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EP-4737460-A1 - CONDENSED HETEROCYCLIC COMPOUND, LIGHT-EMITTING DEVICE AND ELECTRONIC DEVICE

EP4737460A1EP 4737460 A1EP4737460 A1EP 4737460A1EP-4737460-A1

Abstract

A light-emitting device includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, where the emission layer includes a condensed heterocyclic compound represented by Chemical Formula 1. In addition, an electronic device that includes the light-emitting device, an electronic apparatus that includes the light-emitting device, and the condensed heterocyclic compound are also provided.

Inventors

  • SIM, MUNKI
  • SUNG, Minjae
  • PAK, Hankyu
  • JANG, TAEHOON
  • JUNG, Minjung
  • BAE, SUNGSOO
  • HWANG, SEOKHWAN
  • KIM, Hyungjong
  • MIYASHITA, HIROKAZU
  • PARK, JUNHA

Assignees

  • Samsung Display Co., Ltd.

Dates

Publication Date
20260506
Application Date
20251020

Claims (15)

  1. A condensed heterocyclic compound represented by Chemical Formula 1: wherein, in Chemical Formula 1, X 1 and X 2 are each independently O, S, or Se, and R 1 and R 2 are each independently a group represented by Chemical Formula 2: and wherein, in Chemical Formulae 1 and 2, R 3 to R 10 are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O) 2 R; and/or optionally, two or more selected from among R 3 to R 10 are combined with each other to form a substituted or unsubstituted C 3 -C 60 cycloalkyl ring, a substituted or unsubstituted C 5 -C 60 cycloalkenyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl ring, a substituted or unsubstituted C 6 -C 60 aryl ring, or a substituted or unsubstituted C 2 -C 60 heteroaryl ring, wherein R, R', and R" are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group or a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, n, q, and s are each independently an integer from 0 to 3, m and p are each independently an integer from 0 to 4, r is an integer from 0 to 2, t and u are each independently an integer from 0 to 5, and * represents a bonding point.
  2. The condensed heterocyclic compound of claim 1, wherein the group represented by Chemical Formula 2 is represented by Chemical Formula 2-1 or Chemical Formula 2-2: and wherein, in Chemical Formulae 2-1 and 2-2, R 8 , R 10 , s, and u are the same as those defined in Chemical Formula 2, R 11 and R 12 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, - SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O) 2 R, R, R', and R" are the same as those defined in Chemical Formulae 1 and 2, and v and w are each independently an integer from 0 to 5.
  3. The condensed heterocyclic compound of claim 1 or claim 2, wherein the condensed heterocyclic compound is represented by one of Chemical Formulae 1-1 to 1-11: in Chemical Formulae 1-1 to 1-11, X 1 , X 2 , and R 1 to R 6 being the same as those defined in Chemical Formulae 1 and 2, R 31 to R 33 are each as described in connection with R 3 , R 41 to R 44 are each as described in connection with R 4 , R 51 to R 54 are each as described in connection with R 5 , R 61 to R 63 are each as described in connection with R 6 , R 71 and R 72 are each as described in connection with R 7 , m' is 0 to 2, n' is 0 or 1, p' is 0 to 2, q' is 0 or 1, 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, T 1 to T 4 are each independently a single bond, O, S or Se, and Z 1 to Z 12 may each as described in connection with R 3 .
  4. The condensed heterocyclic compound of any one of claims 1 to 3, wherein: (i) in Chemical Formula 1, at least two selected from among R 3 to R 6 are the same; and/or (ii) in Chemical Formulae 1 and 2, R 3 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group or a substituted or unsubstituted C 2 -C 15 heteroaryl group.
  5. The condensed heterocyclic compound of any one of claims 1 to 4, wherein: (i) in Chemical Formula 1, n, m, p, and q are each independently 0, 1 or 2; and/or (ii )in Chemical Formula 2, s, t, and u are each independently 0 or 1.
  6. The condensed heterocyclic compound of any one of claims 1 to 5, wherein, in Chemical Formulae 1 and 2, R 3 to R 10 are each independently hydrogen, deuterium, a C 4 -C 15 tert-alkyl group substituted or unsubstituted with deuterium, a phenyl group substituted or unsubstituted with deuterium, a C 7 -C 20 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, or a pyridine group substituted or unsubstituted with deuterium.
  7. The condensed heterocyclic compound of claim 1, wherein the condensed heterocyclic compound is any one selected from among compounds represented by the following chemical formulae:
