Organic compound and organic electroluminescent element containing the same

Abstract

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

Description

Technical Field

[0001] The present invention relates to an organic compound and an organic electroluminescent element comprising the same. Background Art

[0002] Compared with other flat panel display elements such as existing liquid crystal displays (LCDs), plasma display panels (PDPs) and field emission displays (FEDs), organic electroluminescent elements (OLEDs) have a simple structure and many advantages in the manufacturing process. They have high brightness and excellent field of view characteristics, fast response speed and low driving voltage. Therefore, they are actively developed and commercialized so that they can be used as light sources for flat panel displays such as wall-mounted TVs or display backlights, lighting, billboards, etc.

[0003] As for organic electroluminescent elements, the initial organic EL element was reported by CW Tang et al. of Eastman Kodak Company (CW Tang, SAVanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987). The luminescence principle thereof is generally based on that, when voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form excitons, i.e., electron-hole pairs, and the energy of the excitons is converted into light by transferring the energy of the excitons to the luminescent material.

[0004] More specifically, the organic electroluminescent element has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode) and one or more organic layers between the two electrodes. At this time, the organic electroluminescent element is stacked in the order of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) or an electron injection layer (ELL) from the anode, and in order to improve the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) may be further included before and after the light emitting layer, respectively.

[0005] Most of the materials used in the organic layer of organic electroluminescent elements are pure organic materials or complexes formed by organic materials and metals. According to their uses, they can be divided into hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc.

[0006] Among them, organic substances that are easily oxidized and electrochemically stable during oxidation are mainly used as hole injection substances or hole transport substances, and organic substances that are easily reduced and electrochemically stable during reduction are mainly used as electron injection substances or electron transport substances.

[0007] On the other hand, the luminescent layer material is preferably a material having a stable form in both the oxidized and reduced states, preferably a material with high luminescent efficiency in converting excitons into light when they are formed. More specifically, the luminescent layer is composed of two materials, a host and a dopant, the dopant must have a high quantum efficiency, and preferably, the energy gap of the host material is greater than that of the dopant material, so as to facilitate the transfer of energy to the dopant. Displays used for televisions (TV), mobile phones, etc. achieve full color (Full color) through three colors of red, green, and blue, and the luminescent layers are composed of a red host / dopant, a green host / dopant, and a blue host / dopant, respectively.

[0008] In the past, fluorescent molecules such as perylene, coumarine, anthracene, and pyrene were used as blue dopants. However, since the emission spectrum and full width half the maximum of the dopant are wide, there is a disadvantage that pure blue light cannot be used when manufacturing components. This characteristic not only reduces the efficiency of blue in the cavity structure of the component, but also makes it difficult to use the deep blue range.

[0009] Recently, a document using a boron-based dopant with a narrow emission spectrum of a device and high device efficiency has been published (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. In the case of the boron-based blue dopant substances introduced in the past, the boron atom is contained in the center and cyclized, and the boron forms only a three-coordinate bond, so that the molecular structure remains in a planar state.

[0010] The advantage of this planar structure dopant is that the emission spectrum and half-peak width are narrowed due to the similarity of the energy levels of the molecular vibration modes, thereby emitting pure light.

[0011] [Prior art literature]

[0012] [Patent Document]

[0013] (Non-patent document 1) Krebs, Frederik C., et al., "Synthesis, Structure, and Properties of 4,8,12-Triox a-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

[0014] Problem that the invention aims to solve

[0015] An object of the present invention is to provide a novel organic compound and an organic electroluminescent device comprising the organic compound.

[0016] Another object of the present invention is to provide a novel compound which is an organic compound having a narrow emission spectrum and a half-value width and can be used as a light-emitting layer material or the like.

[0017] Another object of the present invention is to use organic compounds with excellent lifespan, efficiency, electrochemical stability and thermal stability to provide an organic electroluminescent element with low driving voltage, high efficiency in low-doping areas, and relatively suppressed efficiency reduction in high-doping areas, especially excellent characteristics such as lifespan.

[0018] Another object of the present invention is to use the above organic compounds to provide a blue host / dopant system and an organic electroluminescent element suitable for an active matrix organic light emitting diode panel (AM-OLED).

[0019] Means used to solve problems

[0020] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1.

[0021] [Chemical formula 1]

[0022]

[0023] in,

[0024] n, m, o and p are the same or different from each other and are each independently an integer of 0 or 1,

[0025] n+m+o+p is an integer greater than 2,

[0026] Y1 and Y2 are the same or different from each other, and are each independently B, N, C(R1)(R2), P=O or P=S,

[0027] X1 to X4 are the same as or different from each other, and are each independently B(R3), N(R4), O, S or Se,

[0028] A, B, C, D and E are the same as or different from each other, and are each independently 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,

[0029] At least one of A, B, C, D and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0030] The above R1 to R4 are the same as or different from each other, and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, The invention further comprises a group consisting of a substituted or unsubstituted heteroarylalkyl group having 3 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring.

