KR20160107669A - Novel organic light-emitting diode including antracene derivatives - Google Patents

Abstract

Provided is an organic light-emitting device which comprises: a first electrode; a second electrode facing the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode and including a compound which is represented by chemical formula A. More specifically, the purpose of the present invention is to provide an organic light-emitting device exhibiting excellent device properties including luminous efficiency while ensuring low driving voltage, by applying an anthracene derivative having a specific structure to a light-emitting layer in the organic light-emitting device. In the chemical formula A, R_1 to R_10, L, and M are the same as defined in the present specification.

Description

[0001] The present invention relates to novel organic light-emitting diode (OLED) including antracene derivatives,

The present invention relates to a novel organic electroluminescent device comprising an anthracene derivative, and more particularly, to a novel organic electroluminescent device comprising an anthracene derivative, which can be driven at a low voltage and has excellent device characteristics such as luminous efficiency, 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.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. 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.

A material used as an organic material layer in an organic light emitting device can 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, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light emitting material to increase the efficiency of light emission through the transition.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

As a prior art related to the host compound in such a light emitting layer, Japanese Patent Registration No. 10-1092006 (Dec. 12, 2011) discloses an organic light emitting device comprising an anthracene derivative in which a phenyl group having a substituent is bonded at both ends of an anthracene structure, And Patent Document 10-2006-0113954 (Nov. 3, 2006) discloses a technique relating to an organic light emitting device including an asymmetric anthracene derivative of a specific structure in a light emitting medium layer.

However, despite the fact that various kinds of compounds for use in the light emitting medium layer have been prepared including the above-mentioned conventional arts, there is still a need to develop organic light emitting devices capable of driving at a low voltage, .

Patent Registration No. 10-1092006 (December, 2011)

Patent Document 10-2006-0113954 (November 3, 2006)

Therefore, the first technical object of the present invention is to provide an organic light emitting device which can be driven at a low voltage by using an anthracene derivative having a specific structure in a light emitting layer in an organic light emitting device, and has excellent device characteristics such as light emitting efficiency.

According to an aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And a light emitting layer interposed between the first electrode and the second electrode, wherein the light emitting layer comprises a compound represented by the following formula (A).

(A)

In the above formula (A)

Each of R ₁ to R ₁₀ is the same or different and is 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 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 cycloalkyl group having 3 to 30 carbon atoms, 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 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms An alkylamine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having O, N or S A nitro group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a substituted or unsubstituted aliphatic group, A carboxyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, an amide group, an ether group and 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, Lt; / RTI > may be substituted with a heteroatom;

Any one of R ₁ to R ₁₀ is a single bond which bonds with the linking group L,

The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted C2 to C60 A heteroarylene group;

n is an integer of 1 to 3,

And M is any one substituent selected from the following general formulas (1) to (6).

[Chemical Formula 1] (2) (3)

[Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6]

In the above Chemical Formulas 1 to 6,

Substituents Z ₁ to Z ₁₂ are the same or different from each other and each independently represents 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 heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 or less carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted A nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group and an ester group may be selected from the group consisting of a halogen atom, a fluorine atom, a fluorine atom, a fluorine atom, ≪ / RTI >

Wherein _{one of} Z ₁ to Z ₁₂ is a single bond which binds to L,

Wherein X is S or O.

The organic light emitting device including the compound represented by the formula (A) in the light emitting layer according to the present invention can be driven at a low voltage as compared with the conventional organic light emitting device, and has excellent characteristics such as luminous efficiency.

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 present invention provides a plasma display panel comprising a first electrode, a second electrode facing the first electrode, And a light emitting layer interposed between the first electrode and the second electrode, wherein the light emitting layer comprises a compound represented by the following formula (A).

(A)

In the above formula (A)

Each of R ₁ to R ₁₀ is the same or different and is 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 alkinyl 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 cycloalkyl group having 3 to 30 carbon atoms, 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 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms An alkylamine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic group having O, N or S A nitro group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a substituted or unsubstituted aliphatic group, A carboxyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, an amide group, an ether group and 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, Lt; / RTI > may be substituted with a heteroatom;

Any one of R ₁ to R ₁₀ is a single bond which bonds with the linking group L,

The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted C2 to C60 A heteroarylene group;

n is an integer of 1 to 3,

And M is any one substituent selected from the following general formulas (1) to (6).

