Novel light-emitting layer material and organic light-emitting diode comprising same

Abstract

The present invention relates to a novel light-emitting layer material and an organic light-emitting diode comprising same. More specifically, the present invention relates to: a novel complex light-emitting compound comprising, around a spiro structure, a moiety having light-emitting properties and a moiety having triplet energy transfer properties, thereby improving light-emitting performance; and an organic light-emitting diode providing high efficiency and long lifespan by using the material.

Description

Novel light-emitting layer material and organic light-emitting diode containing the same

[0001] The present invention relates to a novel light-emitting layer material and an organic light-emitting diode including the same. More specifically, the present invention relates to a novel composite light-emitting compound capable of improving light-emitting performance by being composed of a moiety having light-emitting characteristics centered on a spiro structure and a moiety having triplet energy transfer characteristics, and to an organic light-emitting diode that provides high efficiency and a long lifespan by introducing one or more host materials satisfying specific conditions into the light-emitting layer.

[0002] OLEDs (Organic Light Emitting Diodes) are devices in which holes injected from the anode and electrons injected from the cathode combine in the emissive layer through a charge transport layer to form excitons and emit light; they were first reported in 1987 by CW Tang in *Appl. Phys. Lett 51, 913*. At that time, the emissive layer consisted of a single material, Alq3. However, in 1989 in *J. Appl. Phys., Vol 65, 3610*, Alq3 was doped with small amounts of DCM as a red emissive compound and Coumarine 540 as a green emissive compound to adjust the emission wavelength and increase efficiency. Subsequently, in 1995 in *Nature, V 395, 151*, PtOEP was used as an emissive compound to convert triplet energy into light, and subsequently, phosphorescent green, red, and blue compounds based on Ir were developed to increase luminescence efficiency.

[0003] In particular, the inventors completed the present invention by focusing on the fact that when using composite luminescent compounds composed of a moiety having luminescent properties centered on a spiro structure and a moiety having triplet energy transfer properties, it is possible to obtain an organic light-emitting diode with increased luminescent efficiency or improved luminescent stability by improving the disadvantages of existing blue light-emitting materials.

[0004] The objective of the present invention is to provide an organic light-emitting diode that increases luminescence efficiency or improves luminescence stability by introducing a composite luminescent compound composed of a moiety having luminescence characteristics centered on a spiro structure and a moiety having triplet energy transfer characteristics, and one or more host materials satisfying specific conditions into the luminescent layer.

[0005] The objects of the present invention are not limited to those mentioned above, and other unmentioned objects and advantages of the present invention may be understood from the following description and will be more clearly understood by the embodiments of the present invention. Furthermore, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof set forth in the claims.

[0006] The novel light-emitting layer material compound of the present invention is characterized as a composite light-emitting compound comprising a light-emitting moiety and a triplet energy transfer moiety centered on a spiro structure.

[0007] In one embodiment of the present invention, an organic light-emitting diode comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, wherein

[0008] The above-mentioned light-emitting layer comprises a composite light-emitting compound in which a light-emitting moiety and a triplet energy transfer moiety are connected around a spiro structure, and one or more host materials.

[0009] When the triplet energy of the luminescence moiety of the above composite luminescent compound is denoted as E(T1EM), the triplet energy of the triplet energy transfer moiety as E(T1TR), and the triplet energy of the above host material as E(T1HOST), the following conditions are satisfied, and

[0010] E(T1EM) ≤ E(T1TR) ≤ E(T1HOST)

[0011] The above-described host material provides an organic light-emitting device characterized by being able to form a triplet energy transfer moiety and an exaplex.

[0012] In one embodiment of the present invention, when the above-described one or more host materials are a mixture of a p-type host material and an n-type host material, the HOMO energy of the p-type host material is denoted as E(HOMO-p) and the LUMO energy as E(LUMO-p), and the HOMO energy of the n-type host material is denoted as E(HOMO-n) and the LUMO energy as E(LUMO-n), and an organic light-emitting device is provided that satisfies the following conditions between the p-type host material and the n-type host material:

[0013] | E(HOMO-p)| ≤ |E(HOMO-n)| or |E(LUMO-p)| ≤ |E(LUMO-n)|

[0014] In one embodiment of the present invention, the light-emitting layer comprises a composite light-emitting compound having a p-type triplet energy transfer moiety and an n-type host material, and

[0015] If we denote the triplet energy of the p-type triplet energy transfer moiety as E(T1TR-p) and the triplet energy of the n-type host material as E(T1HOST-n),

[0016] An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-p) ≤ E(T1HOST-n) is provided.

[0017] In one embodiment of the present invention, the light-emitting layer comprises a composite light-emitting compound comprising an n-type triplet energy transfer moiety and a p-type host material, and

[0018] If we denote the triplet energy of the n-type triplet energy transfer moiety as E(T1TR-n) and the triplet energy of the p-type host material as E(T1HOST-p),

[0019] An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-n) ≤ E(T1HOST-p) is provided.

[0020] In one embodiment of the present invention, the organic light-emitting diode comprises a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, and

[0021] The above-mentioned light-emitting layer comprises a complex light-emitting compound represented by the following chemical formula 1, and

[0022] The above-mentioned complex luminescent compound comprises a luminescent moiety and a triplet energy transfer moiety, wherein the luminescent moiety and the triplet energy transfer moiety are connected by including an atom X, and the atom X is X as shown in Chemical Formula 1 below.

[0023] The above luminescent moiety is A, Y in the following chemical formula 1. 1 ~Y 5 It includes a conjugated ring formed including and Q, and

[0024] The above triplet energy transfer moiety is Y in the following Chemical Formula 1. 6 ~Y 10 A ring formed including, Y 11 ~Y 15 A ring formed including, including Z and X,

[0025] Provides an organic light-emitting diode:

[0026] <Chemical Formula 1>

[0027]

[0028] In the above chemical formula 1,

[0029] A is a structure represented by the following chemical formula 2, and is connected through a first connecting site in A, or is connected through a first connecting site and a second connecting site in A, and

[0030] X is C, Si, Ge, Sn, or Pb, and the first connection position among A is connected to X, and

[0031] Q 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- and, where, Ar 1 and Ar 2 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 1 and Ar 2 They are connected to each other to form a loop, or each Y 2 , Y 2 It can be connected to R or A connected to form a fusion ring, and

[0032] If Q is a single connection, A is Y at the second connection position among A. 1 Connected by a single bond,

[0033] If Q is not a single bond and exists as any one defined as above, A is connected to Q at the second connection location among A, and

[0034] If Q is not a single bond and exists as any one defined as above, then Q is A and Y 1 and are each connected by a single bond,

[0035] Y 1 to Y 15 are, each independently, boron, carbon, nitrogen, oxygen, sulfur, Se, or Te, and

[0036] Z does not exist, or 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- and, where, Ar 3 and Ar 4Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, an aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, and Ar 3 and Ar 4 They are connected to each other to form a loop, or each Y 7 , Y 12 , Y 7 R or Y connected to 12 It can form a fusion ring by connecting to any one of the Rs connected to it, and

[0037] If Z does not exist, Y 6 and Y 11 This is not directly connected,

[0038] If Z is a single bond, Y 6 and Y 11 It is connected by a single bond,

[0039] If Z is not a single bond and exists as any one defined as above, then Z is Y 6 and Y 11 and each are connected by a single bond,

[0040] m, n, and o are each independently integers from 0 to 5, and

[0041] R is, each independently, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent,

[0042] Allyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and

[0043] R 101 to R 124 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 101 to R 124 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0044] When m, n, or o is 2 or more, at least 2 Rs existing therein can be connected to each other to form a ring, and

[0045] p, q, and r each independently represent 0 or 1, and if p, q, or r is 0, it means that a 5-membered ring is formed, and if p, q, or r is 1, it means that a 6-membered ring is formed, and

[0046] <Chemical Formula 2>

[0047]

