KR20180014985A - Novel organic compounds derivatives and organic light-emitting diode therewith - Google Patents

Abstract

The present invention relates to an organic compound represented by the chemical formula (A) or (B) and to an organic light-emitting device comprising the same. In the chemical formulas (A) and (B), R_1 to R_14, L1, L2, Ar1 to Ar3, n and m are as described in detailed description of the invention. The first object of the present invention is to provide the organic compound having a specific structure capable of having high efficiency, low voltage and long life characteristics by using the compound in an electron transporting layer or a hole transporting layer in the organic light emitting device.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic compound and an organic light emitting diode (OLED)

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic compound and an organic light emitting device including the organic compound. More particularly, the present invention relates to a novel organic compound capable of realizing device characteristics such as high efficiency, long life and low- To an organic light emitting device.

The organic light emitting diode (OLED) is a display using a self-luminous phenomenon. The organic light emitting diode (OLED) has a wide viewing angle and is thinner and lighter than a liquid crystal display and has a fast response speed. ) Applications for display or illumination are expected.

Generally, an organic light emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy. The organic light emitting device using the organic light emitting phenomenon typically has a structure including an anode, an anode, and an organic layer between the anode and the cathode.

Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, Or a hole blocking layer may be added.

Of these, in order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent luminous efficiency and high stability in a thin film state, as a prior art related to an electron transporting layer material, it is disclosed in Korean Patent Publication No. 10-2012-0104204 (2012.09.20) describes an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure, and in JP-A-2010-168363 (2010.08.05), an external quantum efficiency and a driving voltage Discloses an anthracene derivative having a pyridine naphthyl group, which has excellent characteristics.

On the other hand, as a conventional technique related to the hole transporting layer, JP-A 10-1074193 (Oct. 2011, Oct. 14, 2011) discloses a method for producing a hole transporting layer comprising a compound having a gore structure in which at least one benzene ring is condensed in a carbazole structure Emitting device is disclosed in Japanese Patent Application Laid-Open No. 10-1455156 (Publication Date: Oct. 24, 2014, Oct. 27, 2014), an emission assistant having a HOMO energy level between a hole transport layer HOMO energy level and a light emission layer HOMO energy level is provided between a hole transport layer and a light emission layer Emitting layer having a layer formed thereon is disclosed.

However, although various methods for manufacturing an organic light emitting device having more efficient light emitting characteristics have been attempted in the prior art including the above-mentioned prior arts, it is still possible to operate at a low voltage, and the organic light emitting device having improved luminous efficiency and long life There is a continuing need to develop a material that can be used as an electron transport layer and a hole transport layer for a light emitting device.

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20)

Japanese Unexamined Patent Application Publication No. 2010-168363 (Aug. 05, 2010)

Patent Registration No. 10-1074193 (Published on October 14, 2011)

Patent Registration No. 10-1455156 (Publication date: Oct. 27, 2014)

Accordingly, the first technical object of the present invention is to provide an organic compound having a specific structure capable of having high efficiency, low voltage, and long life characteristics by using it in an electron transporting layer or a hole transporting layer in an organic light emitting device.

A second object of the present invention is to provide a novel organic light emitting device including the organic compound in an electron transport layer or a hole transport layer.

In order to achieve the above technical problems, the present invention provides an organic compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

The substituents R 1 to R 14 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,

In the above formula (A), one or two substituents of the substituents R 1 to R 12 are a single bond which binds to the above-mentioned Al

 In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic compound of the present invention.

The organic light emitting device comprising the compound represented by the formula (A) or (B) according to the present invention in the electron transporting layer or the hole transporting layer can have high efficiency, low voltage and long life characteristics as compared with the conventional organic light emitting device.

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

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

The organic compound according to the present invention has a structure represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

The substituents R 1 to R 14 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,

In the above formula (A), one or two substituents of the substituents R 1 to R 12 are a single bond which binds to the above-mentioned Al

 In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms,

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms.

On the other hand, in consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted C1-C30 alkyl group" or "substituted or unsubstituted C6-C50 aryl group" in the present invention, The carbon number of the alkyl group of 1 to 30 and the aryl group of the carbon number of 6 to 50 means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety . For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" each independently represent an alkyl group having 1 to 10 carbon atoms 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, a halogenated alkyl group having 1 to 24 carbon atoms, an alkyl group having 2 to 20 carbon atoms, An alkenyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, It may be substituted with a heteroaryl group of a small number of 6 to 24 aryl group, having 7 to 24 of the arylalkyl group, having 2 to 24 carbon atoms or heteroaryl group having 2 to 24.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 2 to 24 carbon atoms in which the heteroaryl group includes 1,2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Refers to a ring aromatic system, which rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

In the present invention, the aromatic heterocyclic ring means that at least one of aromatic carbons in the aromatic hydrocarbon ring is substituted with at least one hetero atom selected from N, O, P, Si, S, Ge, Se and Te.

Specific examples of the alkyl group as the substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl and hexyl. The hydrogen atom may be substituted with a substituent similar to that of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

More specifically, the compounds represented by the above formula (A) or (B) according to the present invention will be described in more detail. They include 5-membered rings R5 to R12 including 6-membered ring aromatic rings R13 and R14 (Phenanthrene skeleton) 'having a carbon number of 14 is condensed with each other, and one or two substituents of the substituents R 1 to R 21 in these condensed rings are single bonds bonded to the A 1 or A 2. .

In one embodiment, the substituents Ar1 to Ar3 are the same or different and each independently selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, .

The substituents R13 and R14 may be the same or different and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

The substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and the substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms is selected from the following structural formulas A to Q It can be either.

[Structural Formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

[Structural formula P] [Structural formula Q]

Substituent R in the structural formulas A to Q is the same as R1 to R14 defined above,

K is an integer of 1 to 7, and when k is 2 or more, each substituent R is the same or different,

When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring.