[Chemical Formula 1] (2) (3)

[Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6]

In the above Chemical Formulas 1 to 6,

Substituents Z ₁ to Z ₁₂ are the same or different from each other and each independently represents 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 heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted A nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group and an ester group may be selected from the group consisting of a halogen atom, a fluorine atom, a fluorine atom, a fluorine atom, ≪ / RTI >

Wherein _{one of} Z ₁ to Z ₁₂ is a single bond which binds to L,

X is S or O;

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 1 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 6 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 having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, The carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms 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 will be. 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.

An aryl group, which is a substituent used in the compound of the present invention, refers to an aromatic system composed of a hydrocarbon containing at least one ring, and when the aryl group has a substituent, it is fused with neighboring substituents to further 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 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 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 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

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 the same substituent as in the case 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, iso-amyloxy, 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, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

The compound represented by Formula A in the organic light emitting device according to the present invention is characterized in that the linking group L is bonded to the anthracene ring and the substituent M is connected thereto.

The linking group L is preferably bonded to the 9-position of the anthracene ring.

Here, as shown in the following FIG. 1, the substituent M is a phenanthrene ring in which X is S or O, and a substituted or unsubstituted phenanthrene ring is fused and bonded to carbon atoms at positions 2 and 3 in a benzofuran or benzothiophene ring Thereby forming an aromatic condensation ring.

[그림 1]

[Figure 1]

Meanwhile, the light emitting layer of the organic light emitting device according to the present invention includes a fluorescent host and a fluorescent dopant, and the compound represented by the formula (A) is used as a fluorescent host, so that it can be driven at a low voltage And the device characteristics such as luminous efficiency and the like can be excellently exerted.

In the present invention, the substituent R ₁₀ in the above formula (A) may be bonded to the 9-position of the anthracene ring as a single bond to which the linking group L is bonded.

The substituent R ₉ in the above formula (A) may be a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, wherein the 10-position of the anthracene ring is substituted with an aryl group.

In the present invention, the linking group L in the formula (A) may be a single bond or any one selected from the following formulas (21) to (29).

[Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24]

[Structural Formula 25] [Structural Formula 26] [Structural Formula 27] [Structural Formula 28]

[Structural Formula 29]

The carbon residue of the aromatic ring in the linking group L may be bonded to hydrogen or deuterium.

In the present invention, the number n of connecting linking groups L in the formula (A) is 1 or 2, and X in the substituent M may be 0.

In the present invention, the compound represented by the formula (A) may be any one selected from the group consisting of the following compounds [1] to [248].

[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] [95] [Compound 96]

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

[Compound 100] [Compound 101] [Compound 102]

[Compound 103] [Compound 104] [105]

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

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

[Compound 112] [Compound 113] [Compound 114]

[115] [Compound 116] [Compound 117]

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

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

[Compound 124] [125] [Compound 126]

[Compound 127] [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 142]

[Compound 143] [Compound 144] [145]

[Compound 146] [Compound 147] [Compound 148]

[Compound 149] [Compound 150] [Compound 151]

[Compound 152] [Compound 153] [Compound 154]

[Compound 155] [Compound 156] [Compound 157]

[Compound 158] [159] [Compound 160]

[Compound 161] [Compound 162] [Compound 163]

[Compound 164] [Compound 165] [Compound 166]

[Compound 167] [Compound 168] [Compound 169]

[Compound 170] [Compound 171] [Compound 172]

[Compound 173] [Compound 174] [Compound 175]

[Compound 176] [Compound 177] [Compound 178]

[Compound 179] [Compound 180] [Compound 181]

[Compound 182] [Compound 183] [184]

[Compound 185] [Compound 186] [Compound 187]

[Compound 188] [Compound 189] [Compound 190]

[191] [Compound 192] [193]

[194] [Compound 195] [196]

[Compound 197] [Compound 198] [199]

[Compound 200] [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]

The present invention, as described above, comprises a first electrode; A second electrode facing the first electrode; And a light-emitting layer interposed between the first electrode and the second electrode, wherein the organic compound represented by the formula (A) in the present invention may be contained in the light-emitting layer as a host.

Herein, "(organic layer) contains at least one organic compound" in the present invention means that one or more organic compounds belonging to the category of the present invention (organic layer) Compound "as used herein.

In this case, the light emitting layer may further include a dopant other than a host, and 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 .

At this time, the organic layer containing the compound of the present invention may further 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, an electron transport layer, and an electron injection layer .

In the present invention, as the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- but are not limited to, materials such as olate: Bebq2), ADN, compound 201, compound 202, BCP, oxadiazole derivative PBD, BMD, BND and the like.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > < BCP &

In addition, the electron transporting layer used in the present invention can be used alone or in combination with the electron transporting layer material as the organometallic compound represented by the formula (F).

[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 A ligand chelated by coordination bond with the single bond, and

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 A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted hetero atom selected from O, N, S and Si And a heteroaryl group having 2 to 50 carbon atoms,

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

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

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 alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 30 carbon atoms, 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 And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

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.

The material of the hole injection layer is not particularly limited and can be used as is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) NPD [N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)], TPD [ -4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- (phenyl- Etc. However, the present invention is not limited thereto.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

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 an 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.

Further, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

In the present invention, at least one layer selected from the functional layer having the hole injecting layer, the hole transporting layer, the hole injecting function and the hole transporting function, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer, A deposition method 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.

Further, in the present invention, the light emitting layer may include a compound represented by the following formula (B) or (C) as a dopant, and may further include other commonly used dopant materials.

[Chemical Formula B]  &Lt; RTI ID = 0.0 &

In the above formulas (B) and (C)

A represents 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, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom, 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, Phenylene, perylene, pentacene. At this time, A may be a compound represented by 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 (B)

X ₁ to X ₂ are the same or different and are 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 to Y ₂ each independently represent 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 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 A substituted or unsubstituted aryloxy group having 6 to 24 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, deuterium and hydrogen Y ₁ to Y ₂ are the same or different from each other and form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group You can.

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 (C)

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.

The above B is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3, and when p is 2 or more, R ₅ and R ₆ , Different;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are and independently of one another identical or different and are hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone 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 C2-C20 alkenyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C1 to C60 alkylthio group, a substituted or unsubstituted C3 to C60 cycloalkyl group, Substituted or unsubstituted aryloxy groups having 6 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted C2 to C60 hetero Ah (Substituted or unsubstituted C1-C60 alkyl) amino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C1-C60 alkylamino group, (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, 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, or boron Lt; / RTI &gt;

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 above formulas [B] and [C] may be represented by any one selected from the group consisting of 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.

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 2

Synthesis Example 1- (1): Synthesis of <Intermediate 1-a>

                         <Intermediate 1-a>

48 g (227 mmol) of dibenzofuran-4-boronic acid, 60 g (227 mmol) of 2,6-dibromobenzaldehyde, 5.2 g (4.5 mmol) of tetrakistriphenylphosphine palladium, g (454 mmol), toluene (700 ml) and water (200 ml) were added under a nitrogen atmosphere and refluxed for 12 hours. After completion of the reaction, the reaction product was separated into layers. The organic layer was concentrated under reduced pressure, and then separated and dried to obtain 55.8 g (yield: 70%).

Synthesis Example 1- (2): Synthesis of <Intermediate 1-b>

<Intermediate 1-b>

To a round bottom flask containing 200 ml of tetrahydrofuran is added 100 ml (110 mmol) of 1M potassium tartar latex and the temperature is lowered to 0 ° C under a nitrogen atmosphere. Then, 36 g (110 mmol) of (methoxymethyl) triphenylphosphonium chloride is dissolved in 200 ml of tetrahydrofuran, and the solution is slowly added dropwise. After 30 minutes, 20 g (73.4 mmol) of Intermediate 1-a was dissolved in 200 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction product was washed with water, extracted with ethyl acetate, and layered. The organic layer was concentrated under reduced pressure, and then separated by column separation to obtain 21 g (yield 95%).

Synthesis Example 1- (3): Synthesis of <Intermediate 1-c>

                             <Intermediate 1-c>

16 g (53.2 mmol) of Intermediate 1-b, 1.6 g (2.6 mmol) of bismuth (III) trifluoromethanesulfonate and 100 ml of 1,2-dichloroethane were added to a round bottom flask under nitrogen atmosphere for 3 hours Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane and water, and the organic layer was concentrated and separated by column chromatography. As a result of drying, 7.4 g was obtained. (Yield: 51%)

Synthesis Example 1- (4): Synthesis of Compound 2

    &Lt; Formula 1-a > < Compound 2 &

5 g (14.4 mmol) of Intermediate 1-c, 5.9 g (15.8 mmol) of <Formula 1-a>, 0.3 g (0.29 mmol) of tetrakistriphenylphosphine palladium and 4 g mmol), 25 ml of toluene, 25 ml of 1,4-dioxane and 15 ml of water were added under nitrogen and 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 separated organic layer was dried to obtain 6.8 g (yield: 70%).

