Organic compound and organic electroluminescent device containing the same

Abstract

To provide an organic compound and an organic electroluminescent element comprising the same, which are excellent in the lifespan, efficiency, electrochemical stability, and thermal stability.SOLUTION: A compound is represented by chemical formula 1, where n, m, o and p are 1; Y1 and Y2 are B; X1 to X4 are each O or the like; and A, B, C, D and E are each an aryl group or the like, where at least one of the A, C and E is a heteroaryl group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device containing the same. [Background technology]

[0002] Organic electroluminescent devices (OLEDs) have a simpler structure and various advantages in manufacturing processes compared to conventional flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs). They have excellent brightness and viewing angle characteristics, a fast response speed, and a low driving voltage, so they are being actively developed and commercialized for use as flat panel displays such as wall-mounted TVs or as light sources for display backlights, lighting, and advertising boards.

[0003] The first organic electroluminescent device was reported by CW Tang and others at Eastman Kodak (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987). The principle of light emission is generally based on the fact that when a voltage is applied, holes injected from the positive electrode and electrons injected from the negative electrode recombine to form excitons, which are electron-hole pairs, and the energy of these excitons is transferred to the light-emitting material and converted into light.

[0004] More specifically, an organic electroluminescent device has a structure including a negative electrode (electron injection electrode), a positive electrode (hole injection electrode), and one or more organic layers between the electrodes. The organic electroluminescent device may include a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), and an electron transport layer (ETL) or an electron injection layer (EIL) stacked in this order from the positive electrode. To enhance the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) may be additionally included before or after the light emitting layer.

[0005] Materials used in the organic layer of an organic electroluminescent device are mostly pure organic materials or complex compounds in which an organic material and a metal form a complex, and can be classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. depending on their applications.

[0006] Here, organic substances that are easily oxidized and electrochemically stable when oxidized are mainly used as hole injection materials and hole transport materials, while organic substances that are easily reduced and electrochemically stable when reduced are mainly used as electron injection materials and electron transport materials.

[0007] On the other hand, materials that are stable in both oxidized and reduced states are preferred as materials for the light-emitting layer, and materials with high luminescence efficiency that converts excitons into light when they are formed are preferred. More specifically, the light-emitting layer is composed of two materials: a host and a dopant. The dopant should have high quantum efficiency, and the host material should have a larger energy gap than the dopant material, facilitating energy transfer to the dopant. Displays used in TVs, mobile devices, etc. achieve full color with three colors: red, green, and blue, and the light-emitting layers are composed of red host / dopant, green host / dopant, and blue host / dopant, respectively.

[0008] The majority of materials used as blue dopants in the past have been fluorescent molecules such as parylene, coumarine, anthracene, and pyrene, but the dopants have a drawback in that they cannot utilize pure blue light during device manufacturing due to their wide emission spectrum and full width half maximum. This characteristic not only reduces the blue efficiency in the device's resonant structure, but is also the main reason why it is difficult to utilize the deep blue range.

[0009] In recent years, literature on the use of boron-based dopants that provide narrow device emission spectra 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 Publication No. 10-2016-0119683. Previously introduced boron-based blue dopant materials are cyclized with a boron atom at the center, which means that boron forms only three-coordinate bonds, maintaining a planar molecular structure.

[0010] Such a dopant with a planar structure has the advantage that the energy levels of the molecular vibration modes are similar, resulting in a narrow emission spectrum and a narrow half-width, and thus emitting pure light. [Prior art documents] [Non-patent literature]

[0011] [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. Summary of the Invention [Problem to be solved by the invention]

[0012] An object of the present invention is to provide a novel organic compound and an organic electroluminescent device containing the same.

[0013] Another object of the present invention is to provide a novel organic compound having a narrow emission spectrum and a narrow half-width, which can be used as a material for a light-emitting layer, etc.

[0014] Another object of the present invention is to provide an organic electroluminescent device that uses an organic compound having excellent lifetime, efficiency, electrochemical stability, and thermal stability, and that has a low driving voltage, high efficiency in a low-doping region, relatively little efficiency decrease even in an over-doping region, and is particularly excellent in properties such as lifetime.

