units.

[0293] A plurality of organic light-emitting units may be stacked in sequence, and a charge generation layer (CGL) may be included between each organic light-emitting unit to distribute charges smoothly to the light-emitting layer of each organic light-emitting unit.

[0294] In the tandem organic light emitting diode, the organic light emitting unit may include an organic layer selected from the group consisting of a light emitting layer, 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 a combination thereof.

[0295] The tandem organic light emitting diode includes a light emitting layer, wherein at least one organic light emitting unit comprises the composite light emitting compound.

[0296] In the series-connected organic light-emitting diode, the detailed description of the composite light-emitting compound is as described above.

[0297] Synthesis example

[0298] Synthesis of comparative compound 1

[0299]

[0300] Under a nitrogen atmosphere, 7.00 g of comparative compound 1-1 (8.3 mmol), 3.72 g of dichloro(cycloocta-1,5-diene)platinum (II) (9.9 mmol) and 2.04 g of sodium acetate (24.8 mmol) were dissolved in 1,4-dioxane (83 ml), then heated to 115-120° C. and stirred for 16 hours.

[0301] The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The organic layer was extracted with dichloromethane, the solvent was dried over MgSO 4 , and the mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0302] Then, the product was purified by recrystallization using a DCM / hexane mixed solvent to obtain 2.21 g of the comparative compound 1 with a yield of 30%.

[0303] MS(ACPI)m / z:890[M+H]

[0304] NMR: δH (500MHz; CDCl3; Me4Si) 8.71 (d, J = 6.3Hz, 1H), 8.15 (d, J = 8.3Hz, 1H), 7.99-7.9 8(m,1H),7.82(d,J=8.3Hz,1H),7.60-7.58(m,1H),7.54(s,1H),7.51-7.47(m,3H),7. 43(d,J=8.38Hz,1H),7.36-7.33(m,2H),7.29-7.26(m,4H),7.09(d,J=8.1Hz,1H),7.0 1(t,J=7.7Hz,1H),5.52(d,J=3.2Hz,1H),1.50(br,9H),0.99(br,s.9H),0.82(s,9H).

[0305] Synthesis of compound 2

[0306]

[0307] The same procedure as above (Synthesis of Comparative Example Compound 1) was carried out except that Compound 2-1 was used instead of Comparative Example Compound 1-1 at the same molar ratio.

[0308] Finally, 2.04 g of compound 2 was obtained after purification, with a yield of 20%.

[0309] MS(ACPI)m / z:1231[M+H]

[0310] NMR: δH (500MHz; CDCl3; Me4Si) 8.95-8.93 (1H, d, J = 7.78Hz), 8.78-8.77 (1H, d, J = 5.95Hz) ,8.69(1H,s),8.28-8.26(1H,d,J=8.23Hz),8.22-8.20(1H,d,J=8.23Hz),8.12-8.10(1H,d ,J=7.55Hz),7.70-7.33(15H,m),7.25-7.21(2H,m),7.02-6.98(3H,m),6.88-6.85(2H,m), 6.74-6.72(1H,d,J=8.00),6.67-6.63(2H,d),3.48(3H,s),1.55(9H,s),1.01(18H,br.s).

[0311] Synthesis of compound 3

[0312]

[0313] The same procedure as above (Synthesis of Comparative Example Compound 1) was carried out except that Compound 3-1 was used instead of Comparative Example Compound 1-1 at the same molar ratio.

[0314] Finally, 1.86 g of comparative example compound 3 was obtained after purification, with a yield of 20%.

[0315] MS(ACPI)m / z:1125[M+H]

[0316] NMR: δH (500MHz; CDCl3; Me4Si) 9.40-9.38 (1H, d, J = 6.18Hz), 8.93-8.91 (1H, d, J = 7.78Hz), 8. 17-8.15(3H,d,J=7.78Hz),8.00-7.96(2H,m),7.70-7.68(1H,d,J=8.23Hz),7.51-7.37(9H,m) ,7.32-7.28(2H,m),7.19-7.15(2H,m),7.12-7.08(2H,m),7.05(2H,s),6.94-6.92(2H,m),6. 88-6.92(2H,t,J=7.55Hz,7.55Hz),6.76-6.73(2H,m),3.91(3H,s),1.51(9H,s),1.26(9H,s).

