Using the generating function of $\displaystyle\{H_k^2\}_{k=1}^\infty$:
$$
\frac{\text{Li}_2(x) +\ln^2(1-x)}{1-x} = \sum_{k=1}^\infty H_k^2 x^k
$$ we can observe that
\begin{align*}
S =& \sum_{k=1}^\infty {H_k^2 \over 2^k} \frac 1{k^2}\\
=& \sum_{k=1}^\infty {H_k^2 \over 2^k} \frac 1 2\int_0^1 x^{k-1}\ln^2 x\ dx\\
=&\frac 1 2 \int_0^1 \left(\sum_{k=1}^\infty H_k^2\left(\frac x 2\right)^k\right)\frac{\ln^2 x}{x} dx\\
=& \frac 1 2 \int_0^{\frac 1 2}\left(\sum_{k=1}^\infty H_k^2 x ^k\right) \frac{\ln^2 (2x)}{x} dx \\
=& \frac 1 2 \int_0^{\frac 1 2} \frac{\text{Li}_2(x) +\ln^2(1-x)}{1-x} \frac{\ln^2 x}{x} dx \\
&+ \ln 2\int_0^{\frac 1 2} \frac{\text{Li}_2(x) +\ln^2(1-x)}{1-x} \frac{\ln x}{x} dx \\
&+\frac{\ln^2 2}{2}\int_0^{\frac 1 2} \frac{\text{Li}_2(x) +\ln^2(1-x)}{1-x} \frac{dx}{x}\\
=&: I_1 + I_2 + I_3.
\end{align*}
For $I_1$, we have
\begin{align*}
I_1=&\frac 1 2 \int_0^{\frac 12 } \frac{\big[\text{Li}_2(x)+\ln^2(1-x)\big]\ln^2 x}{x(1-x)}dx \\
=& \frac 1 2 \int_0^{\frac 12 } \frac{\text{Li}_2(x)\ln^2 x}{x}dx+\frac 1 2 \int_0^{\frac 12 } \frac{\text{Li}_2(x)\ln^2 x}{1-x}dx +\frac 1 2 \int_0^{\frac 1 2} \frac{\ln^2 (1-x)\ln^2 x}{x(1-x)} dx\\
=&:I_1'+I_1''+I_1'''.
\end{align*}
For $I_1'$, we integrate by parts twice to get
\begin{align*}
I_1' \underset{\text{IBP}}{=}& \frac 1 2\left[ \text{Li}_3(x)\ln^2 x\right]^{1/2}_0 -\int_0^{\frac 1 2}\frac{\text{Li}_3(x) \ln x}{x} dx\\
\underset{\text{IBP}}{=}&\frac{\ln^2 2\ \text{Li}_3(1/2)}2 - \left[\text{Li}_4(x)\ln x\right]^{1/2}_0 +\int_0^{\frac 1 2 }\frac{\text{Li}_4(x)}x dx\\
=&\frac{\ln^2 2\ \text{Li}_3(1/2)}2 + \ln 2\ \text{Li}_4(1/2)+\text{Li}_5(1/2)\\
=&\boxed{\text{Li}_5(1/2)+\ln 2\ \text{Li}_4(1/2)+\frac{7\ln^2 2}{16}\zeta(3)-\frac {\pi^2\ln^3 2}{24}+\frac{\ln^5 2}{12}}
\end{align*} where the well-known value of
$
\text{Li}_3(1/2) = \frac 78 \zeta(3) -\frac{\pi^2\ln 2}{12}+\frac{\ln^3 2}{6}
$ is used to simplify.
For $I_1''$, by integrating by parts,
\begin{align*}
I_1'' \underset{\text{IBP}}{=}& \frac 1 2 \int_0^{\frac 1 2} \ln(1-x)\left[\frac{2\ln x\text{Li}_2(x)}{x} - \frac{\ln(1-x)\ln^2 x}{x}\right]dx +\frac{\ln^3 2}{2}\text{Li}_2(1/2)\\
=& {\int_0^{\frac 1 2} \ln x\frac{\ln(1-x)\text{Li}_2(x)}{x} dx}-\underbrace{\frac 1 2 \int_0^{\frac 1 2} \frac{\ln^2(1-x)\ln^2 x}{x}dx}_{=:J} +\frac{\ln^3 2}{2}\text{Li}_2(1/2)\\
\underset{\text{IBP}}{=}&\frac{\ln 2}2\text{Li}_2^2(1/2) +{\frac 1 2\int_0^{\frac 1 2}\frac{\text{Li}_2^2(x)}{x} dx}-J +\frac{\ln^3 2}{2}\text{Li}_2(1/2)\\
=&\frac{\pi^4\ln 2}{288} -\frac{\ln^5 2}{8}+{\frac 1 2\int_0^{\frac 1 2}\frac{\text{Li}_2^2(x)}{x} dx}-J.