[0031] Furthermore, the present invention provides an organic electroluminescent element, which is an organic light-emitting element comprising a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the one or more organic layers contains a compound represented by the above Chemical Formula 1.

[0032] For example, the organic electroluminescent element 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, etc. However, the structure of the organic electroluminescent element is not limited thereto and may include a smaller number of organic layers.

[0033] According to a preferred embodiment of the present invention, the organic layer is a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1.

[0034] According to a preferred specific example of the present invention, it is characterized in that the above-mentioned organic layer is a hole injection layer, a hole transport layer or an electron blocking layer, and the above-mentioned hole injection layer, hole transport layer or electron blocking layer contains the compound represented by the above-mentioned chemical formula 1.

[0035] In the present invention, "hydrogen" means hydrogen, protium, deuterium or tritium.

[0036] In the present specification, the "halogen group" is fluorine, chlorine, bromine or iodine.

[0037] In the present invention, "alkyl" refers to 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, isopentyl, and hexyl.

[0038] 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 include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0039] 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 and 2-propynyl.

[0040] In the present invention, the "alkylthio group" refers to the above-mentioned alkyl group bonded via a sulfur bond (-S-).

[0041] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or two or more rings. In addition, two or more rings may be pendant or fused. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, dimethylfluorenyl, and the like.

[0042] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S or Se. In addition, it can include a form in which two or more rings are pendant or fused to each other, and can also include a form fused to an aryl. As examples of such heteroaryl groups, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, such as pheno xathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc. can be cited, but it is not limited thereto.

[0043] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, where R is an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenoxy, naphthoxy, and diphenoxy.

[0044] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' refers to an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentyloxy, and the like.

[0045] In the present invention, "alkoxy" can be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, and preferably the number of carbon atoms is 1 to 20. Specifically, it can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but it is not limited thereto.

[0046] In the present invention, "aralkyl" refers to an aryl-alkyl group as described above consisting of an aryl group and an alkyl group. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of preferred aralkyl groups include benzyl, 2-phenylethyl and naphthylmethyl. The bonding to the parent residue is achieved through the alkyl group.

[0047] In the present invention, the "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

[0048] In the present invention, the "alkylamino group" refers to an amine substituted by an alkyl group having 1 to 30 carbon atoms.

[0049] In the present invention, the "aralkylamino group" refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

[0050] In the present invention, "heteroarylamino" refers to an amino group substituted by an aryl group having 6 to 30 carbon atoms and a heterocyclic group.

[0051] In the present invention, "heteroaralkyl" refers to an aryl-alkyl group substituted by a heterocyclic group.

[0052] 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, and adamantine.

[0053] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include morpholine, piperazine, etc., but are not limited thereto.

[0054] In the present invention, an “alkylsilyl group” refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and an “arylsilyl group” refers to a silyl group substituted by an aryl group having 6 to 60 carbon atoms.

[0055] In the present invention, the "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring or a combination thereof.

[0056] In the present invention, "bonding with adjacent groups to form a ring" means bonding with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof.

[0057] In the present specification, the term "alicyclic compound" has the same meaning as "aliphatic hydrocarbon ring", and refers to a non-aromatic ring consisting only of carbon and hydrogen atoms.

[0058] In the present specification, the "heteroalicyclic compound" refers to an alicyclic compound in which one or more carbon atoms of an "aliphatic hydrocarbon ring" are replaced by a heteroatom, and thus contains at least one heteroatom.

[0059] In the present specification, examples of the "aromatic hydrocarbon ring" include phenyl, naphthyl, anthracenyl and the like, but are not limited thereto.

[0060] In the present specification, the "aliphatic heterocycle" refers to an aliphatic ring containing one or more hetero atoms.

[0061] In the present specification, an "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms.

[0062] In the present specification, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocyclic ring, and an aromatic heterocyclic ring may be a monocyclic ring or a polycyclic ring.

[0063] In this specification, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. As for the position of substitution, there is no limitation on the position of substitution as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same or different from each other. The above substituents may be substituted by one or more substituents selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 24 carbon atoms, heteroalkyl having 2 to 30 carbon atoms, aralkyl having 6 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, alkylamino having 1 to 30 carbon atoms, arylamino having 6 to 30 carbon atoms, aralkylamino having 6 to 30 carbon atoms and heteroarylamino having 2 to 24 carbon atoms, but are not limited to the above examples.

[0064] In the present specification, "bonding to adjacent groups to form a ring" means bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle or a condensed ring thereof.

[0065] Effects of the Invention

[0066] The present invention provides a novel compound which is an organic compound having a narrow emission spectrum and a half-value width and can be used as a light-emitting layer material or the like.

[0067] The present invention provides an organic electroluminescent element which can realize a low driving voltage and significantly improve the color gamut by using an organic compound having excellent lifespan, efficiency, electrochemical stability and thermal stability.

