KR20150064500A - Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same - Google Patents

Abstract

The present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same. The organic electroluminescent compounds of the present invention can manufacture the organic electroluminescent device having excellent driving lifespan, and improved current efficiency and power efficiency since driving voltage is low.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent compound and an organic electroluminescent compound including the same,

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

Among display devices, an electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, an excellent contrast, and a high response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. Fluorescent materials have been widely used as luminescent materials to date, but the development of phosphorescent materials has been widely studied in that phosphorescent materials can improve luminous efficiency up to 4 times the theoretical efficiency of phosphorescent materials in terms of the mechanism of electroluminescence . Until now, an iridium (III) complex series has been widely known as a phosphorescent material. Each RGB has bis (2- (2'-benzothienyl) -pyridinate-N, C-3 ') iridium (acetylacetonate ) [(acac) Ir (btp ) 2], tris (2-phenylpyridine) iridium [Ir (ppy) _3] and bis (4,6-difluorophenyl pyridinyl Nei Sat -N, C2) avoid collision Ney And materials such as tolidium (Firpic) are known.

In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer et al. Of Japan have been using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material and developed a high-performance organic electroluminescent device.

However, existing materials are advantageous in terms of luminescent properties, but they have the following disadvantages: (1) the material is changed when the glass transition temperature is low and the thermal stability is low and the material is subjected to a high temperature deposition process under vacuum. (2) In the organic electroluminescent device, the power efficiency is in the relation of [(? / Voltage) x current efficiency], so that the power efficiency is inversely proportional to the voltage. In the organic electroluminescent device using the phosphorescent host material, The current efficiency (cd / A) is higher than that of the light emitting device, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). (3) In addition, when used in an organic electroluminescent device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.

Korean Patent Laid-Open Publication No. 10-2013-0064001 discloses a pyrrole-carbazole skeleton in which a pyrrole is fused to a (1, 2), (2,3) or (3,4) A compound in which a substituent is connected to each nitrogen atom in the sol portion is disclosed as a host compound for an organic electroluminescence device.

However, the above document does not specifically disclose a compound in which a substituent is connected to the carbon atom of the 5-membered heteroaryl portion in the skeleton formed by fusing a 5-membered heteroaryl group to a carbazole.

Korean Patent Laid-Open Publication No. 10-2013-0064001 (published on June 17, 2013)

An object of the present invention is to provide an organic electroluminescent compound capable of producing an organic electroluminescent device having a low driving voltage, a high luminous efficiency and a high power efficiency.

As a result of intensive studies to solve the above technical problems, the present inventors have found that an organic electroluminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.

[Chemical Formula 1]

In Formula 1,

A represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-30 membered) , A substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group;

L is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5-30 membered) heteroarylene group;

R ₁ to R ₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl group, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted (C1-C30) alkylsilyl group, substituted or unsubstituted (C6- Substituted or unsubstituted (C6-C30) arylamino groups, substituted or unsubstituted (C6-C30) arylsilyl groups, substituted or unsubstituted Or an unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, or may form a monocyclic or polycyclic alicyclic or aromatic ring by being connected to adjacent substituents, and the carbon atom of the alicyclic or aromatic ring May be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;

X is -O-, -S-, -CR ₁₁ R ₁₂ -, -NR ₁₃ -, or -SiR ₁₄ R ₁₅ -;

R ₁₁ to R ₁₅ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-30 membered) And the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a is an integer of 0 to 4, and when a is 2 or more, each R ₁ may be the same or different;

b is an integer of 0 to 2, and when b is 2, each R ₃ may be the same or different;

n is an integer of 1 or 2, and when n is 2, each L may be the same or different;

m is an integer of 0 to 3, and when m is 2 or more, each A may be the same or different.

The organic electroluminescent compound according to the present invention is advantageous in manufacturing an organic electroluminescent device having a low driving voltage and excellent luminous efficiency and power efficiency.

The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.

The present invention relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the compound.

The organic electroluminescent compound represented by Formula 1 of the present invention will be described in more detail as follows.

The organic electroluminescent compound represented by Formula 1 may be one or more compounds represented by the following Formulas 2 to 3.

(2)

(3)

In the above Formulas 2 to 3,

R ₁ to R ₃ , L, A, X, m, n, a and b are the same as defined in the formula (1).

Specific examples of the "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Specific examples of the "alkenyl" herein include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. Examples of "alkynyl" herein include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2- Examples of "cycloalkyl" herein include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "(5-7 membered) heterocycloalkyl" as used herein means an aromatic heterocycle having 5 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (= O) Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, " aryl (phenylene) " means a single ring or fused ring radical derived from an aromatic hydrocarbon, including spiro compounds in which two rings are connected through one atom. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, Naphthyl, naphthyl, phenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crycenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl and the like. The term "(3-30) heteroaryl (phenylene)" used herein refers to a heteroaryl group having 3 to 30 ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, P Quot; means an aryl group containing an atom. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, And fused ring heteroaryl such as furanyl, quinazolinyl, quinoxalinyl, carbazolyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl, dihydroacrylidinyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Also, in the phrase "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. Substituents further substituted by A, L, R ₁ to R ₃ , and R ₁₁ to R ₁₅ in the general formulas 1 to 3 are each independently selected from the group consisting of deuterium; halogen; (C1-C30) alkyl unsubstituted or substituted with halogen; (C1-C30) alkoxy; (C5-C30) aryl; (3-30 membered) heteroaryl, unsubstituted or substituted by (C6-C30) aryl; (C3-C30) cycloalkyl; (5-7 membered) heterocycloalkyl; Tri (C1-C30) alkylsilyl; Tri (C6-C30) arylsilyl; Di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; (C2-C30) alkenyl; (C2-C30) alkynyl; Cyano; Di (C1-C30) alkylamino; Di (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) aryl; Carboxyl; Nitro; And hydroxy, each independently selected from the group consisting of deuterium; halogen; (C1-C10) alkyl; (C1-C10) alkoxy; (C3-C12) cycloalkyl; (C5-C18) aryl; (5-18 member) heteroaryl; Tri (C6-C12) arylsilyl; (C1-C6) alkyldi (C6-C12) arylsilyl; Di (C6-C12) arylamino; And (C1-C10) alkyl (C5-C18) aryl.

A represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-30 membered) (C 1 -C 30) alkylamino group, a substituted or unsubstituted (C 6 -C 30) arylamino group, or a substituted or unsubstituted (C 1 -C 30) alkyl (C 6 -C 30) arylamino group, Substituted or unsubstituted (C6-C21) aryl group, substituted or unsubstituted (5-21) heteroaryl group, substituted or unsubstituted (C6-C21) C10) alkyl (C6-C21) arylamino group, more preferably an unsubstituted (C1-C10) alkyl group; (C5-C18) aryl group, a (5-18 member) heteroaryl group or a tri (C6-C12) arylsilyl group substituted with at least one substituent selected from the group consisting of hydrogen, halogen, cyano, Or an unsubstituted (C6-C22) aryl group; (5-18 member) heteroaryl group substituted or unsubstituted with (C5-C18) aryl group; Or an unsubstituted (C6-C18) arylamino group. Specifically, A represents an unsubstituted (C1-C4) alkyl group; Which is unsubstituted or substituted with halogen, cyano, (C1-C4) alkyl, (C5-C8) cycloalkyl, phenyl, naphthyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or triphenylsilyl Phenyl, biphenyl, terphenyl, naphthyl or triphenylenyl; Fluorenyl group substituted or unsubstituted with a (C1-C4) alkyl group, 9,9'-spirobifluorenyl, or spiro [benzo [c] fluorene-7,9'-fluorene] group; Pyridyl; Carbazolyl, dibenzofuranyl or dibenzothiophenyl substituted or unsubstituted with phenyl; Benzo [b] naphtho [2,1-d] thiophenyl; Benzoimidazolyl substituted with phenyl; Benzothiazolyl; N, N-diphenylamino; Or N- (2-naphthyl) -N-phenylamino.

