Organic optoelectronic device and display apparatus
The present invention relates to an organic optoelectronic device and a display apparatus comprising same, the organic optoelectronic device comprising: an anode and a cathode facing each other; a light-emitting layer located between the anode and cathode; a hole transport layer located between the anode and light-emitting layer; an auxiliary hole transport layer located between the hole transport layer and light-emitting layer; an electron transport layer located between the cathode and light-emitting layer; and an auxiliary electron transport layer between the electron transport layer and light-emitting layer, wherein the auxiliary electron transport layer comprises at least one type of a first compound expressed by a particular Chemical Formula, and the auxiliary hole transport layer comprises at least one type of a second compound expressed by a particular Chemical Formula.
1. An organic optoelectronic device, comprising
an anode and a cathode facing each other,
a light-emitting layer located between the anode and cathode,
a hole transport layer located between the anode and light-emitting layer,
an auxiliary hole transport layer located between the hole transport layer and light-emitting layer,
an electron transport layer located between the cathode and light-emitting layer, and
an auxiliary electron transport layer between the electron transport layer and light-emitting layer,
wherein the auxiliary electron transport layer includes at least one type of a first compound expressed by Chemical Formula 1, and
the auxiliary hole transport layer includes at least one type of a second compound expressed by Chemical Formula 2:
wherein, in Chemical Formula 1,
Z is independently N, C, or CR a ,
at least one of Z is N,
R 1 to R 6 and R a are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L 1 to L 6 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof, and
s1 to s6 are independently an integer ranging from 0 to 5,
wherein, in Chemical Formula 2,
R 10 to R 19 are independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
L 7 is a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
“substituted” refers replacement of at least one hydrogen by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
2. The organic optoelectronic device of claim 1 , wherein the first compound is expressed by one of Chemical Formula 1-i to Chemical Formula 1-ix:
wherein in Chemical Formula 1-i,
R a1 and R a2 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n1 and n2 are independently an integer of 0 or 1, provided that n1 and n2 are not simultaneously 0,
wherein, in Chemical Formula 1-ii,
R b1 to R b6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
n3 to n8 are independently an integer of 0 or 1, but n3 to n5 are not 0 simultaneously and n6 to n8 are not 0 simultaneously,
wherein in Chemical Formula 1-iii,
R c1 to R c4 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n9 to n12 are independently an integer of 0 or 1,
wherein in Chemical Formula 1-iv,
R d1 to R d8 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n13 to n20 are independently an integer of 0 or 1,
In Chemical Formula 1-v,
X a to X f are independently N or CH,
at least one of X a to X c is N,
at least one of X d to X f is N,
R e1 to R e6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n21 to n26, ml and m2 are independently an integer of 0 or 1,
wherein in Chemical Formula 1-vi,
R f1 to R f6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n27 to n32 are independently an integer of 0 or 1, but n27 to n29 are not 0 simultaneously and n30 to n32 are not 0 simultaneously,
wherein, in Chemical Formula 1-vii,
X g to X l are independently N or CH,
at least one of X g to X i is N,
at least one of X g to X i is N,
R g1 and R g2 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
n33 and n34 are independently an integer of 0 or 1,
wherein in Chemical Formula 1-viii,
R h1 to R h6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
n35 to n40 are independently an integer of 0 or 1,
wherein in Chemical Formula 1-ix,
R i1 R i3 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
n41 to n43 are independently an integer ranging of 0 or 1,
in Chemical Formulae 1-i to 1-v and 1-ix, X 1 to X 9 is CH or N, at least one of the X 1 to X 9 is N, and
in Chemical Formulae 1-vi, 1-vii, and 1-viii, X 1 to X 3 is CH or N, at least one of the X 1 to X 3 is N, and
“substituted” refers to replacement of at least one hydrogen by deuterium. a halogen. a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
3. The organic optoelectronic device of claim 1 , wherein the first compound is expressed by Chemical Formula Y:
wherein, in Chemical Formula Y,
Z is independently N or CH,
at least one of Z is N,
R 1 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L 1 to L 6 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof, and
s1 to s6 are independently an integer of 0 to 5,
“substituted” refers to replacement of at least one hydrogen by deuterium, halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
