KR20210055589A - Organic electroluminescence device and polycyclic compound for organic electroluminescence device - Google Patents

Abstract

The organic electroluminescent device of an embodiment includes a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode. The light emitting layer includes a polycyclic compound represented by the following chemical formula 1 to exhibit improved luminous efficiency with a low driving voltage.

Description

Polycyclic compound for an organic electroluminescent device and an organic electroluminescent device {ORGANIC ELECTROLUMINESCENCE DEVICE AND POLYCYCLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE}

The present invention relates to an organic electroluminescent device and a polycyclic compound used therein.

Recently, as an image display device, an organic electroluminescence display has been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and realizes display by recombining holes and electrons injected from the first electrode and the second electrode in the emission layer to emit light in a light emitting material containing an organic compound in the emission layer. It is a so-called self-luminous display device.

In the application of an organic electroluminescent device to a display device, low driving voltage, high luminous efficiency and long life of the organic electroluminescent device are required, and development of a material for an organic electroluminescent device capable of stably realizing this is continuously required. have.

In particular, recently, in order to implement a high-efficiency organic electroluminescent device, phosphorescence emission using triplet state energy, or delayed fluorescence using a phenomenon in which singlet excitons are generated by collision of triplet excitons (Triplet-triplet annihilation, TTA). Technology for light emission is being developed, and development of a thermally activated delayed fluorescence (TADF) material using a delayed fluorescence phenomenon is in progress.

An object of the present invention is to provide an organic electroluminescent device exhibiting excellent luminous efficiency.

Another object of the present invention is to provide a polycyclic compound for an organic electroluminescent device having high efficiency and long lifespan.

One embodiment provides a polycyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1, X ₁ and X ₂ are each independently NR ₉ , O or S, Y is a hydrogen atom or BR ₁₀ R ₁₁ , a is an integer of 0 or more and 5 or less, and b is 0 or more and 3 or less. Is an integer, and R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or Unsubstituted amine group, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C2-C60 alkenyl group, substituted or unsubstituted C2-C60 alkynyl group, substituted or unsubstituted A substituted or unsubstituted aliphatic heterocyclic group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less ring carbon atoms, or adjacent Groups are bonded to each other to form a ring.

The polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescent light emitting material.

The polycyclic compound represented by Formula 1 may be a blue dopant.

At least one of X ₁ and X ₂ may be _{NR 9.}

Formula 1 may be represented by the following Formula 1-1 or Formula 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, c and d are each independently an integer of 0 or more and 5 or less, e to j are each independently an integer of 0 or more and 4 or less, and R ₁₂ to R ₁₅ and R ₂₁ To R ₂₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group , A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted C1 or more An aliphatic heterocyclic group of 10 or less, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less carbon atoms, or bonded to an adjacent group to form a ring And X ₁ , X ₂ , R ₁ , R ₂ , R ₅ and b are the same as defined in Formula 1 above.

Formula 1-1 may be represented by any one of Formulas 1-1A to 1-1C below.

[Formula 1-1A]

[Formula 1-1B]

[Formula 1-1C]

In Formula 1-1A, R ₁₆ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted Amine group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted An aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or an adjacent group and each other Bond to form a ring, and in Formulas 1-1A to 1-1C, X ₂ , R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are as defined in Formula 1-1 same.

Formula 1-1 may be represented by the following Formula 1-1D.

[Formula 1-1D]

In Formula 1-1D, R ₁₆ and R ₁₇ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted An oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkyne having 2 or more and 60 or less carbon atoms Nyl group, substituted or unsubstituted aliphatic heterocyclic group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms Or, or bonded to each other with an adjacent group to form a ring, and R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are the same as defined in Formula 1-1.

Formula 1-2 may be represented by any one of Formulas 1-2A to 1-2C below.

[Formula 1-2A]

[Formula 1-2B]

[Formula 1-2C]

In Formula 1-2A, R ₂₅ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted Amine group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted An aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or an adjacent group and each other Bond to form a ring, and in Formulas 1-2A to 1-2C, X ₂ , R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the formulas 1-2 It is the same as defined in.

Formula 1-2 may be represented by the following Formula 1-2D.

[Formula 1-2D]

In Formula 1-2D, R ₂₅ and R ₂₆ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted jade. Group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms , Or bonded to each other with adjacent groups to form a ring, and R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as defined in Formula 1-2.

Another embodiment includes a first electrode; A second electrode disposed on the first electrode; And a light emitting layer disposed between the first electrode and the second electrode and including the polycyclic compound of the above-described embodiment. It provides an organic electroluminescent device comprising a.

The emission layer may emit delayed fluorescence.

The emission layer may include a host and a dopant, and the dopant may include the polycyclic compound.

The emission layer may emit light having a central wavelength of 430 nm or more and 470 nm or less.

The organic electroluminescent device of an embodiment may exhibit improved device characteristics with low driving voltage and high efficiency.

The polycyclic compound of one embodiment may be included in the emission layer of the organic electroluminescent device, thereby contributing to high efficiency of the organic electroluminescent device.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
3 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
4 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

In the present invention, various modifications can be made and various forms can be obtained, and specific embodiments will be illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to a specific form disclosed, it should be understood to include all changes, equivalents, and substitutes included in the spirit and scope of the present invention.

In the present specification, when a component (or region, layer, part, etc.) is referred to as “on”, “connected”, or “coupled” to another component, it is placed directly on the other component/ It means that it may be connected/coupled or a third component may be disposed between them.

