Polycyclic compound, light-emitting device, electronic device, and electronic apparatus

Abstract

The invention relates to a polycyclic compound, a light-emitting device, an electronic device, and an electronic apparatus. The polycyclic compound may be represented by Chemical Formula 1. All variables in Chemical Formula 1 are described herein. The light-emitting device may include a polycyclic compound, the electronic device may include the light-emitting device, and the electronic device may include the light-emitting device. The light emitting device includes a first electrode, a second electrode, and an intermediate layer between the first electrode and the second electrode. The intermediate layer includes an emission layer and an organic layer. At least one of the emission layer and the organic layer includes a polycyclic compound represented by Chemical Formula 1. [Chemical Formula 1]

Description

[0001] Cross-references to related applications

[0002] This application claims priority to Korean Patent Application No. 10-2024-0160532, filed on November 12, 2024, with the Korean Intellectual Property Office (KIPO), the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] This disclosure relates to polycyclic compounds, light-emitting devices, electronic devices, and electronic devices. Background Technology

[0004] Organic light-emitting devices are self-emissive and offer improved viewing angles and contrast characteristics. Additionally, they provide high response times and high brightness.

[0005] An organic light-emitting device may include an intermediate layer comprising an emitting layer disposed between a first electrode and a second electrode. The intermediate layer may further include an organic layer. Holes moving from the first electrode and electrons moving from the second electrode can recombine in the emitting layer to generate excitons. When the excitons transition from an excited state to a ground state, light emission is achieved.

[0006] Heterocyclic compounds containing heteroatoms can have different properties depending on their chemical structure, and can be used as materials for organic light-emitting devices in various layers. Summary of the Invention

[0007] According to aspects of this disclosure, polycyclic compounds with improved electron transfer properties and lifetime properties are provided.

[0008] According to aspects of this disclosure, a light-emitting device having improved light-emitting characteristics (e.g., luminous efficiency) and lifetime characteristics is provided.

[0009] According to aspects of this disclosure, an electronic device including a light-emitting device is provided.

[0010] According to aspects of this disclosure, an electronic device including a light-emitting device is provided.

[0011] Provide polycyclic compounds represented by chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1, any one or two of Y1 to Y4 are C or N, and the remaining Y1 to Y4 are C. When Y1, Y2, Y3, or Y4 are N, R is the N bonded to Y1, Y2, Y3, or Y4. 1 R 2 R 3 Or R4 The quantity k is 0. When Y1, Y2, Y3, or Y4 is C, R is the bonded element to Y1, Y2, Y3, or Y4. 1 R 2 R 3 Or R 4 The quantity k is 1.

[0015] R 1 To R 10 Each of these groups is independently hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups.

[0016] Multiple n2s are integers selected from 0 to 2, and may be the same as or different from each other. Multiple n3s are integers selected from 0 to 3, and may be the same as or different from each other. When n2 and n3 are integers 1 or greater, R... 5 To R 10 Two or more adjacent groups in a ring may optionally combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

[0017] When any two, any three, or all four k are 1, R 1 To R 4 Any two, any three, or all four corresponding groups in the ring combine with each other to form at least one substituted or unsubstituted saturated or unsaturated ring.

[0018] L1 and L2 are independently substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C4-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Fused arylene or substituted or unsubstituted C4-C 60 Dense heteroaryl groups.

[0019] The aromatic cyclic groups, including Y1 to Y4, that are directly bonded to L1 and L2, as well as the substituted or unsubstituted 1,10-phenanthroline groups that are directly bonded to L1 or L2, each independently satisfy a meta or para relationship.

[0020] In some respects, R 1 and R 2 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; R 2 and R 3 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; R 3 and R 4 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; or R 1 and R 2 They can combine with each other and R 3 and R 4 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0021] In some respects, by R 1 and R 2 The combination of R 2 and R 3 The combination of R 3 and R 4 The combination or R 1 and R 2 The combination of and R 3 and R 4 The substituted or unsubstituted saturated or unsaturated rings formed by the combination can be selected from substituted or unsubstituted C5-C. 30 Aliphatic hydrocarbon rings, substituted or unsubstituted C6-C 60 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 60 Aromatic heterocycles or substituted or unsubstituted C 12 -C 60 Fused ring.

[0022] In some respects, groups derived from aromatic cycloalkanes including Y1 to Y4 may be represented by any one of chemical formulas 2-1 to 2-41, which will be described below.

[0023] In some respects, groups derived from aromatic cycloalkanes including Y1 to Y4 may be represented by any one of chemical formulas 2-31 to 2-41, which will be described below.

[0024] In some respects, L1 and L2 can each be independently represented by any one of the chemical formulas 3-1 to 3-44, which will be described below.

[0025] In some respects, a polycyclic compound represented by chemical formula 1 may be represented by any one of chemical formulas 4-1 to 4-13, which will be described below.

[0026] In some respects, a polycyclic compound represented by chemical formula 1 may be represented by any one of chemical formulas 4-1 to 4-6, which will be described below.

[0027] The light-emitting device may include a first electrode, a second electrode, and an intermediate layer between the first and second electrodes. The intermediate layer may include an emitting layer and an organic layer. At least one of the emitting layer and the organic layer may include a polycyclic compound represented by the above-described chemical formula 1.

[0028] In some aspects, the intermediate layer may include a light-emitting structure. The light-emitting structure may include: a hole transfer region, including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; an emission layer; and an electron transfer region, including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. At least one of the hole transfer region, the emission layer, and the electron transfer region may include a polycyclic compound represented by Formula 1.

[0029] In some aspects, the light-emitting structure may include multiple light-emitting structures, and the intermediate layer may include a charge-generating layer between adjacent light-emitting structures. At least one of the emitting layer and the charge-generating layer may include a polycyclic compound represented by Formula 1.

[0030] In some aspects, the charge generation layer may include an n-type charge generation layer and a p-type charge generation layer.

[0031] In some aspects, the emitter layer may include a first emitter layer and a second emitter layer, and the organic layer may include a first hole injection layer, a first hole transport layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron transport layer, and a second electron injection layer. The first hole injection layer, the first hole transport layer, the first emitter layer, the first electron transport layer, the n-type charge generation layer, the p-type charge generation layer, the second hole transport layer, the second emitter layer, the second electron transport layer, and the second electron injection layer may be stacked sequentially in the direction from the first electrode to the second electrode.

[0032] In some aspects, at least one of the first electron transport layer, the first emitter layer, the n-type charge generation layer, the second emitter layer, and the second electron transport layer may include a polycyclic compound represented by chemical formula 1.

[0033] In some aspects, at least two of the first electron transport layer, the n-type charge generation layer, and the second electron transport layer may include a polycyclic compound represented by chemical formula 1.

[0034] In some aspects, the n-type charge-generating layer may include: a polycyclic compound represented by chemical formula 1; and at least one metal selected from the group consisting of alkali metals, alkaline earth metals, lanthanides, rare earth metals, transition metals, post-transition metals and their alloys.

[0035] Electronic devices include light-emitting devices.

[0036] Electronic devices include light-emitting devices. Electronic devices may be one of the following: flat panel displays, curved displays, computer monitors, medical monitors, televisions (TV), billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable 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 comprising multiple displays joined together, theater screens, stadium screens, phototherapy devices, and signage.

[0037] The polycyclic compounds represented by chemical formula 1 according to aspects of this disclosure can provide improved electron transfer properties and lifetime properties.

[0038] The light-emitting devices according to this disclosure, as well as electronic devices and electronic equipment including the light-emitting devices, can provide improved light-emitting characteristics and lifetime characteristics. Attached Figure Description

[0039] Figures 1 to 6 A schematic cross-sectional view illustrating the light-emitting device according to aspects of this disclosure.

[0040] Figure 7 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0041] Figure 8 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0042] Figure 9 A schematic cross-sectional view illustrating the stacked structure of the light-emitting structures in a display device according to aspects of this disclosure.

[0043] Figure 10 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0044] Figure 11 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0045] Figure 12 A block diagram of an electronic device according to aspects of this disclosure.

[0046] Figure 13 A schematic diagram of an electronic device according to various aspects of this disclosure.

[0047] Figure 14 A schematic exploded perspective view illustrating an electronic device according to aspects of this disclosure.

[0048] Figure 15 A schematic diagram illustrating an electronic device according to aspects of this disclosure.

[0049] Figure 16 A graph showing the results of lifetime evaluation of the light-emitting devices with a single light-emitting structure manufactured in Example 3, Comparative Example 1, and Comparative Example 2.

[0050] Figure 17 A graph showing the results of evaluating the luminous efficiency of the light-emitting devices with a series structure manufactured in Examples 6, 7, and 8, and Comparative Example 3.

[0051] Figure 18 A graph showing the results of lifetime evaluation of the light-emitting devices with tandem structures manufactured in Examples 6, 7, and 8, and Comparative Example 3. Detailed Implementation

[0052] According to this disclosure, a polycyclic compound represented by Formula 1 is provided in which two linkers comprising aromatic ring structures are connected to two adjacent carbon atoms on a core comprising a fused ring structure, and a substituted or unsubstituted 1,10-phenanthroline group is connected to each of the linkers via a meta- or para-cyclic atom relative to the cyclic atom connected to the core comprising the fused ring structure. The polycyclic compound represented by Formula 1 may possess improved electron transfer properties. For example, the nitrogen atom of the substituted or unsubstituted 1,10-phenanthroline can readily form strong bonds with alkali metals, thereby improving electron injection properties.

[0053] Provide light-emitting devices, display devices, electronic devices, and electronic devices that include polycyclic compounds represented by chemical formula 1.

[0054] <Terminology Limitations>

[0055] 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 (e.g., -F, -Cl, -Br or -I), cyano, nitro, amino, amine, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, selenyl, phosphine oxide, phosphine sulfide, alkyl (e.g., C1-C1) 60 Alkyl or C1-C 10 Alkyl), alkenyl (e.g., C2-C) 60 alkenyl or C2-C 10 alkenyl), alkynyl (e.g., C2-C) 60 Alkyne group or C2-C 10 alkynyl), alkoxy (e.g., C1-C) 60 Alkoxy or C1-C 10 alkoxy), hydrocarbon cyclic group, aryl (e.g., C6-C) 60 Aryl or C6-C 30 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.