  8. A light-emitting device (ED), comprising: a first electrode (110); a second electrode (150); and an intermediate layer (ITL) between the first electrode (110) and the second electrode (150), the intermediate layer (ITL) comprising an emission layer (130) that comprises a condensed heterocyclic compound represented by Chemical Formula 1: wherein, in Chemical Formula 1, X 1 and X 2 are each independently O, S, or Se, and R 1 and R 2 are each independently a group represented by Chemical Formula 2 : wherein, in Chemical Formulae 1 and 2, R 3 to R 10 are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O) 2 R; and/or optionally, two or more of R 3 to R 10 are combined with each other to form a substituted or unsubstituted C 3 -C 60 cycloalkyl ring, a substituted or unsubstituted C 5 -C 60 cycloalkenyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl ring, a substituted or unsubstituted C 6 -C 60 aryl ring, or a substituted or unsubstituted C 2 -C 60 heteroaryl ring, wherein R, R', and R" are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, or a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, n, q, and s are each independently an integer from 0 to 3, m and p are each independently an integer from 0 to 4, r is an integer from 0 to 2, t and u are each independently an integer from 0 to 5, and * represents a bonding point.
  9. The light-emitting device (ED) of claim 8, wherein the emission layer (130) comprises a host and a dopant, the dopant comprising the condensed heterocyclic compound as a thermally activated delayed fluorescence dopant, optionally wherein the dopant further comprises a phosphorescent dopant.
  10. The light-emitting device (ED) according to claim 9, wherein the host comprises a hole transporting host represented by Chemical Formula HT and an electron transporting host represented by Chemical Formula ET: wherein, in Chemical Formula HT, L HT1 , L HT2 , and L HT3 are each independently a direct linkage, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 2 -C 30 heteroarylene group, Ix1 to Ix3 are each independently be an integer from 0 to 10, Ar HT1 and Ar HT2 are each independently a substituted or unsubstituted C 6 -C 30 aryl group or a substituted or unsubstituted C 2 -C 30 heteroaryl group, and Ar HT3 is a substituted or unsubstituted C 6 -C 30 aryl group. and wherein, in Chemical Formula ET, at least one selected from among X ET1 to X ET3 is N, and the remainder of X ET1 to X ET3 are each independently C(R ET ), R ET is hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group, Ix1 to Ix3 are each independently an integer from 0 to 10, L ET1 to L ET3 are each independently be a direct linkage, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 2 -C 30 heteroarylene group, and Ar ET1 to Ar ET3 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group.
  11. The light-emitting device (ED) of claim 10, wherein the intermediate layer (ITL) further comprises: a hole transport layer (124) between the emission layer (130) and the first electrode (110); and an electron transport layer (144) between the emission layer (130) and the second electrode (150).
  12. The light-emitting device (ED) of claim 14, wherein the intermediate layer (ITL) further comprises: an electron blocking layer (126) between the hole transport layer (124) and the emission layer (130); and a hole blocking layer (146) between the emission layer (130) and the electron transport layer (144).
  13. The light-emitting device (ED) of claim 12, wherein: (i) the hole transport layer (124) or the electron blocking layer (126) comprises a compound represented by Chemical Formula HT; and/or (ii) the electron transport layer (144) or the hole blocking layer (146) comprises a compound represented by Chemical Formula ET.
  14. The light-emitting device (ED) of any one of claims 8 to 13, wherein the emission layer (130) is to emit a green light with a maximum emission wavelength in a range of about 510 nm to about 540 nm.
  15. An electronic apparatus comprising a light-emitting device (ED), wherein, the light-emitting device (ED) comprises: a first electrode (110); a second electrode (150); and an intermediate layer (ITL) between the first electrode (110) and the second electrode (150), the intermediate layer (ITL) comprising an emission layer (130) that comprises a condensed heterocyclic compound represented by Chemical Formula 1: wherein, in Chemical Formula 1, X 1 and X 2 are each independently O, S, or Se, and R 1 and R 2 are each independently a group represented by Chemical Formula 2: and wherein, in Chemical Formulae 1 and 2, R 3 to R 10 are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O) 2 R; and/or optionally, two or more of R 3 to R 10 are combined with each other to form a substituted or unsubstituted C 3 -C 60 cycloalkyl ring, a substituted or unsubstituted C 5 -C 60 cycloalkenyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl ring, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl ring, a substituted or unsubstituted C 6 -C 60 aryl ring, or a substituted or unsubstituted C 2 -C 60 heteroaryl ring, wherein R, R', and R" are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 5 -C 60 cycloalkenyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 60 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, or a substituted or unsubstituted C 8 -C 60 condensed polycyclic group, n, q, and s are each independently an integer from 0 to 3, m and p are each independently an integer from 0 to 4, r is an integer from 0 to 2, t and u are each independently an integer from 0 to 5, and * represents a bonding point, optionally wherein the electronic apparatus is at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a light for signaling, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, 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 micro display, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signage.

Description

BACKGROUND 1. Field One or more embodiments of the present application relate to a condensed heterocyclic compound, a light-emitting device, and an electronic device. 2. Description of the Related Art An organic light-emitting device has a self-luminous property under a driving voltage, and may provide improved viewing angle and contrast properties. Additionally, the organic light-emitting device has characteristics of high response speed and high luminance compared to other light-emitting devices of the comparable art. The organic light-emitting device may include an emission layer arranged between a first electrode and a second electrode. Holes provided from the first electrode and electrons provided from the second electrode may be recombined in the emission layer to generate excitons. Light emission properties are implemented as the excitons transition and decay from an excited state to a ground state, emitting light from the emission layer. The emission layer may include a host material and a dopant material to implement the above-described light emitting mechanism. SUMMARY One or more aspects of embodiments of the present disclosure are directed toward a condensed heterocyclic compound that has improved spectroscopic and luminescent properties. One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device that has improved luminescent properties and reliability. One or more aspects of embodiments of the present disclosure are directed toward an electronic device including the light-emitting device. Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure. According to one or more embodiments of the present disclosure, a condensed heterocyclic compound represented by Chemical Formula 1 is provided. In Chemical Formula 1, X1 and X2 are each independently O, S, or Se. R1 and R2 are each independently a group represented by Chemical Formula 2. In Chemical Formulae 1 and 2, R3 to R10 are each independently hydrogen, deuterium, a halogen, a hydroxyl group, a cyano group, an amidino group, a hydrazine group, a hydrazone group, 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 C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl 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, - SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R; and/or two or more selected from among R3 to R10 are combined with 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, a halogen, a hydroxyl group, a cyano group, 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 C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, or a substituted or unsubstituted C8-C60 condensed polycyclic group. n, q, and s are each independently an integer from 0 to 3, m and p are each independently an integer from 0 to 4, r is an integer from 0 to 2, and t and u are each independently an integer from 0 to 5. When n, m, p, q, r, s, t, and u are each 2 or greater, two or more selected from among respective R3(s) to R10(s) may each independently be the same as or different from each other. * represents a bonding point. In one or more embodiments, the group represented by Chemical Formula 2 may be represented by Chemical Formula 2-1 or 2-2. In Chemical Formulae 2-1 and 2-2, R8, R10, s, and u are each independently the same as those defined in Chemical Formula 2. R11 and R12 are each independently