The same reference numerals refer to the same elements. In addition, in the drawings, thicknesses, ratios, and dimensions of components are exaggerated for effective description of technical content.

"And/or" includes all combinations of one or more that the associated configurations may be defined.

Terms such as first and second may be used to describe various elements, but the elements should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another component. For example, without departing from the scope of the present invention, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element. Singular expressions include plural expressions unless the context clearly indicates otherwise.

In addition, terms such as “below”, “lower”, “above”, and “upper” are used to describe the relationship between the components shown in the drawings. The terms are relative concepts and are described based on the directions indicated in the drawings.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition, terms such as terms defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related technology, and unless interpreted as an ideal or excessively formal meaning, explicitly defined herein. do.

Terms such as "comprise" or "have" are intended to designate the presence of features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, but one or more other features, numbers, or steps. It is to be understood that it does not preclude the possibility of addition or presence of, operations, components, parts, or combinations thereof.

Hereinafter, an organic electroluminescent device according to an embodiment of the present invention and a polycyclic compound of an embodiment included therein will be described with reference to the drawings.

1 to 4 are cross-sectional views schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.

1 to 4, in the organic electroluminescent device 10 of an embodiment, the first electrode EL1 and the second electrode EL2 are disposed to face each other, and the first electrode EL1 and the second electrode The light emitting layer EML may be disposed between the EL2.

In addition, the organic electroluminescent device 10 according to an exemplary embodiment further includes a plurality of functional layers in addition to the emission layer EML between the first electrode EL1 and the second electrode EL2. The plurality of functional layers may include a hole transport region HTR and an electron transport region ETR. That is, in the organic electroluminescent device 10 according to an exemplary embodiment, the first electrode EL1, the hole transport region HTR, the emission layer EML, the electron transport region ETR, and the second electrode are sequentially stacked. EL2) may be included. In addition, the organic electroluminescent device 10 according to an exemplary embodiment may include a capping layer CPL disposed on the second electrode EL2.

The organic electroluminescent device 10 according to an exemplary embodiment may include a polycyclic compound according to an exemplary embodiment described later in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment is not limited thereto, and the organic electroluminescent device 10 of the embodiment includes a hole transport region that is a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2 in addition to the emission layer EML. A polycyclic compound according to an exemplary embodiment described below may be included in the (HTR) or electron transport region (ETR).

Meanwhile, FIG. 2 shows that, compared to FIG. 1, a hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and an electron transport region ETR is an electron injection layer EIL and an electron transport layer. A cross-sectional view of the organic electroluminescent device 10 of an embodiment including (ETL) is shown. In addition, FIG. 3 shows that, compared to FIG. 1, the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR is electron injection. A cross-sectional view of an organic electroluminescent device 10 according to an exemplary embodiment including a layer EIL, an electron transport layer ETL, and a hole blocking layer HBL is shown. 4 is a cross-sectional view of an organic electroluminescent device 10 according to an exemplary embodiment including a capping layer CPL disposed on the second electrode EL2 compared to FIG. 2.

The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode. Also, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium zinc oxide (ITZO). tin zinc oxide). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg) may be included. Alternatively, a plurality of layer structures including a reflective film or a semi-transmissive film formed of the material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. Can be For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 1000 Å to about 10000 Å, for example, about 1000 Å to about 3000 Å.

The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 50 Å to about 1500 Å.

The hole transport region HTR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single layer structure made of a hole injection material and a hole transport material. In addition, the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer (HIL)/hole transport layer (HTL) sequentially stacked from the first electrode EL1, and hole injection. Layer (HIL)/hole transport layer (HTL)/hole buffer layer (not shown), hole injection layer (HIL)/hole buffer layer (not shown), hole transport layer (HTL)/hole buffer layer or hole injection layer (HIL)/hole transport layer It may have a structure of (HTL)/electron blocking layer (EBL), but embodiments are not limited thereto.

The hole transport area (HTR) uses various methods such as vacuum evaporation, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It can be formed by using.

The hole injection layer (HIL) is, for example, a phthalocyanine compound such as copper phthalocyanine, or DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl). -amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA(4,4'4"- Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT/PSS(Poly(3, 4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline/Camphor sulfonicacid), PANI/PSS(Polyaniline/Poly(4-styrenesulfonate)), NPB(N ,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), polyetherketone containing triphenylamine (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate ], HAT-CN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile), etc. may be included.

The hole transport layer (HTL) is, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, TPD(N,N'-bis(3-methylphenyl)-N, Triphenylamine derivatives such as N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), NPB(N ,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4 ,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP(1,3-Bis(N-carbazolyl)benzene), etc. may be further included.

The hole transport region HTR may have a thickness of about 50 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. The thickness of the hole injection layer HIL may be, for example, about 30 Å to about 1000 Å, and the thickness of the hole transport layer HTL may be about 30 Å to about 1000 Å. For example, the electron blocking layer EBL may have a thickness of about 10 Å to about 1000 Å. When the thickness of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) satisfies the above-described range, satisfactory hole transport characteristics without a substantial increase in driving voltage Can be obtained.

In addition to the aforementioned materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane), And metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.

As described above, the hole transport region HTR may further include at least one of a hole buffer layer (not shown) and an electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL. The hole buffer layer (not shown) may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML. As a material included in the hole buffer layer (not shown), a material capable of being included in the hole transport region HTR may be used. The electron blocking layer EBL serves to prevent injection of electrons from the electron transport region ETR to the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have a thickness of, for example, about 100 Å to about 1000 Å or about 100 Å to about 300 Å. The emission layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

In the organic electroluminescent device 10 of one embodiment, the emission layer EML may include the polycyclic compound of one embodiment.