4. The organic optoelectronic device of claim 1 , wherein the first compound is expressed by Chemical Formula Z:
wherein, in Chemical Formula Z,
Z is independently N or CH,
at least one of Z is N,
R 1 to R 6 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L 1 to L 6 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted heteroarylene group, or a combination thereof, and
s1 to s6 are independently an integer ranging from 0 to 5,
“substituted” refers to replacement of at least one hydrogen by deuterium, halogen, a hydroxy group, an amino group. a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
5. The organic optoelectronic device of claim 1 , wherein the second compound is expressed by one of Chemical Formula 2-i to Chemical Formula 2-iii:
wherein, in Chemical Formula 2-i,
L 7 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof, and
R j1 R j6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof,
p1 to p4 are independently an integer of 0 to 5, provided that 0≤p1+p2≤5, and 0≤p3+p4≤5,
wherein, in Chemical Formula 2-ii,
L 7 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R k1 to R k6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof,
R k7 and R k8 are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof,
p5 and p6 are independently an integer of 0 to 5, provided that 0≤p5+p6≤5, and
p7 and p8 are independently an integer of 0 to 4, provided that 0≤p7+p8≤4,
wherein, in Chemical Formula 2-iii,
L 7 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof,
R m1 to R m6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof,
R m7 to R m10 are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetero arylene group, or a combination thereof, and
p9 to p12 are independently an integer ranging from 0 to 4, provided that 0≤p9+p10≤4 and 0≤p11+p12≤4,
“substituted” refers replacement of at least one hydrogen by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
6. The organic optoelectronic device of claim 5 , wherein L 7 is one of linking groups of Group A:
wherein, in Group A,
R n1 to R n13 are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
q1 to q6 and q13 are independently an integer ranging from 0 to 4, and
q9 and q10 are independently an integer ranging from 0 to 3,
“substituted” refers replacement of at least one hydrogen by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
7. The organic optoelectronic device of claim 5 , wherein in [Chemical Formula 2-i], [Chemical Formula 2-ii], and [Chemical Formula 2-iii],
the C6 to C30 arylene group is a phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, a fluorenylene group, or a combination thereof, and
the C6 to C30 aryl group is a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a fluorenyl group, or a combination thereof.
8. The organic optoelectronic device of claim 1 , wherein
the auxiliary electron transport layer is
a first compound expressed by Chemical Formula 1-i or 1-ii, and
the auxiliary hole transport layer includes a second compound expressed by Chemical Formula 2-i:
wherein, in Chemical Formula 1i,
R a1 and R a2 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n1 and n2 are independently an integer of 0 or 1, provided that n1 and n2 are not simultaneously 0, and
X 1 to X 9 are CH or N, provided that at least one of X 1 to X 9 is N,
wherein, in Chemical Formula 1ii,
R b1 to R b6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
n3 to n8 are independently an integer of 0 or 1, but n3 to n5 are not 0 simultaneously and n6 to n8 are not 0 simultaneously, and
X 1 to X 9 are CH or N, provided that at least one of X 1 to X 9 is N,
wherein in Chemical Formula 2-i,
L 7 is a substituted or unsubstituted C6 to C30 arylene group,
R j1 to R j6 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
p1 to p4 are independently an integer of 0 to 5, provided that 0≤p1+p2≤5, and 0≤p3+p4≤5,
“substituted” refers replacement of at least one hydrogen by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a fluorenyl group, or a cyano group.
9. The organic optoelectronic device of claim 1 , wherein the first compound is one of compounds of Group 1:
10. The organic optoelectronic device of claim 1 , wherein the auxiliary hole transport layer contacts the hole transport layer and the light-emitting layer respectively, and
the auxiliary electron transport layer contacts the electron transport layer and the light-emitting layer respectively.
11. The organic optoelectronic device of claim 1 , wherein the light-emitting layer further includes a fluorescent dopant.
12. The organic optoelectronic device of claim 1 , wherein in [Chemical Formula 2],
the C6 to C30 arylene group is a phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, a fluorenylene group, or a combination thereof, and
the C6 to C30 aryl group is a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a fluorenyl group, or a combination thereof.
13. A display apparatus comprising the organic optoelectronic device of claim 1 .
14. The organic optoelectronic device of claim 1 , wherein the organic optoelectronic device is selected from an organic light emitting diode, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photo conductor drum, and an organic memory device.