KR102140005B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light-emitting device represented by the following [Formula 1] and an organic electroluminescent device comprising the same, the organic light-emitting compound according to the present invention is excellent in luminous efficiency and lifetime characteristics of the material, and at the same time excellent in luminous efficiency An organic light emitting device having power efficiency and long life characteristics can be manufactured.
[Formula 1]

Description

An organic light emitting compound and an organic electroluminescent device comprising the same{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 comprising the same.

Recently, the organic light emitting device capable of driving a low voltage as a self-emission type has superior viewing angle, contrast ratio, etc., and does not require a backlight, is lightweight and thin, is advantageous in terms of power consumption, and reproduces color compared to a liquid crystal display, which is a mainstream of flat panel display elements. The wide range has attracted attention as a next-generation display device.

An organic electroluminescent device is a device that emits light while extinguishing after pairing electrons and holes when a charge is 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 not only form the device on a transparent substrate that can be bent, such as plastic, but can also be driven at a voltage lower than 10 V, and consumes less power than a plasma display panel or an inorganic electroluminescent display. , Has the advantage of excellent color. In addition, the organic electroluminescent device can display three colors: green, blue, and red, and is a subject of great interest as a next-generation rich color display device.

The most important factor in determining the luminous efficiency in an organic light emitting device is a light emitting material. Fluorescent materials are currently widely used as luminescent materials, but the development of phosphorescent materials is one of the methods that can theoretically improve the luminous efficiency due to the luminescence mechanism. Accordingly, various phosphorescent materials have been developed to date. In particular, CBP is the most widely known phosphorescent host material to date, and an organic electroluminescent device using a BALq derivative as a host is known.

However, the organic light emitting device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material, but when using a material such as BAlq, CBP as a host for the phosphorescent material, it is driven compared to a device using a fluorescent material. Since the voltage is high, there is no great advantage in terms of power efficiency, and the level of life of the device is not satisfactory, so there is a need to develop a more stable and high-performance host material.

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

In addition, the present invention is to provide an organic electroluminescent device having high efficiency and long life 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 [Formula 1],

It provides an organic thin film layer for an organic light emitting device, characterized in that it comprises at least one organic light-emitting compound in the organic light-emitting compound.

[Formula 1]

Each substituent in [Formula 1] will be described later.

In addition, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer is represented by [Formula 1] It characterized in that it comprises an organic thin film layer containing at least one organic light emitting compound.

The organic layer may include at least one selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The organic light emitting compound is used as a host for the light emitting layer, and the light emitting layer may further include one or more dopant compounds.

Further, the organic light emitting device according to the present invention may be an organic light emitting device that emits white light by further including one or more organic light emitting layers that emit blue, red, or green light.

The organic light emitting compound according to the present invention is excellent in luminous efficiency and lifespan characteristics of a material, and thus can produce an organic electroluminescent device having excellent luminous efficiency and power efficiency and long life characteristics.

1 is a schematic diagram of an organic light emitting device 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 [Formula 1].

[Formula 1]

In the above [Formula 1],

The L _a is a chemical bond, substituted or unsubstituted alkylene having 1 to 60 carbon atoms, substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted heterocycloalkylene having 2 to 60 carbon atoms and a substituted or unsubstituted arylene having 6 to 50 carbon atoms, including one or more selected from cycloalkylene having 3 to 60 carbon atoms, N, O and S; And substituted or unsubstituted heteroarylene having 3 to 50 carbon atoms, n is an integer from 0 to 6, and when n is 2 or more, a plurality of L _{a s} are the same or different from each other.

According to a preferred embodiment, L _a may be a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms, and specifically, an aryl group having 6 to 50 carbon atoms, or The heteroaryl group having 3 to 50 carbon atoms is a divalent linking group, and when L _a is an arylene group, a phenylene group, a biphenylene group, a terphenylene group, a quarterphenylene group, a naphthylene group, anthraceneylene group, and a phenanthrene group , A chrysylene group, a pyrylene group, a perylene group, a fluorene group, etc., more preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenanthrene group or a fluorene group , When L _a is a heteroarylene group, a pyrroline group, a furanylene group, a thiophenyl group, a silrolylene group, a pyridylene group, an imidazolylene group, a pyrimidylene group, a carbazolylene group, a selenophenyl group, It may be an oxadiazolylene group, a triazolylene group, and the like, and these arylene groups and heteroarylene groups may be connected to each other identically or differently.

In addition, Y may be any one selected from CR ₁ R ₂ , SiR ₃ R _{4 ,} NR ₅ , PR ₆ , P(=OR ₇ ), BR ₈ , O and S, and X ¹ to X ⁵ are each Independently N or CR ₉ , and Z ¹ to Z ⁸ are each independently N or CR ₁₀ .

R ₁ to R ₁₀ are each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or Unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms Amino 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 carbon number 1 To 50 arylalkylamino groups, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, hydroxyl groups , A nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a cyano group, a halogen group, selected from the group consisting of deuterium and hydrogen, each adjacent substituents They may combine with each other to form a saturated or unsaturated ring.

In addition, the R ₉ and R ₁₀ are a plurality of R ₉ and R _10, if multiple individuals each of which may be the same or different, respectively.