Meanwhile, in the present specification, “substituted or unsubstituted” refers to a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, and a phosphonyl group. It may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a pin oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group and a heterocyclic group. . In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, the biphenyl group may be interpreted as an aryl group, or may be interpreted as a phenyl group substituted with a phenyl group.

In the present specification, "bonding with adjacent groups to form a ring" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring by bonding with an adjacent group. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Hetero rings include aliphatic hetero rings and aromatic hetero rings. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. In addition, a ring formed by bonding to each other may be connected to another ring to form a spiro structure.

In the present specification, “adjacent group” may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, another substituent substituted on an atom where the corresponding substituent is substituted, or a substituent that is three-dimensionally adjacent to the substituent. have. For example, in 1,2-dimethylbenzene, two methyl groups can be interpreted as “adjacent groups”, and in 1,1-diethylcyclopentane, 2 The two ethyl groups can be interpreted as "adjacent groups".

In the present specification, the alkyl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl group is 1 or more and 60 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-oxy Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-trico A group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, etc. are mentioned, It is not limited to these.

In the present specification, an aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 or more and 60 or less, 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of aryl groups include phenyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, quincphenyl group, sexyphenyl group, triphenylenyl group, pyrenyl group, benzofluoranthenyl group , Chrysenyl group, etc. can be illustrated, but the present invention is not limited thereto.

In the present specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as a hetero atom. The number of ring carbon atoms in the aliphatic heterocyclic group may be 1 or more and 30 or less, 1 or more and 20 or less, or 1 or more and 10 or less. Examples of the aliphatic heterocyclic group include an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiane group, a tetrahydropyran group, a 1,4-dioxane group, And the like, but are not limited thereto.

In the present specification, the heteroaryl group may include one or more of B, O, N, P, Si, and S as a hetero atom. When the heteroaryl group contains two or more hetero atoms, the two or more hetero atoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 1 or more and 60 or less, 1 or more and 30 or less, or 1 or more and 20 or less. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl Group, quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, N-aryl carba Sol group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran Group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilol group and a dibenzofuran group, but are not limited thereto.

In the present specification, the silyl group includes an alkyl silyl group and an aryl silyl group. Examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Not limited.

In the present specification, the oxy group may include an alkoxy group and an aryloxy group. The alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less or 1 or more and 10 or less. The number of carbon atoms of the aryloxy group is not particularly limited, but may be, for example, 1 or more and 20 or less or 1 or more and 10 or less. Examples of the oxy group include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc. It is not.

In the present specification, the boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, diphenyl boron group, and phenyl boron group.

In the present specification, the alkenyl group may be linear or branched, or cyclic. The number of carbon atoms is not particularly limited, but is 2 or more and 60 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the alkenyl group include, but are not limited to, a vinyl group, 1-butenyl group, 1-pentenyl group, 1,3-butadienyl aryl group, styrenyl group, and styrylvinyl group.

In the present specification, the alkynyl group may be linear, branched or cyclic. The number of carbon atoms is not particularly limited, but is 2 or more and 60 or less, 2 or more and 30 or less, or 2 or more and 20 or less. Examples of the alkynyl group include, but are not limited to, an ethynyl group, 1-propynyl group, 2-butynyl group, and 2-pentynyl group.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include an alkyl amine group and an aryl amine group. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, and a triphenylamine group.

In the present specification, direct linkage may mean a single bond.

The polycyclic compound of one embodiment included in the organic electroluminescent device 10 of one embodiment may be represented by Formula 1 below.

[Formula 1]

In Formula 1, X ₁ and X ₂ may each independently be NR ₉ , O or S. In Formula 1, Y may be a hydrogen atom or BR ₁₀ R ₁₁ .

In Formula 1, a may be an integer of 0 or more and 5 or less, and b may be an integer of 0 or more and 3 or less. When a is an integer of 2 or more, a plurality of R ₃ may be the same as or different from each other. When b is an integer of 2 or more, a plurality of R ₅ may be the same as or different from each other.

In Formula 1, R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted Or an unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or An unsubstituted aliphatic heterocyclic group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less ring carbon atoms, or adjacent It can combine with each other to form a ring.

For example, in Formula 1, R ₆ and R ₆ and adjacent R ₇ or R ₆ and R ₆ and adjacent R ₈ may be bonded to each other to form an azaborine group. In addition, it is possible to form a group when Y is BR ₁₀ R _11, R ₄ and R _4, R ₁₀ or R ₄ and R ₁₁ are R-aza borin bonded to each other adjacent to the ₄ adjacent in the formula (I). However, the embodiment is not limited thereto.

The polycyclic compound of an embodiment may include a plurality of B (boron) and N (nitrogen), and include an ether group and a hetero atom connected thereto. The hetero atom may be a nitrogen atom, an oxygen atom, or a sulfur atom. The polycyclic compound of one embodiment may include 2 to 3 B, 2 to 3 N, and an ether group, and at least 6 rings may be condensed. The polycyclic compound of one embodiment may be used as a light emitting material that emits blue light in a wavelength range of 470 nm or less. For example, the polycyclic compound of the exemplary embodiment represented by Formula 1 may be a light-emitting material having an emission center wavelength in a wavelength region of 430 nm or more and 470 nm or less.

The polycyclic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2 below.

