KR102352576B1 - An organic compound and an organic light emitting diode - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light emitting device including the same, and more particularly, to an organic compound having excellent lifespan, efficiency, electrochemical stability and thermal stability, and an organic electroluminescent device including the same.

Description

An organic compound and an organic light emitting diode comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.

Organic light emitting diodes (OLEDs) have a simpler structure than other flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), and have various advantages in manufacturing processes. It has excellent high luminance and viewing angle characteristics, fast response speed, and low driving voltage, so it is being actively developed and commercialized to be used as a light source for flat panel displays such as wall-mounted TVs, backlights of displays, lighting, and billboards.

The first organic EL device was reported (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51 p. 913, 1987) by CW Tang of Eastman Kodak Co., Ltd., and its light emitting principle is generally, When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form excitons, which are electron-hole pairs, which are converted into light by transferring the energy of the excitons to the light emitting material.

More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent device is a hole injection layer (HIL, hole injection layer), a hole transport layer (HTL, hole transport layer), a light emitting layer (EML, light emitting layer), an electron transport layer (ETL, electron transport layer) or electrons from the anode. It is stacked in the order of the electron injection layer (EIL), and an electron blocking layer (EBL) or hole blocking layer (HBL) is added before and after the light emitting layer, respectively, to increase the efficiency of the light emitting layer can be included as

Most of the materials used in the organic layer of the organic electroluminescent device are pure organic materials or complex compounds formed by complexing organic materials and metals. It can be divided into injection materials, etc.

Here, as a hole injection material or a hole transport material, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. As an electron injection material or an electron transport material, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used.

On the other hand, as the light emitting layer material, a material having a stable form in both oxidation and reduction states is preferable, and a material having high luminous efficiency for converting excitons into light when they are formed is preferable. More specifically, the light emitting layer is composed of two materials, a host and a dopant, and the dopant must have high quantum efficiency, and the host material has a larger energy gap than the dopant material, which facilitates energy transfer to the dopant. it is preferable The display used for TV and mobile implements full color with three colors of red, green, and blue, and the light emitting layer is made up of a red host/dopant, a green host/dopant, and a blue host/dopant, respectively. is composed

As for the material used as the existing blue dopant, fluorescent molecules such as perylene, coumarin, anthracene, and pyrene accounted for a large proportion, but the dopant's emission spectrum and full width at half maximum width half the maximum) is wide, so there is a disadvantage that pure blue light cannot be used when manufacturing a device. This characteristic is the main reason that not only reduces the efficiency of blue in the resonance structure of the device, but also makes it difficult to utilize the deep blue section.

Recently, a literature utilizing boron-based dopants with a narrow emission spectrum and high device efficiency has been published in Adv. Mater. 2016, 28, 2777-2781 and Angew. Chem. Int. Ed 2017, 56, 5087-5090, and disclosed in Korean Patent Application Laid-Open No. 10-2016-0119683. In the case of the previously introduced boron-based blue dopant material, a boron atom is contained in the center and is cyclized, so that the boron forms only a three-coordinated bond and the molecular structure is maintained in a planar state.

The dopant of such a planar structure has the advantage of emitting pure light because the energy level of the vibration mode of the molecule is similar, and the emission spectrum and half maximum width are narrowed.

(Non-Patent Document 1) Krebs, Frederik C., et al. "Synthesis, Structure, and Properties of 4, 8, 12-Trioxa-12c-phospha-4, 8, 12, 12c-tetrahydrodibenzo [cd, mn] pyrene, a Molecular Pyroelectric." Journal of the American Chemical Society 119.6 (1997): 1208-1216.

An object of the present invention is to provide a novel organic compound and an organic electroluminescent device including the same.

Another object of the present invention is to provide a novel compound that has a narrow emission spectrum and a half maximum width and can be used as a material for an emission layer, a hole injection layer, a hole transport layer or an electron blocking layer as an organic compound.

Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage and, in particular, excellent characteristics such as life, using an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability.

