Fused ring compound, light-emitting device including the same, and electronic device including the light-emitting device

Abstract

This application provides a fused-ring compound represented by Formula 1, a light-emitting device comprising the fused-ring compound, and an electronic device comprising the light-emitting device. The light-emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first and second electrodes. The intermediate layer includes a hole transfer region, an emission layer, and an electron transfer region, and the hole transfer region includes a fused-ring compound represented by Formula 1. Formula 1 is as defined herein.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2025-0004185, filed on January 10, 2025, with the Korean Intellectual Property Office (KIPO), the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of this disclosure relate to fused ring compounds, light-emitting devices including fused ring compounds, and electronic devices including light-emitting devices. Background Technology

[0004] Organic light-emitting diode (OLED) displays are self-emissive and offer improved viewing angles and contrast. They also provide high response times and high brightness.

[0005] The light-emitting device may include an emitting layer disposed between a first electrode and a second electrode. Holes moving from the first electrode and electrons moving from the second electrode can recombine in the emitting layer to generate excitons. When the excitons transition from the excited state to the ground state, the light-emitting property is achieved. Summary of the Invention

[0006] According to one aspect, fused ring compounds with improved driving voltage, luminous efficiency and lifetime characteristics are provided.

[0007] On the one hand, a light-emitting device with improved driving voltage, luminous efficiency, and lifetime characteristics is provided.

[0008] On the one hand, electronic devices with improved driving voltage, luminous efficiency, and lifetime characteristics are provided.

[0009] Fused ring compounds are represented by chemical formula 1.

[0010] Chemical Formula 1

[0011]

[0012] In chemical formula 1, X1 and X2 are each independently oxygen, sulfur, or selenium; and Ar1 and Ar2 are each independently C6-C containing an aromatic ring. 60 A fused ring.

[0013] In chemical formula 1, R1 and R2 are each independently hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C1-C 60 Heterocyclic alkyl, substituted or unsubstituted C1-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups. Silicyl groups may be as defined herein.

[0014] In chemical formula 1, at least one of R1 in number a1 and / or at least one of R2 in number a2 is an electron-withdrawing group or a group substituted by an electron-withdrawing group, wherein the electron-withdrawing group has a para-Hammett substituent constant (σ) greater than 0 according to the Hammett equation. p ).

[0015] In chemical formula 1, a1 and a2 are each an integer selected from 1 to 6.

[0016] In chemical formula 1, when R1 and R2 are each two or more independently, the two or more of each of R1 and R2 are the same or different.

[0017] In Formula 1, two or more adjacent R1s are optionally combined with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring, and two or more adjacent R2s are optionally combined with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring.

[0018] In some embodiments, the electron-withdrawing groups may be independently -F, -Cl, -Br, -I, -SF5, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, or substituted or unsubstituted π-electron-deficient nitrogen-containing C3-C groups. 30 Cyclic groups.

[0019] The light-emitting device may include a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode. The intermediate layer may include a hole transfer region, an emission layer, and an electron transfer region, and the hole transfer region may include a fused-ring compound represented by chemical formula 1.

[0020] Electronic devices may include light-emitting devices.

[0021] The fused-ring compound represented by chemical formula 1 according to embodiments of this disclosure can provide improved driving voltage, luminous efficiency, and lifetime characteristics.

[0022] The light-emitting device and the electronic device including the light-emitting device according to the embodiments of the present disclosure can provide improved driving voltage, luminous efficiency and lifetime characteristics. Attached Figure Description

[0023] Figures 1 to 6 A schematic cross-sectional view illustrating a light-emitting device according to one or more exemplary embodiments.

[0024] Figure 7 A schematic cross-sectional view illustrating a display device according to one or more exemplary embodiments.

[0025] Figure 8 A schematic cross-sectional view illustrating a display device according to one or more exemplary embodiments.

[0026] Figure 9 A schematic cross-sectional view illustrating the stacked configuration of light-emitting structures in a display device according to one or more exemplary embodiments.

[0027] Figure 10 A schematic cross-sectional view illustrating a display device according to one or more exemplary embodiments.

[0028] Figure 11 A schematic cross-sectional view illustrating a display device according to one or more exemplary embodiments.

[0029] Figure 12 A schematic exploded perspective view for illustrating an electronic device according to one or more exemplary embodiments.

[0030] Figure 13 A schematic diagram illustrating an electronic device according to one or more exemplary embodiments.

[0031] Figure 14 This is a block diagram of an electronic device according to one or more exemplary embodiments.

[0032] Figure 15 This is a schematic diagram of an electronic device according to one or more exemplary embodiments. Detailed Implementation

[0033] Fused-ring compounds represented by Formula 1 comprise a core containing a 5-membered ring containing X1 and a 5-membered ring containing X2 fused together (e.g., two dihydrofuran groups fused together), and two or more aromatic ring structures fused to the core, and have one or more electron-withdrawing groups bonded to the aromatic ring structures or one or more groups substituted with electron-withdrawing groups. Accordingly, the HOMO and LUMO energy levels can be tuned to levels suitable for exciton formation in the emitter layer. Additionally, fused-ring compounds represented by Formula 1 can provide improved hole mobility and lower electron mobility.

[0034] Fused ring compounds represented by chemical formula 1 have increased conjugation lengths to achieve improved structural and chemical stability.

[0035] In an example implementation, a fused-ring compound represented by Formula 1 can be used in the hole transfer region of a light-emitting device to improve the luminous efficiency and lifetime characteristics of the device.

[0036] According to this disclosure, light-emitting devices and electronic devices including fused-ring compounds represented by chemical formula 1 are also provided.

[0037] Definition of terminology

[0038] This disclosure may have various modifications and may be embodied in different forms, and exemplary embodiments will be explained in more detail with reference to the accompanying drawings. However, this disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, all modifications, equivalents, and alternatives that are included within the spirit and scope of this disclosure should be included herein.

[0039] The same reference numerals refer to the same elements throughout the drawings, and their repeated descriptions are not required. In the drawings, the dimensions of the structures may be enlarged for clarity of explanation. 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. Therefore, without departing from the teachings of this disclosure, a first element may alternatively be referred to as a second element. Similarly, a second element may be referred to as a first element. As used herein, unless the context clearly indicates otherwise, the singular forms such as “a,” “an,” and “described” are intended to also include the plural forms.

[0040] It will be further understood that, when used in this specification, the terms “includes,” “including,” “comprises,” and / or “comprising” indicate the presence of a described feature, number, step, operation, element, part, or combination thereof, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, parts, or combinations thereof.

[0041] As used herein, expressions such as “at least one of,” “one of,” and “selected from” before / after a list of elements modify the entire list of elements and do not modify any individual element in the list. As used herein, the term “and / or” includes any and all combinations of one or more associated enumerated items. Furthermore, when describing embodiments of this disclosure, the use of “may” refers to “one or more embodiments of this disclosure.”

[0042] It will also be understood that when a layer, film, region, plate, etc., is referred to as being "on" or "above" another part, it may be "directly on" the other part, or an intermediary layer may also be present. When a layer, film, region, plate, etc., is referred to as being "below" or "under" another part, it may be "directly below" the other part, or an intermediary layer may also be present. Furthermore, when an element is referred to as being disposed "on" another element, it may be disposed below the other element.

[0043] As used herein, the term "substituted or unsubstituted" may mean unsubstituted or substituted with one or more of the following substituents: for example, deuterium, halogen, cyano, nitro, amino, amine, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, phosphine oxide, phosphine sulfide, alkyl (e.g., C1-C) 60 Alkyl or C1-C 10 Alkyl), alkenyl (e.g., C2-C) 60 alkenyl or C2-C 10 alkenyl), alkynyl (e.g., C2-C) 60 Alkyne group or C2-C 10 alkynyl), alkoxy (e.g., C1-C) 60 Alkoxy or C1-C 10 alkoxy), hydrocarbon cyclic group, aryl (e.g., C6-C) 60 Aryl) or heterocyclic (e.g., C1-C) 60 Heterocyclic groups). For example, the term "substituted alkyl" can refer to a group in which at least one of the hydrogen atoms of the alkyl group is replaced by the aforementioned substituent, and thus the substituent is further bonded to the carbon atom of the alkyl group.

[0044] Substituents may include combinations of substituents selected from the above-mentioned groups. For example, at least one hydrogen atom in the alkyl, aryl, etc. group that is a substituent may be replaced by deuterium, halogen, cyano, nitro, amino, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or combinations thereof.

[0045] Among the substituents mentioned above, polyvalent substituents (such as amino, phosphine sulfide, phosphine oxide, sulfinyl, sulfonyl, oxygen, carbonyl, ester, etc.) can each be independently converted from C1 to C2. 10 Alkyl, C2-C 10 alkenyl, C2-C 10 alkynyl or C6-C 10 Aryl substitution.

[0046] In this disclosure, the oxygen group may be an alkyl or aryl group as defined herein, bonded to an oxygen atom. The oxygen group may be an alkoxy or aryloxy group. The alkoxy group may be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited and may be, for example, 1 to 60, 1 to 30, 1 to 20, or 1 to 10. The number of carbon atoms in the aryloxy group is not specifically limited, but may be, for example, 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of oxygen groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc., but the embodiments are not limited thereto.

[0047] In this disclosure, the thio group may be alkylthio or arylthio. The thio group may be an alkyl or aryl group bonded to a sulfur atom as defined herein. The alkyl group in the alkylthio group may be straight-chain, branched, or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 60, 1 to 30, 1 to 20, or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of thio groups may include methylthio, ethylthio, propanethio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthio, etc., but the embodiments are not limited thereto.

[0048] In this disclosure, the number of carbon atoms in the carbonyl group is not particularly limited and can be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may include one of the following structures, but the embodiments are not limited thereto.

[0049]

[0050] In this disclosure, the ester group may refer to -COOR, where R may be, for example, alkyl or aryl, such as C1-C 10 alkyl.

[0051] In this disclosure, the boron group may be an alkyl or aryl group as defined herein, bonded to a boron atom. The boron group may be an alkylboron group or an arylboron group. The alkyl group in the alkylboron group may be linear, branched, or cyclic. The number of carbon atoms in the alkylboron group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylboron group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the boron group may include dimethylboron, diethylboron, tert-butylmethylboron, diphenylboron, phenylboron, etc., but the embodiments are not limited thereto.

[0052] In this disclosure, the sulfinyl group may be an alkyl or aryl group as defined herein, bonded to -S (=O)-. The number of carbon atoms in the sulfinyl group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include alkylsulfinyl groups and arylsulfinyl groups. For example, the sulfinyl group may have the following structures, but is not limited thereto.

[0053]

[0054] In this disclosure, the sulfonyl group may be an alkyl or aryl group as defined herein, bonded to -S(=O)2-. The number of carbon atoms in the sulfonyl group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfonyl group may include alkylsulfonyl and arylsulfonyl groups. For example, the sulfonyl group may have the following structures, but is not limited thereto.

[0055]

[0056] In this disclosure, the phosphine oxide group may be an alkyl or aryl group as defined herein, bonded to -P (=O)-. The number of carbon atoms in the phosphine oxide group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include alkylphosphine oxide groups and arylphosphine oxide groups. For example, the phosphine oxide group may have the following structures, but is not limited thereto.

[0057]

[0058] In this disclosure, the phosphine sulfide group may be an alkyl or aryl group as defined herein, bonded to -P (=S)-. The number of carbon atoms in the phosphine sulfide group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine sulfide group may include alkylphosphine sulfide groups and arylphosphine sulfide groups. For example, the phosphine sulfide group may have the following structures, but is not limited thereto.

[0059]

[0060] In this disclosure, symbols and Each represents a bond that connects to an adjacent atom in the corresponding formula or part.

[0061] As used herein, in the term "substituted or unsubstituted C" a -C b In the "Y group", the range from a to b refers to the number of carbon atoms in the unsubstituted Y group, and may exclude the number of carbon atoms of the substituents bonded to it.

[0062] As used herein, the term "alkyl" can be a monovalent hydrocarbon group in which one hydrogen atom is removed from a straight-chain or branched hydrocarbon group. The number of carbon atoms in an alkyl group can be 1 to 60, 1 to 50, 1 to 40, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups may include methyl, ethyl, propyl, sec-butyl, tert-butyl, isobutyl, pentyl (e.g., neopentyl), 2-ethylbutyl, 3,3-dimethylbutyl, hexyl, heptyl, or octyl, etc.

[0063] As used herein, the term "alkylene" may refer to a divalent hydrocarbon group in which two hydrogen atoms have been removed from a straight-chain hydrocarbon group or a branched hydrocarbon group.

[0064] As used herein, the term "alkenyl" may have the same skeleton as an alkyl group and may be a monovalent hydrocarbon group comprising at least one carbon-carbon double bond. There is no particular limitation on the number of carbon atoms in an alkenyl group and it may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. As used herein, the term "alkenyl" may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkenyl group.

