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KR-102962646-B1 - Heterocyclic compound and organic light emitting device including the same

KR102962646B1KR 102962646 B1KR102962646 B1KR 102962646B1KR-102962646-B1

Abstract

A heterocyclic compound having a predetermined chemical formula and an organic light-emitting device containing the same are presented.

Inventors

  • 전순옥
  • 정연숙
  • 이하섭
  • 심명선
  • 인수강
  • 코이시카와 야스시

Assignees

  • 삼성전자주식회사

Dates

Publication Date
20260508
Application Date
20240520

Claims (14)

  1. Heterocyclic compound represented by the following chemical formula 1: <Chemical Formula 1> Among the above chemical formula 1 X1 is N or C( R1 ), X2 is N or C( R2 ), and X3 is N or C( R3 ), provided that i) one of X1 to X3 is N and the others are not N; or ii) X1 to X3 are all not N, R1 to R3 are independently hydrogen, deuterium, a C1 - C20 alkyl group, a C1 - C20 alkyl group substituted with at least one deuterium, a C1- C20 alkoxy group, a C1 - C20 alkoxy group substituted with at least one deuterium, or -Si( Q101 )( Q102 )( Q103 ), and L1 to L3 are each single bonds, and a1 to a3 are independently selected from integers 1 to 5, and Ar 1 is a group represented by one of the following chemical formulas D'-1 to D'-7, and Ar 2 is a group represented by one of the following chemical formulas D001 to D279, and In the above chemical formulas D'-1 to D'-7 and D001 to D279, * is a bonding site with an adjacent atom, and The group represented by is a group represented by one of the following chemical formulas A1 to A38, and Among the groups marked with *, * is a bonding site with an adjacent atom, and In the above chemical formulas A1 to A38, * is each a bonding site with an adjacent atom, and The above Q 101 to Q 103 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, biphenyl group, terphenyl group, C6 - C60 aryloxy group, C6 -C It is selected from 60 arylthio groups, C1 - C60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic heterocondensed polycyclic groups.
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  5. In paragraph 1, The singlet energy level (eV) of the above heterocyclic compound is 2.5 eV or higher and 3.0 eV or lower, and The above singlet energy level is a heterocyclic compound evaluated using a DFT method structure-optimized at the B3LYP/6-31G(d,p) level.
  6. In paragraph 1, The difference between the triplet energy level (eV) of the above heterocyclic compound and the singlet energy level (eV) of the above heterocyclic compound is 0 eV or more and 0.5 eV or less, and The above triplet energy level and the above singlet energy level are heterocyclic compounds evaluated using a DFT method that structure-optimized at the B3LYP/6-31G(d,p) level.
  7. First electrode; Second electrode; and An organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; Includes, An organic light-emitting device in which the above organic layer comprises one or more heterocyclic compounds represented by the chemical formula 1 of any one of claims 1, 5, and 6.
  8. In Paragraph 7, The first electrode is an anode, and the second electrode is a cathode, and The organic layer comprises a hole transport region disposed between the first electrode and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode, and The hole transport region above includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and The above electron transport region comprises an organic light-emitting device including a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  9. In Paragraph 7, An organic light-emitting device in which a heterocyclic compound represented by the above chemical formula 1 is included in the light-emitting layer.
  10. In Paragraph 9, The above-mentioned light-emitting layer includes a host and a dopant, and The above dopant comprises a heterocyclic compound represented by the above chemical formula 1, and An organic light-emitting device in which the content of the above host is greater than the content of the above dopant.
  11. In Paragraph 9, An organic light-emitting device in which the above-mentioned light-emitting layer emits blue light.
  12. In Paragraph 9, An organic light-emitting device in which the delayed fluorescence component emitted from the heterocyclic compound accounts for 90% or more of the total light-emitting components emitted from the light-emitting layer.
  13. In Paragraph 10, The above host comprises at least one of a first substance and a second substance, and The first material comprises at least one π electron-deficient nitrogen-free cyclic group and does not comprise an electron-transporting moiety, and The second material comprises at least one π electron-deficient nitrogen-free cyclic group and at least one electron-transporting moiety, and An organic light-emitting device in which the above electron transport moiety is selected from a cyano group, a π electron-deficient nitrogen-containing cyclic group, and a group represented by one of the following chemical formulas: Among the above chemical formulas, *, *', and *" are each bonding sites with any adjacent atom.
  14. In Paragraph 13, The first substance comprises a cyano-group-free benzene group and a cyano-group-free carbazole group, and The above second material is an organic light-emitting device comprising at least one of a cyano group-containing benzene group and a cyano group-containing carbazole group.

