Organic electroluminescence device and fused polycyclic compound for use thereof

Abstract

Provided are an organic electroluminescent device and a fused polycyclic compound for an organic electroluminescent device. The organic electroluminescent device includes a first electrode and a second electrode facing each other and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the plurality of organic layers includes a fused polycyclic compound represented by Formula 1, and the organic electroluminescent device exhibits improved luminous efficiency. Formula 1

Description

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2020-0039162, filed on March 31, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more aspects of embodiments of this disclosure relate to an organic electroluminescent device and a fused polycyclic compound for the organic electroluminescent device, such as a fused polycyclic compound used as a luminescent material and an organic electroluminescent device comprising the fused polycyclic compound. Background Technology

[0003] Organic electroluminescent displays (OLEDs) are being developed as image display devices. Unlike liquid crystal displays (LCDs), OLEDs are a type of self-emissive display device in which holes and electrons injected from a first electrode and a second electrode recombine in an emitting layer, and luminescent organic compounds in the emitting layer emit light to achieve the display.

[0004] Display device applications require organic electroluminescent devices with low driving voltage, high luminous efficiency, and / or long lifespan, and new materials that can stably obtain these properties in organic electroluminescent devices are desired.

[0005] In recent years, in order to realize efficient organic electroluminescent devices, technologies related to phosphorescence emission (utilizing triplet energy) and / or delayed fluorescence emission (utilizing the generation of singlet excitons through triplet exciton collisions (triplet-triplet annihilation, TTA)) are being developed, and materials for thermally activated delayed fluorescence (TADF) are being developed. Summary of the Invention

[0006] One or more aspects of embodiments of this disclosure relate to an organic electroluminescent device having improved luminous efficiency.

[0007] One or more aspects of embodiments of this disclosure relate to a fused polycyclic compound that can improve the luminous efficiency of organic electroluminescent devices.

[0008] One or more exemplary embodiments of this disclosure provide an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, and a plurality of organic layers between the first electrode and the second electrode. At least one of the plurality of organic layers comprises a fused polycyclic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In Equation 1, R1 to R 12 Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R1 to R 12 It can combine with adjacent groups to form a ring; and two or more pairs of adjacent R1 to R 12 All groups are fused with the substituents represented by Formula 2:

[0012] Formula 2

[0013]

[0014] In Equation 2, -* represents the two or more pairs of adjacent R1 to R2 in Equation 1. 12 The positions of a pair of fused groups; X1 and X2 can each be independently NAr1, O, or S; Ar1 ​​can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, Ar1 can combine with an adjacent group to form a ring; R a and R b Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R a and R b It can combine with adjacent groups to form a ring; n1 can be an integer from 0 to 4; and n2 can be an integer from 0 to 3. For example, two or more substituents represented by Formula 2 can be fused with Formula 1.

[0015] In an embodiment, the plurality of organic layers may include a hole transport region on the first electrode, an emitter layer on the hole transport region, and an electron transport region on the emitter layer. The emitter layer may include a fused polycyclic compound.

[0016] In one embodiment, the emitting layer can emit delayed fluorescence.

[0017] In an embodiment, the emission layer may be a delayed fluorescence emission layer comprising a host and a dopant, and the dopant may be (or include) a fused polycyclic compound.

[0018] In the embodiments, two or three substituents represented by Formula 2 may be fused with a fused polycyclic compound represented by Formula 1, and the two or three fused substituents represented by Formula 2 may be identical to each other.

[0019] In the embodiments, the substituent represented by Formula 2 can be represented by any one of Formulas 2-1 to 2-8:

[0020] Equation 2-1

[0021]

[0022] Equation 2-2

[0023]

[0024] Equation 2-3

[0025]

[0026] Equation 2-4

[0027]

[0028] Formula 2-5

[0029]

[0030] Formula 2-6

[0031]

[0032] Formula 2-7

[0033]

[0034] Formula 2-8

[0035]

[0036] In equations 2-1 to 2-8, Ar 11 and Ar 12 Each group can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, Ar 11 and Ar 12 It can combine with adjacent groups to form a ring. R a and R b And n1 and n2 can both be independently the same as those defined in Equation 2.

[0037] In the embodiments, the substituent represented by Formula 2 can be represented by Formula 2-a:

[0038] Equation 2-a

[0039]

[0040] In equation 2-a, X1 and X2, as well as R a and R b They can all be independently identical to those defined in Equation 2.

[0041] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by any one of Formulas 3-1 to 3-5:

[0042] Equation 3-1

[0043]

[0044] Equation 3-2

[0045]

[0046] Equation 3-3

[0047]

[0048] Equation 3-4

[0049]

[0050] Formula 3-5

[0051]

[0052] In Formulas 3-1 to 3-5, A1 to A8 can each be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Optionally, A1 to A8 can be combined with adjacent groups to form a ring. B1 and B2, B3 and B4, and B5 and B6 can all be fused with the substituents represented by Formula 2.

[0053] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by any one of Formulas 4-1 to 4-8:

[0054] Equation 4-1

[0055]

[0056] Equation 4-2

[0057]

[0058] Equation 4-3

[0059]

[0060] Equation 4-4

[0061]

[0062] Equation 4-5

[0063]

[0064] Equation 4-6

[0065]

[0066] Equation 4-7

[0067]

[0068] Equation 4-8

[0069]

[0070] In equations 4-1 to 4-8, X 11 X 12 X 13 X 21 X 22 and X 23 They can all be independently NAr1, O, or S; R a1 R a2 R a3 R b1 R b2 and R b3 Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R a1 R a2 R a3 R b1 R b2 and R b3 It can combine with adjacent groups to form a ring; n 11 n 12 and n 13 Each can be an independent integer from 0 to 4; n 21 n 22 and n 23 They can all be independent integers from 0 to 3; Ar1 ​​and A1 to A8 can all be independent and the same as those defined in Equations 2 and 3-1 to 3-5.

[0071] In the embodiment, Ra and R b (and for example R) a1 R a2 R a3 R b1 R b2 and R b3 Each of these can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0072] In the embodiment, R1 to R 12 Each of these can be a hydrogen atom, a deuterium atom, or a position fused with a substituent represented by Formula 2, independently.

[0073] In some embodiments, the organic electroluminescent device may further include a capping layer located on the second electrode and having a refractive index of 1.6 or greater.

[0074] In the organic electroluminescent device according to embodiments of the present disclosure, the first electrode and the second electrode may each independently comprise any one, two or more compounds of silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF, molybdenum (Mo), titanium (Ti), indium (In), zinc (Zn), tin (Sn), and ytterbium (Yb), a mixture of two or more of them, or at least an oxide thereof.

[0075] The fused polycyclic compounds according to embodiments of this disclosure can be represented by Formula 1. Attached Figure Description

[0076] The accompanying drawings are included to provide a further understanding of this disclosure and are incorporated in and constitute a part of this specification. The drawings illustrate exemplary embodiments of this disclosure and, together with the description, serve to explain the principles of this disclosure. In the drawings:

[0077] Figure 1 This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure;

[0078] Figure 2 This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure;

[0079] Figure 3 This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure; and

[0080] Figure 4This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure. Detailed Implementation

[0081] The foregoing, other objects, features, and advantages of this disclosure will be readily understood through exemplary embodiments with reference to the accompanying drawings. However, this disclosure may be implemented in various forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of this disclosure to those skilled in the art.

[0082] When interpreting each drawing, the same reference numerals are used to denote the same elements, and their repeated descriptions may be omitted. In the drawings, the dimensions and sizes of elements may be exaggerated for clarity. It will be understood that although the terms "first," "second," etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of this disclosure, a first element may alternatively be referred to as a second element, and similarly, a second element may alternatively be referred to as a first element. Unless the context clearly indicates otherwise, the singular form includes the plural form, and vice versa.

