KR20170056425A - Heterocyclic compound comprising aromatic amine group and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound comprising an aromatic amine group and an organic light-emitting diode including the same. The heterocyclic compound can express excellent diode properties such as light emitting efficiency when being used as an organic light emitting material.

Description

BACKGROUND ART Heterocyclic compounds containing aromatic amine groups and organic light emitting devices containing the same are well known to those skilled in the art.

The present invention relates to a heterocyclic compound containing an aromatic amine group and an organic light emitting device comprising the same. More particularly, the present invention relates to a heterocyclic compound having excellent luminous efficiency and exhibiting improved properties when used as an organic light emitting material, And an organic light emitting device including the same.

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 electric energy into light energy. The organic light emitting device using the organic light emitting device 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.

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 .

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.

An organic light emitting device using an arylamine-bonded indenofluorene derivative or the like is disclosed as a prior art related to a dopant compound in such a light emitting layer in Patent Document 10-2008-0015865 (2008.02.20) No. 10-2012-0047706 (20012.05.14) discloses a compound having a structure in which dibenzofuran or dibenzothiophene is present together with fluorene or benzofuran or dibenzothiophene is present together with carbazole in one molecule An organic electroluminescent device using the same.

However, despite the above efforts, there is a continuing need for the development of a novel organic light emitting material having improved luminous efficiency and improved effect as compared with the organic light emitting materials manufactured by the prior art including the prior art .

Published Patent Application No. 10-2008-0015865 (Feb. 20, 2008)

Japanese Patent Application Laid-Open No. 10-2012-0047706 (20012.05.14)

Therefore, the first technical object of the present invention is to provide a novel organic luminescent material which can be used in the luminescent layer of an organic light emitting diode (OLED), and can show improved device characteristics.

A second object of the present invention is to provide an organic light emitting device including the organic light emitting material.

In order to achieve the first technical object, the present invention provides an amine compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring, An aromatic heterocycle having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a fused ring together with the W to form a 5-membered ring;

The linking groups L1 to L12 are the same or different from each other and each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 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 heteroarylene group having 2 to 60 carbon atoms;

W is selected from SiR ₁ R ₂ , GeR ₁ R ₂ , O, S, NR ₁ ,

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

The substituents R ₁ to R ₉ and Ar ₁ to Ar 8 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkoxy group, An 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, An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkyl germanium group, a substituted or unsubstituted C6-C30 aryl germanium group, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

Each of p1 to p4, r1 to r4 and s1 to s4 is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L12 is the same or different from each other,

X is an integer of 1 or 2, y and z are the same or different and independently of one another an integer of 0 to 3,

Ar1 and Ar2, Ar3 and Ar4, Ar5 and Ar6, and Ar7 and Ar8 may be connected to each other to form a ring;

In the formula (A), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) to form a condensed ring,

In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) ≪ / RTI >

The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , 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 or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 6 to 24 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 light emitting compound represented by Formula A or Formula B of the present invention .

According to the present invention, the amine compound represented by the above-mentioned formula (A) or (B) can exhibit improved device characteristics with high efficiency as compared with the existing materials, and can be used for an 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. In the drawings of the present invention, the sizes and dimensions of the structures are enlarged or reduced from the actual size in order to clarify the present invention, and the known structures are omitted so as to reveal the characteristic features, and the present invention is not limited to the drawings .

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. In the following description, well-known functions or constructions are not described in detail to avoid obscuring the subject matter of the present invention.

It is to be understood that both the foregoing general description and the following detailed description of the present invention are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. Respectively. In the drawings, for the convenience of explanation, the thicknesses of some layers and regions are exaggerated. It will be understood that when a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the other portion "directly on" but also the other portion in between.

Also, throughout the specification, when an element is referred to as "including" an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. Also, throughout the specification, the term " on " means located above or below a target portion, and does not necessarily mean that the target portion is located on the upper side with respect to the gravitational direction.

The present invention provides an organic compound represented by the following formula (A) or (B) as an organic luminescent compound that can be used in a light emitting layer of an organic light emitting device.