[0056] Substituents may include combinations of substituents selected from the above-mentioned groups. For example, at least one hydrogen atom in the alkyl, aryl, etc. group that is a substituent may be replaced by deuterium, halogen, cyano, nitro, amino, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, selenyl, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or combinations thereof.

[0057] Among the substituents mentioned above, polyvalent substituents (such as amino, phosphine sulfide, phosphine oxide, sulfinyl, sulfonyl, oxygen, carbonyl, ester, etc.) can each be independently converted from C1 to C2. 10 Alkyl, C2-C 10 alkenyl, C2-C 10 alkynyl or C6-C 10 Aryl substitution.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064]

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069]

[0070] 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.

[0071]

[0072] 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.

[0073]

[0074] 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.

[0075]

[0076] In the instruction manual, symbols and Each represents a bond that connects to an adjacent atom in the corresponding formula or part.

[0077] 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 not include the number of carbon atoms in the substituents.

[0078] 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, octyl, etc.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] In the instruction manual, the term "C7-C" 60 "Aryl" can be composed of -(A 101 (A) 102 (where A) 101 Can be C1-C 54 Alkylene, and A 102 It can be C6-C 59 Aryl groups, for example, C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30 Aryl group, C7-C 20 Aryl or C7-C 15 Aryl alkyl groups, and as used herein, the term "C3-C" 60 "Heteroarylene" can be composed of (A) 103 (A) 104 (where A) 103 Can be C1-C 59 Alkylene, and A 104 Can be C1-C 59 (Heteroaryl) groups, for example, C2-C 50 Heteroaryl, C2-C 40 Heteroaryl, C2-C 30 Heteroaryl, C2-C 20 Heteroaryl or C2-C 15 Heteroaryl alkyl groups.

[0083] 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.

[0084] 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.

[0085] In the instruction manual, the term "C3-C" 60A "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.

[0086] In the specification, 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. The number of carbon atoms in the alkynyl 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 alkynyl group may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkynyl group.

[0087] 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 cyclic groups are directly linked (e.g., biphenyl). The number of cyclic carbon atoms in the aryl group can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, for example, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, tetraphenyl, biphenyl, terphenyl, tetraphenyl, 1,2-benzophenanthryl, etc.

[0088] In the specification, groups in which two or more aryl rings are fused together or connected to each other by aliphatic hydrocarbon rings (such as fluorenyl) may be included in the definition of aryl.

[0089] For example, biphenyl can be interpreted as aryl, or as a phenyl group substituted with a phenyl group.

[0090] In the specification, arylene can be a divalent hydrocarbon group in which two hydrogen atoms are removed from an aryl group.

[0091] 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, or 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, or 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.

[0092] 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.

[0093] 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.

[0094] 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, fused structures, etc.

[0095] 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, helicene, etc.

[0096] In the specification, the term "carbocyclic group (e.g., C3-C50)" is used. 60 "Carbocyclic group" can be a cyclic group in which the carbon atom is the only cyclic atom. In the specification, heterocyclic groups (e.g., C1-C1) are also used. 60 A heterocyclic group can be a cyclic group that includes at least one heteroatom as a cyclic atom in addition to a carbon atom.

[0097] In the specification, carbocyclic and heterocyclic groups can each be independently a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused together.

[0098] 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.

[0099] <Polycyclic compounds>

[0100] The polycyclic compounds according to aspects of this disclosure can be represented by the following chemical formula 1.

[0101] [Chemical Formula 1]

[0102]

[0103] In chemical formula 1, any one or two of Y1 to Y4 are C or N, and the remaining Y1 to Y4 are C. When Y1, Y2, Y3, or Y4 are N, R is the N bonded to Y1, Y2, Y3, or Y4. 1 R 2 R 3 Or R 4 The quantity k is 0. When Y1, Y2, Y3, or Y4 is C, R is the bonded element to Y1, Y2, Y3, or Y4. 1 R 2 R 3 Or R 4 The quantity k is 1.

[0104] R 1 To R 10 Each group can independently be hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups.

[0105] Multiple n2 are each integer selected from 0 to 2, and may be the same or different from each other. Multiple n3 are each integer selected from 0 to 3, and may be the same or different from each other.

[0106] When n2 and n3 are integers of 1 or greater, R 5 To R 10Two or more adjacent groups may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0107] When any two, any three, or all four k are 1, R 1 To R 4 Any two, any three, or all four corresponding groups may combine with each other to form at least one substituted or unsubstituted saturated or unsaturated ring. When two or more substituted or unsubstituted saturated or unsaturated rings are formed, they may be the same as or different from each other.

[0108] L1 and L2 can each independently be substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C4-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Fused arylene or substituted or unsubstituted C4-C 60 Dense heteroaryl groups.

[0109] C6-C 60 Fused arylene refers to an arylene group with 6 to 60 carbon atoms in which two or more benzene rings (or other aromatic rings) are fused (condensed) together by sharing adjacent carbon atoms.

[0110] C6-C 60 Examples of fused aryl groups include, but are not limited to, naphthylene, anthracene, phenanthrene, pyrene, trehalyl, perylene, myristyl and other polycyclic aromatic groups having a fused benzene ring.

[0111] C4-C 60 Fused heteroaryl refers to a heteroaryl group having 4 to 60 carbon atoms in which two or more aromatic rings are fused (condensed) together by sharing adjacent carbon atoms, and at least one ring contains one or more heteroatoms (such as nitrogen, oxygen or sulfur).

[0112] C4-C 60 Examples of fused heteroaryl groups include, but are not limited to, indolyl, benzothiophene, benzofuranyl, carbazolyl, phenanimidazolyl, dibenzothiophene, dibenzofuranyl, phenoxazinyl, phenthiazinyl, and thiaanthryl, as well as higher-order fused heteroaryl systems containing up to about 60 carbon atoms.

[0113] The aromatic cyclic groups including Y1 to Y4 that are directly bonded to L1 and L2, as well as the substituted or unsubstituted 1,10-phenanthroline groups that are directly bonded to L1 or L2, can each independently satisfy the meta or para relationships with each other.

[0114] In the polycyclic compound represented by Formula 1, two carbon atoms in the adjacent positions on the core of the structure derived from the aromatic cyclic group including Y1 to Y4 can be connected to the linker L1 and L2, and the substituted or unsubstituted 1,10-phenanthroline group can be connected to L1 and L2 through the cyclic atom in the meta or para position relative to the cyclic atom connected to the core of the linker including the fused ring structure, thereby effectively improving the electron transfer properties.

[0115] In some respects, substituted or unsubstituted C8-C 60 Fused polycyclic groups can be C4-C 10 Aliphatic hydrocarbon rings and C6-C 50 Fused polycyclic aromatic hydrocarbon rings. For example, substituted or unsubstituted C8-C rings. 60 Fused polycyclic groups can have one C4-C6 aliphatic hydrocarbon ring fused to two C6-C6 rings. 15 The structure between aromatic hydrocarbon rings. For example, substituted or unsubstituted C8-C. 60 The fused polycyclic group can be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted spirodifluorenyl.

[0116] In some respects, the silyl group can be -Si(R) S1 (R) S2 (R) S3 ), and R S1 To R S3 It can be independently hydrogen, deuterium, 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 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, 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.

[0117] In some respects, R 1 and R 2They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; R 2 and R 3 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; R 3 and R 4 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings; or R 1 and R 2 They can combine with each other and R 3 and R 4 They can combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0118] The substituted or unsubstituted saturated or unsaturated ring may be selected from the substituted or unsubstituted C5-C. 60 Cycloalkanes, substituted or unsubstituted C5-C 60 Cycloolefins, substituted or unsubstituted C5-C 60 Heterocyclic alkanes, substituted or unsubstituted C5-C 60 Heterocyclic alkenes, substituted or unsubstituted C6-C 60 Aromatic hydrocarbons, or substituted or unsubstituted C5-C hydrocarbons 60 Heteroaromatic hydrocarbons. Substituted or unsubstituted saturated or unsaturated rings can be substituted or unsubstituted monocyclic or substituted or unsubstituted polycyclic.

[0119] In some respects, by R 1 and R 2 The combination of R 2 and R 3 The combination of R 3 and R 4 The combination or R 1 and R 2 The combination of and R 3 and R 4 The substituted or unsubstituted saturated or unsaturated rings formed by the combination can be selected from substituted or unsubstituted C5-C. 30 Aliphatic hydrocarbon rings, substituted or unsubstituted C6-C 60 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 60 Aromatic heterocycles and substituted or unsubstituted C 12 -C 60 Fused ring.

[0120] The saturated or unsaturated rings mentioned above may be selected from, for example, cyclopentane, cyclohexane, cycloheptane, cyclooctane, benzene, pyrrole, furan, thiophene, pyridine, imidazole, pyrimidine, pyridazine, pyrazine, furazolidone, oxazole, isoxazole, oxazine, thiazole, oxazine ...

[0121] In some respects, groups derived from aromatic cycloalkanes including Y1 to Y4 may be represented by any one of the following chemical formulas 2-1 to 2-41.

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] In chemical formulas 2-1 to 2-41, each of the multiple n1 can be 0 or 1, and can be the same or different from each other. Each of the multiple n2 can be an integer selected from 0 to 2, and can be the same or different from each other. Each of the multiple n3 can be an integer selected from 0 to 3, and can be the same or different from each other. Each of the multiple n4 can be an integer selected from 0 to 4, and can be the same or different from each other.

[0137] Multiple R aEach group can independently be hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups. Two or more adjacent groups among the groups mentioned above may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0138] The two asterisks (*-) represent the bonding sites with L1 and L2, respectively.

[0139] Accordingly, the electron transfer properties of polycyclic compounds represented by chemical formula 1 can be further improved.

[0140] In some respects, groups derived from aromatic cycloalkanes including Y1 to Y4 may be represented by any one of chemical formulas 2-31 to 2-41.

[0141] Therefore, the lifetime characteristics of polycyclic compounds represented by chemical formula 1 can be further improved.

[0142] In some respects, groups derived from aromatic cycloalkanes including Y1 to Y4 may be represented by any one of chemical formulas 2-31, 2-34, 2-37 or 2-41.

[0143] In some respects, L1 and L2 can each be independently represented by any one of the following chemical formulas 3-1 to 3-44.

