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KR-20260065494-A - CONDENSED HETEROCYCLIC COMPOUND, LIGHT EMITTING ELEMENT AND ELECTRONIC DEVICE

KR20260065494AKR 20260065494 AKR20260065494 AKR 20260065494AKR-20260065494-A

Abstract

A condensed heterocyclic 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 condensed heterocyclic compound. An electronic device comprising the light-emitting element is provided. <Chemical Formula 1> Refer to the detailed description of the above chemical formula 1 as set forth in this specification.

Inventors

  • 심문기
  • 성민재
  • 박한규
  • 장태훈
  • 정민정
  • 배성수
  • 황석환
  • 김형종
  • 미야시타 히로카즈
  • 박준하

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260508
Application Date
20250818
Priority Date
20241031

Claims (16)

  1. Condensed heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In Chemical Formula 1, X1 and X2 are each independently O, S, or Se, and R1 and R2 are each independently represented by the following chemical formula 2, and [Chemical Formula 2] In formulas 1 and 2, R3 to R10 are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, 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 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 - C60 A heteroaryl group, a substituted or unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 aryltio group, a substituted or unsubstituted C8 - C60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)RR' or -S(=O) 2 R; Two or more are bonded to each other to form a substituted or unsubstituted C3 - C60 cycloalkyl ring, a substituted or unsubstituted C5 - C60 cycloalkenyl ring, a substituted or unsubstituted C3 -C60 heterocycloalkyl ring, a substituted or unsubstituted C3 - C60 heterocycloalkenyl ring, a substituted or unsubstituted C6 -C60 aryl ring, or a substituted or unsubstituted C2 - C60 heteroaryl ring; R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, 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 heterocycloalkenyl group, substituted or unsubstituted C6- C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C It is a 6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, or a substituted or unsubstituted C8 - C60 condensed polycyclic group, and n, q, and s are each independently integers of 0 or 1 to 3, and m and p are each independently integers of 0 or 1 to 4, and r is 0, 1, or 2, and t and u are each independently integers of 0 or 1 to 5, and If n, m, p, q, r, s, t, and u are each 2 or more, multiple R3 to R10 are each independently identical or different from each other, and * indicates a joint point.
  2. In paragraph 1, The above Chemical Formula 2 is a condensed heterocyclic compound represented by the following Chemical Formula 2-1 or Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In chemical formulas 2-1 to 2-2, the definitions of R8 , R10 , s, and u are the same as in claim 1, and R11 and R12 are each independently hydrogen, deuterium, halogen, cyano group, hydroxyl group, 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 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 -C60 heteroaryl group, substituted or An unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, a substituted or unsubstituted C8 - C60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)RR' or -S(=O) 2R , and R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, 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 heterocycloalkenyl group, substituted or unsubstituted C6- C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C It is a 6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, or a substituted or unsubstituted C8 - C60 condensed polycyclic group, and v and w are each independently integers of 0 or 1 to 5, and If v and w are 2 or more, multiple R 11 and R 12 are each independently identical or different from each other.
  3. In paragraph 1, Condensed heterocyclic compounds represented by any one of the following chemical formulas 1-1 to 1-11: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] In chemical formulas 1-1 to 1-11, The definitions of X 1 , X 2 , R 1 through R 6 are the same as in paragraph 1, and The definitions of R 31 to R 33 are the same as the description of R 3 in Paragraph 1, and The definitions for R 41 to R 44 are the same as the description of R 4 in Paragraph 1, and The definitions for R 51 to R 54 are the same as the description of R 5 in Paragraph 1, and The definitions for R 61 to R 63 are the same as the description of R 6 in Paragraph 1, and m' is an integer from 0 to 2, and n' is 0 or 1, and p' is an integer from 0 to 2, and q' is 0 or 1, and Y 1 is C(Z 1 ) or N, Y 2 is C(Z 2 ) or N, Y 3 is C(Z 3 ) or N, Y 4 is C(Z 4 ) or N, Y 5 is C(Z 5 ) or N, Y 6 is C(Z 6 ) or N, Y 7 is C(Z 7 ) or N, Y 8 is C(Z 8 ) or N, Y 9 is C(Z 9 ) or N, Y 10 is C(Z 10 ) or N, Y 11 is C(Z 11 ) or N, Y 12 is C(Z 12 ) or N, and T1 to T4 are independently single bonds, O, S, or Se, and The descriptions for Z 1 to Z 12 are each identical to the description for R 3 in Paragraph 1.
  4. In paragraph 1, In the above chemical formula 1, at least two of R3 to R6 are identical to each other, condensed heterocyclic compounds.
  5. In paragraph 1, A condensed heterocyclic compound in which, in the above chemical formulas 1 and 2, R3 to R10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 - C60 alkyl group, a substituted or unsubstituted C6 - C20 aryl group, or a substituted or unsubstituted C2 to C15 heteroaryl group.
  6. In paragraph 1, A condensed heterocyclic compound in which, in the above chemical formula 1, n, m, p, and q are each independently 0, 1, or 2.
  7. In paragraph 1, A condensed heterocyclic compound in which, in the above chemical formula 2, s, t, and u are each independently 0 or 1.