[0065] As used herein, the term "alkynyl" may have the same skeleton as an alkyl group and may be a monovalent hydrocarbon group comprising at least one carbon-carbon triple bond. There is no particular limitation on the number of carbon atoms in the alkynyl group and it may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. As used herein, the term "ynynyl" may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkynyl group.

[0066] As used herein, the term "cycloalkyl" refers to a monovalent saturated hydrocarbon group having carbon atoms as cyclic atoms, and the number of carbon atoms in a cycloalkyl group can be 3 to 60, 3 to 50, 3 to 30, 3 to 20 or 3 to 10, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, etc.

[0067] As used herein, the term "heterocyclic alkyl" refers to a monovalent saturated group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclizing atom and a carbon atom as a cyclizing atom, wherein the number of carbon atoms in the heterocyclic alkyl group may be 1 to 60, 1 to 30, 1 to 20, or 1 to 10, and non-limiting examples include tetrahydrofuranyl or tetrahydrothiophenyl.

[0068] As used herein, the term "cycloalkenyl" refers to a monovalent group having a carbon atom as a cyclic atom and having at least one carbon-carbon double bond in its ring and being non-aromatic. The number of carbon atoms in a cycloalkenyl group can be 5 to 60, 5 to 30, 5 to 20, or 5 to 10, and non-limiting examples include cyclopentenyl, cyclohexenyl, or cycloheptenyl, etc.

[0069] As used herein, the term "heterocyclic alkenyl" refers to a monovalent group having at least one heteroatom selected from B, N, O, P, Si, Ge, Se, and S as a cyclizing atom and a carbon atom as a cyclizing atom, and having at least one double bond in its ring. The number of carbon atoms in a heterocyclic alkenyl group can be 1 to 60, 1 to 30, 1 to 20, or 1 to 10. Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl or 2,3-dihydrothiophenyl, etc.

[0070] As used herein, the term "aryl" can refer to a monovalent hydrocarbon group in which a hydrogen atom has been removed from a hydrocarbon group having an aromatic structure. The definition of aryl can also encompass groups in which multiple aromatic rings are directly linked, such as biphenyl. The number of cyclic carbon atoms in an aryl group can be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups may include, for example, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, tetraphenyl, biphenyl, terphenyl, tetraphenyl, or 1,2-benzophenanthryl.

[0071] As used herein, groups in which two or more aryl rings are fused or linked to each other by alicyclic hydrocarbon rings (e.g., fluorenyl) may be included in the definition of aryl. In some embodiments, the alicyclic hydrocarbon ring may be an aliphatic hydrocarbon ring. The aliphatic hydrocarbon ring may have 5 to 50 carbon atoms or 5 to 30 carbon atoms, and may be, for example, a 5-membered ring or a 6-membered ring.

[0072] For example, biphenyl can be interpreted as aryl, or as a phenyl group substituted with a phenyl group.

[0073] As used herein, the term "aryl" may refer to a divalent hydrocarbon group in which one hydrogen atom is removed from an aryl group.

[0074] As used herein, the term "alkylaryl" refers to an aryl group substituted with at least one alkyl group, wherein the number of carbon atoms in the alkylaryl group may be 7 to 60, 7 to 50, 7 to 40, 7 to 30, 7 to 20, or 7 to 15. As used herein, the term "aralkyl" refers to an alkyl group substituted with at least one aryl group, wherein the number of carbon atoms in the aralkyl group may be 7 to 60, 7 to 50, 7 to 40, 7 to 30, 7 to 20, or 7 to 15.

[0075] As used herein, the term "heteroaryl" can be a monovalent group having an aromatic structure comprising at least one heteroatom selected from B, O, N, P, S, Si, Se, and Ge as a cyclic atom, wherein the number of cyclic carbon atoms in the heteroaryl can be 1 to 60, 1 to 50, 1 to 40, 1 to 30, 1 to 20, or 1 to 15. As used herein, the term "hybrid aryl" can be a divalent group having an aromatic structure comprising at least one heteroatom (e.g., B, O, N, P, S, Si, Se, or Ge) as a cyclic atom. When a heteroaryl or hybrid aryl comprises two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. Non-limiting examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl or dibenzofuranyl, etc.

[0076] As used herein, groups in which two or more aryl rings are fused or attached to non-aromatic heterocyclic groups (such as carbazole groups) may also be included in the definition of heteroaryl.

[0077] As used herein, the term "alkylheteroaryl" refers to a heteroaryl group substituted with at least one alkyl group, and the number of carbon atoms in the alkylheteroaryl group can be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20, or 2 to 15. As used herein, the term "heteroarylalkyl" refers to an alkyl group substituted with at least one heteroaryl group, and the number of carbon atoms in the heteroarylalkyl group can be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20, or 2 to 15.

[0078] As used in this document, the term "aryloxy group" indicates -OA 102 (where A) 102 (Aryl), wherein the number of carbon atoms in the aryl group can be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20 or 6 to 15, and as used herein, the term "arylthio" indicates -SA 103 (where A) 103 (For aryl), the number of carbon atoms in the arylthio group can be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20 or 6 to 15.

[0079] As used herein, the term "heteroaryloxy" indicates -OA 104 (where A) 104 (For heteroaryl groups), the number of carbon atoms in the heteroaryl group can be 1 to 60, 1 to 50, 1 to 40, 1 to 30 or 1 to 20, and as used herein, the term "heteroaryl thio" indicates -SA 105 (where A) 105 (For heteroaryl groups), the number of carbon atoms in the heteroaryl thio group can be 1 to 60, 1 to 50, 1 to 40, 1 to 30 or 1 to 20.

[0080] As used herein, the term "cyclic group" may include monocyclic or polycyclic groups, and may also include alicyclic or aromatic rings. Cyclic groups may include carbocyclic and heterocyclic groups.

[0081] As used herein, the term "polycyclic group" can be a group in which two or more rings are connected or fused together by one or more atoms. For example, a polycyclic structure (i.e., two or more rings) can include bicyclic structures, spiro structures, or fused structures formed by bridging carbons.

[0082] As used herein, the terms "fused polycyclic group" or "fused ring structure" can each refer to a group in which two or more adjacent rings in the aforementioned polycyclic structure share two or more atoms. For example, C8-C 60 Fused polycyclic groups may include C8-C 50 Fused polycyclic groups, C8-C 40 Fused polycyclic groups, C8-C 30 Fused polycyclic groups or C8-C 20 Fused polycyclic groups. Non-limiting examples of fused polycyclic groups or fused ring structures may include naphthyl, anthracene, phenanthrene, fluorenyl, pyrene, benzo[a]pyrene, pentaphenyl, poly[a]phenyl or helicenyl, etc.

[0083] As used herein, the term "carbocyclic group (e.g., C3-C)" 60 "Carbocyclic group" can be a cyclic group in which the carbon atom is the only cyclic atom. As used herein, the term "heterocyclic group" (e.g., C1-C1) refers to a cyclic group in which the carbon atom is the only cyclic atom. 60 A heterocyclic group can be a cyclic group that includes at least one heteroatom as a cyclic atom in addition to the carbon atom that serves as the cyclic atom.

[0084] As used herein, carbocyclic and heterocyclic groups can each be independently a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused together.

[0085] As used herein, the term "hydrocyclotridecyl" may refer to any optional functional group or substituent derived from an aliphatic or aromatic hydrocarbon ring. The hydrocyclotridecyl may be a saturated hydrocyclotridecyl group with 5 to 30 carbon atoms for forming the ring.

[0086] As used herein, the term "silyl" includes alkylsilyl and arylsilyl. The number of carbon atoms in an alkylsilyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in an arylsilyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Non-limiting examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, or phenylsilyl, etc. However, embodiments of this disclosure are not limited thereto.

[0087] As used herein, an amino group may include an alkylamino group, an arylamino group, or a heteroarylamino group. The alkyl group may be straight-chain, branched, or cyclic. The number of carbon atoms in the alkylamino group is not specifically limited, but may be, for example, 1 to 30, 1 to 20, or 1 to 10. The number of carbon atoms in the arylamino group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. The number of carbon atoms in the heteroarylamino group is not specifically limited, but may be, for example, 1 to 30, 1 to 20, or 1 to 15. Non-limiting examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, or 9-methyl-anthraylamino, etc.

[0088] In this disclosure, "integers selected from 0 to 10" refers to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of numerical ranges also applies to any other numerical ranges appearing in the specification, such as integers selected from 0 and 1, integers selected from 0 to 2, integers selected from 0 to 3, integers selected from 0 to 4, integers selected from 0 to 5, integers selected from 0 to 6, integers selected from 0 to 7, integers selected from 0 to 8, integers selected from 0 to 9, and integers selected from 0 to 10, etc.

[0089] Fused ring compounds

[0090] Fused ring compounds are represented by chemical formula 1.

[0091] Chemical Formula 1

[0092]

[0093] In chemical formula 1, X1 and X2 are each independently oxygen, sulfur, or selenium. Ar1 and Ar2 are each independently C6-C atoms including an aromatic ring. 60 A fused ring.

[0094] In chemical formula 1, R1 and R2 are each independently hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C1-C 60 Heterocyclic alkyl, substituted or unsubstituted C1-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups.

[0095] In chemical formula 1, at least one of the R1 groups in number a1 and / or at least one of the R2 groups in number a2 are electron-withdrawing groups or groups substituted by electron-withdrawing groups. Electron-withdrawing groups are those having a para-Hammett substituent constant (σ) greater than 0 according to the Hammett equation. p ) group.

[0096] In chemical formula 1, a1 and a2 are each an integer selected from 1 to 6.

[0097] In chemical formula 1, when R1 and R2 are each two or more independently, the two or more of each of R1 and R2 are the same or different.

[0098] In Formula 1, two or more adjacent R1s are optionally combined with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring, and two or more adjacent R2s are optionally combined with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring.

[0099] Fused ring compounds represented by chemical formula 1 can have high structural and chemical stability through extended conjugation lengths, and can easily generate excitons by improving hole mobility and reducing electron mobility.

[0100] Light-emitting devices, including those containing fused-ring compounds represented by Formula 1, can provide sufficient luminous efficiency and improved lifetime at relatively low driving voltages.

[0101] In some embodiments, the saturated ring may be independently selected from 5-membered, 6-membered, and 7-membered rings, and the ring may be a hydrocarbon ring or a ring containing heteroatoms. The saturated ring may be unsubstituted or substituted with deuterium, -F, -Cl, -CD3, -CD2H, -CDH2, or Cl-C. 10 Straight-chain alkyl, C3-C 10 Branched alkyl, C2-C 10 Straight-chain alkenyl, C3-C 10 Branched alkenyl and C6-C 10 At least one substitution of the aryl group.

[0102] In some embodiments, the unsaturated ring may be independently selected from 5-membered, 6-membered, and 7-membered rings, and the ring may be a hydrocarbon ring or a ring containing heteroatoms. The unsaturated ring may be, for example, a cycloalkene or aromatic ring containing a C=C unsaturated double bond. The unsaturated ring may be unsubstituted or substituted with deuterium, -F, -Cl, -CD3, -CD2H, -CDH2, or C1-C. 10 Straight-chain alkyl, C3-C 10 Branched alkyl, C2-C 10 Straight-chain alkenyl, C3-C 10 Branched alkenyl and C6-C 10 At least one substitution of the aryl group.

[0103] In some embodiments, the saturated or unsaturated ring may be selected from, for example, cyclopentane, cyclohexane, cycloheptane, cyclooctane, benzene, pyrrole, furan, thiophene, pyridine, imidazole, pyrimidine, pyridazine, pyrazine, furazolidone, oxazole, isoxazole, oxazine, thiazole, benzoxazine, benzothiazole, benzonaphthalene, dibenzofuran, dibenzothiophene, benzopyran, coumarin, phenanthrene, benzophenanthrene, anthracene, fluorene, pyrene, quinoline, isoquinoline, carbazole, indole, isoindole, or quinoxaline, each of which may be independently substituted or unsubstituted.

[0104] Fused ring compounds represented by Formula 1 include at least one electron-withdrawing group to improve hole mobility.

[0105] The Hammett equation can be used to measure the degree to which a functional group withdraws or donates electrons. The para-Hammett substituent constant (σ) is determined by the Hammett equation. p The information can be found in literature (e.g., "A survey of Hammett substituent constants and resonance and field parameters"), but even without referring to such literature, the para-Hamett substituent constant (σ) can be measured based on the Hammett equation. p ).

[0106] In some embodiments, the electron-withdrawing group may have a para-Hammett substituent constant (σ) greater than 0.05 according to the Hammett equation. p ).