Synthesis Example 2. Synthesis of Compound 10

Synthesis Example 2- (1): Synthesis of Compound 10

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

<Synthesis of Intermediate 1-c> except that 2-iodo-5-bromobenzaldehyde was used instead of 2,6-dibromobenzaldehyde used in Synthesis Example 1- (1) <Compound 10> was synthesized in the same manner as in Synthesis Example 1- (4) except that <Formula 1-a> was used instead of <Intermediate 1-c>>, The compound 10 was obtained.

Synthesis Example 3 Synthesis of Compound 13

Synthesis Example 3- (1): Synthesis of Compound 13

&Lt; Formula 3-a > < Formula 3-a &

Synthesis of Intermediate 1-c> except that 2-iodo-4-bromobenzaldehyde was used instead of 2,6-dibromobenzaldehyde used in Synthesis Example 1- (1) Was used instead of <Intermediate 1-c> used in Synthesis Example 1- (4), and <Formula 3-a> was used instead of <Formula 1-a>>, The compound 13 was obtained.

Synthesis Example 4. Synthesis of Compound 67

Synthesis Example 4- (1): Synthesis of Compound 67

&Lt; Formula 3-a > < Formula 4-a &

<Formula 4-a> is a method for synthesizing <Intermediate 1-c> except that dibenzofuran-3-boronic acid was used in place of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) The compound 67 was synthesized in the same manner as in Synthesis Example 1- (4) except that <Formula 4-a> was used in place of <Intermediate 1-c> Synthesis was conducted in the same manner except that the compound 67 was used.

Synthesis Example 5. Synthesis of Compound 80

Synthesis Example 5- (1): Synthesis of Compound 80

<Formula 1-a> <Formula 5-a> <Compound 80>

(5-a) was prepared by using dibenzofuran-3-boronic acid instead of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) and replacing 2,6- Was prepared in the same manner as in the synthesis of Intermediate 1-c except for using 4-bromobenzaldehyde instead of Intermediate 1-c. Was synthesized in the same way except that the compound represented by the formula (5-a) was used to obtain a compound (80).

Synthesis Example 6 Synthesis of Compound 96

Synthesis Example 6- (1): Synthesis of <Intermediate 6-a>

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

(6-a) was prepared by using dibenzofuran-3-boronic acid instead of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) and replacing 2-bromobenzaldehyde Synthesis was carried out in the same manner as in the synthesis of <Intermediate 1-c> except for using the mo benzaldehyde.

10 g (37.2 mmol) of <Formula 6-a> is added to a round bottom flask, 100 ml of acetic acid is added under nitrogen atmosphere, and the temperature is lowered to 0 ° C. 5.2 g (37.2 mmol) of bromine is slowly added dropwise. After 15 minutes, the temperature was raised to room temperature and stirred. After completion of the reaction, the reaction product was separated into layers. The organic layer was concentrated under reduced pressure, and the residue was subjected to column separation using hexane to obtain 11.6 g (yield: 90%).

Synthesis Example 6- (2): Synthesis of Compound 96

<Formula 6-b> <Intermediate 6-a> <Compound 96>

Synthesis was carried out in the same manner except that <Intermediate 6-a> was used instead of <Intermediate 1-c> instead of <Intermediate 6-b> instead of Intermediate 1-a used in Synthesis Example 1- (4) 96 was obtained.

Synthesis Example 7 Synthesis of Compound 166

Synthesis Example 7- (1): Synthesis of Compound 166

<Formula 7-a> <Formula 7-b> <Compound 166>

(7-b) was prepared by using dibenzofuran-1-boronic acid instead of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) and replacing 2,6-dibromobenzaldehyde with 2- Was prepared in the same manner as in the synthesis of Intermediate 1-c except that 4-bromobenzaldehyde was used instead of Intermediate 1-c. The above compound 166 was synthesized in the same manner as Intermediate 1-c used in Synthesis Example 1- (4) The compound 166 was synthesized in the same way except that the compound of the formula 7-b> was used and the compound of the formula 7-a was used instead of the compound of the formula 1-a.