When L _a and R ₁ to R ₁₀ are each substituted, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, 1 to 1 carbon atom 60 alkoxy group, 6 to 30 carbon atoms aryloxy group, 1 to 20 carbon atoms alkyl group, 6 to 30 carbon atoms arylamino group, 1 to 20 carbon atoms alkylsilyl group, 6 to 30 carbon atoms arylsilyl group, carbon number 1 Arylalkylamino group of 50 to 50, arylthio group of 5 to 60 carbon atoms, alkenyl group of 2 to 60 carbon atoms, alkynyl group of 2 to 60 carbon atoms, hydroxyl group, nitro group, amino group, amidino group, hydrazine, hydrazone, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a cyano group, a halogen group, deuterium, and hydrogen may be substituted with one or more selected from the group consisting of substituents substituted with R ₁ to R ₁₀ are adjacent substituents And may combine with each other to form a saturated or unsaturated ring.

은 하기 [구조식 1] 중에서 선택되는 어느 하나일 수 있다.According to a preferred embodiment, connected to the L _a

May be any one selected from the following [Structural Formula 1].

[Structural Formula 1]

In [Structural Formula 1], the Y and R ₁₀ are the same as defined above, and the plurality of R ₁₀ may be the same or different, respectively.

은 하기 [구조식 2] 중에서 선택되는 어느 하나일 수 있다.According to a preferred embodiment, connected to the L _a

May be any one selected from the following [Structural Formula 2].

[Structural Formula 2]

In [Structural Formula 2], R ₉ is the same as defined above, and a plurality of R ₉ may be the same or different, respectively.

According to a preferred embodiment of the present invention, the [Formula 1] may be selected from compounds represented by the following [Formula 2] to [Formula 293].

[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]

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

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

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

[Formula 58] [Formula 59] [Formula 60] [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]

[Formula 78] [Formula 79] [Formula 80] [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]

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

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

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

[Chemical Formula 130] [Chemical Formula 131] [Chemical Formula 132] [Chemical 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]

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

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

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

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

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

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

[Chemical Formula 182] [Chemical Formula 183] [Chemical Formula 184] [Chemical 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]

[Formula 202] [Formula 203] [Formula 204] [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]

[Chemical Formula 226] [Chemical Formula 227] [Chemical Formula 228] [Chemical Formula 229]

[Formula 230] [Formula 231] [Formula 232] [Formula 233]

[Formula 234] [Formula 235] [Formula 236] [Formula 237]

[Formula 238] [Formula 239] [Formula 240] [Formula 241]

[Formula 242] [Formula 243] [Formula 244] [Formula 245]

[Formula 246] [Formula 247] [Formula 248] [Formula 249]

[Formula 250] [Formula 251] [Formula 252] [Formula 253]

[Formula 254] [Formula 255] [Formula 256] [Formula 257]

[Formula 258] [Formula 259] [Formula 260] [Formula 261]

[Formula 262] [Formula 263] [Formula 264] [Formula 265]

[Chemical Formula 266] [Chemical Formula 267] [Chemical Formula 268] [Chemical Formula 269]

[Formula 270] [Formula 271] [Formula 272] [Formula 273]

[Formula 274] [Formula 275] [Formula 276] [Formula 277]

[Formula 278] [Formula 279] [Formula 280] [Formula 281]

[Formula 282] [Formula 283] [Formula 284] [Formula 285]

[Formula 286] [Formula 287] [Formula 288] [Formula 289]

[Formula 290] [Formula 291] [Formula 292] [Formula 293]

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 organic light emitting compound represented by [Formula 1].

The organic thin film layer is to host the organic light-emitting compound represented by the above [Formula 1], and further comprising at least one dopant compound represented by the following [General Formula A-1] to [General Formula J-1] It is characterized by.

[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 are the same as or different from each other as a ligand, and each independently 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 above [Formula D],

R is different from or the same as each other, 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 Heteroaryl group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms It may be any one selected from groups.

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

In addition, R may be connected to each adjacent substituent 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 by alkylene or alkenylene to form a spiro ring or 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, oxygen atom, or sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as previously defined, and Q ^A11 , Q ^A12 represent a partial structure containing an atom that binds to M ^A1 .

The 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, 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 the partial structure containing the atom couple|bonded with M ^B1 .

The 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 a metal ion as 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, and forms a five-membered ring, without any connection to each other. Represents a substituent, R ^C13 , R ^C14 each independently represents a hydrogen atom, a substituent that connects to each other to form a 5-membered ring, or a substituent that does not have anything to connect to each other, G ^C11 , G ^C12 each independently represents a nitrogen atom, a substitution Or represents an unsubstituted carbon atom, L ^C11 , L ^C12 represents a linking group, and Q ^C11 , Q ^C12 represents a partial structure containing an atom bonded to M ^C1 .

The 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 J ^D14 represents a group of atoms required to form a 5-membered ring independently of each other, and L ^D11 and L ^D12 represent a linking group.

The 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 a group of atoms necessary to form a 5-membered ring, 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.

The 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, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to each other to form a ring, wherein the rings formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 are 5-membered rings. In addition, Q ^F11 and Q ^F12 represent partial structures containing atoms that bind to M ^F1 .