[0107] In some embodiments, the electron-withdrawing group may be -F, -Cl, -Br, -I, -SF5, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, or a substituted or unsubstituted π-electron-deficient nitrogen-containing C3-C group. 30 Cyclic groups. Accordingly, the HOMO and LUMO energy levels of the fused-ring compound represented by Formula 1 can be adjusted to further increase hole mobility and further decrease electron mobility.

[0108] As used in this article, “nitrogen-containing C3-C lacking π electrons” 30 "Cyclic group" refers to a cyclic group having 3 to 30 carbon atoms and including *-N=*' as the cyclic part.

[0109] In some embodiments, the electron-withdrawing group may independently be -F, -Cl, -Br, -I, -SF5, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, substituted or unsubstituted triazine, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoxenolinyl, substituted or unsubstituted phenanthrolinel, or substituted or unsubstituted acridineyl.

[0110] In some embodiments, the substitution may further include substitution with an electron-withdrawing group. For example, the substituted triazine, substituted thiazolyl, substituted benzothiazolyl, substituted pyrazinyl, substituted pyridinyl, substituted pyridazinyl, substituted pyrimidinyl, substituted naphridinyl, substituted phthalazinyl, substituted quinolinyl, substituted quinazolinyl, substituted benzozolinyl, substituted phenanthrolinel, and substituted acridineyl may be triazine, thiazolyl, benzothiazolyl, pyrazinyl, pyridinyl, pyridinyl, pyrimidinyl, naphridinyl, or substituted triazine, thiazolyl, benzothiazolyl, pyridinyl, naphridinyl, or substituted benzothiazolyl may be substituted with at least one of the following: Phthalasinyl, Quinolinyl, Quinazolinyl, Benzo[a]-Cal, Phenanthrolineyl, and Acridineyl: -F, -Cl, -Br, -I, -SF5, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, Triazinyl, Thiazolyl, Benzo[a]-Thiazolyl, Pyrazinyl, Pyridinyl, Pyridinyl, Pyridinyl, Pyrimidinyl, Naphridinyl, Phthalasinyl, Quinolinyl, Quinazolinyl, Benzo[a]-Cal, Phenanthrolineyl, and Acridineyl.

[0111] In some embodiments, Ar1 and Ar2 may each independently represent the groups in which the benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, tetraphenyl ring, pyrene ring, or benzo[a]pyrene ring is fused.

[0112] In some embodiments, Ar1 and Ar2 may each independently represent the groups in which the benzene ring or naphthalene ring is fused.

[0113] Accordingly, fused-ring compounds represented by Formula 1 can have extended conjugation lengths, thereby further improving structural and chemical stability.

[0114] In some embodiments, the fused-ring compound represented by chemical formula 1 may be represented by chemical formula 1-1.

[0115] Chemical Formula 1-1

[0116]

[0117] In chemical formula 1-1, a1 and a2 are each independently an integer selected from 1 to 4. The constraints on X1, X2, R1, and R2 are the same as those provided for chemical formula 1.

[0118] In some embodiments, the fused ring compound represented by chemical formula 1 may be represented by chemical formula 1-2, chemical formula 1-3 or chemical formula 1-4.

[0119] Chemical formula 1-2

[0120]

[0121] Chemical formulas 1-3

[0122]

[0123] Chemical formulas 1-4

[0124]

[0125] In chemical formulas 1-2, 1-3, and 1-4, a1 is an integer selected from 1 to 4, and a2 is an integer selected from 1 to 6. The constraints on X1, X2, R1, and R2 are the same as those provided for chemical formula 1.

[0126] In some embodiments, the fused-ring compound represented by formula 1 may be represented by formulas 1-5, 1-6, 1-7, 1-8, 1-9 or 1-10.

[0127] Chemical formulas 1-5

[0128]

[0129] Chemical formulas 1-6

[0130]

[0131] Chemical formulas 1-7

[0132]

[0133] Chemical formulas 1-8

[0134]

[0135] Chemical formulas 1-9

[0136]

[0137] Chemical formulas 1-10

[0138]

[0139] In chemical formulas 1-5, 1-6, 1-7, 1-8, 1-9, and 1-10, the constraints on X1, X2, R1, R2, a1, and a2 are the same as those provided for chemical formula 1.

[0140] In some embodiments, the fused-ring compound represented by Formula 1 may have a 1.30 × 10⁻⁶ Ω·cm². -3 square centimeters per volt-second (cm) 2 / V·s) to 2.50×10 -2 cm 2 Hole mobility per V·s. In an embodiment, the hole mobility of the fused-ring compound represented by Formula 1 can be 1.35 × 10⁻⁶. -3 cm2 / V·s up to 2.30×10 -2 cm 2 / V·s. Hole mobility can be determined using the space charge confined current (SCLC) method.

[0141] In some embodiments, the fused-ring compound represented by Formula 1 may have a 4.00 × 10⁻⁶ Ω·cm². -3 cm 2 / V·s up to 3.00×10 -2 cm 2 The electron mobility is 4.10 × 10⁻⁶ V·s. In embodiments, the electron mobility of the fused-ring compound represented by Formula 1 can be 4.10 × 10⁻⁶ V·s. -3 cm 2 / V·s up to 2.80×10 -2 cm 2 / V·s. Electron mobility can be determined using the space charge confinement current (SCLC) method.

[0142] Within the aforementioned range of hole and electron mobilities, the fused-ring compound represented by Formula 1 can generate excitons more efficiently. In some embodiments, the fused-ring compound represented by Formula 1 may have a glass transition temperature of 110°C to 190°C. In other embodiments, the glass transition temperature of the fused-ring compound represented by Formula 1 may be 120°C to 180°C. Within the aforementioned range of glass transition temperatures, lifetime characteristics can be further improved. The glass transition temperature can be determined by differential scanning calorimetry (DSC).

[0143] In some embodiments, the fused-ring compound represented by Formula 1 may have a highest occupied molecular orbital (HOMO) energy level from -9.0 eV to -6.0 eV. In some embodiments, the HOMO energy level of the fused-ring compound represented by Formula 1 may be from -8.5 eV to -6.2 eV. The HOMO energy level can be determined by cyclic voltammetry (CV).

[0144] In some embodiments, the fused-ring compound represented by Formula 1 may have a lowest unoccupied molecular orbital (LUMO) energy level of -5.8 eV to -4.9 eV. In other embodiments, the LUMO energy level of the fused-ring compound represented by Formula 1 may be -5.6 eV to -5.0 eV. The LUMO energy level can be determined by cyclic voltammetry (CV).

[0145] The fused-ring compound represented by Formula 1 may have HOMO and / or LUMO energy levels within the above range, so that light-emitting devices comprising the fused-ring compound represented by Formula 1 can have improved luminous efficiency and lifetime characteristics at relatively low driving voltages.

[0146] In some embodiments, the fused-ring compound represented by Formula 1 may be one of compounds 1 to 36:

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] .

[0159] Light-emitting device

[0160] Figures 1 to 6 A schematic cross-sectional view is provided to illustrate the light-emitting device according to an exemplary embodiment.

[0161] refer to Figure 1 The light-emitting device ED may include a first electrode 110, a second electrode 150, and an intermediate layer ITL disposed between the first electrode 110 and the second electrode 150. The intermediate layer ITL may include a hole transfer region 120, an emission layer 130, and an electron transfer region 140.

[0162] Hole transfer region 120 may include the fused ring compound represented by chemical formula 1 to achieve improved driving voltage and lifetime characteristics, and provide sufficient luminous efficiency.

[0163] In some embodiments, the hole transfer region 120 may include at least one of a hole injection layer 122, a hole transport layer 124, and an electron blocking layer 126, and at least one of the hole injection layer 122, the hole transport layer 124, and the electron blocking layer 126 may include a fused ring compound represented by chemical formula 1.

[0164] In some embodiments, at least one of the hole injection layer 122, the hole transport layer 124, and the electron blocking layer 126 may include at least one of the fused ring compounds represented by chemical formula 1 described above.

[0165] In some embodiments, the fused-ring compound represented by Formula 1 may include at least one compound represented by any one of Formulas 1-1 to 1-10 described herein.

[0166] In some embodiments, the fused-ring compound represented by Formula 1 may include at least one of Compound 1 to Compound 36.

[0167] In some embodiments, the emitting layer 130 may emit blue light with a maximum emission center wavelength of 430 nanometers (nm) to 490 nm.

[0168] The light-emitting device ED may include, for example, two or more light-emitting structures, each of which includes an emitting layer 130 between a first electrode 110 and a second electrode 150. The light-emitting structures may include, for example, a stacked structure of a hole transfer region 120, an emitting layer 130, and an electron transfer region 140. A charge-generating layer may be disposed between the light-emitting structures. The charge-generating layer may include a p-type charge-generating layer and / or an n-type charge-generating layer.

[0169] The first electrode 110 may be an anode or a cathode. In some embodiments, the first electrode 110 may be used as an anode and may also be used as a pixel electrode. In this case, the first electrode 110 may include a conductive material with a high work function that facilitates hole injection.

[0170] In this embodiment, the first electrode 110 may be a transmission electrode. The first electrode 110 may include a transparent conductive oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).

[0171] In an embodiment, the first electrode 110 may be a semi-transparent electrode or a reflective electrode. The first electrode 110 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, In, Sn, and Zn, or an alloy or compound containing at least one of them (e.g., LiF). For example, the first electrode 110 may include Li, Ca, LiF / Ca (a stacked structure of LiF and Ca), LiF / Al (a stacked structure of LiF and Al), or a mixture of Ag and Mg, etc., but the embodiments are not limited thereto.

[0172] The first electrode 110 may have a single-layer structure or a multi-layer structure. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0173] The thickness of the first electrode 110 can be from about 700 Å to about 10,000 Å. For example, the thickness of the first electrode 110 can be from about 1,000 Å to about 3,000 Å.

[0174] The second electrode 150 may be a cathode or an anode. In some embodiments, the second electrode 150 may be used as an electron injection electrode or as a cathode. The second electrode 150 may include metals, alloys, or conductive compounds, each having a low work function.

[0175] For example, the second electrode 150 may include lithium (Li), sodium (Na), silver (Ag), magnesium (Mg), aluminum (Al), silver-lithium (Ag-Li), silver-sodium (Ag-Na), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, or IZO, etc. The second electrode 150 may include one or a combination of the aforementioned materials.

[0176] The second electrode 150 can be a transmission electrode, a semi-transparent electrode, or a reflection electrode. The second electrode 150 can have a single-layer structure or a multi-layer structure.

[0177] The emitter layer 130 may include a host and a dopant.

[0178] In a non-limiting example, the emitter layer 130 may include dopant in an amount of about 0.01 parts by weight to about 15.00 parts by weight or about 0.01 parts by weight to about 12.00 parts by weight based on 100 parts by weight of the body.

[0179] The emitting layer 130 may emit red, green, blue, and / or white light. For example, the emitting layer 130 may emit blue light.

[0180] In some implementations, the emission half-width (FWHM) of blue light can be about 30 nm or less, or about 28 nm or less.

[0181] For example, the emitter layer 130 may include a host material, such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzoanthene derivatives, or triphenylene derivatives.

[0182] In some embodiments, the emitting layer 130 may include a host material, for example, represented by the chemical formula FH. For example, a compound represented by the chemical formula FH may be used as a fluorescent host material.

[0183] Chemical formula FH

[0184]

[0185] In the chemical formula FH, RFH1 To R FH4 Each can independently be a hydrogen atom, deuterium, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted thio group, substituted or unsubstituted oxygen group, or substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C1-C 30 Heteroaryl groups or cyclic groups formed by combinations of these groups. In embodiments, in the chemical formula FH, R FH1 To R FH4 At least one of them can form a fused ring with the bonded benzene ring.

[0186] In the chemical formula FH, x1a and x1b can each be an integer selected from 0 to 5; and x2a and x2b can each be an integer selected from 0 to 4. When x1a, x1b, x2a, and x2b are each 2 or greater, R FH1 To R FH4 Each of the two or more of them can be the same as or different from each other.

[0187] In some embodiments, the emitting layer 130 may include a host material, for example, represented by the chemical formula pH. For example, a compound represented by the chemical formula pH may be used as a host material for a phosphorescent device.

[0188] Chemical formula pH

[0189]

[0190] In the chemical formula pH, R PH It can be a substituted or unsubstituted carbazole group. L PH It can be directly connected, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C1-C 30 Hybrid aryl. Ar PH C6-C can be substituted or unsubstituted. 30 aryl or substituted or unsubstituted C1-C 30 Mixed aromatic compounds.

[0191] As described in the definition of the term above, the term "C6-C" 30 "Aryl" can encompass groups in which multiple aryl rings are fused or bonded together by cyclic groups (e.g., alicyclic hydrocarbon rings). For example, C6-C 30 Aryl groups may include fluorene groups.

