Polycyclic compound, light-emitting device, and electronic apparatus

Abstract

The light emitting device includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a polycyclic compound represented by Chemical Formula 1 explained in the specification. In addition, an electronic device including the light-emitting device, an electronic apparatus including the light-emitting device, and the polycyclic compound are also provided. Chemical formula 1

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0151691, filed with the Korean Intellectual Property Office on October 31, 2024, the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] One or more embodiments of this application relate to polycyclic compounds, light-emitting devices, and electronic devices. Background Technology

[0004] Organic light-emitting devices (OLEDs) exhibit self-emissive properties under driving voltage and can provide improved viewing angle and contrast properties. Furthermore, compared to other light-emitting devices of similar technology, OLEDs offer high response speed and high brightness.

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

[0006] The emitting layer may contain a host material and a dopant material to achieve the light emission mechanism described above. Summary of the Invention

[0007] One or more aspects of embodiments of this disclosure relate to polycyclic compounds having improved oxidative stability and intramolecular charge transfer (CT) properties.

[0008] One or more aspects of the embodiments of this disclosure relate to light-emitting devices having improved luminescent properties and / or lifespan properties.

[0009] One or more aspects of the embodiments of this disclosure relate to electronic devices including the light-emitting device.

[0010] Other aspects will be set forth in part in the description which follows and will be apparent in part from the description, or may be learned by practice of the embodiments presented in this disclosure.

[0011] According to one or more embodiments of this disclosure, a polycyclic compound represented by chemical formula 1 is provided.

[0012] Chemical Formula 1

[0013] In chemical formula 1, X1 and X2 can each be N(R) independently.17 S, O, or Se. Y1 to Y 13 Each can be C or N independently. R1 to R 13 and R 17 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups. Selected from R2 to R 13 Two adjacent groups in the ring can optionally be bonded to each other to form a saturated ring. The electron-withdrawing group is a group having a para-Hammett substituent constant (σp) greater than 0 according to Hammett's rule. n can be independently 0 or 1 each time it appears. R 14 To R 16 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups. Ar1 and Ar2 can each be independently substituted or unsubstituted C6-C. 60 The aryl group is either substituted or unsubstituted C2-C. 60 Heteroaryl groups. Selected from Y1 to Y... 13 At least one of them is N; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group; or is selected from Y1 to Y... 13 At least one of them is N, selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted by an electron-withdrawing group. When the number of electron-withdrawing groups and / or the number of groups substituted by electron-withdrawing groups are each two or more, the electron-withdrawing groups may be independently the same as or different from each other, and / or the groups substituted by electron-withdrawing groups may be independently the same as or different from each other.

[0014] In one or more embodiments, the electron-withdrawing group may be selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C2-C with depleted π electrons 30 Cyclic group. R 18 To R 21Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0015] In one or more implementations, R 14 To R 16 It may not be an electron-withdrawing group, nor may it be a group that has been replaced by an electron-withdrawing group.

[0016] In one or more implementations, R 14 To R 16 It may not be an electron-donating group, nor may it be a group substituted by an electron-donating group. The electron-donating group is a group having a substituent constant (σp) of less than -0.23 according to the Hammett rule.

[0017] In one or more embodiments, the electron-donating group may be -NH2, -NH(R) 22 ), -N(R 23 (R) 24 -OR 25 Or C3-C rich in π electrons 30 Cyclic group. R 22 To R 25 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0018] In one or more embodiments, at least one selected from Y2 to Y9 may be N; at least one selected from R2 to R9 may be an electron-withdrawing group; at least one selected from R2 to R9 may be a group substituted with an electron-withdrawing group; at least one selected from Y2 to Y9 may be N, and at least one selected from R2 to R9 may be an electron-withdrawing group; at least one selected from R2 to R9 may be N, and at least one selected from R2 to R9 may be a group substituted with an electron-withdrawing group; at least one selected from R2 to R9 may be an electron-withdrawing group, and at least one of the remainder selected from R2 to R9 may be a group substituted with an electron-withdrawing group; or at least one selected from Y2 to Y9 may be N, at least one selected from R2 to R9 may be an electron-withdrawing group, and at least one of the remainder selected from R2 to R9 may be a group substituted with an electron-withdrawing group.

[0019] In one or more embodiments, the polycyclic compound may be represented by any one of chemical formulas 1-1 to 1-4.

[0020] Chemical Formula 1-1

[0021] Chemical formula 1-2

[0022] Chemical formulas 1-3

[0023] Chemical formulas 1-4

[0024] In chemical formulas 1-1 to 1-4, X1 and X2 can each be N(R) independently. 17 ) or O. Y2, Y3, Y5, Y6, Y8, Y9, Y 10 Y 11 and Y 13 Each can be C or N independently. R1 to R 13 and R 17 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups. Selected from R2 to R 13 Two adjacent groups in the form may not be bonded to each other. n can be 0 or 1 independently each time it appears. R 14 To R 16 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups. m1 can be an integer from 0 to 5 each time it appears. Single or multiple R a Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups, substituted or unsubstituted C5-C 30 Cycloalkenyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 30 heteroaryl groups, or substituted or unsubstituted C8-C 30 Fused polycyclic groups. When R a When the number is 2 or greater, select from multiple R a Two adjacent groups in the ring can optionally combine with each other to form a saturated ring or an unsaturated ring.

[0025] In one or more embodiments, the components selected are R1 to R2. 13 and R 17 At least one of them may be selected from any group represented by chemical formula 2-1 to chemical formula 2-25.

[0026] (2-1) (2-2) (2-3) (2-4) (2-5) (2-6) (2-7) (2-8) (2-9) (2-10) (2-11) (2-12) (2-13) (2-14) (2-15) (2-16) (2-17) (2-18) (2-19) (2-20) (2-21) (2-22) (2-23) (2-24) (2-25) In chemical formulas 2-1 to 2-25, 'o' can be an integer from 0 to 2 independently each time it appears. Single or multiple 'R' EWG Each can be independently selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C3-C with depleted π electrons 30 Cyclic group. R 18 To R 21 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group. m1 can be an independent integer from 0 to 5 each time it appears, m2 can be an independent integer from 0 to 4 each time it appears, and m3 can be an independent integer from 0 to 3 each time it appears. Single or multiple R bEach can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 Aryl group. When R b When the number is 2 or greater than 2, multiple R b They can be independently the same as or different from each other, and are selected from the plurality of R. b Two adjacent groups in the ring can optionally combine with each other to form a saturated ring or an unsaturated ring. - Indicates the binding site.

[0027] In one or more embodiments, Ar1 and Ar2 can each be independently represented by any one of chemical formulas 3-1 to 3-12.

[0028]

[0029] (3-1) (3-2) (3-3)

[0030] (3-4) (3-5) (3-6)

[0031] (3-7) (3-8) (3-9)

[0032] (3-10) (3-11) (3-12)

[0033] In chemical formulas 3-1 to 3-12, m1 can independently be an integer from 0 to 5 each time it appears, m2 can independently be an integer from 0 to 4 each time it appears, and m3 can independently be an integer from 0 to 3 each time it appears. Single or multiple R c Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 Aryl group. When it contains multiple R c At that time, the plurality of Rc They can be independently the same as or different from each other, and are selected from the plurality of R. c Two adjacent groups in the ring can optionally combine with each other to form a saturated ring or an unsaturated ring. - Indicates a binding site. In chemical formulas 3-9 to 3-11, - The binding site is one of the carbons designated as numbers 1 to 4, and in chemical formulas 3-12. - The binding site is one of the carbons designated as numbers 1 to 3.

[0034] In one or more implementations, R 17 It can be represented by any group selected from chemical formulas 2-14 to 2-25; R 12 It can be a group represented by any one of chemical formulas 2-2, 2-3, and 2-8 to 2-12; or R 17 It can be a group represented by any one of chemical formulas 2-14 to 2-25, and R 12 It can be a group represented by any one of chemical formulas 2-2, 2-3, and 2-8 to 2-12.

[0035] In one or more embodiments, Ar1 and Ar2 can each be independently represented by any one of chemical formulas 3-5 to 3-12.

[0036] In one or more embodiments, Ar1 and Ar2 may each be independently represented by groups of chemical formulas 3-5.

[0037] In one or more embodiments, the electron-withdrawing group may be selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, substituted or unsubstituted triazine group, substituted or unsubstituted thiazole group, substituted or unsubstituted benzothiazole group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted naphthidine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted benzo[a]crylonitrile group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group. R 18 To R 21 Each can be either substituted or unsubstituted C1-C independently. 10Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups or substituted or unsubstituted C6-C 10 Aryl group.

[0038] According to one or more embodiments, the light-emitting device may include a first electrode, a second electrode, and an emitting layer disposed between the first electrode and the second electrode. The emitting layer may comprise a polycyclic compound represented by chemical formula 1.

[0039] In one or more embodiments, the light-emitting device may further include a charge-generating layer between the first electrode and the second electrode. The emitting layer may include multiple emitting layers, and the charge-generating layer may be arranged between adjacent emitting layers. At least one of the multiple emitting layers may contain the polycyclic compound represented by Formula 1.

[0040] In one or more embodiments, the polycyclic compound may be included as a thermally activated delayed fluorescence (TADF) dopant or as the body for a phosphorescent device (e.g., for a phosphorescent dopant).

[0041] In one or more embodiments, the emitting layer may be designed to emit blue light having a maximum emission wavelength of about 440 nm to about 480 nm (e.g., the wavelength at maximum emission intensity or peak emission wavelength).

[0042] In one or more embodiments, the polycyclic compound may be represented by any one of chemical formulas 1-1 to 1-4.

[0043] According to one or more embodiments of this disclosure, an electronic device including the light-emitting device is provided.

[0044] The electronic device may be at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, portable telephone, tablet computer, tablet phone, personal information terminal (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall with multiple displays spliced ​​together, theater screen, stadium screen, phototherapy device, and signage.

[0045] The polycyclic compound according to one or more embodiments of this disclosure may contain at least one of an electron-withdrawing group and an electron-deficient nitrogen atom at a least unoccupied molecular orbital (LUMO) site.

[0046] Therefore, both the oxidative stability and intramolecular charge transfer (CT) properties of the polycyclic compound can be improved (e.g., simultaneously).

[0047] For example, the polycyclic compound can be used as a thermally activated delayed fluorescence (TADF) dopant in the emitter layer to enhance the luminescence properties and lifetime properties of the light-emitting device.

[0048] The light-emitting device, and the electronic devices and electronic equipment that each include one or more embodiments of the light-emitting device according to this disclosure, may have improved light-emitting properties and lifespan properties. Attached Figure Description

[0049] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated into and constitute a part of this disclosure. The drawings illustrate embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure. The above and / or other aspects of this disclosure will become apparent and understandable from the following description of the embodiments adopted in conjunction with the accompanying drawings.

[0050] Figures 1 to 6 Each is a schematic cross-sectional view illustrating one or more embodiments of a light-emitting device according to the present disclosure.

[0051] Figure 7 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0052] Figure 8 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0053] Figure 9 This is a schematic cross-sectional view illustrating a stacked configuration of light-emitting structures in a display device according to one or more embodiments of the present disclosure.

[0054] Figure 10 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0055] Figure 11 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0056] Figure 12 It is a block diagram of an electronic device according to one or more embodiments of the present disclosure.

[0057] Figure 13 These are schematic diagrams illustrating one or more embodiments of an electronic device according to the present disclosure.

[0058] Figure 14 This is a schematic exploded perspective view illustrating one or more embodiments of an electronic device according to the present disclosure.

[0059] Figure 15 This is a schematic cross-sectional view illustrating an electronic device according to one or more embodiments of the present disclosure. Detailed Implementation

[0060] According to one or more embodiments of this disclosure, the polycyclic compound comprises at least one electron-withdrawing group or an electron-deficient nitrogen atom at a lowest unoccupied molecular orbital (LUMO) site. According to one or more embodiments of this disclosure, light-emitting devices, display devices, electronic devices, and electronic devices, each comprising a polycyclic compound, are provided.

[0061] <Terminology Definition>

[0062] In this disclosure, the term "substituted or unsubstituted" can mean a group selected from one or more of the following: deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, phosphine oxide, phosphine sulfide, or alkyl (e.g., C1-C1). 60 Alkyl, C1-C 10 alkyl groups), alkenyl groups (e.g., C2-C) 60 alkenyl groups, C2-C 10 alkenyl groups), alkynyl groups (e.g., C2-C) 60 alkynyl group, C2-C 10 alkynyl groups), alkoxy groups (e.g., C1-C) 60 alkoxy groups, C1-C 10 alkoxy groups), hydrocarbon ring groups, aryl groups (e.g., C6-C...) 60 aryl groups) and heterocyclic groups (e.g., C1-C) 60 The substituents in the group consisting of heterocyclic groups are either substituted or unsubstituted. For example, the term "substituted alkyl group" may refer to a group in which at least one of the hydrogen atoms of the alkyl group is substituted by the aforementioned substituents, and thus the substituents are bonded to the carbon atoms of the alkyl group.

[0063] Substituents may include combinations of substituents selected from the above-mentioned groups. For example, at least one hydrogen atom of an alkyl group, aryl group, etc., included as a substituent may be a deuterium, halogen, cyano group, nitro group, amino group, silyl group, oxy group, thio group, sulfinyl group, sulfonyl group, carbonyl group, ester group, boron, phosphine oxide group, phosphine sulfide group, alkyl group, alkenyl group, alkynyl group, hydrocarbon cyclic group, aryl group, heterocyclic group, or any suitable combination thereof.

[0064] Among the substituents mentioned above, polyvalent substituents (such as amino groups, phosphine sulfide groups, phosphine oxide groups, sulfinyl groups, sulfonyl groups, oxygen groups, carbonyl groups, ester groups, etc.) can each be independently converted from C1 to C2. 10 Alkyl groups, C1-C 10 alkenyl groups, C1-C 10 alkynyl groups and / or C6-C 10 Aryl group substitution.

[0065] In this disclosure, the term "substituted or unsubstituted C" is used. a -C b "Y group", the range from a to b refers to the number of carbon atoms in the unsubstituted Y group, and may exclude (e.g., may exclude) the number of carbon atoms of its substituents.

[0066] In this disclosure, alkyl groups (e.g., C1-C) 60 Alkyl groups, C1-C 30 Alkyl groups, C1-C 20 Alkyl groups, C1-C 15 Alkyl groups, C1-C 10 An alkyl group (or C1-C6 alkyl group) can be a monovalent hydrocarbon group in which one of its hydrogen atoms has been removed from a straight-chain or branched hydrocarbon group. Non-limiting examples of alkyl groups may include methyl groups, ethyl groups, propyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, pentyl groups, neopentyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, hexyl groups, heptyl groups, octyl groups, etc.

[0067] In this disclosure, alkylene groups (e.g., C1-C) 60 alkylene groups, C1-C 30 alkylene groups, C1-C 20 alkylene groups, C1-C 15 alkylene groups, C1-C 10 An alkylene group (or C1-C6 alkylene group) can be a divalent hydrocarbon group in which two hydrogen atoms have been removed from a straight-chain or branched hydrocarbon group.

[0068] In this disclosure, alkenyl groups (e.g., C2-C) 60 alkenyl groups, C2-C 30 alkenyl groups, C2-C 20 alkenyl groups, C2-C 15 alkenyl groups, C2-C 10 The alkenyl group (or C2-C6 alkenyl group) may have a skeleton substantially the same as that of the alkyl group and may be a monovalent hydrocarbon group including at least one carbon-carbon double bond. In this disclosure, the alkenyl group (e.g., C2-C6 alkenyl group) 60 imide groups, C2-C 30 imide groups, C2-C 20 imide groups, C2-C 15 imide groups, C2-C 10 An alkenyl group (or a C2-C6 alkenyl group) can be a divalent hydrocarbon group in which one of the hydrogen atoms is further removed from the alkenyl group.

[0069] In this disclosure, the alkynyl group (e.g., C2-C) 60 alkynyl group, C2-C 30 alkynyl group, C2-C 20 alkynyl group, C2-C 15 alkynyl group, C2-C 10 The alkynyl group (or C2-C6 alkynyl group) may have a skeleton substantially the same as that of the alkyl group and may be a monovalent hydrocarbon group containing at least one carbon-carbon triple bond. In this disclosure, the alkynyl group (e.g., C2-C6 alkynyl group) 60 acetylenic group, C2-C 30 acetylenic group, C2-C 20 acetylenic group, C2-C 15 acetylenic group, C2-C 10 An alkynyl group (or a C2-C6 alkynyl group) can be a divalent hydrocarbon group in which one of the hydrogen atoms is further removed from the alkynyl group.

[0070] In this disclosure, aryl groups (e.g., C6-C) 60 aryl group, C6-C 30 aryl group, C6-C 20 aryl group, C6-C 15 aryl group or C6-C 10An aryl group can be a monovalent hydrocarbon group in which one hydrogen atom is removed from a hydrocarbon group having an aromatic structure. The definition of an aryl group can also encompass groups in which multiple aromatic rings are directly linked, such as a biphenyl group. Non-limiting examples of aryl groups can include, for example, phenyl groups, naphthyl groups, anthraceneyl groups, phenanthrene groups, pyrene groups, fluorenyl groups, tetraphenyl groups, biphenyl groups, terphenyl groups, tetraphenyl groups, alkyl groups, etc.