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] In chemical formulas 3-1 to 3-44, each n1 can be 0 or 1, and can be the same or different from each other. Each n2 can be an integer selected from 0 to 2, and can be the same or different from each other. Each n3 can be an integer selected from 0 to 3, and can be the same or different from each other. Each n4 can be an integer selected from 0 to 4, and can be the same or different from each other.

[0159] Multiple R b Each group can independently be hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups. Two or more adjacent groups among the groups mentioned above may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0160] One of the two *- may be a bonding site with a group derived from an aromatic cyclic group including Y1 to Y4, and the other may be a bonding site with a substituted or unsubstituted 1,10-phenanthroline group.

[0161] Accordingly, the electron transfer properties of polycyclic compounds represented by chemical formula 1 can be further improved.

[0162] In some aspects, multiple R b Each can be independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Aryl, substituted or unsubstituted C4-C 30 heteroaryl, substituted or unsubstituted C5-C 30 Heteroaryl or substituted or unsubstituted C 10 -C 30 Fused polycyclic groups.

[0163] In some respects, the polycyclic compound represented by chemical formula 1 may be represented by any one of the following chemical formulas 4-1 to 4-13.

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] In chemical formulas 4-1 to 4-13, the plurality of n2 can each be an integer selected from 0 to 2, and can be the same as or different from each other. The plurality of n3 can each be an integer selected from 0 to 3, and can be the same as or different from each other. The plurality of n4 can each be an integer selected from 0 to 4, and can be the same as or different from each other.

[0172] Multiple Xs can be CH, CD, or N, and can be the same as or different from each other.

[0173] Multiple R c Each group can independently be hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups. Two or more adjacent groups among the groups mentioned above may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

[0174] In some aspects, multiple R c Each can be independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, substituted or unsubstituted C1-C 30Alkyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C7-C 30 Aryl, substituted or unsubstituted C4-C 30 heteroaryl, substituted or unsubstituted C5-C 30 Heteroaryl or substituted or unsubstituted C 10 -C 30 Fused polycyclic groups.

[0175] In some respects, a polycyclic compound represented by chemical formula 1 may be represented by any one of chemical formulas 4-1 to 4-6.

[0176] Accordingly, polycyclic compounds represented by Formula 1 can provide enhanced electron transfer and lifetime properties.

[0177] In some respects, the polycyclic compound represented by chemical formula 1 may be any one of compounds 1-1 to 1-36 below.

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] In some respects, the polycyclic compound represented by Formula 1 can be provided as a compound for a hole injection layer, a compound for a hole transport layer, a compound for an emitter layer, a compound for an auxiliary emitter layer, a compound for a hole blocking layer, a compound for an electron transport layer, a compound for an electron injection layer, and / or a compound for a charge generation layer.

[0188] In some respects, the polycyclic compounds represented by Formula 1 can be provided as compounds for electron transport layers and / or for charge generation layers.

[0189] In the polycyclic compound represented by Formula 1, two linkers comprising aromatic ring structures can be attached to two adjacent carbon atoms on the core comprising a fused ring structure. Furthermore, the substituted or unsubstituted 1,10-phenanthroline group can be attached to each linker via meta- or para-cyclic atoms relative to the cyclic atoms attached to the core comprising the fused ring structure, thereby improving electron transfer properties and facilitating electron transport. Additionally, the nitrogen atom of the substituted or unsubstituted 1,10-phenanthroline can form strong bonds with alkali metals, thereby reducing the band gap between the p-type and n-type charge-generating layers, enabling efficient electron injection and suppressing interface degradation.

[0190] <Light-emitting device>

[0191] According to this disclosure, a light-emitting device is provided comprising a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode. The intermediate layer may include an emitting layer and an organic layer, and at least one of the emitting layer and the organic layer may include a polycyclic compound represented by Chemical Formula 1 as described above.

[0192] Accordingly, the light-emitting device can provide improved luminous efficiency and lifespan characteristics.

[0193] In some aspects, the polycyclic compound represented by Formula 1 may include at least one of the compounds represented by Formulas 4-1 to 4-13 as described above.

[0194] In some aspects, the polycyclic compound represented by chemical formula 1 may include at least one of compounds 1-1 to 1-36 as described above.

[0195] Figures 1 to 6 A schematic cross-sectional view illustrating the light-emitting device according to aspects of this disclosure.

[0196] refer to Figure 1 The light-emitting device ED may include a first electrode 110, a second electrode 150, and an intermediate layer ITL between the first electrode 110 and the second electrode 150. The intermediate layer ITL may include an emitting layer 130, and may further include a hole transfer region 120 and an electron transfer region 140.

[0197] In some aspects, the intermediate ITL may include a light-emitting structure comprising: a hole transfer region 120 including at least one of a hole injection layer 122, a hole transport layer 124, and an electron blocking layer 126; an emission layer 130; and an electron transfer region 140 including at least one of a hole blocking layer 146, an electron transport layer 144, and an electron injection layer 142. At least one of the hole transfer region 120, the emission layer 130, and the electron transfer region 140 may include a polycyclic compound represented by Formula 1.

[0198] In some aspects, the intermediate layer (ITL) may include two or more light-emitting structures (ES), and may include a charge-generating layer (CGL) between adjacent light-emitting structures.

[0199] The light-emitting device ED may include two or more light-emitting structures between the first electrode 110 and the second electrode 150. Each light-emitting structure may include an emitting layer 130. The light-emitting structure may include, for example, a stacked structure of a hole transfer region 120, an emitting layer 130, and an electron transfer region 140. The charge generation layer may include, for example, a p-type charge generation layer and / or an n-type charge generation layer.

[0200] In some aspects, the light-emitting device ED may be a series-structured light-emitting device, which may include m light-emitting structures (m is an integer of 2 or greater) between the first electrode 110 and the second electrode 150 and (m-1) charge-generating layers disposed between adjacent light-emitting structures.

[0201] exist Figure 5 The text describes a 3-stacked series structure including three light-emitting structures, but the light-emitting device ED can have 2-stacked, 4-stacked, 5-stacked or more series structures.

[0202] In some aspects, at least one of the emission layer 130, the electron transport layer 144, and the charge generation layer (CGL) may include a polycyclic compound represented by chemical formula 1.

[0203] In some aspects, the charge generation layer (CGL) may include an n-type charge generation layer and a p-type charge generation layer.

[0204] In some aspects, the emitter layer may include a first emitter layer and a second emitter layer, and the organic layer may include a first hole injection layer, a first hole transport layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron transport layer, and a second electron injection layer. The first hole injection layer, the first hole transport layer, the first emitter layer, the first electron transport layer, the n-type charge generation layer, the p-type charge generation layer, the second hole transport layer, the second emitter layer, the second electron transport layer, and the second electron injection layer may be stacked sequentially in the direction from the first electrode to the second electrode.

[0205] In some aspects, the first hole injection layer, the first hole transport layer, the first emitter layer, the first electron transport layer (or the first electron transport layer and the first electron injection layer), the n-type charge generation layer, the p-type charge generation layer, the second hole transport layer (or the second hole injection layer and the second hole transport layer), the second emitter layer, the second electron transport layer and the second electron injection layer may be stacked sequentially in the direction from the first electrode 110 to the second electrode 150.

[0206] In some aspects, at least one of the first electron transport layer, the first emitter layer, the n-type charge generation layer, the second emitter layer, and the second electron transport layer may include a polycyclic compound represented by chemical formula 1.

[0207] In some aspects, two or more of the first electron transport layer, the n-type charge generation layer, and the second electron transport layer may include a polycyclic compound represented by chemical formula 1.

[0208] In some aspects, the n-type charge-generating layer may include: a polycyclic compound represented by Formula 1; and at least one metal selected from the group consisting of alkali metals, alkaline earth metals, lanthanides, rare earth metals, transition metals, post-transition metals, and alloys thereof. The metal may include, for example, Li, Na, K, Sc, Mg, Sr, Ba, Al, Ag, Yb, Ti, Zr, Hf, Zn, Cu, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, or Lu.

[0209] The weight ratio of the polycyclic compound represented by Formula 1 to the total metal, included in the n-type charge-generating layer, can be, for example, from 99.9:0.1 to 90:10. The polycyclic compound represented by Formula 1 can form a robust complex with the metal to reduce the band gap with the p-type charge-generating layer, and thus improve electron transfer properties.

[0210] The p-type charge-generating layer may include, for example, organic materials containing electron-withdrawing groups. The p-type charge-generating layer may include, for example, quinone derivatives, such as TCNQ (tetracyanoquinone dimethyl) or F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl); metal oxides, such as tungsten oxide or molybdenum oxide; cyano-containing compounds, such as HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile), but the materials included in the p-type charge-generating layer are not limited to these.

[0211] For example, the hole injection layer, hole transport layer, emitter layer, auxiliary emitter layer, hole blocking layer, electron transport layer, electron injection layer and / or charge generation layer may further include other compounds as will be described in this specification.

[0212] The first electrode 110 may be an anode or a cathode. In some aspects, 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.

[0213] In one aspect, 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), indium tin zinc oxide (ITZO), etc.

[0214] In one aspect, 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), a mixture of Ag and Mg, etc.

[0215] 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.

[0216] The thickness of the first electrode 110 can be in the range of about 700 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.

[0217] The second electrode 150 may be a cathode or an anode. In some aspects, the second electrode 150 may be used as an electron injection electrode or as a cathode. The second electrode 150 may include metals, alloys, conductive compounds, etc., having a low work function.

[0218] 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, IZO, etc. The second electrode 150 may include one or a combination of the aforementioned materials.

[0219] 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.

[0220] The emitter layer 130 may include a host material and dopants.

[0221] The emission layer 130 may include a polycyclic compound represented by chemical formula 1 as described above.

[0222] In some aspects, the polycyclic compound represented by Formula 1 may include at least one of the compounds represented by Formulas 4-1 to 4-13 described above.

[0223] In a non-limiting example, based on 100 parts by weight of the host material, the emitter layer 130 may include dopants in an amount of about 0.01 parts by weight to about 15.00 parts by weight or about 0.01 parts by weight to about 12.00 parts by weight.

[0224] The emitting layer 130 may emit red, green, blue, and / or white light. For example, the emitting layer 130 may emit blue light.