[0192] As described in the definition of the term above, the term "C1-C" 30"Heteroaryl" can encompass groups in which multiple aryl rings are fused or bonded together by heterocyclic groups. For example, C1-C 30 The heteroaryl group may include carbazole, dibenzofuran, or dibenzothiophene, etc. In the embodiments, C1-C 30 A heteroaryl group can be a group in which multiple aryl rings are fused or bonded to each other by the same or different heterocyclic groups.

[0193] In the implementation, it includes Ar PH The substituents in it may include those derived from -Si(R) sa (R) sb (R) sc ) represents silyl group; and R sa R sb and R sc Each can be independently hydrogen, deuterium, halogen, hydroxyl, or C1-C. 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C6-C 60 Aryl or C1-C 30 Mixed aromatics. R sa R sb and R sc At least one of them can be C6-C 60 Aryl or C1-C 30 heteroaryl. For example, R sa R sb and R sc Each can be independently C6-C 60 Aryl or C1-C 30 Mixed aromatic compounds.

[0194] In the chemical formula pH, lx can be an integer selected from 0 to 10. When lx is 2 or greater, two or more L... PH They may be the same as or different from each other.

[0195] The emitter layer 130 may include, for example, BCPDS (bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), mCBP (3,3'-bis(9H-carbazole-9-yl)-1,1'-biphenyl), CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphospho)dibenzo[b,d]furan), TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine), TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), Alq3 (Tris(8-hydroxyquinoline)aluminum), ADN (9,10-bis(naphthyl-2-yl)anthracene), TBADN (2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene), DSA (stilbene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthyl-2-yl)anthracene), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane) or DPSiO4 (octaphenylcyclotetrasiloxane) etc. are used as main materials.

[0196] In an implementation, the body in the emitting layer 130 may include one or any combination of the body materials described above.

[0197] The following are non-limiting examples of main materials:

[0198]

[0199]

[0200]

[0201]

[0202] .

[0203] The emitter layer 130 may further include dopants that interact with the host material.

[0204] In some embodiments, the emitter layer 130 may include a dopant represented by the chemical formula FD. For example, a compound represented by the chemical formula FD may be used as a fluorescent dopant.

[0205] Chemical formula FD

[0206]

[0207] In the chemical formula FD, Ar FD R FD1 and R FD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic base. Ax can be an integer selected from 1 to 6.

[0208] In some implementations, Ar FD It may include fused ring structures in which three or more aryl rings (e.g., benzene rings) are fused together (e.g., anthracene, 1,2-benzophenanthrene, pyrene, etc.).

[0209] In some embodiments, the emitting layer 130 may include a phosphorescent dopant. The phosphorescent dopant may include an organometallic compound comprising a central metal and at least one ligand coordinated to the central metal. The central metal may include, for example, a transition metal, and the ligand may include, for example, a monodentate ligand, a bidentate ligand, a tripentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a combination thereof.

[0210] Phosphorescent dopants may include, for example, compounds represented by the chemical formula PD.

[0211] Chemical formula PD

[0212] M(L d 1 ) dx1 (L d 2 ) dx2

[0213] In the chemical formula PD, M can be a transition metal atom, such as iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), ruthenium (Ru), copper (Cu), or thulium (Tm).

[0214] In the chemical formula PD, L d 1 It can be a ligand represented by the chemical formula LD1.

[0215] Chemical formula LD1

[0216]

[0217] In the chemical formula LD1, X PD1 and X PD2 Each can be either C or N independently.

[0218] In the implementation method, X PD1 and X PD2 One of them can be C, and X PD1 and X PD2 The other one in X can be N. In the implementation, X PD1 and X PD2 Each can be N.

[0219] In the chemical formula LD1, CG PD1 and CG PD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic groups. For example, CG. PD1 and CG PD2 Each of these can independently be pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, phenyl, pyridinyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, fluorenyl, dibenzothiopyrroleyl, naphthobenzofuranyl, naphthobenzothiopheneyl, benzocarbazoleyl, benzofluorenyl, naphthobenzothiopyrroleyl, dinaphthofuranyl, dinaphthothiopheneyl, diphenyl α-carbazolyl, dibenzofluorenyl, dinaphthothiol, azidobenzofuranyl, azidobenzothiopheneyl, azidocarbazolyl, azidofluorenyl, azidobenzothiol, azidobenzobenzofuranyl, azidobenzobenzothiopheneyl, azidocarbazolyl, azidobenzofluorenyl, azidobenzobenzothiol, azidobenzofuranyl, azidobenzothiopheneyl, azidobenzocarbazolyl, or azidobenzothiol.

[0220] In the chemical formula LD1, L PD It can be a single bond, a substituted or unsubstituted methylene, a substituted or unsubstituted ethylene, *-O-*', *-S-*', *-C(=O)-*', or *-N(R) PD3 )-*'、*-C(R PD4 )=*' or *=C(R) PD5 )-*'.

[0221] In the chemical formula LD1, X PD3 and X PD4 Each can independently form a chemical bond, O, S, N (R) PD6 ), B(R) PD7 ), P(R PD8 ), C(R PD9 (R) PD10 ) or Si(R PD11 (R) PD12 Chemical bonds can be, for example, covalent bonds or coordinate bonds.

[0222] In the chemical formula LD1, R PD1 and R PD2 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C1-C 60 Heterocyclic alkyl, substituted or unsubstituted C1-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, substituted or unsubstituted aniline groups, -B(R) PD13 (R) PD14 -C(=O)(R) PD15 -S(=O)2(R) PD16 ), -P(R PD17 (R) PD18 ) or -P(=O)(R PD17 (R) PD18 As explained above, silyl groups can be formed from -Si(R) sa (R) sb (R) sc )express.

[0223] R PD3 To R PD18Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C1-C 60 Heterocyclic alkyl, substituted or unsubstituted C1-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0224] In the chemical formula LD1, cx1 and cx2 can each be an integer selected from 0 to 10 independently. When at least one of cx1 and cx2 is 2 or greater, two or more R... PD1 Or two or more R PD2 They may be the same as or different from each other.

[0225] The symbols -* and -*' in the chemical formula LD1 each represent the bonding sites where the ligand represented by chemical formula LD1 is bonded to M in chemical formula PD.

[0226] In the chemical formula PD, dx1 can be an integer selected from 1 to 3. When dx1 is 2 or 3, it represents two or three L... d 1 They can be the same or different from each other. In two or three Ls d 1 In the middle, CGs that are adjacent to each other PD1 and / or CGPD2 It can be connected by a linking group (such as L) PD1 or L PD2 (etc.) are connected to each other. Connecting groups (e.g., L...) PD1 L PD2 (etc.) can each independently relate to the reference L PD The same as the one that is defined.

[0227] In the chemical formula PD, L d 2 It can be an organic ligand. L d 2 It may include, for example, halogen groups, CO, NO, CS, pyridinecarboxyl groups, acetate groups, oxalate groups, diketone groups, isonitrile groups, isothiocyanate-N groups, thiosulfate-S groups, alkylphosphin groups, arylphosphin groups (e.g., phenylphosphin groups), phosphine oxide groups, phosphite groups, or combinations thereof.

[0228] In the chemical formula PD, dx2 is an integer selected from 0 to 4. When dx2 is 2 or greater, two or more L d 2 They may be the same as or different from each other.

[0229] Non-limiting examples of phosphorescent dopants are as follows:

[0230]

[0231]

[0232]

[0233]

[0234] .

[0235] In some embodiments, the emitting layer 130 may include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (NBDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), etc.), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) or pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene or 1,4-bis(N,N-diphenylamino)pyrene, etc.) as fluorescent dopant materials.

[0236] In addition to the materials mentioned above, the emitting layer 130 may also include a metal composite containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) as a phosphorescent dopant. For example, FIrpic (bis(4,6-difluorophenylpyridinyl-N,C2')pyridinecarboxyiridium(III)), FIr6 (bis(2,4-difluorophenylpyridinyl)-tetra(1-pyrazolyl)iridium(III)) or PtOEP (octaethylporphyrin platinum) can be used as phosphorescent dopant.

[0237] In one embodiment, the emitter layer 130 may include a boron-containing dopant represented by the chemical formula BD.

[0238] Chemical formula BD

[0239]

[0240] In the chemical formula BD, X BD1 and X BD2 Each can be independently N(R) BD1 ), P(R BD2 ), C(R BD3 (R) BD4 ), Si(R) BD5 (R) BD6 ), S or O. In the implementation, X BD1 and X BD2 Each can be N(R) BD1 R BD1 To R BD6 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C1-C 30 Mixed aromatics. R BD7 R BD8 and R BD9 Each can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted oxygen, substituted or unsubstituted thio, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C1-C 30 Mixed aromatics. R BD7 R BD8 and / or R BD9 It can bond with adjacent groups to form a ring.

[0241] In the chemical formula BD, CG BD1 and CGBD2 Each represents a cyclic group, and CG BD1 and CG BD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group. In some embodiments, CG BD1 and CG BD2 Each can be independently substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C1-C 30 Mixed aromatic compounds.

[0242] In the implementation method, CG BD1 and CG BD2 Each can be a substituted or unsubstituted benzene ring independently. In this case, boron-containing dopants can be used as thermally activated delayed fluorescence (TADF) dopants.

[0243] In the implementation method, CG BD1 and CG BD2 One of them can be a non-fused aryl or a non-fused heteroaryl, and the other can be a fused polycyclic aryl or a fused polycyclic heteroaryl. In this case, the boron-containing dopant can be used as a fluorescent dopant.

[0244] In an embodiment, the emitter layer 130 may include one or any combination of the dopant materials described above.

[0245] In some embodiments, the emitting layer 130 may include two or more host materials. For example, the emitting layer 130 may include a hole transport host compound and an electron transport host compound. In this case, the emitting layer 130 may include a hole transport host compound, an electron transport host compound, a photosensitizer, and a dopant. In an example embodiment, the hole transport host compound and the electron transport host compound may form an excited-state complex, and energy may be transferred from the excited-state complex to the photosensitizer and from the photosensitizer to the dopant, thereby inducing luminescence.

[0246] Non-limiting examples of hole transport host compounds may include compounds represented by the chemical formula HT as described herein. Non-limiting examples of electron transport host compounds may include compounds represented by the chemical formula ET as described herein.

[0247] In some embodiments, the emitter layer 130 may include quantum dots. Quantum dots may include group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, or combinations thereof.

[0248] Quantum dots may include a core comprising a compound as described above and a shell surrounding the core. The shell may include inorganic oxides or semiconductor compounds. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSe, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, or AlSb, etc.

[0249] In an example implementation, the color of the emitted light can be adjusted according to the particle size of the quantum dots. The quantum dots can be blue, red, or green.

[0250] Hole transfer region 120 may be formed between first electrode 110 and emitter layer 130. Hole transfer region 120 may have a single-layer structure or a multi-layer structure comprising different materials.

[0251] Hole transfer region 120 may include the aforementioned fused ring compound. For example, the fused ring compound may be used as a p-type dopant.

[0252] The hole transfer region 120 may include a hole injection layer, a hole transport layer and / or an electron blocking layer, and may further include an auxiliary emission layer.

[0253] In some implementations, such as Figure 2 As explained in the text, the hole transfer region 120 may include a hole injection layer 122 and a hole transport layer 124 stacked sequentially from the first electrode 110.

[0254] In some implementations, such as Figure 3 As illustrated, the hole transfer region 120 may include a hole injection layer 122, a hole transport layer 124, and an electron blocking layer 126 stacked sequentially from the first electrode 110. The electron blocking layer 126 can block electrons from transferring from the electron transfer region 140 to the hole transfer region 120. Accordingly, the generation of excitons in the emission layer 130 can be increased, and the luminescence efficiency can be further increased.

[0255] In some embodiments, the hole injection layer 122 may include a fused ring compound represented by Formula 1 in an amount of 1 wt% to 5 wt% based on its total weight.

[0256] In some embodiments, the hole transfer region 120 may further include the fused ring compound described herein.

[0257] For example, the hole transfer region 120 may further include a compound represented by the chemical formula HT.

[0258] Chemical formula HT

[0259]

[0260] In the chemical formula HT, L HT1 L HT2 and L HT3 Each can be independently a directly connected, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C1-C 30 Hybrid aryl.

[0261] In the chemical formula HT, lx1 to lx3 can each be an integer selected from 0 to 10 independently. When lx1, lx2, or lx3 is 2 or greater, L HT1 L HT2 and L HT3 Two or more of each of them can be obtained through, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C1-C 30 Hybrid aryl.

[0262] In the chemical formula HT, Ar HT1 and Ar HT2 Each can be independently substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C1-C 30 Mixed aromatic compounds. Ar HT3 C6-C can be substituted or unsubstituted. 30 Aryl.

[0263] In embodiments, the compound represented by the chemical formula HT may be a monoamine compound. In embodiments, the compound represented by the chemical formula HT may be a compound in which Ar... HT1 To Ar HT3 At least one of the diamine compounds includes an amino group as a substituent.

