Heterocyclic compound and organic light-emitting device including the same

• US 10,640,522 B2
• Filed: 11/09/2017
• Issued: 05/05/2020
• Est. Priority Date: 04/27/2017
• Status: Active Grant

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Inventors: Ahn, Heechoon, Ko, Soobyung, Jun, Mieun, Kim, Sungbum, Jeon, Mina, Kim, Youngkook, Hwang, Seokhwan
• Primary Examiner(s): Nguyen, Vu A
• Application Number:
  US15/808,091
• Publication Number:
  US 20180312533A1
• Time in Patent Office: 908 Days
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07F 7/0816 said ring comprising Si as a ring atom
• CPC Class Codes: C07F 9/657163 the ring phosphorus atom being bound to at least one carbon atom
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/20 Delayed fluorescence emission
• CPC Class Codes: H10K 2101/30 Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A heterocyclic compound and an organic light-emitting device, the heterocyclic compound being represented by Formula 1:

Claims

1. A heterocyclic compound represented by Formula 1:

2. The heterocyclic compound as claimed in claim 1, wherein L₂₁ and L₃₁ in Formulae 2, 3-1, and 3-2 are each independently selected from:

a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a triazinylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a triazinylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

3. The heterocyclic compound as claimed in claim 1, wherein L₂₁ and L₃₁ in Formulae 2, 3-1 and 3-2 are each independently selected from a single bond and a group represented by one of Formulae 4-1 to 4-28:

4. The heterocyclic compound as claimed in claim 1, wherein, in Formulae 1, 2, 3-1, and 3-2,

R₁ to R₈ are each independently a group represented by Formula 2, a group represented by Formula 3-1, a group represented by Formula 3-2, hydrogen, deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and —

Si(Q₁)(Q₂)(Q₃), and

R₉ to R₁₂, R₂₁ to R₂₆, and R₃₁ to R₃₆ are each independently selected from hydrogen, deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and —

Si(Q₁)(Q₂)(Q₃),

wherein Q₁ to Q₃ are each independently selected from hydrogen, deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C_r C₆₀ alkyl group substituted with at least one selected from deuterium, —

F, and a cyano group, a C₆-C₆₀ aryl group substituted with at least one selected from deuterium, —

F, and a cyano group, a biphenyl group, and a terphenyl group.

6. The heterocyclic compound as claimed in claim 1, wherein the group represented by Formula 2 is a group represented by any one of Formulae 2-2 to 2-5:

7. The heterocyclic compound as claimed in claim 1, wherein at least one selected from R₁ and R₈ is a group represented by Formula 2.

8. The heterocyclic compound as claimed in claim 1, wherein at least one selected from R₃ to R₆ is a group represented by Formula 3-1.

9. The heterocyclic compound as claimed in claim 1, wherein:

at least one selected from R₁ and R₈ is a group represented by Formula 2, and

at least one selected from R₃ to R₆ is a group represented by Formula 3-1.

10. The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is a compound represented by one of Formulae 1-1 to 1-4:

11. The heterocyclic compound as claimed in claim 10, wherein R₂ to R₈ are each independently selected from hydrogen, deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and —

Si(Q₁)(Q₂)(Q₃), in which Q₁ to Q₃ are each independently selected from hydrogen, deuterium, —

F, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkyl group substituted with at least one selected from deuterium, —

F, and a cyano group, a C₆-C₆₀ aryl group substituted with at least one selected from deuterium, —

F, and a cyano group, a biphenyl group, and a terphenyl group.

13. The heterocyclic compound as claimed in claim 1, wherein:

at least one selected from R₁ to R₈ is a group represented by Formula 3-1, the group represented by Formula 3-1 being a group represented by Formula 3-1-1,

14. The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is one of the following Compounds 1 to 48:

15. An organic light-emitting device, comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,

wherein the organic layer includes the heterocyclic compound as claimed in claim 1.

16. The organic light-emitting device as claimed in claim 15, wherein:

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer further includes 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 includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and

the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

17. The organic light-emitting device as claimed in claim 15, wherein the emission layer includes the heterocyclic compound.

18. The organic light-emitting device as claimed in claim 17, wherein:

the heterocyclic compound included in the emission layer is a host, and

the emission layer further includes a phosphorescent dopant.

19. The organic light-emitting device as claimed in claim 17, wherein:

the heterocyclic compound included in the emission layer is a host, and

the emission layer further includes a delayed fluorescent dopant that satisfies Equation 1;

|E_D,S1−

E_D,T1|≤

0.3 eV. 

 

<

Equation 1>

in Equation 1,

E_{D, S1} is a singlet energy (eV) level of the delayed fluorescent dopant, and

E_{D, T1} is a triplet energy (eV) level of the delayed fluorescent dopant.

20. The organic light-emitting device as claimed in claim 17, wherein:

the heterocyclic compound included in the emission layer is a host, and

the emission layer further includes a delayed fluorescent dopant,

wherein the delayed fluorescent dopant and the host satisfy Equation 2 or Equation 3;

|E_H,HOMO−

E_D,HOMO|≤

0.5 eV 

 

<

Equation 2>

|E_H,LUMO−

E_D,LUMO|≤

0.5 eV. 

 

<

Equation 3>

in Equations 2 and 3,

E_{H, HOMO} is a highest occupied molecular orbital level of the host,

E_{D, HOMO} is a highest occupied molecular orbital level of the delayed fluorescent dopant,

E_{H, LUMO} is a lowest unoccupied molecular orbital level of the host, and

E_{D, LUMO} is a lowest unoccupied molecular orbital level of the delayed fluorescent dopant.

5. A heterocyclic compound represented by Formula 1:

12. A heterocyclic compound represented by one of Formulae 1-1 to 1-4: