Polycyclic compound, light emitting element and electronic device

Abstract

A polycyclic compound represented by chemical formula 1 or 2 is provided. A light-emitting element comprising said polycyclic compound and an electronic device comprising said light-emitting element are provided. [[Chemical Formula 1] [Chemical Formula 2]

Description

Technology Field

[0001] The embodiments of the present application relate to polycyclic compounds, light-emitting elements, and electronic devices. Background Technology

[0003] Organic light-emitting diodes possess self-luminous characteristics and can provide enhanced viewing angle and contrast characteristics. In addition, they can provide high response speed and high brightness.

[0004] It may include a light-emitting layer disposed between a first electrode and a second electrode. Holes moved from the first electrode and electrons moved from the second electrode may recombine in the light-emitting layer to generate excitons. As the excitons change from an excited state to a ground state, light emission characteristics are realized. The problem to be solved

[0006] One objective of the present disclosure is to provide a polycyclic compound having improved driving voltage, luminous efficiency, and lifespan characteristics.

[0007] One objective of the present disclosure is to provide a light-emitting element having improved driving voltage, luminous efficiency, and lifespan characteristics.

[0008] One objective of the present disclosure is to provide an electronic device having improved driving voltage, luminous efficiency, and lifespan characteristics. means of solving the problem

[0010] Polycyclic compounds according to the embodiments of the present disclosure are represented by the following formula 1 or formula 2.

[0011] [Chemical Formula 1]

[0012]

[0013] [Chemical Formula 2]

[0014]

[0015] In the above chemical formulas 1 and 2, Z1 to Z 10Each is independently hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C7-C 60 arylalkyl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C3-C 60 heteroarylalkyl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 It is a condensed polycyclic group, or a substituted or unsubstituted silyl group, and two or more adjacent groups among these may optionally combine to form a saturated or unsaturated ring, and Z1 to Z 10 At least one of them is selected from a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group and a substituted or unsubstituted carbazole group, and at least one of the remainder is an electron-withdrawing group or a group substituted with an electron-withdrawing group, wherein the electron-withdrawing group is a group in which the para Hammett substituent constant (σp) is greater than 0.

[0016] A light-emitting element according to embodiments of the present disclosure comprises a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises one or more light-emitting structures including a hole transport region, a light-emitting layer, and an electron transport region, and the hole transport region comprises the polycyclic compound described above.

[0017] In some embodiments, the intermediate layer comprises two or more of the light-emitting structures, and one or more of the hole transport regions may comprise the polycyclic compound.

[0018] In some embodiments, the hole transport region includes a hole injection layer, and the hole injection layer may include the polycyclic compound.

[0019] An electronic device according to embodiments of the present disclosure includes the light-emitting element described above. Effects of the invention

[0021] Polycyclic compounds according to the embodiments of the present disclosure can achieve improved driving voltage, enhanced luminous efficiency, and lifetime characteristics.

[0022] A light-emitting element according to the embodiments of the present disclosure and an electronic device including the same can achieve improved driving voltage, improved luminous efficiency, and lifespan characteristics. Brief explanation of the drawing

[0024] FIGS. 1 to 6 are schematic cross-sectional views showing light-emitting elements according to exemplary embodiments. FIG. 7 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 8 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 9 is a schematic cross-sectional view showing a stacked form of a light-emitting structure in a display device according to exemplary embodiments. FIG. 10 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 11 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 12 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 13 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 14 is a block diagram of an electronic device according to one embodiment. FIGS. 15 and 16 are schematic diagrams of electronic devices according to various embodiments. Specific details for implementing the invention

[0025] According to the present disclosure, a polycyclic compound may include one or more groups comprising two or more benzene rings capable of protecting the core, thereby inhibiting or preventing interactions with surrounding compounds. The polycyclic compound may not form by-products, such as charge transfer complexes, through unnecessary reactions with surrounding compounds, and thus may not be consumed as by-products, and may achieve enhanced stability.

[0026] Accordingly, the above polycyclic compound can have deep LUMO energy levels, high hole mobility, low electron mobility, and a high glass transition temperature.

[0027] According to the present disclosure, a light-emitting element comprising the polycyclic compound and an electronic device comprising the same are provided. The light-emitting element to which the polycyclic compound is applied and the electronic device comprising the same can achieve high luminous efficiency and improved lifetime characteristics at a low driving voltage.

[0028] Definition of Terms

[0029] In this specification, "substituted or unsubstituted" refers, for example, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group (for example, C1-C 60 , C1-C 10 alkyl groups), alkenyl groups (e.g., C2-C 60 , C2-C 10 alkenyl group), alkenyl group (e.g., C2-C 60 , C2-C 10 alkynyl group), alkoxy group (e.g., C1-C 60 , 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 It may refer to one that is substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups. For example, "substituted alkyl group" may refer to one in which at least one of the hydrogen atoms of the alkyl group is substituted with the substituent described above, thereby further bonding a substituent to a carbon atom of the alkyl group.

[0030] The above substituent may include a combination selected from the groups described above. For example, at least one of the hydrogen atoms included as a substituent, such as an alkyl group or an aryl group, may be substituted with a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, or a heterocyclic group.

[0031] Among the above substituents, multivalent substituents such as amino groups, phosphine sulfide groups, phosphine oxide groups, sulfinyl groups, sulfonyl groups, oxy groups, carbonyl groups, and ester groups are C1-C 10 alkyl group of, C1-C 10alkenyl group of, C1-C 10 The alkynyl group or C6-C 10 It can be replaced by an aryl group.

[0032] The term "substituted or unsubstituted C" as used in this specification a -C b In the "Y period of", C a -C b refers to the number of carbon atoms of the unsubstituted Y group, and does not include the number of carbon atoms of the substituent.

[0033] An alkyl group refers to a monovalent hydrocarbon group from which one hydrogen atom has been removed from a straight-chain or branched-chain hydrocarbon group. For example, the alkyl group may include a methyl group, an ethyl group, a propyl group, a sec-butyl group, a tert-butyl group, an iso-butyl group, a pentyl group, a neopentyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, a hexyl group, a heptyl group, an octyl group, etc.

[0034] An alkylene group may refer to a divalent hydrocarbon group from which two hydrogen atoms have been removed from a straight-chain or branched-chain hydrocarbon group.

[0035] The alkenyl group may refer to a monovalent hydrocarbon group having the same skeleton as the alkyl group described above and having at least one of the bonds between carbon atoms as a double bond. The alkenylene group may refer to a divalent hydrocarbon group in which one additional hydrogen atom has been removed from the alkenyl group described above.

[0036] The alkynyl group may refer to a monovalent hydrocarbon group having the same skeleton as the alkyl group described above and having at least one of the bonds between carbon atoms as a triple bond. The alkynylene group may refer to a divalent hydrocarbon group in which one additional hydrogen atom has been removed from the alkynyl group described above.

[0037] An aryl group may refer to a monovalent hydrocarbon group from which one hydrogen atom has been removed from a hydrocarbon group having an aromatic structure. An aryl group may include a group in which multiple aromatic rings are directly connected, such as a biphenyl group. The aryl group may include, for example, a phenyl group, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group, tetracenyl group, biphenyl group, terphenyl group, quarterphenyl group, pyrenyl group, crisenyl group, etc.

[0038] Groups in which two or more aryl rings are condensed / connected to each other by a hydrocarbon ring, such as fluorenyl groups, are also included in the category of aryl groups.

[0039] For example, the biphenyl group can be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0040] An arylene group can refer to a divalent hydrocarbon group from which two hydrogen atoms have been removed from an aryl group.

[0041] A heteroaryl group may refer to a monovalent group comprising at least one heteroatom such as B, O, P, S, and Si among the atoms forming a ring having an aromatic structure. A heteroarylene group may refer to a divalent group comprising at least one heteroatom such as B, O, P, S, and Si among the atoms forming a ring having an aromatic structure. When a heteroaryl group or a heteroarylene group comprises two or more heteroatoms, the two or more heteroatoms may be identical or different from each other.

[0042] Structures in which two or more aryls are condensed / connected by a non-aromatic heterocyclic ring, such as the carbazole group, are also included in the category of heteroaryls.

[0043] For example, "cyclic structure" can be used as a designation referring to both monocyclic and polycyclic structures, and alicyclic and aromatic rings.

[0044] "Polycyclic structure" may refer to a structure in which two or more rings are connected through one or more atoms. For example, polycyclic structures may include bicyclic structures, spiro structures, fused structures, etc., through bridge carbons.

[0045] "Condensation structure" or "condensed ring structure" may refer to a structure among the polycyclic structures described above in which two or more adjacent rings share two or more atoms. Examples of condensed ring structures include naphnalene, anthracene, phenanthrene, fluorene, pyrene, benzopyrene, pentacene, polyacene, helicene, etc.

[0046] Carbocyclic groups (e.g., C3-C 60 "Carbocyclic groups" refers to cyclic groups in which the ring-forming atoms are carbon. Heterocyclic groups (e.g., C1-C 60 A heterocyclic group refers to a cyclic group that includes a heteroatom as a ring-forming atom in addition to carbon.

[0047] Each of the above carbocyclic groups and heterocyclic groups may be a monocyclic group composed of one ring or a polycyclic group in which two or more rings are condensed together.

[0049] Polycyclic compounds

[0050] Polycyclic compounds according to the embodiments of the present disclosure are represented by the following formula 1 or formula 2.

[0051] [Chemical Formula 1]

[0052]

[0053] [Chemical Formula 2]

[0054]

[0055] In the above chemical formulas 1 and 2, Z1 to Z 10Each is independently hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C7-C 60 arylalkyl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C3-C 60 heteroarylalkyl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 The condensed polycyclic group, or a substituted or unsubstituted silyl group, and two or more adjacent groups among these may optionally combine to form a saturated or unsaturated ring.

[0056] Z1 to Z 10 At least one of them is selected from a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group and a substituted or unsubstituted carbazole group, and at least one of the remainder is an electron-withdrawing group or a group substituted with an electron-withdrawing group.

[0057] The above electron-withdrawing group is a group in which the para Hammett substituent constant (σp) of the Hammett rule is greater than 0.

[0058] The above polycyclic compound can generate excitons with high efficiency by improving hole mobility and reducing electron mobility, and has a high glass transition temperature, so degradation at high temperatures can be prevented or suppressed.

[0059] In one embodiment, the saturated ring may each be independently selected from five-membered, six-membered, and seven-membered rings, and the ring may be a hydrocarbon ring or a heteroatom-containing ring. The saturated ring may each be independently unsubstituted or deuterium, -F, -Cl, -CD3, -CD2H, -CDH2, C1-C 10 straight-chain alkyl group, C1-C 10 branched alkyl group of, C2-C 10 linear alkenyl group, C2-C 10 The branched alkenyl group and C6-C 10 It can be substituted with at least one selected from the group consisting of aryl groups.

[0060] In one embodiment, the unsaturated ring may each be independently selected from five-membered, six-membered, and seven-membered rings, and the ring may be a hydrocarbon ring or a heteroatom-containing ring. The unsaturated ring may be, for example, a cycloalkene or aromatic ring containing a C=C unsaturated double bond. The unsaturated ring and the saturated ring may each be independently unsubstituted or deuterium, -F, -Cl, -CD3, -CD2H, -CDH2, C1-C 10 straight-chain alkyl group, C1-C 10 branched alkyl group of, C2-C 10 linear alkenyl group, C2-C 10 The branched alkenyl group and C6-C 10 It can be substituted with at least one selected from the group consisting of aryl groups.

[0061] In one embodiment, for example, substituted or unsubstituted C8-C 60 The condensed polycyclic group of is C4-C 10 The aliphatic hydrocarbon ring of, and C6-C 50 The aromatic hydrocarbon ring may be a condensed polycyclic group. The condensed polycyclic group is, for example, two C6-C 15 It may have a structure in which one C4-C6 aliphatic hydrocarbon ring is condensed between aromatic hydrocarbon rings. The condensed polycyclic group may be, for example, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, or a spiro-bifluorene group.

[0062] In one embodiment, for example, the silyl group is -Si(R Sa )(R Sb )(R Sc It can be ), and R Sa , R Sb , R Sc 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 groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 The arylthio group of, or substituted or unsubstituted C8-C 60It may be a condensed polycyclic group. The condensed polycyclic group is as described above.