[0264] In some embodiments, the compound represented by the chemical formula HT may be Ar. HT1 and Ar HT2 At least one of the carbazole-containing compounds includes a substituted or unsubstituted carbazole group, or wherein Ar HT1 and Ar HT2 At least one of the fluorene-containing compounds includes a substituted or unsubstituted fluorene group.

[0265] In some implementations, Ar HT1 To Ar HT3 Two adjacent groups in a ring can fuse together to form a ring.

[0266] In a non-limiting example, the hole transfer region 120 may further include at least one of the following compounds, but the implementation is not limited thereto:

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274] .

[0275] For example, hole transfer region 120 may include 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), NPB (N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine), TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), spiroTPD, spiroNPB, DNTPD (N 1 N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) 1 -Phenyl-N 4 N 4-di-m-tolylphenyl-1,4-diamine), TAPC (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / CSA (polyaniline / camphor sulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine compounds, carbazole compounds (N-phenylcarbazole, polyvinylcarbazole, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole) or mDCP (1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene, etc.) or fluorene compounds, etc., may be used as hole transfer materials. Hole transfer region 120 may include one or a combination of the hole transfer materials described herein.

[0276] The hole transfer material described herein may be included in at least one of the hole injection layer 122, the hole transport layer 124, and the electron blocking layer 126.

[0277] The hole transfer region 120 may further include a charge-generating material. The charge-generating material may be a dopant material (such as a p-type dopant) to improve the conductivity of the hole transfer region 120.

[0278] Examples of dopant materials may include: metal halide compounds, such as LiF, NaCl, CsF, RbCl, RbI, CuI, or KI; quinone derivatives, such as TCNQ (tetracyanoquinone dimethyl) or F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl); cyano-containing compounds, such as HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile) or NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile); tungsten (W) oxides; or molybdenum (Mo) oxides, etc. Hole transfer region 120 may include one or a combination of the dopant materials described herein.

[0279] The thickness of the hole transfer region 120 can be from about 100 Å to about 10,000 Å. For example, the thickness of the hole transfer region 120 can be from about 100 Å to about 1,500 Å.

[0280] When the hole transfer region 120 includes a hole injection layer 122 or a hole transport layer 124, the thickness of the hole injection layer 122 may be about 100 Å to about 9,000 Å, about 100 Å to about 3,000 Å, or about 100 Å to about 1,000 Å. The thickness of the hole transport layer 124 may be about 50 Å to about 2,000 Å, about 100 Å to about 1,500 Å, about 100 Å to about 1,000 Å, or about 100 Å to about 600 Å.

[0281] Within the thickness range described herein, hole transfer characteristics are enhanced even under low-voltage operation, and the lifespan of the light-emitting device can be further improved.

[0282] Each layer of the hole transfer region 120 can be formed by processes such as thermal evaporation deposition, vacuum deposition, spin coating, inkjet printing, laser printing, casting, or laser thermal transfer.

[0283] The electron transfer region 140 may be disposed between the second electrode 150 and the emitter layer 130. The electron transfer region 140 may have a single-layer structure or a multi-layer structure comprising different materials.

[0284] The electron transfer region 140 may include an electron injection layer, an electron transport layer and / or a hole blocking layer, and may further include an auxiliary emission layer.

[0285] In the implementation method, such as Figure 2 As explained in the text, the electron transfer region 140 may include an electron injection layer 142 and an electron transport layer 144 stacked sequentially from the second electrode 150 to the emitter layer 130.

[0286] In some implementations, such as Figure 3 As illustrated, the electron transfer region 140 may include an electron injection layer 142, an electron transport layer 144, and a hole blocking layer 146 stacked sequentially from the second electrode 150. The hole blocking layer 146 can block or suppress hole injection from the hole transfer region 120. Accordingly, the emission energy and luminous efficiency of the emission layer 130 can be further improved.

[0287] For example, electron transfer region 140 may include a compound represented by the chemical formula ET.

[0288] Chemical formula ET

[0289]

[0290] In the chemical formula ET, X ET1 To X ET3 At least one of them can be N; and X ET1 To X ET3 The remaining groups in the formula can each be independently C(R) ET RET It can be hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 60 aryl or substituted or unsubstituted C1-C 60 Mixed aromatic compounds.

[0291] When X ET1 To X ET3 When one of them is N, compounds represented by the chemical formula ET may include pyridinyl groups. When X ET1 To X ET3 When both of X are N, compounds represented by the chemical formula ET may include pyrimidinyl groups. ET1 To X ET3 When each is N, compounds represented by the chemical formula ET may include triazine groups.

[0292] In the chemical formula ET, lx1 to lx3 can each be an integer selected from 0 to 10 independently. ET1 To L ET3 Each can be independently a directly connected, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C1-C 30 Hybrid aryl.

[0293] When lx1, lx2, or lx3 is 2 or greater, L ET1 L ET2 and L ET3 Each of the two or more can be, for example, through the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C1-C 30 Hybrid aryl.

[0294] In the chemical formula ET, Ar ET1 To Ar ET3 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C1-C 30 Heteroaryl or substituted or unsubstituted silyl groups. For example, Ar ET1 To Ar ET3 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted silyl group. As explained herein, a silyl group can be derived from -Si(R sa (R) sb (R) sc )express.

[0295] Non-limiting examples of electron transfer materials included in electron transfer region 140 include the following:

[0296]

[0297]

[0298]

[0299]

[0300]

[0301] .

[0302] For example, electron transfer region 140 may include anthracene compounds, Alq3 (tris(8-hydroxyquinoline)aluminum), 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-dinaphthane, TPBi (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole) t Bu-PBD (2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum), Bebq2 (bis(benzoquinoline-10-hydroxy)beryllium), ADN (9,10-di(naphthyl-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), or TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), etc., are used as electron transfer materials. Electron transfer region 140 may include one or a combination of the electron transfer materials described herein.

[0303] The electron transfer material mentioned above may be included in at least one of the electron injection layer 142, the electron transport layer 144, and the hole blocking layer 146.

[0304] The electron transfer region 140 may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof. In an embodiment, the materials mentioned above may be included in the electron injection layer 142.

[0305] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkali earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, or Gd, or any combination thereof.

[0306] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may include oxides of alkali metals, alkaline earth metals, and rare earth metals, halides (e.g., fluorides, chlorides, bromides, or iodides), tellurides, or combinations thereof.

[0307] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include a metal ion (such as an alkali metal ion, alkaline earth metal ion, or rare earth metal ion) and a ligand bonded to the metal ion. The ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or combinations thereof.

[0308] The thickness of the electron transfer region 140 can be from about 100 Å to about 1,000 Å, for example from about 150 Å to about 500 Å.

[0309] When the electron transfer region 140 includes an electron injection layer 142 or an electron transport layer 144, the thickness of the electron injection layer 142 may be about 1 Å to about 100 Å, about 1 Å to about 90 Å, or about 5 Å to about 50 Å, and the thickness of the electron transport layer 144 may be about 10 Å to about 900 Å, about 10 Å to about 500 Å, or about 100 Å to about 400 Å.

[0310] Within any of the thickness ranges described herein, electron injection and electron transport characteristics can be further improved without significantly increasing the driving voltage, and the stability of the electron transfer region 140 can be improved.

[0311] Each layer of the electron transfer region 140 can be formed by processes such as thermal evaporation deposition, vacuum deposition, spin coating, inkjet printing, laser printing, casting, or laser thermal transfer.

[0312] The light-emitting device ED may further include a capping layer. The capping layer can improve the light emission efficiency to the outside of the light-emitting device ED.

[0313] like Figure 4 As illustrated, the second capping layer 160b may be formed on the outer surface of the second electrode 150. In some embodiments, the first capping layer 160a may be formed on the outer surface of the first electrode 110.

[0314] The refractive index of the first capping layer 160a and / or the second capping layer 160b may be about 1.6 or greater. For example, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the first capping layer 160a and / or the second capping layer 160b may be 1.6 or greater, 1.8 or greater, or 2.0 or greater.

[0315] The first capping layer 160a and the second capping layer 160b may each be formed as an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic mixed capping layer including both organic and inorganic materials.

[0316] The first capping layer 160a and / or the second capping layer 160b may each have a single-layer structure or a multi-layer structure comprising different materials.

[0317] In some embodiments, the first capping layer 160a and the second capping layer 160b may each independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalene phthalocyanine derivative, an alkali metal complex, or an alkaline earth metal complex, etc. The first capping layer 160a and the second capping layer 160b may each independently comprise one or a combination of the aforementioned materials.

[0318] In an embodiment, the first capping layer 160a and / or the second capping layer 160b may each independently comprise an amine-containing compound.

[0319] In a non-limiting example, the first capping layer 160a and / or the second capping layer 160b may include at least one of the compounds represented by chemical formulas P1 to P4 and / or at least one of the compounds HT-7, HT-8 and HT-14.

[0320]

[0321]

[0322] refer to Figure 5 The light-emitting device ED may include multiple light-emitting structures (e.g., light-emitting structures ES1, ES2, and ES3). Each of the light-emitting structures ES1, ES2, and ES3 may include, as shown in the reference... Figures 1 to 4 The stacked structure of the hole transfer region 120, the emitter layer 130, and the electron transfer region 140 is described. In the example embodiment, Figure 5The light-emitting device ED can be a light-emitting device with a series structure.

[0323] Charge generation layers CGL1 and CGL2 can each be disposed between adjacent structures in the light-emitting structures ES1, ES2, and ES3. Charge generation layers CGL1 and CGL2 can each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0324] The p-type charge generation layer may include hole transport host compounds, such as NPB. For example, the p-type charge generation layer may include compounds represented by the chemical formula HT as described herein. The p-type charge generation layer may further include p-type dopants, such as TCNQ, etc.

[0325] In some embodiments, the n-type charge generation layer may include at least one of alkali metals, alkaline earth metals, lanthanides, rare earth metals, transition metals, post-transition metals, and alloys thereof.

[0326] The n-type charge-generating layer may further include, for example, a metal complex, and the metal complex may include the aforementioned metal and at least one organic ligand. The organic ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, or cyclopentadiene, etc.

[0327] The n-type charge-generating layer may further include an electron transport host compound. For example, the n-type charge-generating layer may include a compound represented by the chemical formula ET as described herein. In embodiments, the n-type charge-generating layer may include a phenanthroline-containing compound.

[0328] For example, the thickness of the n-type charge generation layer and the thickness of the p-type charge generation layer can each be independently 20 Å to 1000 Å, 20 Å to 700 Å, or 30 Å to 500 Å.

[0329] The charge generation layers CGL1 and CGL2 may include a first charge generation layer CGL1 disposed between the first light-emitting structure ES1 and the second light-emitting structure ES2, and a second charge generation layer CGL2 disposed between the second light-emitting structure ES2 and the third light-emitting structure ES3.

[0330] In an example implementation, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, the third light-emitting structure ES3, and the second electrode 150 may be stacked sequentially from the top surface of the first electrode 110.

[0331] The colors emitted from the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may be the same or different from each other. In some embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may respectively include a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer, and a white light-emitting structure may be implemented through a series structure, but is not limited thereto.

[0332] exist Figure 5 The text uses a 3-stacked series structure with three light-emitting structures as an example, but the series structure of the light-emitting device is not limited to this. Figure 5 The structure described in the text. For example, a 2-stacked structure or as referenced... Figure 6 The described 4-stacked structure, 5-stacked structure or more stacked structure.

[0333] refer to Figure 6 For reference Figure 5 The described tandem structure, in which the light-emitting structure and the charge-generating layer are alternately and repeatedly stacked, may be disposed between the first electrode 110 and the second electrode 150.

[0334] In an example implementation, the first to m-th light-emitting structures ES1 to ESm may be stacked sequentially from the top surface of the first electrode 110, with one or more charge-generating layers inserted between these light-emitting structures. The one or more charge-generating layers may include a first charge-generating layer CGL1 to a (m-1)-th charge-generating layer CGLm-1 stacked sequentially from the top surface of the first electrode 110.

[0335] like Figure 6 As explained in the text, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, ..., the (m-1)th light-emitting structure ESm-1, the (m-1)th charge-generating layer CGLm-1, the mth light-emitting structure ESm, and the second electrode 150 can be stacked sequentially from the top surface of the first electrode 110.

[0336] In some embodiments, m may be 4, and the intermediate layer of the light-emitting device may have a 4-stacked series structure, and may include first to fourth light-emitting structures ES1, ES2, ES3 (not shown) and ES4 (not shown), and first to third charge-generating layers CGL1, CGL2 and CGL3 (not shown). The colors of the light generated from the first to fourth light-emitting structures ES1, ES2, ES3 and ES4 may be the same or different from each other.

