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US-12624045-B2 - Condensed cyclic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

US12624045B2US 12624045 B2US12624045 B2US 12624045B2US-12624045-B2

Abstract

Provided are a condensed cyclic compound represented by Formula 1, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the light-emitting device: wherein details of Formula 1 are the same as described in the present specification.

Inventors

  • Keisuke KORAI
  • Norifumi KISHI
  • Wataru Sotoyama
  • Atsushi Imamura
  • Eigo MIYAZAKI
  • Jiwhan Kim
  • Juhyun Kim
  • Tomoya Hirose

Assignees

  • SAMSUNG ELECTRONICS CO., LTD.

Dates

Publication Date
20260512
Application Date
20211222
Priority Date
20201225

Claims (18)

  1. 1 . A condensed cyclic compound represented by Formula 1: wherein, in Formula 1, Ar 1 to Ar 5 are each independently a C 6 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, R 1 to R 5 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), wherein R 1 (s) in the number of n1, R 2 (s) in the number of n2, R 3 (s) in the number of n3, R 4 (s) in the number of n4, and R 5 (s) in the number of n5 are respectively identical to or different from each other, n1 to n5 are each independently an integer from 0 to 8, the sum of n1 to n5 is 1 or more, two of two or more R 1 (s) when n1 is 2 or more; two of two or more R 2 (s) when n2 is 2 or more; two of two or more R 3 (s) when n3 is 2 or more; two of two or more R 4 (s) when n4 is 2 or more; and two of two or more R 5 (s) when n5 is 2 or more are respectively optionally linked to each other or linked together via a single bond to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a , R 10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof; a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, wherein the condensed cyclic compound represented by Formula 1 has: (i) a highest occupied molecular orbital (HOMO) energy level of about −6.0 eV or more and a lowest unoccupied molecular orbital (LUMO) energy level of about −2.5 eV or less, and the HOMO energy level and the LUMO energy level are values measured using a photoelectron spectrometer and a spectrophotometer, respectively, (ii) a difference between a singlet (S 1 ) energy level and a triplet (T 1 ) energy level of about 0.5 eV or less, or (iii) a combination thereof.
  2. 2 . The condensed cyclic compound of claim 1 , wherein Ar 1 to Ar 5 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
  3. 3 . The condensed cyclic compound of claim 1 , wherein a group represented by in Formula 1 is represented by one of Formulae 1-2-1 to 1-2-19:
  4. 4 . The condensed cyclic compound of claim 1 , wherein R 1 to R 5 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 30 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 30 arylthio group unsubstituted or substituted with at least one R 10a , or —N(Q 1 )(Q 2 ), and Q 1 and Q 2 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 20 alkyl group; a C 2 -C 20 alkenyl group; a C 2 -C 20 alkynyl group; a C 1 -C 20 alkoxy group; or a C 3 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
  5. 5 . The condensed cyclic compound of claim 1 , wherein at least one of R 1 to R 4 is —N(Q 1 )(Q 2 ), and Q 1 and Q 2 are each independently a benzene group or a naphthalene group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
  6. 6 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 2: wherein, in Formula 2, Ar 1 to Ar 4 , R 1 to R 5 , and n1 to n4 are respectively the same as described in claim 1 , X 1 and X 2 are each independently C or N, n52 is an integer from 0 to 2, the sum of n1 to n4 and n52 is 1 or more, and two of two or more R 1 (s) when n1 is 2 or more; two of two or more R 2 (s) when n2 is 2 or more; two of two or more R 3 (s) when n3 is 2 or more; two of two or more R 4 (s) when n4 is 2 or more; and two R 5 (s) when n52 is 2 are respectively optionally linked to each other or linked together via a single bond to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a .
  7. 7 . The condensed cyclic compound of claim 6 , wherein each of X 1 and X 2 is C.
  8. 8 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound represented by Formula 1 is represented by Formula 3: wherein, in Formula 3, R 11 to R 14 are respectively the same as described in connection with R 1 in claim 1 , R 21 to R 23 are respectively the same as described in connection with R 2 in claim 1 , R 31 to R 34 are respectively the same as described in connection with R 3 in claim 1 , R 41 to R 43 are respectively the same as described in connection with R 4 in claim 1 , R 51 and R 52 are respectively the same as described in connection with R 5 in claim 1 , wherein at least one of R 11 to R 14 , R 21 to R 23 , R 31 to R 34 , R 41 to R 43 , R 51 , and R 52 is not hydrogen, and two of R 11 to R 14 , R 21 to R 23 , R 31 to R 34 , R 41 to R 43 , R 51 , and R 52 are optionally linked to each other or linked together via a single bond to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a .
