KR102148870B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light-emitting compound represented by the following [Chemical Formula 1] and an organic light-emitting device comprising the same, wherein the organic light-emitting compound according to the present invention has excellent luminous efficiency and lifespan characteristics of a material, thus exhibiting excellent luminous efficiency and It is possible to manufacture an organic light emitting device having power efficiency and long life characteristics.
[Formula 1]

Description

An electroluminescent compound and an electroluminescent device comprising the same}

The present invention relates to an organic light emitting compound and an organic electroluminescent device including the same.

Recently, organic light emitting devices capable of low voltage driving by self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays, which are the mainstream of flat panel display devices, do not require a backlight, are lightweight and thin, and are advantageous in terms of power consumption and color reproduction. Due to its wide range, it is drawing attention as a next-generation display device.

The organic electroluminescent device is a device that emits light while electrons and holes form a pair and then disappear when electric charges are injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode).

The organic light emitting device can be formed on a transparent substrate that can bend like plastic, and can be driven at a voltage lower than 10 V compared to a plasma display panel or an inorganic light emitting display, and consumes relatively little power. , It has the advantage of excellent color. In addition, the organic electroluminescent device can display three colors of green, blue, and red, and thus has attracted much attention as a next-generation rich color display device.

The most important factor determining the luminous efficiency in an organic light emitting device is a light emitting material. Currently, a fluorescent material is widely used as a light emitting material, but the development of a phosphorescent material is one of the methods that can theoretically improve luminous efficiency more due to the light emitting mechanism, and accordingly, various phosphorescent materials have been developed up to now. In particular, as a phosphorescent host material, CBP is the most widely known until now, and an organic electroluminescent device using a BALq derivative as a host is known.

However, organic electroluminescent devices using phosphorescent materials have significantly higher current efficiency than devices using fluorescent materials, but when materials such as BAlq and CBP are used as the host of phosphorescent materials, they are driven compared to devices using fluorescent materials. Since the voltage is high, there is no great advantage in terms of power efficiency, and the lifespan of the device is not satisfactory, and thus, development of a more stable and high-performance host material is required.

Accordingly, the problem to be solved by the present invention is to solve the above problem, and to provide an organic light-emitting compound having superior luminous efficiency and improved power efficiency and long lifespan than conventional materials.

In addition, the present invention is to provide a high-efficiency and long-life organic electroluminescent device by employing the organic light emitting compound as a light emitting material.

In order to solve the above problems, the present invention provides an organic light-emitting compound represented by the following [Chemical Formula 1], and comprises at least one organic light-emitting compound as the organic light-emitting compound. Provides a thin layer.

[Formula 1]

The definition of each substituent or skeleton atom will be described later.

In addition, the present invention provides an organic thin film layer for an organic electroluminescent device including at least one or more organic electroluminescent compounds represented by [Chemical Formula 1] and an organic electroluminescent device including the same.

The organic light-emitting compound according to the present invention has excellent luminous efficiency and lifespan characteristics of a material, so that it is possible to manufacture an organic electroluminescent device having excellent luminous efficiency and power efficiency and long lifespan characteristics.

1 is a schematic diagram of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

One aspect of the present invention relates to an organic light emitting compound represented by the following [Chemical Formula 1].

[Formula 1]

In the above [Formula 1],

X is a single bond or CR ₃ R ₄ , NR ₅ , O, S and SiR ₆ R ₇ It is any one selected from among.

L is a single bond or a substituted or unsubstituted C 1 to C 30 alkylene group, a substituted or unsubstituted C 2 to C 30 alkenylene group, a substituted or unsubstituted C 2 to C 30 alkynylene group, substituted or unsubstituted Is a linking group selected from a cycloalkylene group having 3 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and n is an integer of 0 to 3 , When n is 2 or more, a plurality of L may be the same or different from each other.

Ar is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms.

A represents a pentagonal ring or a hexagonal ring including Se represented by the following [Structural Formula A-1] or [Structural Formula A-2].

[Structural Formula A-1] [Structural Formula A-2]

R ₁ To R ₇ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted 1 to carbon number 20 alkylamino group, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, substituted or unsubstituted Arylalkylamino group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amidino group, hydrazine, hydra It is selected from the group consisting of a zone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen.

a and b are integers of 1 to 4, and when a and b are 2 or more, a plurality of R ₁ And R ₂ are the same as or different from each other, and L, R ₁ to R ₇ and Ar may be bonded to each other or with an adjacent substituent to form a saturated or unsaturated ring.