[0083] In this specification, it will be understood that the terms "comprising," "including," and / or "having," and variations thereof, indicate the presence of features, fixed quantities, steps, processes, elements, components, or combinations thereof disclosed in the specification, but do not preclude the presence or addition of one or more other features, quantities, steps, processes, elements, or components. It will also be understood that when a layer, film, region, or plate is referred to as being "on (below)" another layer, film, region, or plate, the layer, film, region, or plate may be directly on or below the other layer, film, region, or plate, or intermediate layers, intermediate films, intermediate regions, or intermediate plates may also be present. When an element is referred to as being "directly on," "directly connected to," or "directly bonded to" another element, no intermediate element is present.

[0084] As used herein, when expressions such as “at least one of…”, “one of…”, and “selected from…” follow (or are chosen from…) a list of elements, they modify the entire list of elements without modifying any individual elements within that list. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Furthermore, when describing embodiments of this disclosure, “may” is used to mean “one or more embodiments of this disclosure”.

[0085] In the following description, an organic electroluminescent device according to an embodiment of the present disclosure and a fused polycyclic compound included therein will be described with reference to the accompanying drawings.

[0086] Figures 1 to 4 This is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure. (Refer to...) Figures 1 to 4 In each organic electroluminescent device 10 according to embodiments of the present disclosure, a first electrode EL1 and a second electrode EL2 are disposed facing each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers may include a hole transport region (HTR), an emitter layer (EML), and an electron transport region (ETR). For example, each of the organic electroluminescent devices 10 according to embodiments may include a first electrode EL1, a hole transport region (HTR), an emitter layer (EML), an electron transport region (ETR), and a second electrode EL2 stacked sequentially. In some embodiments, a capping layer (CPL) may be disposed on the second electrode EL2.

[0087] The organic electroluminescent device 10 may include a fused polycyclic compound, as described below, in at least one of a plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2. For example, the organic electroluminescent device 10 may include a fused polycyclic compound in the emitter layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiments are not limited thereto, and the organic electroluminescent device 10 may include a fused polycyclic compound in at least one of the hole transport region HTR and the electron transport region ETR in the plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2, or in the capping layer CPL disposed on the second electrode EL2.

[0088] Compared to Figure 1 , Figure 2 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Compared to Figure 1 , Figure 3 A cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein 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 includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Compared to Figure 2 , Figure 4 A cross-sectional view of an organic electroluminescent device 10, including a capping layer CPL disposed on a second electrode EL2, is shown.

[0089] In the following description, the organic electroluminescent device 10 includes a fused polycyclic compound according to an embodiment in the emitter layer EML, but the embodiments are not limited thereto, and in some embodiments, the fused polycyclic compound may be included in the hole transport region HTR, the electron transport region ETR, and / or the capping layer CPL.

[0090] The first electrode EL1 may be conductive. The first electrode EL1 may be formed of a metal alloy and / or a conductive compound. The first electrode EL1 may be an anode. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it may include a transparent metal oxide (such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). When the first electrode EL1 is a transmissive-reflective electrode or a reflective electrode, it may include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF, molybdenum (Mo), titanium (Ti), compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the first electrode EL1 may have a multilayer structure, including a reflective or transflective layer formed of the aforementioned materials and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. 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 approximately up to approximately For example, approximately up to approximately

[0091] A hole transport region (HTR) is disposed on the first electrode EL1. The HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, and an electron blocking layer (EBL). The thickness of the HTR may be, for example, approximately... up to approximately

[0092] The hole transport region (HTR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure including multiple layers formed of multiple different materials.

[0093] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR can have a single-layer structure formed of a variety of different materials, or it can have a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are sequentially stacked from the first electrode EL1, but the embodiments are not limited thereto.

[0094] Hole transport regions (HTRs) can be formed using any suitable method, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI).

[0095] Hole injection layer HIL can include, for example, phthalocyanine compounds (such as copper phthalocyanine), N,N'-diphenyl-N,N'-bis[4-(di-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecyl Benzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPD), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexaonitrile (HAT-CN), etc.

[0096] Hole transport layers (HTLs) can include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-1-yl)-N,N'- Diphenyl-benzidine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), etc.

[0097] The thickness of the hole transport region (HTR) can be approximately up to approximately For example, approximately up to approximately The thickness of the hole injection layer (HIL) can be, for example, approximately up to approximately The thickness of the hole transport layer (HTL) can be approximately up to approximately For example, the thickness of the electron blocking layer (EBL) can be approximately up to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the above-mentioned ranges, satisfactory hole transport properties can be achieved without significantly increasing the driving voltage.

[0098] In addition to the materials described above, the hole transport region (HTR) may also include a charge-generating material to improve conductivity. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doped agent. The p-doped agent may be, but is not limited to, a quinone derivative, a metal oxide, or a cyano-containing compound. For example, non-limiting examples of p-doped agents may include quinone derivatives (such as tetracyanoquinone dimethyl (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), etc., but are not limited to these.

[0099] As described above, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may also include at least one of a hole buffer layer and an electron blocking layer (EBL). The hole buffer layer can compensate for the resonant distance of the light wavelength emitted from the emitter layer (EML), thereby improving luminous efficiency. Materials that can be included in the hole transport region (HTR) may also be included in the hole buffer layer. The electron blocking layer (EBL) can prevent or reduce the injection of electrons from the electron transport region (ETR) into the hole transport region (HTR).

[0100] The emitter layer EML is disposed on the hole transmission region HTR. The thickness of the emitter layer EML can be, for example, approximately... up to approximately or approximately up to approximately The emitter layer (EML) can be a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure with multiple layers made of multiple different materials.

[0101] The emission layer EML in the organic electroluminescent device 10 of the embodiment may include the fused polycyclic compound of the embodiment.

[0102] In the specification, the term "substituted or unsubstituted" may indicate an unsubstituted state or a state substituted with at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonium oxide, phosphonium sulfide, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Each of these example substituents may be further substituted or unsubstituted. For example, biphenyl may be interpreted as being aryl itself, or as a phenyl group substituted with a phenyl group.

[0103] In the specification, the phrase "bonded with adjacent groups to form a ring" can refer to a state where a ring is bonded with adjacent groups to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The ring formed by bonding with adjacent groups can be monocyclic or polycyclic. In some embodiments, the rings formed by bonding with each other can connect to another ring to form a spirostructure.

[0104] In the specification, the term "adjacent groups" can refer to substituents on the same atom or point, substituents on atoms directly connected to the base atom or point, or substituents spatially positioned relative to the corresponding substituent (e.g., within intramolecular bonding distance). For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other.

[0105] In the instruction manual, the term "direct-connected key" can refer to a single key.

[0106] In the specification, non-limiting examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0107] In the specification, the alkyl group can be a straight-chain alkyl group, a branched alkyl group, or a cycloalkyl group. The number of carbon atoms in the alkyl group can be from 1 to 50, from 1 to 30, from 1 to 20, from 1 to 10, or from 1 to 6. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl 2-Hexyldecyl, 2-Octylide, n-Undecyl, n-Dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octylide, n-Tridecyl, n-Tetradecyl, n-Pentadedecyl, n-Hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylide, n-Heptadedecyl, n-Octadedecyl, n-Nondecyl, n-Eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octylide, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, n-Iconodecyl, etc.

[0108] In this specification, the term "alkenyl" refers to a hydrocarbon group comprising at least one carbon-carbon double bond in the middle or at the end of an alkyl group having two or more carbon atoms. Alkenyl groups can be straight-chain or branched. There is no particular limitation on the number of carbon atoms, and it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styryl, styrylvinyl, etc.

[0109] In this specification, the term "hydrocarbon ring" includes aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The term "heterocycle" includes aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can each be independently monocyclic or polycyclic.