The 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 alkyl, aryl or heteroaryl substituents; In addition, it is possible to form a fused ring with a substituent adjacent to each other, q11, q12 is an integer 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, or a halogen ligand, and more preferably an ortho metal. It is a ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

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

Moreover, it is preferable that n ¹ and m ¹ are such that the metal complex represented by the general formula H-1 is 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 , L ¹ , respectively, and q ²¹ is an integer from 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 , L ¹ , respectively, q ³¹ represents an integer of 0 to 8, 0 to 2 is preferable, and 0 is more desirable.

Examples of specific compounds of the above [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 substituents, and the other two rings are aryl rings or heterocycles where rings may have substituents It represents and represents an aryl ring, and may form a condensed ring with ring A and ring B, ring A and ring C, and/or ring B and ring D. In X ¹ , X ² , X ³ and X ⁴ , any two of them represent a nitrogen atom that coordinates with 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 (mono) or bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. Z ¹ , Z ² , Z ³ and Z ⁴ , which 2 represents a coordination bond, and the other 2 represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compound of [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-) that bind to the M In, the nitrogen atom (N) each binds to the M, and as a whole forms a tridentate ligand 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 or different from each other, and each represents a substituted or unsubstituted alkyl or aryl group, and L represents a monodentate ligand.

In [General Formula J-1], it is preferable that M is Pt. Moreover, as said Ar1, it is preferable to select from 5-membered ring, 6-membered ring, and these condensed ring groups.

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

In addition, the organic thin film layer according to the present invention may further include various host and various dopant materials in addition to the dopant compound and the host compound represented by [Formula 1].

When the dopant compound is simultaneously included with the host compound as described above, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first and second electrodes, the organic layer according to the present invention It includes an organic thin film layer containing a compound represented by [Formula 1].

The organic layer may further include at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer, and the hole injection layer and the hole transport layer , One of the functional layer, the light emitting layer, the electron transport layer, and the electron injection layer having the hole injection function and the hole transport function simultaneously may be the organic thin film layer according to the present invention, preferably, the light emitting layer may be the organic thin film layer according to the present invention. .

Hereinafter, an embodiment of the organic light emitting device according to the present invention will be described in more detail with reference to FIG. 1.

1 is a cross-sectional view showing the structure of the organic light emitting device of the present invention, the organic light emitting device according to the present invention is an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode (80), may further include a hole injection layer 30 and an electron injection layer 70, if necessary, in addition, it is also possible to further form an intermediate layer of one or two layers, hole blocking layer Alternatively, an electron blocking layer may be further formed, and an organic layer having various functions may be further included according to device characteristics.

Referring to FIG. 1, an organic electroluminescent device of the present invention and a manufacturing method thereof are as follows.

First, an anode 20 is formed by coating a material for the anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic light emitting device is used, but an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO) are used as the anode electrode material, which is transparent and has excellent conductivity.

A hole injection layer 30 is formed by vacuum thermal vapor deposition or spin coating the hole injection layer material on the anode 20 electrode. Next, a hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer 30.

The hole injection layer material may be used without particular limitation, as long as it is commonly used in the art, and as a specific example, 2-TNATA[4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] Etc. can be used.

In addition, as long as it is a material commonly used in the art as the material for the hole transport layer, it is not particularly limited, 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'-diphenylbenzidine (α-NPD) or the like can be used.

Subsequently, an organic light emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 to form a thin film as a vacuum deposition method or a spin coating method. can do. The hole blocking layer serves to prevent this problem by using a material with a very low level of HOMO (Highest Occupied Molecular Orbital) because the life and efficiency of the device is reduced when holes pass through the organic light emitting layer and enter the cathode. . At this time, the hole-blocking material used is not particularly limited, but has an electron transporting ability and has a higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, etc. can be used.

As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq and [Formula 301] to [Formula 307] may be used, but is not limited thereto. It does not work.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

[Chemical Formula 301] [Chemical Formula 302] [Chemical Formula 303]

[Formula 304] [Formula 305] [Formula 306]

[Formula 307]

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

As the electron transport layer material, a known electron transport material may be used as a function of stably transporting electrons injected from the electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis (benzoquinolin-10- olate: Bebq2), ADN, [Chemical Formula 401], [Chemical Formula 402], oxadiazole derivatives such as PBD, BMD, BND and the like may also be used.

TAZ BAlq

[Compound 401] [Compound 402] BCP

Further, in the electron transport layer used in the present invention, the organometallic compound represented by the following [Chemical Formula C] may be used alone or in combination with the electron transport layer material.

[Chemical Formula C]

In the above [Formula C],

Y is a portion selected from C, N, O, and S directly bonded to M to form a single bond, and a portion selected from C, N, O, and S forming a coordination bond to M. And a ligand chelated by the single bond and coordination bond. M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination with the M, wherein O is oxygen, and A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms It is any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

In addition, m=1, n=0 when M is one metal selected from alkali metals, or m=1, n=1 when M is one metal selected from alkaline earth metals, or m =2, n=0, and when M is boron or aluminum, m=1 to 3, n is any one of 0 to 2, and m+n=3 is satisfied.

The'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

In addition, each of Y is the same or different, and may be any one selected from the following [Structural C1] to [Structural C39] independently of each other, but is not limited thereto.