[0071] In this disclosure, groups in which two or more aryl rings are fused together or connected to each other via alicyclic hydrocarbon rings (e.g., fluorenyl groups) may be included in the definition of aryl groups.

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

[0073] In this disclosure, arylene groups (e.g., C6-C) 60 arylene group, C6-C 30 arylene group, C6-C 20 arylene group, C6-C 15 arylene group or C6-C 10 An aryl group can be a divalent hydrocarbon group in which one of the hydrogen atoms is further removed from the aryl group.

[0074] In this disclosure, heteroaryl groups (e.g., C1-C) 60 heteroaryl groups, C2-C 60 heteroaryl groups, C1-C 30 heteroaryl groups, C1-C 20 heteroaryl groups, C1-C 15 heteroaryl groups, C1-C 10 The heteroaryl group (or C1-C6 heteroaryl group) can be a monovalent group having an aromatic structure comprising at least one heteroatom (e.g., B, O, P, S, and / or Si) as a cyclic atom. In this disclosure, the heteroaryl group (e.g., C1-C6 heteroaryl group) 60 heteroaryl group, C2-C 60 heteroaryl groups, C1-C 30 heteroaryl groups, C1-C 20 heteroaryl groups, C1-C 15 heteroaryl groups, C1-C 10A heteroaryl group (or a C1-C6 heteroaryl group) can be a divalent group having an aromatic structure comprising at least one heteroatom (e.g., B, O, P, S, and / or Si) as a cyclic atom. When a heteroaryl group or a heteroaryl group comprises two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other.

[0075] In this disclosure, groups in which two or more aryl rings are fused or linked to non-aromatic heterocycles, such as carbazole groups, may also be included in the definition of heteroaryl groups.

[0076] In this disclosure, the term "cyclic group (e.g., C3-C)" is used. 60 Cyclic groups, C3-C 30 Cyclic groups, C3-C 20 Cyclic groups, C3-C 15 Cyclic groups, C3-C 10 "Cyclic groups (or C3-C6 cyclic groups)" can encompass monocyclic or polycyclic groups, and can also encompass alicyclic or aromatic rings.

[0077] In this disclosure, the term "polycyclic group" can be a group in which two or more rings are connected to each other or fused together by one or more atoms. For example, polycyclic structures can include bicyclic structures, spirocyclic structures, fused structures, etc., with bridging carbons.

[0078] In this disclosure, the terms "fused group" or "fused ring structure" can each be a group in which two or more adjacent rings share two or more atoms in the aforementioned polycyclic structure. Non-limiting examples of fused ring structures may include naphthalene, anthracene, phenanthrene, fluorene, pyrene, benzo[a]pyrene, pentacene, poly[a]benzene, helicene, etc.

[0079] In this disclosure, the term "carbocyclic group (e.g., C3-C50)" is used. 60 Carbocyclic groups, C3-C 30 Carbocyclic groups, C3-C 20 Carbocyclic groups, C3-C 15 Carbocyclic groups, C3-C 10 "Carbocyclic group or C3-C6 carbocyclic group" can be a cyclic group in which only carbon atoms are cyclic atoms. In this disclosure, heterocyclic groups (e.g., C1-C6 carbocyclic groups) 60 Heterocyclic groups can be cyclic groups that contain at least one heteroatom as a cyclic atom in addition to a carbon atom.

[0080] In this disclosure, the carbocyclic group and the heterocyclic group can each be a monocyclic group comprising one (e.g., exactly one) ring (e.g., composed of one ring) or a polycyclic group in which two or more rings are fused together.

[0081] Polycyclic compounds

[0082] The polycyclic compound according to one or more embodiments comprises at least one of an electron-withdrawing group and an electron-deficient N at the LUMO site.

[0083] According to one or more embodiments, a polycyclic compound can be represented by chemical formula 1: Chemical Formula 1

[0084] In chemical formula 1, X1 and X2 can each be N(R) independently. 17 S, O, or Se. Y1 to Y 13 Each can be either C or N independently.

[0085] R1 to R 13 and R 17 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 Two adjacent groups in the ring can optionally bond to each other to form a saturated ring.

[0086] The saturated ring can be, for example, a substituted or unsubstituted C4-C6 cycloalkane ring, or a substituted or unsubstituted 5- or 6-membered ring.

[0087] If selected from R2 to R 13 Two adjacent groups in the ring bond together to form an unsaturated ring (e.g., selected from R2 to R). 13 When two adjacent groups in a polycyclic compound bond to each other to form an unsaturated ring, the triplet energy level of the polycyclic compound can be lowered, and the triplet excitons generated in the emitter layer may not easily be converted into singlet excitons.

[0088] In one or more implementations, X2 and R 10 They don't have to bond with each other. When X2 is N(R) 17 When R 17 and R 10 They don't have to bond with each other.

[0089] In one or more embodiments, C8-C is substituted or not substituted. 60 Fused polycyclic groups can be C4-C 10 Aliphatic hydrocarbon rings and C6-C 50 A fused polycyclic aromatic hydrocarbon ring. In one or more embodiments, the fused polycyclic aromatic hydrocarbon ring may have, for example, one C4-C6 aliphatic hydrocarbon ring in two C6-C6 rings. 15 A structure in which aromatic hydrocarbon rings are fused together. In one or more embodiments, the fused polycyclic group may be, for example, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted spiro-difluorene group.

[0090] In one or more embodiments, the silyl group may be -Si(R 26 (R) 27 (R) 28 ), and R 26 To R 28 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, or substituted or unsubstituted C8-C 60 Fused polycyclic groups. The description of fused polycyclic groups can also be applied here.

[0091] Electron-withdrawing groups can be groups having a para-Hammett substituent constant (σp) greater than 0 according to the Hammett rule.

[0092] In one or more embodiments, the electron-withdrawing group may be a group having a para-Hammett substituent constant (σp) greater than 0.05 according to the Hammett rule.

[0093] In one or more embodiments, the electron-withdrawing group may be a group having a para-Hammett substituent constant (σp) according to the Hammett rule of greater than 0.10, greater than 0.20, greater than 0.30, greater than 0.40 or greater than 0.42.

[0094] Hammett's rule can be used as a standard to indicate the degree to which a functional group is electron-withdrawing or electron-donating. The para-Hammett substituent constant (σp) determined by Hammett's rule can be found in the literature, for example, "A survey of Hammett substituent constants and resonance and field parameters", Chem. Rev. 1991, 91(2), pp. 165-195, the entire contents of which are incorporated herein by reference, but the para-Hammett substituent constant (σp) can be measured based on Hammett's rule even without reference.

[0095] n can be 0 or 1 independently each time it appears.

[0096] R 14 To R 16 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups. p-Si(R 26 (R) 27 (R) 28 The above description can also be applied to silyl groups.

[0097] Ar1 and Ar2 can be substituted or unsubstituted C6-C independently. 60 The aryl group is either substituted or unsubstituted C2-C. 60 heteroaryl groups.

[0098] Selected from Y1 to Y 13 At least one of them is N; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group; or is selected from Y1 to Y... 13 At least one of them is N, selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group that has been replaced by an electron-withdrawing group.

[0099] Based on R1 to R in chemical formula 1 13 and R 17 By definition, the groups substituted by electron-withdrawing groups can each be independently C1-C groups substituted by electron-withdrawing groups. 60 Alkyl groups, C2-C groups substituted with electron-withdrawing groups 60alkenyl groups, C2-C groups substituted with electron-withdrawing groups 60 Alkyne group, C1-C substituted with electron-withdrawing group 60 alkoxy groups, C3-C groups substituted with electron-withdrawing groups 60 Cycloalkyl groups, C5-C groups substituted with electron-withdrawing groups 60 Cycloalkenyl groups, C3-C groups substituted with electron-withdrawing groups 60 Heterocyclic alkyl groups, C3-C groups substituted with electron-withdrawing groups 60 Heterocyclic alkenyl groups, C6-C groups substituted with electron-withdrawing groups 60 aryl groups, C2-C groups substituted with electron-withdrawing groups 60 heteroaryl groups, C6-C groups substituted with electron-withdrawing groups 60 aryloxy groups, C6-C groups substituted with electron-withdrawing groups 60 Aryl thio groups, C8-C groups substituted with electron-withdrawing groups 60 Fused polycyclic groups or silyl groups substituted with electron-withdrawing groups.

[0100] When the number of electron-withdrawing groups and / or the number of groups replaced by electron-withdrawing groups are each two or more, the electron-withdrawing groups may be the same or different from each other, and / or the groups replaced by electron-withdrawing groups may be the same or different from each other.

[0101] Polycyclic compounds can have a structure in which boron and nitrogen are arranged alternately, which allows for multiple resonance effects in polycyclic compounds, thus narrowing the half-width of their emission spectra.

[0102] Polycyclic compounds have at least one of electron-withdrawing groups and electron-deficient N at the LUMO site, and therefore the depth of the highest occupied molecular orbital (HOMO) level can be increased, and the absolute value (ΔEst) of the difference between the lowest singlet excited state level (S1 level) and the lowest triplet excited state level (T1 level) of the polycyclic compound can become smaller.

[0103] Therefore, polycyclic compounds can have improved oxidative stability and can convert triplet excitons into singlet excitons more quickly via the reverse intersystem crossing (RISC) mechanism.

[0104] In one or more embodiments, the electron-withdrawing group may be selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C2-C with depleted π electrons 30 Cyclic group. R 18 To R21 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0105] In one or more embodiments, the electron-withdrawing group may be selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, substituted or unsubstituted triazine group, substituted or unsubstituted thiazole group, substituted or unsubstituted benzothiazole group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted naphthidine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted benzo[a]crylonitrile group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group. R 18 To R 21 Each can be either substituted or unsubstituted C1-C independently. 10 Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups or substituted or unsubstituted C6-C 10 Aryl group.

[0106] In one or more embodiments, the electron-withdrawing groups can each be independently selected from -CF3, -COR 18' -CO2R 19' -SOR 20' -SO2R 21' -CN, -SCN, substituted or unsubstituted triazine group, substituted or unsubstituted thiazole group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted naphthidine group, substituted or unsubstituted quinazoline group, and substituted or unsubstituted phenanthroline group. R 18' To R 21’ Each can be C1-C independently. 10 Alkyl groups or C3-C6 cycloalkyl groups.

[0107] In one or more implementations, R 14 To R 16The dopant may not be an electron-withdrawing group, nor may it be a group substituted by an electron-withdrawing group. Therefore, the depth of the HOMO level in a polycyclic compound can be increased to improve intramolecular charge transfer (CT) properties. If the HOMO level of the dopant is shallow, it can induce hole trapping in the emitter layer, reducing the efficiency of the light-emitting device.

[0108] In one or more implementations, R 14 To R 16 It may not be an electron-donating group, nor may it be a group substituted by an electron-donating group. The electron-donating group may be a group with a substituent constant (σp) of less than -0.23 according to the Hammett rule.

[0109] Electron-donating groups can have substituent constants (σp) according to Hammett rules, for example, less than -0.25, less than -0.30, or less than -0.40.

[0110] In one or more embodiments, the electron-donating group may be -NH2, -NH(R) 22 ), -N(R 23 (R) 24 -OR 25 Or C3-C rich in π electrons 30 Cyclic groups.

[0111] R 22 To R 25 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0112] In one or more embodiments, the electron-donating group may be -NH2, -NH(R) 22 ), -N(R 23 (R) 24 -OR 25 Substituted or unsubstituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted benzonaphthothiophene group, substituted or unsubstituted pyrrole group, substituted or unsubstituted furan group, or substituted or unsubstituted benzofuran group. R 22 To R 25 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0113] In one or more embodiments, at least one selected from Y2 to Y9 may be N; at least one selected from R2 to R9 may be an electron-withdrawing group; at least one selected from R2 to R9 may be a group substituted with an electron-withdrawing group; at least one selected from Y2 to Y9 may be N, and at least one selected from R2 to R9 may be an electron-withdrawing group; at least one selected from R2 to R9 may be N, and at least one selected from R2 to R9 may be a group substituted with an electron-withdrawing group; at least one selected from R2 to R9 may be an electron-withdrawing group, and at least one of the remainder selected from R2 to R9 may be a group substituted with an electron-withdrawing group; or at least one selected from Y2 to Y9 may be N, at least one selected from R2 to R9 may be an electron-withdrawing group, and at least one of the remainder selected from R2 to R9 may be a group substituted with an electron-withdrawing group.

[0114] In one or more embodiments, the polycyclic compound may be represented by any one of chemical formulas 1-1 to 1-4.

[0115] Chemical Formula 1-1

[0116] Chemical formula 1-2

[0117] Chemical formulas 1-3

[0118] Chemical formulas 1-4

[0119] In chemical formulas 1-1 to 1-4, X1 and X2 can each be N(R) independently. 17 ) or O. Y2, Y3, Y5, Y6, Y8, Y9, Y 10 Y 11 and Y 13 Each can be either C or N independently.

[0120] R1 to R 13 and R 17 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups.

[0121] Selected from R2 to R 13 Two adjacent groups in a given structure may not be bonded to each other.

[0122] n can be 0 or 1 independently each time it appears.

[0123] R 14 To R 16 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups. In Formulas 1-1 to 1-4, the silyl group described with reference to Formula 1 may also be used.

[0124] Each occurrence of m1 can be an integer from 0 to 5 independently.

[0125] Single or multiple R a Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups, substituted or unsubstituted C5-C 30 Cycloalkenyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl groups, or substituted or unsubstituted C8-C 30 Fused polycyclic groups. When R a When the number is 2 or greater than 2, multiple R a They can be the same or different from each other, and two adjacent groups can optionally combine with each other to form a saturated ring or an unsaturated ring.

[0126] In one or more embodiments, the components selected are R1 to R2. 13 and R 17 At least one of them may be selected from any group represented by chemical formula 2-1 to chemical formula 2-25.

[0127] (2-1) (2-2) (2-3) (2-4) (2-5) (2-6) (2-7) (2-8) (2-9) (2-10) (2-11) (2-12) (2-13) (2-14) (2-15) (2-16) (2-17) (2-18) (2-19) (2-20) (2-21) (2-22) (2-23) (2-24) (2-25) In chemical formulas 2-1 to 2-25, o can be an integer from 0 to 2 each time it appears. - Indicates the binding site.

[0128] Single or multiple R EWG Each can be independently selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C3-C with depleted π electrons 30 Cyclic group. R 18 To R 21 Each can be either substituted or unsubstituted C1-C independently. 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

[0129] When R EWG When the number is 2 or greater than 2, multiple R EWG They can be the same as or different from each other.

[0130] m1 can be an integer from 0 to 5 each time it appears, m2 can be an integer from 0 to 4 each time it appears, and m3 can be an integer from 0 to 3 each time it appears.

[0131] o+m1, o+m2, and o+m3 can each be an integer from 0 to 5 independently. For example, o, m1, m2, and m3 can satisfy 0≤o+m1≤5, 0≤o+m2≤5, and 0≤o+m3≤5, and o+m1, o+m2, and o+m3 can be integers that are the same as or different from each other.

[0132] Single or multiple R b Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 Aryl group.

[0133] When Rb When the number is 2 or greater than 2, multiple R b They can be the same or different from each other, and two adjacent groups can optionally combine with each other to form a saturated ring or an unsaturated ring.

[0134] In one or more embodiments, Ar1 and Ar2 can each be independently represented by any one of chemical formulas 3-1 to 3-12.

[0135]

[0136] (3-1) (3-2) (3-3)

[0137] (3-4) (3-5) (3-6)

[0138] (3-7) (3-8) (3-9)

[0139] (3-10) (3-11) (3-12)

[0140] In chemical formulas 3-1 to 3-12, m1 can be an integer from 0 to 5 each time it appears, m2 can be an integer from 0 to 4 each time it appears, and m3 can be an integer from 0 to 3 each time it appears. - Indicates the binding site.

[0141] Single or multiple R c Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 Aryl group.

[0142] When containing multiple R c At that time, multiple R c They can be the same or different from each other, and two adjacent groups can optionally combine with each other to form a saturated ring or an unsaturated ring.

[0143] In chemical formulas 3-9 to 3-11 - The binding site can be one of the carbons designated as numbers 1 to 4. In one or more embodiments, in chemical formulas 3-9 to 3-10, - The binding site can be one of the carbons designated as numbers 1, 2, and 4.

[0144] In chemical formula 3-12, - The binding site can be one of the carbons designated as numbers 1 to 3.

[0145] In one or more implementations, R 17 It can be represented by any of the groups selected from chemical formulas 2-14 to 2-25.

[0146] In one or more implementations, R 12 It can be any one of the chemical formulas 2-2, 2-3, and 2-8 to 2-12.

[0147] In one or more implementations, R 17 It can be represented by any group selected from chemical formulas 2-14 to 2-25; R 12 It can be represented by any group selected from chemical formulas 2-2, 2-3, and 2-8 to 2-12. Therefore, the oxidative stability of polycyclic compounds can be further improved.

[0148] In one or more embodiments, Ar1 and Ar2 may each be independently represented by a group selected from any one of chemical formulas 3-5 to 3-12.

[0149] In one or more embodiments, Ar1 and Ar2 can each be independently represented by groups of chemical formulas 3-5. Therefore, aggregation between molecules of the polycyclic compound can be further prevented or reduced.