[0317] Synthesis of compound 4

[0318]

[0319]

[0320] The same procedure as above (Synthesis of Comparative Example Compound 1) was carried out except that Compound 4-1 was used instead of Comparative Example Compound 1-1 at the same molar ratio.

[0321] Finally, 2.24 g of comparative example compound 4 was obtained after purification, with a yield of 21%.

[0322] MS(ACPI)m / z:1293[M+H]

[0323] NMR: δH (500MHz; CDCl3; Me4Si) 8.97-8.95 (1H, d, J = 7.55Hz), 8.82-8.81 (1H, d, J = 6.40Hz), 8.27-8.25 (1H,d,J=8.23Hz),8.17-8.16(3H,d,J=5.72Hz),7.98-7.96(1H,d,J=7.55Hz),7.70(1H,s),7.59-7.3 8(17H,m),7.32-7.28(3H,d,J=8.00Hz),7.24-7.22(1H,d,J=6.63Hz),7.13-7.10(3H,t,J=7.32Hz),6 .92-6.91(1H,m),6.87-6.83(1H,t,J=7.66Hz,7.66Hz),6.77-6.75(2H,d),1.55(9H,s),0.98(18H,s).

[0324] Device Examples

[0325] The ITO surface was treated with UV ozone for 3 minutes under normal pressure.

[0326] The device was processed in a 10-7 Torr vacuum chamber according to the following sequence.

[0327]

[0328] Device 1 (Comparative Example 1)

[0329] As a hole injection material, PEDOT:PSS was spin coated at 4000 rpm for 1 minute and then heated at 120°C for 10 minutes. As a light-emitting layer, 0.0046 g of comparative compound 1 and 0.0154 g of compound A were dissolved in 2 ml of toluene, spin coated at 1000 rpm for 1 minute, and then heated at 60°C for 10 minutes under vacuum. Compound B and LiQ were deposited in a ratio of 1:1 as an electron transport layer to a thickness of Deposit Al as electrode to a thickness of

[0330] Device 2 (Example 1)

[0331] The device was prepared in the same manner as device 1, except that the light-emitting layer of device 1 was doped with compound 2 (20 mol %).

[0332] The following devices are at 10mA / cm 2 The doping mol% that exhibits the maximum luminescence efficiency is measured under the conditions of .

[0333] Table 1

[0334]

[0335] As can be seen from the table above, the devices using the present invention exhibit high efficiency. The difference between Compound 1 and Compound 2 lies in whether they contain a carbazole unit. The advantage of the charge stabilizing unit mentioned in the present invention is that it has the excellent property of improving the luminescence stability of the luminescent material. Compound 2, by including a carbazole unit containing a non-shared electron pair, improves the luminescence stability of the luminescent material and exhibits higher efficiency. By minimizing the concentration quenching phenomenon between the luminescent units, it can be judged that it exhibits a deeper blue characteristic under the CIE y value of the CIE standard color coordinate system.

[0336] While the present invention has been described with reference to the exemplary drawings, the present invention is not limited to the embodiments and drawings disclosed in this specification. It is apparent that those skilled in the art may make various modifications within the scope of the technical concept of the present invention. Furthermore, although the effects of the configurations of the present invention are not explicitly described when describing the embodiments of the present invention, the effects that can be anticipated from such configurations should be recognized.