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

[Structural C4] [Structural C5] [Structural C6]

[Structural C7] [Structural C8] [Structural C9] [Structural C10]

[Structural C11] [Structural C12] [Structural C13]

[Structural C14] [Structural C15] [Structural C16]

[Structural C17] [Structural C18] [Structural C19] [Structural C20]

[Structural C21] [Structural C22] [Structural C23]

[Structural C24] [Structural C25] [Structural C26]

[Structural C27] [Structural C28] [Structural C29] [Structural C30]

[Structural C31] [Structural C32] [Structural C33]

[Structural C34] [Structural C35] [Structural C36]

[Structural C37] [Structural C38] [Structural C39]

In the above [Structural Formula C1] to [Structural Formula C39],

R are the same or different from each other, 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 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms. It is selected from groups, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

L is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 30 carbon atoms Heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is 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, 3 to 20 carbon atoms It is further substituted with one or more substituents selected from heteroaryl groups, cyano groups, halogen groups, deuterium, and hydrogen, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

One or more layers selected from the hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer and electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method is the Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is a material used as a material for forming each layer. Means mixing with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.

In addition, the organic light emitting device according to the present invention may include one or more organic light emitting layers that emit blue, red, or green light to emit white light, and a flat panel display device, a flexible display device, or a flat or white flat panel lighting device And it can be used in a device selected from a monochromatic or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to illustrate the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications can be made within the scope and technical scope of the present invention. It will be obvious to those who have knowledge.

Synthetic example 1. Synthesis of Formula 18

Synthetic example 1-1. Synthesis of <1-a>

<1-a> was synthesized by the following reaction formula 1.

[Scheme 1]

<1-a>

In a 2000 mL round-bottom flask, 39.5 g (1.7 mol) of magnesium, 10 g of iodine and 100 mL of tetrahydrofuran were added under nitrogen, and refluxed for 2 hours. After cooling to room temperature, 212.8 g (1.4 mol) of bromobenzene was dissolved in 200 mL of tetrahydrofuran and slowly added dropwise. After dropwise addition, the mixture was refluxed for 2 hours and cooled to room temperature. After dissolving 100 g (0.54 mol) of cyanuric chloride in 200 mL of tetrahydrofuran in another 2 L round bottom flask, the reaction solution was cooled to 0°C. The previous reaction solution was added dropwise while maintaining the temperature at 0°C. After the reaction was completed, the reaction was terminated with a 4 M aqueous hydrochloric acid solution, extracted, and then the organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain 100 g (68.9%) of <1-a>.

Synthetic example 1-2. Synthesis of <1-b>

<1-b> was synthesized by the following scheme 2.

[Scheme 2]

<1-b>

100.0 g (373.5 mmol) of the compound represented by Formula 1-a obtained from Scheme 1, 75.0 g (373.5 mmol) of 3-bromophenylboronic acid, 8.6 mg (7.5 mmol) of tetrakis(triphenylphosphine)palladium, Potassium carbonate 103.0 g (747.0 mmol), 500 mL of 1,4-dioxane, 500 mL of toluene and 200 mL of distilled water were added and stirred at 100° C. for 24 hours. When the reaction is complete, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized with methylene chloride and acetone to obtain 63.0 g (43%) of the compound represented by <1-b>.

Synthetic example 1-3. Synthesis of <1-c>

<1-c> was synthesized by the following scheme 3.

[Scheme 3]

<1-c>

73.8 g (0.0.488 mol) of methylanthranyrate under nitrogen in a 5000 mL round bottom flask, 100.0 g (0.326 mol) of 2-bromo-triphenylene, palladium acetate (Pd(OAc) ₂ ) 0.7 g (0.003 mol), Xantfoss 5.7 g (0.010 mol), cesium carbonate 212.1 g (0.651 mol), toluene 1500 mL was added and refluxed for 6 hours. When the reaction was completed, the resultant product was layer-separated to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to obtain 108.6 g (88.4%) of <1-c> through column chromatography.

Synthetic example 1-4. Synthesis of <1-d>

<1-d> was synthesized by the following scheme 4.

[Scheme 4]

<1-d>

70 g (0.185 mol) of the compound represented by Chemical Formula 1-d obtained from Scheme 3 and 700 mL of diisopropyl ether were added thereto, and after stirring, 205 mL of methyl magnesium bromide was slowly added dropwise. After dropping, the mixture was stirred at 50°C. When the reaction was completed, the resultant product was layer-separated to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to obtain 58.0 g (82.8%) of <1-d> through column chromatography.

Synthetic example 1-5. Synthesis of <1-e>

<1-e> was synthesized by the following Reaction Scheme 5.

[Scheme 5]

<1-e>

58 g (0.154 mol) of a compound represented by Chemical Formula 1-d obtained from Scheme 4 and 150 mL of phosphoric acid were added and stirred at room temperature. When the reaction was completed, water was poured over the result of the reaction and stirred. After stirring, it was filtered and washed with water and methanol. 44.8 g (81.1%) of <1-e> was obtained by column chromatography.

Synthetic example 1-6. Synthesis of <18>

<18> was synthesized by the following Reaction Scheme 6.