In addition, the'substituted' in the'substituted or unsubstituted' is Ar, L and R ₁ To R ₇ And the like are each substituted with one or more substituents, wherein the at least one substituent is an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, and 3 to 50 carbon atoms. Heteroaryl group, C 1 to C 30 alkoxy group, C 6 to C 30 aryloxy group, C 1 to C 20 alkylamino group, C 6 to C 30 arylamino group, substituted or unsubstituted C 1 to C 20 alkylsilyl Group, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted 2 carbon atoms To 50 alkynyl group, hydroxyl group, nitro group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms , A cyano group, a halogen group, and deuterium.

According to a preferred embodiment of the present invention, [Chemical Formula 1] may be selected from compounds represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-11].

[Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6] [Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10] [Formula 1-11]

In the [Formula 1-1] to [Formula 1-11], R ₁ and R ₂ , a and b are the same as the definition in claim 1, * is bonded to L or Ar of the [Formula 1] Means site.

According to a preferred embodiment of the present invention, [Chemical Formula 1] may be selected from compounds represented by the following [Chemical Formula 1-12] to [Chemical Formula 1-24].

[Formula 1-12] [Formula 1-13] [Formula 1-14] [Formula 1-15]

[Formula 1-16] [Formula 1-17] [Formula 1-18] [Formula 1-19]

[Formula 1-20] [Formula 1-21] [Formula 1-22]

[Formula 1-23] [Formula 1-24]

In the [Formula 1-12] to [Formula 1-24], R ₁ and R ₂ , a and b are the same as the definition in claim 1, * is bonded to L or Ar of the [Formula 1] Means site.

According to a preferred embodiment of the present invention, L may be any one selected from the following [Structural Formula C1] to [Structural Formula C14].

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3] [Structural Formula C4]

[Structural Formula C5][Structural Formula C6][Structural Formula C7][Structural Formula C8][Structural Formula C9]

[Structural Formula C10] [Structural Formula C11] [Structural Formula C12] [Structural Formula C13] [Structural Formula C14]

In the [Structural Formulas C1] to [Structural Formulas C14], hydrogen or deuterium may be bonded to the carbon site of the ring in each structural formula, and R is R ₁ in the [Formula 1] To R ₇ is the same as the definition.

On the other hand, the aryl group contained in the organic light-emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4 -Ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, And aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a 2 to 24 heteroaryl group or a C 2 to 24 heteroarylalkyl group.

On the other hand, the heteroaryl group included in the organic light-emitting compound according to the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 10], and in particular, Ar connected to the L is the following [Structural Formula 1] to [Structural Formula 10] may be any one selected from.

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In the [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and each independently, is selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O and S, and the R ₄₁ To R ₄₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number of 5 to It is selected from an aryl group of 30 and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom.

In addition, the [Structural Formula 1] to [Structural Formula 10] may be any one selected from the following [Structural Formula 11].

[Structural Formula 11]

In [Structural Formula 11],

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms From an amine group, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, a cyano group, a nitro group, and a halogen group Is selected, m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other.

Specific examples of the alkyl group as a substituent used in the present invention include methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc., and at least one hydrogen atom of the alkyl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (In this case, referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each Independently, it is an alkyl group having 1 to 24 carbon atoms (referred to as "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, and Halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group as a substituent used in the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like. May be substituted with the same substituent as in the case of the alkyl group.

Specific examples of the halogen group that is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group may be further substituted.

Specific examples of the silyl group as a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl, etc. are mentioned.

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

According to a preferred embodiment of the present invention, [Chemical Formula 1] may be selected from compounds represented by the following [Chemical Formula 2] to [Chemical Formula 225].

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63] [Formula 64] [Formula 65]

[Formula 66] [Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96] [Formula 97]

[Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103] [Formula 104] [Formula 105]

[Formula 106] [Formula 107] [Formula 108] [Formula 109]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Formula 114] [Formula 115] [Formula 116] [Formula 117]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125]

[Formula 126] [Formula 127] [Formula 128] [Formula 129]

[Formula 130] [Formula 131] [Formula 132] [Formula 133]

[Formula 134] [Formula 135] [Formula 136] [Formula 137]

[Formula 138] [Formula 139] [Formula 140] [Formula 141]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Formula 146] [Formula 147] [Formula 148] [Formula 149]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

[Formula 158] [Formula 159] [Formula 160] [Formula 161]

[Formula 162] [Formula 163] [Formula 164] [Formula 165]