[0068] Furthermore, the present invention provides a blue host / dopant system and an organic electroluminescent element of a blue series suitable for an active matrix organic light emitting diode panel (AM-OLED) using the above organic compound. DETAILED DESCRIPTION

[0069] The present invention relates to a compound represented by the following chemical formula 1:

[0070] [Chemical formula 1]

[0071]

[0072] in,

[0073] n, m, o and p are the same or different from each other and are each independently an integer of 0 or 1,

[0074] n+m+o+p is an integer greater than 2,

[0075] Y1 and Y2 are the same or different from each other, and are each independently B, N, C(R1)(R2), P=O or P=S,

[0076] X1 to X4 are the same as or different from each other, and are each independently B(R3), N(R4), O, S or Se,

[0077] A, B, C, D and E are the same as or different from each other, and are each independently 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,

[0078] At least one of A, B, C, D and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0079] The above R1 to R4 are the same as or different from each other, and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, The invention further comprises a group consisting of a substituted or unsubstituted heteroarylalkyl group having 3 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring. Specific embodiments

[0081] The embodiments of the present invention are described in detail below to facilitate implementation by those skilled in the art. However, the present invention can be implemented in various forms and is not limited to the embodiments described in this specification.

[0082] The organic compound according to the present invention has a planar structure, which minimizes the (π-π) mutual attraction of molecules within the molecule and makes the energy levels of the molecular vibration modes almost similar, resulting in a narrower emission spectrum and half-peak width, thereby significantly improving the color gamut.

[0083] The organic compound according to the present invention includes atoms (eg, boron-based elements) providing a planar structure to prevent the generation of intramolecular excited state dimers (Excimers) and to increase the efficiency and life of the device by increasing the electron density of the core and the stability of the dopant.

[0084] Specifically, it relates to a compound represented by the following chemical formula 1:

[0085] [Chemical formula 1]

[0086]

[0087] in,

[0088] n, m, o and p are the same or different from each other and are each independently an integer of 0 or 1,

[0089] n+m+o+p is an integer greater than 2,

[0090] Y1 and Y2 are the same or different from each other, and are each independently B, N, C(R1)(R2), P=O or P=S,

[0091] X1 to X4 are the same as or different from each other, and are each independently B(R3), N(R4), O, S or Se,

[0092] A, B, C, D and E are the same as or different from each other, and are each independently 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,

[0093] At least one of A, B, C, D and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0094] The above R1 to R4 are the same as or different from each other and are independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, The present invention further comprises a group consisting of a substituted or unsubstituted heteroaralkyl group having 3 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring.

[0095] At least one of A, C and E may be a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0096] Specifically, the heteroaryl group may be selected from substituted or unsubstituted pyrrole, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted dioxin, substituted or unsubstituted oxathiine, substituted or unsubstituted dithiin, The invention also comprises a group consisting of substituted or unsubstituted indole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzodioxin, substituted or unsubstituted benzoxathiin, substituted or unsubstituted benzodithiine, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzodioxin, substituted or unsubstituted phenoxathiin, and substituted or unsubstituted thianthrene. When the above heteroaryl groups are substituted, adjacent substituents may be connected to each other to form a cyclic compound.

[0097] More specifically, the above A, C and E are the same or different from each other, and each independently can be a compound represented by the following Chemical Formula 2 or Chemical Formula 3:

[0098] [Chemical formula 2]

[0099]

[0100] [Chemical formula 3]

[0101]

[0102] in,

[0103] X5 to X 10 and X 12 To X 15 are the same as or different from each other, and are independently selected from the group consisting of C(R5), N, S and O,

[0104] X 11 is selected from the group consisting of C(R6)(R7), N(R8), S and O,

[0105] R5 to R8 are the same as or different from each other, and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted The present invention further comprises a group consisting of a substituted or unsubstituted heteroarylalkyl group having 6 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring.

[0106] Specifically, when A, C and E are all formed according to Chemical Formula 2, X5 to X 10 Neither is C(R5).

[0107] When A, C and E all form Chemical Formula 3, X 11 When C(R6)(R7) is 12 To X 15 None of them can be C(R5).

[0108] In the above X5 to X 10 and X 12 To X 15 When both are C(R5), X 11 Not C(R6)(R7).

[0109] The above C may be selected from the group consisting of Chemical Formula 4 to Chemical Formula 7 below.