[0015] It is still another object of the present invention to provide a blue host / dopant system suitable for AM-OLED and an organic electroluminescent device using the organic compound. [Means for solving the problem]

[0016] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0017] [ka] where: n, m, o, and p are the same or different and each independently represents an integer of 0 or 1; n+m+o+p are integers equal to or greater than 2, Y1 and Y2 are the same or different and each independently represents B, N, C, (R1)(R2), P=O or P=S; X1 to X4 are the same or different and each independently represent B(R3), N(R4), O, S, or Se; A, B, C, D, and E are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; At least one of A, B, C, D, and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; R1 to R4 are the same or different and each independently represent a hydrogen atom, 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, 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, or a substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms. a substituted or unsubstituted heteroarylamino group having from 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having from 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, and which may bond to adjacent groups to form a substituted or unsubstituted ring.

[0018] The present invention also provides an organic electroluminescent device including a first electrode, a second electrode facing the first electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the one or more organic material layers contains a compound represented by Chemical Formula 1.

[0019] For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic electroluminescent device is not limited thereto and may include fewer organic material layers.

[0020] According to a preferred embodiment of the present invention, the organic layer is a light-emitting layer, and the light-emitting layer may be characterized by including a compound represented by Chemical Formula 1.

[0021] According to a preferred embodiment of the present invention, the organic layer is a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer may be characterized by including a compound represented by Chemical Formula 1.

[0022] In the present invention, "hydrogen" refers to hydrogen, protium, deuterium, or tritium.

[0023] As used herein, a "halogen group" is fluorine, chlorine, bromine, or iodine.

[0024] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl.

[0025] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0026] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of alkynyl include, but are not limited to, ethynyl and 2-propynyl.

[0027] As used herein, "alkylthio" refers to an alkyl group as described above attached through a sulfur linkage (-S-).

[0028] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. It may also include a pendant or fused ring structure. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and dimethylfluorenyl.

[0029] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monocyclic heterocyclic or polycyclic heterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, one or more carbon atoms, preferably one to three carbon atoms, in the ring are substituted with a heteroatom such as N, O, S, or Se. In addition, it may include a form in which two or more rings are pendant or fused to each other, and may further include a form in which they are fused to an aryl group. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0030] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, where R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0031] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl having 1 to 40 carbon atoms and may have a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0032] In the present invention, "alkoxy" may be linear, branched, or cyclic. The number of carbon atoms in alkoxy is not particularly limited, but alkoxy having 1 to 20 carbon atoms is preferred. Specific examples include, but are not limited to, 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, and p-methylbenzyloxy.

[0033] As used herein, "aralkyl" refers to an aryl-alkyl group in which aryl and alkyl are as defined above. Preferred aralkyls contain a lower alkyl group. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthalenylmethyl. The bond to the parent moiety is through the alkyl.

[0034] In the present invention, the term "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

[0035] In the present invention, the term "alkylamino group" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.

[0036] In the present invention, the term "aralkylamino group" means an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

[0037] In the present invention, the term "heteroarylamino group" refers to an amine group substituted with an aryl group and a heterocyclic group having 6 to 30 carbon atoms.

[0038] In the present invention, the term "heteroaralkyl group" means an aryl-alkyl group substituted with a heterocyclic group.

[0039] In the present invention, "cycloalkyl" means 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, and adamantine.

[0040] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, in which one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with a heteroatom such as N, O, S, or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0041] In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.

[0042] In the present invention, the term "fused ring" refers to a fused alicyclic ring, a fused aromatic ring, a fused heteroalicyclic ring, a fused heteroaromatic ring, or a combination thereof.

[0043] In the present invention, the phrase "adjacent groups bond to each other to form a ring" means that adjacent groups bond to each other to form a substituted or unsubstituted alicyclic hydrocarbon, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted heteroalicyclic ring, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof.

[0044] In this specification, the term "alicyclic compound" has the same meaning as "alicyclic hydrocarbon" and refers to a non-aromatic ring consisting only of carbon and hydrogen atoms.

[0045] As used herein, the term "heteroalicyclic compound" refers to an alicyclic compound in which one or more carbon atoms of an "alicyclic hydrocarbon" are replaced with a heteroatom, and the alicyclic compound contains at least one heteroatom.

[0046] In this specification, examples of the "aromatic hydrocarbon ring" include, but are not limited to, a phenyl group, a naphthyl group, an anthracenyl group, and the like.

