Fused heterocyclic compound, light-emitting device, and electronic device

Abstract

The invention provides a fused heterocyclic compound, a light-emitting device including the fused heterocyclic compound, and an electronic device including the light-emitting device. The light emitting device includes a first electrode, a second electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer includes a fused heterocyclic compound represented by Chemical Formula 1. Chemical formula 1

Description

[0001] This application claims priority to Korean Patent Application No. 10-2024-0152226, filed on October 31, 2024, with the Korean Intellectual Property Office (KIPO), the contents of which are incorporated herein by reference in their entirety. Technical Field

[0002] Embodiments of this application relate to fused heterocyclic compounds, light-emitting devices, and electronic devices. Background Technology

[0003] Organic light-emitting devices are self-emissive and offer improved viewing angles and contrast characteristics. Additionally, they provide high response times and high brightness.

[0004] An organic light-emitting device may include an emission 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 emission layer to generate excitons. When the excitons transition from an excited state to a ground state, light emission is achieved.

[0005] The emitting layer may include a host material and a dopant material for realizing the above-described light emission mechanism. Summary of the Invention

[0006] According to aspects of this disclosure, fused heterocyclic compounds with improved spectral and luminescent properties (e.g., luminescence efficiency) are provided.

[0007] According to aspects of this disclosure, a light-emitting device with improved light-emitting characteristics and reliability is provided.

[0008] According to aspects of this disclosure, an electronic device including a light-emitting device is provided.

[0009] Fused heterocyclic compounds are represented by chemical formula 1:

[0010] Chemical Formula 1

[0011] .

[0012] In chemical formula 1, X1 and X2 are each independently O, S, or Se, and R1 and R2 are each independently represented by chemical formula 2:

[0013] Chemical formula 2

[0014] .

[0015] In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C7-C 60 Alkylphenyl, substituted or unsubstituted C8-C 60 Fused polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; or R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl ring, substituted or unsubstituted C6-C 60 The aryl ring is either substituted or unsubstituted C2-C. 60 Mixed aromatic rings.

[0016] R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60Aryloxy group, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0017] n, q, and s are each independent integers selected from 0 to 3. m and p are each independent integers selected from 0 to 4. r is an integer selected from 0 to 2. t and u are each independent integers selected from 0 to 5. When n, m, p, q, r, s, t, and u are each 2 or greater, R3 to R 10 In each of the two or more elements, they may be the same or different from each other, and * indicates the bonding position.

[0018] The light-emitting device includes a first electrode, a second electrode, and an intermediate layer between the first and second electrodes. The intermediate layer includes an emitting layer comprising a fused heterocyclic compound represented by chemical formula 1:

[0019] Chemical Formula 1

[0020] .

[0021] In chemical formula 1, X1 and X2 are each independently O, S, or Se, and R1 and R2 are each independently represented by chemical formula 2:

[0022] Chemical formula 2

[0023] .

[0024] In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C7-C 60 Alkylphenyl, substituted or unsubstituted C8-C60 Fused polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; or R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl ring, substituted or unsubstituted C6-C 60 The aryl ring is either substituted or unsubstituted C2-C. 60 Mixed aromatic rings.

[0025] R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0026] n, q, and s are each independent integers selected from 0 to 3. m and p are each independent integers selected from 0 to 4. r is an integer selected from 0 to 2. t and u are each independent integers selected from 0 to 5. When n, m, p, q, r, s, t, and u are each 2 or greater, R3 to R 10 In each of the two or more elements, they may be the same or different from each other, and * indicates the bonding position.

[0027] An electronic device including a light-emitting device is provided.

[0028] The electronic device may be at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television (TV), billboard, lamp for indoor lighting, lamp for outdoor lighting, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, mobile phone, tablet computer, phablet computer, personal information terminal (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, three-dimensional (3D) display, virtual reality display, augmented reality display, vehicle, video wall including multiple displays spliced ​​together, theater screen, stadium screen, phototherapy device, and signage.

[0029] Fused heterocyclic compounds according to embodiments of the present invention may have large depths of highest occupied molecular orbital (HOMO) energy levels and may have improved luminescence efficiency.

[0030] Fused heterocyclic compounds can possess a three-dimensional chemical structure, thereby increasing the distance from the host and reducing side reactions caused by intermolecular interactions. Therefore, light-emitting devices with improved lifetime characteristics can be implemented.

[0031] Fused heterocyclic compounds possess a balanced molecular structure due to their chalcogenide elements, enabling the provision of light-emitting devices with improved luminous efficiency and lifetime characteristics. Attached Figure Description

[0032] Figures 1 to 6 A schematic cross-sectional view illustrating the light-emitting device according to the embodiment.

[0033] Figure 7 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0034] Figure 8 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0035] Figure 9 A schematic cross-sectional view illustrating the stacked structure of the light-emitting structures in a display device according to an embodiment.

[0036] Figure 10 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0037] Figure 11 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0038] Figure 12 This is a block diagram of an electronic device according to an embodiment.

[0039] Figure 13This is a schematic diagram of an electronic device according to an embodiment.

[0040] Figure 14 A schematic exploded perspective view illustrating an electronic device according to an embodiment.

[0041] Figure 15 A schematic diagram illustrating an electronic device according to an embodiment. Detailed Implementation

[0042] According to this disclosure, the fused heterocyclic compound includes a terphenyl bonded to a nitrogen atom forming the fused ring. Furthermore, a light-emitting device comprising a fused heterocyclic compound and an electronic device comprising the light-emitting device are provided.

[0043] Terminology limitations

[0044] The invention will now be described more fully below with reference to the accompanying drawings, in which various embodiments are illustrated. However, the invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. The same reference numerals denote the same elements throughout.

[0045] It will be understood that although the terms “first,” “second,” or “third,” etc., may be used herein to describe various elements, components, areas, layers, and / or parts, these elements, components, areas, layers, and / or parts should not be limited by these terms. These terms are used only to distinguish one element, component, area, layer, or part from another. Therefore, without departing from the teachings of this document, the first element, component, area, layer, or part discussed below may be referred to as the second element, component, area, layer, or part.

[0046] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms containing “at least one,” unless that is otherwise clearly indicated. Thus, reference to the element “the” following a reference to “a” in the claims includes one element as well as multiple elements.

[0047] “At least one” is not to be construed as limited to “a” or “an”. “Or” means “and / or”. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items.

[0048] It will be further understood that when the terms “comprises” and / or “comprising” or “includes” and / or “includes” are used in this specification, they indicate the presence of the described features, areas, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, areas, integers, steps, operations, elements, components and / or groups thereof.

[0049] Exemplary embodiments are described herein with reference to schematic cross-sectional views illustrating preferred embodiments. Therefore, variations in the shapes depicted in the drawings are expected due to factors such as manufacturing techniques and / or tolerances. Consequently, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but will include deviations in shape resulting from manufacturing processes. For example, regions illustrated or described as flat may generally have rough and / or non-linear characteristics. Furthermore, sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate precise shapes of the regions and are not intended to limit the scope of the claims.

[0050] In this specification, the term "substituted or unsubstituted" may refer to a substance substituted or unsubstituted by one or more substituents selected from the group consisting of: for example, deuterium, halogen, cyano, nitro, amino, amine, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, selenyl, phosphine oxide, phosphine sulfide, alkyl (e.g., C1-C1), halogen, cyano, phosphine oxide, alkyl (e.g., C1-C1), alkyl group. 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 alkynyl 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) and heterocyclic groups (e.g., C1-C) 60 Heterocyclic groups or C2-C 60 (Heteroaryl). 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.

[0051] Substituents may include combinations of substituents selected from the above-mentioned groups. For example, at least one hydrogen atom in the alkyl or aryl group, etc., that is a substituent may be replaced by deuterium, halogen, cyano, nitro, amino, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, selenyl, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or combinations thereof.

[0052] Among the substituents mentioned above, polyvalent substituents (such as amino, phosphine sulfide, phosphine oxide, sulfinyl, sulfonyl, oxy, carbonyl, or ester groups, 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.

[0053] In the specification, the hydrocarbon cyclogroup can be any functional group or substituent derived from an aliphatic or aromatic hydrocarbon ring. For example, the hydrocarbon cyclogroup can be a saturated hydrocarbon cyclogroup having 5 to 30 or 5 to 20 cyclic carbon atoms.

[0054] In the specification, the amino group may be alkylamino or arylamino. The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkylamino group is not specifically limited, but may be, for example, 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. Examples of amino groups may include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., but the embodiments are not limited thereto.

[0055] In the specification, silane may be alkylsilane or arylsilane. The alkyl group in alkylsilane may be straight-chain, branched, or cyclic. The number of carbon atoms in alkylsilane is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in arylsilane is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of silane may include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but the embodiments are not limited thereto.

[0056] In the specification, the oxygen group may be an alkyl or aryl group as defined above, 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 20 or 1 to 10. The number of cyclic carbon atoms in the aryloxy group is not specifically limited, but may be, for example, 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.

[0057] In the specification, the thio group may be alkylthio or arylthio. The thio group may be an alkyl or aryl group as defined above, bonded to a sulfur atom. 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 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 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.