[0110] [Chemical formula 4]

[0111]

[0112] [Chemical formula 5]

[0113]

[0114] [Chemical formula 6]

[0115]

[0116] [Chemical formula 7]

[0117]

[0118] in,

[0119] Four groups among Y1 to Y6 are portions that are bonded to adjacent groups,

[0120] The groups not bonded to the adjacent groups among Y1 to Y6 are the same as or different from each other, and are independently selected from the group consisting of C(R9), N, S and O,

[0121] Y7 to Y 10 The second group in the two groups is a portion bonded to the adjacent groups,

[0122] Y7 to Y 10 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 10 ), N, S and O,

[0123] Y 11 To Y 14 The two groups in are the parts bonded to the adjacent groups,

[0124] Y 11 To Y 14 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 11 ), N, S and O,

[0125] Y 15 To Y 18 The two groups in are the parts bonded to the adjacent groups,

[0126] Y 15 To Y 18 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 12 ), N, S and O,

[0127] Y 19 To Y 22 The two groups in are the parts bonded to the adjacent groups,

[0128] Y 19 To Y 22 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 13 ), N, S and O,

[0129] Y 23 To Y 26The two groups in are the parts bonded to the adjacent groups,

[0130] Y 23 To Y 26 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 14 ), N, S and O,

[0131] Y 27 To Y 30 The two groups in are the parts bonded to the adjacent groups,

[0132] Y 27 To Y 30 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 15 ), N, S and O,

[0133] X 16 To X 18 are the same or different from each other and are each independently C(R 16 )(R 17 )N(R 18 ), S and O,

[0134] R9 to R 18 The same as or different from each other, and each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 3 The present invention further comprises a group consisting of 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring.

[0135] The above A and E are the same or different from each other, and each independently can be a compound selected from the group consisting of the following Chemical Formulas 8 to 11:

[0136] [Chemical formula 8]

[0137]

[0138] [Chemical formula 9]

[0139]

[0140] [Chemical formula 10]

[0141]

[0142] [Chemical formula 11]

[0143]

[0144] in,

[0145] q and r are integers from 0 to 4,

[0146] Y 31 To Y 36 The two groups in are the parts bonded to the adjacent groups,

[0147] Y 31 To Y 36 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 21 ), N, S and O,

[0148] Y 37 To Y 40 The two groups in are the parts bonded to the adjacent groups,

[0149] Y 37 To Y 40 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 22 ), N, S and O,

[0150] Y 41 and Y 42 is the part that bonds to the adjacent group,

[0151] Y 43 To Y 46 The two groups in are the parts bonded to the adjacent groups,

[0152] Y 43 To Y 46 The groups not bonded to the adjacent groups are the same or different from each other and are independently selected from C(R 23 ), N, S and O,

[0153] X 19and X 21 The same or different from each other, each independently selected from C(R 24 )(R 25 )、N(R 26 ), S and O,

[0154] R 19 To R 26 The same as or different from each other, and each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 3 The present invention further comprises a group consisting of 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 arylalkylamino 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 can bond to adjacent groups to form a substituted or unsubstituted ring.

[0155] The above Y1 and Y2 are the same as or different from each other, and are each independently B or N.

[0156] The above B and D are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0157] The compound represented by Chemical Formula 1 according to the present invention may be represented by the following compounds, but is not limited thereto:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] The compound of the above chemical formula 1 of the present invention can be usefully used as a dopant substance of the light-emitting layer. Specifically, the above organic compound as a dopant substance can provide an organic compound with good thermal stability and narrow emission spectrum and half-peak width compared with existing boron dopants, thereby significantly improving the color gamut.

[0167] The organic compound of the present invention can be usefully used as a material for forming a light-emitting layer. The material for forming a light-emitting layer as described above may further contain a substance generally added when the organic compound is prepared into a form required for forming a light-emitting layer, for example, a host substance.

[0168] The light-emitting layer-forming material may be a dopant material.

[0169] The present invention provides an organic electroluminescent element including the compound represented by the above Chemical Formula 1.

[0170] 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.

[0171] Furthermore, the present invention relates to a light-emitting layer-forming material comprising the above-mentioned organic compound.

[0172] The above-mentioned material for forming a light-emitting layer may further contain a substance usually added when the above-mentioned organic compound is prepared into a form required for forming a light-emitting layer, for example, a host substance.

[0173] Furthermore, the present invention relates to an organic electroluminescent element in which an organic thin film layer composed of one or more layers including at least a light-emitting layer is stacked between a cathode and an anode, characterized in that the light-emitting layer contains a single organic compound represented by the above chemical formula 1 or a combination of two or more organic compounds.

[0174] The organic electroluminescent element may have a structure of stacking 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, and may further stack an electron blocking layer, a hole blocking layer and the like as required.

[0175] Hereinafter, the organic electroluminescent device of the present invention will be described with examples, but the contents of the following examples do not limit the organic electroluminescent device of the present invention.

[0176] The organic electroluminescent element 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 stacked in sequence. Preferably, an electron blocking layer (EBL) may be further included between the anode and the light-emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the cathode and the light-emitting layer. Furthermore, a hole blocking layer (HBL) may be further included between the cathode and the light-emitting layer.

[0177] As the manufacture method of organic electroluminescent element according to the present invention, first, anode is formed by applying anode material on substrate surface in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and water resistance. And, as anode material, transparent and excellent conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) etc. can be used.

[0178] Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal evaporation or spin coating in a conventional manner. Examples of such a hole injection layer material include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA) as a starburst amine, 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), or IDE406 available from Idemitsu Kosan Co., Ltd.

