CONDENSED CYCLIC COMPOUND, COMPOSITION INCLUDING THE SAME AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

• US 20200131150A1
• Filed: 10/22/2019
• Published: 04/30/2020
• Est. Priority Date: 10/25/2018
• Status: Active Application

• Current Assignee: Samsung Electronics Co. Ltd., Samsung SDI Company Limited
• Original Assignee: Samsung Electronics Co. Ltd., Samsung SDI Company Limited
• Inventors: JUNG, Yongsik, KWON, Eunsuk, KIM, Sangmo, SON, Jhunmo, LEE, Dongseon, JEON, Soonok, CHUNG, Yeonsook, KIM, Jongsoo
• Application Number:
  US16/660,021
• Publication Number:
  US 20200131150A1
• Time in Patent Office: Days
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 417/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/048 the oxygen-containing ring being five-membered
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07F 7/0816 said ring comprising Si as a ring atom
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene
• 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

Abstract

A condensed cyclic compound represented by Formula 1 or Formula 2:

• • wherein ring A₁, ring A₂, T₁, L₁, a1, R₁ to R₉, b1 to b3, and c1 in Formulae 1 and 2 are the same as described in the specification.

Claims

1. A condensed cyclic compound represented by Formula 1 or Formula 2:

2. The condensed cyclic compound of claim 1, wherein

ring A₁ and ring A₂ are each independently a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a cyclopentene group, a pyrrole group, a furan group, a thiophene group, a silole group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzocarbazole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, an acridine group, a dihydroacridine group, or a triindolobenzene group.

3. The condensed cyclic compound of claim 1, wherein

a group represented by

4. The condensed cyclic compound of claim 1, wherein

L₁ is a single bond;

or a group represented by one of Formulae 4-1 to 4-38;

5. The condensed cyclic compound of claim 1, wherein

L₁ is a single bond;

or a group represented by one of Formulae 5-1 to 5-9;

6. The condensed cyclic compound of claim 1, wherein

i) L₁ is a single bond, or

ii) L₁ is not a single bond, and a1 is 1, 2, or 3.

7. The condensed cyclic compound of claim 1, wherein

R₁ to R₉ are each independently selected from:

hydrogen, deuterium, —

F, a hydroxyl group, a cyano group, and a nitro group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each unsubstituted or substituted with at least one selected from deuterium, —

F, a hydroxyl group, a cyano group, and a nitro group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, and a pyridobenzothiazinyl group, each unsubstituted or substituted with at least one selected from deuterium, —

F, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group; and

—

N(Q₄)(Q₅), —

S(Q₁), and —

C(═

O)(Q₁),

Q₁, Q₄, and Q₅ are each independently selected from hydrogen, deuterium, a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group.

8. The condensed cyclic compound of claim 1, wherein

a group represented by

9. The condensed cyclic compound of claim 1, wherein

c1 is 1 or 2.

10. The condensed cyclic compound of claim 1, wherein

a group represented by

11. The condensed cyclic compound of claim 1, wherein

a group represented by

12. The condensed cyclic compound of claim 1, wherein

the condensed cyclic compound is selected from Compounds 1 to 1000:

13. A composition comprising a first compound and a second compound,

wherein the first compound is the condensed cyclic compound of claim 1,

the second compound is different from the first compound,

the second compound comprises at least one selected from a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, an acridine group, a dihydroacridine group, and a triindolobenzene group, and does not comprise an electron withdrawing group, and

the electron withdrawing group is selected from:

F, —

CFH₂, —

CF₂H, —

CF₃, —

CN, and —

NO₂;

a C₁-C₆₀ alkyl group substituted with at least one selected from —

F, —

CFH₂, —

CF₂H, —

CF₃, —

CN, and —

NO₂;

a C₁-C₆₀ heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group, each comprising *═

N—

*′

as a ring-forming moiety; and

a C₁-C₆₀ heteroaryl group and a monovalent non-aromatic condensed polycyclic heterocyclic group, each of which comprises *═

N—

*′

as a ring-forming moiety and is substituted with at least one selected from deuterium, —

F, —

CFH₂, —

CF₂H, —

CF₃, —

Cl, —

Br, —

I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀ heteroarylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

14. The composition of claim 13, wherein

the second compound is selected from compounds represented by Formula H-1:

15. The composition of claim 14, wherein

Ar₁₁ is a group represented by one of Formulae 11-1 to 11-8 and 12-1 to 12-8,

Ar₁₂ is selected from

a group represented by one of Formulae 11-1 to 11-8 and 12-1 to 12-8, a phenyl group, and a naphthyl group;

and

a phenyl group and a naphthyl group, each substituted with at least one selected from deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a biphenyl group;

16. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises at least one condensed cyclic compound represented by Formula 1 of claim 1.

17. The organic light-emitting device of claim 16, wherein

the emission layer comprises the at least one condensed cyclic compound.

18. The organic light-emitting device of claim 16, wherein

the emission layer comprises a host and a dopant,

the host comprises the at least one condensed cyclic compound, and

the dopant comprises a phosphorescent dopant.

19. The organic light-emitting device of claim 17, wherein

the emission layer emits blue light.

20. The organic light-emitting device of claim 16, wherein

the organic layer comprises an electron transport region disposed between the emission layer and the second electrode,

the electron transport region comprises a hole blocking layer and an electron transport layer,

the hole blocking layer is disposed between the emission layer and the electron transport layer, and

the hole blocking layer comprises the at least one condensed cyclic compound.