Polycyclic compound and organic light-emitting device using the same

Abstract

The present invention relates to an organic light-emitting device with high efficiency and long life. The organic light-emitting device uses a polycyclic compound that can be used in various organic layers of the organic light-emitting device as a dopant for the light-emitting layer, and uses an anthracene derivative compound with a specific structure and substituent as the main body of the light-emitting layer, thereby improving the color purity and significantly improving the luminous efficiency and life characteristics.

Description

Technical Field

[0001] The present invention relates to a polycyclic compound and an organic light-emitting device having improved luminous efficiency and life characteristics produced using the same. In addition, the present invention relates to a high-efficiency and long-life organic light-emitting device, which uses the polycyclic compound of the present invention as a dopant and an anthracene derivative compound as a host, and in particular, when an anthracene derivative compound having a structure containing deuterium in the anthracene skeleton is used, the life characteristics and luminous efficiency are significantly improved, and excellent color purity can be achieved. Background Art

[0002] An organic light-emitting device is a self-luminous device in which electrons (electrons) injected from an electron injection electrode (cathode) and holes (holes) injected from a hole injection electrode (anode) combine in a light-emitting layer to form excitons, which emit light while releasing energy. The organic light-emitting device as described above has low driving voltage, high brightness, wide viewing angle and fast response time, and because of its suitability for full-color flat-panel light-emitting displays, it has attracted much attention as the next generation of light sources.

[0003] In order for such an organic light-emitting device to exert the characteristics as described above, it is first necessary to optimize the structure of the organic layers in the device, and the hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, electron blocking materials, etc. that constitute each organic layer must be supported by stable and effective materials. However, in fact, it is still necessary to continue to develop stable and effective organic layer structures and materials for organic light-emitting devices.

[0004] In particular, to obtain maximum efficiency in the light-emitting layer, the energy band gaps of the host and the dopant must form a suitable combination so that holes and electrons are each transferred to the dopant through a stable electrochemical pathway to form excitons.

[0005] In fact, there is a continuous demand for the development of a structure of a device that can improve the light-emitting characteristics of an organic light-emitting device as described above and a new material supporting such a structure.

[0006] In addition, the improvement of stable PL quantum efficiency, efficiency improvement and color purity improvement is an important factor in the FWHM (Full width at half maximum, hereinafter referred to as "half width") of the luminescent spectrum. Displays of mobile phones, TVs, etc. use resonant structures to achieve high color reproduction rates. When the light path is designed to resonate at a specific wavelength (hereinafter referred to as "resonance filtering"), the line width becomes narrower and the color purity improves (RH Jordan et al, Appl. Phys. Lett. 1996, v6, 1997, Huajun Peng et al, Appl. Phys. Lett. 2005, v87, 173505). The half width of the luminescent spectrum of organic matter is generally 30 to 100nm (BMKrasovitskii et al. Organic luminescent materials, VCH publishers), so luminescent materials with smaller half width can be expected to further increase efficiency in resonant devices.

[0007] Among the substances used as blue dopants in the past, fluorescent molecules such as perylene, coumarine, anthracene, and pyrene account for a large proportion, but the emission spectrum and full width half the maximum of the dopant are wide, so there is a disadvantage that pure blue light cannot be used when making devices. Such characteristics can not only reduce the efficiency of blue in the resonance structure of the device, but also are the main reason for making the application of the deep blue range difficult.

[0008] In addition, short-wavelength blue light (Blue Light) below 455nm can damage retinal cells, and in severe cases can cause diseases such as cataracts and macular degeneration. Therefore, in order to solve this problem that is harmful to the human body, a technology called Bio Blue has also been developed. Bio Blue is a technology that shifts the central wavelength of a blue OLED device that presents blue light from a short wavelength to a long wavelength, thereby minimizing harmful wavelengths of blue light while expressing accurate colors. If the harmful wavelength ratio is reduced by more than 6%, it is interpreted that the impact of blue light on the retina is actually almost zero, so research and development are also ongoing for vision protection for consumers who use display devices such as computers, mobile phones, and augmented reality (AR) and virtual reality (VR) devices for a long time. Summary of the invention

[0009] Therefore, the present invention provides a compound which is used in the organic layer of a device, thereby realizing a device with high efficiency and long life characteristics, and the half width of the luminescence spectrum is further reduced, thereby realizing additional efficiency increase and improved color purity. The present invention also provides an organic light-emitting device which uses the above-mentioned compound as a dopant and simultaneously uses a host compound of a specific structure.

[0010] In order to solve the above problems, the present invention provides a polycyclic compound represented by the following [Chemical Formula 1] or [Chemical Formula 2].

[0011]

[0012] In addition, in order to solve the above-mentioned problems, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode opposite to the first electrode, and an organic layer between the first electrode and the second electrode, the organic layer includes a light-emitting layer including a main body and a dopant, the dopant includes at least one of the compounds represented by [Chemical Formula 1] and [Chemical Formula 2], and the main body is an anthracene compound represented by [Chemical Formula 3].

[0013]

[0014] [Chemical formula 3]

[0015]

[0016] The compound represented by the above [Chemical Formula 3] is characterized by a structure containing deuterium, that is, the above R 11 To R 18 At least one of them is deuterium, and the additional Ar 1 To Ar 4 The hydrogen can be replaced by deuterium.

[0017] The characteristic structures of the above-mentioned [Chemical Formula 1], [Chemical Formula 2] and [Chemical Formula 3] and the definitions of each substituent and specific compounds realized by them are described below.

[0018] The polycyclic compound according to the present invention is a boron-containing polycyclic compound having a silyl group as a substituent. By using it in the organic layer within the device, a high-efficiency, long-life organic light-emitting device with improved color purity and excellent luminous efficiency and long life characteristics can be realized.