[0179] The hole transport layer (HTL) material is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating in a conventional manner. In this case, the hole transport layer material may be bis(N-(1-naphthyl-orthophenyl))benzidine (α-NPD), N,N'-di(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).

[0180] The surface of the hole transport layer is vacuum-evaporated or spin-coated with an emitting layer (EML) material by conventional methods to form an emitting layer. At this time, the emitting layer material used may be a single emitting material or a emitting main material, such as tris(8-hydroxyquinolyl)aluminum (Alq3) for green, or Alq3, 4,4'-N,N'-dicarbazole-biphenyl (4,4'-N,N'-dicabazole-biphenyl, CBP), poly(n-vinylcabazole), PVK, 9,10-di(naphthalene-2-yl)anthracene (9,10-di(naphthalene-2-yl)anthracene, ADN), 4,4',4"-tri(8-hydroxyquinolyl)aluminum (Alq3) for blue. (N-carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene, TPBI), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (3-tert-butyl-9,10-di(naphth-2-yl)anthracene, TBADN), E3, distyrylarylene (DSA) or a mixture of two or more thereof, but not limited thereto.

[0181] As a dopant that can be used together with a light-emitting host in a light-emitting layer substance, the compound of the present invention can be preferably used.

[0182] Optionally, an electron blocking layer (EBL) may be further formed between the hole transport layer and the light emitting layer.

[0183] The electron transport layer (ETL) material is formed by vacuum thermal evaporation or spin coating on the surface of the light emitting layer in a conventional manner. At this time, there is no particular limitation on the electron transport layer material used, and preferably, tris(8-hydroxyquinoline)aluminum (Alq3) can be used.

[0184] Optionally, a hole blocking layer (HBL) is further formed between the light emitting layer and the electron transport layer and a phosphorescent dopant is used in the light emitting layer to prevent triplet excitons or holes from diffusing into the electron transport layer.

[0185] The formation of the hole blocking layer can be carried out by vacuum thermal evaporation or spin coating of the hole blocking layer material by conventional methods. There is no particular limitation on the hole blocking layer material, but (8-hydroxyquinolyl) lithium (Liq), bis(8-hydroxy-2-methylquinolyl)-biphenyloxyaluminum (BAlq), bathocuproine (BCP) and lithium fluoride (LiF) can be preferably used.

[0186] The electron injection layer (EIL) material is formed by vacuum thermal evaporation or spin coating on the surface of the electron transport layer in a conventional manner. At this time, the electron injection layer material can use LiF, Liq, Li2O, BaO, NaCl, CsF and other materials.

[0187] A cathode material is formed by vacuum thermal evaporation on the surface of the electron injection layer in a conventional manner.

[0188] At this time, the cathode material used 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, the front-emitting organic electroluminescent element may use indium tin oxide (ITO) or indium zinc oxide (IZO) to form a transparent cathode that can transmit light. A capping layer (CPL) may be formed on the surface of the cathode.

[0189] Hereinafter, the synthesis method of the above-mentioned compound will be described by representative examples. However, the synthesis method of the compound of the present invention is not limited to the method exemplified below, and the compound of the present invention can be prepared by the method exemplified below and methods known in the art.

[0190] [Synthesis Example 1-1]

[0191]

[0192] Starting material 1-1 Compound 1

[0193] 11.94 g (10.0 mmol) of the starting material 1-1, o-dichlorobenzene (30 ml) and 4.82 mL (50.0 mmol) of boron tribromide were added to the high pressure reactor and stirred, and the reaction mixture was heated to 180° C. to 190° C. and stirred for 12 hours.

[0194] After the reaction solution was cooled to room temperature, cooling water was added and the organic layer was extracted with ethyl acetate. The solvent of the extracted organic layer was dried with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane / hexane (DCM / Hexane)).

[0195] Subsequently, after recrystallization using a dichloromethane / acetone (DCM / Acetone) mixed solvent, 0.97 g of the above-mentioned compound 1 was obtained with a yield of 8%.

[0196] MS (MALDI-TOF) m / z: 1209[M]+

[0197] [Synthesis Example 1-2]

[0198]

[0199] Starting material 1-2 Compound 2

[0200] The same method as that for Compound 1 was used except that 11.61 g (10.0 mmol) of Starting Material 1-2 was used instead of Starting Material 1-1, and 1.06 g of Compound 2 was obtained in a yield of 9%.

[0201] MS (MALDI-TOF) m / z: 1176[M]+

[0202] [Synthesis Example 1-3]

[0203]

[0204] Starting material 1-3 Compound 66

[0205] The same method as that for Compound 1 was used except that 12.47 g (10.0 mmol) of Starting Material 1-3 was used instead of Starting Material 1-1, and 1.14 g of Compound 66 was obtained in a yield of 9%.

[0206] MS (MALDI-TOF) m / z: 1262[M]+

[0207] [Synthesis Example 1-4]

[0208]

[0209] Starting materials 1-4 Compound 46

[0210] The same method as that for Compound 1 was used except that 12.89 g (10.0 mmol) of Starting Material 1-4 was used instead of Starting Material 1-1, and 1.30 g of Compound 46 was obtained in a yield of 10%.