\end{align*}
The well-known value of $\text{Li}_2(1/2) = \frac{\pi^2}{12} - \frac{\ln^2 2}{2}$ is used to simplify. In fact, the integral ${\int_0^{1/2}\frac{\text{Li}_2^2(x)}{x} dx}$ was already evaluated in my previous answer here:
\begin{align*}
{\int_0^{\frac 1 2}\frac{\text{Li}_2^2(x)}{x} dx} = &-2\text{Li}_5(1/2) -2\ln 2\ \text{Li}_4(1/2)+\frac{27}{32}\zeta(5) +\frac{7\pi^2}{48}\zeta(3)-\frac{7\ln^2 2}{8}\zeta(3) \\
&-\frac{\pi^4\ln 2}{144} +\frac{\pi^2\ln^3 2}{12} - \frac{7\ln^5 2}{60}.
\end{align*}
For $J$, we make substitution $y= \frac{x}{1-x}$ to get
\begin{align*}
J=&\frac 1 2\int_0^1 \frac{\ln^2(1+y)\ln^2\left(\frac{y}{1+y}\right)}{y(1+y)}dy\\
=&\frac 1 2\int_0^1 \frac{\ln^2(1+y)\ln^2\left(\frac{y}{1+y}\right)}{y}dy-\frac 1 2\int_0^1 \frac{\ln^2(1+y)\ln^2\left(\frac{y}{1+y}\right)}{1+y}dy\\
=&:K-L.
\end{align*}
For $K$, expanding $\ln^2\left(\frac y {1+y}\right)=\big[\ln y -\ln(1+y)\big]^2$ and integrating by parts we get
\begin{align*}
K =&\frac 1 2\int_0^1 \frac{\ln^2(1+y)\ln^2\left(\frac{y}{1+y}\right)}{y}dy\\
=& \frac 12{ \int_0^1\frac{\ln^2 y\ln^2(1+y)}{y} dy}-{\int_0^1 \frac{\ln y\ln^3(1+y)}{y} dy}+\frac 12 \int_0^1 \frac{\ln^4(1+y)}{y}dy\\
\underset{\text{IBP}}{=}&-\frac 1 3 \int_0^1 \frac{\ln^3 y \ln(1+y)}{1+y}dy + \frac 3 2\int_0^1 \frac{\ln^2 y\ln^2(1+y)}{1+y}dy +\frac 12 \int_0^1 \frac{\ln^4(1+y)}{y}dy
\end{align*} Doing the same thing for $L$,
\begin{align*}
L = & \frac 1 2\int_0^1 \frac{\ln^2(1+y)\ln^2\left(\frac{y}{1+y}\right)}{1+y}dy\\
=& \frac 12 \int_0^1 \frac{\ln^2 y\ln^2(1+y)}{1+y}dy- {\int_0^1 \frac{\ln y\ln^3(1+y)}{1+y} dy} +\frac 12 \int_0^1 \frac{\ln^4(1+y)}{1+y} dy\\
\underset{\text{IBP}}{=}& \frac 12 \int_0^1 \frac{\ln^2 y\ln^2(1+y)}{1+y}dy+\frac 1 4 \int_0^1 \frac{\ln^4(1+y)}y dy +\frac{\ln^5 2}{10}.
\end{align*} This gives that
\begin{align*}
J=&K-L\\
=&-\frac 1 3 \int_0^1 \frac{\ln^3 y \ln(1+y)}{1+y}dy + \int_0^1 \frac{\ln^2 y\ln^2(1+y)}{1+y}dy +\frac 14 \int_0^1 \frac{\ln^4(1+y)}{y}dy -\frac{\ln^5 2}{10}\\
=&:-V_1+V_2+V_3 -\frac{\ln^5 2}{10}.