[0019] In addition, the organic light-emitting device according to the present invention uses a boron-containing polycyclic compound having a silyl group as a substituent as a dopant, and an anthracene derivative compound as a main body. In particular, when an anthracene derivative compound having a structure containing deuterium in the anthracene skeleton is used as a main body for the light-emitting layer, a long-life, high-efficiency organic light-emitting device can be achieved. Therefore, it can be usefully applied not only to lighting devices, but also to various display devices such as flat panels, flexible, and wearable displays. DETAILED DESCRIPTION

[0020] Hereinafter, the present invention will be described in more detail.

[0021] The present invention relates to a polycyclic compound represented by the following [Chemical Formula 1] or [Chemical Formula 2], and by using the compound, an organic light-emitting device with improved color purity and high efficiency and long life can be realized.

[0022]

[0023] In the above [Chemical Formula 1] and [Chemical Formula 2],

[0024] X is B, P=O, P=S or Al, Y 1 and Y 2 Each independently is NR 1 , O, S, CR 2 R 3 or SiR 4 R 5 , Y 3 It is O or S.

[0025] According to an embodiment of the present invention, X may be B (boron).

[0026] A 1 To A 3 The rings are each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring having 5 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and a substituted or unsubstituted aliphatic-aromatic mixed ring having 3 to 30 carbon atoms.

[0027] According to one embodiment of the present invention, the above A 2 The ring is characterized by having a substituted or unsubstituted amine group having 0 to 30 carbon atoms as a substituent.

[0028] According to one embodiment of the present invention, the amine group may be a diarylamine group, at least one of the aryl groups of the diarylamine group may be a substituted or unsubstituted phenyl group, and the substituent of the phenyl group may be an aryl group having 6 to 20 carbon atoms substituted at the ortho position.

[0029] In addition, the above R and R1 To R 5 the same as or different from each other, and each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio having 1 to 30 carbon atoms Substituted or unsubstituted arylthio group having 5 to 30 carbon atoms Any one of a substituted or unsubstituted amino group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, a nitro group, a cyano group and a halogen group, but excluding the case where the plurality of Rs consist only of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0030] According to an embodiment of the present invention, at least one of the plurality of Rs may be a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms.

[0031] In addition, the above R 1 To R 5 Can be combined with the above A 1 To A 3 The rings are connected to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0032] In addition, the above-mentioned plural Rs may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0033] In addition, the above R 2 and R 3 and R 4 and R 5 They may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0034] According to an embodiment of the present invention, at least one of the hydrogen atoms in the compound represented by the above-mentioned [Chemical Formula 1] or [Chemical Formula 2] may be substituted by deuterium.

[0035] According to one embodiment of the present invention, the above-mentioned [Chemical Formula 1] is represented by the following [Chemical Formula 1-1], and the above-mentioned [Chemical Formula 2] may be a polycyclic compound represented by the following [Chemical Formula 2-1].

[0036]

[0037] In the above [Chemical Formula 1-1] and [Chemical Formula 2-1], A 1 , A 2 , X, Y 1 To Y 3 and R are as defined in the above-mentioned [Chemical Formula 1] and [Chemical Formula 2], but at least one of the plurality of Rs is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms.

[0038] In addition, the present invention relates to an organic light-emitting device, characterized in that it is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, the organic layer comprising a light-emitting layer comprising a main body and a dopant, the dopant comprising at least one of the compounds represented by [Chemical Formula 1] and [Chemical Formula 2], and the main body is an anthracene compound represented by the following [Chemical Formula 3].

[0039] [Chemical formula 3]

[0040]

[0041] In the above [Chemical Formula 3],

[0042] The above R 11 To R 18 The same as or different from each other, and each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, a nitro group, a cyano group and a halogen group.

[0043] However, the characteristic is that the above R 11 To R 18 At least one of them is deuterium. According to one embodiment of the present invention, R 11 To R 18 At least 4 of them may be deuterium.

[0044] Ar 1 and Ar 3They are the same as or different from each other and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

[0045] Ar 2 and Ar 4 The same as or different from each other, and each is independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms.

[0046] D n Ar 1 To Ar 4 The number of hydrogen atoms replaced by deuterium atoms, n being an integer from 0 to 50.

[0047] As described above, the compound represented by the above [Chemical Formula 3] according to the present invention is a compound in which at least one deuterium is introduced into anthracene, and may further contain additional deuterium.

[0048] According to one embodiment of the present invention, R in the above-mentioned [Chemical Formula 3] 11 To R 18 At least four of them may be deuterium.

[0049] On the other hand, in the above-mentioned [Chemical Formula 1], [Chemical Formula 2] and [Chemical Formula 3], the term "substituted or unsubstituted" means A 1 To A 3 , R and R 1 To R 5 The following are each substituted by one or more substituents selected from deuterium, cyano, halogen, hydroxyl, nitro, amino, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, heteroalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryloxy, or a substituent formed by connecting two or more of the above substituents, or having no substituent.

[0050] In addition, the carbon number range of the alkyl or aryl group in the above-mentioned "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 6 to 50 carbon atoms", etc. refers to the total carbon number of the alkyl or aryl group when the substituted part is considered to be unsubstituted without considering the substituted part of the above-mentioned substituent. For example, a phenyl group substituted with a butyl group at the para position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0051] In addition, in the present invention, the meaning of combining with adjacent groups to form a ring is that it can combine with adjacent groups to form a substituted or unsubstituted alicyclic or aromatic ring, and the "adjacent substituent" can refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in terms of stereostructure, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent substituents" to each other.

[0052] In the present invention, the alkyl group may be linear or branched, and specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0053] In the present invention, the alkenyl group includes a straight chain or a branched chain, and may be further substituted by other substituents, specifically, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalene-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, styryl, etc., but are not limited to these.