[0211] MS (MALDI-TOF) m / z: 1304[M]+

[0212] [Synthesis Example 1-5]

[0213]

[0214] Starting materials 1-5 Compound 161

[0215] 1.32 g of Compound 161 was obtained in a yield of 11% by the same method as that of Compound 1, except that 11.88 g (10.0 mmol) of Starting Material 1-5 was used instead of Starting Material 1-1.

[0216] MS (MALDI-TOF) m / z: 1203[M]+

[0217] [Synthesis Example 1-6]

[0218]

[0219] Starting materials 1-6 Compound 121

[0220] 1.07 g of Compound 121 was obtained in a yield of 9% by performing the synthesis 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.

[0221] MS (MALDI-TOF) m / z: 1187[M]+

[0222] [Synthesis Example 1-7]

[0223]

[0224] Starting materials 1-7 Compound 111

[0225] 11.82 g (10.0 mmol) of the starting material 1-7 was dissolved in tert-butylbenzene (42 mL), and then cooled to 0° C. 12.0 mL (30.0 mmol) of a 2.5 M n-butyllithium solution (in hexane) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 hours.

[0226] Subsequently, the reaction mixture was 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 cooled to 0°C, 6.97 mL (40 mmol) of N,N-diisopropylethylamine was added, and the mixture was stirred at 60 to 70°C for 2 hours.

[0227] The reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. The solvent of the extracted organic layer was dried with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane / hexane (DCM / Hexane)).

[0228] Subsequently, after recrystallization using a dichloromethane / acetone (DCM / Acetone) mixed solvent, 0.94 g of the compound 111 was obtained with a yield of 9%.

[0229] MS (MALDI-TOF) m / z: 1039[M]+

[0230] [Synthesis Example 1-8]

[0231]

[0232] Starting materials 1-8 Compound 47

[0233] 0.66 g of the compound 47 was obtained in a yield of 7% by performing the synthesis in the same manner as in the preparation of compound 111 except that 10.86 g (10.0 mmol) of the starting material 1-8 was used instead of the starting material 1-7.

[0234] MS (MALDI-TOF) m / z: 943[M]+

[0235] [Synthesis Example 1-9]

[0236]

[0237] Compound 47 Compound 48

[0238] 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl and 100 mL of toluene were added, and the mixture was refluxed while stirring. After the reaction was completed, the toluene layer was extracted with 50 mL of water.

[0239] The reaction solution was cooled to room temperature and the organic layer was extracted with ethyl acetate and water. The solvent of the extracted organic layer was dried with MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane / hexane (DCM / Hexane)).

[0240] Subsequently, after recrystallization using a dichloromethane / acetone (DCM / Acetone) mixed solvent, 0.84 g of the above-mentioned compound 48 was obtained with a yield of 68%.

[0241] MS (MALDI-TOF) m / z: 1237[M]+

[0242] [Synthesis Example 1-10]

[0243]

[0244] Compound 1-9 Compound 49

[0245] The same method as that for Compound 48 was used except that 0.42 g (2.5 mmol) of carbazole was used instead of phenoxazine, and 0.84 g of Compound 49 was obtained in a yield of 70%.

[0246] MS (MALDI-TOF) m / z: 1205[M]+

[0247] [Synthesis Example 1-11]

[0248]

[0249] Starting materials 1-11 Compound 112

[0250] 0.86 g of the compound 112 was obtained in a yield of 8% by performing the synthesis in the same manner as in the preparation of compound 111 except that 12.19 g (10.0 mmol) of the starting material 1-11 was used instead of the starting material 1-7.

[0251] MS (MALDI-TOF) m / z: 1076[M]+

[0252] [Synthesis Example 1-12]

[0253]

[0254] Compound 112 Compound 114

[0255] 0.85 g of Compound 114 was obtained in a yield of 72% by the same method as that of Compound 48 except that 0.21 g (2.5 mmol) of piperidine was used instead of phenoxazine.

[0256] MS (MALDI-TOF) m / z: 1174[M]+

[0257] [Synthesis Example 1-13]

[0258]

[0259] Compound 112 Compound 115

[0260] The same method as that for Compound 48 was used except that 0.18 g (2.5 mmol) of pyrrolidine was used instead of phenoxazine to obtain 0.84 g of Compound 115 in a yield of 73%.

[0261] MS (MALDI-TOF) m / z: 1145[M]+

[0262] [Synthesis Example 1-14]

[0263]

[0264] Starting materials 1-14 Compound 117

[0265] 0.93 g of Compound 117 was obtained in a yield of 12% by performing the synthesis 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.

[0266] MS (MALDI-TOF) m / z: 771[M]+

[0267] [Synthesis Example 1-15]

[0268]

[0269] Compound 117 Compound 118

[0270] The same method as that for Compound 48 was used except that 0.5 g (1.0 mmol) of xylylamine was used instead of phenoxazine, and 0.87 g of Compound 118 was obtained in a yield of 80%.