[Formula 1-1]

[Formula 1-2]

Formula 1-1 shows a case where Y is a hydrogen atom and includes 2 B, and Formula 1-2 shows a case where Y is B and includes 3 B. In addition, Formula 1-2 shows that while Y is B, it is bonded to an adjacent group to form a ring.

In Formulas 1-1 and 1-2, the same contents as described in Formula 1 may be applied to _{X 1} , X ₂ , R ₁ , R ₂ , R _{5 and b.} In Formulas 1-1 and 1-2, at least one of _{X 1} and X ₂ may be _{NR 9.} When X ₁ includes N, X ₂ may be O or S. For example, when X ₁ is NR ₉ , X ₂ may be O. However, the embodiment is not limited thereto.

In Formulas 1-1 and 1-2, c and d may each independently be an integer of 0 or more and 5 or less, and e to j may each independently be an integer of 0 or more and 4 or less. For example, when c is an integer of 2 or more, a plurality of R ₁₂ may be the same or different from each other. When e is an integer of 2 or more, a plurality of R ₁₄ may be the same as or different from each other.

In Formulas 1-1 and 1-2, R ₁₂ to R ₁₅ and R ₂₁ to R ₂₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Boron group, substituted or unsubstituted oxy group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted aliphatic heterocyclic group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms, and a substituted or unsubstituted ring formation It is a heteroaryl group having 1 or more and 60 or less carbon atoms, or may be bonded to each other with adjacent groups to form a ring.

In one embodiment, Formula 1-1 may be represented by any one of Formulas 1-1A to 1-1C below.

[Formula 1-1A]

[Formula 1-1B]

[Formula 1-1C]

Formula 1-1A shows a case where X ₁ is NR ₁₆ , 1-1B shows a case where X ₁ is O, and 1-1C shows a case where X ₁ is S.

In Formulas 1-1A to 1-1C, the same contents as described in Formula 1 may be applied to _{X 2} , R ₁ , R ₂ , R ₅ , R ₁₂ to R _{15, and b to f.}

In Formula 1-1A, R ₁₆ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less cyclic carbon atoms, or are bonded to each other with adjacent groups To form a ring.

In addition, Formula 1-1 may be represented by the following Formula 1-1D.

[Formula 1-1D]

Formula 1-1D shows the case where X ₁ and X ₂ are NR ₁₆ and NR ₁₇ , respectively. _{R 16} and R ₁₇ connected to each N may be the same as each other or different from each other. For example, R ₁₆ and R ₁₇ may be the same as a phenyl group. However, the embodiment is not limited thereto.

In Formula 1-1D, the same contents as described in Formula 1-1 may be applied to _{R 1} , R ₂ , R ₅ , R ₁₂ to R _{15, and b to f.}

R ₁₆ and R ₁₇ is each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group , A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted C1 or more An aliphatic heterocyclic group of 10 or less, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less carbon atoms, or bonded to an adjacent group to form a ring Can be formed.

Meanwhile, Formula 1-2 may be represented by any one of Formulas 1-2A to 1-2C below.

[Formula 1-2A]

[Formula 1-2B]

[Formula 1-2C]

Formula 1-2A shows a case where X ₁ is NR ₂₅ , Formula 1-2B shows a case where X ₁ is O, and Formula 1-2C shows a case where X ₁ is S.

In Formulas 1-2A to 1-2C, X ₂ , R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as those described in Formula 1-2 above. I can.

In Formula 1-2A, R ₂₅ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less cyclic carbon atoms, or are bonded to each other with adjacent groups To form a ring.

In addition, Formula 1-2 may be represented by the following Formula 1-2D.

[Formula 1-2D]

Formula 1-2D shows the case where X ₁ and X ₂ are NR ₂₅ and NR ₂₆ , respectively. _{R 25} and R ₂₆ linked to each N may be the same as each other or different from each other. For example, R ₂₅ and R ₂₆ may be the same as a phenyl group. In addition, it may have a structure in which the left and right of Formula 1-2D are symmetrical around the O of the ether group. However, the embodiment is not limited thereto.

In Formula 1-2D, the same contents as described in Formula 1-2 may be applied to _{R 1} , R ₂ , R ₅ , R ₂₁ to R _{24, b and g to j.}

R ₂₅ and R ₂₆ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted Amine group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted An aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or an adjacent group and each other Can be combined to form a ring.

The polycyclic compound of one embodiment may include an ether group and a hetero atom connected to 3 to 4 azaborine groups and azaborine groups. For example, the polycyclic compound of an embodiment may have a structure in which two nitrogen atoms are connected to a phenyl group based on an ether group, and 10 aromatic rings are condensed. The 10 condensed rings may contain 3 azaborin groups. However, the embodiment is not limited thereto.

The polycyclic compound of an embodiment may be any one of the compounds shown in Compound Group 1 below. The organic electroluminescent device 10 according to an exemplary embodiment may include at least one polycyclic compound among polycyclic compounds indicated in compound group 1 in the emission layer EML.

[Compound group 1]

The polycyclic compound of an embodiment may be a thermally activated delayed fluorescent light emitting material. The organic electroluminescent device 10 according to an embodiment may exhibit high-efficiency device characteristics by including the polycyclic compound of the embodiment described above in the emission layer (EML).

The polycyclic compound of the exemplary embodiment represented by Formula 1 may be a blue thermally active delayed fluorescent dopant.

In the organic electroluminescent device 10 according to an exemplary embodiment, the emission layer EML may emit delayed fluorescence. For example, the emission layer EML may emit light of thermally activated delayed fluorescence (TADF).