In the above Formulas 1 to 3, L is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5-30 membered heteroarylene group), preferably a substituted or unsubstituted (C6- C21) aryl group or a substituted or unsubstituted (5-21 member) heteroarylene group, more preferably, when n is 1, L is substituted or unsubstituted with a (C1-C10) (5-18) heteroarylene group unsubstituted or substituted by (C6-C18) arylene group or (C1-C10) alkyl group or (C6-C18) aryl group, and when n is 2, And L is a substituted or unsubstituted C1-C10 alkyl group or a (C6-C18) aryl group, and the other L is a substituted or unsubstituted C6-C18 aryl group, Or a (5-18 member) heteroarylene group substituted or unsubstituted with a (C6-C18) arylene group or a (C1-C10) alkyl group or a (C6-C18) aryl group. Specifically, when n is 1, L is phenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl; when n is 2, L, which is directly linked to A, is phenyl, pyridyl, pyrimidinyl, triazinyl, indolyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl, C4) alkyl group or a phenyl group.

R ₁ to R ₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) A substituted or unsubstituted (C1-C30) alkylsilyl group, a substituted or unsubstituted (C1-C30) alkylsilyl group, A substituted or unsubstituted (C6-C30) arylsilyl group, a substituted or unsubstituted (C6-C30) aryl (C1-C30) alkylsilyl group, a substituted or unsubstituted (C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group or may be connected with adjacent substituents to form a monocyclic or polycyclic alicyclic or aromatic ring, Group or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur And; Preferably a substituted or unsubstituted (C1-C10) alkyl group or a substituted or unsubstituted (C6-C21) aryl group; More preferably a (C6-C18) aryl group substituted or unsubstituted with (C1-C10) alkyl. Specifically, R ₁ is phenyl substituted or unsubstituted with (C ₁ -C 4) alkyl, and R ₂ is phenyl or biphenyl.

Wherein X is -O-, -S-, -CR ₁₁ R ₁₂ -, -NR ₁₃ -, or -SiR ₁₄ R ₁₅ -; Preferably -O-, -S-, -CR ₁₁ R ₁₂ -, or -NR ₁₃ -; More preferably -NR < ₁₃ > -.

Wherein R ₁₁ to R ₁₅ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-30) A heteroaryl group or a substituent adjacent to each other to form a monocyclic or polycyclic alicyclic or aromatic ring and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, Can be replaced; Is preferably a substituted or unsubstituted (C1-C10) alkyl group, or a substituted or unsubstituted (C6-C21) aryl group, or may be connected with adjacent substituents to form a monocyclic or polycyclic alicyclic or aromatic ring ; (C6-C18) aryl group which is unsubstituted or substituted with a (C1-C6) alkyl group or a substituted or unsubstituted C6-C18 aryl group which is substituted with a An aromatic ring can be formed. Specifically, R ₁₁ and R ₁₂ are each independently a (C 1 -C 6) alkyl group; R ₁₃ may be phenyl substituted or unsubstituted with (C 1 -C 4) alkyl, or the phenyl may be connected to adjacent substituents to form a single or multiple aromatic ring.

In the above Formulas 1 to 3, a is an integer of 0 to 4, preferably 0 to 2, more preferably 0 or 1.

In the above Formulas 1 to 3, b is an integer of 0 to 2, preferably 0 or 1, more preferably 0.

In the above formulas (1) to (3), n is 1 or 2.

In the above general formulas (1) to (3), m is an integer of 0 to 3, preferably 1 or 2.

According to an embodiment of the present invention, A represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted A substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group; L is a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-21 member) heteroarylene group; R ₁ to R ₃ are each independently a substituted or unsubstituted (C1-C10) alkyl group or a substituted or unsubstituted (C6-C21) aryl group; X is -O-, -S-, -CR ₁₁ R ₁₂ -, or -NR ₁₃ -; R ₁₁ to R ₁₅ each independently represent a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C21) aryl group, or may be connected to adjacent substituents to form a monocyclic or polycyclic alicyclic or aromatic ring ≪ / RTI > a is 0 to 2, and when a is 2, each R < ₁ > may be the same or different; b is 0 or 1; n is 1 or 2, and when n is 2, each L may be the same or different; m is 1 or 2, and when m is 2, each A may be the same or different.