In formula (B), Ar2 and Ar3 may be the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment according to the present invention, in the above formula (A) and formula (B), one of the substituents R 1 to R 4 is a single bond bonding to A 1 or A 2, or one of the substituents R 5 to R 12 is bonded to A 1 or A 2 May be a single bond.

In an embodiment according to the present invention, the substituent which is not connected to A1 or A2 among the substituents R1 to R12 may be hydrogen or deuterium.

In one embodiment of the present invention, the linking groups L 1 and L 2 may be the same or different from each other, and each may be a single bond or any one selected from the following structural formulas 1 to 9.

[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]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium.

On the other hand, the organic compound represented by the above-mentioned formula (A) of the present invention may be a compound in which only one substituent of the substituent groups R 1 to R 12 is a single bond to the above-mentioned Al

Specific examples of the organic compound represented by the above formula (A) or (B) according to the present invention may be a compound represented by any one selected from the following [compounds 1] to [144] Do not.

[Compound 1] [Compound 2] [Compound 3] [Compound 4]

[Compound 5] [Compound 6] [Compound 7] [Compound 8]

[Compound 9] [Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15] [Compound 16]

[Compound 17] [Compound 18] [Compound 19] [Compound 20]

[Compound 21] [Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27] [Compound 28]

[Compound 29] [Compound 30] [Compound 31] [Compound 32]

[Compound 33] [Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39] [Compound 40]

[Compound 41] [Compound 42] [Compound 43] [Compound 44]

[Compound 45] [Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51] [Compound 52]

[Compound 53] [Compound 54] [Compound 55] [Compound 56]

[Compound 57] [Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63] [Compound 64]

[Compound 65] [Compound 66] [Compound 67] [Compound 68]

[Compound 69] [Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75] [Compound 76]

[Compound 77] [Compound 78] [Compound 79] [Compound 80]

[Compound 81] [Compound 82] [Compound 83] [Compound 84]

[Compound 85] [Compound 86] [Compound 87] [Compound 88]

[Compound 89] [Compound 90] [Compound 91] [Compound 92]

[Compound 93] [Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99] [Compound 100]

[Compound 101] [Compound 102] [Compound 103] [Compound 104]

[Compound 105] [Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111] [Compound 112]

[Compound 113] [Compound 114] [Compound 115] [Compound 116]

[Compound 117] [Compound 118] [Compound 119] [Compound 120]

[Compound 121] [Compound 122] [Compound 123] [Compound 124]

[Compound 125] [Compound 126] [Compound 127] [Compound 128]

[Compound 129] [Compound 130] [Compound 131] [Compound 132]

[Compound 133] [Compound 134] [Compound 135] [Compound 136]

[Compound 137] [Compound 138] [Compound 139] [Compound 140]

[Compound 141] [Compound 142] [Compound 143] [Compound 144]

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the organic compound according to the present invention described above.

Herein, " an organic layer includes at least one organic compound " in the present invention means that one organic compound belonging to the category of the present invention or two or more different compounds belonging to the category of the organic compound May be included.

At this time, the organic layer containing the organic compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer .

Further, the organic compound of the present invention can be used for a hole transporting layer or for an electron transporting layer.

As the material of the hole transporting layer according to the present invention, organic compounds represented by the above formula (A) or (B) can be used. In addition, compounds other than the organic compound represented by the above-mentioned formula (A) or (B) can be additionally used, and electron-donating molecules having a low ionization potential can be used, and diamine, triamine Or tetraamine derivatives are widely used, and for example, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl] -4,4'-diamine ), N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD)

A hole injection layer (HIL) may be additionally formed on the lower part of the hole transport layer. The hole injection layer material may be an organic compound represented by the formula (A) or (B) In the case where the organic compound represented by the above formula (A) or (B) is not used, a hole injection layer commonly used in the art can be used.

Such conventionally used hole injection layers include, for example, copper phthalocyanine (CuPc) or starburst type amine TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m- 4 ', 4 "-tris- (3-methylphenylphenylamino) triphenylamine) and the like can be used.

In addition, the light emitting layer in the organic light emitting device of the present invention may be composed of a host and a dopant. In this case, the host used in the light emitting layer may include at least one compound represented by the following formula (H) .

[Formula H] <

In the above formula (H)

X ₁ to X ₁₀ are the same or different from each other and each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted 5 A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted hetero atom, a substituted Is a group selected from the group consisting of an unsubstituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group And the groups adjacent to each other may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero.

More specifically, the host may be represented by any one selected from the group consisting of [compounds 201] to [396], but is not limited thereto.

[Compound 201] [Compound 202] [Compound 203] [Compound 204]

[Compound 205] [Compound 206] [Compound 207] [Compound 208]

[Compound 209] [Compound 210] [Compound 211] [Compound 212]

[Compound 213] [Compound 214] [Compound 215] [Compound 216]

[Compound 217] [Compound 218] [Compound 219] [Compound 220]

[Compound 221] [Compound 222] [Compound 223] [Compound 224]

[Compound 225] [Compound 226] [Compound 227] [Compound 228]

[Compound 229] [Compound 230] [Compound 231] [Compound 232]

[Compound 233] [Compound 234] [Compound 235] [Compound 236]

[Compound 237] [Compound 238] [Compound 239] [Compound 240]

[Compound 241] [Compound 242] [Compound 243] [Compound 244]

[Compound 245] [Compound 246] [Compound 247] [Compound 248]

[Compound 249] [Compound 250] [Compound 251] [Compound 252]

[Compound 253] [Compound 254] [Compound 255] [Compound 256]

[Compound 257] [Compound 258] [Compound 259] [Compound 260]

[Compound 261] [Compound 262] [Compound 263] [Compound 264]

[Compound 265] [Compound 266] [Compound 267] [Compound 268]

[Compound 269] [Compound 270] [Compound 271] [Compound 272]