[0048] In the above chemical formula 2,

[0049] M is a transition metal, and

[0050] V 1 , V 2 , V 3 and V4 a, each independently, not existing, or 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- and, where, Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 5 and Ar 6 They are connected to each other to form a ring, or each adjacent E 1 , E 2 , E 3 or E 4 It can be connected to form a fusion ring, and

[0051] However, V 1 , V 2 , V 3 and V 4 At least one of them is a single bond, and

[0052] V 1 , V 2 , V 3 and V 4 If does not exist, the adjacent E 1 , E 2 , E 3 and E 4 Two of them are not directly connected,

[0053] V 1 , V 2 , V 3 and V 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 and E 4 Two of them are directly connected by a single bond, and V 1 , V 2 , V 3 and V 4 If is not a single bond and exists as any one defined as above, then the adjacent E 1 , E 2 , E 3 and E 4 Connected to each of the two of them by a single bond, or adjacent E 1 , E 2 , E 3 and E 4 Two bonds connected to two of them can form a conjugated structure together, and

[0054] J 1 , J 2 , J 3 and J 4 are a single bond, O or S, respectively, and

[0055] J 1 , J 2 , J 3 and J 4 If is a single bond, E connected thereto 1 , E 2 , E 3 and E 4 One of them is directly bonded to M via a coordinate bond or a covalent bond, and

[0056] J 1 , J 2 , J 3 and J 4 If is O or S, the bond with M is a coordinate bond or a covalent bond, and

[0057] E 1 , E 2 , E 3 and E 4 is defined as a monovalent, divalent, or trivalent group, each independently, as follows, provided that E 1 , E 2 , E 3 and E 4 If 1 is a factor, V 1 , V 2 , V 3 and V 4 Of these, neither of the two adjacent ones exists; E 1 , E 2 , E 3 and E 4 In the case where 2 is the basis, V 1 , V 2 , V 3 and V 4 Of the two adjacent ones, neither exists; E 1 , E 2 , E 3 and E 4 In the case where 3 is the same, V 1 , V 2 , V 3 and V 4 Among them, both adjacent two exist,

[0058] E 1 , E 2 , E 3 and E 4Each is independently a saturated or unsaturated aliphatic hydrocarbon having 1 to 50 carbon atoms, which is a monovalent group of halogen or cyano, or is substituted or not substituted with additional substituents; a saturated or unsaturated heteroatom-containing aliphatic hydrocarbon having 1 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic carbon ring having 5 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents; a saturated or unsaturated alicyclic carbon ring having 3 to 50 carbon atoms, which is substituted or not substituted with additional substituents; or a saturated or unsaturated alicyclic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents, and

[0059] E 1 , E 2 , E 3 and E 4 At least two additional substituents included in can be connected to form a ring, and

[0060] However, J 1 , J 2 , J 3 or J 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 or E 4 The atom at the connection position from to M is carbon, nitrogen, oxygen, sulfur, or phosphorus; or J 1 , J 2 , J 3 or J 4 If is O or S, then the adjacent E 1 , E 2 , E 3 or E 4 In J 1 , J 2 , J 3 or J 4 The atom at the connection position to O or S is carbon;

[0061] E 1, E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 or J 4 The connection location to the road and its adjacent V 1 , V 2 , V 3 or V 4 The connection locations of the roads are adjacent, and

[0062] E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent V 1 , V 2 , V 3 and V 4 The connection locations to the two of them are each different, and

[0063] The atom capable of bonding according to the stoichiometric ratio, excluding M in the above Chemical Formula 2, may be the first connecting position or the second connecting position in A of the above Chemical Formula 1, provided that the first connecting position and the second connecting position are each (i) E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 , J 4 , V 1 , V 2 , V 3 or V 4 It differs from the connection location of the road, and (ii) V 1 , V 2 , V 3 and V 4 In any one of them, the adjacent E 1 , E 2 , E 3 or E 4 Different from the connection location of the road,

[0064] The first connection location and the second connection location are adjacent, and

[0065] The above additional substituents may exist in a number capable of bonding according to stoichiometric ratios, and each independently deuterium, halogen, cyano, -NO2, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 30 carbon atoms, heteroalkenyl having 2 to 30 carbon atoms, heterocycloalkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, allyl having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, -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 Selected from the group consisting of ) and combinations thereof, and R 201 to R 224Each is independently hydrogen, deuterium, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, a heteroalkyl having 1 to 30 carbon atoms, a heterocycloalkyl having 2 to 30 carbon atoms, an alkenyl having 2 to 30 carbon atoms, a cycloalkenyl having 3 to 30 carbon atoms, a heteroalkenyl having 2 to 30 carbon atoms, a heterocycloalkenyl having 2 to 30 carbon atoms, an aryl having 6 to 30 carbon atoms, or a heteroaryl having 2 to 30 carbon atoms.

[0066] According to the present invention, an organic light-emitting diode is provided that increases luminous efficiency or improves luminous stability by introducing a composite luminescent compound composed of a moiety having luminescent properties centered on a spiro structure and a moiety having triplet energy transfer properties, and one or more host materials satisfying specific conditions into the luminescent layer.

[0067] Figures 1 and 2 are graphs showing the emission spectrum characteristics of a device according to the present invention.

[0068] The present invention is described in detail below so that those skilled in the art can easily implement it. The present invention may be embodied in various different forms and is not limited to the embodiments described herein.

[0069] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom in a compound is replaced by another substituent. The location where substitution occurs refers to the location where the hydrogen atom is substituted. The location is not limited to any location where the hydrogen at the location can be replaced by a substituent. If two or more substitutions occur, the two or more substituents may be the same or different.

[0070] Substituents referred to as "substituted" in this specification, unless otherwise noted, are, for example, hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a halogen, a cyano group, a carboxyl group, a carbonyl group, an amine group, an alkyl amine group having 1 to 20 carbon atoms, a nitro group, an alkyl silyl group having 1 to 20 carbon atoms, an alkoxysilyl group having 1 to 20 carbon atoms, a cycloalkylsilyl group having 3 to 30 carbon atoms, an aryl silyl group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryl amine group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an aryl phosphine oxide group having 6 to 30 carbon atoms, an aryl phosphinyl group having 6 to 30 carbon atoms, and a group having 6 to 30 carbon atoms. It may be one selected from the group consisting of alkylphosphine oxide, an alkylsulfonyl group having 6 to 30 carbon atoms, and combinations thereof, but is not limited thereto.

[0071] In the definitions of substituents in this specification, "combinations thereof" means that, unless otherwise defined, two or more substituents exist, or two or more divalent substituents are connected or condensed and combined.

[0072] In this specification, cases in which two substituents are connected to form a ring include cases where one of the two substituents is hydrogen and the connection is made as the hydrogen is removed.

[0073] In this specification, unless otherwise distinguished, "alkyl" includes straight chains or branched chains and, unless otherwise distinguished, collectively refers to "cycloalkyl and heterocycloalkyl." In this specification, unless otherwise distinguished, "alkenyl" includes straight chains or branched chains and, unless otherwise distinguished, collectively refers to "cycloalkenyl and heterocycloalkenyl." For example, unless otherwise distinguished, alkyl amines collectively refer to cycloalkyl amines and heterocycloalkyl amines.

[0074] In this specification, "heteroalkyl" or "heteroalkylene" refers to a case where at least one carbon atom among alkyl or alkylene is substituted with a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0075] In this specification, "heteroalkenyl" refers to an alkenyl in which at least one carbon atom not double-bonded is substituted with a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0076] In this specification, "heterocycloalkyl" refers to a case where at least one carbon atom among cycloalkyls is substituted with a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0077] In this specification, "heterocycloalkenyl" refers to a case in which at least one carbon atom not double-bonded among cycloalkenyls is substituted with a heteroatom, and the number of carbon atoms refers to the number of carbon atoms excluding the heteroatom.