Claims

1. An organic light emitting diode, characterized in that: comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, The light-emitting layer includes a composite light-emitting compound represented by the following chemical formula 1: The composite light-emitting compound comprises a light-emitting portion and a charge stabilizing portion, wherein the light-emitting portion and the charge stabilizing portion are connected via an atom X, wherein the atom X is X shown in the following chemical formula 1: The light emitting portion comprises A in the following chemical formula 1, 1 ~Y 5 The conjugated ring and Q, The charge stabilizing portion comprises the following chemical formula 1: 6 ~Y 10 The ring composed of Y 11 ~Y 15 The ring and Z, The charge stabilizing moiety comprises at least one atom having an unshared electron pair, Chemical formula 1: In the chemical formula 1, A is a structure represented by the following chemical formula 2, and is connected through the first connection position in A, or through the first connection position and the second connection position in A, X is C, Si, Ge, Sn or Pb, the first connecting position in A is connected to X, Q does not exist, or is a single bond, -B(Ar 1 )-、-C(Ar 1 )(Ar 2 )-、-Si(Ar 1 )(Ar 2 )-、-Ge(Ar 1 )(Ar 2 )-、-N(Ar 1 )-、-P(Ar 1 )-、-PO(Ar 1 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 1 and Ar 2 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 1 and Ar 2 can be connected to each other to form a ring, or by respectively with Y 2 , and Y 2 The connected R or A are connected to form a fused ring, When Q is absent, A is not directly connected to Y at the second connection position in A. 1 connect, When Q is a single bond, A is connected to Y at the second connecting position in A through a single bond. 1 connect, When Q is not a single bond and is present as any one of the above definitions, A is linked to Q at the second linking position in A, When Q is not a single bond and exists as any one of the above definitions, Q is respectively connected to A and Y through a single bond. 1 connect, Y 1 To Y 15 are each independently boron, carbon, nitrogen, oxygen, sulfur, Se or Te, Z does not exist, or is a single bond, -B(Ar 3 )-、-C(Ar 3 )(Ar 4 )-、-Si(Ar 3 )(Ar 4 )-、-Ge(Ar 3 )(Ar 4 )-、-N(Ar 3 )-、-P(Ar 4 )-、-PO(Ar 3 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 3 and Ar 4 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 3 and Ar 4 can be connected to each other to form a ring, or by respectively with Y 7 、Y 12 , and Y 7 Connect R or Y 12 Any of the connected R's are connected to form a condensed ring, When Z does not exist, Y 6 Not directly with Y 11 connect, When Z is a single bond, Y 6 By single bond with Y 11 connect, When Z is not a single bond and exists as any one of the above definitions, Z is respectively connected to Y by a single bond. 6 and Y 11 connect, m, n and o are each independently an integer from 0 to 5, R is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 101 )(R 102 )、-C(R 103 )(R 104 )(R 105 )、-Si(R 106 )(R 107 )(R 108 )、-Ge(R 109 )(R 110 )(R 111 )、-N(R 112 )(R 113 )、-P(R 114 )(R 115 )、-PO(R 116 )(R 117 )、-O(R 118 )、-S(R 119 )、-SO(R 120 )、-SO2(R 121 )、Se(R 122 )、-SeO(R 123 )、-SeO2(R 124 ) and combinations thereof, R 101 to R 124 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 101 to R 124 At least two atoms connected to each other can be connected to form a ring, When m, n or o is 2 or more, at least two R present can be linked 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. The condition is that Y 6 To Y 15 and at least one atom in Z is an atom containing an unshared electron pair, or R in combination thereof contains at least one atom containing an unshared electron pair, Chemical formula 2: In the chemical formula 2, M is a transition metal, V 1 、V 2 、V 3 and V 4 Each independently does not exist, or is a single bond, -B(Ar 5 )-、-C(Ar 5 )(Ar 6 )-、-Si(Ar 5 )(Ar 6 )-、-Ge(Ar 5 )(Ar 6 )-、-N(Ar 5 )-、-P(Ar 5 )-、-PO(Ar 5 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 5 and Ar 6 Can connect to