[0063] Hammett's rule can be used as a measure of the degree to which a functional group attracts or donates electrons. Substituent constants (σp) determined by Hammett's rule can be found in literature, for example, such as *A survey of Hammett substituent constants and resonance and field parameters*; however, even if they are not listed in such literature, substituent constants (σp) can be measured based on Hammett's rule.

[0064] In some embodiments, the electron-withdrawing group may have a Hammett rule substituent constant (σp) greater than 0.05.

[0065] In some embodiments, Z1 in Formulas 1 and 2, At least one of Z3, Z5, and Z6 may each be independently selected from the group represented by the following chemical formulas 3-1 to 3-4:

[0066]

[0067]

[0068] In the above chemical formulas 3-1 to 3-4, R a Each is independently hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C2-C 30 alkenyl groups, substituted or unsubstituted C2-C 30 alkynyl groups, substituted or unsubstituted C1-C 30 alkoxy groups, substituted or unsubstituted C3-C 30 cycloalkyl groups, substituted or unsubstituted C5-C 30cycloalkenyl groups of, substituted or unsubstituted C3-C 30 heterocycloalkyl groups, substituted or unsubstituted C3-C 30 heterocycloalkenyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 heteroaryl groups, substituted or unsubstituted C3-C 30 heteroarylalkyl groups, substituted or unsubstituted C6-C 30 The aryloxy group, or substituted or unsubstituted C6-C 30 It is an arylthio group of, and the above R a If there are 2 or more, they are identical or different, and among them, 2 or more adjacent groups may optionally combine with each other to form a saturated or unsaturated ring.

[0069] n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 3, and if n1, n2, or n3 is 2 or more, they are the same or different.

[0070] X 1 and X 2 Each is independently CR1R2, NR3, O, S, or Se.

[0071] R1 to R3 are each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 The heteroaryl group of, or substituted or unsubstituted C3-C 30 It is a heteroarylalkyl group. *- indicates the bonding position.

[0072] In some embodiments, Z1 and Z3 may each be independently selected from the group represented by the above chemical formulas 3-1 to 3-4, or Z5 and Z6 may each be independently selected from the group represented by the above chemical formulas 3-1 to 3-4. Accordingly, the electron distribution region of the core of the polycyclic compound is protected, so that unnecessary side reactions with surrounding compounds can be suppressed or prevented.

[0073] In some embodiments, the electron-withdrawing groups are each independently -F, -Cl, -Br, -I, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, and π electron-deficient nitrogen-containing C3-C 30 cyclic group of (ð electron-depleted nitrogen-containing C3-C 30 It can be selected from among cyclic groups. Accordingly, the HOMO and LUMO energy levels of the polycyclic compound can be formed to the required level to further improve hole mobility and further reduce electron mobility.

[0074] In some embodiments, the electron-withdrawing group may each be independently selected from -F, -Cl, -Br, -I, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, 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 pyrimidine group, substituted or unsubstituted naphthiridine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazolin group, substituted or unsubstituted benzosinolin group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group.

[0075] Accordingly, the hole mobility of the above polycyclic compound can be further improved.

[0076] In some embodiments, the polycyclic compound may be represented by any one of the following formulas 1-1 to 1-10:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087] In the above chemical formulas 1-1 to 1-10, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 3, and when n2 and n3 are 2 or more, they are the same or different.

[0088] R c is hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C3-C 30 cycloalkyl groups, substituted or unsubstituted C3-C 30 heterocycloalkyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 The heteroaryl group of, or substituted or unsubstituted C3-C 30 It is a heteroarylalkyl group of, and the above R cIf there are 2 or more, they are identical or different, and among them, 2 or more adjacent groups may optionally combine with each other to form a saturated or unsaturated ring.

[0089] R of 2 or more b1 and R b2 are identical or different, and these are each independently hydrogen, deuterium, -CN, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group.

[0090] Ar1 and Ar2 are each independently substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group.

[0091] R of 2 or more e They are identical or different, and each is independently selected from the above electronic turning-off devices.

[0092] R4 and R5 are each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 It is selected from the alkyl group and the electron-withdrawing group.

[0093] R d1 to R d4 Each is independently the electron-withdrawing group, the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophen group, or the substituted or unsubstituted carbazole group, and two or more of these are independently selected from the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophen group, and the substituted or unsubstituted carbazole group.

[0094] Accordingly, the LUMO energy level of the above polycyclic compound becomes deep, hole mobility is improved, and high-temperature stability can also be improved.

[0095] In some embodiments, in the formulas 1-1 to 1-6, 2 or more R b1 Each is independently substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group, and 2 or more R b2 Each can independently be hydrogen, deuterium, -CN, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, or -CFH2.

[0096] In some embodiments, 2 or more R b1 C6-C with substituted or unsubstituted components 30 It may be an aryl group, and the aryl group may include one or more electron-withdrawing groups.

[0097] R b1 The phenylene group is bonded to another arylene group bonded to the phenylene group at a meta position, and compared to when it is bonded at a para position, it can increase the core protection effect of the polycyclic compound through rotation via a single bond.

[0098] In some embodiments, in the formulas 1-1 and 1-7, R4 is selected from the electron-withdrawing groups, and R5 is each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, and substituted or unsubstituted C1-C 30 It can be selected from the alkyl groups. Accordingly, the polarity of the polycyclic compound can be increased, thereby further improving the hole injection characteristics.

[0099] In some embodiments, in the formulas 1-7 to 1-10, R d1 and R d2 At least one of, and R d3 and R d4At least one of them may be, independently, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, or a substituted or unsubstituted carbazole group.

[0100] In some embodiments, the degree of deuterium according to Formula 1 below with respect to the polycyclic compound may be 10% to 100%:

[0101] [Equation 1]

[0102] Deuterium (%) = (Number of deuterium atoms) / (Number of deuterium atoms + Number of hydrogen atoms) x 100

[0103] In the above formula 1, the number of deuterium atoms and the number of hydrogen atoms refer to the number of each deuterium and hydrogen atom included in the polycyclic compound.

[0104] The above degree of deuterium may be, for example, 50% or more, 70% or more, 80% or more, or 90% or more, and the higher the degree of deuterium, the higher the high-temperature stability may be improved.

[0105] In some embodiments, the polycyclic compound is 2.5 x 10 -4 cm 2 / Vs or higher and 1.0 x 10 -3 cm 2 It can have a hole mobility of / Vs or less, and the said hole mobility is, for example, 3.0 x 10 -4 cm 2 / Vs can be more than

[0106] In some embodiments, the polycyclic compound is 8.0 x 10 -4 cm 2 / Vs or more and 2.5 x 10 -3 cm 2 It can have an electron mobility of / Vs or less, and said electron mobility is, for example, 2.0 x 10⁻⁶ -3 cm 2 / Vs can be less than

[0107] Accordingly, the hole injection characteristics of the above polycyclic compound can be further improved.

[0108] In some embodiments, the polycyclic compound may have a glass transition temperature of 125°C or higher. Accordingly, high high-temperature stability can be achieved, and degradation during high-temperature manufacturing processes can be suppressed or reduced.

[0109] In some embodiments, the polycyclic compound may have a LUMO energy level of -5.0 eV to -6.0 eV.

[0110] Accordingly, the driving voltage and lifespan characteristics of the light-emitting device to which the above-mentioned polycyclic compound is applied can be further improved.

[0111] In some embodiments, the polycyclic compound may be any one of the following compounds 1 to 93:

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0133] Light-emitting element

[0134] FIGS. 1 to 6 are schematic cross-sectional views showing light-emitting elements according to exemplary embodiments.

[0135] Referring to FIG. 1, the light-emitting element (ED) includes a first electrode (110), a second electrode (150), and an intermediate layer (ITL) disposed between the first electrode (110) and the second electrode (150), and the intermediate layer (ITL) includes a light-emitting structure comprising a hole transport region (120), a light-emitting layer (130), and an electron transport region (140).

[0136] In some embodiments, the intermediate layer (ITL) may include two or more of the light-emitting structures.

[0137] One or more of the hole transport regions (120) may include the polycyclic compound described above, thereby achieving improved driving voltage and lifespan characteristics and sufficient luminous efficiency.

[0138] In some embodiments, the hole transport region (120) comprises at least one of a hole injection layer (122), a hole transport layer (124), and an electron blocking layer (126), and the hole injection layer (122) may comprise the polycyclic compound. Accordingly, the hole injection characteristics and stability of the light-emitting device may be improved.

[0139] In some embodiments, the polycyclic compound may include one or more compounds represented by any one of the above-described formulas 1-1 to 1-10.

[0140] In some embodiments, the polycyclic compound may include one or more of the compounds 1 to 93.

[0141] In some embodiments, the light-emitting layer (130) may emit blue light with a maximum light-emitting center wavelength of 430 nm to 490 nm.

[0142] A charge generation layer may be included between two or more light-emitting structures, and the charge generation layer may include, for example, a p-type charge generation layer and / or an n-type charge generation layer.

[0143] In some embodiments, the polycyclic compound may be included in an amount of 1% to 40% by weight based on the total weight of the hole injection layer, for example, in an amount of 1% to 30% by weight.

[0144] First electrode and second electrode

[0145] The first electrode (110) may be an anode or a cathode. In some embodiments, the first electrode (110) may be provided as an anode and may be provided as a pixel electrode. In this case, the first electrode (110) may include a high work function conductive material that promotes hole injection.

[0146] The first electrode (110) may be provided as a transparent electrode. The first electrode (110) may include a transparent conductive oxide such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0147] The first electrode (110) may be provided as a semi-transparent electrode or a reflective electrode. The first electrode (110) may include a metal selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, or an alloy of two or more of these. For example, the first electrode (110) may include Li, Ca, LiF / Ca (a stacked structure of LiF and Ca), LiF / Al (a stacked structure of LiF and Al), a mixture of Ag and Mg, etc.

[0148] The first electrode (110) may have a single-layer structure or a multi-layer structure. For example, the first electrode (110) may have a three-layer structure of ITO / Ag / ITO.

[0149] The thickness of the first electrode (110) may be about 700 Å to about 10,000 Å or about 1,000 Å to about 3,000 Å.

[0150] The second electrode (150) may be provided as a cathode or an anode. In some embodiments, the second electrode (150) may be provided as an electron injection electrode or a cathode. The second electrode (150) may include a metal, alloy, electrically conductive compound, etc., having a low work function.

[0151] For example, the second electrode (150) may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, etc. These may be used alone or in combination of two or more.

[0152] The second electrode (150) may be provided as a transparent electrode, a semi-transparent electrode, or a reflective electrode. The second electrode (150) may have a single-layer structure or a multi-layer structure.

[0153] light-emitting layer

[0154] The light-emitting layer (130) may include a host and a dopant.

[0155] As a non-limiting example, the light-emitting layer (130) may contain about 0.01 to about 15.00 parts by weight, or about 0.01 to about 12.00 parts by weight, of a dopant with respect to 100 parts by weight of a host.

[0156] The light-emitting layer (130) can emit red light, green light, blue light and / or white light. For example, the light-emitting layer (130) can emit blue light.

[0157] In some embodiments, the emission full width at half maximum of the blue light may be 30 nm or less, or 28 nm or less.

[0158] The light-emitting layer (130) may include a host material. For example, the light-emitting layer (130) may include known host materials such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, chrysene derivatives, dihydrobenzanthracene derivatives, triphenylene derivatives, etc.

[0159] In some embodiments, the light-emitting layer (130) may include, for example, a host material represented by the following formula FH. For example, a compound represented by the formula FH may be used as a fluorescent host material.

[0160] [Chemical Formula FH]

[0161]

[0162] In the chemical formula FH, R FH1 to R FH4 Each independently consists of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted ox group, and a substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C6-C30 Aryl group, substituted or unsubstituted C2-C 30 It may be a heteroaryl group, or a cyclic group formed through a combination thereof. R FH1 to R FH4 At least one of them may form a condensed ring with a bonded benzene ring.