[0110] In the specification, the hydrocarbon cyclogroup can be any functional group or substituent derived from an aliphatic hydrocarbon ring or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of carbons in the hydrocarbon cyclogroup used to form the ring can be from 5 to 60.

[0111] In the specification, the heterocyclic group can be a functional group or substituent derived from a heterocycle and including at least one heteroatom as an atom for forming the ring. The number of carbon atoms in the heterocyclic group for forming the ring can be from 5 to 60.

[0112] In this specification, the term "aryl" refers to any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of cyclic carbon atoms in an aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Basic, etc., but not limited to this.

[0113] In the specification, the fluorene group can be substituted, and the two substituents can combine with each other to form a spirostructure. Examples of substituted fluorene groups are given below, but the embodiments disclosed herein are not limited thereto:

[0114]

[0115] In the specification, the heteroaryl group may include at least one of boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S) as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiaphenyl, dibenzothiaphenyl, thienothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl, dibenzofuranyl, etc.

[0116] In this specification, the term "silyl" includes alkylsilyl and arylsilyl. Examples of silyl compounds include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0117] In this specification, the term "boron-based" includes alkylboron-based and arylboron-based. Examples of boron-based compounds include, but are not limited to, dimethylboron-based, diethylboron-based, tert-butylmethylboron-based, diphenylboron-based, phenylboron-based, etc.

[0118] In the specification, there is no particular limitation on the number of carbon atoms in the amino group (or "amino group"), but it can be 0 or 1 to 30. The term "amino group" can include alkylamino groups and arylamino groups. Examples of amino groups include, but are not limited to, methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc.

[0119] In this specification, the term "hydrocyclic group" refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. A hydrocyclic group can be a saturated hydrocyclic group having 5 to 20 cyclic carbon atoms.

[0120] In the specification, the heterocyclic group may include at least one of B, O, N, P, Si, and S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and may include heteroaryl groups. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0121] In the instruction manual, -* indicates the location of the connection.

[0122] The fused polycyclic compounds of the embodiments include structures in which two or more polycyclic heterocycles are fused to a central benzo[9,10]phenanthrene nucleus via two heteroatoms (including one boron atom). Thus, the polycyclic heterocycle can be augmented with four fused rings, each comprising a boron atom and two heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur. For example, in the fused polycyclic compounds of the embodiments, the polycyclic heterocycle can be fused to the benzo[9,10]phenanthrene nucleus using one boron atom and one heteroatom as bidentate linkers.

[0123] The fused polycyclic compound of the embodiment can be represented by Formula 1:

[0124] Formula 1

[0125]

[0126] In Equation 1, R1 to R 12Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, R1 to R 12 Any adjacent pair can combine with an adjacent group to form a ring. In some embodiments, R1 to R 12 Each can be an independent hydrogen atom or a deuterium atom.

[0127] Any pair of adjacent R1 to R 12 The group can be fused with substituents represented by Formula 2. For example, two or more substituents represented by Formula 2 can be fused with the nucleus of Formula 1. In Formula 1, R1 to R 12 At least two pairs of these substituents can be fused with substituents represented by Formula 2. For example, two or three substituents represented by Formula 2 can be fused with a fused polycyclic compound represented by Formula 1. The plurality of substituents represented by Formula 2 can be identical (e.g., the same). However, the embodiments are not limited thereto, and in some embodiments, at least one of the plurality of substituents represented by Formula 2 may have a structure different from the other substituents.

[0128] Formula 2

[0129]

[0130] In Equation 2, -* represents two or more pairs of adjacent R1 to R in Equation 1. 12 The positions of a pair of fused groups. The substituent represented by Formula 2 can be connected to adjacent R1 to R1 in Formula 1 via a boron atom and X1. 12 Any pair of groups fused together.

[0131] X1 and X2 can each be independently NAr1, O, or S. For example, X1 and X2 can each be independently NAr1 or O. X1 and X2 can be the same as or different from each other. For example, both X1 and X2 can be NAr1 or O. In some embodiments, one of X1 and X2 can be NAr1, while the other can be O.

[0132] Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, Ar1 can be combined with an adjacent group to form a ring. For example, Ar1 can be a substituted or unsubstituted phenyl group.

[0133] R a and R bEach of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, R a and R b Each can independently combine with adjacent groups to form a ring. For example, R a and R b Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group. R a and R b At least one of them may be a substituted or unsubstituted methyl, a substituted or unsubstituted tert-butyl, a substituted or unsubstituted arylamino, a substituted or unsubstituted phenyl, or a substituted or unsubstituted carbazole.

[0134] n1 can be an integer from 0 to 4. n2 can be an integer from 0 to 3. When each of n1 and n2 is 0, the fused polycyclic compound according to the embodiment is in R a and R b Each position in the matrix is ​​not substituted (e.g., all positions are hydrogen). When n1 and / or n2 are integers of 2 or greater, R... a and / or R b It can be the same, or multiple Rs a and / or multiple R b At least one of them can be different.

[0135] The fused polycyclic compounds of the embodiments comprise structures in which two or more of the Formula 2 structure, each comprising one boron atom and two heteroatoms, are fused to a central benzo[9,10]phenanthrene nucleus. Therefore, the fused polycyclic compounds of the embodiments comprise two or more boron atoms, and the two or more of the Formula 2 structure are linked at the central benzo[9,10]phenanthrene nucleus to form an extended conjugated structure, thereby stabilizing the structure of the polycyclic aromatic ring. The resulting compounds have a half-width and wavelength range suitable for blue luminescent materials, and when the fused polycyclic compounds of the embodiments are applied to light-emitting devices, the efficiency of the light-emitting devices can be improved.

[0136] The substituent represented by Equation 2 can be represented by any one of Equations 2-1 to 2-8:

[0137] Equation 2-1

[0138]

[0139] Equation 2-2

[0140]

[0141] Equation 2-3

[0142]

[0143] Equation 2-4

[0144]

[0145] Formula 2-5

[0146]

[0147] Formula 2-6

[0148]

[0149] Formula 2-7

[0150]

[0151] Formula 2-8

[0152]

[0153] Equations 2-1 to 2-8 are examples of Equation 2 in which each of X1 and X2 is designated as O, S, or NAr1.

[0154] In equations 2-1 to 2-8, Ar 11 and Ar 12 Each is independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, Ar 11 and Ar 12 Each can independently combine with adjacent groups to form a ring. Ar 11 and Ar 12 They can all be independently identical to Ar1 described in Associative Formula 2.

[0155] R a and R b And n1 and n2 can both be independently identical to those described by combination 2.

[0156] In some embodiments, the substituent represented by Formula 2 can be represented by Formula 2-a:

[0157] Equation 2-a

[0158]

[0159] Equation 2-a is where R is specified. a and R bAn example of the substitution position in Equation 2. As shown in Equation 2-a, R a and R b Each substitution occurs at the para position of a boron atom.

[0160] In equation 2-a, X1 and X2, as well as R a and R b They can all be independently identical to those described in combination 2.

[0161] The fused polycyclic compound represented by Formula 1 can be represented by any one of Formulas 3-1 to 3-5:

[0162] Equation 3-1

[0163]

[0164] Equation 3-2

[0165]

[0166] Equation 3-3

[0167]

[0168] Equation 3-4

[0169]

[0170] Formula 3-5

[0171]

[0172] Equations 3-1 to 3-5 are examples of Equation 1 in which the number of substituents and the fusion positions in Equation 1 are specified.

[0173] In Formulas 3-1 to 3-5, A1 to A8 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, A1 to A8 can be combined with adjacent groups to form a ring.