[Formula 166] [Formula 167] [Formula 168] [Formula 169]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical Formula 173]

[Formula 174] [Formula 175] [Formula 176] [Formula 177]

[Formula 178] [Formula 179] [Formula 180] [Formula 181]

[Formula 182] [Formula 183] [Formula 184] [Formula 185]

[Formula 186] [Formula 187] [Formula 188] [Formula 189]

[Formula 190] [Formula 191] [Formula 192] [Formula 193]

[Formula 194] [Formula 195] [Formula 196] [Formula 197]

[Formula 198] [Formula 199] [Formula 200] [Formula 201]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical Formula 205]

[Formula 206] [Formula 207] [Formula 208] [Formula 209]

[Formula 210] [Formula 211] [Formula 212] [Formula 213]

[Formula 214] [Formula 215] [Formula 216] [Formula 217]

[Formula 218] [Formula 219] [Formula 220] [Formula 221]

[Formula 222] [Formula 223] [Formula 224] [Formula 225]

Another aspect of the present invention relates to an organic thin film layer for an organic light emitting device, characterized in that it comprises at least one compound according to the present invention [Formula 1].

According to one embodiment of the present invention, the organic thin film layer is characterized in that it further comprises at least one or more compounds represented by the following [Chemical Formula A-1] to [Chemical Formula J-1].

[General Formula A-1]

ML ₁ L ₂ L ₃

The M is selected from the group consisting of metals of groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and may each independently include any one selected from the following [Structural Formula D], but is not limited thereto. In addition, * in the following [structural formula D] represents a site that binds to the metal ion M.

[Structural Formula D]

In the [Structural Formula D],

R is different from each other or the same, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It may be any one selected from group.

Each of R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen It may be further substituted with one or more substituents.

In addition, the R may be connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

As a specific example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[General Formula B-1]

In the above [general formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as previously defined, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonded to M ^A1 .

An exemplary structure of the compound represented by [General Formula B-1] is as follows, but is not limited thereto.

[General Formula C-1]

In the above [general formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 And Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, and Q ^B11 , Q ^B12 are It shows a partial structure containing an atom bonded to M ^B1 .

An exemplary structure of the compound represented by [General Formula C-1] is as follows, but is not limited thereto.

[General Formula D-1]

In the above [general formula D-1],

M ^C1 represents the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 are each independently a hydrogen atom, a substituent that connects to each other to form a 5-membered ring, and does not have any Represents a substituent, and R ^C13 and R ^C14 are each independently a hydrogen atom, a substituent that connects to each other to form a five-membered ring, and represents a substituent that does not have anything that connects to each other, and G ^C11 and G ^C12 are each independently a nitrogen atom, substituted Or an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

An exemplary structure of the compound represented by [General Formula D-1] is as follows, but is not limited thereto.

[General Formula E-1]

In the above [general formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and Each of J ^D14 represents an atomic group required to form a five-membered ring independently, and L ^D11 and L ^D12 represent a linking group.

An exemplary structure of the compound represented by [General Formula E-1] is as follows, but is not limited thereto.

[General Formula F-1]

In the above [general formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent an atomic group required to form a 5-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

An exemplary structure of the compound represented by [General Formula F-1] is as follows, but is not limited thereto.

[General Formula G-1]

In the above [general formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be linked to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

An exemplary structure of the compound represented by [General Formula G-1] is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the above [General Formula H-1] to [General Formula H-3],

R ¹¹ , R ¹² are substituents of alkyl, aryl or heteroaryl; In addition, a fused ring may be formed with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, a halogen ligand, and more preferably an ortho metal. ) A ligand, a bipyridyl ligand or a phenanthroline ligand that forms a platinum complex.

n ¹ is an integer of 0 to 3, preferably 0, and m ¹ is 1 or 2, preferably 2.

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the general formula H-1 become a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2 , 0 is preferred.

In the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more than 0 desirable.

Examples of specific compounds of the [General Formula H-1] to [General Formula H-3] are as follows, but are not limited thereto.

[General Formula I-1]

In the above [general formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two rings of rings A to D may have a substituent, and the other two rings are an aryl ring or heterocycle that may have a substituent. Represents and represents an aryl ring, and a condensed ring can be formed by ring A and ring B, ring A and ring C, and/or ring B and ring D. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (term) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of specific compounds of the [General Formula I-1] are as follows, but are not limited thereto.