\end{align*}
For $V_1$, we can use the Maclaurin series of $\frac{\ln (1+y)}{1+y} = \sum_{k=0}^\infty (-1)^{k-1} H_k y^k$ to get
\begin{align*}
V_1=&\frac 1 3\int_0^1 \frac{\ln^3 y\ln(1+y)}{1+y} dy \\
=& \frac 1 3\sum_{k=0}^\infty (-1)^{k-1}H_k {\int_0^1 y^k\ln^3 y\ dy} \\
=& \frac{-6}{3}\sum_{k=0}^\infty \frac{(-1)^{k-1}H_k}{(k+1)^4}\\
=&2\sum_{k=0}^\infty \frac{(-1)^k \left(H_{k+1}-\frac 1{k+1}\right)}{(k+1)^4} \\
=&2 \sum_{k=1}^\infty \frac{(-1)^{k-1}H_k}{k^4} -2 \sum_{k=1}^\infty \frac{(-1)^{k-1}}{k^5}\tag{$k+1\mapsto k$}\\
=&2\left(\frac{59}{32}\zeta(5) - \frac{\pi^2\zeta(3)}{12}\right)-2\cdot \frac{15}{16}\zeta(5)\\
=&\frac{29}{16}\zeta(5) - \frac{\pi^2}{6}\zeta(3)
\end{align*} where the known value of alternating Euler sum $\sum_{k=1}^\infty \tfrac{(-1)^{k-1}H_k}{k^4}$ is used.
For $V_2$, we consider the algebraic identity
$$
6a^2b^2 = (a-b)^4 - a^4 +4a^3b +4ab^3 -b^4
$$ with $a=\ln y$ and $b = \ln(1+y)$ to get
\begin{align*}
V_2 =&\frac 1 6{\int_0^1 \frac{\ln^4\left(\frac y{1+y}\right)}{1+y} dy}-\frac 1 6\int_0^1 \frac{\ln^4 y}{1+y} dy +\underbrace{\frac 2 3\int_0^1 \frac{\ln^3 y\ln(1+y)}{1+y} dy}_{=2V_1}\\
&+\frac 2 3\underbrace{\int_0^1 \frac{\ln y\ln^3(1+y)}{1+y} dy}_{=- V_3\text{ by IBP}} -\frac 1 6\int_0^1 \frac{\ln^4(1+y)}{1+y} dy\\
=&\frac 1 6 \int_0^{\frac 1 2} \frac{\ln^4 x}{1-x} dx -\frac 1 6\int_0^1 \frac{\ln^4 y}{1+y} dy +2V_1-\frac 2 3 V_3 -\frac{\ln^5 2}{30}.\tag{$\tfrac y{1+y}= x$}
\end{align*}
For the first integral, we have
\begin{align*}
W:=&\frac 1 6{\int_0^{\frac 1 2 }\frac{\ln^4 x}{1-x} dx}\tag{$2x\mapsto x$} \\
=& \frac 1 6\int_0^1 \frac{\ln^4(\tfrac x 2)}{2-x}dx\\
=&\frac 1 6\sum_{k=1}^\infty \frac{1}{2^k}\int_0^1 x^{k-1}\Big[\ln^4 x -4\ln 2 \ln^3 x + 6\ln^2 2\ln^2 x - 4\ln^3 2 \ln x + \ln^4 2\Big]dx\\
=&\frac 1 6\sum_{k=1}^\infty \frac{1}{2^k}\left[\frac{24}{k^5} + \frac{24\ln 2}{k^4} +\frac {12\ln^2 2}{k^3} +\frac{4\ln^3 2}{k^2} +\frac{\ln^4 2}{k}\right]\\
=&4\text{Li}_5(1/2) +4\ln 2\text{Li}_4(1/2) + 2\ln^2 2\text{Li}_3(1/2) + \frac{2\ln^3 2}{3}\text{Li}_2(1/2) + \frac{\ln^5 2}6\\
=&4\text{Li}_5(1/2) +4\ln 2\text{Li}_4(1/2) + \frac{7\ln^2 2}{4}\zeta(3)-\frac{\pi^2\ln^3 2}{9}+ \frac{\ln^5 2}6.