  8. In paragraph 1, A condensed heterocyclic compound, wherein in the above formulas 1 and 2, R3 to R10 are each independently selected from the group consisting of hydrogen, deuterium, a C4 - C15 tert-alkyl group substituted or unsubstituted with deuterium, a phenyl group substituted or unsubstituted with deuterium, a C7 - C20 alkylphenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group substituted or unsubstituted with deuterium, a naphthalene group substituted or unsubstituted with deuterium, a carbazole group substituted or unsubstituted with deuterium, a dibenzofuran group substituted or unsubstituted with deuterium, and a pyridine group substituted or unsubstituted with deuterium.
  9. In paragraph 1, Condensed heterocyclic compounds comprising at least one of the compounds represented by the following chemical formulas: .
  10. First electrode; Second electrode; and A light-emitting device comprising an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer comprising a light-emitting layer comprising a condensed heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] In Chemical Formula 1, X1 and X2 are each independently O, S, or Se, and R1 and R2 are each independently represented by the following chemical formula 2, and [Chemical Formula 2] In formulas 1 and 2, R3 to R10 are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, 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 heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C2 - C60 A heteroaryl group, a substituted or unsubstituted C6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 aryltio group, a substituted or unsubstituted C8 - C60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)RR' or -S(=O) 2 R; Two or more are bonded to each other to form a substituted or unsubstituted C3 - C60 cycloalkyl ring, a substituted or unsubstituted C5 - C60 cycloalkenyl ring, a substituted or unsubstituted C3 -C60 heterocycloalkyl ring, a substituted or unsubstituted C3 - C60 heterocycloalkenyl ring, a substituted or unsubstituted C6 -C60 aryl ring, or a substituted or unsubstituted C2 - C60 heteroaryl ring; R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, 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 heterocycloalkenyl group, substituted or unsubstituted C6- C60 aryl group, substituted or unsubstituted C2 - C60 heteroaryl group, substituted or unsubstituted C It is a 6 - C60 aryloxy group, a substituted or unsubstituted C6 - C60 arylthio group, or a substituted or unsubstituted C8 - C60 condensed polycyclic group, and n, q, and s are each independently integers of 0 or 1 to 3, and m and p are each independently integers of 0 or 1 to 4, and r is 0, 1, or 2, and t and u are each independently integers of 0 or 1 to 5, and If n, m, p, q, r, s, t, and u are each 2 or more, multiple R3 to R10 are each independently identical or different from each other, and * indicates a joint point.
  11. In Paragraph 10, A light-emitting device comprising a light-emitting layer including a host and a dopant, wherein the condensed heterocyclic compound is provided as a Thermally Activated Delayed Fluorescence (TADF) dopant.
  12. In Paragraph 11, The above dopant is a light-emitting element that further includes a phosphorescent dopant.
  13. In Paragraph 11, A light-emitting device comprising a hole-transporting host represented by the chemical formula HT and an electron-transporting host represented by the chemical formula ET, wherein the above host: [Chemical Formula HT] In the chemical formula HT, LHT1 , LHT2 , and LHT3 are each independently a directly linked, substituted, or unsubstituted C6 - C30 arylene group, or a substituted or unsubstituted C2 - C30 heteroarylene group, and lx1 to lx3 are each independently integers from 0 to 10, and Ar HT1 and Ar HT2 are each independently a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heteroaryl group, and Ar HT3 is a substituted or unsubstituted C6 - C30 aryl group, and [Chemical Formula ET] In the chemical formula ET, at least one of X ET1 to X ET3 is N and the remainders are each independently CR ET , and R ET is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 - C20 alkyl group, a substituted or unsubstituted C6 - C60 aryl group, or a substituted or unsubstituted C2 - C60 heteroaryl group, and lx1 to lx3 are each independently integers from 0 to 10, and LET1 to LET3 are each independently direct linkage, substituted or unsubstituted C6 - C30 arylene groups, or substituted or unsubstituted C2 - C30 heteroarylene groups, and Ar ET1 to Ar ET3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 - C20 alkyl group, a substituted or unsubstituted C6 - C30 aryl group, or a substituted or unsubstituted C2 - C30 heteroaryl group.
  14. In Paragraph 10, A light-emitting device in which the light-emitting layer emits green light, and the maximum emission wavelength of the green light is 510 nm to 540 nm.
  15. An electronic device comprising a light-emitting element according to paragraph 10.
  16. Includes a light-emitting element according to Clause 10, 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

Condensed heterocyclic compound, light-emitting element and electronic device The embodiments of the present application relate to condensed heterocyclic 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. An organic light-emitting device 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-emitting 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 block diagram of an electronic device according to one embodiment. FIG. 13 is a schematic diagram of an electronic device according to various embodiments. FIG. 14 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 15 is a schematic diagram showing an electronic device according to exemplary embodiments. According to the present disclosure, a condensed heterocyclic compound comprising a terphenyl structure bonded to nitrogen forming a condensed ring is provided. Additionally, a light-emitting element and an electronic device comprising said condensed heterocyclic 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 hydroxyl 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. For example, it may refer to one that is substituted or unsubstituted with one or more substituents selected from the group consisting of C1 - C60 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 3,3-dimethylbutyl group, a hexyl group, a heptyl group,