Organic optoelectronic device and display device
An organic optoelectronic device and a display device, the organic optoelectronic device including an anode and a cathode facing each other, a light emitting layer between the anode and the cathode, a hole transport layer between the anode and the light emitting layer, and a hole transport auxiliary layer between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and a second compound represented by Chemical Formula 3, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 4:
1. An organic optoelectronic device, comprising:
an anode and a cathode facing each other,
a light emitting layer between the anode and the cathode,
a hole transport layer between the anode and the light emitting layer, and
a hole transport auxiliary layer between the light emitting layer and the hole transport layer,
wherein:
the light emitting layer includes:
a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and
a second compound represented by Chemical Formula 3, and
the hole transport auxiliary layer includes a third compound represented by Chemical Formula 4,
in Chemical Formula 1 and Chemical Formula 2,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
adjacent two of a 1 * to a 4 * are carbon (C) linked at b 1 * and b 2 * respectively,
the other two of a 1 * to a 4 * not linked at b 1 * and b 2 * are each independently C-L a -R a ,
L a and L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R a and R 1 to R 4 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
at least one of R a and R 1 to R 4 is a group represented by Chemical Formula a,
in Chemical Formula a,
L b and L c are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R b and R c are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
* is a linking point with one of L a and L 1 to L 4 ;
in Chemical Formula 3,
Z 1 is N or C-L 5 -R 5 ,
Z 2 is N or C-L 6 -R 6 ,
Z 3 is N or C-L 7 -R 7 ,
Z 4 is N or C-L 8 -R 8 ,
Z 5 is N or C-L 9 -R 9 ,
Z 6 is N or C-L 10 -R 10 ,
at least two of Z 1 to Z 6 are N,
L 5 to L 10 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R 5 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
at least one of R 5 to R 10 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, or a substituted or unsubstituted triphenylene group, and
R 5 to R 10 are separately present or adjacent ones thereof are linked with each other to form a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic monocyclic ring or a substituted or unsubstituted aliphatic, aromatic, or heteroaromatic polycyclic ring;
in Chemical Formula 4,
X 1 is O or S,
L 11 to L 16 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R 11 to R 14 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
R 15 and R 16 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C10 alkyl group.
2. The organic optoelectronic device as claimed in claim 1 , wherein:
the first compound is represented by Chemical Formula 1A or Chemical Formula 1C:
in Chemical Formula 1A and Chemical Formula 1C,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L a and L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R a and R 1 to R 4 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
at least one of R a and R 1 to R 4 is a group represented by Chemical Formula a,
in Chemical Formula a,
L b and L c are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R b and R c are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
* is a linking point with one of L a and L 1 to L 4 .
3. The organic optoelectronic device as claimed in claim 1 , wherein:
the first compound is represented by one of Chemical Formula 1A-1 to Chemical Formula 1A-3 and Chemical Formula 1C-1 to Chemical Formula 1C-3:
in Chemical Formula 1A-1 to Chemical Formula 1A-3 and Chemical Formula 1C-1 to Chemical Formula 1C-3,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L a and L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R a and R 1 to R 4 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L b and L c are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and
R b and R c are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
4. The organic optoelectronic device as claimed in claim 1 , wherein:
the first compound is represented by one of Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, Chemical Formula 1A-2-a, Chemical Formula 1A-3-b, and Chemical Formula 1A-3-c:
in Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, Chemical Formula 1A-2-a, Chemical Formula 1A-3-b, and Chemical Formula 1A-3-c,
Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L a and L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R a , R 1 , R 2 , and R 4 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L b and L c are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and
R b and R c are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
5. The organic optoelectronic device as claimed in claim 1 , wherein:
the second compound is represented by one of Chemical Formula 3-1 to Chemical Formula 3-3:
in Chemical Formula 3-1 to Chemical Formula 3-3,
Z 1 is N or C-L 5 -R 5 ,
Z 3 is N or C-L 7 -R 7 ,
Z 4 is N or C-L 8 -R 8 ,
Z 5 is N or C-L 9 -R 9 ,
Z 6 is N or C-L 10 -R 10 ,
at least two of Z 1 and Z 3 to Z 6 are N,
L 5 to L 10 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R 5 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
at least one of R 5 to R 10 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, or a substituted or unsubstituted triphenylene group, and
R d , R e , R f , and R g are each independently hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof.
6. The organic optoelectronic device as claimed in claim 1 , wherein:
R 5 to R 10 are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group, and
at least one of R 5 to R 10 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, or a substituted or unsubstituted triphenylene group.
