IP Library › Granted Patent US 11,737,357
Granted Patent B2
US 11,737,357 · App. 15/770,633 · Granted Aug 22, 2023

Compound and organic light-emitting device comprising same

Inventors: Miyeon Han (Daejeon, KR); Dong Hoon Lee (Daejeon, KR); Jungoh Huh (Daejeon, KR); Boonjae Jang (Daejeon, KR); Minyoung Kang (Daejeon, KR); Dong Uk Heo (Daejeon, KR); Min Woo Jung (Daejeon, KR)
H10K85/654C07D235/06C07D251/12C07D251/24C07D263/52C07D277/60C07D403/10C07D405/10C07D409/10C07D413/10C07D471/04C09K11/06H10K50/12H10K50/15H10K50/16H10K50/171H10K50/18H10K50/81H10K50/82H10K71/164H10K85/615H10K85/626H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 11,737,357
App. No.
15/770,633
Granted
Aug 22, 2023
Kind
B2
Abstract

The present application relates to a compound of Chemical Formula 1 and an organic light emitting device including the same.

Claims (45)

1. A compound represented by the following Chemical Formula 1:

in Chemical Formula 1,

Ar 1 and Ar 2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

L 1 is represented by Chemical Formulae 2 or 5,

S 1 is deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

p is an integer of 0 to 6, and

when p is an integer of 2 or more, each occurrence of S 1 is the same as or different from each other,

S 4 is deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

y is an integer of 0 to 4, and

when y is an integer of 2 or more, each occurrence of S 4 is each the same as or different from each other,

in Chemical Formulae 2 and 5,

a dotted line “- - - - - -” is each a moiety bonded to a triazine group or L 2 of Chemical Formula 1,

L 2 is a direct bond; or a substituted or unsubstituted arylene group, and

Ar 3 is represented by a substituted phenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted spirofluoreneindenophenanthrene group; a substituted or unsubstituted dispirofluoreneanthracenefluorene group; a substituted or unsubstituted triphenylene group; a heterocyclic group including S or O, which is unsubstituted or substituted; an unsubstituted carbazole group; or any one of the following Chemical Formulae 6 to 9, 10-1 and 10-2, when L 1 is Chemical Formula 2, provided that the compound is not

and provided that when Ar 3 is a fluorenyl substituted with an alkyl group, L 2 is a substituted or unsubstituted arylene group,

Ar 3 is represented by a cyano-substituted phenyl group; a substituted or unsubstituted fluorenyl group, wherein adjacent substituents of the fluorenyl group do not combine with each other to form a ring; a substituted or unsubstituted benzofluorenyl group; a substituted spirobifluorenyl group, wherein the substitutions of spirobifluorenyl group do not combine with each other to form a 5-membered to 8-membered hetero ring; a substituted or unsubstituted spirofluoreneindenophenanthrene group; a substituted or unsubstituted dispirofluoreneanthracenefluorene group; an unsubstituted dibenzofuran group; an unsubstituted dibenzothiophene group; a substituted or unsubstituted benzonaphthofuran group; a substituted or unsubstituted benzonaphthothiophene group; or any one of Chemical Formulae 6, 9, 10-1 and 10-2, when L 1 is Chemical Formula 5,

in Chemical Formulae 6 to 9, 10-1 and 10-2,

X 1 is O, S, or NR,

at least two of X 2 to X 6 are N, and the others are each independently CR′,

R and R′ are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

R 1 to R 6 , R 9 , and R 10 are each independently deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

at least one of Y 1 to Y 4 is N, and the others are CR″,

R″ is each independently hydrogen or deuterium,

m, n, t, u, v, and x are each independently an integer of 0 to 4, w is an integer of 0 to 3, and when m, n, t, u, v, w, and x are each an integer of 2 or more, R 1 to R 6 , R 9 , and R 10 in each occurrence are the same as or different from each other, respectively,

s is an integer of 0 to 2, and when s is 2, two R 3 s are the same as or different from each other, and

“- - - - - -” means a moiety bonded to L 2 of Chemical Formula 1, and the bonding moiety of Chemical Formula 10-1 is R6, R9, or R10.

2. The compound of claim 1 , wherein L 2 is a direct bond; or a substituted or unsubstituted C 6 to C 20 arylene group.

3. The compound of claim 1 , wherein Ar 3 is a substituted phenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted spirofluoreneindenophenanthrene group; a substituted or unsubstituted dispirofluoreneanthracenefluorene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrimidyl group; a substituted or unsubstituted pyridazinyl group; a substituted or unsubstituted triazinyl group; a substituted or unsubstituted benzocarbazolyl group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted benzonaphthofuran group; or a substituted or unsubstituted benzonaphthothiophene group, when L 1 is Chemical Formula 2,

provided that the compound is not

and

Ar 3 is a cyano-substituted phenyl group; a substituted or unsubstituted fluorenyl group, wherein adjacent substituents of the fluorenyl group do not combine with each other to form a ring; a substituted or unsubstituted benzofluorenyl group; a substituted spirobifluorenyl group; a substituted or unsubstituted spirofluoreneindenophenanthrene group; a substituted or unsubstituted dispirofluoreneanthracenefluorene group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; an unsubstituted dibenzofuran group; an unsubstituted dibenzothiophene group; a substituted or unsubstituted benzonaphthofuran group; or a substituted or unsubstituted benzonaphthothiophene group, when L 1 is Chemical Formula 5.

4. The compound of claim 1 , wherein Ar 1 and Ar 2 are the same as or different from each other, and are each independently a substituted or unsubstituted C 6 to C 20 aryl group.

5. A compound represented by the following structural formulae:

6. An organic light emitting device comprising:

a first electrode;

a second electrode provided to face the first electrode; and

one or more organic material layers provided between the first electrode and the second electrode,

wherein the one or more organic material layers comprise the compound of claim 1 .

7. The organic light emitting device of claim 6 , wherein the one or more organic material layers comprise an electron transport layer or an electron injection layer, and

the electron transport layer or the electron injection layer comprises the compound.

8. The organic light emitting device of claim 6 , wherein the one or more organic material layers comprise a light emitting layer, and

the light emitting layer comprises the compound.

9. The organic light emitting device of claim 6 , wherein the one or more organic material layers comprise a hole injection layer or a hole transport layer, and

the hole injection layer or the hole transport layer comprises the compound.

10. The organic light emitting device of claim 6 , wherein the one or more organic material layers comprise an electron transport layer, and the electron transport layer comprises the compound, and the one or more organic material layers further comprise one or two or more layers selected from a group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2018
From: HAN, MIYEON; LEE, DONG HOON; HUH, JUNGOH; JANG, BOONJAE; KANG, MINYOUNG; HEO, DONG UK; JUNG, MIN WOO
To: LG CHEM, LTD.
Reel/Frame 045632/0968 →
Priority Claims (1)
KR 10-2015-0149714 · Oct 27, 2015 · national
Continuity (1)
Related Publication 20190055222A1 · Feb 21, 2019