According to another embodiment of the present invention, A represents an unsubstituted (C1-C10) alkyl group; (C5-C18) aryl group, a (5-18 member) heteroaryl group or a tri (C6-C12) arylsilyl group substituted with at least one substituent selected from the group consisting of hydrogen, halogen, cyano, Or an unsubstituted (C6-C22) aryl group; (5-18 member) heteroaryl group substituted or unsubstituted with (C5-C18) aryl group; An unsubstituted (C6-C18) arylamino group; L is a (C6-C18) arylene group or a (C1-C10) alkyl group or (C6-C18) aryl group which is substituted or unsubstituted with a (C1-C10) A substituted or unsubstituted (5-18 member) heteroarylene group, and when n is 2, L directly bonded to A is an unsubstituted (C6-C18) arylene group or an unsubstituted (5-18 member) heteroaryl group (C 1 -C 10) alkyl group or (C 6 -C 18) aryl group which is unsubstituted or substituted with a (C 1 -C 10) alkyl group or a (C 6 -C 18) aryl group, An unsubstituted (5-18 member) heteroarylene group; R ₁ to R ₂ are each independently a (C6-C18) aryl group substituted or unsubstituted with (C1-C10) alkyl; X is -O-, -S-, -CR ₁₁ R ₁₂ -, or -NR ₁₃ -; R ₁₁ to R ₁₅ are each independently a (C6-C18) aryl group unsubstituted or substituted by a (C1-C6) alkyl group or a substituted or unsubstituted aryl group, An alicyclic or aromatic ring of the ring; a is 0 or 1; b is 0; n is 1 or 2, and when n is 2, each L may be the same or different; m is 1 or 2, and when m is 2, each A may be the same or different.

The organic electroluminescent compounds of the above formulas (1) to (3) are more specifically exemplified by the following compounds, but are not limited thereto.

The organic electroluminescent compound according to the present invention can be prepared by a synthesis method known to a person skilled in the art and can be prepared, for example, as shown in the following Reaction Scheme 1.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

A, L, X, R ₁ to R ₃ , m, n, a and b are as defined in the above formula (1), and Hal is halogen.

A, L, X, R ₁ to R ₃ , m, n, a and b are as defined in the above formula (1), and Hal is halogen.

The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the same.

The material may be made of the organic electroluminescent compound of the present invention alone, and may further include common materials included in the organic electroluminescent material.

An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include at least one organic electroluminescent compound represented by Formula 1.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.

The organic electroluminescent compound of the present invention may be included in the light emitting layer. When used in a light emitting layer, the organic electroluminescent compound of the present invention can be included as a host material. Preferably, the light emitting layer may further include at least one dopant, and if necessary, a compound other than the organic electroluminescent compound of Formula 1 of the present invention may be further included as a second host material.

The second host material may be any known phosphorescent host, but is preferably selected from the group consisting of compounds represented by the following formulas (4) to (8) in view of luminous efficiency.

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 4 to 8,

Cz has the following structure,

X 'is -O- or -S-; R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Heteroaryl, or R ₂₅ R ₂₆ R ₂₇ Si-; R ₂₅ to R ₂₇ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, or a substituted or unsubstituted (C 6 -C 30) aryl; L ₄ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y ₁ and Y ₂ are -O-, -S-, -N (R ₃₁ ) - or -C (R ₃₂ ) (R ₃₃ ) -, and Y ₁ and Y ₂ are not simultaneously present; R ₃₁ to R ₃₃ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (5-30 membered) ₃₂ and R ₃₃ may be the same or different; h and i are each independently an integer of 1 to 3; j, k, l and p are each independently an integer of 0 to 4; (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R _23, or each R ₂₄ when each of h, i, j, k, May be the same or different.

Specifically, preferred examples of the second host material are as follows.

As the dopant included in the organic electroluminescent device of the present invention, compounds represented by the following formulas (9) to (11) can be used.

[Chemical Formula 9]

[Chemical formula 10]

(11)

In Formulas 9 to 11, L is selected from the following structures;

R ₁₀₀ is hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl; R ₁₀₁ to R ₁₀₉ And R ₁₁₁ To R < ₁₂₃ > are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, C1-C30) alkoxy; R ₁₂₀ to R ₁₂₃ may be adjacent to each other to form a fused ring; R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 1 -C 30) aryl; When R ₁₂₄ to R ₁₂₇ are aryl groups, the adjacent groups may be connected to each other to form a fused ring; R ₂₀₁ To R < ₂₁₁ > are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen or substituted or unsubstituted (C3-C30) cycloalkyl; f and g are each independently an integer of 1 to 3, and when f or g is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other; q is an integer of 1 to 3;

Specific examples of the dopant material are as follows.