[0174] B1 and B2, B3 and B4, and B5 and B6 can all be positions fused with the substituents represented by Formula 2. In Formulas 3-1 and 3-2, two substituents represented by Formula 2 are connected (fused), and one of the two substituents represented by Formula 2 is fused at positions B1 and B2, while the other is fused at positions B3 and B4. In Formulas 3-3 to 3-5, three substituents represented by Formula 2 are connected (fused), and one of the three substituents represented by Formula 2 is fused at positions B1 and B2, another is fused at positions B3 and B4, and yet another is fused at positions B5 and B6.

[0175] The fused polycyclic compound represented by Formula 1 can be represented by any one of Formulas 4-1 to 4-8:

[0176] Equation 4-1

[0177]

[0178] Equation 4-2

[0179]

[0180] Equation 4-3

[0181]

[0182] Equation 4-4

[0183]

[0184] Equation 4-5

[0185]

[0186] Equation 4-6

[0187]

[0188] Equation 4-7

[0189]

[0190] Equation 4-8

[0191]

[0192] Formulas 4-1 to 4-8 are examples of Formula 1 in which the substituents represented by Formula 2 are fused at specific positions and have specific stereochemistry (e.g., the positions of boron atoms and heteroatoms).

[0193] In equations 4-1 to 4-8, X 11 X 12 X 13 X 21X 22 and X 23 They can all be independently NAr1, O, or S. X 11 X 12 X 13 X 21 X 22 and X 23 They can all be independently described by X1 and X2 in combination 2.

[0194] R a1 R a2 R a3 R b1 R b2 and R b3 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, R a1 R a2 R a3 R b1 R b2 and R b3 It can combine with adjacent groups to form a ring. R a1 R a2 R a3 R b1 R b2 and R b3 Each can be independently combined with R in Formula 2 a and R b The descriptions are the same.

[0195] n 11 n 12 and n 13 Each of the integers n can be an independent integer from 0 to 4. 21 n 22 and n 23 Each of the integers n can be an independent integer from 0 to 3. 11 n 12 n 13 n 21 n 22 and n 23 They can all be independently described as the same as those for n1 and n2 in Equation 2.

[0196] Ar1 and A1 to A8 can all be independently identical to those described in Equations 2 and 3-1 to 3-5.

[0197] The fused polycyclic compound in the embodiments can be any of the compounds represented by compound group 1. The organic electroluminescent device 10 of the embodiments may include at least one fused polycyclic compound represented by compound group 1 in the emitting layer EML:

[0198] Compound group 1

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217] The emission spectrum of the fused polycyclic compound represented by Formula 1 can have a half-width of about 10 nm to about 50 nm, for example, it can have a half-width of about 20 nm to about 40 nm. When the emission spectrum of the fused polycyclic compound has the above-mentioned half-width, the luminous efficiency of the organic electroluminescent device 10 including the fused polycyclic compound can be improved. Furthermore, when the fused polycyclic compound of the embodiment is used as a blue light-emitting device material of the organic electroluminescent device 10, the lifetime of the organic electroluminescent device 10 can be improved.

[0218] The fused polycyclic compound represented by Formula 1 in the embodiments can be a thermally activated delayed fluorescence (TADF) emission material. Furthermore, the fused polycyclic compound represented by Formula 1 in the embodiments can be a singlet-triplet level difference (ΔE) between the lowest triplet excitation level (T1 level) and the lowest singlet excitation level (S1 level) having a singlet-triplet energy difference of approximately 0.6 eV or less. ST Thermally activated delayed fluorescence dopant.

[0219] The fused polycyclic compound represented by Formula 1 in the embodiments can be a luminescent (light-emitting) material having a light emission center wavelength of about 430 nm to about 490 nm. For example, the fused polycyclic compound represented by Formula 1 in the embodiments can be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiments are not limited thereto, and when the fused polycyclic compound of the embodiments is used as a luminescent material, the fused polycyclic compound can be used as a dopant material to emit light with any suitable wavelength, such as a red luminescent dopant or a green luminescent dopant.

[0220] The emitting layer EML in the organic electroluminescent device 10 of the embodiment can emit delayed fluorescence. For example, the emitting layer EML can emit thermally activated delayed fluorescence (TADF).

[0221] In some embodiments, the emitting layer EML of the organic electroluminescent device 10 can emit blue light. For example, the emitting layer EML of the organic electroluminescent device 10 in the embodiment can emit blue light in the range of approximately 490 nm or larger. However, the embodiments are not limited to this, and the emitting layer EML can also emit green or red light.

[0222] In some embodiments, the organic electroluminescent device 10 may include multiple emitting layers. The multiple emitting layers may be stacked sequentially; for example, the organic electroluminescent device 10 including multiple emitting layers may emit white light. The organic electroluminescent device 10 including multiple emitting layers may be an organic electroluminescent device with a tandem structure. When the organic electroluminescent device 10 includes multiple emitting layers, at least one emitting layer may include a fused polycyclic compound as described in the embodiments above.

[0223] In embodiments, the emitter layer EML includes a host and a dopant, and may include the aforementioned fused polycyclic compound as a dopant. For example, the emitter layer EML in the organic electroluminescent device 10 of the embodiment may include a host for emitting delayed fluorescence and a dopant for emitting delayed fluorescence, and may include the aforementioned fused polycyclic compound as a dopant for emitting delayed fluorescence. The emitter layer EML may include at least one of the fused polycyclic compounds represented by compound group 1 as a thermally activated delayed fluorescence dopant.

[0224] Any suitable material can be used as the host material for the emitter layer EML, such as fluoranthene derivatives, pyrene derivatives, arylaceyne derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, etc. Derivatives, etc., are not specifically limited. In some embodiments, the host material may include pyrene derivatives, perylene derivatives, and / or anthracene derivatives. In some embodiments, anthracene derivatives represented by Formula 5 may be used as the host material of the emitter layer EML:

[0225] Formula 5

[0226]

[0227] In Equation 5, R 31 To R 40 Each of the following can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R 31 To R 40 It can combine with adjacent groups to form a ring. In some embodiments, R 31 To R 40 It can combine with adjacent groups to form a ring.

[0228] In Equation 5, c and d can both be independent integers from 0 to 5.

[0229] The anthracene derivative represented by Formula 5 can be represented by any one of compounds 5-1 to 5-16:

[0230]

[0231]

[0232] In embodiments, the emitter layer EML may include tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4”-tris(carbazolyl-9-yl)triphenylamine (TCTA), 1,3,5-tris(1-phenyl-1H-benzis[d]imidazol-2-yl)benzene (TPBi), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), distyrylarylene (DSA), and 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CD). BP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphospho)dibenzofuran (PPF), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(N-carbazolyl)benzene (mCP), etc., can be used as host materials. However, the examples are not limited to these and may include any suitable delayed fluorescence emission host material other than those listed.

[0233] In some embodiments, the emitter layer (EML) in the organic electroluminescent device 10 of the embodiment may also include any other suitable dopant material. In the embodiments, the emitter layer (EML) may also include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]benzene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene), etc., as dopant materials.

[0234] In some embodiments, the emitter layer EML may include two dopant materials, each dopant material having a different lowest triplet excitation energy level (T1 level). The emitter layer EML of the organic electroluminescent device 10 in this embodiment may include a body having a first lowest triplet excitation energy level, a first dopant having a second lowest triplet excitation energy level lower than the first lowest triplet excitation energy level, and a second dopant having a third lowest triplet excitation energy level lower than the second lowest triplet excitation energy level. In this embodiment, the emitter layer EML may include the fused polycyclic compound described above as the first dopant.

[0235] In the organic light-emitting device 10 of the embodiment that includes a host, a first dopant, and a second dopant in the emitter layer EML, the first dopant may be a delayed fluorescence dopant, and the second dopant may be a fluorescent dopant. In some embodiments, a fused polycyclic compound represented by Formula 1 may be used as an auxiliary dopant in the organic light-emitting device 10 of the embodiment.

