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KR-20260065042-A - CONDENSED HETEROCYCLIC COMPOUND, LIGHT EMITTING ELEMENT, ELECTRONIC DEVICE AND APPARATUS

KR20260065042AKR 20260065042 AKR20260065042 AKR 20260065042AKR-20260065042-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]

Inventors

  • 심문기
  • 황석환
  • 김세란
  • 김형종
  • 박준하
  • 박한규
  • 성민재
  • 신효섭
  • 이재용
  • 정민정

Assignees

  • 삼성디스플레이 주식회사

Dates

Publication Date
20260508
Application Date
20241031

Claims (20)

  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 claim 1, a condensed heterocyclic 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 chemical formulas 1-1 to 1-6, the definitions of X 1 to X 2 , R 1 to R 7 , n, m, p, q, and r are the same as in claim 1, and X3 and X4 are each independently directly coupled, O, S, Se, NR, or CRR', and R, R', 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 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, 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 4, and p' and m' are each independently integers of 0 or 1 to 3, and p'' and m'' are independently 0, 1, or 2, respectively, and If v, w, p', m', p'' and m'' are 2 or more, multiple R 4 , R 5 , R 11 and R 12 are each independently identical or different from each other.
  3. A condensed heterocyclic compound according to claim 1, wherein R 8 to R 10 in Chemical Formula 2 are each independently hydrogen or deuterium.
  4. In claim 1, a condensed heterocyclic compound represented by the following chemical formula 1-7: [Chemical Formula 1-7] In Chemical Formula 1-7, the definitions of X 1 to X 2 , R 1 to R 7 , m, p, and r are the same as in Claim 1, and D1 to D4 are each independently hydrogen or deuterium.
  5. A condensed heterocyclic compound according to claim 1, wherein in the above formulas 1 and 2, R3 to R10 are each independently a substituted or unsubstituted C6 - C20 aryl group or a substituted or unsubstituted C2 to C15 heteroaryl group.
  6. A condensed heterocyclic compound according to claim 1, wherein in the above chemical formula 1, n, m, p, and q are each independently 0 or 1.
  7. A condensed heterocyclic compound according to claim 1, wherein in the above chemical formula 2, s, t, and u are each independently 0 or 1.
  8. In claim 1, wherein in Formula 1 and Formula 2, R3 to R10 are each independently hydrogen, deuterium, a cyano group, a C4 - C15 tert-alkyl group substituted or unsubstituted with deuterium, a C3 - C15 trialkylsilyl group substituted or unsubstituted with deuterium, a C18 - C40 triarylsilyl group substituted or unsubstituted with deuterium, a phenyl group substituted or unsubstituted with deuterium, a cyanophenyl 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 tetrahydronaphthalene group substituted or unsubstituted with deuterium, or a C11 - C40 group substituted or unsubstituted with deuterium A condensed heterocyclic compound selected from the group consisting of an alkyltetrahydronaphthalene group, a C12 - C20 diarylamine group substituted or unsubstituted with deuterium, a carbazole group substituted or unsubstituted with deuterium, a dibenzofuran group substituted or unsubstituted with deuterium, a phenothiazine group substituted or unsubstituted with deuterium, and a pyridine group substituted or unsubstituted with deuterium.
  9. In claim 1, a condensed heterocyclic compound comprising at least one of the compounds represented by the following chemical formulas: .
  10. A condensed heterocyclic compound having a HOMO (highest occupied molecular orbital) energy level of -5.3 eV or less in claim 1.
  11. 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] 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 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) 2 R or; Two or more of R3 to R10 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.
  12. A light-emitting device according to claim 11, wherein the light-emitting layer comprises a host and a dopant, and the condensed heterocyclic compound is provided as a Thermally Activated Delayed Fluorescence (TADF) dopant.
  13. In Clause 12, the light-emitting element further comprises a phosphorescent dopant.
  14. In claim 12, the light-emitting device comprises a hole-transporting host represented by the chemical formula HT and an electron-transporting host represented by the chemical formula ET: [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.
  15. A light-emitting device according to claim 11, wherein the light-emitting layer emits blue light, and the maximum emission wavelength of the blue light is 440 nm to 470 nm.
  16. An electronic device comprising a light-emitting element according to paragraph 11.
  17. In claim 16, the light-emitting element comprises a first electrode, a second electrode, and two or more light-emitting layers disposed between the first electrode and the second electrode, and An electronic device comprising at least one of the above light-emitting layers, the condensation heterocyclic compound of the above chemical formula 1.
  18. An electronic device according to claim 17, further comprising a color control unit including a light converter.
  19. In paragraph 16, the light-emitting element comprises a blue light-emitting element, a red light-emitting element, and a green light-emitting element, and An electronic device comprising at least one selected from the group consisting of the blue light-emitting element, the red light-emitting element, and the green light-emitting element, the condensed heterocyclic compound of Formula 1.
  20. Includes a light-emitting element according to Clause 11, 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, electronic device and apparatus 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 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 condensed heterocyclic compound comprising terphenyl groups 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, an octyl group, etc. An alkylene group may refer to a divalent hydrocarbon group from which two hydrogen atoms have been removed from a straight-chain or branched