\end{align*}
For the second integral, we have
\begin{align*}
\frac 1 6\int_0^1 \frac{\ln^4 y}{1+y} dy
=& \frac 1 6\sum_{k=1}^\infty (-1)^{k-1} \int_0^1 y^{k-1}\ln^4 y \ dy \\
=& \frac 1 6 \sum_{k=1}^\infty(-1)^{k-1} \frac{24}{k^5}\\
=&\frac{15}{4}\zeta(5).
\end{align*}
This gives
$$
V_2 = W +2V_1-\frac 2 3 V_3-\frac{15}{4}\zeta(5)-\frac{\ln^5 2}{30}.
$$
For $V_3$ we have
\begin{align*}
V_3=&\frac 14 \int_0^1 \frac{\ln^4(1+y)}{y}dy \tag{$y\mapsto y+1$}\\
=& \frac 1 {4}{ \int_1^2 \frac{\ln^4 y }{y-1} dy} \tag{$\tfrac 1 y\mapsto y$}\\
=&\frac 1 {4} \int_{\frac 1 2}^1 \frac{\ln^4 y}{y(1-y)} dy\\
=&\frac 1 {4} \int_{\frac 1 2}^1 \frac{\ln^4 y}{y} dy+\frac 1 {4} \int_{\frac 1 2}^1 \frac{\ln^4 y}{1-y} dy\\
=&\frac{\ln^5 2}{20} + \frac 1 {4} \int_0^1 \frac{\ln^4 y}{1-y} dy -\frac 1 {4} \underbrace{\int_0^{\frac 1 2}\frac{\ln^4 y}{1-y}dy}_{=6 W}\\
=&\frac{\ln^5 2}{20} +\frac 1 {4} \sum_{k=1}^\infty \int_0^1 y^{k-1}\ln^4 y\ dy- \frac 3 2 W\\
=&\frac{\ln^5 2}{20} +6\zeta(5)- \frac 3 2 W.
\end{align*}
Combining $V_1$, $V_2$ and $V_3$, we get
\begin{align*}
J = & V_2 -V_1+V_3 -\frac{\ln^5 2}{10}\\
=& \left[W+2V_1 -\frac 2 3 V_3-\frac{15}{4}\zeta(5)-\frac{\ln^5 2}{30}\right]-V_1+V_3 -\frac{\ln^5 2}{10}\\
=& W+V_1+\frac 1 3 V_3-\frac{15}{4}\zeta(5)-\frac{2\ln^5 2}{15}\\
=&\frac 1 2 W+V_1 -\frac 7 4\zeta(5) -\frac{7\ln^5 2}{60}\\
=&2\text{Li}_5(1/2) +2\ln 2\ \text{Li}_4(1/2) +\frac 1 {16}\zeta(5) -\frac{\pi^2}6 \zeta(3) +\frac {7\ln^2 2}{8} \zeta(3) -\frac{\ln^2 2\pi^3}{18}-\frac{\ln^5 2}{30}.
\end{align*}
This gives
\begin{align*}
I_1'' =&\frac{\pi^4\ln 2}{288} -\frac{\ln^5 2}{8}+\frac 1 2\int_0^{\frac 1 2}\frac{\text{Li}_2^2(x)}{x} dx-J\\
=&\boxed{\small -3\text{Li}_5(1/2) -3\ln 2\text{Li}_4(1/2) +\frac{23}{64}\zeta(5) +\frac {23\pi^2}{96}\zeta(3) -\frac {21\ln^2 2}{16}\zeta(3) +\frac{7\pi^2\ln^3 2}{72} - \frac{3\ln^5 2}{20}.}
\end{align*}
For $I_1'''$, we exploit the symmetric nature of the integrand to write
\begin{align*}
I_1''' :=& \frac 1 2\int_0^{\frac 1 2} \frac{\ln^2 x \ln^2 (1-x)}{x(1-x)} dx\\
=& \frac 1 4\int_0^1 \frac{\ln^2 x \ln^2 (1-x)}{x(1-x)} dx \\
=& \frac 1 4\underbrace{\int_0^1 \frac{\ln^2 x \ln^2 (1-x)}{x} dx}_{1-x\mapsto x}+\frac 1 4{\int_0^1 \frac{\ln^2 x \ln^2 (1-x)}{1-x} dx}\\
=&\frac 1 2\int_0^1 \frac{\ln^2 x \ln^2 (1-x)}{1-x} dx\\
=&\frac 1 2 \left[\frac{\partial^4}{\partial x^2 \partial y^2 } \text{B}(x,y)\right]_{x=1,y=0^+}