[0078] In this specification, "hetero" means containing a heteroatom within a compound or substituent unless otherwise defined, and said heteroatom means an atom other than carbon and hydrogen, and may be, for example, N, O, Si, Ge, S, P, B, Se, Te, etc., but is not limited thereto; and if two or more heteroatoms are contained within a compound or substituent, they may contain the same or different heteroatoms, for example, one or two or more heteroatoms. For example, a heteroaryl or heterocycloalkyl contains at least one heteroatom as a ring-forming atom.

[0079] In this specification, "aryl," "arylene," or "aromatic" may be a monocyclic or polycyclic ring according to commonly known definitions and may include a conjugated structure in part or all of them. The polycyclic ring may be a fused ring or a linked form, and, for example, the aryl or aromatic carbon ring includes biphenyl.

[0080] Substituents other than those defined as above as substituents mentioned in this specification shall follow the known definitions of substituents.

[0081] In this specification, when substituents or connecting positions in a chemical formula are adjacent, it means that the atoms connected by the substituents or the atoms at the connecting positions are directly connected.

[0082] In this specification, unless otherwise noted, where the definition of a substituent includes cases where an additional substituent is substituted, the additional substituent belongs to the category of the defined substituent. For example, Z in Formula 1 is -N(Ar 1 )- and, Ar 1 In the case where the methyl as an additional substituent is substituted with phenyl, the methyl as an additional substituent belongs to Z. That is, the category of Z here includes the methyl as an additional substituent. Here, although Z has been described as an example, for all substituents defined in the formulas herein, if an additional substituent can be substituted, it should be understood that the additional substituent is included in the category of the defined substituent. As another example, the first or second linking position in A of Formula 1 may be located in an additional substituent defined within the category of A, and likewise, E in Formula 2 1 The connection location on the back is E 1 It can be located in additional substituents belonging to the category of.

[0083] In this specification, the number of additional substituents may exist as the number of bonds that can be formed according to the stoichiometric ratio unless otherwise noted.

[0084] In this specification, unless otherwise noted, a ring includes a fused ring.

[0085] In this specification, when two entities (substituents, etc.) are connected, one of them is hydrogen, and the connection is made while the hydrogen is dropped.

[0086] In this specification, dotted lines indicate that they may or may not be present.

[0087] In this specification, HOMO / LOMO energies were measured using cyclic voltammetry (CV) with the ionization energy based on Ferrocene (oxidation potential 4.8 eV) via differential pulse voltammetry (DPV). The LUMO energy level was obtained by measuring the UV absorption spectrum to determine the absorption edge onset, obtaining the band gap, and adding it to the HOMO level. The triplet energy was calculated based on the short-wavelength onset position of the PL spectrum measured under low-temperature conditions.

[0088] In one embodiment of the present invention, an organic light-emitting diode comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, wherein

[0089] The above-mentioned light-emitting layer comprises a composite light-emitting compound in which a light-emitting moiety and a triplet energy transfer moiety are connected around a spiro structure, and one or more host materials.

[0090] When the triplet energy of the luminescence moiety of the above composite luminescent compound is denoted as E(T1EM), the triplet energy of the triplet energy transfer moiety as E(T1TR), and the triplet energy of the above host material as E(T1HOST), the following conditions are satisfied, and

[0091] E(T1EM) ≤ E(T1TR) ≤ E(T1HOST)

[0092] The above-described host material provides an organic light-emitting device characterized by being able to form a triplet energy transfer moiety and an exaplex.

[0093] In one embodiment of the present invention, when the above-described one or more host materials are a mixture of a p-type host material and an n-type host material, the HOMO energy of the p-type host material is denoted as E(HOMO-p) and the LUMO energy as E(LUMO-p), and the HOMO energy of the n-type host material is denoted as E(HOMO-n) and the LUMO energy as E(LUMO-n), and an organic light-emitting device is provided that satisfies the following conditions between the p-type host material and the n-type host material:

[0094] | E(HOMO-p)| ≤ |E(HOMO-n)| or |E(LUMO-p)| ≤ |E(LUMO-n)|

[0095] In this specification, a p-type material or p-type host material is responsible for the primary transport or injection of holes within an organic electronic device, particularly an OLED device. The p-type material has a relatively high HOMO (Highest Occupied Molecular Orbital) energy level, effectively injecting or transporting holes from adjacent layers or electrodes, and has the characteristic that hole mobility is relatively dominant compared to electron transport. When adjacent to an emissive layer, it can contribute to the positional control of exciton recombination regions and charge balance regulation, and can be used as a hole transport component within the emissive layer.

[0096] For example, the above p-type substance can be represented by the following chemical formula.

[0097] <Chemical Formula 9>

[0098]

[0099] In the above chemical formula 9,

[0100] Each Ar may independently be a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and the two Ars may be connected to form a fused ring having 12 to 30 carbon atoms.

[0101] At least one hydrogen atom in the above chemical formula 9 is substituted with deuterium or is not substituted.

[0102] Below are examples of compounds used as p-type substances.

[0103]

[0104]

[0105]

[0106] In this specification, the terms n-type material or n-type host material refer to a material responsible for the primary transport or injection of electrons within an organic electronic device, particularly an OLED device. The n-type material possesses a relatively low LUMO (Lowest Unoccupied Molecular Orbital) energy level, allowing it to effectively receive or transport electrons from adjacent layers or electrodes, and exhibits characteristics in which electron mobility is relatively dominant compared to hole transport. It can be used as an electron transport component within the emissive layer and can perform the function of controlling electron-hole recombination efficiency and exciton density distribution within the emissive region. It is a structure in which nitrogen is primarily located within an aromatic ring.

[0107] For example, the above n-type material may be any one of the structures represented by the following chemical formula 10.

[0108] <Chemical Formula 10>

[0109]

[0110] In the above chemical formula 10,

[0111] X can be nitrogen or carbon, and

[0112] n and m are integers from 0 to 6, provided that if X is nitrogen, n+m is an integer from 1 to 3, and if X is carbon, n+m is an integer from 1 to 6, and

[0113] Each Ar may independently be a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, a substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms including phosphine or phosphine oxide, and the two Ars may be connected to form a fused ring having 12 to 30 carbon atoms.

[0114] At least one hydrogen atom in the above chemical formula 10 is substituted with deuterium or is not substituted.

[0115] Below are examples of compounds used as n-type materials.

[0116]

[0117]

[0118]

[0119] In one embodiment of the present invention, the light-emitting layer comprises a composite light-emitting compound having a p-type triplet energy transfer moiety and an n-type host material, and

[0120] If we denote the triplet energy of the p-type triplet energy transfer moiety as E(T1TR-p) and the triplet energy of the n-type host material as E(T1HOST-n),

[0121] An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-p) ≤ E(T1HOST-n) is provided.

[0122] In one embodiment of the present invention, the light-emitting layer comprises a composite light-emitting compound comprising an n-type triplet energy transfer moiety and a p-type host material, and

[0123] If we denote the triplet energy of the n-type triplet energy transfer moiety as E(T1TR-n) and the triplet energy of the p-type host material as E(T1HOST-p),

[0124] An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-n) ≤ E(T1HOST-p) is provided.

[0125] In one embodiment of the present invention:

[0126] An organic light-emitting diode comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, and

[0127] The above-mentioned light-emitting layer comprises a complex light-emitting compound represented by the following chemical formula 1, and

[0128] The above-mentioned complex luminescent compound comprises a luminescent moiety and a triplet energy transfer moiety, wherein the luminescent moiety and the triplet energy transfer moiety are connected by including an atom X, and the atom X is X as shown in Chemical Formula 1 below.

