Heterocyclic compound and organic light-emitting device including the same
View Patent ↗Derivatives of benzo[h]naphtho[1,2-f]quinoline and organic light emitting devices (OLEDs) including them are disclosed. The subject compounds impart high efficiency, low driving voltage, high luminance and long lifespan to the OLEDs. The subject compounds may be used as light emitting materials, as electron transporting materials, or as electron injecting materials. Because the subject compounds have high glass transition temperatures or high melting points, OLEDs including them exhibit high durability in storage or operation. Suitable substituents may be selected from deuterium, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, aryloxy, arylthio, aryl, aryl- or heteroaryl-substituted amino, heteroaryl, condensed polycyclic, halogen, cyano, nitro, hydroxyl and carboxyl groups.
1. A heterocyclic compound represented by Formula 1 below:
R 1 to R 13 in Formula 1 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 60 aryl or C 3 -C 60 heteroaryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group, where R 1 to R 13 are not all hydrogen atoms and R 8 is not a halogen atom when R 1 -R 7 and R 9 -R 13 are all hydrogen atoms; and
R 1 and R 2 are optionally linked to form an aromatic ring.
2. The heterocyclic compound of claim 1 , wherein R 1 , R 2 , and R 8 in Formula 1 are each independently a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, or a substituted or unsubstituted C 5 -C 20 condensed polycyclic group.
3. The heterocyclic compound of claim 1 , wherein R 3 to R 7 , and R 9 to R 13 in Formula 1 are each independently a hydrogen atom or a deuterium atom.
4. The heterocyclic compound of claim 1 , R 1 and R 2 in Formula 1 each being independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, and groups represented by Formulae 2a to 2e below:
Q 1 in Formulae 2a to 2e is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;
Y 1 , Y 2 , and Y 3 are each independently a linking group represented by —N═, —N(R 17 )—, or —C(R 18 )═;
Z 1 , Z 2 , R 14 , R 15 , R 16 , R 17 , and R 18 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;
p is an integer from 1 to 7; and
* indicates a binding site.
5. The heterocyclic compound of claim 1 , R 8 in Formula 1 being one of the groups represented by Formulae 3a to 3j below:
Q 1 in Formulae 3a to 3j is a linking group represented by —C(R 14 )(R 15 )—, —N(R 16 )—, —S—, or —O—;
Y 1 , Y 2 , and Y 3 are each independently a linking group represented by —O—, —N═, —N(R 17 )—, or —C(R 18 )═;
Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , R 17 , and R 18 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;
A 11 is a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 6 -C 20 arylene group, or a substituted or unsubstituted C 3 -C 20 heteroarylene group;
p is an integer from 1 to 9;
r is an integer from 0 to 5; and
* indicates a binding site.
6. The heterocyclic compound of claim 1 , R 1 and R 2 in Formula 1 each being independently selected from the group consisting of a hydrogen atom, a deuterium atom, and groups represented by Formulae 4a to 4g below, or are linked to form a benzene ring:
Z 1 and Z 2 in Formulae 4a to 4g are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;
p is an integer from 1 to 6; and
* indicates a binding site.
7. The heterocyclic compound of claim 1 , R 8 in Formula 1 being one of the groups represented by Formulae 5a to 5o below:
Z 1 , Z 2 , Ar 12 , and Ar 13 in Formulae 5a to 5o are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;
p is an integer from 1 to 7; and
* indicates a binding site.
8. The heterocyclic compound of claim 1 , the compound of Formula 1 comprising one of the compounds below:
9. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, the organic layer comprising a first layer including the heterocyclic compound of claim 1 .
10. The organic light-emitting device of claim 9 , wherein the first layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, an emission layer, an electron injection layer, an electron transport layer, and a functional layer having both electron injection and electron transport capabilities.
11. The organic light-emitting device of claim 9 , wherein the first layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, an emission layer, an electron injection layer, an electron transport layer, and a functional layer having both electron injection and electron transport capabilities, and the first layer further comprises a charge generating material.
12. The organic light-emitting device of claim 9 , wherein the organic layer further comprises a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination of at least two thereof.
13. The organic light-emitting device of claim 12 , wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having hole injection and hole transport capabilities further comprises a charge generating material.
14. The organic light-emitting device of claim 12 , wherein the emission layer comprises a host and a dopant, the dopant comprising a fluorescent dopant or a phosphorescent dopant.
15. The organic light-emitting device of claim 14 , wherein the phosphorescent dopant comprises an organometallic complex including at least one selected from the group consisting of iridium (Ir), platinum (Pt), osmium (Os), rhenium (Re), titanium (Ti), zirconium (Zr), hafnium (Hf), and a combination of at least two thereof.
16. The organic light-emitting device of claim 12 , wherein the electron transport layer comprises an electron transporting organic material and a metal-containing material.
17. The organic light-emitting device of claim 16 , wherein the metal-containing material comprises a lithium (Li) complex.
18. The organic light-emitting device of claim 9 , wherein the first layer comprising the heterocyclic compound of Formula 1 of claim 1 is formed using a wet process.
19. A flat panel display device comprising the organic light-emitting device of claim 9 , wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin-film transistor.