[0058] In the specification, 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 implementation is not limited thereto.

[0059]

[0060] In the specification, the ester group may refer to -COOR, where R may be, for example, an alkyl or aryl group, such as C1-C. 10 alkyl.

[0061] In the specification, the boron group may be an alkyl or aryl group as defined above, 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 boron groups may include dimethylboron, diethylboron, tert-butylmethylboron, diphenylboron, phenylboron, etc., but the embodiments are not limited thereto.

[0062] In the specification, the selenoyl group may be alkylselenoyl or arylselenoyl. The selenoyl group may be an alkyl or aryl group as defined above, bonded to a selenium atom. The number of carbon atoms in the alkylselenoyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylselenoyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of selenoyl groups may include methylselenoyl, ethylselenoyl, propylselenoyl, pentylselenoyl, hexylselenoyl, octylselenoyl, dodecylselenoyl, cyclopentylselenoyl, cyclohexylselenoyl, phenylselenoyl, or naphthylselenoyl, etc., but the embodiments are not limited thereto.

[0063] In this specification, sulfinyl group may refer to the above-defined alkyl or aryl group 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.

[0064]

[0065] In this specification, sulfonyl group may refer to the above-defined alkyl or aryl group 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 groups and arylsulfonyl groups. For example, the sulfonyl group may have the following structures, but is not limited thereto.

[0066]

[0067] In this specification, phosphine oxide may refer to the above-defined alkyl or aryl group 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 oxides and arylphosphine oxides. For example, the phosphine oxide group may have the following structures, but is not limited thereto.

[0068]

[0069] In this specification, phosphine sulfide may refer to the above-defined alkyl or aryl group bonded to -P (=S)-. The number of carbon atoms in the phosphine sulfide is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. Phosphine sulfide may include alkylphosphine sulfide and arylphosphine sulfide. For example, phosphine sulfide may have the following structures, but is not limited thereto.

[0070]

[0071] In the instruction manual, symbols and Each represents a bond that connects to an adjacent atom in the corresponding formula or part.

[0072] In the instruction manual, the term "substituted or unsubstituted C" is used. 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 in the substituents.

[0073] In the specification, an alkyl group may be a monovalent hydrocarbon group in which a hydrogen atom has been removed from a straight-chain hydrocarbon group or a branched hydrocarbon group. The number of carbon atoms in the alkyl group may be 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. 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.

[0074] In the specification, alkylene may be a divalent hydrocarbon group in which two hydrogen atoms have been removed from a straight-chain hydrocarbon group or a branched hydrocarbon group.

[0075] In the specification, cycloalkyl can be a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group can be 3 to 60, 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, dicycloheptyl, etc.

[0076] In the instruction manual, the term "C3-C" 60 "Heterocyclic alkyl" can be a monovalent cyclic group having 3 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms, and examples of such groups may include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, tetrahydrothiophenyl, etc.

[0077] In the specification, the alkenyl group may have the same skeleton as the alkyl group and may be a monovalent hydrocarbon group including at least one carbon-carbon double bond. The number of carbon atoms in the alkenyl group is not particularly limited and may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. In the specification, the alkenyl group may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkenyl group.

[0078] In the instruction manual, the term "C5-C" 60 "Cycloalkenyl" can be a monovalent cyclic group having 5 to 60 carbon atoms and at least one carbon-carbon double bond in its cyclic structure, and is non-aromatic. The number of carbon atoms in the cycloalkenyl is not particularly limited and can be 5 to 60, 5 to 30, 5 to 20, or 5 to 10. Examples of cycloalkenyl groups include cyclopentenyl, cyclohexenyl, and cycloheptenyl.

[0079] In the instruction manual, the term "C3-C"60 A "heterocyclic alkenyl" can be a monovalent cyclic group having 3 to 60 carbon atoms, further comprising at least one heteroatom as a cyclic atom in addition to the carbon atoms, and having at least one double bond in its ring structure. The number of carbon atoms in the cyclic alkenyl is not particularly limited and can be 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Examples of heterocyclic alkenyls include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl.

[0080] The alkynyl group may have the same skeleton as the alkyl group and may be a monovalent hydrocarbon group including 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. In the specification, the alkynyl group may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkynyl group.

[0081] In the specification, aryl can be a monovalent hydrocarbon group in which a hydrogen atom is 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 (e.g., biphenyl). There is no particular limitation on the number of carbon atoms in the alkynyl group, and it can be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of aryl groups include, for example, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, tetraphenyl, biphenyl, terphenyl, tetraphenyl, or 1,2-benzophenanthryl.

[0082] In the specification, groups in which two or more aryl rings are fused or linked to each other by aliphatic hydrocarbon rings (such as fluorenyl) may be included in the definition of aryl.

[0083] For example, biphenyl can be interpreted as aryl, or as a phenyl group substituted with a phenyl group.

[0084] In the specification, arylene can be a divalent hydrocarbon group in which two hydrogen atoms are removed from an aryl group.

[0085] In the specification, a heteroaryl group may be a monovalent group having an aromatic structure comprising at least one heteroatom (e.g., B, O, P, S, N, Se, and Si) as a cyclic atom. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. In the specification, a heteroaryl group may be a divalent group having an aromatic structure comprising at least one heteroatom (e.g., B, O, P, S, N, Se, and Si) as a cyclic atom. When a heteroaryl or heteroaryl group comprises two or more heteroatoms, these two or more heteroatoms may be the same as or different from each other.

[0086] In the specification, 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.

[0087] In the instruction manual, the term "C7-C" 60 "Aryl group" can refer to -A 104 A 105 (where A) 104 For C1-C 54 Alkylene, and A 105 For C6-C 59 Aryl), and may include C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30 Aryl group, C7-C 20 Aryl or C7-C 15 Aryl group.

[0088] In this specification, the term "cyclic group" may encompass monocyclic or polycyclic groups, and may also include aliphatic or aromatic rings. Cyclic groups may include carbocyclic and heterocyclic groups.

[0089] In this specification, 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 a bicyclic structure formed by bridging carbons, spiro structures, or fused structures.

[0090] In the specification, the terms "fused polycyclic group" or "fused ring structure" can each refer to a group in which two or more adjacent rings share two or more atoms in the aforementioned polycyclic structure. 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. Examples of fused ring structures may include naphthalene, anthracene, phenanthrene, fluorene, pyrene, benzo[a]pyrene, pentanebenzene, poly[a]benzene, or helicene, etc.

[0091] In the specification, the terms "cycloalkyl" and "cycloalkenyl" refer to saturated and unsaturated cyclic groups, respectively, in which the cyclic atoms are composed of carbon atoms. Heterocyclic groups (e.g., C1-C1) 60 Heterocyclic groups can be cyclic groups that include heteroatoms as cyclic atoms in addition to carbon atoms.

[0092] Each of the cycloalkyl, cycloalkenyl, and heterocyclic groups can be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused together.

[0093] In this specification, "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 this 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.

[0094] Fused heterocyclic compounds

[0095] Fused heterocyclic compounds represented by chemical formula 1 are provided.

[0096] Chemical Formula 1

[0097]

[0098] In chemical formula 1, X1 and X2 can each be independently O, S, or Se. In embodiments, X1 and X2 can be the same as or different from each other.

[0099] In one implementation, X1 and X2 can be 0. In another implementation, X1 and X2 can be S. In another implementation, X1 and X2 can be Se. In another implementation, X1 can be 0, and X2 can be S. In another implementation, X1 can be 0, and X2 can be Se. In another implementation, X1 can be S, and X2 can be 0. In another implementation, X1 can be S, and X2 can be Se. In another implementation, X1 can be Se, and X2 can be 0. In another implementation, X1 can be Se, and X2 can be S.

[0100] R1 and R2 can each be represented independently by chemical formula 2.

[0101] Chemical formula 2

[0102]

[0103] In chemical formulas 1 and 2, R3 to R 10 Each can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C7-C 60 Alkylphenyl, substituted or unsubstituted C8-C 60 Fused polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0104] In the implementation, R3 to R 10 Each can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C2-C 20 Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C5-C 40 Cycloalkenyl, substituted or unsubstituted C3-C 40 Heterocyclic alkyl, substituted or unsubstituted C3-C 40 Heterocyclic alkenyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C2-C 40 heteroaryl, substituted or unsubstituted C6-C 40 Aryloxy group, substituted or unsubstituted C6-C 40 Arylthio, substituted or unsubstituted C8-C 40 Fused polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0105] In the implementation, R3 to R 10 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C3-C 20 Cycloalkyl, substituted or unsubstituted C5-C 20 Cycloalkenyl, substituted or unsubstituted C3-C 20Heterocyclic alkyl, substituted or unsubstituted C3-C 20 Heterocyclic alkenyl, substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C2-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Aryloxy group, substituted or unsubstituted C6-C 20 Arylthio, substituted or unsubstituted C8-C 20 Fused polycyclic groups, -SiRR'R'' or -NRR'.