[Compound 273] [Compound 274] [Compound 275] [Compound 276]

[Compound 277] [Compound 278] [Compound 279] [Compound 280]

[Compound 281] [Compound 282] [Compound 283] [Compound 284]

[Compound 285] [Compound 286] [Compound 287] [Compound 288]

[Compound 289] [Compound 290] [Compound 291] [Compound 292]

[Compound 293] [Compound 294] [Compound 295] [Compound 296]

[Compound 297] [Compound 298] [Compound 299] [Compound 300]

[Compound 301] [Compound 302] [Compound 303] [Compound 304]

[Compound 305] [Compound 306] [Compound 307] [Compound 308]

[Compound 309] [Compound 310] [Compound 311] [Compound 312]

[Compound 313] [Compound 314] [Compound 315] [Compound 316]

[Compound 317] [Compound 318] [Compound 319] [Compound 320]

[Compound 321] [Compound 322] [Compound 323] [Compound 324]

[Compound 325] [Compound 326] [Compound 327] [Compound 328]

[Compound 329] [Compound 330] [Compound 331] [Compound 332]

[Compound 333] [Compound 334] [Compound 335] [Compound 336]

[Compound 337] [Compound 338] [Compound 339] [Compound 340]

[Compound 341] [Compound 342] [Compound 343] [Compound 344]

[Compound 345] [Compound 346] [Compound 347] [Compound 348]

[Compound 349] [Compound 350] [Compound 351] [Compound 352]

[Compound 353] [Compound 354] [Compound 355] [Compound 356]

[Compound 357] [Compound 358] [Compound 359] [Compound 360]

[Compound 361] [Compound 362] [Compound 363] [Compound 364]

[Compound 365] [Compound 366] [Compound 367] [Compound 368]

[Compound 369] [Compound 370] [Compound 371] [Compound 372]

[Compound 373] [Compound 374] [Compound 375] [Compound 376]

[Compound 377] [Compound 378] [Compound 379] [Compound 380]

[Compound 381] [Compound 382] [Compound 383] [Compound 384]

[Compound 385] [Compound 386] [Compound 387] [Compound 388]

[Compound 389] [Compound 390] [Compound 391] [Compound 392]

[Compound 393] [Compound 394] [Compound 395] [Compound 396]

Meanwhile, the dopant used in the light emitting layer in the organic light emitting device of the present invention may be a compound represented by the following formula (1) or (2), and various known dopant materials may be used.

            [Chemical Formula 1] < EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, It is a single bond or _{[C (R 5) (R} 6)] p, wherein p is an integer and are from 1 to 3, p is 2 or more two or more of R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1]  [Substituent 2]    [Substituent 3]   

  [Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7]     [Substituent group 8] [Substituent group 9]

 [Substituent 10] [Substituent group 11]       [Substituent group 12]

 [Substituent group 13] [Substituent group 14] [Substituent 15]

 [Substituent group 16] [Substituent group 17] [Substituent 18]

 [Substituent group 19] [Substituent group 20] [Substituent group 21]

 [Substituent 22]     [Substituent group 23] [Substituent group 24]

[Substituent 25]        [Substituent 26]     [Substituent 27]

[Substituent 28]     [Substituent group 29] [Substituent group 30]

[Substituent 31]  [Substituent group 32]     [Substituent group 33]

[Substituent 34] [Substituent 35]      [Substituent 36]

[Substituent group 37]    [Substituent group 38] [Substituent group 39]

[Substituent 40]  [Substituent 41]  [Substituent 42]

[Substituent 43] [Substituent 44]       [Substituent 45]

[Substituent group 46] [Substituent group 47]     [Substituent group 48]

[Substituent 49]     [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

The light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

When the light emitting layer according to the present invention includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

On the other hand, in the electron transport layer used in the present invention, when the organometallic compound represented by the formula (F) is used in combination with the organic compound material of the present invention, or when the organic compound represented by the above formula (A) or The organometallic compound represented by Formula F may be used singly.

[Chemical Formula F]

In the above formula (F)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond; Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

M is 1 to 3 when M is boron or aluminum, and n is any of 0 to 2 and satisfies m + n = 3.

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

[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] [Structural formula C15] [Structural formula C16]

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

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

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

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

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

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

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

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring. Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term " substituted aryl group "

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the related art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

As the electron injection layer forming material, any material known as an electron injection layer forming material such as CsF, NaF, LiF, NaCl, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer may vary depending on the compound used, but may generally be selected from the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injecting layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

In the present invention, the negative electrode may be formed of a material selected from the group consisting of Li, Mg, Al, Al-Li, Ca, Mg- Mg-Ag), or a transmissive negative electrode using ITO or IZO can be used to obtain a top-emitting device.

In the present invention, at least one layer selected from the functional layer having the hole injection layer, the hole transport layer, the hole injection function and the hole transport function, the light emitting layer, the electron transport layer, and the electron injection layer may be formed by a deposition process or a solution process .

Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing a structure of an organic light emitting device of the present invention. The organic light emitting 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, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

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 to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus 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 . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

Synthesis Example 1. Synthesis of Compound 1

Synthesis Example 1-1. Synthesis of <Intermediate 1-a>

<Intermediate 1-a> was synthesized by the following Reaction Scheme 1.

[Reaction Scheme 1]

                      <Intermediate 1-a>

4-bromo-2-iodobenzoate (31.7 g, 93 mmol), phenylboronic acid (20 g, 164 mmol), potassium carbonate (26.4 g, 191 mmol), tetrakis triphenylphosphine (2.2 g, 2 mmol), water (80 mL), toluene (150 mL) and 1,4-dioxane (150 mL), and the mixture was refluxed for 12 hours. After the completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure. The resultant product was separated by column chromatography to obtain <Intermediate 1-a> (21.5 g, 79.4%).