[Scheme 6]

<Formula 18>

In a 100 mL round-bottom flask, 7.0 g (15.0 mmol) of the compound represented by Formula 1-e obtained from Scheme 5, 15.9 g (41.0 mmol) of Formula 1-b obtained from Scheme 2, tris(dibenzylideneacetone)dipalladium 0.7 g (1.0 mmol), 1,1'-bis (diphenylphosphino) ferrocene 0.5 g (1.0 mmol), sodium tertiary butoxide 7.9 g (82.0 mmol) and toluene 105 mL were added and refluxed and stirred for 24 hours. . After the reaction was completed, the temperature was adjusted to room temperature, and then the crystals were filtered. The crystal was recrystallized from methylene chloride and acetone to obtain 7.3 g (56.2%) of a compound represented by <Formula 18>.

MS (MALDI-TOF): m/z 666.28 [M] ⁺

Anal. Calc. for C ₄₈ H ₃₄ N ₄ : C, 86.46; H, 5.14; N, 8.40. Found C, 86.45; H, 5.15; N, 8.42.

Synthetic example 2. Synthesis of Formula 107

Synthetic example 2-1. Synthesis of <2-a>

<2-a> was synthesized by the following scheme 7.

[Scheme 7]

<2-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-a to obtain <2-a> 108.3 g (88.3%).

Synthetic example 2-2. Synthesis of <2-b>

<2-b> was synthesized by the following scheme 8.

[Scheme 8]

<2-b>

In a 1000 mL round-bottom flask, 6.8 g of sodium hydride was dissolved in 100 mL of N,N-diethylamide under nitrogen, and cooled to 0°C. 63.9 g (0.283 mol) of the compound represented by the formula 2-a obtained from Scheme 7 at 0° C. was dissolved in 200 mL of N,N-diethylamide and slowly added dropwise. After dropping, the mixture was stirred for 1 hour. At 0° C., 20 g (0.189 mol) of carbazole was dissolved in 100 mL of N,N-diethylamide and slowly added dropwise. After dropping, the mixture was stirred at room temperature. When the reaction was completed, the resultant product was poured into water, stirred, filtered and washed with water and methanol to obtain 45.2 g (67.3%).

Synthetic example 2-3. Synthesis of <2-c>

<2-c> was synthesized by the following Reaction Scheme 9.

[Scheme 9]

<2-c>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b, to obtain 32.7 g (81.5%) of <2-c>.

Synthetic example 2-4. Synthesis of <2-d>

<2-d> was synthesized by the following scheme 10.

[Scheme 10]

<2-d>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b to obtain 54.3 g (78.7%) of <2-d>.

Synthetic example 2-5. Synthesis of <2-f>

<2-f> was synthesized by the following scheme 11.

[Scheme 11]

<2-f>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-c to obtain <2-f> 41.60 g (86.7%).

Synthetic example 2-5. Synthesis of <Formula 107>

<107> was synthesized by the following Reaction Scheme 12.

[Scheme 12]

<Formula 107>

It was synthesized in the same manner as in the compound synthesis method represented by Chemical Formula 18, to obtain 9.4 g (70.1%) of <Chemical Formula 18>.

MS (MALDI-TOF): m/z 829.32 [M] ⁺

Anal. Calc. for C ₆₀ H ₃₉ N ₅ : C, 86.63; H, 4.74; N, 8.44. Found C, 86.65; H, 4.72; N, 8.43.

Synthetic example 3. Synthesis of Formula 141

Synthetic example 3-1. Synthesis of <3-a>

<3-a> was synthesized by the following scheme 13.

[Scheme 13]

<3-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 2-a to obtain 42.6 g (85.9%) of <3-a>.

Synthetic example 3-2. Synthesis of <3-b>

<3-b> was synthesized by the following scheme 14.

[Scheme 14]

<3-b>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b to obtain <3-b> 15.3g (77.1%).

Synthetic example 3-3. Synthesis of <3-c>

<3-c> was synthesized by the following Reaction Scheme 15.

[Scheme 15]

<3-c>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-c to obtain <3-c> 107.30 g (86.0%).

Synthetic example 3-4. Synthesis of <3-d>

<3-d> was synthesized by the following Reaction Scheme 16.

[Scheme 16]

<3-d>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-d to obtain <3-d> 42.30 g (84.6%).

Synthetic example 3-5. Synthesis of <3-f>

<3-f> was synthesized by the following scheme 17.

[Scheme 17]

<3-f>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-e to obtain 35.0 g (87.8%) of <3-f>.

Synthetic example 3-6. Synthesis of <Formula 141>

<Formula 141> was synthesized by Reaction Scheme 18 below.

[Reaction Scheme 18]

<Formula 141>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18 to obtain 10.2 g (65.3%).

MS (MALDI-TOF): m/z 748.27 [M] ⁺

Anal. Calc. for C ₅₂ H ₃₆ N ₄ S: C, 83.39; H, 4.84; N, 7.48. Found C, 83.41H, 4.83 N, 7.47.

Synthetic example 4. Synthesis of Formula 192

Synthetic example 4-1. Synthesis of <4-a>

<4-a> was synthesized by the following Reaction Scheme 19.

[Scheme 19]

<4-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-a to obtain 45.8 g (77.3%) of <4-a>.

Synthetic example 4-2. Synthesis of <4-b>

<4-b> was synthesized by the following scheme 20.

[Scheme 20]

<4-b>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b to obtain <4b> 31.5 g (86.8%).

Synthetic example 4-3. Synthesis of <4-c>

<4-c> was synthesized by the following Reaction Scheme 21.