  9. 9 . The condensed cyclic compound of claim 8 , wherein at least one of R 13 , R 22 , R 33 , and R 42 is not hydrogen.
  10. 10 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound represented by Formula 1 is one of Compounds 1 to 24: wherein D in Compound 22 is deuterium, and “D=52” in Compound 24 means that all 52 hydrogen atoms in Compound 24 are substituted with deuterium atoms.
  11. 11 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound emits blue light or cyan light.
  12. 12 . An organic light-emitting device comprising: a first electrode; a second electrode; and an interlayer arranged between the first electrode and the second electrode and comprising an emission layer, wherein the interlayer comprises at least one condensed cyclic compound of claim 1 .
  13. 13 . The organic light-emitting device of claim 12 , wherein the first electrode is an anode, the second electrode is a cathode, the interlayer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  14. 14 . The organic light-emitting device of claim 12 , wherein the emission layer comprises the at least one condensed cyclic compound.
  15. 15 . The organic light-emitting device of claim 14 , wherein the at least one condensed cyclic compound comprised in the emission layer acts as a delayed fluorescence dopant, such that delayed fluorescence is emitted from the emission layer.
  16. 16 . The organic light-emitting device of claim 14 , wherein the emission layer further comprises a host, and the host is represented by Formula 4: wherein, in Formula 4, X 41 to X 56 are each independently C or N, L 41 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , R 61 to R 64 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), n61 to n64 are each independently an integer from 0 to 4, R 10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof; a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
  17. 17 . An electronic apparatus comprising the organic light-emitting device of claim 12 .
  18. 18 . The electronic apparatus of claim 17 , further comprising a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the light-emitting device is electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of Japanese Patent Application No. 2020-216557, filed on Dec. 25, 2020, in the Japanese Patent Office and Korean Patent Application No. 10-2021-0087429, filed on Jul. 2, 2021, in the Korean Intellectual Property Office, the disclosures of which are incorporated by reference herein in their entirety. BACKGROUND 1. Field The present disclosure relates to condensed cyclic compounds, organic light-emitting devices including the condensed cyclic compounds, and electronic apparatuses including the organic light-emitting devices. 2. Description of the Related Art Organic light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, and short response times, exhibit excellent characteristics in terms of luminance, driving voltage, and response speed, and produce full-color images. In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is arranged between the anode and the cathode and includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light. SUMMARY Provided are condensed cyclic compounds having excellent luminescence efficiency and high color purity and organic light-emitting devices including the condensed cyclic compounds. 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 an aspect of an embodiment, provided is a condensed cyclic compound represented by Formula 1: In Formula 1, Ar1 to Ar5 are each independently a C6-C60 carbocyclic group or a C1-C60 heterocyclic group,R1 to R5 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2), wherein R1(s) in the number of n1, R2(s) in the number of n2, R3(s) in the number of n3, R4(s) in the number of n4, and R5(s) in the number of n5 are identical to or different from each other,n1 to n5 are each independently an integer from 0 to 8,the sum of n1 to n5 is 1 or more,two of two or more R1(s) when n1 is 2 or more; two of two or more R2(s) when n2 is 2 or more; two of two or more R3(s) when n3 is 2 or more; two of two or more R4(s) when n4 is 2 or more; and two of two or more R5(s) when n5 is 2 or more are respectively optionally linked to each other or linked together via a single bond to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,R10a is:deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), andQ1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with