[0236] For example, when the emitting layer EML of the organic electroluminescent device 10 of the embodiment includes multiple dopants, the emitting layer EML may include the polycyclic compound of the above embodiments as a first dopant and one of the suitable dopant materials described above as a second dopant. For example, when the emitting layer EML emits blue light, the emitting layer EML may also include any one selected from the group consisting of spiro-DPVBi, spiro-6P, styrene (DSB), styrene arylidene (DSA), polyfluorene (PFO) polymers and poly(p-phenylenevinylene) (PPV) polymers as a second dopant. Organometallic complexes or metal complexes (such as (4,6-F2ppy)2Irpic) and / or perylene and its derivatives may also be used as second dopants.

[0237] In some embodiments, in the organic electroluminescent device 10, which includes a fused polycyclic compound as the first dopant of the emission layer EML, the emission layer EML can emit green or red light, and the second dopant material can be the suitable dopant, green fluorescent dopant, or red fluorescent dopant described above.

[0238] The emission layer EML in the organic electroluminescent device 10 of the embodiment can be a phosphorescent emission layer. For example, a fused polycyclic compound according to the embodiment can be included in the emission layer EML as a phosphorescent host material.

[0239] exist Figures 1 to 4 In the organic electroluminescent device 10 of the embodiment shown, the electron transport region (ETR) is disposed on the emitter layer (EML). The electron transport region (ETR) may include at least one of the hole blocking layer (HBL), the electron transport layer (ETL), and the electron injection layer (EIL), but the embodiment is not limited thereto.

[0240] The electronic transport region (ETR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multi-layer structure including multiple layers formed of multiple different materials.

[0241] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it can have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the ETR can have a single-layer structure formed of a variety of different materials, or it can have a structure in which an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are sequentially stacked from the emitter layer (EML), but is not limited thereto. The thickness of the ETR can be, for example, approximately up to approximately

[0242] The electron transport region (ETR) can be formed using any suitable method, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI), etc.

[0243] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may include anthracene compounds. However, the embodiments are not limited thereto, and the ETL may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4 The electron transport layer (ETL) can be approximately 1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthyl-2-yl)anthracene (ADN), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), or mixtures thereof. up to approximately For example, approximately up to approximately When the thickness of the electron transport layer (ETL) meets the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0244] When the electron transport region (ETR) includes an electron injection layer (EIL), the EIL can be formed using metal halides (such as LiF, NaCl, CsF, RbCl, RbI, and / or CuI), lanthanides (such as Yb), metal oxides (such as Li₂O and / or BaO), lithium hydroxyquinoline (LiQ), etc., but the embodiments are not limited thereto. The EIL can also be formed from a mixture of an electron injection material and an insulating organometallic salt. The organometallic salt can be a material having a band gap of approximately 4 eV or greater. The organometallic salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the EIL can be approximately... up to approximately For example, approximately up to approximately When the thickness of the electron injection layer (EIL) meets the above range, satisfactory electron injection performance can be obtained without significantly increasing the driving voltage.

[0245] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may include, but is not limited to, at least one of, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen).

[0246] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 can be a common electrode or a cathode. The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, the second electrode EL2 can be formed of a transparent metal oxide such as ITO, IZO, ZnO, ITZO, etc.

[0247] When the second electrode EL2 is a transmissive or reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the second electrode EL2 may have a multilayer structure, which includes a reflective or transmissive layer formed of the above-described materials and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc.

[0248] In some embodiments, the second electrode EL2 can be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0249] In some embodiments, the organic electroluminescent device 10 may include a buffer layer between the emitter layer (EML) and the electron transport region (ETR). The buffer layer may control or influence the concentration of excitons generated in the emitter layer (EML). In some embodiments, the buffer layer may include at least some of the emitter layer materials. For example, the buffer layer may include the host material of the emitter layer material (e.g., the same host material included in the emitter layer (EML)). Depending on the combination of the host material and dopant material included in the emitter layer (EML), the lowest triplet excitation energy level of the buffer layer material may be controlled or selected to be higher than or substantially equal to the lowest triplet excitation energy level of the second dopant or lower than or substantially equal to the lowest triplet excitation energy level of the first dopant.

[0250] In some embodiments, a capping layer CPL may be further disposed on the second electrode EL2 of the organic electroluminescent device 10 according to the embodiment. The capping layer CPL may include an organic layer and / or an inorganic layer. The capping layer CPL may be a single layer, such as an organic layer or an inorganic layer, or a layer in which organic and inorganic layers are sequentially stacked. The capping layer CPL may have a refractive index of about 1.6 or greater in a wavelength range of about 560 nm to about 600 nm. The capping layer CPL may include amine compound CPL1 and / or amine compound CPL2:

[0251]

[0252] In some embodiments, the capping CPL may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc. In some embodiments, the capping CPL may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, etc.

[0253] The fused polycyclic compounds of the embodiments described above include structures in which two or more of Formula 2 structures are fused with a central benzo[9,10]phenanthrene nucleus, each of the two or more Formula 2 structures comprising a boron atom and two heteroatoms. The fused polycyclic compounds of Formula 1 according to the embodiments have extended conjugated structures, and therefore, when the fused polycyclic compounds of the embodiments are used as luminescent materials for organic electroluminescent devices, high efficiency of the organic electroluminescent devices can be achieved.

[0254] In the following description, fused polycyclic compounds according to embodiments of the present disclosure will be described in more detail with reference to examples and comparative examples. Examples are provided as illustrations to aid in understanding the present disclosure, and the scope of the disclosure is not limited thereto.

[0255] Example

[0256] 1. Synthesis of fused polycyclic compounds

[0257] Example synthetic methods for the fused polycyclic compounds according to this embodiment will be described with reference to compounds 9, 25, 27, 53, 58, 59, 76, and 81. The synthetic methods for fused polycyclic compounds are provided as examples and are not limited thereto.

[0258] (1) Synthesis of compound 9

[0259] Synthesis of intermediate compound A

[0260]

[0261] 2,11-Dibromobenzo[9,10]phenanthrene (20.0 g, 51.8 mmol), 3-phenoxyphenol (20.3 g, 109 mmol), CuI (0.49 g, 2.59 mmol), K₂CO₃ (28.6 g, 207 mmol), and tris(2,4-pentanedione)ferro(III) (Fe(III)(acac)₃, 1.67 g, 5.2 mmol) were added to 1-methyl-2-pyrrolidone (NMP, 117 mL) and heated and stirred at 180 °C for 24 hours. The mixture was cooled, filtered through diatomaceous earth (Celite), and separated by adding toluene and water to obtain an organic layer. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, and washed with additional hexane to obtain intermediate compound A (25.3 g, yield: 82%). The molecular weight of intermediate compound A was determined to be 597 by FAB-MS.

[0262] Synthesis of Compound 9

[0263]

[0264] In an argon (Ar) atmosphere, intermediate compound A (23 g, 38.5 mmol) was added to tert-butylbenzene (96 mL) and cooled to -30 °C. Tert-butyllithium (1.6 M / L pentane, 96 mL, 154 mmol) was then slowly added. The mixture was allowed to approach room temperature for approximately 1 hour, then heated and stirred at approximately 60 °C for 3 hours. The reaction solution was cooled to -30 °C, and BBr3 (38.6 g, 154 mmol) was slowly added, while heating and stirring at an internal temperature of 30 °C for 1 hour. The reaction solution was then ice-chilled, and N,N-diisopropylethylamine (20.0 g, 154 mmol) was added, followed by heating and stirring at 100 °C for 2 hours. After cooling and the addition of water, the resulting mixture was filtered through diatomaceous earth, and the organic layer was concentrated. The concentrated organic layer was purified by silica gel column chromatography to obtain compound 9 (7.79 g, yield: 33%). The molecular weight of compound 9 was determined to be 612 by FAB-MS. The obtained compound 9 was further purified by sublimation (300℃, 8.7×10⁻⁶). -3 Pa) and used as a sample for evaluation.