[Scheme 21]

<4-c>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-c to obtain <4-c> 115.70 g (86.4%).

Synthetic example 4-4. Synthesis of <4-d>

<4-d> was synthesized by the following scheme 22.

[Scheme 22]

<4-d>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-d to obtain 98.70 g (85.8%) of <4-c>.

Synthetic example 4-5. Synthesis of <4-f>

<4-f> was synthesized by the following scheme 23.

[Scheme 23]

<4-f>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-e to obtain <4-f> 80.9 g (91.1 %).

Synthetic example 4-6. Synthesis of <192>

<192> was synthesized by the following Reaction Scheme 24.

[Scheme 24]

<Formula 192>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18 to obtain 8.7g (56.9%).

MS (MALDI-TOF): m/z 565.25 [M] ⁺

Anal. Calc. for C ₄₁ H ₃₁ N ₃ : C, 87.05; H, 5.52; N, 7.43. Found C, 87.04; H, 5.53; N, 7.44.

Synthetic example 5. Synthesis of Formula 222

Synthetic example 5-1. Synthesis of <5-a>

<5-a> was synthesized by the following Reaction Scheme 25.

[Reaction Scheme 25]

<5-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-c to obtain <4-a> 95.4 g (74.9%).

Synthetic example 5-2. Synthesis of <5-b>

<5-b> was synthesized by the following Reaction Scheme 26.

[Scheme 26]

<5-b>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-d to obtain 87.3 g (92.0%) of <5-b>.

Synthetic example 5-3. Synthesis of <5-c>

<5-c> was synthesized by the following Reaction Scheme 27.

[Scheme 27]

<5-c>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-e, to obtain 86.7 g (85.6%) of <5-c>.

Synthetic example 5-4. Synthesis of <5-d>

<5-d> was synthesized by the following scheme 28.

[Scheme 28]

<5-d>

In a 1000 mL round-bottom flask, add 250 mL of N,N-dimethylamide to 50 g (0.162 mol) of the compound represented by 5-d obtained in Scheme 27, stir for 30 minutes under nitrogen and cool the reaction to 0°C. Order. 29.5 g (0.178 mol) of N-bromosuccinimide was dissolved in 2500 mL of N,N-dimethylamide and added dropwise. After dropping, the mixture was stirred at room temperature. When the reaction was completed, the resultant product was poured into water, stirred, filtered and washed with water and methanol to obtain 56.1 g (89.4%) of the compound represented by Chemical Formula 5-d.

Synthetic example 5-5. Synthesis of <5-f>

<5-f> was synthesized by Reaction Scheme 29 below.

[Scheme 29]

<5-f>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18, to obtain 8.6 g (70.4%) of <5-f>.

Synthetic example 5-6. Synthesis of <222>

<222> was synthesized by the following Reaction Scheme 30.

[Scheme 30]

<Formula 222>

In a 500 mL round-bottom flask, 0.5 g of sodium hydride was dissolved in 35 mL of N,N-diethylamide under nitrogen, and cooled to 0°C. At 0°C, 7.0 g (0.018 mol) of the compound represented by the formula 5-d obtained from Scheme 29 was dissolved in 35 mL of N,N-diethylamide and slowly added dropwise. After dropping, the mixture was stirred for 1 hour. 5.9 g (0.022 mol) of the compound represented by Formula 1-a obtained from Scheme 1 at 0° C. was dissolved in 60 mL of N,N-diethylamide and slowly added dropwise. After dropping, the mixture was stirred at room temperature. When the reaction was completed, the resultant product was poured into water, stirred, filtered and washed with water and methanol to obtain 7.6 g (73.0%).

MS (MALDI-TOF): m/z 705.29 [M] ⁺

Anal. Calc. for C ₅₀ H ₃₅ N ₅ : C, 85.08; H, 5.00; N, 9.92. Found C, 85.09; H, 5.01; N, 9.93.

Synthetic example 6. Synthesis of Formula 242

Synthetic example 6-1. Synthesis of <6-a>

<6-a> was synthesized by the following scheme 30.

[Scheme 30]

<6-a>

In a 500 mL three-necked flask, 100 mL (100 mmol) of a 1 M tetrahydrofuran solution of phenylmagnesium bromide was added, and 100 mL of dry tetrahydrofuran was added and heated at 45°C. In it, a 50 mL solution of 5.91 g (50 mmol) of 2-cyanoaniline was added dropwise. After refluxing for 1.5 hours, a solution of 100 mL of dry ether of 13.2 g (60 mL) of 4-bromobenzoic acid chloride was added dropwise by cooling to 0°C. After heating at 45° C. for 2 hours, cooled to 0° C. and then saturated aqueous ammonium chloride solution is added. After the precipitated solid was filtered and washed with methanol, 10.8 g (60%) of dried <6-a> was obtained.

Synthetic example 6-2. Synthesis of <242>

<242> was synthesized by the following Reaction Scheme 31.

[Scheme 31]

<Formula 242>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18 to obtain 8.7g (69.8%) of <Chemical Formula 242>.

MS (MALDI-TOF): m/z 639.27 [M] ⁺

Anal. Calc. for C ₄₇ H ₃₃ N ₃ : C, 88.23; H, 5.22; N, 10.36. Found C, 88.22; H, 5.21; N, 10.37.