(A)

[Chemical Formula B]

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring, An aromatic heterocycle having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a fused ring together with the W to form a 5-membered ring;

The linking groups L1 to L12 are the same or different from each other and each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 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 heteroarylene group having 2 to 60 carbon atoms;

W is selected from SiR ₁ R ₂ , GeR ₁ R ₂ , O, S, NR ₁ ,

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

The substituents R ₁ to R ₉ and Ar ₁ to Ar 8 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkoxy group, An 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, An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkyl germanium group, a substituted or unsubstituted C6-C30 aryl germanium group, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

Each of p1 to p4, r1 to r4 and s1 to s4 is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L12 is the same or different from each other,

X is an integer of 1 or 2, y and z are the same or different and independently of one another an integer of 0 to 3,

Ar1 and Ar2, Ar3 and Ar4, Ar5 and Ar6, and Ar7 and Ar8 may be connected to each other to form a ring;

In the formula (A), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) to form a condensed ring,

In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) ≪ / RTI >

The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , 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 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 6 to 24 carbon atoms.

In the compound represented by the above formula (A) or (B) in the present invention, when the formula (Q1) is connected to the A2 ring in the above formula (A), the amine group including Ar1 and Ar2 is necessarily bonded to the A2 ring , And the structural formula Q2 is connected to the A1 ring in formula (B) and the A2 ring is connected to the A2 ring in the structural formula (B), the amine group including Ar1 and Ar2 is necessarily bonded to the A2 ring.

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 6 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 6 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.

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 the removal of one hydrogen, 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 phenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, a halogen atom (-NH ₂₎ , -NH (R), -N (R ') (R "), R' and R" are independently of each other 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 24 carbon atoms 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 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 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, 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, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

As an embodiment, A1, A2, E and F in the formula (A) or formula (B) of the present invention may be the same or different and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms.

As described above, in the case where A1, A2, E and F in Formula (A) or Formula (B) are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, the aromatic hydrocarbon The rings may be the same or different and independently selected from [Structural formulas 10] to [Structural formula 21].

[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

 [Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above-mentioned structural formulas 10 to 21, "- *" means a bonding site for forming a 5-membered ring including W or a 5-membered ring including M in the structures Q1 and Q2 ,

When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q1 or the structural formula Q2 with the ring corresponding to the A1 ring or the A2 ring, two adjacent carbon atoms of the aromatic hydrocarbon ring are bonded to * Or combine with * of formula Q2 to form a condensed ring;

In the above Structural Formulas 10 to 21, R is the same as R1 and R2 defined above, m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, each R is the same Or may be different.

As an embodiment, A1, A2, E and F in the above formula (A) or formula (B) of the present invention may be the same or different and each independently represent a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.

The linking groups L1 to L12 may each be a single bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In this case, the couplers L1 to L12 may be a single coupling, Is any one selected from the following Structural Formulas 22 to 30,

p1 to p4, r1 to r4, s1 to s4 are each 1 or 2, and x may be 1, and in this case, more specifically, y may be 1 and z may be 0.

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

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

[Structural Formula 30]

Here, the carbon position of the aromatic ring in the linking group of the above-mentioned [structural formulas 22] to [structural formula 30] may be bonded to hydrogen or deuterium.

The substituents R 1 and R 2 in the above formula (A) or (B) may be the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms.

In this case, the substituents R1 and R2 may be connected to each other to form a ring, or may not be connected to each other to form a ring.

The substituents R 1 to R 9 and Ar 1 to R 8 in the present invention are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms having at least one hetero atom selected from O, N, S and Si, a cyano group, and a halogen group.

In one embodiment, W in the amine compound represented by the above formulas (A) and (B) of the present invention may be any one selected from O, S and NR ₃ .

In the formula (A) or (B) of the present invention, the "substituent" in the above Al, A2, E, F, Ar1 to Ar8, L1 to L12 and R1 to R9 is more preferably a cyano group, a halogen group, An alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, May be selected.

The amine compound of the present invention may be any one selected from the following formulas (1) to (45), but is not limited thereto .