[0054] In the present invention, the alkynyl group also includes a straight chain or a branched chain, and may be further substituted with other substituents, examples of which include ethynyl and 2-propynyl, but are not limited thereto.

[0055] In the present invention, the aromatic hydrocarbon ring or aromatic group may be monocyclic or polycyclic. Examples of monocyclic aromatic groups include phenyl, biphenyl, terphenyl, stilbene, etc. Examples of polycyclic aromatic groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, naphthyl, phenanthrenyl, pyrenyl, peryl, tetraphenyl, phenyl, fluorenyl, acenaphthophenyl However, the scope of the present invention is not limited to these examples.

[0056] In the present invention, an aromatic heterocyclic ring or a heteroaryl group is an aromatic ring containing one or more heteroatoms, and examples thereof include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, Oxazolyl triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline, thiazolyl different Azolyl, Oxazolyl Thiadiazolyl, benzothiazolyl, phenothiazinyl, etc., but not limited thereto.

[0057] In the present invention, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms, and examples thereof include monocyclic or polycyclic rings, which may be further substituted by other substituents, and polycyclic rings refer to groups formed by direct connection or fusion with other cyclic groups, and other cyclic groups may also refer to aliphatic hydrocarbon rings, but may also be other types of cyclic groups, such as aliphatic heterocyclic rings, aryl groups, heteroaryl groups, etc. Specifically, it includes cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; and cycloalkanes such as cyclohexane and cyclopentane; and cycloalkenes such as cyclohexene and cyclobutene, but is not limited thereto.

[0058] In the present invention, aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms, including heteroatoms such as O, S, Se, N or Si, and also includes monocyclic or polycyclic rings, and may be further substituted by other substituents. Polycyclic rings refer to heterocycloalkyl, heterocycloalkane, heterocycloalkene, The other ring groups may also refer to aliphatic heterocyclic rings, but may also be other types of ring groups, such as aliphatic hydrocarbon rings, aryl groups, heteroaryl groups, and the like.

[0059] In the present invention, an aliphatic aromatic mixed ring or an aliphatic aromatic mixed ring group refers to a ring in which two or more rings are fused to each other and the molecule as a whole has non-aromaticity. In addition, a polycyclic non-aromatic fused heterocycle refers to a non-aromatic fused hydrocarbon ring containing a heteroatom selected from N, O, P and S in addition to C. Examples thereof include tetrahydronaphthalene, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, 1,2,3,4,4a,9b-hexahydrodibenzofuran, 2,3,4,4a,9,9a-hexahydro-4a,9a-dimethyl-1H-carbazole, 5,6,7,8-tetrahydroquinoline, etc., but are not limited thereto.

[0060] In the present invention, the alkoxy group may specifically be methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, etc., but is not limited thereto.

[0061] In the present invention, the silyl group may include -SiH 3 , alkylsilyl, arylsilyl, alkylarylsilyl, arylheteroarylsilyl, heteroarylsilyl, etc., arylsilyl refers to -SiH 3 A silyl group in which one, two or three hydrogen atoms are replaced by aryl groups; an alkylsilyl group refers to -SiH 3 A silyl group in which one, two or three hydrogen atoms are replaced by an alkyl group; an alkylarylsilyl group refers to a -SiH 3 At least one hydrogen in each of the alkyl and aryl groups is replaced by an alkyl group and an aryl group, thereby comprising a silyl group of 1 or 2 alkyl groups and 2 or 1 aryl groups corresponding thereto, and an arylheteroarylsilyl group refers to -SiH 3 At least one hydrogen in each of the silyl groups is replaced by an aryl group or a heteroaryl group, thereby comprising a silyl group containing 1 or 2 aryl groups and corresponding 2 or 1 heteroaryl groups, wherein the heteroaryl silyl group refers to -SiH 3 A silyl group in which one, two or three hydrogen atoms are replaced by a heteroaryl group. Examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group. The same is true for the alkylsilyl group and the heteroarylsilyl group.

[0062] Here, the aryl group in each of the above arylsilyl group, heteroarylsilyl group and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and the heteroaryl group in each of the above arylsilyl group, heteroarylsilyl group and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0063] In addition, specific examples of the above-mentioned silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl and the like, and one or more hydrogen atoms in the above-mentioned silyl group may be substituted with the same substituents as in the case of the above-mentioned aryl group.

[0064] In the present invention, the amine group may include -NH 2 , alkylamino, arylamino, alkylarylamino, arylheteroarylamino, heteroarylamino, etc., wherein arylamino refers to -NH 2 An amine in which one or both hydrogen atoms are replaced by an aryl group. An alkylamine group refers to an -NH 2 An amine in which one or both hydrogen atoms are replaced by an alkyl group. An alkylarylamine group refers to an -NH 2 An amine in which one hydrogen is replaced by an alkyl group and the other hydrogen is replaced by an aryl group. Arylheteroarylamine refers to -NH 2 An amine in which one hydrogen is replaced by an aryl group and the other hydrogen is replaced by a heteroaryl group. A heteroarylamine group refers to -NH 2 An amine in which one or two hydrogen atoms are replaced by a heteroaryl group. Examples of the above-mentioned arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The above-mentioned alkylamine groups and heteroarylamine groups are also applicable.

[0065] Here, the aryl group in each of the above-mentioned arylamine, heteroarylamine and arylheteroarylamine groups may be a monocyclic aryl group or a polycyclic aryl group, and the heteroaryl group in each of the above-mentioned arylamine, heteroarylamine and arylheteroarylamine groups may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Alternatively, it may be a polycyclic aryl group, and the heteroaryl group in each of the above-mentioned arylamine, heteroarylamine and arylheteroarylamine groups may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0066] In the present invention, the aryl group in the aryloxy group and the arylthio group is the same as the examples of the aryl group described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-phenanthracenyl group, a 3-phenanthracenyl group, and a 9-phenanthracenyl group. Examples of the arylthio group include, but are not limited to, a phenylthio group, a 2-methylphenylthio group, and a 4-tert-butylphenylthio group.