[0271] MS (MALDI-TOF) m / z: 1092[M]+

[0272] [Synthesis Example 1-16]

[0273]

[0274] Compound 117 Compound 119

[0275] 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 the mixture was refluxed with stirring.

[0276] The reaction solution was cooled to room temperature and the organic layer was extracted with ethyl acetate and water. The solvent of the extracted organic layer was dried with MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane / hexane (DCM / Hexane)).

[0277] Subsequently, after recrystallization using a dichloromethane / acetone (DCM / Acetone) mixed solvent, 0.87 g of the compound 119 was obtained with a yield of 76%.

[0278] MS (MALDI-TOF) m / z: 886[M]+

[0279] [Synthesis Example 1-17]

[0280]

[0281] Starting material 1-17 Compound 120

[0282] 0.81 g of the compound 120 was obtained in a yield of 11% by the same method as that of the compound 111 except that 10.19 g (10.0 mmol) of the starting material 1-17 was used instead of the starting material 1-7.

[0283] MS (MALDI-TOF) m / z: 738[M]+

[0284] [Synthesis Example 1-18]

[0285]

[0286] Compound 120 Compound 196

[0287] The same method as that for Compound 48 was used except that 0.74 g (1.0 mmol) of Compound 120 was used instead of Starting Material 1-8 to obtain 0.77 g of Compound 196 in a yield of 75%.

[0288] MS (MALDI-TOF) m / z: 1031[M]+

[0289] [Synthesis Example 1-19]

[0290]

[0291] Compound 120 Compound 133

[0292] 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 H2O (1 mL) were added and refluxed with stirring.

[0293] The reaction solution was cooled to room temperature and the organic layer was extracted with ethyl acetate and water. The solvent of the extracted organic layer was dried with MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane / hexane (DCM / Hexane)).

[0294] Subsequently, after recrystallization using a dichloromethane / acetone (DCM / Acetone) mixed solvent, 0.66 g of the compound 133 was obtained with a yield of 80%.

[0295] MS (MALDI-TOF) m / z: 821[M]+

[0296] <Example 1: Method for manufacturing a back-emitting organic electroluminescent element>

[0297] After the substrate with ITO (100nm) as the anode of the organic electroluminescent element was divided into the cathode, anode area and insulating layer and patterned by photolithography, UV ozone treatment was performed for the purpose of improving the work function of the anode (ITO) and cleaning, and surface treatment was performed with O2:N2 plasma. On top of it, HAT-CN was formed with a thickness of 10nm as a hole injection layer (HIL). Next, N4,N4,N4',N4'-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was vacuum-deposited to a thickness of 90 nm on the hole injection layer to form a hole transport layer, and N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine was formed to a thickness of 15 nm on the hole transport layer (HTL) as an electron blocking layer (EBL). 9-(naphthalene-1-yl)-10-(naphthalene-2-yl)anthracene (α,β-ADN) was vapor-deposited on the electron blocking layer (EBL) as a host of the light-emitting layer, and about 2% of compound 1 was doped as a dopant to form a light-emitting layer (EML) with a thickness of 25 nm.

[0298] On top of it, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and LiQ were mixed in a weight ratio of 1:1 and evaporated to 25nm as an electron transport layer (ETL), 1nm of electron injection layer was evaporated on the electron transport layer, and aluminum was evaporated to a thickness of 100nm as a cathode. Subsequently, a seal cap containing an adsorbent (getter) was attached using an ultraviolet (UV) curable adhesive to protect the organic electroluminescent element from oxygen or moisture in the atmosphere, thereby manufacturing an organic electroluminescent element.

[0299] <Examples 2 to 10: Production of Organic Electroluminescent Element>

[0300] An organic electroluminescent element was manufactured in the same manner as in Example 1, except that Compound 2, 66, 46, 161, 121, 48, 49, 114, or 115 was used as a dopant instead of Compound 1.

[0301] <Comparative Example 1: Production of Organic Electroluminescent Element>

[0302] An organic electroluminescent element was produced in the same manner as in Example 1 except that Compound A was used instead of Compound 1 as a dopant.

[0303] <Compound A>

[0304]

[0305] <Analysis of Characteristics of Organic Electroluminescent Element>

[0306] Next, a 10 mA / cm 2 The current detection electro-optical characteristics of 10mA / cm 2 The lifetime was measured by constant current driving, and the results were compared and shown in the following Table 1.