[General Formula J-1]

In the above [general formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) bound to the M In this case, the nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand that is bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

In the above [general formula J-1], it is preferable that M is Pt. In addition, it is preferable that Ar1 is selected from a 5-membered ring, a 6-membered ring and a condensed ring group thereof.

Examples of specific compounds of the [General Formula J-1] are as follows, but are not limited thereto.

In addition, the organic thin film layer may further include various host compounds and various dopant compounds in addition to the organic electroluminescent compound and the dopant compound according to the present invention.

Another aspect of the present invention relates to an organic electroluminescent device including the organic thin film layer, wherein at least one organic thin film layer including a light emitting layer is sandwiched between a cathode and an anode of the organic electroluminescent device, and at least one layer of the organic thin film layer The organic light-emitting compound of [Chemical Formula 1] according to the present invention may be included alone or as a component of a mixture, and the dopant compound illustrated above may be further included.

The organic electroluminescent device according to the present invention may further include one or more layers 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, and an electron injection layer in addition to the emission layer. In addition to the light emitting layer, the organic light emitting compound may be used for a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The hole transport layer Silver is laminated to make it easier to inject holes from the anode, and an electron donating molecule having a small ionization potential is used as a material for the hole transport layer, mainly diamine, triamine or tetraamine derivatives having triphenylamine as a basic skeleton. It is used a lot.

In the present invention, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1, 1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenyl benzidine (α-NPD), and the like can be used.

A hole injection layer (HIL) may be additionally stacked under the hole transport layer, and the hole injection layer material is not particularly limited as long as it is commonly used in the art. For example, CuPc (copper phthalocyanine) or Starburst-type amines TCTA (4,4',4"-tri(N-carbazolyl)triphenyl-amine), m-MTDATA(4,4',4"-tris- (3-methylphenylphenylamino)triphenylamine) can be used.

In addition, the electron transport layer used in the organic light emitting device according to the present invention smoothly transports electrons supplied from the cathode to the organic light emitting layer and inhibits the movement of holes that could not be combined in the organic light emitting layer to recombine in the light emitting layer. It serves to increase.

The electron transport layer material is not particularly limited and may be used as long as it is commonly used in the art. For example, oxadiazole derivatives such as PBD, BMD, BND, or Alq3 may be used.

On the other hand, on the top of the electron transport layer, an electron injecting layer (EIL) that facilitates electron injection from the cathode and ultimately improves power efficiency may be further stacked. The material of the electron injection layer Also, as long as it is commonly used in the art, it may be used without particular limitation, and for example, materials such as LiF, NaCl, CsF, Li2O, and BaO may be used.

The organic electroluminescent device according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, and if necessary, the hole injection layer 30 and An electron injection layer 70 may be further included, and in addition to that, a first or second intermediate layer may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic light emitting device of the present invention and a method of manufacturing the same will be described as follows. First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and the like are used, which are transparent and have excellent conductivity.

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, a hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport capability and an ionization potential higher than that of a light-emitting compound, and representatively, BAlq, BCP, TPBI, and the like may be used.

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode-forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form the cathode 80 electrode. Here, the cathode-forming metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

In addition, according to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a monomolecular deposition method or a solution process. The organic electroluminescent device according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for describing the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.

Synthesis example 1. Synthesis of Formula 54

[Scheme 1]

<1-a>

Dilute 2-aminobiphenyl (4.98 g, 29.4 mmol) in 80 mL of water in 20 mL of water containing 5.0 mL of sulfuric acid, lower the temperature to 0 °C, and add sodium nitrite (2.5 g, 36.2 mmol) while stirring. Then, add sodium acetate until it turns dark yellow (pH = 6). Potassium selenocyanate (4.2 g, 29.1 mmol) is dissolved in 20 mL of water and slowly added dropwise. After stirring for about an hour, it was diluted with 70 mL of toluene, and separated by column chromatography to obtain 3.7 g of <1-a>. (Yield 49%)

[Scheme 2]

<1-b>

Potassium hydroxide (0.78 g, 13.9 mmol) was diluted in 4 mL of methanol, <1-a> 1.06 g was slowly added, stirred for 30 minutes, and then added to a mixture of 50 mL of toluene and 50 mL of saturated boric acid, and filtered under reduced pressure. After recrystallization from acetone, <1-b> 1.05 g was obtained. (Yield 55%)

[Scheme 3]