each other to form a ring, or connect to adjacent E 1 、E 2 、E 3 or E 4 Connected to form a fused ring, The condition is that V 1 、V 2 、V 3 and V 4 At least one of is a single bond, When V 1 、V 2 、V 3 and V 4 When it does not exist, its adjacent E 1 、E 2 、E 3 and E 4 The two are not directly connected, When V 1 、V 2 、V 3 and V 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 and E 4 The two are directly connected by a single bond. When V 1 、V 2 、V 3 and V 4 When it is not a single bond and exists as any one of the above definitions, it can be adjacent to E 1 、E 2 、E 3 and E 4 The two of them are connected by a single bond, or the adjacent E 1 、E 2 、E 3 and E 4 The two connected bonds in the form a conjugated structure together. J 1 、J 2 、J 3 and J 4 are single bonds, O or S, respectively, When J 1 、J 2 、J 3 and J 4 When it is a single bond, the connected E 1 、E 2 、E 3 and E 4 Any one of them is directly bound to M through a coordination bond or a covalent bond, When J 1 、J 2 、J 3 and J 4 When it is O or S, the bond formed with M is a coordination bond or a covalent bond. E 1 、E 2 、E 3 and E 4 are each independently a monovalent, divalent or trivalent group and are defined as follows, provided that when E 1 、E 2 、E 3 and E 4 When V is a monovalent group, 1 、V 2 、V 3 and V 4 The two adjacent ones do not exist; when E 1 、E 2 、E 3 and E 4 When V is a divalent group, 1 、V 2 、V 3 and V 4 In which any of the two adjacent ones does not exist; when E 1 、E 2 、E 3 and E 4 When it is a trivalent group, V 1 、V 2 、V 3 and V 4 In which both adjacent ones exist, E 1 、E 2 、E 3 and E 4 each independently a monovalent group that is a halogen or cyano group, or a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C1-50 saturated or unsaturated aliphatic hydrocarbon that is substituted or unsubstituted with an additional substituent; a C5-50 aromatic carbocyclic ring that is substituted or unsubstituted with an additional substituent; a C2-50 aromatic heterocyclic ring that is substituted or unsubstituted with an additional substituent; a C3-50 saturated or unsaturated alicyclic carbocyclic ring that is substituted or unsubstituted with an additional substituent; or a C2-50 saturated or unsaturated alicyclic heterocyclic ring that is substituted or unsubstituted with an additional substituent, E 1 、E 2 、E 3 and E 4 At least two additional substituents contained therein can be linked to form a ring, The condition is that when J 1 、J 2 、J 3 or J 4 When it is a single bond, the adjacent E 1 、E 2 、E 3 or E 4 The atom at the position where it is connected to M is carbon, nitrogen, oxygen, sulfur or phosphorus; or, when J 1 、J 2 、J 3 or J 4 When it is O or S, its adjacent E 1 、E 2 、E 3 or E 4 With J 1 、J 2 、J 3 or J 4 The atom at the O or S bonding position is carbon; E 1 、E 2 、E 3 and E 4 Any one of the adjacent J 1 、J 2 、J 3 or J 4 The connection position and the adjacent V 1 、V 2 、V 3 or V 4 The connection positions are adjacent, E 1 、E 2 、E 3 and E 4 Any one of the adjacent V 1 、V 2 、V 3 and V 4 The connection positions of the two are different. In the chemical formula 2, in addition to M, atoms that can be bonded in a stoichiometric ratio can serve as the first bonding position or the second bonding position in A of the chemical formula 1, provided that the first bonding position and the second bonding position are each different from (i) E 1 、E 2 、E 3 and E 4 Any one of the adjacent J 1 、J 2 、J 3 、J 4 、V 1 、V 2 、V 3 or V 4 The connection position of V 1 、V 2 、V 3 and V 4 Any one of the adjacent E 1 、E 2 、E 3 or E 4 The connection location, The first connection position and the second connection position are adjacent to each other, The additional substituents can be present in an amount that can be combined in a stoichiometric ratio and are each independently selected from the group consisting of deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211 )、-N(R 212 )(R 213 )、-P(R 214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 Each is independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl or C2-30 heteroaryl.