[0129] The above luminescent moiety is A, Y in the following chemical formula 1. 1 ~Y 5 It includes a conjugated ring formed including and Q, and

[0130] The above triplet energy transfer moiety is Y in the following Chemical Formula 1. 6 ~Y 10 A ring formed including, Y 11 ~Y 15 A ring formed including, including Z and X,

[0131] Provides an organic light-emitting diode:

[0132] <Chemical Formula 1>

[0133]

[0134] In the above chemical formula 1,

[0135] A is a structure represented by the following chemical formula 2, and is connected through a first connecting site in A, or is connected through a first connecting site and a second connecting site in A, and

[0136] X is C, Si, Ge, Sn, or Pb, and the first connection position among A is connected to X, and

[0137] Q 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- and, where, Ar 1 and Ar 2Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 1 and Ar 2 They are connected to each other to form a loop, or each Y 2 , Y 2 It can be connected to R or A connected to form a fusion ring, and

[0138] If Q is a single connection, A is Y at the second connection position among A. 1 Connected by a single bond,

[0139] If Q is not a single bond and exists as any one defined as above, A is connected to Q at the second connection location among A, and

[0140] If Q is not a single bond and exists as any one defined as above, then Q is A and Y 1 and are each connected by a single bond,

[0141] Y 1 to Y 15 are, each independently, boron, carbon, nitrogen, oxygen, sulfur, Se, or Te, and

[0142] Z does not exist, or 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- and, where, Ar 3 and Ar 4 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, an aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, and Ar 3 and Ar 4 They are connected to each other to form a loop, or each Y 7 , Y 12 , Y 7 R or Y connected to 12 It can form a fusion ring by connecting to any one of the Rs connected to it, and

[0143] If Z does not exist, Y 6 and Y 11 This is not directly connected,

[0144] If Z is a single bond, Y 6 and Y 11 It is connected by a single bond,

[0145] If Z is not a single bond and exists as any one defined as above, then Z is Y 6 and Y 11 and each are connected by a single bond,

[0146] m, n, and o are each independently integers from 0 to 5, and

[0147] R is, each independently, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent,

[0148] Allyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, -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 )(R115 ), -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 At least one selected from the group consisting of ) and combinations thereof, and

[0149] R 101 to R 124 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 101 to R 124 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0150] When m, n, or o is 2 or more, at least 2 Rs existing therein can be connected to each other to form a ring, and

[0151] p, q, and r each independently represent 0 or 1, and if p, q, or r is 0, it means that a 5-membered ring is formed, and if p, q, or r is 1, it means that a 6-membered ring is formed, and

[0152] <Chemical Formula 2>

[0153]

[0154] In the above chemical formula 2,

[0155] M is a transition metal, and

[0156] V 1 , V 2 , V 3 and V 4 a, each independently, not existing, or 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- and, where, Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 5 and Ar 6 They are connected to each other to form a ring, or each adjacent E 1 , E 2 , E 3or E 4 It can be connected to form a fusion ring, and

[0157] However, V 1 , V 2 , V 3 and V 4 At least one of them is a single bond, and

[0158] V 1 , V 2 , V 3 and V 4 If does not exist, the adjacent E 1 , E 2 , E 3 and E 4 Two of them are not directly connected,

[0159] V 1 , V 2 , V 3 and V 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 and E 4 Two of them are directly connected by a single bond, and V 1 , V 2 , V 3 and V 4 If is not a single bond and exists as any one defined as above, then the adjacent E 1 , E 2 , E 3 and E 4 Connected to each of the two of them by a single bond, or adjacent E 1 , E 2 , E 3 and E 4 Two bonds connected to two of them can form a conjugated structure together, and

[0160] J 1 , J 2 , J 3 and J 4 are a single bond, O or S, respectively, and

[0161] J 1 , J 2, J 3 and J 4 If is a single bond, E connected thereto 1 , E 2 , E 3 and E 4 One of them is directly bonded to M via a coordinate bond or a covalent bond, and

[0162] J 1 , J 2 , J 3 and J 4 If is O or S, the bond with M is a coordinate bond or a covalent bond, and

[0163] E 1 , E 2 , E 3 and E 4 is defined as a monovalent, divalent, or trivalent group, each independently, as follows, provided that E 1 , E 2 , E 3 and E 4 If 1 is a factor, V 1 , V 2 , V 3 and V 4 Of these, neither of the two adjacent ones exists; E 1 , E 2 , E 3 and E 4 In the case where 2 is the basis, V 1 , V 2 , V 3 and V 4 Of the two adjacent ones, neither exists; E 1 , E 2 , E 3 and E 4 In the case where 3 is the same, V 1 , V 2 , V 3 and V 4 Among them, both adjacent two exist,

[0164] E 1 , E 2 , E 3 and E 4Each is independently a saturated or unsaturated aliphatic hydrocarbon having 1 to 50 carbon atoms, which is a monovalent group of halogen or cyano, or is substituted or not substituted with additional substituents; a saturated or unsaturated heteroatom-containing aliphatic hydrocarbon having 1 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic carbon ring having 5 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents; a saturated or unsaturated alicyclic carbon ring having 3 to 50 carbon atoms, which is substituted or not substituted with additional substituents; or a saturated or unsaturated alicyclic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents, and

[0165] E 1 , E 2 , E 3 and E 4 At least two additional substituents included in can be connected to form a ring, and

[0166] However, J 1 , J 2 , J 3 or J 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 or E 4 The atom at the connection position from to M is carbon, nitrogen, oxygen, sulfur, or phosphorus; or J 1 , J 2 , J 3 or J 4 If is O or S, then the adjacent E 1 , E 2 , E 3 or E 4 In J 1 , J 2 , J 3 or J 4 The atom at the connection position to O or S is carbon;

[0167] E 1, E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 or J 4 The connection location to the road and its adjacent V 1 , V 2 , V 3 or V 4 The connection locations of the roads are adjacent, and

[0168] E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent V 1 , V 2 , V 3 and V 4 The connection locations to the two of them are each different, and

[0169] The atom capable of bonding according to the stoichiometric ratio, excluding M in the above Chemical Formula 2, may be the first connecting position or the second connecting position in A of the above Chemical Formula 1, provided that the first connecting position and the second connecting position are each (i) E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 , J 4 , V 1 , V 2 , V 3 or V 4 It differs from the connection location of the road, and (ii) V 1 , V 2 , V 3 and V 4 In any one of them, the adjacent E 1 , E 2 , E 3 or E 4 Different from the connection location of the road,

[0170] The first connection location and the second connection location are adjacent, and

[0171] The above additional substituents may exist in a number capable of bonding according to stoichiometric ratios, and each independently deuterium, halogen, cyano, -NO2, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 30 carbon atoms, heteroalkenyl having 2 to 30 carbon atoms, heterocycloalkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, allyl having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, -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 Selected from the group consisting of ) and combinations thereof, and R 201 to R 224Each is independently hydrogen, deuterium, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, a heteroalkyl having 1 to 30 carbon atoms, a heterocycloalkyl having 2 to 30 carbon atoms, an alkenyl having 2 to 30 carbon atoms, a cycloalkenyl having 3 to 30 carbon atoms, a heteroalkenyl having 2 to 30 carbon atoms, a heterocycloalkenyl having 2 to 30 carbon atoms, an aryl having 6 to 30 carbon atoms, or a heteroaryl having 2 to 30 carbon atoms.

[0172] In the definition of Chemical Formula 1 above, Ar in Q is not hydrogen and deuterium. 1 or Ar 2 Ga Y 2 or Y 2 In the case where it is connected to R connected to form a fusion ring, Y 2 The R connected to is hydrogen, and as that hydrogen R is dropped, Ar 1 or Ar 2 Ga Y 2 Includes cases where it is connected to.

[0173] In the definition of Chemical Formula 1 above, Ar in Z 3 or Ar 4 Ga Y 7 , Y 12 , Y 7 R or Y connected to 12 In the case where it forms a fusion ring by connecting to any one of the Rs connected to it, Y 7 R or Y connected to 12 The R connected to is hydrogen, and as that hydrogen R is dropped, Ar 3 or Ar 4 Ga Y 7 or Y 12 Includes cases where it is connected to.