[0337] In an implementation, the first to fourth light-emitting structures ES1, ES2, ES3, and ES4 may include at least one blue light-emitting structure and at least one green light-emitting structure. In a non-limiting example, the first to third light-emitting structures ES1, ES2, and ES3 may correspond to a blue light-emitting structure, and the fourth light-emitting structure ES4 may correspond to a green light-emitting structure.

[0338] In some embodiments, m may be 5, and the intermediate layer of the light-emitting device may have a 5-stacked series structure, and may include first to fifth light-emitting structures ES1, ES2, ES3, ES4 and ES5 (not shown), and first to fourth charge-generating layers CGL1, CGL2, CGL3 and CGL4 (not shown). The colors of the light generated from the first to fifth light-emitting structures ES1, ES2, ES3, ES4 and ES5 may be the same or different from each other.

[0339] In this embodiment, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include at least one blue light-emitting structure and at least one green light-emitting structure. In a non-limiting example, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include three blue light-emitting structures and two green light-emitting structures. For example, the first light-emitting structure ES1, the third light-emitting structure ES3, and the fifth light-emitting structure ES5 may correspond to blue light-emitting structures, and the second light-emitting structure ES2 and the fourth light-emitting structure ES4 may correspond to green light-emitting structures.

[0340] Electronic devices

[0341] The aforementioned light-emitting device ED can be applied to electronic devices and can be provided as a light-emitting part or light-emitting unit of electronic devices.

[0342] Electronic devices may include light-emitting devices (EDs) comprising fused-ring compounds represented by chemical formula 1 as described herein, thereby providing improved luminous efficiency and lifetime characteristics.

[0343] The electronic device may further include, for example, a functional layer disposed on a light-emitting device, and the functional layer may include a sensor layer, a polarization layer, a color conversion layer, a color filter layer, or a combination of at least two of them.

[0344] Examples of electronic devices may include display devices, billboards, signs, light sources, lighting fixtures, personal computers (PCs) (such as laptops or desktops), mobile phones, e-books, electronic dictionaries, electronic notebook computers, healthcare devices (including diagnostic devices and various sensors), or various display components for vehicles (cars, aircraft, ships, trains, etc.). For example, electronic devices may be flat panel displays, curved displays, computer monitors, medical monitors, televisions (TVs), billboards, lights for indoor lighting, lights for outdoor lighting, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, retractable displays, laser printers, telephones, mobile phones, tablet computers, phablet computers, personal information terminals (PDAs), wearable devices, laptops, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicles, video walls including multiple displays pieced together, theater screens, stadium screens, light therapy devices, or signage.

[0345] In an example implementation, the light-emitting device ED can be applied to an organic light-emitting diode (OLED) display device or a quantum dot (QD)-OLED display device.

[0346] Figure 7 A schematic cross-sectional view illustrating a display device according to an example embodiment.

[0347] refer to Figure 7 The display device may include a circuit layer CL disposed on a substrate 200, and light-emitting devices ED1, ED2 and ED3 disposed on the circuit layer CL.

[0348] The substrate 200 can be used as a support substrate or backplate substrate for a display device. The substrate 200 can be a glass substrate or a plastic substrate.

[0349] In some embodiments, the substrate 200 may include a polymer material having both transparent and flexible properties. When the substrate 200 includes a polymer material, it can be used in a transparent flexible display device. For example, the substrate 200 may include a polymer material such as polyimide, polysiloxane, epoxy resin, acrylic resin, or polyester. In one embodiment, the substrate 200 may include polyimide.

[0350] The circuit layer CL may include transistors TR1, TR2, and TR3. The circuit layer CL may include wiring layers and insulating layers for forming a thin-film transistor array (TFT-array).

[0351] The circuit layer CL may further include a buffer layer 205 on the top surface of the substrate 200. The buffer layer 205 can block the penetration of moisture through the substrate 200 and can also block the diffusion of impurities between the substrate 200 and the structures formed thereon.

[0352] The buffer layer 205 may include, for example, silicon oxide, silicon nitride, or silicon oxynitride. The buffer layer 205 may include one or a combination of the aforementioned materials. In some embodiments, the buffer layer 205 may have a stacked structure including a silicon oxide layer and a silicon nitride layer.

[0353] Transistors TR1, TR2, and TR3 may be disposed on buffer layer 205. The first transistor TR1, the second transistor TR2, and the third transistor TR3 may be electrically connected to the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3, respectively.

[0354] Transistors TR1, TR2 and TR3 may each include an active layer 210, a gate insulating layer 220 and a gate electrode 230.

[0355] The active layer 210 may be disposed on the buffer layer 205 and may be patterned for each pixel region. The active layer 210 may include silicon compounds, such as amorphous silicon or polycrystalline silicon. p-type dopants or n-type dopants may be doped in corresponding regions of the active layer 210, and the active layer 210 may include source regions, drain regions, and channel regions.

[0356] The active layer 210 may include an oxide semiconductor, such as indium gallium zinc oxide (IGZO), zinc tin oxide (ZTO), or indium tin zinc oxide (ITZO).

[0357] The gate insulating layer 220 may be formed on the active layer 210, and the gate electrode 230 may be stacked on the gate insulating layer 220. For example... Figure 7 As illustrated, the gate insulating layer 220 can be patterned to partially cover each active layer 210. Alternatively, the gate insulating layer 220 can extend continuously across multiple pixel regions or light-emitting regions, and can be provided as a common layer for the first transistor TR1, the second transistor TR2, and the third transistor TR3.

[0358] The gate electrode 230 may overlap with the channel region of the active layer 210 in the thickness direction.

[0359] An insulating interlayer 240 may be formed on the active layer 210 to cover the gate electrode 230 and the gate insulating layer 220. Connection electrodes 250 and 260, which may contact or be electrically connected to the active layer 210, may each be disposed on the insulating interlayer 240.

[0360] Connecting electrodes 250 and 260 may extend through insulating interlayer 240 to contact or electrically connect with active layer 210. When gate insulating layer 220 is provided as a common layer for multiple light-emitting regions, connecting electrodes 250 and 260 may also extend through gate insulating layer 220.

[0361] The connecting electrodes 250 and 260 may include a source electrode 250 that can contact or be electrically connected to the source region of the active layer 210, and a drain electrode 260 that can contact or be electrically connected to the drain region of the active layer 210.

[0362] The gate insulating layer 220 and the insulating interlayer 240 may each independently comprise silicon oxide, silicon nitride, or silicon oxynitride, and may each have a stacked structure comprising a silicon oxide layer and a silicon nitride layer.

[0363] The gate electrode 230 and the connecting electrodes 250 and 260 may include metals (such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, etc.), their alloys, or their nitrides.

[0364] A through-hole insulating layer 270 may be formed on the insulating interlayer 240 to cover the connecting electrodes 250 and 260.

[0365] The via insulating layer 270 can accommodate a via structure electrically connecting the first electrode 110 and the drain electrode 260. The via insulating layer 270 can be used as a planarization layer for the circuit layer CL. In embodiments, the via insulating layer 270 may include polymeric materials such as polyimide, polysiloxane, epoxy resin, acrylic resin, or polyester, or combinations thereof.

[0366] Light-emitting devices ED1, ED2, and ED3 can be disposed on the through-hole insulating layer 270. For example, as shown in the reference... Figures 1 to 4 The light-emitting devices ED1, ED2 and ED3 described may include a first electrode 110, a hole transfer region 120, an emission layer 130, an electron transfer region 140 and a second electrode 150, which are stacked sequentially from the through-hole insulating layer 270.

[0367] The first electrode 110 can be electrically connected to transistors TR1, TR2, and TR3 in circuit layer CL via a through-hole structure, or connected to electrodes 250 and 260. For example... Figure 7 As illustrated, the first electrode 110 may be in contact with or electrically connected to the drain electrode 260 to serve as a patterned pixel electrode for each light-emitting area or pixel region.

[0368] A pixel defining layer 280 may be formed on the via insulating layer 270 to define each light-emitting area or pixel region. The red light-emitting area, green light-emitting area and blue light-emitting area may be separated and defined by the pixel defining layer 280, and the light-emitting devices ED1, ED2 and ED3 may correspond to the red light-emitting device, the green light-emitting device and the blue light-emitting device, respectively.

[0369] The pixel-defining layer 280 can partially cover the first electrode 110 in each light-emitting area.

[0370] like Figure 7 As illustrated, hole transfer region 120 and electron transfer region 140 may each be provided as a common layer extending continuously over pixel defining layer 280 and first electrode 110. Emitting layer 130 may be formed in each light-emitting region or pixel region and may be separated by pixel defining layer 280.

[0371] In some embodiments, the emitting layer 130 may also be provided as a common layer that extends continuously throughout the light-emitting area or pixel area. In some embodiments, the hole transfer area 120, the emitting layer 130, and the electron transfer area 140 may be patterned and formed separately for each light-emitting area or pixel area.

[0372] The second electrode 150 can be provided as a common electrode that extends continuously throughout the light-emitting area or pixel area.

[0373] The encapsulation layer 290 may be disposed on the pixel limiting layer 280 and the light-emitting devices ED1, ED2 and ED3 to protect the light-emitting devices ED1, ED2 and ED3 from the effects of moisture and / or oxygen. The encapsulation layer 290 may be a thin-film encapsulation (TFE) having a single-layer structure or a multi-layer structure.

[0374] Encapsulation layer 290 may include: an inorganic layer, the inorganic layer including silicon nitride (SiN) x ), silicon dioxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; an organic layer comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate or polyacrylic acid), epoxy resins (e.g., aliphatic glycidyl ether (AGE)), or any combination thereof; or a combination of an inorganic layer and an organic layer.

[0375] The display device may further include a functional layer 300 disposed on the encapsulation layer 290. The functional layer 300 may include a sensor layer (such as a touch sensor layer), an optical layer (such as a polarizing layer), a color conversion layer, a color filter layer, a window film, or any combination thereof.

[0376] Figure 8 A schematic cross-sectional view illustrating a display device according to an example embodiment.

[0377] refer to Figure 8 Each of the light-emitting devices ED1, ED2 and ED3 may have a series structure, for example, a 2-stacked series structure.

[0378] In some embodiments, the hole transfer region 120 and the electron transfer region 140 may be continuously formed and co-formed and included in the intermediate layer of each light-emitting structure. Additionally, the charge generation layer CGL may extend continuously across multiple pixel regions and may co-enclose in the intermediate layer of each light-emitting structure.

[0379] The first light-emitting device ED1 may include a first lower emitting layer 130-1a disposed between the hole transfer region 120 and the charge generation layer CGL, and a first upper emitting layer 130-1b disposed between the charge generation layer CGL and the electron transfer region 140.

[0380] The second light-emitting device ED2 may include a second lower emitting layer 130-2a disposed between the hole transfer region 120 and the charge generation layer CGL, and a second upper emitting layer 130-2b disposed between the charge generation layer CGL and the electron transfer region 140.

[0381] The third light-emitting device ED3 may include a third lower emitting layer 130-3a disposed between the hole transfer region 120 and the charge generation layer CGL, and a third upper emitting layer 130-3b disposed between the charge generation layer CGL and the electron transfer region 140.

[0382] The lower and upper emitting layers in each light-emitting structure can generate light of the same color. In an embodiment, each of the first lower emitting layer 130-1a and the first upper emitting layer 130-1b in the first light-emitting device ED1 can correspond to a red emitting layer. Each of the second lower emitting layer 130-2a and the second upper emitting layer 130-2b in the second light-emitting device ED2 can correspond to a green emitting layer. Each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b in the third light-emitting device ED3 can correspond to a blue emitting layer.

[0383] Figure 9 This is a schematic cross-sectional view illustrating the stacked structure of the light-emitting structures in a display device according to an exemplary embodiment. For ease of explanation and description, [the following is a simplified description]. Figure 9 Explanations of circuit layers, substrates, pixel-defining layers, etc., are omitted, and the shape of each layer or element in the light-emitting structure is simply shown as a rectangle.

[0384] refer to Figure 9 At least one of the light-emitting devices ED1, ED2 and ED3 or at least one of the pixel regions PA1, PA2 and PA3 may have a series structure including multiple emission layers, and at least one of the others may have a single emission layer structure.

[0385] In some embodiments, one of the light-emitting devices ED1, ED2, and ED3 or one of the pixel regions PA1, PA2, and PA3 may have a series structure including multiple emission layers, and the others may have a single emission layer structure.

[0386] like Figure 9 As explained herein, the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 may be respectively included in the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3. In some embodiments, the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3 may correspond to the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0387] Hole transfer region 120, electron transfer region 140 and second electrode 150 may each be provided as a common layer that extends continuously throughout the first pixel region PA1, the second pixel region PA2 and the third pixel region PA3.