2. The organic light emitting diode according to claim 1, wherein: M is Rh, Ir, Pd, Pt, Ni, Rh, Co or Au.

3. The organic light emitting diode according to claim 1, wherein The chemical formula 1 is any one of the chemical formulas represented by the following B-1 to B-28: In said B-1 to B-28, A and X are as defined in Chemical Formula 1, Each X' linked by =X'- is independently =C(Ar 7 )-, =N- or =B-, Each of the X's connected by -X'- is independently -O-, -S-, -Se-, -C(Ar 7 )(Ar 8 )-、-Si(Ar 7 )(Ar 8 ) or -N(Ar 7 )-, In the definition of X', Ar 7 and Ar 8 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 7 and Ar 8 can be connected to each other to form a ring, or connected to adjacent rings to form a condensed ring, R' can be present in an amount capable of being combined in a stoichiometric ratio, and each is independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 101 )(R 102 )、-C(R 103 )(R 104 )(R 105 )、-Si(R 106 )(R 107 )(R 108 )、-Ge(R 109 )(R 110 )(R 111 )、-N(R 112 )(R 113 )、-P(R 114 )(R 115 )、-PO(R 116 )(R 117 )、-O(R 118 )、-S(R 119 )、-SO(R 120 )、-SO2(R 121 )、Se(R 122 )、-SeO(R 123 )、-SeO2(R 124 ) and combinations thereof, R 101 to R 124 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 101 to R 124 At least two atoms connected to each other can be connected to form a ring, The additional substituents are as defined in Chemical Formula 1.

4. The organic light emitting diode according to claim 1, wherein The A is represented by the following chemical formula 3: Chemical formula 3: In the chemical formula 3, M is Pt, V 1 、V 2 and V 3 As defined in Chemical Formula 2, s', p', q' and r' are 0 or 1 respectively, m1, m2, m3 and m4 are integers from 1 to 5, respectively. Y 21 To Y 44 are each independently B, N, C, O, P, Si, S, Ge or Se, and the ring containing the circle represented by the dotted line may not be a conjugated structure, or may have a partially or completely conjugated structure, R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R 318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof, R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324 At least two atoms connected to each other can be connected to form a ring, The additional substituents are as defined in Chemical Formula 1.

5. The organic light emitting diode according to claim 1, wherein The A is represented by any one of the following chemical formulas 4 to 8: Chemical formula 4: Chemical formula 5: Chemical formula 6: Chemical formula 7: Chemical formula 8: In the Chemical Formula 4 to the Chemical Formula 8, M is Pt, V 2 and V 3 Each independently does not exist, or is a single bond, -B(Ar 5 )-、-N(Ar 5 )-, -O-, -S- or -Se-, Ar 5 each independently represents a C6-30 aryl group which may be substituted or unsubstituted by an additional substituent, a C2-30 heteroaryl group which may be substituted or unsubstituted by an additional substituent, a C1-30 alkyl group which may be substituted or unsubstituted by an additional substituent, a C3-30 cycloalkyl group which may be substituted or unsubstituted by an additional substituent, a C2-30 heterocycloalkyl group which may be substituted or unsubstituted by an additional substituent, a C3-30 cycloalkenyl group which may be substituted or unsubstituted by an additional substituent, or a C2-30 heterocycloalkenyl group which may be substituted or unsubstituted by an additional substituent, m5, m6, m8, m10, m12, m13, m14, m18, m21, m22, and m24 are each an integer from 1 to 4, m15, m16, m19 and m20 are integers from 1 to 5, respectively. m7, m11 and m23 are integers from 1 to 7, respectively. m9 and m17 are integers from 1 to 3 respectively, Y 45 To Y 74 、Y 80 To Y 127 、Y 133 To Y 150 and Y 156 To Y 183 are each independently B, N or C, Y 75 To Y 79 、Y 128 To Y 132 and Y 151 To Y 155 are each independently B, N, C, O, S, Se, Te, Si, Ge or Sn, In Chemical Formula 5, Chemical Formula 7, and Chemical Formula 8, the ring including the circle indicated by the dotted line may not be a conjugated structure, or may have a partially or completely conjugated structure. R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R 318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof, R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324 At least two atoms connected to each other can be connected to form a ring, The additional substituents are as defined in Chemical Formula 1.