[0163] x1a and x1b may each be independently integers from 0 to 5, and x2a and x2b may each be independently integers from 0 to 4. If x1a, x1b, x2a, and x2b are each 2 or more integers, each of multiple R FH1 to R FH4 They may be the same or different from each other.

[0164] In some embodiments, the light-emitting layer (130) may include a host material represented by, for example, the following chemical formula PH. For example, a compound represented by the chemical formula PH may be used as a host material for a phosphorescent light-emitting layer or a phosphorescent light-emitting device.

[0165] [Chemical Formula PH]

[0166]

[0167] In the chemical formula pH, R PH may be a substituted or unsubstituted carbazole group. L PH C6-C6 with direct bonding, substitution, or non-substitution 30 Aryllene group, or substituted or unsubstituted C2-C 30 It can be a heteroarylene group. Ar PH C6-C with substituted or unsubstituted components 30 Aryl group, substituted or unsubstituted C2-C 30 It can be a heteroaryl group.

[0168] As mentioned in the definition of terms, "C6-C 30 The term "aryl group" is used to encompass structures in which multiple aryls are condensed or bonded through a cyclic group (e.g., a dicyclic hydrocarbon ring). For example, C6-C 30An aryl group can encompass a fluorenyl group.

[0169] As mentioned in the definition of terms, "C2-C 30 The term "heteroaryl group" is used to encompass structures in which multiple aryls are condensed or bonded through a heterocyclic ring. For example, C2-C 30 Heteroaryl groups can encompass carbazole groups, dibenzofuran groups, dibenzothiophen groups, etc. In addition, C2-C 30 The term heteroaryl group is used to encompass a structure in which multiple aryls are condensed or bonded to one another through identical or different heterocyclic rings.

[0170] In one embodiment, Ar PH The substituents included in may include silyl groups. As a substituent, the silyl group is -Si(R sa )(R sb )(R sc It is indicated by ), and R sa , R sb and R sc Each independently consists of hydrogen, halogen, hydroxyl group, and C1-C 60 Alkyl group, C1-C 60 Alkoxy group, C6-C 60 aryl group, or C2-C 30 It can be a heteroaryl group. R sa , R sb and R sc At least one of them is C6-C 60 aryl group or C2-C 30 It can be a heteroaryl group. R sa , R sb and R sc Each independently C6-C 60 aryl group or C2-C 30 It can be a heteroaryl group.

[0171] lx can be an integer from 0 to 10 or more. If lx is an integer of 2 or more, multiple L PH They may be the same or different from each other.

[0172] 발광층(130)은 호스트 물질로서, 예를 들어, BCPDS (bis (4-(9H-carbazol-9-yl) phenyl) diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-phosphine oxide), DPEPO(bis[2-(diphenylphosphino)phenyl] ether oxide), mCBP(3,3'-Di(9H-carbazol-9-yl)-1,1'-biphenyl), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP(1,3-bis(carbazol-9-yl)benzene), PPF (2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), Alq3(tris(8-hydroxyquinolino)aluminum), ADN(9,10-di(naphthalene-2-yl)anthracene), TBADN(2-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN(2-methyl-9,10-bis(naphthalen-2-yl)anthracene), CP1(mexaphenyl cyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane), DPSiO4 (octaphenylcyclotetrasiloxane) 등을 포함할 수도 있다.

[0173] The aforementioned host materials may be used alone or in combination of two or more.

[0174] Non-limiting examples of compounds represented by the chemical formula PH are as follows.

[0175]

[0177] The light-emitting layer (130) may further include a dopant that interacts with the host described above.

[0178] In some embodiments, the light-emitting layer (130) may include a dopant represented by the following chemical formula FD. For example, a compound represented by the following chemical formula FD may be used as a fluorescent dopant.

[0179] [Chemical Formula FD]

[0180]

[0181] In the chemical formula FD, Ar FD , R FD1 and R FD2 Each is independently substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. Ax may be an integer from 1 to 6.

[0182] In some embodiments, Ar FD It may include a condensed ring structure of three or more aryl rings or benzene rings (e.g., anthracene group, chrysene group, pyrene group, etc.).

[0183] In some embodiments, the light-emitting layer (130) may include a phosphorescent dopant. The phosphorescent dopant may include an organometallic compound comprising a central metal and at least one ligand coordinately bonded to the central metal. The central metal may include, for example, a transition metal, and the ligand may include, for example, a monodenate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a combination thereof.

[0184] The above phosphorescent dopant may include, for example, a compound represented by the chemical formula PD.

[0185] [Chemical PD]

[0186] M(L d 1 ) dx1 (L d 2 ) dx2

[0187] Among the chemical formula PD,

[0188] M can be a transition metal atom, for example, 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).

[0189] L d 1 may be a ligand represented by the following chemical formula LD1.

[0190] [Chemical Formula LD1]

[0191]

[0192] In the chemical formula LD1, X PD1 and X PD2 Each can be independently C or N.

[0193] In one embodiment, X PD1 and X PD2 One of them may be C and the other may be N. In one embodiment, X PD1 and X PD2 All can be N.

[0194] CG PD1 and CG PD2 Each is independently substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. CG PD1 and CG PD2 For example, each independently pyrrole group, pyrazol group, imidazole group, triazole group, oxazole group, isooxazole group, thiazole group, isothiaazole group, oxadiazole group, thiadiazole group, benzene group, pyridine group, pyrimidine group, naphthalene group, dibenzofuran group, dibenzothiophen group, carbazole group, fluorene group, dibenzocilol group, naphthobenzofuran group, naphthobenzothiophen group, benzocarbazole group, benzoffluorene group, naphthobenzocilol group, dinaphthofuran group, dinaphthiophen group, dibenzoffluorene group, dinaphthiophenol group, azadibenzofuran group, azadibenzothiophen group, azacarbazole group, azafluorene group, azadibenzocilol group, It may be an azanaphthofenzofuran group, an azanaphthofenzothiophene group, an azabenzocarbazole group, an azabenzoflurene group, an azanaphthofenzosilol group, an azadinafthofenzofuran group, an azadinafthofenzothiophene group, an azadibenzocarbazole group, an azadibenzoflurene group, or an azadinaftholol group.

[0195] L PD is a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethenyllene group, *-O-*', *-S-*', *-C(=O)-*', *-N(R PD3 )-*', *-C(R PD4)=*' or *=C(R PD5 )=*'can be.

[0196] X PD3 and X PD4 Each is independently chemically bonded, O, S, N(R PD6 ), B(R PD7 ), P(R PD8 ), C(R PD9 )(R PD10 ) or Si(R PD11 )(R PD12 It can be. Chemical bonds can be, for example, covalent bonds or coordinate bonds.

[0197] R PD1 and R PD2 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 Condensed polycyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted aniline group, -B(R PD13 )(R PD14 ), -C(=O)(R PD15), -S(=O)2(R PD16 ), or -P(=O)(R PD17 )(R PD18 It can be ). The definition of a silyl group is -Si(R sa )(R sb )(R sc Refer to the definition of ).

[0198] R PD3 to R PD18 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 The arylthio group of, or substituted or unsubstituted C8-C 60 It can be a condensed polycyclic group.

[0199] cx1 and cx2 are each independently integers from 0 to 10, and if at least one of them is 2 or more, multiple R PD1 or multiple R PD2 They may be the same or different from each other.

[0200] -* and -*` are binding sites where the ligand represented by the chemical formula LD1 binds to M.

[0201] dx1 is an integer from 1 to 3. For example, if dx1 is 2 or 3, multiple L d 1 They may be identical or different from each other. Multiple L d 1 Among them, mutually adjacent CGs PD1 and / or CG PD2 y L PD1 , L PD2 They can be connected to each other through connectors such as L. PD1 , L PD2 The definition of a connector for the back is L PD Refer to the definition of.

[0202] L d 2 can be an organic ligand. L d 2 It may include, for example, a halogen group, CO, NO, CS, picolinate, acetate, oxalate, diketone group, isonitrile group, isothiocyanato-N, thiosulfato-S, alkylphosphine, phenylphosphine, arylphosphine, phosphine oxide, phosphite, or a combination thereof.

[0203] dx2 is an integer from 1 to 4. For example, if dx2 is 2 or greater, multiple L d 2 They may be the same or different from each other.

[0204] Non-limiting examples of compounds represented by the chemical formula PD1 are as follows.

[0205]

[0206]

[0207] In some embodiments, the light-emitting layer (130) is a fluorescent dopant material, styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (NBDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., It may include 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.

[0208] The light-emitting layer (130) may include a metal complex comprising 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 in addition to the materials described above. For example, FIrpic (iridium(III) bis(4,6-difluorophenylpyridinato-N,C2')picolinate), FIr6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), PtOEP (platinum octaethyl porphyrin), etc., may be used as a phosphorescent dopant.

[0209] In some embodiments, the light-emitting layer (130) may include a boron-containing dopant. The boron-containing dopant may be represented by the following chemical formula BD.

[0210] [Chemical Formula BD]

[0211]

[0212] Among the chemical formula BD, X BD1 and X BD2 Each can independently be N, S, O, or C. In one embodiment, X BD1 and X BD2 can be N. R BD1 and R BD2 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. R BD3 , R BD4 and R BD5 Each independently consists of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted amine group, substituted or unsubstituted boryl group, substituted or unsubstituted oxy group, substituted or unsubstituted thio group, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. R BD3 , R BD4 and / or R BD5 It can combine with adjacent tiles to form a ring.

[0213] CG BD1 and CG BD2 represents a cyclic group, each independently, a substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. In some embodiments, CG BD1 and CG BD2 Each is independently substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C30 It can be a heteroaryl group.

[0214] In one embodiment, CG BD1 and CG BD2 Each may be an independently substituted or unsubstituted phenyl group. In this case, the boron-containing dopant may be provided as a heat-activated delayed fluorescence (TADF) dopant.

[0215] In one embodiment, CG BD1 and CG BD2 One of them may be a non-condensing aryl group or a non-condensing heteroaryl group, and the other may be a condensing polycyclic aryl group or a condensing polycyclic heteroaryl group. In this case, the boron-containing dopant may be provided as a fluorescent dopant.

[0216] The above-described dopant materials can be used alone or in combination of two or more.

[0217] In some embodiments, the light-emitting layer (130) may include two or more host materials. For example, the light-emitting layer (130) may include a hole-transporting host and an electron-transporting host. In this case, the light-emitting layer (130) may include a hole-transporting host, an electron-transporting host, a photosensitive material, and a dopant. According to exemplary embodiments, the hole-transporting host and the electron-transporting host form an exciplex, and an energy transfer occurs from the exciplex to the photosensitive material, and from the photosensitive material to the dopant, thereby inducing light emission.

[0218] As a non-limiting example, the hole-transporting host may include a compound of the formula HT described below. As a non-limiting example, the electron-transporting host may include a compound represented by the formula ET described below.

[0219] In some embodiments, the light-emitting layer (130) may include quantum dots. The quantum dots may include a Group II-VI compound, a Group III-VI compound, a Group I-III-VI compound, a Group III-V compound, a Group III-II-V compound, a Group IV-VI compound, a Group IV element, a Group IV compound, or a combination thereof.

[0220] The above quantum dot comprises a core containing the aforementioned compound and may include a shell surrounding the core. The shell may include an inorganic oxide or a semiconductor compound. The semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc.

[0221] For example, the color of the emitted light can be controlled according to the particle size of the above quantum dots. The above quantum dots can be classified into blue quantum dots, red quantum dots, green quantum dots, etc.

[0222] Hole transmission zone

[0223] A hole transport region (120) may be formed between the first electrode (110) and the light-emitting layer (130). The hole transport region (120) may have a single layer or a multilayer structure comprising a plurality of layers each containing different materials.

[0224] The hole transport region (120) includes the polycyclic compound described above.

[0225] 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 a light-emitting auxiliary layer.

[0226] The hole injection layer described above includes the polycyclic compound described above.

[0227] In some embodiments, as shown in FIG. 2, the hole transport region (120) may include a hole injection layer (122) and a hole transport layer (124) sequentially stacked from the first electrode (110).