[0150] In one or more embodiments, the electron-withdrawing group may be selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21-CN, -SCN, substituted or unsubstituted triazine group, substituted or unsubstituted thiazole group, substituted or unsubstituted benzothiazole group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted naphthidine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted benzoxenoline group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group.

[0151] R 18 To R 21 Each can be either substituted or unsubstituted C1-C independently. 10 Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups or substituted or unsubstituted C6-C 10 Aryl group.

[0152] R 14 and R 16 They can be, independently, for example, hydrogen, deuterium, or straight-chain C1-C. 10 Alkyl groups, branched C3-C 10 Alkyl groups, straight-chain C2-C 10 alkenyl groups or branched C3-C 10 Alkenyl group.

[0153] R 15 It can be, for example, hydrogen, deuterium, or straight-chain C1-C. 10 Alkyl groups or branched C3-C 10 Alkyl groups.

[0154] In one or more implementations, R 15 It can be a branched C3-C 10 Alkyl groups. For example, in one or more embodiments, R 15 It can be a tert-butyl group.

[0155] According to one or more embodiments, the polycyclic compound can be any one of the compounds represented by chemical formula 1 to chemical formula 100.

[0156]

[0157] As described above, the polycyclic compound may contain at least one of an electron-withdrawing group and an electron-deficient nitrogen at the LUMO site. The polycyclic compound may possess a multiple resonance effect enhanced by appropriately or suitably arranged boron and nitrogen.

[0158] Polycyclic compounds can possess deep HOMO levels to suppress or reduce trap-assisted recombination, where holes and electrons recombine in the emitter layer. Therefore, the lifespan of light-emitting devices can be improved.

[0159] In one or more embodiments, the HOMO level of the polycyclic compound may be about -5.30 eV or less, about -5.50 eV or less, or about -5.60 eV or less.

[0160] Polycyclic compounds can have a lower absolute value (ΔEst) between the lowest singlet excited state level (S1 level) and the lowest triplet excited state level (T1 level), which can improve the RISC and CT properties of the molecule.

[0161] In one or more embodiments, the absolute value (ΔEst) of the difference between the lowest singlet excited state level (S1 level) and the lowest triplet excited state level (T1 level) in the polycyclic compound can be about 0.14 eV or less, about 0.12 eV or less, or about 0.11 eV or less.

[0162] In one or more embodiments, the polycyclic compound can be used as a thermally activated delayed fluorescence (TADF) dopant or as the host for a phosphorescent device.

[0163] Polycyclic compounds can improve the luminescence properties and lifetime properties of light-emitting devices by enhancing both the exciton generation efficiency and oxidation stability of the emitter layer (e.g., simultaneously).

[0164] Polycyclic compounds can have narrow half-width emission spectra to provide improved color purity.

[0165] In one or more embodiments, a polycyclic compound can be used as a blue luminescent dopant.

[0166] In one or more embodiments, the maximum emission wavelength of blue light (e.g., peak emission wavelength) may be, for example, about 430 nm to about 480 nm, about 440 nm to about 475 nm, about 440 nm to about 465 nm, or about 445 nm to about 465 nm.

[0167] In one or more embodiments, the emission half-width of blue light may be about 28 nm or less, about 25 nm or less, about 20 nm or less, about 18 nm or less, about 10 nm to about 20 nm, or about 10 nm to about 18 nm, or about 10 nm to about 15 nm.

[0168] Light-emitting device

[0169] Figures 1 to 6Each is a schematic cross-sectional view illustrating one or more embodiments of a light-emitting device according to the present disclosure.

[0170] refer to Figure 1 The light-emitting device ED may include a first electrode 110, a second electrode 150, and an emitting layer 130 inserted between the first electrode 110 and the second electrode 150. The emitting layer 130 may include a polycyclic compound of the above-described chemical formula 1, and may have improved color properties, luminous efficiency, and lifespan properties.

[0171] The light-emitting device ED may include an intermediate layer ITL, which includes an emitting layer 130 disposed between a first electrode 110 and a second electrode 150. The intermediate layer ITL may further include a hole transport region 120 and an electron transport region 140.

[0172] In one or more embodiments, multiple emission layers may be arranged between the first electrode 110 and the second electrode 150, and charge generating layers may be arranged between adjacent emission layers. At least one of the emission layers may contain a polycyclic compound of Formula 1 described above.

[0173] Therefore, light-emitting devices (EDs) can have improved color properties, luminous efficiency, and lifespan.

[0174] In one or more embodiments, the light-emitting device ED may include two or more light-emitting structures, each of which may include an emitting layer 130 between a first electrode 110 and a second electrode 150. The light-emitting structure may include, for example, a stacked structure of a hole transport region 120, an emitting layer 130, and an electron transport region 140. The charge generation layer may include, for example, a p-type charge generation layer and / or an n-type charge generation layer.

[0175] In one or more embodiments, the light-emitting device ED can be a series-connected light-emitting device, which may include m light-emitting structures (m is 2 or an integer greater than 2) between the first electrode 110 and the second electrode 150, and (m-1) charge-generating layers respectively arranged between adjacent light-emitting structures.

[0176] exist Figure 5 The present invention provides a 3-stacked series structure including three light-emitting structures, but the light-emitting device ED can have a 2-stacked, 4-stacked, 5-stacked or more than 5-stacked series structure.

[0177] The first electrode 110 can be an anode or a cathode. In one or more embodiments, the first electrode 110 can be an anode and can be used as a pixel electrode. In these embodiments, the first electrode 110 can comprise a conductive material having a high work function that promotes hole injection.

[0178] In one or more embodiments, the first electrode 110 may be a transmission electrode. The first electrode 110 may comprise a transparent conductive oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0179] In one or more embodiments, the first electrode 110 may be a semi-transparent reflective electrode or a reflective electrode. The first electrode 110 may contain at least one element selected from silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), zinc (Zn), and alloys containing at least two of these elements. For example, in one or more embodiments, 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.

[0180] The first electrode 110 may have a single-layer structure or a multi-layer structure. For example, in one or more embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0181] The thickness of the first electrode 110 can be from about 700 Å to about 10,000 Å. For example, in one or more embodiments, the thickness of the first electrode 110 can be from about 1,000 Å to about 3,000 Å.

[0182] The second electrode 150 can be a cathode or an anode. In one or more embodiments, the second electrode 150 can be used as an electron injection electrode or as a cathode. The second electrode 150 can comprise a metal, alloy, conductive compound, etc., having a low work function.

[0183] For example, in one or more embodiments, the second electrode 150 may comprise 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 comprise one of the aforementioned materials, or a combination thereof (e.g., any suitable combination).

[0184] The second electrode 150 can be a transmission electrode, a semi-transmissive reflection electrode, or a reflection electrode. The second electrode 150 can have a single-layer structure or a multi-layer structure.

[0185] The emitter layer 130 may contain a polycyclic compound of chemical formula 1 as described above.

[0186] Polycyclic compounds can be included as a host or dopant in the emitter layer 130. Polycyclic compounds can be used, for example, as thermally activated delayed fluorescence (TADF) dopants or as a host for phosphorescent devices.

[0187] In one or more embodiments, a polycyclic compound may be used as a TADF dopant.

[0188] Therefore, the emitter layer 130 can have improved color purity and oxidation stability.

[0189] In one or more embodiments, the polycyclic compound may comprise at least one compound selected from those represented by chemical formulas 1-1 to 1-4 as described above.

[0190] In a non-limiting example, based on 100 parts by weight of the body, the emitter layer 130 may contain dopant in amounts 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.

[0191] The emitting layer 130 may be designed to emit blue light. For example, the maximum emission center wavelength of blue light may be about 430 nm to about 480 nm, about 440 nm to about 475 nm, about 440 nm to about 465 nm, or about 445 nm to about 465 nm.

[0192] In one or more embodiments, the emitter layer 130 may further comprise a host material and / or dopants, which will be described in more detail herein.

[0193] For example, in one or more embodiments, the emitter layer 130 may comprise a host material widely applicable to the relevant field, such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, β-derived derivatives, dihydrobenzanthene derivatives, benzophenanthrene derivatives, etc.

[0194] In one or more embodiments, the emitting layer 130 may comprise a host material, for example, represented by the chemical formula FH. For instance, a compound represented by the chemical formula FH may be used as a fluorescent host material.

[0195] Chemical formula FH

[0196] In the chemical formula FH, R FH1 To R FH4 Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted thio group, substituted or unsubstituted oxy group, or substituted or unsubstituted C1-C group. 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C6-C 30 A heteroaryl group, or a cyclic group formed by combination thereof. In one or more embodiments, in the chemical formula FH, the group is selected from R. FH1 To R FH4 At least one of them can form a fused ring with the bonded benzene ring.

[0197] In the chemical formula FH, x1a and x1b can each be an integer from 0 to 5 independently; and x2a and x2b can each be an integer from 0 to 4 independently. When x1a, x1b, x2a, and x2b are each 2 or greater than 2, the corresponding R... FH1 To R FH4 Two or more of them can be the same as or different from each other.

[0198] In one or more embodiments, the emitting layer 130 may comprise 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 (e.g., a phosphorescent dopant).

[0199] Chemical formula pH

[0200] In the chemical formula pH, R PH It can be a substituted or unsubstituted carbazole group. L PH It can be a direct-connect key, a replaced or unreplaced C6-C. 30 arylene groups, or substituted or unsubstituted C2-C 30 Hypoaryl group. Ar PH It can be substituted or unsubstituted C6-C 30 The aryl group is either substituted or unsubstituted C2-C. 30heteroaryl groups.

[0201] As stated in the definition of the term above, the term "C6-C" 30 "Aryl group" can encompass groups in which multiple aryl rings are fused or bonded together by cyclic groups (e.g., alicyclic hydrocarbon rings). For example, C6-C 30 The aryl group can be a fluorenyl group.

[0202] As stated in the definition of the term above, the term "C2-C" 30 "Heteroaryl group" can encompass groups in which multiple aryl rings are fused or bonded together via heterocyclic fusion. For example, C2-C 30 The heteroaryl group can be a carbazole group, a dibenzofuran group, a dibenzothiophene group, etc. In one or more embodiments, C2-C 30 A heteroaryl group can be a group in which multiple aryl rings are fused or bonded to each other through the same or different heterocycles.

[0203] In one or more implementation schemes, Ar PH The substituents contained therein can be -Si(R) sa (R) sb (R) sc ) represents a silyl group; and R sa R sb and R sc Each can be independently hydrogen, halogen, hydroxyl group, C1-C 60 Alkyl groups, C1-C 60 alkoxy group, C6-C 60 aryl group or C2-C 30 Heteroaryl groups. Selected from R sa R sb and R sc At least one of them can be C6-C 60 aryl group or C2-C 30 Heteroaryl groups. For example, in one or more embodiments, R sa R sb and R sc Each can be C6-C independently. 60 aryl group or C2-C 30 heteroaryl groups.

[0204] In the chemical formula pH, lx can be an integer from 0 to 10. When lx is 2 or greater than 2, L... PH Two or more of them can be the same as or different from each other.

[0205] In one or more embodiments, the emitter layer 130 may include, for example, BCPDS (bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane), POPPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphospho)dibenzo[b,d]furan), TCTA (4,4',4''-tris(carbazole-9-yl)-triphenylamine), TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), Alq3 Tris(8-hydroxyquinoline)aluminum, ADN (9,10-di(naphthyl-2-yl)anthracene), TBADN (2-tert-butyl-9,10-di(naphthyl-2-yl)anthracene), DSA (stilbeneyl arylene), 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), DPSiO4 (octaphenylcyclotetrasiloxane), etc. are used as main materials.

[0206] In one or more embodiments, the body in the emission layer 130 may include one of the materials described above, or any combination thereof.

[0207] Non-limiting examples of compounds represented by the chemical formula PH are as follows.

[0208]

[0209] In one or more embodiments, the emitter layer 130 may further include dopants that interact with the host.

[0210] In one or more embodiments, the emitter layer 130 may contain 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.

[0211] Chemical formula FD

[0212] In the chemical formula FD, Ar FD R FD1 and R FD2 Each can be either substituted or unsubstituted C3-C independently. 60 The carbocyclic group may or may not be substituted C1-C 60 Heterocyclic group. Ax can be an integer from 1 to 6.

[0213] In one or more implementation schemes, Ar FD It may contain fused ring structures in which three or more aryl rings or benzene rings are fused together (e.g., anthracene group, alkyl group, pyrene group, etc.).

[0214] In one or more embodiments, the emitting layer 130 may contain a dopant (e.g., a phosphorescent dopant) for a phosphorescent device. The dopant for the phosphorescent device may include an organometallic compound comprising a central metal and at least one ligand bonded to the central metal via a coordination bond. The central metal may include, for example, a transition metal, and the ligand may include, for example, monodentate, bidentate, tripentate, tetradentate, pentadentate, hexadentate, and / or combinations thereof (e.g., any suitable combination).

[0215] In one or more embodiments, the dopant for the phosphorescent device (e.g., a phosphorescent dopant) may include, for example, a compound represented by the chemical formula PD.

[0216] Chemical formula PD

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

[0218] In the chemical formula PD, M can be a transition metal, such as iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), ruthenium (Ru), copper (Cu), or thulium (Tm).

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

[0220] Chemical formula LD1

[0221] In the chemical formula LD1, X PD1 and X PD2 Each can be either C or N independently.

[0222] In one or more implementation schemes, X PD1 and X PD2 One of them can be C and the other can be N. In one or more implementations, X PD1 and X PD2 Each can be N.

[0223] In the chemical formula LD1, CG PD1 and CG PD2 Each can be either substituted or unsubstituted C3-C independently. 60 The carbocyclic group may or may not be substituted C1-C 60 Heterocyclic groups.

[0224] For example, CG PD1 and CG PD2 These groups can be pyrrole groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, phenyl groups, pyridine groups, pyrimidine groups, naphthyl groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, fluorene groups, dibenzothiophene groups, naphthanobenzofuran groups, naphthanobenzothiophene groups, benzocarbazole groups, benzofluorene groups, naphthanobenzothiophene groups, dinaphthofuran groups, dinaphthothiophene groups. Group, dibenzocarbazole group, dibenzofluorene group, dinaphthothiophene group, azidobenzofuran group, azidobenzothiophene group, azidocarbazole group, azidofluorene group, azidobenzothiophene group, azidobenzobenzofuran group, azidobenzobenzothiophene group, azidobenzocarbazole group, azidobenzofluorene group, azidobenzobenzothiophene group, azidobenzofuran group, azidobenzothiophene group, azidobenzocarbazole group, azidobenzofluorene group or azidobenzothiophene group.

[0225] In the chemical formula LD1, L PD It can be a single bond, a substituted or unsubstituted methylene group, or a substituted or unsubstituted ethylene group. -O- '、 -S- '、 -C(=O)- '、 -N(R PD3 )- '、 -C(R PD4 )= 'or =C(R PD5 )- '. and Each represents a binding site.

[0226] In the chemical formula LD1, X PD3 and X PD4 Each can be an independent chemical bond, O, S, N (R) PD6 ), B(R) PD7 ), P(R PD8 ), C(R PD8 (R) PD9 ) or Si(R PD10 (R) PD11 Chemical bonds can be, for example, covalent bonds or coordinate bonds.

[0227] In the chemical formula LD1, R PD1 and R PD2 They can be hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C atoms, each independently. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted aniline groups, -B(R) PD12 (R) PD13 -C(=O)(R) PD14 -S(=O)2(R)PD15 ), or -P(=O)(R PD16 (R) PD17 The silyl group can be derived from -Si(R) sa (R) sb (R) sc ) indicates, as explained above.

[0228] R PD3 To R PD17 They can be hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C atoms, each independently. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, or substituted or unsubstituted C8-C 60 Fused polycyclic groups.

[0229] In the chemical formula LD1, cx1 and cx2 can each be an integer from 0 to 10 independently. R is calculated when at least one of cx1 or cx2 is 2 or greater than 2. PD1 Two or more of the following and / or R PD2 Two or more of them can be the same as or different from each other.

[0230] symbol- and- Each represents the binding site of the ligand represented by the chemical formula LD1 to M.

[0231] In the chemical formula PD, dx1 is an integer from 1 to 3. When dx1 is 2 or 3, L d 1 Two or three of them can be the same as or different from each other. In L d 1 Among two or three CGs, those that are adjacent to each other PD1 and / or CGPD2 Through, such as L PD1 L PD2 Linking groups such as L are connected to each other. PD1 L PD2 The linking groups, etc., can each independently bind with L. PD The definitions are the same.

[0232] In the chemical formula PD, L d 2 It can be an organic ligand. L d 2 It may include, for example, halogens, CO, NO, CS, pyridine carboxylates, acetates, oxalates, diketone groups, isonitrile groups, isothiocyano-N, thiosulfate-S, alkylphosphine, phenylphosphine, arylphosphine, phosphine oxide, phosphites, or any suitable combination thereof.

[0233] In the chemical formula PD, dx2 is an integer from 1 to 4. When dx2 is 2 or greater than 2, L d 2 Two or more of them can be the same as or different from each other.

[0234] Non-limiting examples of compounds represented by the chemical formula PD are as follows.

[0235]

[0236] In one or more embodiments, the emitter layer 130 may comprise a styrene derivative (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) One or more of the following can be used as fluorescent dopant materials: 1,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.).