Synthesis Example 8 Synthesis of Compound 181

Synthesis Example 8- (1): Synthesis of Compound 181

<Formula 6-b> <Formula 8-b> <Compound 181>

<Formula 8-b> is a method for synthesizing <Intermediate 1-c> except that dibenzofuran-1-boronic acid was used in place of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) The compound 181 was synthesized in the same manner as in Synthesis Example 1-7 except that <Formula 8-b> was used in place of <Intermediate 1-c> used in Synthesis Example 1- The compound 181 was synthesized by the same method except for using it.

Synthesis Example 9. Synthesis of Compound 182

Synthesis Example 9- (1): Synthesis of <Intermediate 9-a>

&Lt; Formula 9-a > < Intermediate 9-a &

<Formula 9-a> was prepared by using dibenzofuran-1-boronic acid instead of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1), replacing 2,6-dibromobenzaldehyde with 2- Synthesis was carried out in the same manner as in the synthesis of <Intermediate 1-c> except for using the mo benzaldehyde.

<Intermediate 9-a> was synthesized in the same manner as in Synthesis Example 6- (1).

Synthesis Example 9- (2): Synthesis of Compound 182

<Formula 3-a> <Intermediate 9-a> <Compound 182>

Synthesis was conducted in the same manner except that <Intermediate 9-a> was used in place of <Intermediate 1-c> instead of <Intermediate 3-a> instead of Intermediate 1-a used in Synthesis Example 1- (4) 182 < / RTI >

Synthesis Example 10. Synthesis of Compound 243

Synthesis Example 10- (1): Synthesis of Compound 243

<Formula 1-a> <Formula 10-a> <Compound 243>

<Compound 243> was prepared in the same manner as in the synthesis of <compound 2> except that dibenzothiophene-4-boronic acid was used in place of dibenzofuran-4-boronic acid used in Synthesis Example 1- (1) To give compound 243.

Examples: Production of organic light emitting device ( Examples 1 to 9 and Comparative Examples 1 and 2)

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 substrate was adjusted to have a pressure of 1 x 10 &lt; ^-6 &gt; torr. Then, organic substances were added to the ITO using DNTPD (700 ANGSTROM), NPD (300 ANGSTROM) (E-1): [Formula E-2] = 1: 1, Formula E-1] (5 Å), and A1 (1,000 Å) . The structures of DNTPD (700 Å), NPD (300 Å), E-1, E-2 and BD 1 are as follows.

<DNTPD> <NPD>

<Formula E-1><FormulaE-2><BD1>

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that BH1 and BH2, which are commonly used as fluorescent host materials, were used instead of the compound prepared by the invention in the device structure of the above embodiment, and the structures of BH1 and BH2 Are as follows.

<BH1> <BH2>

The voltage, current density, luminance, and color coordinates were measured for the organic light emitting devices manufactured according to Examples 1 to 9 and Comparative Examples 1 and 2, and the results are shown in Table 1 below.

Host Dopant Voltage Luminance
(cd / m ² ) CIEx CIEy Comparative Example 1 BH1 BD1 4.2 630 0.133 0.137 Comparative Example 2 BH2 BD1 4.1 615 0.132 0.129 Example 1 Compound 2 BD1 3.7 680 0.131 0.131 Example 2 Compound 10 BD1 3.8 675 0.132 0.131 Example 3 Compound 13 BD1 3.7 665 0.131 0.131 Example 4 Compound 67 BD1 3.8 685 0.130 0.137 Example 5 Compound 80 BD1 3.7 670 0.130 0.138 Example 6 Compound 96 BD1 3.6 660 0.132 0.131 Example 7 Compound 166 BD1 3.7 655 0.132 0.129 Example 8 Compound 181 BD1 3.8 680 0.133 0.136 Example 9 Compound 182 BD1 3.6 675 0.132 0.130

As shown in Table 1, the organic compound obtained according to the present invention exhibits a lower driving voltage than the host materials BH1 and BH2, which are widely used as fluorescent host materials used in the prior art, have.

Claims (11)

A first electrode;
A second electrode facing the first electrode; And
And an emission layer interposed between the first electrode and the second electrode,
Wherein the light emitting layer comprises a compound represented by the following formula (A).
(A)

In the above formula (A)
Each of R ₁ to R ₁₀ is the same or different and is 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 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 cycloalkyl group having 3 to 30 carbon atoms, 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 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms An alkylamine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic group having O, N or S A nitro group, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a substituted or unsubstituted aliphatic group, A carboxyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, an amide group, an ether group and 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, Lt; / RTI &gt; may be substituted with a heteroatom;
Any one of R ₁ to R ₁₀ is a single bond which bonds with the linking group L,
The linking group L is a single bond, 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 alkynylene group having 2 to 60 carbon atoms, A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted C2 to C60 A heteroarylene group;
n is an integer of 1 to 3,
And M is any one substituent selected from the following general formulas (1) to (6).