[0265] (2) Synthesis of compound 25

[0266] Synthesis of intermediate compound B

[0267]

[0268] Except that 3-(diphenylamino)phenol (18.9 g) was used instead of 3-phenoxyphenol, the reaction was carried out under essentially the same conditions as those used for the synthesis of intermediate compound A. As a result, intermediate compound B (15.6 g, yield: 72%) was obtained.

[0269] Synthesis of Compound 25

[0270]

[0271] Except that intermediate compound B (15.0 g) was used instead of intermediate compound A, the reaction was carried out under essentially the same conditions as those used for the synthesis of compound 9. As a result, compound 25 (4.44 g, yield: 29%) was obtained. The molecular weight of compound 25 was determined to be 762 by FAB-MS. Compound 25 was purified by sublimation (300 °C, 8.7 × 10⁻⁶). -3 Pa) is used for evaluation.

[0272] (3) Synthesis of compound 27

[0273] Synthesis of intermediate compound C and intermediate compound D

[0274]

[0275] In an Ar atmosphere, 1,3-dibromo-5-methoxybenzene (25.0 g, 94.0 mmol), diphenylamine (33.4 g, 197 mmol), Pd(dba)2 (1.62 g, 2.82 mmol), and P( t Bu)3HBF4 (0.68g, 3.76mmol) and t BuONa (27.1 g, 282 mmol) was added to 470 mL of toluene and heated and stirred at 80 °C for 2 hours. After adding water, the resulting mixture was filtered through diatomaceous earth, and the organic layer was separated and concentrated. The concentrated organic layer was purified by silica gel column chromatography to obtain intermediate compound C (41.6 g, yield: 80%). Subsequently, intermediate compound C was dissolved in 500 mL of CH2Cl2, and BBr3 (46.4 g, 185 mmol) was added, and the mixture was stirred at 0 °C for 24 hours. After adding water, the resulting mixture was filtered through diatomaceous earth, and the organic layer was concentrated and purified by silica gel column chromatography to obtain intermediate compound D (29.8 g, yield: 75%). The molecular weight of intermediate compound D was determined to be 429 by FAB-MS.

[0276] Synthesis of intermediate compound E

[0277]

[0278] Except that intermediate compound D (28.3 g) was used instead of 3-phenoxyphenol, the reaction was carried out under essentially the same conditions as those used to synthesize intermediate compound A. As a result, intermediate compound E (20.0 g, yield: 70%) was obtained. The molecular weight of intermediate compound E was determined to be 1080 by FAB-MS.

[0279] Synthesis of Compound 27

[0280]

[0281] Intermediate compound E (18.0 g, 16.7 mmol) was dissolved in 180 mL of ODCB, and BBr3 (13.4 g, 53.6 mmol) was added. The mixture was stirred at 180 °C for 10 hours. The reaction solution was chilled, and N,N-diisopropylethylamine (20.0 g, 154 mmol) was added. The resulting mixture was filtered through diatomaceous earth, and the organic layer was concentrated. The concentrated organic layer was purified by silica gel column chromatography to obtain compound 27 (12.8 g, yield: 70%). The molecular weight of compound 27 was determined to be 1097 by FAB-MS. Compound 27 was purified by sublimation (300 °C, 8.7 × 10⁻⁶).-3 Pa) is used for evaluation.

[0282] (4) Synthesis of compound 53

[0283] Synthesis of intermediate compound F

[0284]

[0285] 1,3-Dibromo-5-chlorobenzene (35.0 g, 129 mmol), diphenylamine (43.8 g, 259 mmol), Pd2(dba)3 (2.49 g, 2.72 mmol), Sphos (2.23 g, 5.44 mmol) and t BuONa (37.9 g, 394 mmol) was added to 500 mL of toluene and heated and stirred at 80 °C for 5 hours. The mixture was cooled, filtered through diatomaceous earth, and separated by adding toluene and water to obtain an organic layer. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, and washed with additional hexane to obtain intermediate compound F (45.0 g, yield: 78%). The molecular weight of intermediate compound F was determined to be 447 by FAB-MS.

[0286] Synthesis of intermediate compound G

[0287]

[0288] Intermediate compound F (35.0 g, 78.3 mmol), aniline (7.29 g, 78.3 mmol), Pd(dba)2 (1.80 g, 3.13 mmol), P( t Bu)3HBF4 (1.82g, 6.26mmol) and t BuONa (11.29 g, 117 mmol) was added to 200 mL of toluene, and then heated and stirred at 80 °C for 5 hours. The mixture was cooled, filtered through diatomaceous earth, and separated by adding toluene and water to obtain an organic layer. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, and washed with additional hexane to obtain intermediate compound G (28.0 g, yield: 71%). The molecular weight of intermediate compound G was determined to be 504 by FAB-MS.

[0289] Synthesis of intermediate compound H

[0290]

[0291] The reaction was carried out under essentially the same conditions as those used for the synthesis of intermediate C to obtain intermediate H (25.0 g, yield: 78%) from 2,11-dibromobenzo[9,10]phenanthrene (10.0 g, 25.9 mmol) and intermediate G (26.1 g, 51.8 mmol). The molecular weight of intermediate H was determined to be 1232 by FAB-MS.

[0292] Synthesis of Compound 53

[0293]

[0294] Intermediate compound H (15.0 g, 12.2 mmol) was added to 162 mL of ODCB, followed by the addition of BBr3 (18.3 g, 73 mmol). The mixture was then heated and stirred at 180 °C for 6 hours. The mixture was cooled, and N,N-diisopropylethylamine (47.0 g, 365 mmol) was added. After adding 1 L of acetonitrile, the mixture was filtered. The resulting product was purified by silica gel column chromatography to obtain compound 53 (8.0 g, yield: 53%). The molecular weight of compound 53 was determined to be 1247 by FAB-MS. Compound 53 was further purified by sublimation (430 °C, 8.2 × 10⁻⁶). -3 Pa) is used for evaluation.

[0295] (5) Synthesis of compound 58

[0296] Synthesis of intermediate compound I

[0297]

[0298] 1-Bromo-3-fluorobenzene (16.0 g, 91.4 mmol), 3-(diphenylamino)phenol (35.8 g, 137 mmol), and K3PO4 (58.2 g, 274 mmol) were added to 160 mL of NMP, and then heated and stirred at 180 °C for 8 hours. The mixture was cooled, filtered through diatomaceous earth, and separated by adding toluene and water to obtain an organic layer. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, and washed with additional hexane to obtain intermediate compound I (30.0 g, yield: 79%). The molecular weight of intermediate compound I was determined to be 416 by FAB-MS.

[0299] Synthesis of intermediate compound J

[0300]

[0301] Intermediate compound I (28.0 g, 67.3 mmol) and aniline (6.26 g, 67.3 mmol) were reacted under essentially the same conditions as those used to synthesize intermediate compound G to obtain intermediate compound J (22.0 g, yield: 76%). The molecular weight of intermediate compound J was determined to be 429 by FAB-MS.

[0302] Synthesis of intermediate compound K

[0303]

[0304] The reaction was carried out under essentially the same conditions as those used for the synthesis of intermediate C to obtain intermediate K (21.0 g, yield: 75%) from 2,11-dibromobenzo[9,10]phenanthrene (10.0 g, 25.9 mmol) and intermediate J (22.2 g, 51.8 mmol). The molecular weight of intermediate K was determined to be 1081 by FAB-MS.