<1-c>

<1-b> (1.13 g, 2.4 mmol) was dissolved in 20 mL of chloroform and refluxed. Bromine (0.1 mL, 2.0 mmol) was added, and after stirring for about 4 hours, the temperature was lowered to 65 ℃ and stirred for 18 hours. When the reaction was completed, the solvent was removed and separated by column chromatography to obtain 0.745 g of <1-c>. (Yield 99%)

[Scheme 4]

<1-d>

<1-c> (2.0 g, 8.654 mmol) was dissolved in 50 mL of tetrahydrofuran, and n-butyllithium (10 mL, 16.5 mmol) was slowly added at -78 °C. After 1 hour, iodine (4.18 g, 16.5 mmol) was added and stirred at room temperature for 12 hours. After the reaction was completed, the organic layer was washed with a saturated sodium thiosulfate solution and filtered under reduced pressure to obtain 2 g of <1-d>. (Yield 67%)

[Scheme 5]

<1-e>

In a 5L round bottom flask <1-d> (224.94 g, 0.63 mol) and 2-bromoaniline (122.1 g, 0.789 mol), tris(dibenzideneacetone)dipalladium(0) (12 g, 0.013 mol) , 1,1'-bis(diphenylphosphino)ferrocene (14.5 g, 0.026 mol), sodium tertiarybutoxide (94.1 g, 0.979 mol) and 2100 mL of toluene were added and refluxed for 12 hours. After completion of the reaction, the mixture was filtered, concentrated under reduced pressure, and separated by column chromatography to obtain 164 g of <1-e>. (Yield 69%)

[Scheme 6]

<1-f>

In a 2 L round bottom flask <1-e> (61.22 g, 0.19 mol), tricyclohexylphosphinium tetrafluoroborate (1.4 g, 0.004 mol), palladium acetate (0.431 g, 0.002 mol), potassium carbonate (53.1) g, 0.384 mol) and 700 mL of yen, en-dimethylacetamide and refluxed for 12 hours. After completion of the reaction, the mixture was extracted and recrystallized with hexane to obtain 46.3 g of <1-f>. (Yield 85%)

[Scheme 7]

<1-g>

In a 100 mL reactor, magnesium (3.36 g, 0.138 mol), 40 mL of tetrahydrofuran, and a small amount of iodine were added and stirred for 30 minutes. A solution in which bromobenzene (19.2 g, 0.122 mol) was dissolved in 20 mL of tetrahydrofuran was added dropwise to the mixed pressure solution at 0°C. Stir while heating at 65° C. for about 2 hours. 2,4,6-trichloro-1,3,5-triazine (18 g, 0.06 mol) was dissolved in 100 mL of tetrahydrofuran, and then added dropwise at 0 °C. Stir at room temperature for 12 hours. When the reaction was completed, 200 mL of 2N hydrochloric acid was added, followed by extraction, and then separated by column chromatography to obtain 9.8 g of <1-g>. (Yield 65%)

[Scheme 8]

[Chemical Formula 54]

In a 500 mL round bottom flask, add 60% sodium hydride (0.8 g, 0.022 mol) and 90 mL of N,N-dimethylformamide and lower the temperature to 0 °C. A solution of <1-f> (4.8 g, 0.015 mol) dissolved in 90.0 mL of N,N-dimethylformamide was slowly added dropwise, and the mixture was stirred at 0° C. for 1 hour. A solution of <1-g> (6.5 g, 0.018 mol) in 130 mL of N,N-dimethylformamide is slowly added dropwise. After raising the reaction solution to room temperature, it is stirred. When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate a solid and then filtered. It was recrystallized from toluene to obtain 7.1 g of [Chemical Formula 54]. (Yield 55%)

MS(MALDI-TOF): m/z 551.50[M] ⁺

Synthesis example 2. Synthesis of Chemical Formula 63

[Scheme 9]

<2-a>

[Scheme 7] and [Scheme 7] except that 2,4,6-trichloro-1-pyridine was used instead of 2,4,6-trichloro-1,3,5-triazine in [Scheme 7] of Synthesis Example 1 It was synthesized by the same method to obtain 34 g of <2-a>. (Yield 78%)

[Scheme 10]

[Chemical Formula 63]

Except for using <2-a> instead of <1-g> used in [Scheme 8] of Synthesis Example 1, it was synthesized in the same manner to obtain 10.4 g of [Chemical Formula 63]. (Yield 56%)

MS(MALDI-TOF): m/z 549.52[M] ⁺

Synthesis example 3. Synthesis of Formula 94

[Scheme 11]

<3-a>

Except for using 4-fluoro-bromobenzene instead of bromobenzene used in Scheme 7, <4-a> 31.2g (yield 60.4%) was obtained by synthesis in the same manner.