[0067] In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0068] More specifically, the polycyclic compound represented by [Chemical Formula 1] and [Chemical Formula 2] according to the present invention may be any one selected from the following compounds, thereby clearly determining the structure and specific substituents of [Chemical Formula 1] and [Chemical Formula 2], but the scope of [Chemical Formula 1] and [Chemical Formula 2] according to the present invention is not limited thereto.

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080] It can be confirmed from the above-mentioned specific compounds that according to the present invention, a polycyclic ring containing boron (B) and the like and simultaneously forming a characteristic structure is introduced thereinto, and an organic light-emitting device material having the inherent characteristics of the substituent is synthesized, thereby making it possible to manufacture a substance that meets the conditions required in each organic layer. Preferably, a substance for a light-emitting layer can be manufactured, thereby realizing a high-efficiency and long-life organic light-emitting device.

[0081] In addition, the half width (FWHM) of the EL emission spectrum of the compound according to the present invention has a value of less than 20 nm, preferably, a value of 15 nm to 20 nm. Thus, when the compound according to the present invention is used as a dopant compound in the light-emitting layer of a device, the efficiency is increased and the color purity improved by the reduction of the half width can be obtained.

[0082] In addition, the host of the organic light-emitting device according to the present invention may be any one selected from the following anthracene derivative compounds, but the scope thereof is not limited thereto.

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] According to one embodiment of the present invention, it is characterized in that it includes a light-emitting layer including a host and a dopant, the dopant includes at least one of the polycyclic compounds represented by the above [Chemical Formula 1] and [Chemical Formula 2], and the host is an anthracene compound represented by the above [Chemical Formula 3].

[0106] According to an embodiment of the present invention, the anthracene host compound represented by the above-mentioned [Chemical Formula 3] may be any one selected from the following anthracene derivative compounds having a structure containing deuterium in the anthracene skeleton, but the scope is not limited thereto.

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

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[0115]

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[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] At this time, the content of the dopant in the light-emitting layer can generally be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0127] In addition, the light-emitting layer may further contain various hosts and various dopant substances in addition to the dopant and host compound according to the present invention. In particular, the light-emitting layer host may be used by mixing or stacking two or more different compounds.

[0128] An organic light-emitting device according to an embodiment of the present invention may be composed of a structure including a first electrode, a second electrode and an organic layer arranged therebetween, and may be manufactured using conventional device manufacturing methods and materials except that the polycyclic compound according to [Chemical Formula 1] or [Chemical Formula 2] and the anthracene compound represented by [Chemical Formula 3] of the present invention are used in the organic layer of the device.

[0129] The organic layer of the organic light-emitting device according to the present invention may be composed of a single-layer structure, but may also be composed of a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, it is not limited thereto, and may also include a smaller number or a larger number of organic layers. The preferred organic layer structure of the organic light-emitting device according to the present invention is described in more detail in the embodiments described below.

[0130] The organic light-emitting device according to the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode. If necessary, a hole injection layer may be included between the anode and the hole transport layer. In addition, an electron injection layer may be included between the electron transport layer and the cathode. In addition, one or two intermediate layers may be formed, and a hole blocking layer or an electron blocking layer may also be formed.

[0131] As a preferred embodiment of the present invention, the organic layer between the first electrode and the second electrode of the present invention includes a light-emitting layer, which is composed of a main body and a dopant, and may contain a polycyclic compound represented by the above-mentioned [Chemical Formula 1] or [Chemical Formula 2] according to the present invention as a dopant in the light-emitting layer.

[0132] In addition, the light-emitting layer may further include various hosts and various dopant substances in addition to the above-mentioned dopant and host.

[0133] On the other hand, the specific structure of the organic light emitting device according to an embodiment of the present invention, its manufacturing method and each organic layer material are studied as follows.

[0134] First, an anode electrode material is applied to the upper part of the substrate to form an anode. Here, as the substrate, a substrate commonly used in an organic light-emitting device is used, but an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferred. In addition, transparent and highly conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc. are used as anode electrode materials.

[0135] A hole injection layer material is vacuum-evaporated or spin-coated on the anode electrode to form a hole injection layer, and then a hole transport layer material is vacuum-evaporated or spin-coated on the hole injection layer to form a hole transport layer.

[0136] The hole injection layer material can be used without particular limitation as long as it is a material commonly used in the art. As specific examples, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine, 4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine, N,N'-di(1-naphthyl)-N, N'-diphenylbenzidine], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-dia mine, N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile], etc.

[0137] In addition, the hole transport layer material is not particularly limited as long as it is a material commonly used in the art. For example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD) can be used.

[0138] Next, the hole auxiliary layer and the light-emitting layer are continuously stacked on the upper part of the hole transport layer, and the hole blocking layer is selectively formed into a thin film on the upper part of the light-emitting layer by a vacuum evaporation method or a spin coating method. When the holes in the hole blocking layer flow into the cathode through the organic light-emitting layer, the life and efficiency of the device decrease. Therefore, by using a substance with a very low HOMO (Highest Occupied Molecular Orbital) level, this problem is prevented. At this time, the hole blocking substance used is not particularly limited, but must have electron transport capability and at the same time have an ionization potential higher than that of the light-emitting compound. Representative BAlq, BCP, TPBI, etc. can be used.

[0139] As the material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq, etc., but are not limited to these.