Description

Heterocyclic compound and organic light emitting device including the same A heterocyclic compound and an organic light-emitting device containing the same are presented. Organic light-emitting devices are self-emissive devices that, compared to conventional devices, have a wide viewing angle and excellent contrast, as well as a fast response time, excellent characteristics in brightness, driving voltage and response speed, and are capable of multi-color. According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode, the organic layer including a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. FIG. 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. The above heterocyclic compound can be represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, X1 is N or C( R1 ), X2 is N or C( R2 ), and X3 is N or C( R3 ), wherein i) one of X1 to X3 is N and the others are not N; or ii) X1 to X3 may all not be N. According to one embodiment, X1 is C( R1 ), X2 is C( R2 ), and X3 is C( R3 ); X1 is N, X2 is C( R2 ), and X3 is C( R3 ); or X 1 is C(R 1 ) and X 2 is N and X 3 is C(R 3 ) but is not limited thereto. The above R1 to R3 may independently be hydrogen, deuterium, a C1 - C20 alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, or pentyl group, etc.), a C1 - C20 alkyl group substituted with at least one deuterium, a C1 - C20 alkoxy group (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, or pentoxy group, etc.), a C1 - C20 alkoxy group substituted with at least one deuterium, or -Si( Q101 )( Q102 )( Q103 ). For descriptions of the above Q101 to Q103 , refer to those described in the present specification. Among the above chemical formula 1, L1 and L2 are independent of each other, single bond; and At least one C5 - C60 carbocyclic group, pyridine group, and π-electron-deficient nitrogen-free C1 - C60 heterocyclic group substituted or unsubstituted with R10a ; Selected from among, L3 to L5 are independent of each other, single bond; and A C5 - C60 carbocyclic group and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a ; It may be selected from among. Refer to the description of the above R 10a below. According to one embodiment, L1 to L5 are independently of each other, single bond; and A benzene group, fluorene group, pyridine group, dibenzofuran group, dibenzothiophen group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, acridine group and dihydroacridine group substituted or unsubstituted with at least one R 10a; It can be selected from among them. According to another embodiment, L3 of Formula 1 may be independently selected from a single bond and the group represented by Formulas 2-1 to 2-4 below, but is not limited thereto: Among the above chemical formulas 2-1 to 2-4, R 11 to R 13 are independently hydrogen, deuterium, or C 1 -C 10 alkyl groups, and * is the binding site with the left six-membered ring in the above chemical formula 1, and *' is the binding site with the right six-membered ring in the above chemical formula 1. a1 to a5 of the above chemical formula 1 each represent the number of L1 to L5 and can be independently selected from integers 1 to 5. If a1 to a5 are each 2 or more, each of the 2 or more L1 to L5 may be identical or different from each other. a1 to a5 may be independently 1 or 2, but are not limited thereto. Ar 1 and Ar 2 may independently be a group represented by the following formula 3A, a group represented by the following formula 3B, a group represented by the following formula 3C, a group represented by the following formula 3D, a group represented by the following formula 3E, a group represented by the following formula 3F, or a C 6 -C 60 aryl group substituted or unsubstituted with at least one Z 31 . According to one embodiment, Ar 1 and Ar 2 in the above chemical formula 1 may be identical to each other. According to another embodiment, Ar 1 and Ar 2 in the above chemical formula 1 may be different from each other. According to another embodiment, at least one of Ar 1 and Ar 2 of the above formula 1 may be independently selected from the group represented by the