[0237] In one or more embodiments, in addition to one or more of the materials described above, the emitting layer 130 may comprise a metal complex, including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) as a phosphorescent dopant. For example, FIrpic (bis(4,6-difluorophenylpyridyl-N,C2')iridium pyridinecarboxylate(III)), Fir6 (bis(2,4-difluorophenylpyridyl)-tetra(1-pyrazolyl)boronate(III)), PtOEP (platinum octaethylporphyrin), etc., can be used as phosphorescent dopants.

[0238] In one or more embodiments, the emitter layer 130 may contain a boron-containing dopant represented by the chemical formula BD.

[0239] Chemical formula BD

[0240] In the chemical formula BD, X BD1 and X BD2 Each can be N(R) independently. BD1 ), P(R BD2 ), C(R BD3 (R) BD4 ), Si(R) BD5 (R) BD6 ), S or O. In one or more implementations, X BD1 and X BD2 Each can be N. R BD1 To R BD6 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20Alkyl groups, substituted or unsubstituted C6-C 30 aryl group, or substituted or unsubstituted C2-C 30 heteroaryl group. R BD7 R BD8 and R BD9 Each of these can be independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted boron group, substituted or unsubstituted oxygen group, substituted or unsubstituted thio group, or substituted or unsubstituted C1-C group. 20 Alkyl groups, substituted or unsubstituted C6-C 30 aryl group, or substituted or unsubstituted C2-C 30 heteroaryl group. R BD7 R BD8 and / or R BD9 It can be optionally bonded to adjacent groups to form a ring.

[0241] In the chemical formula BD, CG BD1 and CG BD2 Each represents a cyclic group, and CG BD1 and CG BD2 Each can be either substituted or unsubstituted C3-C independently. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups. In one or more embodiments, CG BD1 and CG BD2 Each can be either substituted or unsubstituted C6-C independently. 30 The aryl group is either substituted or unsubstituted C2-C. 30 heteroaryl groups.

[0242] In one or more implementation schemes, CG BD1 and CG BD2 Each of the benzene rings can be substituted or unsubstituted, independently. In these embodiments, boron-containing dopants can be used as thermally activated delayed fluorescence (TADF) dopants.

[0243] In one or more implementation schemes, CG BD1 and CG BD2 One of them can be a non-fused aryl group or a non-fused heteroaryl group, and the other can be a fused polycyclic aryl group or a fused polycyclic heteroaryl group. In these embodiments, the boron-containing dopant can be used as a fluorescent dopant.

[0244] In one or more embodiments, the emitter layer 130 may comprise one or any combination of the dopant materials described above.

[0245] In one or more embodiments, the emitter layer 130 may comprise two or more host materials. For example, in one or more embodiments, the emitter layer 130 may comprise a hole transport host and an electron transport host. In these embodiments, the emitter layer 130 may comprise a hole transport host, an electron transport host, a photosensitizer, and a dopant. In one or more embodiments, the hole transport host and the electron transport host may form an excimer complex, and energy can be transferred from the excimer complex to the photosensitizer and from the photosensitizer to the dopant, thereby inducing light emission.

[0246] Non-limiting examples of hole transport entities may include compounds represented by the chemical formula HT, which will be described in more detail later. Non-limiting examples of electron transport entities may include compounds represented by the chemical formula ET, which will be described in more detail later.

[0247] In one or more embodiments, the emitter layer 130 may comprise quantum dots. The quantum dots may comprise II-VI compounds, III-VI compounds, I-III-VI compounds, III-V compounds, III-II-V compounds, IV-VI compounds, group IV elements, group IV compounds, and / or any suitable combinations thereof.

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

[0249] In one or more embodiments, the color of light emanating from the quantum dots can be adjusted according to the particle size of the quantum dots. The quantum dots can be blue quantum dots designed to emit blue light, red quantum dots designed to emit red light, or green quantum dots designed to emit green light.

[0250] The hole transport region 120 can be formed between the first electrode 110 and the emitter layer 130. The hole transport region 120 can have a single-layer structure or a multi-layer structure containing different materials.

[0251] The hole transport region 120 may include a hole injection layer, a hole transport layer and / or an electron blocking layer, and may further include an emission assist layer.

[0252] In one or more implementation schemes, such as Figure 2As shown, the hole transport region 120 may include a hole injection layer 122 and a hole transport layer 124 stacked sequentially from the first electrode 110.

[0253] In one or more implementation schemes, such as Figure 3 As shown, the hole transport 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 flowing from the electron transport region 140 to the hole transport region 120. Accordingly, the generation of excitons in the emission layer 130 can be increased, and the luminous efficiency can be further increased.

[0254] In one or more embodiments, hole transport region 120 may contain a compound represented by the chemical formula HT.

[0255] Chemical formula HT

[0256] In the chemical formula HT, L HT1 L HT2 and L HT3 Each can be a direct bond, substituted or unsubstituted C6-C, independently. 30 arylene groups, or substituted or unsubstituted C2-C 30 Hybrid aryl group.

[0257] In the chemical formula HT, lx1 to lx3 can each be an integer from 0 to 10 independently. When lx1, lx2, or lx3 is 2 or greater than 2, the corresponding L... HT3 L HT1 or L HT2 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 arylene groups or substituted or unsubstituted C2-C 30 Hypoaryl groups. For example, when lx3 is 2 or greater than 2, L HT3 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 arylene groups or substituted or unsubstituted C2-C 30 Hypoaryl group. When lx1 is 2 or greater, L HT1 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30arylene groups or substituted or unsubstituted C2-C 30 Hypoaryl group. When lx2 is 2 or greater, L HT2 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 arylene groups or substituted or unsubstituted C2-C 30 Hybrid aryl group.

[0258] In the chemical formula HT, Ar HT1 and Ar HT2 Each can be either substituted or unsubstituted C6-C independently. 30 The aryl group is either substituted or unsubstituted C2-C. 30 heteroaryl group. Ar HT3 It can be substituted or unsubstituted C6-C 30 Aryl group.

[0259] In one or more embodiments, the compound represented by the chemical formula HT can be a monoamine compound. In one or more embodiments, the compound represented by the chemical formula HT can be a diamine compound, wherein the compound is selected from Ar. HT1 To Ar HT3 At least one of them includes an amine group as a substituent.

[0260] In one or more embodiments, the compound represented by the chemical formula HT can be Ar. HT1 and Ar HT2 At least one of the carbazole-based compounds comprising a substituted or unsubstituted carbazole group, or wherein Ar HT1 and Ar HT2 At least one of the fluorene-based compounds includes a substituted or unsubstituted fluorene group.

[0261] In one or more implementation schemes, Ar HT1 To Ar HT3 Two adjacent groups in a ring can fuse together to form a ring.

[0262] Non-limiting examples of compounds represented by the formula HT are as follows.

[0263]

[0264] For example, in one or more embodiments, the hole transport region 120 may contain a material selected from 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), spiro-TPD, spiro-NPB, DNTPD (N 1 N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) 1 -Phenyl-N 4 N 4 The hole transport region 120 may include one or more of the following: di-m-methylphenylphenyl-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(N-carbazolyl)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.), fluorene compounds, etc. The hole transport region 120 may include one or more of the above-mentioned hole transport materials, or (e.g., any suitable combination thereof).

[0265] The aforementioned hole transport 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.

[0266] In one or more embodiments, the hole transport region 120 may further comprise a charge-generating material. The charge-generating material may be a dopant material such as a p-doper, which can improve the conductivity of the hole transport region 120.

[0267] Non-limiting examples of dopant materials may include metal halide compounds (e.g., metal halides) such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / 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 HATCN (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-tetrafluorobenzylnitrile), etc.; tungsten (W) oxides; molybdenum (Mo) oxides; etc. Hole transport region 120 may contain one of the dopant materials described above, or a combination thereof (e.g., any suitable combination).

[0268] The thickness of the hole transport region 120 can be from about 100 Å to about 10,000 Å. For example, the thickness of the hole transport region 120 can be from about 100 Å to about 1,500 Å.

[0269] When the hole transport region 120 includes a hole injection layer 122 and / or a hole transport layer 124, the thickness of the hole injection layer 122 may be about 100 Å to about 9,000 Å, about 100 Å to about 3,000 Å, or about 100 Å to about 1,000 Å. The thickness of the hole transport layer 124 may be about 50 Å to about 2,000 Å, about 100 Å to about 1,500 Å, about 100 Å to about 1,000 Å, or about 100 Å to about 600 Å.

[0270] Within the aforementioned thickness range, hole transport properties can be enhanced even under low-voltage operation, and the lifespan of the device can be further improved.

[0271] Each constituent layer of the hole transport region 120 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, and laser thermal transfer.

[0272] The electron transport region 140 can be formed between the second electrode 150 and the emitter layer 130. The electron transport region 140 can have a single-layer structure or a multi-layer structure containing different materials.

[0273] The hole transport region 140 may include an electron injection layer, an electron transport layer and / or a hole blocking layer, and may further include an emission assist layer.

[0274] In one or more implementation schemes, such as Figure 2As shown, the electron transport region 140 may include an electron injection layer 142 and a hole transport layer 144 stacked from the second electrode 150 to the emitter layer 130.

[0275] In one or more implementation schemes, such as Figure 3 As shown, the electron transport region 140 may include an electron injection layer 142, an electron transport layer 144, and a hole blocking layer 146 stacked from the second electrode 150 to the emitter layer 130. The hole blocking layer 146 can block, suppress, or reduce the flow of holes from the hole transport region 120 to the electron transport region 140. Therefore, the emission energy and luminous efficiency in the emitter layer 130 can be further improved.

[0276] For example, in one or more embodiments, the electron transport region 140 may contain a compound represented by the chemical formula ET.

[0277] Chemical formula ET

[0278] In the chemical formula ET, X is selected. ET1 To X ET3 At least one of them can be N, and X ET1 To X ET3 The remainder can each be independently C(R) ET R ET It can be hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 60 aryl group, or substituted or unsubstituted C2-C 60 heteroaryl groups.

[0279] When X ET1 To X ET3 When one of them is N, a compound represented by the chemical formula ET can contain a pyridine group. When X ET1 To X ET3 When both of X are N, compounds represented by the chemical formula ET can include pyrimidine groups. ET1 To X ET3 When each is N, a compound represented by the chemical formula ET can contain a triazine group.

[0280] In the chemical formula ET, lx1 to lx3 can each be an integer from 0 to 10 independently. ET1 To L ET3 Each can be a direct bond, substituted or unsubstituted C6-C, independently. 30 arylene groups, or substituted or unsubstituted C2-C 30 Hybrid aryl group.

[0281] When lx1, lx2, or lx3 is 2 or greater than 2, the corresponding L ET1 L ET2 or L ET3 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 arylene groups or substituted or unsubstituted C2-C 30 Hypoaryl groups. For example, when lx1 is 2 or greater than 2, L ET1 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 arylene groups or substituted or unsubstituted C2-C 30 Heteroaryl group. When lx2 is 2 or greater than 2, L ET2 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 arylene groups or substituted or unsubstituted C2-C 30 Heteroaryl group. When lx3 is 2 or greater than 2, L ET3 Two or more of the atoms in the aryl ring can be represented by, for example, the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 arylene groups or substituted or unsubstituted C2-C 30 Hybrid aryl group.

[0282] In the chemical formula ET, Ar ET1 To Ar ET3 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 aryl group, or substituted or unsubstituted C2-C 30 Heteroaryl groups. For example, in one or more embodiments, Ar ET1 To Ar ET3 Each of these groups can be independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted silyl group. The silyl group can be composed of -Si(R) as explained above. sa (R) sb (R) sc )express.

[0283] Non-limiting examples of compounds represented by the formula ET are as follows.

[0284]

[0285] In one or more embodiments, the electron transport region 140 may comprise an anthracene compound, Alq3 (tris(8-hydroxyquinoline)aluminum), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum), Bebq2 (bis(benzoquinoline-10-oline)beryllium), ADN (9,10-bis(naphthyl-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene), etc. The electron transport region 140 may include one of the above-mentioned electron transport materials, or (e.g., any suitable combination thereof).

[0286] The aforementioned material may be contained in at least one of the electron injection layer 142, the electron transport layer 144, and the hole blocking layer 146.

[0287] In one or more embodiments, the electron transport region 140 may comprise alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof (e.g., any suitable combination). In one or more embodiments, one or more of the above materials may be included in the electron injection layer 142.

[0288] 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.

[0289] Compounds containing alkali metals, compounds containing alkaline earth metals, and compounds containing rare earth metals may respectively contain oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, and / or combinations thereof (e.g., any suitable combination).

[0290] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may comprise their respective metal ions, such as alkali metal ions, alkaline earth metal ions, or rare earth metal ions, and ligands bound to their respective metal ions. Ligands may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, and / or combinations thereof (e.g., any suitable combination).

[0291] The thickness of the electron transport region 140 can be from about 100 Å to about 1,000 Å, for example from about 150 Å to about 500 Å.

[0292] When the electron transfer region 140 includes an electron injection layer 142 or an electron transport layer 144, the thickness of the electron injection layer 142 may be about 1 Å to about 100 Å, about 1 Å to about 90 Å, or about 5 Å to about 50 Å, and the thickness of the electron transport layer 144 may be about 10 Å to about 900 Å, about 10 Å to about 500 Å, or about 100 Å to about 400 Å.

[0293] Within any of the aforementioned thickness ranges, electron injection and electron transport properties can be further improved without excessively increasing the driving voltage, and the stability of the electron transport region 140 can be improved.

[0294] Each constituent layer of the electron transport region 140 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, and laser thermal transfer.

[0295] In one or more embodiments, the light-emitting device ED may further include a cover layer. The cover layer can improve the light emission efficiency of the exterior of the light-emitting device ED.

[0296] like Figure 4 As shown, in one or more embodiments, a second capping layer 160b may be formed on the outer surface of the second electrode 150. In one or more embodiments, a first capping layer 160a may be formed on the outer surface of the first electrode 110.

[0297] The refractive index of the first capping layer 160a and / or the second capping layer 160b may be 1.6 or greater than 1.6. For example, in one or more embodiments, the refractive index of the first capping layer 160a and / or the second capping layer 160b for light in the wavelength range of 550 nm to 660 nm may be 1.6 or greater than 1.6, 1.8 or greater than 1.8, or 2.0 or greater than 2.0.

[0298] The first capping layer 160a and the second capping layer 160b may each be formed as an organic capping layer containing organic materials, an inorganic capping layer containing inorganic materials, or an organic-inorganic composite capping layer containing both organic and inorganic materials (e.g., simultaneously).

[0299] The first cover layer 160a and / or the second cover layer 160b may each have a single-layer structure or a multi-layer structure containing different materials.

[0300] In one or more embodiments, the first capping layer 160a and the second capping layer 160b may each independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthylphthalocyanine 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 of the aforementioned materials, or a combination thereof (e.g., any suitable combination).

[0301] In one or more embodiments, the first capping layer 160a and / or the second capping layer 160b may each independently contain a compound containing an amine group.

[0302] In a non-limiting example, the first capping layer 160a and / or the second capping layer 160b may contain at least one compound selected from chemical formulas P1 to P4 and / or at least one compound selected from compounds HT-7, HT-8, HT-14, HT-15 and HT-16.

[0303]

[0304] refer to Figure 5 In one or more embodiments, the light-emitting device ED may include multiple light-emitting structures (e.g., a first light-emitting structure ES1, a second light-emitting structure ES2, and a third light-emitting structure ES3). The first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may each include a stacked structure comprising a hole transport region 120, an emission layer 130, and an electron transport region 140, as shown in reference [reference needed]. Figures 1 to 3 As described above. In one or more embodiments, Figure 5 The light-emitting device ED can be a light-emitting device with a series structure.

[0305] The first charge generation layer CGL1 and the second charge generation layer CGL2 can each be arranged between adjacent structures in the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3, respectively. The first charge generation layer CGL1 and the second charge generation layer CGL2 can independently include a p-type (e.g., P-charge) generation layer and / or an n-type (e.g., N-charge) generation layer.

[0306] The p-type charge generation layer may contain a hole transport host compound, such as NPB. For example, in one or more embodiments, the p-type charge generation layer may contain a compound represented by the above chemical formula HT. In one or more embodiments, the p-type charge generation layer may further contain a p-doper, such as TCNQ.

[0307] The n-type (or charge-generating) layer may contain an electron transport host compound. For example, in one or more embodiments, the n-type (or charge-generating) layer may contain a compound represented by the above-described chemical formula ET. In one or more embodiments, the n-type (or charge-generating) layer may contain a phenanthroline-based compound.

[0308] The first charge generation layer CGL1 and the second charge generation layer CGL2 may respectively include the first charge generation layer CGL1 arranged between the first light-emitting structure ES1 and the second light-emitting structure ES2 and the second charge generation layer CGL2 arranged between the second light-emitting structure ES2 and the third light-emitting structure ES3.

[0309] In one or more embodiments, 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.

[0310] 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 one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may respectively include a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer, and a white light-emitting structure may be achieved through a series structure, but the embodiments disclosed herein are not limited thereto.

[0311] exist Figure 5 In the example, a 3-stacked series structure of three light-emitting structures is illustrated, but the series structure of the light-emitting device in this disclosure is not limited to this. Figure 5 The structure is illustrated in the example. For example, referencing... Figure 6 The described stacking structures of 2, 4, 5, or 6 or more can also be implemented.