Meanwhile, although not shown in the drawings, the organic electroluminescent device 10 according to an exemplary embodiment may include a plurality of emission layers. A plurality of emission layers may be sequentially stacked and provided, and for example, the organic electroluminescent device 10 including a plurality of emission layers may emit white light. When the organic electroluminescent device 10 includes a plurality of emission layers, at least one emission layer EML may include the polycyclic compound of the above-described exemplary embodiment.

In one embodiment, the emission layer EML includes a host and a dopant, and may include the above-described polycyclic compound as a dopant. For example, in the organic electroluminescent device 10 of an embodiment, the emission layer (EML) may include a host for delayed fluorescence emission and a dopant for delayed fluorescence emission, and the polycyclic compound described above may be included as a dopant for delayed fluorescence emission. I can. The emission layer EML may include at least one of the polycyclic compounds shown in compound group 1 as a thermally activated delayed fluorescent dopant.

In an embodiment, the emission layer EML may be a thermally active delayed fluorescent emission layer, and the emission layer EML may include a known host material and the above-described polycyclic compound. For example, in one embodiment, the polycyclic compound may be used as a TADF dopant.

Meanwhile, in an embodiment, the emission layer EML may include a known host material. For example, in one embodiment, the light emitting layer (EML) is a host material, Alq ₃ (tris(8-hydroxyquinolino)aluminum), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl) , PVK(poly(n-vinylcabazole), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN(2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO (bis[2- (diphenylphosphino)phenyl] ether oxide), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO ₃ (Hexaphenylcyclotrisiloxane), DPSiO ₄ (Octaphenylcyclotetra siloxane), or PPF (2,8-Bis( diphenylphosphoryl)dibenzofuran), mCBP(3,3'-bis(N-carbazolyl)-1,1'-biphenyl), mCP(1,3-Bis( N- carbazolyl)benzene), etc. However, The embodiment is not limited thereto, and a known delayed fluorescent light emitting host material may be included in addition to the host material provided.

Meanwhile, in the organic electroluminescent device 10 according to an exemplary embodiment, the emission layer EML may further include a known dopant material. In one embodiment, the emission layer (EML) is a styryl derivative (eg, 1, 4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino) -4'-[(di-p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2- yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi), perylene and its derivatives (e.g. 2, 5, 8, 11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g. For example, 1, 1-dipyrene, 1, 4-dipyrenylbenzene, 1, 4-Bis (N, N-Diphenylamino) pyrene)) may be included.

Referring back to FIGS. 1 to 4, in the organic electroluminescent device 10 according to an exemplary embodiment, the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but embodiments are not limited thereto.

The electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure made of an electron injection material and an electron transport material. In addition, the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL) and a hole blocking layer (EIL) sequentially stacked from the light emitting layer EML. HBL)/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å to about 1500 Å.

The electron transport area (ETR) is a vacuum evaporation method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser induced thermal imaging (LITI), and various methods. It can be formed by using.

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include an anthracene compound. However, the present invention is not limited thereto, and the electron transport region is, for example, Alq ₃ (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9, 10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP(2,9-Dimethyl-4,7-diphenyl-1,10 -phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ( 4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1 ,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq ₂ (berylliumbis(benzoquinolin-10-olate) ), ADN (9,10-di (naphthalene-2-yl) anthracene), and a mixture thereof The thickness of the electron transport layers (ETLs) is about 100 Å to about 1000 Å, for example, about 150 Å to about It may be 500 Å When the thickness of the electron transport layers (ETLs) satisfies the above-described range, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

When the electron transport region (ETR) includes the electron injection layer (EIL), the electron transport region (ETR) is a halogenated metal such as LiF, NaCl, CsF, RbCl, and RbI, a lanthanum group metal such as Yb, Li ₂ O, A metal oxide such as BaO or LiQ (Lithium quinolate) may be used, but is not limited thereto. The electron injection layer EIL may also be formed of a material in which an electron transport material and an insulating organo metal salt are mixed. The organometallic salt may be a material having an energy band gap of approximately 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. I can. The electron injection layers EIL may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layers EIL satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

As mentioned above, the electron transport region ETR may include a hole blocking layer HBL. Hole blocking layer (HBL), for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline) It may include, but is not limited thereto.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium zinc oxide (ITZO). tin zinc oxide).

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture containing them (eg, a mixture of Ag and Mg) may be included. Alternatively, a plurality of layer structures including a reflective film or a semi-transmissive film formed of the material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. Can be

Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

Meanwhile, a capping layer CPL may be further disposed on the second electrode EL2 of the organic electroluminescent device 10 according to an exemplary embodiment. The capping layer (CPL) is, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra (biphenyl-4-yl) biphenyl-4, 4'-diamine), TCTA(4,4',4"-Tris (carbazol sol-9-yl) triphenylamine), N, N'-bis (naphthalen-1-yl), and the like.

The organic electroluminescent device 10 according to the embodiment includes the polycyclic compound of the above-described embodiment in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2 to exhibit excellent luminous efficiency. I can. In addition, the compound according to an exemplary embodiment may be a thermally activated delayed fluorescent dopant, and the emission layer (EML) includes the compound of an exemplary embodiment to emit thermally activated delayed fluorescence, thereby exhibiting good luminous efficiency characteristics.

Meanwhile, the compound of the above-described exemplary embodiment may be included as a material for the organic electroluminescent device 10 in an organic layer other than the emission layer EML. For example, the organic electroluminescent device 10 according to an embodiment of the present invention may include the above-described compound in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. have.

Hereinafter, a compound according to an exemplary embodiment of the present invention and an organic electroluminescent device according to an exemplary embodiment will be described in detail with reference to Examples and Comparative Examples. In addition, the examples shown below are examples for aiding understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

1. Synthesis of polycyclic compound of one embodiment

First, the method for synthesizing the polycyclic compound according to the present embodiment will be described in detail by exemplifying the method for synthesizing compounds 1 and 31. In addition, the synthesis method of the polycyclic compound described below is an example, and the synthesis method of the compound according to the embodiment of the present invention is not limited to the following examples.

(1) Synthesis of compound 1

(Synthesis of Intermediate I-1)

3,5-DiBromo-phenol (1 equivalent), Diphenylamine (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), Tri-tert-butylphosphine (0.1 equivalent), Sodium tert-butoxide (1.5 equivalent) to toluene After melting, the mixture was stirred at 80 degrees Celsius for 12 hours. After cooling, the resulting organic layer was washed with ethyl acetate and water three times, separated, and then dried over MgSO ₄ and dried under reduced pressure. Intermediate I-1 was obtained by purification by column chromatography with methylene chloride and hexane (n-hexane). (Yield: 62%)

(Synthesis of Intermediate I-2)

Intermediate I-1 (1 equivalent), N ¹ ,N ³ -diphenylbenzene-1,3-diamine (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), Tri-tert-butylphosphine (0.1 equivalent), Sodium tert After dissolving -butoxide (3 equivalents) in toluene, the mixture was stirred at 80 degrees Celsius for 12 hours. After cooling, the resulting organic layer was washed with ethyl acetate and water three times, separated, and then dried over MgSO ₄ and dried under reduced pressure. Intermediate I-2 was obtained by purification by column chromatography with methylene chloride and hexane (n-hexane). (Yield: 56%)

(Synthesis of Intermediate I-3)

Intermediate I-2 (1 equivalent), 3,5-dibromo-N,N-diphenylaniline (1 equivalent), Pd ₂ (dba) ₃ (0.1 equivalent), Tri-tert-butylphosphine (0.2 equivalent), Sodium tert-butoxide After dissolving (3 equivalents) in o-Xylene, the mixture was stirred at 130 degrees Celsius for 12 hours. After cooling, the resulting organic layer was washed with ethyl acetate and water three times, separated, and then dried over MgSO ₄ and dried under reduced pressure. Intermediate I-3 was obtained by purification by column chromatography with methylene chloride and hexane (n-hexane). (Yield: 52%)

(Synthesis of Intermediate I-4)

Intermediate I-3 (1 equivalent), CuI (0.1 equivalent), K ₂ CO ₃ (3 equivalent) was dissolved in dimethylformamide (DMF) and stirred at 150 degrees Celsius for 24 hours. After cooling, the reactant was poured into water, precipitated, and filtered. The obtained solid was washed three times with ethyl acetate and water, separated, and the obtained organic layer _{was dried over MgSO 4 and} then dried under reduced pressure. Intermediate I-4 was obtained by purification by column chromatography with methylene chloride and hexane (n-hexane). (Yield: 13%)

(Synthesis of compound 1)

Intermediate I-4 (1 equivalent) was dissolved in o-dichlorobenzene, cooled to 0 degrees Celsius, and then BI ₃ (2 equivalents) was slowly injected in a nitrogen atmosphere. After the dropping was completed, the temperature was raised to 150 degrees Celsius and stirred for 24 hours. After cooling, the reaction was terminated by slowly dropping trimethylamine into the flask containing the reactant, and then ethyl alcohol was added to the reactant, precipitated, and filtered to obtain a reactant. The obtained solid was purified by column chromatography with methylene chloride and hexane (n-hexane), and then compound 1 was obtained by recrystallization using toluene and acetone. (Yield: 5%) The resulting compound was confirmed through MS/FAB. (C ₅₄ H ₃₄ B ₂ N ₄ O cal.776.29, found 776.30)

(2) Synthesis of compound 31

Intermediate I-4 (1 equivalent) was dissolved in o-dichlorobenzene, cooled to 0 degrees Celsius, and then BI ₃ (3 equivalent) was slowly injected in a nitrogen atmosphere. After completion of the dropping, the temperature was raised to 180 degrees Celsius and stirred for 24 hours. After cooling, triethylamine was slowly dropped into the flask containing the reactant to terminate the reaction, and ethyl alcohol was added to the reactant to precipitate and filter to obtain a reactant. The obtained solid was purified by column chromatography with methylene chloride and hexane (n-hexane), and then compound 1 was obtained by recrystallization using toluene and acetone. (Yield: 2%) The resulting compound was confirmed through MS/FAB. (C ₅₄ H ₃₁ B ₃ N ₄ O cal.784.28, found 784.29)

2. Fabrication and evaluation of organic electroluminescent devices containing polycyclic compounds

The organic electroluminescent device of an example including the polycyclic compound of an example in the emission layer was manufactured by the following method. The organic electroluminescent devices of Examples 1 and 2 were manufactured using the polycyclic compounds of Compound 1 and Compound 31 as a dopant material for the emission layer.

Comparative Example 1 corresponds to an organic electroluminescent device manufactured by using Comparative Example Compound C1 as a dopant material for a light emitting layer in place of the Example compounds.

The compounds used in Example 1, Example 2, and Comparative Example 1 are shown in Table 1.