[0106] R, R', and R'' can each independently be hydrogen, deuterium, halogen, hydroxyl, cyano, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0107] In the implementation, R3 to R 10 Each can be independently hydrogen, deuterium, cyano, or a deuterated or unsubstituted C4-C group. 15 Tertiary alkyl groups (e.g., deuterated or unsubstituted tert-butyl groups), deuterated or unsubstituted C3-C 15 Trialkylsilyl (e.g., deuterated or unsubstituted trimethylsilyl), deuterated or unsubstituted C 18 -C 40 Triarylsilyl (e.g., deuterated or unsubstituted triphenylsilyl), deuterated or unsubstituted phenyl, deuterated or unsubstituted cyanophenyl, deuterated or unsubstituted C7-C 20Alkylphenyl (e.g., deuterated or unsubstituted methylphenyl, deuterated or unsubstituted di-tert-butylphenyl, or deuterated or unsubstituted thiophene), deuterated or unsubstituted biphenyl, deuterated or unsubstituted terphenyl, deuterated or unsubstituted naphthyl, deuterated or unsubstituted tetrahydronaphthyl, deuterated or unsubstituted C 11 -C 40 Alkyl tetrahydronaphthyl (e.g., deuterated or unsubstituted tetramethylhydronaphthyl), deuterated or unsubstituted C 12 -C 20 Diarylamine (e.g., deuterated or unsubstituted diphenylamine), deuterated or unsubstituted carbazolyl, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted phenothiazineyl, or deuterated or unsubstituted pyridinyl.

[0108] In the implementation, R3 to R 10 Each can be independently hydrogen, deuterium, or C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl Phthalatazinyl, naphthidyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cenylinyl, carbazole, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiopheneyl, azafluorenyl, or azadibenzothiopheneyl. These can be unsubstituted or substituted with the substituents mentioned above.

[0109] In the implementation, R3 to R 10 Each can be independently substituted or unsubstituted C6-C. 20 aryl or substituted or unsubstituted C2-C 15 heteroaryl. For example, R3 to R 10 Each can be independently either deuterated or unsubstituted C6-C. 20 aryl or deuterated or unsubstituted C2-C 15 Mixed aromatic compounds.

[0110] Accordingly, fused heterocyclic compounds may include aryl structures, which can improve the resonance and electron transport properties of fused heterocyclic compounds.

[0111] In chemical formulas 1 and 2, R3 to R 10 Two or more of them can combine with each other to form a ring. The remaining groups that do not form a ring can be selected from those listed groups.

[0112] In the implementation, R3 to R 10 Two or more of them can combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl ring, substituted or unsubstituted C6-C 60 The aryl ring is either substituted or unsubstituted C2-C. 60 Mixed aromatic rings.

[0113] In the implementation, R3 to R 10 Two or more of them can combine with each other to form substituted or unsubstituted C3-C 40 Cycloalkyl ring, substituted or unsubstituted C5-C 40 Cycloalkenyl ring, substituted or unsubstituted C3-C 40 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 40 Heterocyclic alkenyl ring, substituted or unsubstituted C6-C 40 The aryl ring is either substituted or unsubstituted C2-C. 40 Heteroary aromatic rings. For example, when R3 to R... 10 When two or more of them combine to form a ring, substituted or unsubstituted C2-C can be formed. 40 Dense heteroaryl rings.

[0114] In the implementation method, when R3 to R 10 When each of the elements exists in multiple forms, adjacent groups can combine to form a ring, or non-adjacent groups can combine to form a ring.

[0115] For example, when multiple R3s exist, they can combine to form a loop. When multiple R4s exist, they can combine to form a loop. When multiple R5s exist, they can combine to form a loop.

[0116] For example, R4 and R5 can be combined to form a ring.

[0117] In chemical formulas 1 and 2, n, q, and s can each be an integer selected from 0 to 3 independently. For example, n, q, and s can each be 0 or 1 independently.

[0118] When each of n, q, and s is 2 or greater, two or more of each of R3, R6, and R8 may be independently the same or different from each other.

[0119] In chemical formula 1, m and p can each be an integer selected from 0 to 4 independently. For example, m and p can each be 0 or 1 independently.

[0120] When m and p are each 2 or greater, two or more of each of R4 and R5 can be independently the same or different from each other.

[0121] In chemical formula 1, r can be 0, 1, or 2. For example, r can be 0 or 1.

[0122] When r is 2, multiple R7s can be the same or different from each other.

[0123] In chemical formula 2, t and u can each be an integer selected from 0 to 5 independently. For example, t and u can each be 0 or 1 independently.

[0124] When t and u are both 2 or greater, R9 and R 10 Each of the two or more in the group can be independently the same as or different from each other.

[0125] In chemical formula 2, * indicates the bonding site, and may also indicate the bonding site in the description below.

[0126] In the implementation, R3 to R 10 At least one of them can be deuterium.

[0127] The fused heterocyclic compound according to the embodiments can be represented by any one of chemical formulas 1-1 to 1-6.

[0128] Chemical Formula 1-1

[0129]

[0130] Chemical formula 1-2

[0131]

[0132] Chemical formulas 1-3

[0133]

[0134] Chemical formulas 1-4

[0135]

[0136] Chemical formulas 1-5

[0137]

[0138] Chemical formulas 1-6

[0139]

[0140] In chemical formulas 1-1 to 1-6, the above limitations on X1 and X2, R1 to R7, n, m, p, q, and r also apply.

[0141] In chemical formulas 1-1 to 1-6, X3 and X4 can each be independently a direct bond, O, S, Se, NR, or CRR'. For example, X3 and X4 can each be independently a direct bond, O, S, or CRR'.

[0142] In the implementation, in chemical formula 1-1, the two X3s may be the same as or different from each other, and the two X4s may be the same as or different from each other. The two X3s and the two X4s may be the same as or different from each other.

[0143] In the embodiments, in chemical formulas 1-3 to 1-6, one of X3 and X4 may be a direct bond, and the other may be O, S, Se, NR, or CRR'. For example, in chemical formulas 1-3 to 1-6, one of X3 and X4 may be a direct bond, and the other may be O or S.

[0144] In chemical formulas 1-1 to 1-6, R 11 and R 12 Each can be independently hydrogen, deuterium, halogen, cyano, hydroxyl, 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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C8-C 60Fused polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0145] In the implementation, R 11 and R 12 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2-C 20 Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C5-C 40 Cycloalkenyl, substituted or unsubstituted C3-C 40 Heterocyclic alkyl, substituted or unsubstituted C3-C 40 Heterocyclic alkenyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C2-C 40 heteroaryl, substituted or unsubstituted C6-C 40 Aryloxy group, substituted or unsubstituted C6-C 40 Arylthio, substituted or unsubstituted C8-C 40 Fused polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0146] The qualifiers R, R', and R'' can also be applied.

[0147] For example, R and R' can each independently be substituted or unsubstituted C6-C. 20 aryl or substituted or unsubstituted C2-C 20 Mixed aromatic compounds.

[0148] In chemical formulas 1-1 and 1-3 through 1-6, v and w can each be independently integers selected from 0 to 4. When v and w are 2 or greater, R 11 and R 12 Each of the two or more in the group can be independently the same as or different from each other.

[0149] In chemical formulas 1-2, p' and m' can each be an integer selected from 0 to 3 independently. When p' and m' are 2 or greater, two or more of each of R4 and R5 can be independently the same or different from each other.

[0150] In chemical formulas 1-3 to 1-6, p'' and m'' can each be 0, 1, or 2 independently. When p'' and m'' are 2 or greater, two or more of each of R4 and R5 can each be independently the same or different from each other.

[0151] The fused heterocyclic compounds according to the embodiments can be represented by chemical formulas 1-7.

[0152] Chemical formulas 1-7

[0153]

[0154] In chemical formulas 1-7, the above limitations for X1 and X2, R1 to R7, m, p and r also apply.

[0155] In chemical formulas 1-7, D1 to D4 can each be hydrogen or deuterium independently. In an embodiment, D1 to D4 can be hydrogen. In an embodiment, at least one of D1 to D4 can be deuterium.

[0156] The degree of deuterium substitution of the fused heterocyclic compound according to the embodiments can range from 0% to 100%. The degree of deuterium substitution can be calculated as a percentage of the number of deuterium atoms relative to the sum of the number of hydrogen atoms and the number of deuterium atoms included in the compound. For example, the degree of deuterium substitution of benzene substituted with 5 deuterium atoms can be about 83.33%.

[0157] The degree of deuteration of the fused heterocyclic compound according to the embodiments can be in the range of 1% to 100%, 5% to 100%, 20% to 100%, 30% to 100%, 40% to 100%, or 50% to 100%.

[0158] The degree of deuteration of the fused heterocyclic compound according to the embodiments can be in the range of 0% to 90%, 0% to 80%, 0% to 70%, 0% to 60%, or 0% to 50%.

[0159] The fused heterocyclic compound according to the embodiments may include at least one of the compounds represented by the following chemical formulas:

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185] .

[0186] Fused heterocyclic compounds may have a heterocyclic core structure comprising a boron atom, a nitrogen atom, and a chalcogenide atom (such as O, S, or Se), and may include an o-terphenyl moiety bonded to the nitrogen atom. The nitrogen atom includes a non-shared electron pair so that the o-terphenyl moiety can be formed in a direction perpendicular to the luminescent core plane of the compound. Accordingly, the distance to the host in the emitting layer can be increased, and side reactions due to intermolecular interactions can be reduced, thereby improving the lifetime characteristics of luminescent devices comprising fused heterocyclic compounds.