[0312] refer to Figure 6 For reference Figure 5 The description states that a series structure in which the light-emitting structure and the charge-generating layer are stacked alternately and repeatedly can be arranged between the first electrode 110 and the second electrode 150.

[0313] In one or more embodiments, the first light-emitting structures ES1 to the m-th light-emitting structures ESm can be sequentially stacked from the top surface of the first electrode 110, with charge-generating layers interposed therebetween. The charge-generating layers may include the first charge-generating layers CGL1 to the (m-1)-th charge-generating layers CGLM-1 sequentially stacked from the top surface of the first electrode 110.

[0314] like Figure 6 As illustrated, 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.

[0315] In one or more embodiments, 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, and first to third charge-generating layers CGL1, CGL2 and CGL3. The colors of the light generated by the first to fourth light-emitting structures ES1, ES2, ES3 and ES4 may be the same or different from each other.

[0316] In one or more embodiments, 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 the blue light-emitting structure, and the fourth light-emitting structure ES4 may correspond to the green light-emitting structure.

[0317] In one or more embodiments, 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, and first to fourth charge-generating layers CGL1, CGL2, CGL3 and CGL4. The colors of the light generated by the first to fifth light-emitting structures ES1, ES2, ES3, ES4 and ES5 may be the same or different from each other.

[0318] In one or more embodiments, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include at least one blue-emitting structure and at least one green-emitting structure. In a non-limiting example, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include three blue-emitting structures and two green-emitting structures. For example, in one or more embodiments, the first light-emitting structure ES1, the third light-emitting structure ES3, and the fifth light-emitting structure ES5 may correspond to blue-emitting structures, and the second light-emitting structure ES2 and the fourth light-emitting structure ES4 may correspond to green-emitting structures.

[0319] Electronic devices

[0320] 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 an electronic device.

[0321] Electronic devices may include light-emitting devices (EDs) that contain polycyclic compounds of the above-described chemical formula 1, thereby achieving improved color properties, luminous efficiency, and lifespan properties.

[0322] In one or more embodiments, the electronic device may further include, for example, a functional layer disposed on the 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 (e.g., any suitable combination).

[0323] Non-limiting examples of electronic devices may include display devices, billboards, signs, light sources, lighting devices, personal computers such as laptop or desktop computers, mobile phones, e-books, electronic dictionaries, electronic notebooks, healthcare devices including diagnostic devices and one or more suitable sensors, and one or more suitable display components for transportation equipment (cars, airplanes, ships, trains, etc.).

[0324] In one or more embodiments, the light-emitting device ED can be applied to an organic light-emitting diode (OLED) display device or a quantum dot (QD)-OLED display device.

[0325] Figure 7 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0326] refer to Figure 7 The display device may include a circuit layer CL disposed on a substrate 200, and a first light-emitting device ED1, a second light-emitting device ED2 and a third light-emitting device ED3 disposed on the circuit layer CL.

[0327] The substrate 200 can be used as a support substrate or backplane substrate for a display device. The substrate 200 can be a glass substrate or a plastic substrate.

[0328] In one or more embodiments, the substrate 200 may comprise a polymeric material having both transparent and flexible properties. If the substrate 200 comprises a polymeric material (e.g., when the substrate 200 comprises a polymeric material), then the substrate 200 can be used in a transparent flexible display device. For example, in one or more embodiments, the substrate 200 may comprise a polymeric material such as polyimide, polysiloxane, epoxy resin, acrylic resin, polyester, etc. In one or more embodiments, the substrate 200 may comprise polyimide.

[0329] The circuit layer CL may include a first transistor TR1, a second transistor TR2, and a third transistor TR3. The circuit layer CL may include wiring layers and insulating layers for forming a thin-film transistor array (TFT-array).

[0330] In one or more embodiments, the circuit layer CL may include a buffer layer 205 on the top surface of the substrate 200. The buffer layer 205 may prevent moisture from penetrating through the substrate 200 and may also prevent the diffusion of impurities between the substrate 200 and the structures formed thereon.

[0331] Buffer layer 205 may comprise, for example, silicon oxide, silicon nitride, and / or silicon oxide nitride. Buffer layer 205 may comprise one of the aforementioned materials, or (e.g., any suitable) combination thereof. In one or more embodiments, buffer layer 205 may have a stacked structure comprising silicon oxide layers and silicon nitride layers.

[0332] The first transistor TR1, the second transistor TR2, and the third transistor TR3 can be arranged on the buffer layer 205. The first transistor TR1, the second transistor TR2, and the third transistor TR3 can be electrically connected to the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3, respectively.

[0333] The first transistor TR1, the second transistor TR2, and the third transistor TR3 may each include an active layer 210, a gate insulating layer 220, and a gate electrode 230.

[0334] The active layer 210 may be disposed on the buffer layer 205 and may be patterned for each pixel. In one or more embodiments, the active layer 210 may comprise a silicon compound, such as amorphous silicon or polysilicon. A p-type or n-type dopant may be doped in regions of the active layer 210, and the active layer 210 may include source regions, drain regions, and channel regions.

[0335] In one or more embodiments, the active layer 210 may comprise an oxide semiconductor, such as indium gallium zinc oxide (IGZO), zinc tin oxide (ZTO), or ITZO.

[0336] The gate insulating layer 220 can be formed on the active layer 210, and the gate electrode 230 can be stacked on the gate insulating layer 220. For example... Figure 7 As illustrated, the gate insulating layer 220 may be patterned to partially cover each active layer 210. In one or more embodiments, the gate insulating layer 220 may extend continuously over multiple pixels or light-emitting regions and may be provided as a common layer for the first transistor TR1, the second transistor TR2, and the third transistor TR3.

[0337] The gate electrode 230 can overlap the channel region of the active layer 210 in the thickness direction.

[0338] An insulating intermediate layer 240 may be formed on the active layer 210 to cover the gate electrode 230 and the gate insulating layer 220. A first connection electrode 250 and a second connection electrode 260 that may be in contact with or electrically connected to the active layer 210 may each be arranged on the insulating intermediate layer 240.

[0339] The first connecting electrode 250 and the second connecting electrode 260 may extend through the insulating intermediate layer 240 to contact or be electrically connected to the active layer 210. When the gate insulating layer 220 is provided as a common layer for multiple light-emitting regions, the first connecting electrode 250 and the second connecting electrode 260 may also extend through the gate insulating layer 220.

[0340] The first connecting electrode 250 and the second connecting electrode 260 may each include a source electrode 250 that can contact or be connected to the source region of the active layer 210, and a drain electrode 260 that can contact or be connected to the drain region of the active layer 210.

[0341] The gate insulating layer 220 and the insulating intermediate layer 240 may each independently comprise silicon oxide, silicon nitride and / or silicon nitride, and may each have a stacked structure including silicon oxide layer and silicon nitride layer.

[0342] The gate electrode 230, the first connection electrode 250, and the second connection electrode 260 may each independently contain a metal, such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, their alloys, or their nitrides.

[0343] The through-hole insulating layer 270 can be formed on the insulating intermediate layer 240 to cover the first connecting electrode 250 and the second connecting electrode 260.

[0344] 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 serve as a planarization layer for the circuit layer CL. In one or more embodiments, the via insulating layer 270 can comprise an organic material, such as polyimide, epoxy resin, acrylic resin, polyester, etc.

[0345] The first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 can be arranged on the through-hole insulating layer 270. For example, as shown in the reference... Figures 1 to 4 As described, the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 may each include a first electrode 110, a hole transport region 120, an emission layer 130, an electron transport region 140, and a second electrode 150, which are stacked sequentially from the through-hole insulating layer 270.

[0346] The first electrode 110 can be electrically connected via a through-hole structure to the corresponding first transistor TR1, second transistor TR2, and third transistor TR3 in the circuit layer CL, or to the corresponding first connection electrode 250 or second connection electrode 260. For example... Figure 7 As illustrated, in one or more embodiments, the first electrode 110 may contact or be connected to the drain electrode 260 to serve as a pixel electrode for patterning each light-emitting area or pixel.

[0347] A pixel defining layer 280 may be formed on the via insulating layer 270 to define each light-emitting area or pixel. Blue light-emitting area, red light-emitting area and green light-emitting area may be separated and defined by pixel defining layer 280, and the first light-emitting device ED1, the second light-emitting device ED2 and the third light-emitting device ED3 may correspond to the blue light-emitting device, the red light-emitting device and the green light-emitting device, respectively.

[0348] The pixel-defining layer 280 can partially cover the first electrode 110 of each light-emitting area.

[0349] like Figure 7 As illustrated, hole transport region 120 and electron transport region 140 can each be provided as a common layer extending continuously over pixel defining layer 280 and first electrode 110. Emitting layer 130 can be formed within each light-emitting region or pixel and can be separated by pixel defining layer 280.

[0350] In one or more embodiments, the emitting layer 130 may also be provided as a common layer extending continuously over the light-emitting area or pixel. In one or more embodiments, the hole transport area 120, the emitting layer 130, and the electron transport area 140 may each be patterned and formed individually for each light-emitting area or pixel.

[0351] The second electrode 150 can be provided as a common electrode that extends continuously over the light-emitting area or pixel.

[0352] The encapsulation layer 290 can be disposed on the pixel defining layer 280 and the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 to protect the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 from moisture and / or oxygen. The encapsulation layer 290 can be a thin-film encapsulation (TFE) with a single-layer structure or a multi-layer structure.

[0353] Encapsulation layer 290 may include: an inorganic layer comprising silicon nitride (SiN). x ), silicon oxide (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), etc.) or any combination thereof; or a combination of an inorganic layer and an organic layer (e.g., any suitable one).

[0354] 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 (e.g., a touch sensor layer), an optical layer (e.g., such as a polarizing layer), a color conversion layer, a color filter layer, a window film, or any combination thereof.

[0355] Figure 8 This is a schematic cross-sectional view illustrating one or more embodiments of a display device according to this disclosure. The detailed description of the components and structures is substantially consistent with the references. Figure 7 Those described are the same or similar.

[0356] refer to Figure 8 Each of the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 can have a series structure, such as a 2-stacked series structure.

[0357] In one or more embodiments, hole transport region 120 and electron transport region 140 may be continuously and jointly formed and included in the intermediate layer of each light-emitting structure. Furthermore, charge generation layer CGL may continuously extend through multiple pixels and may be jointly included in the intermediate layer of each light-emitting structure.

[0358] The first light-emitting device ED1 may include a first lower emitting layer 130-1a disposed between the hole transport 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 transport region 140.

[0359] The second light-emitting device ED2 may include a second lower emitting layer 130-2a disposed between the hole transport 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 transport region 140.

[0360] The third light-emitting device ED3 may include a third lower emitting layer 130-3a disposed between the hole transport 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 transport region 140.

[0361] The lower and upper emitting layers included in each light-emitting structure (i.e., in each tandem light-emitting structure) can produce light of the same color. In one or more embodiments, 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.

[0362] Figure 9 This is a schematic cross-sectional view illustrating the stacked configuration of the light-emitting structures in a display device according to one or more embodiments of the present disclosure. For ease of illustration and description, in Figure 9 Descriptions of circuit layers, substrates, pixel-defining layers, etc., are omitted, and the shape of each layer or element in the light-emitting structure is simply shown as a rectangle.

[0363] refer to Figure 9 In one or more embodiments, at least one of the first light-emitting device ED1, the second light-emitting device ED2 and the third light-emitting device ED3 or at least one of the first pixel region PA1, the second pixel region PA2 and the third pixel region PA3 may have a series structure including multiple emission layers, and at least one of the others may have a single emission layer structure.

[0364] In one or more embodiments, the first light-emitting device ED1, the second light-emitting device ED2 and the third light-emitting device ED3 or the first pixel region PA1, the second pixel region PA2 and the third pixel region PA3 may have a series structure, and the others may have a single emission layer structure.

[0365] like Figure 9 As illustrated, 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 one or more embodiments, the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3 may correspond to the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0366] Hole transport region 120, electron transport region 140 and second electrode 150 may each be provided as a common layer extending continuously over the first pixel region PA1, the second pixel region PA2 and the third pixel region PA3.

[0367] 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-layer emitting layer.

[0368] The third light-emitting device ED3, included in the third pixel region PA3, may have, for example, a two-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-generating layer CGL interposed therebetween. For example, each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b may correspond to a blue emitting layer.

[0369] The lower electron transport region 140a can be arranged between the charge generation layer CGL and the third lower emitter layer 130-3a. The upper hole transport region 120b can be arranged between the charge generation layer CGL and the third upper emitter layer 130-3b.

[0370] Therefore, the tandem light-emitting structure in which the first electrode 110, hole transport region 120, third lower emission layer 130-3a, lower electron transport region 140a, charge generation layer CGL, upper hole transport region 120b, third upper emission layer 130-3b, electron transport region 140, and second electrode 150 are stacked in sequence can be arranged in the third pixel region PA3.

[0371] Figure 10 This is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0372] Figure 10 Examples of display devices with QD-OLED structures according to one or more embodiments are shown. Detailed descriptions and references are provided for the components and structures. Figure 7 Those descriptions that are the same or substantially similar will not be repeated for the sake of simplicity.

[0373] refer to Figure 10 The pixel limiting layer 280 and the light-emitting device ED can be arranged on the circuit layer CL, as shown in the above reference. Figure 7 Description. In one or more embodiments, each pixel may be designed to emit light in the same wavelength range. In one or more embodiments, each light-emitting device (ED) may emit blue light.

[0374] In one or more embodiments, each light-emitting region may include a light-emitting device ED having a series structure, as described above. Figure 5As described. In these embodiments, the intermediate layer of each light-emitting device ED can be provided as a common layer that extends continuously over multiple light-emitting areas.

[0375] The color control layer CCL can be disposed on the encapsulation layer 290, and the color control layer CCL can include a first color control portion CCP1, a second color control portion CCP2 and a third color control portion CCP3.

[0376] The first color control section CCP1, the second color control section CCP2, and the third color control section CCP3 may each include a light transducer, such as a quantum dot and / or a phosphor. In each of the first color control section CCP1, the second color control section CCP2, and the third color control section CCP3, the light transducer can convert the wavelength of the supplied light and emit the resulting light.

[0377] The first color control portion CCP1, the second color control portion CCP2, and the third color control portion CCP3 can be separated or partitioned from each other by the embankment BM (e.g., partitioned or separated). The embankment BM can substantially overlap with the pixel defining layer 280, and the first color control portion CCP1, the second color control portion CCP2, and the second color control portion CCP3 can substantially overlap with each of the emission layers 130.

[0378] The color control layer (CCL) may include a first color control portion (CCP1) containing 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) containing a second quantum dot that converts the first color light into a third color light, and a third color control portion (CCP3) that transmits the first color light.

[0379] In one or more embodiments, 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.

[0380] The first color control portion CCP1, the second color control portion CCP2, and the third color control portion CCP3 may each further include a scattering material, such as inorganic particles. The third color control portion CCP3 may not contain (e.g., may exclude) quantum dots and may contain a scattering material. The scattering material may include TiO2, ZnO, Al2O3, SiO2, hollow silica, etc. The scattering material may be one of the aforementioned materials or a combination thereof (e.g., any suitable combination).

[0381] The first color control portion CCP1, the second color control portion CCP2, and the third color control portion CCP3 may each further include an adhesive resin for dispersing quantum dots and scattering materials. The adhesive resin may include acrylic resin, urethane resin, silicone resin, or epoxy resin, etc.

[0382] A color filter layer CFL, including a first color filter CF1, a second color filter CF2, and a light-shielding component CP, can be arranged on a color control layer CCL.

[0383] 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.

[0384] The first color filter CF1 and the second color filter CF2 may each contain a photosensitive adhesive resin and a colorant containing pigments and / or dyes. The first color filter CF1 may contain red pigments and / or red dyes, and the second color filter CF2 may contain green pigments and / or green dyes.

[0385] The light-shielding component CP can be arranged between the color filters. In one or more embodiments, the light-shielding component CP may include a first light-shielding component CP1 and a second light-shielding component CP2 containing colorants of different colors.

[0386] In one or more embodiments, the first light-shielding component CP1 may include a blue colorant, and the second light-shielding component CP2 may include a red or black colorant. In one or more embodiments, in the blue light-emitting region, a portion of the first light-shielding component CP1 may be provided as a blue color filter and may be exposed between the second light-shielding components CP2, such that no additional color filter (e.g., a third color filter) may be provided.

[0387] The first barrier layer 310 can be disposed between the color control layer CCL and the light-emitting device ED (or encapsulation layer 290). The second barrier layer 320 can be disposed between the color control layer CCL and the color filter layer CFL.

[0388] The first barrier layer 310 and the second barrier layer 320 may each include at least one inorganic layer. For example, the first barrier layer 310 and the second barrier layer 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 nitride, etc.

[0389] In one or more embodiments, the first barrier layer 310 and the second barrier layer 320 may each have a multilayer structure that further includes an organic layer.

[0390] Figure 11 This is a schematic cross-sectional view illustrating one or more embodiments of a display device according to the present disclosure. Terms substantially related to the references are omitted herein. Figure 10 A detailed description of those identical or similar elements and structures.

[0391] refer to Figure 11 The light-emitting devices ED corresponding to the first color control section CCP1, the second color control section CCP2 and the third color control section CCP3 can each be arranged on the first electrode 110, which serves as a pixel electrode, and the light-emitting devices ED can have a series structure.