Another object of the present invention is to provide a blue-based blue host/dopant system and an organic electroluminescent device suitable for AM-OLED using the organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1) or formula (2), or a multimer compound comprising the structure of a compound represented by the following formula (1) or formula 2:

[Formula 1]

[Formula 2]

here,

n is an integer from 0 to 2,

1이고,a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

1,

1이고,e + f

1,

Y ₁ and Y ₂ are the same as or different from each other, and are each independently B, N, P=O or P=S,

Rings A to G are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 30 aryl group or a substituted or unsubstituted C 3 to C 60 heteroaryl group,

X _{1 To} X _{3 Are} the same as or different from each other, and each independently B, N, O, S, Se or Si,

X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,

Z _{1 To} Z _{6 Are} the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), a substituted or unsubstituted C 1 to C 10 alkylene group, It is selected from the group consisting of a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

R ₁ to R ₉ are the same as or different from each other, and each independently represent hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 20 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 24 alkynyl group , a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C6 to C30 of a heteroarylalkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number An aralkylamino group of 6 to 30, a substituted or unsubstituted heteroarylamino group having 2 to 24 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, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can form a substituted or unsubstituted ring by bonding with an adjacent group to each other,

When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxyl group, alkylthio group having 1 to 4 carbon atoms, carbon number 1 to 30 alkyl group, C 1 to C 20 cycloalkyl group, C 2 to C 30 alkenyl group, C 2 to C 24 alkynyl group, C 7 to C 30 aralkyl group, C 6 to C 30 aryl group, C 2 to C 60 Heteroaryl group, C6-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 of a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms of It may form a cyclic ring, and when substituted with a plurality of substituents, they are the same or different from each other.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers is a compound represented by Formula 1 or Formula 2, or Formula 1 or It provides an organic electroluminescent device comprising a compound that is a multimer including the structure of the compound represented by Chemical Formula 2.

For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic material layers.

According to a preferred embodiment of the present invention, the organic material layer is a light emitting layer, and the light emitting layer is a compound represented by Formula 1 or Formula 2, or a compound represented by Formula 1 or Formula 2, which is a multimeric compound including the structure of the compound. It may be characterized by including.

According to a preferred embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer or an electron blocking layer, the hole injection layer, the hole transport layer or the electron blocking layer is a compound represented by Formula 1 or Formula 2, or It may be characterized in that it includes a compound that is a multimer including the structure of the compound represented by Formula 1 or Formula 2.

In the present invention, "hydrogen" is hydrogen, light hydrogen, deuterium or tritium.

As used herein, the “halogen group” is fluorine, chlorine, bromine or iodine.

In the present invention, “alkyl” refers to a monovalent substituent derived from a saturated hydrocarbon having 1 to 40 carbon atoms in a straight or branched chain. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, “alkenyl” refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, "alkylthio" refers to the above-described alkyl group bonded through a sulfur linkage (-S-).

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, dimethylfluorenyl, and the like.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, “alkoxy” may be a straight chain, branched chain or cyclic chain. Although the number of carbon atoms of alkoxy is not particularly limited, it is preferably from 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.

As used herein, "aralkyl" refers to an aryl-alkyl group wherein aryl and alkyl are as described above. Preferred aralkyls include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl. Binding to the parent moiety is through an alkyl.

In the present invention, “arylamino group” refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, “alkylamino group” refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, “aralkylamino group” refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, “heteroarylamino group” refers to an amine group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.

In the present invention, “heteroaralkyl group” refers to an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, “heterocycloalkyl” means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “condensed ring” refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, 　 "adjacent 　 groups are combined with each other to form a ring" means 　 adjacent 　 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof.

As used herein, “alicyclic compound” has the same meaning as “aliphatic hydrocarbon ring”, and refers to a non-aromatic ring and a ring composed of only carbon and hydrogen atoms.

As used herein, the term “heteroalicyclic compound” refers to an alicyclic compound including at least one hetero atom in which one or more carbons of the “aliphatic hydrocarbon ring” are substituted with a hetero atom.

Examples of the "aromatic hydrocarbon ring" in the present specification include, but are not limited to, a phenyl group, a naphthyl group, an anthracenyl group, and the like.