Synthesis Example 1-2. Synthesis of <Intermediate 1-b>

<Intermediate 1-b> was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

<Intermediate 1-a> <Intermediate 1-b>

<Intermediate 1-a> (15 g, 52 mmol) and 100 mL of tetrahydrofuran are added to a dry 300 mL round-bottom flask reactor under nitrogen atmosphere, and methyl magnesium bromide (10 mL, 300 mmol) is added dropwise at 0 ° C. After completion of dropwise addition, the mixture is stirred at room temperature for 3 hours. After completion of the reaction, add 100 mL of 2 N HCl aqueous solution at 0 ° C and stir for 30 minutes. The layers were separated with ethyl acetate, and the organic layer was concentrated. Immediately, 100 mL of acetic acid and 10 mL of hydrochloric acid were added, and the mixture was refluxed with stirring for 10 hours. After completion of the reaction, excess water was added and stirred for 30 minutes, followed by filtration and separation by column chromatography to obtain <Intermediate 1-b> (12.1 g, 86%).

Synthesis Example 1-3. Synthesis of <Intermediate 1-c>

<Intermediate 1-c> was synthesized by the following Reaction Scheme 3.

[Reaction Scheme 3]

<Intermediate 1-b> <Intermediate 1-c>

<Intermediate 1-b> (42 g, 154 mmol) was dissolved in 420 mL of tetrahydrofuran in a nitrogen stream, and 1.6 M n-butyl lithium (155 mL, 247 mmol) is slowly added dropwise. When dropping is completed, stirring is continued for 1 hour and a half while maintaining the temperature at -78 ° C. After that, trimethyl borate (30.8 g, 297 mmol) was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 200 mL of a 2N hydrochloric acid aqueous solution is added dropwise at room temperature, followed by stirring for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and recrystallized to obtain <Intermediate 1-c> (34 g, 93%).

Synthesis Example 1-4. Synthesis of <Intermediate 1-d>

<Intermediate 1-d> was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

         <Intermediate 1-c> <Intermediate 1-d>

Synthesis was conducted in the same manner as in Synthesis Example 1-1, except that 2,5-dibromobenzaldehyde was used instead of 4-bromo-2-iodobenzoate and Intermediate 1-c> was used in place of phenylboronic acid <Intermediate 1-d> (21.3 g, 71%).

Synthesis Example 1-5. Synthesis of <Intermediate 1-e>

Intermediate 1-e &gt; was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

<Intermediate 1-d> <Intermediate 1-e>

To a 2 L round bottom flask reactor was added potassium tertiary butoxide (23.4 g, 192 mmol) and tetrahydrofuran (200 ml), stirred and cooled to 0 ° C under a nitrogen atmosphere. Methoxymethyltriphenylphosphonium chloride (65.8 g, 192 mmol) was dissolved in 300 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes. <Intermediate 1-d> (47 g, 125 mmol) was dissolved in 500 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water, and the organic layer was concentrated under reduced pressure. The resultant product was separated by column chromatography to obtain <Intermediate 1-e> (46.5 g, 92%).

Synthesis Example 1-6. Synthesis of <Intermediate 1-f>

<Intermediate 1-f> was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

<Intermediate 1-e> <Intermediate 1-f>

(46 g, 114 mmol), Bismuth (III) trifluoromethanesulfonate (3.8 g, 5.8 mmol) and 500 ml of 1,2-dichloroethane were added to a 1 L round bottom flask reactor under nitrogen atmosphere And the mixture is stirred at room temperature for 3 hours. After completion of the reaction, methanol was used to form a precipitate, and the solid was filtered to obtain <Intermediate 1-f> (37.8 g, 89%).

Synthesis Example 1-7. Synthesis of <Intermediate 1-g>

<Intermediate 1-g> was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

<Intermediate 1-f> <Intermediate 1-g>

Intermediate 1-g> (31.3 g, 81%) was obtained in the same manner as in Synthesis Example 1-3, except that Intermediate 1-f was used instead of Intermediate 1-b.

Synthesis Example 1-8. Synthesis of Compound 1

<Compound 1> was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

               <Intermediate 1-g> <Compound 1>

Synthesis Example 1-1 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 4-bromo-2-iodobenzoate and Intermediate 1-g> Was used to synthesize <compound 1> (3.7 g, 41%).

MS (MALDI-TOF): m / z 525.22 [M ^&lt; ⁺ &^gt;

Synthesis Example 2. Synthesis of Compound 9

Synthesis Example 2-1. Synthesis of <Intermediate 2-a>

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

[Reaction Scheme 9]

          <Intermediate 1-c> <Intermediate 2-a>

The procedure of Synthesis Example 1-4 was repeated except that 2,6-dibromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde to obtain Intermediate 2-a (23.3 g, 69.1%).

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

<Intermediate 2-b> was synthesized by the following Reaction Scheme 10.

[Reaction Scheme 10]

&Lt; Intermediate 2-a > < Intermediate 2-b &

Intermediate 2-b> (18.6 g, 82.1%) was obtained in the same manner as in Synthesis Example 1-5, except that <Intermediate 2-a> was used instead of <Intermediate 1-d>.

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

&Lt; Intermediate 2-c > was synthesized by the following Reaction Scheme 11.

[Reaction Scheme 11]

<Intermediate 2-b> <Intermediate 2-c>

Intermediate 2-c &gt; (15.6 g, 85.1%) was obtained in the same manner except that Intermediate 2-b was used instead of Intermediate 1-e in Synthesis Example 1-6.

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

<Intermediate 2-d> was synthesized according to the following Reaction Scheme 12.

[Reaction Scheme 12]

<Intermediate 2-c> <Intermediate 2-d>

Intermediate 2-d> (15.4 g, 82.1%) was obtained in the same manner as in Synthesis Example 1-3, except that <Intermediate 2-c> was used instead of <Intermediate 1-b>.

Synthetic example  2-5. <Compound 9>  synthesis

<Compound 9> was synthesized according to the following Reaction Scheme 13.