[0228] In some embodiments, as illustrated in FIG. 3, the hole transport region (120) may include a hole transport layer (124) and an electron blocking layer (126) sequentially stacked from the first electrode (110). The electron blocking layer (126) can block electron movement from the electron transport region (140) to the hole transport region (120). Thus, exciton generation in the light-emitting layer (130) can be increased, and the light emission efficiency can be further increased.

[0229] In some embodiments, the hole transport region (120) may further include the compound described below.

[0230] For example, the hole transport region (120) may include a compound represented by the following chemical formula HT.

[0231] [Chemical Formula HT]

[0232]

[0233] In the chemical formula HT, L HT1 , L HT2 and L HT3 Each is independently directly linked, substituted, or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0234] lx1 to lx3 may each be an integer from 0 to 10 independently. If lx1, lx2, or lx3 is an integer of 2 or more, multiple L HT1 and L HT2For example, they are directly connected by carbon atoms of each aryl ring (e.g., sp2 carbons), and each is independently substituted or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0235] Ar HT1 and Ar HT2 Each independently, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. Ar HT3 C6-C with substituted or unsubstituted components 30 It could be Arilgi.

[0236] In one embodiment, the compound represented by the chemical formula HT may be a monoamine compound. In one embodiment, the compound represented by the chemical formula HT is Ar HT1 or Ar HT3 At least one of them may be a diamine compound containing an amine group as a substituent.

[0237] In some embodiments, the compound represented by the chemical formula HT is Ar HT1 and Ar HT2 A carbazole compound comprising a carbazole group substituted or unsubstituted in at least one of the following, or Ar HT1 and Ar HT2 It may be a fluorene-based compound comprising a substituted or unsubstituted fluorene group in at least one of them.

[0238] In some embodiments, Ar HT1 or Ar HT3 Two adjacent groups may condense to form a single ring.

[0239] Non-limiting examples of compounds represented by the chemical formula HT are as follows.

[0240]

[0241]

[0242] 예를 들어, 정공 전달 영역(120)은 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(naphthalene-l-yl)-N,N'-diphenyl-benzidine), NPD(N,N'-Bis(naphthalen-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), 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-di-m-tolylbenzene-1,4-diamine), TAPC(4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), 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 / Camphor sulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine compounds, carbazole compounds (N-phenylcarbazole, polyvinylcarbazole, It may include CzSi (9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole), mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), fluorene compounds, etc. These may be used alone or in combination of two or more.

[0243] The above-described material may be included in at least one layer among the hole injection layer (122), the hole transport layer (124), and the electron blocking layer (126).

[0244] The hole transport region (120) may further include a charge generating material. A dopant material such as a p-dopant may be used as the charge generating material, and accordingly, the conductivity of the hole transport region (120) may be improved.

[0245] Examples of the above dopant materials include metal halide compounds such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane); cyano-containing compounds such as HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile); W oxide, Mo oxide, etc. These can be used individually or in combination of two or more.

[0246] The thickness of the hole transport region (120) can be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,500 Å.

[0247] When the hole transport region (120) includes a hole injection layer (122) and a hole transport layer (124), the thickness of the hole injection layer (122) may be about 100 Å to about 9000 Å, about 100 Å to about 3000 Å, or about 100 Å to about 1000 Å, and the thickness of the hole transport layer (124) may be about 50 Å to about 2000 Å, about 100 Å to about 1500 Å, about 100 Å to about 1000 Å, or about 100 Å to about 600 Å.

[0248] In the above thickness range, hole transport characteristics are enhanced even at low voltage driving, and the lifespan of the device can be further improved.

[0249] Each layer of the hole transport region (120) can be formed through processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, laser thermal transfer, etc.

[0250] Electron transfer region

[0251] An electron transfer region (140) may be formed between the second electrode (150) and the light-emitting layer (130). The electron transfer region (140) may have a single layer or a multilayer structure comprising a plurality of layers each containing different materials.

[0252] The electron transport region (140) may include an electron injection layer, an electron transport layer and / or a hole blocking layer, and may further include a light-emitting auxiliary layer.

[0253] In some embodiments, as shown in FIG. 2, the electron transfer region (140) may include an electron injection layer (142) and an electron transport layer (144) sequentially stacked from the second electrode (150) toward the light-emitting layer (130).

[0254] In some embodiments, as illustrated in FIG. 3, the electron transfer region (140) may include an electron injection layer (142), an electron transport layer (144), and a hole blocking layer (146) sequentially stacked from the second electrode (150). The injection of holes from the hole transfer region (120) may be suppressed or blocked by the hole blocking layer (146). Thus, the emission energy and luminescence efficiency in the light-emitting layer (130) may be further improved.

[0255] For example, the electron transfer region (140) may include a compound represented by the following chemical formula ET.

[0256] [Chemical Formula ET]

[0257]

[0258] In the chemical formula ET, X ET1 To X ET3At least one of them is N and the others are each independently CR ET It could be. R ET is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 60 Aryl groups, or substituted or unsubstituted C2-C 60 It can be a heteroaryl group.

[0259] X ET1 To X ET3 If either one is N, the compound represented by the chemical formula ET may contain a pyridine group. X ET1 To X ET3 If either of the two are N, the compound represented by the chemical formula ET may contain a pyrimidine group. X ET1 To X ET3 When all of these are N, the compound represented by the chemical formula ET may contain a triazine group.

[0260] lx1 to lx3 can each independently be an integer from 0 to 10. L ET1 to L ET3 Each is independently a directly linked, substituted, or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted C2-C 30 It can be a heteroarylen group.

[0261] If lx1, lx2, or lx3 is an integer greater than or equal to 2, multiple L ET1 L ET2 S, or L ET3 For example, they are directly connected by carbon atoms of each aryl ring (e.g., sp2 carbons), and each is independently substituted or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0262] Ar ET1 or Ar ET3Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. For example, Ar ET1 or Ar ET3 Each may independently be 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 definition of a silyl group is -Si(R sa )(R sb )(R sc Refer to the definition of ).

[0263] Non-limiting examples of compounds represented by the chemical formula ET are as follows.

[0264]

[0265]

[0266] For example, the electron transfer region (140) is an anthracene compound, Alq3 (tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-diphenyl-1,10-phenanthroline), TAZ(3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq2(beryllium bis(benzoquinolin-10-olate)), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), It may include TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), etc. These may be used alone or in combination of two or more.

[0267] The above-described material may be included in at least one of the electron injection layer (142), the electron transport layer (144), and the hole blocking layer (146).

[0268] The electron transfer region (140) may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof. In one embodiment, the above-described material may be included in the electron injection layer (142).

[0269] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0270] The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or combinations thereof of the alkali metal, alkaline earth metal, and rare earth metal, respectively.

[0271] The above alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include a metal ion of the aforementioned alkali metal, alkaline earth metal, or rare earth metal, and a ligand bound to said metal ion. The ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

[0272] The thickness of the electron transfer region (140) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å.

[0273] When the electron transfer region (140) includes an electron injection layer (142) and 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.

[0274] In the above thickness range, electron injection characteristics and electron transport characteristics can be further improved without an excessive increase in driving voltage, and the stability of the electron transport region (140) can be improved.

[0275] Each layer of the electron transfer region (140) can be formed through processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, laser thermal transfer.

[0276] The light-emitting element (ED) may further include a capping layer. The light emission efficiency to the outside of the light-emitting element (ED) can be enhanced through the capping layer.

[0277] As illustrated in FIG. 4, a second capping layer (160b) may be formed on the outer surface of the second electrode (150). In some embodiments, a first capping layer (160a) may be formed on the outer surface of the first electrode (110).

[0278] The refractive index of the first capping layer (160a) and / or the second capping layer (160b) may be 1.6 or higher. For example, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the first capping layer (160a) and / or the second capping layer (160b) may be 1.6 or higher, 1.8 or higher, or 2.0 or higher.

[0279] The first capping layer (160a) and the second capping layer (160b) may each be formed as an organic capping layer containing an organic material, an inorganic capping layer containing an inorganic material, or an organic-inorganic composite capping layer containing both organic and inorganic materials.

[0280] The first capping layer (160a) and / or the second capping layer (160b) may each have a single-layer structure or a multi-layer structure comprising multiple materials.

[0281] In some embodiments, the first capping layer (160a) and / or the second capping layer (160b) may comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, etc. These may be used alone or in combination of two or more.

[0282] According to one embodiment, the first capping layer (160a) and / or the second capping layer (160b) may include the amine group-containing compound.

[0283] As a non-limiting example, the first capping layer (160a) and / or the second capping layer (160b) may include the compounds HT-7, HT-8, etc.

[0284] Referring to FIG. 5, the light-emitting element (ED) may include a plurality of light-emitting structures (ES1, ES2, ES3). Each of the light-emitting structures (ES1, ES2, ES3) may include a stacked structure of a hole transport region (120), a light-emitting layer (130), and an electron transport region (140) as described with reference to FIG. 1 to 4. According to exemplary embodiments, the light-emitting element (ED) of FIG. 5 may be a light-emitting element with a tandem structure.

[0285] A charge generation layer (CGL1, CGL2) may be disposed between adjacent light-emitting structures (ES1, ES2, ES3). The charge generation layer (CGL1, CGL2) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0286] The p-type charge generation layer may include a compound that can be utilized as a hole transport host, such as NPB. For example, the p-type charge generation layer may include a compound represented by the chemical formula HT described above. The p-type charge generation layer may further include a p-dopant, such as TCNQ.

[0287] In some embodiments, the n-type charge generating layer may comprise at least one selected from the group consisting of alkali metals, alkaline earth metals, lanthanide metals, rare earth metals, transition metals, post-transition metals, and alloys thereof.

[0288] The n-type charge generating layer may further include, for example, a metal complex, and said metal complex may include the metal described above and at least one organic ligand. The said organic ligand may be, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, etc.

[0289] The n-type charge generating layer may further include a compound that can be utilized as an electron transport host. For example, the n-type charge generating layer may further include a compound represented by the chemical formula ET described above. In one embodiment, the n-type charge generating layer may include a phenanthroline-based compound.

[0290] For example, the thickness of the n-type charge generation layer and the thickness of the p-type charge generation layer may each be independently 20 Å to 1000 Å, 20 Å to 700 Å, or 30 Å to 500 Å.

[0291] The charge generation layer (CGL1, CGL2) may include a first charge generation layer (CGL1) disposed between a first light-emitting structure (ES1) and a second light-emitting structure (ES2), and a second charge generation layer (CGL2) disposed between a second light-emitting structure (ES2) and a third light-emitting structure (ES3).

[0292] According to exemplary embodiments, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), a third light-emitting structure (ES3), and a second electrode (150) may be sequentially stacked from the upper surface of a first electrode (110).

[0293] The colors emitted from the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) may be the same or different from each other. In some embodiments, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) each 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 realized through a tandem structure, but is not limited thereto.

[0294] In FIG. 5, a 3-stack tandem structure in which three light-emitting structures are stacked is illustrated as an example, but the tandem structure of the light-emitting element of the present disclosure is not limited to the structure illustrated in FIG. 5. For example, it may be extended to a 2-stack, or a 4-stack, 5-stack, or more structures as described later with reference to FIG. 6.

[0295] Referring to FIG. 6, as described with reference to FIG. 5, a tandem structure in which a light-emitting structure and a charge-generating layer are alternately and repeatedly stacked can be arranged between the first electrode (110) and the second electrode (150).

[0296] According to exemplary embodiments, a first light-emitting structure (ES1) to an m-th light-emitting structure (ESm) may be sequentially stacked from the upper surface of the first electrode (110) with a charge generating layer in between. The charge generating layer may include a first charge generating layer (CGL1) to an m-1 charge generating layer (CGLm-1) sequentially stacked from the upper surface of the first electrode (110).

[0297] As shown in FIG. 6, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), ..., an m-1 light-emitting structure (ESm-1), an m-1 charge-generating layer (CGLm-1), an m-1 light-emitting structure (ESm), and a second electrode (150) can be sequentially stacked from the upper surface of the first electrode (110).

[0298] In some embodiments, m is 4, and the intermediate layer (ITL) of the light-emitting element has a 4-stack tandem structure and may include first to fourth light-emitting structures (ES1, ES2, ES3, ES4) and first to third charge-generating layers (CGL1, CGL2, CGL3). The colored light generated from the first to fourth light-emitting structures (ES1, ES2, ES3, ES4) may be the same or different from one another.