[0225] In some aspects, the emitting layer 130 may emit light having a maximum emission center wavelength in the range of 430 nm to 490 nm. The maximum emission center wavelength may, for example, be in the range of 430 nm to 490 nm, 440 nm to 480 nm, 440 nm to 465 nm, or 445 nm to 456 nm.

[0226] In some aspects, the full width at half maximum (FWHM) of blue light can be 30 nm or less, 28 nm or less, 25 nm or less, 10 nm to 30 nm, or 10 nm to 28 nm.

[0227] The emitter layer 130 may further include a host material and / or dopants as described below.

[0228] For example, the emitter layer 130 may include a host material that is widely known in the relevant field, such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzoanthracene derivatives, or triphenylene derivatives.

[0229] In some aspects, 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.

[0230] [Chemical formula FH]

[0231]

[0232] 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.10 Alkyl, 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 one aspect, 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.

[0233] 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.

[0234] In some aspects, 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.

[0235] [Chemical formula pH]

[0236]

[0237] 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.

[0238] 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 to each other by cyclic groups (e.g., aliphatic hydrocarbon rings). For example, C6-C 30 Aryl groups can be fluorene groups.

[0239] As described above in the definition of terms, 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, dibenzothiophene, etc. In one aspect, C2-C 30A heteroaryl group can be a group in which multiple aryl rings are fused or bonded to each other through the same or different heterocyclic groups.

[0240] In one aspect, including 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.

[0241] 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.

[0242] 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.

[0243] In one aspect, in the emitting layer 130, the body may include one or any combination of the body materials described above.

[0244] The emitter layer 130 may further include dopants that interact with the host.

[0245] In some aspects, the emitter layer 130 may include a dopant represented by the chemical formula FD. For example, a compound represented by the chemical formula FD may be used as a fluorescent dopant.

[0246] [Chemical Formula FD]

[0247]

[0248] 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.

[0249] In some respects, 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, pyrene, etc.).

[0250] In some aspects, 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.

[0251] Dopants used in phosphorescent devices may include, for example, compounds represented by the chemical formula PD.

[0252] [Chemical formula PD]

[0253] M(L d 1 ) dx1 (L d 2 ) dx2

[0254] 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).

[0255] In the chemical formula PD, L d 1 It can be a ligand represented by the chemical formula LD1.

[0256] [Chemical formula LD1]

[0257]

[0258] In the chemical formula LD1, X PD1 and X PD2 Each can be either C or N independently.

[0259] In one respect, X PD1 and X PD2 One of them can be C and the other can be N. In one aspect, X PD1 and X PD2 Each can be N.

[0260] In the chemical formula LD1, CG PD1 and CG PD2 Each can be independently C3-C 60 carbon cyclo group or C1-C 60 Heterocyclic group.

[0261] 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.

[0262] 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 )-*'.

[0263] 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.

[0264] 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 explained above. sa (R) sb (R) sc )express.

[0265] 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.

[0266] 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.

[0267] 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.

[0268] 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 L PD2 (etc.) are connected to each other. Connecting groups (e.g., L) PD1 L PD2 (etc.) can each independently relate to the reference L PD The same restrictions apply.

[0269] 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.

[0270] In the chemical formula PD, dx2 is an integer selected from 0 to 4. When dx2 is 2 or greater, two or more L d 2 They may be the same as or different from each other.

[0271] In some aspects, the emitting layer 130 may include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (NBDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), etc.), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, or 1,4-bis(N,N-diphenylamino)pyrene, etc.) as fluorescent dopant materials.

[0272] 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')pyridinecarboxylated iridium(III)), FIr6 (bis(2,4-difluorophenylpyridinyl)-tetra(1-pyrazolyl)boronate(III)), PtOEP (octaethylporphyrin platinum) and the like can be used as phosphorescent dopants.

[0273] In various aspects, the emitter layer 130 may include a boron-containing dopant represented by the chemical formula BD.

[0274] [Chemical formula BD]

[0275]

[0276] In the chemical formula BD, X BD1 and X BD2 Each can be independently N(R) BD1 ), P(R BD2 ), C(R BD3 (R) BD4 ), Si(R) BD5 (R) BD6 ), S or O. In one aspect, X BD1 and X BD2 Each can be N(R) BD1 R BD1 To R BD6 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C30 Mixed aromatics. R BD7 R BD8 and R BD9 Each can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted oxygen, substituted or unsubstituted thio, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatics. R BD7 R BD8 and / or R BD9 It can bond with adjacent groups to form a ring.

[0277] In the chemical formula BD, CG BD1 and CG BD2 Indicates a cyclic group, and CG BD1 and CG BD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic groups. In some respects, CG BD1 and CG BD2 Each can be independently substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0278] In one aspect, CG BD1 and CG BD2 Each can be a substituted or unsubstituted benzene ring independently. In this case, boron-containing dopants can be used as thermally activated delayed fluorescence (TADF) dopants.

[0279] In one aspect, CG BD1 and CG BD2 One of them can be a non-fused aryl or a non-fused heteroaryl, and the other can be a fused polycyclic aryl or a fused polycyclic heteroaryl. In this case, the boron-containing dopant can be used as a fluorescent dopant.

[0280] In one aspect, the emitter layer 130 may comprise one or any combination of the dopant materials described above.

[0281] In some aspects, the emitting layer 130 may include two or more host materials. For example, the emitting layer 130 may include a hole transport host compound and an electron transport host compound. In this case, the emitting layer 130 may include a hole transport host compound, an electron transport host compound, a photosensitizer, and a dopant. In an exemplary aspect, 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.

[0282] Non-limiting examples of hole transport host compounds may include compounds represented by the chemical formula HT, as described below. Non-limiting examples of electron transport host compounds may include compounds represented by the chemical formula ET, as described below.

[0283] In some aspects, 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.

[0284] Quantum dots may include a core comprising the elements or compounds 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, AlSb, etc.

[0285] In one example, the color of the emitted light can be adjusted based on the particle size of the quantum dots. The quantum dots can be blue, red, or green.

[0286] 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.

[0287] 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.

[0288] In some aspects, such as Figure 2 As explained in the text, the hole transfer region 120 may include a hole injection layer 122 and a hole transport layer 124 stacked sequentially from the first electrode 110.

[0289] In some aspects, such as Figure 3As illustrated, the hole transfer region 120 may include a hole injection layer 122, a hole transport layer 124, and an electron blocking layer 126 stacked sequentially from the first electrode 110. The electron blocking layer 126 can block electrons from 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.

[0290] For example, the hole transfer region 120 may include a compound represented by the chemical formula HT.

[0291] [Chemical formula HT]

[0292]

[0293] In the chemical formula HT, L HT1 L HT2 and L HT3 Each can be independently a directly connected, substituted, or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0294] 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.

[0295] 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.

[0296] In one aspect, compounds represented by the chemical formula HT can be monoamine compounds. In another aspect, compounds represented by the chemical formula HT can be compounds in which Ar... HT1 To Ar HT3 At least one of the diamine compounds includes an amino group as a substituent.

[0297] In some respects, compounds represented by the chemical formula HT can be Ar. HT1 and ArHT2 At least one of the carbazole compounds 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.

[0298] In some respects, Ar HT1 To Ar HT3 Two adjacent groups in a ring can fuse together to form a ring.

[0299] For example, hole transfer region 120 may include m-MTDATA (4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine), TDATA (4,4',4"-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine), NPB (N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine), TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), spiroTPD, spiroNPB, DNTPD (N 1 N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) 1 -Phenyl-N 4 N 4 Hole transfer regions 120 may include one or a combination of the above-mentioned hole transfer materials, such as di-m-tolylphenyl-1,4-diamine, TAPC (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine compounds, carbazole compounds (N-phenylcarbazole, polyvinylcarbazole, etc.), and fluorene compounds.

[0300] 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.

[0301] 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.

[0302] Examples of dopant materials may include metal halide compounds such as LiF, NaCl, CsF, RbCl, RbI, CuI, or KI; quinone derivatives such as TCNQ (tetracyanoquinone dimethyl), F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl), etc.; cyano-containing compounds such as HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile), NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), etc.; tungsten (W) oxides; or molybdenum (Mo) oxides, etc. Hole transfer region 120 may include one or a combination of the above dopant materials.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] Each layer of the hole transfer region 120 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, and laser thermal transfer.

[0307] 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.

[0308] 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.

[0309] The electron transport region 140 may include the polycyclic compound represented by chemical formula 1. Accordingly, the luminous efficiency and lifetime characteristics of the light-emitting device can be improved.

[0310] In some aspects, at least one of the electron injection layer and the electron transport layer may include the polycyclic compound represented by chemical formula 1 described above.

[0311] In some aspects, the polycyclic compound represented by Formula 1 may include at least one of the compounds represented by Formulas 4-1 to 4-13. Accordingly, the luminous efficiency and lifetime characteristics of the light-emitting device can be further improved.

[0312] In some aspects, the polycyclic compound represented by chemical formula 1 may include at least one of compounds 1-1 to 1-36 described above.

[0313] In some aspects, such as Figure 2 As explained in the text, the electron transfer region 140 may include an electron injection layer 142 and an electron transport layer 144 stacked sequentially from the second electrode 150 to the emitter layer 130.

[0314] In some aspects, such as Figure 3 As illustrated, the electron transfer region 140 may include an electron injection layer 142, an electron transport layer 144, and a hole blocking layer 146, 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.

[0315] For example, electron transfer region 140 may include a compound represented by the chemical formula ET.

[0316] [Chemical formula ET]

[0317]

[0318] In the chemical formula ET, X ET1 To X ET3 At least one of them can be N; and the rest of X ET1 To X ET3 Each can 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.

[0319] 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. ET1To X ET3 When each is N, compounds represented by the chemical formula ET may include triazine groups.

[0320] 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.

[0321] 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.

[0322] In the chemical formula ET, Ar ET1 To Ar ET3 Each can be independently hydrogen, deuterium, substituted or unsubstituted silyl group, 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 carbazole, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted silyl group. The silyl group can be derived from -Si(R) as explained above. sa (R) sb (R) sc )express.

[0323] Non-limiting examples of compounds included in electron transfer region 140 are as follows.

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330] 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), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene), etc., are used as electron transfer materials. The electron transfer region 140 may include one or a combination of the above-mentioned electron transfer materials.

[0331] 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.

[0332] 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 one aspect, the materials mentioned above may be included in the electron injection layer 142.

[0333] 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.

[0334] 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, iodides, etc.), tellurides, or combinations thereof.

[0335] 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.

[0336] The thickness of the electron transfer region 140 can be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å.

[0337] 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.

[0338] Within any of the aforementioned thickness ranges, the electron injection and electron transport characteristics can be further improved without significantly increasing the driving voltage, and the stability of the electron transfer region 140 can be improved.

[0339] Each layer of the electron transfer region 140 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, and laser thermal transfer.

[0340] 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.

[0341] like Figure 4 As explained herein, the second capping layer 160b may be formed on the outer surface of the second electrode 150. In some aspects, the first capping layer 160a may be formed on the outer surface of the first electrode 110.

[0342] 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.

[0343] 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.

[0344] 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.

[0345] In some aspects, the first capping layer 160a and the second capping layer 160b may each independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalene phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, etc. The first capping layer 160a and the second capping layer 160b may each independently comprise one or a combination of the aforementioned materials.

[0346] In one aspect, the first capping layer 160a and / or the second capping layer 160b may each independently include an amine-containing compound.

[0347] 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 The described light-emitting structures ES1, ES2, and ES3 may each comprise a stacked structure of a hole transfer region 120, an emission layer 130, and an electron transfer region 140. In some aspects, Figure 5 The light-emitting device ED can be a light-emitting device with a series structure.

[0348] 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.

[0349] The p-type charge generation layer may include a hole transport host compound (such as NPB). For example, the p-type charge generation layer may include a compound represented by the chemical formula HT as described above. The p-type charge generation layer may further include a p-type dopant (such as TCNQ).

[0350] The n-type charge generation layer may include the polycyclic compound represented by chemical formula 1.

[0351] In some aspects, the polycyclic compound represented by Formula 1 may include the compound represented by at least one of Formulas 4-1 to 4-13. Accordingly, the luminous efficiency and lifetime characteristics of the light-emitting device can be further improved.

[0352] In some aspects, the polycyclic compound represented by chemical formula 1 may include at least one of compounds 1-1 to 1-36 described above.

[0353] In some aspects, the n-type charge-generating layer may include: a polycyclic compound represented by chemical formula 1; and at least one metal selected from the group consisting of alkali metals, alkaline earth metals, lanthanides, rare earth metals, transition metals, post-transition metals and their alloys.

[0354] The weight ratio of the polycyclic compound represented by Formula 1 and all metals included in the n-type charge-generating layer can, for example, be in the range of 99.9:0.1 to 90:10.

[0355] The n-type charge-generating layer may further include, for example, a metal complex, and the metal complex may include the aforementioned metal and at least one organic ligand. The organic ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, or cyclopentadiene, etc.

[0356] The n-type charge-generating layer may further include an electron transport host compound. For example, the n-type charge-generating layer may include compounds represented by the chemical formula ET as described above. In one aspect, the n-type charge-generating layer may include phenanthroline-like compounds.

[0357] For example, the thickness of the n-type charge generation layer and the thickness of the p-type charge generation layer can be in the range of 20 Å to 1000 Å, 20 Å to 700 Å, or 30 Å to 500 Å.

[0358] 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.

[0359] In some aspects, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, the third light-emitting structure ES3, and the second electrode 150 may be stacked sequentially on the top surface of the first electrode 110.

[0360] The colors emitted from the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may be the same or different from each other. In some aspects, 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.

[0361] exist Figure 5The 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 in the text. For example, a 2-stack structure can also be implemented, or as referenced... Figure 6 The described 4-stack structure, 5-stack structure or more stacked structure.

[0362] refer to Figure 6 For reference Figure 5 The described structure, in which the light-emitting structure and the charge-generating layer are alternately and repeatedly stacked in series, can be disposed between the first electrode 110 and the second electrode 150.

[0363] In some aspects, the first to m-th light-emitting structures ES1 to ESm may be stacked sequentially from the top surface of the first electrode 110, with a charge-generating layer inserted between them. The charge-generating layer may include a first charge-generating layer CGL1 to a (m-1)-th charge-generating layer CGLm-1 stacked sequentially from the top surface of the first electrode 110.

[0364] like Figure 6 As explained in the text, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, ..., the (m-1)th light-emitting structure ESm-1, the (m-1)th charge-generating layer CGLm-1, the mth light-emitting structure ESm, and the second electrode 150 can be stacked sequentially from the top surface of the first electrode 110.

[0365] In some aspects, m is 4, and the intermediate layer of the light-emitting device may have a 4-stacked series structure, and may include first to fourth light-emitting structures ES1, ES2, ES3 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.

[0366] In one aspect, 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.

[0367] In some aspects, m is 5, and the intermediate layer of the light-emitting 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.

[0368] In one aspect, 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.

[0369] <Electronic Devices>

[0370] 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.

[0371] Electronic devices may include light-emitting devices (EDs) comprising the polycyclic compounds represented by the above-described chemical formula 1, thereby achieving improved luminous efficiency and lifetime characteristics.

[0372] The electronic device may further include, for example, a functional layer disposed on a light-emitting device, and may include a sensor layer, a polarization layer, a color conversion layer, a color filter layer, or a combination of at least two of them.

[0373] 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, trains, etc.).

[0374] In some applications, light-emitting devices (EDs) can be used in organic light-emitting diode (OLED) display devices or quantum dot (QD)-OLED display devices.

[0375] Figure 7 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0376] refer to Figure 7The 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.

[0377] 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.

[0378] In some aspects, the substrate 200 may include a polymer material having both transparent and flexible properties. When the substrate 200 includes a polymer material, the substrate 200 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, polyester, etc.). In one aspect, the substrate 200 may include polyimide.

[0379] 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).

[0380] 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.

[0381] The buffer layer 205 may include, for example, silicon oxide, silicon nitride, or silicon oxynitride. The buffer layer 205 may include one or a combination of the aforementioned materials. In some aspects, the buffer layer 205 may have a stacked structure comprising a silicon oxide layer and a silicon nitride layer.

[0382] 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.

[0383] Transistors TR1, TR2 and TR3 may each include an active layer 210, a gate insulating layer 220 and a gate electrode 230.

[0384] The active layer 210 may be disposed on the buffer layer 205 and may be patterned for each pixel. The active layer 210 may include silicon compounds, such as amorphous silicon or polycrystalline silicon. p-type dopants or n-type dopants may be doped in corresponding regions of the active layer 210, and the active layer 210 may include source regions, drain regions, and channel regions.

[0385] The active layer 210 may include an oxide semiconductor, such as indium gallium zinc oxide (IGZO), zinc tin oxide (ZTO), or ITZO.

[0386] The gate insulating layer 220 may be formed on the active layer 210, and the gate electrode 230 may be stacked on the gate insulating layer 220. For example... Figure 7 As illustrated, the gate insulating layer 220 can be patterned to partially cover each active layer 210. Optionally, the gate insulating layer 220 can extend continuously across multiple pixel regions or light-emitting regions, and can be provided as a common layer for the first transistor TR1, the second transistor TR2, and the third transistor TR3.

[0387] The gate electrode 230 may overlap with the channel region of the active layer 210 in the thickness direction.

[0388] 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.

[0389] 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.

[0390] 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.

[0391] 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.

[0392] The gate electrode 230 and the connecting electrodes 250 and 260 may include metals (such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, etc.), their alloys, or their nitrides.

[0393] A through-hole insulating layer 270 may be formed on the insulating interlayer 240 to cover the connecting electrodes 250 and 260.

[0394] 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 various aspects, the via insulating layer 270 may include polymer materials (such as polyimide, polysiloxane, epoxy resin, acrylic resin, polyester, etc.).

[0395] 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 4The light-emitting devices ED1, ED2 and ED3 described may include a first electrode 110, a hole transfer region 120, an emission layer 130, an electron transfer region 140 and a second electrode 150, which are stacked sequentially from the through-hole insulating layer 270.

[0396] 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, the first electrode 110 may be in contact with or electrically connected to the drain electrode 260 to serve as a pixel electrode patterned for each light-emitting area or pixel region.

[0397] 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.

[0398] The pixel-defining layer 280 can partially cover the first electrode 110 in each light-emitting area.

[0399] like Figure 7 As illustrated, hole transfer region 120 and electron transfer region 140 may each be provided as a common layer extending continuously over pixel defining layer 280 and first electrode 110. Emitting layer 130 may be formed in each light-emitting region or pixel region and may be separated by pixel defining layer 280.

[0400] In some aspects, the emitting layer 130 may also be provided as a common layer that extends continuously throughout the light-emitting area or pixel area. In some aspects, 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.

[0401] The second electrode 150 can be provided as a common electrode that extends continuously throughout the light-emitting area or pixel area.

[0402] 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.

[0403] Encapsulation layer 290 may include: an inorganic layer, the inorganic layer including silicon nitride (SiN) x ), silicon dioxide (SiO) xIndium tin oxide, indium zinc oxide, or any combination thereof; an organic layer comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE)), or any combination thereof; or a combination of an inorganic layer and an organic layer.

[0404] The display device may further include a functional layer 300 disposed on the encapsulation layer 290. The functional layer 300 may include a sensor layer (such as a touch sensor layer), an optical layer (such as a polarizing layer), a color conversion layer, a color filter layer, a window film, or any combination thereof.

[0405] Figure 8 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0406] 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.

[0407] In some aspects, 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.

[0408] 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.

[0409] 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.

[0410] 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.

[0411] The lower and upper emitting layers included in each light-emitting structure can generate light of the same color. In one aspect, each of the first lower emitting layer 130-1a and the first upper emitting layer 130-1b included 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 included 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 included in the third light-emitting device ED3 can correspond to a blue emitting layer.

[0412] Figure 9 A schematic cross-sectional view illustrating the stacked structure of the light-emitting structures in a display device according to aspects of this disclosure. For ease of explanation and description, from... Figure 9 The explanation of circuit layers, substrate, pixel limiting layers, etc. is omitted, and the shape of each layer or element in the light-emitting structure is simply shown as a rectangle.

[0413] 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.

[0414] In some aspects, 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 comprising multiple emission layers, and the others may have a single emission layer structure.