As used herein, the term “aliphatic heterocycle” refers to an aliphatic ring including one or more heteroatoms.

As used herein, the term “aromatic heterocycle” refers to an aromatic ring including one or more heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

As used herein, the term “concentration quenching” means that the luminous efficiency of a device decreases as the concentration of dopant molecules increases.

As used herein, the terms “boron-based element”, “boron-based compound”, and “boron-based dopant” mean a boron (B) element having an atomic number of 5, a compound or dopant containing boron.

As used herein, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other. The substituent is hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, a heteroalkyl group having 6 to carbon atoms. 30 aralkyl group, C5-30 aryl group, C2-30 heteroaryl group, C3-30 heteroarylalkyl group, C1-30 alkoxy group, C1-C30 alkylamino group, C6-C30 heteroaryl group It may be substituted with one or more substituents selected from the group consisting of a 30 arylamino group, an aralkylamino group having 6 to 30 carbon atoms, and a heteroarylamino group having 2 to 24 carbon atoms, but is not limited thereto.

The present invention provides a novel compound that can be used as a material for a light emitting layer, a hole injection layer, a hole transport layer, or an electron blocking layer as an organic compound having a narrow emission spectrum and a half maximum width.

The present invention provides an organic electroluminescent device having a low driving voltage and particularly excellent characteristics such as lifespan by using an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability.

In addition, the present invention provides a blue-based blue host/dopant system and an organic electroluminescent device suitable for AM-OLED using the organic compound.

Hereinafter, embodiments of the present invention will be described in detail so that those of ordinary skill in the art can easily carry out the present invention. However, the present invention may be embodied in several different forms and is not limited to the embodiments described herein.

The organic compound according to the present invention has a planar structure and minimizes the pi (π -π) mutual attraction of molecules in the molecule, and the energy level of the vibration mode of the molecule is almost similar, so that the emission spectrum is narrow. And it is characterized in that it has a full width at half maximum.

The organic compound according to the present invention contains an atom that provides a planar structure, such as a boron-based element, prevents the generation of an excimer in a molecule, and increases the electron density of the core and the stability of the dopant, thereby increasing the efficiency and lifespan of the device can make possible

Specifically, a compound represented by Formula 1 or Formula 2, or a compound represented by Formula 1 or Formula 2, which is a multimeric compound including the structure of a compound represented by Formula 2, is as follows:

[Formula 1]

[Formula 2]

here,

n is an integer from 0 to 2,

1이고,a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

1,

1이고,e + f

1,

Y ₁ and Y ₂ are the same as or different from each other, and are each independently B, N, P=O or P=S,

Rings A to G are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 30 aryl group or a substituted or unsubstituted C 3 to C 60 heteroaryl group,

X _{1 To} X _{3 Are} the same as or different from each other, and each independently B, N, O, S, Se or Si,

X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,

Z _{1 To} Z _{6 Are} the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), a substituted or unsubstituted C 1 to C 10 alkylene group, It is selected from the group consisting of a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

R ₁ to R ₉ are the same as or different from each other, and each independently represent hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 20 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 24 alkynyl group , a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C6 to C30 of a heteroarylalkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number An aralkylamino group of 6 to 30, a substituted or unsubstituted heteroarylamino group having 2 to 24 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, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can form a substituted or unsubstituted ring by bonding with an adjacent group to each other,

When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxyl group, alkylthio group having 1 to 4 carbon atoms, carbon number 1 to 30 alkyl group, C 1 to C 20 cycloalkyl group, C 2 to C 30 alkenyl group, C 2 to C 24 alkynyl group, C 7 to C 30 aralkyl group, C 6 to C 30 aryl group, C 2 to C 60 Heteroaryl group, C6-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 of a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms of It may form a cyclic ring, and when substituted with a plurality of substituents, they are the same or different from each other.

Preferably, the compound may be a compound selected from the group consisting of a compound represented by Formula 1, a compound represented by Formula 2, and a compound having a unit structure represented by Formula 1 or Formula 2 in a condensed form. .