\end{align*} where $\text{B}(x,y)=\tfrac{\Gamma(x)\Gamma(y)}{\Gamma(x+y)}$ is Euler's Beta function. Now we can use the fact that
\begin{align*}
\lim_{y\to 0^+}\frac{\partial^3 }{\partial x\partial y^2 }\text{B}(x,y)
=&-\frac 1 3\psi'''(x)+\psi''(x)\Big[\psi(x) +\gamma\Big] + \psi'(x)\Big[\psi'(x)-\zeta(2) - \big[\psi(x) + \gamma\big]^2\Big]
\end{align*} to obtain
\begin{align*}
I_1'''=& \frac 1 2\frac d{dx}\left[\frac{\partial^3 }{\partial x\partial y^2 }\text{B}(x,0^+)\right]_{x=1} \\
=& -\frac 1 6 \psi''''(1) +\psi'(1)\psi''(1) \\
=&\boxed{4\zeta(5) -\frac{\pi^2}3 \zeta(3)}
\end{align*} where the values of $\psi(1) +\gamma = 0$, $\psi'(1) =\zeta(2)$, $\psi''(1) =-2\zeta(3)$ and $\psi''''(1) = -24\zeta(5)$ are used.
Finally, from $I_1 = I_1'+I_1''+I_1'''$ we get
\begin{align*}
I_1 =& -2\text{Li}_5(1/2) - 2\ln 2\text{Li}_4(1/2) + \frac {279}{64}\zeta(5) -\frac {3\pi^2}{32}\zeta(3)-\frac {7\ln^2 2}{8} \zeta(3)+\frac {\pi^2\ln^3 2}{18}-\frac{\ln^5 2}{15}.
\end{align*}
For $I_2$, we observe that
\begin{align*}\require{cancel}
I_2 =& \ln 2 \int_0^{\frac 12} \frac{\big[\text{Li}_2(x) + \ln^2(1-x)\big]\ln x}{x(1-x)} dx \\
=& \ln 2 {\int_0^{\frac 12} \frac{\text{Li}_2(x) \ln x}{1-x} dx}+\ln 2\int_0^{\frac 12} \frac{\ln^2(1-x)\ln x}{1-x} dx+ \ln 2 \int_0^{\frac 12} \frac{\big[\text{Li}_2(x) + \ln^2(1-x)\big]\ln x}{x} dx\\
\underset{\text{IBP}}{=}&-\ln^3 2\ \text{Li}_2(1/2)+\ln 2 \int_0^{\frac 12} \ln(1-x)\frac{-\cancel{\ln(1-x)\ln x}+\text{Li}_2(x)}{x} dx \\
&+\ln2 \int_0^{\frac 1 2} \frac{\ln^2(1-x)\ln x}{1-x} dx + \ln 2{ \int_0^{\frac 12} \frac{\big[\text{Li}_2(x)+\cancel{ \ln^2(1-x)}\big] \ln x}{x} dx}\\
\underset{\text{IBP}}{=}&\small-\ln^3 2 \text{Li}_2(1/2)-\tfrac{\ln 2}{2} \left[\text{Li}^2_2(x)\right]^{1/2}_0-\frac{\ln^5 2}3+{\frac{\ln 2}3{\int_0^{\frac 1 2} \frac{\ln^3(1-x)}{x} dx}} -\ln^2 2\ \text{Li}_3(1/2)-\ln 2\int_0^{\frac 1 2} \frac{\text{Li}_3(x)}{x} dx\normalsize\\
=&-\ln^3 2\ \text{Li}_2(1/2) -\tfrac{\ln 2}{2} \text{Li}^2_2(1/2)-\frac{\ln^5 2}3+ \small\underbrace{\frac{\ln 2}3{\int_{\frac 1 2}^1 \frac{\ln^3 x}{1-x} dx}}_{1-x\mapsto x, \ =:I_2'}\normalsize-\ln^2 2\ \text{Li}_3(1/2)-\ln 2\ \text{Li}_4(1/2)\\
=&-\ln 2\ \text{Li}_4(1/2) -\frac{7\ln^2 2}8 \zeta(3) -\frac{\pi^4 \ln 2}{288}+\frac {\pi^2\ln^3 2}{24} -\frac{\ln^5 2}{8} + I_2'.