≪ Formula 1 > (2) (3)

≪ Formula 4 > ≪ Formula 5 > (6)

≪ Formula 7 > (8) ≪ Formula 9 >

≪ Formula 10 > ≪ Formula 11 > ≪ Formula 12 >

≪ Formula 13 > ≪ Formula 14 > ≪ Formula 15 >

≪ Formula 16 > ≪ Formula 17 > ≪ Formula 18 >

(19) (20) ≪ Formula 21 >

(22) ≪ Formula 23 > ≪ EMI ID =

≪ Formula 25 > (26) ≪ Formula 27 >

(28) (29) (30)

 &Lt; Formula 31 > < EMI ID = &Lt; Formula 33 &gt;

(34)  &Lt; Formula 35 > &Lt; EMI ID =

(37) &Lt; Formula 380 & &Lt; EMI ID =

&Lt; EMI ID = &Lt; EMI ID = (42)

&Lt; Formula 43 > &Lt; Formula 44 > <Formula 45>

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 comprises at least one organic electroluminescent compound according to the present invention.

In the present invention, the phrase "(organic layer) contains at least one organic compound" means that one organic compound belonging to the category of the present invention (organic layer) or two or more different compounds belonging to the category of organic compound May be included.

The organic layer containing the organic luminescent compound of the present invention may include 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, have.

At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, and the organic light emitting compound of the present invention may be used as a dopant.

In the present invention, a host material may be used for the light emitting layer, in addition to a dopant. When the light emitting layer 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.

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 transport materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolin-10- olate: Bebq2), compound 201, compound 202, BCP, oxadiazole derivative PBD, BMD, BND, and the like may be used, but the present invention is not limited thereto.

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 (C).

&Lt; RTI ID = 0.0 &

In the above formula (C)

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 6 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 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.

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 hole injection layer material is not particularly limited as long as it is commonly used in the art. For example, HATCN (2-naphthylphenyl) phenylamino) -triphenylamine], NPD [N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine] N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4 , 4'-diamine], 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 (naphthalene-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 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.

The light emitting layer may be made of a host and a dopant.

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

Here, the host used in the light emitting layer may be a compound represented by the following Chemical Formulas 1A to 1D.

&Lt; EMI ID =

In the above formula (1A)

Ar _{7 ,} Ar ₈ and Ar ₉ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaromatic linking group;

R ₂₁ to R ₃₀ are the same or different and each independently represents hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a 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 aryl group, 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 aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, A substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Or an 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, boron Each substituent may form a fused ring with the adjacent groups;

E, f and g are the same as or different from each other and each independently 0 or an integer of 1 to 4;

The two sites indicated by * in the anthracene may be the same as or different from each other, and may independently form an anthracene derivative selected from the following formulas (1Aa-1) to (1Aa-3) in combination with the P or Q structure.

[Chemical Formula 1Aa-1] [Chemical Formula 1Aa-2] Chemical Formula 1Aa-3]

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 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, a heteroaryl group having 2 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 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 6 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.

&Lt; RTI ID = 0.0 &

In the above formula (1B)

Wherein Ar ₁₇ to Ar ₂₀ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are the same as defined in R ₂₁ to R ₃₀ in Formula 1A Lt; / RTI &gt;

W and ww are the same as or different from each other, x and xx are the same as or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3; Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

[Chemical Formula 1C]

In the above formula (1C)

Wherein Ar ₂₁ to Ar ₂₄ are the same or different and are made of the same substituents as defined for Ar ₇ to Ar ₈ in the (1A) each independently from each other, wherein R ₆₄ to R ₆₇ is at R ₂₁ to R ₃₀ of Formula 1A Lt; / RTI &gt; is as defined above.

The above ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and the above-mentioned II to 11 are the same or different and independently an integer of 0 to 4.