[0299] In one embodiment, the first to fourth light-emitting structures (ES1, ES2, ES3, ES4) may include at least one blue light-emitting structure and at least one green light-emitting structure. As a non-limiting example, the first to third light-emitting structures (ES1, ES2, ES3) correspond to blue light-emitting structures, and the fourth light-emitting structure (ES4) corresponds to a green light-emitting structure.

[0300] In some embodiments, m is 5 and the intermediate layer (ITL) of the light-emitting element has a 5-stack tandem structure and may include first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) and first to fourth charge-generating layers (CGL1, CGL2, CGL3, CGL4). The colored light generated from the first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) may be the same or different from one another.

[0301] In one embodiment, the first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) may include at least one blue light-emitting structure and at least one green light-emitting structure. As a non-limiting example, the first to fifth light-emitting structures (ES, ES2, ES3, ES4, ES5) may include three blue light-emitting structures and two green light-emitting structures. For example, the first, third, and fifth light-emitting structures (ES1, ES3, ES5) correspond to blue light-emitting structures, and the second and fourth light-emitting structures (ES2, ES4) correspond to green light-emitting structures.

[0302] Electronic device

[0303] The light-emitting element (ED) described above can be applied to an electronic device and provided as a light-emitting part or light-emitting unit of the electronic device.

[0304] The above electronic device includes a light-emitting element (ED) having a light-emitting layer comprising a polycyclic compound of Chemical Formula 1 described above, and can achieve improved light-emitting efficiency and lifespan characteristics.

[0305] The electronic device may further include, for example, a functional layer disposed on the light-emitting element and comprising a sensor layer, a polarizing layer, a color conversion layer, a color filter layer, or a combination of at least two of these.

[0306] The above electronic device may include a display device, an advertising board, a guide sign, a light source / lighting, a personal computer such as a notebook computer or a desktop computer, a mobile phone, an e-book, an e-dictionary, an e-notebook, various sensors, a diagnostic device, a healthcare device, and various display parts of a means of transportation (automobile, aircraft, ship, train).

[0307] According to exemplary embodiments, the light-emitting element (ED) can be applied to an organic light-emitting diode (OLED) display device or a quantum dot (QD)-OLED display device.

[0308] FIG. 7 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0309] Referring to FIG. 7, the display device may include a circuit layer (CL) disposed on a base substrate (200) and light-emitting elements (ED1, ED2, ED3) disposed on the circuit layer (CL).

[0310] The base substrate (200) may be provided as a support substrate or back-plane substrate of an image display device. A glass substrate or a plastic substrate may be used as the base substrate (100).

[0311] In some embodiments, the base substrate (200) may comprise a polymer material having transparency and flexibility. In this case, the base substrate (200) may be employed in a transparent flexible display device. For example, the base substrate (200) may comprise a polymer material such as polyimide, polysiloxane, epoxy resin, acrylic resin, or polyester. In one embodiment, the base substrate (200) may comprise polyimide.

[0312] The circuit layer (CL) may include transistors (TR1, TR2, TR3). The circuit layer (CL) may include wiring layers and insulating layers that form a thin-film transistor array (TFT-Array).

[0313] The circuit layer (CL) may further include a buffer layer (205) formed on the upper surface of the base substrate (200). Moisture penetrating through the base substrate (200) can be blocked by the buffer layer (205), and the diffusion of impurities between the base substrate (200) and the structure formed on the base substrate (200) can be blocked.

[0314] The buffer layer (205) may include, for example, silicon oxide, silicon nitride, or silicon oxynitride. These may be used alone or in combination of two or more. In some embodiments, the buffer layer (205) may have a stacked structure including a silicon oxide film and a silicon nitride film.

[0315] Transistors (TR1, TR2, TR3) may be disposed on the buffer layer (205). The first transistor (TR1), the second transistor (TR2), and the third transistor (TR3) may be electrically connected to the first light-emitting element (ED1), the second light-emitting element (ED2), and the third light-emitting element (ED3), respectively.

[0316] The transistors (TR1, TR2, TR3) may each include an active layer (210), a gate insulating layer (220), and a gate electrode (230).

[0317] The active layer (210) is disposed on the buffer layer (205) and may be arranged repeatedly / regularly for each pixel. The active layer (210) may include a silicon compound such as amorphous silicon or polysilicon. Some regions of the active layer (210) may be doped with a p-type dopant or an n-type dopant and may include a source region, a drain region, and a channel region.

[0318] The active layer (210) may include an oxide semiconductor such as indium-gallium-zinc oxide (IGZO), zinc-tin oxide (ZTO), or ITZO.

[0319] A gate insulating layer (220) is formed on an active layer (210), and a gate electrode (230) may be laminated on the gate insulating layer (220). As shown in FIG. 6, the gate insulating layer (220) may be formed in a pattern shape that partially covers each active layer (210). Alternatively, the gate insulating layer (220) may extend continuously across a plurality of pixels or light-emitting regions and may be commonly included for the first to third transistors (TR1, TR2, TR3).

[0320] The gate electrode (230) can be overlapped in a vertical direction with the channel region of the active layer (210).

[0321] An interlayer insulating layer (240) covering a gate insulating layer (220) and a gate electrode (230) may be formed on the active layer (210). Connecting electrodes (250, 260) that are in contact with or electrically connected to the active layer (210) may be disposed on the interlayer insulating layer (240).

[0322] The connecting electrodes (250, 260) penetrate the interlayer insulating layer (240) and can be connected to the active layer (210). When the gate insulating layer (220) is formed continuously and commonly across a plurality of light-emitting regions, the connecting electrodes (250, 260) can penetrate the gate insulating layer (220) together.

[0323] The connecting electrodes (250, 260) may include a source electrode (250) that is connected to or in contact with the source region of the active layer (210) and a drain electrode (260) that is connected to or in contact with the drain region of the active layer (210).

[0324] The gate insulating layer (220) and the interlayer insulating layer (240) may include silicon oxide, silicon nitride, or silicon oxynitride, and may have a stacked structure including a silicon oxide film and a silicon nitride film.

[0325] The gate electrode (230) and connecting electrodes (250, 260) may include metals such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, alloys thereof, or nitrides thereof.

[0326] The via insulating film (270) can be formed on the interlayer insulating layer (240) to cover the connecting electrodes (250, 260).

[0327] The via insulating film (270) may accommodate a via structure that electrically connects the first electrode (110) and the drain electrode (260). The via insulating film (270) may be provided as a flattening film of the circuit layer (CL). In some embodiments, the via insulating film (270) may comprise an organic material such as polyimide, epoxy resin, acrylic resin, or polyester.

[0328] A light-emitting element (ED1, ED2, ED3) may be disposed on the via insulating layer (270). For example, as described with reference to FIGS. 1 to 4, the light-emitting element (ED1, ED2, ED3) may include a first electrode (110), a hole transport region (120), a light-emitting layer (130), an electron transport region (140), and a second electrode (150) sequentially stacked from the via insulating layer (170).

[0329] The first electrode (110) can be electrically connected to a transistor (TR1, TR2, TR3) or a connecting electrode (250, 260) included in the circuit layer (CL) through the via structure. As shown in FIG. 7, the first electrode (110) can be in contact with or connected to a drain electrode (260) to be provided as a patterned pixel electrode for each light-emitting region or pixel region.

[0330] A pixel defining film (280) can be formed on a via insulating film (270) to define a light-emitting region or a pixel region. For example, a red light-emitting region, a green light-emitting region, and a blue light-emitting region are separated and defined by the pixel defining film (280), and light-emitting elements (ED1, ED2, ED3) can correspond to a red light-emitting element, a green light-emitting element, and a blue light-emitting element, respectively.

[0331] The pixel defining film (280) can partially cover the first electrode (110) of each light-emitting region.

[0332] As illustrated in FIG. 7, the hole transport region (120) and the electron transport region (140) can be formed continuously and commonly on the pixel defining film (280) and the plurality of first electrodes (110). The light-emitting layer (130) can be formed in the form of separate islands for each light-emitting region or pixel region and can be defined by the pixel defining film (280).

[0333] In some embodiments, the light-emitting layer (130) may also be formed continuously and commonly across a plurality of light-emitting regions or pixel regions. In some embodiments, the hole transport region (120), the light-emitting layer (130), and the electron transport region (140) may all be formed separately and selectively for each light-emitting region or pixel region.

[0334] The second electrode (150) may be provided as a common electrode formed continuously across a plurality of light-emitting regions or pixel regions.

[0335] The encapsulation layer (290) is disposed on the pixel defining film (280) and the light-emitting elements (ED1, ED2, ED3) to protect the light-emitting elements (ED1, ED2, ED3) from moisture or oxygen. The encapsulation layer (290) may be formed as a thin film encapsulation (TFE) having a single layer or a multilayer structure.

[0336] The encapsulation layer (290) may comprise an inorganic film comprising silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0337] The display device may further include a functional layer (300) disposed on the encapsulation layer (290). The functional layer (300) may include a sensor layer such as a touch sensor layer; or an optical layer such as a polarizing layer, a color conversion layer, or a color filter layer.

[0338] FIG. 8 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0339] Referring to FIG. 8, each light-emitting element (ED1, ED2, ED3) may have a tandem structure, for example, a 2-stack tandem structure.

[0340] In some embodiments, the hole transport region (120) and the electron transport region (140) may be formed continuously and commonly included in the intermediate layer of each light-emitting structure. Additionally, a charge generation layer (CGL) may be continuously extended across a plurality of pixels and commonly included in the intermediate layer of each light-emitting structure.

[0341] The first light-emitting element (ED1) may include a first lower light-emitting layer (130-1a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a first upper light-emitting layer (130-1b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0342] The second light-emitting element (ED2) may include a second lower light-emitting layer (130-2a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a second upper light-emitting layer (130-2b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0343] The third light-emitting element (ED3) may include a third lower light-emitting layer (130-3a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a third upper light-emitting layer (130-3b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0344] The lower light-emitting layer and the upper light-emitting layer included in each light-emitting structure can generate light of the same color. In one embodiment, the first lower light-emitting layer (130-1a) and the first upper light-emitting layer (130-1b) included in the first light-emitting element (ED1) may each correspond to a red light-emitting layer. The second lower light-emitting layer (130-2a) and the second upper light-emitting layer (130-2b) included in the second light-emitting element (ED2) may each correspond to a green light-emitting layer. The third lower light-emitting layer (130-3a) and the third upper light-emitting layer (130-3b) included in the third light-emitting element (ED3) may each correspond to a blue light-emitting layer.

[0345] FIG. 9 is a schematic cross-sectional view showing the stacked form of a light-emitting structure in a display device according to exemplary embodiments. For convenience of illustration and explanation, the circuit layer, base substrate, pixel defining film, etc., are omitted in FIG. 9, and the shape of each layer or configuration of the light-emitting structure is briefly illustrated as a rectangle.

[0346] Referring to FIG. 9, at least one of the light-emitting structures (ED1, ED2, ED3) or pixel regions (PA1, PA2, PA3) has a tandem structure including a plurality of light-emitting layers, and at least one may have a single light-emitting layer structure.

[0347] In some embodiments, one of the light-emitting structures (ED1, ED2, ED3) or pixel regions (PA1, PA2, PA3) may have a tandem structure, and the others may have a single light-emitting layer structure.

[0348] As illustrated in FIG. 9, a first pixel area (PA1), a second pixel area (PA2), and a third pixel area (PA3) may each include a first light-emitting element (ED1), a second light-emitting element (ED2), and a third light-emitting element (ED3). In some embodiments, the first pixel area (PA1), the second pixel area (PA2), and the third pixel area (PA3) may correspond to a red pixel area, a green pixel area, and a blue pixel area, respectively.

[0349] The hole transport region (120), electron transport region (140), and second electrode (150) may be provided as a common layer that extends continuously across the first pixel region (PA1), the second pixel region (PA2), and the third pixel region (PA3).