\end{align*}
For $I_2'$, by integrating by parts, we have
\begin{align*}
I_2'
=& \frac{\ln 2}3\int_{\frac 1 2}^1 \frac{\ln^3 x}{1-x} dx\\
=&\frac{\ln 2}3\int_{0}^1 \frac{\ln^3 x}{1-x} dx -\frac{\ln 2}3{\int_{0}^{\frac 12} \frac{\ln^3 x}{1-x} dx}\tag{$x=\tfrac y 2$}\\
=&\frac{\ln 2}3\sum_{k=1}^\infty {\int_0^1 x^{k-1}\ln^3 x\ dx}-\underbrace{\frac{\ln 2}3\int_{0}^{1} \frac{\ln^3 (\tfrac y 2)}{2-y} dy}_{=:A}\\
=&-\frac{\pi^4\ln 2}{45}-A.
\end{align*}
\begin{align*}
A=&\frac{\ln 2}3\sum_{k=1}^\infty \frac 1 {2^k}\int_{0}^{1} y^{k-1}\ln^3 (\tfrac y 2) dy\\
=&\frac{\ln 2}3\sum_{k=1}^\infty \frac 1 {2^k}\int_{0}^{1} y^{k-1}\left[\ln^3 y - 3\ln 2\ln^2 y +3\ln^2 2\ln y -\ln^3 2\right]dy\\
=&-\frac{\ln 2}3\sum_{k=1}^\infty \frac 1 {2^k}\left[\frac 6 {k^4}+\frac{6\ln 2}{k^3} +\frac{3\ln^2 2}{k^2} +\frac{\ln^3 2}{k}\right]\\
=& -2\ln 2\ \text{Li}_4(1/2) - 2\ln^2 2\ \text{Li}_3(1/2)-\ln^3 2\ \text{Li}_2(1/2)-\frac{\ln^5 2}3\\
=&-2\ln 2\ \text{Li}_4(1/2)-\frac{7\ln^2 2}{4}\zeta(3)+\frac{\pi^2\ln^3 2}{12}-\frac{\ln^5 2}{6}.
\end{align*}
This gives
$$
I_2'= 2\ln 2\ \text{Li}_4(1/2)+\frac{7\ln^2 2}{4}\zeta(3)-\frac{\pi^4\ln 2}{45}-\frac{\pi^2\ln^3 2}{12}-\frac{\ln^5 2}{6}
$$ and
\begin{align*}
I_2=\ln 2\ \text{Li}_4(1/2)+\frac{7\ln^2 2}{8}\zeta(3)-\frac{37\pi^4\ln 2}{1440}-\frac{\pi^2\ln^3 2}{24}+\frac{\ln^5 2}{24}.
\end{align*}
For $I_3$, we have
\begin{align*}
I_3=&\frac{\ln^2 2}{2}\int_0^{\frac 1 2} \frac{\text{Li}_2(x)+\ln^2(1-x)}{x(1-x)}dx\\
=&\frac{\ln^2 2}{2}\int_0^{\frac 1 2} \frac{\text{Li}_2(x)}{x}dx+\frac{\ln^2 2}{2}\int_0^{\frac 1 2} {\left[\frac{\ln^2(1-x)}{x}+\frac{\text{Li}_2(x)}{1-x}\right]}dx+\frac{\ln^2 2}{2}\int_0^{\frac 1 2} \frac{\ln^2(1-x)}{1-x}dx\\
=&\frac{\ln^2 2}{2}\text{Li}_3(1/2) +\frac{\ln^2 2}{2}\big[-\ln(1-x)\text{Li}_2(x)\big]^{1/2}_0+\frac{\ln^5 2}6.
\end{align*} Using the well-known values of $\text{Li}_3(1/2)$ and $\text{Li}_2(1/2)$, this simplifies to
$$
I_3 =\frac {7\ln^2 2}{16}\zeta(3).
$$
From $S = I_1+I_2 + I_3$, we finally get
\begin{align*}
\sum_{k=1}^\infty \frac{H_k^2}{k^32^k} =& -2\text{Li}_5(1/2) -\ln 2\ \text{Li}_4(1/2) + \frac{279}{64}\zeta(5) - \frac{3\pi^2}{32}\zeta(3) + \frac{7\ln^2 2}{16}\zeta(3) - \frac{37\pi^4 \ln 2}{1440}\\
& + \frac{\pi^2 \ln^3 2}{72} - \frac{\ln^5 2}{40}.