[0415] like Figure 9 As explained herein, the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 may be included in the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3, respectively. In some aspects, 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.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] 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.

[0420] 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.

[0421] Figure 10 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure.

[0422] Figure 10 This describes a display device having a QD-OLED structure according to an embodiment. (Regarding references...) Figure 7 Detailed descriptions of components and structures that are substantially the same or substantially similar will not be repeated here.

[0423] refer to Figure 10 The pixel limiting layer 280 and the light-emitting device ED can be disposed on the circuit layer CL, as shown in the reference above. Figure 7 Described. In some respects, each pixel can emit light in the same wavelength range. In one respect, each light-emitting device (ED) can emit blue light.

[0424] In some aspects, as referenced above 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.

[0425] The color control layer CCL can be disposed on the encapsulation layer 290, and the color control layer CCL can include color control portions CCP1, CCP2 and CCP3.

[0426] Color control sections CCP1, CCP2, and CCP3 may each include a light converter, such as a quantum dot or a phosphor. In each of the color control sections CCP1, CCP2, and CCP3, the light converter can convert the wavelength of the supplied light and emit the resulting light.

[0427] 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.

[0428] 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.

[0429] In some respects, 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.

[0430] 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, hollow silica, etc. The scattering material may be one or a combination of the aforementioned materials.

[0431] 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, epoxy resin, etc.

[0432] 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.

[0433] 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.

[0434] Color filters CF1 and CF2 may each include a photosensitive adhesive resin and a colorant, the 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.

[0435] The light-blocking portion CP can be disposed between the color filters. In some aspects, the light-blocking portion may include a first light-blocking portion CP1 and a second light-blocking portion CP2 containing colorants of different colors.

[0436] In some aspects, 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 one aspect, 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.

[0437] The first isolation layer 310 may be disposed between the color control layer CCL and the light-emitting device ED (or encapsulation layer 290). The second isolation layer 320 may be disposed between the color control layer CCL and the color filter layer CFL.

[0438] 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, silicon oxynitride, etc.

[0439] In one aspect, the isolation layers 310 and 320 may each have a multilayer structure that further includes an organic layer.

[0440] Figure 11 A schematic cross-sectional view illustrating a display device according to aspects of this disclosure. (Refer to reference...) Figure 10 Detailed descriptions of components and structures that are substantially the same or similar are omitted here.

[0441] 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.

[0442] In some aspects, such as reference Figure 5As 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.

[0443] In one aspect, 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 aspect, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can all generate blue light.

[0444] In some aspects, such as reference Figure 6 As described, the light-emitting device ED may include a series structure with 4 stacks, 5 stacks or more stacks.

[0445] Figure 12 A block diagram of an electronic device according to aspects of this disclosure.

[0446] refer to Figure 12 According to one aspect, the electronic device 10 may include a display module 11, a processor 12, a memory 13, and a power module 14.

[0447] 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.

[0448] 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.

[0449] 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).

[0450] At least one of the components of the electronic device 10 described above may be included in the display device according to the above aspects. 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 in the form of another device different from the display device.

[0451] Figure 13 A schematic diagram of an electronic device according to various aspects of this disclosure.

[0452] 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 computers 10_1b, laptop computers 10_1c, TVs 10_1d, or desktop monitors 10_1e, etc.); wearable electronic devices including display modules (such as smart glasses 10_2a, head-mounted displays 10_2b, or 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, dashboards, etc., or in-vehicle mirror displays, etc.). Electronic devices may include virtual reality glasses or augmented reality glasses.

[0453] Figure 14 A schematic exploded perspective view illustrating an electronic device according to aspects of this disclosure.

[0454] Depending on some aspects, the electronic device can be implemented in the form of a mobile phone (smartphone), tablet computer, or PC, which includes the aforementioned display device.

[0455] refer to Figure 14 The electronic device may include a window structure WS, a display panel DP, and a rear structure RS.

[0456] 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.

[0457] 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.

[0458] 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.

[0459] In some aspects, 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.

[0460] 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.

[0461] 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.

[0462] Figure 15 A schematic diagram illustrating an electronic device according to aspects of this disclosure.

[0463] 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 vehicle described 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, trains, etc. Other examples of vehicle 400 may include electric vehicles, hybrid vehicles, etc.

[0464] 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.

[0465] In some respects, 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.

[0466] 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).

[0467] The third display device DP3 can be installed on the center console 420 of the vehicle 400. The center console 420 can display buttons or switches for controlling the image display or music player, air conditioning, heater, etc., and can also display vehicle information.

[0468] 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.

[0469] 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.

[0470] <Electronic Devices>

[0471] 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.

[0472] Electronic devices may include light-emitting devices (EDs) comprising polycyclic compounds represented by the above chemical formula 1, thereby achieving improved luminous efficiency and lifetime characteristics.

[0473] In some respects, electronic devices may include the aforementioned electronic devices.

[0474] Electronic devices may include, for example, flat panel displays, curved displays, computer monitors, medical monitors, televisions (TV), billboards, indoor lights, outdoor lights, 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 comprising multiple displays joined together, theater screens, stadium screens, phototherapy devices, and signage.

[0475] The polycyclic compounds according to aspects of this disclosure will now be described in detail with reference to embodiments and comparative examples. While embodiments are provided to aid in understanding this disclosure, 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.

[0476] Synthesis example

[0477] Synthesis Example 1: Synthesis of Compounds 1-4

[0478] 1) Synthesis of intermediate compounds 1-4a

[0479]

[0480] i) Synthesis of 7-methyl-8-nitro-2-phenylquinoline

[0481]

[0482] In a 250 mL round-bottom flask, 2-chloro-7-methyl-8-nitroquinoline (10.0 g, 44.9 mmol), phenylboronic acid (5.7 g, 47.2 mmol), K₂CO₃ (18.7 g, 134.7 mmol), Pd(PPh₃)₄ (2.6 g, 2.2 mmol), THF (120 mL), and water (H₂O) (60 mL) were added and purged with argon for 15 minutes while mixing at room temperature. The resulting mixture was stirred at 85 °C for 12 hours and then cooled to room temperature.

[0483] The obtained product was washed with excess water and dichloromethane, and the organic layer was extracted and separated. The separated organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtered solution. The obtained product was purified and separated by column chromatography to obtain 7-methyl-8-nitro-2-phenylquinoline (7.5 g, yield 63.2%).

[0484] ii) Synthesis of intermediate compounds 1-4a

[0485]

[0486] 7-Methyl-8-nitro-2-phenylquinoline (7.0 g, 26.5 mmol) and DMFDMA (N,N-dimethylformamide dimethyl acetal, 12.0 g) were added to a 100 mL round-bottom flask and reacted at 140°C for 16 hours, and then cooled to room temperature.

[0487] The obtained product was washed with water (300 mL) and dichloromethane, and the organic layer was extracted and separated. The separated organic layer was dried with MgSO4 and filtered. The solvent was removed from the obtained product, and intermediate compound 1-4a (5.2 g, yield 61.4%) was obtained by recrystallization using methanol.

[0488] 2) Synthesis of intermediate compounds 1-4b

[0489]

[0490] i) Synthesis of 8-nitro-2-phenylquinoline-7-carboxaldehyde

[0491]

[0492] In a 250 mL round-bottom flask, intermediate compound 1-4a (5.0 g, 15.6 mmol), sodium periodate (16.7 g, 78.3 mmol), and THF (100 mL) were added, and the mixture was stirred at room temperature (RT) for 12 hours. The mixture was then neutralized with sodium hydroxide solution. The resulting product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0493] The solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and 8-nitro-2-phenylquinoline-7-carboxaldehyde (3.8 g, 87.6% yield) was obtained by recrystallization with ethanol.

[0494] ii) Synthesis of intermediate compounds 1-4b

[0495]

[0496] In a 100 mL round-bottom flask, 3.5 g (12.6 mmol) of 8-nitro-2-phenylquinoline-7-carboxaldehyde, 2.1 g (18.9 mmol) of calcium chloride (CaCl2), 3.5 g (3.5 mmol) of iron powder (Fe), and 60 mL of ethanol (EtOH) were added and refluxed for 12 hours. The mixture was then cooled to room temperature. The resulting product was diluted with dichloromethane, and the solvent was removed using a silica gel / diatomaceous earth pad.

[0497] The obtained product was purified and separated by column chromatography, and intermediate compound 1-4b (1.7 g, yield 54.3%) was obtained by recrystallization using methanol.

[0498] 3) Synthesis of intermediate compounds 1-4c

[0499]

[0500] i) Synthesis of 1-(3-(1-bromonaphth-2-yl)phenyl)ethyl-1-one

[0501]

[0502] 1,2-Dibromonaphthalene (10.0 g, 35.0 mmol), 3-(acetylphenyl)boronic acid (6.0 g, 36.7 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and water (40 mL) were added to a 250 mL round-bottom flask and reacted with stirring at room temperature for 15 minutes. The reaction mixture was refluxed for an extended period. The resulting product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0503] Solvents were removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified by column chromatography and separated to obtain 1-(3-(1-bromonaphth-2-yl)phenyl)ethyl-1-one (7.1 g, yield 62.4%).

[0504] ii) Synthesis of intermediate compounds 1-4c

[0505]

[0506] In a 250 mL round-bottom flask, add 1-(3-(1-bromonaphth-2-yl)phenyl)ethyl-1-one (7.1 g, 21.8 mmol), 4-(acetylphenyl)boronic acid (3.7 g, 22.9 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and water (40 mL) and react at room temperature for 15 minutes. Reflux the reaction mixture for an extended period.

[0507] The obtained product was washed with excess water and dichloromethane, and the organic layer was extracted and separated. The solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography to obtain intermediate compound 1-4c (5.5 g, yield 69.2%).

[0508] 4) Synthesis of compounds 1-4

[0509]

[0510] In a 100 mL round-bottom flask, intermediate compound 1-4b (3.2 g, 12.9 mmol), intermediate compound 1-4c (2.0 g, 5.5 mmol), potassium hydroxide (KOH, 1.8 g, 32.2 mmol), toluene (50 mL), and ethanol (10 mL) were added. The mixture was stirred at room temperature for 15 minutes and then refluxed for 6 hours. The resulting product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0511] Solvents were removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and compounds 1-4 (3.0 g, 69.8% yield) were obtained by recrystallization using toluene / hexane.