[0174] In the case where at least two Rs in Chemical Formula 1 are connected to form a ring, such a ring includes a fused ring. Additionally, in the case where two Rs are connected, either of the two connected Rs is hydrogen, and as that hydrogen R is removed, the connected Y is formed by the removal of that hydrogen R.1 to Y 15 Includes cases where one of the other two Rs is directly connected to either of them.

[0175] In the above chemical formula 2, E 1 , E 2 , E 3 and E 4 If at least two additional substituents included in are connected to form a ring, such a ring includes a fused ring. The two additional substituents forming such a ring are E 1 , E 2 , E 3 and E 4 It may be an additional substituent connected to either one or two of them. Additionally, the case where two additional substituents are connected includes the case where one of the two connected is a hydrogen and the connection is made while the hydrogen is dropped.

[0176] In the definition of Chemical Formula 2 above, E 1 , E 2 , E 3 and E 4 Middle J 1 , J 2 , J 3 , J 4 Or the atom at the connection position connected by M is E 1 , E 2 , E 3 and E 4 It may be an aliphatic hydrocarbon defined for, a heteroatom-containing aliphatic hydrocarbon, an aromatic carbon ring, an aromatic hetero ring, a cycloaliphatic carbon ring or a cycloaliphatic hetero ring, or an atom contained in an additional substituent connected thereto.

[0177] In one embodiment of the present invention, the light-emitting layer of an organic light-emitting diode according to the present invention comprises a composite light-emitting compound and at least one host material. The host material of the light-emitting layer may be composed of a p-type host material, an n-type host material, or a mixture of a p-type host material and an n-type host material.

[0178] A p-type host material is a material in which, for example, when atoms such as nitrogen connect aromatic rings, the non-covalent electrons of nitrogen provide electrons through a resonance effect with the pi electrons of the aromatic rings, thereby relatively raising the HOMO energy level and making the hole mobility higher than the electron mobility.

[0179] n-type host materials refer to materials that facilitate electron movement rather than hole movement by relatively lowering the LUMO energy level and increasing electronegativity due to the property of pulling electrons through sigma bonds, such as when atoms like nitrogen participate as members forming an aromatic ring to form a hetero-fused ring.

[0180] When the aforementioned p-type host material and n-type host material are mixed together, let the HOMO energy of the p-type host material be denoted as E(HOMO-p) and the LUMO energy as E(LUMO-p), and the HOMO energy of the n-type host material be denoted as E(HOMO-n) and the LUMO energy as E(LUMO-n). Then, the following correlation exists between the p-type host material and the n-type host material.

[0181] | E(HOMO-p)| ≤ |E(HOMO-n)| or |E(LUMO-p)| ≤ |E(LUMO-n)|

[0182] In addition, when the triplet energy of the luminescence moiety of the composite luminescent compound used in the organic light-emitting diode according to the present invention is denoted as E(T1EM), the triplet energy of the triplet energy transfer moiety as E(T1TR), and the triplet energy of the host material as E(T1HOST), the following characteristics must be satisfied:

[0183] E(T1EM) ≤ E(T1TR) ≤ E(T1HOST)

[0184] In particular, when the component constituting the light-emitting layer of the organic light-emitting diode according to the present invention is a mixture of two or more p-type host materials and n-type host materials, each material can form an exaplex, and if the triplet energy of the exaplex is denoted as E(T1EX), the following conditions must be satisfied:

[0185] E(T1EM) ≤ E(T1TR) ≤ E(T1EX)

[0186] When these conditions are satisfied, the triplet energy generated in the host is transferred directly to the luminescence moiety of the complex luminescent compound or to the triplet energy transfer moiety. At this time, the energy transferred to the triplet energy transfer moiety is transferred again to the luminescence moiety, and as a result, luminescence occurs in the luminescence moiety.

[0187] The triplet energy transfer moiety can be selected from a p-type host material or an n-type host material. For example, if a composite luminescent compound contains a p-type triplet energy transfer moiety and forms an emissive layer together with an n-type host material, the exaplex is formed right next to the luminescent compound unit. In this case, if the triplet energy of the p-type triplet energy transfer moiety is denoted as E(T1TR-p) and the triplet energy of the n-type host material is denoted as E(T1HOST-n), the following conditions must be satisfied:

[0188] E(T1EM) ≤ E(T1TR-p) ≤ E(T1HOST-n).

[0189] In addition, when a composite luminescent compound contains an n-type triplet energy transfer moiety and forms an emissive layer together with a p-type host material, the exaplex is formed right next to the luminescent compound unit; in this case, if the triplet energy of the n-type triplet energy transfer moiety is denoted as E(T1TR-n) and the triplet energy of the p-type host material is denoted as E(T1HOST-p), the following conditions must be satisfied:

[0190] E(T1EM) ≤ E(T1TR-n) ≤ E(T1HOST-p).

[0191] When the above conditions are satisfied, all triplet energy formed in the emissive layer is transferred to the emissive moiety, thereby maintaining stable luminescence characteristics. In particular, since the triplet energy transfer moiety transfers energy while maintaining a constant distance from the emissive moiety through spiro-coupling, it not only provides three-dimensional protection to the emissive moiety but also reduces concentration quenching between the emissive moiety and efficiently transfers triplet energy, thereby contributing to the stabilization of luminescence characteristics.

[0192] The process of energy transfer from the host to the dopant is explained by the light-based method (FRET, Fφrster Resonance Energy transfer) of Equation 1 below and the electron-based method (Dexter Electron Transfer) of Equation 2 below.

[0193] FRET (Frster Resonance Energy transfer)

[0194] [Mathematical Formula 1]

[0195]

[0196] Dexter Electron Transfer

[0197] [Mathematical Formula 2]

[0198]

[0199] kET : Rate constant

[0200] r: Distance between the energy donor and the energy acceptor

[0201] τ D : PL decay time of energy donor

[0202] κ : Orientation factor

[0203] Q D : PL quantum efficiency of energy donors

[0204] N A Avogadro's number

[0205] n: refractive index

[0206] J : Defined by the following mathematical formula 3.

[0207] [Mathematical Formula 3]

[0208]

[0209] f D : Emission spectrum of energy donor

[0210] ε A Absorption coefficient according to the wavelength of the energy receiver

[0211] L: the sum of Van der Waals radii

[0212] λ: Wavelength

[0213] As shown in the equation above, as the distance between the energy donor and the energy acceptor approaches zero, the energy transfer efficiency converges to infinity. Therefore, the energy transfer efficiency can be maximized by making the distance between the luminescent moiety and the triplet energy transfer moiety very close through spiro coupling.

[0214] Specifically, in the luminescent compound of the present invention represented by the above chemical formula 1, the luminescent moiety described above is A, Y in the following chemical formula 1. 1 ~Y 5The triplet energy transfer moiety of the present invention comprises a conjugated ring formed including and Q, wherein Y in the following Chemical Formula 1 6 ~Y 10 Conjugated ring formed including, Y 11 ~Y 15 It includes a conjugated ring formed including and Z, which form a spiro bond through the X atom.

[0215] More specifically, the luminescent moiety described above is A and Y in Chemical Formula 1. 1 ~Y 5 It includes a conjugated ring formed including and Q.

[0216] The above-mentioned luminescent moiety can be derived from a luminescent material (referred to as a luminescent compound in this specification) capable of emitting light by the movement of electrons in an organic light-emitting diode.

[0217] The above-mentioned luminescent compound (luminescent material) may be a compound that can typically be used as a dopant in an organic light-emitting diode. A dopant capable of realizing a desired color can be selected as the luminescent compound according to the purpose, and the above-mentioned luminescent moiety can be induced therefrom.

[0218] In one embodiment, M in the above formula 2 may be Rh, Ir, Pd, Pt, Ni, Rh, Co, or Au.