[0047] As used herein, "heteroalicyclic" means an alicyclic ring containing one or more heteroatoms.

[0048] As used herein, the term "aromatic heterocycle" refers to an aromatic ring that contains one or more heteroatoms.

[0049] As used herein, alicyclic hydrocarbons, aromatic hydrocarbon rings, heteroalicyclics, and aromatic heterocycles may be monocyclic or polycyclic.

[0050] As used herein, "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent. The substitution position is not limited to the position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted. When two or more substituents are present, the two or more substituents may be the same or different. The substituent may be one or more selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, alkynyl groups having 2 to 24 carbon atoms, heteroalkyl groups having 2 to 30 carbon atoms, aralkyl groups having 6 to 30 carbon atoms, aryl groups having 5 to 30 carbon atoms, heteroaryl groups having 2 to 30 carbon atoms, heteroarylalkyl groups having 3 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, alkylamino groups having 1 to 30 carbon atoms, arylamino groups having 6 to 30 carbon atoms, aralkylamino groups having 6 to 30 carbon atoms, and heteroarylamino groups having 2 to 24 carbon atoms, but is not limited to the above examples.

[0051] As used herein, the phrase "adjacent groups bond to each other to form a ring" means that adjacent groups bond to each other to form a substituted or unsubstituted alicyclic hydrocarbon, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted heteroalicyclic ring, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof. [Effects of the Invention]

[0052] The present invention provides novel organic compounds having a narrow emission spectrum and a narrow half-width, which can be used as a light-emitting layer material or the like.

[0053] The present invention provides an organic electroluminescent device that uses an organic compound that is excellent in lifespan, efficiency, electrochemical stability, and thermal stability, and that can achieve a low driving voltage and a significantly improved color reproduction rate.

[0054] The present invention also provides a blue host / dopant system suitable for AM-OLED and an organic electroluminescent device using the organic compound. DETAILED DESCRIPTION OF THE INVENTION

[0055] Although the present invention may be embodied in various different forms, it is to be understood that the invention is not limited to the embodiments set forth herein, and that the invention may be embodied in various different forms, rather than in a limited sense.

[0056] The organic compound according to the present invention has a planar structure, minimizes intramolecular π-π interactions, and has nearly similar energy levels of molecular vibration modes, resulting in a narrow emission spectrum and half-width, thereby significantly improving color reproduction.

[0057] The organic compound according to the present invention contains atoms that provide a planar structure, such as boron-based elements, which inhibit the formation of excimers within the molecule, increase the electron density of the core and the stability of the dopant, and can enable an increase in the efficiency and lifetime of the device. Specifically, it relates to a compound represented by the following chemical formula 1.

[0058] [ka] where: n, m, o, and p are the same or different and each independently represents an integer of 0 or 1; n+m+o+p are integers equal to or greater than 2, Y1 and Y2 are the same or different and each independently represents B, N, C, (R1)(R2), P=O or P=S; X1 to X4 are the same or different and each independently represent B(R3), N(R4), O, S, or Se; A, B, C, D, and E are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; At least one of A, B, C, D, and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; R1 to R4 are the same or different and each independently represent a hydrogen atom, 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, 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, or a substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms. a substituted or unsubstituted heteroarylamino group having from 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having from 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, and which may bond to adjacent groups to form a substituted or unsubstituted ring.

[0059] At least one of A, C, and E may be a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0060] Specifically, the heteroaryl group is selected from the group consisting of substituted or unsubstituted pyrrole, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted dioxin, substituted or unsubstituted oxathin, substituted or unsubstituted ditin, substituted or unsubstituted indole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzodioxin, substituted or unsubstituted benzooxathin, substituted or unsubstituted benzoditin, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzodioxin, substituted or unsubstituted phenoxanthin, and substituted or substituted thianthrene. When the heteroaryl group is substituted, adjacent substituents may be bonded to each other to form a cyclic compound.

[0061] More specifically, A, C, and E may be the same or different and may each independently be a compound represented by the following Chemical Formula 2 or Chemical Formula 3:

[0062] [ka] where: X5~X 10 and X 12 ~X 15 are the same or different and are each independently selected from the group consisting of C(R5), N, S, and O; X 11 is selected from the group consisting of C(R6)(C7), N(R8), S, and O; R5 to R8 are the same or different and each independently represent a hydrogen atom, 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, 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 6 ...30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl a substituted or unsubstituted heteroarylalkyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having from 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, and adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

[0063] Specifically, when A, C, and E are all represented by Chemical Formula 2, X5 to X 10 None of these are C(R5).

[0064] When A, C, and E are all represented by Chemical Formula 3, X 11 is C(R6)(C7) and X 12 ~X 15 However, none of them can be C(R5).

[0065] Said X5~X 10 and X 12 ~X 15 If both are C(R5), then X 11 is not C(R6)(C7).

[0066] The C may be selected from the group consisting of the following Chemical Formulas 4 to 7.

[0067] [ka] where: four groups among Y1 to Y6 are moieties bonded to adjacent groups, Among Y1 to Y6, those that are not bonded to adjacent groups are the same or different and are each independently selected from the group consisting of C(R9), N, S, and O; Y7~Y 10 two of the groups are moieties that bond to adjacent groups, Y7~Y 10 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 10 ), N, S, and O; Y 11 ~Y 14 two of the groups are moieties that bond to adjacent groups, Y 11 ~Y 14 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 11 ), N, S, and O; Y 15 ~Y 18 two of the groups are moieties that bond to adjacent groups, Y 15 ~Y 18 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 12 ), N, S, and O; Y 19 ~Y 22 two of the groups are moieties that bond to adjacent groups, Y 19 ~Y 22 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 13 ), N, S, and O; Y 23 ~Y 26 two of the groups are moieties that bond to adjacent groups, Y23 ~Y 26 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 14 ), N, S, and O; Y 27 ~Y 30 two of the groups are moieties that bond to adjacent groups, Y 27 ~Y 30 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 15 ), N, S, and O; X 16 ~X 18 are the same or different, and each independently represents C(R 16 )(C 17 )N(R 18 ), S, and O; R9~R 18 are the same or different and each independently represent a hydrogen atom, 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, 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 aryl group having 6 to 3 ... a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, 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 a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

[0068] The A and E may be the same or different and may each independently be a compound selected from the group consisting of the following Chemical Formulas 8 to 11.

[0069] [ka] where: q and r are integers of 0 to 4, Y 31 ~Y 36 two of the groups are moieties that bond to adjacent groups, Y 31 ~Y 36 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 21 ), N, S, and O; Y 37 ~Y 40 two of the groups are moieties that bond to adjacent groups, Y 37 ~Y 40 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 22 ), N, S, and O; Y 41 and Y 42- is the moiety that is bonded to the adjacent group, Y 43 ~Y 46 two of the groups are moieties that bond to adjacent groups, Y 43 ~Y 46 those that are not bonded to adjacent groups are the same or different, and each independently represents C(R 23 ), N, S, and O; X 19 and X 21 are the same or different, and each independently represents C(R 24 )(C 25 )N(R 26 ), S, and O; R 19 ~R 26are the same or different and each independently represent a hydrogen atom, 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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, 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 aryl group having 6 to 3 ... a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, 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 a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

[0070] The Y1 and Y2 are the same or different and each independently represents B or N.

[0071] The B and D may be the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0072] The compound represented by Chemical Formula 1 according to the present invention may be represented by the following compounds, but is not limited thereto.

[0073] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0074] The compound of Formula 1 of the present invention can be useful as a dopant material for an emitting layer. Specifically, the organic compound has thermal stability and a narrow emission spectrum and half-width compared to existing boron-based dopants, thereby providing an organic compound that can significantly improve color gamut.

[0075] The organic compound of the present invention can be useful as a material for forming an emitting layer. The material for forming an emitting layer may further contain a substance, such as a host substance, that is usually added when the organic compound is prepared in a form required for use in forming an emitting layer.

[0076] The material for forming the light-emitting layer may be a dopant material.

[0077] The present invention provides an organic electroluminescent device comprising the compound represented by Chemical Formula 1.

[0078] 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.

[0079] The present invention also relates to an organic electroluminescent device in which one or more organic thin film layers including at least an emitting layer are stacked between a negative electrode and a positive electrode, wherein the emitting layer contains one or more organic compounds represented by Chemical Formula 1 above, either singly or in combination.

[0080] The organic electroluminescent device has a structure in which a positive electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a negative electrode are stacked, and an electron blocking layer, a hole blocking layer, etc. may be further stacked as necessary.