6. The organic light emitting diode according to claim 1, wherein The A is represented by any one of the following structural formulas A-1 to A-27: In the above A-1 to A-27, Y is each independently B, N, C, O, P, Si, S, Ge or Se, m is an integer from 0 to the maximum number that can be obtained according to the stoichiometric ratio, R" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl substituted or unsubstituted with an additional substituent, C2-30 alkenyl substituted or unsubstituted with an additional substituent, C2-30 alkynyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkyl substituted or unsubstituted with an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted with an additional substituent, C1-30 heteroalkyl substituted or unsubstituted with an additional substituent, C2-30 heteroalkenyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted with an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted with an additional substituent, C3-30 allyl substituted or unsubstituted with an additional substituent, C6-30 aryl substituted or unsubstituted with an additional substituent, C2-30 heteroaryl substituted or unsubstituted with an additional substituent, -B(R 301 )(R 302 )、-C(R 303 )(R 304 )(R 305 )、-Si(R 306 )(R 307 )(R 308 )、-Ge(R 309 )(R 310 )(R 311 )、-N(R 312 )(R 313 )、-P(R 314 )(R 315 )、-PO(R 316 )(R 317 )、-O(R 318 )、-S(R 319 )、-SO(R 320 )、-SO2(R 321 )、Se(R 322 )、-SeO(R 323 )、-SeO2(R 324 ) and combinations thereof, R 301 to R 324 Each of them is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, and R 301 to R 324 At least two atoms connected to each other can be connected to form a ring, The additional substituents are as defined in Chemical Formula 1.

7. The organic light emitting diode according to claim 1, wherein: The Y 6 To Y 15 and Y 6 and Y 11 At least one atom of the attached Z is an atom having an unshared electron pair contained in the HOMO or LUMO wave function of the charge stabilizing moiety; or Y 6 To Y 15 At least one of them has R represented by the following chemical formula 9 or the following chemical formula 10, Chemical formula 9: Chemical formula 10: In the Chemical Formula 9 or Chemical Formula 10, L is a single bond, or a divalent group selected from the group consisting of C1-20 alkylene, C3-20 cycloalkylene, C3-20 cycloalkenylene, C1-20 heteroalkylene, C2-20 heterocycloalkylene, C2-20 heterocycloalkenylene, C2-20 alkenylene, -O-, -S-, -P(R 401 )-、-PO(R 402 )-, C6-20 arylene, C5-20 heteroarylene and combinations thereof, Ar 11 and Ar 12 Each is independently a C1-20 saturated or unsaturated aliphatic hydrocarbon substituted or unsubstituted with an additional substituent; a C1-20 saturated or unsaturated aliphatic hydrocarbon containing a heteroatom substituted or unsubstituted with an additional substituent; a C5-20 aromatic carbocyclic ring substituted or unsubstituted with an additional substituent; a C2-20 aromatic heterocyclic ring substituted or unsubstituted with an additional substituent; a C3-20 saturated or unsaturated alicyclic carbocyclic ring substituted or unsubstituted with an additional substituent; or a monovalent or divalent group of a C2-20 saturated or unsaturated alicyclic heterocyclic ring substituted or unsubstituted with an additional substituent, Z' does not exist, or is a single bond, -B(Ar 13 )-、-C(Ar 13 )(Ar 14 )-、-Si(Ar 13 )(Ar 14 )-、-Ge(Ar 13 )(Ar 14 )-、-N(Ar 13 )-、-P(Ar 13 )-、-PO(Ar 13 )-, -O-, -S-, -SO-, -SO2-, -Se-, -SeO-, -SeO2-, -CO-, -CS- or -CSe-, in which case Ar 13 and Ar 14 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkyl substituted or unsubstituted by an additional substituent, C3-30 cycloalkenyl substituted or unsubstituted by an additional substituent, C1-30 heteroalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkyl substituted or unsubstituted by an additional substituent, C2-30 heterocycloalkenyl substituted or unsubstituted by an additional substituent, C6-30 aryl substituted or unsubstituted by an additional substituent, or C2-30 heteroaryl substituted or unsubstituted by an additional substituent, Ar 13 and Ar 14 can be connected to each other to form a ring, or respectively with Ar 11 and Ar 12 Any one of them is connected to form a condensed ring, When Z' does not exist, Ar 11 and Ar 12 No direct connection, When Z' is a single bond, Ar 11 and Ar 12 Connect with one click. t is an integer from 0 to 5, v is 0 or 1, R'" is each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl, C1-30 heteroalkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 501 )(R 502 )、-C(R 503 )(R 504 )(R 505 )、-Si(R 506 )(R 507 )(R 508 )、-Ge(R 509 )(R 510 )(R 511 )、-N(R 512 )(R 513 )、-P(R 514 )(R 515 )、-PO(R 516 )(R 517 )、-O(R 518 )、-S(R 519 )、-SO(R 520 )、-SO2(R 521 )、Se(R 522 )、-SeO(R 523 )、-SeO2(R 524 ) and combinations thereof, in which case at least two of the R'" can be connected to each other to form a ring, R 401 to R 402 and R 501 to R 524 Each is independently hydrogen, deuterium, halogen, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C6-30 aryl or C2-30 heteroaryl, and R 401 to R 402 and R 501 to R 524 At least two atoms connected to each other can be connected to form a ring, Y is each independently nitrogen, oxygen, sulfur or carbon, Indicates the connection part, The additional substituents can be present in an amount that can be combined in a stoichiometric ratio and are each independently selected from the group consisting of deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 201 )(R 202 )、-C(R 203 )(R 204 )(R 205 )、Si(R 206 )(R 207 )(R 208 )、-Ge(R 209 )(R 210 )(R 211 )、-N(R 212 )(R 213 )、-P(R 214 )(R 215 )、-PO(R 216 )(R 217 )、-O(R 218 )、-S(R 219 )、-SO(R 220 )、-SO2(R 221 )、Se(R 222 )、-SeO(R 223 )、-SeO2(R 224 ) and their combinations, R 201 to R 224 are each independently hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 heterocycloalkenyl, C6-30 aryl or C2-30 heteroaryl, Provided that, in the Chemical Formula 10, L or R'" includes at least one atom having an unshared electron pair included in the HOMO or LUMO wave function of the charge stabilizing portion, or at least one of Y is nitrogen, oxygen, or sulfur.