[0219] In one embodiment, the above A can be represented by the following chemical formula 3.

[0220] <Chemical Formula 3>

[0221]

[0222] In the above chemical formula 3,

[0223] M is Pt, and

[0224] V 1 , V 2 and V 3 is defined identically to that in Chemical Formula 2 above, and

[0225] s', p', q', and r' are 0 or 1, respectively, and

[0226] m1, m2, m3, and m4 are each integers from 1 to 5, and

[0227] Y 21 to Y 44 Each is independently B, N, C, O, P, Si, S, Ge, or Se, and the ring containing the circle indicated by the dotted line is not a conjugated structure, or may have a partially or wholly conjugated structure, and

[0228] R" is, respectively, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and a group having 3 to 30-carbon allyl, 6 to 30-carbon aryl substituted or unsubstituted with additional substituents, 2 to 30-carbon heteroaryl substituted or unsubstituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and

[0229] R 301 to R 324 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 301 to R 324 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0230] The above additional substituent is defined in the same way as in Chemical Formula 1.

[0231] In one embodiment, the above A may be represented by any one of the following chemical formulas 4 to 8.

[0232] <Chemical Formula 4>

[0233]

[0234] <Chemical Formula 5>

[0235]

[0236]

[0237]

[0238]

[0239]

[0240] <Chemical Formula 6>

[0241]

[0242] <Chemical Formula 7>

[0243]

[0244] <Chemical Formula 8>

[0245]

[0246] In the above chemical formulas 4 to 8,

[0247] M is Pt, and

[0248] V 2 and V 3 is, each independently, does not exist, a single bond, -B(Ar 5 )-, -N(Ar 5 )-, -O-, -S- or -Se- and, Ar 5Each is independently an aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, an alkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, or a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents.

[0249] m5, m6, m8, m10, m12, m13, m14, m18, m21, m22, and m24 are each integers from 1 to 4, and

[0250] m15, m16, m19, and m20 are each integers from 1 to 5, and

[0251] m7, m11, and m23 are integers from 1 to 7, respectively, and

[0252] m9 and m17 are integers from 1 to 3, respectively, and

[0253] Y 45 to Y 74 , Y 80 to Y 127 , Y 133 to Y 150 and Y 156 to Y 183 Each is independently B, N, or C, and

[0254] Y 75 to Y 79 , Y 128 to Y 132 and Y 151 to Y 155 are, respectively, B, N, C, O, S, Se, Te, Si, Ge, or Sn, and

[0255] The ring containing the circle indicated by the dotted line in Chemical Formulas 5, 7, and 8 is not a conjugated structure, or may have a partially or wholly conjugated structure, and

[0256] R" is, respectively, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and a group having 3 to 30-carbon allyl, 6 to 30-carbon aryl substituted or unsubstituted with additional substituents, 2 to 30-carbon heteroaryl substituted or unsubstituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and

[0257] R 301 to R 324 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 301 to R 324 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0258] The above additional substituent is defined in the same way as in Chemical Formula 1.

[0259] In one embodiment, A may be represented by any one of the following structural formulas A-1 to A-27.

[0260]

[0261]

[0262]

[0263]

[0264] In the above A-1 to A-27,

[0265] Y is, each independently, B, N, C, O, P, Si, S, Ge, or Se, and

[0266] m is an integer ranging from 0 to the maximum number that can be taken according to the stoichiometric ratio, and

[0267] R" is, respectively, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl group having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl group having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl group having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and a group having 3 to 30-carbon allyl, 6 to 30-carbon aryl substituted or unsubstituted with additional substituents, 2 to 30-carbon heteroaryl substituted or unsubstituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and

[0268] R 301 to R 324 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 301 to R 324 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0269] The above additional substituent is defined in the same way as in Chemical Formula 1.

[0270] In the above A-1 to A-27, when at least two of the R" are connected to each other to form a ring, such a ring includes a fused ring. Additionally, the case where two of the R" are connected includes a case where one of the two R" is hydrogen, and as the hydrogen is removed, the other R" is directly connected through the reduction of the ring connected to the hydrogen.

[0271] In one embodiment, the above chemical formula 1 may be any one of the chemical formulas represented by B-1 to B-28 below.

[0272]

[0273]

[0274] In the above B-1 to B-28,

[0275] A and X are defined as in Chemical Formula 1 above, and

[0276] X' are, respectively, -B-, -O-, -S-, -Se-, -C(Ar 7 )(Ar 8 )-, -Si(Ar 7 )(Ar 8 ) or -N(Ar 7 )-and, Ar 7 and Ar 8 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 7 and Ar 8 They can be connected to each other to form a ring, or each can be connected to an adjacent ring to form a fused ring, and

[0277] R' may exist in the number of bonds possible according to the stoichiometric ratio, and each independently hydrogen, deuterium, halogen, cyano, -NO2, alkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, alkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, alkynyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, heteroalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, additional Allyl having 3 to 30 carbon atoms substituted or unsubstituted with substituents, aryl having 6 to 30 carbon atoms substituted or unsubstituted with additional substituents, heteroaryl having 2 to 30 carbon atoms substituted or unsubstituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and

[0278] R 101 to R 124 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 101 to R 124 At least two atoms connected to one of the atoms can be connected to form a ring, and

[0279] The above additional substituent is defined in the same way as in Chemical Formula 1.

[0280] In one embodiment, the luminescent compound may include at least one deuterium.

[0281] In one embodiment, the light-emitting layer may include at least two types of the light-emitting compound.

[0282] The above organic light-emitting diode may contain the light-emitting compound at a level greater than the usual dopant content. This means that the content of the light-emitting moiety may be greater than the dopant content level. The content of the light-emitting compound in the light-emitting layer may have a range of, for example, 0.1 to 100 mol% among the total materials constituting the light-emitting layer, and the content may be appropriately adjusted according to the application.

[0283] In one embodiment, the light-emitting layer may further include at least one selected from the group consisting of a host, additional dopants, and combinations thereof.

[0284] The above host may be a material generally known as a host material capable of forming a light-emitting layer.

[0285] The additional dopant mentioned above may be a material known as a luminescent material or a material generally known as a dopant doped as a luminescent material into the luminescent layer. The additional dopant may serve to absorb the luminescence energy of the luminescent moiety and re-luminize it. Therefore, the maximum luminescence wavelength energy of the additional dopant may be smaller than the maximum luminescence wavelength energy of the luminescent moiety. Low-energy luminescence can be obtained through the use of the additional dopant.

[0286] The peak emission wavelength energy refers to the wavelength in the emission spectrum where the photon energy is greatest. The peak emission wavelength is obtained from the onset value at the position where emission begins.

[0287] The above organic light-emitting diode may include, as the organic layer, one selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and combinations thereof.

[0288] In one embodiment, the organic light-emitting diode may sequentially 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.

[0289] The above organic light-emitting diode may be a tandem type organic light-emitting diode comprising a plurality of organic light-emitting units.

[0290] Multiple organic light-emitting units can be stacked sequentially, and a charge generation layer (CGL) may be included between each organic light-emitting unit. The charge generation layer is located between the organic light-emitting units to facilitate the smooth distribution of charge to the light-emitting layer of each organic light-emitting unit.

[0291] In the above tandem type 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.

[0292] The above tandem type organic light-emitting diode comprises at least one organic light-emitting unit including a light-emitting layer containing the light-emitting compound.

[0293] In the above tandem organic light-emitting diode, the detailed description of the light-emitting compound is as described above.

[0294] It is obvious that various modifications can be made by a person skilled in the art within the scope of the technical concept of the present invention. Furthermore, even if the effects of the configuration according to the present invention were not explicitly described while describing the embodiments of the present invention above, it is natural that the effects predictable by said configuration should also be acknowledged.