[0350] A first light-emitting element (ED1) included in a first pixel area (PA1) may include a first light-emitting layer (130-1), and a second light-emitting element (ED2) included in a second pixel area (PA2) may include a second light-emitting layer (130-2). The first light-emitting layer (130-1) and the second light-emitting layer (130-2) may each be a single-layer light-emitting layer.

[0351] The third light-emitting element (ED3) included in the third pixel area (PA3) may have, for example, a 2-stack tandem structure. The third light-emitting element (ED3) may include a third lower light-emitting layer (130-3a) and a third upper light-emitting layer (130-3b) separated by a charge generation layer (CGL). The third lower light-emitting layer (130-3a) and the third upper light-emitting layer (130-3b) may each correspond to a blue light-emitting layer.

[0352] A lower electron transfer region (140a) may be disposed between the charge generation layer (CGL) and the third lower light-emitting layer (130-3a). An upper hole transfer region (120b) may be disposed between the charge generation layer (CGL) and the third upper light-emitting layer (130-3b).

[0353] Accordingly, a tandem structure of light-emitting structures in which a first electrode (110), a hole transport region (120), a third lower light-emitting layer (130-3a), a lower electron transport region (140a), a charge generation layer (CGL), an upper hole transport region (120b), a third upper light-emitting layer (130-3b), an electron transport region (140), and a second electrode (150) are sequentially stacked may be disposed in the third pixel region (PA3).

[0354] FIG. 10 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0355] FIG. 10 illustrates a display device with a QD-OLED structure according to exemplary embodiments. Detailed descriptions of configurations and structures that are substantially the same or similar as those described with reference to FIG. 7 are omitted.

[0356] Referring to FIG. 10, a pixel defining film (280) and a light-emitting element (ED) may be disposed on the circuit layer (CL) as described with reference to FIG. 6. According to exemplary embodiments, light of the same wavelength range may be emitted for each pixel. In one embodiment, blue light may be emitted from each light-emitting element (ED).

[0357] In some embodiments, a light-emitting element of the tandem structure described with reference to FIG. 5 may be disposed in each light-emitting region. In this case, an intermediate layer (ITL) included in the light-emitting element (ED) may be formed continuously and commonly across a plurality of light-emitting regions.

[0358] A color control layer (CCL) including color control units (CCP1, CCP2, CCP3) may be disposed on the packaging layer (290).

[0359] The color control units (CCP1, CCP2, CCP3) may include a phototransformer such as a quantum dot or a phosphor. The wavelength of light introduced into each color control unit (CCP1, CCP2, CCP3) may be converted and emitted by the phototransformer.

[0360] Color control units (CCP1, CCP2, CCP3) can be separated or spaced apart from each other by a bank (BM). The bank (BM) can substantially overlap with the pixel definition film (280), and the color control units (CCP1, CCP2, CCP3) can substantially overlap with the light-emitting layer (130).

[0361] The color control layer (CCL) may include a first color control unit (CCP1) comprising a first quantum dot that converts a first color light provided by a light-emitting element (ED) into a second color light, a second color control unit (CCP2) comprising a second quantum dot that converts the first color light into a third color light, and a third color control unit (CCP3) that transmits the first color light.

[0362] In some embodiments, the first color light, the second color light, and the third color light may each be blue light, red light, and green light. The first quantum dot and the second quantum dot may each be a red quantum dot and a green quantum dot.

[0363] The color control units (CCP1, CCP2, CCP3) may further include scatterers such as inorganic particles. The third color control unit (CCP3) may not include quantum dots and may include scatterers. The scatterers may include TiO2, ZnO, Al2O3, SiO2, hollow silica, etc. These may be used individually or in combination of two or more.

[0364] The color control units (CCP1, CCP2, CCP3) may further include a binder resin that disperses the quantum dots and scatterers. The binder resin may include acrylic resin, urethane resin, silicone resin, epoxy resin, etc.

[0365] A color filter layer (CFL) including color filters (CF1, CF2) and a light-blocking portion (CP) may be disposed on the color control layer (CCL).

[0366] The color filter layer (CFL) may include a first filter (CF1) that transmits second color light, a second filter (CF2) that transmits third color light, and a third filter that transmits first color light. For example, the first filter (CF1) may be a red filter, the second filter (CF2) may be a green filter, and the third filter may be a blue filter.

[0367] Color filters (CF1, CF2) may include a photosensitive binder resin and a colorant comprising a pigment and / or dye. The first filter (CF1) may include a red pigment or dye, and the second filter (CF2) may include a green pigment or dye.

[0368] A light-blocking section (CP) may be disposed between the above color filters. In some embodiments, the light-blocking section may include a first light-blocking section (CP1) and a second light-blocking section (CP2) comprising color materials of different colors.

[0369] In some embodiments, the first light-blocking part (CP1) includes a blue color material, and the second light-blocking part (CP2) may include a red color material or a black color material. In one embodiment, in the blue light-emitting region, the portion of the first light-blocking part (CP1) exposed between the second light-blocking parts (CP2) may be provided as a blue color filter, and a separate color filter (third filter) may be omitted.

[0370] A first barrier layer (310) may be disposed between the color control layer (CCL) and the light-emitting element (ED) (or encapsulation layer (290)). A second barrier layer (320) may be disposed between the color control layer (CCL) and the color filter layer (CFL).

[0371] The barrier layer (310, 320) may include at least one inorganic layer. For example, the barrier layer (310, 320) may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, etc.

[0372] The barrier layer (310, 320) may have a multilayer structure that further includes an organic layer.

[0373] FIG. 11 is a schematic cross-sectional view showing a display device according to exemplary embodiments. Detailed descriptions of configurations and structures substantially identical or similar to those described with reference to FIG. 10 are omitted.

[0374] Referring to FIG. 11, a light-emitting element (ED) corresponding to color control units (CCP1, CCP2, CCP3) is disposed on a first electrode (110) provided as a pixel electrode, and the light-emitting element (ED) may have a tandem structure.

[0375] In some embodiments, as described with reference to FIG. 5, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), and a third light-emitting structure (ES3) may be sequentially stacked between a first electrode (110) and a second electrode (150). The first light-emitting structure (ES1), the first charge-generating layer (CGL1), the second light-emitting structure (ES2), the second charge-generating layer (CGL2), and the third light-emitting structure (ES3) may be formed continuously in a plurality of pixel regions or light-emitting regions.

[0376] In one embodiment, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) generate different colored light, and the light-emitting element (ED) can generate white light. In one embodiment, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) can all generate blue light.

[0377] In some embodiments, as described with reference to FIG. 6, the light-emitting element (ED) may include a tandem structure with a stack of 4, 5, or more stacks.

[0378] FIG. 12 is a schematic diagram showing an electronic device according to exemplary embodiments.

[0379] According to exemplary embodiments, the electronic device may be implemented in the form of a mobile phone (smartphone), tablet, PC, etc., including the display device described above.

[0380] Referring to FIG. 12, the electronic device may include a window structure (WS), a display panel (DP), and a rear structure (RS).

[0381] The window structure (WS) provides an external display surface perceived by a user, such as the viewing surface of a mobile phone, for example, and may include a transparent material film. For example, the window structure (WS) may include glass (e.g., ultra-thin glass (UTG)), a hard coating film, a plastic film, etc.

[0382] The outer surface of the window structure (WS) may include an active area (AA) and a peripheral area (PA). The active area (AA) may provide a surface on which an image of the display device is substantially displayed and where a user's touch / command is input. The peripheral area (PA) may substantially correspond to the bezel area of ​​the display device.

[0383] The display panel (DP) includes the display device described above and may include a display area (DA) and a non-display area (NDA). The display area (DA) of the display panel (DP) may substantially correspond to or overlap with the active area (AA) of the window structure (WS). The non-display area (NDA) of the display panel (DP) may substantially correspond to or overlap with the peripheral area (PA) of the window structure (WS).

[0384] In some embodiments, functional element regions (E1, E2) may be included within an active region (AA) of a window structure (WS). For example, the first functional element 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 element region (E2) may be provided as a fingerprint sensing region.

[0385] For example, a sensor structure for touch sensing or fingerprint sensing may be placed within the display panel (DP), or between the window structure (WS) and the display panel (DP).

[0386] The rear structure (RS) may be provided as a chassis structure or housing of the display device or electronic device. A cover panel may be disposed between the rear structure (RS) and the display panel (DP).

[0387] FIG. 13 is a schematic diagram showing an electronic device according to exemplary embodiments.

[0388] The electronic device may be installed, embedded, attached, or integrated into the vehicle (400). The vehicle (400) is not limited to the structure shown in FIG. 13 and may include means of transportation such as a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a motor device, a bicycle, a train, etc. Additionally, electric vehicles, hybrid vehicles, etc. may be included in the vehicle (400).

[0389] Referring to FIG. 13, at least one of the first to fifth display devices (DP1, DP2, DP3, DP4, DP5) can be applied to a vehicle (400).

[0390] According to exemplary embodiments, the first display device (DP1) may be placed in the cluster area (410). In the cluster area (410), driving information such as mileage and speed, and various warning lights may be displayed.

[0391] The second display device (DP2) may be placed on the front window (FW) of the vehicle (400). For example, the second display device (DP2) may be installed in the form of a head-up display (HUD).

[0392] A third display device (DP3) may be placed on the center fascia (420) of the vehicle (400). On the center fascia (420), buttons or switches for controlling the operation of a video / music player, air conditioner, heater, etc., may be displayed, and vehicle information may be displayed.

[0393] The fourth display device (DP4) may be applied to the side mirror (430) of the vehicle (400). The side mirror (430) is installed on both sides, inside and / or outside the vehicle, respectively, and the fourth display device (DP4) may be applied to at least one of the side mirrors (430) on both sides.

[0394] The fifth display device (DP5) may be placed on the passenger seat dashboard (440). Information / images identical or different from those displayed on the cluster area (410) and / or the center fascia (420) may be displayed through the passenger seat dashboard (440).

[0395] In some embodiments, the electronic device may be, for example, a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and / or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

[0396] A display device according to the embodiments of the present disclosure can be applied to various electronic devices. An electronic device according to one embodiment includes the display device described above and may further include a module or device having additional functions other than the display device.

[0397] FIG. 14 is a block diagram of an electronic device according to one embodiment. Referring to FIG. 14, an electronic device (10) according to one embodiment may include a display module (11), a processor (12), a memory (13), and a power module (14).

[0398] The processor (12) may include at least one of a central processing unit (CPU), an application processor (AP), a graphic processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0399] The memory (15) may store data information necessary for the operation of the processor (12) or the display module (11). When the processor (12) executes an application stored in the memory (15), a video data signal and / or an input control signal is transmitted to the display module (11), and the display module (11) can process the received signal and output video information through a display screen.

[0400] The power module (14) may include a power supply module, such as a power adapter or battery device, and a power conversion module that converts the power supplied by the power supply module to generate power required for the operation of the electronic device (10).

[0401] At least one of each component of the electronic device (11) described above may be included in a display device according to the embodiments described above. Additionally, some of the individual modules functionally included in one module may be included in the display device, while others may be provided separately from the display device. For example, the display device may include a display module (11), and the processor (12), memory (13), and power module (14) may be provided in the form of other devices within the electronic device (11) that are not the display device.

[0402] FIG. 15 is a schematic diagram of an electronic device according to various embodiments.

[0403] Referring to FIG. 15, various electronic devices to which display devices according to the embodiments described above are applied may include not only image display electronic devices such as smartphones (10_1a), tablet PCs (10_1b), laptops (10_1c), TVs (10_1d), and desk monitors (10_1e), but also wearable electronic devices including display modules such as smart glasses (10_2a), head-mounted displays (10_2b), and smart watches (10_2c), and automotive electronic devices (10_3) including display modules such as CID (Center Information Display) and room mirror displays placed on the instrument panel, center fascia, and dashboard of a car.

[0404] FIG. 16 illustrates a case where an electronic device including a display module is applied to a vehicle. For example, the electronic device (10_3) may be applied to the instrument panel, center fascia, etc. of a vehicle, or may be applied to a Center Information Display (CID) placed on the dashboard of a vehicle or a room mirror display that replaces a side mirror.