[0388] The first light-emitting device ED1 included in the first pixel region PA1 may include a first emitting layer 130-1, and the second light-emitting device ED2 included in the second pixel region PA2 may include a second emitting layer 130-2. Each of the first emitting layer 130-1 and the second emitting layer 130-2 may be a single emitting layer.

[0389] The third light-emitting device ED3, included in the third pixel region PA3, may have, for example, a 2-stacked series structure. The third light-emitting device ED3 may include a third lower emitting layer 130-3a and a third upper emitting layer 130-3b separated therebetween by a charge generation layer CGL. Each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b may correspond to a blue emitting layer.

[0390] The lower electron transfer region 140a can be disposed between the charge generation layer CGL and the third lower emitter layer 130-3a. The upper hole transfer region 120b can be disposed between the charge generation layer CGL and the third upper emitter layer 130-3b.

[0391] Accordingly, the tandem light-emitting structure in which the first electrode 110, hole transfer region 120, third lower emission layer 130-3a, lower electron transfer region 140a, charge generation layer CGL, upper hole transfer region 120b, third upper emission layer 130-3b, electron transfer region 140, and second electrode 150 are stacked in sequence can be disposed in the third pixel region PA3.

[0392] Figure 10 A schematic cross-sectional view illustrating a display device according to an example embodiment.

[0393] Figure 10This describes a display device having a QD-OLED structure according to an embodiment. (Regarding references...) Figure 7 Detailed descriptions of components and structures that are substantially the same or similar will not be repeated here.

[0394] refer to Figure 10 As shown in the reference above Figure 7 As described, a pixel defining layer 280 and a light-emitting device ED can be disposed on a circuit layer CL. In an example embodiment, each pixel region can emit light in the same wavelength range. In an embodiment, each light-emitting device ED can emit blue light.

[0395] In some implementations, each light-emitting region may include the features described above. Figure 5 The described light-emitting device has a series structure. In this case, the intermediate layer of each light-emitting device ED can be provided as a common layer that extends continuously throughout multiple light-emitting areas.

[0396] The color control layer CCL can be disposed on the encapsulation layer 290, and the color control layer CCL can include color control portions CCP1, CCP2 and CCP3.

[0397] Color control sections CCP1, CCP2, and CCP3 may each include a light converter, such as a quantum dot or a phosphor. In each of the color control sections CCP1, CCP2, and CCP3, the light converter can convert the wavelength of the supplied light and emit the resulting light.

[0398] The color control portions CCP1, CCP2, and CCP3 may be separated from or spaced apart by the barrier BM. The barrier BM may substantially overlap with the pixel defining layer 280, and the color control portions CCP1, CCP2, and CCP3 may substantially overlap with each emission layer 130.

[0399] The color control layer (CCL) may include: a first color control portion CCP1, which includes a first quantum dot that converts a first color light provided by the light-emitting device ED into a second color light; a second color control portion CCP2, which includes a second quantum dot that converts the first color light into a third color light; and a third color control portion CCP3 that transmits the first color light.

[0400] In some embodiments, the first color light, the second color light, and the third color light may be blue light, red light, and green light, respectively. The first quantum dot and the second quantum dot may be red quantum dot and green quantum dot, respectively.

[0401] Color control components CCP1, CCP2, and CCP3 may each further include a scattering material, such as inorganic particles. For example, the third color control component CCP3 may not include quantum dots and may include a scattering material. The scattering material may include TiO2, ZnO, Al2O3, SiO2, or hollow silica, etc. The scattering material may be one or a combination of the aforementioned materials.

[0402] The color control components CCP1, CCP2, and CCP3 may each further include a binder resin for dispersing quantum dots and scattering materials. The binder resin may include acrylic resin, urethane resin, silicone resin, or epoxy resin, etc.

[0403] A color filter layer CFL, including color filters CF1 and CF2 and a light-blocking portion CP, can be set on the color control layer CCL.

[0404] The color filter layer CFL may include a first color filter CF1 that transmits a second color light, a second color filter CF2 that transmits a third color light, and a third color filter that transmits a first color light. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter may be a blue color filter.

[0405] Color filters CF1 and CF2 may each include a photosensitive adhesive resin and a colorant including pigments and / or dyes. The first color filter CF1 may include red pigments and / or red dyes, and the second color filter CF2 may include green pigments and / or green dyes.

[0406] The light-shielding portion CP can be disposed between the color filters. In some embodiments, the light-shielding portion CP may include a first light-shielding portion CP1 and a second light-shielding portion CP2 containing colorants of different colors.

[0407] In some embodiments, the first light-shielding portion CP1 may include a blue colorant, and the second light-shielding portion CP2 may include a red or black colorant. In one embodiment, a portion of the first light-shielding portion CP1 may be provided as a blue color filter in the blue emitting region and may be exposed between a plurality of second light-shielding portions CP2 so that an additional color filter (e.g., a third color filter) may be omitted.

[0408] The first isolation layer 310 may be disposed between the color control layer CCL and the light-emitting device ED (or encapsulation layer 290). The second isolation layer 320 may be disposed between the color control layer CCL and the color filter layer CFL.

[0409] The isolation layers 310 and 320 may each include at least one inorganic layer. For example, the isolation layers 310 and 320 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, or silicon oxynitride.

[0410] In an embodiment, the isolation layers 310 and 320 may each have a multilayer structure that further includes an organic layer.

[0411] Figure 11 A schematic cross-sectional view illustrating a display device according to an exemplary embodiment. (Refer to reference...) Figure 10 Detailed descriptions of components and structures that are substantially the same or similar are omitted here.

[0412] refer to Figure 11 The light-emitting device ED corresponding to the color control portions CCP1, CCP2 and CCP3 may correspond to the light-emitting device including the first electrode 110 used as a pixel electrode, and the color control portions CCP1, CCP2 and CCP3 may be disposed above the first electrode 110, and the light-emitting device ED may have a series structure.

[0413] In some implementations, such as reference Figure 5 As described, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, and the third light-emitting structure ES3 can be stacked sequentially between the first electrode 110 and the second electrode 150. The first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, and the third light-emitting structure ES3 can be continuously and jointly formed in multiple pixel regions or light-emitting areas.

[0414] In one embodiment, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can generate light of different colors, and the light-emitting device ED can generate white light. In another embodiment, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can all generate blue light.

[0415] In some implementations, such as reference Figure 6 As described, the light-emitting device ED may include a series structure with 4-stack, 5-stack or more stacks.

[0416] Figure 12 A schematic exploded perspective view illustrating an electronic device according to an example embodiment.

[0417] According to the example implementation, the electronic device can be implemented in the form of a mobile phone (smartphone), tablet computer, or PC, which includes the display device described above.

[0418] refer to Figure 12 The electronic device may include a window structure WS, a display panel DP, and a rear structure RS.

[0419] The window structure WS provides an external display surface that can be recognized by the user (such as the visible surface of a mobile phone) and may include a transparent material film. For example, the window structure WS may include glass (e.g., ultra-thin glass (UTG)), a hard coating, or a plastic film.

[0420] The outer surface of the window structure WS may include an active region AA and a peripheral region PA. The active region AA provides a surface on which the image of the display device is displayed and on which the user's touch / command input is applied. The peripheral region PA may substantially correspond to the bezel area of ​​the display device.

[0421] The display panel DP may include the aforementioned display device and may have a display area DA and a non-display area NDA. The display area DA of the display panel DP may substantially correspond to or overlap with the active area AA of the window structure WS. The non-display area NDA of the display panel DP may substantially correspond to or overlap with the peripheral area PA of the window structure WS.

[0422] In some implementations, functional device regions E1 and E2 may be included in the active region AA of the window structure WS. For example, the first functional device region E1 may be included at one end of the active region AA and may be implemented, for example, in the form of a camera hole. The second functional device region E2 may be used as a fingerprint sensing region.

[0423] For example, the sensor structure for touch sensing or fingerprint sensing can be set in the display panel DP or between the window structure WS and the display panel DP.

[0424] The rear structure RS can be used as a frame structure or housing for a display device or electronic device. A cover panel can be disposed between the rear structure RS and the display panel DP.

[0425] Figure 13 A schematic diagram illustrating an electronic device according to an example embodiment.

[0426] Electronic devices may be installed in, embedded in, attached to, or integrated with vehicle 400. However, vehicle 400 is not limited to... Figure 13 The implementation method is illustrated in the text. Further examples of vehicle 400 may include vehicles such as three- or four-wheeled vehicles, construction machinery, two-wheeled vehicles, motor vehicles, bicycles, trains, etc. Other examples of vehicle 400 may include electric vehicles, hybrid vehicles, etc.

[0427] refer to Figure 13At least one of the first to fifth display devices DP1, DP2, DP3, DP4 and DP5 may be applied to vehicle 400.

[0428] In an example implementation, a first display device DP1 may be located in the instrument panel area 410. Driving information (such as driving distance and driving speed) and various warning lights may be displayed in the instrument panel area 410.

[0429] The second display device DP2 can be installed on the windshield (FW) of the vehicle 400. For example, the second display device DP2 can be installed as a head-up display (HUD).

[0430] The third display device DP3 can be installed on the center console 420 of the vehicle 400. The center console 420 can display buttons or switches for controlling the image display or music player, air conditioning, heater, etc., and can also display vehicle information.

[0431] The fourth display device DP4 can be applied to the side mirror 430 of the vehicle 400. The side mirror 430 can be installed on each of the two sides of the exterior of the vehicle 400, and the fourth display device DP4 can be applied to at least one of the side mirrors 430 installed on each of the two sides.

[0432] A fifth display device DP5 may be installed on the passenger seat instrument panel 440. Information / images that are the same as or different from those displayed on the instrument panel area 410 and / or the center console 420 may be displayed on the passenger seat instrument panel 440.

[0433] Electronic devices may include, for example, flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor lighting, lights for outdoor lighting, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, retractable displays, laser printers, telephones, mobile phones, tablet computers, phablet computers, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicles, video walls including multiple displays spliced ​​together, theater screens, stadium screens, light therapy devices, or signs.

[0434] The display device according to the embodiments of this disclosure can be applied to various electronic devices. The electronic device according to the embodiments includes the aforementioned display device, and may further include modules or devices with additional functions in addition to the display device.

[0435] Figure 14 This is a block diagram of an electronic device according to an embodiment.

[0436] refer to Figure 14 The electronic device 10 according to the embodiment may include a display module 11, a processor 12, a memory 13 and a power module 14.

[0437] The processor 12 may include a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and / or a controller.

[0438] Data information for the operation of processor 12 or display module 11 can be stored in memory 13. When processor 12 executes the application program stored in memory 13, image data signals and / or input control signals can be transmitted to display module 11, and display module 11 can process the received signals and output image information through the display screen.

[0439] The power module 14 may include a power supply module (such as a power adapter or battery device) and a power conversion module that converts the power supplied by the power supply module to generate the power required for the operation of the electronic device 10.

[0440] At least one component of the electronic device 10 described above may be included in the display device according to the above embodiments. Additionally, several individual modules functionally included in one module may be included in the display device, and other modules may be provided separately from the display device. For example, display module 11 may be included in the display device, and processor 12, memory 13, and power module 14 may be provided in the electronic device 10 as a separate device from the display device.

[0441] Figure 15 This is a schematic diagram of an electronic device according to various embodiments.

[0442] refer to Figure 15 Non-limiting examples of various electronic devices that utilize the display device according to the above embodiments include electronic devices for displaying images, such as smartphones 10_1a, tablet PCs 10_1b, laptop computers 10_1c, TVs 10_1d, or desktop monitors 10_1e; wearable devices including display modules, such as smart glasses 10_2a, head-mounted displays 10_2b, or smartwatches 10_2c; and vehicle electronic devices 10_3 including display modules, such as center information displays (CIDs) located on vehicle instrument panels, center consoles, dashboards, etc., in-vehicle mirror displays, or head-up displays. Electronic devices may include virtual reality glasses or augmented reality glasses.

[0443] The fused-ring compounds according to embodiments will be described in further detail below with reference to examples and comparative examples. Examples are provided to aid in understanding this disclosure, but they are provided by way of non-limiting examples, and the scope of this disclosure is not limited thereto. Those skilled in the art will appreciate that various changes and modifications can be made to the disclosed examples within the scope of this disclosure.

[0444] Example

[0445] Synthesis Example 1: Synthesis of Compound 10

[0446] Reaction Scheme 1

[0447]

[0448] In an inert gas atmosphere, 10.00 g (39 mmol) of 6,7-dicyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-carboxylic acid was added to deionized (DI) water, and 12.68 g (47 mmol) of PBr3 was added to the stirred solution. The reaction was carried out at 120°C to obtain intermediate compound 10-a (11.6 g) (yield: 93.1%).