[Chemical Formula 1D]

In the above formula (1D)

Wherein Ar ₂₅ to Ar ₂₇ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in formula (1A), and R ₆₈ to R ₇₃ are the same or different from each other, consists of the same substituents as defined in R 1A of ₂₁ to R _30, each substituent may form a saturated or unsaturated cyclic structure each other adjacent haneungeot. In addition, the mm to ss are the same or different from each other and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group consisting of the following [host 1] to [host 56], but is not limited thereto.

[Host 1] [Host 2] [Host 3] [Host 4]

[Host 5] [Host 6] [Host 7] [Host 8]

[Host 9] [Host 10] [Host 11] [Host 12]

[Host 13] [Host 14] [Host 15] [Host 16]

[Host 17] [Host 18] [Host 19] [Host 20]

[Host 21] [Host 22] [Host 23] [Host 24]

[Host 25] [Host 26] [Host 27] [Host 28]

[Host 29] [Host 30] [Host 31] [Host 32]

[Host 33] [Host 34] [Host 35] [Host 36]

[Host 37] [Host 38] [Host 39] [Host 40]

[Host 41] [Host 42] [Host 43] [Host 44]

[Host 45] [Host 46] [Host 47] [Host 48]

[Host 49] [Host 50] [Host 51] [Host 52]

[Host 53] [Host 54] [Host 55] [Host 56]

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

Also, in the present invention, at least one layer selected from the respective layers may be formed by a deposition process or a solution process. Here, the deposition process 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 a vacuum or a 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 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.

(Example)

Synthetic example  1: Synthesis of formula (1)

Synthesis Example 1 - (1): Synthesis of intermediate 1-a

Intermediate 1-a was synthesized according to Scheme 1 below:

<Reaction Scheme 1>

<Intermediate 1-a>

In a 1 L round bottom flask reactor, morpholino-1-cyclohexene (25 g, 0.157 mol) and benzoquinone (14 g, 0.13 mol) were added dropwise to the toluene solution at 0 ° C over a period of one hour and stirred at the same temperature. The precipitate was filtered, washed with toluene, and then hydrochloric acid was added thereto. The mixture was stirred for 6 hours and then separated by column chromatography to obtain <Intermediate 1-a> (13 g, 44%).

Synthesis Example 1 - (2): Synthesis of intermediate 1-b

Intermediate 1-b was synthesized according to Scheme 2 below:

<Reaction Scheme 2>

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

 <Intermediate 1-a> (12 g, 0.064 mol), tert-butyl chloride (18 g, 0.195 mol) and zinc chloride (21.4 g, 0.16 mol) were dissolved in 280 ml of dichloromethane in a 1 L round bottom flask reactor and heated for 9 hours The residue was hydrolyzed with water and extracted with dichloromethane. The reaction product was dehydrated and the solvent was removed to obtain Intermediate 1-b (13 g, 83%).

Synthesis Example 1 - (3): Synthesis of intermediate 1-c

Intermediate 1-c was synthesized according to Scheme 3 below:

<Reaction Scheme 3>

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

<Intermediate 1-b> (10 g, 0.041 mol), carnitrate (0.095 g, 0.001 mol) and benzylamine (0.88 ml, 0.008 mol) were stirred in 130 ml of dichloromethane for 18 hours in a 1 L round bottom flask under an oxygen atmosphere . After completion of the reaction, the reaction mixture was washed with a 1M aqueous hydrochloric acid solution and then concentrated under reduced pressure to obtain Intermediate 1-c (8 g, 40%).

Synthesis Example 1 - (4): Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Scheme 4 below:

<Reaction Scheme 4>

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

     <Intermediate 1-c> (8 g, 0.016 mol) was dissolved in 55 ml of toluene, and 2,3-dichloro-5-6-dicyanobenzoquinone (14.5 g, 0.064 mol) was added to a 1 L round- And the mixture was stirred for 3 hours. The toluene is removed from the reaction product and the organic material is dissolved in chloroform. The organic layer was washed with sodium hydroxide solution and separated on a column chromatograph to obtain <Intermediate 1-d> (4.5 g, 59%).