[0187] Additionally, fused heterocyclic compounds may include two nitrogen atoms and may include an o-terphenyl moiety bonded to each nitrogen atom. Accordingly, fused heterocyclic compounds may have a balanced molecular structure and can prevent compound decay due to excitons or polarons.

[0188] In an embodiment, the fused heterocyclic compound may be included as a dopant in the emitting layer of the light-emitting device as described below.

[0189] In embodiments, the HOMO energy level of the fused heterocyclic compound can be -5.30 electron volts (eV) or lower, within the ranges of -5.50 eV to -5.30 eV, -5.45 eV to -5.30 eV, or -5.40 eV to -5.30 eV. Within these ranges, the lifetime of the light-emitting device can be improved. In the above chemical formula 1, chalcogen elements (such as O, S, and Se) can be arranged at the X1 and X2 positions to achieve deep HOMO energy levels.

[0190] The luminescence efficiency (photoluminescence quantum yield, PLQY) of fused heterocyclic compounds can be 95% or greater, 96% or greater, or 97% or greater.

[0191] The difference (Stokes shift) between the maximum wavelength at which the fused heterocyclic compound absorbs energy and the maximum wavelength at which it emits energy can be 10 nanometers (nm) or less, 9 nm or less, or 7 nm or less.

[0192] The triplet-singlet energy values ​​of fused heterocyclic compounds can be 0.2 eV or less. Accordingly, triplet excitons can be rapidly converted into singlet excitons via the anti-intersystem crossing (RISC) mechanism, which can further improve the luminescence efficiency and lifetime characteristics of the light-emitting device.

[0193] In this embodiment, the fused heterocyclic compound can be used as a blue luminescent dopant.

[0194] In an implementation, the maximum emission wavelength of blue light can be in the range of 430nm to 475nm, 440nm to 470nm, 440nm to 460nm, 445nm to 460nm, or 450nm to 460nm.

[0195] In an implementation, the full width at one-quarter peak (FWQM) of the emitted blue light can be 40 nm or less, 5 nm to 40 nm, 10 nm to 40 nm, 15 nm to 40 nm, 20 nm to 40 nm, 5 nm to 35 nm, 10 nm to 35 nm, 15 nm to 35 nm, 20 nm to 35 nm, 5 nm to 30 nm, 10 nm to 30 nm, 15 nm to 30 nm, 20 nm to 30 nm, 5 nm to 25 nm, 10 nm to 25 nm, 15 nm to 25 nm, or 20 nm to 25 nm.

[0196] Light-emitting device

[0197] Figures 1 to 6 A schematic cross-sectional view illustrating the light-emitting device according to the embodiment.

[0198] refer to Figure 1 The light-emitting device ED may include a first electrode 110, a second electrode 150, and an intermediate layer ITL inserted between the first electrode 110 and the second electrode 150. The intermediate layer ITL may include an emitting layer 130. The intermediate layer ITL may further include a hole transfer region 120 and an electron transfer region 140.

[0199] The first electrode 110 may be an anode or a cathode. In one embodiment, the first electrode 110 may be an anode and may 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.

[0200] 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).

[0201] In this 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, LiF, Mo, Ti, W, In, Sn, and Zn, or an alloy containing at least two of these. 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.

[0202] 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.

[0203] The thickness of the first electrode 110 can be in the range of about 700 angstroms (Å) to about 10,000 Å. For example, the thickness of the first electrode 110 can be in the range of about 1,000 Å to about 3,000 Å.

[0204] The second electrode 150 can be a cathode or an anode. In an embodiment, the second electrode 150 can be used as an electron injection electrode or as a cathode. The second electrode 150 may include a metal, alloy, or conductive compound having a low work function.

[0205] For example, the second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), 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.

[0206] 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.

[0207] The emitter layer 130 may include the aforementioned fused heterocyclic compound. In one embodiment, the fused heterocyclic compound may be used as a dopant. In another embodiment, the fused heterocyclic compound may be used as a fluorescent dopant. For example, the fused heterocyclic compound may be used as a thermally activated delayed fluorescence (TADF) dopant.

[0208] In some embodiments, fused heterocyclic compounds may be included as blue luminescent dopants. For example, fused heterocyclic compounds may be included as luminescent materials having a maximum emission wavelength in the range of 430 nm to 490 nm.

[0209] In an embodiment, the emitter layer 130 may further 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.

[0210] Chemical formula FD

[0211]

[0212] 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.

[0213] In the implementation, Ar FDIt 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, or pyrene).

[0214] In one embodiment, 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 coordinatingly bonded 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.

[0215] Phosphorescent dopants may include, for example, compounds represented by the chemical formula PD.

[0216] Chemical formula PD

[0217] M(L d 1 ) dx1 (L d 2 ) dx2

[0218] 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).

[0219] In the chemical formula PD, L d 1 It can be a ligand represented by the chemical formula LD1.

[0220] Chemical formula LD1

[0221]

[0222] In the chemical formula LD1, X PD1 and X PD2 They can be carbon (C) or nitrogen (N) independently.

[0223] In the implementation method, X PD1 and X PD2 One of them can be C and the other can be N. In the implementation, X PD1 and X PD2 Each can be N.

[0224] In the chemical formula LD1, CG PD1 and CG PD2 Each can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.

[0225] 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.

[0226] 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 )-*'.

[0227] 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.

[0228] In the chemical formula LD1, R PD1 and R PD2 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 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 ) or -P(=O)(R PD17 (R) PD18 ). Silicates can be derived from -Si(R) as described below. sa (R) sb (R) sc )express.

[0229] R PD3 To R PD18 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -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 C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0230] 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.

[0231] The symbols -* and -*' in the chemical formula LD1 each represent the bonding site where the ligand represented by chemical formula LD1 bonds to M in chemical formula PD.

[0232] 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 CG PD2 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 or L PD2 (etc.) can each independently relate to the reference L PD The same restrictions apply.

[0233] 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, pyridine carboxylates, acetates, oxalates, diketones, isonitriles, isothiocyanates-N, thiosulfates-N, alkylphosphines, arylphosphines (e.g., phenylphosphine), phosphine oxides, phosphites, or combinations thereof.

[0234] In the chemical formula PD, dx2 is an integer selected from 1 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.

[0235] In an embodiment, 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) or 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), 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) as fluorescent dopant materials.

[0236] In addition to the materials mentioned above, the emitting layer 130 may also include a metal composite as a phosphorescent dopant, which may include iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). 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] The aforementioned dopant materials may be used alone or in combination of two or more of them.

[0238] The emitter layer 130 may include a host material that can interact with the aforementioned dopants. For example, the emitter layer 130 may include host materials well known in the relevant art, such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzanthene derivatives, or triphenylene derivatives.

[0239] In an embodiment, 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.

[0240] Chemical formula FH

[0241]

[0242] In the chemical formula FH, R FH1 To R FH4 Each can be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted thio group, substituted or unsubstituted oxy group, substituted or unsubstituted C1-C group. 10Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 Heteroaryl groups or cyclic groups formed by the combination 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.

[0243] 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 Two or more of each of them may be the same as or different from each other.

[0244] In an embodiment, 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.

[0245] Chemical formula pH

[0246]

[0247] 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 C2-C 30 Hybrid aryl. Ar PH C6-C can be substituted or unsubstituted. 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0248] As described above in the definition of terminology, the term "C6-C" 30 "Aryl" can encompass groups in which multiple aryl rings are fused or bonded together by cyclic groups (e.g., aliphatic hydrocarbon rings). For example, C6-C 30 Aryl groups can be fluorene groups.

[0249] As described above in the definition of terminology, the term "C2-C" 30 "Heteroaryl" can encompass groups in which multiple aryl rings are fused or bonded together by heterocyclic groups. For example, C2-C 30 The heteroaryl group can be carbazole, dibenzofuran, or dibenzothiophene, etc. In the embodiments, C2-C 30A 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.

[0250] In the implementation, it includes Ar PH The substituents in it can be -Si(R) sa (R) sb (R) sc ) represents silyl group; and R sa R sb and R sc Each can be independently hydrogen, halogen, hydroxyl, or C1-C. 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl or C2-C 30 Mixed aromatics. R sa R sb and R sc At least one of them can be C6-C 60 Aryl or C2-C 30 heteroaryl. For example, R sa R sb and R sc Each can be independently C6-C 60 Aryl or C2-C 30 Mixed aromatic compounds.

[0251] 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.

[0252] 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)phenyl), PPF (2,8-bis(diphenylphosphino)dibenzo[b,d]furan), TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine), T PBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), Alq3 (tris(8-hydroxyquinoline)aluminum), ADN (9,10-di(naphthyl-2-yl)anthracene), TBADN (2-tert-butyl-9,10-di(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) are used as main materials.

[0253] In an embodiment, the body in the emitting layer 130 may include one or a combination of the body materials described above.

[0254] In one embodiment, 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 another 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.