[0081] The organic electroluminescent device of the present invention will be described below with reference to examples, but the organic electroluminescent device of the present invention is not limited to the following examples.

[0082] The organic electroluminescent device of the present invention may have a structure in which a positive electrode (hole-injection electrode), a hole-injection layer (HIL), a hole-transport layer (HTL), an emitting layer (EML), and a negative electrode (electron-injection electrode) are sequentially stacked. Preferably, an electron-blocking layer (EBL) is further included between the positive electrode and the emitting layer, and an electron-transporting layer (ETL) and an electron-injection layer (EIL) are further included between the negative electrode and the emitting layer. Alternatively, a hole-blocking layer (HBL) may be further included between the negative electrode and the emitting layer.

[0083] In the method for manufacturing an organic electroluminescent device according to the present invention, a cathode is formed by coating a cathode material on the surface of a substrate using a conventional method. The substrate is preferably a glass substrate or a transparent plastic substrate, which has excellent transparency, surface smoothness, ease of handling, and water resistance. The cathode material may be transparent and highly conductive, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO), or zinc oxide (ZnO).

[0084] Next, a hole injection layer (HIL) material is formed on the surface of the positive electrode by vacuum thermal deposition or spin coating using a conventional method. Examples of such HIL materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), starburst amines such as 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA) and 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), or IDE406 available from Idemitsu.

[0085] A hole transport layer (HTL) material is formed on the surface of the hole injection layer by vacuum thermal deposition or spin coating using a conventional method, such as 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).

[0086] An emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the sole emitting material or emitting host material used in the emitting layer may be tris(8-hydroxyquinolinolato)aluminum (Alq3) for green, and Alq3, 4,4'-N,N'-dicabazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA (tris( Examples of suitable amines include, but are not limited to, 4-carbazoyl-9-ylphenyl)amine, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), E3, distyrylarylene (DSA), or a mixture of two or more thereof.

[0087] Among the light-emitting layer materials, the compounds of the present invention can be preferably used as dopants that can be used together with a light-emitting host.

[0088] If necessary, an electron blocking layer (EBL) may further be formed between the hole transporting layer and the light emitting layer.

[0089] An electron transport layer (ETL) material is formed on the surface of the light-emitting layer by vacuum thermal deposition or spin coating using a conventional method. The electron transport layer material is not particularly limited, but preferably tris(8-hydroxyquinolinolato)aluminum (Alq3).

[0090] Alternatively, a hole-blocking layer (HBL) may be additionally formed between the light-emitting layer and the electron-transporting layer, and a phosphorescent dopant may be used in the light-emitting layer to prevent triplet excitons or holes from diffusing into the electron-transporting layer.

[0091] The hole-blocking layer can be formed by conventional vacuum thermal evaporation and spin coating of a hole-blocking layer material. The hole-blocking layer material is not particularly limited, but preferably includes (8-hydroxyquinolinolato)lithium (Liq), bis(8-hydroxy-2-methylquinolinolato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF.

[0092] An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method, and examples of the EIL material include LiF, Liq, LiO, BaO, NaCl, and CsF.

[0093] A negative electrode is formed by vacuum thermal deposition of a negative electrode material on the surface of the electron injection layer using a conventional method.

[0094] In this case, materials for the anode may include lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. In addition, in the case of a top-emitting organic electroluminescent device, a transparent anode that can transmit light may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO). A capping layer (CPL) may be formed on the surface of the anode.

[0095] The synthesis method of the compound of the present invention will be described below using representative examples. However, the synthesis method of the compound of the present invention is not limited to the methods exemplified below, and the compound of the present invention can be prepared by the methods exemplified below and methods known in the art.

[0096] [ka]

[0097] 11.94 g (10.0 mmol) of starting material 1-1, 30 mL of orthodichlorobenzene, and 4.82 mL (50.0 mmol) of boron tribromide were added to a high-pressure reactor and stirred. The reaction mixture was heated to 180-190°C and stirred for 12 hours.