The present invention further provides a material for manufacturing an organic electroluminescent device in a further aspect. The material includes a compound of the present invention as a host material or an electron transporting material. When the compound of the present invention is contained as a host material, the material may further comprise a second host material, wherein the weight ratio of the first host material to the second host material is in the range of 1:99 to 99: 1.

Further, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include the material for the organic electroluminescence device of the present invention.

The organic electroluminescent device of the present invention may include an organic electroluminescent compound having the general formula (1), and at the same time, at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds.

In addition, in the organic electroluminescent device of the present invention, in addition to the compound of Formula 1, an organic compound selected from the group consisting of Group 1, Group 2, Group 4, Group 5 transition metal, Lanthanide series metal and d- The organic layer may further include at least one light-emitting layer and a charge-generating layer, which are further included.

In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

In the organic electroluminescent device of the present invention, one layer (hereinafter referred to as a "surface layer") of a chalcogenide layer, a metal halide layer and a metal oxide layer is formed on at least one inner surface of a pair of electrodes ) Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO _X (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transport compound and the oxidative dopant, may be disposed on at least one surface of the pair of electrodes thus manufactured desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The formation of each layer of the organic electroluminescent device of the present invention may be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dip coating or flow coating Can be applied.

Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention.

[ Example  1] Preparation of compound H-22

Preparation of Compound 1-1

50 g (225 mmol) of 4-bromo-1-fluoro-2-nitrobenzene, 65.6 ml (720 mmol) of aniline and 450 ml (DMF) of dimethylformamide (DMF) were added to a 2 L round bottom flask ), And the mixture was stirred at 100 占 폚 overnight. The reaction mixture was distilled under reduced pressure. The crude product was subjected to column chromatography using methylene chloride (MC): hexane (Hx) to obtain Compound 1-1 (66 g, 99%).

Preparation of Compound 1-2

Compound 1 (66 g, 225 mmol), tin hydroxide (II) (254 g) and ethanol (1,100 ml) were added to 3 L of RBF and stirred at 70 ° C for 2 hours. The reaction mixture was neutralized with 4N NaOH (aq), worked up with ethyl acetate (EA) / H ₂ O, and water was removed with MgSO ₄ , followed by distillation under reduced pressure to obtain 54 g , 91%).

Preparation of compounds 1-3

Compound 2 (54 g, 205 mmol), benzaldehyde (21 ml, 205 mmol) and nitrobenzene (410 ml) were added to 2 L of RBF, and the mixture was stirred at 180 캜 for 5 hours. The reaction mixture was subjected to vacuum distillation to obtain Compound 1-3 (45 g, 63%).

Preparation of compounds 1-4

To a solution of 2L of RBF was added compound 1-3 (45 g, 129 mmol), chloroaniline (20 ml, 193 mmol), palladium (II) acetate [Pd (OAc) ₂ ] -butylphosphine _{[P (tBu) 3] (} 5 ml, 10 mmol), sodium tert-butoxide ^{(NaO t Bu) (31 g} , 322 mmol) the rear dissolved in toluene (650 ml), at 130 ℃ Stir for 1.5 hours. The reaction mixture was worked up with EA / H ₂ O, the water was removed with MgSO ₄ , and the residue was subjected to vacuum distillation to obtain Compound 1-4 (41 g, 80%).

Preparation of compounds 1-5

To a solution of 1L of RBF was added compound 1-4 (39 g, 108 mmol), Pd (OAc) ₂ (2.4 g, 10.8 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (8 g, 21.6 mmol) ₂ CO ₃ (90 g, 650 mmol) and dimethylacetamide (DMA) (540 ml) were added and the mixture was stirred at 190 ° C for 4 hours. The reaction mixture was poured into water to give a solid. The obtained solid compound was subjected to column separation using MC: Hx to obtain Compound 1-5 (8 g, 23%).