[Reaction Scheme 13]

<중간체 2-d> <화합물 9>

<Intermediate 2-d><Compound9>

Synthesis was conducted in the same manner as in Synthesis Example 1-8, except that <Intermediate 2-d> was used instead of <Intermediate 1-g> to obtain Compound 9 (4.1 g, 44.2%).

MS (MALDI-TOF): m / z 525.22 [M ^&lt; ⁺ &^gt;

Synthetic example  3. Synthesis of Compound 13

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

Intermediate 3-a &gt; was synthesized according to the following Reaction Scheme 14.

[Reaction Scheme 14]

         <Intermediate 1-c> <Intermediate 3-a>

The procedure of Synthesis Example 1-4 was repeated except that 2-bromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde to obtain Intermediate 3-a (24.3 g, 72.1%).

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

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

[Reaction Scheme 15]

&Lt; Intermediate 3-a > < Intermediate 3-b &

Intermediate 3-b> (19.6 g, 78.1%) was obtained by the same method except that <Intermediate 3-a> was used instead of <Intermediate 1-d> in Synthesis Example 1-5

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

Intermediate 3-c &gt; was synthesized according to the following Reaction Scheme 16.

[Reaction Scheme 16]

<Intermediate 3-b> <Intermediate 3-c>

Intermediate 3-c> (14.7 g, 82.1%) was obtained in the same manner as in Synthesis Example 1-6, except that <Intermediate 3-b> was used instead of <Intermediate 1-e>.

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

Intermediate 3-d &gt; was synthesized by the following Reaction Scheme 17.

[Reaction Scheme 17]

<Intermediate 3-c> <Intermediate 3-d>

<Intermediate 3-c> (14.7 g, 87.9 mmol) and 150 ml of dichloromethane are added to a 1 L round bottom flask reactor and stirred. Bromine (2.5 g, 102 mmol) was slowly added dropwise at room temperature and stirred for 5 hours. After completion of the reaction, precipitation was carried out using methanol, followed by filtration to obtain <Intermediate 3-d> (17.1 g, 82%).

Synthetic example  3-5. Synthesis of <Intermediate 3-e>

Intermediate 3-e &gt; was synthesized by the following Reaction Scheme 18.

[Reaction Scheme 18]

<Intermediate 3-d> <Intermediate 3-e>

Intermediate 3-e> (14.7 g, 79.1%) was obtained in the same manner as in Synthesis Example 1-3, except that <Intermediate 3-d> was used instead of <Intermediate 1-b>.

Synthetic example  3-6. <Compound 13>  synthesis

<Compound 13> was synthesized by the following Reaction Scheme 19.

[Reaction Scheme 19]

                  <Intermediate 3-e> <Compound 13>

Compound (13) (3.7 g, 37.2%) was obtained in the same manner as in Synthesis Example 1-8, except that <Intermediate 3-e> was used instead of <Intermediate 1-g>.

MS (MALDI-TOF): m / z 525.22 [M ^&lt; ⁺ &^gt;

Synthetic example  4. Synthesis of Compound 33

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

<Intermediate 4-a> was synthesized according to the following Reaction Scheme 20.

[Reaction Scheme 20]

                 <Intermediate 4-a>

 A dry 2 L round bottom flask reactor was charged with ethyl cyanoacetate (139.8 g, 1.236 mol), potassium cyanide (29.5 g, 0.453 mol), potassium hydroxide (46.2 g, 0.824 mol), dimethylformamide Dissolved in 920 mL, and stirred at 10 ° C for 20 minutes. Then, 1-nitronaphthalene (92 g, 531 mol) was added to the reaction mixture and stirred at 60 ° C for 4 hours. After completion of the reaction, the solvent was concentrated, 600 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was refluxed with stirring for 1 hour. The solid was filtered and separated by column chromatography to obtain <Intermediate 4-a> (50 g, 56%).

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

<Intermediate 4-b> was synthesized according to the following Reaction Scheme 21

[Reaction Scheme 21]

&Lt; Intermediate 4-a > < Intermediate 4-b &

 The reactor was filled with nitrogen, and then 3M-phenylmagnesium bromide (113 mL, 623 mmol) was slowly added dropwise at 0 ° C. to the reaction mixture with the addition of <Intermediate 4-a> (20.0 g, 169 mmol) and 200 mL of tetrahydrofuran And then refluxed for 3 hours. When the starting material disappeared, the temperature was lowered again, and then 3-bromobenzoyl chloride (44.58 g, 0.203 mmol) was dissolved in 200 mL of tetrahydrofuran, and the mixture was slowly added dropwise, followed by stirring under reflux for 2 hours. After completion of the reaction, an aqueous ammonium chloride solution was added to stop the reaction. The reaction mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 4-b> (37 g, 30.3%).

Synthetic example  4-3. <Compound 33>  synthesis

<Compound 33> was synthesized by the following Reaction Formula 22

[Reaction Scheme 22]

<Intermediate 4-b> <Intermediate 1-g> <Compound 33>

Synthesis was conducted in the same manner as in Synthesis Example 1-8, except that <Intermediate 4-b> was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain <Compound 33> , 45.1%).

MS (MALDI-TOF): m / z 624.26 [M ^&lt; ⁺ &^gt;

Synthetic example  5. Synthesis of Compound 44

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

Intermediate 5-a &gt; was synthesized according to the following Reaction Scheme 23.

[Reaction Scheme 23]

                 <Intermediate 5-a>

  2-Hydroxymethylphenol (100 g, 806 mmol), sodium cyanide (43.4 g, 886 mmol) and dimethylformamide (1000 mL) were added to a 2 L reactor, and the mixture was stirred at 120 ° C for 4 hours. After completion of the reaction, the reaction mixture is extracted with water and ethyl acetate. Concentrated and then separated by column chromatography to obtain <Intermediate 5-a> (90 g, 84%).