[0406] Hereinafter, experimental examples including examples and comparative examples are presented to aid in understanding the present disclosure; however, these examples are merely illustrative of the present disclosure and are not intended to limit the appended claims. It is obvious to those skilled in the art that various changes and modifications to the examples are possible within the scope and spirit of the present disclosure, and that such variations and modifications fall within the scope of the appended claims.

[0408] Synthesis Example 1: Synthesis of Compound 1

[0409] Compound 1 according to one embodiment can be synthesized, for example, as follows.

[0410]

[0411]

[0412] 1) Synthesis of Intermediate 1-1

[0413] 2,2'-(4,6-dibromo-2-fluoro-1,3-phenylene)diacetonitrile (1 eq), 2'-ethynyl-[1,1':3',1''-terphenyl]-4,4'',5'-tricarbonitrile (2 eq), PdCl2(PPh3)2 (0.05 eq), copper iodide (0.05 eq), triphenylphosphine (0.1 eq), and diisopropylamine (0.2 eq) were dissolved in toluene under a nitrogen atmosphere and stirred at 50°C for 24 hours. After cooling, the mixture was washed three times with ethyl acetate and water, separated, and the resulting organic layer was dried with MgSO4 and then vacuum dried. Intermediate 1-1 was obtained by purification using column chromatography (yield 59%).

[0414] 2) Synthesis of Intermediate 1-2

[0415] Intermediate 1-1 (1 eq), PdCl2 (0.05 eq), Silver hexafluoroantimonate (V) (0.1 eq), and Diphenylsulfoxide (3 eq) were dissolved in dichloroethylene and stirred at 60°C for 24 hours. Subsequently, Cs2CO3 (0.1 eq) was added and stirred for 12 hours. The mixture was then extracted with dichloromethane, added to 35% hydrochloric acid, and stirred for 2 hours. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Intermediate 1-2 was obtained by column chromatography. (Yield 38%)

[0416] 3) Synthesis of Compound 1

[0417] Intermediate 1-2 (1 eq), malononitrile (2 eq), and dichloromethane were stirred under a nitrogen atmosphere for 30 minutes. Titanium tetrachloride (3 eq) was slowly injected, followed by the addition of pyridine and stirring at room temperature. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Compound 1 was obtained by column chromatography (yield 2.2%).

[0418] The generated compound was confirmed via MS / FAB.

[0419] C 62 H 21 FN 12 cal. 952.20, found 952.21

[0421] Synthesis Example 2: Synthesis of Compound 36

[0422] Compound 36 according to one embodiment can be synthesized, for example, as follows.

[0423]

[0424]

[0425]

[0426] 1) Synthesis of intermediate 36-1

[0427] 2,2'-(2-bromo-5-iodo-1,4-phenylene)diacetonitrile (1 eq), 5'-(4-cyanophenyl)-2'-ethynyl-[1,1':3',1''-terphenyl]-4,4''-dicarbonitrile (1 eq), PdCl2(PPh3)2 (0.05 eq), copper iodide (0.05 eq), triphenylphosphine (0.1 eq), and diisopropylamine (0.2 eq) were dissolved in toluene under a nitrogen atmosphere and stirred at 50°C for 24 hours. After cooling, the mixture was washed three times with ethyl acetate and water, separated, and the resulting organic layer was dried with MgSO4 and then vacuum dried. The mixture was purified by column chromatography to obtain intermediate 36-1 (yield 65%).

[0428] 2) Synthesis of Intermediate 36-2

[0429] Under a nitrogen atmosphere, intermediate 36-1 (1 eq), 6-ethynyl-5-(trifluoromethyl)-[1,1'-biphenyl]-3,4'-dicarbonitrile (1 eq), PdCl2(PPh3)2 (0.05 eq), copper iodide (0.05 eq), triphenylphosphine (0.1 eq), and diisopropylamine (0.2 eq) were dissolved in toluene and stirred at 50°C for 24 hours. After cooling, the mixture was washed three times with ethyl acetate and water, separated, and the resulting organic layer was dried with MgSO4 and then vacuum dried. The mixture was purified by column chromatography to obtain intermediate 36-2 (yield 58%).

[0430] 3) Synthesis of intermediate 36-3

[0431] Intermediate 36-2 (1 eq), PdCl2 (0.05 eq), Silver hexafluoroantimonate (V) (0.1 eq), and Diphenylsulfoxide (3 eq) were dissolved in dichloroethylene and stirred at 60°C for 24 hours. Subsequently, Cs2CO3 (0.1 eq) was added and stirred for 12 hours. The mixture was then extracted with dichloromethane, added to 35% hydrochloric acid, and stirred for 2 hours. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Intermediate 36-3 was obtained by column chromatography. (Yield 36%)

[0432] 4) Synthesis of Compound 36

[0433] Intermediate 36-3 (1 eq), malononitrile (2 eq), and dichloromethane were stirred under a nitrogen atmosphere for 30 minutes. Titanium tetrachloride (3 eq) was slowly injected, followed by the addition of pyridine and stirring at room temperature. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Compound 36 was obtained by column chromatography. (Yield 2.0%)

[0434] The generated compound was confirmed via MS / FAB.

[0435] C 62 H 22 F3N 11 cal. 977.20, found 977.22

[0437] Synthesis Example 3: Synthesis of Compound 77

[0438] Compound 77 according to one embodiment can be synthesized, for example, as follows.

[0439]

[0440]

[0441] 1) Synthesis of intermediate 77-1

[0442] Under a nitrogen atmosphere, 2'-(3,5-dibromo-2,6-bis(cyanomethyl)phenyl)-[1,1':3',1''-terphenyl]-4,4'',5'-tricarbonitrile (1 eq), 4-ethynyl-2,6-bis(trifluoromethyl)benzonitrile (2 eq), PdCl2(PPh3)2 (0.05 eq), copper iodide (0.05 eq), triphenylphosphine (0.1 eq), and diisopropylamine (0.2 eq) were dissolved in toluene and stirred at 50°C for 24 hours. After cooling, the mixture was washed three times with ethyl acetate and water, separated, and the resulting organic layer was dried with MgSO4 and then vacuum dried. The mixture was purified by column chromatography to obtain intermediate 77-1 (yield 60%).

[0443] 2) Synthesis of intermediate 77-2

[0444] Intermediate 77-1 (1 eq), PdCl2 (0.05 eq), Silver hexafluoroantimonate (V) (0.1 eq), and Diphenylsulfoxide (3 eq) were dissolved in dichloroethylene and stirred at 60°C for 24 hours. Subsequently, Cs2CO3 (0.1 eq) was added and stirred for 12 hours. The mixture was then extracted with dichloromethane, added to 35% hydrochloric acid, and stirred for 2 hours. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Intermediate 77-2 was obtained by column chromatography. (Yield 39%)

[0445] 3) Synthesis of Compound 77

[0446] Intermediate 77-2 (1 eq), malononitrile (2 eq), and dichloromethane were stirred under a nitrogen atmosphere for 30 minutes. Titanium tetrachloride (3 eq) was slowly injected, followed by the addition of pyridine and stirring at room temperature. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Compound 77 was obtained by column chromatography (yield 2.3%).

[0447] The generated compound was confirmed via MS / FAB.

[0448] C 59 H 15 F 12 N 11 cal. 1105.13, found 1105.12

[0450] Synthesis Example 4: Synthesis of Compound 89

[0451] Compound 89 according to one embodiment can be synthesized, for example, as follows.

[0452]

[0453]

[0454] 1) Synthesis of intermediate 89-1

[0455] 2'',5''-dibromo-3'',6''-bis(cyanomethyl)-3',6'''-bis(trifluoromethyl)-[1,1':2',1'':4'',1''':2''',1''''-quinquephenyl]-4,4'',4'''',5'-tetracarbonitrile (1 eq), 5-ethynyl-2-isocyano-1,3-bis(trifluoromethyl)benzene (2 eq), PdCl2(PPh3)2 (0.05 eq), Copper iodide (0.05 eq), Triphenylphosphine (0.1 eq), and Diisopropylamine (0.2 eq) were dissolved in toluene under a nitrogen atmosphere and stirred at 50 degrees Celsius for 24 hours. After cooling, the organic layer obtained by separating the liquids was washed three times with ethyl acetate and water, dried with MgSO4, and then dried under reduced pressure. The intermediate 89-1 was obtained by purification by column chromatography (yield 56%).

[0456] 2) Synthesis of Intermediate 89-2

[0457] Intermediate 89-1 (1 eq), PdCl2 (0.05 eq), Silver hexafluoroantimonate (V) (0.1 eq), and Diphenylsulfoxide (3 eq) were dissolved in dichloroethylene and stirred at 60°C for 24 hours. Subsequently, Cs2CO3 (0.1 eq) was added and stirred for 12 hours. The mixture was then extracted with dichloromethane, added to 35% hydrochloric acid, and stirred for 2 hours. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Intermediate 89-2 was obtained by column chromatography (yield 37%).

[0458] 3) Synthesis of Compound 89

[0459] Intermediate 89-2 (1 eq), malononitrile (2 eq), and dichloromethane were stirred under a nitrogen atmosphere for 30 minutes. Titanium tetrachloride (3 eq) was slowly injected, followed by the addition of pyridine and stirring at room temperature. After cooling, the organic layer obtained by extraction with an aqueous solution of dichloromethane and NH4Cl was dried under reduced pressure with MgSO4. Compound 89 was obtained by column chromatography (yield 1.7%).

[0460] The generated compound was confirmed via MS / FAB.

[0461] C 68 H 16 F 18 N2cal. 1342.13, found 1342.12

[0463] Fabrication of light-emitting devices

[0464] As an anode, 15Ω / cm 2 A glass substrate (Corning product) having an ITO electrode (1300 Å) formed thereon was cut to a size of 50 mm x 50 mm x 0.7 mm, and the cut substrate was ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water. After cleaning the ultrasonically cleaned substrate by irradiating it with ultraviolet light for 30 minutes and exposing it to ozone, it was mounted in a vacuum deposition apparatus.

[0465] Subsequently, a hole injection layer with a thickness of 100 Å was formed by vacuum depositing a p-dopant compound and HT-7 in a weight ratio of 3:97 on the anode. A hole transport layer with a thickness of 1250 Å was formed by vacuum depositing HT-8 on the hole injection layer. A emitting layer with a thickness of 300 Å was formed by vacuum depositing PH-8, PH-7, and PD1-9 in a weight ratio of 45:45:10 on the hole transport layer.

[0466] A hole blocking layer with a thickness of 50 Å was formed by vacuum depositing ET-4 on the above-mentioned light-emitting layer. An electron transport layer with a thickness of 310 Å was formed by vacuum depositing ET-4 and LiQ in a weight ratio of 5:5 on the above-mentioned hole blocking layer.

[0467] On the electron transport layer, Yb was vacuum deposited to form an electron injection layer with a thickness of 15 Å. On the electron injection layer, Ag and Mg were vacuum deposited in a weight ratio of 5:5 to form a cathode with a thickness of 1,000 Å.

[0469] As the above p-dopant compounds, compounds of the examples synthesized according to the synthesis examples described above and commercially available comparative example compounds were used, and these are as follows.

[0470] <Example Compounds>

[0471]

[0472]

[0474] Comparative Examples Compounds

[0475]

[0476]

[0477]

[0478] The following materials used in the fabrication of the above-mentioned light-emitting device were commercially available materials that had been sublimated and purified.

[0479]

[0481] Evaluation example

[0482] Evaluation Example 1. Evaluation of Physical Properties of Polycyclic Compounds

[0483] The physical properties of the compounds of the above-described examples and the compounds of the comparative examples were evaluated as follows, and the results are shown in Table 1 below.

[0484] Specifically, each evaluation condition was as follows.

[0485] - Method for evaluating HOMO energy levels: After obtaining a potential (V)-current (A) graph of each compound using cyclic voltammetry (CV) (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylforamide) / electrode: 3-electrode system (working electrode: GC, reference electrode: Ag / AgCl, auxiliary electrode: Pt)), the HOMO energy level of each compound is calculated from the oxidation onset of the graph.

[0486] - LUMO energy level evaluation method: After obtaining a potential (V)-current (A) graph of each compound using cyclic voltammetry (CV) (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylforamide) / electrode: 3-electrode system (working electrode: GC, reference electrode: Ag / AgCl, auxiliary electrode: Pt)), the LUMO energy level of each compound is calculated from the reduction onset of the graph.