[0140] After an electron transport layer is evaporated on such a hole blocking layer by a vacuum evaporation method or a spin coating method, an electron injection layer is formed, and a cathode forming metal is vacuum thermally evaporated on the upper part of the above-mentioned electron injection layer to form a cathode electrode, thereby completing an organic light-emitting device according to one embodiment of the present invention.

[0141] Here, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used. In order to obtain a top-emitting device, a transmissive cathode using ITO or IZO can be used.

[0142] The electron transport layer material has the function of stably transporting electrons injected from the cathode, and known electron transport materials can be used. As examples of known electron transport materials, quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2) can be used; Materials such as PBD, BMD, BND, etc. of oxadiazole derivatives.

[0143] In addition, the above-mentioned organic layers can each be formed using a single molecule evaporation method or a solution process. Here, the above-mentioned evaporation method refers to a method of forming a thin film by evaporating the substance used as the material for forming the above-mentioned layers by heating or the like under a vacuum or low pressure state, and the above-mentioned solution process refers to a method of mixing the substance used as the material for forming the above-mentioned layers with a solvent and forming a thin film by inkjet printing, roll coating, screen printing, spraying, dip coating, spin coating, etc.

[0144] In addition, the organic light emitting device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochrome or white flat panel lighting device, and a monochrome or white flexible lighting device.

[0145] The present invention will be described in more detail below with reference to preferred embodiments. However, it is obvious to those skilled in the art that these embodiments are intended to more specifically describe the present invention and that the scope of the present invention is not limited thereto.

[0146] Synthesis Example 1: Synthesis of [2]

[0147] Synthesis Example 1-1: Synthesis of A-1

[0148]

[0149] 50 g of <a-1a>After adding 50 mL of tetrahydrofuran, 140 mL of 2.0 M lithium diisopropylamide solution was added dropwise at -78 °C. After stirring at -78 °C for 3 hours, hexachloroethane was slowly added, and the temperature was raised to room temperature and stirred for 16 hours. Ethyl acetate and water were added and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-1>(42.5 g, 78.9%)

[0150] Synthesis Example 1-2: Synthesis of A-2

[0151]

[0152] Add 37.5 g of <a-1>, 12.7g <a-2a>, 1.42 g of tris(dibenzylideneacetone)dipalladium(0), 0.96 g of bis(diphenylphosphine)-1,1'-binaphthyl, 14.9 g of sodium tert-butoxide, and 375 mL of toluene were stirred under reflux for 3 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-2>(24g, 56%)

[0153] Synthesis Example 1-3: Synthesis of A-3

[0154]

[0155] 24 g of <a-2>, 16.3g <a-3a>, 0.4 g of bis(tri-tert-butylphosphine)palladium(0), 8.3 g of sodium tert-butoxide, and 240 mL of toluene were added and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-3>(31.4 g, 97.5%)

[0156] Synthesis Example 1-4: Synthesis of A-4

[0157]

[0158] 50 g of <a-4a>, 75.4g <a-4b>, 0.8 g of palladium acetate, 2.05 g of 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene 25.6 g of sodium tert-butoxide and 500 mL of toluene were added and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-4>(55g, 71.0%)

[0159] Synthesis Example 1-5: Synthesis of A-5

[0160]

[0161] 55 g of <a-4>, 20.6g <a-2a>, 2.3 g of tris(dibenzylideneacetone)dipalladium(0), 24.2 g of sodium tert-butoxide, 1.5 g of bis(diphenylphosphine)-1,1'-binaphthyl, and 550 mL of toluene were added and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-5>(46.8 g, 84.7%)

[0162] Synthesis Example 1-6: Synthesis of A-6

[0163]

[0164] 30 g of <a-3>, 19.4g <a-5>, 0.6 g of bis(tri-tert-butylphosphine)palladium(0), 5.8 g of sodium tert-butoxide, and 350 mL of toluene were added and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added and the organic layer was separated. Purification was performed by silica gel column chromatography to obtain <a-6>(48g, 98%)

[0165] Synthesis Example 1-7: Synthesis of [2]

[0166]

[0167] 35 g of <a-6>and 420 mL of tert-butylbenzene, then drop 51 mL of 1.7 M tert-butyllithium pentane solution at -78°C. After heating to 60°C and stirring for 2 hours, nitrogen was blown in at 60°C to completely remove pentane. After cooling to -78°C, drop 14.5 mL of boron tribromide. After heating to room temperature and stirring for 2 hours, cool to 0°C and drop 7.5 mL of N,N-diisopropylethylamine. After heating to 120°C and stirring for 16 hours. After cooling to room temperature, add 10% sodium acetate aqueous solution and ethyl acetate, separate the organic layer, and concentrate under reduced pressure. Purify by silica gel column chromatography to obtain [2]. (4.5 g, 13.1%)

[0168] MS (MALDI-TOF): m / z 1181.62 [M + ]

[0169] Synthesis Example 2: Synthesis of [6]

[0170] Synthesis Example 2-1: Synthesis of B-1

[0171]

[0172] In the above-mentioned synthesis examples 1-5, the <b-1a>replace <a-4>And by the same method we get <b-1>. (yield 85.1%)

[0173] Synthesis Example 2-2: Synthesis of B-2

[0174]

[0175] In the above-mentioned synthesis examples 1-4, the <b-1>replace <a-4a>And by the same method we get <b-2>. (Yield 46.2%)

[0176] Synthesis Example 2-3: Synthesis of B-3

[0177]

[0178] In the above-mentioned synthesis examples 1-5, the <b-2>replace <a-4>,use <b-3a>replace <a-2a>And by the same method we get <b-3>. (yield 89.4%)

[0179] Synthesis Example 2-4: Synthesis of B-4

[0180]