[0392] In one or more implementation schemes, as referenced Figure 5 As described, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, and the third light-emitting structure ES3 can be stacked sequentially between the first electrode 110 and the second electrode 150. In one or more embodiments, 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.

[0393] In one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can produce light of different colors, and the light-emitting device ED can produce white light (e.g., combined white light). In one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can all produce blue light.

[0394] In one or more implementation schemes, as referenced Figure 6 As described, the light-emitting device ED may include a series structure with 4 stacks, 5 stacks, or more than 5 stacks.

[0395] Figure 12 It is a block diagram of an electronic device according to one or more embodiments of the present disclosure.

[0396] refer to Figure 12 An electronic device 10 according to one or more embodiments may include a display module 11, a processor 12, a memory 13, and a power module 14.

[0397] 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.

[0398] Data information for the operation of processor 12 and / or display module 11 can be stored in memory 13. When processor 12 executes the application stored in memory 13, image data signals and / or input control signals can be sent to display module 11, and display module 11 can process the received signals and output image information through the display screen.

[0399] The power module 14 may include a power supply module and / or battery device such as a power adapter, and a power conversion module that converts the power supplied by the power supply module to generate the power desired or required for the operation of the electronic device 10.

[0400] At least one of the components selected from the electronic device 10 described above may be included in the display device according to the above embodiment. Furthermore, some of the individual modules functionally included in a single module may be included in the display device, while other modules may be provided separately from the display device. For example, display module 11 may include the display device, and processor 12, memory 13, and power module 14 may be provided in the form of a different device from the electronic device 10 that is the display device.

[0401] Figure 13 This is a schematic diagram illustrating one or more suitable embodiments of an electronic device according to the present disclosure.

[0402] refer to Figure 13 Non-limiting examples of suitable electronic devices that utilize one or more of the display devices according to the above embodiments may include electronic devices for displaying images, such as smartphones 10_1a, tablet PCs 10_1b, laptop computers 10_1c, TVs 10_1, desktop monitors 10_1e, etc.; wearable electronic devices including display modules, such as smart glasses 10_2a, head-mounted displays 10_2b, smartwatches 10_2c, etc.; and vehicle electronic devices 10_3 including display modules, such as central information displays (CIDs) arranged on vehicle dashboards, center consoles, instrument panels, etc., interior mirror displays, etc. Electronic devices may include virtual reality glass or augmented reality glass.

[0403] Figure 14 This is a schematic exploded perspective view illustrating one or more embodiments of an electronic device according to the present disclosure.

[0404] According to one or more embodiments, the electronic device may be implemented in the form of a mobile phone (smartphone), tablet computer, PC, etc., and the electronic device includes the aforementioned display device.

[0405] refer to Figure 14 The electronic device may include a window structure (WS), a display panel (DP), and a rear structure (RS).

[0406] The window structure WS can provide an external display surface that can be recognized by the user, such as the viewing surface of a mobile phone, and can include a transparent material film. For example, the window structure WS can include glass (e.g., ultra-thin glass (UTG), hard coating film, plastic film, etc.).

[0407] The outer surface of the window structure WS may include an active region AA and a surrounding region PA. The active region AA can provide a surface from which an image of the display device is substantially displayed, and from which user touches / commands are input. The surrounding region PA may substantially correspond to the bezel area of ​​the display device.

[0408] 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 surrounding area PA of the window structure WS.

[0409] In one or more embodiments, a first functional device region E1 and a second functional device region 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.

[0410] For example, in one or more embodiments, the sensor structure for touch sensing or fingerprint sensing may be arranged in the display panel DP, or between the window structure WS and the display panel DP.

[0411] The rear structure (RS) can be used as a frame structure or housing for a display device or electronic device. A cover plate can be arranged between the rear structure (RS) and the display panel (DP).

[0412] Figure 15 This is a schematic cross-sectional view illustrating an electronic device according to one or more embodiments of the present disclosure.

[0413] Electronic devices can be installed in, embedded in, connected to, or integrated with the vehicle 400. However, the vehicle 400 is not limited to... Figure 15 The embodiments illustrated herein are one or more. Other examples of vehicle 400 may include transportation equipment such as three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, motorcycles, bicycles, trains, etc. Other examples of vehicle 400 may also include electric vehicles, hybrid vehicles, etc.

[0414] refer to Figure 15 At least one of the first to fifth display devices DP1, DP2, DP3, DP4 and DP5 can be applied to the vehicle 400.

[0415] In one or more embodiments, a first display device DP1 may be arranged in cluster area 410. Driving information such as driving distance and speed, as well as one or more suitable warning lights, may be displayed in cluster area 410.

[0416] The second display device DP2 can be mounted on the front windshield (FW) of the vehicle 400. For example, the second display device DP2 can be installed as a head-up display (HUD).

[0417] The third display device DP3 can be arranged on the central panel 420 of the vehicle 400. The central panel 420 can display buttons and / or switches for controlling image display or music player, air conditioner, heater, etc., and can display vehicle information thereon.

[0418] The fourth display device DP4 can be applied to the side mirrors 430 of the vehicle 400. The side mirrors 430 can be installed on each of the two sides (e.g., two opposite 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.

[0419] A fifth display device DP5 may be arranged on the passenger seat instrument panel 440. Information / images that are the same as or different from those displayed on the cluster area 410 and / or the central panel 420 may be displayed on the passenger seat instrument panel 440.

[0420] electronic devices

[0421] The aforementioned light-emitting device ED can be applied to electronic devices and can be used as a light-emitting component or light-emitting unit of electronic devices.

[0422] Electronic devices may include light-emitting devices (EDs) comprising polycyclic compounds of Formula 1, thereby achieving improved color properties, light emission efficiency, and lifespan properties.

[0423] In one or more embodiments, the electronic device may include the aforementioned electronic device.

[0424] Electronic devices may include, for example, video walls, flat panel displays, flexible displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, laser printers, telephones, mobile phones, tablet computers, tablet phones, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicles, video walls including multiple displays spliced ​​together, theater screens, stadium screens, phototherapy devices, and / or signage.

[0425] The polycyclic compounds according to one or more embodiments will be described in more detail below with reference to examples and comparative examples. Examples are provided to aid in understanding this disclosure, but they are provided as non-limiting examples, and the scope of this disclosure is not limited thereto. Those skilled in the art will appreciate that one or more suitable changes and modifications can be made to the disclosed examples within the scope of this disclosure.

[0426] Synthesis Example 1: Synthesis of Compound 13

[0427] Synthesis of intermediate compound 13-a

[0428] Under an argon atmosphere, a reaction solution was prepared by dissolving N1-([1,1'-biphenyl]-3-yl)-5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-tert-phenyl]-2'-yl)phenyl-1,3-diamine (20 g, 22.6 mmol), 4,4'-((5-bromo-1,3-phenylene)bis(oxy))bis(chlorobenzene) (11.1 g, 27.1 mmol), tris(dibenzylideneacetone)palladium (Pd2dba3) (1.0 g, 1.1 mmol), tritert-butylphosphine (P(t-Bu)3)) (0.6 mL, 2.3 mmol) and sodium tert-butoxide (Na tBuO) (4.3 g, 45 mmol) in 300 mL of o-xylene in a 1 L flask. The reaction solution was stirred at 120°C for 2 hours. 4,4'-((5-bromo-1,3-phenylene)bis(oxy))bis(chlorobenzene) is the following compound.

[0429]

[0430] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0431] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 13-a (white solid, 14.0 g, yield 51%).

[0432] Electrospray ionization-liquid chromatography-mass spectrometry (ESI-LCMS): [M]+: C 84 H 74 Cl2N2O2. 1214.43.

[0433] Synthesis of intermediate compound 13-b

[0434] Compound 13-a (13.0 g, 10.7 mmol) was dissolved in 200 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours. After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0435] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 13-b (yellow solid, 2.6 g, yield 20%).

[0436] ESI-LCMS: [M]+: C 84 H 68 B2Cl2N2O2. 1230.00

[0437] Synthesis of Compound 13

[0438] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving compound 13-b (1.0 g, 0.8 mmol), (4-cyanophenyl)boronic acid (0.4 g, 2.4 mmol), Pd2dba3 (0.1 g, 0.1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sphos) (0.1 g, 0.2 mmol), and potassium phosphate (0.4 g, 1.7 mmol) in 20 mL toluene and 2 mL H2O. The reaction solution was stirred at 100 °C for 12 h. After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H2O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0439] The solid obtained therefrom was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 13 (yellow solid, 0.6 g, yield 58%).

[0440] ESI-LCMS: [M]+: C 98 H 76 B2N4O2. 1363.33

[0441] Proton nuclear magnetic resonance spectroscopy ( 1 H-NMR) (CDCl3): = 7.99 (s, 4H), 7.84-7.63 (m,15H), 7.49-7.41 (m, 18H), 7.27-7.19 (m, 3H), 7.08 (m, 8H), 7.06 (s, 2H), 6.58(s, 1H), 1.32 (s, 27H).

[0442] Synthesis Example 2: Synthesis of Compound 12

[0443] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving compound 13-b (1.0 g, 0.8 mmol), (3-cyanophenyl)boronic acid (0.4 g, 2.4 mmol), Pd2dba3 (0.1 g, 0.1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.1 g, 0.2 mmol), and potassium phosphate (0.4 g, 1.7 mmol) in 20 mL toluene and 2 mL H2O. The reaction solution was stirred at 100 °C for 12 hours.

[0444] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0445] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 12 (yellow solid, 0.4 g, yield 40%).

[0446] ESI-LCMS: [M]+: C 98 H 76 B2N4O2. 1363.33

[0447] 1 H-NMR (CDCl3): = 7.99 (s, 4H), 8.02-7.63 (m, 15H), 7.49-7.41 (m,18H), 7.27-7.19 (m, 3H), 7.08 (m, 8H), 7.06 (s, 2H), 6.58 (s, 1H), 1.32 (s,27H).

[0448] Synthesis Example 3: Synthesis of Compound 46

[0449] Synthesis of intermediate compound 46-a

[0450] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving 30 g (40.9 mmol) of 5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)phenyl-1,3-diamine, 3-iodo-1,1'-biphenyl-2,2',3',4,4',5,5',6,6'-d9, 2.4 g (42.9 mmol), Pd2dba3, 2.0 g (2.2 mmol), tritert-butylphosphine, 1.2 mL (4.5 mmol), and sodium tert-butoxide, 5.9 g (61.4 mmol) in 400 mL of o-xylene. The reaction solution was stirred at 120 °C for 2 hours.

[0451] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H2O (1 L) and ethyl acetate (500 mL). The separated organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0452] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 46-a (white solid, 21.9 g, yield 60%).

[0453] ESI-LCMS: [M]+: C 66 H 55 D9N2.894.31

[0454] Synthesis of intermediate compound 46-b

[0455] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N-(3-(([1,1'-biphenyl]-4-yl-d9)oxy)-5-bromophenyl)-5'-chloro-[1,1':3',1''-terphenyl]-2'-amine (35 g, 57.1 mmol), 4-iodo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (24.7 g, 85.6 mmol), Pd2dba3 (2.0 g, 2.2 mmol), tri-tert-butylphosphine (1.2 mL, 4.5 mmol), and sodium tert-butoxide (8.2 g, 85.6 mmol) in 500 mL of o-xylene. The reaction solution was stirred at 120 °C for 2 hours.

[0456] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H2O (1 L) and ethyl acetate (500 mL). The separated organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0457] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 46-b (white solid, 23.4 g, yield 53%).

[0458] ESI-LCMS: [M]+: C 48 H 15 D 18 BrClNO. 773.26

[0459] Synthesis of intermediate compound 46-c

[0460] Under an argon atmosphere, compound 46-a (20.0 g, 22.4 mmol), compound 46-b (22.2 g, 27.1 mmol), Pd2dba3 (1.0 g, 1.1 mmol), tri-tert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were dissolved in 300 mL of o-xylene in a 1 L flask to prepare a reaction solution. The reaction solution was stirred at 120 °C for 2 hours.

[0461] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0462] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 46-c (white solid, 17.0 g, yield 48%).

[0463] ESI-LCMS: [M]+: C 114 H 69 D 27 ClN3O. 1586.66

[0464] Synthesis of intermediate compound 46-d

[0465] Compound 46-c (15.0 g, 9.5 mmol) was dissolved in 200 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0466] Cool the stirred solution to room temperature. Add triethylamine to the cooled solution to terminate the reaction, and remove the solvent under reduced pressure.

[0467] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 46-d (yellow solid, 2.4 g, yield 16%).

[0468] ESI-LCMS: [M]+: C 114 H 66 D 24 B₂ClN₃O. 1599.21

[0469] Synthesis of Compound 46

[0470] Under an argon atmosphere, compound 46-d (1.0 g, 0.6 mmol), (4-cyanophenyl)boronic acid (0.2 g, 0.9 mmol), Pd2dba3 (0.03 g, 0.03 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.03 g, 0.06 mmol), and potassium phosphate (0.3 g, 1.3 mmol) were dissolved in 20 mL of toluene and 2 mL of H2O to prepare a reaction solution. The reaction solution was stirred at 100 °C for 12 hours.

[0471] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0472] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 46 (yellow solid, 0.5 g, 51%).

[0473] ESI-LCMS: [M]+: C 121 H 70 D 24 B2N4O. 1665.88

[0474] 1 H-NMR (CDCl3): = 7.99 (s, 4H), 8.00-7.84 (m, 6H), 7.43-7.41 (m,18H), 7.08 (m, 12H), 7.06 (s, 2H), 6.55 (s, 1H), 1.32 (s, 27H).

[0475] Synthesis Example 4: Synthesis of Compound 47

[0476] Under an argon atmosphere, compound 46-d (1.0 g, 0.6 mmol), (4-cyano-2-methylphenyl)boronic acid (0.2 g, 0.9 mmol), Pd2dba3 (0.03 g, 0.03 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.03 g, 0.06 mmol), and potassium phosphate (0.3 g, 1.3 mmol) were dissolved in 20 mL of toluene and 2 mL of H2O to prepare a reaction solution. The reaction solution was stirred at 100 °C for 12 hours.

[0477] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0478] The solid obtained therefrom was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 47 (yellow solid, 0.4 g, yield 36%).

[0479] ESI-LCMS: [M]+: C 122 H 72 D 24 B2N4O. 1679.90

[0480] 1 H-NMR (CDCl3): = 7.99 (s, 4H), 8.00-7.72 (m, 5H), 7.43-7.41 (m,18H), 7.08 (m, 12H), 7.06 (s, 2H), 6.55 (s, 1H), 2.57 (s, 3H), 1.32 (s, 27H).

[0481] Synthesis Example 5: Synthesis of Compound 34

[0482] Synthesis of intermediate compound 34-a

[0483] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving 5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)phenyl-1,3-diamine (30 g, 40.9 mmol), 1-chloro-3-iodophenyl-2,4,5,6-d4 (11.9 g, 49.1 mmol), Pd2dba3 (2.0 g, 2.2 mmol), tri-tert-butylphosphine (1.2 mL, 4.5 mmol), and sodium tert-butoxide (5.9 g, 61.4 mmol) in 400 mL of o-xylene. The reaction solution was stirred at 120 °C for 2 hours.

[0484] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H2O (1 L) and ethyl acetate (500 mL). The separated organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0485] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 24-a (white solid, 22.5 g, yield 65%).

[0486] ESI-LCMS: [M]+: C 60 H 55 D4ClN2. 847.62

[0487] Synthesis of intermediate compound 34-b

[0488] Under an argon atmosphere, a reaction solution was prepared by dissolving 2-fluoro-5-phenylpyridine (50 g, 289.0 mmol), 3-([1,1'-biphenyl]-4-yloxy)-5-bromophenol (108 g, 317.9 mmol), and cesium carbonate (141.3 g, 433.5 mmol) in 600 mL of dimethylformamide (DMF) in a 1 L flask. The reaction solution was stirred at 150 °C for 5 hours.

[0489] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (2 L). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0490] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 34-b (colorless, transparent, viscous substance, 105.6 g, yield 74%).

[0491] ESI-LCMS: [M]+: C 29 H 20 BrNO2. 494.39

[0492] Synthesis of compound 34-c

[0493] Under an argon atmosphere, compound 34-a (20.0 g, 23.6 mmol), compound 34-b (17.5 g, 35.4 mmol), Pd2dba3 (1.0 g, 1.1 mmol), tri-tert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (3.4 g, 35.4 mmol) were dissolved in 250 mL of o-xylene to prepare a reaction solution. The reaction solution was stirred at 140 °C for 5 hours.

[0494] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H2O (1 L) and ethyl acetate (300 mL).

[0495] The separated organic layer was dried over anhydrous MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0496] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 34-c (white solid, 14.3 g, yield 48%).

[0497] ESI-LCMS: [M]+: C 89 H 74 D4ClN3O2. 1261.10

[0498] Synthesis of intermediate compound 34-d

[0499] Compound 34-c (13.0 g, 10.3 mmol) was dissolved in 200 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0500] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0501] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 34-d (yellow solid, 2.7 g, yield 21%).