Synthesis Example 1 - (5): Synthesis of intermediate 1-e

Intermediate 1-e was synthesized according to Scheme 5 below:

<Reaction Scheme 5>

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

<Intermediate 1-d> (4.5 g, 0.09 mol) and trichloroaluminum (3.6 g, 0.03 mol) were dissolved in 125 ml of toluene in a 1 L round bottom flask and stirred for 11 hours under nitrogen. The reaction mixture was filtered, and the solvent was removed under reduced pressure. The reaction mixture was extracted with chloroform, washed with an aqueous ammonium chloride solution and recrystallized with hexane to obtain Intermediate 1-e (8 g, 24%).

Synthesis Example 1 - (6): Synthesis of Intermediate 1-f

Intermediate 1-f was synthesized according to Scheme 6 below:

<Reaction Scheme 6>

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

(2.5 g, 0.007 mol) and para-toluenesulfonic acid (1.3 g, 0.007 mol) were added to a 50 mL round bottom flask, and the mixture was stirred at 110 ° C. Potassium carbonate aqueous solution is added and neutralized to pH 5 and extracted. The reaction mixture was concentrated under reduced pressure and the obtained organic layer was separated by column chromatography to obtain <Intermediate 1-f> (2 g, 82%).

Synthesis Example 1 - (7): Synthesis of Intermediate 1-g

Intermediate 1-g was synthesized according to Scheme 7 below:

<Reaction Scheme 7>

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

(2 g, 0.005 mmol) and 150 ml of dichloromethane were placed in a 1 L round bottom flask reactor, and the mixture was stirred at room temperature. Bromine (0.6 ml, 0.012 mol) was added dropwise to 8 ml of dichloromethane, and the mixture was stirred for 8 hours at room temperature After completion of the reaction, 15 ml of acetone was added and stirred, and the resulting solid was washed with acetone after filtration and recrystallized from monochlorobenzene to obtain <Intermediate 1-g> (2 g, 79%).

Synthesis Example 1 - (8): Synthesis of Intermediate 1-h

Intermediate 1-h was synthesized according to Scheme 8 below:

<Reaction Scheme 8>

       <Intermediate 1-h>

(10.0 g, 0.035 mol), 4-tertiarybutylaniline (5.8 g, 0.039 mol), tris (dibenzylideneacetone) di (0.65 g, 0.0007 mol), sodium tertiary butoxide (6.79 g, 0.0706 mol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthalene (0.44 g, 0.0007 mol) mol) and toluene (100 ml) were added, and the mixture was refluxed and stirred for 3 hours. After completion of the reaction, the mixture was cooled at room temperature and extracted. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The reaction mixture was separated by column chromatography to obtain <Intermediate 1-h> (10 g, 80%).

Synthesis Example 1 - (9): Synthesis of Chemical Formula 1

Formula 1 was synthesized according to Scheme 9 below:

<Reaction Scheme 9>

&Lt; Intermediate 1-g > < Intermediate 1-h &

<Intermediate 1-g> (2.0 g, 0.004 mol), <Intermediate 1-h> (2.5 g, 0.010 mol), palladium (II) acetate (0.03 g, 0.002 mol), sodium tertiary Butoxide (1.4 g, 0.015 mol), triturated butylphosphine (0.03 g, 0.002 mol) and toluene (30 ml) were added and the mixture was refluxed and stirred for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was extracted with dichloromethane and water, treated with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The reaction mixture was separated by column chromatography, and recrystallized from dichloromethane and acetone to obtain 1.5 g (36%) of the compound of formula (1).

MS (MALDI-TOF): m / z 1046.44 [M ^&lt; ⁺ &^gt;].

Synthetic example  2: Synthesis of Compound (26)

Synthesis Example 2 - (1): Synthesis of intermediate 2-a

Intermediate 2-a was synthesized according to Scheme 10 below:

<Reaction formula 10>

<Intermediate 1-e> <Intermediate 2-a>

(4.5 g, 0.012 mol) was dissolved in 50 ml of dimethylacetamide, and then methanesulfonyl chloride (2.8 ml, 0.036 mol) was added to a 500 ml round bottom flask, and pyridine (4.8 ml, 0.06 mol) And stirred at 70 < 0 > C for 4 hours. An excess amount of water is added to the reaction product, which is then extracted with ethyl acetate. The extracted organic layer was recrystallized with ethanol to obtain <Intermediate 2-a> (4 g, 62%).