The A to G rings may be the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 5 to 15 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

The compound may be a compound selected from the group consisting of a compound represented by Formula 3 or Formula 4, or a compound having a unit structure represented by Formula 3 or Formula 4 in a condensed form:

[Formula 3]

[Formula 4]

here,

n, a, b, c, d, e, f, Y ₁ , Y ₂ , X ₁ to X ₄ , Z ₁ to Z ₆ , R ₁ and R ₂ are as defined in claim 1,

m, p, q, r and u are the same as or different from each other, and are each independently an integer of 0 to 3,

t is an integer from 0 to 4,

R ₁₀ to R ₁₆ are the same or different from each other, and each independently represent a hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 20 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 24 alkynyl group , a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C6 to C30 of a heteroarylalkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number An aralkylamino group of 6 to 30, a substituted or unsubstituted heteroarylamino group having 2 to 24 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, and It is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be combined with an adjacent group to form a substituted or unsubstituted ring,

When R ₁₀ to R ₁₆ are substituted, hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, an alkylthio group having 1 to 4 carbon atoms, an alkyl group having 1 to 30 carbon atoms, 1 to 20 carbon atoms Cycloalkyl group, C2-30 alkenyl group, C2-C24 alkynyl group, C7-30 aralkyl group, C6-C30 aryl group, C2-60 heteroaryl group, C6-C30 hetero Arylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 hetero arylamino group, C1-30 It is substituted with a substituent selected from the group consisting of an alkylsilyl group, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms, and may combine with adjacent groups to form a substituted or unsubstituted ring, and a plurality of When substituted with two substituents, they are the same as or different from each other.

The compound in which the unit structure represented by Formula 1 or Formula 2 is condensed or the form in which the unit structure represented by Formula 3 or Formula 4 is condensed is a form in which the cyclic compound included in the unit structure is shared, It is a form in which the rings of the rings included in the unit structure are bonded to each other so as to be condensed.

The form of the condensed compound may be a compound in which the unit structure is condensed as illustrated below, but may include ranges apparent to those skilled in the art:

The Y ₁ and Y ₂ may be B.

The X ₁ to X ₃ may be the same as or different from each other, and may each independently be N or O.

The compound represented by Formula 1 or Formula 2 according to the present invention may be represented by the following compound, but is not limited thereto:

The compound of Formula 1 or Formula 2 of the present invention may be usefully used as a dopant material for the emission layer. Specifically, the organic compound may provide a thermally stable organic compound as a dopant material compared to the conventional boron-based dopant.

The organic compound of the present invention can be usefully used as a material for forming a light emitting layer. In the above, the material for forming the light emitting layer may further include a material, for example, a host material, which is usually added when preparing the organic compound in a form required for use in forming the light emitting layer.

The material for forming the emission layer may be a material for a dopant.

The present invention provides an organic electroluminescent device including a compound represented by Formula 1 or Formula 2, or a compound represented by Formula 1 or Formula 2, which is a multimer compound having a structure of the compound represented by Formula 2.

The organic compound of the present invention can be usefully used as a material for forming a hole injection layer, a hole transport layer, or an electron blocking layer.

In addition, the present invention relates to a material for forming a light emitting layer comprising the organic compound.

In the above, the material for forming the light emitting layer may further include a material, for example, a host material, which is usually added when preparing the organic compound in a form required for use in forming the light emitting layer.

In addition, the present invention provides an organic electroluminescent device in which an organic thin film layer comprising at least a light emitting layer or a plurality of layers is laminated between a cathode and an anode,

It relates to an organic electroluminescent device, characterized in that the light emitting layer contains the organic compound represented by Formula 1 or Formula 2 alone or in combination of two or more.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are stacked, and if necessary, an electron blocking layer, a hole blocking layer, etc. are further stacked can be

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the contents exemplified below are not intended to limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML) and a cathode (electron injection electrode) are sequentially stacked, Preferably, it may further include an electron blocking layer (EBL) between the anode and the light emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the light emitting layer. In addition, a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer.