[0502] ESI-LCMS: [M]+: C 89 H 69 D3B2ClN3O2. 1275.66

[0503] Synthesis of Compound 34

[0504] Under an argon atmosphere, compound 34-d (2.0 g, 1.5 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.5 g, 3.1 mmol), Pd2dba3 (0.06 g, 0.06 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.06 g, 0.12 mmol), and potassium phosphate (0.6 g, 3.1 mmol) were dissolved in 20 mL of toluene to prepare a reaction solution. The reaction solution was stirred at 100 °C for 12 hours.

[0505] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0506] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 34 (yellow solid, 1.1 g, 52%).

[0507] ESI-LCMS: [M]+: C 101 H 69 D 11 B2N4O2. 1414.46

[0508] 1 H-NMR (CDCl3): = 7.99 (s, 4H), 8.00-7.84 (m, 6H), 7.43-7.41 (m,18H), 7.08 (m, 12H), 7.06 (s, 2H), 6.55 (s, 1H), 1.32 (s, 27H).

[0509] Synthesis Example 6: Synthesis of Compound 18

[0510] Synthesis of intermediate compound 18-a

[0511] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N1-([1,1'-biphenyl]-3-yl)-5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-tert-phenyl]-2'-yl)phenyl-1,3-diamine (20 g, 22.6 mmol), 1-(4-chlorophenoxy)-3-iodo-5-phenoxybenzene (11.4 g, 27.1 mmol), Pd2dba3 (1.0 g, 1.1 mmol), tritert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) in 300 mL of o-xylene. The reaction solution was stirred at 120 °C for 2 hours.

[0512] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0513] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 18-a (white solid, 14.4 g, yield 54%).

[0514] ESI-LCMS: [M]+: C 84 H 75 ClN2O2. 1179.99.

[0515] Synthesis of intermediate compound 18-b

[0516] Compound 18-a (10.0 g, 8.5 mmol) was dissolved in 150 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0517] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0518] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 18-b (yellow solid, 1.8 g, yield 18%).

[0519] ESI-LCMS: [M]+: C 84 H 69 B₂ClN₂O₂. 1195.56

[0520] Synthesis of Compound 18

[0521] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving compound 18-b (1.0 g, 0.8 mmol), (4-cyanophenyl)boronic acid (0.2 g, 1.2 mmol), Pd2dba3 (0.1 g, 0.1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.1 g, 0.2 mmol), and potassium phosphate (0.4 g, 1.7 mmol) in 20 mL of toluene and 2 mL of H2O. The reaction solution was stirred at 100 °C for 12 hours.

[0522] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0523] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 18 (yellow solid, 0.6 g, yield 64%).

[0524] ESI-LCMS: [M]+: C 91 H 73 B2N3O2. 1262.22

[0525] 1H-NMR (CDCl3): = 7.99 (s, 4H), 7.90-7.63 (m, 8H), 7.43-7.41 (m,13H), 7.27-7.19 (m, 3H), 7.08 (m, 8H), 7.06 (s, 2H), 7.00 (d, 1H), 6.58 (s,1H), 1.32 (s,27H).

[0526] Synthesis Example 7: Synthesis of Compound 27

[0527] Synthesis of intermediate compound 27-a

[0528] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N1-([1,1'-biphenyl]-3-yl)-5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-tert-phenyl]-2'-yl)phenyl-1,3-diamine (20 g, 22.6 mmol), 3-(4-(3-([1,1'-biphenyl]-3-yloxy)-5-bromophenoxy)-[1,1'-biphenyl]-3-yl)pyridine (15.4 g, 27.1 mmol), Pd2dba3 (1.0 g, 1.1 mmol), tritert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) in 300 mL of o-xylene. The reaction solution was stirred at 120 °C for 2 hours.

[0529] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0530] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 27-a (white solid, 26.1 g, yield 43%).

[0531] ESI-LCMS: [M]+: C 101 H 87 N3O2. 1374.83.

[0532] Synthesis of Compound 27

[0533] Compound 27-a (20.0 g, 14.5 mmol) was dissolved in 300 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0534] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0535] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 27 (yellow solid, 1.8 g, yield 9%).

[0536] ESI-LCMS: [M]+: C 101 H 81 B2N3O2. 1390.40

[0537] 1 H-NMR (CDCl3): = 9.24 (s, 1H), 8.70 (dd, 1H), 8.42 (dd, H), 7.99-7.97 (m, 5H), 7.90 (d, 2H), 7.75-7.57 (m, 8H), 7.49-7.41 (m, 23H), 7.33 (s,1H), 7.27 (d, 1H), 7.09-7.06 (m, 10H), 1.32 (s, 27H).

[0538] Synthesis Example 8: Synthesis of Compound 32

[0539] Synthesis of intermediate compound 32-c

[0540] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N1-([1,1':3',1''-terphenyl]-2'-yl)-5-(tert-butyl)-N3-(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)-N1-(3-chlorophenyl)benzene-1,3-diamine (20.0 g, 25.4 mmol) as compound 32-a, 2-(3-([1,1'-biphenyl]-4-yloxy)-5-bromophenoxy)-5-phenylpyridine (18.8 g, 18.8 g) as compound 32-b, Pd2dba3 (1.0 g, 1.1 mmol), tritert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (3.6 g, 38.1 mmol) in 250 mL of o-xylene. The reaction solution was stirred at 140 °C for 5 hours.

[0541] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0542] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 32-c (white solid, 15.8 g, yield 52%).

[0543] ESI-LCMS: [M]+: C 85 H 70 ClN3O2. 1200.96

[0544] Synthesis of intermediate compound 32-d

[0545] Compound 32-c (10.0 g, 8.3 mmol) was dissolved in 200 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0546] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0547] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 32-d (yellow solid, 2.0 g, yield 20%).

[0548] ESI-LCMS: [M]+: C 85H 64 B₂ClN₃O₂. 1216.54

[0549] Synthesis of Compound 32

[0550] Under an argon atmosphere, a reaction solution was prepared by dissolving compound 32-d (1.5 g, 1.2 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.4 g, 2.4 mmol), Pd2dba3 (0.06 g, 0.06 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.06 g, 0.12 mmol), and potassium phosphate (0.6 g, 3.1 mmol) in 20 mL of toluene in a 1 L flask. The reaction solution was stirred at 100 °C for 12 hours.

[0551] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0552] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 32 (yellow solid, 0.8 g, 55%).

[0553] ESI-LCMS: [M]+: C 97 H 64 D8B2N4O2. 1355.34

[0554] 1 H-NMR (CDCl3): = 8.20 (d, 2H), 7.99-7.97 (m, 3H), 7.85-7.75 (m,4H), 7.67-7.63 (m, 2H), 7.51-7.39 (m, 21H), 7.23 (s, 1H), 7.19 (d, 1H), 7.08-7.06 (m, 10H), 1.32 (s, 18H).

[0555] Synthesis Example 9: Synthesis of Compound 63

[0556] Synthesis of intermediate compound 63-c

[0557] Under an argon atmosphere, in a 1 L flask, 5-(tert-butyl)-N1,N3-bis(5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-yl)-N1-(3-chlorophenyl)phenyl-1,3-diamine (20.0 g, 23.7 mmol) as compound 63-a, N-(3-([1,1'-biphenyl]-4-yloxy)-5-bromophenyl)-N-(3'-fluoro-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (26.3 g, 35.6 mmol) as compound 63-b, Pd2dba3 (1.0 g, 1.1 mmol), tritert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added. The mmol) was dissolved in 300 mL of o-xylene to prepare the reaction solution. The reaction solution was stirred at 140 °C for 5 hours.

[0558] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0559] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 63-c (white solid, 14.5 g, yield 41%).

[0560] ESI-LCMS: [M]+: C 108 H 91 ClFN3O. 1501.38

[0561] Synthesis of intermediate compound 63-d

[0562] Compound 63-c (10.0 g, 6.7 mmol) was dissolved in 150 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0563] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0564] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 63-d (yellow solid, 1.9 g, yield 19%).

[0565] ESI-LCMS: [M]+: C 108 H 85 B₂ClFN₃O. 1516.96

[0566] Synthesis of Compound 63

[0567] Under an argon atmosphere, a reaction solution was prepared by dissolving compound 63-d (1.5 g, 1.0 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.4 g, 2.0 mmol), Pd2dba3 (0.06 g, 0.06 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.06 g, 0.12 mmol), and potassium phosphate (0.6 g, 3.1 mmol) in 20 mL of toluene in a 1 L flask. The reaction solution was stirred at 100 °C for 12 hours.

[0568] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0569] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 63 (yellow solid, 1.0 g, 62%).

[0570] ESI-LCMS: [M]+: C 120 H 85 D8B2FN4O. 1655.76

[0571] 1 H-NMR (CDCl3): = 8.20 (d, 2H), 7.99 (s, 4H), 7.90 (d, 1H), 7.85(d, 1H), 7.75-7.63 (m, 6H), 7.52-7.39 (m, 26H), 7.28 (d, 1H), 7.27 (d, 1H), 7.23 (d, 1H), 7.22 (dd, 1H), 7.08-7.06 (m, 14H), 6.55 (s, 1H), 1.32 (s, 27H).

[0572] Synthesis Example 10: Synthesis of Compound 84

[0573] Synthesis of intermediate compound 84-c

[0574] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N1,N3-bis([1,1':3',1''-terphenyl]-4'-yl)-5-(tert-butyl)-N1-(3-chlorophenyl)benzene-1,3-diamine (20.0 g, 27.3 mmol) as compound 84-a, 4'-(3-([1,1'-biphenyl]-2-yl([1,1'-biphenyl]-3-yl)amino)-5-bromophenoxy)-[1,1'-biphenyl]-3-carboxynitrile (27.4 g, 41.0 mmol), Pd2dba3 (1.0 g, 1.1 mmol), tritert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) in 300 mL of o-xylene. The reaction solution was stirred at 140 °C for 5 hours.

[0575] The organic layer was extracted and separated from the stirred solution using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0576] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 84-c (white solid, 13.7 g, yield 38%).

[0577] ESI-LCMS: [M]+: C 95 H 71 ClN4O. 1320.09

[0578] Synthesis of intermediate compound 84-d

[0579] Compound 84-c (10.0 g, 7.6 mmol) was dissolved in 150 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0580] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0581] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 84-d (yellow solid, 1.1 g, yield 11%).

[0582] ESI-LCMS: [M]+: C 95 H 65 B2ClN4O. 1335.66

[0583] Synthesis of Compound 84

[0584] Under an argon atmosphere, a reaction solution was prepared by dissolving compound 84-d (1.0 g, 0.6 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.2 g, 1.4 mmol), Pd2dba3 (0.06 g, 0.06 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.06 g, 0.12 mmol), and potassium phosphate (0.6 g, 3.1 mmol) in 20 mL of toluene in a 1 L flask. The reaction solution was stirred at 100 °C for 12 hours.

[0585] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0586] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 84 (yellow solid, 0.3 g, 39%).

[0587] ESI-LCMS: [M]+: C 107 H 65 D8B2N5O. 1474.46

[0588] 1 H-NMR (CDCl3): = 8.10 (dd, 1H), 8.02 (dd, 1H), 7.90-7.65 (m, 18H), 7.49-7.41 (m, 21H), 7.27-7.08 (m, 12H), 6.55 (s, 1H), 1.32 (s, 9H).

[0589] Synthesis Example 11: Synthesis of Compound 96

[0590] Synthesis of intermediate compound 96-c

[0591] Under an argon atmosphere, a reaction solution was prepared in a 1 L flask by dissolving N1-([1,1'-biphenyl]-3-yl)-5-(tert-butyl)-N1,N3-bis(dibenzo[b,d]thiophene-3-yl)phenyl-1,3-diamine (15.0 g, 22.1 mmol) as compound 96-a, 3-(3-bromo-5-(3-chlorophenoxy)phenoxy)-1,1'-biphenyl (14.9 g, 33.1 mmol) as compound 96-b, Pd2dba3 (1.0 g, 1.1 mmol), tri-tert-butylphosphine (0.6 mL, 2.3 mmol), and sodium tert-butoxide (3.2 g, 33.1 mmol) in 250 mL of o-xylene. The reaction solution was stirred at 140 °C for 5 hours.

[0592] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0593] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 96-c (white solid, 13.2 g, yield 57%).

[0594] ESI-LCMS: [M]+: C 70 H 51 ClN2O2S2. 1051.76

[0595] Synthesis of intermediate compound 96-d

[0596] Compound 96-c (10.0 g, 9.5 mmol) was dissolved in 150 mL of o-dichlorobenzene in a 1 L flask under an argon atmosphere, and BBr3 (3.0 equivalents) was added to prepare a reaction solution. The reaction solution was stirred at 140 °C for 12 hours.

[0597] After cooling the stirred solution to room temperature, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure.

[0598] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain intermediate compound 96-d (yellow solid, 1.8 g, yield 18%).

[0599] ESI-LCMS: [M]+: C 70 H 45B₂ClN₂O₂S₂. 10⁶⁷.3³

[0600] Synthesis of Compound 96

[0601] Under an argon atmosphere, a reaction solution was prepared by dissolving compound 96-d (1.0 g, 0.9 mmol), 9H-carbazole-3-carboxynitrile (0.3 g, 1.4 mmol), Pd2dba3 (0.06 g, 0.06 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.06 g, 0.12 mmol), and potassium phosphate (0.6 g, 3.1 mmol) in 20 mL of toluene in a flask. The reaction solution was stirred at 100 °C for 12 hours.

[0602] After cooling the stirred solution to room temperature, the organic layer was extracted and separated using H₂O (1 L) and ethyl acetate (300 mL). The separated organic layer was dried over anhydrous MgSO₄ and filtered. The solvent was removed from the filtered solution under reduced pressure.

[0603] The obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 96 (yellow solid, 0.5 g, 51%).

[0604] ESI-LCMS: [M]+: C 83 H 52 B2N4O2S2.1223.10

[0605] 1 H-NMR (CDCl3): = 8.55 (dd, 1H), 8.45 (dd, 2H), 8.01-7.75 (m, 14H), 7.64 (d, 2H), 7.49-7.33 (m, 18H), 7.27 (d, 1H), 7.16 (ddd, 1H), 7.11 (d, 1H), 7.06 (s, 1H), 6.58 (s, 1H), 1.32 (s, 9H).

[0606] Manufacturing of light-emitting devices

[0607] As the first electrode, a 15 Ω / cm electrode is formed on it. 2The 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 with isopropanol and then with pure water for 5 minutes. 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.

[0608] Subsequently, NPB (N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine) was deposited on the first electrode to form a hole injection layer with a thickness of 300 Å. HT-13 was then deposited on the hole injection layer to form a hole injection layer with a thickness of 200 Å. A hole transport layer of thickness of 100 Å was formed. CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) was deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0609] A bulk mixture of PH-13 and ET-16 in a weight ratio of 1:1; PD1-13; and one of the compounds from the examples or comparative examples were co-deposited on an electron blocking layer in a weight ratio of 85:14:1 to form an emission layer with a thickness of 200 Å.

[0610] TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide) was deposited on the emitter layer to form an electron transport layer with a thickness of 200 Å. Subsequently, TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene) was deposited on the electron transport layer to form a buffer layer with a thickness of 300 Å, and then LiF was deposited on the buffer layer to form an electron injection layer with a thickness of 10 Å. Al was then deposited on the electron injection layer to form a second electrode with a thickness of 3000 Å, and then HT-7 was deposited on the second electrode to form a capping layer with a thickness of 700 Å, thereby fabricating the light-emitting device. Each layer was formed by vacuum deposition.

[0611] As shown below, commercially available products purified by sublimation are used in the manufacture of the device.

[0612]

[0613] Evaluation example

[0614] Evaluation Example 1. Evaluation of the properties of polycyclic compounds

[0615] The properties of the compounds in the examples and comparative examples shown below were evaluated.

[0616] Compounds in the Examples

[0617] Comparative compound

[0618] The HOMO energy level (eV) was measured using Smart Manager software on an SP2 electrochemical workstation manufactured by ZIVE LAB.

[0619] The absolute value (ΔEst) of the energy difference between the lowest singlet excited state (S1 level) and the lowest triplet excited state (T1 level), and the maximum emission wavelength.

[0620] The lowest triplet excitation level (T1 level), the lowest singlet excitation level (S1 level), and the maximum emission wavelength (nm) were measured using a HORIBA fluoroMax+ spectrometer equipped with a xenon light source and monochromator and FluorEssence software.

[0621] The absolute value of the difference between the lowest singlet excited state level (S1 level) and the lowest triplet excited state level (T1 level) was calculated.

[0622] The evaluation results are shown in Table 1.

[0623] Table 1

[0624] Referring to Table 1, the polycyclic compounds according to one or more embodiments of this disclosure are each evaluated to have a deep HOMO level, a small ΔEst, and a maximum emission wavelength of 445 nm to 465 nm. The polycyclic compounds according to one or more embodiments of this disclosure are evaluated to have an even deeper HOMO level while inducing a short-wavelength effect.

[0625] The polycyclic compounds in Comparative Examples 1, 2, and 3 were each evaluated as having shallow HOMO energy levels.

[0626] The polycyclic compounds in Comparative Examples 5 and 6 were each evaluated as having shallow HOMO energy levels and large ΔEst.

[0627] According to Comparative Example 7, the polycyclic compound was evaluated to have a large ΔEst.