[Formula 3] &lt; EMI ID =

[Chemical Formula 4] &lt; EMI ID =
In the above Chemical Formulas 1 to 6,
Substituents Z ₁ to Z ₁₂ are the same or different from each other and each independently represents 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 heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 6 or less carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron A halogen atom, a selenium atom, a tellurium atom, an amide group, an ether group, and an ester group, which is selected from the group consisting of an alkyl group, a substituted or unsubstituted aliphatic group, Any one of the substituents;
Wherein _{one of} Z ₁ to Z ₁₂ is a single bond which binds to L,
X is S or O;
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 1 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 6 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 having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
Wherein the light emitting layer comprises a fluorescent host and a fluorescent dopant, and the compound represented by the formula (A) is used as a fluorescent host. The method according to claim 1,
Wherein the substituent R _{10 in} the formula (A) is a single bond to which the linking group L is bonded. The method of claim 3,
Wherein the substituent R ₉ in the formula A is a substituted or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The method according to claim 1,
Wherein the linking group L in the formula (A) is a single bond or any one selected from the following formulas (21) to (29).
[Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24]

[Structural Formula 25] [Structural Formula 26] [Structural Formula 27] [Structural Formula 28]

[Structural Formula 29]

The carbon residue of the aromatic ring in the linking group L may be bonded to hydrogen or deuterium. The method according to claim 1,
n is 1 or 2, and X in the substituent M is O. The method according to claim 1,
Wherein the compound represented by the formula (A) is any one selected from the group consisting of the following compounds [1] to [248].

[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 142]

[Compound 143] [Compound 144] [Compound 145]

[Compound 146] [Compound 147] [Compound 148]

[Compound 149] [Compound 150] [Compound 151]

[Compound 152] [Compound 153] [Compound 154]

[Compound 155] [Compound 156] [Compound 157]

[Compound 158] [Compound 159] [Compound 160]

[Compound 161] [Compound 162] [Compound 163]

[Compound 164] [Compound 165] [Compound 166]

[Compound 167] [Compound 168] [Compound 169]

[Compound 170] [Compound 171] [Compound 172]

[Compound 173] [Compound 174] [Compound 175]

[Compound 176] [Compound 177] [Compound 178]

[Compound 179] [Compound 180] [Compound 181]

[Compound 182] [Compound 183] [Compound 184]

[Compound 185] [Compound 186] [Compound 187]

[Compound 188] [Compound 189] [Compound 190]

[Compound 191] [Compound 192] [Compound 193]

[Compound 194] [Compound 195] [Compound 196]

[Compound 197] [Compound 198] [Compound 199]

[Compound 200] [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] The method according to claim 1,
Wherein the organic light emitting device further 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, an electron transporting layer, and an electron injecting layer in addition to the light emitting layer. 9. The method of claim 8,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. The method according to claim 1,
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. The method according to claim 1,
Wherein the light emitting layer further comprises at least one compound selected from the group consisting of compounds represented by the following formulas (B) and (C) as a dopant.
[Chemical Formula B] [Chemical Formula C]

In the above formulas (B) and (C)
A represents 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 6 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S,
In the above formula (B)
X ₁ and X ₂ are the same or different and 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 each independently represent 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 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 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, heavy hydrogen, and hydrogen Y ₁ to Y ₂ are the same or different from each other and form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group You can.
Wherein l and m are each a number of 1 to 20,
n is a number of from 1 to 4;
In the above formula (C)
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 fused form, and the hydrogen sites in the cycloalkane may each be substituted with deuterium or alkyl of 1 to 20 carbon atoms, The same or different;
B is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, two or more R ₅ and R ₆ are the same or different;
Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are and independently of one another identical or different and are hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone 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 C2-C20 alkenyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C1 to C60 alkylthio group, a substituted or unsubstituted C3 to C60 cycloalkyl group, Substituted or unsubstituted aryloxy groups having 6 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted C2 to C60 hetero Ah (Substituted or unsubstituted C1-C60 alkyl) amino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C1-C60 alkylamino group, (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, 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, or boron Lt; / RTI &gt;
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 a fused form,
n is an integer of 1 to 4;

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