[0295] [Synthetic Example]

[0296] Synthesis of Comparative Compound 1

[0297]

[0298] Comparative Compound 1-1 Comparative Compound (BD-02)

[0299] Comparative compound 1-1 7.00 g (8.8 mmol), dichloro(cycloocta-1,5-diene)platinum(II) 3.72 g (9.9 mmol), sodium acetate 2.04 g (24.8 mmol) and 1,4-dioxane (83 ml) were dissolved under a nitrogen atmosphere, then the temperature was raised to 115–120°C and stirred for 16 hours.

[0300] The reaction solution was cooled to room temperature and concentrated under reduced pressure. The solvent of the organic layer extracted with dichloromethane was dried with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified using silica gel column chromatography (DCM / Hexane).

[0301] Afterwards, the above comparative compound 1 was recrystallized and purified with a DCM / Hexane mixed solvent to obtain 2.21 g of the compound in a 20% yield.

[0302] MS(ACPI) m / z: 890[M+H]

[0303] NMR: δH (500 MHz; CDCl3; Me4Si) 8.71 (d, J = 6.3 Hz, 1H), 8.15 (d, J = 8.3 Hz, 1H), 7.99-7.98 (m, 1H), 7.82 (d, J = 8.3 Hz, 1H), 7.60-7.58 (m, 1H), 7.54 (s, 1H), 7.51-7.47 (m, 3H), 7.43 (d, J = 8.38 Hz, 1H), 7.36-7.33 (m, 2H), 7.29-7.26 (m, 4H), 7.09 (d, J = 8.1 Hz, 1H), 7.01 (t, J = 7.7 Hz, 1H), 5.52 (d, J = 3.2 Hz, 1H), 1.50 (br, 9H), 0.99 (br, s. 9H), 0.82 (s, 9H)

[0304] Synthesis of Compound 2

[0305]

[0306] Compound 2-1 Compound 2

[0307] The process was carried out in the same manner, except that Compound 2-1 was used instead of Comparative Example Compound 1-1 in the same molar ratio as in the above (synthesis of Comparative Example Compound 1).

[0308] After final purification, 1.93 g of compound 2 was obtained in a 17% yield.

[0309] MS(ACPI) m / z: 1294[M+H]

[0310] Synthesis of Compound 3

[0311]

[0312] Compound 3-1 Compound 3

[0313] The process was carried out in the same manner, except that Compound 3-1 was used instead of Comparative Example Compound 1-1 in the same molar ratio as in the above (synthesis of Comparative Example Compound 1).

[0314] After final purification, 1.70g of compound 3 was obtained in a 15% yield.

[0315] MS(ACPI) m / z: 1294[M+H]

[0316] Synthesis of Compound 4

[0317]

[0318] Compound 4-1 Compound 4

[0319] The process was carried out in the same manner, except that Compound 4-1 was used instead of Comparative Example Compound 1-1 in the same molar ratio as in the above (synthesis of Comparative Example Compound 1).

[0320] After final purification, 2.33g of compound 4 was obtained in a 20% yield.

[0321] MS(ACPI) m / z: 1218[M+H]

[0322] [Sojaye]

[0323] The ITO surface was treated with UV Ozone for 3 minutes at atmospheric pressure.

[0324] 10 -7The device was processed in the following order in a torr vacuum chamber.

[0325]

[0326]

[0327] The triplet energy values ​​of each material are shown below.

[0328] The triplet energy was obtained based on the onset value of the emission wavelength in THF solvent.

[0329] Material Triplet Energy Compound C3.02 Compound 1 Luminescent Unit 2.85 Compound 2 Luminescent Unit 2.84 Compound 3 Luminescent Unit 2.84 Compound 4 Luminescent Unit 2.84 Compound E2.80 Compound F2.90 Compound G2.95

[0330] Device 1 (Comparative Example 1) HATCN was deposited to a thickness of 50 Å as a hole injection material.

[0331] Compound A was deposited as a hole-moving material to a thickness of 1200 Å.

[0332] Compound B was deposited as an electron blocking layer to a thickness of 50 Å.

[0333] Compound C was doped with Comparative Compound 1 at 10 mol% to form a light-emitting layer with a thickness of 400 Å.

[0334] Compound C was deposited as a hole blocking layer to a thickness of 50 Å.

[0335] Compound D and LiQ were deposited as an electron transfer layer in a 1:1 ratio to a thickness of 300 Å.

[0336] LiQ was deposited as an electron injection layer with a thickness of 15 Å.

[0337] 500 Å of Al was deposited as an electrode.

[0338] Device 2 (Example 1)

[0339] The device was fabricated in the same manner as device 1, except that compound 2 was doped into the light-emitting layer of device 1 at 10 mol%.

[0340] Device 3 (Example 2)

[0341] The device was fabricated in the same manner as device 1, except that compound 3 was doped into the light-emitting layer of device 1 at 10 mol%.

[0342] Device 4 (Example 3)

[0343] The device was fabricated in the same manner as device 1, except that compound 4 was doped into the light-emitting layer of device 1 at 10 mol%.

[0344] Measurements were taken at 500 nits for each of the following elements.

[0345] Device (10mA / cm²) 2 )Dopant Doping mol%EQE(%)CIE xCIE yλmax Comparative Example 1 Device 1 Comparative Compound 11013.440.1550.182460 Example 1 Device 2 Compound 21011.860.1460.139460 Example 2 Device 3 Compound 31014.320.1450.136460 Example 3 Device 4 Compound 41014.670.1440.133460

[0346] As can be seen from the table above, the device utilizing the present invention exhibits high efficiency characteristics. Although the present invention has been described above with reference to the illustrated drawings, the present invention is not limited by the embodiments and drawings disclosed in this specification, and it is obvious that various modifications can be made by a person skilled in the art within the scope of the technical concept of the present invention. Furthermore, even if the effects of the configuration according to the present invention were not explicitly described while explaining the embodiments of the present invention above, it is natural to acknowledge that the effects predictable by said configuration should also be recognized.