[0255] Non-limiting examples of hole transport host compounds may include compounds represented by the chemical formula HT.

[0256] Chemical formula HT

[0257]

[0258] In the chemical formula HT, L HT1 L HT2 and L HT3 Each can be independently a directly connected, substituted, or unsubstituted C6-C. 30aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0259] 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 HT3 L HT1 and L HT2 Two or more of each of the aryl rings can be directly linked, for example, by carbon atoms of each aryl ring (e.g., sp2 carbons), to form substituted or unsubstituted C6-C rings. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0260] 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 C2-C 30 Mixed aromatic compounds. Ar HT3 C6-C can be substituted or unsubstituted. 30 Aryl.

[0261] 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.

[0262] In the embodiments, the compound represented by the chemical formula HT may be Ar. HT1 and Ar HT2 At least one of them is a carbazole compound comprising a substituted or unsubstituted carbazole group, or wherein Ar HT1 and Ar HT2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorene group.

[0263] In the implementation, Ar HT1 To Ar HT3 Two adjacent groups in a ring can fuse together to form a ring.

[0264] In a non-limiting example, the electron transport host compound may include a compound represented by the chemical formula ET.

[0265] Chemical formula ET

[0266]

[0267] In the chemical formula ET, X ET1 To XET3 At least one of them can be N; and X ET1 To X ET3 The remaining groups in the [structure] can each be independently C(R) ET R ET It can be hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 60 aryl or substituted or unsubstituted C2-C 60 Mixed aromatic compounds.

[0268] 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.

[0269] 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 C2-C 30 Hybrid aryl.

[0270] When lx1, lx2, or lx3 is 2 or greater, L ET1 L ET2 and L ET3 Two or more of each of the aryl rings can be directly linked together, for example, through the carbon atoms of each aryl ring (e.g., sp2 carbons), to form substituted or unsubstituted C6-C rings. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0271] 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 or substituted or unsubstituted C2-C 30 Mixed aryl groups. For example, Ar ET1 To Ar ET3 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted fluorenel, and Ar ET1 To ArET3 It may be substituted with or not substituted with a silyl group. The silyl group can be formed from -Si(R) as explained above. sa (R) sb (R) sc )express.

[0272] In one embodiment, 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.

[0273] Quantum dots may include a core comprising compounds 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.

[0274] In this 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.

[0275] 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.

[0276] 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.

[0277] In the implementation method, such as Figure 2 As illustrated herein, 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.

[0278] In the implementation method, such as Figure 3 As illustrated herein, 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 being injected from the electron transfer region 140 into 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.

[0279] For example, the hole transfer region 120 may include the compound represented by the chemical formula HT.

[0280] 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, NPD), 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 Hole transfer regions 120 may include one or a combination of the above-mentioned hole transfer materials, such as 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 / camphorsulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine compounds, carbazole compounds (N-phenylcarbazole or polyvinylcarbazole, etc.), or fluorene compounds.

[0281] The aforementioned hole transfer material may be included in at least one of the hole injection layer 122, the hole transport layer 124, and the electron blocking layer 126.

[0282] 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.

[0283] Examples of dopant materials may include metal halide compounds such as LiF, NaCl, CsF, RbCl, RbI, CuI, and 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]cyclopropyl]cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile); tungsten (W) oxides; or molybdenum (Mo) oxides; etc. The hole transfer region 120 may include one or a combination of the above-mentioned dopant materials.

[0284] The thickness of the hole transfer region 120 can be in the range of about 100 Å to about 10,000 Å. For example, the thickness of the hole transfer region 120 can be in the range of about 100 Å to about 1,500 Å.

[0285] 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 in the range of 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 in the range of 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.

[0286] Within the aforementioned thickness range, hole transfer characteristics can be enhanced even under low-voltage operation, and the lifespan of the light-emitting device can be further improved.

[0287] Each layer of the hole transfer region 120 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, or laser thermal transfer.

[0288] The electron transfer region 140 may be formed 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.

[0289] 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.

[0290] In the implementation method, such as Figure 2 As illustrated herein, 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.

[0291] In the implementation method, such as Figure 3 As illustrated herein, the electron transfer region 140 may include an electron injection layer 142, an electron transport layer 144, and a hole blocking layer 146, which are stacked sequentially from the second electrode 150 to the emitter layer 130. The hole blocking layer 146 can block or suppress holes from the hole transfer region 120. Accordingly, the emission energy and luminous efficiency of the emitter layer 130 can be further improved.

[0292] For example, the electron transfer region 140 may include the compound represented by the chemical formula ET.

[0293] For example, electron transfer region 140 may include anthracene compounds, Alq3 (tris(8-hydroxyquinoline)aluminum), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridyl)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-benzo[d]imidazol-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-bis(naphthyl-2-yl)anthracene), or BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene) are used as electron transfer materials. The electron transfer region 140 may include one or a combination of the above-mentioned electron transfer materials.

[0294] 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.

[0295] 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.

[0296] 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, Gd, or any combination thereof.

[0297] 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.

[0298] 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.

[0299] The thickness of the electron transfer region 140 can be in the range of about 100 Å to about 1,000 Å (e.g., about 150 Å to about 500 Å).

[0300] 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 in the range of 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 in the range of about 10 Å to about 900 Å, about 10 Å to about 500 Å, or about 100 Å to about 400 Å.

[0301] Within any of the aforementioned thickness ranges, without significantly increasing the driving voltage, the electron injection and electron transport characteristics can be further improved, and the stability of the electron transfer region 140 can be enhanced.

[0302] Each layer of the electron transfer region 140 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, or laser thermal transfer.

[0303] 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.

[0304] like Figure 4 As explained herein, a second capping layer 160b may be formed on the outer surface of the second electrode 150. In an embodiment, a first capping layer 160a may be formed on the outer surface of the first electrode 110.

[0305] The refractive index of the first capping layer 160a and / or the second capping layer 160b may be 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.

[0306] The first capping layer 160a and the second capping layer 160b can 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.

[0307] 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.

[0308] In the embodiments, the first capping layer 160a and the second capping layer 160b may each independently include 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 include one or a combination of the aforementioned materials.

[0309] In an embodiment, the first capping layer 160a and / or the second capping layer 160b may each independently comprise an amine-containing compound.

[0310] refer to Figure 5 The light-emitting device ED may include multiple light-emitting structures (e.g., light-emitting structures ES1, ES2, and ES3). See reference... Figures 1 to 4 As described, the light-emitting structures ES1, ES2, and ES3 may each include a stacked structure of a hole transfer region 120, an emission layer 130, and an electron transfer region 140. In an embodiment, Figure 5 The light-emitting device ED can be a light-emitting device with a series structure.

[0311] The charge generation layers CGL1 and CGL2 can each be disposed between adjacent structures in the light-emitting structures ES1, ES2, and ES3. The charge generation layers CGL1 and CGL2 can each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0312] The p-type charge generation layer may include a hole transport host compound, such as N,N'-bis(naphthyl-1-yl)-N,N'-diphenylbenzidine (NPB). For example, the p-type charge generation layer may include compounds represented by the chemical formula HT as described above. The p-type charge generation layer may further include a p-type dopant (such as tetracyanoquinone dimethyl ether (TCNQ)).

[0313] The n-type charge-generating layer may 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 above. In embodiments, the n-type charge-generating layer may include phenanthroline compounds.

[0314] 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.

[0315] In the embodiment, 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 can be stacked sequentially on the top surface of the first electrode 110.

[0316] 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 an embodiment, 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.

[0317] exist Figure 5 The example illustrates a 3-stacked series structure of three light-emitting structures, but the series structure of the light-emitting device disclosed herein is not limited to this. Figure 5 The structure described herein. For example, a 2-stacked structure can also be implemented, or as referenced Figure 6 The described 4-stack structure, 5-stack structure or more stacked structure.

[0318] refer to Figure 6 For reference Figure 5 As described, a series structure in which the light-emitting structure and the charge-generating layer are alternately and repeatedly stacked can be disposed between the first electrode 110 and the second electrode 150.

[0319] In this embodiment, the first to m-th light-emitting structures ES1 to ESm can be stacked sequentially from the top surface of the first electrode 110, with a charge generation layer inserted between them. The charge generation layer may include a first charge generation layer CGL1 to a (m-1)-th charge generation layer CGLm-1 stacked sequentially from the top surface of the first electrode 110.

[0320] like Figure 6As explained in the document, 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.

[0321] In the implementation, m is 4, and the intermediate layer ITL of the light-emitting device (see...) Figure 1 The device may have a 4-layer stacked series structure and may include first to fourth light-emitting structures ES1, ES2, ES3 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.

[0322] 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.

[0323] In the implementation, m is 5, and the intermediate layer ITL of the light-emitting device (see...) Figure 1 The device may have a 5-layer 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.

[0324] 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.

[0325] Electronic devices

[0326] 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.

[0327] Examples of electronic devices may include display devices, billboards, signs, light sources, lighting fixtures, personal computers (PCs) (such as laptops or desktop computers), mobile phones, e-books, electronic dictionaries, electronic notebook computers, healthcare devices (including diagnostic devices and various sensors), or various display components for transportation devices (cars, aircraft, ships, or trains, etc.).