8. The organic light emitting diode according to claim 1, wherein: At least one R is represented by any one of the following chemical formulas D-1 to D-38: In the chemical formulas D-1 to D-38, Y is each independently carbon or nitrogen, X'" are each independently oxygen, nitrogen, sulfur or selenium, R"" are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, -NO2, C1-30 alkyl, C3-30 cycloalkyl, C1-30 heteroalkyl, C2-30 heterocycloalkyl, C2-30 alkenyl, C3-30 cycloalkenyl, C2-30 heteroalkenyl, C2-30 alkynyl, C3-30 allyl, C6-30 aryl, C2-30 heteroaryl, -B(R 601 )(R 602 )、-C(R 603 )(R 604 )(R 605 )、-Si(R 606 )(R 607 )(R 608 )、-Ge(R 609 )(R 610 )(R 611 )、-N(R 612 )(R 613 )、-P(R 614 )(R 615 )、-PO(R 616 )(R 617 )、-O(R 618 )、-S(R 619 )、-SO(R 620 )、-SO2(R 621 )、Se(R 622 )、-SeO(R 623 )、-SeO2(R 624 ) and their combinations, R 601 to R 624 are each independently selected from hydrogen, deuterium, C1-30 alkyl, C3-30 cycloalkyl, C2-30 heterocycloalkyl, C6-30 aryl, C2-30 heteroaryl, and combinations thereof, u are each independently an integer from 0 to 20, Dashed lines indicate connection sites.

9. The organic light emitting diode according to claim 1, wherein: The complex luminescent compound comprises at least one deuterium.

10. The organic light emitting diode according to claim 1, wherein The composite luminescent compound represented by Chemical Formula 1 is any one of the following compounds:

11. The organic light emitting diode according to claim 1, wherein: The light-emitting layer comprises at least two of the composite light-emitting compounds.

12. The organic light emitting diode according to claim 1, wherein: The light emitting layer further comprises at least one selected from the group consisting of a host, an additional dopant, and a combination thereof.

13. The organic light emitting diode according to claim 1, wherein: The light-emitting layer further includes a phosphorescent material containing Ir or Pt.

14. The organic light emitting diode according to claim 1, wherein: The light-emitting layer further includes a delayed fluorescent substance having an energy difference between a singlet state and a triplet state of 0.3 eV or less.

15. The organic light emitting diode according to claim 1, wherein The organic light emitting diode is an organic light emitting diode comprising a plurality of organic light emitting units connected in series. At least one of the plurality of organic light emitting units includes the light emitting layer.

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