Claims

An organic light-emitting diode comprising a first electrode, a second electrode, and a light-emitting layer located between the first electrode and the second electrode, The above-mentioned light-emitting layer comprises a composite light-emitting compound in which a light-emitting moiety and a triplet energy transfer moiety are connected around a spiro structure, and one or more host materials. When the triplet energy of the luminescence moiety of the above composite luminescent compound is denoted as E(T1EM), the triplet energy of the triplet energy transfer moiety as E(T1TR), and the triplet energy of the above host material as E(T1HOST), the following conditions are satisfied, and E(T1EM) ≤ E(T1TR) ≤ E(T1HOST) An organic light-emitting device characterized in that the above-described host material can form a triplet energy transfer moiety and an exaplex. In claim 1, where the above one or more host materials are a mixture of a p-type host material and an n-type host material, let the HOMO energy of the p-type host material be denoted as E(HOMO-p) and the LUMO energy as E(LUMO-p), and the HOMO energy of the n-type host material be denoted as E(HOMO-n) and the LUMO energy as E(LUMO-n), and between the p-type host material and the n-type host material, an organic light-emitting device satisfying the following conditions: | E(HOMO-p)| ≤ |E(HOMO-n)| or |E(LUMO-p)| ≤ |E(LUMO-n)|. In claim 1, the light-emitting layer comprises a composite light-emitting compound including a p-type triplet energy transfer moiety and an n-type host material, and If we denote the triplet energy of the p-type triplet energy transfer moiety as E(T1TR-p) and the triplet energy of the n-type host material as E(T1HOST-n), An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-p) ≤ E(T1HOST-n). In claim 1, the light-emitting layer comprises a composite light-emitting compound including an n-type triplet energy transfer moiety and a p-type host material, and If we denote the triplet energy of the n-type triplet energy transfer moiety as E(T1TR-n) and the triplet energy of the p-type host material as E(T1HOST-p), An organic light-emitting device satisfying the condition E(T1EM) ≤ E(T1TR-n) ≤ E(T1HOST-p). An organic light-emitting device according to claim 1, wherein the light-emitting layer comprises a complex light-emitting compound represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, A is a structure represented by the following chemical formula 2, and is connected through a first connecting site in A, or is connected through a first connecting site and a second connecting site in A, and X is C, Si, Ge, Sn, or Pb, and the first connection position among A is connected to X, and Q 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- and, where, Ar 1 and Ar 2 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 1 and Ar 2 They are connected to each other to form a loop, or each Y 2 , Y 2 It can be connected to R or A connected to form a fusion ring, and If Q is a single connection, A is Y at the second connection position among A. 1 Connected by a single bond, If Q is not a single bond and exists as any one defined as above, A is connected to Q at the second connection location among A, and If Q is not a single bond and exists as any one defined as above, then Q is A and Y 1 and are each connected by a single bond, Y 1 to Y 15 are, each independently, boron, carbon, nitrogen, oxygen, sulfur, Se, or Te, and Z does not exist, or 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- and, where, Ar 3 and Ar 4 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, an aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, and Ar 3 and Ar 4 They are connected to each other to form a loop, or each Y 7 , Y 12 , Y 7 R or Y connected to 12 It can form a fusion ring by connecting to any one of the Rs connected to it, and If Z does not exist, Y 6 and Y 11 This is not directly connected, If Z is a single bond, Y 6 and Y 11 It is connected by a single bond, If Z is not a single bond and exists as any one defined as above, then Z is Y 6 and Y 11 and each are connected by a single bond, m, n, and o are each independently integers from 0 to 5, and R is, each independently, hydrogen, deuterium, halogen, cyano, -NO2, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an alkynyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, Allyl having 3 to 30 carbon atoms substituted or not substituted with additional substituents, aryl having 6 to 30 carbon atoms substituted or not substituted with additional substituents, heteroaryl having 2 to 30 carbon atoms substituted or not substituted with additional substituents, -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 At least one selected from the group consisting of ) and combinations thereof, and R 101 to R 124 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and R 101 to R 124 At least two atoms connected to one of the atoms can be connected to form a ring, and When m, n, or o is 2 or more, at least 2 Rs existing therein can be connected to each other to form a ring, and p, q, and r each independently represent 0 or 1, and if p, q, or r is 0, it means that a 5-membered ring is formed, and if p, q, or r is 1, it means that a 6-membered ring is formed, and <Chemical Formula 2> In the above chemical formula 2, M is a transition metal, and V 1 , V 2 , V 3 and V 4 a, each independently, not existing, or 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- and, where, Ar 5 and Ar 6 Each is independently hydrogen, deuterium, halogen, an alkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a cycloalkenyl having 3 to 30 carbon atoms substituted or not substituted with an additional substituent, a heteroalkyl having 1 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, a heterocycloalkenyl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, an aryl having 6 to 30 carbon atoms substituted or not substituted with an additional substituent, or a heteroaryl having 2 to 30 carbon atoms substituted or not substituted with an additional substituent, and Ar 5 and Ar 6 They are connected to each other to form a ring, or each adjacent E 1 , E 2 , E 3 or E 4 It can be connected to form a fusion ring, and However, V 1 , V 2 , V 3 and V 4 At least one of them is a single bond, and V 1 , V 2 , V 3 and V 4 If does not exist, the adjacent E 1 , E 2 , E 3 and E 4 Two of them are not directly connected, V 1 , V 2 , V 3 and V 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 and E 4 Two of them are directly connected by a single bond, and V 1 , V 2 , V 3 and V 4 If is not a single bond and exists as any one defined as above, then the adjacent E 1 , E 2 , E 3 and E 4 Connected to each of the two of them by a single bond, or adjacent E 1 , E 2 , E 3 and E 4 Two bonds connected to two of them can form a conjugated structure together, and J 1 , J 2 , J 3 and J 4 are a single bond, O or S, respectively, and J 1 , J 2 , J 3 and J 4 If is a single bond, E connected thereto 1 , E 2 , E 3 and E 4 One of them is directly bonded to M via a coordinate bond or a covalent bond, and J 1 , J 2 , J 3 and J 4 If is O or S, the bond with M is a coordinate bond or a covalent bond, and E 1 , E 2 , E 3 and E 4 is defined as a monovalent, divalent, or trivalent group, each independently, as follows, provided that E 1 , E 2 , E 3 and E 4 If 1 is a factor, V 1 , V 2 , V 3 and V 4 Of these, neither of the two adjacent ones exists; E 1 , E 2 , E 3 and E 4 In the case where 2 is the basis, V 1 , V 2 , V 3 and V 4 Of the two adjacent ones, neither exists; E 1 , E 2 , E 3 and E 4 In the case where 3 is the same, V 1 , V 2 , V 3 and V 4 Among them, both adjacent two exist, E 1 , E 2 , E 3 and E 4 Each is independently a saturated or unsaturated aliphatic hydrocarbon having 1 to 50 carbon atoms, which is a monovalent group of halogen or cyano, or is substituted or not substituted with additional substituents; a saturated or unsaturated heteroatom-containing aliphatic hydrocarbon having 1 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic carbon ring having 5 to 50 carbon atoms, which is substituted or not substituted with additional substituents; an aromatic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents; a saturated or unsaturated alicyclic carbon ring having 3 to 50 carbon atoms, which is substituted or not substituted with additional substituents; or a saturated or unsaturated alicyclic heterocyclic ring having 2 to 50 carbon atoms, which is substituted or not substituted with additional substituents, and E 1 , E 2 , E 3 and E 4 At least two additional substituents included in can be connected to form a ring, and However, J 1 , J 2 , J 3 or J 4 If is a single bond, then the adjacent E 1 , E 2 , E 3 or E 4 The atom at the connection position from to M is carbon, nitrogen, oxygen, sulfur, or phosphorus; or J 1 , J 2 , J 3 or J 4 If is O or S, then the adjacent E 1 , E 2 , E 3 or E 4 In J 1 , J 2 , J 3 or J 4 The atom at the connection position to O or S is carbon; E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 or J 4 The connection location to the road and its adjacent V 1 , V 2 , V 3 or V 4 The connection locations of the roads are adjacent, and E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent V 1 , V 2 , V 3 and V 4 The connection locations to the two of them are each different, and The atom capable of bonding according to the stoichiometric ratio, excluding M in the above Chemical Formula 2, may be the first connecting position or the second connecting position in A of the above Chemical Formula 1, provided that the first connecting position and the second connecting position are each (i) E 1 , E 2 , E 3 and E 4 In any one of them, the adjacent J 1 , J 2 , J 3 , J 4 , V 1 , V 2 , V 3 or V 4 It differs from the connection location of the road, and (ii) V 1 , V 2 , V 3 and V 4 In any one of them, the adjacent E 1 , E 2 , E 3 or E 4 Different from the connection location of the road, The first connection location and the second connection location are adjacent, and The above additional substituents may exist in a number capable of bonding according to stoichiometric ratios, and each independently deuterium, halogen, cyano, -NO2, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, heteroalkyl having 1 to 30 carbon atoms, heterocycloalkyl having 2 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 30 carbon atoms, heteroalkenyl having 2 to 30 carbon atoms, heterocycloalkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 30 carbon atoms, allyl having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, -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 Selected from the group consisting of ) and combinations thereof, and R 201 to R 224 Each is independently hydrogen, deuterium, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, a heteroalkyl having 1 to 30 carbon atoms, a heterocycloalkyl having 2 to 30 carbon atoms, an alkenyl having 2 to 30 carbon atoms, a cycloalkenyl having 3 to 30 carbon atoms, a heteroalkenyl having 2 to 30 carbon atoms, a heterocycloalkenyl having 2 to 30 carbon atoms, an aryl having 6 to 30 carbon atoms, or a heteroaryl having 2 to 30 carbon atoms.

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