[0512] Synthetic Example 2: Synthesis of Compounds 1-13

[0513]

[0514] i) Synthesis of 9,10-bis(4-acetylphenyl)phenanthrene

[0515]

[0516] In a 100 mL round-bottom flask, 9,10-dibromophenanthrene (1.0 g, 3.0 mmol), 4-acetylphenylboronic acid (1.0 g, 6.8 mmol), K₂CO₃ (1.3 g, 9.4 mmol), Pd(PPh₃)₄ (0.4 g, 0.3 mmol), toluene (20 mL), and ethanol (7 mL) were added and stirred at room temperature while purging with argon for 10 minutes. The resulting mixture was refluxed vigorously for 6 hours and then mixed with methanol to obtain a solid.

[0517] The obtained solid was dissolved in dichloromethane, washed with water, and the solvent was removed under reduced pressure using a silica gel pad. The obtained solid was purified by column chromatography and separated to obtain 9,10-bis(4-acetylphenyl)phenanthrene (0.9 g, yield 75.0%) as a white solid.

[0518] ii) Synthesis of compounds 1-13

[0519]

[0520] In a 100 mL round-bottom flask, 9,10-bis(4-acetylphenyl)phenanthrene (0.5 g, 1.2 mmol), 8-aminoquinoline-7-carboxaldehyde (0.45 g, 2.6 mmol), potassium hydroxide (0.3 g, 5.4 mmol), toluene (25 mL), and ethanol (5 mL) were added and stirred at room temperature while being purged with argon for 10 minutes. The resulting mixture was refluxed vigorously for 12 hours and then mixed with methanol to obtain a solid.

[0521] The obtained solid was dissolved in dichloromethane, washed with water, and the solvent was removed under reduced pressure using a silica gel pad. The obtained solid was purified and separated by column chromatography, and recrystallized from methanol to give compound 1-13 as a white solid (0.5 g, yield 61.0%).

[0522] Synthesis Example 3: Synthesis of Compounds 1-15

[0523]

[0524] 1) Synthesis of 9,10-bis(3-acetylphenyl)phenanthrene

[0525]

[0526] In a 100 mL round-bottom flask, add 9,10-dibromophenanthrene (1.0 g, 3.0 mmol), 3-acetylphenylboronic acid (1.0 g, 6.8 mmol), K2CO3 (1.3 g, 9.4 mmol), Pd(PPh3)4 (0.4 g, 0.3 mmol), toluene (20 mL), and ethanol (7 mL) and stir at room temperature while purging with argon for 10 minutes.

[0527] The resulting mixture was refluxed vigorously for 6 hours and then mixed with methanol to obtain a solid. The obtained solid was dissolved in dichloromethane, washed with water, and the solvent was removed under reduced pressure using a silica gel pad. The obtained solid was purified by column chromatography and separated to obtain 9,10-bis(3-acetylphenyl)phenanthrene (0.8 g, yield 66.7%).

[0528] 2) Synthesis of compounds 1-15

[0529]

[0530] In a 100 mL round-bottom flask, 9,10-bis(3-acetylphenyl)phenanthrene (0.5 g, 1.2 mmol), 8-aminoquinoline-7-carboxaldehyde (0.45 g, 2.6 mmol), potassium hydroxide (0.3 g, 5.4 mmol), toluene (25 mL), and ethanol (5 mL) were added, and the mixture was purged with argon for 10 minutes while mixing at room temperature. The resulting mixture was refluxed vigorously for 12 hours and then mixed with methanol to obtain a solid.

[0531] The obtained solid was dissolved in dichloromethane, washed with water, and the solvent was removed under reduced pressure using a silica gel pad. The obtained solid was purified and separated by column chromatography, and recrystallized from methanol to obtain solid compound 1-15 (0.5 g, yield 61.0%).

[0532] Synthesis Example 4: Synthesis of Compounds 1-30

[0533] 1) Synthesis of intermediate compounds 1-30a and 1-30b

[0534]

[0535] i) Synthesis of intermediate compounds 1-30a

[0536]

[0537] In a 250 mL round-bottom flask, 5,6-dibromo-1,10-phenanthroline (10.0 g, 35.0 mmol), 3-(acetylphenyl)boronic acid (6.0 g, 36.7 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and water (40 mL) were added and reacted at room temperature for 15 minutes. The reaction mixture was refluxed for an extended period. The resulting product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0538] Solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified by column chromatography and separated to obtain intermediate compound 1-30a (7.1 g, yield 62.4%).

[0539] ii) Synthesis of intermediate compounds 1-30b

[0540]

[0541] In a 250 mL round-bottom flask, intermediate compound 1-30a (7.1 g, 21.8 mmol), 4-(acetylphenyl)boronic acid (3.7 g, 22.9 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and water (40 mL) were added and stirred at room temperature for 15 minutes to allow the reaction to proceed. The reaction mixture was refluxed for an adequate time. The resulting product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0542] Solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified by column chromatography and separated to obtain intermediate compound 1-30b (3.7 g, yield 41.6%).

[0543] 2) Synthesis of compounds 1-30

[0544]

[0545] 8-Aminoquinoline-7-carboxaldehyde (2.8 g, 15.9 mmol), intermediate compound 1-30b (3.0 g, 7.2 mmol), potassium hydroxide (1.8 g, 32.2 mmol), toluene (50 mL) and ethanol (10 mL) were added to a 100 mL round-bottom flask, stirred at room temperature for 15 minutes, and refluxed for 6 hours.

[0546] The obtained product was washed with excess water and dichloromethane, and the organic layer was extracted and separated. The solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and compound 1-30 (1.5 g, yield 30.2%) was obtained by recrystallization from toluene / hexane.

[0547] Synthesis Example 5: Synthesis of Compounds 1-31

[0548] 1) Synthesis of intermediate compounds 1-31a and 1-31b

[0549]

[0550] i) Synthesis of intermediate compounds 1-31a

[0551]

[0552] In a 250 mL round-bottom flask, 9,10-dibromophenanthrene (10.0 g, 29.8 mmol), 4-acetylphenylboronic acid (6.4 g, 31.2 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and ethanol (40 mL) were added, and the mixture was stirred at room temperature for 10 min. The resulting mixture was refluxed vigorously for 6 hours, the product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0553] Solvents were removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and 1-(4-(10-bromophenanthroline-9-yl)phenyl)ethyl-1-one (7.4 g, yield 66.2%) was obtained by recrystallization using methanol.

[0554] ii) Synthesis of intermediate compounds 1-31b

[0555]

[0556] In a 250 mL round-bottom flask, 1-(4-(10-bromophenanthroline-9-yl)phenyl)ethyl-1-one (6.0 g, 16.0 mmol), 2-(acetylpyridin-6-yl)boronic acid (2.8 g, 16.8 mmol), K₂CO₃ (14.5 g, 104.9 mmol), Pd(PPh₃)₄ (2.0 g, 1.7 mmol), THF (80 mL), and ethanol (40 mL) were added, and the mixture was stirred at room temperature for 10 min. The resulting mixture was refluxed vigorously for 6 hours, the product was washed with excess water and dichloromethane, and the organic layer was extracted and separated.

[0557] Solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and intermediate compound 1-31b (4.8 g, 72.3% yield) was obtained by recrystallization using methanol.

[0558] 2) Synthesis of compounds 1-31

[0559]

[0560] In a 100 mL round-bottom flask, 8-aminoquinoline-7-carboxaldehyde (3.2 g, 12.9 mmol), intermediate compound 1-31b (2.0 g, 5.5 mmol), potassium hydroxide (1.8 g, 32.2 mmol), toluene (50 mL), and ethanol (10 mL) were added, and the mixture was stirred at room temperature for 15 minutes and refluxed for 6 hours.

[0561] The obtained product was washed with excess water and dichloromethane, and the organic layer was extracted and separated. The solvent was removed from the obtained product using a silica gel / diatomaceous earth pad. The obtained product was purified and separated by column chromatography, and compound 1-31 (3.2 g, yield 36.1%) was obtained by recrystallization from toluene / hexane.

[0562] Manufacturing of light-emitting devices

[0563] 1) Manufacturing of light-emitting devices with a single light-emitting structure

[0564] As the first electrode, a 15Ω / cm electrode is formed on it. 2 The glass substrate (Corning product) for the (1200 Å) ITO electrode was cut to a size of 50 mm × 50 mm × 0.7 mm, and the cut substrate was ultrasonically cleaned for 10 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.

[0565] Subsequently, HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile) was deposited at a thickness of 7 nm, and NPB (N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine) was deposited at a thickness of 70 nm to form hole transfer regions.

[0566] An anthracene-based blue host and a pyrene-based dopant in a weight ratio of 95:5 were co-deposited on the hole transfer region to form an emission layer with a thickness of 25 nm. Compounds from the examples or comparative examples shown in Table 1 were deposited on the emission layer with a thickness of 35 nm to form an electron transport layer, and then Liq (lithium 8-hydroxyquinoline) was deposited on the electron transport layer with a thickness of 3 nm to form an electron injection layer, thereby forming the electron transfer region. Al was deposited on the electron transfer region with a thickness of 100 nm to form a second electrode, thus obtaining a light-emitting device.

[0567] The following compounds were used as anthracene-based blue hosts and pyrene-based dopants.

[0568] <Anthracene-based blue body>

[0569]

[0570] <Pyrene dopants>

[0571]

[0572] 2) Manufacturing of light-emitting devices with a series structure

[0573] As the first electrode, a 15Ω / cm electrode is formed on it. 2 The glass substrate (Corning product) for the (1200 Å) ITO electrode was cut to a size of 50 mm × 50 mm × 0.7 mm, and the cut substrate was ultrasonically cleaned for 10 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.

[0574] Subsequently, HAT-CN was deposited at a thickness of 7 nm, and NPB was deposited at a thickness of 70 nm to form the first hole transfer region.

[0575] An anthracene blue host and a pyrene dopant in a weight ratio of 95:5 were co-deposited on the hole transfer region to form the first emission layer with a thickness of 25 nm. The same anthracene blue host and pyrene dopant used in the light-emitting device described in 1) above were used.