[0181] In the above-mentioned synthesis examples 1-6, the <b-3>replace <a-5>And by the same method we get <b-4>. (yield 98.9%)

[0182] Synthesis Example 2-5: Synthesis of [6]

[0183]

[0184] In the above-mentioned synthesis examples 1-7, the <b-4>replace <a-6>And [6] was obtained by the same method. (yield 13.8%)

[0185] MS (MALDI-TOF): m / z 1277.62 [M + ]

[0186] Synthesis Example 3: Synthesis of

[18]

[0187] Synthesis Example 3-1: Synthesis of C-1

[0188]

[0189] In the above-mentioned synthesis examples 1-6, the <c-1a>replace <a-3>And by the same method we get <c-1>. (yield 95.3%)

[0190] Synthesis Example 3-2: Synthesis of

[18]

[0191]

[0192] In the above-mentioned synthesis examples 1-7, the <c-1>replace <a-6>And

[18] was obtained by the same method. (yield 12.4%)

[0193] MS (MALDI-TOF): m / z 1161.66 [M + ]

[0194] Synthesis Example 4: Synthesis of

[21]

[0195] Synthesis Example 4-1: Synthesis of D-1

[0196]

[0197] 50 g of <d-1b>After adding 250 mL of tetrahydrofuran, 98.5 mL of 1.6 M n-butyl lithium solution was added dropwise at -78°C. After stirring at -78°C for 2 hours, <d-1a>The product was dissolved in 250 mL of tetrahydrofuran and slowly added. After the temperature was raised to room temperature, the product was stirred for 16 hours. Ethyl acetate and water were added and the organic layer was separated. The product was purified by silica gel column chromatography to obtain <d-1>(46.8 g, 72.6%)

[0198] Synthesis Example 4-2: Synthesis of D-2

[0199]

[0200] In the above-mentioned synthesis example 1-1, the <d-1>replace <a-1a>And by the same method we get <d-2>. (Yield 68.4%)

[0201] Synthesis Example 4-3: Synthesis of D-3

[0202]

[0203] In the above-mentioned synthesis example 1-2, using <d-2>replace <a-1>,use <b-3a>replace <a-2a>And by the same method we get <d-3>. (Yield 52.3%)

[0204] Synthesis Example 4-4: Synthesis of D-4

[0205]

[0206] In the above-mentioned synthesis examples 1-6, the <d-3>replace <a-3>And by the same method we get <d-4>. (yield 97.7%)

[0207] Synthesis Example 4-5: Synthesis of

[21]

[0208]

[0209] In the above-mentioned synthesis examples 1-7, the <d-4>replace <a-6>And

[21] was obtained by the same method. (Yield 10.5%)

[0210] MS (MALDI-TOF): m / z 1217.72 [M + ]

[0211] Synthesis Example 5: Synthesis of

[27]

[0212] Synthesis Example 5-1: Synthesis of E-1

[0213]

[0214] In the above-mentioned synthesis example 2-3, using <e-1a>replace <b-3a>And by the same method we get <e-1>. (yield 90.4%)

[0215] Synthesis Example 5-2: Synthesis of E-2

[0216]

[0217] In the above-mentioned synthesis examples 1-6, the <e-1>replace <a-5>And by the same method we get <e-2>. (yield 95.2%)

[0218] Synthesis Example 5-3: Synthesis of

[27]

[0219]

[0220] In the above-mentioned synthesis examples 1-7, the <e-2>replace <a-6>And

[27] was obtained by the same method. (yield 10.5%)

[0221] MS (MALDI-TOF): m / z 1235.54 [M + ]

[0222] Synthesis Example 6: Synthesis of

[31]

[0223] Synthesis Example 6-1: Synthesis of F-1

[0224]

[0225] In the above-mentioned synthesis examples 1-5, the <f-1a>replace <a-2a>And by the same method we get <f-1>. (yield 82.7%)

[0226] Synthesis Example 6-2: Synthesis of F-2

[0227]

[0228] In the above-mentioned synthesis example 1-2, using <f-2a>replace <a-2a>And by the same method we get <f-2>. (yield 86.2%)

[0229] Synthesis Example 6-3: Synthesis of F-3

[0230]

[0231] In the above-mentioned synthesis examples 1-3, the <f-2>replace <a-2>And by the same method we get <f-3>. (yield 94.7%)

[0232] Synthesis Example 6-4: Synthesis of F-4

[0233]

[0234] In the above-mentioned synthesis examples 1-6, the <f-3>replace <a-3>,use <f-1>replace <a-5>And by the same method we get <f-4>. (yield 87.6%)

[0235] Synthesis Example 6-5: Synthesis of

[31]

[0236]

[0237] In the above-mentioned synthesis examples 1-7, the <f-4>replace <a-6>And

[31] was obtained by the same method. (Yield 11.6%)

[0238] MS (MALDI-TOF): m / z 1159.51 [M + ]

[0239] Synthesis Example 7: Synthesis of

[32]

[0240] Synthesis Example 7-1: Synthesis of G-1

[0241]

[0242] In the above-mentioned synthesis example 2-1, the <f-1a>replace <a-2a>And by the same method we get <g-1>. (yield 86.2%)

[0243] Synthesis Example 7-2: Synthesis of G-2

[0244]

[0245] In the above-mentioned synthesis examples 1-4, the <g-1>replace <a-4a>And by the same method we get <g-2>. (Yield 49.3%)

[0246] Synthesis Example 7-3: Synthesis of G-3

[0247]

[0248] In the above-mentioned synthesis example 2-3, using <g-2>replace <b-2>,use <g-3a>replace <b-3a>And by the same method we get <g-3>. (Yield 87.8%)

[0249] Synthesis Example 7-4: Synthesis of G-4

[0250]