[Scheme 12]

[Formula 94]

Except for using <3-a> instead of <1-g> used in [Scheme 8] of Synthesis Example 1, it was synthesized in the same manner to obtain 10.4 g of <Chemical Formula 94>. (Yield 56%)

MS(MALDI-TOF): m/z 588.07[M] ⁺

Synthesis example 4. Synthesis of Formula 211

[Scheme 13]

<4-a>

Methyl-2-aminobenzoate (87 g, 0.58 mol), <1-d> (171.4 g, 0.48 mol), palladium acetate (1.3 g, 0.006 mol), xantphos (10 g, 0.02 mol), cesium carbonate (217.5 g, 0.67 mol), 2500 mL of toluene was added and refluxed for 6 hours. After extraction with ethyl acetate and separation by column chromatography, 136.9 g of <4-a> was obtained. (Yield 75%)

[Scheme 14]

<4-b>

<4-b> (136.9 g, 0.36 mol) was added to 1650 mL of diisopropyl ether and stirred. After slowly adding 419 mL of methyl magnesium bromide, the mixture was stirred at 50° C. for 12 hours. After extraction with ethyl acetate and recrystallization with dichloromethane and hexane, <4-b> 134 g (yield 98%) was obtained.

[Scheme 15]

<4-c>

<4-b> (134 g, 0.35 mol) and 400 mL of phosphoric acid were added and stirred for 6 hours. When the reaction was completed, an excess of distilled water was added, stirred, filtered, and separated by column chromatography to give <4-c> 95.7 g (75% yield).

[Scheme 16]

<4-d>

1-nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol), potassium hydroxide (62.9 g, 1.12 mol) were added and stirred. Then, 970 mL of dimethylformamide was added and stirred at 60°C overnight. After removing the solvent by concentrating under reduced pressure at room temperature, 500 mL of a 10% aqueous sodium hydroxide solution was added and refluxed for about 1 hour. After extraction with ethyl acetate, separation by column chromatography and recrystallization from toluene and heptane gave <4-d> 50.8 g. (Yield 75%)

[Scheme 17]

<4-e>

<4-d> (25.1 g, 149 mmol) was added to 200 mL of tetrahydrofuran and stirred. Phenyl magnesium bromide (3.0 M in Et ₂ O) (87.4 mL, 297 mmol) was added dropwise and refluxed at 0° C. for about 1 hour. After adding ethyl chloroformate (19.4 g, 179 mmol) dropwise, it was refluxed for about 1 hour. An aqueous ammonium chloride solution was added until it became slightly acidic, and washed with water and heptane to obtain 32.4 g of <4-e>. (Yield 80%)

[Scheme 18]

<4-f>

<4-e> (30 g, 110 mmol) was added to about 80 mL of phosphorus oxychloride and refluxed overnight. After cooling the temperature to -20 °C, about 400 mL of distilled water was slowly added. Washed with water, methanol and heptane, and recrystallized from toluene and heptane to give <4-f> 14.5 g. (Yield 45%).

[Scheme 19]

<4-g>

<4-f> (20 g, 0.07 mol), 4-iodophenyl boronic acid (20.5 g, 0.08 mol), tetrakis (triphenylphosphine) palladium (4 g, 0.003 mol), potassium carbonate (19 g , 0.14 mol), 1,4-dioxane 100 mL, toluene 100 mL, distilled water 40 mL, and refluxed overnight. After extraction with ethyl acetate and recrystallization with dichloromethane and acetone, <4-g> 19.9 g was obtained. (Yield 80%)

[Scheme 20]

[Chemical Formula 211]

Except for using <4-c> instead of <1-f> used in [Scheme 8] of Synthesis Example 1, and using <4-g> instead of <1-g>, it was synthesized in the same manner and <Chemical Formula 211 > 25 g was obtained. (Yield 52%)

MS(MALDI-TOF): m/z 693.17[M] ⁺

Synthesis example 5. Synthesis of Formula 212

[Scheme 21]

<5-a>

Except for using phenyl magnesium bromide instead of methyl magnesium bromide used in [Scheme 14] of Synthesis Example 4, it was synthesized in the same manner to obtain <5-a> 102 g. (Yield 94%)

[Scheme 22]

<5-b>

Except for using <5-a> instead of <4-b> used in [Scheme 15] of Synthesis Example 4, it was synthesized in the same manner to obtain 70.8 g of <5-b>. (Yield 72%)