Compound 1

Compound 31

Comparative example
Compound C1

Comparative example
Compound C2

(Production of organic electroluminescent device)

After patterning ITO having a thickness of 1200 Å on a glass substrate, it was washed with ultrapure water, washed with ultrasonic waves, and irradiated with UV for 30 minutes, followed by ozone treatment. Thereafter, NPD was deposited to a thickness of 300 Å to form a hole injection layer, and TCTA was deposited to a thickness of 200 Å to form a hole transport layer. CzSi was deposited to a thickness of 100 Å as a hole transport layer compound.

Next, a light emitting layer was formed with a thickness of 200 Å by co-depositing a polycyclic compound of an embodiment or a comparative compound and DPEPO at a ratio of 10:90. That is, the light emitting layer formed by co-deposition was deposited by mixing Compounds 1 and 31 with DPEPO in Examples 1 and 2, respectively, and in Comparative Example 1, Compound C1 of Comparative Example was mixed and deposited with DPEPO. Subsequently, a layer having a thickness of 300 Å was formed with TPBi on the emission layer, and a layer having a thickness of 10 Å was formed with LiF to form an electron transport region. Next, a second electrode having a thickness of 3000 Å was formed of aluminum (Al).

In Examples, the hole transport region, the light emitting layer, the electron transport region, and the second electrode were formed using a vacuum evaporation apparatus.

(Evaluation of organic electroluminescent device)

Table 2 shows the evaluation results of the organic electroluminescent device for Example 1, Example 2, and Comparative Example 1. In Table 2, the driving voltage and luminous efficiency of the fabricated organic electroluminescent device are compared and shown. In the characteristic evaluation results for the Examples and Comparative Examples shown in Table 2, the luminous efficiency indicates a current efficiency value for a current ^{density of 10 mA/cm 2.}

Element creation example Emitting layer dopant material Driving voltage (V) Luminous efficiency (cd/A) Luminous color Example 1 Compound 1 4.45 20.3 blue Example 2 Compound 31 4.53 22.5 blue Comparative Example 1 Comparative Example Compound C1 6.7 15.7 blue Comparative Example 2 Comparative Example Compound C2 5.20 16.1 green

Referring to the results of Table 2, it can be seen that the examples of the organic electroluminescent device using the polycyclic compound of the embodiment as a material for the emission layer exhibit high luminous efficiency with a lower driving voltage than that of the comparative example. Since Examples 1 and 2 exhibit higher luminous efficiency than Comparative Example 1, it can be seen that the polycyclic compounds of the Examples emit thermally active delayed fluorescence emission.

Comparative Example 1 contains TXO-TPA, a known fluorescent light-emitting dopant material, in the light-emitting layer. It can be seen that Comparative Example 2 emits a green wavelength, unlike Examples 1, 2, and 1. Comparative Example Compound C2, unlike Compound 1 and Compound 31 of the present invention, does not contain an oxygen atom at the B and para positions. Accordingly, it is determined that the emission wavelength of the compound C2 of Comparative Example 2 is shifted to a long wavelength, and it is difficult to be used as a blue light emitting material.

The polycyclic compound of an embodiment is a structure in which B (boron) is substituted on an aromatic ring containing an ether group, and a plurality of unsubstituted or substituted aromatic rings adjacent thereto and substituted or unsubstituted with a hetero atom (N, O, or S) are connected. As such, it is applied to the organic electroluminescent device according to an exemplary embodiment and can exhibit excellent luminous efficiency with a low driving voltage.

Although the above has been described with reference to the preferred embodiments of the present invention, those skilled in the art or those of ordinary skill in the relevant technical field will not depart from the spirit and scope of the present invention described in the claims to be described later. It will be appreciated that various modifications and changes can be made to the present invention within the scope of the invention.

Therefore, the technical scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be determined by the claims.

10: organic electroluminescent element EL1: first electrode
EL2: second electrode HTR: hole transport region
EML: light emitting layer ETR: electron transport region

Claims (20)

A first electrode;
A second electrode disposed on the first electrode; And
A light emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by the following formula (1); Organic electroluminescent device comprising:
[Formula 1]

In Formula 1 above
X ₁ and X ₂ are each independently NR ₉ , O or S,
Y is a hydrogen atom or BR ₁₀ R ₁₁ ,
a is an integer of 0 or more and 5 or less,
b is an integer of 0 or more and 3 or less,
R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less cyclic carbon atoms, or are bonded to each other with adjacent groups To form a ring. The method of claim 1,
The emission layer is an organic electroluminescent device that emits delayed fluorescence. The method of claim 1,
The emission layer includes a host and a dopant,
The dopant is an organic electroluminescent device comprising a polycyclic compound represented by Formula 1. The method of claim 1,
The emission layer is an organic electroluminescent device that emits light having a center wavelength of 430 nm or more and 470 nm or less. The method of claim 1,
Formula 1 is an organic electroluminescent device represented by Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
c and d are each independently an integer of 0 or more and 5 or less,
e to j are each independently an integer of 0 or more and 4 or less,
R ₁₂ to R ₁₅ and R ₂₁ to R ₂₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group , A substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, A substituted or unsubstituted aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less cyclic carbon atoms, Or combine with adjacent groups to form a ring,
X ₁ , X ₂ , R ₁ , R ₂ , R ₅ and b are the same as defined in Formula 1 above. The method of claim 5,
Formula 1-1 is an organic electroluminescent device represented by any one of the following Formulas 1-1A to 1-1C:
[Formula 1-1A]