Synthesis Example 2 - (2): Synthesis of intermediate 2-b

Intermediate 2-b was synthesized according to Scheme 11 below:

<Reaction Scheme 11>

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

<Intermediate 2-a> (4g, 0.008mol) and aniline (0.58ml, 0.006mol) were dissolved in 15ml of xylene, and potassium phosphate (8.12g, 0.038mol), tri-dibenzylidineacetone dipalladium (0.7 g, 0.0008 mol) and Zanphos (0.89 g, 0.0015 mol) were added, and the mixture was stirred at 120 ° C for 72 hours. After cooling to room temperature, distillate under reduced pressure to remove xylene and extract with dichloromethane. The water was removed and hexane was added to leave a small amount of the solvent. <Intermediate 2-b> (2 g, 62%) was obtained.

Synthesis Example 2 - (3): Synthesis of intermediate 2-c

Intermediate 2-c was synthesized according to Scheme 12 below:

<Reaction Scheme 12>

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

Bromine (1.2 ml, 0.023 mol) was added dropwise to 15 ml of dichloromethane, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was stirred at room temperature for 4 hours, After completion of the reaction, 30 ml of acetone was added and stirred, and the resulting solid was washed with acetone after filtration and recrystallized from monochlorobenzene to obtain <Intermediate 2-c> (4 g, 76%).

Synthesis Example 2 - (4): Synthesis of Chemical Formula 26

26 was synthesized according to Scheme 13 below:

<Reaction Scheme 13>

  <Intermediate 2-c> <Formula 26>

(5.0g, 0.009mol), bis (4-tert-butylphenyl) amine (6.0g, 0.021mol), palladium (II) acetate (0.08g, 0.4mmol) in a 250ml round bottom flask reactor, , Sodium tertiary butoxide (3.4 g, 0.035 mol), triturated butyl phosphine (0.07 g, 0.4 mmol), and toluene (60 ml) were added and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was extracted with dichloromethane and water. After anhydrous treatment with magnesium sulfate, the mixture was concentrated under reduced pressure. The reaction mixture was separated by column chromatography, and recrystallized from dichloromethane and acetone to obtain (4g, 45%).

MS (MALDI-TOF): m / z 981.25 [M ^&lt; ⁺ &^gt;].

Example  1 to 2: Preparation of Organic Light Emitting Diode

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. Organic materials were deposited on the ITO in the order of HATCN (50 Å) and NPD (650 Å) (E-1) as an electron transporting layer (300 Å), Liq as an electron injecting layer (10 Å), Al (1,000 Å) as an electron injecting layer, ) To form an organic light emitting device. The luminescent characteristics of the organic light emitting device were measured at 10 mA / cm ² .

[HATCN] [NPD]             [BH]

[Formula E-1] [Liq]

Comparative Example  One

Except for using [BD1] as a dopant in the light emitting layer used in Examples 1 and 2, an organic light emitting device was fabricated in the same manner, and the light emitting characteristics of the organic light emitting device were measured at 10 mA / cm ² . The structure of [BD1] is as follows.

[BD1]

Dopant V CIEx CIEy EQE Example 1 Formula 1 3.8 0.138 0.118 8.4 Example 2 26 3.9 0.138 0.120 8.0 Comparative Example 1 BD1 4.2 0.139 0.122 6.2

According to the results of Examples 1 and 2, the organic light emitting device according to the present invention exhibits higher efficiency characteristics than the organic light emitting device according to Comparative Example 1, and thus is highly applicable to organic light emitting devices .