[Scheme 23]

<5-c>

After placing nitrogen in the dried 2L reactor, 2-aminobenzonitrile (45.0 g, 381 mmol) and 405 mL of tetrahydrofuran were added, and 3 M pentadeutereo phenylmagnesium bromide (287 mL, 838 mmol) was slowly added at 0°C. After adding dropwise, the mixture was stirred under reflux for 3 hours. After lowering to low temperature, ethylchloroformate (62 g, 0.571 mmol) was dissolved in 200 mL of tetrahydrofuran, slowly added dropwise, and stirred under reflux for 2 hours. Separated by column chromatography to obtain 50 g. (Yield 58%)

[Scheme 24]

<5-d>

Except for using <5-c> instead of <4-e> used in [Scheme 18] of Synthesis Example 4, it was synthesized in the same manner to obtain 42 g of <5-d>. (Yield 75%)

[Scheme 25]

[Compound 212]

Except for using <5-b> instead of <1-f> used in [Scheme 8] of Synthesis Example 1, and using <5-d> instead of <1-g>, <Chemical Formula 212 > 64 g was obtained. (Yield 54%)

MS(MALDI-TOF): m/z 696.18[M] ⁺

Example : Preparation of organic light emitting diode

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in a vacuum chamber, the base pressure is 1×10 ^-6 torr, and then the organic material is placed on the ITO DNTPD (700 Å), NPD (300 Å), the compound prepared by the present invention + Ir (ppy) Films were formed in the order of ₃ (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å), and measured at 0.4 mA.

Comparative example

The organic light emitting diode device for the comparative example was fabricated in the same manner, except that CBP, which is commonly used as a phosphorescent host material, was used instead of the compound prepared according to the invention in the device structure of the above example, and the structure of the CBP is as follows.

division Host Dopant Doping concentration% V Cd/㎡ CIEx CIEy T ₈₀ (Hr) Comparative Example 1 CBP Ir(ppy) ₃ 10 7.93 3801 0.297 0.624 68 Example 1 54 Ir(ppy) ₃ 10 4.08 5267 0.277 0.626 180 - Example 3 94 Ir(ppy) ₃ 10 4.03 5177 0.298 0.624 110 Example 4 211 Ir(ppy) ₃ 10 3.99 5019 0.296 0.622 98 Example 5 212 Ir(ppy) ₃ 10 4.13 4879 0.304 0.629 170 Example 6 2 Ir(ppy) ₃ 10 4.34 5061 0.301 0.629 73 Example 7 33 Ir(ppy) ₃ 10 3.96 5260 0.293 0.634 173 Example 8 39 Ir(ppy) ₃ 10 4.07 5379 0.291 0.626 201 Example 9 63 Ir(ppy) ₃ 10 4.03 5017 0.294 0.626 175 Example 10 78 Ir(ppy) ₃ 10 4.14 4978 0.284 0.631 107 Example 11 107 Ir(ppy) ₃ 10 4.24 4896 0.296 0.622 93 Example 12 127 Ir(ppy) ₃ 10 4.24 4896 0.299 0.621 140 Example 13 151 Ir(ppy) ₃ 10 4.24 4896 0.297 0.635 150 Example 14 198 Ir(ppy) ₃ 10 4.24 4896 0.307 0.637 70 Example 15 202 Ir(ppy) ₃ 10 4.24 4896 0.297 0.626 120

In [Table 1], T80 refers to the time required for the luminance to be reduced to 80% compared to the initial luminance.

As shown in [Table 1], when the organic light-emitting compound embodied according to the present invention is used as the host compound of the light-emitting layer of the organic light-emitting device, the lifespan characteristics are remarkably improved, the light-emitting characteristics are excellent, and the driving voltage is reduced. By lowering it, power consumption can be improved by inducing an increase in power efficiency.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (14)

Organic light-emitting compound represented by the following [Formula 1]:
[Formula 1]

In the above [Formula 1],
X is a single bond or CR ₃ R ₄ (wherein R ₃ to R ₄ are hydrogen, an alkyl group having 1 to 7 carbon atoms, or an aryl group having 6 to 20 carbon atoms),
L is a single bond or a linking group selected from a substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, n is an integer of 0 to 3, wherein n is In the case of 2 or more, a plurality of L is the same or different from each other
Ar is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms,
A represents a pentagonal ring or a hexagonal ring including Se represented by the following [Structural Formula A-1] or [Structural Formula A-2],
[Structural Formula A-1] [Structural Formula A-2]