[Formula 1-1B]

[Formula 1-1C]

In Formula 1-1A,
R ₁₆ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, and a substituted or unsubstituted aliphatic having 1 or more and 10 or less carbon atoms. A heterocyclic group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or bonded to an adjacent group to form a ring,
In Formula 1-1A to Formula 1-1C,
X ₂ , R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are the same as defined in Formula 1-1. The method of claim 5,
Formula 1-1 is an organic electroluminescent device represented by the following Formula 1-1D:
[Formula 1-1D]

In Formula 1-1D,
R ₁₆ and R ₁₇ is each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group , A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted C1 or more An aliphatic heterocyclic group of 10 or less, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less carbon atoms, or bonded to an adjacent group to form a ring To form,
R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are the same as defined in Formula 1-1. The method of claim 5,
Formula 1-2 is an organic electroluminescent device represented by any one of the following Formulas 1-2A to 1-2C:
[Formula 1-2A]

[Formula 1-2B]

[Formula 1-2C]

In Formula 1-2A,
R ₂₅ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, and a substituted or unsubstituted aliphatic having 1 or more and 10 or less carbon atoms. A heterocyclic group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or bonded to an adjacent group to form a ring,
In Formula 1-2A to Formula 1-2C,
X ₂ , R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as defined in Formula 1-2. The method of claim 5,
Formula 1-2 is an organic electroluminescent device represented by the following Formula 1-2D:
[Formula 1-2D]

In Formula 1-2D,
R ₂₅ and R ₂₆ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less cyclic carbon atoms, or are bonded to each other with adjacent groups To form a ring,
R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as defined in Formula 1-2. The method of claim 1,
The polycyclic compound is an organic electroluminescent device comprising at least one of the compounds of the following compound group 1:
[Compound group 1]

. Polycyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ and X ₂ are each independently NR ₉ , O or S,
Y is a hydrogen atom or BR ₁₀ R ₁₁ ,
a is an integer of 0 or more and 5 or less,
b is an integer of 0 or more and 3 or less,
R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less cyclic carbon atoms, or are bonded to each other with adjacent groups To form a ring. The method of claim 11,
The polycyclic compound represented by Formula 1 is a polycyclic compound of a thermally activated delayed fluorescent light-emitting material. The method of claim 11,
The polycyclic compound represented by Formula 1 is a blue dopant. The method of claim 11,
At least one of X ₁ and X _{2 is NR 9} . The method of claim 11,
Formula 1 is a polycyclic compound represented by Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formula 1-1 and Formula 1-2,
c and d are integers of 0 or more and 5 or less,
e to j are integers of 0 or more and 4 or less,
R ₁₂ to R ₁₅ and R ₂₁ to R ₂₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group , A substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, A substituted or unsubstituted aliphatic heterocyclic group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less cyclic carbon atoms, Or combine with adjacent groups to form a ring,
X ₁ , X ₂ , R ₁ , R ₂ , R ₅ and b are the same as defined in Formula 1 above. The method of claim 15,
Formula 1-1 is a polycyclic compound represented by any one of the following Formulas 1-1A to 1-1C:
[Formula 1-1A]

[Formula 1-1B]

[Formula 1-1C]

In Formula 1-1A,
R ₁₆ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, and a substituted or unsubstituted aliphatic having 1 or more and 10 or less carbon atoms. A heterocyclic group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or bonded to an adjacent group to form a ring,
In Formula 1-1A to Formula 1-1C,
X ₂ , R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are the same as defined in Formula 1-1. The method of claim 15,
Formula 1-1 is a polycyclic compound represented by the following Formula 1-1D:
[Formula 1-1D]

In Formula 1-1D,
R ₁₆ and R ₁₇ is each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group , A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted C1 or more An aliphatic heterocyclic group of 10 or less, a substituted or unsubstituted aryl group having 6 or more and 60 or less carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 1 or more and 60 or less carbon atoms, or bonded to an adjacent group to form a ring To form,
R ₁ , R ₂ , R ₅ , R ₁₂ to R ₁₅ , and b to f are the same as defined in Formula 1-1. The method of claim 15,
Formula 1-2 is a polycyclic compound represented by any one of the following Formulas 1-2A to 1-2C:
[Formula 1-2A]

[Formula 1-2B]

[Formula 1-2C]

In Formula 1-2A,
R ₂₅ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 or more and 60 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted alkynyl group having 2 or more and 60 or less carbon atoms, a substituted or unsubstituted aliphatic having 1 or more and 10 or less carbon atoms A heterocyclic group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, or bonded to an adjacent group to form a ring,
In Formula 1-2A to Formula 1-2C,
X ₂ , R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as defined in Formula 1-2. The method of claim 15,
Formula 1-2 is a polycyclic compound represented by the following Formula 1-2D:
[Formula 1-2D]

In Formula 1-2D,
R ₂₅ and R ₂₆ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted An amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 or more and 10 or less aliphatic heterocyclic groups, substituted or unsubstituted aryl groups having 6 or more and 60 or less ring carbon atoms, substituted or unsubstituted heteroaryl groups having 1 or more and 60 or less ring carbon atoms, or are bonded to each other with adjacent groups To form a ring,
R ₁ , R ₂ , R ₅ , R ₂₁ to R ₂₄ , b and g to j are the same as defined in Formula 1-2. The method of claim 11,
Formula 1 is a polycyclic compound of any one of the compounds represented in the following compound group 1:
[Compound group 1]

.

Images