\end{align*}
We can observe that the values of $I_2$ and $I_3$ can be used to evaluate sums of lower order in a similar way:
\begin{eqnarray*}
&\sum_{k=1}^\infty \frac{H_k^2}{k^2 2^k} = -\frac 1{\ln 2} I_2 - \frac{2}{\ln 2} I_3=-\text{Li}_4(1/2) -\frac{7\ln 2}4\zeta(3) +\frac{37 \pi^4}{1440} +\frac{\pi^2\ln^2 2}{24} -\frac{\ln^4 2}{24},\\
&\sum_{k=1}^\infty \frac{H_k^2}{k 2^k} = \frac{2}{\ln^2 2} I_2 = \frac{7}{8}\zeta(3).
\end{eqnarray*}
Best Answer
\begin{align} I&=\int_0^1\frac{\operatorname{Li}_2(-x^2)}{1+x^2}\ dx\\ &=-\frac{\pi^3}{48}+2\int_0^1\frac{\arctan x\ln(1+x^2)}{x}\ dx\tag1\\ &=-\frac{\pi^3}{48}-4\sum_{n=0}^\infty\frac{(-1)^nH_{2n}}{2n+1}\int_0^1 x^{2n}\ dx\tag2\\ &=-\frac{\pi^3}{48}-4\sum_{n=0}^\infty\frac{(-1)^nH_{2n}}{(2n+1)^2}\tag3\\ &=-\frac{\pi^3}{48}-4\sum_{n=0}^\infty\frac{(-1)^nH_{2n+1}}{(2n+1)^2}+4\underbrace{\sum_{n=0}^\infty\frac{(-1)^n}{(2n+1)^3}}_{\beta(3)=\frac{\pi^3}{32}}\tag4\\ &=\frac{5\pi^3}{48}-4\Im\sum_{n=1}^\infty\frac{(i)^nH_n}{n^2}\tag5\\ &=\frac{5\pi^3}{48}-4\left(-\frac{\pi}{16}\ln^22-\frac12\ln2\ G-\Im\operatorname{Li}_3(1-i)\right)\tag6\\ &=\frac{5\pi^3}{48}+\frac{\pi}{4}\ln^22+2\ln2\ G+4\Im\operatorname{Li}_3(1-i) \end{align}
The related sum can be obtained from the the generating function
$$\sum_{n=1}^\infty H_n^{(q)}x^n=\frac{\operatorname{Li}_q(x)}{1-x}$$
set $q=2$ and replace $x$ with $-x^2$ we get
$$\sum_{n=1}^\infty (-1)^nH_n^{(2)}x^{2n}=\frac{\operatorname{Li}_2(-x^2)}{1+x^2}$$
now integrate both sides from $x=0$ to $1$
$$\sum_{n=1}^\infty \frac{(-1)^nH_n^{(2)}}{2n+1}=\int_0^1\frac{\operatorname{Li}_2(-x^2)}{1+x^2}\ dx$$
The index $n$ can start from $0$ as $H_{0}^{(2)}=0$
.
Explanation:
$(1)$ Integration by parts.
$(2)$ Using the identity $\arctan x\ln(1+x^2)=-2\sum_{n=0}^\infty\frac{(-1)^nH_{2n}}{2n+1}x^{2n+1}$.
$(3)$ $\int_0^1 x^{a-1}\ dx=\frac1a$
$(4)$ Using $H_n=H_{n+1}-\frac1{n+1}$
$(5)$ Using $\sum_{n=0}^\infty (-1)^n a_{2n+1}=\Im\sum_{n=1}^\infty i ^n a_n$
$(6)$ Using the generating function $\sum_{n=1}^\infty\frac{H_{n}}{n^2}x^{n}=\operatorname{Li}_3(x)-\operatorname{Li}_3(1-x)+\ln(1-x)\operatorname{Li}_2(1-x)+\frac12\ln x\ln^2(1-x)+\zeta(3)$