[0307] [Table 1]

[0308] distinguish Dopant Voltage (V) Current efficiency (Cd / A) Lifespan T95(hr) Example 1 Compound 1 3.98 7.7 188 Example 2 Compound 2 3.95 7.6 147 Example 3 Compound 66 3.96 8.1 105 Example 4 Compound 46 4.00 8.2 101 Example 5 Compound 161 3.88 8.1 123 Example 6 Compound 121 3.92 8.0 140 Example 7 Compound 48 3.90 7.7 105 Example 8 Compound 49 3.89 7.8 140 Example 9 Compound 114 3.95 7.7 127 Example 10 Compound 115 3.94 7.7 114 Comparative Example 1 Compound A 3.95 6.5 94

[0309] Compared with the organic electroluminescent element using the compound A as a dopant, the organic electroluminescent element using the compound of the present invention as a dopant material showed excellent effects in current efficiency and life while having the same voltage.

[0310] <Example 11: Method for manufacturing a back-emitting organic electroluminescent element>

[0311] After the substrate with ITO (100nm) stacked as the anode of the organic electroluminescent element was divided into the cathode, anode area and insulating layer and patterned by the photolithography process, UV ozone treatment was carried out for the purpose of improving the work function and cleaning of the anode (ITO), and surface treatment was carried out with O2:N2 plasma. On top of it, HAT-CN was formed with a thickness of 10nm as a hole injection layer (HIL). Then, N4,N4,N4',N4'-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-bi]-4,4'-diamine was vacuum evaporated with a thickness of 90nm on the upper part of the above-mentioned hole injection layer to form a hole transport layer, and 1,3-bis(N-carbazolyl)benzene (mCP) was formed with a thickness of 15nm as an electron blocking layer (EBL) on the upper part of the above-mentioned hole transport layer (HTL). Compound B was deposited on the electron blocking layer (EBL) as the main component of the light-emitting layer, and about 2% of compound 1 was doped as a dopant to form a light-emitting layer (EML) with a thickness of 20 nm.

[0312] On top of it, 5nm of diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1) was evaporated as a hole blocking layer (HBL), and then 30nm of 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TP BI) was evaporated as an electron transport layer (ETL), 1nm of LIF was evaporated on the top of the electron transport layer, and aluminum was evaporated with a thickness of 50nm as a cathode. Subsequently, a seal cap containing an adsorbent (getter) was attached using an ultraviolet (UV) curable adhesive to protect the organic electroluminescent element from oxygen or moisture in the atmosphere, thereby manufacturing an organic electroluminescent element.

[0313] <Compound B>

[0314]

[0315] <Examples 12 to 20: Production of Organic Electroluminescent Element>

[0316] An organic electroluminescent element was manufactured in the same manner as in Example 11, except that Compound 2, 66, 46, 161, 121, 48, 49, 114, or 115 was used as a dopant instead of Compound 1.

[0317] <Comparative Example 2: Production of Organic Electroluminescent Element>

[0318] An organic electroluminescent element was manufactured in the same manner as in Example 8 except that Compound A was used as a dopant instead of Compound 1.

[0319] <Compound A>

[0320]

[0321] <Analysis of Characteristics of Organic Electroluminescent Element>

[0322] In addition, for the back-emitting organic electroluminescent elements manufactured in Examples 11 to 20 and Comparative Example 2, 10 mA / cm 2 The current detection electro-optical characteristics of 10mA / cm 2 The lifetime was detected by constant current driving, and the test results were compared and shown in the following Table 2.

[0323] [Table 2]

[0324] distinguish Dopant Voltage (V) Current efficiency (Cd / A) Embodiment 11 Compound 1 6.89 15.1 Example 12 Compound 2 6.95 14.8 Example 13 Compound 66 6.98 15.4 Embodiment 14 Compound 46 7.03 15.7 Embodiment 15 Compound 161 6.90 14.8 Example 16 Compound 121 6.94 15.0 Embodiment 17 Compound 48 7.02 15.2 Embodiment 18 Compound 49 7.00 15.4 Embodiment 19 Compound 114 7.01 15.2 Embodiment 20 Compound 115 7.02 15.0 Comparative Example 2 Compound A 7.05 12.6

[0325] The organic electroluminescent element using the compound of the present invention as a dopant material showed a superior effect in current efficiency while the voltage was at the same level as that of the organic electroluminescent element using the compound A as a dopant.

[0326] The preferred embodiments of the present invention are described in detail above, but the scope of protection of the present invention is not limited thereto. Various modifications and improvements made by technical personnel in the field using the basic concepts of the present invention as defined in the above scope of protection of the present invention are also included in the scope of protection of the present invention.

[0327] Industrial Applicability

[0328] The present invention relates to a novel organic compound and an organic electroluminescent element comprising the organic compound.

Claims

1. A compound, characterized in that Selected from the following compounds:

2. An organic electroluminescent element, characterized in that: The first electrode, a second electrode, opposite to the first electrode, and One or more organic layers are disposed between the first electrode and the second electrode; At least one of the organic layers comprises the compound according to claim 1 .

3. The organic electroluminescent element according to claim 2, characterized in that: 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.

4. The organic electroluminescent element according to claim 2, characterized in that: The organic layer is a light-emitting layer.

5. The organic electroluminescent element according to claim 2, characterized in that ， The compound according to claim 1 is contained in the organic electroluminescent element as a dopant for a light-emitting layer.

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