R ₁ to R ₂ are the same as or different from each other, each independently hydrogen or deuterium, a and b are integers of 1 to 4, and when a and b are 2 or more, a plurality of R ₁ and R ₂ are each the same Or different. The method of claim 1,
[Chemical Formula 1] is an organic light emitting compound, characterized in that selected from the compounds represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-11]:

[Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4]

[Formula 1-5] [Formula 1-6] [Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10] [Formula 1-11]
In the above [Formula 1-1] to [Formula 1-11],
R ₁ and R ₂ , a and b are the same as defined in claim 1, and * means a site bonding to L or Ar of the [Chemical Formula 1]. The method of claim 1,
[Chemical Formula 1] is an organic light-emitting compound, characterized in that selected from compounds represented by the following [Chemical Formula 1-12] to [Chemical Formula 1-24]:

[Formula 1-12] [Formula 1-13] [Formula 1-14] [Formula 1-15]

[Formula 1-16] [Formula 1-17] [Formula 1-18] [Formula 1-19]

[Formula 1-20] [Formula 1-21] [Formula 1-22]

[Formula 1-23] [Formula 1-24]
In the above [Formula 1-12] to [Formula 1-24],
R ₁ and R ₂ , a and b are the same as defined in claim 1, and * means a site bonding to L or Ar of the [Chemical Formula 1]. The method of claim 1,
When Ar and L are each further substituted, deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted C 1 to C 20 An organic light-emitting compound, characterized in that it is substituted with at least one selected from an alkylsilyl group and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms. delete delete delete The method of claim 1,
[Chemical Formula 1] is an organic light-emitting compound, characterized in that any one selected from compounds represented by the following formula:

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63] [Formula 64] [Formula 65]

[Formula 66] [Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96] [Formula 97]

[Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103] [Formula 104] [Formula 105]

[Formula 106] [Formula 107] [Formula 108] [Formula 109]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Formula 114] [Formula 115] [Formula 116] [Formula 117]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125]

[Formula 126] [Formula 127] [Formula 128] [Formula 129]

[Formula 130] [Formula 131] [Formula 132] [Formula 133]

[Formula 134] [Formula 135] [Formula 136] [Formula 137]

[Formula 138] [Formula 139] [Formula 140] [Formula 141]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Chemical Formula 146]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

[Formula 158] [Formula 159] [Formula 160] [Formula 161]

[Formula 162] [Formula 163] [Formula 164] [Formula 165]

[Formula 166] [Formula 167] [Formula 168] [Formula 169]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical Formula 173]

[Formula 174] [Formula 175] [Formula 176] [Formula 177]

[Formula 178] [Formula 179] [Formula 180] [Formula 181]

[Formula 182] [Formula 183] [Formula 184] [Formula 185]

[Formula 186] [Formula 187] [Formula 188] [Formula 189]

[Formula 190] [Formula 191] [Formula 192] [Formula 193]

[Formula 196] [Formula 197]

[Formula 198] [Formula 199] [Formula 200] [Formula 201]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical Formula 205]

[Formula 206] [Formula 207] [Formula 208] [Formula 209]

[Formula 210] [Formula 211] [Formula 212]

[Formula 214] [Formula 215] [Formula 216] [Formula 217]

[Formula 218] [Formula 219] [Formula 220] [Formula 221]

[Formula 222] [Formula 223] [Formula 224] [Formula 225] An organic thin film layer for an organic electroluminescent device comprising at least one organic light emitting compound according to claim 1. The method of claim 9,
The organic thin film layer is an organic thin film layer, characterized in that the host comprises an organic light emitting compound represented by [Formula 1] and further comprises at least one dopant compound. Anode; A cathode facing the anode; And the organic thin film layer according to claim 9 interposed between the anode and the cathode. The method of claim 11,
The organic electroluminescent device further includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron blocking layer between the anode and the cathode,
An organic electroluminescent device, characterized in that one of the emission layer, the hole injection layer, the hole transport layer, the hole blocking layer, the electron transport layer, the electron injection layer and the electron blocking layer is the organic thin film layer according to claim 9. The method of claim 12,
An organic electroluminescent device, wherein the emission layer is the organic thin film layer according to claim 9. The method of claim 11,
The organic light-emitting device is an organic light-emitting device, characterized in that it emits white light by including at least one organic light-emitting layer emitting blue, red, or green light.

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