Claims (15)

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

[Chemical Formula B]

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring, An aromatic heterocycle having 2 to 40 carbon atoms;
Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a fused ring together with the W to form a 5-membered ring;
The linking groups L1 to L12 are the same or different from each other and each independently represent a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 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 heteroarylene group having 2 to 60 carbon atoms;
W is selected from SiR ₁ R ₂ , GeR ₁ R ₂ , O, S, NR ₁ ,
M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;
The substituents R ₁ to R ₉ and Ar ₁ to Ar 8 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkoxy group, An 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, An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkyl germanium group, a substituted or unsubstituted C6-C30 aryl germanium group, a cyano group, a nitro group, and a halogen group,
The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;
Each of p1 to p4, r1 to r4 and s1 to s4 is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L12 is the same or different from each other,
X is an integer of 1 or 2, y and z are the same or different and independently of one another an integer of 0 to 3,
Ar1 and Ar2, Ar3 and Ar4, Ar5 and Ar6, and Ar7 and Ar8 may be connected to each other to form a ring;
In the formula (A), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) to form a condensed ring,
In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) &Lt; / RTI &gt;
The "substituted" in the above "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , 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 or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
A1, A2, E and F in the above-mentioned formula (A) or (B) are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms. 3. The method of claim 2,
Wherein the aromatic hydrocarbon rings are the same or different and independently of one another selected from the group consisting of Structural Formulas 10 to 21.
[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above-mentioned structural formulas 10 to 21, "- *" means a bonding site for forming a 5-membered ring including W or a 5-membered ring including M in the structures Q1 and Q2 ,
When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q1 or the structural formula Q2 with the ring corresponding to the A1 ring or the A2 ring, two adjacent carbon atoms of the aromatic hydrocarbon ring are bonded to * Or combine with * of formula Q2 to form a condensed ring;
In the above Structural Formulas 10 to 21, R is the same as R1 and R2 defined in Claim 1, and m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, each R May be the same or different from each other. The method according to claim 1,
Wherein each of the linking groups L1 to L12 is any one selected from the group consisting of a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, compound. 5. The method of claim 4,
The linking groups L1 to L12 may be a single bond or any one selected from the following Structural Formulas 22 to 30,
p1 to p4, r1 to r4, s1 to s4 are each 1 or 2,
and x is 1.
[Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25]

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

[Structural Formula 30]

The carbon position of the aromatic ring in the linking group may be bonded with hydrogen or deuterium. 6. The method of claim 5,
y is 1, and z is 0. The method according to claim 1,
The substituents R 1 and R 2 in the above formula (A) or (B) are the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms. The method according to claim 1,
And W is any one selected from the group consisting of O, S and NR ₃ . The method according to claim 1,
The substituents R1 to R9 and Ar1 to Ar8 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl, a substituted or unsubstituted C3 to C30 cycloalkyl, A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms having at least one hetero atom selected from O, N, S and Si, a cyano group, and a halogen group. The method according to claim 1,
Is any one selected from the following formulas (1) to (45).
&Lt; Formula 1 >< EMI ID =

&Lt; Formula 4 &gt;&lt; EMI ID =

&Lt; Formula 7 >< EMI ID =

&Lt; Formula 10 &gt;&lt; EMI ID =

&Lt; Formula 13 >< EMI ID =

&Lt; Formula 16 &gt;&lt; EMI ID =

&Lt; Formula 19 >< EMI ID =

&Lt; Formula 22 &gt;&lt; EMI ID =

&Lt; Formula 25 >< EMI ID = 26.0 >

&Lt; Formula 28 >< EMI ID = 29.0 >

&Lt; Formula 31 >< EMI ID =

&Lt; Formula 34 &gt;&lt; EMI ID =

&Lt; Formula 37 >< EMI ID =

&Lt; Formula 40 &gt;&lt; EMI ID =

&Lt; General Formula 43 >

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 at least one organic electroluminescent compound selected from the group consisting of the organic electroluminescent compounds according to any one of claims 1 to 10. 12. The method of claim 11,
Wherein the organic layer 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. 13. The method of claim 12,
An organic layer interposed between the first electrode and the second electrode includes a light emitting layer,
Wherein the light emitting layer comprises a host and a dopant, and the organic light emitting compound is used as a dopant. 13. The method of claim 12,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 12. The method of claim 11,
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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