Synthetic example 7. Synthesis of Formula 239

Synthetic example 7-1. Synthesis of <7-a>

<7-a> was synthesized by the following scheme 32.

[Scheme 32]

<7-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 5-d to obtain 51.3 g (84.1%) of <7-a>.

Synthetic example 7-2. Synthesis of <7-b>

<7-b> was synthesized by the following Reaction Scheme 33.

[Reaction Scheme 33]

<7-b>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18, to obtain 11.6 g (68.2%) of <7-b>.

Synthetic example 7-5. Synthesis of <239>

<239> was synthesized by the following Reaction Scheme 34.

[Scheme 34]

<Formula 239>

10.0 g (15.0 mmol) of the compound represented by Chemical Formula 7-b obtained from Scheme 34 was dissolved in 80 mL of tetrahydrofuran under a stream of nitrogen, and slowly stirred 10.7 mL (16.05 mmol) of 1.6 M normal-butyllithium while stirring at -78°C. It was added dropwise, and when the dropwise addition was completed, it was stirred for 1 hour while maintaining -78 deg. Thereafter, 2.2 g (22.0 mmol) of chloro-trimethyl silane was slowly added dropwise, stirred at room temperature for 2 hours, extracted with ethyl acetate and water, the organic layer was concentrated under reduced pressure, and recrystallized from methylene chloride and nucleic acid to give 7.9 g ( 39.2%).

MS (MALDI-TOF): m/z 738.32 [M] ⁺

Anal. Calc. for C ₅₁ H ₄₂ N ₄ Si: C, 82.89; H, 5.73; N, 7.58. Si, 3.80. Found C, 82.88; H, 5.74; N, 7.57. Si, 3.81.

Synthetic example 8. Synthesis of Formula 266

Synthetic example 8-1. Synthesis of <8-a>

<8-a> was synthesized by the following scheme 35.

[Scheme 35]

<8-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18 to obtain <8-a> 115.40 g (88.1%).

Synthetic example 8-2. Synthesis of <8-b>

<8-b> was synthesized by the following scheme 36.

[Scheme 36]

<8-b>

50.0 g (15.5 mmol) of the compound represented by Formula 8-a obtained from Scheme 35 was dissolved in 400 mL of tetrahydrofuran under a stream of nitrogen, and then slowly stirred 106.7 mL (17.07 mmol) of 1.6 M normal-butyllithium while stirring at -78°C. It was added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78 deg. Then, 24.2 g (0.233 mmol) of trimethylborate was slowly added dropwise, and then raised to room temperature and stirred for 3 hours. When the reaction is over, 300 mL of 1M aqueous hydrochloric acid solution is added dropwise at room temperature and stirred for 30 minutes. Then extracted with ethyl acetate and water, the organic layer was concentrated under reduced pressure, and recrystallized from methylene chloride and nucleic acid to obtain 36.5 g (81.2%) of the compound represented by <8-b>.

Synthetic example 8-5. Synthesis of <8-c>

<8-c> was synthesized by the following scheme 37.

[Scheme 37]

<8-c>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b to obtain 15.60 g (74.6%) of <8-c>.

Synthetic example 8-6. Synthesis of <266>

<266> was synthesized by the following Reaction Scheme 38.

[Scheme 38]

<Formula 266>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18 to obtain 6.5g (67.0%).

MS (MALDI-TOF): m/z 831.34 [M] ⁺

Anal. Calc. for C ₆₀ H ₄₁ N ₅ : C, 86.62; H, 4.97; N, 8.42. Found C, 86.64; H, 4.96; N, 8.43.

Synthesis Example 9 . Synthesis of Formula 274

Synthetic example 9-1. Synthesis of <274>

<274> was synthesized by the following Reaction Scheme 39.

[Scheme 39]

<Formula 274>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 2-b to obtain 11.4 g (65.2%).

MS (MALDI-TOF): m/z 540.23 [M] ⁺

Anal. Calc. for C ₃₈ H ₂₈ N ₄ : C, 84.42; H, 5.22; N, 10.26. Found C, 84.44; H, 5.23; N, 10.27.

Synthetic example 10. Synthesis of Formula 279

Synthetic example 10-1. Synthesis of <10-a>

<10-a> was synthesized by the following scheme 40.

[Reaction Scheme 40]

<10-a>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-a to obtain <10-a> 66.30 g (90.9%).

Synthetic example 10-2. Synthesis of <10-b>

<10-b> was synthesized by the following scheme 41.

[Scheme 41]

<10-b>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 1-b to obtain 27.2 g (75.2%) of <10-b>.

Synthetic example 10-3. Synthesis of <279>

<279> was synthesized by the following scheme 42.

[Reaction Scheme 42]

<Formula 279>

Synthesis was performed in the same manner as in the compound synthesis method represented by Chemical Formula 18, to obtain 8.7g (68.6%).

MS (MALDI-TOF): m/z 618.25 [M] ⁺

Anal. Calc. for C ₄₂ H ₃₀ N ₆ : C, 81.53; H, 4.89; N, 13.58. Found C, 81.55; H, 4.87; N, 13.59.

