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1. EP3162806 - HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING SAME

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Claims

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

in Formula 1,

Y is S or O,

X1 and X2 are the same as or different from each other, and are each independently N or R10, and

R1, R2, and R4 to R10 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; straight-chained or branched substituted or unsubstituted C1 to C60 alkyl; straight-chained or branched substituted or unsubstituted C2 to C60 alkenyl; straight-chained or branched substituted or unsubstituted C2 to C60 alkynyl; straight-chained or branched substituted or unsubstituted C1 to C60 alkoxy; monocyclic or polycyclic substituted or unsubstituted C3 to C60 cycloalkyl; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heterocycloalkyl; monocyclic or polycyclic substituted or unsubstituted C6 to C60 aryl; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heteroaryl; 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.


  2. The hetero-cyclic compound of claim 1, wherein one of X 1 and X 2 is N and the other is CR 10,
at least one of R 1, R 2, and R 10 is -(L)m-(Z)n,
L is straight-chained or branched substituted or unsubstituted C 2 to C 60 alkylene; monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 arylene; or monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 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 C 6 to C 60 aryl; monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 heteroaryl; -SiR 11R 12R 13; -P(=O)R 14R 15; and amine which is unsubstituted or substituted with C 1 to C 20 alkyl, monocyclic or polycyclic substituted or unsubstituted C 6 to C 60 aryl, or monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 heteroaryl, and
R 11 to R 15 are the same as or different from each other, and are each independently selected from the group consisting of straight-chained or branched C 1 to C 60 alkyl; monocyclic or polycyclic C 6 to C 60 aryl; and monocyclic or polycyclic C 2 to C 60 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-dihydrodibenzo[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, - SiR 11R 12R 13 and -P(=O)R 14R 15, and
R 11 to R 15 are the same as those defined in claim 2.
  4. The hetero-cyclic compound of claim 1, wherein R 4 to R 9 are hydrogen or deuterium.
  5. The hetero-cyclic compound of claim 1, wherein Formula 1 is represented by the following Formula 2 or 3:





in Formulae 2 and 3, the definitions of Y, X 1, X 2, R 1, R 2, and R 4 to R 9 are the same as those defined in Formula 1.
  6. The hetero-cyclic compound of claim 1, wherein Formula 1 is represented by any one of the following Formulae 4 to 7:









in Formulae 4 to 7,

Y, R1, R2, and R4 to R9 are the same as those defined in Formula 1, and

R3 is the same as the definition of R10 of Formula 1.


  7.  The hetero-cyclic compound of claim 6, wherein at least one of R 1 to R 3 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 C 2 to C 60 alkylene; monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 arylene; or monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 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 C 6 to C 60 aryl; monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 heteroaryl; -SiR 11R 12R 13; -P(=O)R 14R 15; and amine which is unsubstituted or substituted with C 1 to C 20 alkyl, monocyclic or polycyclic substituted or unsubstituted C 6 to C 60 aryl, or monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 heteroaryl,
R 11 to R 15 are the same as or different from each other, and are each independently selected from the group consisting of straight-chained or branched C 1 to C 60 alkyl; monocyclic or polycyclic C 6 to C 60 aryl; and monocyclic or polycyclic C 2 to C 60 heteroaryl, and
the definitions of Y and R 4 to R 9 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-dihydrodibenzo[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, - SiR 11R 12R 13 and -P(=O)R 14R 15, and
L, m, n, and R 11 to R 15 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:









in Formulae 8 to 11,

A is selected from the group consisting of a direct bond; straight-chained or branched substituted or unsubstituted C2 to C60 alkylene; straight-chained or branched substituted or unsubstituted C2 to C60 alkenylene; straight-chained or branched substituted or unsubstituted C2 to C60 alkynylene; monocyclic or polycyclic substituted or unsubstituted C3 to C60 cycloalkylene; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heterocycloalkylene; monocyclic or polycyclic substituted or unsubstituted C6 to C60 arylene; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heteroarylene; 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,

R16 to R19 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; straight-chained or branched substituted or unsubstituted C1 to C60 alkyl; straight-chained or branched substituted or unsubstituted C2 to C60 alkenyl; straight-chained or branched substituted or unsubstituted C2 to C60 alkynyl; straight-chained or branched substituted or unsubstituted C1 to C60 alkoxy; monocyclic or polycyclic substituted or unsubstituted C3 to C60 cycloalkyl; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heterocycloalkyl; monocyclic or polycyclic substituted or unsubstituted C6 to C60 aryl; monocyclic or polycyclic substituted or unsubstituted C2 to C60 heteroaryl; 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,

p, q, r, and s are an integer of 0 to 4, and

the definitions of Y and R 6 to R 9 are the same as those defined in Formula 1.
  10. The hetero-cyclic compound of claim 9, wherein A is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted C 6 to C 60 arylene; and monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 heteroarylene.
  11. The hetero-cyclic compound of claim 2, wherein Y is

and X3 and X4 are a monocyclic or polycyclic substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring; or a monocyclic or polycyclic substituted or unsubstituted C 2 to C 60 aromatic heterocyclic ring.
  12. The hetero-cyclic compound of claim 11, wherein

is represented by any one of the following structural formulae:



in the structural formulae, Z 1 to Z 3 are the same as or different from each other, and are each independently S or O,

Z4 to Z9 are the same as or different from each other, and are each independently CR'R", NR', S, or O, and

R' and R" are the same as or different from each other, and are each independently hydrogen; straight-chained or branched substituted or unsubstituted C1 to C60 alkyl; or monocyclic or polycyclic substituted or unsubstituted C6 to C60 aryl.


  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 any one of claims 1 to 13.


  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.