Organic light-emitting diode

1. An organic light emitting device comprising:

a first electrode;

a second electrode;

a light emitting layer between the first electrode and the second electrode; and

one or more organic material layers provided between the first electrode and the light emitting layer,

wherein the one or more organic material layers include a cured material of a coating composition including an ionic compound including an anion group represented by the following Chemical Formula 1; and a compound of the following Chemical Formula 2-1, or a compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4:

in Chemical Formula 1,

at least one of R1 to R20 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group;

at least one of the remaining R1 to R20 is a curing group;

the remaining R1 to R20 if present are the same as or different from each other, and each independently hydrogen; deuterium; a nitro group; —C(O)R 100 ; —OR 101 ; —SR 102 ; —SO 3 R 103 ; —COOR 104 ; —OC(O)R 105 ; —C(O)NR 106 R 107 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;

R 100 to R 107 are the same as or different from each other, and each independently hydrogen;

deuterium; or a substituted or unsubstituted alkyl group;

in Chemical Formulae 2-1 to 2-4,

Ar1 and L7 to L9 are the same as or different from each other, and each independently an arylene group unsubstituted or substituted with a curing group;

m1 is 0 or 1, and when m1 is 0, Ar1 is an aryl group unsubstituted or substituted with a curing group;

L2 to L6 and L14 to L19 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;

L10 to L13 are the same as or different from each other, and each independently a direct bond; — 0 —; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; a substituted or unsubstituted divalent aryloxy group; or a substituted or unsubstituted divalent heterocyclic group;

Y1 and Y2 are the same as or different from each other, and each independently N(Ar2) or C(Ar3)(Ar4);

Ar2 to Ar16 are the same as or different from each other, and each independently a curing group; an alkyl group unsubstituted or substituted with a curing group; an aryl group unsubstituted or substituted with a curing group; or a heterocyclic group unsubstituted or substituted with a curing group;

R201 to R206 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a curing group;

wherein R201 to R206 are a curing group, or at least one of Ar2 to Ar16 is the curing group, an aryl group substituted with the curing group, or a heterocyclic group substituted with the curing group;

R301 to R312 are the same as or different from each other, and each independently hydrogen; or a substituted or unsubstituted alkyl group;

s1 is an integer of 1 to 4, and when s1 is 2 or greater, Ar1s are the same as or different from each other;

s7, s8 and s10 to s13 are each an integer of 1 to 4, and when s7, s8 and s10 to s13 are 2 or greater, L7s, L8s, L10s to L13s are the same as or different from each other;

t1 and t2 are each an integer of 0 to 7, and when t1 and t2 are 2 or greater, R201s and R202s are the same as or different from each other;

t3, t4 and t6 are each an integer of 0 to 3, and t5 is an integer of 0 to 4, and when t3 to t6 are 2 or greater, R203s to R206s are the same as or different from each other;

m2 to m4 and n2 to n4 represent a mole fraction of the structure in the parenthesis, and m2+n2=m3+n3=m4+n4≤100%; and

m2:n2=99:1 to 50:50, m3:n3=99:1 to 50:50, and m4:n4=99:1 to 50:50.

2. The organic light emitting device of claim 1 , wherein the organic material layer is a hole injection layer.

3. The organic light emitting device of claim 1 , wherein, in the coating composition, the compound of Chemical Formula 1; and the compound of Chemical Formula 2-1 or the compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4 are included in a weight ratio of 1:1 to 1: 99.

4. The organic light emitting device of claim 1 , wherein the curing group is selected from the group consisting of the following curing groups:

in the group of the curing groups, L is a direct bond; O; S; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;

k is an integer of 1 or 2, and when k is 2, the Ls are the same as or different from each other; and

R21 is a substituted or unsubstituted alkyl group.