Example : Preparation of organic light emitting diodes

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

Comparative example

The organic light emitting diode device for the comparative example was manufactured in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound prepared by the invention in the device structure of the above embodiment, 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 18 Ir(ppy) ₃ 10 4.31 4874 0.265 0.624 154 Example 2 107 Ir(ppy) ₃ 10 4.65 5201 0.295 0.618 141 Example 3 141 Ir(ppy) ₃ 10 5.06 4658 0.281 0.629 131 Example 4 192 Ir(ppy) ₃ 10 4.60 4751 0.305 0.624 145 Example 5 222 Ir(ppy) ₃ 10 4.25 5031 0.309 0.628 172 Example 6 242 Ir(ppy) ₃ 10 4.85 4875 0.289 0.626 102 Example 7 239 Ir(ppy) ₃ 10 4.24 4956 0.291 0.620 174 Example 8 266 Ir(ppy) ₃ 10 4.35 5351 0.314 0.619 164 Example 9 274 Ir(ppy) ₃ 10 4.47 5241 0.296 0.618 178 Example 10 279 Ir(ppy) ₃ 10 4.84 5102 0.309 0.624 106

In [Table 1], T80 means the time required for the luminance to decrease to 80% compared to the initial luminance.

As shown in [Table 1], when the organic light emitting compound embodied in accordance with the present invention is used as the host compound of the light emitting layer of the organic electroluminescent device, the lifespan characteristics are significantly improved, the light emission characteristics are excellent, and the driving voltage is also improved. By lowering, it is possible to improve power consumption 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 (12)

The organic light emitting compound represented by any one of the following [Formula 1-1] to [Formula 1-5]:
[Formula 1-1] [Formula 1-2]

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

[Formula 1-5]

In the above [Formula 1-1] to [Formula 1-5],
L _a is any one selected from substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted heteroarylene having 3 to 50 carbon atoms (n is an integer of 1 to 2),
Connected to the L _a

Is any one selected from the following [Structural Formula 2],
[Structural Formula 2]

Y is CR ₁ R ₂ , and R ₁ and R ₂ are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms and substituted or unsubstituted aryl groups having 6 to 40 carbon atoms,
R ₉ and R ₁₀ are each independently hydrogen, deuterium, hydroxyl group, nitro group, amino group, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted 6 to 40 carbon atoms. Any one selected from an aryl group, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; (A plurality of R ₉ and R ₁₀ are the same or different from each other),
Each of R ₁ , R ₂ , R ₉ and R ₁₀ may combine with adjacent substituents to form a saturated or unsaturated ring,
The'*' in [Formula 2] is _a site in which any one of a plurality of R ₉ is connected to L _a . According to claim 1,
When L _a , R ₁ , R ₂ , R ₉ and R ₁₀ are each substituted, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 40 carbon atoms, a hetero group having 3 to 20 carbon atoms It is substituted with one or more selected from the group consisting of an aryl group, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a hydroxyl group, a nitro group, an amino group, a cyano group, a halogen group, and deuterium, and substituted An organic light-emitting compound characterized in that the substituted substituents can form a saturated or unsaturated ring by combining with adjacent substituents. delete delete delete According to claim 1,
[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]

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

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

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

[Formula 58] [Formula 59] [Formula 60] [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]

[Formula 78] [Formula 79] [Formula 80] [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]

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

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

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

[Chemical Formula 130] [Chemical Formula 131] [Chemical Formula 132] [Chemical 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]

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

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

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

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

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

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

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

[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]

[Chemical Formula 226] [Chemical Formula 227] [Chemical Formula 228] [Chemical Formula 229]

[Formula 234] [Formula 235] [Formula 236] [Formula 237]

[Formula 238] [Formula 239] [Formula 240] [Formula 241]

[Formula 242] [Formula 243] [Formula 244] [Formula 245]

[Formula 246] [Formula 247] [Formula 248] [Formula 249]

[Formula 250] [Formula 251] [Formula 252] [Formula 253]

[Formula 254] [Formula 255] [Formula 256] [Formula 257]

[Formula 258] [Formula 259] [Formula 260] [Formula 261]

[Formula 262] [Formula 263] [Formula 264] [Formula 265]

[Chemical Formula 266] [Chemical Formula 267] [Chemical Formula 268] [Chemical Formula 269]

[Formula 270] [Formula 271] [Formula 272] [Formula 273]

[Formula 274] [Formula 275] [Formula 276] [Formula 277]

[Formula 278] [Formula 279] [Formula 280] [Formula 281]

[Formula 282] [Formula 283] [Formula 284] [Formula 285]

[Formula 286] [Formula 287] [Formula 288] [Formula 289]

[Formula 290] [Formula 291] [Formula 292] [Formula 293] An organic thin film layer for an organic light emitting device comprising at least one organic light emitting compound represented by [Formula 1] according to claim 1. The method of claim 7,
The organic thin film layer is an organic thin film layer, characterized in that the organic light emitting compound represented by the [Formula 1] as a host, further comprising at least one dopant compound. A first electrode; A second electrode; And an organic thin film layer according to claim 7 interposed between the first electrode and the second electrode. The method of claim 9,
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 first electrode and the second electrode. ,
The organic electroluminescent device, characterized in that one of the light emitting layer, hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer and electron blocking layer is the organic thin film layer. The method of claim 10,
An organic electroluminescent device characterized in that the light emitting layer is the organic thin film layer. The method of claim 9,
The organic electroluminescent device comprises at least one organic light emitting layer that emits blue, red or green light, and emits white light.

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