[0098] After the reaction mixture was cooled to room temperature, cooled water was added and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0099] Thereafter, the product was purified by recrystallization using a DCM / acetone mixed solvent to obtain 0.97 g of the compound 1 with a yield of 8%. MS (MALDI-TOF) m / z: 1209 [M] +

[0100] [ka]

[0101] Compound 2 was synthesized in the same manner as in the preparation of compound 1, except that 11.61 g (10.0 mmol) of starting material 1-2 was used instead of starting material 1-1, to give 1.06 g of compound 2 in a 9% yield. MS (MALDI-TOF) m / z: 1176 [M]+

[0102] [ka]

[0103] Compound 66 was synthesized in the same manner as in the preparation of Compound 1, except that 12.47 g (10.0 mmol) of starting material 1-3 was used instead of starting material 1-1, to give 1.14 g of the compound 66 in a 9% yield. MS (MALDI-TOF) m / z: 1262 [M]+

[0104] [ka]

[0105] Compound 46 was synthesized in the same manner as in the preparation of compound 1, except that 12.89 g (10.0 mmol) of starting material 1-4 was used instead of starting material 1-1, to give 1.30 g of compound 46 in a 10% yield. MS (MALDI-TOF) m / z: 1304 [M]+

[0106] [ka]

[0107] Compound 161 was synthesized in the same manner as in the preparation of Compound 1, except that 11.88 g (10.0 mmol) of starting material 1-5 was used instead of starting material 1-1, to give 1.32 g of the compound 161 in an 11% yield. MS (MALDI-TOF) m / z: 1203 [M]+

[0108] [ka]

[0109] Compound 121 was synthesized in the same manner as in the preparation of Compound 1, except that 11.71 g (10.0 mmol) of starting material 1-6 was used instead of starting material 1-1, to give 1.07 g of the compound 121 in a 9% yield. MS (MALDI-TOF) m / z: 1187 [M]+

[0110] [ka]

[0111] A solution of 11.82 g (10.0 mmol) of starting material 1-7 in tert-butylbenzene (42 ml) was cooled to 0° C. Under a nitrogen atmosphere, 12.0 mL (30.0 mmol) of a 2.5 M n-butyllithium solution (in hexane) was added, and the mixture was stirred at room temperature for 3 hours.

[0112] The reaction mixture was then cooled to 0°C, 2.89 mL (30.0 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was then cooled to 0°C, 6.97 mL (40 mmol) of N,N-diisopropylethylamine was added, and the mixture was stirred at 60°C to 70°C for 2 hours.

[0113] The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. The extracted organic layer was dried over MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0114] Thereafter, the product was purified by recrystallization using a DCM / acetone mixed solvent to obtain 0.94 g of the compound 111 in a yield of 9%. MS (MALDI-TOF) m / z: 1039 [M]+

[0115] [ka]

[0116] Compound 47 was synthesized in the same manner as in the preparation of compound 111, except that 10.86 g (10.0 mmol) of starting material 1-8 was used instead of starting material 1-7, to give 0.66 g of compound 47 in a 7% yield. MS (MALDI-TOF) m / z: 943 [M]+

[0117] [ka]

[0118] 0.94 g (1.0 mmol) of compound 47, 0.46 g (2.5 mmol) of phenoxazine, 0.288 g (3.0 mmol) of sodium tert-butoxide, 0.046 g (0.05 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.041 g (0.1 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and 100 mL of toluene were added and refluxed with stirring. After the reaction was completed, the toluene layer was extracted with 50 mL of water.

[0119] The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. The extracted organic layer was dried over MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0120] Thereafter, the product was purified by recrystallization using a DCM / acetone mixed solvent to obtain 0.84 g of the compound 48 in a yield of 68%. MS (MALDI-TOF) m / z: 1237 [M]+

[0121] [ka]

[0122] Compound 49 was synthesized in the same manner as in the preparation of Compound 48, except that 0.42 g (2.5 mmol) of carbazole was used instead of phenoxazine, to give 0.84 g of Compound 49 in a 70% yield. MS (MALDI-TOF) m / z: 1205 [M]+

[0123] [ka]

[0124] Compound 112 was synthesized in the same manner as in the preparation of compound 111, except that 12.19 g (10.0 mmol) of starting material 1-11 was used instead of starting material 1-7, to give 0.86 g of compound 112 in an 8% yield. MS (MALDI-TOF) m / z: 1076 [M]+

[0125] [ka]

[0126] Compound 114 was synthesized in the same manner as in the preparation of Compound 48, except that 0.21 g (2.5 mmol) of piperidine was used instead of phenoxazine, to give 0.85 g of Compound 114 in a 72% yield. MS (MALDI-TOF) m / z: 1174 [M]+

