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US-12628549-B2 - Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device

US12628549B2US 12628549 B2US12628549 B2US 12628549B2US-12628549-B2

Abstract

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device, the compound being represented by Chemical Formula 1:

Inventors

  • Byoungkwan LEE
  • Dong Min Kang
  • Jiyun KWON
  • Junmo Park
  • Hansol Seo
  • Kipo JANG
  • Seungin Park
  • Sung-Hyun Jung
  • Ho Kuk Jung

Assignees

  • SAMSUNG SDI CO., LTD.

Dates

Publication Date
20260512
Application Date
20220706
Priority Date
20210707

Claims (18)

  1. 1 . A composition for an organic optoelectronic device, the composition comprising: a first compound; and a second compound, wherein: the first compound is a compound for an organic optoelectronic device represented by Chemical Formula 1, and the second compound is a compound for an organic optoelectronic device represented by Chemical Formula 2: wherein, in Chemical Formula 1, X 1 is O or S, Z 1 to Z 3 are each independently N or CR a , at least two of Z 1 to Z 3 being N, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R a and R 1 to R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, R 6 and R 7 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, m1 and m2 are each independently an integer of 2 to 4, m3 and m4 are each independently an integer of 1 to 4, and n1 and n2 are each independently 0 or 1; and in Chemical Formula 2, X 2 is O, S, NR b , CR c R d , or SiR e R f , R b , R c , R d , R e , R f , and R 8 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m5 is an integer of 1 to 4, and ring A is a ring of Group II, in Group II, * is a linking carbon, X 3 is O, S, NR g , CR h R i , or SiR j R k , R g , R h , R i , R j , R k , and R 9 to R 16 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m6, m8, m11, and m13 are each independently an integer of 1 to 4, m7, m9, m10, and m12 are each independently 1 or 2, and at least one of R 8 to R 16 is a substituted amine group represented by Chemical Formula a, in Chemical Formula a, L 4 to L 6 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and * is a linking point.
  2. 2 . The composition as claimed in claim 1 , wherein: Chemical Formula 1 is represented by Chemical Formula 1A or Chemical Formula 1B: in Chemical Formula 1A and Chemical Formula 1B, X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 7 , m1 to m4, n1, and n2 are defined the same as those of Chemical Formula 1.
  3. 3 . The composition as claimed in claim 1 , wherein: Chemical Formula 1 is represented by one of Chemical Formula 1-1 to Chemical Formula 1-7: in Chemical Formula 1-1 to Chemical Formula 1-7, X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 7 , and m1 to m4 are defined the same as those of Chemical Formula 1.
  4. 4 . The composition as claimed in claim 1 , wherein L 1 to L 3 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
  5. 5 . The composition as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
  6. 6 . The composition as claimed in claim 1 , wherein: moieties -L 2 -Ar 1 and -L 3 -Ar 2 of Chemical Formula 1 are each independently a moiety of Group I: in Group I, D is deuterium, m14 is an integer of 0 to 5, m15 is an integer of 0 to 4, m16 is an integer of 0 to 7, m17 is an integer of 0 to 3, m18 is an integer of 0 to 6, m19 is an integer of 0 to 2, and * is a linking point.
  7. 7 . The composition as claimed in claim 1 , wherein the first compound is a compound of Group 1:
  8. 8 . The composition as claimed in claim 1 , wherein: Chemical Formula 2 is represented by one of Chemical Formula 2-I to Chemical Formula 2-IX: in Chemical Formula 2-I to Chemical Formula 2-IX, X 2 , X 3 , R 8 to R 11 , R 15 , R 16 , m5 to m8, m12, and m13 are defined the same as those of Chemical Formula 2.
  9. 9 . The composition as claimed in claim 8 , wherein: the second compound is represented by one of Chemical Formula 2-IA to Chemical Formula 2-IXA, Chemical Formula 2-IIB to Chemical Formula 2-IXB, and Chemical Formula 2-IIC to Chemical Formula 2-IXC: in Chemical Formula 2-IA to Chemical Formula 2-IXA, X 2 , X 3 , L 4 to L 6 , Ar 3 , Ar 4 , R 8 to R 11 , R 15 , R 16 , m6 to m8, m12, and m13 are defined the same as those of Chemical Formula 2, and m5′ is an integer of 1 to 3; X 2 , X 3 , L 4 to L 6 , R 8 , R 10 , R 11 , R 15 , R 16 , Ar 3 , Ar 4 , m5, m7, and m12 are defined the same as those of Chemical Formula 2, and m8′ and m13′ are each independently an integer of 1 to 3; in Chemical Formula 2-IIC to Chemical Formula 2-IXC, X 2 , X 3 , L 4 to L 6 , Ar 3 , Ar 4 , R 8 , R 10 , R 11 , R 15 , R 16 , m5, m8, and m13 are defined the same as those of Chemical Formula 2.
  10. 10 . The composition as claimed in claim 1 , wherein R 8 to R 16 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.
  11. 11 . The composition as claimed in claim 8 , wherein the second compound is represented by Chemical Formula 2-IVB-2 or Chemical Formula 2-VIIIB-2: in Chemical Formula 2-IVB-2 and Chemical Formula 2-VIIIB-2, L 4 to L 6 are each independently a single bond or a substituted or unsubstituted phenylene group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, X 2 is NR b , O, or S, X 3 is CR h R i or SiR j R k , R b , R h , R i , R j , and R k are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, R 8 , R 10 , R 11 , R 15 , and R 16 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, m5 is an integer of 1 to 4, m7 and m12 are each independently 1 or 2, and m8′ and m13′ are each independently an integer of 1 to 3.
  12. 12 . An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes a light emitting layer, and the light emitting layer includes the composition for the organic optoelectronic device as claimed in claim 1 .
  13. 13 . The organic optoelectronic device as claimed in claim 12 , wherein the composition for the organic optoelectronic device is a host of the light emitting layer.
  14. 14 . A display device comprising the organic optoelectronic device as claimed in claim 12 .
  15. 15 . A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: wherein, in Chemical Formula 1, X 1 is O or S, Z 1 to Z 3 are each independently N or CR a , at least two of Z 1 to Z 3 being N, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R a and R 1 to R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, R 6 and R 7 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, m1 and m2 are each independently an integer of 2 to 4, m3 and m4 are each independently an integer of 1 to 4, and n1 and n2 are each independently 0 or 1, provided that at least one of n1 and n2 is 1.
  16. 16 . An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes a light emitting layer, and the light emitting layer includes the compound for the organic optoelectronic device as claimed in claim 15 .
  17. 17 . The organic optoelectronic device as claimed in claim 16 , wherein the compound for the organic optoelectronic device is a host of the light emitting layer.
  18. 18 . A display device comprising the organic optoelectronic device as claimed in claim 16 .