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

<Intermediate 5-b> was synthesized according to the following Reaction Scheme 24.

[Reaction Scheme 24]

&Lt; Intermediate 5-a > < Intermediate 5-b &

In a 2 L reactor, add <Intermediate 5-a> (90 g, 676 mmol), 4-dimethylaminopyridine (68.8 g, 338 mmol), triethylamine (137 g, 1352 mmol) and 900 mL of methylene chloride. Chloride (82.4 g, 676 mmol) is added dropwise. After the dropwise addition, the mixture is stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was concentrated and separated by column chromatography to obtain <Intermediate 5-b> (90 g, 56%).

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

<Intermediate 5-c> was synthesized according to the following Reaction Scheme 25.

[Reaction Scheme 25]

<Intermediate 5-b> <Intermediate 5-c>

To a dry 1 L round bottom flask reactor was added <intermediate 5-b> (40 g, 169 mmol), tricyclohexylphosphine (9.5 g, 34 mmol), zinc powder (1.9 g, 17 mmol), palladium acetate , 17 mmol) and dimethylformamide (400 mL), and the mixture was refluxed under nitrogen for 12 hours. After completion of the reaction, the reaction product was added dropwise to an excess amount of water at room temperature. When brown crystals were formed, the reaction mixture was filtered and separated by column chromatography to obtain <Intermediate 5-c> (22 g, 55%).

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

<Intermediate 5-d> was synthesized according to the following Reaction Scheme 26.

[Reaction Scheme 26]

<Intermediate 5-c> <Intermediate 5-d>

<Intermediate 5-c> (37 g, 156 mmol), urea (16.9 g, 281 mmol) and acetic acid (300 mL) were added to a 500 mL reactor and the mixture was refluxed for 12 hours. After completion of the reaction, excess water is added to the reaction product, which is then filtered out. The mixture was hot-slurryed with methanol, filtered, hot-slurried with toluene, and then filtered to obtain <Intermediate 5-d> (24 g, 59%).

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

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

[Reaction Scheme 27]

<Intermediate 5-d> <Intermediate 5-e>

<Intermediate 5-d> (24 g, 94 mmol) and phosphorus oxychloride (240 mL) were added to a 500 mL reactor, and the mixture was refluxed with stirring for 3 hours. After completion of the reaction, slowly add the reactant to an excess of water at 0 ° C, precipitate it, and filter it. The intermediate was separated by column chromatography to obtain Intermediate 5-e (19 g, 74%).

Synthetic example  5-6. <Compound 44>  synthesis

<Compound 44> was synthesized by the following Reaction Formula 28.

[Reaction Scheme 28]

<Intermediate 5-e> <Intermediate 1-g> <Compound 44>

Synthesis was conducted in the same manner as in Synthesis Example 1-8, except that <Intermediate 5-e> was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain < , 41.1%).

MS (MALDI-TOF): m / z 538.2 [M ^&lt; ⁺ &^gt;

Synthetic example  6. Synthesis of Compound 107

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

<Intermediate 6-a> was synthesized by the following Reaction Scheme 29.

[Reaction Scheme 29]

                      <Intermediate 6-a>

<Intermediate 6-a> (40 g, 60%) was obtained using the same method except that diphenylamine was used in place of <Intermediate 3-c> in Synthesis Example 3-4.

Synthetic example  6-2. Synthesis of <Intermediate 6-b>

<Intermediate 6-b> was synthesized by the following Reaction Scheme 30.

[Reaction Scheme 30]

&Lt; Intermediate 6-a > < Intermediate 6-b &

<Intermediate 6-b> (9.9 g, 75.2%) was obtained using the same method except that <Intermediate 6-a> was used instead of 4-bromo-2-iodobenzoate in Synthesis Example 1-1 .

Synthetic example  6-3. Synthesis of <Intermediate 6-c>

<Intermediate 6-c> was synthesized by the following Reaction Scheme 31.

[Reaction Scheme 31]

<Intermediate 6-b> <Intermediate 6-c>

To a 250 ml reactor were added <Intermediate 6-b> (7.9 g, 24.6 mmol), 4-bromoiodobenzene (8.3 g, 30 mmol), palladium acetate (0.4 g, 0.3 mmol), sodium tertiary butoxide , Tertiary butyl phosphine (0.1 g, 0.3 mmol) and toluene (100 ml) were added, and the mixture was stirred under reflux for 13 hours. After completion of the reaction, the reaction mixture is filtered and the filtrate is concentrated. The reaction mixture was separated by column chromatography to obtain <Intermediate 6-c> (4.0 g, 34%).

Synthetic example  6-4. Synthesis of <Intermediate 6-d>

&Lt; Intermediate 6-d >

[Reaction Scheme 32]

<Intermediate 6-c> <Intermediate 6-d>

(25 g, 52.5 mmol), bispinacolatodiboron (12 g, 132 mmol), palladium (II) chloride-1,1'-bis (diphenylphosphino) ferrocene 2.5 g, 3 mmol), potassium acetate (20.2 g, 224.9 mmol) and toluene (250 ml), and the mixture was refluxed with stirring for 12 hours. After completion of the reaction, the solid is filtered off and the filtrate is concentrated under reduced pressure. The reaction mixture was separated by column chromatography to obtain <Intermediate 6-d> (19.4 g, 71%).

Synthetic example  6-5. <Compound 107>  synthesis

<Compound 107> was synthesized by the following Reaction Formula 33

[Reaction Scheme 33]

<Intermediate 1-f> <Intermediate 6-d> <Compound 107>

 Synthesis was conducted in the same manner as in Synthesis Example 1-1, except that <Intermediate 1-f> was used instead of 4-bromo-2-iodobenzoate and <Intermediate 6-d> was used instead of phenylboronic acid, 107> (3.9 g, 31.1%).

MS (MALDI-TOF): m / z 689.31 [M ^&lt; ⁺ &^gt;].