In the method of manufacturing an organic light emitting diode according to the present invention, first, a material for an anode is coated on the surface of a substrate in a conventional manner to form an anode. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and waterproofing properties. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. which are transparent and have excellent conductivity may be used.

Next, a hole injection layer (HIL) material is vacuum-deposited or spin-coated on the surface of the anode by a conventional method to form a hole injection layer. Examples of the hole injection layer material include copper phthalocyanine (CuPc), 4,4′,4″-tris(3-methylphenylamino)triphenylamine (m-MTDATA), and 4,4′,4″-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer (HTL) material on the surface of the hole injection layer by a conventional method. In this case, as the hole transport layer material, bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N′-di(naphthalen-1-yl)-N,N′-biphenyl -benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD) are exemplified.

The light emitting layer is formed by vacuum thermal evaporation or spin coating of the light emitting layer (EML) material on the surface of the hole transport layer in a conventional manner. In this case, as the light emitting material or the light emitting host material used in the light emitting layer, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), etc. may be used in the case of green, and in the case of blue, Alq ₃ , CBP (4, 4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-biphenyl), PVK (poly(n-vinylcabazole), poly (n-vinylcarbazole)), ADN ( 9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalen-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene , 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene, 3-tert-butyl -9,10-di(naphth-2yl)anthracene), E3, DSA (distyrylarylene, distyrylarylene), or a mixture of two or more thereof may be used, but is not limited thereto.

In the case of a dopant that can be used together with a light emitting host among the materials of the light emitting layer, the compound of the present invention may be preferably used.

Optionally, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the light emitting layer.

An electron transport layer (ETL) is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material in a conventional manner. In this case, the material for the electron transport layer used is not particularly limited, and tris(8-hydroxyquinolinolato)aluminum (Alq ₃ ) may be preferably used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer together, it is possible to prevent the diffusion of triplet excitons or holes into the electron transport layer. .

The formation of the hole blocking layer can be carried out by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but preferably (8-hydroxyquinolinola Earth) lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF, and the like may be used.

An electron injection layer is formed by vacuum thermal evaporation or spin coating of an electron injection layer (EIL) material on the surface of the electron transport layer in a conventional manner. In this case, as the electron injection layer material used, a material such as LiF, Liq, Li ₂ O, BaO, NaCl, CsF, etc. may be used.

A cathode is formed by vacuum thermal evaporation of a material for a cathode on the surface of the electron injection layer in a conventional manner.

At this time, as the material for the anode used, lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like can be used. In addition, in the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

A capping layer (CPL) may be formed on the surface of the negative electrode by the composition for forming a capping layer.

Hereinafter, a method for synthesizing the compounds will be described below with representative examples. However, the method for synthesizing the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention may be prepared by the methods illustrated below and methods known in the art.

[Synthesis Example 1: Preparation of compound 55]

Starting material 1-1 compound 55

6.18 g (10 mmol) of the starting material 1-1 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours. After that, the reaction mass was cooled to 0 °C again, 1.93 mL (20 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with a DCM/Acetone mixed solvent, the compound 55 was obtained in a 9% yield (0.53 g).

MS (MALDI-TOF) m/z: 592 [M]+

[Synthesis Example 2: Preparation of compound 271]

Starting material 1-2 compound 271

Starting material 1-2 5.02 g (10 mmol ) was dissolved in tert- Butylbenzene (42 ml) and cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere and stirred at 60 to 70° C. for 2 hours.

After that, the reaction mass was cooled to 0 °C again, 1.93 mL (20 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with DCM/Acetone mixed solvent, 0.52 g of compound 271 was obtained in 11% yield.

MS (MALDI-TOF) m/z: 475 [M]+

[Synthesis Example 3: Preparation of compound 270]

Starting material 1-3 compound 270

After dissolving 4.51 g (10 mmol) of starting material 1-3 in tert- Butylbenzene (42 ml), it was cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere and stirred at 60 to 70° C. for 2 hours.

