HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING SAME

• US 20170141325A1
• Filed: 06/26/2015
• Published: 05/18/2017
• Est. Priority Date: 06/27/2014
• Status: Active Grant

• Current Assignee: Lt Materials Co., Ltd.
• Original Assignee: Heesung Material Ltd.
• Inventors: EUM, Sung-Jin, LEE, Joo-Dong, NO, Young-Seok, PARK, Geon-Yu, KIM, Dong-Jun, LEE, Jung-Hyun, KIM, Kee-Yong, CHOI, Jin-Seok, CHOI, Dae-Hyuk
• Granted Patent: US 10,644,244 B2
• Time in Patent Office: Days
• 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: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 9/6561 containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/171 Electron injection 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 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/636 comprising heteroaromatic 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

The present application provides a hetero-cyclic compound which may significantly improve the service life, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device in which the hetero-cyclic compound is contained in an organic compound layer.

Claims

1. A hetero-cyclic compound represented by the following Formula 1:

2. The hetero-cyclic compound of claim 1, wherein one of X₁ and X₂ is N and the other is CR₁₀,

at least one of R₁, R₂, and R₁₀ is -(L)m-(Z)n,

L is straight-chained or branched substituted or unsubstituted C₂ to C₆₀ alkylene;

monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ arylene;

or monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroarylene,

m is an integer of 0 to 3,

n is an integer of 1 or 2,

Z is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted C₆ to C₆₀ aryl;

monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroaryl;

—

SiR₁₁R₁₂R₁₃;

—

P(═

O)R₁₄R₁₅; and

amine which is unsubstituted or substituted with C₁ to C₂₀ alkyl, monocyclic or polycyclic substituted or unsubstituted C₆ to C₆₀ aryl, or monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroaryl, and

R₁₁ to R₁₅ are the same as or different from each other, and are each independently selected from the group consisting of straight-chained or branched C₁ to C₆₀ alkyl;

monocyclic or polycyclic C₆ to C₆₀ aryl; and

monocyclic or polycyclic C₂ to C₆₀ heteroaryl.

3. The hetero-cyclic compound of claim 2, wherein Z is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted acenaphthalenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted pyrrole, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolinyl, a substituted or unsubstituted 10,11-dihydro-dibenzo[b,f]azepine group, a substituted or unsubstituted 9,10-dihydroacridine group, a substituted or unsubstituted spiro group in which 2,3-dihydro-1H-indene or cyclohexane is spiro-bonded to fluorene, substituted or unsubstituted dialkylamine, substituted or unsubstituted diarylamine, substituted or unsubstituted alkylarylamine, a substituted or unsubstituted acetophenone group, a substituted or unsubstituted benzophenone group, —

SiR₁₁R₁₂R₁₃ and —

P(═

O)R₁₄R₁₅, and

R₁₁ to R₁₅ are the same as those defined in claim 2.

4. The hetero-cyclic compound of claim 1, wherein R₄ to R₉ are hydrogen or deuterium.

5. The hetero-cyclic compound of claim 1, wherein Formula 1 is represented by the following Formula 2 or 3:

6. The hetero-cyclic compound of claim 1, wherein Formula 1 is represented by any one of the following Formulae 4 to 7:

7. The hetero-cyclic compound of claim 6, wherein at least one of R₁ to R₃ is -(L)m-(Z)n, and the others are the same as those defined in Formula 1,

L is straight-chained or branched substituted or unsubstituted C₂ to C₆₀ alkylene;

monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ arylene;

or monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroarylene,

m is an integer of 0 to 3,

n is an integer of 1 or 2,

Z is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted C₆ to C₆₀ aryl;

monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroaryl;

—

SiR₁₁R₁₂R₁₃;

—

P(═

O)R₁₄R₁₅; and

amine which is unsubstituted or substituted with C₁ to C₂₀ alkyl, monocyclic or polycyclic substituted or unsubstituted C₆ to C₆₀ aryl, or monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroaryl,

R₁₁ to R₁₅ are the same as or different from each other, and are each independently selected from the group consisting of straight-chained or branched C₁ to C₆₀ alkyl;

monocyclic or polycyclic C₆ to C₆₀ aryl; and

monocyclic or polycyclic C₂ to C₆₀ heteroaryl, and

the definitions of Y and R₄ to R₉ are the same as those defined in Formula 1.

8. The hetero-cyclic compound of claim 7, wherein Z is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted acenaphthalenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted pyrrole, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolinyl, a substituted or unsubstituted 10,11-dihydro-dibenzo[b,f]azepine group, a substituted or unsubstituted 9,10-dihydroacridine group, a substituted or unsubstituted spiro group in which 2,3-dihydro-1H-indene or cyclohexane is spiro-bonded to fluorene, substituted or unsubstituted dialkylamine, substituted or unsubstituted diarylamine, substituted or unsubstituted alkylarylamine, a substituted or unsubstituted acetophenone group, a substituted or unsubstituted benzophenone group, —

SiR₁₁R₁₂R₁₃ and —

P(═

O)R₁₄R₁₅, and

L, m, n, and R₁₁ to R₁₅ are the same as those defined in claim 7.

9. The hetero-cyclic compound of claim 1, wherein Formula 1 is represented by any one of the following Formulae 8 to 11:

10. The hetero-cyclic compound of claim 9, wherein A is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted C₆ to C₆₀ arylene;

and monocyclic or polycyclic substituted or unsubstituted C₂ to C₆₀ heteroarylene.

11. The hetero-cyclic compound of claim 2, wherein Y is

12. The hetero-cyclic compound of claim 11, wherein

13. The hetero-cyclic compound of claim 1, wherein Formula 1 is selected from the following compounds:

14. An organic light emitting device comprising:

a positive electrode;

a negative electrode; and

one or more organic material layers provided between the positive electrode and the negative electrode, wherein one or more layers of the organic material layers comprise the hetero-cyclic compound of claim 1.

15. The organic light emitting device of claim 14, wherein the organic material layer comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

16. The organic light emitting device of claim 15, wherein the organic material layer comprising the hetero-cyclic compound is an electron transport layer.

17. The organic light emitting device of claim 15, wherein the organic material layer comprising the hetero-cyclic compound is a light emitting layer.

18. The organic light emitting device of claim 15, wherein the organic material layer comprising the hetero-cyclic compound is a hole blocking layer.