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KR-20260065003-A - POLYCYCLIC COMPOUND, LIGHT EMITTING ELEMENT AND ELECTRONIC DEVICE

KR20260065003AKR 20260065003 AKR20260065003 AKR 20260065003AKR-20260065003-A

Abstract

A polycyclic compound represented by Chemical Formula 1 is provided. A light-emitting element is provided, comprising a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and comprising a light-emitting layer. The light-emitting layer comprises the polycyclic compound. An electronic device comprising the light-emitting element is provided. [Chemical Formula 1]

Inventors

  • 김세란
  • 김현득
  • 김회림
  • 박준하
  • 백승인
  • 유동선
  • 윤석규

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260508
Application Date
20241031

Claims (20)

  1. Polycyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, X 1 and X 2 are each independently N(R 10 ), S, O, or Se, and R1 to R10 are each independently hydrogen, deuterium, hydroxyl group, cyano group, -F, -Cl, -Br, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , a substituted or unsubstituted C1- C60 alkyl group, a substituted or unsubstituted C2 - C60 alkenyl group, a substituted or unsubstituted C2 - C60 alkynyl group, a substituted or unsubstituted C1 - C60 alkoxy group, a substituted or unsubstituted C3 - C60 cycloalkyl group, a substituted or unsubstituted C5 - C60 cycloalkenyl group, a substituted or unsubstituted C3 - C60 heterocycloalkyl group, a substituted or unsubstituted C3 - C60 heterocycloalkenyl group, a substituted or unsubstituted C3 - C60 heterocycloalkenyl group, or An unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C6 - C60 arylalkyl group, a substituted or unsubstituted C2- C60 heteroaryl group, a substituted or unsubstituted C2 - C60 heteroarylalkyl group, a substituted or unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, a substituted or unsubstituted C8 - C60 condensed polycyclic group, or a substituted or unsubstituted silyl group, wherein two or more adjacent groups among R1 to R9 may optionally bond to each other to form a saturated or unsaturated ring, and RA and RB are identical or different from each other, and are each independently substituted or unsubstituted carbazole groups, and At least one of RA and RB is selected from the group consisting of carbazole groups comprising a structure in which a cycloaliphatic hydrocarbon ring is condensed to one or two of two six-membered benzene rings fused to both sides of one five-membered nitrogen-containing ring of the carbazole group).
  2. In claim 1, the alicyclic hydrocarbon ring is a polycyclic compound selected from a 5-membered ring to a 9-membered ring.
  3. In claim 1, the polycyclic compound wherein the alicyclic hydrocarbon ring is each independently selected from substituted or unsubstituted cycloalkane, substituted or unsubstituted bicycloalkane, and substituted or unsubstituted spiroalkane.
  4. A polycyclic compound according to claim 1, wherein R A is represented by the following chemical formula 2-1 and R B is represented by the following chemical formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] (In the above chemical formulas 2-1 and 2-2, R 11 to R 14 are identical or different from one another and are each independently hydrogen, deuterium, -F, -Cl, -Br , -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , a substituted or unsubstituted C1 - C60 alkyl group, a substituted or unsubstituted C3 - C60 cycloalkyl group, a substituted or unsubstituted C6 - C60 arylalkyl group, a substituted or unsubstituted C2 - C60 heteroarylalkyl group, or a substituted or unsubstituted silyl group, and i, o, k, and p are each independently integers from 0 to 4, and Two or more adjacent R 11s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 12s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 13s can optionally combine to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 14s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and RA comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R11s and a cycloaliphatic hydrocarbon ring formed by 2 or more R12s ; R B comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R 13s and a cycloaliphatic hydrocarbon ring formed by 2 or more R 14s ; RA comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R11s and a cycloaliphatic hydrocarbon ring formed by 2 or more R12s , and RB comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R13s and a cycloaliphatic hydrocarbon ring formed by 2 or more R14s ).
  5. A polycyclic compound according to claim 4, wherein at least one of the alicyclic hydrocarbon ring formed by 2 or more R11 , the alicyclic hydrocarbon ring formed by 2 or more R12 , the alicyclic hydrocarbon ring formed by 2 or more R13 , and the alicyclic hydrocarbon ring formed by 2 or more R14 is each independently selected from substituted or unsubstituted C1 - C9 cycloalkane, substituted or unsubstituted C1 - C30 bicycloalkane, and substituted or unsubstituted C1 - C30 spiroalkane.
  6. In claim 5, at least one of the alicyclic hydrocarbon ring formed by 2 or more R 11 , the alicyclic hydrocarbon ring formed by 2 or more R 12 , the alicyclic hydrocarbon ring formed by 2 or more R 13 , and the alicyclic hydrocarbon ring formed by 2 or more R 14 is, respectively, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted bicyclo[2.1.0]pentane, substituted or unsubstituted bicyclo[2.2.0]hexane, substituted or unsubstituted bicyclo[4.1.0]heptane, substituted or unsubstituted spiro[5.5]undecae, substituted or unsubstituted spiro[4.4]nonane, substituted or unsubstituted spiro[3.4]octane, substituted or unsubstituted spiro[4.5]decane, and polycyclic compounds selected from the group consisting of substituted or unsubstituted spiro[6.6]tridecanes.
  7. In claim 4, a polycyclic compound wherein R A and R B are identical or different from each other and each independently represented by any one of the following chemical formulas 3-1 to 3-6: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] (In the above chemical formulas 3-1 to 3-6, R c1 and R c2 are identical or different from each other and are each independently hydrogen, deuterium, -F, -Cl, -Br, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , a substituted or unsubstituted C1 - C30 alkyl group, or a substituted or unsubstituted C3 - C30 cycloalkyl group, and R c3 and R c4 are identical or different from each other and are each independently hydrogen, deuterium, -CD3 , -CD2H , -CDH2 , a substituted or unsubstituted C1 - C30 alkyl group, or a substituted or unsubstituted C3 - C30 cycloalkyl group, and n1 and n2 are identical or different from each other, and each independently is an integer from 0 to 2, and n3 and n4 are identical or different from each other, and each independently is an integer from 0 to 4, and Two or more adjacent R c3s can optionally combine to form a saturated ring, and Two or more adjacent R c4 can optionally combine to form a saturated ring).
  8. A polycyclic compound according to claim 1, wherein R A and R B are identical or different from each other and each independently represented by either Formula 3-2 and Formula 3-3.