Afterwards, the reaction mass was cooled to 0° C., and 1.93 mL (20 mmol) of boron tribromide was added thereto, followed by stirring at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with a DCM/Acetone mixed solvent, the compound 270 was obtained in 14% yield (0.6 g).

MS (MALDI-TOF) m/z: 425 [M]+

[Synthesis Example 4: Preparation of compound 220]

Starting material 1-4 compound 220

7.0 g (10 mmol) of starting material 1-4 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours.

After that, the reaction mixture was cooled to 0° C., and 1.93 mL (20 mmol) of boron tribromide was added thereto, followed by stirring at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with DCM/Acetone mixed solvent, the compound 220 was obtained in 10% yield, 0.67 g.

MS (MALDI-TOF) m/z: 673 [M]+

[Synthesis Example 5: Preparation of compound 366]

Starting material 1-5 compound 366

After dissolving 7.52 g (10 mmol) of the starting material 1-5 in tert- butylbenzene (42 ml), it was cooled to 0°C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, 0.94 g of compound 366 was obtained in 13% yield.

MS (MALDI-TOF) m/z: 725 [M]+

[Synthesis Example 6: Preparation of compound 156]

Starting material 1-6 compound 156

After dissolving 7.59 g (10 mmol) of the starting material 1-6 in tert- butylbenzene (42 ml), it was cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, the compound 156 was obtained in 15% yield, 1.10 g.

MS (MALDI-TOF) m/z: 704 [M]+

[Synthesis Example 7: Preparation of compound 263]

Starting material 1-7 compound 263

After dissolving 9.06 g (10 mmol) of the starting material 1-7 in tert- butylbenzene (42 ml), it was cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, the compound 263 was obtained in 5% yield, 0.44 g.

MS (MALDI-TOF) m/z: 880 [M]+

[Synthesis Example 8: Preparation of compound 187]

Starting material 1-8 compound 187

After dissolving 7.40 g (10 mmol) of the starting material 1-8 in tert- butylbenzene (42 ml), it was cooled to 0°C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, the compound 187 was obtained in 10% yield, 0.74 g.

MS (MALDI-TOF) m/z: 638 [M]+

[Synthesis Example 9: Preparation of compound 367]

Starting material 1-9 compound 367

After dissolving 7.27 g (10 mmol) of the starting material 1-9 in tert- butylbenzene (42 ml), it was cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, the compound 367 was obtained in 7% yield, 0.49 g.

MS (MALDI-TOF) m/z: 700 [M]+

[Synthesis Example 10: Preparation of compound 368]

Starting material 1-10 compound 368

8.31 g (10 mmol) of the starting material 1-10 was dissolved in tert- butylbenzene (42 ml), and then cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, 0.88 g of compound 368 was obtained in 11% yield.

MS (MALDI-TOF) m/z: 654 [M]+

[Synthesis Example 11: Preparation of compound 338]

Starting material 1-11 compound 338

After dissolving 5.72 g (10 mmol) of the starting material 1-11 in tert- Butylbenzene (42 ml), it was cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 2 hours. After that, the reaction mass was cooled to 0° C., 1.90 mL (20 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with DCM/Acetone mixed solvent, the compound 338 was obtained in 8% yield, 0.44 g.

MS (MALDI-TOF) m/z: 546 [M]+

[Synthesis Example 12: Preparation of compound 369]

Starting material 1-12 compound 369

6.54 g (10 mmol) of the starting material 1-12 was dissolved in tert- butylbenzene (42 ml), and then cooled to 0°C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with DCM/Acetone mixed solvent, 1.0 g of compound 369 was obtained in 16% yield.

MS (MALDI-TOF) m/z: 627 [M]+

[Synthesis Example 1-13: Preparation of compound 61]

Starting material 1-13 compound 61

After dissolving 7.97 g (10 mmol) of the starting material 1-13 in tert- butylbenzene (42 ml), it was cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with a DCM/Acetone mixed solvent, the compound 61 was obtained in a 9% yield (0.65 g).