[0328] In 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.

[0329] Figure 7 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0330] 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.

[0331] 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.

[0332] 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 some embodiments, the substrate 200 may include polyimide.

[0333] 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).

[0334] 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 structure formed thereon.

[0335] 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 an embodiment, the buffer layer 205 may have a stacked structure comprising a silicon oxide layer and a silicon nitride layer.

[0336] 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.

[0337] Transistors TR1, TR2 and TR3 may each include an active layer 210, a gate insulating layer 220 and a gate electrode 230.

[0338] For each pixel, an active layer 210 may be disposed on the buffer layer 205 and may be patterned. The active layer 210 may include a silicon material (such as amorphous silicon or polycrystalline silicon). p-type 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.

[0339] 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).

[0340] 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 herein, the gate insulating layer 220 may be patterned to partially cover each active layer 210. Optionally, the gate insulating layer 220 may extend continuously across multiple pixel regions or light-emitting regions and may be provided as a common layer for the first transistor TR1, the second transistor TR2, and the third transistor TR3.

[0341] The gate electrode 230 may overlap with the channel region of the active layer 210 in the thickness direction.

[0342] 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.

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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 or Sc, etc.), alloys thereof, or nitrides thereof.

[0347] A through-hole insulating layer 270 may be formed on the insulating interlayer 240 to cover the connecting electrodes 250 and 260.

[0348] 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 an embodiment, the via insulating layer 270 may include a polymer material (such as polyimide, polysiloxane, epoxy resin, acrylic resin, or polyester).

[0349] 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 As described, the light-emitting devices ED1, ED2 and ED3 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.

[0350] The first electrode 110 can be electrically connected to transistors TR1, TR2, and TR3 in circuit layer CL, or to connecting electrodes 250 and 260, via a through-hole structure. Figure 7 As illustrated herein, 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.

[0351] A pixel defining layer 280 may be formed on the via insulating layer 270 to define each light-emitting area or pixel region. The blue light-emitting area, the red light-emitting area, and the green 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 blue light-emitting device, the red light-emitting device, and the green light-emitting device, respectively.

[0352] In an embodiment, the emitting layer of at least one of the red, green, and blue light-emitting devices may comprise a fused heterocyclic compound represented by Chemical Formula 1. In an embodiment, the emitting layer of the blue light-emitting device may comprise a fused heterocyclic compound represented by Chemical Formula 1.

[0353] The pixel-defining layer 280 can partially cover the first electrode 110 in each light-emitting area.

[0354] like Figure 7As illustrated herein, 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.

[0355] In one embodiment, the emitting layer 130 may also be provided as a common layer that extends continuously throughout the light-emitting area or pixel area. In another embodiment, for each light-emitting area or pixel area, the hole transfer area 120, the emitting layer 130, and the electron transfer area 140 may be patterned and formed separately.

[0356] The second electrode 150 can be provided as a common electrode that extends continuously throughout the light-emitting area or pixel area.

[0357] 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.

[0358] 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 combinations thereof; an organic layer comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate or polyacrylic acid), epoxy resin (e.g., aliphatic glycidyl ether (AGE)), or combinations thereof; or a combination of an inorganic layer and an organic layer.

[0359] 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 polarization layer), a color conversion layer, a color filter layer, a window film, or a combination thereof.

[0360] Figure 8 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0361] 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.

[0362] In this embodiment, 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 pixels and may be co-included in the intermediate layer of each light-emitting structure.

[0363] 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.

[0364] 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.

[0365] 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.

[0366] 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.

[0367] 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 embodiment. For ease of explanation and description, [the following is a simplified description]. Figure 9 The explanation of circuit layers, substrates, or pixel-defining layers is omitted, and the shape of each layer or element in the light-emitting structure is simply shown as a rectangle.

[0368] 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.

[0369] In an embodiment, 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 rest may have a single emission layer structure.

[0370] like Figure 9As 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 the embodiment, 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.

[0371] 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.

[0372] 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.

[0373] 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 by a charge generation layer CGL between them. Each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b may correspond to a blue emitting layer.

[0374] 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.

[0375] 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.

[0376] Figure 10 A schematic cross-sectional view illustrating the display device according to the embodiment.

[0377] Figure 10 This describes a display device having a QD-OLED structure according to an embodiment. (Regarding references...) Figure 7 Detailed descriptions of those substantially the same or similar components and structures will not be repeated here.

[0378] refer to Figure 10The pixel limiting layer 280 and the light-emitting device ED can be disposed on the circuit layer CL, as shown in the above reference. Figure 7 As described. In an embodiment, each pixel may emit light in the same wavelength range. In an embodiment, each light-emitting device (ED) may emit blue light.

[0379] In the implementation method, as described above for Figure 5 As described, each light-emitting region may include light-emitting devices with a series structure. In this case, the intermediate layer ITL (see...) of each light-emitting device ED... Figure 1 It can provide a common layer that extends continuously across multiple light-emitting areas.

[0380] The color control layer CCL can be disposed on the encapsulation layer 290, and the color control layer CCL may include color control portions CCP1, CCP2 and CCP3.

[0381] Color control sections CCP1, CCP2, and CCP3 may each include a light converter (such as a quantum dot or 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.

[0382] Color control portions CCP1, CCP2, and CCP3 may be separated from or spaced apart from each other by a 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.

[0383] 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) which transmits the first color light.

[0384] In this embodiment, the first color light, the second color light, and the third color light can be blue light, red light, and green light, respectively. The first quantum dot and the second quantum dot can be red quantum dot and green quantum dot, respectively.

[0385] Color control components CCP1, CCP2, and CCP3 may each further include a scattering material (such as inorganic particles). The third color control component CCP3 may not include quantum dots but 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.

[0386] 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.

[0387] 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.

[0388] 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.

[0389] 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.

[0390] The light-shielding portion CP can be disposed between the color filters. In an embodiment, the light-shielding portion may include a first light-shielding portion CP1 and a second light-shielding portion CP2 containing colorants of different colors.

[0391] In one embodiment, the first light-shielding portion CP1 may include a blue colorant, and the second light-shielding portion CP2 may include a red colorant or a black colorant. In another embodiment, in the blue emitting region, a portion of the first light-shielding portion CP1 may be provided as a blue color filter and may be exposed between a plurality of second light-shielding portions CP2, such that an additional color filter (e.g., a third color filter) may be omitted.

[0392] The first isolation layer 310 may be disposed between the color control layer CCL and the light-emitting device ED (or the encapsulation layer 290). The second isolation layer 320 may be disposed between the color control layer CCL and the color filters CF1 and CF2.

[0393] 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.

[0394] In an embodiment, the isolation layers 310 and 320 may each have a multilayer structure that further includes an organic layer.

[0395] Figure 11 A schematic cross-sectional view illustrating the display device according to an embodiment. (See reference) Figure 10Detailed descriptions of those substantially the same or similar elements and structures are omitted here.

[0396] refer to Figure 11 The light-emitting devices ED corresponding to the color control sections CCP1, CCP2 and CCP3 can be disposed on the first electrode 110, which serves as the pixel electrode, and the light-emitting devices ED can have a series structure.

[0397] In the implementation method, as referenced 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.

[0398] 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.

[0399] In the implementation method, as referenced Figure 6 As described, the light-emitting device ED may include a series structure with 4 stacks, 5 stacks or more stacks.

[0400] Figure 12 This is a block diagram of an electronic device according to an embodiment.

[0401] refer to Figure 12 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.

[0402] 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.

[0403] Data information for the operation of processor 12 or display module 11 can be stored in memory 13. When processor 12 executes the application stored in memory 13, it can transmit image data signals and / or input control signals to display module 11, and display module 11 can process the received signals and output image information through the display screen.

[0404] The power module 14 may include a power supply module (such as a power adapter or battery device) and a power conversion module (which converts the power supplied by the power supply module to generate the power required for the operation of the electronic device 10).

[0405] At least one of the components of the electronic device 10 described above may be included in the display device according to the above embodiment. Additionally, some 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.

[0406] Figure 13 This is a schematic diagram of an electronic device according to various embodiments.

[0407] refer to Figure 13 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, laptops 10_1c, TVs 10_1d, and desktop monitors 10_1e, etc.); wearable electronic devices including display modules (such as smart glasses 10_2a, head-mounted displays 10_2b, and smartwatches 10_2c, etc.); and vehicle electronic devices 10_3 including display modules (such as central information displays (CIDs) located on vehicle instrument panels, center consoles, or dashboards, and interior mirror displays, etc.). The electronic devices may include virtual reality glasses or augmented reality glasses.

[0408] Figure 14 A schematic exploded perspective view illustrating an electronic device according to an embodiment.

[0409] According to the implementation method, the electronic device can be implemented in the form of a mobile phone (smartphone), tablet computer, or PC, which includes the above-described display device.

[0410] refer to Figure 14 The electronic device may include a window structure WS, a display panel DP, and a rear structure RS.

[0411] The window structure WS provides an external display surface that can be recognized by the user (such as the viewing 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.

[0412] 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 user touch / command input is made. The peripheral region PA may substantially correspond to the bezel area of ​​the display device.