Synthetic example  7. Synthesis of Compound 109

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

&Lt; Intermediate 7-a >

[Reaction Scheme 34]

                                            <Intermediate 7-a>

Except that biphenyl-4-amine was used instead of <Intermediate 6-b> in Synthesis Example 6-3 and 2-bromo-9,9-dimethyl-9H-fluorene was used in place of 4-bromoiodobenzene Were synthesized in the same manner to give <Intermediate 7-a> (47 g, 71.2%).

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

<Intermediate 7-b> was synthesized by the following Reaction Scheme 35.

[Reaction Scheme 35]

<Intermediate 7-a> <Intermediate 7-b>

 Intermediate 7-b> (34.1 g, 71.1%) was obtained in the same manner as in Synthesis Example 6-3, except that <Intermediate 7-a> was used instead of <Intermediate 6-b>.

Synthetic example  7-3. <Synthesis of intermediate 7-c>

<Intermediate 7-c> was synthesized according to the following reaction scheme 36.

[Reaction Scheme 36]

<Intermediate 7-b> <Intermediate 7-c>

 Intermediate 7-c> (26.4 g, 70.1%) was obtained in the same manner except that <Intermediate 7-b> was used in place of <Intermediate 6-c> in Synthesis Example 6-4.

Synthetic example  7-4. <Compound 109>  synthesis

&Lt; Compound 109 > was synthesized according to the following Reaction Scheme 37

[Reaction Scheme 37]

<Intermediate 2-c> <Intermediate 7-c> <Compound 109>

Synthesis was conducted in the same manner as in Synthesis Example 1-1, except that <Intermediate 2-c> was used instead of 4-bromo-2-iodobenzoate and <Intermediate 7-c> was used instead of phenylboronic acid, 109> (4.1 g, 43.1%).

MS (MALDI-TOF): m / z 729.34 [M ^&lt; ⁺ &^gt;].

Synthetic example  8. Synthesis of Compound 125

Synthetic example  8-1. <Compound 125> of  synthesis

<Compound 125> was synthesized by the following Reaction Scheme 38.

[Reaction Scheme 38]

<Intermediate 3-d> <Intermediate 7-c> <Compound 125>

Synthesis was conducted in the same manner as in Synthesis Example 1-1, except that <Intermediate 3-d> was used instead of 4-bromo-2-iodobenzoate and <Intermediate 7-c> was used instead of phenylboronic acid, 125> (4.7 g, 44.1%).

MS (MALDI-TOF): m / z 729.34 [M ^&lt; ⁺ &^gt;].

Synthetic example  9. Synthesis of Compound 129

Synthetic example  9-1. <Compound 129>  synthesis

<Compound 129> was synthesized by the following Reaction Scheme 39.

[Reaction Scheme 39]

<Intermediate 1-f> <Compound 129>

Intermediate 1-f> was used instead of 4-bromo-2-iodobenzoate in Synthesis Example 1-1 and (9-phenyl-9H-carbazol-3-yl) boronic acid was used in place of phenylboronic acid , The compound (129) (3.7 g, 38.1%) was obtained.

MS (MALDI-TOF): m / z 535.23 [M ^&lt; ⁺ &^gt;

Synthetic example  10. Synthesis of Compound 141

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

&Lt; Intermediate 10-a >

 [Reaction Scheme 40]

   &Lt; Compound 129 > < Intermediate 10-a &

<Intermediate 10-a> (11.5 g, 80%) was obtained using the same method except that <compound 129> was used in place of <intermediate 3-c> in Synthesis Example 3-4.

Synthetic example  10-2. <Compound 141>  synthesis

<Compound 141> was synthesized by the following Reaction Scheme 41.

[Reaction Scheme 41]

<Intermediate 10-a> <Intermediate 7-a> <Compound 141>

Synthesis Example 6-3 was repeated except that <Intermediate 7-a> was used instead of <Intermediate 6-b> and Intermediate 10-a> was used instead of 4-bromoiodobenzene to obtain Compound 141 > (5.1 g, 41.4%).

MS (MALDI-TOF): m / z 894.4 [M ^&lt; ⁺ &^gt;].

Example  1 to 5: Organic light emitting device Manufacturing (ETL) Electronics Transport layer  Usage

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to ¹ × 10 ^-6 torr. Then, the organic material was doped on the ITO with HATCN (50 Å), NPD (650 Å), blue host (BH) + blue dopant To form a light-emitting layer having a thickness of 200 ANGSTROM. Liq (1: 1) (300 Å), Liq (10 Å), and Al (1,000 Å) were used as the electron transport layer in the following order: 0.4 mA. The structures of [HATCN], [NPD], [BH], [BD], and [Liq] are as follows

[HATCN] [NPD] [BD]

[BH] [Liq]

Comparative Example  One

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner except that ET, which is generally used as an electron transport layer material, was used instead of the compound manufactured by the present invention in the device structure of the above embodiment. same.

 [ET]

The voltage, current, luminance, color coordinates, and lifetime of the organic light-emitting device manufactured according to Examples 1 to 5 and Comparative Example 1 of the present invention were measured, and the results are shown in Table 1 below. . T95 means the time required for the luminance to be reduced to 95% compared to the initial luminance (2000 cd / m ² )

division ETL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 1 ET 4.3 6.5 0.133 0.129 13 Example 1 Compound 1 3.6 8.1 0.132 0.130 32 Example 2 Compound 9 3.7 8.2 0.133 0.128 35 Example 3 Compound 13 3.8 8.3 0.132 0.126 30 Example 4 Compound 33 3.7 8.3 0.133 0.125 33 Example 5 Compound 44 3.6 8.1 0.132 0.126 32

As shown in Table 1, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer life than ET, which is widely used as an electron transport layer material according to the prior art.