[0127] [ka]

[0128] Compound 115 was synthesized in the same manner as in the preparation of Compound 48, except that 0.18 g (2.5 mmol) of pyrrolidine was used instead of phenoxazine, to give 0.84 g of Compound 115 in a 73% yield. MS (MALDI-TOF) m / z: 1145 [M]+

[0129] [ka]

[0130] Compound 117 was synthesized in the same manner as in the preparation of compound 111, except that 9.13 g (10.0 mmol) of starting material 1-14 was used instead of starting material 1-7, to give 0.93 g of compound 117 in a 12% yield. MS (MALDI-TOF) m / z: 771 [M]+

[0131] [ka]

[0132] Compound 118 was synthesized in the same manner as in the preparation of Compound 48, except that 0.5 g (1.0 mmol) of ditolylamine was used instead of phenoxazine, to give 0.87 g of Compound 118 in 80% yield. MS (MALDI-TOF) m / z: 1092 [M]+

[0133] [ka]

[0134] 0.77 g (1.0 mmol) of compound 117, 0.24 g (2.5 mmol) of phenol, 1.6 g (5.0 mmol) of cesium carbonate, 0.03 g (0.2 mmol) of copper (I) chloride, and 10 mL of methylpyrrolidone were added and refluxed with stirring.

[0135] The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. The extracted organic layer was dried over MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0136] Thereafter, the product was purified by recrystallization using a DCM / acetone mixed solvent to obtain 0.87 g of the compound 119 in a 76% yield. MS (MALDI-TOF) m / z: 886 [M]+

[0137] [ka]

[0138] Compound 120 was synthesized in the same manner as in the preparation of compound 111, except that 10.19 g (10.0 mmol) of starting material 1-17 was used instead of starting material 1-7, to give 0.81 g of compound 120 in an 11% yield. MS (MALDI-TOF) m / z: 738 [M]+

[0139] [ka]

[0140] Compound 196 was synthesized in the same manner as in the preparation of compound 48, except that 0.74 g (1.0 mmol) of compound 120 was used instead of starting material 1-8, to give 0.77 g of compound 196 in a 75% yield. MS (MALDI-TOF) m / z: 1031 [M]+

[0141] [ka]

[0142] 0.74 g (1.0 mmol) of compound 120, 0.31 g (2.5 mmol) of phenylboronic acid, 1.06 g (5.0 mmol) of tripotassium phosphate, 0.01 g (0.06 mmol) of palladium(II) acetate, 0.05 g (0.12 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, toluene (10 mL), and HO (1 mL) were added and refluxed with stirring.

[0143] The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. The extracted organic layer was dried over MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane).

[0144] Thereafter, the product was purified by recrystallization using a DCM / acetone mixed solvent to obtain 0.66 g of the compound 133 in a yield of 80%. MS (MALDI-TOF) m / z: 821 [M]+

[0145] (Example) (Example 1: Manufacturing method of organic electroluminescent device with bottom emission structure) A substrate with ITO (100nm) laminated on it, which is the anode of the organic electroluminescent device, was patterned by photolithography to separate it into cathode, anode, and insulating layer. Then, to increase the work function of the anode (ITO) and to clean it, the surface was treated with UV ozone and O2:N2 plasma. A 10nm thick HAT-CN was then formed on top of it as a hole injection layer (HIL). Next, a hole-transporting layer (HTL) of N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was vacuum-deposited on top of the HTL to a thickness of 90 nm, and an electron-blocking layer (EBL) of N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine was deposited on top of the HTL to a thickness of 15 nm. A 25 nm-thick light-emitting layer (EML) was formed on top of the EBL by simultaneously depositing α,β-AND as a host for the light-emitting layer and doping it with 2% Compound 1 as a dopant.

[0146] A 25-nm thick electron transport layer (ETL) was formed thereon by mixing 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and LiQ in a 1:1 weight ratio. An electron injection layer was then deposited on the electron transport layer by 1 nm, and aluminum was then deposited to a thickness of 100 nm as a negative electrode. A seal cap containing a getter was then attached using a UV-curable adhesive to protect the organic electroluminescent device from atmospheric oxygen and moisture, thereby completing the production of an organic electroluminescent device.