[0628] The polycyclic compounds in Comparative Examples 4, 8, and 9 were each evaluated to have shallow HOMO energy levels, large ΔEst, and a maximum emission wavelength greater than 480 nm (green emission region).

[0629] Evaluation Example 2. Performance Evaluation of Light-Emitting Devices

[0630] Using the V7000 OLED IVL testing system (Polaronix) at 10 mA / cm² 2 The properties of each light-emitting device manufactured as described above were measured at a current density of 10 mA / cm². 2 The light-emitting device was continuously driven at a current density, and the time until the brightness decreased to 95% of the initial value was measured. The relative value of the time measured in the light-emitting device using the compound of Comparative Example 1 is expressed as the lifetime (T95) of each light-emitting device.

[0631] Table 2

[0632] Referring to Table 2, in one or more embodiments of the light-emitting device according to this disclosure, the intramolecular electron mobility (charge transfer, CT) of the polycyclic compound is improved, thereby improving the front efficiency, and the oxidation of the polycyclic compound is suppressed or reduced, thereby improving the lifetime properties.

[0633] In the light-emitting device according to the comparative example, the front efficiency was reduced to 455 (cd / A / y) or less than 455 (cd / A / y), and the lifespan (T95) was evaluated as 1 or less.

[0634] In this disclosure, it should be understood that if an element (or region, layer, portion, etc.) is referred to as being "on" or "connected" to another element (e.g., when an element (or region, layer, portion, etc.) is referred to as being "on" or "connected" to another element), it may be directly disposed on or connected to the other element, or an intermediate element may be disposed therebetween. Conversely, "directly on" can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other components. For example, "directly on" can mean that two layers or two components are disposed without the use of additional components, such as adhesive components, between them.

[0635] As used herein, the terms “and / or” or “or” can include any combination and all combinations of one or more of the items in the relevant list. Expressions such as “at least one of…”, “one of…”, and “selected from” modify the entire list of elements when preceding it, and do not modify any individual element in the list. For example, “at least one of a, b, and c”, “selected from at least one of a, b, and c”, and “selected from at least one of a through c” can mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variations thereof. The “ / ” used herein may be interpreted as “and” or “or” depending on the context.

[0636] It should be understood that although the terms “first,” “second,” etc., may be used herein to describe one or more suitable elements, components, areas, layers, and / or portions, these elements, components, areas, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, area, layer, or portion from another element, component, area, layer, or portion. Therefore, without departing from the scope of this disclosure, the first element, first component, first area, first layer, or first portion discussed herein may be referred to as a second element, second component, second area, second layer, or second portion, respectively. Similarly, the second element, second component, second area, second layer, or second portion may be referred to as a first element, first component, first area, first layer, or first portion, respectively. As used herein, the singular forms “a,” “an,” “one,” and “the” are intended to also include the plural forms unless the context clearly indicates otherwise. Furthermore, the use of “may” when describing embodiments of this disclosure means “one or more embodiments of this disclosure.”

[0637] It should be further understood that if the terms “comprise(s)”, “include(s)”, and / or “have(has)” are used in this disclosure (e.g., when the terms “comprise(s)”, “include(s)”, and / or “have(has)” are used in this disclosure), then the terms “comprise(s)”, “include(s)”, and / or “have(has)” indicate the presence of the specified feature, integer, step, operation, element, component, and / or group thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. Additionally, the terms “comprise(s)”, “include(s)”, “have(s)”, “has(s)”, or other similar terms include or support the terms “composed of” and “substantially composed of”, indicating the presence of the specified feature, integer, step, operation, element, and / or component, while other features, integers, steps, operations, elements, components, and / or groups thereof are absent or substantially absent.

[0638] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be further understood that terms (e.g., those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and should not be interpreted in an idealized or overly formal sense, unless expressly defined herein.

[0639] As used herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation rather than as terms of degree, and are intended to explain the inherent bias in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. As used herein, “about” includes a specified value and means within an acceptable range of deviation from a particular value, as determined by one of ordinary skill in the art considering the relevant measurement and the error associated with the measurement of the particular quantity (i.e., the limits of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the specified value.

[0640] In the context of this application, and unless otherwise defined, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0641] Any numerical ranges listed herein are intended to include all subranges of the same numerical precision falling within the listed range. For example, the range “1.0 to 10.0” is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this disclosure (including the claims) to expressly list any subranges falling within the scope expressly listed herein.

[0642] The light-emitting devices, display devices / apparatus, electronic devices / apparatus, means for manufacturing them, or any other related devices / apparatus or components according to embodiments of the present disclosure described herein can be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, various components of the device can be formed on an integrated circuit (IC) chip or on separate IC chips. Furthermore, various components of the device can be implemented on flexible printed circuit films, tape-and-carrier packages (TCPs), printed circuit boards (PCBs), or formed on a substrate. Additionally, various components of the device can be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions, and interacting with other system components for performing the various functions described herein. The computer program instructions are stored in memory, which can be implemented in the computing device using standard memory devices such as random access memory (RAM). The computer program instructions can also be stored in other non-transitory computer-readable media, such as CD-ROMs, flash drives, etc. Furthermore, those skilled in the art will recognize that, without departing from the scope of embodiments of this disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed across one or more other computing devices.

[0643] In this disclosure, each suitable feature of the various embodiments of this disclosure may be combined or partially or completely combined with each other, and may be technically interlocked and operated in various suitable ways, and each embodiment may be implemented independently of each other or in combination with each other in any suitable way, unless otherwise stated or implied.

[0644] Although one or more embodiments of this disclosure have been described, it should be understood that this disclosure is not intended to be limited to these embodiments, and that one or more suitable changes and modifications may be made by those skilled in the art within the spirit and scope of this disclosure as claimed in the appended claims.

[0645] Therefore, the technical scope of this disclosure is not intended to be limited to what is set forth in the detailed description of this disclosure, but is intended to be defined by the appended claims and their equivalents.

Claims

1. Polycyclic compounds represented by chemical formula 1: Chemical Formula 1 ， in, In chemical formula 1, X1 and X2 are each independently N(R) 17 ), S, O or Se, Y1 to Y 13 Each is either C or N independently. R1 to R 13 and R 17 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 Two adjacent groups in the ring may optionally bond to each other to form a saturated ring. The electron-withdrawing group is a group having a para-Hammett substituent constant greater than 0 according to the Hammett rule. n is 0 or 1 independently each time it appears. R 14 To R 16 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, Ar1 and Ar2 are independently substituted or unsubstituted C6-C. 60 The aryl group is either substituted or unsubstituted C2-C. 60 heteroaryl groups, Selected from Y1 to Y 13 At least one of them is N; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group; or is selected from Y1 to Y... 13 At least one of them is N, selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group, and When the number of electron-withdrawing groups and / or the number of groups replaced by electron-withdrawing groups are each two or more, the electron-withdrawing groups are the same or different from each other, and / or the groups replaced by electron-withdrawing groups are the same or different from each other.

2. The polycyclic compound of claim 1, wherein the electron-withdrawing group is selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C2-C with depleted π electrons 30 Cyclic groups, and R 18 To R 21 Each is independently either substituted or unsubstituted C1-C 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

3. The polycyclic compound of claim 1, wherein R 14 To R 16 It is not an electron-withdrawing group, nor is it a group that has been replaced by an electron-withdrawing group.

4. The polycyclic compound of claim 1, wherein R 14 To R 16 It is not an electron-donating group, nor is it a group substituted by an electron-donating group, and The electron-donating group is a group having a substituent constant of less than -0.23 according to the Hammett rule.

5. The polycyclic compound of claim 4, wherein the electron-donating group is -NH2, -NH(R) 22 ), -N(R 23 (R) 24 -OR 25 Or C3-C rich in π electrons 30 Cyclic groups, and R 22 To R 25 Each is independently either substituted or unsubstituted C1-C 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 Aryl group.

6. The polycyclic compound of claim 1, wherein: At least one of Y2 to Y9 is N; At least one of R2 to R9 is an electron-withdrawing group; At least one of R2 to R9 is a group substituted by an electron-withdrawing group; At least one selected from Y2 to Y9 is N, and at least one selected from R2 to R9 is an electron-withdrawing group; At least one selected from Y2 to Y9 is N, and at least one selected from R2 to R9 is a group substituted by an electron-withdrawing group; At least one selected from R2 to R9 is an electron-withdrawing group, and at least one of the remaining selected from R2 to R9 is a group substituted by an electron-withdrawing group; or At least one selected from Y2 to Y9 is N, and at least one selected from R2 to R9 is an electron-withdrawing group, and at least one of the remaining selected from R2 to R9 is a group substituted by an electron-withdrawing group.

7. The polycyclic compound of claim 1, wherein the polycyclic compound is represented by any one of formulas 1-1 to 1-4: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 ,as well as in, In chemical formulas 1-1 to 1-4, X1 and X2 are each independently N(R) 17 ) or O, Y2, Y3, Y5, Y6, Y8, Y9, Y 10 Y 11 and Y 13 Each is either C or N independently. R1 to R 13 and R 17 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 The two adjacent groups in the structure are not bonded to each other. n is 0 or 1 independently each time it appears. R 14 To R 16 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, m1 is an integer from 0 to 5 each time it appears. Single or multiple R a Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups, substituted or unsubstituted C5-C 30 Cycloalkenyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl groups, or substituted or unsubstituted C8-C 30 Fused polycyclic groups, and When R a When the number is 2 or greater than 2, then it is selected from the plurality of R. a Two adjacent groups in the ring may optionally combine with each other to form a saturated or unsaturated ring.

8. The polycyclic compound of claim 1, wherein the compound is selected from R1 to R2. 13 and R 17 At least one of the groups is selected from any one of the groups represented by chemical formulas 2-1 to 2-25: (2-1) (2-2) (2-3) (2-4) (2-5) (2-6) (2-7) (2-8) (2-9) (2-10) (2-11) (2-12) (2-13) (2-14) (2-15) (2-16) (2-17) (2-18) (2-19) (2-20) (2-21) (2-22) (2-23) (2-24) (2-25), and in, In chemical formulas 2-1 to 2-25, 'o' is an integer from 0 to 2 each time it appears. - indicates the binding site. Single or multiple R EWG Each is independently selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, -NO2 and nitrogen-containing C3-C with depleted π electrons 30 Cyclic groups, R 18 To R 21 Each is independently either substituted or unsubstituted C1-C 30 Alkyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups or substituted or unsubstituted C6-C 30 aryl group, m1 is an independent integer from 0 to 5 each time it appears, m2 is an independent integer from 0 to 4 each time it appears, and m3 is an independent integer from 0 to 3 each time it appears. Single or multiple R b Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 aryl groups, and When R b When the number is 2 or greater than 2, then multiple R b They are the same as or different from each other, and are selected from the plurality of R. b Two adjacent groups in the ring may optionally combine with each other to form a saturated or unsaturated ring.

9. The polycyclic compound of claim 1, wherein Ar1 and Ar2 are each independently represented by a group selected from any one of chemical formulas 3-1 to 3-12: (3-1)(3-2)(3-3) (3-4)(3-5)(3-6) (3-7)(3-8)(3-9) (3-10)(3-11)(3-12)， in, In chemical formulas 3-1 to 3-12, m1 is an independent integer from 0 to 5 each time it appears, m2 is an independent integer from 0 to 4 each time it appears, and m3 is an independent integer from 0 to 3 each time it appears. - indicates the binding site. Single or multiple R c Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, or substituted or unsubstituted C6-C 10 aryl group, When containing multiple R c When, then the multiple R c They are the same as or different from each other, and are selected from the plurality of R. c Two adjacent groups in the ring may optionally combine with each other to form a saturated or unsaturated ring, and Among them, in chemical formulas 3-9 to 3-11, - The binding site is one of the carbons designated as numbers 1 to 4, and in chemical formulas 3-12. - The binding site is one of the carbons designated as numbers 1 to 3.

10. The polycyclic compound of claim 8, wherein: R 17 It is a group represented by any one of the chemical formulas 2-14 to 2-25; R 12 It is a group represented by any one of chemical formulas 2-2, 2-3, and 2-8 to 2-12; or R 17 It is a group represented by any one of chemical formulas 2-14 to 2-25, and R 12 It is represented by any one of the chemical formulas 2-2, 2-3, and 2-8 to 2-12.

11. The polycyclic compound of claim 9, wherein Ar1 and Ar2 are each independently represented by a group selected from any one of chemical formulas 3-5 to 3-12.

12. The polycyclic compound of claim 11, wherein Ar1 and Ar2 are each independently represented by groups of chemical formulas 3-5.

13. The polycyclic compound of claim 1, wherein the electron-withdrawing group is selected from -F, -Cl, -Br, -I, -CF3, -COR 18 -CO2R 19 -SOR 20 -SO2R 21 -CN, -SCN, substituted or unsubstituted triazine group, substituted or unsubstituted thiazole group, substituted or unsubstituted benzothiazole group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted naphthidine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazoline group, substituted or unsubstituted benzo[a]cenline group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group, and R 18 To R 21 Each is independently either substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups or substituted or unsubstituted C6-C 10 Aryl group.

14. A light-emitting device, comprising: First electrode; Second electrode; as well as An emission layer, situated between the first electrode and the second electrode, comprises a polycyclic compound represented by Formula 1: Chemical Formula 1 ， In chemical formula 1, X1 and X2 are each independently N(R) 17 ), S, O or Se, Y1 to Y 13 Each is either C or N independently. R1 to R 13 and R 17 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 Two adjacent groups in the ring may optionally bond to each other to form a saturated ring. The electron-withdrawing group is a group having a para-Hammett substituent constant greater than 0.05 according to the Hammett rule. n is 0 or 1 independently each time it appears. R 14 To R 16 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, Ar1 and Ar2 are independently substituted or unsubstituted C6-C. 60 The aryl group is either substituted or unsubstituted C2-C. 60 heteroaryl groups, Selected from Y1 to Y 13 At least one of them is N; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group; or is selected from Y1 to Y... 13 At least one of them is N, selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group, and When the number of electron-withdrawing groups and / or the number of groups replaced by electron-withdrawing groups are each two or more, the electron-withdrawing groups are the same or different from each other, and / or the groups replaced by electron-withdrawing groups are the same or different from each other.

15. The light-emitting device of claim 14, further comprising a charge-generating layer between the first electrode and the second electrode. The emitting layer comprises multiple emitting layers, and the charge generating layer is located between adjacent emitting layers. At least one of the plurality of emitter layers contains the polycyclic compound represented by chemical formula 1.

16. The light-emitting device of claim 14, wherein the polycyclic compound is included as a thermally activated delayed fluorescence dopant or as a host for a phosphorescent dopant.

17. The light-emitting device of claim 14, wherein the emitting layer is designed to emit blue light having a maximum emission wavelength of 440 nm to 480 nm.

18. The light-emitting device of claim 14, wherein the polycyclic compound is represented by any one selected from chemical formulas 1-1 to 1-4: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 ,as well as in, In chemical formulas 1-1 to 1-4, X1 and X2 are each independently N(R) 17 ) or O, Y2, Y3, Y5, Y6, Y8, Y9, Y 10 Y 11 and Y 13 Each is either C or N independently. R1 to R 13 and R 17 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 The two adjacent groups in the structure are not bonded to each other. n is 0 or 1 independently each time it appears. R 14 To R 16 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, m1 is an integer from 0 to 5 each time it appears. Single or multiple R a Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 30 Cycloalkyl groups, substituted or unsubstituted C5-C 30 Cycloalkenyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 30 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl groups, or substituted or unsubstituted C8-C 30 Fused polycyclic groups, and When R a When the number is 2 or greater than 2, then it is selected from the plurality of R. a Two adjacent groups in the ring may optionally combine with each other to form a saturated or unsaturated ring.

19. An electronic device including a light-emitting device, wherein: The light-emitting device includes: First electrode; Second electrode; and An emission layer, situated between the first electrode and the second electrode, comprises a polycyclic compound represented by Formula 1: Chemical Formula 1 ， In chemical formula 1, X1 and X2 are each independently N(R) 17 ), S, O or Se, Y1 to Y 13 Each is either C or N independently. R1 to R 13 and R 17 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups, substituted or unsubstituted silyl groups, or electron-withdrawing groups, and selected from R2 to R3. 13 Two adjacent groups in the ring may optionally bond to each other to form a saturated ring. The electron-withdrawing group is a group having a para-Hammett substituent constant greater than 0.05 according to the Hammett rule. n is 0 or 1 independently each time it appears. R 14 To R 16 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 60 Cycloalkyl groups, substituted or unsubstituted C5-C 60 Cycloalkenyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thiols, substituted or unsubstituted C8-C 60 Fused polycyclic groups or substituted or unsubstituted silyl groups, Ar1 and Ar2 are independently substituted or unsubstituted C6-C. 60 The aryl group is either substituted or unsubstituted C2-C. 60 heteroaryl groups, and Selected from Y1 to Y 13 At least one of them is N; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group; selected from Y1 to Y 13 At least one of them is N, and is selected from R1 to R 13 and R 17 At least one of them is a group substituted with an electron-withdrawing group; selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group substituted with an electron-withdrawing group; or is selected from Y1 to Y... 13 At least one of them is N, selected from R1 to R 13 and R 17 At least one of them is an electron-withdrawing group, and is selected from R1 to R2. 13 and R 17 At least one of the remaining groups is a group that has been replaced by an electron-withdrawing group.

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

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