MS (MALDI-TOF) m/z: 726 [M]+

[Synthesis Example 1-14: Preparation of compound 76]

Starting material 1-14 compound 76

8.43 g (10 mmol) of the starting material 1-14 was dissolved in tert- Butylbenzene (42 ml), and then cooled to 0 °C. 11.8 ml (20 mmol) of a 1.7 M tert- Butyllithium solution (in Pentane) was added under a nitrogen atmosphere and stirred at 60 to 70° C. for 2 hours. After that, the reaction mass was cooled to 0 °C, 1.90 mL (20 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 60 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method. After recrystallization and purification with DCM/Acetone mixed solvent, 0.82 g of compound 76 was obtained in 10% yield.

MS (MALDI-TOF) m/z: 816 [M]+

[Synthesis Example 1-15: Preparation of compound 75]

Starting material 1-15 compound 75

After dissolving 7.97 g (10 mmol) of the starting material 1-15 in tert- butylbenzene (42 ml), it was cooled to 0 °C. 8.0mL (20.0mmol) of a 2.5M n- butyllithium solution (in hexane) is added under a nitrogen atmosphere, and the mixture is stirred at room temperature for 3 hours.

After that, the reaction mass was cooled to 0° C., 1.90 mL (20.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mass was cooled to 0 °C again, and 3.51 mL (20 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at 70 °C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and filtered. After the filtrate was concentrated under reduced pressure, it was purified by silica gel column chromatography (DCM/Hexane) method.

Thereafter, recrystallization was performed using a DCM/Acetone mixed solvent to obtain 1.04 g of compound 75 in 13% yield.

MS (MALDI-TOF) m/z: 799 [M]+

<Example 1: Method of manufacturing an organic electroluminescent device with a bottom light emitting structure>

The substrate on which ITO (100 nm), which is the anode of the organic light emitting diode, was laminated was patterned by dividing the substrate into a cathode, an anode region, and an insulating layer through a photo-lithograph process, and then the work function of the anode (ITO) ( For the purpose of increasing work-function) and cleaning, the surface was treated with _{UV Ozone treatment and O 2} :N _{2 plasma.} A hole injection layer (HIL) was formed thereon to a thickness of 10 nm. Then, a hole transport layer was vacuum deposited on the hole injection layer to have a thickness of 90 nm, and an electron blocking layer (EBL) was formed to a thickness of 10 nm on the hole transport layer (HTL). While depositing a host of the emission layer on the electron blocking layer (EBL), 2% of compound 55 was doped as a dopant to form an emission layer (EML) to a thickness of 25 nm.

An electron transport layer (ETL) was deposited to a thickness of 25 nm thereon, an electron injection layer was deposited to a thickness of 1 nm on the electron transport layer, and aluminum was deposited to a thickness of 100 nm as a cathode. Then, an organic electroluminescent device was manufactured by bonding a seal cap including a getter with a UV-curable adhesive to protect the organic electroluminescent device from oxygen or moisture in the atmosphere.

<Examples 2 to 14: Preparation of organic electroluminescent device>

An organic electric field was used in the same manner as in Example 1, except that compounds 61, 75, 76, 271, 270, 220, 366, 156, 263, 187, 367, 338, and 369 were used instead of compound 55 as a dopant. A light emitting device was manufactured.

<Comparative Example 1: Preparation of organic electroluminescent device>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 55 as a dopant.

<Compound A>

<Characteristics analysis of organic light emitting device>

^{Hereinafter, 10 mA/cm 2} current was applied to the bottom light emitting structure organic light emitting device prepared in Examples 1 to 14 and Comparative Example 1 to measure the electro-optical characteristics, and the result of measuring the lifespan by driving a constant current of ^{40 mA/cm 2 is as follows.} It was compared with Table 1 and shown.