[0305] Synthesis of Compound 58

[0306]

[0307] The reaction was carried out under essentially the same conditions as for the synthesis of compound 53 to obtain compound 58 (3.0 g, yield: 14%) from intermediate compound K (21.0 g, 19.4 mmol). The molecular weight of compound 58 was determined to be 1097 by FAB-MS. The obtained compound 58 was purified by sublimation (415 °C, 8.7 × 10⁻⁶ mmol / L). -3 Pa) is used for evaluation.

[0308] (6) Synthesis of compound 59

[0309] Synthesis of intermediate compound L

[0310]

[0311] The reaction was carried out under essentially the same conditions as those used to synthesize intermediate I to obtain intermediate L (14.0 g, yield: 72%) from 1,3-dibromo-5-fluorobenzene (15.0 g, 59.1 mmol) and phenol (8.34 g, 88.6 mmol). The molecular weight of intermediate L was determined to be 328 by FAB-MS.

[0312] Synthesis of intermediate compound M

[0313]

[0314] The intermediate compound L (13.9 g, 42.6 mmol), diphenylamine (6.0 g, 35.5 mmol), Pd2(dba)3 (0.81 g, 0.89 mmol), XantPhos (0.86 mmol) and t BuONa (4.1 g, 42.6 mmol) was added to 79 mL of toluene and stirred at 80 °C for 5 h and / or at 100 °C for 3 h. The mixture was cooled, filtered through diatomaceous earth, and separated by adding toluene and water to obtain an organic layer. The organic layer was concentrated, purified by column chromatography (silica gel), concentrated, and washed with additional hexane to obtain intermediate compound M (12.0 g, yield: 81%). The molecular weight of intermediate compound M was determined to be 416 by FAB-MS.

[0315] Synthesis of intermediate compound N

[0316]

[0317] Intermediate compound M (28.0 g, 67.3 mmol) and aniline (6.26 g, 67.3 mmol) were reacted under essentially the same conditions as those used to synthesize intermediate compound G to obtain intermediate compound N (22.0 g, yield: 76%). The molecular weight of intermediate compound N was determined to be 429 by FAB-MS.

[0318] Synthesis of intermediate compound O

[0319]

[0320] The reaction was carried out under essentially the same conditions as those used for the synthesis of intermediate C to yield intermediate O (20.0 g, yield: 71%) from 2,11-dibromobenzo[9,10]phenanthrene (10.0 g, 25.9 mmol) and intermediate N (22.2 g, 51.8 mmol). The molecular weight of intermediate O was determined to be 1081 by FAB-MS.

[0321] Synthesis of Compound 59

[0322]

[0323] The reaction was carried out under essentially the same conditions as for the synthesis of compound 53 to obtain compound 59 (1.2 g, yield: 6%) from intermediate compound O (19.0 g, 17.6 mmol). The molecular weight of compound 59 was determined to be 1097 by FAB-MS. The obtained compound 59 was purified by sublimation (405 °C, 8.2 × 10⁻⁶ mmol / L). -3 Pa) is used for evaluation.

[0324] (7) Synthesis of compound 76

[0325] Synthesis of intermediate compound P

[0326]

[0327] The reaction was carried out under essentially the same conditions as those used to synthesize intermediate A to yield intermediate P (12.6 g, yield: 75%) from 2,6,10-tribromobenzo[9,10]phenanthrene (10.0 g, 21.5 mmol) and 3-phenoxyphenol (13.2 g, 71.0 mmol). The molecular weight of intermediate P was determined to be 781 by FAB-MS.

[0328] Synthesis of Compound 76

[0329]

[0330] Except for using the obtained intermediate compound P (23.0 g, 29.5 mmol), the reaction was carried out under essentially the same conditions as those used for the synthesis of compound 9. As a result, compound 76 (5.50 g, yield: 23%) was obtained. The molecular weight of compound 76 was determined to be 804 by FAB-MS. Compound 76 was purified by sublimation (320 °C, 8.3 × 10⁻⁶ mmol / L). -3 Pa) is used for evaluation.

[0331] (8) Synthesis of compound 81

[0332] Synthesis of intermediate compound Q

[0333]

[0334] The reaction was carried out under essentially the same conditions as those used to synthesize intermediate A to obtain intermediate Q (12.1 g, yield: 70%) from 2,6,10-tribromobenzo[9,10]phenanthrene (8.0 g, 17.2 mmol) and 3-(diphenylamino)phenol (14.8 mmol). The molecular weight of intermediate Q was determined to be 1006 by FAB-MS.

[0335] Synthesis of Compound 81

[0336]

[0337] The reaction was carried out under essentially the same conditions as for the synthesis of compound 53 to obtain compound 81 (2.2 g, yield: 22%) from intermediate compound Q (10.0 g, 9.94 mmol). The molecular weight of compound 81 was determined to be 1029 by FAB-MS. The obtained compound 81 was purified by sublimation (390 °C, 8.4 × 10⁻⁶ mmol / L). -3 Pa) is used for evaluation.

[0338] 2. Fabrication and evaluation of organic electroluminescent devices, including fused polycyclic compounds.

[0339] Manufacturing of organic electroluminescent devices

[0340] In the fabrication of the organic electroluminescent devices in Examples 1 to 8, compounds 9, 25, 27, 53, 58, 59, 76 and 81 were used as emitter layer dopant materials, respectively.

[0341] Example compounds

[0342]

[0343] Organic electroluminescent devices of the comparative examples were fabricated using comparative example compounds X-1 to X-5:

[0344] Comparative example compounds

[0345]

[0346] Organic electroluminescent devices comprising the fused polycyclic compounds of the embodiments in the emitting layer are fabricated as follows. Examples 1 to 8 correspond to organic electroluminescent devices fabricated using the respective compounds 9, 25, 27, 53, 58, 59, 76, and 81 as luminescent materials. Comparative Examples 1 to 5 correspond to organic electroluminescent devices fabricated using the respective comparative example compounds X-1 to X-5 as luminescent materials.

[0347] A 150 nm thick first electrode was formed using ITO, a 10 nm thick hole injection layer was formed using 1,4,5,8,9,12-hexaazabenzo[9,10]phenanthrenehexacarbonitrile (HAT-CN), an 80 nm thick first hole transport layer was formed using N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (α-NPD), and a 5 nm thick hole transport layer was formed using 1,3-bis(N-carbazolyl)benzene (mCP). A second hole transport layer of thickness m is formed, a 20 nm thick emitter layer is formed by doping 1% of the corresponding example compound or comparative example compound in 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), a 30 nm thick electron transport layer is formed by 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), a 0.5 nm thick electron injection layer is formed by LiF, and a 100 nm thick second electrode is formed by Al. A 70 nm thick capping layer is formed on the second electrode by N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine (CPL1). Each layer is formed by deposition under a vacuum atmosphere.

[0348] Compounds for manufacturing example and comparative examples of organic electroluminescent devices are disclosed.

[0349]

[0350] Experimental Example

[0351] The efficiency of organic electroluminescent devices fabricated using experimental example compounds 9, 25, 27, 53, 58, 59, 76, and 81, as well as comparative example compounds X-1 to X-5, was evaluated. The evaluation results are shown in Table 1. The maximum emission wavelength in the emission spectrum is expressed in terms of λ. max This indicates that the maximum external quantum efficiency is expressed in terms of EQE. max This indicates that at 1000 cd / m 2 The value of the lower external quantum efficiency is expressed in terms of EQE. 1000nit express.

[0352] Table 1

[0353]

[0354]

[0355] Referring to the results in Table 1, it can be seen that, compared to the comparative examples, the examples of organic electroluminescent devices using fused polycyclic compounds as luminescent materials according to embodiments of the present disclosure all exhibit improved luminous efficiency while maintaining the emission wavelength of blue light.