[0487] - Method for evaluating hole and electron mobility: Evaluated using the space-charge-limited current (SCLC) method described in the literature “Hole mobility of N,N'-bis(naphtanlen-1-yl)-N,N'-bis(phenyl)benzidine investigated by using space-charge-limited currents, ‘Appl. Phys. Lett. 90, 203512 (2007)”.

[0488] The glass transition temperature (Tg) was analyzed by Differential Scanning Calorimetry (DSC). Analysis conditions: Scan rate 10 for a sample weighing 5 mg 300 at room temperature After heating to 300 from 25 It cooled down to 300 again. Heating was performed until. The glass transition temperature was measured from the inflection point on the graph obtained during the second heating.

[0489] compound HOMO(eV) LUMO(eV) Hole mobility (cm²) 2 / Vs) Electron mobility (cm²) 2 / Vs) Glass transition temperature (°C) Comparative Example 1 C1 -9.05 -4.81 1.7E-03 5.0E-03 119 Comparative Example 2 C2 -7.91 -5.22 5.4E-04 4.7E-03 118 Comparative Example 3 C3 -7.76 -5.29 1.8E-04 3.3E-03 120 Comparative Example 4 C4 -7.76 -5.25 1.2E-04 4.6E-03 114 Comparative Example 5 C5 -7.66 -5.32 7.6E-05 5.1E-03 117 Example 1 1 -7.87 -5.56 3.3E-04 1.6E-03 152 Example 2 36 -7.84 -5.58 3.0E-04 1.3E-03 138 Example 3 77 -8.03 -5.62 5.9E-04 8.8E-04 141 Example 4 89 -7.95 -5.65 8.3E-04 1.3E-03 147

[0491] From Table 1 above, the polycyclic compounds according to the examples achieved deep LUMO energy, high hole mobility, low electron mobility, and a high glass transition temperature by introducing a substituent capable of protecting the core. Accordingly, the polycyclic compounds according to the examples can increase the generation efficiency of excitons in the emissive layer, and the high glass transition temperature prevents the degradation of the polycyclic compounds during high-temperature processes.

[0492] Compounds according to comparative examples were evaluated to have shallow LUMO energy levels, with their hole mobility decreasing or electron mobility increasing, and the glass transition temperature not improving.

[0494] Evaluation Example 2. Performance evaluation of a light-emitting device

[0495] The characteristics of the light-emitting device fabricated according to the above-described embodiments and comparative examples are a current density of 10 mA / cm² 2 Measurements were taken based on the V7000 OLED IVL Test System (Polaronix).

[0496] Specifically, luminance of 1000 cd / m² 2 The driving voltage (V) was measured using a source meter (Keithley Instrument, 2400 series), and the luminous efficiency (Cd / A) was measured using a luminance meter CS-2000 (Konica Minolta). The light-emitting element was continuously driven at a current density of 10 mA / cm2, and the time until the luminance dropped from an initial value to 95% of that value was measured. The relative value based on the time measured in the light-emitting element using the compound of Comparative Example 2 was expressed as the lifetime (T95) of each light-emitting element.

[0497] The results are shown in Table 2 below.

[0498] p-dopant Relative driving voltage (V) Relative efficiency (cd / A / y) Relative lifespan (T95) Comparative Example 1 C1 4.2 16.9 115% Comparative Example 2 C2 3.8 17.4 121% Comparative Example 3 C3 3.7 17.6 122% Comparative Example 4 C4 3.7 17.5 121% Comparative Example 5 C5 3.6 17.5 123% Example 1 1 3.3 18.7 133% Example 2 36 3.4 18.4 130% Example 3 77 3.3 18.6 133% Example 4 89 3.2 18.8 135%

[0500] From Table 2 above, the driving voltage was reduced while the luminous efficiency and relative lifetime were improved in the light-emitting devices to which the polycyclic compounds according to the examples were applied. It was confirmed that the hole injection performance was further improved in the polycyclic compounds of the examples by suppressing or preventing interactions with surrounding compounds within the hole injection layer.

[0501] In the light-emitting devices using compounds according to the comparative examples, the driving voltage was high, and the luminous efficiency and relative lifespan were also low. Explanation of the symbols

[0503] ED: Light-emitting element 110: First electrode 120: Hole transfer region 122: Hole injection layer 124: Precision transport layer 130: Emissive layer 140: Electron transport region 142a: First electron injection layer 142b: Second electron injection layer 144: Electron transport layer 150: Second electrode 160a: First capping layer 160b: Second capping layer 200: Base board 205: Buffer layer 210: Active layer 220: Gate insulation layer 230: Gate electrode 240: Interlayer insulation film 250, 260: Connecting electrodes 270: via insulating film 280: Pixel definition membrane 290: Bag layer 300: Functional layer 310, 320: Barrier layer 400: Vehicle 10: Electronic devices 11: Display Module 12: Processor 13, 15: Memory 14: Power Module 15: Memory

Claims

Claim 1 Polycyclic compounds represented by the following Chemical Formula 1 or Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] (In the above chemical formulas 1 and 2, Z1 to Z 10 Each is independently hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C7-C 60 arylalkyl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C3-C 60 heteroarylalkyl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 A condensed polycyclic group, or a substituted or unsubstituted silyl group, wherein two or more adjacent groups among these may optionally combine to form a saturated or unsaturated ring, and Z1 to Z 10 At least one of them is selected from a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, and a substituted or unsubstituted carbazole group, and at least one of the remainder is an electron-withdrawing group or a group substituted with an electron-withdrawing group, wherein the electron-withdrawing group is a group in which the para-Hammett substituent constant (σp) is greater than 0). Claim 2 In paragraph 1, Z1, Polycyclic compounds, wherein at least one of Z3, Z5, and Z6 is each independently selected from the group represented by the following chemical formulas 3-1 to 3-4: (In the above chemical formulas 3-1 to 3-4, R a Each is independently hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C2-C 30 alkenyl groups, substituted or unsubstituted C2-C 30 alkynyl groups, substituted or unsubstituted C1-C 30 alkoxy groups, substituted or unsubstituted C3-C 30 cycloalkyl groups, substituted or unsubstituted C5-C 30 cycloalkenyl groups of, substituted or unsubstituted C3-C 30 heterocycloalkyl groups, substituted or unsubstituted C3-C 30 heterocycloalkenyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 heteroaryl groups, substituted or unsubstituted C3-C 30 heteroarylalkyl groups, substituted or unsubstituted C6-C 30 The aryloxy group, or substituted or unsubstituted C6-C 30 It is an arylthio group of, and the above R a If α is 2 or more, they are identical or different, and among them, 2 or more adjacent groups may optionally combine with each other to form a saturated or unsaturated ring, n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 3, and if n1, n2, or n3 is 2 or more, they are identical or different, and X 1 and X 2 are each independently CR1R2, NR3, O, S, or Se, and R1 to R3 are each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 The heteroaryl group of, or substituted or unsubstituted C3-C 30 It is a heteroarylalkyl group, and *- indicates the bonding position). Claim 3 In paragraph 2, Z1 and A polycyclic compound in which Z3 is each independently selected from the group represented by the above chemical formulas 3-1 to 3-4, or Z5 and Z6 are each independently selected from the group represented by the above chemical formulas 3-1 to 3-4. Claim 4 In claim 1, the electron-withdrawing groups are each independently -F, -Cl, -Br, -I, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, and π electron-deficient nitrogen-containing C3-C 30 cyclic group of (ð electron-depleted nitrogen-containing C3-C 30 A polycyclic compound selected from cyclic groups. Claim 5 A polycyclic compound according to claim 4, wherein the electron-withdrawing group is each independently selected from -F, -Cl, -Br, -I, -CF3, -CN, -SCN, -SOCH3, -SOCH2CH3, -SCH(CH3)2, -NO2, 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 pyrimidine group, substituted or unsubstituted naphthiridine group, substituted or unsubstituted phthalazine group, substituted or unsubstituted quinoline group, substituted or unsubstituted quinazolin group, substituted or unsubstituted benzosinnoline group, substituted or unsubstituted phenanthroline group, and substituted or unsubstituted acridine group. Claim 6 In claim 1, a polycyclic compound represented by any one of the following chemical formulas 1-1 to 1-10: (In the above chemical formulas 1-1 to 1-10, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 3, and when n2 and n3 are 2 or more, they are the same or different, and R c is hydrogen, deuterium, -CN, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C3-C 30 cycloalkyl groups, substituted or unsubstituted C3-C 30 heterocycloalkyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C7-C 30 arylalkyl groups, substituted or unsubstituted C2-C 30 The heteroaryl group of, or substituted or unsubstituted C3-C 30 It is a heteroarylalkyl group of, and the above R c If α is 2 or more, they are identical or different, and among them, 2 or more adjacent groups may optionally combine to form a saturated or unsaturated ring, and 2 or more R b1 and R b2 are identical or different, and these are each independently hydrogen, deuterium, -CN, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group, where Ar1 and Ar2 are each independently substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group, and 2 or more R e are identical or different, and are each independently selected from the electron-withdrawing groups, and R4 and R5 are each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, substituted or unsubstituted C1-C 30 Selected from the alkyl group and the electron-withdrawing group, and R d1 to R d4 Each is independently the electron-withdrawing group, the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophen group, or the substituted or unsubstituted carbazole group, and two or more of these are each independently the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophen group, and the substituted or unsubstituted carbazole group, and are selected from among). Claim 7 In claim 6, in the above chemical formulas 1-1 to 1-6, 2 or more R b1 Each is independently substituted or unsubstituted C6-C 30 The aryl group of, or a substituted or unsubstituted C2-C 30 It is a heteroaryl group, and 2 or more R b2 Polycyclic compounds, each independently hydrogen, deuterium, -CN, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, or -CFH2. Claim 8 In claim 6, in the above chemical formulas 1-1 and 1-7, R4 is selected from the electron-withdrawing groups, and R5 is each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, and substituted or unsubstituted C1-C 30 A polycyclic compound selected from the alkyl groups of Claim 9 In claim 6, in the above chemical formulas 1-7 to 1-10, R d1 and R d2 At least one of, and R d3 and R d4 A polycyclic compound, wherein at least one of which is independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, or a substituted or unsubstituted carbazole group. Claim 10 In claim 6, a polycyclic compound having a degree of deuteration of 10% to 100% according to the following Formula 1: [Formula 1] Degree of deuteration (%) = (Number of deuterium atoms) / (Number of deuterium atoms + Number of hydrogen atoms) x 100 (in Formula 1 above, the number of deuterium atoms and the number of hydrogen atoms refer to the respective number of deuterium and hydrogen atoms contained in the polycyclic compound). Claim 11 In paragraph 1, 2.5 x 10 -4 cm 2 / Vs or higher and 1.0 x 10 -3 cm 2 Polycyclic compounds having hole mobility of / Vs or less. Claim 12 In paragraph 1, 8.0 x 10 -4 cm 2 / Vs or more and 2.5 x 10 -3 cm 2 Polycyclic compounds having electron mobility of / Vs or less. Claim 13 A polycyclic compound having a glass transition temperature of 125°C or higher, according to claim 1. Claim 14 A polycyclic compound according to claim 1, having LUMO energy levels of -5.0 eV to -6.0 eV. Claim 15 A light-emitting device comprising: a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises one or more light-emitting structures including a hole transport region, a light-emitting layer, and an electron transport region, and wherein the hole transport region comprises a polycyclic compound of claim 1. Claim 16 A light-emitting device according to claim 15, wherein the intermediate layer comprises two or more of the light-emitting structures, and one or more of the hole transport regions comprises the polycyclic compound. Claim 17 A light-emitting device according to claim 15 or 16, wherein the hole transport region comprises a hole injection layer, and the hole injection layer comprises the polycyclic compound. Claim 18 A light-emitting device according to claim 17, comprising 1% to 40% by weight of the polycyclic compound based on the total weight of the hole injection layer. Claim 19 An electronic device comprising the light-emitting element of claim 15 or 16. Claim 20 In the 19th, the electronic device is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and / or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

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