7. The organic optoelectronic device as claimed in claim 6 , wherein:
R 5 to R 10 are each independently a group of Group I or Group II, and
at least one of R 5 to R 10 is a group of Group II
wherein, in Group I and Group II,
X 3 and X 101 is O or S,
R 101 to R 123 and R 125 to R 184 are each independently hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof, and
* is a linking point.
8. The organic optoelectronic device as claimed in claim 1 , wherein:
the second compound is represented by Chemical Formula 3-1a or Chemical Formula 3-3a:
in Chemical Formula 3-1a,
L 6 , L 8 , and L 10 are each independently a single bond or a substituted or unsubstituted phenylene group,
R 6 , R 8 , and R 10 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group,
at least one of R 6 , R 8 , and R 10 is a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group;
in Chemical Formula 3-3a,
X 2 is O or S,
L 5 and L 9 are each independently a single bond or a substituted or unsubstituted phenylene group,
R 5 and R 9 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group,
at least one of R 5 and R 9 is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
R f and R g are each independently hydrogen, deuterium, a C1to C10 alkyl group, a C6 to C12 aryl group, or a combination thereof.
9. The organic optoelectronic device as claimed in claim 8 , wherein:
the first compound is represented by Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, or Chemical Formula 1A-2-a:
in Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, and Chemical Formula 1A-2-a,
Ar is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group,
L a and L 1 to L 4 are each independently a single bond or a substituted or unsubstituted phenylene group,
R a and R 1 to R 4 are each independently hydrogen or the group represented by Chemical Formula a,
L b and L c are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and
R b and R c are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, in which a substituent of the substituted phenyl group, the substituted biphenyl group, the substituted naphthyl group, the substituted fluorenyl group, the substituted dibenzofuranyl group, or the substituted dibenzothiophenyl group is a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
10. The organic optoelectronic device as claimed in claim 1 , wherein:
the third compound is represented by one of Chemical Formula 4-1 to Chemical Formula 4-4:
in Chemical Formula 4-1 to Chemical Formula 4-4,
X 1 is O or S,
L 11 to L 16 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R 11 to R 14 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
R 15 and R 16 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C10 alkyl group.
11. The organic optoelectronic device as claimed in claim 1 , wherein:
the third compound is represented by one of Chemical Formula 4-1b, Chemical Formula 4-2b, Chemical Formula 4-2c, Chemical Formula 4-3b, Chemical Formula 4-3c, and Chemical Formula 4-3d:
in Chemical Formula 4-1b, Chemical Formula 4-2b, Chemical Formula 4-2c, Chemical Formula 4-3b, Chemical Formula 4-3c, and Chemical Formula 4-3d,
X 1 is O or S,
L 11 to L 16 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R 11 to R 14 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
R 15 and R 16 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C10 alkyl group.
12. The organic optoelectronic device as claimed in claim 11 , wherein:
the first compound is represented by Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, or Chemical Formula 1A-2-a, and
the second compound is represented by Chemical Formula 3-1a or Chemical Formula 3-3a:
in Chemical Formula 1A-1-b, Chemical Formula 1A-1-c, or Chemical Formula 1A-2-a,
Ar is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group,
L a and L 1 to L 4 are each independently a single bond or a substituted or unsubstituted phenylene group,
R a and R 1 to R 4 are each independently hydrogen or the group represented by Chemical Formula a,
L b and L c are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and
R b and R c are each independently substituted or unsubstituted, phenyl group, a substituted or unsubstituted biphenyl group, substituted or naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group;
in Chemical Formula 3-1a,
L 6 , L 8 , and L 10 are each independently a single bond or a substituted or unsubstituted phenylene group,
R 6 , R 8 , and R 10 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and
at least one of R 6 , R 8 , and R 10 is a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group;
in Chemical Formula 3-3a,
X 2 is O or S,
L 5 and L 9 are each independently a single bond or a substituted or unsubstituted phenylene group,
R 5 and R 9 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group,
at least one of R 5 and R 9 is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
R f and R g are each independently hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C12 aryl group, or a combination thereof.
13. The organic optoelectronic device as claimed in claim 1 , wherein at least one of R 11 to R 14 of Chemical Formula 4 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
14. The organic optoelectronic device as claimed in claim 1 , wherein the first compound and the second compound are phosphorescent hosts of the light emitting layer.
15. The organic optoelectronic device as claimed in claim 14 , wherein the light emitting layer further includes a dopant.
16. A display device comprising the organic optoelectronic device as claimed in claim 1 .