[0413] 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.

[0414] In this implementation, 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.

[0415] 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.

[0416] 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.

[0417] Figure 15 A schematic diagram illustrating an electronic device according to an embodiment.

[0418] Electronic devices may be installed in, embedded in, attached to, or integrated with vehicle 400. However, vehicle 400 is not limited to... Figure 15 The implementation methods illustrated herein. Further examples of vehicle 400 may include transportation devices such as three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, motor vehicles, bicycles, or trains. Other examples of vehicle 400 may include electric vehicles or hybrid vehicles.

[0419] refer to Figure 15 At least one of the first to fifth display devices DP1, DP2, DP3, DP4 and DP5 may be applied to vehicle 400.

[0420] In this embodiment, the 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.

[0421] 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).

[0422] 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 or heater, etc., and can also display vehicle information.

[0423] 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.

[0424] 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.

[0425] The electronic device may be at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, lamp for indoor lighting, lamp for outdoor lighting, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, mobile phone, tablet computer, phablet computer, personal information terminal (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall including multiple displays spliced ​​together, theater screen, stadium screen, phototherapy device, and signage.

[0426] The aforementioned light-emitting device ED can be applied to electronic devices and can be used as a light-emitting part or light-emitting unit of electronic devices.

[0427] In some embodiments, the electronic device may include the electronic device described above.

[0428] 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, phototherapy devices, and / or signage.

[0429] The fused heterocyclic compounds according to embodiments will now be described in detail 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.

[0430] Example 1: Synthesis of Compound 23

[0431]

[0432]

[0433] (1) Synthesis of intermediate compound 23-a

[0434] Compound 23-a is prepared by any of the following methods.

[0435] (1) Under an argon atmosphere, N-([1,1'-biphenyl]-3-yl)-N-(3,5-dibromophenyl)-[1,1':3',1''-terphenyl]-2'-amine (10 g, 16 mmol), (phenyl-d5)-boronic acid (2 g, 16 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), potassium carbonate (8.3 g, 60 mmol), and toluene / H2O (3:1, 200 mL) were added to a 2 L flask. The reaction mixture was stirred at 100 °C for 4 hours.

[0436] (2) Under an argon atmosphere, N-([1,1'-biphenyl]-3-yl)-N-(3,5-dibromophenyl)-[1,1':3',1''-terphenyl]-2'-amine (10 g, 16 mmol), (phenyl-d5)-boronic acid (2 g, 16 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (5.8 g, 60 mmol) were added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction mixture was stirred at 140 °C for 2 hours.

[0437] After any reaction is completed, perform the same post-processing and purification steps as follows.

[0438] After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as the developing solvent to obtain intermediate compound 23-a (white solid, 7 g, yield: 70%).

[0439] ESI-LCMS: [M] + :C 42 H 25 D5BrN, 633.6496.

[0440] 2) Synthesis of intermediate compound 23-b

[0441] Under an argon atmosphere, intermediate compound 23-a (7 g, 11 mmol), 3-([1,1':3',1''-terphenyl]-2'-ylamino)phenol (3.7 g, 11 mmol), CuI (2 g, 11 mmol), pyridinecarboxylic acid (1.3 g, 11 mmol), and potassium carbonate (4.1 g, 30 mmol) were added to a 2 L flask, dissolved in 200 mL of DMF, and the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction. The organic layer was collected, dried over MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as the eluent to obtain intermediate compound 23-b (white solid, 7.2 g, yield: 72%).

[0442] ESI-LCMS: [M] + :C 66 H 43 D5N2O, 890.1542.

[0443] 3) Synthesis of intermediate compound 23-c

[0444] Under an argon atmosphere, intermediate compound 23-b (7 g, 7.8 mmol), 3-([1,1'-biphenyl]-3-yloxy)-5-iodo-1,1'-biphenyl-2',3',4',5',6'-d5 (3.5 g, 7.8 mmol), Pd2dba3 (0.7 g, 0.78 mmol), tri-tert-butylphosphine (PtBu3, 0.7 mL, 1.5 mmol), and sodium tert-butoxide (2.9 g, 30 mmol) were added to a 2 L flask, dissolved in 100 mL of o-xylene, and the reaction solution was stirred at 140°C for 2 h. Alternatively, toluene was used instead of o-xylene. When toluene was used, the reaction mixture was heated to reflux (110°C) and stirred for 4 h. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction. The organic layer was collected, dried over MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel and CH2Cl2 and hexane as the developing solvent to obtain intermediate compound 23-c (white solid, 6.1 g, yield: 63%).

[0445] ESI-LCMS: [M]+: C 90 H 54 D 10 N2O2, 1215.5833.

[0446] 4) Synthesis of compound 23

[0447] Under an argon atmosphere, intermediate compound 23-c (6 g, 5 mmol) was added to a 1 L flask, dissolved in 120 mL of o-dichlorobenzene, and then BBr3 (4 equivalents) was added. Alternatively, BI3 could be used instead of BBr3 under the same conditions, with the reaction temperature and / or reaction time adjusted as appropriate. The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was purified and separated by column chromatography using silica gel and CH2Cl2 and hexane as the eluent to obtain compound 23 (yellow solid, 1.5 g, yield: 25%).

[0448] ESI-LCMS: [M]+: C 90 H 48 D 10 B2N2O2, 1231.1558

[0449] Compound 23 1H-NMR (CDCl3): δ=8.20 (m, 4H), 7.90 (d, 2H), 7.75 (d, 4H), 7.43 (m, 12H), 7. 33(m, 8H), 7.21(m, 4H), 7.25(s, 1H), 7.08(m, 8H), 6.99(s, 4H), 6.86(s, 1H)

[0450] Examples 2 to 8

[0451] Fused heterocyclic compounds were prepared by essentially the same method as in Example 1, except that intermediate compound a was changed to intermediate compound c as shown in Table 1 below.

[0452] Table 1

[0453]

[0454] Comparative Examples 1 to 7

[0455] The compounds represented by the following chemical formulas C1 to C7 are used as comparative examples.

[0456]

[0457]

[0458] Measurement Examples

[0459] For each compound in the examples and comparative examples, the HOMO (highest occupied molecular orbital) energy level and the maximum emission wavelength (λ) in the film phase were measured. Emi The maximum absorption wavelength (λ) in the solution phase Abs ) and maximum emission wavelength (λ) emi The difference between the maximum wavelength when energy is absorbed and the maximum wavelength when energy is emitted in the solution phase (λ) Emi -λ Abs Stokes shift), luminescence efficiency (photoluminescence quantum yield, PLQY), and FWQM were calculated, and the results are shown in Table 2.

[0460] (1) Using a SHIMADZU UV-1800 ultraviolet vision (UV) / visible scanning spectrophotometer equipped with a deuterium / tungsten-halogen light source and a silicon photodiode, λ was measured using Labsolution UV-Vis software. Abs .

[0461] (2) Using a HORIBA fluoromax+ spectrometer equipped with a xenon light source and monochromator, λ was measured using FluorEssence software. Emi .

[0462] (3) PLQY was measured using the PLQY measurement software with the Hamamatsu Quantaurus-QY Absolute PL quantum yield spectrometer equipped with a xenon light source, monochromator, photon multichannel analyzer and integrating sphere.

[0463] Table 2

[0464]

[0465] Manufacturing of light-emitting devices

[0466] As the anode, it forms a 15 ohm / cm² anode. 2 The glass substrate (Corning product) for the (1200Å) 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 pure 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.

[0467] Subsequently, NPD was vacuum deposited on the anode to form a hole injection layer with a thickness of 300 Å. HTL-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 200 Å, and then CzSi was deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0468] The host mixture compound (in which HT-1 and ET-1 are mixed in a 1:1 weight ratio), PS-1, and the dopant compounds shown in Table 3 below are co-deposited in a weight ratio of 85:14:1 to form an emitter layer with a thickness of 300 Å. TSPO1 is deposited on the emitter layer to form a hole-blocking layer with a thickness of 200 Å.

[0469] TPBi was deposited on a hole-blocking layer to form an electron transport layer with a thickness of 300 Å, and then LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al was deposited on the electron injection layer to form a LiF / Al electrode (cathode) with a thickness of 3000 Å. Subsequently, a capping layer with a thickness of 700 Å was formed on the LiF / Al electrode by CPL-1. Each layer was formed by vacuum deposition. The compounds used to fabricate the light-emitting device are shown below. The following materials are commercially available products and were purified by sublimation.

[0470]

[0471] Evaluation Example

[0472] The characteristics of the light-emitting device were measured as follows, and the results are shown in Table 3 below.

[0473] 1) Measured 10 mA / cm² using the V7000 OLED IVL testing system (Polaronix). 2 The driving voltage (V) and luminous efficiency (candela per ampere (cd / A)) at the current density.

[0474] 2) When at 10mA / cm 2 When continuously driven at a current density, the time it takes for the initial brightness to decay to 95% of its original brightness is measured relative to the value from Comparative Example 1 as the relative device lifetime (T). 95 ).