[0147] Examples 2 to 10: Production of organic electroluminescent devices Organic electroluminescent devices were manufactured in the same manner as in Example 1, except that compounds 2, 66, 46, 161, 121, 48, 49, 114, and 115 were used instead of compound 1 as the dopant.

[0148] (Comparative Example 1: Production of Organic Electroluminescent Device) An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 1 as the dopant.

[0149] [ka]

[0150] <Characteristics analysis of organic electroluminescent devices> Hereinafter, the organic electroluminescent devices with a bottom emission structure manufactured in Examples 1 to 10 and Comparative Example 1 were subjected to an electric current of 10 mA / cm 2 The light-emitting characteristics were measured by applying a current of 10 mA / cm 2 The results of measuring the life span by constant current drive are shown in Table 1 below.

[0151] [Table 1]

[0152] It was confirmed that, compared with an organic electroluminescent device using the compound A as a dopant, an organic electroluminescent device using the compound of the present invention as a dopant material exhibits superior effects in current efficiency and lifespan, although the voltage is at the same level.

[0153] Furthermore, the emission wavelengths of the embodied compounds 1 and 2 of the present invention and the comparative compound 1 (compound A) were measured, and it was confirmed that the compounds of the present invention had narrower half-value widths than the comparative compounds.

[0154] (Example 11: Manufacturing method of organic electroluminescent device with bottom emission structure) A substrate with a 100nm ITO layer, which serves as the anode of an organic electroluminescent device, was patterned using a photolithography process to separate the cathode, cathode, and insulating layer. The cathode (ITO) was then surface-treated using UV ozone and O2:N2 plasma to increase its work function and clean it. A 10nm thick HAT-CN hole-injection layer (HIL) was then formed on top of the HIL. A 90nm thick hole-transport layer (HIL) of N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was then vacuum-deposited on top of the HIL. A 15nm thick mCP electron-blocking layer (EBL) was then formed on top of the HTL. Compound B was deposited on the electron blocking layer (EBL) as a host for the light emitting layer, and at the same time, Compound 1 was doped at 2% as a dopant to form an emission layer (EML) with a thickness of 20 nm.

[0155] TSPO1 was deposited thereon to a thickness of 5 nm as a hole-blocking layer (HBL), followed by TPBI to a thickness of 30 nm as an electron-transporting layer (ETL). LIF was deposited on the ETL to a thickness of 1 nm, and aluminum was deposited to a thickness of 50 nm as a negative electrode. A seal cap containing a getter was then attached using a UV-curable adhesive to protect the organic electroluminescent device from atmospheric oxygen and moisture, thereby completing the production of an organic electroluminescent device.

[0156] [ka]

[0157] (Examples 12 to 20: Production of organic electroluminescent devices) Organic electroluminescent devices were fabricated in the same manner as in Example 11, except that compounds 2, 66, 46, 161, 121, 48, 49, 114, and 115 were used instead of compound 1 as the dopant.

[0158] (Comparative Example 2: Production of Organic Electroluminescent Device) An organic electroluminescent device was manufactured in the same manner as in Example 8, except that Compound A was used instead of Compound 1 as the dopant.

[0159] [ka]

[0160] <Characteristics analysis of organic electroluminescent devices> Hereinafter, the organic electroluminescent devices with a bottom emission structure manufactured in Examples 11 to 20 and Comparative Example 2 were subjected to an electric current of 10 mA / cm 2 The light-emitting characteristics were measured by applying a current of 10 mA / cm 2 The results of measuring the life span by constant current drive are shown in Table 2 below.

[0161] [Table 2]

[0162] It was confirmed that, compared with an organic electroluminescent device using the compound A as a dopant, an organic electroluminescent device using the compound of the present invention as a dopant material exhibits a superior effect in current efficiency, although the voltage is at the same level.

[0163] Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited to these, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. A compound selected from the following compounds 1 to 10, 14, 15, 19, 24 to 30, 35 to 37, 40, 42, 47 to 49, and 197. 【Chemistry 1】 【Chemistry 2】 【Transformation 3】

2. A first electrode; a second electrode provided opposite the first electrode; An organic electroluminescent device including one or more organic material layers provided between the first electrode and the second electrode, An organic electroluminescent device, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound according to claim 1 .

3. The organic electroluminescent device according to claim 2 , wherein the organic 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.

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