division DOPANT Voltage (V) current efficiency
(Cd/A) color characteristics life span
T95
(hr) CIE x CIE y Example 1 compound 55 4.00 6.5 0.129 0.097 95 Example 2 compound 61 4.02 5.6 0.128 0.106 100 Example 3 compound 75 3.93 8.6 0.1238 0.1102 75 Example 4 compound 76 3.97 8.2 0.1241 0.180 110 Example 5 compound 271 3.86 4.9 0.14 0.059 70 Example 6 compound 270 3.85 5.2 0.139 0.059 75 Example 7 compound 220 3.96 7.4 0.113 0.118 85 Example 8 compound 366 3.97 6.7 0.129 0.095 80 Example 9 compound 156 3.91 7.78 0.114 0.115 72 Example 10 compound 263 3.78 5.0 0.1166 0.136 86 Example 11 compound 187 3.83 6.1 0.1155 0.1404 70 Example 12 compound 367 3.84 6.1 0.1144 0.1455 78 Example 13 compound 338 3.94 6.9 0.114 0.114 95 Example 14 compound 369 4.04 6.4 0.1284 0.100 80 Comparative Example 1 compound A 4.10 4.4 0.1387 0.0635 45

According to the experimental results, compared to Comparative Example 1, when the compound of the example of the present invention was used, an organic compound having excellent efficiency and electrochemical stability was used, and the driving voltage was low, the color characteristic was excellent, and characteristics such as a long lifespan This excellent organic electroluminescent device can be provided.

Although preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention as defined in the following claims are also provided. is within the scope of the

Claims (8)

A compound represented by Formula 1 or Formula 2, or a multimer comprising the structure of a compound represented by Formula 1 or Formula 2
compound:
[Formula 1]

[Formula 2]

here,
n is an integer from 0 to 2,
a to f are the same as or different from each other, each independently an integer of 0 or 1, a + b + c + d

1,
e + f

1,
Y ₁ and Y ₂ are B;
Rings A to G are the same as or different from each other, and each independently represents a substituted or unsubstituted C5 to C15 aryl group or a substituted or unsubstituted C3 to C20 heteroaryl group,
X _{1 To} X _{3 Are} the same as or different from each other, and each independently B, N, O, S, Se or Si,
X ₄ is B, O, S, NR ₃ , Si(R ₄ )(R ₅ ) or Se,
Z ₁ , Z ₂ and Z ₅ are the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), B(R ₈ ), N(R ₉ ), substituted or unsubstituted C2-10 It is selected from the group consisting of an alkenylene group and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
Z ₃ , Z ₄ and Z ₆ are the same as or different from each other, and each independently Si(R ₆ )(R ₇ ), N(R ₉ ), a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms and a substituted or It is selected from the group consisting of an unsubstituted arylene group having 6 to 30 carbon atoms,
R ₁ to R ₉ are the same as or different from each other, and each independently represent hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, A substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 20 cycloalkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 24 alkynyl group , a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 6 to 30 of a heteroarylalkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number It is selected from the group consisting of a 6 to 30 aralkylamino group, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and is bonded to an adjacent group to form a substituted or unsubstituted group can form a cyclic ring,
When A to G, Z ₁ to Z ₆ and R ₁ to R ₉ are substituted, hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxyl group, alkylthio group having 1 to 4 carbon atoms, carbon number 1 to 30 alkyl group, C 1 to C 20 cycloalkyl group, C 2 to C 30 alkenyl group, C 2 to C 24 alkynyl group, C 7 to C 30 aralkyl group, C 6 to C 30 aryl group, C 2 to C 60 Heteroaryl group, C6-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 substituted with a substituent selected from the group consisting of a heteroarylamino group and an aryloxy group having 6 to 30 carbon atoms of same or different delete delete The method of claim 1,
Wherein X _{One To} X _{3 Are} the same as or different from each other, and each independently N or O
compound. a first electrode; a second electrode provided to face the first electrode; And an organic electroluminescent device comprising one or more organic material layers provided between the first electrode and the second electrode,
At least one of the one or more organic material layers comprising the compound according to claim 1
organic electroluminescent device. 6. The method of claim 5,
The organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.
Organic electroluminescent device. 6. The method of claim 5,
The organic material layer is an organic light emitting layer. 6. The method of claim 5,
The organic material layer is an organic electroluminescent device that is a hole injection layer, a hole transport layer, or an electron blocking layer.