[0475] Table 3

[0476]

[0477] Referring to Tables 2 and 3, the fused heterocyclic compounds of the examples exhibit a HOMO level of -5.3 eV or lower, luminous efficiency of 97% or greater, a Stokes shift of 10 nm or less, and a full width at half maximum (FWQM) of 22 nm or less. Correspondingly, this resulted in a low driving voltage of 3.8 V or lower, high luminous efficiency of 550 cd / A or greater, improved CIE color coordinate characteristics of 0.05 or less, and a lifetime (TL) comparable to Comparative Example 1. 95 2.7 times or more of the lifespan (T) 95 ( ) light-emitting device.

[0478] The compounds of the comparative examples do not satisfy the structure of chemical formula 1, and the light-emitting devices of the comparative examples provide characteristics that are inferior to those of the light-emitting devices from the embodiments.

[0479] In compound C1 of Comparative Example 1 and compound C2 of Comparative Example 2, the nitrogen bonded to the aryl group is located at the X1 and / or X2 positions of Formula 1, and the HOMO energy level is significantly reduced, resulting in a slight deterioration in luminescence efficiency. Consequently, the lifetime and luminescence efficiency of the light-emitting device also deteriorate.

[0480] In compound C4 of Comparative Example 4, the X1 position of Formula 1 shifts, and oxygen atoms concentrate on one side of the molecule, resulting in an imbalance within the molecule. Accordingly, the luminous efficiency of the compound is significantly reduced, and the driving voltage of the light-emitting device increases. The luminous efficiency of the light-emitting device also deteriorates. Furthermore, the color coordinate characteristics of the light-emitting device are significantly worse than those of the light-emitting devices from the Examples.

[0481] In compound C3 of Comparative Example 3 and compound C5 of Comparative Example 5, phenyl or biphenyl (not terphenyl) is bonded at the R1 and / or R2 positions of Formula 1, and the HOMO energy level is reduced, resulting in a deterioration in the lifetime or luminous efficiency of the light-emitting device.

[0482] In compound C6 of Comparative Example 6, the nitrogen bonded to the aryl group is located at positions X1 and X2 of Formula 1, and the biphenyl (not terphenyl) is bonded at positions R1 and / or R2 of Formula 1. In compound C7 of Comparative Example 7, a nuclear structure different from that of Formula 1 is included. In Comparative Examples 6 and 7, the HOMO energy level is slightly decreased and the Stokes shift is increased. Accordingly, the lifetime of the light-emitting device deteriorates.

Claims

1. A fused heterocyclic compound represented by chemical formula 1: Chemical Formula 1 in, In chemical formula 1, X1 and X2 are each independently O, S, or Se, and R1 and R2 are each independently represented by chemical formula 2: Chemical formula 2 In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 Alkyl, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C7-C 60 Alkylphenyl, substituted or unsubstituted C8-C 60 Fused polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; or R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl ring, substituted or unsubstituted C6-C 60 The aryl ring is either substituted or unsubstituted C2-C. 60 heteroaryl rings, Where R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, 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 Alkyl, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Fused polycyclic groups, n, q, and s are each an independent integer selected from 0 to 3. m and p are each an independent integer selected from 0 to 4. r is an integer selected from 0 to 2. t and u are each an independent integer selected from 0 to 5. When n, m, p, q, r, s, t, and u are each 2 or greater, R3 to R 10 Two or more of each of them are the same as or different from each other, and * indicates the bonding location.

2. The fused heterocyclic compound according to claim 1, wherein the fused heterocyclic compound is represented by any one of chemical formulas 1-1 to 1-6: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 Chemical formulas 1-5 Chemical formulas 1-6 in, In chemical formulas 1-1 to 1-6, X1 and X2, R1 to R7, n, m, p, q, and r are the same as those defined in chemical formulas 1 and 2. X3 and X4 are each independently a direct bond, O, S, Se, NR, or CRR'. R 11 and R 12 Each is independently hydrogen, deuterium, halogen, cyano, hydroxyl, 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 Alkyl, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, 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 C8-C 60 Fused polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R, R, R', and R'' are the same as those defined in Chemical Formula 1 and Chemical Formula 2. v and w are each an independent integer selected from 0 to 4. p' and m' are each an independent integer selected from 0 to 3. p'' and m'' are each an independent integer selected from 0 to 2. When v, w, p', m', p'', and m'' are 2 or greater, R4, R5, and R 11 and R 12 Each of the two or more in the group is independently the same as or different from each other.

3. The fused heterocyclic compound according to claim 1, wherein, In chemical formula 2, R8 to R 10 Each is either hydrogen or deuterium.

4. The fused heterocyclic compound according to claim 1, wherein the fused heterocyclic compound is represented by chemical formulas 1-7: Chemical formulas 1-7 in, In chemical formulas 1-7, X1 and X2, R1 to R7, m, p and r are the same as those defined in chemical formula 1, and D1 to D4 are each independently hydrogen or deuterium.

5. The fused heterocyclic compound according to claim 1, wherein, In chemical formulas 1 and 2, R3 to R 10 Each is independently either substituted or unsubstituted C6-C. 20 aryl or substituted or unsubstituted C2-C 15 Mixed aromatic compounds.

6. The fused heterocyclic compound according to claim 1, wherein, In chemical formula 1, n, m, p, and q are each independently 0 or 1.

7. The fused heterocyclic compound according to claim 1, wherein, In chemical formula 2, s, t, and u are each independently 0 or 1.

8. The fused heterocyclic compound according to claim 1, wherein, In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, cyano, or a C4-C group that is either deuterated or unsubstituted. 15 Tertiary alkyl groups, deuterated or unsubstituted C3-C 15 Trialkylsilyl, deuterated or unsubstituted C 18 -C 40 Triarylsilyl, deuterated or unsubstituted phenyl, deuterated or unsubstituted cyanophenyl, deuterated or unsubstituted C7-C 20 Alkylphenyl, deuterated or unsubstituted biphenyl, deuterated or unsubstituted terphenyl, deuterated or unsubstituted naphthyl, deuterated or unsubstituted tetrahydronaphthyl, deuterated or unsubstituted C 11 -C 40 Alkyl tetrahydronaphthyl, deuterated or unsubstituted C 12 -C 20 Diarylamine, deuterated or unsubstituted carbazolyl, deuterated or unsubstituted dibenzofuranyl, deuterated or unsubstituted phenothiazinyl, or deuterated or unsubstituted pyridinyl.

9. The fused heterocyclic compound according to claim 1, wherein the fused heterocyclic compound comprises at least one of the compounds represented by the following chemical formulas: 。 10. The fused heterocyclic compound of claim 1, wherein the fused heterocyclic compound has a highest occupied molecular orbital energy level of -5.3 electron volts or lower.

11. A light-emitting device, comprising: First electrode; Second electrode; as well as An intermediate layer between the first electrode and the second electrode, the intermediate layer comprising an emission layer comprising a fused heterocyclic compound represented by chemical formula 1 according to any one of claims 1 to 10.

12. The light-emitting device of claim 11, wherein the emitting layer comprises a host and a dopant, and includes the fused heterocyclic compound as a thermally activated delayed fluorescence dopant.

13. The light-emitting device according to claim 12, wherein the dopant further comprises a phosphorescent dopant.

14. The light-emitting device according to claim 12, wherein the host comprises a hole transport host compound represented by the chemical formula HT and an electron transport host compound represented by the chemical formula ET: Chemical formula HT in, In the chemical formula HT, L HT1 L HT2 and L HT3 Each is independently a directly linked, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl, lx1 to lx3 are each an independent integer selected from 0 to 10. Ar HT1 and Ar HT2 Each is independently either substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 heteroaryl, and Ar HT3 For substituted or unsubstituted C6-C 30 Aryl, Chemical formula ET In the chemical formula ET, X ET1 To X ET3 At least one of them is N, and X ET1 To X ET3 The remaining groups in each are independently C(R) ET ), R ET Hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 60 aryl or substituted or unsubstituted C2-C 60 Mixed aromatics, lx1 to lx3 are each an independent integer selected from 0 to 10. L ET1 To L ET3 Each is independently a directly linked, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl, and Ar ET1 To Ar ET3 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

15. The light-emitting device of claim 11, wherein the emitting layer emits blue light, and the maximum emission wavelength of the blue light is in the range of 430 nanometers to 475 nanometers.

16. An electronic device comprising a light-emitting device according to any one of claims 11 to 15.

17. The electronic device of claim 16, wherein the emitting layer of the light-emitting device exists in the form of two or more emitting layers, and at least one of the two or more emitting layers comprises the fused heterocyclic compound represented by chemical formula 1.

18. The electronic device of claim 17, further comprising a color control portion, the color control portion comprising a light converter.

19. The electronic device of claim 16, wherein the light-emitting device comprises a blue light-emitting device, a red light-emitting device, and a green light-emitting device, and At least one of the blue light-emitting device, the red light-emitting device, and the green light-emitting device includes the fused heterocyclic compound represented by chemical formula 1.

20. The electronic device of claim 19, wherein the electronic device is at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, lamp for indoor lighting, lamp for outdoor lighting, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, mobile phone, tablet computer, tablet PC, personal information terminal, wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall comprising multiple displays joined together, theater screen, stadium screen, phototherapy device, and signage.

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