Example  6 to 10: Manufacturing (HTL) Precision Transport layer  Usage

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to ¹ × 10 ^-6 torr, an organic material was coated on the ITO using HATCN (50 Å) as the hole transport layer, the compound (650 Å) Doped with a host (BH) + blue dopant (BD) of 5% to form a 200 Å thick light emitting layer. Thereafter, the compound ET: Liq = 1: 1 (300 ANGSTROM), the electron injecting layer Liq (10 ANGSTROM) and Al (1,000 ANGSTROM) were sequentially deposited as the electron transporting layer. The structures of [HATCN], [ET], [BD], [BH] and [Liq] are as follows.

[HATCN] [ET] [BD]

[BH] [Liq]

Comparative Example  2

The organic light-emitting diode device for Comparative Example 2 was fabricated in the same manner as in Examples 6 to 10 except that NPD, which is widely used as a hole transport layer material in the prior art, was used instead of the compound prepared by the present invention The structure of the NPD is as follows.

[NPD]

The voltage, current, luminance, color coordinates, and lifetime of the organic light-emitting device manufactured according to Examples 6 to 10 and Comparative Example 2 were measured, and the results are shown in Table 2 below. T95 means the time required for the luminance to be reduced to 95% compared to the initial luminance (2000 cd / m ² )

division HTL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 2 NPD 4.3 6.5 0.133 0.129 13 Example 6 Compound 107 3.7 8.2 0.132 0.130 33 Example 7 Compound 109 3.6 8.1 0.133 0.128 29 Example 8 Compound 125 3.8 8.3 0.132 0.126 30 Example 9 Compound 129 3.7 8.3 0.132 0.126 32 Example 10 Compound 141 3.8 8.4 0.133 0.125 33

As shown in Table 2, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer life time than NPD, which is widely used as a hole transport layer material.

Claims (18)

An organic compound represented by the following formula (A) or (B).
(A)

[Chemical Formula B]

In the above formulas (A) and (B)
The substituents R 1 to R 14 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,
And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,
In the above formula (A), one or two substituents of the substituents R 1 to R 12 are a single bond which binds to the above-mentioned Al
In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,
The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, And an unsubstituted heteroarylene group having 2 to 60 carbon atoms;
n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,
Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms,
The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein the substituents Ar1 to Ar3 are the same or different and are each independently any one selected from the group consisting of an unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. compound. The method according to claim 1,
Wherein the substituents R13 and R14 are the same or different and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The method according to claim 1,
Wherein Ar 1 in the above [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. 5. The method of claim 4,
Wherein the substituent Ar1 in the formula [A] is any one selected from the following structural formulas A to Q:
[Structural formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

[Structural formula P] [Structural formula Q]

The substituents R in the structural formulas A to Q are the same as those of R 1 to R 14 defined in claim 1,
K is an integer of 1 to 7, and when k is 2 or more, each R is the same or different,
When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring. The method according to claim 1,
Wherein one of the substituents R 1 to R 4 is a single bond bonded to A 1 or A 2 in the above formulas (A) and (B). The method according to claim 1,
Wherein in the above formulas A and B, one of the substituents R5 to R12 is a single bond bonding with Al or A2. The method according to claim 1,
In the formula (B), Ar2 and Ar3 are the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The method according to claim 1,
Wherein the substituent which is not connected to A1 or A2 among the substituents R1 to R12 is hydrogen or deuterium. The method according to claim 1,
Wherein the linking groups L 1 and L 2 are the same or different and are each independently a single bond or any one selected from the following structural formulas 1 to 9.
[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]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium. The method according to claim 1,
In the above formula (A), only one substituent of the substituents R 1 to R 12 is a single bond which binds to the above-mentioned Al. The method according to claim 1,
Wherein the compound represented by the above formula (A) or (B) is any one selected from the group consisting of the following compounds [1] to [144].

[Compound 1] [Compound 2] [Compound 3] [Compound 4]

[Compound 5] [Compound 6] [Compound 7] [Compound 8]

[Compound 9] [Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15] [Compound 16]

[Compound 17] [Compound 18] [Compound 19] [Compound 20]

[Compound 21] [Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27] [Compound 28]

[Compound 29] [Compound 30] [Compound 31] [Compound 32]

[Compound 33] [Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39] [Compound 40]

[Compound 41] [Compound 42] [Compound 43] [Compound 44]

[Compound 45] [Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51] [Compound 52]

[Compound 53] [Compound 54] [Compound 55] [Compound 56]

[Compound 57] [Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63] [Compound 64]

[Compound 65] [Compound 66] [Compound 67] [Compound 68]

[Compound 69] [Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75] [Compound 76]

[Compound 77] [Compound 78] [Compound 79] [Compound 80]

[Compound 81] [Compound 82] [Compound 83] [Compound 84]

[Compound 85] [Compound 86] [Compound 87] [Compound 88]

[Compound 89] [Compound 90] [Compound 91] [Compound 92]

[Compound 93] [Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99] [Compound 100]

[Compound 101] [Compound 102] [Compound 103] [Compound 104]

[Compound 105] [Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111] [Compound 112]

[Compound 113] [Compound 114] [Compound 115] [Compound 116]

[Compound 117] [Compound 118] [Compound 119] [Compound 120]

[Compound 121] [Compound 122] [Compound 123] [Compound 124]

[Compound 125] [Compound 126] [Compound 127] [Compound 128]

[Compound 129] [Compound 130] [Compound 131] [Compound 132]

[Compound 133] [Compound 134] [Compound 135] [Compound 136]

[Compound 137] [Compound 138] [Compound 139] [Compound 140]

[Compound 141] [Compound 142] [Compound 143] [Compound 144] A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises the organic compound according to any one of claims 1 to 12. 14. The method of claim 13,
Wherein the organic layer in the organic light emitting device comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 14. The method of claim 13,
Wherein the organic compound is used for a hole transport layer. 14. The method of claim 13,
Wherein the organic organic compound is used for an electron transport layer. 15. The method of claim 14,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 14. The method of claim 13,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

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