Preparation of Compound H-22

To a solution of compound 1-5 (4 g, 11 mmol), 2- (3-bromophenyl-4,6-diphenyl-1,3,5-triazine (5.2 g, 13 mmol), Pd _{(OAc) 2 (125 mg,} 0.5 mmol), 2- dicyclohexylphosphino-2 ', 6'-methoxy-phenyl fertilization (s-phos) (457 mg , 1.1 mmol), NaO t Bu (3.2 g, 33 mmol) and o-xylene (110 ml) were added, and the mixture was stirred for 5 hours at 160 ° C. The reaction mixture was worked up with EA / H ₂ O, water was removed with MgSO ₄ and the residue was distilled under reduced pressure. Was subjected to column separation with MC: Hx to obtain Compound H-22 (4.3 g, 53%).

Properties ^{data: mp = 328 o C, UV} = ( in toluene) 384nm, PL = 469nm (in toluene), MS / EIMS = 667

[device Production Example 1 ] The organic Field  Using a luminescent compound OLED  Device fabrication

An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N ¹ , N ^{1 '} - ([1,1'-biphenyl] -4,4'-diyl) bis ¹ - (naphthalene- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine) was added and the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr. And evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'- diaminobiphenyl was added to another cell in the vacuum vapor- And evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The compound H-22 of the present invention was added as a host to one cell in a vacuum vapor deposition apparatus and the compound D-1 as a dopant was introduced into another cell. Then, the two substances were evaporated at different rates, A dopant was doped in an amount of 15 wt% to deposit a 30 nm thick light emitting layer on the hole transport layer. Then, on one side of the luminescent layer, an electron transport layer was formed by adding a solution of 2- (4- (9,10-di (naphthalen-2-yl) anthracen- And lithium quinolate was added to another cell. Then, the two materials were evaporated at the same rate and doped in an amount of 50 wt% to deposit an electron transport layer of 30 nm. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

As a result, a power efficiency of 38.2 lm / W was obtained at a voltage of 2.6 V, and green light emission of 660 cd / m ² was confirmed.

[device Production Example 2 ] The organic Field  Using a luminescent compound OLED  Device fabrication

Except that Compound H-22 was used as a host material and Compound D- 88 was used as a dopant, dopants were doped into the dopant and the host in an amount of 4 wt% to deposit the light emitting layer. An OLED device was fabricated in the same manner as in Example 1.

As a result, a power efficiency of 8.2 lm / W was obtained at a voltage of 3.5 V, and red light emission of 990 cd / m ² was confirmed.

[ Comparative Example 1 ] Using a conventional light emitting material OLED  Device fabrication

As a light emitting material, 4,4'-N, N'-dicarbazole-biphenyl was used as a host, D-86 was used as a dopant, a 30 nm thick light emitting layer was deposited on the hole transport layer, Aluminum (III) bis (2-methyl-8-quinolinato) OLED device was fabricated in the same manner as in Device Manufacturing Example 1 except that 4-phenylphenolate was deposited to a thickness of 10 nm.

As a result, the power efficiency was 19.2 lm / W at a voltage of 5.8 V, and green light emission of 3000 cd / m ² was confirmed.

 [ Comparative Example 2 ] Using a conventional light emitting material OLED  Device fabrication

A luminescent layer of 30 nm in thickness was deposited on the hole transport layer using 4,4'-N, N'-dicarbazole-biphenyl and D-1 as a dopant, and aluminum (III ) Bis (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm, an OLED device was fabricated in the same manner as in Example 1.

As a result, a power efficiency of 1.9 lm / W was obtained at a voltage of 8.2 V, and red luminescence of 1000 cd / m ² was confirmed.

It was confirmed that the luminescent characteristics of the organic luminescent compounds developed in the present invention are superior to those of the conventional materials. In addition, the device using the compound for organic electronic material according to the present invention as a host material for luminescence not only excels in luminescence characteristics but also can lower the driving voltage, thereby inducing an increase in power efficiency and improving power consumption.