[0449] Reaction Scheme 2

[0450]

[0451] A solution was prepared by dissolving phenylboronic acid (4.59 g, 38 mmol), sodium carbonate (3.04 g, 38 mmol), and palladium catalyst (1 mol%) supported on 1,3,5-triphenylbenzene-1,2-bis(diphenylphosphino)ethane-dimethoxymethane in ethanol / water (2:3 volume ratio) in an inert gas environment.

[0452] Intermediate compound 10-a (10.00 g, 31 mmol) was added to the solution and stirred at 80°C for 2 hours. The solution was cooled and extracted with dichloromethane (DCM). The obtained product and Nafion-H catalyst were added to toluene, stirred, and heated under reflux for 36 hours to obtain intermediate compound 10-b (5.6 g) (yield: 80.8%).

[0453] Reaction scheme 3

[0454]

[0455] Intermediate compound 10-b (5.50 g, 12 mmol) and cyanogen bromide (2.90 g, 27 mmol) were dissolved in pentane / water (5:2 v / v) and cooled to 0°C. The solution was stirred for 10 minutes, and triethylamine (4 mL) was added dropwise. The mixture was stirred at 0°C for 1 hour and filtered to obtain compound 10 (4.9 g) (yield: 85.6%).

[0456] Synthesis Example 2: Synthesis of Compound 8

[0457] Reaction scheme 4

[0458]

[0459] The process was substantially the same as that used in Synthesis Example 1 for intermediate compound 10-b, except that 5,6,7,8-tetracyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-carboxylic acid (10.00 g, 33 mmol) was used instead of 6,7-dicyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-carboxylic acid in the synthesis of intermediate compound 10-a to obtain intermediate compound 8-b (6.7 g) (yield: 88.3%).

[0460] Intermediate compound 8-b (6.50 g, 12 mmol) and 50 mg of CoMo nanosulfide catalyst were added to 50 mL of naphthalene solvent and purged with nitrogen for 2 h to remove air. The reaction vessel was heated to 300°C and hydrogen was added at 4.0 MPa, and the mixture was stirred at high speed to obtain compound 8 (4.9 g) (yield: 80.1%).

[0461] Synthesis Example 3: Synthesis of Compound 13

[0462] The process was essentially the same as that of reaction scheme 3 in Synthesis Example 1, except that intermediate compound 8-b (10.00 g, 18 mmol) and 4-bromobenzonitrile (7.38 g, 41 mmol) were used instead of intermediate compound 10-b and cyanogen bromide to obtain compound 13 (8.5 g) (yield: 64.7%).

[0463]

[0464] Synthesis Example 4: Synthesis of Compound 16

[0465] The process was substantially the same as that used in Synthesis Example 1 for intermediate compound 10-b, except that 5,6,7,8-tetracyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-thiocarboxylic acid (10.00 g, 31 mmol) was used instead of 6,7-dicyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-carboxylic acid in the synthesis of intermediate compound 10-a to obtain intermediate compound 16-b (7.50 g).

[0466] Subsequently, the process was carried out in essentially the same manner as that of reaction scheme 3 in Synthesis Example 1, except that intermediate compound 16-b (7.50 g, 13 mmol) and 4-bromobenzonitrile (5.41 g, 30 mmol) were used instead of intermediate compound 10-b and cyanogen bromide to obtain compound 16 (6.7 g) (yield: 58.0%).

[0467]

[0468] Synthesis Example 5: Synthesis of Compound 17

[0469] The process was substantially the same as that of Synthesis Example 1, except that (E)-7-hydroxy-8-(hydroxymethylene)-7,8-dihydronaphthalene-1,2,3,4,5,6-hexacarboxynitrile (10.00 g, 31 mmol) was used instead of 6,7-dicyano-3,4-dihydroxy-3,4-dihydronaphthalene-2-carboxylic acid in the synthesis of intermediate compound 10-a in Synthesis Example 1 to obtain compound 17 (3.8 g) (yield: 40.4%).

[0470]

[0471] The compounds synthesized in Synthetic Examples 1 to 5 above 1 The H NMR and MS / FAB results are shown in Table 1. For 1 1H NMR data, these values ​​are reported as chemical shifts (δ, ppm), where s is a singlet and d is a doublet.

[0472] Table 1

[0473]

[0474] Manufacturing of light-emitting devices

[0475] As the anode, it is formed with 15 ohms per square centimeter (Ω / cm). 2The glass substrate (Corning product) for the 1,300 Å ITO electrode was cut to a size of 50 mm × 50 mm × 0.7 mm, and the cut substrate was ultrasonically cleaned for 5 minutes using isopropanol and DI water. The ultrasonically cleaned substrate was then irradiated with ultraviolet light for 30 minutes and exposed to ozone, and then mounted on a vacuum deposition apparatus.

[0476] Subsequently, p-type dopant compound and compound HT-15 were vacuum-deposited on the anode at a weight ratio of 3:97 to form a hole injection layer with a thickness of 100 Å. Compound HT-16 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 1,250 Å. Compounds PH-14, PH-15, and PD1-15 were vacuum-deposited on the hole transport layer at a weight ratio of 45:45:10 to form an emitter layer with a thickness of 300 Å.

[0477] Compound ET-14 was vacuum-deposited onto the emitter layer to form a hole-blocking layer with a thickness of 50 Å. Compounds ET-17 and Liq were vacuum-deposited onto the hole-blocking layer in a 5:5 weight ratio to form an electron transport layer with a thickness of 310 Å.

[0478] Yb was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of 15 Å. Ag and Mg were vacuum deposited on the electron injection layer in a 5:5 weight ratio to form a cathode with a thickness of 1,000 Å.

[0479] The compounds mentioned above used in the manufacture of the light-emitting device are shown below. The compounds are purified by sublimation from commercially available products.

[0480]

[0481]

[0482]

[0483] The p-type dopant compounds used in the fabrication of light-emitting devices are shown in Table 2 below.

[0484] Table 2

[0485]

[0486] The compounds for comparative examples are shown below. The compounds were purified by sublimation from commercially available products.

[0487]

[0488] Evaluation Example

[0489] Evaluation Example 1: Evaluation of the properties of fused-ring compounds

[0490] The properties of the compounds in the examples and comparative examples were evaluated below. The evaluation results are shown in Table 3.

[0491] (1) HOMO level assessment

[0492] Cyclic voltammetry (CV) was used (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylformamide) / electrode: 3-electrode system (working electrode: GC (glassy carbon), reference electrode: Ag / AgCl, auxiliary electrode: Pt)) to obtain potential (V)-current (A) plots for each compound. Subsequently, the HOMO level of each compound was calculated from the oxidation initiation points in the plots.

[0493] (2) LUMO level assessment

[0494] Cyclic voltammetry (CV) was used (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylformamide) / electrode: 3-electrode system (working electrode: GC, reference electrode: Ag / AgCl, auxiliary electrode: Pt)) to obtain potential (V)-current (A) plots for each compound. The LUMO level for each compound was then calculated from the reduction initiation points of the plots.

[0495] (3) Assessment of hole mobility and electron mobility

[0496] Hole and electron mobility were assessed using the space charge-limited current (SCLC) method described in the literature “Hole mobility of N,N'-bis(naphtanlen-1-yl)-N,N'-bis(phenyl)benzidine investigated by using space-charge-limited currents, 'Appl. Phys. Lett. 90, 203512 (2007)”.

[0497] (4) Evaluation of glass transition temperature

[0498] The glass transition temperature (Tg) was measured by DSC (differential scanning calorimetry). g Specifically, 5 mg of the sample was heated from room temperature to 300 °C at a heating rate of 10 °C / min, cooled from 300 °C to 25 °C, and then reheated to 300 °C. The glass transition temperature was obtained from the inflection point of the graph during the second heating.

[0499] Table 3

[0500]

[0501] Referring to Table 3, in the fused-ring compounds according to the embodiments, the HOMO and LUMO energy levels are appropriately controlled to improve hole mobility and electron mobility. Accordingly, the fused-ring compounds according to the embodiments can increase the exciton generation efficiency in the emitter layer. In addition, the fused-ring compounds according to the embodiments have high glass transition temperatures and can effectively prevent the degradation of the fused-ring compounds during high-temperature processes.

[0502] Evaluation Example 2: Performance Evaluation of Light-Emitting Devices

[0503] Using the V7000 OLED IVL Test System (Polaronix) at 10 mA / cm 2 The characteristics of the light-emitting device manufactured as described above were measured at a current density.

[0504] Specifically, a source meter (Keithley Instrument, 2400 series) was used to measure 1000 cd / m³. 2 The driving voltage (V) at the brightness was determined, and the luminous efficiency (Cd / A) was measured using a CS-2000 (Konica Minolta) luminance meter.

[0505] The light-emitting device is set at 10 mA / cm 2 The light-emitting device was continuously driven at a current density, and the time until the brightness dropped to 95% of the initial value was measured as the lifetime. The relative values ​​relative to the measurements from the light-emitting device using the compound of Comparative Example 1 are expressed as the relative driving voltage, relative luminous efficiency, and relative lifetime for each light-emitting device.

[0506] The results are shown in Table 4.

[0507] Table 4

[0508]

[0509] Referring to Table 4, in the light-emitting device using the fused ring compound according to the embodiment, the driving relative voltage is reduced, and the relative lifetime is improved without reducing the relative luminous efficiency.

[0510] In the light-emitting device using the fused-ring compound according to the comparative example, the relative driving voltage is high and the relative lifetime is low.

[0511] Although exemplary embodiments of this disclosure have been described, it should be understood that this disclosure is not limited to these exemplary embodiments, but rather various changes and modifications can be made by those skilled in the art within the spirit and scope of this disclosure as set forth in the appended claims and their equivalents.

Claims

1. A fused-ring compound represented by chemical formula 1: Chemical Formula 1 in, In chemical formula 1, X1 and X2 are each independently oxygen, sulfur, or selenium. Ar1 and Ar2 are each independently C6-C containing aromatic rings. 60 fused rings, R1 and R2 are each independently hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C1-C 60 Heterocyclic alkyl, substituted or unsubstituted C1-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, At least one of R1 in number a1 and / or at least one of R2 in number a2 is an electron-withdrawing group or a group substituted by an electron-withdrawing group, wherein the electron-withdrawing group has a para-Hammett substituent constant σ greater than 0 according to the Hammett equation. p , a1 and a2 are each independent integers selected from 1 to 6. When R1 and R2 are each two or more independent entities, the two or more identical or different entities in each of R1 and R2 are... Two or more adjacent R1s may optionally combine with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring, and Two or more adjacent R2s may optionally combine with each other to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring.

2. The fused-ring compound according to claim 1, wherein each of the electron-withdrawing groups is independently -F, -Cl, -Br, -I, -SF5, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, or a substituted or unsubstituted π-electron-deficient nitrogen-containing C3-C group. 30 Cyclic groups.

3. The fused-ring compound according to claim 1, wherein Ar1 and Ar2 are each independently a group in which a benzene ring, naphthyl ring, anthracene ring, phenanthrene ring, tetraphenyl ring, pyrene ring or benzo[a]pyrene ring is fused.

4. The fused-ring compound according to claim 1, wherein the fused-ring compound is represented by chemical formula 1-1: Chemical Formula 1-1 in, In chemical formula 1-1, a1 and a2 are each independent integers selected from 1 to 4, and The definitions of X1, X2, R1, and R2 are the same as those in Formula 1.

5. The fused-ring compound according to claim 1, wherein the fused-ring compound is represented by chemical formula 1-2, chemical formula 1-3 or chemical formula 1-4: Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 in, In chemical formulas 1-2, 1-3, and 1-4, a1 is an integer selected from 1 to 4. a2 is an integer selected from 1 to 6, and The definitions of X1, X2, R1, and R2 are the same as those in Formula 1.

6. The fused-ring compound according to claim 1, wherein the fused-ring compound is represented by chemical formulas 1-5, 1-6, 1-7, 1-8, 1-9, or 1-10: Chemical formulas 1-5 Chemical formulas 1-6 Chemical formulas 1-7 Chemical formulas 1-8 Chemical formulas 1-9 Chemical formulas 1-10 in, In chemical formulas 1-5, 1-6, 1-7, 1-8, 1-9, and 1-10, The definitions of X1, X2, R1, R2, a1, and a2 are the same as those in chemical formula 1.

7. The fused-ring compound according to claim 1, wherein the fused-ring compound is one of compounds 1 to 36: 。 8. A light-emitting device, comprising: First electrode; Second electrode; as well as An intermediate layer disposed between the first electrode and the second electrode. The intermediate layer comprises a hole transfer region, an emission layer, and an electron transfer region, and the hole transfer region comprises a fused ring compound represented by chemical formula 1 according to any one of claims 1 to 7.

9. The light-emitting device of claim 8, wherein the emitting layer emits blue light having a maximum emission center wavelength in the range of 430 nm to 490 nm.

10. An electronic device comprising a light-emitting device according to claim 8 or 9.

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