  9. In claim 1, a polycyclic compound represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] (In the above chemical formulas 1-1 to 1-6, R1 to R9 , R10a , and R10b are each independently hydrogen, deuterium, hydroxyl group, cyano group, -F, -Cl, -Br, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C60 cycloalkyl group, substituted or unsubstituted C5 - C60 cycloalkenyl group, substituted or unsubstituted C3 -C60 heterocycloalkyl group, substituted or unsubstituted C3 -C60 of A heterocycloalkenyl group, a substituted or unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C6- C60 arylalkyl group, a substituted or unsubstituted C2 - C60 heteroaryl group, a substituted or unsubstituted C2 - C60 heteroarylalkyl group, a substituted or unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C8-C60 condensed polycyclic group , or a substituted or unsubstituted silyl group, wherein two or more adjacent groups among R1 to R9 may optionally bond to each other to form a saturated or unsaturated ring, and R 15 to R 18 are identical or different from one another and are each independently hydrogen, deuterium, -CD3 , a substituted or unsubstituted C1 - C30 alkyl group, or a substituted or unsubstituted C3 - C30 cycloalkyl group, and R 19 to R 22 are identical or different from one another and are each independently hydrogen, deuterium, -F, -Cl, -Br , -CD3, -CD2H , -CDH2 , a substituted or unsubstituted C1 - C30 alkyl group, or a substituted or unsubstituted C3 - C30 cycloalkyl group, and A plurality of m1s are each independently integers from 0 to 4, and a plurality of m2s are each independently integers from 0 to 2, and Two or more adjacent R15s may optionally combine to form a saturated ring, two or more adjacent R16s may optionally combine to form a saturated ring, two or more adjacent R17s may optionally combine to form a saturated ring, and two or more adjacent R18s may optionally combine to form a saturated ring).
  10. In claim 9, a polycyclic compound represented by either of the above chemical formulas 1-5 and 1-6.
  11. In claim 9, a polycyclic compound wherein R 10a and R 10b are each independently represented by any one of the following chemical formulas 4-1 to 4-12: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6] [Chemical Formula 4-7] [Chemical Formula 4-8] [Chemical Formula 4-9] [Chemical Formula 4-10] [Chemical Formula 4-11] [Chemical Formula 4-12] (In the above chemical formulas 4-1 to 4-12, A plurality of m3s are identical or different from each other and are each independently integers from 0 to 5, a plurality of m4s are identical or different from each other and are each independently integers from 0 to 4, a plurality of m5s are identical or different from each other and are each independently integers from 0 to 3, and The singular or plural R d are identical or different from one another and are each independently hydrogen, deuterium, a substituted or unsubstituted C1 - C10 alkyl group, a substituted or unsubstituted C2 - C10 alkenyl group, a substituted or unsubstituted C3 - C10 cycloalkyl group, or a substituted or unsubstituted C6 - C10 aryl group, and If R d is plural, two adjacent of them may optionally combine to form a saturated or unsaturated ring, and In chemical formulas 4-9 to 4-11, the *- bonding site is one of carbons 1 to 4, and in chemical formula 4-12, the *- bonding site is one of carbons 1 to 3).
  12. A polycyclic compound according to claim 1, wherein K RISC is 1.00 x 10⁵ s⁻¹ or greater.
  13. A polycyclic compound according to claim 1, wherein the oscillator strength (f) is 0.36 or higher and △E ST is 0.39 eV or lower.
  14. First electrode; Second electrode; and A light-emitting element comprising a light-emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound of the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, X 1 and X 2 are each independently N(R 10 ), S, O, or Se, and R1 to R10 are each independently hydrogen, deuterium, hydroxyl group, cyano group, -F, -Cl, -Br, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , a substituted or unsubstituted C1- C60 alkyl group, a substituted or unsubstituted C2 - C60 alkenyl group, a substituted or unsubstituted C2 - C60 alkynyl group, a substituted or unsubstituted C1 - C60 alkoxy group, a substituted or unsubstituted C3 - C60 cycloalkyl group, a substituted or unsubstituted C5 - C60 cycloalkenyl group, a substituted or unsubstituted C3 - C60 heterocycloalkyl group, a substituted or unsubstituted C3 - C60 heterocycloalkenyl group, a substituted or unsubstituted C3 - C60 heterocycloalkenyl group, or An unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C6 - C60 arylalkyl group, a substituted or unsubstituted C2- C60 heteroaryl group, a substituted or unsubstituted C2 - C60 heteroarylalkyl group, a substituted or unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, a substituted or unsubstituted C8 - C60 condensed polycyclic group, or a substituted or unsubstituted silyl group, wherein two or more adjacent groups among R1 to R9 may optionally bond to each other to form a saturated or unsaturated ring, and RA and RB are identical or different from each other, and are each independently substituted or unsubstituted carbazole groups, and At least one of RA and RB is selected from the group consisting of carbazole groups comprising a structure in which a cycloaliphatic hydrocarbon ring is condensed to one or two of two six-membered benzene rings fused to both sides of one five-membered nitrogen-containing ring of the carbazole group).
  15. A light-emitting device according to claim 14, wherein a plurality of light-emitting layers are disposed between the first electrode and the second electrode, a charge-generating layer is disposed between adjacent light-emitting layers, and at least one of the plurality of light-emitting layers comprises a polycyclic compound of Formula 1.
  16. In claim 14, the polycyclic compound is provided as a thermally activated delayed fluorescence (TADF) dopant, a phosphorescent host, or a fluorescent host, for a light-emitting device.
  17. In claim 14, the light-emitting layer is a light-emitting device having a maximum light-emitting center wavelength of 440 nm to 490 nm.
  18. In claim 14, a light-emitting element in which RA is represented by the following chemical formula 2-1 and RB is represented by the following chemical formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] (In the above chemical formulas 2-1 and 2-2, R 11 to R 14 are identical or different from one another and are each independently hydrogen, deuterium, -F, -Cl, -Br, -CD3 , -CD2H , -CDH2 , -CF3 , -CF2H , -CFH2 , a substituted or unsubstituted C1 - C60 alkyl group, a substituted or unsubstituted C3 - C60 cycloalkyl group, a substituted or unsubstituted C6 - C60 arylalkyl group, a substituted or unsubstituted C2 - C60 heteroarylalkyl group, or a substituted or unsubstituted silyl group, and i, o, k, and p are each independently integers from 0 to 4, and Two or more adjacent R 11s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 12s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 13s can optionally combine to form a cycloaliphatic hydrocarbon ring, and Two or more adjacent R 14s can optionally combine with each other to form a cycloaliphatic hydrocarbon ring, and RA comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R11s and a cycloaliphatic hydrocarbon ring formed by 2 or more R12s ; R B comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R 13s and a cycloaliphatic hydrocarbon ring formed by 2 or more R 14s ; RA comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R11s and a cycloaliphatic hydrocarbon ring formed by 2 or more R12s , and RB comprises at least one of a cycloaliphatic hydrocarbon ring formed by 2 or more R13s and a cycloaliphatic hydrocarbon ring formed by 2 or more R14s ).
  19. An electronic device comprising the light-emitting element of claim 14 or 15.
  20. Includes the light-emitting element of claim 14 or 15, An electronic device that is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, 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.