[0356] The example compounds have a structure in which two or more tetracyclic fused polycyclic heterocycles (each containing boron atoms and heteroatoms as bidentate linkers) are fused to a central benzo[9,10]phenanthrene nucleus with a high T1 energy level, thereby possessing a half-width and wavelength range suitable for blue luminescent materials, as well as an extended conjugated system, thus improving the stability of the compound molecules. Therefore, the example organic light-emitting devices can exhibit improved luminous efficiency compared to the comparative example organic light-emitting devices. The example organic light-emitting devices include fused polycyclic compounds as thermally activated delayed fluorescence (TADF) dopants, thus enabling high device efficiency in the blue wavelength region (e.g., the deep blue wavelength region).

[0357] Comparative example compounds X-1 (included in Comparative Example 1) and X-2 (included in Comparative Example 2) do not possess the benzo[9,10]phenanthrene moiety, and their stability is reduced compared to the example compounds. Therefore, the organic electroluminescent devices of Comparative Example 1 and Comparative Example 2 exhibit reduced device efficiency compared to the examples.

[0358] Comparative example compounds X-3 to X-5, included in Comparative Examples 3 to 5, all possess a benzo[9,10]phenanthrene moiety, but have a structure in which only one tetracyclic fused polycyclic heterocycle containing a boron atom and a heteroatom is fused to the benzo[9,10]phenanthrene nucleus. The polycyclic compound structures of Comparative Example Compounds X-3 to X-5, containing one boron atom, all have wavelengths that are too short, approximately 440 nm or less, and their stability is reduced compared to the example compounds. Therefore, the organic electroluminescent devices of Comparative Examples 3 to 5 all exhibit reduced device efficiency compared to the examples.

[0359] The organic electroluminescent devices of the embodiments can exhibit improved high-efficiency device characteristics.

[0360] The fused polycyclic compounds of the embodiments may be included in the emitting layer of the organic electroluminescent device to contribute to the high efficiency of the organic electroluminescent device.

[0361] As used herein, the terms “basic,” “approximately,” and similar terms are used as approximate terms rather than terms of degree and are intended to account for inherent biases in measurements or calculations that will be recognized by one of ordinary skill in the art.

[0362] Any numerical range stated herein is intended to include all subranges with the same numerical precision contained within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the stated minimum value of 1.0 and the stated maximum value of 10.0 (and including both the stated minimum value of 1.0 and the stated maximum value of 10.0), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly state any subranges included within the scope expressly stated herein.

[0363] Although this disclosure has been described with reference to exemplary embodiments thereof, it will be understood that this disclosure is not limited to these embodiments, and various changes and modifications can be made by those skilled in the art without departing from the spirit and scope of this disclosure.

[0364] Therefore, the scope of this disclosure is not intended to be limited to the specific embodiments described in the specification, but rather to be defined by the appended claims and their equivalents.

Claims

1. An organic electroluminescent device, the organic electroluminescent device comprising: First electrode; The second electrode faces the first electrode; as well as Multiple organic layers are located between the first electrode and the second electrode. Wherein, both the first electrode and the second electrode independently comprise any one, two or more compounds of, two or more of the elements selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Zn, Sn, and Yb, or at least one oxide of the elements selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Zn, Sn, and Yb. At least one of the plurality of organic layers comprises a fused polycyclic compound represented by any one of formulas 3-1 to 3-5: Equation 3-1 Equation 3-2 Equation 3-3 Equation 3-4 Formula 3-5 and Among them, in equations 3-1 to 3-5, A1 through A8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring; and B1 and B2, B3 and B4, and B5 and B6 are all fused with the substituents represented by Formula 2: Formula 2 ， In Equation 2, The positions that are confluent with adjacent B1 and B2, adjacent B3 and B4, and adjacent B5 and B6 in Equations 3-1 to 3-5; X1 and X2 are both independently NAr1, O or S; Ar1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, Ar1 is combined with an adjacent group to form a ring; R a and R b Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R a and R b It can combine with adjacent groups to form a ring; n1 is an integer from 0 to 4; and n2 is an integer from 0 to 3.

2. The organic electroluminescent device according to claim 1, wherein The plurality of organic layers include: The hole transport region is located on the first electrode; The emission layer is located on the hole transport region; and The electron transport region is located on the emission layer, and The emission layer includes the fused polycyclic compound.

3. The organic electroluminescent device according to claim 2, wherein The emission layer emits delayed fluorescence.

4. The organic electroluminescent device according to claim 2, wherein, The emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and the dopant comprises the fused polycyclic compound represented by one of Formulas 3-1 to 3-5.

5. The organic electroluminescent device according to claim 1, wherein Two or three substituents represented by Formula 2 are fused with the fused polycyclic compound represented by one of Formulas 3-1 to 3-5, and the two or three fused substituents represented by Formula 2 are identical to each other.

6. The organic electroluminescent device according to claim 1, wherein The substituent represented by Equation 2 is any one selected from Equations 2-1 to 2-8: Equation 2-1 Equation 2-2 Equation 2-3 Equation 2-4 Formula 2-5 Formula 2-6 Formula 2-7 Formula 2-8 ， Among them, in equations 2-1 to 2-8, Ar 11 and Ar 12 All are independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, and optionally, Ar 11 and Ar 12 It combines with adjacent groups to form a ring, and R a and R b Both n1 and n2 are independently identical to those defined in Equation 2.

7. The organic electroluminescent device according to claim 1, wherein The substituent represented by Equation 2 is represented by Equation 2-a: Equation 2-a ， In equation 2-a, X1and X2and R a and R b are each independently the same as defined in Formula 2.

8. The organic electroluminescent device according to claim 1, wherein The fused polycyclic compound represented by any one of formulas 3-1 to 3-5 is represented by any one of formulas 4-1 to 4-8: Equation 4-1 Equation 4-2 Equation 4-3 Equation 4-4 Equation 4-5 Equation 4-6 Equation 4-7 Equation 4-8 ， Among them, in equations 4-1 to 4-8, X 11 X 12 X 13 X 21 X 22 and X 23 Each is independently NAr1, O, or S; R a1 R a2 R a3 R b1 R b2 and R b3 Each of these elements is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R a1 R a2 R a3 R b1 R b2 and R b3 It can combine with adjacent groups to form a ring; n 11 , n 12 , and n 13 are each independently an integer from 0 to 4; n 21 , n 22 , and n 23 are each independently an integer from 0 to 3; and Ar1 and A1 through A8 are all independently identical to those defined in Equations 2 and 3-1 through 3-5.

9. The organic electroluminescent device according to claim 1, wherein, R a and R b Each of these groups is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

10. The organic electroluminescent device according to claim 1, wherein A1 through A8 are each independently a hydrogen atom or a deuterium atom.

11. The organic electroluminescent device according to claim 1, further comprising a capping layer on the second electrode and having a refractive index of 1.6 or greater.

12. The organic electroluminescent device according to claim 1, wherein The fused polycyclic compound represented by one of formulas 3-1 to 3-5 is at least one selected from the compounds represented by group 1 of compounds: Compound group 1 。 13. A fused polycyclic compound, said fused polycyclic compound being represented by any one of formulas 3-1 to 3-5: Equation 3-1 Equation 3-2 Equation 3-3 Equation 3-4 Formula 3-5 and wherein In equations 3-1 to 3-5, A1 through A8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxygen group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring; and B1 and B2, B3 and B4, and B5 and B6 are all fused with the substituents represented by Formula 2: Formula 2 ， In Equation 2, The positions that are confluent with adjacent B1 and B2, adjacent B3 and B4, and adjacent B5 and B6 in Equations 3-1 to 3-5; X1 and X2 are both independently NAr1, O or S; Ar1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, Ar1 is combined with an adjacent group to form a ring; R a and R b Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, R a and R b It can combine with adjacent groups to form a ring; n1 is an integer from 0 to 4; and n2 is an integer from 0 to 3.

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