Claims (7)

An organic electroluminescent compound represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,
A represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-30 membered) , A substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group;
L is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5-30 membered) heteroarylene group;
R ₁ to R ₃ each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl group, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted (C1-C30) alkylsilyl group, substituted or unsubstituted (C6- Substituted or unsubstituted (C6-C30) arylamino groups, substituted or unsubstituted (C6-C30) arylsilyl groups, substituted or unsubstituted Or an unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, or may form a monocyclic or polycyclic alicyclic or aromatic ring by being connected to adjacent substituents, and the carbon atom of the alicyclic or aromatic ring May be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
X is -O-, -S-, -CR ₁₁ R ₁₂ -, -NR ₁₃ -, or -SiR ₁₄ R ₁₅ -;
R ₁₁ to R ₁₅ each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-30 membered) And the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a is an integer of 0 to 4, and when a is 2 or more, each R ₁ may be the same or different;
b is an integer of 0 to 2, and when b is 2, each R ₃ may be the same or different;
n is an integer of 1 or 2, and when n is 2, each L may be the same or different;
m is an integer of 0 to 3, and when m is 2 or more, each A may be the same or different. The compound according to claim 1, wherein the substituents further substituted in A, L, R ₁ to R ₃ , and R ₁₁ to R ₁₅ are each independently selected from the group consisting of deuterium; halogen; (C1-C30) alkyl unsubstituted or substituted with halogen; (C1-C30) alkoxy; (C5-C30) aryl; (3-30 membered) heteroaryl, unsubstituted or substituted by (C6-C30) aryl; (C3-C30) cycloalkyl; (5-7 membered) heterocycloalkyl; Tri (C1-C30) alkylsilyl; Tri (C6-C30) arylsilyl; Di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; (C2-C30) alkenyl; (C2-C30) alkynyl; Cyano; Di (C1-C30) alkylamino; Di (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) aryl; Carboxyl; Nitro; And hydroxy. ≪ / RTI > The organic electroluminescent compound according to claim 1, wherein the formula (1) is represented by the following formula (2) or (3).
(2)

(3)

In the above Formulas 2 to 3,
R ₁ to R ₃ , L, A, X, m, n, a and b are the same as defined in claim 1. The compound of claim 1, wherein A is a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-30 membered) (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group;
L is a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-21 member) heteroarylene group;
Each of R ₁ to R ₃ is independently a substituted or unsubstituted (C1-C10) alkyl group or a substituted or unsubstituted (C6-C21) aryl group;
X is -O-, -S-, -CR ₁₁ R ₁₂ -, or -NR ₁₃ -;
R ₁₁ to R ₁₅ each independently represents a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C21) aryl group, or a substituted or unsubstituted May form a ring;
Wherein a is 0 to 2, and when a is 2, each R < ₁ > may be the same or different;
B is 0 or 1;
Wherein n is 1 or 2, and when n is 2, each L may be the same or different;
Wherein m is 1 or 2, and when m is 2, each A may be the same or different. The compound according to claim 1, wherein A is an unsubstituted (C1-C10) alkyl group; (C5-C18) aryl group, a (5-18 member) heteroaryl group or a tri (C6-C12) arylsilyl group substituted with at least one substituent selected from the group consisting of hydrogen, halogen, cyano, Or an unsubstituted (C6-C22) aryl group; (5-18 member) heteroaryl group substituted or unsubstituted with (C5-C18) aryl group; An unsubstituted (C6-C18) arylamino group;
L is a (C6-C18) arylene group or a (C1-C10) alkyl group or (C6-C18) aryl group substituted or unsubstituted with a (C1- (5-18) membered heteroarylene group, and when n is 2, L directly bonded to A is an unsubstituted (C6-C18) arylene group or unsubstituted (5-18 member) heteroarylene group, (C6-C18) aryl group or (C6-C18) arylene group substituted or unsubstituted with a (C6-C18) aryl group or a A substituted or unsubstituted (5-18 member) heteroarylene group;
Wherein R ₁ to R ₂ are each independently a (C6-C18) aryl group substituted or unsubstituted with (C1-C10) alkyl;
X is -O-, -S-, -CR ₁₁ R ₁₂ -, or -NR ₁₃ -;
Each of R ₁₁ to R ₁₅ is independently a (C6-C18) aryl group unsubstituted or substituted with a (C1-C6) alkyl group or a substituted or unsubstituted aryl group, A polycyclic alicyclic or aromatic ring;
Wherein a is 0 or 1;
B is 0;
Wherein n is 1 or 2, and when n is 2, each L may be the same or different;
Wherein m is 1 or 2, and when m is 2, each A may be the same or different. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 12.