[0251] In the above-mentioned synthesis examples 1-6, the <g-3>replace <a-5>And by the same method we get <g-4>. (yield 91.1%)

[0252] Synthesis Example 7-5: Synthesis of

[32]

[0253]

[0254] In the above-mentioned synthesis examples 1-7, the <g-4>replace <a-6>And

[32] was obtained by the same method. (Yield 12.1%)

[0255] MS (MALDI-TOF): m / z 1195.46 [M + ]

[0256] Synthesis Example 8: Synthesis of

[33]

[0257] Synthesis Example 8-1: Synthesis of H-1

[0258]

[0259] In the above-mentioned synthesis examples 1-3, the <h-1a>replace <a-3a>And by the same method we get <h-1>. (yield 96.8%)

[0260] Synthesis Example 8-2: Synthesis of H-2

[0261]

[0262] In the above-mentioned Synthesis Example 5-2, the <h-1>replace <a-3>And by the same method we get <h-2>. (yield 94.1%)

[0263] Synthesis Example 8-3: Synthesis of

[33]

[0264]

[0265] In the above-mentioned synthesis examples 1-7, the <h-2>replace <a-6>And

[33] was obtained by the same method. (Yield 12.1%)

[0266] MS (MALDI-TOF): m / z 1260.54 [M + ]

[0267] Examples 1 to 8: Fabrication of organic light-emitting devices

[0268] After patterning the ITO glass so that the light-emitting area is 2 mm × 2 mm, the ITO glass is cleaned. The above ITO glass is installed in a vacuum chamber and the base pressure is set to 1 × 10 -7 After that, a hole injection layer was formed on the ITO layer in such a manner that the electron acceptor of the following structural formula [Acceptor-1] and [Chemical Formula F] were deposited in a ratio of [Acceptor-1]: [Chemical Formula F] = 2:98. As a hole transport layer, [Chemical Formula F] was formed into a film Next, as an electron blocking layer, [Chemical Formula G] was formed into a film The light-emitting layer is a film formed by mixing the host [BH1] described below and the compound of the present invention (2 wt %). Then, as a hole blocking layer, [chemical formula H] was formed into a film As an electron transport layer, [Chemical Formula E-1] and [Chemical Formula E-2] were formed into a film at a ratio of 1:1. As an electron injection layer, [Chemical Formula E-2] is Al The films were formed in sequence to produce an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0269]

[0270] Comparative Examples 1 to 5

[0271] Organic light-emitting devices were prepared by the same method except that the following [BD-1] to [BD-5] were used instead of the dopant compounds according to the present invention used in Examples 1 to 8, and the light emission characteristics of the organic light-emitting devices were measured at 0.4 mA. The structures of the above [BD-1] to [BD-5] are shown below.

[0272]

[0273] [Table 1]

[0274]

[0275] As shown in [Table 1] above, an organic light-emitting device using the compound according to the present invention as a dopant compound for the light-emitting layer in the device has significantly improved life characteristics and excellent external quantum efficiency compared to devices using compounds having characteristic structures compared with the compounds according to the present invention (Comparative Examples 1 to 5), thereby realizing a high-efficiency and long-life organic light-emitting device.

[0276] Experimental example: Half width measurement

[0277] The half widths of the compounds according to the present invention (Compounds 2 and 27) were confirmed under the same conditions as in the above-mentioned Examples.

[0278]

[0279] [Table 2]

[0280] distinguish Compound 2 Compound 27 Comparative Compound 1 Comparative Compound 2 Half Width(nm) 18.9 18.4 21.8 21.6

[0281] As shown in [Table 2] above, it can be confirmed that the half-width of the polycyclic compound substituted with silane, which is a characteristic of the compound according to the present invention, is reduced to less than 20 nm compared with the existing compound. When the compound according to the present invention is used as a dopant in the light-emitting layer of an organic light-emitting device, an increase in efficiency and an improvement in color purity due to the reduction in half-width can be obtained.

[0282] Examples 11 to 14: Fabrication of organic light-emitting devices

[0283] After patterning the ITO glass so that the light-emitting area is 2 mm × 2 mm, the ITO glass is cleaned. The above ITO glass is installed in a vacuum chamber and the base pressure is set to 1 × 10 -7 After that, a hole injection layer was formed on the ITO layer so that the electron acceptor of [Acceptor-1] and [Chemical Formula F] were deposited in a ratio of [Acceptor-1]: [Chemical Formula F] = 2:98. As a hole transport layer, [Chemical Formula F] was formed into a film Next, as an electron blocking layer, [Chemical Formula G] was formed into a film The light-emitting layer is a film formed by mixing the host [BH-1] according to the present invention described below and the compound (2 wt %) of [Chemical Formula 1] or [Chemical Formula 2] according to the present invention. Then, as a hole blocking layer, [chemical formula H] was formed into a film As an electron transport layer, [Chemical Formula E-1] and [Chemical Formula E-2] were formed into a film at a ratio of 1:1. As an electron injection layer, [Chemical Formula E-2] is Al The films were formed in sequence to produce an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0284]

[0285] Comparative Examples 11 to 14

[0286] An organic light-emitting device was prepared by the same method except that the host [BH1] used in Examples 1 to 8 was used instead of the host compound [BH-1] in the light-emitting layer used in Examples 11 to 14, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structure of [BH-2] is shown below.