5. The organic light emitting device of claim 1 , wherein the anion group of Chemical Formula 1 is any one selected from among the following structural formulae:

in the structural formulae, n is an integer of 1 to 3, m is an integer of 1 to 3, and m+n=4;

q is an integer of 0 to 3, r is an integer of 1 to 4, and q+r=4;

Z is deuterium; a halogen group; a nitro group; a cyano group; an amino group; —C(O)R 100 ; —OR 101 ; —SR 102 ; —SO 3 R 103 ; —COOR 104 ; —OC(O)R 105 ; —C(O)NR 106 R 107 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;

1 is an integer of 1 to 4, and when 1 is 2 or greater, Zs are the same as or different from each other; and

R 100 to R 107 are the same as or different from each other, and each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

6. The organic light emitting device of claim 1 , wherein the ionic compound includes a cation group, and the cation group is selected from among monovalent cation groups, onium compounds or the following structural formulae:

in the structural formulae, X 1 to X 75 are the same as or different from each other, and each independently hydrogen; a cyano group; a nitro group; a halogen group; —COOR 104 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group;

R 104 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group;

p is an integer of 0 to 10; and

a is 1 or 2, b is 0 or 1, and a+b=2.

7. The organic light emitting device of claim 6 , wherein the cation group is represented by any one of the following Chemical Formula 10 to Chemical Formula 15:

X 47 to X 50 , X 100 to X 129 and X 133 to X 142 are the same as or different from each other, and each independently hydrogen; a cyano group; a nitro group; a halogen group; —COOR 104 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group; and

R 104 is a substituted or unsubstituted alkyl group.

8. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 2-1, and the compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4 are any one selected from among the following structural formulae:

in the structural formulae, m3 and n3 have the same definitions as in Chemical Formula 2-3.

9. The organic light emitting device of claim 1 , wherein the compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4 has a weight average molecular weight of greater than or equal to 7,000 and less than or equal to 500,000.

10. The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 has a LUMO level from 4.5 eV to 6.5 eV, and

the compound of Chemical Formula 2-1 and the compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4 have HOMO levels from 4.8 eV to 5.8 eV.

11. The organic light emitting device of claim 1 , wherein the number of the curing group of the anion group represented by Chemical Formula 1 is 1, 2 or 4.

12. The organic light emitting device of claim 1 , wherein the number of the F, the cyano group, or the substituted or unsubstituted fluoroalkyl group in the anion group represented by Chemical Formula 1 is from 8 to 20.

13. The organic light emitting device of claim 1 , wherein parts by weight of the F in the anion group is from 15 parts by weight to 50 parts by weight or less with respect to 100 parts by weight of the anion group.

14. The organic light emitting device of claim 1 , wherein at least one benzene ring among the R1 to R5-bonding benzene ring, the R6 to R10-bonding benzene ring, the R11 to R15-bonding benzene ring, and the R16 to R20-bonding benzene ring in Chemical Formula 1 is selected from among the following structural formulae:

15. The organic light emitting device of claim 1 , wherein at least one benzene ring among the R1 to R5-bonding benzene ring, the R6 to R10-bonding benzene ring, the R11 to R15-bonding benzene ring, and the R16 to R20-bonding benzene ring in Chemical Formula 1 is selected from among the following structural formulae:

16. The organic light emitting device of claim 1 , wherein the ionic compound is selected from among the following structural formulae:

17. The organic light emitting device of claim 1 , wherein the repeating unit of Chemical Formula 2-2 to Chemical Formula 2-4 is a random polymerized, alternating polymerized or block polymerized compound.

18. The organic light emitting device of claim 1 , wherein in the repeating units of Chemical Formulae 2-2 to 2-4, the units repeated by m2 and n2 are random polymerized, the units repeated by m3 and n3 are random polymerized, and the units repeated by m4 and n4 are random polymerized.

19. The organic light emitting device of claim 1 , wherein in the repeating units of Chemical Formulae 2-2 to 2-4, the units repeated by m2 and n2 are block polymerized, the units repeated by m3 and n3 are block polymerized, and the units repeated by m4 and n4 are block polymerized.

20. The organic light emitting device of claim 10 , wherein the LUMO level of the compound of Chemical Formula 1 is lower than the HOMO levels of the compound of Chemical Formula 2-1 and the compound including any one repeating unit among Chemical Formula 2-2 to Chemical Formula 2-4.