Description

Polycyclic Compound, Light Emitting Element and Electronic Device The embodiments of the present application relate to polycyclic compounds, light-emitting elements, and electronic devices. 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. 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 above-described light-emitting layer may include a host material and a dopant material for implementing the light-emitting mechanism described above. 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. According to the present disclosure, a polycyclic compound is provided in which a carbazole group is introduced into an aromatic ring of a boron-containing core structure to have an enhanced multiple resonance effect, and a cycloaliphatic hydrocarbon ring is condensed into at least one of the benzene rings fused to both sides of the nitrogen-containing ring of the carbazole group to achieve enhanced luminous efficiency and lifetime characteristics. A light-emitting element, a display device, an electronic device, and an electronic apparatus comprising said polycyclic compound are provided. Definition of Terms 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 (e.g., C1 - C60 , C1 - C10 alkyl group), an alkenyl group (e.g., C2 - C60 , C2 - C10 alkenyl group), an alkynyl group (e.g., C2 -C60, C2- C10 alkynyl group), an alkoxy group (e.g., C1 - C60 , C1 - C10 alkoxy group), a hydrocarbon ring group, an aryl group (e.g., C6 - C60 aryl group), and a heterocyclic group (e.g., C1 It may refer to one that is substituted or unsubstituted with one or more substituents selected from the group consisting of (-C 60 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. 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. 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 may be substituted with C1 - C10 alkyl groups, C1 - C10 alkenyl groups, C1 - C10 alkynyl groups, or C6 - C10 aryl groups. In the term “substituted or unsubstituted C a - C b Y group” as used in this specification, 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. 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