[0287] [Table 3]

[0288] distinguish main body Dopant Voltage (V) Efficiency (EQE,%) Lifespan (T97, hr) Embodiment 11 BH-1 [6] 3.5 10.7 384 Example 12 BH-1

[27] 3.5 11.1 422 Embodiment 13 BH-1

[32] 3.5 10.9 401 Embodiment 14 BH-1

[33] 3.5 11.2 425 Comparative Example 11 BH1 [6] 3.5 10.3 227 Comparative Example 12 BH1

[27] 3.5 10.4 243 Comparative Example 13 BH1

[32] 3.5 10.3 236 Comparative Example 14 BH1

[33] 3.5 10.6 249

[0289] As shown in Examples 11 to 14 of [Table 3] above, by using the boron-containing polycyclic compound according to the present invention as a dopant and a derivative compound having an anthracene skeleton as a main body, when used in the light-emitting layer of the device, an organic light-emitting device with improved luminous efficiency and long life characteristics can be realized.

[0290] In addition, when anthracene in the anthracene derivative structure is substituted with deuterium, further improved device characteristics can be achieved compared to Comparative Examples 11 to 14.

[0291] Examples 15 to 18: Fabrication of organic light-emitting devices

[0292] An organic light-emitting device was prepared by the same method except that the following [BH-3] was used instead of the host compound [BH-1] in the light-emitting layer used in Examples 11 to 14, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structure of the above [BH-3] is shown below.

[0293]

[0294] Comparative Examples 15 to 18

[0295] An organic light-emitting device was prepared by the same method except that the following [BH-4] was used instead of the host compound [BH-3] in the light-emitting layer used in Examples 15 to 18, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structure of the above [BH-4] is shown below.

[0296]

[0297] [Table 4]

[0298] distinguish main body Dopant Voltage (V) Efficiency (EQE,%) Lifespan (T97, hr) Embodiment 15 BH-3 [6] 4.0 10.6 241 Example 16 BH-3

[27] 4.1 10.8 257 Embodiment 17 BH-3

[32] 4.0 10.9 267 Embodiment 18 BH-3

[33] 4.1 11.1 272 Comparative Example 15 BH-4 [6] 4.0 10.5 220 Comparative Example 16 BH-4

[27] 4.0 10.8 234 Comparative Example 17 BH-4

[32] 4.0 10.8 232 Comparative Example 18 BH-4

[33] 4.0 11.0 245

[0299] As shown in Examples 15 to 18 of [Table 4] above, by using the boron-containing polycyclic compound according to the present invention as a dopant and the deuterium-containing anthracene derivative compound as a main body, when used in the light-emitting layer of the device, an organic light-emitting device with improved luminous efficiency and long life characteristics can be realized.

[0300] In addition, compared with Comparative Examples 15 to 18, it was confirmed that the lifespan characteristics were further improved due to the difference in whether deuterium was included in the structure of the anthracene derivative compound.

[0301] As described above, as confirmed by the above [Table 3] and [Table 4], a device using the characteristic dopant compound and the main compound according to the present invention for the light-emitting layer in an organic light-emitting device can realize a long-life, high-efficiency organic light-emitting device with improved luminous efficiency and excellent life characteristics, compared with a device using a compound with a characteristic structure different from the compound according to the present invention.

Claims

1. A polycyclic compound represented by the following Chemical Formula 1-1 or Chemical Formula 2-1: In the chemical formula 1-1 to the chemical formula 2-1, X is B, Y1 and Y2 are each independently NR1, Y3 is O or S, A1 to A2 are each independently selected from substituted or unsubstituted aromatic hydrocarbon rings having 5 to 50 carbon atoms, However, the A2 must contain a substituted or unsubstituted amine group as a substituent. The R and R1 are the same or different and are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 50 carbon atoms, excluding the case where the R consists only of substituted or unsubstituted alkyl having 1 to 30 carbon atoms, "Substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, methyl, isopropyl, tert-butyl, phenyl, biphenyl and naphthyl, or substituted by a substituent formed by connecting two or more of the above substituents, or having no substituent.

2. The polycyclic compound according to claim 1, wherein At least one of the plurality of Rs is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

3. The polycyclic compound according to claim 1, wherein R1 is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

4. The polycyclic compound according to claim 1, wherein At least one of the hydrogen atoms in the compound represented by Chemical Formula 1-1 or Chemical Formula 2-1 is substituted with deuterium.

5. The polycyclic compound according to claim 1, wherein The compound represented by the chemical formula 1-1 or the chemical formula 2-1 is any one selected from the following compounds:

6. An organic light-emitting device, wherein: include: a first electrode, a second electrode opposite to the first electrode, and an organic layer between the first electrode and the second electrode, The organic layer includes a light-emitting layer including a host and a dopant, and the compound represented by Chemical Formula 1-1 or Chemical Formula 2-1 of claim 1 is the dopant in the light-emitting layer.

7. The organic light emitting device according to claim 6, wherein: The full width at half maximum (FWHM) of an EL emission spectrum of the organic light emitting device has a value of 20 nm or less.

8. The organic light emitting device according to claim 6, wherein: The host in the light-emitting layer is an anthracene compound represented by the following chemical formula 3: Chemical formula 3 In the chemical formula 3, R 11 To R 18 are the same as or different from each other and are each independently any one selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, a nitro group, a cyano group and a halogen group, However, the R 11 To R 18 At least one of is deuterium, Ar1 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, Ar2 and Ar4 are the same as or different from each other, and are each independently selected from any one of hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 30 carbon atoms, D n represents the number of hydrogen atoms in Ar1 to Ar4 of Chemical Formula 3 replaced by deuterium atoms, n is an integer from 0 to 50, "Substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, a halogen group, a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a carbazolyl group and a dibenzofuranyl group, or substituted by a substituent formed by connecting two or more of the above substituents, or having no substituent.

9. The organic light emitting device according to claim 8, wherein: R of the chemical formula 3 11 To R 18 At least 4 of them are deuterium.

10. The organic light emitting device according to claim 8, wherein: The compound represented by the chemical formula 3 is any one selected from the following anthracene derivative compounds having a structure containing deuterium in an anthracene skeleton:

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