[0576] The compounds of the embodiments or comparative examples shown in Table 2 below are deposited on the first emission layer with a thickness of 30 nm to form a first electron transport layer (first electron transfer region).

[0577] The compounds of the embodiments or comparative examples shown in Table 2 below: Li was deposited on the first electron transport layer at a weight ratio of 95:5 (Li: 5wt%) with a thickness of 10 nm to form an n-type charge generation layer, and HAT-CN was deposited on the n-type charge generation layer with a thickness of 7 nm to form a p-type charge generation layer.

[0578] NPB was deposited on the p-type charge generation layer with a thickness of 43 nm to form a second hole transfer region.

[0579] An anthracene blue host and a pyrene dopant in a weight ratio of 95:5 were co-deposited on the second hole transfer region to form a second emission layer with a thickness of 25 nm.

[0580] The compounds of the embodiments or comparative examples shown in Table 2 below are deposited on the second emission layer with a thickness of 35 nm to form the second electron transport layer, and Liq is deposited on the second electron transport layer with a thickness of 3 nm to form the electron injection layer (second electron transfer region). Al is deposited on the electron injection layer with a thickness of 100 nm to form the second electrode, thereby obtaining the light-emitting device.

[0581] Evaluation Example

[0582] Performance evaluation of light-emitting devices

[0583] The properties of the compounds in the examples and the comparative examples shown below were evaluated.

[0584] <Compounds in the Examples>

[0585]

[0586]

[0587] <Comparative Compounds>

[0588]

[0589] The light-emitting device manufactured by the above method was measured at 1000 cd / m² using a spectrophotometer (Konica Minolta, CS-2000). 2 The driving voltage (V), luminous efficiency (cd / A), and maximum emission center wavelength (color) at the specified brightness.

[0590] Additionally, the light-emitting device is set at 10 mA / cm2 The device was continuously driven at a current density, and the time until the brightness decreased to 95% of the initial brightness was measured. The lifetime (T2) of each light-emitting device was evaluated based on the relative value of the time measured in the light-emitting device using the compound of Comparative Example 1. 95 ).

[0591] The results are shown in Tables 1 and 2, and Figures 16 to 18 middle. Figure 16 The results of lifetime evaluation of the light-emitting devices with a single light-emitting structure manufactured in Example 2, Comparative Example 1, and Comparative Example 2 are shown. Figure 17 The results of the luminous efficiency evaluation of the light-emitting devices with tandem structures manufactured in Examples 6, 7, 8 and Comparative Example 3 are shown. Figure 18 The results of lifetime evaluation of the light-emitting devices with tandem structures manufactured in Examples 6, 7, 8 and Comparative Example 3 are shown.

[0592] [Table 1]

[0593]

[0594] Refer to Table 1 and Figure 16 The light-emitting devices, including those using electron transport layers formed from the polycyclic compounds of the embodiments, provide improved luminous efficiency and lifetime characteristics. In the light-emitting device according to Example 3 (where the nucleus and 1,10-phenanthroline groups are attached to all linkers at meta-position cyclic atoms), luminous efficiency is further improved. In the light-emitting device according to Example 2 (where the nucleus and 1,10-phenanthroline groups are attached to all linkers at para-position cyclic atoms), lifetime characteristics are further improved.

[0595] The light-emitting device, including the one using the electron transport layer formed by the compound of Comparative Example 1, exhibits significantly degraded luminous efficiency and lifetime characteristics.

[0596] The luminous efficiency or lifetime characteristics of the light-emitting device according to Comparative Example 2 (where the core does not have a fused ring structure) are lower than those of the embodiment.

[0597] [Table 2]

[0598]

[0599] Refer to Table 2 and Figure 17 and Figure 18 Light-emitting devices, including those using an electron transport layer or charge generation layer formed from the polycyclic compound of the embodiments, provide improved luminous efficiency and lifetime characteristics. Lifetime characteristics are further improved in light-emitting devices where both the electron transport layer and charge generation layer include the polycyclic compound of the embodiments.

[0600] The luminous efficiency or lifetime characteristics of the light-emitting device according to Comparative Example 2 (where the core does not have a fused structure) are lower than those of the embodiment.

Claims

1. A polycyclic compound represented by chemical formula 1: Chemical Formula 1 in, In chemical formula 1, any one or two of Y1 to Y4 are C or N, and the rest of Y1 to Y4 are C. When Y1, Y2, Y3, or Y4 is N, k is 0, where k is the R bonded to Y1, Y2, Y3, or Y4. 1 R 2 R 3 Or R 4 Quantity, When Y1, Y2, Y3, or Y4 is C, k is 1. R 1 To R 10 Each of these groups is independently hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups, Multiple n² are integers selected from 0 to 2, and they may be the same or different from each other. Multiple n3s are each an integer selected from 0 to 3, and they may be the same or different from each other. When n2 and n3 are integers of 1 or greater, R 5 To R 10 Two or more adjacent groups in a ring may optionally combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. When any two, any three, or all four k are 1, R 1 To R 4 Any two, any three, or all four corresponding groups in the ring combine with each other to form at least one substituted or unsubstituted saturated or unsaturated ring. L1 and L2 are independently substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C4-C 60 Heteroaryl, substituted or unsubstituted C6-C 60 Fused arylene or substituted or unsubstituted C4-C 60 Dense heteroaryl groups, and The aromatic cyclic groups, including Y1 to Y4, that are directly bonded to L1 and L2, as well as the substituted or unsubstituted 1,10-phenanthroline groups that are directly bonded to L1 or L2, have a meta or para relationship with each other.

2. The polycyclic compound according to claim 1, wherein: R 1 and R 2 They combine with each other to form substituted or unsubstituted saturated or unsaturated rings; or R 2 and R 3 They combine with each other to form substituted or unsubstituted saturated or unsaturated rings; or R 3 and R 4 They combine with each other to form substituted or unsubstituted saturated or unsaturated rings; or R 1 and R 2 Combined with each other and R 3 and R 4 They combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

3. The polycyclic compound according to claim 1, wherein the groups derived from the aromatic cyclic groups comprising Y1 to Y4 are represented by any one of chemical formulas 2-1 to 2-41: in, In chemical formulas 2-1 to 2-41, multiple n1 values ​​are either 0 or 1, and may be the same as or different from each other. Multiple n² are integers selected from 0 to 2, and they may be the same or different from each other. Multiple n3s are each an integer selected from 0 to 3, and they may be the same or different from each other. Multiple n4s are integers selected from 0 to 4, and they may be the same or different from each other. Each R a Independently, it is hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups, two or more adjacent R a They may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings, and The two asterisks (*-) represent the bonding sites with L1 and L2, respectively.

4. The polycyclic compound according to claim 3, wherein the groups derived from the aromatic cyclic groups comprising Y1 to Y4 are represented by any one of chemical formulas 2-31 to 2-41.

5. The polycyclic compound according to claim 1, wherein L1 and L2 are each independently represented by any one of chemical formulas 3-1 to 3-44: in, In chemical formulas 3-1 to 3-44, multiple n1 values ​​are either 0 or 1, and may be the same as or different from each other. Multiple n² are integers selected from 0 to 2, and they may be the same or different from each other. Multiple n3s are each an integer selected from 0 to 3, and they may be the same or different from each other. Multiple n4s are integers selected from 0 to 4, and they may be the same or different from each other. Each R b Independently, it is hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups, two or more adjacent R b They may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings, and One of the two asterisks is a bonding site with a group derived from the aromatic cyclic group comprising Y1 to Y4, and the other of the two asterisks is a bonding site with the substituted or unsubstituted 1,10-phenanthroline group.

6. The polycyclic compound according to claim 1, wherein the polycyclic compound is represented by any one of chemical formulas 4-1 to 4-13: in, In chemical formulas 4-1 to 4-13, each of the multiple n2 is an integer selected from 0 to 2, and they may be the same as or different from each other. Multiple n3s are each an integer selected from 0 to 3, and they may be the same or different from each other. Multiple n4s are integers selected from 0 to 4, and they may be the same or different from each other. Each X is independently CH, CD, or N, and Each R c Independently, it is hydrogen, deuterium, -OH, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, amino, 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 C7-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C3-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 or substituted or unsubstituted silyl groups, and two or more adjacent R groups c They may optionally combine with each other to form substituted or unsubstituted saturated or unsaturated rings.

7. The polycyclic compound according to claim 6, wherein the polycyclic compound is represented by any one of chemical formulas 4-1 to 4-6.

8. 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 and an organic layer, At least one of the emission layer and the organic layer comprises a polycyclic compound according to any one of claims 1 to 7.

9. The light-emitting device according to claim 8, wherein the intermediate layer comprises a light-emitting structure, the light-emitting structure comprising: The hole transfer region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; emission layer; as well as The electron transfer region includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. At least one of the hole transfer region, the emitter layer, and the electron transfer region comprises the polycyclic compound.

10. The light-emitting device according to claim 9, wherein the intermediate layer comprises a plurality of light-emitting structures, and the intermediate layer comprises a charge generation layer between adjacent light-emitting structures, and At least one of the emission layer and the charge generation layer includes the polycyclic compound.

11. The light-emitting device according to claim 9, wherein the emitting layer comprises a first emitting layer and a second emitting layer, and the organic layer comprises a first hole injection layer, a first hole transport layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron transport layer, and a second electron injection layer. The first hole injection layer, the first hole transport layer, the first emission layer, the first electron transport layer, the n-type charge generation layer, the p-type charge generation layer, the second hole transport layer, the second emission layer, the second electron transport layer, and the second electron injection layer are stacked sequentially in the direction from the first electrode to the second electrode.

12. The light-emitting device according to claim 11, wherein at least one of the first electron transport layer, the first emission layer, the n-type charge generation layer, the second emission layer, and the second electron transport layer comprises the polycyclic compound.

13. The light-emitting device according to claim 12, wherein at least two of the first electron transport layer, the n-type charge generation layer, and the second electron transport layer comprise the polycyclic compound.

14. An electronic device comprising the light-emitting device according to any one of claims 8 to 13.

15. An electronic device comprising the light-emitting device of any one of claims 8 to 13, wherein the electronic device is one of the following: a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a telephone, a mobile phone, a tablet computer, a tablet PC, a personal information terminal, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays spliced ​​together, a theater screen, a stadium screen, a phototherapy device, and signage.

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