Description

CROSS-REFERENCE TO RELATED APPLICATION This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0089278 filed in the Korean Intellectual Property Office on Jul. 7, 2021, and Korean Patent Application No. 10-2022-0075164 filed in the Korean Intellectual Property Office on Jun. 20, 2022, the entire contents of which are incorporated herein by reference. BACKGROUND 1. Field Embodiments relate to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. 2. Description of the Related Art An organic optoelectronic device (e.g., organic optoelectronic diode) is a device capable of converting electrical energy and optical energy to each other. Organic optoelectronic devices may be largely divided into two types according to a principle of operation. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes, and transferring the electrons and holes to different electrodes, respectively and the other is light emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes. Examples of the organic optoelectronic device may include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photo conductor drum. SUMMARY The embodiments may be realized by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: wherein, in Chemical Formula 1, X1 is O or S, Z1 to Z3 are each independently N or CRa, at least two of Z1 to Z3 being N, L1 to L3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ra and R1 to R5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, R6 and R7 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, m1 and m2 are each independently an integer of 2 to 4, m3 and m4 are each independently an integer of 1 to 4, and n1 and n2 are each independently 0 or 1. The embodiments may be realized by providing a composition for an organic optoelectronic device, the composition including a first compound; and a second compound, wherein the first compound is the compound for the organic optoelectronic device according to an embodiment, and the second compound is a compound for an organic optoelectronic device represented by Chemical Formula 2: in Chemical Formula 2, X2 is O, S, NRb, CRcRd, or SiReRf, Rb, Rc, Rd, Re, Rf, and R8 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m5 is an integer of 1 to 4, and ring A is a ring of Group II, in Group II, * is a linking carbon, X3 is O, S, NRg, CRhRi, or SiRjRk, Rg, Rh, Ri, Rj, Rk, and R9 to R16 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m6, m8, m11, and m13 are each independently an integer of 1 to 4, m7, m9, m10, and m12 are each independently 1 or 2, and at least one of R8 to R16 is a substituted amine group represented by Chemical Formula a, in Chemical Formula a, L4 to L6 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar3 and Ar4 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and * is a linking point. The embodiments may be realized by providing an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes a light emitting layer, and the light emitting layer includes the compound for the organic optoelectronic device according to an embodiment. The embodiments may be realized by providing an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes a light emitting layer, and the light emitting layer includes the composition for the organic optoelectronic device according to an embodiment. The embodiments may be realized by providing a display device including the organic o